The Pain of It All
Rob waited patiently at the exit to the car park outside Blum
Industries. It had taken him some time and lots of forced courage to
ask Debby out. It was just a Wednesday night. She had refused him
politely many times but he was not discouraged; the more Debbie
dismissed it, the greater his desire to win her over. He was patient.
Finally at lunch on Monday, he was alone with her for an instant and
invited her for a drink at a nice bar he had discovered over the
weekend.
Debby was just as tall as Rob, slim with a small bust line. She has
short blonde hair and wore very little makeup. She was pretty in Rob's
eyes and her reticence to talk or engage with others indicated some
trouble in her life. She appeared to have trouble around people and
particularly men. She did sit with him though at the lunch table but
mostly with others. Ron wondered at her, even wondering if she was a
lesbian and hence the refusals to hook up earlier. Debby had startling
blue eyes and her gaze would fix you. Somehow, his attraction was her
ability to say 'no' to him repeatedly. None of the other guys would
even try to approach her. That penetrating gaze would cut them down.
It was not that Rob was so self-confident and good looking. He was of
average build, height and looks with few friends in this town. He
sensed a kindred spirit in Debbie. Quite often they would sit together
at the same long lunch table and mostly with others. Except for some
comment on the weather or a sports result, their conversation never
progressed much. Occasionally she would smile and this lit up her
face. Both were relatively new to Blum and also to this large city.
Last Saturday, with nothing to do and no particular place in mind, Rob
took a walk downtown towards the busy cafes and bars along the
waterfront. There was a small alleyway connecting the river walkway to
a larger street and Rob decided to walk back along the main road.
Halfway down the alley he heard some laughter and discovered a small
bar. It wasn't overly busy but there was a mixed crowd. He decided to
go in and have a quick beer. There were many young people and it
seemed like everybody was having a good time. He ordered a beer and
the friendly female bartender welcomed him in. He drank his beer
slowly, ordered a burger and fries from the very simple menu and
looked around. He liked the bar and his ability to be alone yet
surrounded by people.
On the following Monday, sitting across from Debby, he mentioned what
he had discovered over the weekend. Debby appeared uninterested as
always. Plucking up courage toward the end of their meal he asked if
she would like to join him for a drink and he would show her this
hidden gem.
Debby didn't respond for a long moment, staring at him with those
startling blue eyes. "OK. What time?" she finally responded.
"Well, we could go directly from work and I can drop you back here
later." Rob was surprised to get an answer - a positive one - and
smiled at the thought of a date, his first in a long time. "I can meet
you at the exit to the building around 5.15 and drive you there."
"OK." Debby arose and left Rob thinking of his good luck. It was a
strange kind of first date to go straight from work to a bar but it
did mean there was no pressure. Hopefully, there would be many more
dates.
Rob watched the staff leave the building. He had parked in front of
the exit as if he was here to pick someone up. He finally saw her
approaching and smiled. It looked like she was going to have a drink
with him. Debby was talking to another girl that Rob recognized from
the corridors but didn't know at all.
Debby had a small smile on her face as she approached Rob. "Hi, Rob, I
asked Tara here to join us. She doesn't live far from me and I can
drop off later. Is that OK?"
"Of course," Rob quickly replied and introduced himself. "My
pleasure." He saw that Tara was a little nervous fearing intrusion
into a 'date' but Rob put her at ease quickly. Tara was a little
shorter than Rob, with dark brown shoulder-length hair and better
curves. She was pretty in a different way to Debby. He thought that
for the initial 'meeting' Debby would be more at ease and then, when
she got to know Rob better, she would be happy on her own. It would
also be a badge for Rob to enter the bar with two girls on his arm.
Debby got into the front and Tara in the back.
On the short drive to the bar, they talked about common contacts in
the office. Debby replied in one-word answers. Tara talked a little
more. They had to walk a few minutes down the alley to enter the bar.
It was not yet 6 pm and the bar was busy but not full. They found a
quiet table and Rob volunteered to get the drinks. One guy with two
pretty girls would always draw attention. Rob basked in that even if
it was not planned.
In that atmosphere, it was a light conversation, mostly about their
respective roles at Blum. Debby was a research assistant and had moved
here a few months ago from Texas. She had graduated from college just
one year ago. Tara was in customer service, was a local girl that had
attended a local community college. She too had graduated a year ago
and Rob assumed that they were both around twenty-two years old. Rob
himself was just a year older and working in administration. It was a
light conversation and Debby responded to questions from Rob in single
sentences. She appeared to know Tara better. Rob spent his time
chatting with Tara who had no problem chatting about their co-workers,
sports of music. Debby just looked on without any emotion showing on
her face. Rob invited them both for dinner but Debby begged off as she
had to call her folks who were two hours ahead. Tara also declined as
she thought Rob's invitation was out of politeness. She didn't want to
butt in between Debby and Rob. As agreed, Rob dropped Tara off first
and then drove back to the office where Debby had parked her car.
"Thanks, see you tomorrow," was Debby's comment as she hastily stepped
out of the car leaving Ron feeling very disappointed. Yet, he wasn't
deterred and promised to try again. It wasn't a date as such but he
expected a kiss on the cheek at least. Still, Debby had not seemed
upset and the 'see you tomorrow' line gave him some hope.
At lunch the next day it was the same routine. Ron asked Debby if she
liked the bar.
"It was nice," was her response as she ate her salad.
"Great, I'm glad. Perhaps we can do that again," Rob said hopefully.
"OK," was Debby's terse reply.
"Would you like to go back there for a drink on Saturday? Perhaps have
some dinner?" Ron asked encouraged by Debby's response.
Debby stared at Rob again. He was getting used to that look. It
appeared she was sizing him up. It was rather unnerving to have those
bright blue eyes stare at him.
"You can pick me up at 6.30 at my apartment. I'll text you the
address." The conversation was over. Debby got up and left Rob staring
at her pert behind.
As promised, Rob got the email with the address and a short note to
say that 'they would be ready by 6.30'. Rob wasn't sure what Debby
meant with 'they'. Was it Tara again? Or was it just an expression on
Debby's part. Tara was very pleasant and Rob liked her, but there was
something mysterious and hidden about Debby that made him even more
curious. He even went so far as to ask himself if Debby and Tara were
in a relationship. But, in that case, why even agree to go out with
Rob? It didn't make sense but her strange behavior was a challenge to
him. He called the restaurant and made the reservation for 3.
On Saturday, Rob dressed in a smart jacket and open shirt and drove to
Debby's apartment. He saw Debby and Tara waiting outside. Both were
dressed smartly for a night out. Debby had even a light application of
lipstick but no other makeup. Tara had applied her makeup skillfully
for a night out. Debby wore a pants suit whilst Tara wore a nice dress
in a dark olive color. Rob was disappointed that he wouldn't get time
alone with Debby. But also pleased that he would have two nice looking
girls at his side. Quite a lot of progress for a guy who hadn't had a
date in many months.
"I thought we could have a drink at that bar and I made a reservation
at a small Italian restaurant a few minutes' walk from the bar. Is
that OK with you ladies?" Rob asked cheerfully.
"Sure," Tara replied first.
"OK," was Debby's short reply.
Rob got them drinks in the crowded bar. Tara seemed genuinely happy to
be out and in company. Debby was her usual taciturn self. It was less
that she was impolite but more that she had very little to say
voluntarily. She answered questions but did not attempt to start a
thread in the conversation. The bar was noisy and after one drink they
decided to head for the restaurant. Rob felt particularly good to be
observed by all that he was accompanied by two ladies.
The small restaurant was busy on a Saturday night and Rob was glad he
had the reservation. The Italian food was great and they shared
plates. Debby was a little more talkative but Tara and Rob kept the
conversation alive. As they all related their backgrounds, Debby
recalled how her family lived on the outskirts of a large city and her
father was a long-distance truck driver. Tara's parent owned a small
hardware store in rural Iowa. Rob described his background from
Washington State. All had diverse backgrounds and were now working on
the outskirts of the Windy City, Chicago. As the dinner progressed,
Debby seemed to retreat after her initial participation in the
discussion.
As they finished dinner, the girls opted out of dessert. Rob ordered
coffee as did Tara. Suddenly Debby rose, told them to take their time
and she would meet them outside when they were done. Rob looked at her
in surprise but couldn't find a speedy response.
Tara pressed Rob's hand. "Debby has some issues and has gone for a
smoke. She does that when she is anxious."
"Oh," was all Rob could say. It would explain a lot but since he had
no idea he couldn't judge. He looked at Tara for more explanation.
They continued to talk and Tara laughed at Rob's silly jokes.
"Rob, there is a lot to explain. Debby has shared some stuff with me.
It seems I am her only friend. I am sorry I don't want to intrude
between you and her. But she insisted I come or she would cancel."
"Tara, I am happy to get to know you. Debby always seems unhappy and
since we were both strangers to Chicago, I thought we could explore
together. I was very happy to meet you. There is nothing between Debby
and me and you are not intruding."
"I am glad," Tara replied. "Let's give her time to finish her
cigarette and join her. Text me your number and I can call you to
explain more. This is not the time and place."
Rob was now more than curious to hear the story and texted Tara his
number. "Yes, do call me anytime." Rob called for the bill and they
left.
They joined Debby who took a deep drag and ground out her cigarette as
they approached. "I needed that," is all she said as they walked back
to Rob's car. As per their last get together, Rob dropped Tara off
first and then took Debby to her apartment which was about a mile
away. Debby was silent and as Rob stopped the car Debby leaned toward
him, kissed him on the cheek with a soft "Thanks" and got out. The
mystery of Debby had deepened and Rob was even more curious now to
hear from Tara. He realized that even though he had wanted to get
closer to Debby, he had more in common and a better dialog with Tara.
She had saved the evening. The kiss on the cheek from Debby also meant
progress.
Rob did his chores the next day, Sunday, and intended to watch sports
that afternoon. In the back of his mind, the mystery of Debby was
never far away. Around 2 pm that afternoon Rob received a call from
Tara.
"Hey, Rob, would you like to have a coffee this afternoon?" she asked.
"Of course," Rob replied. "Where can I meet you? When?"
"Would you mind coming to my apartment? I can make coffee here. Say
around 4?"
"Great. I'll be there." Rob wondered for an instant if Debby would be
there too.
"It'll be just you and me," Tara added finishing Rob's thoughts.
Rob left the apartment a little early and bought some cookies. Tara
invited him into her small but neat apartment. It was a small studio
in a L-shape with a small sofa and two upright chairs. The kitchenette
and dining area were in one space with the living space. The bed- and
bathroom were apparently at the end of the short hallway. The flat
appeared comfortable and neat.
Tara had the coffee percolating and was delighted at the cookies. She
greeted Rob with a kiss on the cheek. They sat down at the small table
and Tara poured coffee into two mugs.
"Rob, first of all, I want to tell you that Debby doesn't know we are
meeting. I know you like her and want to get to know her better but
she has a history you should know. I don't want to intrude but she
likes you and I wanted to share somethings with you that may help you
understand."
Rob took a sip of his coffee. "Tara, I barely know Debby. As you know,
she doesn't say much. I thought we had something in common in this big
city and was interested to know her better but there is nothing more."
Rob paused, "There is some mystery and I think she is troubled by
something. I have no idea what."
Tara took a sip of her coffee and looked at Rob directly. "What I tell
you is between us. I just want to help you guys come together, OK?
Rob nodded.
"It was the first week at Blum and Debby and I were in orientation
together. There were about fifteen of us. For some of the group stuff,
we were paired together. She was new in town as was I. We met for
coffee and then for a drink. We got to talking and became friends.
Neither of us knew anybody here. One Saturday night I was to meet her
in her apartment. She opened the door with tears in her eyes. She had
a drink in one hand and a cigarette in the other. I never knew she
smoked. Her voice was slurred. Of course, I was worried and could see
she was upset. She had finished a bad conversation with someone at
home. As you know, Debby lived in Texas and went to college there for
the first two years." Rob's face was passive.
"Anyway, she forced me to take some shots with her and told me that
she felt terrible. That call was with her ex-boyfriend in Texas.
Apparently, Debby had wanted to celebrate her birthday with this guy.
She had bought a new dress, had her hair done and went to a beauty
salon. She looked great and was looking forward to a great night out.
Her parents were away that weekend and Debby expected that her date
would spend the night. He had arranged dinner at a restaurant and they
planned on going dancing and then later.... well, you know, they would
go back to the house. Debby was ready and waiting for her date to pick
her up. Well, it seemed that when she opened the door to her date, he
was shocked by her appearance. He thought she looked like a slut and
called her all kinds of names. Then he forced her to her knees and
made her do things with her mouth and swallow. She said she hated
sucking - sorry! When he was done, it wasn't over and he forced
himself into her.... in both openings. Debby was left in pain, torn
dress and bad memories." Tara paused and was almost in tears as she
recounted the story.
"Debby was devastated of course. She moved to another college out of
state. She said she spent a year in therapy trying to forget. Since
that time, she hasn't been near a boy on a date. So, I hope this brief
disclosure explains why she is reluctant to be alone with men and
always drags me along when she meets you." Tara paused. "You need to
be patient with her."
Rob stared at Tara for some time. It made some sense now. That's why
Debby had only spent a few minutes alone with him in the car and not
wanted to even kiss Rob.
"I'm really sorry to hear that. Is there anything we can do? Has she
become a les...?" Rob asked quietly.
"No, I don't think she's a lesbian and I am not either but..." Tara's
response was interrupted by the ring of her cellphone. She looked at
it and showed Rob the image. It was Debby.
"Hi Debby," Tara answered motioning Rob to be silent. "What's up?"
"No, my neighbor has come around for a cup of tea."
Tara listened. "No, can we discuss tomorrow?"
Another pause for listening.
"OK, I can give you a call later when I am done." Tara hung up.
"That was Debby wanting to meet. I'll have to call her later," Tara
explained.
"Well, Tara, I do appreciate the insight. Do you think I should ask
her out again? She doesn't say much but I understand why now." Rob got
up to leave.
"Oh, Rob, please don't change your attitude to her. If she didn't like
you she wouldn't have agreed to go out even if you had to put up with
me," Tara replied. "Promise?"
"Of course. She is lucky to have a friend like you. I'll invite her
out in a few days." Rob hugged Tara and kissed her on the cheek and
left. "You are most welcome too. It seems now that you and I have a
common goal to help Debby."
"If she says 'yes', she'll probably ask me too."
Rob picked up a burger on the way home and pondered on the information
he had been given. It explained a lot about Debby's behavior. He
didn't understand how somebody could violate a girl like that but he
knew it happened. Whilst the relationship with Debby wasn't going
anywhere fast, he found that he had more in common with Tara and he
like her a lot for wanting to help both Debby and him. He watched TV
that night but couldn't get the information about Debby out of his
mind. He would like to help her but he didn't want to get into a
complicated relationship. He didn't understand such issues well
enough.
It was 9.00 pm when Rob received a call from Tara. "Rob, sorry to call
you so late but do you have a minute?"
"I have as much time as you want, Tara. It's not late at all. Thanks
for that information although I am not sure what to do about it."
"Well, I called Debby and we had a conversation about an hour long. I
really didn't want to meet her tonight. I too was thinking how to
help. Can you come over again if it is not too much trouble? I guess I
can come to you too. I can take a cab."
"Is it serious? I am in my slops but can be there in 10."
"Yes, please. I think it is better to talk personally about this."
Tara hung up.
Tara opened the door to Rob with a troubled look on her face. "Can I
get you anything? Sorry, have no liquor except Tequila that Debby
brought here."
"Tea?"
"Yes, have that. I'll put the kettle on.
They sat in the small kitchenette. "Rob, this has become more
difficult and personal than I expected. I am sorry to call you over
but I wanted to talk to you before you see Debby tomorrow." The kettle
boiled and Tara poured the water into mugs with tea bags. She put milk
and sugar on the table.
Tara took a sip of tea that she had sweetened with three spoons of
sugar. She looked at Rob. "So Debby called me to talk about you! She
likes you and wants to go out with you alone but can't overcome her
history so easily. She asked me if I liked you and thought you were
interested in her." There was a pause in the conversation.
"Of course, I replied. He has asked you out and you dragged me along.
I told her that you would prefer to be alone with her. Was I right?"
Tara asked.
"Well, I like her and you but it has been very difficult to talk to
her. At lunch, it is simple sentences with others around. When we go
out, you and I have talked more than she and I," Rob answered.
"Yes, well, it seems she has some interest in you but can't face being
alone with you until she gets rid of these demons in her head."
"So what's the solution?" Rob asked. "I mean whether it would go far
or not with her and me, I don't know. I can think of her as a friend
but not much more than that. But if I can help in some way, then I
would do that."
"Really? You would do something to help her? It won't be easy or
comfortable. I am in the middle and I really don't want to be. You're
a nice guy and I like you but this is something that Debby should
discuss with you. But she can't and won't. She made me promise to ask
you."
"Sorry, Tara, I am losing you. What does she want?"
"It's embarrassing to explain." Tara paused and took a big gulp of
tea. Apparently, her therapist thinks she can expel the demons by re-
living the scene."
"What? She wants me to rape her again? Never. I can't do that." Ron
stared at Tara. "How can she expect that from me?"
Tara put her hand over Rob's. "You don't understand. Debby will be the
aggressor and you will be the victim."
"What does that mean? She would rape me?" Ron raised his voice in
disbelief.
"Debby didn't think you would do it. I can't blame you and I told her
that it was a lot to expect of a guy. But she had some suggestions."
"Tara, I am so sorry you are in the middle of this. I want to help
Debby but how can she expect to... to use me like that? I don't
understand."
"I am so sorry to be in the middle of this. I just wanted to help you
both. It is a lot to expect from a guy even if he wants to help." Tara
and Rob took big sips of tea in silence.
"What suggestions did she have? Did she have other ideas?"
"Not really that different. She wanted you to dress like a woman just
as she had done and you would be like Debby ready for her date and she
would act like the boy and do what he did to her. She needs you in a
dress and makeup to look like her. Female anyway."
"I have to dress like a woman? What a stupid idea? How can she expect
any guy to do that and agree to be .. What's the word? Raped?" Rob
looked at Tara. "I should have brought something stronger to hear
this. Can I have a shot of that Tequila to clear my throat and brain?"
