iBimbo
"So, Cassie, "Jack Straw said, "your resume looks good and I'll get back
in touch in the next few days. We would like a quick decision and start."
Jack Straw rose from his corner seat in Starbucks and shook my hand.
"Sorry, I have to rush to another meeting. Talk soon." Jack Straw was a
young CEO of a startup and looking for junior software engineers. I had
just graduated and was interviewing for the position. It was exciting to
have the opportunity and it seemed the company was well financed and
would do well.
I looked at my watch. It was 4.25. If I ran I could make the 4.30 pm bus
to the train station. I gathered my papers in a hurry and put my laptop
away in my backpack, swung it over my shoulders and ran out. I had a few
minutes and it was less than a hundred yards away. I saw the bus approach
and dashed out toward the bus stop. In my haste I didn't see the person
on the sidewalk and crashed into her. I fell on top of her. It took me a
moment to recover and sit up. I was grateful that I had fallen on top of
the lady and my backpack with laptop was still intact. I looked at the
lady in stunned silence. I had bumped into a lady that I can only
describe as a hooker. She looked at me too in shocked silence. The
cigarette she had been smoking lay smoldering a few feet away.
"I'm so sorry," I said. "I was rushing for the bus and wasn't paying
attention. Are you ok?"
The lady looked at me. Even with all that makeup I could see she was in
some pain or discomfort. Luckily, nothing appeared broken. I stood up and
tried to help her up. I don't think she wanted my help but obviously
couldn't get up easily and so allowed me to help. She stood unsteadily on
heels that were at least 4" tall. I had never worn heels that high except
once to a Halloween party where I was dressed a showgirl.
"Are you ok?" I asked again as I saw the lady fumbling with the purse she
had over her shoulder.
"Yes," she said and looked in her purse and brought out a pack of
cigarettes. She took one out and lit it, inhaling deeply and kept it in
her mouth. She took the cigarette out of her mouth and just "I'm OK," She
stuck the cigarette back in her mouth, inhaling and blowing out smoke.
She took out her cellphone and took a selfie and sent it to someone.
Strange way to behave after that knock, I thought. I was glad she wasn't
that badly hurt.
"Can I get you a coffee?" I asked. "I really am sorry it was my fault."
"No, thanks. I'm OK," she replied crushing out the half-smoked cigarette.
"Do you have a car here? I can walk with you to the car." I had missed
the bus and needed to wait at least forty minutes for the next one.
"I live near here. Five minutes to walk, Thanks." Her voice was husky and
I noticed her shift her weight. I think one heel was damaged causing the
lady to be unsteady on her feet.
"I'll be OK." I think she was trying to go back to her apartment. But I
didn't think she would make it with that damaged heel. She found her
balance and tried to walk away and the heel slipped. She was sure to
fall. I wasn't sure why she didn't walk barefoot.
"Look, I have some time until the next bus comes. Let me walk with you."
I truly felt sorry for her. It wasn't deliberate but it was definitely my
fault. Whatever she was doing dressed like that, it was not for me to
judge.
The lady looked at me silently. She was trying to make up her mind. She
looked rather pretty but had make up plastered on with a trowel. Very
heavy pink and dark-blue eyeshadow, large false lashes with heavy mascara
and bright red lips. Large earrings dangled from her ears. Curly dark
blonde hair framed her face. May be she was going to a party. It didn't
matter to me. I just felt guilty.
"Thanks," she replied. "It's not far. My name is Jackie."
"Oh great," I replied threading my elbow through hers. "I'm Cassandra but
everyone calls me Cassie. You can lean on me."
Jackie lit another cigarette and kept it in her mouth. I tightened my
grip on her elbow and we hobbled off. With that cigarette in her mouth
she couldn't talk so I let her guide me. It was slow. Unless she really
meant she didn't live far, I was going to miss the next bus too.
The Starbucks was in a small strip mall along a busy road. There were
some low-end shops and a small Italian bistro. Nothing special. Behind
the row of buildings was a narrow path and through a gap in the hedgerow,
there was access to a modest apartment complex three stories high. It was
just a two minute walk at normal pace but it was six or seven minutes for
us to arrive. There was no talk as Jackie smoked.
I was still wondering why Jackie was dressed like this in broad daylight.
I grew up in a small town of just under 2000 people the only child of a
single mum. She worked hard and encouraged me to go to college. I managed
to get into a local school and just graduated with my Computer Science
degree. Mum was so proud of me. I was also pleased at this interview for
a junior position at this start up. .
Everyone knew there were corners at night where a few ladies displayed
their wares. When I was at community college, I still lived at home and
on a meagre budget couldn't afford to go out much. But there were parties
and sometimes I would get out and see nightlife in the town nearby.
We were at the entrance to the apartment building. Jackie crushed out her
cigarette and said, "Thanks. I can manage."
"No problem," I replied. "Again, I am so sorry."
I turned away to head back and heard another crash. Jackie was thrown
against the hedgerow as her heel snapped. I turned and saw her thrust
against the hedgerow and rushed to her.
"Let me help you in," I said grabbing her around the waist.
Jackie looked at me. I thought she appeared frightened but I couldn't
think why. I wasn't judging her and besides she may be dressing for a
costume party or something. I tightened my grip around her waist. Which
floor?" I asked. It would be a challenge if Jackie lived on the top
floor. These low buildings didn't have elevators.
"Just ground level." Jackie appeared to look scared now as she grabbed a
single key out of her purse and opened the main door. Her apartment was
immediately to the right and she opened it and I walked in with her. She
looked very relieved as she slipped off her shoes, leaned against the
wall and closed her eyes. A short hallway led to a small living area. My
job was done but I needed the restroom first. I had a long journey back
home.
"Jackie, can I use the restroom please?" I asked.
Jackie opened her eyes and looked at me. She looked at the other end of
the hallway and I could see the bathroom.
"Please," she croaked and pointed at the door. I went past the entrance
to the living room to the bathroom and did my business. I took my time
and rinsed my hands. I opened the door and heard voices. Was there
someone else in the apartment? Was that why Jackie appeared scared? Her
husband? Boyfriend? Pimp?
As I took a few steps toward the living space, I heard a man's voice
speak. It was stern and demanding. "Where the fuck were you?" the voice
asked. I heard Jackie say that she had a small accident but was back now
and that's why she was late. The voice went on to describe her as an
ungrateful slut who would get her punishment tomorrow. She was to do
exactly as he had said or else. Did she want all her friends and
colleagues to see the pictures? I heard Jackie sob and repeat, "No, no,
I'll do as you say." I was glad it was a phone call as I didn't want to
meet that guy in person.
The voice said 'good' and the call ended. I didn't know what was going on
but it seemed Jackie was in some kind of trouble. I didn't need to know
her to understand this and the threats.
"Jackie," I said softly. "Sorry, I couldn't help but overhear that. Are
you in trouble?"
Jackie was seated at the small desk and turned around in shock. She had
forgotten I was here. I saw black streaks of mascara filled tears roll
down her cheek. She looked desperate and frightened. I didn't know the
reason but I felt for her. I went up to her and hugged her from behind.
