Sex With Girlfriend 8217 s Roomie
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New Roomie free porn video
Her new roommate
By: Catherine
1
At first I was hesitant when she dropped the idea to me. To move in with
her, and two other girls. One roommate was moving to LA, and they
desperately needed to find another roomie before the end of the month.
She is Katie, we had worked together for about four years. She had
recently turned 24. Her roomies were Jamie and Jonna, 23 and 25,
respectively. Me, I was 29. The only reason I could think of to say no
was the fact I had: a little secret.
After a few days of contemplation I decided to do it. I was month to
month at my place anyway. It was old and needed a lot of work that the
landlord refused to do without raising the rent. This would be a little
bit cheaper, but more importantly much nicer. Plus, I would get to live
with three beautiful young women. One of whom I was pretty much in love
with, and had been for a while. Over the course of a week I moved into
the master bedroom of their spacious house in an upscale neighborhood
west of the city.
At first I was reluctant to practice my little secret. But when they
would all go out of town as a group, which was every so often, I would
live it up. I had so much more to choose from now! Goodness! They had
extensive wardrobes. You see, I am a closet cross dresser, a
transvestite to be more precise. From what I have self-diagnosed on the
web I am a Low to Medium Intensity Transvestite with no desire for re-
assignment. I started cross dressing in my Mother's clothes around ten
or twelve. I would steal articles from friend's sisters or mothers as
well as my own cousins. I really started getting into it after high
school, once removed from the parents house. It was purely sexual,
although sometimes I would stay dressed after an eventful night alone.
My dream was to find a partner understanding of my desires, even
encouraging, but never had the courage to ask girlfriends. I always
dressed up alone and spent the night alone. And every little girly-boy
knows what that leads to. It's embarrassing, but you know you're gonna'
do it again
After living in the house with the girls for about three months it was
spring break time and they were all going to Cabo San Lucas for five
nights and six days. I was asked to go, but really couldn't get out of
work. And, I really wanted nothing more than the entire house to myself
for six days. I drove them to the airport and saw them off on a
Wednesday morning and then went to work. It was hard to concentrate on
work throughout the day, knowing that I would be becoming my feminine
self that night, Michelle. And that I had the next two days off of work
to be her. Plus Sunday and Monday. Five nights to play in my very own
fetish playground.
As soon as I got off I went to Target and bought a few makeup items I
lacked and went straight home. I locked all of the doors, shut all the
blinds, turned on all of the exterior lights and dimmed them all inside.
I ran a bath and used some of Jonna's bubbles.
I used Jamie's shaver and soon had my entire body smooth, save for a
little triangular patch just above my genitals. After lighting several
candles I soaked in the therapeutic bath sipping a glass of wine. After
washing my hair and rinsing, I dried off and used a little powder under
my arms and around my privates.
I had ordered a new complete outfit a month prior, delivered to my PO
Box of course so the girls wouldn't find it. I slipped into my favorite
bra and slipped the silicone falsies in, followed by my new corset. It
was light pink with a lace front and smooth silk everywhere else. It had
twelve rigid bones in it to keep me all in and it pushed up the falsies
and actually gave me cleavage. I pulled up the matching open-front
panties that were the silkiest thing I had ever felt. They both had been
custom made. I had measured myself according to the web sites
specifications and they had done a perfect job. The next pair of panties
were even better. They had a g-string, but in the front there was a
sleeve for my penis that was filled with fluffy softness. A lace mini
skirt of pink lace hung down around everything. It pulled my penis in
and gave the appearance of flatness in my groin and pulled my already
tight butt in even tighter. I went to slip on my new pink hose with
white bows but decided I would paint my toe nails, hell, I'll do my
fingernails too! I thought.
I brushed out my hair and began to set it on my smallest pink foam
rollers. My hair had gotten quite long, I always wore it in a pony tail,
so it had been a while since I had seen it down and wet. After ensuring
the setting lotion covered my wet locks evenly I did a row from my
forehead all the way to my nape, I did two more rows on each side of
that and then ran out of curlers. I used bobby pins, twenty on each
side, around my ears and temples and created little pin curls. I stepped
back and admired my work before slipping a net over the sixty curlers
and forty pin curls and tying it off in the back under the curler at my
nape..
