Best Girlfriends Forever
Chris falls in love with his new roommate Shannon, who is transgender.
Shannon falls in love with Chris too, but she already has a boyfriend and
instead wants to be 'best girlfriends forever'...
* * *
Chapter 1:
"Just two more questions."
"Sure," I responded cheerfully. It seemed like Shannon and I were
connecting which was great because I desperately needed a cheap place to
stay. And besides, who wouldn't want someone as cute and beautiful as
Shannon as a roommate? Just looking at her made my heart flutter.
"First, I have a boyfriend," she said.
"Oh, of course," I said, as if it meant nothing to me.
"He comes over and spends the weekend here about once or twice a month. I
hope that's okay?"
"No problem." I tried to be breezy, but inside I was crushed. Not only
was she off the market, but now I would have to listen to her having sex
in the next room? Wonderful.
"Will you have anyone over?"
"Uh, probably not," I shrugged.
"Well, it's okay if you do. I won't mind, I promise. Okay, last
question." Shannon bit her lip and paused.
"I'm transgender," she said finally.
"You're..." I stared at her, not comprehending.
"I'm transgender. I was born a guy, but I've always felt I was really a
woman. And I thought that was important for you to know."
"But that's impossible. You're so feminine!"
"Oh, sweetie, that's the nicest thing any potential roommate has ever
said to me! But seriously, I'm a T-girl. Is that a problem?"
"No, of course not," I said, my head spinning.
* * *
And just like that, I was living with a transgender roommate.
I don't know what I was expecting, but Sharon turned out to be outgoing,
open, and aggressively friendly.
"Come sit!" she said on my first night. "Let's get to know each other
better."
"Okay." I joined her on the couch. "What would you like to know?"
Shannon draped her legs over my lap.
"Tell me a secret. Something you would only tell your bestest friend."
"A secret?" I racked my brain for something. "Like what?"
"Oh, I don't know. Something salacious. Have you ever kissed a man?"
I blushed and looked away.
"Oh my god, you *have* kissed a man! Tell me about it! Tell me all about
it!"
"Okay," I sighed. "It was at summer camp, and we were playing 'Truth,
Dare, Double Dare, Kiss, Love, or Torture.'"
"Love it!" Shannon said, eyes gleaming.
"Yeah, it's apparently something they play in Australia. Anyway, I got
'Kiss' and I was made to kiss another boy."
"Sweet! What kind of kiss? With tongue?"
I blushed even deeper. "Yes," I admitted, "with tongue."
"Did you like it?"
"Not especially."
"Well, it's hard to enjoy kissing in a big group like that. Could you
ever enjoy kissing a man?"
"I... I don't know," I answered truthfully.
"You don't know?" Shannon teased. "Would you like to find out? I've got
lots of male friends who would love to kiss a cutie like you!"
"No!" I said, a little too loudly. "Really, I'm fine. Okay, now it's your
turn."
"Me? Oh, I've kissed lots of men. Straight men, gay men--"
"No, no. I mean, tell me a secret."
Shannon thought for a second.
"Okay, I have one. But you have to promise never to tell anyone! You
promise?"
"I promise. Cross my heart and hope to die."
"Okay. Here it is. My boyfriend makes me masturbate. Every day."
"*Makes* you masturbate?" I gaped. "Really?"
"Yes," she blushed. "Please don't tell anyone. I mean, it's not like he
has a remote control or anything. It's just something he told me to do."
"But why? I mean..."
"When we first became intimate, I knelt before him, like this," Shannon
sank to her knees on the floor in front of me. "I looked up into his eyes
and said, 'Brandon, I want to be your submissive girly-girl who always
gives you pleasure. Tell me what you most want from me."
Suddenly I was aware of how hard I was. I sat up a bit, trying to make it
less obvious.
"And what did he say?"
"He said he wanted me to be always horny for him. 'Desperately horny' he
said. And so now I have to masturbate while looking at pictures of him.
Every day, except for two days before he comes to visit, when I just look
at the pictures. Would you like to see the pictures?"
"Oh, I don't know..."
"I'll be right back!" Shannon disappeared into her bedroom and returned
with a scrapbook, which she dumped into my lap.
"He's so hot, isn't he?" she sighed, flipping through pictures of
Brandon.
"He likes to take his shirt off a lot," I observed.
"No, that's me. I'm always stripping it off. Oops!"
I caught a quick glimpse of a full-frontal nude shot of Brandon before
Shannon quickly snatched the scrapbook away.
"Sorry about that," she laughed, nervously. "I... ah... you weren't
supposed to see that!"
Shannon was breathing heavily. Her eyes glazed.
"Shannon?"
"Oh hey, Chris. I, ah, need to take a break, okay? You know, to take care
of something I just remembered. Okay? I'll just be a moment, stay right
there!"
Shannon scooted to her bedroom, closing the door. Soon I heard buzzing
and muffled moans.
* * *
I spent that night thinking about Shannon and Brandon.
"Great, and their names rhyme," I muttered. "Sort of."
It was obvious from my reaction that I had a crush on Shannon. Even now,
just thinking about her legs in my lap got me going. She was so feminine
and self-confident.
My mind went back to her kneeling in front of me, looking at me with
those doe eyes and declaring her submissiveness.
Soon I was muffling my own moans.
* * *
Chapter 2:
"Why did you become a transvestite?"
Shannon looked at me for a second, amused.
"Oh sweetie, you have so much to learn, don't you? Did you lead a
sheltered life growing up?"
"I guess," I shrugged. "Catholic school. Small town."
"And now all alone in the big city? Well don't you worry, sister Shannon
will show you the ropes. Okay, to start with, 'transvestite' is for men,
or women, who like to dress in clothing of the opposite sex. 'vestite'
comes from the Latin for 'dressed'. Cross-dressers, essentially."
"Okay," I started, "but don't you like to wear women's clothing?"
"Of course I do! But let me ask you this - ignoring what I'm wearing
right now - do you think of me more as a woman or a man?"
"A woman," I said emphatically.
"You are the best," Shannon's smile was a mile wide. "Do you see the
difference now? A transsexual - or a transgender person - is someone who
is, deep inside, born with the wrong body. A man who is born in a woman's
body, or vice-versa. Does that make sense?"
"I'm sorry! I didn't mean to insult you. I didn't know..."
"Oh honey! I'm not insulted. You just didn't know the terminology. That's
all. It's something of a mission of mine to educate confused young men
from small midwest towns," she smiled. "But now let me ask you a
question: Are you a man or a woman?"
"A man?" I meant it as a statement, but for some reason the end of the
word just curled up all on its own.
"A man?" Shannon repeated, emphasizing the question mark at the end. "You
mean, you're not sure?"
"Of course I'm sure," I huffed. "I just wasn't sure what you meant by the
quest--"
Shannon stopped me with a finger on my lips.
"Shhhh, dearie," she said. She was so close I could smell her. Shampoo,
makeup, light floral perfume, baby powder. It was intoxicating. "Don't
just assume you know. Don't just think that because you have a penis that
you're automatically a man. That's 20th century thinking. Take a serious
moment to look inside yourself. Do you feel more like a man or a woman?"
"Shannon, I--"
"Please. For me."
I could see how serious Shannon was as she looked at me with an intensity
that I hadn't seen before.
"Okay," I closed my eyes and tried to settle my thoughts.
