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Are You Turning Into Your Roomie free porn video
This was a tag for something on AOL. Figured it would
make a good theme for a story.
Are You Turning Into Your Roomie
Chapter 1
My name is Ronnie and I'm now a sophomore in college.
My freshman year had been filled with a huge set of
ups and downs for me. Academically I had done really
well, acing almost my entire freshman course.
Socially it was a disaster; I had not fitted in at
all in the freshman guy's dorm. I was smaller and
skinnier then the rest (it seems that somehow most of
the guys on the hall were jocks or jock-wanna-bes). I
was that interested in sports (although I felt that
soccer was kind of cool) and I really didn't like to
swill beer the way most of the guys did.
I had been home schooled for the most part, my
parents had sent me to a very exclusive, small prep
school my senior of high school. My mom and dad were
pretty well off and because of my good grades my
folks agreed to let me get an apartment my sophomore
year. I decided that it would be nice to have a
roommate so after finding a pretty nice place off
campus I put an ad out. As a result of the ad, I
found myself sharing the 2-bedroom apartment with
Ann, a very pretty and outgoing grad student. She had
gone to undergraduate school somewhere else and had
even worked for a couple years at a Wall Street
trading firm. She was now pursuing her advance
degrees in economics. Ann was tall, 5'10 to my 5'8,
with an athletic build, long blond hair and a
beautiful face. She spent most of her time studying
but did occasionally go out. Over the course of the
first semester, we eventually fell into some patterns
of life around the apartment. Ann ended taking care
of paying the bills and doing the shopping for us
while I tended to the cleaning and cooking. We were
really enjoying spending time together but it felt
like brother and sister more then anything else.
They say that if people live together long enough
they can start to pick up each other's traits. My
hair had always been long but it was usually pretty
unkempt - I just normally pulled it back into a
ponytail each morning. Ann taught me how to wash it
properly, how to brush it out while drying it and
finally convinced me to get it dyed at the salon we
went to get our hair cuts. The hair coloring turned
my mousy light brown hair into a gorgeous blonde that
almost matched hers. The coloring and the daily care
I put into also cured the frizziness of my hair,
leaving me with really full hair that felt so rich in
my fingers. Ann encouraged me to exercise, first
walking each day and then other exercises in our
apartment. Pretty soon I joined the same gym that she
went to and found myself joining her for pilates and
yoga classes. My body quickly started to develop in a
lean, graceful way. My clothes also started to
change; Ann was impeccable dresser even when she
dressed casually. I felt myself starting to emulate
her style but in a slightly masculine way; I found
slacks that I had tailored to fit me in a way to show
off my cute little butt. I wore silk shirts or tight,
light sweaters. I finally started to wear contacts
too. The guys in my classes pretty much shunned me, I
even heard a few whispers of "fag"; the girls turned
out to pretty friendly and I even was able to out to
have coffee or study and such with a number of them.
Living with Ann had given me confidence to deal with
other girls as equals and to be able to have real
conversations with them. A number of them, when
seeing me and Ann together would ask if we were
related, Ann always seemed to get a kick out of that
question and would tease me by saying that I was her
younger sister.
At Christmas break both Ann and I stayed at school.
My parents had decided to go to Europe for a second
honeymoon and Ann had to work on preparing a paper
for a conference that spring. The campus really shut
down during the holiday, Ann spent a lot of the week
before Christmas working on her paper leaving me
alone. I decided to decorate the apartment and I also
spent time shopping. I decided to buy Ann a really
nice dress and some perfume as presents. I made my
now usual trip to the salon to get my hair trimmed
and even let them give me a manicure with clear
polish on my nails. Christmas morning finally came
and I was able to surprise Ann with her gifts. She
absolutely loved the dress and went ecstatic over the
perfume. I was really surprised when she in turn gave
me some presents - I didn't even realize that she had
time to shop.
Before she let me open though she asked me to sit
down and have a talk.
"Ronnie, these presents are kind of special for me
but I want to ask you some things before you open
them."
"Sure Ann", I was nervous about how serious this had
become but she gave my hand a firm squeeze and I
settled down.
"Ronnie, you've changed a lot since we started to
live here and I'd like to try some new things, at
least try them during these next two weeks before
classes start up again. You've really become special
to me, I really do feel like you're almost like a
little sister to me now."
I guess I should have felt a shock at what she was
saying but strangely I didn't. "I guess I do feel
like you're my sister Ann."