Next was makeup. I covered my entire face in foundation. As it dried I
slipped in Katie's toe separators and I put a coat of pink polish on my
toenails. I then filled in my cheeks with blush, also under my chin, and
brushed my nose and forehead. Next was my eye shadow, I started with
purple near my lashes, followed by dark pink and light pink/white
progressively towards my brow and blended it all together. I trimmed the
new growth from my brows and with a brow pencil drew them in darker and
then applied mascara.
I did two coats and then used a liquid eyeliner to get my eyes really
dark and sexy.
I drew an outline of my lips with a lip-liner pencil and then filled it
in with my favorite 'blushing pink' lipstick. After brushing in a little
more blush and curling my lashes I looked at the beautiful woman staring
back at me. I had never looked more realistic. I'm getting pretty good
with the makeup! I thought.
I did one more coat of polish on my toes and got out the domed dryer
that had been boxed up in my closet. After setting it up on the desk in
my bedroom I slipped my roller-filled head under it and began painting
my fingernails in the same pink hue as my toes.
I watched the baseball game, sipping wine and smoking cigarettes as my
new sexiness dried.
After spending almost an hour under the dryer I went to replace it in
the box and decided to leave it out, as I would more than likely use it
again at some point over the next four nights. I slipped into the
silken hose and attached the garter straps in the front and back. I then
slipped on my pink and silver sling back 3" heels. The little bows of
the hose were in the front just below the skirt. I went to get more wine
and felt myself getting harder and harder in the fluffy sleeve under the
tight lace skirt. I had never felt this sexy, and each time I passed one
of the many mirrors in the house I saw just how sexy I was. I thought I
would explode.
2
I was in the kitchen opening a bottle of wine when I thought I heard
something. I sat still a minute and decided it was probably nothing. I
popped the cork and was pouring the wine when Katie turned the corner
from the living room into the kitchen. I dropped the glass into the sink
in disbelief, breaking it. She dropped her purse and put her hand to her
mouth. Her brown eyes were as wide as I had ever seen.
"Oh my God! Mark?"
"Please. Don't tell anyone," I begged. So embarrassed I could barely
speak.
'Oh my God!" she said again, mouth agape. "You are so, beautiful!"
"Please, don't tell anyone, please, I beg you," I pled.
"I won't," she said, just staring. We were both speechless.
She came around the counter and looked at me from head to toe. She
grasped my hand and inspected my nails. She used her other hand to feel
my exposed skin just below my corset and above the skirt. A smile came
to her lips. Her eyes were smiling as well. She ran her fingers around
and cupped my firm rear. Her other hand released mine and she put it on
my breast. I reached down and placed both of my hands on her hips.
It seemed like forever, but was probably just a few seconds, but we
looked into each other's eyes before we began to kiss. Passionately,
deeply. My hand cupped her beautiful butt tight and the other moved to
her hair. I loved her hair. It was straight now, and pulled up. I rubbed
her right at her nape as I kissed her intently. After a moment we
stepped back.
"Please don't tell anyone Katie. No one in the world knows about this."
"Nobody else?"
"No, until now it had always been my secret."
"I won't tell anyone," she mused. "If you let me play with you," she
said.
"I, I don't know, if I can."
"Why, are you, you know, gay or something?"
"No, Goodness no, absolutely not."
"Then what is it? Why couldn't we play, together?"
"Because I've always liked you," I said quickly, in one breath.
She smiled broadly.
"I like you too," she told me as she pulled me closer. "I always have."
She kissed me again, holding me tight. "Come with me, there is something
I have always wanted to do."
I followed her to the stairway leading to her and our other two
roommates rooms upstairs, on the first step she kicked off her sandals
and slid the straps of her dress over her shoulders and it summarily
slid to her waist. Her tan back stared at me. She had to help it the
rest of the way, slipping it over her hips. She stopped for an instant
and I was inches from her rear. She bent over to slip it over her feet
and I could smell her. I had always had a guilty pleasure of smelling a
woman's ass. Her smell was incredible. I followed her to her bathroom
where she removed her bra and I got my first glimpse of her beautiful
breasts. She had gotten them done on her twentieth birthday. They were
perfect. Perfectly rounded C cups. She slid off her panties and tossed
them to me.
"I'll be right back beautiful," she said as she went into her room.
I held her panties to my nose and inhaled the sweet aromas of her butt
and pussy melding into one heavenly scent. I felt myself growing ever
bigger in the fluffy sleeve.
I saw that it was trying to burst from the confines of the tight lace
skirt.
"I was given these when I had my first doctors visit for my breast job.