"Now ask yourself, what feels more natural? Are you more of a man or a
woman?"
To be honest, I had never asked myself these sorts of questions before. I
had always just been a boy. Growing up there was never really a question.
I guess I reached puberty later than others. And I was shy with women and
had never had a girlfriend. Did that make me different somehow? Because I
didn't constantly dream about having sex with women - did that make me
less of a man?
Something was changing, that was certain. I was masturbating a lot more,
thinking about Shannon and Brandon. I felt my heart tug a little bit
whenever I was near her.
"A man," I said, finally.
"Are you sure?"
"Pretty sure."
"Just 'pretty sure'? So there's some doubt?"
I looked at Shannon for a moment. My mouth moved but no words came out.
"Oh Chris," Shannon said, warmly, pulling me into a big hug, my face
nestled into her long red hair. "I knew I felt a connection with you from
the moment we began the roommate interview. Can you feel that doubt in
your head? That's you beginning to listen to yourself about who you
really are. Now I understand you may eventually decide that you're a man
- or more of a man than a woman - and that's perfectly okay. But just the
fact that you've heard that little voice of doubt, that means you
understand."
"Really?"
"Oh yes. I first heard that little voice in my head when I was 5 years
old. And then it got bigger and bigger until it was the only thing I
could think about. Oh sure, I pretended to be a boy all that time, but by
eleven I was certain that I was a girl in a boy's body. And then at some
point, the day after my nineteenth birthday to be exact, I just stopped
pretending. And that was that."
* * *
"Hey Chris, I have a quiz for you!" Shannon plopped down a copy of
'Cosmopolitan' at the kitchen table where I was reading the morning
paper.
I sighed. Once Shannon got something into her head like this she wouldn't
stop. She was always dragging me into new things, like eating sushi. Or
avant-garde theater.
"Why do you always have to get your way?" I sighed, putting my paper
aside.
"Because," she replied, as if she were simply entitled to it.
"Those quizzes are completely unscientific," I complained. "And wait,
aren't you supposed to be the submissive one? Isn't that what you told
me?"
"Only to Brandon," she said with a shiver of pleasure. "My man.
Otherwise, to my girlfriends, I'm the one who's in charge! Now here,
first question--"
"But I'm not your girlfriend," I protested.
"But we have the same type of relationship," she said. "Our souls are
connected, you know what I mean? But not soul mates - that's my Brandon.
I know! Soul sisters! That's perfect."
"Shannon..."
"Be quiet, sis. I finally found the perfect quiz for you: 'How much of a
girly-girl are you?' Let's get started. Now please, answer all of these
questions as if you were a girl. Okay?"
"Sure, why not?" I said sarcastically.
"Excellent. Okay, question number 1: Do you prefer indoor or outdoor
activities?"
"Indoor," I said without hesitation. Why else would I move to New York
City?
"Would you rather go to an art museum or to a football game?"
"Art museum, I guess. But that doesn't mean I don't like sports,"
"Shush, of course not. Okay, next question. Do you prefer a plain T-shirt
or a cami with lace trim?"
"What's a cami?"
"Oh, you know. It's like a T-shirt, but with thin straps that leave your
shoulders bare. Now _if you were a girl_, what would you prefer to wear?"
I squirmed a bit. If I were a girl?
"The T-shirt."
"Oh please. Would you rather see me in a T-shirt or a lace camisole?"
"Camisole," I admitted.
"So let's try again, _if you were a girl_, what would you rather wear? A
T-shirt or a cami?"
I had a feeling like she wasn't going to take T-shirt for an answer, no
matter how much I argued.
"The cami."
"Excellent. Next question, would you rather run charitable foundation, or
a bank?"
"Oh, easy. Charitable foundation."
"Of course, who wouldn't want to go to all of those charity balls?"
"Now wait a minute..."
"Favorite color, pink or black?"
"That's it? I can only choose pink or black?"
"That's right. Which is it? Pink or black?"
"I can't say neither?"
"Nope. Which is it?"
Of course, Shannon had already heard me rail against the standard 'New
York Black'. Did people suddenly become color-blind when they moved to
the city?
"Pink," I sighed.
"Of course! Okay now. Would you rather go shopping, or to the spa?"
"Shopping or Spa? That's my choice?" I grimaced. I wasn't a huge fan of
either. But as a woman? What would I rather do?
"Shopping."
"Really? Does that mean you'd like to go shopping... with me?"
"With you? You mean like..."
"...for clothes?" Shannon completed my sentence. "You know, when I'm
shopping for a new dress to wear out with Brandon? And some shoes? Or
lingerie?"
I gulped. Shopping for lingerie with Shannon?
"That would be... I mean..." I hesitated. "Yeah, I guess," I finally
said, trying to make it sound casual.
"Awesome! Okay, the next two questions are about shoes."
"Please, no!"
"'When you have to wear high heels all day long, do you prefer pumps or
sandals?'"
"Um..."
"Here, let me show you!" Shannon hopped up and fetched two pairs of shoes
from her closet.
"These are pumps," she held out a standard-looking pair of heels. "They
have a closed toe and are low cut, exposing the top of the foot. These
are high-heeled sandals. See? Open toes, and straps. More like bondage
for your foot," she giggled.
"Oh, jeez, I don't know."
"Would you like to try them on to see?"
"No! Shannon! Fine, pumps, then."
"And what are your feelings about toe cleavage?"
"Toe cleavage?" I choked.
She put on the pumps and pointed to the top of her foot where the toes
were just barely revealed.
"See? Toe cleavage."
I looked at her feet in the pumps.
"Okay, that's sexy," I said.
"So, when you wear pumps, you would want to show some toe cleavage?"
"Wait, what? Is that in the quiz?"
"No, sorry! I was just curious. Okay fine. There's just one more question
and then I'll add up your scores. Are you ready?"
"Sure. What the hell."
"If you could choose any type of man to hold you and kiss you, would it
be..."
"Shannon! Are you kidding me? I'm not going to answer that!"
"Please-please-please-please-please! It's the very last question! And
then I can sum up your score. Please! Just this one. I'll do something
super nice for you if you answer it!"
I sat there, feeling annoyed. Shannon looked at me with wide eyes,
excited and hopeful.
"What?"
"What do you mean, 'what'?"
"What 'super nice' thing will you do for me?"
"A kiss."
"A kiss?" my face lit up.
"Hold on there, Romeo. Just a kiss on the cheek. But a super nice one.
Brandon is the only man I'm allowed to kiss on the lips. That's one of
his rules."
"Hmmph," I said, crossing my arms.
Still... a super-nice kiss on the cheek... I thought about it for a
second.
"Okay, fine. What are my options?"
"Yay! Okay, here they are. Now I want you to think seriously about this!
Really internalize it. If you could choose any type of man to hold you
and kiss you, would it be..."
Shannon looked me straight in the eyes.
"One: An all-American baseball player with a charming grin. Two: A
Latino hunk with a smooth chest. Three: A dashing Englishman with
tousled hair. Or Four: A stern fatherly type who smells of pipe
tobacco."
"Oh god, I don't know. The Latino, I guess--"
"Stop! Please, Chris, you haven't really thought about it. Now close your
eyes. Okay?"
I closed my eyes as instructed.
"Good. Now imagine yourself in the arms of each one." Shannon went
through each option slowly. "The baseball player with the charming grin."