Ann then spent some time telling me about her sister
Karen. Karen had been a couple of years younger then
her but had died of cancer when they were in high
school. Ann and Karen had been very close as sisters
and her death had deeply hurt Ann, she had recovered
only by throwing herself deeply into her schoolwork.
"Ronnie, I'd like you to try being my new sister,
will you?"
I could barely breathe. All of the loneliness I had
felt as an only child was washed away. Ann had become
my hero over the last few months and now she wanted
me to be her sister.
"Yes, I'd love to."
We were both crying by then and she took me in her
arms and hugged and rocked me till finally the tears
stopped.
"Now that it's settled, time for your presents."
At that I set to opening each of the boxes she
stacked in front of me. They of course contained two
complete sets of women's clothes. Bra, panties, a
beautiful wool dress, a calf length skirt and silk
blouse. There was also a gorgeous long coat,
pantyhose, breast forms, and a pair of shoes, pumps
with a three inch heel. I kissed her cheek and hugged
her for giving me all of the gifts.
Ann led me through getting ready, first showering and
shaving what little hair I had from my body to trying
on my new lingerie and then the skirt and blouse. She
helped to softly curl my hair and finally put some
makeup on my face. When we stood side by side we did
really did look like sisters. I spent the day cooking
our Christmas dinner while we had a long, long girl-
to-girl talk.
Chapter 2
The rest of the holiday week was wonderful as Ann
really made me feel like her younger sister. We went
shopping each day buying whole new wardrobes. We both
would try on the clothes as it turned out that we
were just about the same size. We'd run in and out of
the dressing room, trying on skirts and dresses. We
made a special shopping trip to buy me new slacks,
not the men's ones I had been wearing, but women's
slacks that had a slight men's styling, Ann had
convinced me that I would be able to wear them to
classes with no one noticing the difference. On one
day Ann took me to a spa where I had a whole day
beauty treatment; my legs were waxed, my skin
pampered, my nails were done, and finally I was given
a full makeover.
Each evening we would get dressed up and go out to
eat at a different restaurants. I started to enjoy
all of the stares that Ann and I got from the men. No
longer was I feeling like some kind of awkward geek
of a guy, now, thanks to my big sister I was a
beautiful young girl. I was surprised at the end of
the holiday week.
?Ronnie, I want us to go out for New Year's eve.? Ann
told me.
?Where do you want to go??
?There's a club across town that has dinner and a
party.?
?Okay but what will I wear?? My wardrobe by now was
pretty large but I had neither a tux nor an evening
dress.
?Oh, I've got us matching dresses, sis.? Ann of
course had everything already planned out.
The dresses were deep red, with long skirts that were
slit almost to the hip. Hers was low cut in the front
with a very deep plunging neckline and a completely
sheer back. Mine was more demure with more coverage
front and back but there was absolutely no mistaking
the fact that the same designer had made both of
them. On that day we spent an incredible amount of
time working on each other's hair and makeup, wanting
to look just perfect. We both wore sheer, silk, tan
pantyhose to show off legs under our dresses. Ann
didn't wear a bra but we both wore are sexiest black
lingerie.
Ann had rented a limousine for the night, and
promptly at 9, dressed to the nines, we departed in
our chariot.
The club turned out to be a private, exclusive club.
Ann had managed to get an invitation through her old
Wall Street connections. We were served champagne and
the dinner buffet was magnificent. There was a very
nice jazz band playing; Ann and I chatted around
while watching all the couples dance.
It was kind of a shock when we were asked to dance.
Two handsome men in their thirties, Dave and Frank
had apparently been watching all evening and finally
come over.
?Well I'm Ann, this is my sister Ronnie and we'd love
to dance.? Ann smiled at me as she took Dave's arm
and let him lead her out to the dance floor.
Frank offered his arm, and almost in a trance I found
myself being led out to the dance floor too.
I had never done very much dancing before but I
quickly found myself being expertly led about the
dance by Frank. He was a tall, very handsome, well-
built man with a very nice smile and sparkling eyes.
From time to time I saw Dave and Ann dancing
together; it turned out that they were both fantastic
dancers and made a spectacular couple out on the
dance floor. I felt a certain pride to realize that
Ann was easily not only the best looking woman out on
the dance floor but probably the best dancer too.
We danced for what seemed to be hours when suddenly
the band leader announced that that it was now time
to get ready to count down the new year. Frank and I
found ourselves back with Ann and Dave as the count
down started. Everyone in the room was loudly
counting down the seconds and then it happened; it
was the new year and I found myself in Frank's arms
being kissed and kissing him back. It was over fairly
quickly but I found my breathe completely taken away.