Jackie pushed back and responded to my embrace. "Sorry," she said,
holding my elbows and drawing me to her. "It's a long story."
"I have nothing on tonight. Let me make a call and then we can talk if
you like." I grabbed my cell and called my mum and told her I am meeting
a friend and would call her later when I was on my way back. I told her
the interview went well and I could hear how happy she was. Jackie had
not moved from her seat at the small desk, the laptop still open in front
of her. She suddenly got up, went to the small kitchen area and brought
back two cans of diet soda.
Silently she sat back at the computer, took a big swig out of the can in
unladylike manner and turned to me.
"You know who I am, right?" Jackie asked.
I looked at her not really understanding her. I had just met her less
than a hour ago. How could I know her? I looked at Jackie's tear smeared
face. Black tracks of mascara stained tears were rolling down her heavily
rouged cheeks. There was a lot going on and Jackie was in trouble with a
guy. I went up to her, still seated at the computer, and hugged her from
behind in a gesture of sympathy. She moved back in response and we
stayed that way for a moment. As i moved away one of my long earrings
got entangled in her hair. As i hurt from the tug in my ear, i used my
hand to disentangle the hair and found a pile of blonde hair in my hand.
I saw short brown hair underneath. Jackie let out a scream and started
sobbing. I didn't mean to remove her wig. It was an accident. Jackie's
hands searched for the wig but it was too late.
I moved back to untangle the hair and it fell in a pile on the floor.
Jackie turned around with the saddest look on her face, with a trail of
tears ruining her makeup.
"I am sorry," i said, "I was trying to disentangle my hair." The look in
Jackie's face still haunts me: surprise, shock and horror. In the space
of an hour I had managed to hurt her twice.
"It doesn't matter anymore," she said, "my life's over."
"Whatever do you mean?" I asked. "Who would care? It's only a wig."
Jackie gave me a haunting look in disbelief. "What?" I asked.
She looked at me strangely and then began to laugh in a wild belly laugh.
After a few minutes, seeing my discomfort, she stopped. "You still don't
know?" She said her laugh subsiding.
"Know what?" I asked unsure between her bouts of tears and laughter.
"I am boy under all these clothes and ruined makeup." Jackie's tone was
serious.
I looked at her in disbelief. She was dressed like a cheap streetwalker
and nothing she did or said gave ne any idea that there was a boy
underneath all that powder, paint and clothes.
Jackie stood up now, she was about my height without her heels and still
had a boyish female figure with short brown hair. She hugged me tightly.
I could feel those massive breasts press into mine. "I need to explain.
Give me a few minutes to change. I can drop you home."
I was too shocked to protest and nodded. It was only 5.30 pm but mum
would be worried. I called her and said i was helping a friend. She only
asked if it was a boy or a girl. I didn't know what to say. I could hear
her pleasure as i said "boy" and that i wouldn't be late. She sounded
happy. How could i tell her who it was?
It wasn't long before a good looking boy stood before me. He was slim and
had nice features. This was quite the contrast to busty Jackie. I had
seen boys dressed as girls before at parties, especially at Halloween,
but i had never met and talked to one. I didn't even know his real name.
He had scrubbed off the makeup but there still smudges around the eyes.
He just wore a plain t-shirt and jeans. He was the image of the 'boy next
door'. I was confused between Jackie and the boy standing in front of me.
He looked at me.
"I am sorry," he said softly. "I really appreciate your help. As you
heard, i am in a lot of trouble."
I looked at him unsure of what to say. "My name is Jason Armstrong."
"Hi," I replied softly, "my name is Cassie Jones. I am sorry I bumped
into you. It seems I caused you problems twice in an hour. Haven't done
that before." I was feeling comfortable with Jason in spite of how he had
looked earlier.
"It's not your fault. I am sorry to put you through all of this." Jason
looked really desperate and I really felt sorry for him. "I owe you an
explanation."
"You don't need to explain anything to me. But it does seem you are in
trouble and need help. I'm here if you want to share. I don't know what I
can do, but I am a good listener." I couldnt help but feel that running
into him caused him more problems.
"Ok," Jason said and sat down at the desk. "I've been cross dressing for
some time now. I don't know what started it. My mom knew but didn't say
much. She is a single mom and works two jobs."
"My mom's the same," i interrupted. Jason looked at me with a surprised
look.
"Mum stayed silent and even saw me dressed. I didn't go out till
Halloween one year and my confidence grew. I used to buy outfits and
shoes in thrift shops. I borrowed lipstick from mom. I dressed
occasionally through college and found a good job here at Cresswell
industries as a graphic designer after I graduated. That was just some
months ago. It is a good job and i met a girl there. We went out a few
times and I was feeling good. On the days i was not meeting Lisa i used
to come home and dress. I was able to afford some new things and so felt
great. I had some money, was able to buy new stuff and had a girlfriend
too. Of course i didn't tell Lisa about Jackie. Last Sunday Lisa was busy
so i decided to try out some new things. I spent a lot of time on my
makeup and I looked good." Jason showed me some pictures of Jackie in
'normal' girl mode on his laptop. She looked great and I wouldn't ever
think of her as anything but female.
"I was sure you were a girl even with the heavy makeup until the wig came
off." I smiled at the memory. "You look really good. I like the dress and
makeup. I cannot tell you are boy underneath." I volunteered. Jackie
looked like a nice girl and I would be happy to be friends with her. Her
dress was normal and her makeup was very subdued and matched her outfit.
"Thanks," Jason replied with a wry smile. "Anyway Lisa came by in a
surprise visit. I guess i had left the door unlocked. She found me all
dressed up, fully made up and ready to party. I wasn't going out just
trying my new clothes. Lisa thought i had another girlfriend and shouted
at me. I was shocked of course and told her that it was I, Jason. After
tears and shouting she told me to wait there and fix my makeup. I didn't
know why but it was better to keep her quiet. Lisa went to the living
room whist I fixed myself up. It didn't take long and i heard voices and
so I stepped out of the bathroom. I saw a large man with many tattoos. It
was Russ, Lisa's brother, who looked at me and broke out into a huge
grin. I had met him once before.
'Lisa. I think the boys would like this sissy. Looks cute, doesn't she?'
Russ said
'I am not sure what i saw in this faggot. Makes me puke to think of it.
Show the bitch what you got.' Lisa was still angry and I could hear it in
her voice, this guy could hurt me badly.
'Well, let's see how she does.' Russ said and dropped his pants in front
of Lisa. There was a growing bulge in his boxers. I was scared and began
to shake. Lisa saw this and pushed me to my knees. She reached down and
put my hands on the waistband of his boxers. I was scared as i was forced
to pull it down.'
'Russ rubbed his thing and moved it to my mouth. "Bite it and you'll need
dentures," he said and forced it deep into my throat holding my head. In
a few minutes he finished all over my face. Lisa was taking pictures with
her cell phone. Lisa laughed and took more pictures. I have never done
that with a man and was thoroughly disgusted. I didn't have a choice.