She paused. "Okay? Now the Latino hunk with the smooth chest," another
pause. "The Englishman with the tousled hair. The fatherly type smelling
of pipe tobacco."
"Have you imagined each one in your head?"
"Yes," I said.
"Okay, now imagine that his arms are around you. They're strong and
masculine. He works out, doesn't he? Now you look up, into his eyes, and
he leans forward and... kisses you."
I opened my eyes and then immediately looked away.
"Who was it? You did think of kissing one of them, didn't you? Who? Who?"
I mumbled something unintelligible.
"I'm sorry, Chris. Who was that? I couldn't hear you. Who did you imagine
holding you and kissing you?"
"The baseball player!" I said, exasperated. "Are you happy? It was the
baseball player."
"Happy? I'm ecstatic! That's who I imagined too! Brandon is *so* like the
baseball player! See? I told you we were compatible souls! Now wait,
while I add up the score... okay, ready?"
"Sure, why not. How much of a girly-girl am I?" I asked, resigned to my
fate.
"On a scale from 1 to 10, you're a 9.5!" she said. "It says here,
'Congratulations on being exceptionally girly-girl! There is not an ounce
of tomboy in you! You want nothing more than to wear pretty things to
show off for your man and do all things feminine!"
"Great."
"Wait, there's more! It goes on to say that if you are, in fact, a man,
then you should reach out to the closest transgender person you know and
get the help you so desperately need to bring our your inner girl to the
surface, since that's what you so obviously want!"
"It does not say that!" I said, snatching the magazine away from her.
"Hey, wait a minute! There's no quiz here at all! You made it all up!"
"I'm sorry, I'm sorry!" Shannon jumped into my lap and wrapped me into a
hug, holding me tight.
"Wha--? I mean, why did you...?"
Shannon shrugged. "I just wanted to know the answers, I guess. I wanted
to know, if you could be - like my former roommate - you know - my BFF -
my roommate sister - and if so, then what kind of girl you would be like.
And also, you know..."
"You know... what?"
"It was important for me to know the answer to that last question. Well,
not the answer so much as knowing that you were open-minded enough to
really consider it. You know, being in a man's arms. And you did, didn't
you? You really thought about it, didn't you?"
"Yes," I admitted. "I really did consider it."
"And it wasn't completely icky, was it? I mean, you don't have to tell me
you're all hot for men or anything. All I want to know is that the idea
of kissing a man - you might imagine, I mean if you were a woman - or
transgender like me - you could at least imagine why I might like it so
much? Being in a man's arms? Kissing him?"
"Yes... I... I mean, no, it's not completely icky. If I were transgender,
like you, yes - I could imagine how kissing a man might be alright."
"Just alright?"
"Okay, fine. More than alright. Sexy, even. *If* I were a woman. Or
transgender," I added quickly. Having Shannon in my lap and so close was
causing my brain to short-circuit. I was getting hard.
"Oh, Chris. I'm so glad. Thank you - you don't know how much that means
to me - to know that my roommate doesn't think less of me for being with
a hunk like Brandon. Now do you want your super-nice kiss?"
"Yes, please."
"Very well."
Shannon pressed her body against me. Her lips started with my ear, which
they gently nibbled, before they moved to my cheek where she gave me a
warm, wet kiss.
"Thank you," I sighed. "That *was* super nice. Brandon is a lucky guy."
"He is, isn't he? So hey, are you busy this afternoon? How 'bout we go
shopping?"
* * *
"Check out my Christmas present from Brandon," Shannon grinned. She held
up a plastic card between her long, delicate fingers.
"No way!" I said, astonished. "He gave you a credit card?"
"Isn't it the most awesome gift ever? Of course, I can only use it for
clothes, and only from certain stores."
"Does it have a limit?"
"Yes, but it's like five thousand dollars. I've never even come close."
"Honey! You aren't really trying."
"I know, I know. And he's always telling me to buy more. But I love him!
I don't want to abuse his generosity. Besides which, I have to be careful
about what I buy because my closets are so small."
Shannon and I had already spent about four hours shopping. At first all I
did was tag along. But soon Shannon was dragging me into the decision
making process.
"Don't you think this makes me look washed out?" she would ask. "How
about compared to this?"
Or, "Are the frills too much? Too tacky? How about compared to this?"
It was fun, actually. Initially I thought she was just being nice. Then
later I began to wonder if she was trying to educate me on fashion in
general. Especially when she started talking about things like
proportions and color matching.
"I know! I can buy something for you!"
"What, on Brandon's credit card?"
"Sure! Why not? I've bought things for my friends before. He said that
was fine, as long as it was women's clothing."
"But I'm a--"
"How about new underwear? I've seen your briefs. They're so thread-bare
you can see through them. Here, let's get you some panties. They'll be so
much better for you."
"Panties?" I gasped. "Are you kidding?"
"But why not? It's what I wear!"
"But you're a woman!"
"Chris!" Shannon squealed, dropping everything on the floor and clutching
me into a vice-like hug. "Oh my god, I can't believe... you are the best!
Just the best!"
"Wha... What did I say?"
"You called me a woman!"
"But, you are!" I protested, confused.
"Oh my god, you don't know," Shannon was breathing deeply, her arms
around my neck, still holding on tight. "I'm transgender, remember?"
"Oh, right," I finally understood. "I'm sorry-- I guess I had forgotten."
"That's the last thing you have to apologize for. Okay, it's settled. Now
I *have* to buy you something. How about these? Nylon, with some lace
trim?"
"Shannon..."
"Please, let me buy these for you. Please??"
"But why?"
"Because... because Brandon wants me to spend more money on clothes.
Because you need new underwear. Because I want to thank you for going
shopping with me. Because it's no fun going shopping unless you have
something of your own when you get home. And because I really, really
just want to buy something for you."
"Can't we just go someplace else and buy me some male briefs?"
"No, not with Brandon's credit card. Besides, I don't want to buy you
male briefs. I want to buy you *these*. Here, just let me buy them for
you and you don't have to wear them if you don't want to."
"But why do they have to be, you know, panties?"
"Because I want them to be special! If I were to buy you some male
briefs, well *yuck*, first I'd feel like I was your mother, and not your
girlfriend."
"Girlfriend?" my eyes went wide.
"A friend who's a girl! Honestly, you're impossible. Like two roommate
girlfriends. And besides, if you put on briefs from me it will be just
like any other underwear you've always worn forever. But not these! If
you put these on, you'll *know*. "
"Know what?"
"You'll know that you're wearing a gift from me, silly. A gift that no
one else on this planet would dare to give you."
"You really want this, don't you?"
"I do. I don't know why it's so important to me," Shannon shrugged. "But
it is."
"Okay, fine," I said. "You can buy them for me. But I won't promise to
wear them."
"But you'll think about it? I mean, you'll seriously consider wearing
them?"
Shannon reached out and grasped my hand in hers. Her touch was soft and
electric.
"Sure," I said, thrown for a second. "I mean, yes. I'll seriously
consider wearing them. For you."
"And you'll at least take them out of the package and put them in your
dresser drawers?"
"Shannon!"
"For me?" She squeezed my hand. "I don't want you to just throw the
packages into the back of the closet where you'll forget about them.
Please?"
"Alright, fine. I'll unpack them and put them into my drawers. But that
doesn't mean that I'll wear them."
"But you'll seriously consider it. Right? You agreed."
"Yes, I'll consider it."