Tara got up silently and went to the adjoining room and came back with
a bottle and two wine glasses. "Sorry, I don't have the right glasses
and I think I need one too. They took two big gulps of the strong
liquor.
"Rob, don't worry. It is asking a lot of any guy to do that. She says
she has thought a lot about it but never met any boy she liked enough.
She will find someone else. I told her to hire a pro but she didn't
like that idea at all. What pro would dress like that and agree to be
taken so roughly? I even suggested she could find a girl who would do
it for money. Debby said it had to be a role reversal and that no girl
would do."
"I am not sure what I can say to Debby if she meets for lunch
tomorrow," Rob said. "I better go before I get drunk,
"Well, you could always use my couch but it is small. Tomorrow is a
working day too. Rob, don't worry. I don't think Debby will bring the
subject up with you. As you said, she doesn't talk much anyway. "
"It may be embarrassing to meet her tomorrow. I'll skip lunch."
"Please don't do that. It is Debby who should be embarrassed. I am
sure she will ask me if I have talked to you. I will tell her that
it's not something you can do. Don't worry." Tara hugged him and
kissed him on the cheek dangerously close to his mouth. It didn't take
long for their mouths to meet and a deep kiss followed.
"This makes it easier to say no," Rob said. "Hope you didn't mind the
kiss."
Tara looked at him. "I wanted that kiss badly. I have to thank Debby
for introducing us." She gave Rob another lingering kiss.
Rob left happy but also guilty. He was happy to have found a kindred
spirit in Tara. He felt guilty he couldn't help Debby. He would try to
think of ways he could help her without being used. He had a fitful
night of how he was going to react to Debby. Even if she didn't bring
up the subject, she would know that he didn't want to help. However
outrageous her solution was, he couldn't do it. He didn't think any
reasonable man would agree. It was indeed terrible what her ex-
boyfriend had done. It would stay with her for a long time if not the
rest of her life. Still, that kiss with Tara made Debby's problem her
own. There was no way he could help.
He was hoping to talk to Tara the next day and dreamed of all the
things he would do with her. It had only been one evening and two
lingering kisses but he felt his life had changed. He hoped very much
that Tara felt that way too. He was anxious to know if Tara had
conveyed his answer to Debby. He would meet her at lunch and find a
way to meet her tonight. He sent her a text message mid=-morning.
Rob sat at lunch in his usual spot. He saw Debby but there was no sign
of Tara yet. As normal, Debby brought her lunch to his table and they
exchanged a brief hello. Rob decided to ignore the question of
yesterday and act as normal as possible. He asked how Debby was. 'OK'
was the terse reply. To all his attempts to start a conversation,
Debby's answers were in monosyllables. In between bites, she continued
her penetrating gaze. Rob couldn't look her in the face for long. He
assumed Debby was wondering if Tara had reached him and explained what
was needed.
Still staring at me with hose blue-grey eyes, Debby rose with her
tray. "Talk to Tara please and let me know," she said and walked away.
Rob breathed a huge sigh of relief and sent a short SMS to Tara that
he had to meet her later discreetly. Debby's voice was soft and tore
at him. She looked and sounded desperate.
Tara replied a little later that she had been in meetings all morning.
She would inform Debby that she and Rob would be meeting later. He
should come around 6.30 and she would order pizza. Rob was looking
forward to see Tara and pushed Debby into the background. It had been
just one day but he still remembered the kiss and Tara's tongue in his
mouth. He had enjoyed it.
Tara greeted Rob with a hug and a kiss on the lips. It was brief
unlike the kiss last night. "I ordered a pizza and will be here
shortly," Tara said and poured out a glass of wine. "I stopped at the
store and got a bottle of wine. I never drink alone."
They sat at the kitchen table eating pizza. Rob was on his second
glass of wine feeling happy to be alone with Tara, eating pizza and
drinking wine. Tara was looking at Rob in a new way. She too was
enjoying the easygoing and happy atmosphere.
"Debby called me as I was leaving the office. She said she met you at
lunch but you never said anything," Tara mentioned looking at Rob.
"Yes, she was staring at me through lunch. I guess she was expecting
me to say something. I didn't of course. As she left she told me to
talk to you."
"Yes, she seems to want an answer from you. Not sure why the rush as
it has been some time since the event." Tara took a small sip of wine.
She was barely down to half of what she had poured out. "Did you think
about it? I know she has was asking a lot."
Rob put down his glass slowly. "Frankly, I was trying hard not to
think about it," he replied slowly. "It's a hell of a thing to ask
somebody."
"Agree, but you will be seeing her around the office so you have to
respond. I think she knows the answer. Why are you even hesitating?
You seemed sure of 'No Way' last night."
"You're right. Honestly, I just don't know how to tell her. She seemed
so desperate when she asked me at lunchtime, so sad, I felt terrible.
What made it worse was what we had done last night as I left." Rob
looked at Tara for a reaction.
"You didn't want to kiss me or didn't like it?"
"On the contrary. I liked it a lot and wanted more. So I guess I am
feeling guilty to kind of dump her," Rob said softly. "It's a stupid
reaction to her idea."
"I feel guilty too for stealing her man. I didn't mean to. It just
happened." Tara placed her hand over Rob's. "Sorry, Rob, if you want
Debby..." Tara never got the chance to finish as Rob leaned over and
pulled her to him and kissed her hard.
"Mum always said that actions speak louder than words," Rob Said
releasing her. "Does that answer the question?"
Tara's soft reply was, "Oh yes. What else did your mum say? How would
she suggest you solve this?"
Rob stared at Tara. "Mum always said that a friend in need was a
friend indeed. But I don't think she ever imagined this scenario." Rob
paused. "Did Debby explain what exactly she needed?"
"Not in detail. The Therapist had suggested that she replicate the
scene of her.. her rape with herself as the aggressor against a man
impersonating her so as to release all pent up anger and frustration."
"What do you think she meant by rape? I don't have the .. the opening
if you know what I mean."
"Rob, I don't know. But you do know that many women use such toys to
pleasure their female and sometimes even male partners."
"You mean a dildo?"
Tara smiled. "I am sure you are trying to be polite. I think she would
use a strap on to simulate a penis."
Rob blushed. He knew the word but had never heard it used especially
by a lady. Tara saw the confusion in Rob's face and grasped his hand
tighter.
"Rob, I grew up in Hicksville but I do know what a strap on is. You
only have one opening and so she'll force it in there. Sorry to be so
direct." Tara paused. "Some men apparently enjoy it."
After a longer pause, Rob answered. "I never had reason to think about
such things. I am sure it hurts."
Tara smiled. "Interesting answer. Most men would reply 'Never!' You
are thinking if it will hurt. It probably would but there are ways to
minimize that with preparation." Tara's smile grew broader. "No, I
have no experience with it but my college roommate had boyfriends and
girlfriends. She would openly tell me how she pleasured other girls.
She even had one boyfriend who came over just to be used like that."
Rob sat there silently with a million thoughts racing through his
mind. He wanted to assuage his feelings of guilt by helping Debby but
he didn't like pain and the thought of what being taken like that
meant. More importantly, he had this nascent relationship with Tara
and didn't want her to feel that he had such hidden desires.
"I would like to help Debby if nothing else to be rid of the guilt of
breaking up with her. Perhaps you can talk to her. Maybe she'll settle
for something else."
"I am so happy to see that you want to help her even if her solution
is extreme. Says a lot about you. I too feel a little guilty but these
things happen. I would also like to help Debby as a person, but I
don't fit the role. I am sure she'll call and ask how you reacted.
I'll see if she has other ideas." Tara got up and held out her hand.
"Let's go to the couch and talk. I can clean up later," Her smile
indicated they wouldn't be talking much.
They spent the next half hour kissing and cuddling on the small sofa.
It was a fierce meeting of lips, tongue and saliva. Their hands didn't
explore the other's body. They were content to let things slowly
develop. It was almost 9 pm when Tara's phone rang. Lips still glued
to Rob's she looked at the caller ID. It was Debby. She broke the kiss
and put her finger to Rob's lips.
"Hi, Debby. All Ok here. Rob is leaving soon and I will call you. OK?"
Rob could hear Debby.
"How did he react?"
"As expected. I'll call you back soon." Tara hung up.
Tara looked at Rob. "What are you going to tell her?" Rob asked.
"I don't think she expected a 'Yippee' when we can do it answer. I'll
see if there is some other way. Now, where were we? Oh yes, I know."
Tara brought her lips to Rob's and their tongues danced.
"If you don't leave now, you'll have to spend the night here. I don't
want that till this Debby thing is behind us, I think I need to talk
to Debby alone. Can I call you later?"
"Anytime. I agree. Let's get this thing with Debby behind us," Rob
said trying to steal another kiss.
"I'll call you." Tara pushed Rob out of the door reluctantly.
Tara called Debby immediately. She picked up on the first ring.
"He said no, didn't he?" Debby said in a slurred voice. Tara thought
she may have been drinking.
"Have you been drinking? Debby, stop it now or I'll come over."
"Nobody cares."
"Debby, stop it and listen." Debby stopped her sniffling. "OK. It is
an unusual request but Rob was open to your ideas. He wanted details.
What do you want and when should this happen?"
"I told you. The therapist says I should reenact the scene. But this
time I would enter the room and find 'her' all dressed up nicely. Just
like I was. I can show you a picture of my dress. Then, I should
attack him and force him to do things like I experienced."
"So, it's not just a dress..."
"No, if 'she' doesn't look good, the attack would never happen. If I
had not looked good, Brad would never have raped me. We had gone out
many times before."
"I don't think Rob has ever dressed as a girl before. I never asked
him. I guess we can find a nice dress for him. He'll need a wig and
some makeup. And shoes, of course:
"Yes, I have some stuff and I would buy it. It'll be cheaper than
therapy."
"So how do you plan to .. I mean to attack him? What should he
expect?"
Debby paused. "I have a strap on and I'll make him suck it and then
thrust it into him." Another pause. "Brad fucked my mouth, cunt and
arse. I know she will only have two openings."
"You'll really attack her aggressively?" Tara asked horrified. "It
will be painful."
"Well, I was hurt pretty bad as I didn't expect it. The mental hurt
lasts longer as you can tell." There was a hard blowing of her nose.
Debby then continued. "Forget it, Tara. No reason for Rob to do it. I
never kissed him or even blew him. Why should I expect him to help?"
"Look Debby, Rob likes you. He wouldn't have invited you out several
times otherwise. He is a nice guy and am sure didn't expect anything
in return."
"Don't bother him. I know how to solve this. I have my dad's gun."
"Debby," Tara shouted into the phone. "Don't you dare. Why waste your
life on that scumbag? Your parents and friends will be devastated."
"I can't live like this either, Tara. How can a man love me if I don't
let him get near me? You don't understand."
"Debby, I never went through what you did. I am sure it was horrible
and has left many scars. I think Rob may be willing to help. Are you
sure that this is the only solution? Is there any other way?"
Tara heard more sniffles. Debby was either pausing to blow her nose or
take another drink. "Yes. There is. I told you. It's quick and will
fix everything."
"Debby, now concentrate and listen. I will talk to Rob and see what he
thinks. I know he wants to help as do I. Now promise me you'll not do
anything stupid and go to bed."
There was a pause with more sniffles. "OK." Then the phone shut off.
Tara wondered if she should rush to Debby's apartment. She believed
that she had convinced Debby to hold off on any hasty action until the
next day at least.
"Rob, hi. I talked to Debby. She was in a bad way. I need to talk to
you before lunch. Can you come over early? I'll make you breakfast.
Around 7 so we have time. I can drive with you to work perhaps."
"What's the matter with Debby? I'll be there. Try to relax. You sound
worried."
"I'll tell you tomorrow. Sleep tight and I'll see you early." Tara
tried to sound calm but she was boiling inside. Neither Rob nor she
would want to feel responsible if Debby did something stupid. Yet,
what Debby wanted was outrageous and she felt uncomfortable to even
explain it to Rob.
Rob was there at 7 as promised. After a restless night, Tara had made
them scrambled eggs and toast. Coffee was percolating. She gave Rob a
big hug and a peck on the lips. She had the toast on and in a few
moments, both sat at the table with their breakfast and coffee.
"OK, tell me about Debby," Rob said. "You look worried and I don't
think you slept much."
Tara looked at Rob. She hadn't had the time to apply any makeup. She
never had much on anyway, just a touch of mascara, blush and lipstick.
"This is difficult, Rob. Sorry, but Debby threatened to do kill
herself. She has her dad's gun. I told her not to be stupid. But I
think she had been drinking, her voice was slurred."
"Oh my God," Rob exclaimed. "I didn't realize she was that desperate.
I'm sorry you are in the middle of this." Rob reached out for Tara's
hand. "So did she tell you what she wants to do? Any other ideas?"
"Rob, it's terrible what she wants. She says the only way for her to
be rid of this desperation and fear of men is to re-live the scene.
She is the aggressor and Brad - that was her ex's name - is the
victim. It's a kind of revenge act." Tara paused for a sip of coffee.
"She wants you all dolled up just like she was. She will even pay for
a makeover and s dress and shoes. She wants to find you like that when
she knocks on the door." Tara was looking at Rob intensely, her hand
tight in Rob's.
"So I need to dress like that. I can pretend it's Halloween, I
suppose. Never dressed as a girl before. Just was Superman when I was
eight, I think."
"Rob, there's more. When Debby enters the room, she will see you as
Brad saw her. Then she will attack you. I think she has or will buy a
strap-on and force you to do things like she experienced. She will
surely penetrate you back there. It will be rough."
"Oh my God. I can't believe she would want that. I know she went
through some stuff like that herself but still."
"It's a terrible thing to ask of anyone," Tara agreed.
"What if I don't agree?"
Tara looked at Rob. "I don't know. Many make threats but never go
through with it. Don't know if Debby is like that. I think if she
starts drinking, feels sorry for herself and sees no way out, she is
not in control and could do things to herself. I can't live with that
thought. But I can't do anything about it either."
Rob paused for a long sip of coffee. "I can deal with the dressing as
nobody will see me except you and Debby. The other part is unknown. I
never experienced anything like that before. I am sure I won't like
it."
"You'll hate it. My roommate told me she had tried it. It hurt the
first time as she didn't have lubrication. So it'll be painful I
think."
"Tara, over these last two days I have grown close to you. I don't
know what I saw in Debby but it wasn't anything romantic. It was
companionship. I feel guilty in breaking up with her even though I
wasn't really with her if you know what I mean."
"I know. That's what makes this request even stranger." Tara squeezed
Rob's hand. "I need a few minutes to put on my face. I'll be back
soon." Tara rose and left the kitchenette.
Rob cleared away the plates and cups into the sink. His mind was on
Debby's request. He had never put anything like that in his mouth,
except a banana. But he bit pieces off. He was torn between wanting to
help and guilt. He had no idea what he could expect. His thoughts were
interrupted by Tara.
"I'm ready. Let's go," she said. She took his arm as they descended
the staircase. Rob felt good. "I'll have to tell Debby something today
before lunch. What do you think?"
"I think I'll feel guilty for the rest of my life if I don't do
anything to help her, especially if she will hurt herself," Rob said
as they got into the car. He didn't drive off. "But I am scared of
what she wants to do."
"I feel the same way and even more helpless as I can't do anything for
her. And then taking you away..."
"Don't think about it," Rob interrupted. "I know my relationship with
Debbie would have been just friends. I am happy she introduced us."
"So, what shall I tell her?"
Rob looked at Tara. "I don't think I have a choice. I don't want to
feel guilty when I am with you. If she does something to herself, it
would be terrible for both of us. I would do it if you are willing to
help," Rob said quietly staring intently at Tara. He started the car.
"Of course I'll help. But what do you need?"
"I have no idea how to do this and pretend to be a woman, an
attractive one that Debby would like. It seems she wants more than me
in a dress. We also need to know where this will take place."
"Yes, she was clear about that. She was willing to pay for a makeover.
I don't have skills in that area but I can help with choosing a dress
and getting you dressed, I guess. And anything else you need. I am
sorry you have to go through this."
"Hey, if this is what I need to do to get a nice girlfriend and more,
it'll be worth it." Rob smiled. The decision was made. Now to execute
the plan so he and Tara could be free to develop the relationship.
"Tara, please chat with Debby and get her ideas down exactly. This is
a one-time thing. No room for errors."
"I know. I'll see what I can do. Will you meet me tonight?" Tara asked
hopefully.
"Well now, I'll have to drive you back too. So let's say at least two
hugs and kisses should do it." Rob sounded much more cheerful now.
"I don't want a cheap ride. I am willing to pay more in kisses,
starting now. I'll try to be there at lunchtime in the canteen." Tara
leaned toward Rob, gave him a hug and a light peck in the lips. "I
don't think you want to start wearing lipstick to work just yet so
I'll save the heavy stuff for later."
"I can't wait," Rob replied as he walked jauntily to his office. He
wondered how his conversation with Debby would proceed. Nothing could
be discussed in the canteen but he would need to confirm his
willingness.
Rob grabbed his soup and sandwich and went to the table he occupied
regularly. He wondered if Debby would show up. He only had thirty
minutes for lunch. Ten minutes into his break, Debby picked up her
salad and joined him. Tara was nowhere in sight.
"Hi," Debby said in that same tone of voice. There was no emotion.
"How are you?" Rob asked politely.
"OK," was the short reply. It was hard to have a conversation with
someone who replied in one-word answers. "You talked to Tara." It was
a statement rather than a question.
"Yes, we need to work out some details but....."
"Rob agrees," like I told you. Tara just joined the conversation and
sat down. "Sorry I am a little late my meeting overran."
"I was just confirming that I agree to do it but we need to work out
details."
"Yes, I will discuss the details with Debby. You can drive me home and
I'll tell you all. 5.15 at the entrance to the car park?"
"Yes, sure. I'll see you later." Rob picked up the tray and left them.
He knew he would be the subject of discussion. He tried to put it out
of his mind. He couldn't believe what he had committed to.
There was plenty of work to wade through all the customers that Rob
dealt with. But he couldn't concentrate and found his thoughts
returning to Tara. She seemed genuinely interested in him and she was
easy to be with. It was hard to concentrate with so much on his mind.