?Hey, little sis, Happy New Year!? I broke out of my
dream as Ann hugged me and gave me a peck on the
cheek. Dave also gave me a quick kiss before I found
myself back in Frank's arms. The music started again,
much slower now, and I felt myself melting into
Frank. The lights had also been dimmed considerably
and in the darkness I turned my face to Frank's and
we kissed again. There was nothing short or quick
about this, it was a long kiss that I eagerly
returned, his tongue teased my lips and I opened my
mouth and sent my tongue to meet his. His arms
completely encircled me as I clung to his shoulders
and neck.
In kissing him, the decision that I had been
struggling with the whole week had been made. Despite
the absolute joy I had felt at becoming Ann's sister
this past week, I had harbored some doubts about what
the new school semester would be bring. I had loved
the feelings I had as a girl but I didn't know if I
could be one at school. I had thought that maybe I
would end up straddling some line between boy and
girl; going to classes as I had as boy, even the
slightly femme boy that had been and being a girl in
the evenings and on the weekends. Now I realized that
none of that would make me happy; that I really did
want and need to be a girl. I also realized something
more, that living with Ann had given me a sense of
what type of confidence I could have in myself as a
girl.
The song we had been dancing to finally came to an
end and we broke our kiss. I excused myself from
Frank and went to find Ann.
?Ann, can we talk? I really need to ask you
something.?
?Sure Ronnie, what is it.?
?Let's find somewhere private.?
Ann led me out of the banquet room and we found a
small alcove off the hall that had a small sofa in
it.
?Is there something wrong Ronnie??
?Ann, you said you wanted me to be your sister
right??
?Sure, honey, why??
?Well, I'd like that but I'd don't want to be a boy
anymore.?
Any doubt that remained was banished as I saw Ann's
face light up, the joy in her eyes was unmistakable.
?Ronnie, are you really sure??
?Yes, I am, is it okay??
?Oh, Ronnie of course it's okay.?
I couldn't help it anymore and tears started to flow
down my face. Ann laughed and drew me into her arms
as I felt such a huge burden being lifted from me.
?Don't worry, you're my baby sister now and we'll
work everything out honey.? Ann took out at tissue
and wiped the tears from my face.
?What prompted all this anyway??
?I was dancing with Frank and as we started to kiss
something seemed to just click in me and I knew what
I wanted with my life. I mean this last week had been
so nice and we had been thinking about something like
this but I guess I had never really faced the
decision before and I was so worried about classes
and what people might say and what my parents would
think and I wasn't even sure if you were really
serious about and I just didn't know about what I
wanted except well you've really been such a hero to
me and when Frank kissed me I just seemed to know
that if I was girl all the time it would be okay.? I
finally ran out of breath and sat there looking at my
hands.
?Ronnie, everything is going to be okay. You've made
your choice and that's the important thing right
now.?
Ann, at that point took my hands in her and gave them
a gentle squeeze.
?Now, what do you think of Frank??
My head jerked up at her question and I felt myself
blushing fiercely. ?Um, well he's nice.?
Ann laughter was infectious, ?Oh Ronnie, don't be so
coy with your big sister, I can see that you really
like him.?
I giggled in response ?Yes I guess I do, I mean he
really is pretty cute.?
?Good, I'm glad that you like him, I was hoping that
you would.?
?Really, wait did you already know him??
?Honey, I'm sorry I didn't tell you ahead of time but
I wanted it to be a surprise and if I had told you
before, you might not have agreed to come. Dave and I
dated some when I was in New York and I asked him and
Frank to come and celebrate with us. Frank is a very
nice and very understanding guy. He's also bisexual
and really adores girls like you.?
?You mean he knows that I'm really a guy underneath.?
?Ronnie, you need to realize that you're not a guy
anymore; you're a girl now, it's just that you're a
special kind of girl.?
?Oh.? It was all starting to sink in now, if I was
going to be a girl then I was really going to be
girl, yes a special girl but I was girl, not a boy
playing at being girl but a girl.
?Yes, Oh. You also need to understand that there are
guys out there too. There will a lot of guys that
will only see a girl, but you'll need to be careful
with them so they don't find out about you but there
are others like Frank that won't care about that or
will even find it exciting too. You understand.?
?Yeah, I mean I just never realized anything about
that.?
?Oh Ronnie, there are plenty of girls like you out
there; some of them go all the way and have surgery
to make them real girls and others just dress only
occasionally dress and there are all sorts of others
too.?
