Brianna
- 2 years ago
- 17
- 0
Brianna's Game (8) free porn video
MEETING KELSEY
1/
I obtained Stephanie's address from Anna and visited her the evening
after her shopping trip. When Anna explained what was happening in
work --- how successful the email had been, the staff meeting that was
arranged so everybody could meet Stephanie, their new Office Girl ---
I wanted to show my girl as much support as I could.
What I didn't expect was for Stephanie to be in the middle of a homing
crisis.
When I arrived and knocked on the apartment door, a male voice called,
"Who's there?"
I could easily imagine Stephanie panicking that she might have to open
her door at an unexpected arrival. I let her stew for a few seconds.
"Relax," I assured her. "It's Brianna."
After a moment the door eased open and she ushered me in.
"What are you doing here?" she asked. "How did you find me?"
I told her Anna had given me her address and that I was only here to
help.
Even though it was late in the day, dark, I'd actually found it easier
to come out. The streets were less crowded; the city less closed in,
not as claustrophobic.
"Look at me. I'm a mess," Stephanie blurted. "I've got to go into the
office tomorrow dressed like a real woman and I'm being introduced as
the new Office Girl. I don't know if I was drunk but somehow an email
landed in work about how I-"
"Take a breath," I told her, gently taking her arm. "Sit."
I moved some of the pretty clothes out of the way. She must have been
working through the outfits, trying to decide which looked best,
getting herself into a proper state.
She was wearing a pencil skirt that fell just beyond her knees, hose
and a blouse that had a delightful floral pattern. It almost worked. I
encouraged her to sit with her legs crossed and she obliged me, trying
not to appear awkward.
"Don't worry. With practise such body language will become familiar to
you. You've got some nice clothes. You've been very busy," I noted.
"That's part of the problem. I have no idea what to wear-"
I smiled. Not.... "I can't wear these clothes" ....She was just
concerned about how she looked.
"-what goes with what. And Kelsey saw me. She-"
"Kelsey?" I asked.
"My land-lady. She knows how I'm dressing and she's a friend but I'm
being evicted because I'm behind on the rent and I don't know where-"
"Okay," I told her softly, placing a hand on her leg. I made a mental
note of the hairs for in a moment. "Listen, you're handling our game
very well. To be honest, it's moving from a punishment to something
I'm enjoying doing with you. I haven't been in-person with a girl for
a long while and you're helping me as much as me you. That said, don't
ever forget you are still my bitch for what you did. Understand? You
stole one of my favorite sets."
Stephanie nodded. "Yes, Mistress, but-"
I held up my hand. It was like she was hypnotized by my false nails.
"You're handling everything about your feminization very well. Better
than many of the girls I used to work with. Your problem tonight is
about your wardrobe, but it is being exacerbated by this stress about
your home."
Stephanie nodded. She was starting to calm down. But tears were
slipping from her eyes.
"Is Kelsey here in the building?"
Stephanie nodded. "She lives in the first apartment. But she's really
nice so please don't-"
"Stephanie, I may be your Mistress, but I'm a woman first. And I may
have made mistakes in life, but I like to think I'm kind and good
natured."
"But you're strict and-"
"Even though this has been forced on you, remember how I've taught you
to respect others and to be responsible. That's how I conduct myself
in the world. I'm just going to chat."
"Okay," she said, relaxing.
"Do you have razors?" I asked her. "Shaving cream?"
She nodded.
"By the time I return I expect your legs, chest, arms and underarms to
be smooth. Now go run a bath and relax."
2/
Stephanie soaked, trying not to worry about what might be happening
downstairs between two of the women in her life.
To distract herself from her concern, and the thoughts of what might
happen at the staff meeting in the morning, she started to shave.
She cut herself a few times and it was a long process, shaving hairy
parts of her body that had never been touched in this way before. It
was also very tricky, she thought, reaching between her thighs, around
her legs, up to her butt.
Why did women go through this?
But then a leg emerged for a moment through the bubbles. She touched
it for a second, her clit getting exciting. So smooth. She imagined
her legs moisturized and trapped in pantyhose or stockings. God, they
were going to feel great.