Rob kept an eye on the clock and finished on time. He didn't want to
keep Tara waiting. He rushed out. To his shock, he saw Debby and Tara.
He had no choice so he approached them and greeted them.
"Ready?" he asked Tara
"Debby wants to tell us something," Tara replied.
Debby was looking in her purse and took out a pack of cigarettes. She
tried to light one but her hands were shaking. Tara took the cigarette
from her and the lighter, lit it inhaling lightly a few times and gave
it to Debby who took several deep puffs.
"Rob, Tara told me you agreed to help. I know that what I am asking is
not normal but I am at the end. I told Tara that I can arrange
everything and we can do it anywhere you are comfortable."
"Yes," Rob said softly. "Debby, to be honest, I don't know how I will
feel after this."
"Well, yes, it may take some time. But if I can get over this I'll be
able ...."
"Debby," Tara interrupted. "I can take care of the clothes and things
with Rob. Send me a picture of a dress you think you'll like. You said
there is a salon that could do the makeover so he will look great. We
need time to do this so I think Saturday in one week is right. Is that
OK? Rob is that OK? So we have some time to arrange this."
Debby was smoking rapidly and had almost finished her cigarette. "OK,"
she said finally. "I'll text you the salon number and a picture. See
you tomorrow." Debby walked away to her car not looking back.
Rob and Tara got into the car. Tara turned to Rob to kiss him.
"Sorry," Tara said. "I saw how nervous she was. Her hands were
shaking. I know how anxious she is. I was nervous too that she wanted
to meet us tonight. I didn't want that."
"OK. So what else did she have to say?"
"Let's stop somewhere and buy some wine. I have a pasta dish I can
bake. Is that OK? I can make a salad too."
The journey to Tara's apartment was mostly in silence. Rob stopped at
a small liquor store and bought a bottle of white and red. He also
purchases some crusty bread and a block of cheese not paying much
attention to what kind. Whilst Tara put the lasagna in the oven, Rob
opened the wine. He poured out two glasses.
"So, what did Miss Debby demand now?"
Tara looked at Rob. "It'd not too late to change your mind. Debby will
have to deal with it. I don't want to be blamed for encouraging you to
do this." Tara's eyes never wavered from Rob's.
"Sorry, I am getting more nervous about this. It was my decision only
but I need your help." Rob looked at Tara and again repeated. "Sorry."
Tara came over to him and hugged him tightly. "You have a right to be
nervous. This is not something a man normally wants. Especially when
someone else is dictating the action. You know I will help but it is
you that must endure her aggression."
"Thanks. So what does she want exactly?"
"She wants you dressed to the nines as she was on that day. You would
have to look good. She will come in and see you waiting for her.
Something triggers a reaction and she will then attack you. I am sure
you know what that means. She has already described what that guy Brad
did to her. So I think she will want to do the same except..."
"Except what?" Rob asked impatiently
"You only have two openings... she has three," Tara replied softly.
"But don't think about that now. Let's eat and then I need to measure
you so I can get the right size of stuff."
Over their dinner, they avoided the event that they were both
dreading. They talked about family and friends; their jobs, interests
and lives. It was the first time they had exchanged such details. They
had met several times but always in the company of Debby. Even if
their kisses had turned passionate, and they shared a deep personal
interest to help Debby, they realized they knew very little about each
other until now. Whilst the conversation was light, and in parts
intimate, the story of Debby was never far from their thoughts.
Dinner over, they stacked their plates and glasses into the sink. Tara
held out her hand to Rob. "Need to measure you so we get the right
outfits." She led Rob into her bedroom. "You need to take off your
clothes down to your boxers. Remove your socks too. I'll be right
back." Rob slowly unbuttoned his shirt and removed it together with
his undershirt. He removed his socks and shoes and dropped his pants.
Tara returned with sheets of paper and a pen.
"OK. First, step on the paper and I'll outline your feet so we get
shoes," Tara said.
"Why do we need shoes? I am not going out dressed like that. People
will laugh at me."
Tara looked at Rob with a smile. "OK, in that case, you'll have to
come back from the salon fully made-up wearing your jeans and T-shirt.
People will laugh at you then, right?" Tara laughed. "Sorry, but I
think that will look funny. You have a slim figure and with the right
clothes, we'll go to the salon, get your makeover and then come back
here to dress. You can go to the salon wearing a simple blouse and
skirt. We don't need you messing up the makeup pulling a T-shirt over
your head. So what's it to be?"
"You'll come with me to the salon?"
"It's the least I can do. I'll see if they can do my hair at the same
time. You'll be wearing a wig."
Rob appeared relieved. Tara had a cloth tape and took his measurements
from neck, bust, waist and hips. For good measure, she even measured
him from neck to knee. "Good job you're not so hairy but we'll need to
depilate your body and legs. It'll grow back soon. Now the shoes. Step
on the paper."
Rob stepped on the paper. Tara knelt at his feet and outlined the
foot. "Your feet are not that big but the width is important. As she
straightened up, the growing bulge behind Ron's boxers was evident.
Tara looked up at Rob. "Does talking about dressing get you so
excited?" Tara asked pulling down his boxers. Rob stood there silent,
embarrassed at his now fully erect penis at 90 degrees to his body.
"All the ladies I know don't have this type of thing sticking out,"
Tara said wrapping both hands around the rigid shaft. "I think I know
a way to make it go down. She kissed the tip and moved one hand to his
sac, Her eyes never left his as she slowly took it in deeper,
salivating to make it slide in and out. It didn't take more than two
minutes and Tara's hands went around Rob's behind as he erupted. She
kept him there until it was soft. She licked the tip clean and looked
up at Rob. "See that's another way I can help you. I hope it was OK.
This was just my second time only." Tara rose and kissed Rob lightly
as she didn't know if he would be repulsed by the taste. Rob pulled
her to him tightly and kissed her deeply. "Thanks," he whispered. "My
second time too."
"You've given two BJs already?" Tara asked with a smile. "You're
ahead...." Tara never got to finish the sentence as Rob's tongue was
deep in her mouth.
It took some time to untangle. Rob pushed Tara onto the bed, lips
still locked. He pushed up her skirt and met little resistance. He
dove down and found Tara's nether lips enlarged and very moist. Rob
inserted his tongue into the slit and slowly licked up and down, then
taking her little knob and sucking on it gently. Tara's hands were on
his head pulling it into her groin. She moved her hips up as if his
tongue were a penis. She exploded with a copious amount of fluid that
Rob drank down. He stayed in that position although Tara's hands were
no longer holding his head. He raised his head, saw Tara smiling at
him and dragged himself up to kiss her. She accepted his tongue with
the remnants of her juices without hesitation. Tara could feel Rob's
penis growing against her stomach.
"Rob, that was wonderful. Where did you learn to do that? The same
place you learned to enjoy BJs?" There was humor in her voice. "I
liked it a lot. But...." Tara paused.
"But what?" Rob asked worried he had done something wrong.
Tara held Rob tightly. "I am very happy we did this and I want more.
But can we wait till this thing with Debby is over before we go
further? "
Rob stared at her blankly, his erection subsiding.
Tara's hands wandered down to his penis. "I would be happy to use my
mouth again...and again."
Rob kissed her hard. "You're right. Not long now and we can then relax
and enjoy without guilt." He kissed her again. "I'd better go or I
will forget what I just said." Rob dressed slowly.
"You have a slim figure and very little hair, "Tara said looking at a
naked Rob. "But we'll need to make sure there is no hair anywhere. I
know what to get and we'll try that tomorrow. We have time but you'll
need to get used to things. I will buy the clothes and stuff at
lunchtime tomorrow when I get Deb's pictures."
"Don't go over the top. This is a one-time thing," Rob reminded her.
"Yes, even more reason to make this look good. I know what you have to
go through but we can have some fun on the way, can't we? Is that
wrong?"
"Not if we both are having fun," Rob replied, kissed Tara hard once
more and left.
The next day at lunch Rob was left to his own. He saw neither Debby
nor Tara. He wondered if that was a coincidence or planned. He was
sure Tara would want to meet tonight. He was amazed by the connection
to her and how his life has changed. Whilst he had initially just
sought company with Debby in this new town, he had never been excited
by her. Sure, he would have gone as far as Debby would have allowed
him, but that was a kiss on the cheek. It was a stark difference with
Tara. There was a bond that was going stronger by their common goal to
resume a normal boy-girl relationship. Rob knew he was in for some
pain by Tara's description of Debby's intended action. The dressing up
part was like a Halloween exercise although he had never been
interested after the age of eight or so. He was comforted by the fact
that he wouldn't have to venture out and make a fool of himself. He
had to suffer the salon visit but if Tara was with him, perhaps he
could pull it off. He desperately wanted this behind him so he could
act normally with Tara. He wouldn't feel bad not asking Debby out
again or even seeing her again after that.
Mid-afternoon Rob received an email from Tara that she still needed to
do some shopping. She suggested they meet at the mini-mall around
6.45. They could have dinner together after that. Tara didn't have a
car so Rob assumed she might be with Debby. He wanted to avoid meeting
Tara and Debby together as Debby would certainly see the changed
relationship between them. He was pleased Tara had made contact.
Rob was there a few minutes early and watched from a corner if Debby
was with Tara. He was pleased to see Tara with several shopping bags
alone. She greeted him with a one-handed hug and a kiss on the lips.
She had several bags without logos so Rob couldn't identify the store.
"So, did you get everything you wanted?" Rob asked. "Was Debby with
you?"
"No. We met at lunchtime. Debby will get the dress but I needed some
other things so I came alone. Disappointed?" Tara asked with a smile.
"Don't ever say that. I just don't know how I should react if I see
her. Maybe OK at lunch with others but alone or with you, I am not
sure."
"Don't worry. Debby said she had some calls to make to her home and so
would be busy. Frankly, I know she wants to do this but she too is
embarrassed she had to ask you."
They chose a small Pizzeria and ordered a pizza they could share with
half a bottle of wine. "So what did you get?" Rob asked losing
patience.
"Most things to turn you into a beautiful girl. Just a few more
things. Will you come back to the apartment and we can take care of
the body hair?" Her smile would melt hearts.
"Yes, I'll take you home," Rob replied.
They went to Tara's apartment and she went immediately to the bedroom
and put the bags in the closet. "You'll see them soon enough," she
said with a laugh. "You'll be wearing them."
It wasn't long before they were in a clinch and deep kiss. "I think we
had better start or we'll never get this done." Tara unbuttoned Ron's
shirt slowly. His pants were next and soon Rob was standing in boxers
and socks. They came off too. Tara removed her blouse and skirt and
was now sown to a bra and panties. It was the first time that Rob saw
her body almost naked. She didn't have the tall slim figure of Debby
but had a nice set of breasts and no fat. She was a very pleasing
sight. Tara grabbed his growing penis and led him into the small
bathroom.
"You don't have much growth but let's do it right," Tara said donning
a plastic glove and rubbed a lotion all over Rob, from neck to toe.
Rob didn't see her face but found her gloved finger in between his
cheeks right around his puckered hole. "You better keep this area
clean and lubricated. You know what she will try," Tara said humor in
your voice. She inserted her index finger into his hole and Rob
jumped. "Just checking if you had some experience down there," she
said. "Now, we'll have to wait a few minutes and then please shower
when it starts to tingle."
Rob did as asked surprised that he didn't protest much. For a one time
event, it seemed like this was way too much. He would accept the
humiliation of dressing up and being 'raped' even. It wasn't rape
technically, as he had agreed to be used like that. The tingling
started and Rob felt good with the warm water cleansing his body. Tara
had left him a large soft towel and the feeling on his smooth skin was
intoxicating.
"Tara?" he called out. "I'm ready,"
"Come into the bedroom," came Tara's reply.
Rob walked into the bedroom towel wrapped around his waist. Tara was
sitting on the edge of the bed completely nude. She looked at him with
a big smile. "I thought you might like to see all after you've shown
me all too."
The growing tent in Rob's towel indicated his surprise. "Wow," was all
he could utter.
Tara beckoned with her finger and Rob shuffled forward. As he
approached the tent became larger. Tara undid the knot and the towel
fell to the floor. She rubbed his body with her hands. "Even though
you didn't have much hair it feels so much nicer now," she stated. Her
hands went to his erect penis and sac. She kissed the tip tightly, her
tongue flicking at the slit. She looked up at him.
"Rob, do you know what Debby will expect when she walks in to see you
all dressed up and waiting?"
"Will she want to kiss me?" he asked quietly.
Tara smiled. "I don't think so. Remember what she described? Her
boyfriend forced his penis into her mouth roughly. Remember?"
Rob nodded. Tara continued, "Well, I have never been forced to do that
and neither have you. So, let's see if we can get your mind on that. I
want you to hold my head in both hands and then thrust hard and deep
into my mouth. OK? Hard and deep as you can."
Rob held Tara's head and gently put the tip between her lips. He
slowly thrust in hesitantly. "No," Tara said. "You're supposed to be
raping my mouth so hard and fast." She took the tip back into her
mouth and looked up at Rob. He looked down at her not really sure how
to do this. Tara saw the look; his gentle nature didn't allow such an
act. She grabbed his cheeks and pulled him into her mouth deeply,
almost choking. She kept up the movement and felt his eruption slide
down her throat. She kept it in her mouth, gently sucking as it grew
soft. Rob stood there helpless staring back at Tara, embarrassed.
"Rob, I love doing this with you as I said before. I wanted you to
know what to expect. Remember, Debby can only do this with a strap-on.
It will be hard and never go soft. It may also be much bigger than
your penis. I love your size but this will be different for you." She
saw Rob's dejected look. He would not hurt anyone. "I knew you would
be like this. You're thoughtful and kind and would never abuse a girl
that way. But I want you to be prepared. Now, sit on the bed and don't
look whilst I get something."
Rob watched as Tara rose and went to the other side of the bed. Her
proud breasts and figure appeared in perfect contrast. A few moments
later Tara walked in front of Rob who stared at her in surprise. Her
right hand was stroking a deep red plastic penis attached to her
crotch. "I talked to my college roommate who suggested I get one of
these. You don't have to do anything of course but I want you to know
what is coming. This will not taste as nice as the one I had in my
mouth but it will probably be close to what you can expect from Debby.
Interested?"
Rob's face was blank. Even as he thought of the promise he had made to
Debby, he never realized that this is how she would look on the night
of the planned event. "Remember, you will be dressed like a girl who,
under normal circumstances, would be happy to suck her guy off. Try to
imagine that your boyfriend gets into a fit and thrusts into your
mouth to get him hard." Tara moved a step closer to Rob and positioned
the tip at his mouth.
"Open your mouth and salivate and lick the head," Tara suggested.
"Forgive me as I have no experience with a strap on. But I am going to
thrust hard so you get a feeling. OK?"
The words were hardly out of her mouth when Tara began thrusting hard.
Rob choked and tried to accept the unyielding object in his mouth.
Tara thrust hard. The plastic penis was just seven inches long but
caused Rob to gag. Tears formed in his eyes as Tara thrust several
times hard and then withdrew immediately. She sat beside Rob and
kissed his tears. "I'm sorry, babe, but it will be easier for you if
you know what to expect. Debby wont expect you to enjoy the sucking
and swallowing - like I do with your penis. She'll just want to get it
wet and show who is in charge." She hugged Rob tight and turned his
face toward her. She kissed him tenderly, her tongue slowly exploring
his mouth. It took a minute but Rob relaxed and enjoyed the moment. By
some strange coincidence, his penis became rock hard again. "Now I can
imagine what it looks like from above when your cock is in my mouth."
The kisses continued.
"What's this?" Tara said sliding to her knees. "It seems like you
enjoyed that. Now relax, I am going to enjoy this." Her mouth slid
over Rob's erection slowly and languorously bringing it to a hardness
Rob had never felt. When he finally shuddered in climax deep in Tara's
mouth, she was looking at him with in ecstasy. She kept him there with
slow sucking movements until he was totally flaccid.
"Can I do...?" Rob began.
"No need. You'll get plenty of opportunities when this is behind us. I
promise. Well, enough for tonight," Tara said standing up and helping
Rob up. She kissed him softly. "You had better leave or this will go
further."
Rob got dressed and started for the door amidst several stops for
kisses. "Be ready for tomorrow. You'll try some clothes and we may
want to experiment back there." Rob's startled look was interrupted
with another kiss and a quiet closing of the door behind him.
That night and the following day Rob's mind was on what had happened
and what was to come. He had not enjoyed the initial thrusting into
his mouth and he knew that Debby would be even more forceful. He was
very happy to have support in Tara but wondered if he was crazy or
stupid or both to have committed to this. He didn't feel he could back
out. With Tara's help, he would see it through and not feel guilty
about breaking with Debby. Then, he wondered why as he never had a
relationship with Debby. A kiss on the cheek wasn't quite what he
expected on a second or third date. The few times they had taken a
drink or a meal, Tara was always there and he was glad. He wasn't sure
how Debby would react. He knew that he had found a soulmate in Tara.
In the short time they had been close, Tara had been more responsive
and understanding than Debby had been. It was also a mystery that
Debby had never trusted him enough to disclose her anxiety and history
to request his help. Instead, she had used Tara as a shield and then
as a go-between.
Again at lunchtime neither Debby nor Tara was to be seen. He could
understand Debby's reluctance but missed Tara's conviviality. Perhaps
they were shopping again but he couldn't imagine what else he would
need. This was a one-time deal. In his mind, he thought that the
relationship with Tara was more than worth any pain or discomfort he
would suffer. He was hoping to hear from Tara this afternoon.
Tara did send Rob a message and asked if he could drive her home. They
could meet as usual after work in the car park. Rob readily agreed.
The afternoon was a blur. He put the thought of what he would
experience next to the back of his mind. He was happy to be with Tara.
In only a few days he was consumed with thoughts of her.
Tara met him with a kiss on the cheek. When they entered the car,
hidden from co-workers, she gave him a deep kiss with her tongue
exploring his mouth. "Can we go to that bar, have a drink and a snack
maybe and then go back to my place?" she asked.
"Of course," Rob replied. "Great idea. Missed you at lunch."
"Yes, Debby wanted me to make arrangements at that salon. Rob, we need
to make sure you are ready for this."
"What more does she want now? I agreed to do this. You were there."