"Thank you," Shannon gave me a quick peck on the cheek. "Thank you *so*
much. And, you know, if you get bored of just wearing panties all day,
here: I'll get you these bras, this slip, and this nightgown as well!
Feel free to just wear them around the apartment. I won't mind!"
"Shannon!"
"Just kidding! Sheesh, don't be so sensitive!"
But although she said it as a joke, Somehow the bras, the slip, and the
nightgown all found their way into my shopping bag, along with a dozen
(!) pairs of new panties.
* * *
Chapter 3:
"So, are all of my 'gifts' unpacked and put away?" Shannon asked,
grinning.
"Yes," I sighed.
"*All* of them?"
"Yes, *all* of them. Even the slip, the bra, and the nightgown. Which I
never agreed to!"
"Awesome! You are so great to put up with me. Whatcha' doin'?"
Shannon settled into the sofa beside me. I tilted my laptop so she could
see.
"We're starting up this new service to do big data analysis for our
customers. So I'm launching a big-data array on our private cloud and
loading up their data to see what I can do."
"Cool, I used to do that."
"What?" I looked at her, amazed. "But I thought..."
"... that I was just a receptionist? Yeah, that's what I am now. But I
used to be the head data scientist for Citibank."
"No way!"
"Yeah way."
"But then, what happened?"
"Well..." Shannon hesitated, "Brandon didn't like it. He said it took me
away from focusing on his needs. And so he made me quit my job."
"Shannon!" I said, shocked. "Head data scientist for Citibank! That's
like-- you must have been pulling in, like..."
"I know. It was a lot."
"How could you let Brandon do that to you? What about your career?"
"I told him I'd do anything for him," she shrugged. "That's what he
wanted, and so I did it."
I was aghast. "No one should make you choose between a career and a
relationship. That's just not right! Leave him!" I exclaimed,
impulsively. "Leave him now! Just... be with me! I won't make you quit
your job for me. I think it's amazing that you're so smart!"
"Oh, Chris, that's such a sweet gesture," Shannon said, hugging me. "But
I'm afraid that you just can't give me what Brandon does. I mean, I do
love you--"
"Love me?" I asked, my heart skipping a bit.
"Oh please," she whacked me playfully on the arm. "Of course, I love you!
You know, like a sister-slash-roommate," Shannon giggled but then turned
serious.
"But not like I love Brandon," she continued. "I mean, he gives me
something I just can't get anywhere else. Maybe you would need to be in
my position - as a transgender girl with a strong, straight male
boyfriend to really understand. You're my roommate - and these last two
weeks getting to know you have been great! But I could never leave
Brandon."
"But he made you quit your job. How could you let him do that to you?"
Shannon held my hand in hers, gently massaging it.
"It's like a drug," she continued. "I'm submissive and he's dominant, and
I just look into his eyes and I just want to do what he tells me to do."
"But he's only here, like every other month."
"He's a director in a multi-billion-dollar multinational corporation. His
office is in London. I couldn't ask him to leave that for me."
"But he made you quit your job for him! It's not fair."
"But Chris, I'm so much happier now! When I worked at Citibank, I was a
mess. I threw up in the alley on the way home I was so stressed out. I
could barely eat. I was down to 97 pounds. Of course, there was a lot of
other shit going on - but the truth is, I'm in a much, much better place
now. My life is so much simpler. I concentrate on beauty, peace, and
happiness - and not that relentless push for accomplishment."
I just sat there for a while, not knowing what to say.
"I just wish there was some way I could help you to understand," she
said, finally.
"Me too."
"And it shouldn't be that hard," Shannon continued. "I think we're a lot
more alike than you realize. I sensed it from the moment we started the
roommate interview. I felt a connection... like you and I were long lost
sisters, separated at birth."
She paused.
"Do you mind if I try an experiment?"
"An experiment?"
"Yes, an experiment. To demonstrate what I'm talking about. Why I'll
never leave Brandon and why I've quit my job for him. So that you'll
realize what I'm all about."
"I don't know..."
"Okay, here goes. For the next hour, you have to do everything I tell you
to do."
"Everything?"
"Yes, everything. And you must do it without hesitation, and you must do
it just because I told you to do it and because you want to please me."
"Of course! I would do anything for you," I blurted out, and then blushed
at my heartfelt admission.
"Oh sweetie, that's perfect! Now are you ready? Just 60 minutes, and then
after that if you still don't 'get it', then we'll just have to agree to
disagree. Okay?"
I took a deep breath.
"Okay."
"Okay. Time starts... now. Let's begin with a question. Tell me
truthfully, do you have a crush on me?"
"Yes," I admitted. "Is it that obvious?"
"Thought so," Shannon smiled warmly. "That will make all this so much
easier. Okay, first command: Kneel before me. And remember, you
promised!"
I sank to my knees before her, feeling silly.
"Very good. Now say that you love me."
"I love you," I muttered, blushing and looking to the side.
"Tell it to my face," she commanded. Holding my face between her hands,
Shannon turned my head so I was forced to look her in the eyes.
"I love you," I repeated. I was trembling.
"Now tell me that you love me and you'll do anything for me."
"I love you and I'll do anything for you."
"Excellent. Now go do the dishes."
"Uh...okay." This was not what I had expected. I moved to get up.
"No Chris, not like that!" Shannon rolled her eyes.
"Not like what?" I asked, confused.
"Chris, why are you going to do the dishes right now?"
"Because you asked me to."
"No, that's not right. Try again."
"Because... because you *told* me to?" The trembling returned.
"You're so smart! That's almost right, but the emphasis is not quite
right."
"Because *you* told me to?" I stammered, my heart beating hard now.
"Exactly," she smiled. "Are you beginning to understand now?"
"I... I don't know."
"Well, go do the dishes anyway. And remember, you're doing them because
*I* told you to."
* * *
Fifteen minutes later and I was back.
"All done? Good. Now tell me something - did it feel different, doing the
dishes for me?"
"Different?"
"Yes, different. You know - more... interesting?"
"Yes," I admitted.
"Were you thinking about me as you did them?"
"Of course I was. How could I not?"
"Did it make it better to know that you were doing them on my orders?
More fun than just doing the dishes?"
"I guess so."
"You guess?" Shannon teased.
"Okay, no. I mean yes. It was much better, doing them because you told me
to," I finally admitted. "It was... sexy."
"Awesome! This is going so well! Okay now I want you to go into your
bedroom and strip naked. Then put on a pair of your new panties and a
bra. Then get dressed again and come back here."
"What? Hey, this was not in the agreement."
"Chriii-iisss!" she mocked me in a sing-song voice. "You said you would
do everything and anything I waaannnted, didn't you? Okay then, I am
telling you to go and swap your male underwear for panties and a bra. Now
scoot!"
* * *
Naked, I held the pair of panties in front of me and debated what to do.
Something inside me felt like I was crossing a line -- a line which might
be difficult to uncross.
'Why do I have to put on panties?' I fretted.
But I knew the answer, of course. It was because Shannon wanted to teach
me a lesson. A lesson as to what it felt like to be a transgender female.
'It's for Shannon,' said the little voice inside my head. 'You promised
to do what she told you to do, and she told you to do this. You pride
yourself on keeping your promises.'
But where will it lead? I worried. What would happen if she asked me to
wear them again? Would I? Just because she asked me too?
