Subject: First Time With My Junior Roomie
Story Codes: F-solo FF oral
Diary Date: November 21, 2005
Author: Kelly <pghpa_girl@yahoo.com>
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!!!WARNING!!!!
This file contains sexually explicit material which may include graphic
depictions of underage, nonconsensual and unprotected sex as well as
incest, adultery, sodomy and bestiality. It is distributed on a website
clearly identified as "For Adults Only". Possession by a minor is
strictly forbidden. If you are not legally empowered to be in possession
of such material, do not read it and delete it immediately.
This work is copyrighted 2016 to the author. It may be posted to non-
commercial "free" sites, or in the "free" area of commercial sites so
long as no changes are made to the content and the Author information is
retained. Any other use of this work is by written permission of the
Author only.
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Summary
=======
Jen was my Junior year roomie and cute as a button. She had a boyfriend
with whom she is definitely no prude but had never been with a girl. From
the day we met I dreamed we could be closer but never actually dared to
hope that our relationship would get as close as it did!
Table of Contents
=================
Chapter 1 – My College Roomies
Chapter 2 – Jen Misses Her Boyfriend
Chapter 3 – Getting Closer To Jen
Chapter 4 – Crossing the Line With Jen
Postlude
Chapter 1 - My College Roomies
==============================
It was the start of my third year of college and I was now a junior!
Finally I was not going to be in a dorm but instead an apartment. No
more RAs breathing down my neck to keep the room clean and police what I
do all the time. It was an on-campus apartment which meant the rules
were still pretty strict – no boys at ANY time for instance, but I was
used to that.
In the past I had to wonder about what my one roomie would be like.
Well, this year I had FIVE. The apartment had three bedrooms so I would
only be sleeping with one and sharing a bathroom with four more. The
bedrooms were all larger than my previous dorms rooms so I wasn't
expecting any issues.
Although I was curious about all five of them, one in particular was on
my mind – Jen. I had gotten her bio and introductory e-mail once the
room assignments were made and we’d chatted a few times so I knew a bit
about her. You never knew what a person was really like until you
actually met them and the introduction letters were so sterile it was
impossible to know how they would be when you actually met. Take my
previous roomies for example...
My freshman year roomie was Brenda. Brenda lives in a nearby town about
ten miles or so away. Her parents thought it would be a good idea for
her to spend her freshman year on campus to help acclimate to college
life. It worked out well for her even though she still went home most
weekends. Sometimes she would let me come along which made for a nice
getaway from the dorm room.
When I first left home for college I had a steady boyfriend with whom I
had thought I would maintain a long-stance relationship and see whenever
I got back. He went to a local college and we had been dating for a few
months and I was starting to think maybe he even loved me.
Brenda took me home with her one weekend shortly after school started and
we had fun taking pictures of me for my boyfriend. The photo session got
pretty hot and eventually led to my first lesbian experience (OK,
technically I have been having sex with my mom and her younger sister
since I was sixteen but that is completely different from doing with a
girl not related to me).
I was about to send them off to my boyfriend when an e-mail arrived from
him telling me he was seeing another girl and just wanted us to be
friends. Naturally I wrote the bastard back telling him what he could do
with that proposal AND he certainly didn't get the pictures I had made up
for him. I felt more hurt than I had ever been in my life. How could I
have been so blind not to realize that he was just like all the other
teenage boy that dated me just for sex?
Brenda was fantastic, though, and she helped me through those times,
helping me forget my ex-boyfriend in a number of ways which including us
sleeping together. We continued that for the rest of the school year and
to this day I still consider her one of my closest friends.
Unfortunately her parents weren't about to pay for another year in the
dorms which meant I had a new roomie my sophomore year – Karen.
Karen was a multitude of conflicts. She was one of the sweetest girls
you could ask for – and one of the most naturally sexy ones as well. On
the one hand she was a confirmed virgin who was so up-tight about sex she
wouldn't even masturbate, but on the other she had a figure I would have
killed for and loved to dress in sexy clothes and skimpy bikinis. She
was wonderful to be around and loved by everyone but was quite demanding
as a roomie.
Things had to be Karen's way, though, which meant me sleeping with
something on instead of nude as I have been since I was twelve. It was
crazy in a way. People talk about their college years as the times they
did wild things and here I was actually being less open about myself than
I had ever been. Needless to say Karen never knew much about my sex life
although I think she suspected I was not everything I portrayed myself as
at school. She certainly never had a clue why I was so happy to spend a
weekend at Brenda's! At the end of the year we parted as close friends
but she transferred to a school closer to home so I never saw her again
and we didn't stay in touch.
From what little I knew of my latest roomie, I expected Jen to be in
between the two extremes I had experienced to date. She was smart and
had skipped a year of grade school when she was younger so she would be a
full year younger than me. She had also been a cheerleader in high
school and I immediately had memories of the little bitches at my high
school that made up the cheerleading squad. I certainly hoped she had
put that behind her but she still seemed quite the perky one when we had
talked on the phone.