For a moment, she teased herself....Stockings and a skirt; a short
skirt showing off her newly shaved legs for all to see.....she played
with herself, applying pressure but not working her small shaft....she
was masturbating like never before, trying to simulate how a woman
might touch herself......her smooth legs, the envy of women and the
delight of men who-
"No, no, no," she panicked. With a girlish cry she pulled her hand
away from her clit, but it was too late. While not reaching orgasm, a
surge of cum had leaked into the water.
And now she was stuck with it, floating around the water as she
continued to shave. Even though now, her pleasure satiated, she was a
little unsure of what she was doing, doubts creeping in.....
How could she possibly have agreed to be the new Office Girl?
3/
The apartment building wasn't a maze and it was easy enough to find
Kelsey's place. She seemed extremely pleasant, a tomboy through and
through and perhaps not somebody I would normally hit it off
with......But who knew what type of person that was after I had lived
a year as a recluse, so I accepted that we got along fine.
"Would you like a drink?" Kelsey asked.
"That would be great," I asked. "Wine?"
Kelsey laughed. "Brianna, I'm not sure who you are except that we have
a mutual friend upstairs, but do I look like a wine kind-of-gal?"
"I was being hopeful," I told her, smiling. I was warming to Kelsey
with each sentence.
"Beer?"
I nodded. "Bottle. No glass."
"Yes, Ma'am," she grinned and returned a moment later with two chilled
bottles.
We each took a sip, getting a sense of each other.
"I want to apologize," I began.
"For what?" Kelsey asked. "Until you knocked on my door and explained
you knew Steve.....Sorry, what did you call him?"
"Her," I corrected. "I called her Stephanie."
Poor Stephanie. Her worlds were colliding again.
"That's so funny. I know he likes dressing up, but I didn't know he
had appropriated our gender. And taken a name."
"A lot of girls do," I told her.
"What are you sorry about?"
"I didn't realize our game was causing you --- or her --- a financial
burden. Had I known, I would have-"
"Wait a second," Kelsey said, draining her bottle. "Another?"
I had barely started and shook my head.
Kelsey left and then returned with her second. "You said game?"
"She hasn't told you?"
"Only that he-shit-she likes to dress up in girl clothes," Kelsey
said, taking a swig of her drink. "Nothing wrong with that."
I considered Kelsey. She was a straight shooter and I decided to let
her in on some of the events that had happened in Stephanie's life.
She didn't need to know about all my history, and, even though I had
shared that unfairly with Deborah.....sweet Deborah....and I was more
comfortable with my past now, it didn't need advertising.
I explained how I met the man she used to know as Steve Mayfield when
I was in the market for a swimming pool.
Kelsey laughed. Quite suddenly and delightfully. "I have a shower and
it has a little bath-tub underneath it. If I crouch and pull my knees
up I can sit in it and-"
"If you want to see the pool when it's complete, you can visit." I
considered her image, and when the following words came out of mouth I
knew I was genuinely finding my way back, "But only if you wear a cute
bikini."
Kelsey considered me, still not fully aware of who I was. But I think
she was getting an idea. "You'd like that, wouldn't you?"
I sipped from the bottle, the cold chilling my lips.
"Yes, I would."
For a moment Kelsey was lost, and then, "Okay. You're on. You get that
pool and send me an invite and I'm there. Bikini and all."
"The pool's already ordered," I grinned.
Kelsey was a little flustered. Not a feeling she was used to. She
bounced back.
"What about Steve-Stephanie? You said about the pool?"
I wasn't sure how to describe what had happened. I had to keep Kelsey
sympathetic to Stephanie. I didn't want to alienate her.
"Do you know much about cross-dressing?" I asked.
She glanced down at her own clothes, gave me a Homer Simpson, "Doh?"