I thought about that for a second and realized that I would. If Shannon
stood in front of me, held my hands, and looked into my eyes and asked me
outright: 'Please Chris, would you please wear panties for me? It would
make me feel so much closer to you.'
Yes, I would probably do it. Something about her made my heart melt.
I slowly slid the panties up my legs. They felt so flimsy and light.
After I pulled them up tight I stroked my fingers across the bulge in
front, shivering at how I could feel even the lightest touch.
And now for the bra. Why was my heart beating so hard? I examined the
hooks in back for a second, and then slipped my arms into the straps.
After a few tries, I finally joined the hooks with the loops. But then it
didn't seem tight enough, so I went a row tighter. But even that wasn't
just right and so I went to the tightest row.
There, *that* felt right.
Was I hard? Damn, I was! Where the fuck did that come from?
'It's because you like it,' said the small voice in my head. 'You like
wearing panties and a bra, and you like doing it for Shannon.'
Confused, I quickly put my jeans and flannel shirt back on.
* * *
"Here she is!" Shannon said, wickedly. "What took you so long? Have a
hard time hooking up the bra?"
"A little," I admitted, blushing at being called a 'she'.
"Well, practice makes perfect!" she teased. "Now come here and I want to
just add a couple of things - to complete the sensory experience, you
know? Now here, sit next to me."
Hesitantly, I walked over and sat beside her on the couch.
"You're shaggy, which is nice, but let's add a clip." The clip kept my
hair to the side and out of my eyes. It had a pretty pink flower on it.
"Sweet!" Shannon enthused. "Now for some lipstick."
"Lipstick? No, I won't!" I stood up.
"Chris, please!" Shannon pleaded, reaching for my hand and pulling me
back down to the sofa. "You'll feel so girly with lipstick on - trust
me."
"But I don't want to feel girly!"
"But I want you to," she said. "And I still have twenty minutes on the
clock. I am telling you to be a nice girl and let me paint your lips with
lipstick. Besides, it's no big deal. After the hour is up, you'll just
wipe it off."
"But Shannon..." I whined. "Why?"
"Because I want you to. That should be enough. Now here, hold still."
Shannon first outlined my lips with a lip liner pencil, and then filled
in the rest with some dark red lipstick. It felt strange, thick, and
greasy on my lips, and it smelled. Like makeup.
"And finally, some perfume."
"Please..." I whined.
"Hush!" She pulled out a bottle and used the stopper to dab some on my
neck (by both ears and in front) and on both wrists.
"There! Now how do you feel?"
"Ridiculous," I said, sourly.
"Now none of that! Close your eyes, and settle your breathing. I'm going
to count to one-hundred and all I want you to do is experience all of
your feelings. Your new panties, the straps of your bra, the lipstick,
the hair clip, and the perfume. Just take it all in. Okay? Now here goes.
One, two, three..."
Her counting went silent, leaving me alone with the feelings, smells, and
thoughts.
"There, One Hundred," Shannon said. "Open your eyes and tell me how you
feel."
I opened my eyes and looked at Shannon. On her face was an expression
of... hope? Pleading? Wishfullness?
"I... I..." I started, but couldn't seem to get the words out.
"Go ahead, sweetie, you can say anything to me," Shannon said, again with
such expectation in her voice.
"It feels nice," I said, giving in.
"Oh, I'm so glad!" Shannon said with a squeal, pulling me into a big hug.
"I'm... I'm thrilled - you have no idea!"
But the truth was that I honestly didn't know how I felt. I knew what
Shannon wanted me to say, and I so wanted to make her happy, that I told
her that it felt nice. But inside, I was confused. I was self-conscious.
I felt like a fool, but also... it wasn't all bad. I had butterflies in
my stomach - or was that because of Shannon? I felt scared, and on edge.
"I just new you would like it!" continued Shannon, giving me a kiss on
the cheek. "I just knew it! We're connected. Our souls... are connected.
I am sure of it. It does feel nice, doesn't it?"
"Yes," I lied, feeling myself sink deeper.
"And you feel so nice and... feminine? Don't you?"
I thought about that for a second. The perfume, the hair clip, the
panties...
"Yes. I suppose. I mean, how could I not?"
"Okay, now we're running out of time and I still have a couple of things
I need to do with you. First, I want you to do something more for me...
something that a wife or girlfriend might do. I want you to make my bed.
"Make your bed?"
"Yes! I want you to do some housework. As if you were a submissive little
wife. Housework as a girl. Okay?"
"Okay," I said, getting up.
"And scurry, scurry! Quick like a bunny. We're running out of time."
And so I scurried into her bedroom and took a look around. What a mess!
Clothes and papers everywhere. She really does need a wife, I thought to
myself, if only to keep this place clean!
Realizing I didn't have much time, I simply moved all of the clothes
(including used bras and panties!) and other items (papers, her laptop, a
sticky vibrator (!) ) off the bed.
And all the while I could smell my perfume, feel the hair clip tugging at
my hair, and feel the straps on the bra and my male parts in the nylon
panties -- all as I moved about cleaning up. And as I was doing the work,
something inside of me shifted, just a bit.
'You're doing this for Shannon' I thought to myself, 'because she told
you to do it.'
'And it's not so bad, is it?' the little voice in my head was talking
again. 'I bet you wouldn't mind making Shannon's bed every day. Isn't
that right?'
Now that the clutter on the bed was cleared I could actually start. I
straightened out the covers, tucked in the corners, and fluffed the
pillows, making everything nice and neat.
And then - and I swear I don't know what came over me - I took her
pillow, the one she lays her head on every night, and placed a big red-
lipstick kiss on it.
I fluffed the pillow one last time for good measure and put it back,
pleased with myself. 'She'll see that when she goes to bed and think of
me,' I thought to myself, with satisfaction.
But then I took another look and realized - 'What the fuck??' What the
hell had I just done?
"Are you done in there?" Shannon called out from the living room.
"All done," I said, resigning myself to the consequences of the kiss on
the pillow. I had no idea how Shannon would react to it.
"Excellent," she said, as I walked back into the living room. "Did you
have fun making my bed?"
"I... yes," I admitted.
"It's nice being a girl and doing housework, isn't it? For someone
special?"
"I suppose."
"And the more girly you are, the nicer it gets."
"The more girly...?" I halted, with a shiver.
"Just teasing," she giggled. "Now, come here, there's one last thing I
want to do."
Shannon motioned me over to the sofa, but this time she wanted me to sit
in front of her (her sofa is quite deep). When I was situated, she hugged
me close from behind, scooting me back so that my back was fully pressed
against her with her legs around my hips.
"Hey!" I said. Shannon had reached around me and had unbuttoned the top
button of my shirt. "Stop that!"
"Oh, hush," she said, slapping my hands away. "I thought you'd enjoy
having me undress you! Now be a good girl and keep those hands in your
lap, young missy!"
My hands fluttered about for a second before they finally sank into my
lap, allowing Shannon to finish unbuttoning my shirt. She pulled the two
halves aside, exposing the mint green bra I had put on.
"Beautiful," she whispered, placing her hands on my breasts and squeezing
gently.
I squirmed in her arms, becoming fully erect in my panties.
"Please, Shannon," I fussed. "Isn't the hour up?"
"Just a few more minutes," she said. "Just enough time."
Shannon reached to the end-table and then placed something in my lap. It
was the scrapbook of her pictures of Brandon.