From her pics she had sent me I could see that she was quite pretty and
even if she had not told me she had been a cheerleader I would have
guessed. She just had THAT look – little miss perky with the brilliant
smile and glowing eyes that had every guy in school drooling over her.
Hopefully that meant she wasn't the prude that Karen had been but I
realized that being so lucky as I had been with Brenda would take a small
miracle.
It was move-in day and for the first time I drove myself to school in my
"new" car. I should say it was my first car as it was mom's old Avalon
that she gave up to get her new BMW. It had over a hundred thousand
miles on it but still ran well and was comfortable to drive. My gear was
packed in the trunk and back seat so I pulled up on the curb outside the
apartment. It was easy to find – right across the street practically
from my old dorm.
I looked at the girls moving into the dorms and smiled to myself. I
should have rightfully been out of there last year but there was room in
the apartments for only about two-thirds of the sophomore class so a
lottery was held and wouldn't you know it but I lost. Better late than
never though and I started carrying my stuff in and in the process met my
new roomies.
Jen hadn't arrived yet so I got to pick out which bed and closet I
wanted. I had everything in and was chatting with my other roomies when
Jen and her parents showed up. They had driven in from Wisconsin where
they lived in some town by a lake so it had taken them longer to get here
than I did. I greeted Jen and in the process did a quick assessment.
She was actually shorter than even I was at barely 5'2" and couldn't have
weighed more than 95 pounds. She was indeed the bouncy perky type but in
a pleasant way. She had a great figure and a smile never seemed to leave
her face.
Jen's parents were wonderful and I noticed that the first piece of
personal stuff she put in the room was a picture of her boyfriend. Later
after she had moved in and said goodbye to her parents we sat down and
got to know one another. Over the course of the next few weeks we grew
closer and told each other more personal things during which I learned
more about Jen and her boyfriend.
First of all, Jen was at least no virgin. This was actually more than
just a minor confession for any girl to make at our school where sex was
outright forbidden and premarital sex considered all but a mortal sin.
We were both relieved to find that the other was actively having sex at
home although we were totally different in that regard.
Jen had not lost her virginity until the summer after her freshman year
of college and since then had only had sex with a total of three boys,
two of them only once. Her most recent boyfriend, Alex, was the first
and only boy she had given a blowjob to.
Needless to say I didn't tell her I had had one-to-one sex with dozens of
guys by then and a total more than 100 if you counted the faceless guys
at various parties I had gone to. It was a bit funny in a way in that
while I played down my sexual history it seemed she was trying to impress
me with hers. Apparently once she found Mr. Right the barriers came down
and they had been fucking like rabbits all summer. It should go without
saying that she missed Alex – a lot, and it wasn't his glowing smile she
was missing already!
Chapter 2 – Jen Misses Her Boyfriend
====================================
As the weeks went by I could tell Jen was missing Alex more and more as
it seemed she was getting hornier with each passing day. This worked in
my favor as gradually we opened up to each other more and more in terms
of discussing sex. I love to sleep nude and I can still vividly remember
the shock on Karen's face the first (and last as it turned out) time she
saw me slip under the sheets with nothing on.
Jen's eyes widened a little bit the first night but she didn't say
anything and in fact the next night I noticed that she was sleeping nude
as well. I smiled at her as she dropped her robe, revealing her petite
nude body before quickly covering herself under her blanket. Her face
reddened as she held the covers up to her chin and told me that sleeping
naked was something she always wanted to do but her parents would have
had a fit! After that night we didn't say anything more about it but it
was the last time either of us wore anything to bed.
I loved to chat with people on-line about sex at night and while I could
never get Jen into it (none of my friends do either unfortunately) at
least she didn't interfere with me. Although she knew I was chatting a
lot she never really knew about what and certainly never knew that at
times I was discussing my incestual relationships!
Sometimes she would get on the phone with her boyfriend as I was chatting
and it was at those times when I could tell she was missing him a LOT,
and in more ways than one judging by the way she squirmed when they
talked. Sometimes she would get up and take her phone to the bathroom.
I would just sigh, wishing she wouldn't feel she had to hide when she
played with herself while she talked to Alex. I would have loved to have
heard what she was saying to him as well!
The real breakthrough came after about a month or so of us being
together. Although I tend to be a night owl, mornings have always been
my peak sexual time. I seem to always wake up horny as hell, my pussy
wet from whatever nasty dreams I must have been having. At home my dad
stops by my room before he goes to work which helps me out but usually he
doesn't have a lot of time and I still will often masturbate even after
he has fucked me. At school I am left to take care of myself –
literally.