"Jason started to cry. I had never done that either but I would have been
happy to try this with someone I liked.
'I got to get to see the boys, Lisa. We have a game starting at the
Boar's Head Bar soon. Why don't you see her outfits and plan on me and
the boys having fun this weekend? We can start Friday.' Russ said pulled
up his pants and left laughing.
"Lisa asked to see my outfits. They were new and outfits for evening
wear. 'We'll have to go shopping tomorrow. And then we can have some fun.
I'll see you tomorrow in the office.' Before she left she took my phone
and emailed all my contacts to her cell. 'Just insurance in case you
decide not to cooperate Bring your credit card, we'll go shopping g at
lunch time.' Lisa left me and I was frightened and also disgusted at what
Russ had made me do."
"On the Monday we went shopping to the cheapest stores in town. Lisa
forced me to buy cheap, tarty outfits with matching shoes and purses.
Also that cheap wig and makeup. Then we went to a special store and she
forced me to buy those massive DD forms. She gave me instructions. Every
afternoon after work i was to change into one of those hooker outfits and
walk up and down the strip mall as if I was a hooker. I was to have a lit
cigarette in my mouth and swish my butt. I had told Lisa i hated her
smoking. I was to face time her at the start, during and after i came
home. Russ would be watching. I would be making my debut with his friends
on Friday and I was to be a party favor. I am not sure what he means but
I know I will be abused."
"Oh Cassie, i don't know what to do. I can't afford to lose my job. I
wish I was dead!" Jason started to cry.
I didn't understand anything about this. I had bumped into Jackie by
accident and now found myself torn between pity and anger that somebody
should be put through this. I didn't want to get involved but i had heard
Russ yell at Jason. I knew Jason was scared. I didn't care how he wanted
to dress. He didn't deserve to be humiliated or hurt.
"Jason, it doesn't matter to me how you choose to dress. Whilst I don't
understand it, you are not hurting anyone. I feel terrible that your so-
called girlfriend started this. Can you drop me off? I want to help but
need to think about this and find the right way."
"Sure. I really am sorry to bother you but I am desperate. I can't take
this. Let's go." Jason grabbed his keys and led the way out. "What's your
cellphone? I'll send you my number." I gave him the number and I heard
the ping of his text.
We drove to my apartment block in twenty minutes in silence. My mind was
racing. I had no idea how to help Jason. I knew mother would have plenty
of questions too. How could I explain Jason and his penchant for female
clothes?
Jason gave me a hug and whispered 'thanks'. I really felt for him. I went
upstairs wondering g how i was going to explain this to my mum. I had
never lied to her nor needed to.
Mum greeted me at the door with smiles. ."So, you had a good day, I see",
she said. "Sit and tell me all. I just made a pot of tea." I was in a
corner and needed to think.
We went to the kitchenette and sat down. Mum poured tea for us and taking
a sip looked at me patiently.
"The interview with AB Soft went well. They are looking to hire a few
junior programmers so I think they will contact me this week. If I get
the job they want a quick start. Money is not bad either for a start." I
took a big gulp of tea.
"That sounds very good, honey, I'll keep my fingers crossed. I'm sure
you're top of the list." Mum was looking at me and I knew she was waiting
for news on my other meeting. "So, who's your friend? Is he nice?"
"Mum," i retorted. "It's not like that."
"What is it like then?" Mum raised her eyebrows emphasizing the question.
"Well, he is a little....different," i started to say
"Oh really. In what way?" I did not know how to respond honestly without
giving the wrong impression.
"Well, after the interview i looked at my watch and saw I had just two
minutes to catch my bus. I dashed out of Starbucks and saw the bus
arriving. I wasn't looking and ran smack into Jac...I mean Jason. I
knocked him down and he was also not paying much attention and fell
down."
"A new way to make friends." I could hear the humor in mum's voice.
"Anyway, i banged into him hard and he was thrown and hurt his ankle. He
didn't live far away so i helped him to his apartment. He was very
grateful and we got talking. He was having problems with his ex-
girlfriends brother and so was not concentrating. "
"That's a new way to make friends. So, he drove you home?"
"Yes. I missed the bus and would have had a long wait. We had a coffee
and he offered to drive me home." I was trying desperately to make it
plausible and not make Jason look like a weirdo.
"Sounds like a very nice boy. You knock him over and he forgives you. He
needs your help home but offers to drive you here. You should try to keep
friends with him." I don't think mum was trying to be funny but it was
her way to show there were holes in my story.
"Yes we exchanged numbers. I said I would call him."
"Good," mum smiled at me. She knew her daughter well. "You look tired.
Get an early night."
I went to my bedroom deep in thought. I took a long shower thinking about
Jason and how I could help. I hated bullies and had confronted them in my
early life. Mum had drilled into me to confront bullies. Jason didn't
have a mum like mine I guess. I was still baffled at his desire to dress
like a woman but I knew that this was not that uncommon and I didn't have
any issue with it. Of course his exaggerated dress and makeup made it
harder to accept Jackie as a normal crossdresser but i realized he was
being blackmailed into this exaggerated role. He had shown me the
pictures when he was dressed as a normal girl and he looked good and very
natural. I felt sorry for him but wasn't sure what I could do to help.
I went to my room and decided to call Shania. She was my closest friend.
I had known her since 2 Grade. Shania was an outgoing girl with a great
figure and tanned complexion from her Latin parents. But Shania was born
here. We talked a long time and decided to meet early to hatch out a
plan. I didn't spare any details and Shania had no issues with Jason's
dressing up. She was also disgusted that he would be blackmailed and
humiliated. I told her how nice Jackie looked when she was dressed
normally. I fell asleep quickly
I had a restless night. I didn't have any inspiration. I woke up much
earlier than normal and needed coffee. I brewed a pot. Just as it was
ready I saw mum in her robe looking at me. "I couldnt sleep either.
What's troubling you, honey? The job?"
"No, mum, it's something else." We both sipped our coffee. "Mum, i didn't
tell you everything last night. Sorry."
"Did you have unprotected sex?" Mum was direct.
"No mum, nothing like that. We didn't do anything. We're just friends." I
didn't recall why I added that.
"In that case there are no problems we cannot solve. What is it?"
"Mum, I left out somethings, bad things." I saw mum's expression change
immediately.
It took some minutes but I managed to tell mum all. I described Jackie
and how Jason was being blackmailed. I didn't go into detail about the
sex part and what Russ had promised Jason or Jackie for Friday. I could
see mum' expression change but she didn't interrupt me. After I was
done, mum filled our cups again and looked at ne intently.
"Does Jason not have any friends or family nearby?" Mum asked.
"I don't think so. I think he would have escaped if he did. What can I
do?"
"Let's think on it. I am happy you want to help and stop the bully but am
also concerned you might get hurt. So be careful. I have to get ready for
work."
"I am meeting Shania this morning and maybe she can help." Mum knew and
liked Shania. She was a bubbly personality and mum and Shania's parent
knew each other.
"Good." "Mum said, "I'm glad you can share that with her. Shania has good
instincts."