"Open it," she whispered, her breath hot in my ear.
On the first page was a picture of Brandon, smiling, in a tailored suit
and tie.
"He's so confident," Shannon said, as we looked at the picture together.
"Look at how crisp and put-together he is. Confident and sure of himself.
Cocky. Now turn the page."
In the next picture he was in jeans and a T-shirt, relaxing on a sofa,
the same one we were on. Shannon's fingers began to trace gentle circles
around the seams of my bra, making me tremble in her arms.
"See how comfortable he is? When he wants something he just asks for it.
No - I take that back. When he wants something, he just tells me to do
it. There are no games, no questions. He just says 'do this' and I do it.
I do it because I want to. For him. Because he deserves it. Don't you
agree? Didn't you find it nice to follow orders, when I gave them to
you?"
"Yes."
"Now look at Brandon. Imagine him telling you to do something. He says
'Christine, clean up the bedroom.' Can you imagine him saying that to
you? Can you imagine him looking you in the eyes and telling you to make
the bed?"
"Shannon, please..."
"You don't have to say you want it. Just tell me you can imagine it."
"I... I can. I can imagine it."
"Excellent," she purred. "Now turn the page."
On the next page were pictures of Brandon in just a pair of tight briefs,
showing off his toned body. Shannon's fingers found my nipples through
the silk of the bra and started gently pinching them.
"Please Shannon," I squirmed. "Please, I want to stop..."
"Now look at how manly he is," she continued, ignoring my protestations,
her breath on my neck giving me goose bumps. "He's all male, isn't he?
And let me tell you, when you're in his arms - you feel safe and yet
vulnerable. So safe, vulnerable, and girly - like all you want to do is
dress pretty for him and hang on his every word, and laugh at his jokes,
and do everything in your power to make his life easy and pleasurable.
You want to be his playmate and his helpmate. And you want to do more...
Now turn the page."
And now Brandon was standing, fully naked. His cock was mostly soft,
hanging down. He was smiling down at the camera, a smile of a man who
knew he would soon be getting exactly what he wanted.
"Shannon..." I moaned.
"Now do you see why I quit my job? Not only is Brandon strong and self-
confident, but I look at that, and all I want to do is worship him. Oh,
I'm getting so horny! All you have to do is place a wet kiss on that cock
of his, and it starts to grow. And soon he's filled with *lust*. Lust for
you because you're so sexy - for him. Lust for your mouth with its red
'fuck me' lipstick. Imagine sinking down on your knees before him. You
can smell his manly musk and it is intoxicating. And you lean forward and
place your lips right on the tip..."
"NO!" I shouted, standing up abruptly, knocking the scrapbook to the
floor. "STOP IT! Shannon - I - I - Okay, I understand why you would quit
your job for Brandon now. Okay?? It's perfectly clear! Thank you! But, I
just can't... I'm just not... It's too..."
Without finishing the sentence, I stomped to my bedroom and slammed the
door.
* * *
About two hours later, I heard Shannon gently knocking on the door.
"Sweetie?" she asked, softly. "I went too far. I'm so sorry. Please come
out. I've made some tortellini and I've opened a really expensive bottle
of Italian Super-Tuscan. Chris? Can you hear me?"
"Yes," I grumbled, through the pillow I had planted face into.
"Okay. Well you take your time and come out when you're ready."
My anger had long ago dissipated, leaving me feeling twitchy and
confused. I really couldn't even process what had happened to me or the
reasons why I had blown up like that. Shannon had touched something raw
and powerful inside of me - but what was it? What did it mean?
I took the pillow off my face and lay back. Obviously I'd have to go out
there at some point. I couldn't just hide in my room forever. Worse, the
smells from the kitchen made me realize how hungry I was.
"Might as well get this over with," I sighed, rolling out of bed. I was
back to wearing my ordinary clothes - standard male briefs and no bra. I
had done my best to wipe the lipstick from my face but my lips still
looked red to me. Perhaps they were just raw from so much rubbing.
"Hey," I said, entering the kitchen.
"Hey," Shannon said, looking up.
It broke my heart to see that she had been crying and was now trying her
best to keep it all in and smile.
"I'm so sorry," Shannon repeated. "I... I don't know what got into me! I
never should have... it was so wrong. I never meant to make you feel
uncomfortable."
"Thanks," I shrugged.
"I'm so sorry!!" Shannon repeated, dissolving into tears.
"Hush, hush! It's okay," I pulled her into a hug and felt her face nestle
into my shoulder. "It was weird, but I'm over it. Really, it's okay."
"I just... I wanted... I mean... I just feel so close to you! Like
sisters. I'm sooo *alone*" she wailed, holding me tight. "My last
roommate - she died in a car accident. Did I tell ever you that? It was
horrible and I was so depressed, I even went back to cutting myself..."
"Cutting?" I gasped.
"I-I've been seeing someone, and we've got it under control. I'm sorry, I
shouldn't have said anything. Now you think I'm a crazy woman toooooo!"
"No! Not at all. It... I've heard... I mean..."
"But then you showed up! I had interviewed at least 40 people. Did you
know that? And you were the only one I wanted. The *only* one! I saw you,
and when we talked, I felt better. I've been so happy since you showed
up. You know? Like now I have someone I can share my life with, all the
great parts and all the crazy parts..."
"But you have Brandon," I said.
"Of course I do, I know. But I can't share *girl* things with him! I
can't unload all of my problems on him - he doesn't want that. I need a
BGFF - a best girlfriend, *forever*. And I know you're a guy, and I'm so
sorry for pressuring you, but please don't leave meeee!!" Shannon
collapsed into racking sobs again, hiding her face in my chest.
"Don't leave me, please don't leave me," she repeated over and over, her
tears soaking into my shirt.
"Shhh, shhh", I did my best to sooth her, stroking her back. "Of course
I'm not leaving you. You... You're so amazing. I... I'm honored you feel
you can trust in me - to tell me all those things. Really."
"Really?" she sniffled.
"Really," I said.
"Will you be my BGFF?"
"Your BGFF?"
"I'm sorry. I meant my BFF. My Best Friend Forever."
Shannon looked me in the eyes, and even I could feel there was a deep
connection between us. It was exactly at that moment when I knew my life
would change forever. The pivot point. For better or for worse, we were
going to be a part of each other's lives from now on. I was sure of it.
"Yes," I said, too overcome to say anything more.
"Forever? BGFF's forever?"
"Yes."
"Say it. Tell me. I need to hear it. Please?"
"I... Oh, Shannon," I was almost crying myself now. "Yes. I will be your
best friend, forever. Through thick and thin. For better or worse.
Through good times and bad times."
"Oh Chris! Thank you! I can't tell you how much this means to me... Let's
promise to always talk to each other, okay? Every day, okay?"
"Absolutely!"
"And never, ever, ever tell a lie. Can you promise to always tell the
truth, as best you can? To always tell me exactly what you feel and to
answer every question as honestly and completely as possible?"
"Of course, Shannon," I said, feeling a lightness flow through me,
lifting me up.
"We have to tell each other *everything*, okay? No secrets, no lies, no
hiding, no hesitation to tell each other *anything*. That's what BGFFs
are all about. That's what I want, is someone who I can confide in
completely and honestly and trust with my life."
"Oh my god," I said, astonished. "That sounds... wonderful. I've never
had a friend like that," I admitted. "I grew up with two older brothers
and a bratty younger sister. I was picked on by everyone because all I
wanted to do was work on computers... I've never really had a close
friend."