"I know. I have been thinking about this and what you have to go
through. We said Saturday in one week. I would love for this to be
over quickly so we can put this behind us."
"What are you suggesting?" Rob asked.
Tara looked at Rob. He was driving so she couldn't see his full face.
"Would you mind if we did it this Saturday? I want to get this over
quickly and be with you normally," Tara replied softly.
Rob thought for a moment. "Tara, I have no idea what to expect. I will
do as I promised. You are right though. Putting this behind us quickly
is best for all. I need your help of course."
"I'll send Debby a text. We'll have to get you dolled up sooner then.
I am looking forward to see you in a dress. With your figure, you'll
look better than me."
"That's not funny and no way would I look better than you. I'm happy I
won't be dragged out somewhere for people to see."
Tara laughed. "First of all, you have to go to that salon dressed.
Debby will tell the salon the story but you can't scare their other
customers away by dressing as a male and then having a makeover. That
would make you a laughing stock. Then you have to leave the salon like
a lady, come back and get dressed as Debby wants. Then you know what
to expect."
"Yes," was Rob's mumbled reply.
"So, still want to go through with it?"
Rob was just parking and didn't respond instantly. He looked at Tara.
"What do you think I should do?"
Tara grabbed his hand. "These last few days have been magical.
Finally, I have found a happiness I didn't know before. What I am
trying to say is that I would like us to be together and see where it
takes us. But, this is asking a lot to assuage our guilt. Whilst I
feel for you, it is you that has to go through with it. I will support
and help you and all fun aside, only you can decide. I will accept you
any way you decide." She leaned forward and kissed him.
"I don't know, Tara, I just feel I have to help her. I also would feel
less guilty because once she knows about us, we will lose a friend."
"You told me she has not sucked you off and not even kissed you on the
mouth, so where does that guilt come from? Do you want her?"
"No, no, no. I told you that Debby and I haven't even talked much. I
only met her with you and sometimes alone at lunch. Over the last few
days we have grown close and I want that to develop very much - if you
want that is." Ron turned to Tara who hugged him and kissed him hard.
"I want that very much too." Tara squeezed Rob's hand. "Let's have a
drink and get some Chinese. We can eat in the apartment."
"Deal.." They held hands as they entered the car and drove to the bar.
Rob ordered two white wines. He gulped his down and ordered another
round quickly.
"Take it easy," Tara cautioned. "It's just 6 pm and we need to do some
things tonight. You can drink at my place but you have to drive - or
stay," she added as an afterthought.
They sipped their drinks, each deep in thought. "Let's go," Tara said
and grabbed Rob's hand.
Tara guided Rob to a take-out Chinese restaurant and ordered two
dishes. She had Rob wait for her in the car. It was less than ten
minutes to her apartment. They drove in silence again. Tara opened the
cartons and served Rob and herself. They still had wine from the day
before just enough for two glasses. They clinked glasses.
"So what are you thinking? You've been silent for the last 45
minutes," Tara asked.
Rob looked up from his noodles. "I really don't know what to think. I
only know that I would like to spend more time with you without guilt.
That may not be the right word, I want to help Debby, but the price
she is asking is high. "
Tara looked at Rob for some minutes. "OK, Rob. You have to decide what
you want to do. I will support you and be with you whatever you
decide. I have told you that. I know how you think and I admire your
willingness to help. What Debby is asking is not simple. It is a
personal decision. I can't take away any pain or hurt, but I will be
with you and try to kiss away your hurt. So decide! Neither you nor I
want regrets."
Rob looked at her with confusion on his face. This was the most
difficult decision he would ever face. He didn't feel he owed Debby
anything, yet he didn't want the responsibility of what she might do
to herself. It was made worse by the fact that he didn't want any
relationship with Debby in the future. Whatever happened with Tara, he
knew he could never have a normal relationship with Debby.
"OK." He said finally. "No more talk. I'll do it if you help."
"OK, finish your wine whilst I get organized in the bedroom. I'll be
back soon." Tara left Rob to finish the last sips of wine. He got up
and put the dishes in the sink and disposed of the remnants of food.
He was determined not to re-examine the decision.
Tara came back into the room a few minutes later. "I laid out some
stuff on the bed. So undress completely and wear what's on the bed.
I'll be in to help you in a minute." She gave him a hug.
When Tara walked back into the bedroom a few minutes later Rob had
undressed completely and was wearing floral panties. The bulge in
front indicated his arousal. "Turn around and put your arms through
these," Tara commanded and help Rob into a bra. "I don't have anything
to stuff those cups with but I can use some panties of mine and
pantyhose." A few minutes later Rob had a bust. It wasn't perfect but
would get him into the mood. Next came a skirt that was well above the
knee and a blouse. Tara kept the top button open and wrapped a broad
belt around his waist, hanging low on his hips. "This next part will
be difficult at first but you'll get it quickly." She pointed out some
shoes with a two-inch heel. "Sorry, I don't wear corsets and stockings
just pantyhose. I never had anybody who wanted to see me in them,"
Tara said shyly.
Tara helped Rob into the shoes and with her arm around his waist made
him take a few steps. It didn't take long for Rob to get used to the
heels. His gait was not feminine but he was steady on his feet. "I
don't know if Debby wants you wearing higher heels but these are good
for practice," Tara said. Whilst Rob would not be mistaken for a lady,
his slim figure was reasonable. Some makeup and a wig would make a big
difference. "Now, this isn't perfect but I am trying to get you used
to what Debby would want to see. Open your mouth, please." Tara took
out a tube of lipstick and applied it carefully to his lips. It wasn't
the dark red she normally wore but a much brighter color. "Not bad but
you'll look great on Saturday." Tara paused for a moment. "Do you
trust me, Rob?" Tara asked
"Yes, of course. I couldn't do this without your help."
"Well, you may not like what will happen tonight but I assure you it
is for the best. "
Rob looked at her glumly and nodded. He didn't understand what Tara
meant as she opened d a small draw in her dresser and took something
out. She also put on a think rubber glove. Rob's mind wasn't accepting
what he was seeing, Tara took out a tube of something and had Ron bend
over the foot of the bed holding on to the low wooden frame. "Trust
me, this might be uncomfortable but you will be grateful later," Tara
slid a well-lubricated finger into his anus. Rob jumped but the finger
sawed in and out. "My college roommate advised that this was the best
preparation for what is to come. I haven't had this experience but I
don't want you to hurt." Even as she was talking rubbing Rob's cheeks
with her left hand, her right hand thrust a hard object deep into Rob.
He grunted in surprise but wasn't really in great pain. Tara
rearranged his panties and skirt leaving the case of the plug seated
firmly against his rear hole.
"Now walk around a few minutes and then sit on the edge of the bed. I
need to change. When we get into this, I am going to try and act
aggressively like Debby might. Sorry, but I don't want you to be
surprised and upset. OK?" Rob just nodded and Tara left the room.
Rob could taste and smell the lipstick. It felt strange and exciting
at the same time. His erection had grown and he remained hard causing
a big bulge at his crotch. He walked around the room and got used to
balancing on those heels. He sat on the edge of the bed and waited for
Tara. The plug settled itself deeper, but he felt little pain. It was
discomfort.
She entered the bedroom completely nude with a big smile on her face.
Her hand was stroking that strap on and Rob knew what she expected.
"Open wide and suck me off, bitch," she said in a gruff voice. The tip
entered Rob's mouth and he tried to salivate and take it in. "Deeper,"
she grunted and thrust hard. Her hands held Rob's head. Tara pushed in
deeper and for an instant, the dildo was buried fully in Rob's mouth.
It touched the back of his throat. After a few minutes of this, the
thrusting stopped and Tara withdrew leaving Rob almost in tears,
lipstick smeared and spittle dribbling down his chin. She leaned down
and kissed him lightly on the lips. "So sorry but we don't know how
long or wide Debby's strap-on will be. But you can assume she will
thrust in hard and impatiently." Rob just nodded glumly. There was
nothing to say as he had agreed to this.
"You know what's coming next, don't you?" Rob looked at her with a
mournful look on his face, scared. Tara looked at the strap-on. The
lipstick marks showed how deep it had been in his mouth. "Not bad for
the first time," Tara said with a sly grin. "It was the first time,
wasn't it?" Rob looked at her glumly. "Just joking."
Tara applied more lipstick to Rob's lips. She took his hand and lifted
him and kissed him very briefly and led him to the foot of the bed.
"Hold hard onto the frame," Tara said, raising his skirt and pulling
down his panty. Suddenly the plug was removed. Rob then felt something
small at his hole and then felt a cooling gel. A moment later the hard
tip was at his hole and Tara thrust somewhat hard and in several
thrust was deep inside. Except for a grunt, Rob made little sound.
Tara moved faster although her movements were not smooth. She was not
used to wearing and using such a device. In less than ten minutes Tara
withdrew turned Rob around and before he could say anything, kissed
him hard. This was the first kiss for Rob wearing lipstick. It felt
different and any pain or discomfort was forgotten.
"Oh Rob, I am so sorry," Tara whispered. "I would never hurt you. I
just wanted to prepare you for the worst. Are you OK?" she said with
her arms around Rob in a strong clinch. "Until yesterday I had never
used a strap-on. I don't know what experience Debby has with one or
what size it will be."
"I guess I know what to expect," he replied softly. "Can you please
keep your promise?"
Tara looked at him with raised eyebrows. "What promise?"
"You promised to kiss away the hurt,,," Rob never got to finish his
sentence as Tara pounced on him thrusting her tongue deep into his
mouth.
They stayed like that for some time. "Know something?" Tara whispered.
"What?" Rob asked kissing her lightly.
"If you can look this good with my inexperience, I think you will look
fantastic with a professional makeover and better clothes - all
courtesy of Debby."
"What do you mean?" Rob asked still holding on to Tara. Her hands
wandered down and she felt the hardness at his crotch. She pushed him
onto the bed. Within seconds she was on her knees.
Tara lifted her head from Rob's hard penis. "I can't talk with a mouth
full." She continued to suck and blow, squeezing his sac until her
rapid movements caused a massive eruption deep in her throat. She kept
sucking softly until he was fully flaccid.
"I mean that Robin could turn me bi," The smile on her face was broad.
"Will you be Robin for me too? Not just for Debby." Tara looked up and
invited his kiss. Even though she had just swallowed his juices, Rob
was not put off. He kissed her tenderly.
Rob looked down at her. She was stroking his penis which speared to be
growing. "Are you serious?"
"Well? What do you say? Your little guy appeared to enjoy it."
Rob thought about it whilst Tara gently stroked his penis. He had
never had a girlfriend who would bring him to a rise moments after he
had erupted. Then again, he had had just one serious girlfriend with
whom he lost his virginity. After one or two dates, a couple of
kisses, all these girls disappeared from his life. He wished so much
that he had met Tara first.
"I'll tell you after Saturday," he replied softly. "Is that OK?"
"I think I'll get a better answer if I ask this little guy. He seems
to like my mouth," Tara said with twinkling eyes. Her mouth swooped
down on his now very erect tool. "I like him filling my mouth too and
can't wait to have him fill my other holes."
Rob couldn't speak he was full of sexual tension, excitement and
trying to control himself so he wouldn't end too soon even though he
had just erupted. He felt it wouldn't be long. Sure enough, it didn't
take long for him to erupt. Tara had managed to get him so deep in her
mouth that her nose was buried in his pubic hair. She kept it there
until he was soft. "Two nice loads," she finally said.
"I'll send Debby a message to ask if she can do this Saturday. I would
like it behind us quickly."
"Thanks, Tara. That would be great and I appreciate the help. I am
still trying to digest all of this,"
"I know. Let's get you changed or the little guy might wake up again.
I really don't mind but there is a danger he won't want to go home."
"I haven't done anything for you," Rob said hugging Tara. "Can I?"
"I promise you that I will want a lot more after this is over. I want
you to relax and even if this is difficult, we will get it behind us,"
Tara kissed Rob back and helped him remove his clothes. When he was
naked, she bent down and kissed his penis. "Till tomorrow, little
guy," she whispered taking the head back into her mouth briefly.
Rob dressed and after several more lingering kisses left. He was still
thinking about the experiences of yesterday and today. He had not felt
the pain as he had expected. He was dressed as a girl today for the
first time but he certainly didn't look nor feel like one. He knew he
had to look better for this to work with Debby. This was his only
experience with a strap-on but he suspected that Tara was being
gentler than Debby. Still, he felt better able to imagine what he had
to endure. It wouldn't be a loving experience. Yet, with Tara's
coaxing, he felt good to simulate what he would experience if he were
to fuck any of her openings, especially her mouth. He loved how she
got him erect in minutes.
On the short drive back he heard his phone ping. He saw that it was
from Tara but he would have to wait to read it. He entered his
apartment and read the message. 'Debby says Saturday works if the
salon has time for you. She'll know tomorrow. Sweet dreams.'
Today was Wednesday and Rob was pleased it would be over. Whatever the
pain or humiliation, he was glad it would be over. He very much wanted
to experience more with Tara. He knew she was someone he wanted to get
very close to. Rob fell asleep dreaming of himself in a dress and
makeup making love to Tara. She seemed to like Robin. He wondered if
she would let him fuck her in the arse.
Rob had a hard time concentrating on his job. He wanted to spend more
time with Tara and develop a normal relationship. He enjoyed the time
with her but there was Debby always at the back of his mind. He had no
idea why.
Lunch approached and Rob waited to see if Debby or more especially
Tara would be there. He knew sometimes meetings overran and lunchtimes
were affected. To his surprise, Debby appeared a few minutes later.
She sat at his table and said a brief 'Hello'. As usual, in between
bites of her salad, she had that same penetrating look which disturbed
Rob. He hadn't realized it before but Debby's stare would put off many
a man. He understood her history and wondered if this was the result
of her experience or her normal look. She never spoke much so her
silence was not a surprise. Just as Rob finished his sandwich, Debby
looked at him.
"The salon can see you at 3.30 on Saturday. They will need about 2 to
3 hours to do everything. So we can meet at about 7. I'll talk to
Tara." Debby got up and left. There were no surprises but he didn't
understand what would take that long. Tara would know.
Rob sent a message to Tara and asked if he could drive her home. Tara
didn't have a car and normally took the bus. Lately, Rob had driven
her back as they spend evenings together. He wondered what more she
was going to make him do tonight. In her company and with her loving
help, Rob felt he could do anything to put this behind him. The prize
was that he could have normal relations with Tara and she promised to
allow him a normal sexual relationship. It sounded exciting.
Tara suggested they meet around 5.15 pm in the parking lot as before.
Rob looked forward to that and completed his work promptly at 5. His
boss needed to talk to him and Rob rushed through his questions and
dashed out to the car park. To his horror he saw Debby standing with
Tara. It was too late as Tara waved to him. He wondered what surprise
she now had for him.
"Him" he greeted them anxious to avoid hugging and kissing Tara in
front of Debby who was nervously smoking a cigarette. She stamped on
the butt as Rob approached.
"Hi Rob," Tara replied. "Debby wanted to suggest something and I
thought you needed to decide."
"I wanted to ask if...." Debby paused for a moment searching in her
bag. She found her pack of cigarettes and lit one. Her hands were not
shaking as much as the last time. Silently Tara grabbed the pack and
took one herself and Debby lit it for her. Her nervousness was
apparent as she inhaled and rapidly blew out smoke. Rob knew Tara was
not a regular smoker.
"I wanted to know if I should reserve a hotel downtown for Saturday.
After your makeover and dressing, we could meet in the bar, have a
drink and then go to the room."
Rob looked at Debby and then at Tara who appeared really upset. He
understood. Tara didn't want Debby to spend more time with Rob than
necessary. It wasn't a date. Her looks showed her anxiety.
"Debby, I promised to help you," Rob said finally. "I will dress and
do as you want but I don't want to be seen by strangers. It seems I
have to come back from the salon to the apartment in a dress. I have
never done this before. I think an apartment is best. I don't want to
be seen in public." Rob paused. Tara was looking at him and taking a
deep drag, blowing out a cloud of smoke. "I would prefer it to be at
my apartment then I can change back easily."
"Or we can do it in my apartment," Tara interrupted. "You can change
into the clothes you went to the salon in. I promised to go with him."
Debby looked at both of them, smoking for a moment. "I understand. You
both can decide where we meet and I'll plan to be there for about 7.30
pm."
"I don't want to be in the apartment when you both meet," Tara said.
"I promised Rob to help him remove the makeup etc."
"Yes, I don't want that either," Debby said. "You can wait in my car.
I can text you as I arrive so you can sit in my car. Keep your front
door open. When I return to the car you'll know I am done." She ground
out her cigarette. "I talked to the salon and will give them all that
you need. Tara gave me the sizes." Debby left abruptly and Tara and
Rob stared after her.
Tara took one last drag on the cigarette. "I know why people smoke
when under pressure," she said. "Sorry, but I didn't expect that." She
went up to Rob and hugged him and kissed him lightly on the lips. "I
am so glad you didn't want to be seen with her in a bar. What the hell
was she thinking? She wanted a date with you in a dress?"
"There was no chance of that," Rob said.
"You will only be Robin for me, right?" Tara said linking arms with
Rob. "Let's go. I need a drink and some food."
"I told you I'll tell you after Saturday. Yes, I could do with a drink
and food. Pizza?"
When they got into the car, Tara gave Rob a long lingering kiss.
"Thanks," she whispered.
"For what?"
"Not wanting to go on a date or whatever with Debby. I still can't
believe she would want to be seen with you in a bar and then rape you
or whatever the word is."
"Yes," Rob replied. "There is more to this than her boyfriend
experience. I am sure she has other issues. So you don't think I'll
look good enough to go out on Saturday? Robin will not look good?" Rob
asked with a smile.
Tara looked at his profile and smiled back. "I think you'd look great
with your figure and what all the salon will do to you. I would be
happy to go out with you in a dress if you wanted. But then I'd take
you home and make love to you, not rape you."
"I think the technical term would be abuse. Since I agreed to let her
do it, I don't think it is rape. Either way, it would be what she
wants not what I want."
They stopped at a small Pizza parlor on the way. They each had a piece
of pizza and a glass of wine. Their talk was about their day and the
office. The subject of Debby would come up later.
"Are you coming back to the apartment?" Tara asked hopefully as they
went back to the car.