Mum gave me a quick kiss on my head and went to her room. I put the cups
in the dishwasher and decided to get ready. I had plenty of time. On
impulse I texted Jason and said I would be in touch later. His one word
reply was 'Thanks'. I spent some time on the Internet and looked up
crossdressing. From major stars to everyday people it appeared to be
commonplace. I hadn't met one directly till yesterday. Some of the images
showed "women" that looked prettier than many females with great figures
too. I thought back to Jackie's normal figure and presentation and I was
astonished. She looked great.
I met Shania at a local coffee shop. She was already there. We got coffee
and started to talk in a low voice. It was busy but not overcrowded.
Shania was all smiles. "So, Cassie, what are you thinking?" she asked
"Don't know. I want to help but don't know how. I told mum everything too
and she had no ideas. I don't know if I should even be getting involved."
Shania looked at me and said, "Think back to 10th Grade. Remember Derek?
Remember Russ?"
I cast my mind back. Shania and I had befriended a boy, Stuart, a small,
skinny kid in our class, who was being bullied all the time. He had a
troubled home life. I think he was drawn to us because we would speak
normally to him. There was a big guy who always picked on him. Russ made
him do humiliating things and run behind him. We had watched this for
some weeks until big Derek showed up. He latched on to us, Shania in
particular, and followed her around like a puppy dog. She would be able
to get him to do anything. He was a gentle giant. Shania and I told him
about Stu and Russ's bullying. Shania indicated she would be very
'grateful' if Derek looked after Stu when we were not around. The result
was that a few days later Russ was off school for some days. When he did
appear, he had a large bandage on his nose. It seems he had "broken it"
whilst playing football. We knew the truth. Ever since that day, Russ
left Stu alone. Today Russ was in some menial job. Stu had gone to
college.
"Well, yes, I remember," I said after a long silence. "So what?"
"Well, Derek is back in town and dying to go out with me. He wants to
meet you too, he knows we are close. I am still playing with him. I am
sure he will come to Jason's aid if I ask him." Shania smiled
confidently. She knew how to keep boys interested. I knew she didn't have
any special boyfriends at the moment but she had had several in the past.
Unlike me. I dated a boy once in college and things went well until he
wanted me to do things with his thing. I refused. He never called again.
"When you mentioned Russ, I remembered that the bully in school was also
called Russ. Don't think they are the same guys though."
"Why would he do that for Jason," I asked stupidly.
"Well, he is not doing it for Jason. He will do it for me, especially if
I agree to go on a date with him." Shania had thought this through.
"How will we get him involved? Don't forget they have threatened Jason
with things for tomorrow, Friday."
"True, so we need to act today. See if Jason will meet us for lunch
somewhere quiet. He should try to find out where Russ and his friends
hang out. I am sure they will meet tonight to discuss and plan the big
event for tomorrow," Shania seemed to be enjoying this.
Without too much thinking I texted Jason. He replied immediately that he
would be available. I told him to come toward our part of town as we
didn't want to take buses and trains. He had no problem with that and so
we agreed 12.30 as a meeting time at a small bakery caf? not far from us.
"So what are you thinking Shania? I can see your eyes twinkle and some
plot hatching." I had no ideas myself and so was grateful she had taken
on the role to plan this.
"Need to be careful of course. Jason/Jackie has to co-operate. She should
come on to Russ in front of his friends. You, Derek and I will be silent
observers at the same place. We should video the whole event. Then when
Russ gets all worked up and wants to have fun, I am sure he will want a
more private place. We will follow them discreetly. We get more photos
and videos and break it up before Russ can hurt Jackie or do anything to
her. He will hate having his friends see that he was making out with a
boy. Hope Jackie agrees to be who Russ wants her to be tonight -
temporarily anyway."
Shania took out her cell and dialed Derek from memory. It was a short
conversation. "Of course he agrees to pick us up, and then go out." I
looked at Shania. "Don't worry, he knows we are like sisters and share
everything and this is not an official date - for the moment anyway."
Shania winked.
"Seems like a lot of risk for Jackie. Will Derek be OK with it?"
Shania smiled. "Of course. I'll call him later to explain. He has a car
too so that would be another advantage for us."
"This will only work if we know where Russ will be. He must also be with
his friends. What about the sister Lisa? We also need to get his
cellphone so we can copy his address book." I had some doubts but I
didn't have a better plan. Shania always came through and I trusted her
implicitly.
We still had some time to kill and so Shania and I went to our apartment.
I called mum and told her I was hanging out with Shania and that we were
probably going to hang out tonight. Her only response was that 'we should
be careful.' I think she suspected we would be up to something. But she
was comforted in that Shania and I would be together.
We walked to the bakery and Jason was waiting. He stood up shyly and
hugged me. I introduced him to Shania who was eyeing him from top to
bottom. I could read her mind: how would this guy look in a dress and
heels? Shania hugged him at once. I think she liked what she saw. He had
no traces of makeup and looked like a typical boy in jeans and open-
necked shirt, quite a contrast to his female self.
Jason bought us sandwiches and sodas and we sat at a quiet table.
Shania's eyes never left Jason.
"I took the afternoon off. Lisa warned me not to forget my afternoon
stroll. She and Russ would be watching. What do you have in mind?" Jason
took a sip of his drink and looked at us expectantly.
"Jason, Shania has been my best friend since 2, Grade. I told her your
story and she reminded me of something that happened in school when we
were in 10th Grade." I was going to let Shania explain the plan.
Shania looked at us and started to talk. "Before we go on, Jason, I am
sorry this has happened. Do you really want to stop this? Otherwise this
could go on for a long time and who knows what they might demand of you.
Also, no guarantee they will not disclose all to your friends and family
anyway." Shania was trying to be the social worker she was aspiring to
be.
Jason looked at me as if I had betrayed his trust. But I was out of my
depth. I wanted to help him but had no idea how. Shania was practical and
for some reason had fully engaged to find a solution. "You can trust
Shani and me," I felt compelled to say. "We are only thinking about you."
"Of course I want to stop this," Jason said quietly. "I don't know how
and I really am dreading tomorrow. I know they will humiliate and hurt
me." Jason sounded really down. I think he decided to meet us in the hope
we could help.
"Jason," Shania said quietly, "I am sure it is very difficult but we have
an idea. We were able to take care of a bully back in school and we
wondered if you wanted to try it."
Jason looked up at us. I could see a tear forming in his eye. "What do
you think? I will move away if I have to. I can't take this."
"Jason, running away won't solve it. They will be more likely to send out
those images if you run away. You may find yourself in the same
situation. You can't run away. You have to confront it. We want to help.
I promise you'll be safe." Shania patted his hand.
"So what do you want me to do?" Jason asked, pleading with his eyes.
"First, do you know where Russ will be tonight?" I asked. "We have to
confront him tonight to avoid the action tomorrow."
"He normally goes to the Boar's Head, it's a dive bar with pool tables. I
heard Lisa talk about how he hangs out there with his cronies most
nights." Jason took out a tissue and blew his nose hard. "I've never been
there. Lisa goes there sometimes."