The realization just slipped out, but as soon as I had uttered the words
I realized how true they were, and how devastating.
I sank to my knees, and this time it was Shannon who was comforting me as
I cried softly, my head in her lap.
"There, there," she said, stroking my hair. "There, there, my darling
Chris. It will be okay. You have Shannon now, and she's never letting you
go. BGFFs forever."
* * *
It was about three thirty in the morning when I woke up with a start.
Shannon and I had spent the entire night talking until about one,
lounging on the sofa in each other's arms, eating tortellini and drinking
wine. She told me all about her prior roommate, her shrink, and
everything she had been hiding from me. For my part, I told her about my
upbringing, the bullying I had been subjected to (by my brothers and
their asshole friends) and my dad's struggles with alcohol.
It was wonderful and cathartic. I think I realized what true love was,
that night.
Finally, Shannon dropped off to sleep in my lap, and not knowing what to
do, I picked her up and gently put her into bed, covering her with a
light blanket, and then went back to my own room.
I lay there, looking at the ceiling. I could hear Shannon asleep in the
next room, snoring. Light from the streetlamp came through the window,
and I could hear an occasional taxi from 8th avenue.
My eyes drifted to my chest of drawers and I knew immediately what I
needed. In a trance, I slipped out of bed and opened the top drawer where
I had stored all of feminine things that Shannon had bought me. I felt my
skin tingle as I touched them, feeling the silky nylon fabrics and sheer
lace trim.
I pulled out the mint-green pair I had worn earlier. Slipping off my
briefs and T-shirt, I stepped into the panties becoming hard as I pulled
them on. Next I slipped my arms into the bra straps and (more quickly
this time, practice does help) fastened it behind my back.
Back in bed I used one hand to stroke my nipples as the other lightly
traced over the nylon covered bulge between my legs. But I wanted
something more, and, as soon as I realized what it was, my heart began
thumping hard in my chest.
"I can't possibly be considering this..."
I lay like that for a while, knowing exactly what I wanted, struggling
with what to do.
"Screw it," I finally said, getting up.
As quietly as possible, I opened the door and stepped into the living
room. It was still there, just like I knew it would be.
Shannon's scrapbook.
I looked quickly towards her bedroom. The door was ajar, but I could
still hear her breathing heavily. Shit, what the fuck was I doing?
Back in my own bed, I flipped slowly through the scrapbook, gently
stroking myself. In addition to pictures of Brandon in various stages of
undress, there were also pictures of Brandon plus Shannon, with her in
his arms, with the two kissing, and with him squeezing her breasts from
behind, and in every one Shannon was the very vision of an adoring,
lustful, completely committed sexual partner.
The last few pages were entirely Brandon, nude, horny and rarin' to go.
"Nooo..." I whimpered, unable to tear my eyes away. "What is wrong with
me?"
I turned the page to a close-up of his member, stiff, large and
circumcised.
"Oh god, oh stop..." I groaned, tensing up and climaxing into my panties,
lost in a sexual fog and down the rabbit hole.
* * *
Chapter 4:
"'Sup", said Brandon.
"Hey, nice to meet you. Shannon's told me all about you." I reached out
my hand, but Brandon didn't move and just looked at me. Eventually I
pulled my hand back, flushed with embarrassment.
Shannon's boyfriend had arrived late. I learned he was in the apartment
when I heard the bed frame bumping against the wall accompanied by
groans, grunts, and "Oh God, yeah baby, that's it, just like that, oh
yeah, I'm coming!" from the next room.
It was pure torture.
Now here he was, Saturday morning, and something was wrong.
"Shannon told me all about you too," Brandon said. "But she missed one
rather important detail."
Brandon turned to look at Shannon, who was sitting at the breakfast table
looking terrified.
"What do you mean?" she said, in a high-pitched squeak.
"He's a guy," Brandon said.
"Of course I'm a guy," I said, trying to help out Shannon as best I
could. "Is that a problem?"
"Yes, it's a problem. Shannon, you never told me your new roommate was a
dude."
"I didn't?" Shannon said, flustered. "But I've talked a lot about
Chris..."
"Right, 'Chris' as in 'Christine' or 'Christina' not..." Brandon looked
at me.
"Christopher," I supplied.
"Right, Christopher. See?"
Shannon looked back and forth between Brandon and me, panic etched on her
face.
"But, I thought you knew! I really thought it was..." she said, her hands
fluttering to her wrists.
"Christopher, could Shannon and I have some privacy?" Brandon asked, his
tone bordering on demand.
"Sure," I said.
"But Brandon," Shannon whined, "Chris hasn't had breakfast yet!"
"He can have breakfast at the diner on the corner," Brandon said, looking
me straight in the eyes. "You don't mind, do you... _Christopher_?"
"No, of course not," I said getting up and grabbing a jacket.
"Probably best if you don't come back until after dinner," Brandon added.
I looked at Shannon, who was blushing bright red and staring straight at
the floor like a repentant schoolgirl.
"Shannon?" I asked, gently.
"Please Chris, I'm sorry. Yes, I think that would be best."
* * *
With nothing better to do, I went to my office in the Bloomberg tower.
The cubicle farm was mostly empty, just me and a couple of operations
guys.
"What are you doing here on the weekend?" Brijesh, my boss, asked.
I shrugged. "I had other plans, but they fell through. Though I'd try and
get caught up a bit. What are you doing here?"
"Moral support for the deployment. We're almost done."
"Cool."
Around nine I figured enough time had passed, so I packed up and took the
subway home.
* * *
"Where have you been?" Shannon cried, flying into my arms as soon as I
entered the door and pulling me into a desperate hug. "I was so worried
about you!"
"In the office," I shrugged. "I was waiting until I thought it was safe
to come home. What happened to you?"
Shannon had a bright purple bruise on her cheek.
"It's nothing," Shannon winced and pulled away, looking to the side, her
hand reaching up to hide it. "Listen, we need to talk," Shannon pulled me
over to the sofa in the living room.
"That bastard! He hit you, didn't he? Shannon! You've got to leave him!"
"Chris, stop that! It's not like that at all. This isn't Brandon's
fault."
"Oh come on, I may be naive, but I'm not that naive. Have you been to the
hospital to get that looked at?"
"I'm telling you, you have it all wrong."
"Shannon!"
"Fine, you want to know what happened? What exactly happened?" Shannon
blushed three shades of red. "We fought. About you. And then we had sex.
Okay? That happens a lot with us. We fight, and then we have sex. And he
can be a little rough, okay? He was doing me doggie style, and thrust in
a bit too hard, and banged my face against the headboard. Satisfied?
That's what happened."
I sat back, stunned. Was that really what had happened? Or was Shannon
lying to protect her boyfriend?
"Now can we please stop talking about my bruise?" she implored. "We have
more important things to talk about."
"More important things?"
"Yes, much more important," Shannon suddenly reached out and held my
hands in hers. "Are we still BGFFs? Best girl-friends forever?"
I saw tears forming in her eyes.
"Yes," I responded quickly, and without thinking. "Yes, of course. Best
friends forever."
"So then you'll tell me the truth - the absolute truth - when I ask you a
question?"
"Of course, anything!"
"When was the last time you wore the panties that I gave you?"
I jerked back, shocked. That was the last question I expected her to ask.