"Yes, if it's OK with you. There is something I need to do," Rob
replied.
"Of course. What do you need to do?"
"I'll show you," Rob replied mysteriously.
They entered the apartment and Tara pulled Rob to her and gave him a
deep kiss. "This will be over soon," she said. "So what do you need to
do?"
"I want to pay you back," Rob said with a smile. He took her hand and
led her to the bedroom. "Just sit on the edge of the bed and relax,"
he said. Tara watched in silent amazement. Rob raised her skirt and
tried to pull down her panties.
"I am very happy you want to do that but I suggest we undress a little
first, don't you? Then we can relax." Tara stood up and unbuttoned her
blouse and unzipped her skirt. Tara was down to bra and panty. She
watched as Rob too undressed and was now in his boxers and socks. The
tent in his boxers showed his excitement. "What the hell, take it all
off," Tara said releasing her bra and dropping her panties. Rob
dropped his boxers,
Tara pulled him to her and hugged him tightly. "I can't wait for
Saturday so we can do what we want. I am sorr....," Tara started but
never finished as Rob thrust his tongue into her mouth. "Rob, I have a
feeling Debby knows we have grown close and she will be more
aggressive. I saw the way she observed us today."
"You think I should back out?"
"I told you, that's your choice. But expect her to be rough."
"OK, you have shown me what to expect so I guess I'll have to suffer
through it."
"Yes, I can't take that away. But it may help if we put that thing in
you so you get used to having something in there. If you want, I can
do what we did last night."
Rob looked at Tara with a puzzled look. "If you think. It sounds
weird. "
"It is, but you may be grateful that you prepared. We'll have to lube
you there too so it is easier on Saturday. Don't look so glum. It
wasn't so bad yesterday, was it?"
"No, I suppose." Rob looked confused.
"OK, let's do that and..." Tara paused.
"And what?" Rob asked when Tara didn't continue.
Tara looked at him shyly. "When this is over, if you want, you can
take me back there too. I never did that before. I have one condition
though."
"What condition?"
"First you have to make love to me normally. Then you can do what you
want. You don't know how badly I want that,"
Rob smiled. "You mean you want it badly back there?" Tara threw her
skirt at him.
Tara lubed and inserted the plug into Rob. It was not comfortable but
there was no pain. He knew what to expect on Saturday. Tara sat on the
edge of the bed as Ron knelt between her feet. They kissed hard. Rob
suckled her breast taking each nipple into his mouth. As his tongue
traveled down her body he inserted his tongue into her navel cavity
which caused Tara to pull him into her hard. He left a trail of
spittle down her body through her pubic hair to her very wet and
swollen lips. At the mere flick of his tongue, Tara shuddered. She was
close as Rob inserted his tongue between her lips moving upward and
finally sucking on her knob. Tara exploded pulling Rob's face deeper
into her groin.
"Oh my God," she exclaimed. "That was a volcano. I've never cum like
that." She lifted Rob's head, looked at him and kissed him hard. It
was the first time she had tasted her juices from a partner. They
hugged for a moment and Rob forgot he had something inside his
passage. He felt it but there was no pain or discomfort.
Tara stood up and helped Rob stand. "That was incredible," she said
kissing him lightly. She then pulled him onto the bed and got on top
of him. It didn't take long for them to be in a 69 position. It took
some time but they savored the moment and exploded again. They lay
like that with their mouths still at the base of the other's groin.
"I'd better go," Rob said rolling off Tara.
Tara didn't say anything and just hugged Rob. "Turn around and bend
over," she said. "Can't have you going home with that thing inside
you." As Rob leaned over the bed, Tara gently pulled on the disc at
his rear passage. The plug came out with a soft squish. "We'll have to
lube you well on Saturday but need to make sure the lube doesn't run
and stain the dress. The panty can be washed. I may need to get a
pad." She slapped his backside lightly. "Nice," she uttered softly.
Debby did not turn up at lunch the next day. Tara did take lunch
sitting across from Rob. Except for discreet, accidental touching of
their feet their contact was normal. They ate slowly each thinking of
the events to come.
"Meet 5.15?" Rob asked.
"Yes, as usual."
Rob looked forward to meet Tara. They had grown close and Rob knew
they were well matched. Tara was interested in him, looked after his
interests and seemed genuinely to want his company. She also enjoyed
sex with him and on Saturday they would break their self-imposed
abstinence. Rob looked forward to that. Without Tara, he would never
have agreed to this act. He wondered if Debby would have asked him
directly.
It was Thursday now and just 2 days before the big event. Rob and Tara
did meet and decided that they would just go to that bar where Rob
first invited Debby. It was the second time they were alone in the
bar. They found a parking spot a ten-minute walk from the bar in a
corner by a large dumpster.
"So have you heard from Debby today?" Rob asked quietly. "Any
surprises?" Rob was drinking a small beer. Tara wanted white wine.
"No, don't think so. She told me she had dropped the outfit and stuff
at the salon and made arrangements for you to change there. I asked
what the outfit was but she wouldn't say. She said you would look
good."
"If I have to walk out of the salon dressed, I hope I don't look like
an ugly hooker," Rob said glumly.
Tara put her hand over Rob's. "First of all, I said I would be with
you at the salon. I made an appointment one hour later than you. We
should both be done by 5.30 or 6. I doubt Debby will want you looking
like a hooker as that means she too would have looked like that. She
said that she looked so hot that Brad lost it and attacked her. You
may get some looks in the salon or on the walk to your car, but you'll
manage it. We can say it's for a prank at a party if anyone asks.
We'll take a low heeled shoe to the salon. If Debby wants you in
matching high heels, you can wear then when you are back in the
apartment."
Rob nodded but was still concerned and mulled over his decision to do
this. It was bizarre, weird, crazy and a lot more things besides. But
he was brought up not to break a promise. He wanted no guilt in
breaking up with Debby but that was illogical: he had never had a
relationship with her!
They had a light dinner at the bar. Most of their conversation was in
short sentences. In some ways, it was a help to be amongst people.
They had already talked about this bizarre plan for many hours. Rob
could still back down but he wanted this behind him and there was no
way he could face Debby after that in the office. He also worried if
Tara might think he wouldn't keep to his commitments. Although she
knew his motive and supported him fully, he didn't want her to feel he
made such promises - bizarre as the request was - lightly.
It wasn't late when they left the bar and it was getting dark. Tara
grabbed his arm. "It'll be over soon," she whispered. "You look
worried and tired. You can come back to the apartment or go get some
rest."
They reached the car, stopped for a moment and looked at each other.
"You're right but I would like to come up..."
They got into the car. Tara turned to Rob, held his head in both hands
and kissed him tenderly. "I would like that very much but you need to
relax and be ready for this. It'll soon be over." She kissed him
lightly again. If you come up, I might not let you go home." Tara's
hands roamed down his body to his crotch feeling the growing bulge.
Whilst stroking his hair with one hand, Tara tried to open his pants.
Rob didn't hesitate to allow her access and soon his growing erection
sprang through the slit in his boxers. Tara stroked him slowly.
"Somebody might see," Rob interrupted.
"It's dark, there is no car near us and who cares," Tara replied
licking the tip. Slowly it disappeared deeper into her mouth. Rob
stroked her back and tried to thrust deeper. It didn't take long and
Rob erupted with a load. Tara's lips were tight around his cock not
letting a drop escape. She moved up and down and kept the deflating
organ in her mouth. It took some minutes and Tara flicked her tongue
at the slit extracting every drop. She looked up. "What a tasty
dessert," she offered. "I hope you're a little relaxed now and within
a few days, you don't need to go back. OK?" She reached up and kissed
him. Some of the ejaculate still on her lips but Rob didn't mind.
"Oh yes," Rob replied.
"Sleep well. Just one more night and we can celebrate." Tara pecked
him on the lips and sat up straightening her blouse. Rob pulled up his
pants and started the car.
"I'll see you tomorrow. I can pick you up at 7.45 and get a coffee."
"Yes, that would be nice," Tara replied. Rob gave Tara a deep kiss and
drove away. He couldn't wait for this to be over. Whatever he had
committed to and he needed to endure, he was very sure he had found a
great partner and lover in Tara.
It was a restless night and the thought he would meet Tara early
cheered him on. She was waiting and greeted him with a kiss. "One more
day," she said softly.
They stopped at a coffee shop for coffee and muffins. The short ride
to the office was in silence.
"Please check with Debby for any changes. Try to see how long she will
need." Rob went to his desk wondering how he could concentrate on the
job today.
"Yes, I'm sure she'll call. Don't worry it'll soon be over. Car park
5.15?" Tara kissed him lightly on the lips and walked away. Their mood
was polar opposites: Tara was glad it would be over and she and Rob
could develop a normal relationship. She thought Rob was a keeper and
they had experienced so much together in a short space of time that
had brought them even closer. For Rob's part, he was nervous and
anxious and unsure about how he would survive all of this.
There was no sign of Debby or Tara at lunch. This was not unusual but
Rob's mind strayed to what else Debby might be expecting. He would see
Tara after work and then this would be the start of the biggest
weekend in his life. That thought made the afternoon bearable.
Rob looked forward to spend the evening with Tara as he shut down his
PC and walked to his car. He was feeling a little easier that Tara had
not sent any messages with changes.
Thankfully, Tara was alone and they got into the car, Tara turned and
gave him a deep kiss. "Soon it'll be over," she whispered. "Why don't
we have a quiet meal and then go to my place," she suggested with a
twinkle in her eye. "I want you to be completely relaxed."
Rob gave a hint of a smile at the thought. "Sure," he replied. "Any
place in particular?"
"How about that food court in the mall? I need a couple of things,"
Tara replied with an enigmatic smile.
"What kind of things?"
"You'll see. I think you will appreciate it later."
It was hard to be nervous with Tara at his side. He was resigned to do
this and put it past him. There were moments when Tara's words and
actions caused him to get excited. He didn't know if this was done
deliberately or accidentally but each day he was more sure that Tara
would be a great partner in and out of the bedroom.
They ate at the food court in the mall. "Why don't you get some wine
or whatever and we can meet back here in 15 minutes," Tara said. Tara
left Rob to finish his meal whilst she went shopping. There was a
small wine bar and Rob purchased a bottle of cold white wine and a
bottle of red.
Tara was back within fifteen minutes with two small bags that had no
logos. She took his hand as they walked to the car. They drove to
Tara's apartment and carried their purchases in.
"You know it's Robin time tonight, right?" Tara asked giving him a
small kiss. "You have to be ready and dressing will help. OK?"
Rob nodded glumly. His happy mood suddenly disappeared. "I know," he
mouthed softly.
"Don't look so glum. It was fun last time and I remember very well how
your little guy was. Think of it as a game between us where we're both
having fun." Tara paused whilst unbuttoning Rob's shirt. "I know
tomorrow will be different but think about how much nicer it will be
for us to enjoy each other without that cloud of guilt. I can't be
with you for those minutes but I will definitely be there in thought.
OK? Now, let's try to enjoy it." She kissed him lightly and stripped
him of his shirt.
The pants and boxers were next. "Your little guy likes the idea, it
seems," Tara said holding the growing member in her hand. "Girls don't
have these things growing so big and hard at their sensitive spot.
We'll have to do something about this, won't we? Well, what I mean is
that I can do something and you have to relax and enjoy it."
Rob saw Tara kiss his nipples, trying to take a nipple into her mouth.
It was too small. She licked down his body until she was on her knees,
looking up at him with his rampant cock at her mouth. A few tentative
licks, the head disappeared between her lips and then he was all the
way in. She certainly knew how to excite him and within a few minutes,
he exploded down her throat. Tara was always insistent to let his
member deflate in her mouth with gentle licks and then using the tip
of the tongue to extract everything from the foreskin and slit.
"There now, he should stay down a little anyway." Tara rose and kissed
Rob who was now used to the taste. "If you need to use the little
boys' room do that and I'll get some things out.
Rob headed for the bathroom and Tara laid out some clothes for him. It
was a simple dress, bra with panty fillers and shoes. Rob came back a
few minutes later and saw the items on the bed. He started to grab the
items when Tara stopped him.
"Turn around and hold the end of the bed. You need lubrication." Tara
inserted her finger into his anus and pushed in a large glob of a cool
gel. Rob couldn't help it and wiggled his bum and invited her finger
in deeper. Tara smiled. "Before you pull up your panty put this in,"
Tara said wiping her finger on a panty liner pad. "I don't think we
need the plugin tonight." Tara had a big smile on her face. "I'll be
putting something else in there." She kissed him on the lips lightly.
Rob did as asked and felt the soft pad. "This will not only help keep
the front flat but will also help absorb any lubricant spoiling your
dress," Tara explained as she pulled the panty up and tight.
Tara held out the bra and Rob put his arms through the straps. "I
think Debby will have some pads for you tomorrow but I only have
panties and hose." Rob buttoned the blouse and pulled up the skirt.
Tara had him step into the shoes. "I am sure it'll be a garter and
stockings tomorrow but you'll manage fine."
"I wonder what kind of wig she has chosen," Tara said. "You'll look
great. Now hold still." Tara applied some dark lipstick, which is what
she usually wore. "We'll need to apply plenty of lipstick and gloss to
make it easier tomorrow. Now, why don't you walk around on those heels
and find your balance whilst I get ready."
Tara kissed Rob lightly on the lips. "Sorry, but I'll try to be rough
as I think Debby will be. But I don't really know how to use the strap
on too well."
Rob looked at her blankly. "I know," he said softly and started to
walk around the small room. Tara went into the bathroom to change.
Rob walked around finding his balance. Whilst he felt strange in this
outfit, he was preparing mentally for the encounter with Debby. He had
accepted that he would be humiliated and even hurt. Yet, this play
with Tara was exciting in an inexplicable way. He didn't feel shy or
afraid to have Tara play with him dressed as he was. It was strange.
In some ways, he felt he understood Tara better and how she used her
mouth and hands to please him. Tomorrow he would get the ultimate
prize: making love to Tara without guilt. He knew Tara felt the same
way.
He saw Tara enter the room trying to keep a stern face. "Looking good,
bitch," she said. Try as she might, the words came out a friendlier
than she wanted. She was stroking the penis strapped to her crotch.
"On your knees. You know where this is going."
Robin looked at her a little startled then went around and fell to her
knees. Tara approached. "Ready for this?" She rubbed the tip of her
plastic penis across Robin's mouth as if it were a giant lipstick.
Robin looked up at her and moved her hands to the hard round part that
resembled a sac. She opened her mouth as Tara thrust in hard. Robin
nearly choked and then began to salivate furiously as Tara began to
thrust as deep as it would go. She kept up the movement for around ten
minutes and then slowed down. Robin was grateful that the plastic
penis was not wider and longer. The layers of lipstick and saliva
helped.
"Stand up and bend over you stupid bitch. You know where this is going
next, don't you? You want to tease men? Well, let me show you how to
enjoy it."
Robin got up stiffly and Tara puller her to the edge of the bed and
pushed her over. Robin's arms and head were on the bed and her rear
end was raised. Tara yanked down the panty and pointed the tip of her
strap on to the entrance of Robin's hole. "Take it, bitch," she
grunted and thrust in.
Robin was ready for the assault but it was still hard at first.
Thankfully, it was more shock than pain. Tara held on to the hips as
she thrust and within a few strokes was flush with Robin's cheeks.
Tara thrust in for another ten minutes and then slowed down. This was
not a natural movement she was used to. Slowly she extracted the
plastic tool and pulled the pad lined panty up Robin's behind. She
then hugged him from behind in silence.
After a few moments, she helped Robin up, turned her around and hugged
her tightly. "Sorry," she whispered in his year. "Did I hurt you?"
"No," Robin whispered back. Their mouths met and they spent a long
moment in a tender tongue battle.
"Let's get a drink," Tara suggested as she held Robin's hand and led
them into the small living area. Tara still had the strap-on swinging
from her hips. "Sit on the couch, I'll get us some wine."
Robin sat there in a bemused condition. It was strange to be dressed
like a girl having had to use her mouth and anus to please someone. In
some strange way, she was excited by what had happened. The rather
prominent bulge at her crotch proved this.
Tara returned with two glasses of wine with that pink object swinging.
She wore nothing else. Neither she nor Robin appeared to consider it
unnatural. "Are you OK?" she asked softly.
Robin nodded. "Yes. I am OK."
Tara leaned down and kissed Robin lightly on the lips. "You do look
good as a girl and probably even better than Debby or me when we're
dolled up. Excited?"
Robin looked up at her not wanting to understand what Tara meant.
"That's silly," is all she managed to say.
"Well, it may be silly to you but I know a way to check."
Robin looked up as Tara sank to her knees between Robin's legs. The
bulge was prominent even though it had been some minutes since Tara
had ended her penetration. Tara looked at Robin as she lifted the
skirt and pulled down her panty exposing a still hard penis.
"This guy will never lie to me," she said licking the tip and planting
a sloppy kiss on the head.
Tara took it in ever deeper and soon was at the root. Her eyes never
left Robin's face. Her other hand massaged the tightening sac and she
knew she would soon be enjoying a mouthful. Robin sat there passively
as her excitement grew and exploded in Tara's mouth. Tara rose
immediately and hovered over Robin. She leaned forward and thrust her
tongue and exchanged a large part of Robin's deposit. She held Robin's
head in both hands and she spread the deposit widely in Robin's mouth.
They had kissed after Tara had accepted his ejaculate, but she had
never deposited such a full load. There was no lack of intensity as
their tongues intertwined.
"I just wanted you to know how much I enjoyed the taste of your
juice," she said with a smile. "I know my juice tastes different."
Rob was surprised that he had no hesitation for the kiss or to accept
his ejaculate. It never struck him as odd. He was growing close to
Tara and any sharing of intimacy was acceptable.
"I can't use this and eject in Robin's mouth," Tara said stroking her
plastic penis. "You'll then know exactly how I feel."
Rob just gave her a wan smile. It was a new experience and in reality
he thought it intimate and exciting rather than strange and repulsive.
"We had better get you changed as we may need to use the skirt
tomorrow to the salon." Tara held out her hand and helped Robin up as
they turned the corner and walked into her bedroom. Robin followed
with a curious smile on her face.