"It's much easier for a woman to dress like a man," I explained. "We
already wear most of the clothes men do, so it's not a big stretch for
us. But for a man to put on lingerie, a bra, or a skirt, a dress.....
for a man to wear make-up.... They're fighting generations of embedded
denial. In themselves. In society. It's a very brave and curageous
thing to see. Whether they pass and pull off a particular look, or
not."
Kelsey nodded, thinking about the first time Stephanie had opened the
door to her; the way she had let her in. The risk of potential
humiliation and damage to their friendship.
"Yes," she nodded. "I see."
"For some men," I continued, "it's a compulsion. They just can't help
themselves. A lot of cross-dressers deny themselves, deny who they
are, spend a life-time fighting guilt and shame and never resolve
their feelings. It's most unhealthy. Once a girl has accepted who she
is, whether she just enjoys dressing or has desires to be feminized,
even forced feminized...... Whatever her proclivities are...... She
might even transition one day.....Once she has accepted herself,
happiness and confidence will follow. Do you understand?"
Kelsey nodded again. "I'm keeping up. Is that what Stephanie is? One
of these guys-girls who wants to be made to dress. Is that the game?"
I had to be careful here. I didn't want to lose Kelsey for Stephanie's
sake. Stephanie had faced an irresistable temptation that had ambushed
her; she had been at the mercy of her own nature, one she had denied
for years. Kelsey had to understand that Stephanie had no doubt built
barriers up to prevent this kind of thing from happening, to stop
herself from dressing....
"I think she does," I said. "For some men that idea comes easily. With
Stephanie I think it is more because she had denied herself for so
long. She had an opportunity that, for her, was impossible to resist.
She stole some of my lingerie."
I let the words sink in, could see different emotions flickering over
Kelsey's face until finally, and this is when I knew we were good, she
laughed.
"That bitch!"
The insult was good humored.
"Tell me about it," I said. Now for the next big revelation, the one
some women balk at. My nature. Who I am. What I am. "She just didn't
realize who she was stealing from."
Kelsey went for her third bottle and when she asked me about a second,
I nodded.
"You're like a spy. Janet Bourne? Jane Bond?" Kelsey asked when she
returned, a little tipsy, which I'm sure was making this conversation
easier.
"Nothing as exotic. I'm a Mistress."
She took a second.
"Like a dominant.....You boss men around and make them....."
I nodded while she took it in.
"For my own reasons I haven't sessioned in-person for a while. I've
been conducting fun stories online that girls seem to love playing.
But Stephanie......"
"Go on," Kelsey encouraged.
"Stephanie's helped bring me back into the world a little," I
confessed, tears springing into my eyes.
It was my turn to be comforted, Kelsey's hand landing instinctively on
my thigh. "Are you okay?"
I nodded. Even though the wounds, both physical and psychological,
were old, my new found freedom was raw and emotional.
"I'm good now," I told her, a tear or two slipping out. "Listen, I
didn't know the game was putting a burden on your business."
From my handbag I pulled out my check book.
"What are you doing?" Kelsey asked.
"I'm covering you for the trouble you've had. This short notice
eviction."
"You can't do that," she exclaimed. "It's his-her......Look, she's
been out buying all those-"
"It's fine. In the back of my mind I figured this would happen
eventually. I have an empty guest house and a girl who needs a place
to stay. I need to continue developing this trust so that I can heal.
This is for me as much as her. I'm going to let her stay with me."
I scribbled a figure on a check and signed it.
"I'm far from rich, but will that cover it?"
Kelsey's eyes went wide at the figure. "That's too much. She's only
overdue one-"
"And the rest will cover the next month or so while you look for a new
tenant. I just need a little help."
"Thank you. What do you need?" Kelsey asked.
"I believe Stephanie is accepting more and more what is happening to
her, even though I'm sure she has limits. But at some point her male
instincts will buck against her and try to fight back. Tomorrow, she's
starting her new job as an Office Girl."
"You're kidding?" Kelsey laughed.
"She's a wreck about what to wear, so I'm going to return and choose
an outfit for her," I explained.
"You're not kidding?" Kelsey whispered.
"She's going to need help with her make-up and hair. Is there anybody
who can help out with that in the building?"