To become acclimated." She slid my straps down from my bra and corset
and removed the A size falsies. "I'm going to use a little adhesive to
keep them in place, okay?" I nodded.
She rubbed around the edges of the form and placed it onto my chest,
followed by the other one. She ran a finger around the edges to remove
excess glue and then pressed them on firmly with both hands. She slid my
bra up carefully, followed by the corset.
"Wow! They are much bigger!" she said, rubbing them. "And they feel sooo
good.
"Don't they?"
"Yes," I stammered. I was short of breath from all of the attention and
excitement.
"It's okay sweetie, I'm not going to hurt you. You are too precious,"
she told me then kissed me. "I want to do my hair, or, I really want you
to do my hair. Will you?"
"Yes," I said, and she kissed me again. She wet her hair in the shower,
toweled it off and brushed it out with setting spray. She sat down at
her vanity and opened a drawer where she pulled out a box. She opened it
and pulled out little curlers like mine.
"I want it just like yours, pin curls and all. This has always been a
fantasy of mine."
"Me too."
I began with the front, just like as if I were doing my own. This was
much easier though.
I had done about ten when she said she would turn around as it would be
easier for me to see in the mirror. I was working on the first one when
I felt my little skirt being lifted.
My penis sprang out and I felt it moving through the sleeve as it grew.
I fumbled with a roller and had to re-roll it when I felt her push the
sleeve back to my scrotum. My shaft was cold, but not for long. I was
clasping down the curler when I felt her tongue on the end. I could
barely comb out her strands for a new curl when she took me all in and
began to suck me softly. I somehow managed to clasp another one down
when I felt my body shudder and I exploded into her. She sucked harder
and I thought I might faint.
After she retracted my sleeve back down and pulled my skirt down she
bent her head down so I could resume her rolling.
"Make the ones at my nape tight, I like them tight."
"Okay," I panted. "Thank you."
"For what? Oh. You are welcome," she said sweetly. "That's just a sign
of things to come," she giggled. "Get it? Things to come?"
"Yes," I said, smiling at my beauty in the mirror.
I started back up on both sides and she turned back around to face the
mirror.
I completed the rows down to her forehead and she had five neat rows of
pink curlers across the top just as I did. She pulled out a box of bobby
pins and I did one side in pin curls and then the other.
"Wow! You're good! Have you ever set anyone besides yourself?"
"No."
"You're a natural," she complemented. "Here," she said as she clipped on
two hoop earrings to my lobes. "That looks better." She slipped her head
into a net and reached up and touched one of my curlers. "How did you
dry them, with a blow dryer?"
"No, I have an old dome dryer in my closet I bought off of E-bay."
"Can I use it too?"
"Of course, you can use anything of mine you want."
"Let's go downstairs then, and find a place to set it up."
I followed her back downstairs. The most beautiful woman I had ever met,
naked in front of me. Her hair up in pink curlers, her gorgeous ass
shimmying down the stairs. Her pert breasts jiggling as she turned to
wink at me. How could I be this lucky? I asked.
I retrieved the hair dryer from my closet and she said to bring it into
the den. She had poured us two glasses of wine and had the bottle in a
bucket on the coffee table. I set it up on the armoire behind the sofa
so she could sit back and relax while she dried.
I sat next to her on the sofa and turned on the TV and handed her the
remote. I reached back and turned the dryer on.
"How high would you like it?"
"As hot as you," she said with a devilish grin, and a cute wink.
I turned it to high. As I reached for my wine she held me back by my
hand. I turned and she looked down towards her navel. Her legs were
spread open slightly and she was glistening. She moved my hand down and
I felt her wetness. She moved one leg onto the table and whispered:
"please me now?"
I knelt in front of her and she moved her other leg around me to confine
me between them, the table and her wetness. I kissed her inner thigh and
moved towards her. She moaned.
I kissed around her wet lips and pulled out her clitoris with my tongue.
I moved it in circular motions as she squirmed on the leather couch. I
could feel her hands pressing on my curlers and she became even more
moist and hot. I reached a hand up and stroked her nipple. She moaned so
loud I thought she may wake up the neighbors and she shook for a second
and fell back into the sofa.
"Oh my God! Ohhhhh!" she let out. Her legs closed a little and I knew
she was done.
"Come here baby," she said.
I rose up to her and she leaned down and kissed me. Licking her juices
off of my lips and face.
"Thank you. That was the most incredible thing I've ever felt."
"You are welcome. And that, is just a taste of things to come."
I sat next to her and handed her her wine. She pulled an afghan over
her.