"Let me ask you. How do you deal with bullies?" Shania took over.
"You have to humiliate or hurt them in front of their friends, I guess. I
don't know."
"Yes. Exactly. That's is the plan. But we need your full cooperation."
Shania was looking at Jason closely to see if he would back out.
"What do you want me to do?" he asked quietly.
"Well, we want you to dress as he wants and go to his bar. Cassie and I
will be there with Derek. He is a big guy, football player, and he will
protect us. We will go in a few minutes earlier and then you come in,
walk up to Russ in front of his buddies and kiss him like a girlfriend
would. He will be surprised and will show off in front of his friends. He
will grope you a little we are sure. You need to come on to him strongly,
rub his crotch etc and then get him high. We will be taking photographs
and videos. You should ask for his phone and then say you would like to
give him a photo together. Give his cell phone to one of us and ask for a
photo. You should get close to him. He is your man, right? He should like
that. Then, when he is hot enough, he will take you somewhere where it is
quiet as he will need release. We will be not be far away. Just before he
does anything, do something near his boy parts to dislodge your wig. You
may have to hold his thing. We will take photos. We believe he won't want
his friends to see that he was getting off with a boy. We can threaten to
send this to all his friends and workplace if he doesn't stop. What do
you think?"
"I'm sure he will like showing me off to his friends. He promised that I
would take care of his friends tomorrow...but if he gets mad, he will
likely hurt me and you also." Jason was not too taken with the idea.
"Don't worry about that. As we said, our friend Derek will prevent that.
We may not be able to avoid humiliation though. I know this is a gamble
but it should shut him and Lisa up."
Shania and I looked at Jason. There was a big risk here. We couldnt
guarantee anything. Jason stared into his coffee cup. He heard his phone
buzz and we saw the message from Russ. 'Waiting for your strut.' Jason
showed us the message.
"I need time to get ready and need to go. I really appreciate your help
but I don't know if this will cause more problems and get you guys hurt
too." Jason stood up.
"Jason, can you give Cassie and me a second please?" Shania took me
aside. "Let's go with him to convince him. I'll call Derek to pick us up
around 6 at Jackie's place. If Jason backs off, we three can go to
dinner. If he agrees to do this, we will be busy making plans. OK?"
I wasn't sure why Shania was pushing this. Jason seemed reluctant and was
right to be careful. But I knew we had to try. "OK." I said.
"Jason, we're going with you," Shania said. It wasn't a question. It was
a statement. "Derek will join us later. If you change your mind, we will
leave you alone." I looked at Shania. There was no way she was going to
let this go. I didn't understand her motivation. She hadn't met Jackie
yet but still seemed all in. I knew she hated bullies as did I.
"OK," he said softly. It seemed that he was easy to impose on. He didn't
fight back. He just accepted we were going there.
We drove to his apartment. Jason was quiet. Shania was thinking aloud.
"We mustn't be seen together," Shania said. "Just drop us off at the
Starbucks and we can come to you a few minutes later. Maybe Lisa or Russ
is watching." It was possible as Jason had taken the afternoon off.
"I'll leave the front door open and the door to my apartment too. Cassie
knows where it is." Jason was playing the game although I suspected he
still wasn't convinced. "I need over an hour to get ready," he said
softly.
Shania and I looked at each other. This had better work or we would both
be in trouble. Jason was deep in thought as he drove us. As agreed, he
dropped us off. We wondered if we should stay in Starbucks or just give
Jason a head start and make our way toward his place. We were impatient
and with looks agreed that we wanted to see Jason transform himself.
Shania suggested we walk around the apartment to see if there was another
entrance. We still couldn't believe that Russ and Lisa would be waiting
and watching. They thought Jason was putty and his FaceTime connections
would allow them to monitor him remotely.
We walked slowly along the path where I had accompanied Jackie yesterday.
We walked along the hedgerow fence and saw that there was another
entrance to the building with space for parking on the other side of the
building. We couldn't tell which was the front or back entrance. As we
approached the door, some boys walked out and held the door open for us.
That was lucky and we could see the door at the other end of the long
corridor where Jason's apartment would be. As he had promised, the
apartment door was unlocked.
We entered the apartment with a soft 'Hello' called out. Jason called
"come in. I'm getting changed. I'm in the last room to the right."
I had not noticed yesterday but there were two rooms on the right that
led right of the hallway which ended at the bathroom. To the left was
the open living room and the small kitchenette in an L shape behind it.
The living room was small but certainly enough for one person or a
couple. I noticed the laptop on the table on the left
"Shania, I don't think our plan will work," I had been thinking the plan
through.
"What do you mean?" She asked a little brusquely. It had been her idea
and I was raining on her parade.
"Well, I mean the part about meeting him at the bar and then trying to
lead him on. What if his friends decide to go outside too? Derek can't
handle all of them, however many there could be." Shania had not thought
of that and was scrunching her eyes, deep in thought.
"You're right," she said slowly. "We have to entice him here tonight. But
how?" I could the cogs at work.
"What would lead a man like Russ to drop everything and come over?"
Shania was thinking aloud.
"What about Russ?" We turned to see Jackie. It was an incredible sight
from the Jason we had left over an hour ago. The waist was small, the
bust quite big, probably 38D or even DD, the dress a bright yellow of a
PVC material that reached only a couple of inches below her crotch. She
wore high heels that were at least 5" tall. I would have fallen down with
smaller heels. I hadn't worn heels more than 2" high till now. The face
was plastered with makeup. Heavy and large false eyelashes, heavy brows
and bright, fire red lipstick. Bright rouge adorned her cheeks. Jackie
looked like a plastic doll. She wore long dangling earrings I her pierced
ears. The wig was the same as she had worn yesterday. She looked unhappy
to present herself to us in this way.
"Wow," Shania gushed. "That's quite an outfit. How'd you manage to grow
those things so quickly? The makeup is quite dramatic. Where did you
learn that?" Shania was impressed with Jackie.
"Lisa wants me to dress like this to humiliate me. She hates the fact
that Jackie looks normal," Jackie looked sad when she said this and we
could understand.
"Show her some normal Jackie pics," I suggested. Jackie brought the
computer out of sleep mode and found albums of Jackie's pictures. She
looked so normal, so confident that it would have been very difficult to
know there were man parts under all those clothes.
"What a beautiful girl you are," Shania said as she scrolled through the
albums. "I can see why Lisa would be jealous."
Whilst Shania browsed through the images, I turned to Jackie. "I think
we need to entice Russ here. I was telling Shania that if his friends
decide to go outside to witness you and him in action, we can't handle
it. I mean whatever Russ will want you to do, it would be bad. Derek is
big but I don't think he can handle two or three guys. What could entice
him to come here tonight?"
"I have to go, it will take about thirty or forty minutes for me to walk
to the other side. They want me to be seen in broad daylight. I have to
FaceTime them as I leave the building with a lit cigarette in my mouth.
Also when I turn to come back and then when I am back here." Jackie had a
small black purse across her shoulder. I had seen her smoking and sending
images yesterday.