"This is really happening?" Kelsey asked.
I nodded. "She'll tell me when to stop."
"I....wow.....Sure, Eve's the complete opposite to me. Real girly
girl. And she knows that Stephanie has been playing dress up."
"Both of you call on Stephanie in the morning. Help her get ready.
She'll be scared. It's a big day for her."
"We will. Steve was a friend before....I mean, she's still a friend.
We'll be there for her. Can I tell Eve why she's dressing like this?"
I nodded. "So long as you're discrete. Maybe I'll meet you both at my
pool. So long as-"
"I know. Bikinis only. You enjoy your games, don't you?"
I smiled. For a long time I had been scared, but now I was getting
back into my groove.
4/
When I returned from my chat with Kelsey, Stephanie was just getting
out of the bath. And what a difference. Except for a small patch of
pubic hair above her little clit, her body --- all her body --- was
quite, quite smooth.
"Dry off," I told her. "Moisturize, if you have any lotion. If not,
don't worry, we'll fix all that kind of stuff soon. And then, naked,
come and see me."
I could see fear in her eyes and smiled before leaving. She was truly
becoming mine. Now it was just a question of what I would do with her,
how far I would go. Not to the extremes of my former peeers and
colleagues with my rapist, of course, but as long as Stephanie was not
complaining I was determined to keep pushing her.
5/
It took ages for Stephanie to towel dry. Her hands were trembling and
she had absolutely no idea what was about to happen. So far, a lot of
Mistress Brianna's game had been conducted at a distance, using Anna
as a kind of surrogate. The fact that she had manipulated
that......the fact that Anna was running with the fake email that had
been sent into work......God, she was good, but when would she stop?
She felt a couple of tears in her eyes and she quickly wiped them
away. Stupid, she thought, not even sure why she was crying. You can
stop this anytime......Just tell her no. Enough. Game's over.
This was a punishment, she remembered, so Mistress Brianna might push
him a little further, but....then it would be over and he could get
back to his job and never play dress up again.
He....It was the first time he'd used that pronoun in a while....
Only....
At the back of his mind......
A soft whisper......
"Don't stop."
She looked in the mirror, wiping condensation away, and realized she
had said the words outloud.
I just need to reassert my authority a little, she thought. Let my
Mistress know she could play the game but it had to be more on my
terms.
Stephanie rummaged in the laundry hamper. Damn it, she thought. There
was no male underwear. There had to be something...... All she needed
was a pair of boxer shorts...... But all she could see were soft, sexy
panties and bras.
This wasn't happening.... The one time she needed....
"Go on. Put them on for your Mistress," she whispered to her
reflection.
That was still rebelling, she thought. Mistress Brianna had said
naked. Well, this would show her....
Stephanie took out a pair of red, lace panties and the matching bra
which she hooked behind her back, just like a real woman......Cursing
how natural it felt to do that.
She balled her fists like an infant, frustrated, and then stepped out
of the bathroom.
6/
"I thought I said naked," Mistress Brianna noted as Stephanie emerged.
"I can't," she said. "I won't. I-Look, I-I'm ashamed. I'm enjoying
what we are doing. But a part of me wants it to stop. I can't go to
work as Stephanie...... As the Office Girl...."
"Do you really want it to stop?" Mistress Brianna asked, a little
surprised, but knowing this day would come eventually. She conducted
herself responsibly, within limits set by clients, whether online or -
-- back in the day --- in person. If Stephanie wanted this to end, she
would respect that?
Stephanie, wearing lingerie before her tormentor, her Mistress......
God, it felt so good just thinking that....felt her penis shifting....
Not a clit, she thought, not caring what anybody said, her thought
process breaking for a minute.
"I'm a man," he said, as strong as he could, the words barely a
whimper.
"Are you?" Mistress Brianna asked.
She watched as Stephanie started to leak pre-cum juices into her
panties, her tiny clit barely stiffening, the panties not even
tenting.
"But this can't be me......"
"Lower your panties," Mistress Brianna instructed.