Tara used a washcloth and removed what little lipstick Robin had left.
She looked at the rather bemused look on Robin. "Would my girlfriend
Robin like to stay the night in my bed? But we can only go so far."
Robin's face broke out into a big smile. "Keep your panty and bra on.
I'll give you a nighty. There's a spare toothbrush in the cabinet."
Tara looked up at Rob as she undid the harness and strap on. "I don't
think we'll be using that again, tonight anyway." She broke out into a
big smile. "I think Robin likes being taken back there and I like
doing it too. I am looking forward to my boyfriend Rob doing that to
me too."
They climbed into the queen-sized bed. It wasn't long before they were
kissing. Tara's hand wandered down to the growing bulge in Rob's
panty. It wasn't long before they reversed positions and turned on
their sides. Tara was licking Rob's growing member. She took it fully
into her mouth, stopping for a moment. "I can't remember the last time
I slept with a pacifier in my mouth. I could get used to it."
Most of the night was spent that way but morning found them spooned
against each other in a tight embrace. Tara kissed the back of Rob's
neck. "This is a nice way to wake-up," she whispered into Ron's ear.
"It might be habit-forming."
Tara's hands wandered down to find a growing bulge at Robin's groin.
"Robin, it seems that this guy is going to cause an unsightly bulge in
your beautiful outfit. I'm going to have to milk you dry today." Tara
paused as she moved down his body. "I like doing this job." Her mouth
engulfed Robins growing member. It didn't take long for it to erupt.
Tara turned and moved up over Robin looking at her face, trying to
decide something. She brought her mouth closer and clamped down on
Robin's mouth exchanging all that she had. It was a long kiss.
"I am glad you enjoy as we share. I am growing to love the taste,"
Tara said as they continued to lie on each other. She felt the bulge
on Robin's chest. "These will be bigger and nicer tonight, I think,"
she said with a smile. "I might be turning bi."
"If you don't mind the taste why should I? I am happy you like doing
that."
Tara thought for a moment. "I am so glad Debby introduced us. Even if
you have to go through with this stupid thing. But tonight it will be
over." She kissed Robin tenderly. "Do you think it strange that we
enjoy each other like this? I never had a boyfriend who would have
allowed that. I love you for it."
Robin looked at Tara. It was the first time any girl had used the word
'love' to him. It was exciting and intimate and seemed perfectly
natural for two people to enjoy each other.
"I'm going to get some breakfast. Just relax. Then we start with the
Nair again to make sure you are smooth and practice walking. OK?"
Tara put on her tracksuit and stepped out. She was back in about
twenty minutes with some breakfast stuff. The coffee had percolated.
Robin got up and straightened out his nightdress and moved the bra
back into place. It looked odd but somehow Tara's acceptance made it
seem OK. She smiled as Robin joined her at the small kitchen table.
They drank their coffee and had a toasted bagel. Tara was deep in
thought. "What about dinner?" she asked. "I don't know how long Debby
will be here but we need to eat something."
Robin had that bemused look again. That was the last thing on her
mind. She was getting anxious ab
Tara smiled. "Yes, I think we'll both need that. I can get everything
at that small supermarket on the corner before we go to the salon."
"You have a driver's license, right? Or will we take a taxi? I don't
want to drive," Robin asked.
Tara thought for a moment. "I can drive but you have a nice parking
spot now. So let's keep the car there and take a taxi. It shouldn't be
that much for an Uber."
Robin nodded. "What do we do now? I think the salon appointment is at
3 pm."
"Yes. If you agree. We should dress you up better with a little makeup
and you should practice walking as we will be walking to the salon. I
don't know what heels you will be getting. You can get you naired and
showered before we go to the salon." Tara paused for a moment. "Do you
want me to insert the plug so it will be easier tonight?"
Robin looked miserable and nodded. "You can wear the same skirt and
blouse. I have the other dress which you can wear to the salon. "Tara
got up and held out her hand. Robin followed her into the bedroom.
Robin's face was a mask. Without a word she went to the foot of the
bed and bent over. Tara inserted the lubricant and then gently
inserted the plug and then hugged Robin from behind. "It'll soon be
over," she whispered.
"I want to brush my teeth," Robin said and walked to the bathroom next
door. Tara busied herself with getting the skirt and blouse ready. She
also sought out the brightly colored sundress and hung it up behind
the bedroom door.
Robin returned and saw the dress. A small smile appeared. She removed
the nightdress and Tara approached and inserted more socks into the
bra cups and straightened the straps. "Not great, but it'll do for
now. Maybe I'll find something like pads or cotton for when we go to
the salon. I am sure the salon has a solution."
Robin pulled up the skirt and then the blouse. Finally, leaning on
Tara she put on the heels. After a moment of finding her balance, she
stood straight. Tara approached with a hairbrush and brushed the
medium length hair to a female style. Lipstick and a touch of mascara
followed. "I don't use much makeup and am not good at it. But this is
just for you to get the feel of it."
"What are you going to do at the salon?" Robin asked thoughtfully.
"I was going to get my hair cut and styled. Why?"
"I thought you might like to also get a makeover. Then when we walk
out of the salon it will be as if we are both going to a party."
"I didn't reserve an appointment for that." Tara saw the look on
Robin's face. But I can call and see if they can fit me in. I know
what you mean. I have only one good outfit though. I'll have to wear
that. It's a dark blue mini-dress. Not sure what Debby has planned for
your outfit. I assume it will also be a dress."
"You don't mind doing that?"
Tara looked at Robin with a smile. "If it will make you feel better, I
will. It's the least that I can do. It will be a celebration of sorts
I guess. "I'll make the call to the salon. They may know what you will
be wearing."
Robin followed Tara into the living area. She got her phone and
called. She spoke to Tiffany who was the person Debby said would be in
charge. Robin heard Tara ask some questions on the pretext that she
wanted to know what else might be needed. All Robin heard was some
'Oh?' and 'I see'.
Tara ended the call with a smile. "It seems Debby thought you might
agree to the drink etc before and wanted the salon to get forms etc
for you. The dress will be similar to the one I described but in a
bright red. She couldn't tell me about the wig because she doesn't
know what would suit. Debby has described she wants Robin to look
elegant." Tara had a big smile on her face. "I am sure this cost a lot
and I am surprised Debby would spring for this amount."
"What do you mean? Why would she spend so much for a one-time event?"
"I have no idea. She must have looked great if Brad raped her on
sight. So she can't simulate it if you looked like a plain Jane." Tara
faced Robin and kissed her lightly on the lips. She had that smile on
her face. "I know it's asking a lot but..."
"But what?" Robin asked with a slightly raised voice. "What now?"
Tara looked at Robin. "I wanted to ask a favor but it's too much to
ask."
"What? Why don't you ask and let me decide?"
"Well," Tara started, "well, if you get through this tonight without
too much trouble or pain, would you like to go out with me as two
girls and have that drink and celebrate? Except Robin will be with me
and not Debby."
Robin stayed silent for a long moment. "You wouldn't mind being seen
with me dressed like that? Even if people see me as a man in a dress?"
"Robin, there is no way you would look like a man in a dress. Not with
all that the salon is planning. Only your voice would be a giveaway.
But this is a friendly city and I see crossdressers in the mall.
Everybody accepts and acts normal. Besides, I would be very happy to
be with you and celebrate whether you are in a dress or pants." Tara
paused. "Or even if you are nude. Only if you feel comfortable, of
course."
"I have no idea what they will do to me, then Debby will attack. But I
do have a very good idea of what you and I could do together however
we are dressed or undressed. If things go as planned, I will take that
drink with you if you don't mind how I will be dressed. I may never
get another chance. Happy?"
"Oh yes, very," Tara said sinking to her knees. "It seems we have to
keep this guy down as he seems very excited at the thought. But I
think I know how to take care of it." Within moments Robin's hard
member was fully immersed in Tara's warm, moist mouth. It didn't take
long for another massive eruption.
Tara rose, looked at Robin with a raised eyebrow. She saw the
acceptance and kissed her deeply with tongue passing the ejaculate to
and from Robin. It was another long kiss and another deeply intimate
moment.
"So, why don't you relax for a little while and practice walking. I'll
go and get some stuff in case we stay home. OK?"
"OK," Robin said quietly. "You had better wipe that lipstick off
before people get the wrong idea."
"What's wrong with kissing my girlfriend on the mouth? It is 2020!"
Tara smiled back enjoying the scene. "I don't care what they think!
It'll be a lot more than kissing by tomorrow. Besides, your lipstick
needs fixing too."
Tara left and Robin was left alone dressed. Her thoughts wandered
again as to why Rob was doing this. Was it really that important? Why
should he have a guilty feeling about Debby when she hadn't even
kissed him on the mouth? It didn't seem right. But he had agreed. He
and Tara had grown quite close and he was sure they would be great
friends and lovers. They both liked the same things. Reluctantly, Rob
concluded that he enjoyed the game of dressing. Whilst hesitant at
first, he had come to enjoy being Robin. It was hard to explain why he
might like the plastic penis in his mouth and anus. He knew that Tara
enjoyed the oral part very much. He had tasted his cum through her
mouth which seemed to even make it a more intimate moment. He was not
at all revolted. It was all very confusing. Finally, in a moment of
madness, he had agreed to go and have a drink with Tara after Debby
left to celebrate. Robin paced the length of the small hallway and
turned into the living area. He tried to sway his hips as Tara had
demonstrated.
Tara returned about an hour later with several bags in her hand. She
had a worried look on her face.
"What's the matter?" Robin asked concerned. "Did something happen?"
"No, no," she replied, placing her bags on the kitchen table and
giving Robin a tight hug.
"You were so happy when you left, what happened? Did Debby call?"
There was a long pause. Then Tara lifted her head and kissed Robin
lightly on the lips. "I'll make some coffee and we can talk." Tara put
away her purchases until the coffee was done.
They sat at the small table sipping their mugs of coffee. Robin felt
the plug sit deeper but there was no pain. "I was thinking that we had
agreed that I would meet Debby in her car and wait until she is done.
But if she sees me all dressed up, she's going to be even madder and
who knows what she will do. Remember, she said she has a gun."
Robin took a few sips of coffee deep in thought. "First of all, she
doesn't know how you'll be dressed or made-up, so I don't think that's
a concern. She does have these strange ideas but I doubt she will walk
around with a gun in her purse. Not sure what she will be wearing but
you could tell her to keep her purse with you when she exits the car.
So, don't worry. We both need to get this behind us and forget Debby."
"I guess she won't be able to carry a gun or weapon in her jacket or
jeans."
"Yes. Also, if you want, you could tell her that I forced you - and
paid - to get a makeover as I didn't want to be in the chair alone.
You can change back into your nice dress when Debby is gone. You
promised to call Debby and tell her when I am ready."
"You're right. I am more nervous than you, it seems."
"I thought about it a lot. It is totally a weird scene but I think we
both need to put this behind us and get to normal." Robin smiled. "We
both made promises we have to keep."
"Oh? What promise did I make," Tara asked a small smile on her face.
"We don't have to wait until tonight I can show you."
"Oh, no, Robin. It hasn't been long but each day has brought me closer
to you and I am desperate to do the things I want. But, I can also
wait a few more hours. I will keep all my promises."
"Deal." Robin leaned forward and gave Tara a tender kiss on the lips.
"No more talk about this. Let's get it done."
Tara hugged Robin. "OK," she said kissing her ear lightly. "It's only
12 so we have about an hour before we need to start getting ready. We
have to be at the salon by three. We told Debby around 7.30 so we will
have time."
"So, what did you get?" Robin asked.
"I got some salad stuff and a gourmet Lasagna. Ice cream and a bottle
of wine and a small bottle of Tequila. Also a big bag of cotton." Tara
pulled a small bag out of her purse. "Tiffany said the dress was red
so I went to the Dollar store and found some clip-on earrings. They
are big red discs and just clip-on." Tara held them out. "Do you
remember I had a room-mate at college who was bi?"
"Yes, why?"
"She said something before. She suggested that you have a douche - an
internal cleaning before lubrication. The cleaner the less pain or
discomfort. I got you a pack if you want to use it. It's up to you."
Robin stared at the wall. "You and I have no experience and idea about
such stuff. I can understand the need for cleanliness."
They sat on the small couch for a little. Robin had her arm around
Tara. There were long moments of silence and some tender kisses. Each
was deep in thought.
"It's time to get ready," Tara said and pecked Robin on the lips. They
went into the bedroom where Tara undressed Robin. Now, it was a naked
Rob that stood there. Tara too undressed completely as Robin watched.
It was the first time they had been totally nude in front of each
other.
Tara opened the pack with the douche and read the instructions. "I
will need to insert his back there and fill you up. You have to wait
for a little and then expel. They suggest doing this twice and holding
it in as long as possible."
Rob looked miserable. "What do you want me to do?"
"Let me fill this bag and then bend over the sink. It has a smaller
nozzle than what you had in there before. Then hold it for as long as
possible. Sorry." Tara kissed his cheek. Rob endured the insertion
twice and expelled it. That Tara was with him helped him accept the
intrusion.
Then Tara applied the nair all over his body even going up to his neck
and cheeks. She also applied it between his cheeks. He waited
patiently and was pleased when he could enter the shower. It was a
small cubicle but Tara joined him rubbing him down.
They dried off, Tara rubbed some lotion all over Rob's body and legs.
Her hands wandered also to the groin area and the growing member.
Holding his member in her hand Tara led them back to the bedroom.
"This guy needs to stay down tonight. Then he can rise at any time and
it won't be a problem."
Tara sat on the edge of the bed and gently licked the head. She
squeezed the foreskin and poked her tongue into the slit. S moment
later the head and slowly she absorbed the whole length. It was slow
with frequent stops. She sucked each ball in the sac and teased the
penis until it was hard. Then she took him from tip to root several
times, massaging the sac. She could feel the pulsing and knew it would
soon erupt. Rob was compelled to hold Tara's head lightly when he had
the biggest orgasm of his life. Tara didn't stop. She swallowed all
and continued to suck. After some minutes she concluded it would be
some time before it could rise.
"I was not ready to share," Tara said planting a small kiss on the
head. "I never enjoyed the two bjs I gave before I met you," Tara
said. "I did it because my friend wanted me to, not because I wanted
to. And I never did swallow. Now, I can't wait to put it in my mouth,
taste it and swallow."
Rob gave a small smile still coming down from his ejaculation. "We'll
have to use that lubrication after the salon," Tara continued. "But I
suggest you use the pad to give a flatter front," Tara suggested and
handed Rob a plain cotton panty and a pad.
Rob pulled up the panty and pushed his flaccid penis back and slipped
in the pad. Tara came to him and pulled it higher and tighter. "I
think he'll sleep for some hours and I'll definitely wake him up
tonight," she said planting a quick kiss on his lips. "I don't wear
stockings as you know and pantyhose may be too much. I am sure the
salon has a garter and stockings planned."
The bra was next and Tara spent some time padding it out with cotton
wool. As much as she was able to pad it in, it still felt softer than
natural breasts. It would have to do. Nobody would touch them except
Tara.
The brightly colored sundress was next. Tara pulled it down so that it
fitted Rob's frame well. A broad stretch belt went around the waist.
Next came the 2" heels. Robin was quite comfortable in them now. Tara
kissed Robin lightly on the lips and applied a dark cherry lipstick.
This was Tara's normal color. She left Robin for a moment and came
back with the clip-on earrings. These were simple red discs but suited
the colors of the dress.
"I don't have a wig for you but we can use a broad straw hat that I
have. It'll cover your head till we get to the salon. I haven't worn
it in years." Tara went to her small cupboard and pulled something
from the top shelf. She straightened out the rim and placed it on
Robin's head. "I can't see any hair but the hat will hide hair
anyway."
Robin looked at the small mirror over the dresser. She could not see
her full figure. The body appeared to have the right curves. The face
with the gash of color was hidden by the brim of the hat and would
pass cursory inspection.
Whilst Robin was admiring herself, Tara was getting ready. She wore
her standard skirt and blouse and low heeled shoes. A dash of lipstick
and she was ready. Earlier she had put her cocktail dress into the
plastic carrier as she wanted to change at the salon. They had
facilities as Robin was going to change there.
Tara called an Uber and waited for it to arrive. She could feel
Robin's anxiety and held his hand tightly. "Don't worry," she said
reassuringly. "I will be with you and we'll have a little time when we
come back here. Just speak softly if you have to. The salon knows who
you are and why you are doing this." She hugged Robin.
They walked down the short flight of stairs to the Uber. It was a
short fifteen-minute drive to the salon. They didn't speak. Tara sat
very close to Robin with thighs touching.
The salon was located in a smaller strip mall with a series of small
shops. It didn't appear to have any distinguishing features. There was
a series of large pictures in the window.
Tara knocked and entered. A small bell rang. She was holding Robin's
hand. As they walked in they could see just four salon chairs, two in
a row opposite each other. Large brightly lit mirrors were on one wall
and the two chairs on the opposite wall had sinks facing them.
Obviously, two chairs were for makeovers and the other for hair
styling. Several rooms were leading off a short corridor.
"Tiffany?" Tara asked the lady wearing a smock. She was about Tara's
height but with a heavier build and rather heavy makeup for daytime
salon work.
"Yes. You must be Tara and Rob." Debby had obviously forgotten to tell
Tiffany that it was Robin. "Alyssa and Martha are at the back getting
everything ready. "
Tara was surprised there were no other clients. Normally a Saturday
should see a busy salon. Tiffany saw Tara's questioning look but
ignored the unasked question.
"Did you depilate thoroughly?" Tiffany asked.
"Yes," Robin said softly.
"Good. It will be easier and quicker."
"What has Debby planned?" Tara asked. "You know we are going to a
party as three girls."
Tiffany's smile indicated that Debby had shared more with Tiffany than
just a regular transformation. "She said she wanted Robin looking a
'hot bitch' if I remember the exact words," Tiffany replied. "It's
good that you also want a makeover so we can try to keep it to a
similar glamour look."
"I brought my dress so I can get changed with Robin if that is OK,"
Tara asked.
"Sure, we have everything planned back there. Alyssa and Martha will
help Robin change. Alyssa and I'll be doing the makeovers. It is
better to change first before the makeover," Tiffany explained. "I can
do your hair whilst they are getting Rob ready."