"Can you delay talking to him when you come back? We may need to think of
some ideas." Shania was still browsing the albums but her mind was
working.
"He doesn't like that and I would need a good excuse. He'll be angry like
yesterday." I had heard that and that is what had led to Jackie telling
me all.
"Do you have other outfits here?" Shania asked.
"Of course." Jackie led us to her bedroom and showed us his closet. It
was full of female attire on one side. A brightly lit dresser held many
pots and brushes. I was surprised how tidy everything was.
"Why," Jackie asked quietly.
"Don't know but it may be too much to resist if Russ saw two women here
that would promise him some action." Shania was hatching a plan.
"Who would that be?" Jackie asked. "I don't have anyone who would do that
for me? I have to go," Jackie said taking a pack of cigarettes out of
her purse. She put it in her mouth but didn't light it. She looked
miserable. Jackie walked out of the apartment. We hurried to the 2nd
bedroom and watched through the curtain as Jackie fumbled in her bag, lit
the cigarette and then FaceTime with her iPhone. She was scared stiff.
Soon she was out of sight.
As soon as Jackie was out of sight, Shania hurried to the closet in
Jason's bedroom and looked at the outfits. There were a few real nice
dresses, some skirts and blouses. To one side there were the slutty and
cheap outfits Lisa had forced upon Jackie. There were several outfits,
gold in color, very short and low cut and a similar one in silver. There
was a red dress too.
"You or me?" Shania asked. "We have to get Russ here and get him hot and
bothered,
"What do you have in mind?" I asked. "I feel sorry for Jackie, very much
so in fact, but I am not going to play with Russ."
"OK, I'll do it," Shania said. No discussion. She accepted my decision.
It seemed almost as if she wanted to be in that position. She took down
the silver outfit too and held it against her. It seemed it would fit
either one of us. Jackie was almost our size, but she had a bigger bust.
Shania took the gold and silver outfits into the bathroom. Shania
appeared a few minutes later in the gold outfit. She looked hot even if I
say so myself. She was smiling enjoying the role. "Let's give Russ a
reason to rush over," she said looking at the matching shoes. They were a
little big for her but she wasn't planning on walking out. I was staring
at her bust, bigger than ever and seemingly ready to burst through. "I
used some cotton I found in the bathroom to give it some prominence. You
like?" She asked coquettishly.
"I like very much but I don't swing that way," I said, "or I would jump
you now."
"Can't let Russ look too close or he'll suspect something. You any good
with makeup?" Shania was fiddling with the pots of paint on Jason's
dresser. "It's got to be like Jackie, way over the top so he thinks I am
like Jackie too." It was said in a matter of fact way. I just nodded my
head in agreement. Russ had to believe that Shania was another
crossdresser friend of Jason.
Shania had some lightly tanned skin, going back to her Latin ancestry.
She applied lots of bronze and gold shadow which seemed totally out of
place with the Shania I knew. But this was like an actress playing a
special role. She drew on thicker eyebrows with a dark pencil, thick at
the broadest part and thin at the tapered end. Jackie appeared to have
plenty of false eyelashes and I watched in fascination as she chose to
glue on the biggest she could find. A heavy application of rouge
highlighted her high cheekbones. Bright red lipstick completed the job.
She looked exactly like an overdone hooker and matched Jackie's look
quite well. I was glad that the dress didn't expose her cleavage too much
but the bulge was unmistakable. There is no other way to describe her:
hooker. But this was the look she had wanted to create. Jackie would be
able to add to her features.
It hadn't taken that long and we were expecting Jackie back soon. She
would be using face time with Russ to show she was back,
"This is the plan," Shania said. "Jackie will have to wait ten minutes
before she calls Russ. This is because her "girlfriend". Shaniqua is
visiting unexpectedly. Shaniqua was looking for a hot night with Jackie
and was waiting at her for when she returned from her strut." Those words
flowed fast and almost in one sentence. "If Russ thinks Jackie and
Shaniqua are going out on the town, he would want to be the first here to
..to sample the wares. What do you think so far?"
I had no words but knew that Jackie would be here any minute and she
would decide what happened. If our guess was right, Russ would be here
within thirty minutes of seeing Jackie and Shaniqua together. But where
was I to go? Derek? So I asked Shania.
"Let's talk to Jackie, but I think Russ will want to play with us both, I
will try to be there but it is Jackie who needs to be released. So as
soon as the action rolls, you and Derek have to start to take
photographs. I am thinking that Jackie should be fully made up but
without her wig so the shot will clearly show Russ with a male in drag."
"Sounds risky," I said cautiously. "I don't know how we will get to take
shots of Russ and you guys without being seen or heard."
"I think you guys should be in the 2nd bedroom, lights off and the door
ajar. If we have read Russ correctly, he will be thinking with his thing
down there and will not inspect the room for others. In fact, I think I
should open the door for him and get him to follow me into the living
room where Jackie will be waiting. He will start to pounce on us
immediately and you guys need to slide out carefully and noiselessly.
We'll try to be loud so he doesn't hear the click of the camera. You must
turn the flash off too." Shania was in form thinking as she went.
We heard the door open and Jackie walked in. She looked in shock as she
saw Shania and looked at her with open mouth.
"We thought that Russ might come over if he thought he could get
attention from two bimbos," Shania said. "I was explaining to Cassie. By
the way Cassie, can you go and get Derek? He is at the Starbucks but
hurry back. I'll explain to Jackie."
I hurried out and left the front door ajar; also the apartment door.
Jackie and Shania would be in the bedroom or living room. All I needed
was a little over five minutes. Derek was waiting as agreed. He greeted
me with a big hug. We hadn't seen each other in an year but that didn't
seem to matter. We rushed back.
As we entered the apartment, I saw that Shania had more makeup. Her mouth
looked bigger and she had heavy black lines around her eyes. Jackie had
her wig off and stood there like a deer in headlights as she met Derek.
They stared at each other a second and Derek gave her a hug. "Don't
worry," he said reassuringly. He was bigger than Russ.
"I explained everything to Jackie. When she face-times Russ, she'll say
that I was waiting for her as she returned and wanted to go out tonight
and have some fun. With Derek here, we don't have to fear Russ. If he
comes, we'll do as we discussed. If he says no, then we'll have time to
find another idea. Ready Jackie? You guys have to be quiet and out of
sight." Shania shooed Derek and me away and I took Derek to the 2nd
bedroom. It was not big but held a single bed. We stayed in the hallway
to be out of sight during the facetime call.
Jackie nodded and sat at her computer with her iPhone. She dialed Russ.
Shania was in the back near the kitchenette.
"Where the fuck have y out been?" We're the first words out of Russ's
mouth. "What happened to your hair?" He asked angrily as he saw Jackie
without the wig.
Jackie was scared and you could hear the quiver in her voice. "I had a
surprise visitor," she began to say
Russ interrupted her. "Who the fuck is she and when did you agree to see
her."