?Ann how do you know so much about this? I guess I
was really sheltered.?
Ann laughed ?Oh Ronnie, I lived in New York where you
see just about everything but I also dated Dave and
he and Frank are roommates and I got to learn about
it from some of the girls that Frank dated.?
?You mean girls like me??
?Yes hon, like you but none of them were nearly as
pretty or femmy as you already are.?
We just sat there for a moment as it all ran through
my mind. There weren't any more doubts in my mind, I
knew I was a girl now and I knew that Frank would be
waiting for me and I also knew that Ann loved me as a
sister.
Chapter 3
We finally went to find the guys. Ann had asked me if
it was okay if Frank and Dave came back to the
apartment with us. She wanted to spend the night with
Dave; she told me that it was up to me entirely
whether I wanted to sleep with Frank or let him sleep
on the sofa. She told me that he understood already
that I was a new girl and that I might not be ready
to go very far. In fact she encouraged me not to get
carried away because everything was so new to me and
so much was happening.
After we found Dave and Frank, we decided that it was
time to get home. Ann had explained that everything
was okay and it was that I had finally made my
decision to start the year as a girl. Both Dave and
Frank congratulated me, Dave gave me a quick kiss and
hug before handing to Frank who also gave me a quick
kiss but also wrapped me in his arms.
We retrieved are coats and all of us piled into our
waiting limousine.
On the way back to the apartment, Dave and Frank
asked us how school was going. Ann talked about her
grad courses and about preparing for the upcoming
conference while I replied to their questions about
being an undergrad.
When we finally got the apartment, Ann gave me a
quick kiss goodnight before leading Dave to her
bedroom.
Frank and I settled on the couch. He had removed his
jacket and tie, loosening his shirt collar. I had
removed my heels and let me hair loose before curling
up next to him.
We began to kiss again. We started slowly and softly
but soon are kissing became more passionate. Our
mouths were open to each other as our tongues dueled
back and forth. My hands roamed over his strong
shoulders, his muscular arms and his broad chest. His
hands held me close to him, he stroked my leg through
the slit of the dress, he gently cupped my ass. His
lips left mine as he kissed his way up my jaw line.
He kissed my ears and made his way down my neck. I
felt my whole body flush as he kissed my shoulders
and the top of my chest. He slowly made his way back
to my mouth, reversing his course as I opened his
shirt and placed my hands on his bare chest. We
kissed more but finally came up for air. I looked
into his eyes but I knew I had to say something to
him, no matter how much my body wanted him right now
I knew I couldn't go all the way with him but I still
wanted to spend the night with him.
?Frank, I really want to but we can't go all the way,
I'm just not ready for that yet.?
?It's all right Ronnie, I really do understand.
Besides Ann would kill me if we did.? He was smiling
down at me as he said but it did touch a certain
warmness in me to know that my big sister would look
out for me. ?If you want I'll sleep out here.?
?No, I don't think that will be necessary, I really
do want to spend the night with you, it's just that
there has to be a limit as to what I'm going to do.
Is that okay with you?? My head was down, looking at
my hands in my lap; I was afraid that he would be
upset that I had led him on and that he really had
expected to have sex with me or wouldn't want to be
with me unless he could have me.
?Ronnie, I'd love that. I can't think of a better way
to spend the first night of a new year then sleeping
next to you.?
?Well why don't we go to bed then, just let me get
changed first.?
I went to my bedroom where I discovered that Ann had
laid out a nightgown for me. It was a long, white,
silk gown with a lace bodice and spaghetti shoulder
straps. I picked up the nightgown, finding some very
pretty white lace panties too, and went into the
bathroom to cleanup and change. I quickly took off my
dress and hung it on a hanger and then removed the
lingerie I had worn that night before putting on my
new panties. I washed my face and then applied some
more perfume before putting on the gown. The silk of
the gown floated down my body and hung gracefully
from my shoulders and the breast forms still glued to
my chest. I turned off the light as I left the
bathroom and slowly made way to my bedroom where
Frank was waiting. He was sitting on the side of the
bed in his silk boxer shorts. Without his clothes I
was able to examine his finely muscular body. He was
muscles were overdone in extreme bodybuilder way but
they were built up nicely and well defined. His
chest, stomach and legs had soft covering of light
brown hair. He had turned down the covers of the bed
and he rose to his feet as I entered.
I went to him and he drew me into his arms.
?You look lovely in that Ronnie.?
?Thanks, I think Ann left it for me.?