"Oh, I wanted to watch what they are doing," Tara said seeing the
anxiety on Robin's face. "I got Robin to dress like this to come here
but she has never dressed before. She is a little nervous." Rob could
have come here in jeans and a T-shirt but Tara couldn't imagine this
salon was empty.
Tiffany had a small grin on her face. "For the first time, she looks
OK. But we have to make her a beautiful doll." Tiffany's smile and
demeanor caused Robin to be even more nervous. "We'll have to start.
We need to finish by six as we have two customers coming then. Let's
go to the back."
Tara and Robin wondered at who might be coming so late. They didn't
ask glad that they might be alone in the shop without outside
observers.
Tiffany led them down the short corridor to a room at the back where
two ladies were waiting. There was a waxing table in the middle of the
room and some curtained cubicles where customers could change. One
cubicle had the curtain drawn, the other three cubicles had open
curtains.
"Rob, why don't you undress and remove everything except your panty or
underwear," Tiffany suggested. "Alyssa and Martha know what we have to
do."
"I think we need to call her Robin," Tara said. "Rob won't fit the
girl he'll become." Tara was trying to reduce Rob's anxiety. Rob hung
up the hat and with Tara's help stepped out of the dress. Tara
unhooked the bra and Rob was now left in the panty.
"OK, Robin. Let's see your body and what we have to do.," Martha said.
She was slim and had a pleasant face.
Robin stepped forward nervously as Martha ran her hands over his nude
body, from the chest to legs. "You did a good job with the hair. We
won't have a problem with the breast forms," she said
Robin looked at Tara for some kind of explanation. She assumed the
dress would cover the breast forms inserted into the bra.
"Robin, please lie down on the table," Martha requested. "Just for
perfection, Martha took a razor and pulling down the panty scraped
away the sparse public hair into a straight line. "If you want, we can
trim the hair down there into a nice shape."
"Why?" was all Robin was able to squeak out. "The dress will cover
everything won't it?"
"Oh yes, but it looks prettier if it is trimmed down. But you can do
that later." Martha was smiling at Robin's discomfort.
Alyssa brought a box to Martha and some sachets. "Now you have to lie
still until this sets."
"What sets?" Tara asked interrupting Robin's question.
"Well, because of the cur of the dress, we are supposed to attach the
forms to the chest with medical adhesive."
"What?" Robin shouted
"Well, the dress is low cut and will show some cleavage. A full bra
would be visible. So we need to use a demi-bra." Martha's explanation
was professional.
"How does she take it off?" Tara asked. "It can't stay on for days."
"Oh, no. You can keep it glued for some hours or up to a week
probably. But we have a solvent that allows easy removal whenever you
want."
"I don't think Robin was expecting that for one night. Can't you just
insert them?" Tara asked moving to Robin and holding his hand.
"I don't think it will work as the dress is cut low. But we'll give
you the solvent and you can help her remove them. Just rub the solvent
around the edges and apply more as you lift them off. It is not too
bad and won't hurt. Alyssa, please get the bottle from the cupboard.
Some Drag performers do this daily," Martha smiled. "We have a few
regulars who come here for makeovers and a body transformation. I
think we have two coming tonight. They like to go out to clubs all
glammed up."
Martha opened the box and took two jelly-like forms that truly
resembled natural breasts. The edges were thin and almost transparent.
Robin couldn't see much but gripped Tara's hands tightly as Martha
laid the forms on his chest. She then used the sachet and cleaned
around the chest area. Then she sprayed the underside of the forms and
positioned them, one at a time on Robin's chest. She pressed down
firmly and ran her fingers around the edge of the form. Even at close
range, Tara had a hard time seeing where the edge and Robin's body
met.
"We were told to use C sized forms," Martha explained. "They are a
little bigger than normal for his frame but that was what the lady
requested. Robin, you can sit up now but be careful of the pull. They
are the weight of a natural breast and move like real ones too."
Martha inspected the edges. "Sometimes we use a little concealer to
hide the edges," she said in a matter of fact voice. "I don't think we
need to do that here."
Robin struggled up and Tara held on to her hand. She was amazed that
the breasts looked so natural and were probably the same size and
shape as her own. Even though she knew they were not real, seeing them
on Robin brought back memories of her college room-mate who walked
about their dorm room bare-breasted from time to time.
"When you stand, you can hold them to relieve the pull on your skin,"
Martha said. "When we have that demi bra and dress on you'll have
plenty of support."
Robin's face had a mixture of horror and curiosity. What else would
she need to endure? Thank God Tara was here and had the solvent. She
felt the weight as soon as she stood up. She understood why ladies
needed to wear bras.
"You are slim so we don't need a full corset. But we will use a
cincher to take your waist in a little. It also has the tabs to hold
up your stockings. Today we will use a special strapless bra as the
dress has no straps."
Alyssa held out a garment and Martha wrapped it around Robin's new
breasts and attached it firmly at the back. Robin felt immediate
relief. She looked dazed at the two rather large globes at her breast.
They looked so natural. Tara had an enigmatic smile on her face as she
stroked a breast. "Wow, it'd hard to tell the difference."
"Yes," Martha smiled. "Some of our customers who dress surprise their
boyfriends until they reach down lower." Martha's smile indicated what
some of her customers liked to do. The difference here was that both
Robin and Debby knew in advance what was down below.
Alyssa then handed Martha a garment with gooks in front and laces
hanging from it. It was tied around Robin's waist and pulled tight.
The waist was drawn in by several inches. The tabs for the stockings
hung down. It was constricting but Robin accepted this torture in
silence.
"Now, if you were going all out to please we would use a longer girdle
and pad out your behind so you would have a truly great figure. We
were told that that was not needed but to use a tight panty to flatten
the front." Martha was a professional but she had dealt with these
crossdressers before. The only reason to not use the girdle was for
easy access to the back. She wondered briefly what the intention was
here but kept a straight face. Robin did not appear the type to want
quick fun. Her girlfriend was also in the act so something was going
on.
Alyssa knelt at Robin's feet and rolled up a shiny pair of stockings
up her legs attaching them firmly to the tabs. Tara watched in
amazement as Robin's female form changed before her eyes. Her figure
was not as shapely and Robin's bust was as big as her own. She was
also surprised at herself for admiring the transformation and the
thought of a lesbian affair. She knew full well what Robin had between
her legs but this was a new and exciting adventure she could never
have imagined.
"We have some shoes you need to try. I hope you will find them
comfortable." Alyssa brought out two shoe boxes. The first box
contained some red heels, probably about 4" in height, with a sequin
finish. Alyssa lifted Robin's leg and fitted the shoe. Then the other
foot,
"How do they feel?" Tara asked helping Robin. "Take a few steps." With
Tara's arm around her waist, Robin took a few steps.
"OK," Robin replied softly.
"Let's try the other and you can decide. You have to spend the whole
evening in them so make sure you are comfortable, especially if you
are dancing or standing around for some time," Martha suggested.
Alyssa slipped off the shoes and replaced them with the other pair.
Once again with Tara's arm around her waist Robin walked a few steps.
"So, what do you think?" Tara asked. "You have to be honest."
Robin looked at Tara and then at her feet. "I think the other pair is
better." It was the first time she said anything since this process
started.
"Makes sense," Martha interrupted. "They are somewhat wider. I am glad
you shoes that pair. They are more stylish for evening wear." Alyssa
took the shoes off and Robin felt the tension in her calves' ease,
Tara's shoes were more comfortable and she hadn't felt any pain.
"Let's get the dress on her," Martha said opening the section that was
curtained off. "Tara, why don't you get dressed too so we can start on
the makeovers at the same time?"
There was the red dress that Tiffany had mentioned to Tara. "We'll
pull this over your head," Martha said and slipped the dress off the
hanger. Meanwhile, Tara was hurrying to change into her cocktail dress
and shoes.
Martha asked her to stretch her hands upwards and pushed the dress
onto Robin. The dress was tugged into place over the bust. It was made
of some stretch material and clung to Robin's slender frame. The
sleeves were off the shoulder and attached to the dress under the arm.
The top of the breast was very evident and the globes looked very
natural. Robin tried to peek down the dress but the globes prevented
her from seeing the full length. It appeared very short and ended well
above the knee.
Tara suddenly appeared and gasped. The dress clung to Robin's narrow
frame and looked extremely sexy. The sleeves off the shoulder added a
touch of glamour. "You look amazing," she said enthusiastically.
Robin's face was blank. She wondered why her new girlfriend found her
in a dress she described as amazing. With Robin's fair coloring, the
red dress would definitely draw attention. The prominent bust line
would only add to the spectacle.
Alyssa knelt at Robin's feet and slipped on the sequined heels. Tara
came immediately to Robin and hugged her and helped her find her
balance and walk a few steps with her arm around Robin's waist. It
didn't take long for Robin to find her balance.
Tara guided Robin to a long mirror on a stand near the curtained area.
For the first time, Rob was able to see 'Robin' in the full-length
mirror. From neck to toe, Robin was the very form of a slender female
with a prominent bust; certainly a magnet of attention anywhere she
went. Whilst Tara looked very pretty in her black velvet cocktail
dress, the two of them side by side was a study in contrast below the
neck: a black velvet cocktail dress and a red outfit; both outfits
hugged the wearer's frame.
"It's past 4.00 and we still have to do the makeovers," Martha said.
"Tara, do you want your hair set and styled? We should have time
depending on what you want."
Tara looked at Robin. "If you can style my hair in a neat bob without
washing that would be great. Then the makeover and I think we should
be done by 6. You said others were coming."
"I think we'll manage," Martha said. "Let's go to the salon. I assume
you both want matching looks. Debby never mentioned that Tara would be
here. But she did tell us to go all out with Robin."
"Yes, well, we want to look good," Tara replied. "Of course we need
Robin looking great."
"Debby said you were going to a party so I guess we'll need you both
with heavier evening makeup."
"Did Debby explain what is happening tonight?" Tara asked quietly.
"Of course," Martha replied with a laugh. "We think it's a hoot to
have her male replacement at work come in drag to her leaving party.
She said Rob was a good sport to agree to dress up."
Tara looked at Robin. So this was the story Debby gad told to explain
Robin's transformation.
Martha and Alyssa were talking in soft tones. Robin and Tara walked to
the salon area trying to absorb their pending transformations.
They were seated side by side in front of the mirrors surrounded by
bright lights. Martha and Alyssa wrapped capes around the two. Robin
had to stop admiration of her upper female form.
Martha felt Robin's face. "It is smooth but we can't risk 5'O clock
shadow. So, I'll have to shave you." Alyssa was instantly at her side
with a bowl of foam which Martha applied liberally to Rob's face and
neck. A cutthroat razor applied in her hand. She began to shave Robin
sat there still. A slip and her throat would be cut. Martha was
obviously experienced in doing this as in a few moments Robin's face
was baby smooth. She rubbed some soothing lotion into the skin.
Meanwhile, Alyssa pulled up a small stool to Tara's chair and began to
work on her nails. She filed and shaped them and then added
extensions. Then, she applied several coats of bright red color. Tara
watched as her bails grew far beyond their original size. Using a
computer and doing chores would be difficult. But for tonight, they
would look fabulous.
"Martha will cut and style your hair whilst I do Robin's nails," Alysa
said. Tara's nails looked fabulous and her fingers longer. "Then I'll
do your evening makeup and Martha will do Robin's."
Martha came to Tara's station. "I don't think we need to do much
unless you want a completely different style. I can trim it and style
it. Or do you want more?"
"No, that would be perfect," Tara said. "I like the current length as
it is easy to maintain. Haven't been to a salon in months."
"Yes, dear, I can see that." Martha went to work on Tara's hair
combing and snipping.
Meanwhile, Robin was having her nails done. Alyssa used the same nails
as for Tara and glued them in place. She painted them the same bright
red color as Tara's. Robin watched with mixed emotions. The nails made
his fingers look slender and longer. She hoped very much Tara gad a
solution to remove them before work on Monday. There was no way he
could turn up for work with nails like that. She tried to look at Tara
who smiled back reassuringly. She was sure Tara had that solution
covered.
"Next time we should also do your toe-nails. They will look fabulous
with open-toe pumps," Alyssa volunteered.
Robin had a hard time explaining that there would not be a next time
and said "Yes" softly. She sat quietly admiring her nails as Martha
finished with Tara's cut.
"OK, ladies, now for the makeup," Martha said. "Obviously we will have
to use a much heavier makeup on Robin as she'll be the star tonight.
But Tara, you'll look fabulous too. First question: eyebrows. We can't
match Tara's thinner eyebrows to Robin's. So we can wax them to look
more arched and feminine or I can cover them up and paint them on.
This is quite popular with our customers."
"I don't think we want to shave or trim Robin's eyebrows," Tara
replied. "If you can cover them it may be better. Agreed, Robin?"
"Yes," was Robin's soft reply. She would never be able to go out as
Rob without eyebrows.
"I guess," Martha said. "Debby may be disappointed as she has really
thin arched brows." Alyssa stood by Martha with something in her hand.
It was a wig cap. Martha pulled this tight over Robin's head and then
use a clear tape across the top from the right forehead corner to the
left corner of the neck and vice versa. The head now looked bald. "We
clip the wig to the net so you can move your head and dance without
the wig becoming askew. It will stay in play even during sexual
games."
Robin and Tara had the same thought: Martha had no idea but guessed
correctly at tonight's planned event.
Martha used a glue stick to pastedown Robin's eyebrows. They now lay
flat against the skin. Robin tried to absorb how Martha applied
concealer and then a thick foundation with many layers of powder to
reduce her face and neck to a blank canvas. Using a stencil, Martha
painted on two eyebrows with a dark brown color. They were perfect
matching arches higher than the natural brow line. Bow there was ample
room for various colors of eyeshadow.
Robin tried to see what Alyssa was doing with Tara but she had to
restrict her head movements. Martha applied shades of grey and red
shadow, blending them with a white highlight below the painted brows.
Robin stared fascinated at the transformation and trying to forget
what would be happening later.
After lining the upper lid with a thick black line, a thinner line was
drawn on the bottom. To her surprise, Martha glued on some rather long
lashes causing the eyes to be large windows of her face. Many layers
of mascara were next. A dark pink rouge was blended up the cheekbones
before Martha painstakingly outlined Robin's lips with a dark red
pencil. A bright red lipstick was applied with a brush. Robin was
asked to press her lips against a tissue and may more layers were
applied. Then, even more layers of gloss sealed in the color.
"Don't look so surprised. With this base girls can kiss or do other
things with their mouth without smudging their lipstick too much,"
Martha explained with a smile. "We'll put a tube of lipstick in your
purse so you can touch up your lips. There is also a small kit for
other repairs to your face in a small kit."
Martha looked at Robin's face and smiled. "Just a few more things and
you'll look gorgeous. See Tara?"
Robin and Tara now looked at each with shock and excitement. Both had
the same lipstick but Tara's eyes looked different. She also had large
eyelashes with many applications of mascara but they seemed shorter
than Robin's. Tara smiled at Robin and mouthed 'beautiful'.
Alyssa stood next to Martha with something in her hand blocking Tara's
view of Robin. In a moment something cool touched her ear and then she
felt a sting. Martha inserted a long earring with three bright ruby
red oval stones. "We need to do the other ear too," Martha said and
moved to the other side. Robin suddenly had two long dangling
earrings.
"Sorry, Robin. But if I asked you may have said 'no'. I can explain
away not reshaping your brows, but not earrings. We are not supposed
to use these long earrings after a piercing, just studs but we have no
time. As you may know, if you take them off and never insert an
earring again, the holes will heal without a mark. You need to clean
them every day and you could try studs at night and remove them at
work. But many young men have pierced ears now." Alyssa placed a ring
on Robin's right hand that had a matching stone to the earrings.
"Now, for the hair." Martha had selected three wigs in different
styles: a curly dark blonde, shorter redhead and shoulder-length
brunette. She placed each on Robin's head.
"I think with Robin's coloring and dress, the blonde is the only fit."
Martha tugged the wig into place and pushed the curls up in an updo
style and secured them with a clip. Some curls fell around Robin's
ears. She was the ultimate starlet with a red carpet look. The wig was
secured by pins clipped discreetly to the cap.
"All set, you both can now get up and admire yourselves. I must say,
you both look fabulous." Martha was very proud of her achievement.
"It's 5.45 and just in time."
Robin and Tara stared at each other. Both their transformations were
spectacular. Tara had a big smile on her face as she pressed herself
to Robin careful not to disturb the makeup.
"You look gorgeous," Tara said. "I can't believe it. Look at me? I
have never had so much makeup and the lashes? My mum wouldn't
recognize me."
"Yes," Robin replied softly blinking her large eyelashes. "You do look
fabulous. Can't wait to see Debby's reaction."
"Shock, surprise and jealousy all missed up. Careful, though, it may
make her more aggressive."
"Martha, can you please take pictures of us individually top half and
a full length? Also two of us together?" Tara asked.
"Yes, but I have a suggestion before we do that. Tara, you look
beautiful but may I suggest garters, stockings and a pair of higher
heels? We have everything here."
Tara looked at Martha and then at Robin. It was true. Robin was a
stunner and she needed to match her style. Robin saw her hesitation.
"Don't worry," said. "I'll be happy to pay for them."
"Don't worry about payment. Debby left her credit card here and said
to do anything we wanted. She didn't mention you but she won't
notice." Martha smiled. "She didn't want a makeover from us which was
a surprise." Obviously Martha suspected there was more to all of this.
"Come with me," She held out her hand to Tara. Robin watched her walk
away with Martha. She did look beautiful and Robin looked forward to
enjoying her Robin time with a glammed up Tara. She tried not to think
of what would happen later. Tara would be at her side and she felt
strength from her support.
Some twenty minutes later Tara returned beaming. She had grey
stockings and heels as tall as Robin's. This was the highest heels
Tara had ever worn. Although her calf muscles were straining, she saw
the look of admiration on Robin's face and decided that if Robin could
endure it, so could she.
Tara gave Martha her iPhone and Martha asked them to pose and took
many pictures in many different poses. Tara and Robin posed hugging
each other and arms around each other's waist. They wanted to share a
kiss and brought their painted mouth close but not touching. Martha
approved and encouraged other sexy poses.