"Sorry Russ, I didn't know she was coming. Her name is Shaniqua and she
is a girl I met online and have met a few times." Jackie was genuinely
nervous and it could be heard in the voice. "We have been out a few times
and.. and partied. Sorry."
Derek and I were crouched in the entrance hall, well out of camera sight,
and saw Shaniqua appear out of the kitchenette. Russ could see her as a
background to Jackie. "Sorry Russ, Shaniqua hugged me from behind whilst
I was dialing you and pulled my wig away. I didn't have time to fix it
yet."
Shaniqua came closer and said in a husky voice, "hey Russ, you want to
party with us?" Shaniqua was in closer view now and Russ would have seen
the overly made-up face and big bust. He would have to think of her as a
fellow crossdresser.
"Wh..what are you guys planning" Russ demanded
"Why don't you come over and we can discuss," Shaniqua said in that husky
voice. "I just need some loooove tonight," Shaniqua cooed. She went
behind Jackie and grabbed her breasts. Russ would see two hands grab
Jackie's massive breasts. We couldn't see Russ but I could just imagine
what was in Russ's mind.
"Don't fucking move," Russ demanded. "I 'm meeting the boys later but
maybe a little action before won't hurt. Girls, don't go anywhere or
Jackie gets it." Russ hung up.
So Russ had fallen into that trap. If everything else went into plan,
then Jackie would be out of her nightmare. "I will try to give you Russ's
phone. Can you get his address base?" Shania was thinking through
everything.
"It can be done but will take time. I will need a few minutes to get some
names at least and will need Derek's help. I only hope he has no password
protection." There was no way to get all his contacts instantly, but if
I could open his contact list, I could photograph some names and emails
at random. 10 or 20 names would be enough. Besides, Russ would not know
how many we had copied.
In all of this I was surprised that Derek went along. He didn't ask
questions and agreed with all our suggestions. He was a gentle giant. I
was wondering about why he was doing this. He didn't know Jackie. He was
doing this for Shania who kept leading him on. I thought he deserved
better, but I knew Shania's flirtatious ways. She could get boys to do
what she wanted. I was grateful and glad he was there with me.
We went over the details. Shaniqua would meet him at the door and lead
him to the living room. Derek and I would observe through the open door
of the darkened 2nd room. Russ would be in a hurry. Jackie would be in
the kitchenette area and open a beer for him and try to get him hot.
Shaniqua would also make comments to get Russ steaming. He would only
have one thing in mind. What we needed was to get Jackie's face close to
Russ's cock. Without a wig, Jackie would look like a boy in a dress,
especially with that massive bosom and overly made up face. That's when
we would spring the trap and take the photographs. Derek and I would both
have cameras ready. Jackie would need to hold Russ's thing very close to
her face or mouth and I could see Shaniqua smile from behind the camera.
We would have to play it by ear.
Shaniqua asked Derek and me to go into the 2nd room. It was dark and the
door was left ajar. Russ would be here soon. I could felt Derek near me
and I reached for his hand to be sure. Shaniqua did not appear to have
any worries. I was scared out of my mind. Derek seemed to go along with
this without question. I was glad he was near me.
We hear the buzzer go. We saw Shaniqua walk to the apartment door and
press the buyer; a moment later Russ was at the door and she let him in.
I wish we could have observed Russ meeting Shaniqua. We could hear them,
but they needed to pass our door before we would have partial vision.
"Hi Russ," we heard Shaniqua say in her husky voice. "You are a big boy."
We heard Shaniqua emphasize "big". They must have hugged or something as
it took a few moments for Shaniqua to pass our door. She was holding his
hand and he looked like he had just won the lottery with a wide grin on
his face. He still hadn't figured if Shaniqua was a boy or girl. They
went past us and entered the living area on the left.
"Hey Jackie, Russ is here." We heard Shaniqua call out to Jackie. "The
poor boy looks thirsty - or is it hungry - so why don't you get him a
beer?"
"OK," is all we heard? Shaniqua was leading the discussion.
Derek and I opened the door a little wider to hear them better. It wasn't
time yet to move out. "Cheers, Russ," we heard Shaniqua's voice. I heard
the clink of bottles. Was Shaniqua drinking beer?
"So Russ, what do you think? Want to go out partying with Jackie and me?
We know this little place that likes people like us and has a big dance
floor." Shaniqua was pushing Russ.
"Er.. No," Russ replied. "Sorry but have a meeting later but I couldn't
resist coming over and meeting you before I go to my meeting." Russ
didn't want to be seen with Jackie and Shaniqua. Dressed as they were, it
would damage Russ's macho image.
"Well, then, we may just have to show him what he is missing, right
Jackie?" Shaniqua was taunting Russ. We couldn't hear Jackie.
Derek and I crouched forward and saw Jackie and Shaniqua face the living
area entrance; Russ had his back to us. Shaniqua and Jackie were close
and had their hand around each other's waist.
"Let's get a selfie, Russ, so you don't forget us." Shaniqua was
provoking Russ. He took out his camera and took several pictures of
Jackie and Shaniqua together. Derek and I slid back as Shaniqua pulled
Russ between her and Jackie and had him take a selfie. He was grinning.
"Take another, Russ," Shaniqua said as she and Jackie kissed Russ on the
cheek simultaneously. We would see the bright red lipstick marks on
Russ's cheeks later.
"I think our boy is in a hurry," Shaniqua suggested. "He may need some..
some relief before he bursts his pants before the meeting. Shaniqua
touched Russ's crotch and we had a good shot of Jackie's and Shaniqua's
hands at Russ's crotch. "He does appear to be a big boy," Shaniqua said
to Jackie. Shaniqua took Russ's phone from his hand, and took another
selfie as she and Jackie snuggled real close to Russ. Jackie planted
another kiss near Russ's mouth. Shaniqua put the phone down on the side
table and handed Russ back his beer. They clinked bottles. Shaniqua had a
bottle in her hand too. I dint know she drank. "To a good evening," she
suggested and took a swig of beer out of the bottle.
"Jackie, I think Russ is in a hurry here, and we had also better get
going to have dinner and then the club. How about we give Russ something
to think about? Let's show him what he is missing." Shaniqua walked over
to the small sofa and threw down two cushions at Russ's feet. Although it
appeared casual, the cushions on the floor would show Jackie's upper body
well and Russ's side view. Shaniqua would be seen only in some images. It
had to be unmistakably Russ. Derek and I saw Jackie looking nervous, not
saying much. Shaniqua was doing all the talking.
"Jackie, I think we need to help Russ here." Jackie and Shaniqua went
down on their knees on the cushions. They both reached for Russ's belt. I
took some pictures and switched my iPhone to video mode. They undid the
big buckle and pulled down his jeans around his ankles; his tartan
patterned boxers were next. Shaniqua and Jackie started rubbing Russ's
stomach and we filmed the rise of Russ's somewhat large tool. From our
viewpoint, we could see Jackie fully and a side view of Russ with rampant
cock. Shaniqua was only partially visible. We saw Russ, bottle of beer in
hand, take a big gulp and look at these two girls who were promising him
a very 'happy ending'.