"I will not," Steve said.... Steve.... That's who I am, he thought,
climbing up out of the game, breaking whatever feminine spells had
been keeping him under. It had all been so wicked and delightful, but
now..... He was so ashamed and ridden by guilt in this embarrassing
moment.
"Lower them," Mistress Brianna whispered, making her step forward to
hear. "Lower them and prove to me you are a man. Show me that big cock
of yours. The one that surely impresses all the girls."
"I've not had many-Listen, it's pretty big okay-but-I-" he protested,
sensing he was getting weaker. Come on, he thought. This was it. A
chance to end the game......
Body shame, Mistress Brianna thought. So many girls had body shame. If
they could only let go and accept who they are, they could truly start
to shine. Confidence would enable them to blossom. Sometimes, they
just needed a little help.
"Lower your panties," she whispered, her voice seducing Stephanie.
"I-it-"
Steve, still Steve and fighting, lowered his panties and stood before
Mistress Brianna, beaming proudly at his size as his cock hardened.
Mistress Brianna laughed.
"What?" Steve said.
"That little clit?" she giggled.
"It's my-look at it-" Steve protested, feeling pre-cum dribbling off.
Mistress Brianna knelt before it.
"Let me show you something," she said, and held her pinkie finger up
to Stephanie's clit. "That's a clit."
"But the water was getting cold," Steve cried defensively. "It can get
bigger."
Mistress Brianna watched her concentrate. The clit barely moved.
"Thinking about fucking a hot chick?" she asked. And then added, "Or
wearing that sexy outfit you're imagining her in?"
"The outfit...." he whispered, knowing he was losing this small
battle.
"Look, it's nothing to be ashamed of. Lots of girls have beautiful,
little clits. And you're one of them," Mistress Brianna said softly.
A little cum started to leak out. Mistress Brianna caught it on her
finger and stood before her.
"Open wide," she whispered, holding her finger up.
Steve clamped his mouth shut. There was no way he was eating that.
"Just a little taste for my favorite girl," Mistress Brianna
continued. "I bet you've thought about it."
"Yes, but-"
Mistress Brianna slipped her finger into Stephanie's mouth. She felt
her resist at first, but then, just for a second, she sucked on the
wet pinkie finger. Licked every drop off.
"That's right," Mistress Brianna said, smiling as more cum leaked out
of the little clit. Poor Stephanie didn't even realize it was
happening. She was so engrossed in the taste. A slight moan from her
and then-
Steve jerked his mouth away.
"That was horrible," he complained. "Don't ever make me do that
again."
Mistress Brianna smiled. He wasn't complaining about stopping anymore.
Just that he didn't want to eat his cum again. Maybe somebody else's,
she mused. One day....
"Let me show you something else," she said, and then asked Stephanie
to remove her bra.
"I don't want to," Steve said.
"Take it off," Mistress Brianna instructed, her tone sterner.
Steve, ever so professionally, unhooked the bra from behind his back
and Mistress Brianna smiled at the brief, habitual action. He then let
the bra fall from his arms to the floor. His hands instinctively
raised to cover his-
"What cute tits you have," Mistress Brianna noted.
"I do not have tits," he argued.
"Lower your hands."
Steve did as he was told. Remember, he thought. Steve....Even though I
have a little clit and not a cock, after all. Even though that cum
was..... Say it..... was quite delicious.... I. Am. A. Man, he
thought.
"Look how perky they are," Mistress Brianna said. "Small, but
wonderful."
She held them for a second, jiggled them slightly in her hands.
"But how?" Stepha-Steve moaned, his arguments about being a man
falling away. It's not fair, she-he thought. "Why have I got these
little breasts?"
Mistress Brianna smiled cruelly. "Would you like them to be bigger?"
"No. Please don't...."
Begging now, Mistress Brianna thought, satisfied. This little revolt
was ending.
"Bigger for all the men to-"
"No, please don't make me have big tits."
Mistress Brianna laughed a little at Stephanie's predicament. She had
gone from making a stand to accepting who she was and begging in
minutes.