"Uh... I..." I sputtered.
"Chris! The truth. You promised!"
"Last night," I said, blushing furiously. "I wore them last night."
"Last night?" Shannon asked, excited. "You wore panties last night? While
listening to Brandon fuck my brains out?"
"Yes."
"And did you masturbate while wearing them? Did you masturbate while
wearing panties like a girl and while listening to your girlfriend get
fucked by her boyfriend?"
"Please Shannon!" I moaned. "Please! Why are you asking me these
questions?"
"Because, it's important, Chris!"
"But why? Why is it so important?"
"Because... Because Brandon has told me that you can no longer be my
roommate."
The news hit me like a sledgehammer. I sank down into the sofa.
"Oh my god... Oh no, Shannon!" I felt my eyes begin to well up.
"Unless..." she hesitated.
"Unless what?" my heart leapt with hope.
"Unless..."
"Oh no..."
"Unless... you transition to become a transgender woman. Like me."
"Ohhhhhhhhhhh, CRAP."
"I know, I know!"
"Where the hell would Brandon have gotten an idea like that?"
"Because," Shannon shifted uncomfortably, "I sort of told him that's what
you wanted."
"SHANNON!"
"I was desperate! I didn't know what to do. You and I are meant to be
together! We're soul-sisters, I just know it! And so, I showed Brandon
what was in your dresser-drawers. And I showed him the nightgown and the
bras. And I told him... well I told him that you had confessed to me that
you wanted to transition, but didn't know how, and that I was going to
help you."
"And he believed you?" I asked, incredulous.
"Yes, he did. His exact words were," she mimed his deep voice, " 'Makes
sense. I could tell he was a pussy. Just like you.' "
"He did not!"
"Yes, he did. Brandon said that you reminded him of a younger version
of... me."
"That's ridiculous."
"Is it? Is it so ridiculous? Don't you feel a special connection between
us?"
I looked into her pleading eyes.
"Well sure," I admitted. "But that doesn't mean I want to transition to
being a woman."
"Oh, of course not! I know you're a man - deep down - even if you were
masturbating while wearing panties at night, listening to your BGFF get
porked by her boyfriend."
"Shannon!"
"The way I see it, all we have to do is convince Brandon, that's all.
Just dress up for him. You know, on weekend when he comes to visit - once
every other month or so, max! I promise! Once he's convinced, then we can
stay together, as roommates."
"This is insane. You're insane! He'll never believe I'm transgender. I'll
never be able to pass as female."
"Of course you can! As long as you do what I tell you to do, you'll have
no problem at all. I can already see the woman in your features, the
woman inside you. It will be easy, as long as I'm there to guide you.
Please believe me."
"There must be a better way. Why don't I move out, and we just continue
to see each other and go out and stuff? What if I move out and just come
over when Brandon is not here?"
"It won't be the same," Shannon said, with a fierceness that surprised
me. "Only if we're in each other's lives, every day, living together...
only then will we be true BGFFs. If you leave now... we'll drift apart.
The moment will be lost. I know it will!!"
"But Shannon..." I whined
"You promised to be best girl-friends forever, didn't you? Just last
week? Now it's time to keep your promise, to go out on a limb - for me.
Besides, what's the worst that can happen? Brandon doesn't believe that
you're actually transgender and you have to move out anyway. How is that
any different than if we didn't try at all?? Don't you see? It's our only
hope. It may be a long shot - but what else can we do? And what do we
have to lose? Only everything! Only each other - forever! Please, please,
please! Let's at least try!"
With a firm grip on my hand, Shannon pulled me up from the sofa and
dragged me into my bedroom.
"What are you doing?" I asked as she reached for my shirt buttons.
"Undressing you," she said simply, slapping my hands away and unbuttoning
my shirt.
"No, please," I moaned as she pulled off my shirt.
"Hush. You don't have anything I haven't seen before." Shannon undid my
belt buckle and then unzipped my pants.
"What are you doing? Are you going to change me now?"
"Don't be ridiculous. I'm just evaluating what needs to be done, okay?
Brandon said he'd be back in a week, and either you had to be dressed as
a woman, or I would need to get a new roommate. So we better get
started."
"Next weekend?" I gasped. "So soon?"
"Yes, it happens sometimes. Usually he comes to visit once a month, or
once every other month, but this time it's just next week. Apparently
something's up at work."
Shannon pulled off my pants, leaving me in underwear and socks.
"Some hair, but not too bad. I'll send you to my laser hair removal lady
on Monday."
"Laser hair removal??"
"Don't worry, it will grow back. Can you talk higher?"
"Higher?" I squeaked.
Shannon giggled. "Yes, higher. Can you pitch your voice a little higher
than normal?"
"Like this?" I tried.
"Good. How about even higher?"
"How about this?"
"Excellent! Now talk like that for the rest of the evening, okay? We need
to get you used to speaking with your lady voice."
"I still sound like a guy."
"Well, yes, but we have to start somewhere. We'll keep working on it and
maybe by Friday you'll be reasonable."
"Brandon will never be fooled."
"But we don't need to fool Brandon."
"What do you mean?"
"Talk higher!"
"What do you mean?" I repeated, speaking higher. "Isn't that the whole
point? Isn't that what we're supposed to be doing?"
"Brandon already knows you're a man trying to be a woman, don't you see?
You don't need to be perfect by next weekend. All you need to be is good
enough to convince Brandon you're really trying. That's not so bad, is
it?"
"I guess not."
"It's a process, and he knows that. Believe me, he knows that. Oooh! What
about a slumber party?!"
"S-s-s-slumber party?" I stuttered, my mind blitzing.
"Didn't you ever wonder what happened when girl-friends got together and
had a slumber party?"
"Yeah, I guess. I mean, what guy hasn't?"
"Then let's have one! Here, let's find you some panties..." Shannon
rummaged through my drawers before pulling out a light pink pair, "and a
nightgown, this one! Put these on and come to my room, okay? And then
we'll do girl stuff and have a slumber party! I'll get the wine."
With a squeal of delight, Shannon skipped out of the room.
I stood there for a minute, just in briefs and socks, breathing heavily.
'What the hell am I doing?' I thought to myself. 'Am I really going to go
through with this?'
I sat down on the bed and removed my socks. I could hear Shannon popping
a cork in the kitchen and fetching some glasses. I stood up and removed
my male briefs.
I looked at the panties Shannon had picked out for me. It was true, what
I had said before. I had worn panties just last night, and I had
masturbated in them while listening to Brandon and Shannon having sex in
the next room.
Why had I done it? The reasons were a mystery to me. Certainly I was in
love with Shannon, that was clear. And she had bought me the panties and
I was wearing them, because she wanted me to...
I pulled on the panties. Shit, my hard penis was clearly visible in
front. What was I going to do? There was no way this was going to work.
I slipped on the nightgown. It was long and comfortable with short
sleeves, made of cotton, and in light pink with white trim.
Oh. I smoothed it over my body. It felt delicious. Thankfully the flowy
fabric hid the bulge in front, which was a good thing since it was pretty
obnoxious.
"Christine!" I heard Shannon call out. "Where are you?"
Christine? Shannon was calling me Christine now? I sat back down on the
bed, trembling. Was I really going to do this? Was I really going to let
her turn me into... a woman?
No, I decided. No I wasn't. We were going to have to find a different
way. I got up and crossed the liv