"Just a moment," Shaniqua said and arose. She went to the table and
produced a tube of lipstick. She gave it to Jackie and pursed her lips.
Jackie got the message and applied several generous coatings of that
bright lipstick on Shaniqua. Jackie handed the lipstick over and Shaniqua
applied several coats of lipstick on Jackie. Derek and I were filming
this and it was getting hot. I was worried that we would make a sound and
spoil the surprise.
Shaniqua led by grabbing Russ's cock and stroking it. She looked up at
Russ. "Do you want us to continue," she asked coquettishly. Russ would
explode in anger if they didn't finish what they started. Russ nodded his
head and his grin was wide from ear to ear. Jackie now held Russ's cock
and was looking up at him with those massive lashes. The short hair made
it look just as we wanted. The bright red lipstick, freshly applied, was
appearing very close to Russ's tool. A look passed between Jackie and
Shaniqua and I saw a big red lipstick mark on the side on Russ' hard
cock. Shaniqua also placed her hand on Russ's tool and turned to Jackie.
"Let's show Russ how we do this," she said and planted a deep kiss on
Jackie's mouth. They were still both holding on to Russ who was looking
down in amazement as Shaniqua and Jackie had their tongues down the
other's throat. They stopped and looked at Russ who must have thought he
died and went to heaven.
They began to stroke him and Jackie moved her face nearer to Russ's
crotch. We had a perfect view and Derek and I were filming the action,
mesmerized by the goings on. Shaniqua grabbed Russ's balls and was
feeling them. She squeezed them looking at Russ. "How does it feel to
have two trannies bring you off?" Shaniqua asked.
"Oh girls this is hot. Until I met Jackie last week, I had never done
this with a boy-girl." I smiled as I had been able to video that and
capture the audio. Shaniqua was smiling. She too had noticed this.
"Do you think Jackie makes a good girl?" Shaniqua teased, still massaging
the sac in her hand.
"Oh yes. I have a small party planned for her tomorrow. Can you be there
too?" Russ was now speaking with gaps as Jackie and Shaniqua were
stroking him faster. Jackie leant forward and gave another big kiss on
the side of Russ's cock. We could clearly see the red mark.
"Do you like Jackie?" Shaniqua asked. Russ nodded his head 'yes'.
"Do you like to be sucked by boys dressed as girls?" Russ nodded again.
"I didn't hear the answer," Shaniqua said "If you want her to put that in
her mouth, you had better tell her you like it." Shaniqua and Jackie
slowed down their stroking and were looking up at Russ, smiles on their
faces.
"Oh yes, I like her to do that?" Russ stuttered. The stroking began in
earnest again, in slow strokes.
"Tell her you like boys dressed as girls sucking you off. They know how
to suck," Russ was close and we could see and hear his labored breathing.
"Plea.." Russ pleaded, wanting Jackie to put it into her mouth. His tip
was close to Jackie's mouth but not quite there
"Say it then," Shaniqua insisted.
"Yes, I like boys dressed as girls sucking me off..."even as he uttered
these words, Jackie stroked him faster and was the recipient of a large
glop that erupted on her face, running down his cheek. One glob actually
hit her forehead.
"Surprise," Shaniqua shouted and pointed to us.
Russ watched with open mouth and shouted expletives. Even as he opened
his mouth and raised his hand to strike, Shaniqua squeezed hard on the
sac in her hand. Derek, rose to his full height and got to Russ quickly.
"Just don't," Derek said softly holding Russ's raised hand.
Even as Jackie had squeezed his cock hard, Shaniqua still was squeezing
Russ's sac even harder and I could see the pain in Russ's face. All
captured on my iPhone. Derek standing there immobilized Russ. The pants
and boxers around his ankles gave Russ no movement as he tried to swing
his hands to strike and he fell backward, hard on his behind.
"If you or Lisa make any more demands on Jackie, be very sure where these
pics and videos are going. I am sure the boys would love to see macho
Russ being handled by a tranny." Shaniqua was still gripping Russ's sac.
Russ looked confused and was grimacing in pain. "Derek here has a mean
streak so any threat from you or Lisa, will get Derek all riled up. You
won't like that," Shaniqua said rising. She let go of Russ and helped
Jackie up. "Go, we know where your boys are."
Russ pulled up his boxers and with belt and shirt hanging rushed out of
the apartment. We watched him rush out red-faced and flushed with anger.
We all looked at each other, pleased that things had gone as planned.
Jackie and Shania held hands. I was pleased that things had gone without
anyone getting hurt. As Derek and I turned we saw Jackie and Shania
kissing deeply. They had shared something special.
I looked at Derek. We stared at each other and then he leaned forward and
kissed me briefly on the lips. It didn't take a second for me to react
and pull his head forward and also give him the biggest kiss I knew to
give. My first serious tongue kiss. It seemed the erotic events a little
while earlier had affected us all. It was like getting excited by
watching a porn movie.
After we calmed down, we all breathed a sigh of relief. Things had gone
as planned. We wanted to celebrate and agreed to meet at that little
Italian bistro next to Starbucks. Jackie and Shania needed time to
change. It was still early and after checking my face, Derek and I left
to go grab a table. As we were walking to the bistro, hand in hand, my
phone rang. The number was unknown. I picked it up and said "Hello." It
was Jack Straw.
"Hey Cassie, it is Jack Straw at AB Soft. I have been trying to reach
you. We would like to offer you the job and hope you can start Monday.
Are you ready for it?"
After all that excitement today, this was the crowning glory. "Oh, yes,
Jack," I said. "I would love that. I'll be there Monday." I was on a
high. Not only had we helped Jackie, I had a new job and also found a
special friend. I called mum and told her that we were having dinner and
celebrating. She was very happy. Derek was beaming too very happy for me.
Sometime later, Jackie and Shania entered the restaurant. Derek and I
hadn't noticed as we were catching up on events. Jackie was dressed very
nicely in a skirt and blouse and high heels. Her makeup was normal and
she looked very attractive. She and Shania were holding hands. We ordered
some wine and toasted the success of our mission and my job.
A thought struck me. "What a shame we couldn't get Russ's contacts," I
said. I had my left hand in Derek's and the right around the stem of a
glass of wine.
Shania smiled that big smile. She was also holding Jackie' hand. With the
other she dug into her purse and pulled out an iPhone. "In his rush to
exit, Russ forgot his phone. Cassie, you better get the data and give it
to Jackie. She can give it to Lisa." She pulled Jackie to her and gave
her a kiss on the lips in full sight of the diners in the restaurant. Two
girls kissing on the mouth in public was not common. Jackie and Shania
didn't appear to care. Neither did Derek and I. I was happy that they had
found each other in these circumstances. Shania didn't appear to have any
issue with Jackie's dressing. I was happy. I had found a special person
too.
"I think I want to get to know Jackie a lot better. We shared a lot
tonight." Shania said softly looking at Jackie. I was happy to have been
a help in bringing Jackie and Shania together.
I squeezed Derek's hand. It seemed that Shania and I had not only helped
Jackie overcome her problem, but also found a way to bring me a close
friend.