We kissed briefly before he slowly guided me onto the
bed. We climbed into the bed, arranging ourselves on
the pillows facing each other before he drew the
covers up over our bodies and turning out the lights.
It seemed so wonderfully to be in bed with him. I
reached out to him and kissed him. My hand traveled
up and down his bare chest as his arms encircled me.
He kissed me tenderly as our legs intertwined beneath
the covers. I could feel that he was hard as his cock
rubbed against my hip. I realized that while I wasn't
going to have sex with him that I did want to give
him some pleasure tonight. As we continued to kiss,
my hand traveled down his chest, I traced the hair
down past his navel till I felt the cool silk of his
boxers. My hand found his cock now, and softly
grasped it through the silk of his boxers.
?Are you sure Ronnie?? His voice was husky in my ear.
I didn't trust myself to answer but instead I quickly
reached up and tried to pull his boxers down. He
lifted his hips a bit and I was able to push the silk
shorts down his thighs. I then reached up and
enfolded his naked cock in my hand as I kissed him. I
started to stroke his cock with my hand and he moaned
into my mouth as we continued to kiss. I pushed him
onto his back and straddle his leg with mine as I
continued to stroke him. I kissed his lips, his nose,
and his eyes. My mouth traveled to his neck, down his
neck below his ear, I kissed my way down his neck to
shoulders. My hand continued to caress his cock, it
was leaking now as my mouth made it's way down to his
chest. I traced out the outline of the muscles of his
chest with my tongue and then kissed his nipples. My
hand and his cock were now moist and slick. My mouth
continued to explore his body, his breathe was rapid
now and his body was tensing.
?Ronnie, I'm going to cum now.?
I looked up and watched his face as his whole body
tensed and went rigid. My hand continued to stroke
his as I used my leg to rub the silk of my nightgown
against his leg. His eyes closed as he threw his head
back, his breathe came in gasps and I felt his cock
in my hand twitch as he came.
He slowly relaxed as his cock stopped twitching in my
hand. His breath became deep and he opened his eyes
as he raised his head to look at me. I rose up beside
him and then leaned in and kissed him deeply. When I
finally pulled back, smiling down at him, he smiled
at me and chuckled.
?You are incredible you know that??
?Thanks, I'm glad you liked it.?
?Liked it? God that's an understatement.?
I got up then and went to the bathroom. I wet a towel
and then came back to clean him up. I softly washed
his chest, stomach and groin before dropping the
towel on the floor. I pulled the covers up over us as
I snuggled up against him. I felt a sense of
contentment and warmth as he wrapped his arms around.
I was almost sure that we would now drop off to sleep
but he pulled me to him and kissed me. He kissed my
lips as he hands explored my body. I was resting on
his chest, which left both his hands free to stroke
my body through the silk of the nightgown. He
massaged my back and shoulders before slowly making
his way downward. His hands caressed my legs and
worked their way up to my ass. His hands felt the
globes of my ass and traced the outline of my
panties. His touch excited me and I felt my passion
building. He must have sensed this and I soon found
myself being rolled over until my back on the bed and
his body was above me. He kissed my ear and neckline
and I felt his hand more up my bare leg and under the
hem of the nightgown. His hand traveled up and
explored my thighs before lightly moving over my
panties and to stomach. He slipped the nightgown off
of me and then kissed me over my chest. His mouth and
tongue made their way down the center of my chest and
wished now that I had real breasts for him to have
licked and sucked on. His breath was hot on my skin
as his tongue flicked at my navel.
Then he was at my panties. I had folded my cock
between my legs to hide it but now he was bending my
legs and was softly stroking me through the material
of my panties. He bent his head down and kissed the
lace panel before he started to lick my cock through
the panties. His hands reached up and lifted my hips
as drew my panties down. My cock immediately unfolded
itself from its hiding place and started to harden. I
was only about 5 inches long and Frank quickly took
me into his mouth. My cock had never been touched by
another person except for the doctor and the pleasure
of Frank's act stunned me. My breath was torn away
from me as Frank licked my shaft and I immediately
came. As I realized I was cumming I tried to lift his
mouth from but he kept it there and drank down my
cum. I was floored, I was grasping for breath and my
heart was racing, the pleasure that Frank had given
me, the discoveries of the whole evening had erupted
through me. I lay there, almost comatose as Frank
rinsed his mouth out in the bathroom and came back to
dress the two of us, slipping his boxers on and
drawing the nightgown over me. He gently drew me to
his body and pulled the covers over us. I felt him
kiss me before we both drifted off to sleep.
Gigi
- 27.06.2021
- 6
- 0