"We need to call an Uber," Tara suggested. "What about the clothes?
When do we return them?"
"Nothing to return. Debby has bought everything. Why don't you both
come back next weekend and we'll do it again?" Martha had a big smile
on her face.
"We'll call," Tara said, linked arms with Robin and thanked Martha and
Alyssa who handed them a bag with their clothes and shoes. Just as
they were leaving two gents arrived. Martha's next customers.
"I can't believe how we look," Tara said. "You're a knockout and much
better looking than Debby or me even when we are dolled up."
"In some strange way, I am excited too. I don't know why and what will
happen later," Robin said softly.
"I am tempted to go back and use my strap-on before Debby does you. I
can't believe how turned on I am by my special boy-girlfriend." Before
Robin could reply, the Uber arrived and they slid in.
They entered the apartment and hugged each other tightly. Tara could
feel the way Robin's breasts pressed against hers. It was a new
experience. They wanted desperately to kiss but knew they couldn't
afford to mess up their lipstick. They just looked at each other and
used the tips of their tongues.
"Robin, it's just 8.20 now. I'll send Debby a text to say you will be
ready by 7.30 pm. Maybe she can come earlier. But, we have to do
something first." Tara saw how Robin's mood changed. "Sorry, but it is
necessary. Then I need to change into a more simple dress. I can't
change the makeup unless you want to stay in."
"Can I decide after Debby leaves?" Robin asked.
"Of course." Tara led Robin by the hand to the bathroom. Robin leaned
over the sink whilst Tara pulled down Robin's panty. She rubbed his
cheeks and stroked the tops of his stockings. With gloved fingers, she
inserted the lubricant into Robin's puckered hole. This was not new
for Robin but she squirmed as Tara went in as deep as she could.
"I think we need to do something else too, Can you please turn?" Tara
sat on the toilet seat and pulled down Robin's panty carefully. She
took out his cock which was still limp and kissed the tip. She tore
open a packet and pulled a condom over his cock. "I'm sure I can bring
you to life again later," Tara said pulling the penis back between
Robin's legs. She put the liner in and pulled the panty up tight. "I
don't think she'll pull down your panty. She just needs access. So she
may not even notice the liber," Tara said thoughtfully.
After straightening out the dress and making sure everything was in
place, Tara led Robin back to the living area. She put some sachets on
the low table. "If possible, get her to use the condom on the strap on
before she puts it back there."
There was a message on Tara's phone. Debby was leaving and would be
there with thirty minutes. She would text Tara as she approached so
Tara could wait in her car. That was ten minutes ago.
Tara saw the nervous look on Robin's face. Despite the heavy makeup,
her anxiety was evident. Tara hugged her tight whispering, "It'll soon
be over." Robin stood there passively.
"Where do you want to be when she enters?" Tara asked. "Standing,
sitting?"
Robin shook her head. "Don't know."
"I suggest you stand around here so she'll see you as she walks into
the living area. I think she will also be nervous and want it over
quickly."
Robin said nothing and had that dejected look. It was just moments
away and she would experience humiliation and even pain.
The ping came. "I am double-parked at the entrance." Tara showed the
message to Robin.
"Be brave, my darling. I'll be thinking of you every second. I promise
you it will be over soon. Let that drive your thoughts - and what will
come later tonight." Tara pecked Robin on the lips, gathered her phone
and purse, blew Robin a kiss and left. The door was unlocked.
Debby was waiting at the entrance. As luck would have it she had
managed to find a spot in the visitor's park of her building. She was
dressed in jeans and a T-Shirt and wore a baseball cap. There was not
a trace of makeup on her face. She threw the keys at Tara and pointed
to her car.
"Is the bitch ready?" she asked in a gruff voice staring at Tara's
normal clothes but fully made up. She stared at Tara's face.
"Robin wanted me to be there and they wouldn't let me sit there
occupying a chair. So Robin asked them to do my face too," Tara
explained.
Tara just nodded. There was no way to change things. Debby knew the
apartment and entered the building. Tara went to the car trying to
imagine what Robin was feeling. She hoped it would be over soon.
Debby's car was just a few steps away and appeared full of boxes on
the back seat and some other items on the passenger seat. Tara climbed
into the driver's seat wondering what Debby had in the boxes. On the
passenger seat, there was a bag that appeared to contain bottles of
water and bags of crisps and snack bars. There was also an open carton
of cigarettes, a lighter and a pack that must have just been opened.
The interior smelled of smoke. Tara didn't wander too much at the
contents of the bag. She was worried about what Robin was
experiencing. She wished she could be there. Robin looked beautiful
and she was surprised at the transformation. With nothing to do she
took out a cigarette and decided to smoke to pass the time. Her mind
was in turmoil. She took deeper drags. She was an occasional smoker
but now needed the cigarette to occupy her fingers as she tried to
imagine Robin's plight. She was barely at the end of the cigarette
when she heard a ping. It sounded like a text message and it wasn't
from her phone. The ping sounded again. Curious, she looked around and
found Debby's phone in the bag with the water and snacks.
She stubbed out her cigarette and pulled out the iPhone. The message
was from Brad. The message was short. 'When are you leaving?" Tara's
fingers were shaking as she lit another cigarette and tapped the
message. She had seen Debby's passcode as she wanted to introduce
Tiffany. Tara had mentioned that the password was not really secure
with 1, 2, 3, and 4.
Tara threw her inner thoughts away and opened the phone looking at the
series of messages. She smoked rapidly as she read through them. A
sudden urge caused her to respond. Was Debby planning to go back to
Texas? Was that the reason for the water and snacks? The boxes at the
back?
Tara felt betrayed. Clearly, Debby had some plans to return to Texas.
As she scrolled through the messages she saw the many messages with
'Sorry for what I did', 'Come back and be my wife', 'I promise I'll do
anything you want'.
A wicked thought entered Tara's mind. She typed a response to Brad.
'Just finishing drinks with my friends and hoping to leave soon. I
hope you keep your promises.'
The reply was instant. 'Can't wait. And yes I will keep my promise to
do whatever you want.'
'I talked to the therapist and she has taught me a lot. She said I
should be more accommodating.' Tara typed.
'What do you want me to do?'
Tara stubbed out the cigarette, immediately lit another, thinking.
'Therapist says I must learn to please you and suck your cock and do
it every day and swallow. She also thinks you should fuck my other
holes as often as you can. That I would learn to like it. I must learn
to give you pleasure.'
'You sure?'
'Yes, it's the best way to put what happened behind me. I reacted
badly in surprise. But I will suck you every day if you want.'
'Well, babe, that's a promise I'll hold you to. I can't wait to see
you. I'll make sure your other holes are filled regularly too.'
'Remember that. If I protest, show me this message and I'll remember
what the therapist said.'
'Absolutely.'
'I have to go back to my friends. I will message you later.'
Tara smiled as she took a deep drag on the cigarette. She had smoked
four cigarettes in rapid succession; some only part smoked. Her smile
was broken by Debby's message that she was done. Tara put the pack of
cigarettes and lighter into her purse and put Debby's phone back into
the bag. She might need some nicotine later depending on how she found
Robin. She hoped Robin was OK and exited the car leaving the keys in
the ignition.
She hurried out and met Debby at the entrance. "Keys are in the
ignition," was all Tara said as she hurried past.
Tara burst through the door into the living space. Robin lay over the
arm of the couch, leaning on her elbows, behind up in the air and
dress pulled up with the strap on still partially buried in her
behind.
"Robin, are you alright?" Tara asked trying to take in the scene.
"Am OK," came the brief response.
"Hold still, babe, let me take this out." Tara gently eased the
plastic penis out of Robin and pulled up the liner and panty.
Tara went around and helped Robin up. They looked at each other and
hugged tightly.
"Are you really OK? Did she hurt you?" Tara asked concerned.
Robin shook her head. "I'm glad we prepared. She was more nervous than
me."
Tara kissed Robin lightly. Her lipstick was barely smudged and Tara
was curious as to what happened. Robin's makeup still looked pretty
good. She couldn't wait to tell Robin of her exploits in the car.
"Are you sore back there?" Tara asked.
"Not really," Robin said softly still standing.
"Want to celebrate? I'll open the prosecco." Tara paused. "You really
do look beautiful."
Robin followed Tara to the kitchenette as she opened the bottle and
poured out two small glasses. They toasted. "I'll save this for
later," Tara said re-sealing the bottle. They walked back to the
living space leaning against each other. Robin sat on the arm of the
couch, Tara remained standing by her side. Each had questions and was
waiting for the right moment.
"You look beautiful. I bet Debby was surprised."
Robin thought for a moment. "In a way, I was glad to look that way.
She spent the first five minutes cursing and calling me all kinds of
names. She pushed me on my knees..."
"Just a moment, babe," Tara said seeing something on the floor. She
bent down and picked up an envelope. It was addressed to Tara and Rob
and obviously from Debby. Tara's hand began to tremble as she tried to
open it.
She stopped for a moment, found her purse and took out the open pack
of cigarettes she had found in Debby's car. She lit one, staring at
the envelope. Robin could see Tara's indecision as she inhaled
rapidly. Robin gently prized the letter from Tara's hands.
"So what did Debby tell you?" Robin asked.
"Nothing. Threw me the keys and walked in. Didn't appear to be in a
good mood. I was nervous waiting in the car. Debby had several packs
of cigarettes open. So I decided to smoke to pass the time. I was
nervous for you and looked for a lighter and heard a beep. She had
left her cell phone in the car. I saw it was from Brad. There was a
whole thread between them over many weeks. Debby had planned this for
some time, I think."
"Didn't you say you wanted to invite your new girlfriend for a drink
tonight to celebrate?" Robin interrupted seeing Tara's anxiety. "You
can tell me later. If you change back into the other dress, and fix my
makeup or whatever, we can have a drink and some food. I am hungry."
Tara continued to smoke looking at Robin. "We can read that note or
whatever tomorrow," Robin continued, standing up and wrapping her arms
around Tara.
Robin took the end of the cigarette from Tara and stubbed it out in
the plastic plant on the table. She led Tara to the bedroom.
It took another thirty minutes for both to get ready. Tara changed
into the cocktail dress and heels, repaired Robin's lipstick and
ensured her dress was sitting perfectly. Robin looked content that the
ordeal was over. Both were curious as to hear about what had
transpired but tried to curb their impatience. It was a Saturday. Just
a little after 8.30 pm and the two girls were ready. They called an
Uber.
Just as they descended the stairs, Tara's mood changed and she began
to laugh.
"What's so funny?" Robin asked.
"I'll tell you and show you later. Debby has left for Texas tonight
and won't be back. I think Brad will have a lot of fun with her. We
can have a drink so I can show you off and then have a snack in the
caf?. OK?"
"OK. I don't understand," Robin replied. "She left for Texas after all
of this?"
Just as Tara was about to reply, the Uber arrived. Tara gave the
driver instructions to a large hotel snout fifteen minutes from her
apartment. Discreetly, she pressed against Robin who didn't speak a
word.
The two ladies were admired as they walked comfortably with arms
linked into the bar. Robin looked straight ahead and avoided eye
contact. Tara was mumbling about how this was a popular bar with
locals and out of town visitors. The bar in the hotel was busy but
some tables were still available and they spotted one in a corner.
Tara went to the bar and got them drinks of a cold Chardonnay.
Tara pulled out her phone and placed it on the small table. "So, Robin
my love, tell me everything and don't miss any details." She paused.
"I could get used to having a drink with my beautiful girlfriend in
hot spots like this. Everybody is looking at us."
Robin took a sip of her wine, noting the smudge mark on the rim of the
glass and spoke in a low voice. "I stood in the same spot when Debby
walked in. She looked at me startled. I don't know what she was
expecting but I don't think she expected me to look good. She
approached me with an angry stare. I thought she was going to hit me.
Then she started shouting at me, calling me a bitch, slut, etc and did
I want to attract men and su....." Robin looked at Tara. She didn't
want to complete the sentence.
"I can imagine," Tara said placing a hand over Robin's.
"This went on for some minutes and she pushed me on my knees. I knew
what was coming. She was wearing a strap on but it was like the one
you have. I expected bigger. You saw it. She pushed it in hard. She
continued to say I was a faggot and only good for pleasing men. It was
probably just a little more than 7 minutes when she removed it." Robin
paused and took a sip of her drink. "I don't think she had used one
before." Tara smiled.
"I hadn't used one until a few days ago either," Tara admitted with a
smile. "Go on."
"Debby asked me to get up which was difficult. I had to grab the edge
of the table. She pushed me over the end of the couch, pulled up the
dress and pushed my panty down. I positioned myself on my elbows to
make it easier. She just thrust in hard but didn't go the full depth.
She was calling me all kinds of names in the process, got tired I
guess and left it in me. You saw that."
"Yes, I'm so glad she didn't go mad and hurt you. Shall we have some
dinner and I can tell you my side?"
"Yes, something small would be good."
They finished their drinks and walked out arm in arm to the caf? at
the other end of the lobby. Tara assumed that onlookers thought they
were a lesbian couple. She didn't care, the ordeal was over and she
could have a normal relationship with Rob or Robin. She was curious
about what was in the envelope but it didn't seem important.
Over a light dinner of soup and a salad with a shared fish dish, Tara
explained what had happened in the car as she waited for Debby to
finish.
"You mean this was some kind of setup? But to what end? If she was
going back to Brad, I don't see the point. She must have spent a lot
of money on this."
"I don't understand it either. But Debby will have some ordeals of her
own when she meets Brad," Tara smiled mischievously.
"Ordeals?" Robin inquired.
"Of course. Just as I found the lighter and lit the cigarette, her
phone pinged with a message. She had left it in the bag with some
snacks and drinks. Brad was asking when Debby was leaving. That
explained the boxes and stuff in the car. I saw her passcode when she
called Tiffany. It was just 1234. Remember how she had told me she
hated doing thigs with her mouth and back hole? Well, Brad will be
demanding that daily. I also told Brad that he should use all of her
openings regularly even if she wasn't in the mood. She'll have fun
every day," Tara looked at Robin for a moment. "So did you make up
your mind yet?"
Robin looked at her. "About what?"
"Well, I want to make plans with my new girlfriend next weekend.
Dinner, dancing and a lot more after that. I'll call Tiffany for an
appointment."
Robin looked serious and thought for a long moment. A big smile broke
out on her red lips. "Well, what you suggested for Debby was quite
wicked, I think. She'll hate it. So, if you want to be with Robin next
weekend and whenever you want, perhaps you should be 'punished' into
doing the same." Robin held up her glass and looked at Tara.
Tara looked pensive for a moment and broke out into a big smile. "I
agree if you promise to use all my openings as Rob or Robin, starting
tonight. Unlike Debby, I am going to enjoy it in all three places."
Tara leaned forward and kissed Robin lightly on the lips, oblivious to
all in the caf?. "Sealed with a kiss and let's go. It seems I have
work to do tonight and I hope my girlfriend is up to it. Also, I want
to read that letter." Robin gave Tara her credit card and asked her to
get the check.
As soon as they were back in her apartment, Tara pounced sealing their
lips in a long, tongue dancing kiss. Robin was pressed against the
door. Slowly, she went down on her knees her eyes never leaving
Robin's. She pulled down Robin's panty and liner and freed Robin's
penis. A few strokes and it began to grow after its long imprisonment.
"I am starting my punishment now," she said as she licked the head and
slowly began to take it in deeper. A few minutes later, Robin was
erupting deep in her throat.
"Let's not spoil that great dress, I am sure you'll need it in the
next few weeks," Tara said and helped Robin out of the dress and left
her standing in bra, panty, stockings and heels. She hung up the dress
and removed all her outer garments too. Both were now similarly
attired. Tara brought Robin to the living space.
"I'll get us a drink and we can read Debby's letter. I need your
little guy fully ready when he gives me my next punishment,"
Tara brought out the two glasses and a saucer and sat at the corner of
the couch. She invited Robin to lie down wither her head on Tara's
lap, legs over the other end. She leaned down and gave Robin a tender
kiss. She reached for her purse and took out a cigarette and lit it.
She gave Robin, Debby's letter. "Please read it out loud."
Robin raised her head, took a sip of her drink and lay down again. She
opened the letter and started reading. It was in a hasty scrawl but
legible.
'Tara and Rob, you are both stupid fucking bitches. You thought I
didn't notice when you guys would talk and leave me out. I know you
have been meeting and I even saw you guys kissing in the carpark as I
left. You were probably laughing at me as you fucked at night.
Tara you are welcome to that stupid sissy who so readily agreed to be
used. Enjoy fucking his mouth and arse as I will be. I will take out
all my anger and frustration and put it all behind me. It was not my
therapist who suggested this. I know Brad wouldn't let me fuck his
arse. He's a man's man unlike that wimp you are interested in. What
man would allow a girl to fuck his arse? Sissy Robin accepted it all
too easily.
By the time you read this letter, I will be on my way back to Texas to
Brad and I will marry him soon. He has promised to do as I ask and not
repeat his mistake.
Have fun with each other. The money I spent on changing Rob was
cheaper than therapy. It will show him what a sissy he can be. As for
you, Tara, I'll leave you my toy so you can fuck him like I will have
done.'
Debby
Tara laughed as Robin finished the letter.
"What's so funny?" Robin asked.
"I was just thinking. Who is the stupidest bitch? When she reads the
texts between herself and Brad she'll be mad. In the texts she asked
Brad to fuck her in all three openings regularly. I mean I asked on
her behalf. Brad loved the idea."
Tara finished her cigarette and drank the last of her drink. Her left
hand went to Robin's exposed penis and began to stroke it. She saw it
stirring and stood up.
"I'm glad it's over and now I think it is time for you to punish me
again. I am ready for you in my normal hole." Tara led a willing Robin
to the bedroom. "If you don't perform well and bring me off, I'll have
to punish you too,"
Robin looked at her with raised eyebrows. It was strange to see those
painted lines move up.
"What do you mean?" she asked softly.
"Just remember who has the solvent. I might like you as Robin until
you punish me properly." Tara smiled. "I would feel very guilty too if
I don't use my strap-on in both of Robin's holes. I will finish what
Debby started."
They both smiled. It was going to be a long night and Sunday. "I guess
we'll both have to accept our punishments as best we can," Robin said
and kissed Tara hard.