"But wouldn't all that attention be nice. You could wear some tight
fitting tops and-"
"Please, Mistress Brianna. I'll do other things, anything, but don't
make my tits too big."
"I'll think about it," she told Stephanie, and then tried to calm her
down a little. "It's your bras. You've been wearing them consistently
for a while now. To get cute, little breasts you don't need to take
hormones or anything. The cups mould whatever fat you have there into
a natural shape, especially if you use inserts which you will be soon.
They won't get much bigger, but you should be proud. They're quite
delightful."
"Are they really?"
"Yes, they are. You are a very special girl. Now, then. Do you have a
little clit?"
"Yes, Mistress Brianna."
"Do you have the cutest, perky breasts?"
"Yes, Mistress Brianna."
All the time Mistress Brianna could see Stephanie's little clit
twitching crazily. The girl didn't even realize cum was leaking
everywhere in these seconds.
"Do you enjoy wearing soft, sexy clothes?"
"Yes, Mistress Brianna."
"What's your name?"
Only a moment's hesitation. "Stephanie. My name is Stephanie."
Mistress Brianna caught some of the cum on her palm and held her hand
up.
Stephanie closed her eyes, but licked the hand clean.
"Do you like the taste of cum?"
She didn't want to say it, but..... "Yes. Please can I.....?"
Mistress Brianna caught some more.
"Open your eyes," she told Stephanie.
Stephanie did as she was told and tried not to look as she licked the
sticky mess from Mistress Brianna's palm.
"Do you want to taste another man's cum?"
"Please don't make me....."
"Maybe another day. Maybe my sweet Stephanie has a sexy, slutty side?
Maybe sweet Stephanie wants to play sexy dress up for a night on the
town? Or in a hotel bar with her own room?" Mistress Brianna whispered
seductively, watching Stephanie's clit make a final effort and burst
back to life.
"God, please..... Yes, please.... Please...."
"We'll see. Where do you work?"
"At the pool company in the city. I'm the new Office Girl...." She
suddenly moaned, breathless, realizing she was climaxing and that her
chance of escape was over. "I'm going to be a secretary."
"Do you want our game to end?"
"No, no....Please don't stop....please...... I'm sorry..... I'm your
girl...." she panted. "Please don't stop."
7/
I put Stephanie to bed. Told her I would leave an outfit ready for the
morning, and that she should expect a surprise visitor or two early to
help her get ready for her big, first day.
"Get some sleep," I told her.
When I left the apartment building, it felt like I breathed for the
first time in hours. That had been so hot. I hadn't played like that
in over a year. Writing assignments for girls, writing stories for
them.....That was fun. Seeing their evidenciary photos, listening to
their ideas and implementing them. Reading their reports. So much
fun.....But nothing compared to this thrill. Having a girl face who
she truly is and accept it.
Poor Stephanie, I thought. She had come so close to escaping, but now
she was mine again.
I wandered the streets --- free to do that now, especially as nearby
church bells tolled the midnight hour. It was so peaceful and quiet
here in the city. A few sleeping vagrants......I dropped money into
their tattered paper cups.
One of them looked up. "Thanks, Love."
"That's okay. You'll get through this," I told him. Anything was
possible. I was living proof of that.
After a few minutes I looked up, realizing where I was. My feet had
taken me to the store where I met Deborah. I touched the dark glass.
She was obviously not there. I was still disappointed.
I wanted to share this moment with her. Not just my heat...... God,
I'd love to be in her young arms..... But the freedom.
I screamed happily, not caring who might hear. The clubs were on the
far side of the city and I was pretty much alone. I screamed again, my
body trembling, so happy to be outside. To be here, thinking about
Deborah......
I wondered if she was at home sleeping. Or if she was awake, thinking
of me..... I didn't question why she had this power over me.... Only
that I loved this sensation of being alive again.
Gert
- 04.06.2022
- 36
- 0
Brianna Benson Hedges Baby
- 3 years ago
- 44
- 0
Brianna and Jayden Episode 2 a TG Dress Shop Story
- 1 year ago
- 20
- 0