I slid my arm behind her and held my hand in the crevice created by her
leg and torso.
She looked at me with her beautiful brown eyes and we kissed. When we
needed air I would kiss her neck and ear. I felt hard once again as I
felt her pin curls on my lips and face. She moved a hand down and
stroked me under the blanket.
"I want you inside me now."
I reached around and turned off the dryer. I rose the dome from her
head, picked her up in my arms and carried her to my room. I lay her on
the bed and began to do what I had always wanted to do: make love to
her. But, she had another idea.
"I want to fuck you," she said with authority. She pulled me into the
pillows, undid my fasteners on the front of my tight fitting corset,
unhooked my bra closure in the front and ran her hands over the breast
forms now attached to my chest. As she kissed my stomach she pulled down
my skirt and removed my hardness from its fluffy sleeve.
She thrust me into her, riding up and down furiously. She grasped a hand
around a cheek of my ass and squeezed, while the other held her up over
me. I reached around and grasped both of her cheeks and held on. Her
breasts swayed over me and she glistened with perspiration from the
light penetrating the blinds.
"Sometimes I just want to fuck, I know you want to make love to me, but
I haven't been with a man for a long time, I need this baby. I need you
to fuck me," she whispered into my ear. I felt her curlers rubbing
against mine as she kissed me deeply. I came like I never had before.
"Oh my God!" she panted as she slipped off of me, pulling the covers
over us.
"You are incredible," I told her.
"So are you," she said as she snuggled up next to me.
After a few quiet moments she broke the silence.
"How long have you been doing this?" she asked.
"Doing what?"
"You know, dressing up. I mean, I love it. I do. I've always had a
secret fantasy to do this with a man. When I first saw you I admit I was
shocked. I never suspected it. But, like a nanosecond later I wanted to
literally just about rape you right there in the kitchen."
"Wow! Rape me?"
"Not rape you, but fuck you to no end. How long have you been doing it?"
"Well, I started experimenting when I was around ten. I would curl my
hair when my folks were gone. In high school I used to steal items from
girlfriends, my friends sisters and such. Sometimes I would steal things
from stores," I confessed. "But, when I went off to school is when it
really began. I started ordering things off of the internet. I would
dress up in my apartment on weekends. I started with the makeup, breast
forms and such."
"Have you ever done this with anyone else?" she asked.
"No, you are the only person in the world who knows I do this."
"Oh yeah. I really feel privileged. Or maybe I'm just lucky."
"No, I'm lucky. I'm glad you found me and not Jamie or Jonna."
"Yeah, they probably would have freaked out."
"Why did you come back tonight? I wasn't expecting you until Monday
night."
"I don't have a passport. With the new laws I wasn't going to be let
back in the country.
Jam and Jon wanted to come home with me but I insisted they go ahead,"
she told me.
"I'm glad now, that I only had a birth certificate, that I didn't get to
go with them."
"I know you wish you could have, but, being entirely selfish I'm glad
you're here."
"Me too."
"So this has always been a fantasy of yours?" I asked her.
"Well, to do it with a woman at first. But I'm so conventional I could
never try to be with another woman. I had thoughts all through high
school. Fantasies about slumber parties turned lesbian orgies and things
like that. But I could never bring myself to do it. Then I had a
boyfriend with long hair and girlish looks my freshman year in college.
I tried to get him to do it with me but he freaked out and never called
me again."
"I'm sorry."
"It's okay, we weren't meant to be I guess," she told me, as she
snuggled up closer.
"I did mess around with a girl when I was really drunk last summer. We
were at a party at a big house on the lake and we started kissing when
some guys egged us on.
I liked it. I don't think she did at first. When we got even drunker I
kept flirting with her and she just thrust herself onto me. She said: 'I
didn't think you wanted it, but now I know you were just timid.' She
tried to rape me. I was scared. Jam grabbed me and took me home."
"I'm sorry."
"I'm fine about it now. We were both just drunk." She paused. "Have you
ever, you know, thought about or been with a guy?"
"No, and no," I stated flatly, and honestly. "I've always been
fascinated by the fairer sex.
"Don't take this the wrong way, but I just wonder why you like to dress
up."
"I have always wondered the same thing," I said. "Perhaps you can help
me understand why. Maybe this was fate that we came together like this
and we have similar fantasies."
"I hope so, but my fantasy carries a bit further sweetie..."
To be continued...
Josephina
- 14.06.2021
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