At first I just fingered myself quietly under the covers, trying not to
wake Jen. Apparently I wasn't totally successful because one morning
when I thought she was sound asleep I must have been a little louder than
I should have been when I came. Jen was on her side turned away from me
but to my complete surprise I could tell from the way she was moving that
she was doing herself!
When she had finished she turned over and we both looked at each other
and then broke out into laughter. Apparently we were both horny in the
morning and each of us had been trying not to let the other know. Well,
from then on we didn't try to hide it when we played with ourselves and
as we grew more comfortable with each other we got more open about it.
It wasn't like we were putting on a show for the each other but at the
same time we didn't hide it either.
For me it was almost like being home where masturbation was nothing to be
ashamed of and I felt free to do whatever I wanted at any time. For Jen,
though it was an entirely new experience. Her mother had always told her
masturbation was something "bad girls" did and so she had always been
shamed when she did it but at the same time couldn't stop herself no
matter how hard she had tried. She had never masturbated, or even
touched herself for that matter, in front of anyone, not even Alex and
certainly never another girl.
I asked Jen if she hadn't done it together with any of her friends during
a sleepover or anything like I had when I was in high school. Jen looked
shocked when I asked as if she couldn't believe a bunch of girls would
ever even consider doing anything like that. Well, I guess they raised
them pretty conservative in mid-Wisconsin!
Although Jen had never been with a girl and so far had really showed no
interest in it, I have to admit that during many of our masturbation
sessions while she was dreaming of Alex I was imagining being closer to
her. Once we started playing in front of each other in the morning she
started being more open about her feelings when she had phone sex with
Alex, something that seemed to get more frequent and naughty as time went
by and she got hornier for him.
While she was fingering herself telling Alex how much she wanted him in
her pussy I would be sitting in bed alone with my laptop, chatting with
people on Yahoo! and fingering myself. I am sure she thought I did it
because of the conversations I was having with my on-line friends but in
reality I was imagining what it would be like to help her get herself off
as she masturbated while she talked to Alex.
Chapter 3 – Getting Closer To Jen
=================================
For the next month or so we grew more and more comfortable with each
other. At first we would wake up and masturbate under the covers, each
knowing what the other was doing but not really showing anything. Over
time we became less inhibited. First the covers dropped to reveal our
boobs and slowly moved downward with each passing day until I could see
her hand between her legs while she played with her pussy.
Finally one day I had my knees up and I let the covers slip over my knees
to reveal my open pussy for her to see. She looked over and saw my hand
in my pussy and at first she quickly looked away, as if having seen
something she shouldn't have. Her curiosity and lust soon overcame her
trepidations and she kept stealing glances back until finally she just
watched. I spread my legs apart to make it easier for her to see and I
was rewarded with the sight of her playing with herself even more
vigorously than usual. It took a few days of this for her to follow suit
but finally she allowed to see her entire nude body as she played with
her clit and pussy.
I love watching other people masturbate – boys and girls, and it makes me
even hotter to see them bring themselves to an orgasm, especially when I
know it is me that is helping them get there. Knowing that I was the
first to see Jen masturbate made it even more special for me and when she
would cum, lifting her hips high off the bed as her back arched and her
eyes were tightly shut. It made me want to just reach over and hold her
tightly to me.
The two of us continued to masturbate regularly but thus far that was as
far as we ever went. Although I noticed she seemed to enjoy watching me,
there was never even the slightest hint that she wanted to do anything
more. If anything, it seemed she just talked about fucking Alex even
more once we started doing it together. Sometimes I would talk about a
boyfriend or two that I had fun with back home but I never even hinted at
the "special" relationships I had with my family.
Chapter 4 – Crossing the Line With Jen
======================================
So it went until it was the week of Thanksgiving break. It was a short
week and everyone was waiting impatiently to go home Wednesday afternoon.
Jen had tickets to fly home and from her most recent phone calls with
Alex, I had a feeling Alex had better be ready for some serious sex when
she got there! She was as horny as I had ever seen a girl be and was
masturbating two and three times a day - at least so far as I knew. I
figured if there was ever going to be a time to try to make that next
step with her, this was it!
Monday morning arrived and we were both up early going at it in our
respective beds. The covers were thrown back and we both were on our
backs with our knees bent and spread apart to let the other see as best
as possible. Neither of us had an early class on Mondays so usually on
this day we would get off and then hit the bed for another hour or so of
sleep to let ourselves wind down. I climaxed first as I dreamed of what
I was about to do with Jen if only I could work up the courage.
Jen was fingering herself with one hand while she cupped one of her small
boobs with the other. I could smell the distinctive odor of her wet
pussy as she stroked two fingers in and out of her. Taking in a deep
breath, I released it slowly as I got out of bed, went over to hers and
sat down next to her. She opened her eyes as the weight of my body
tilted the mattress under her but then just closed them again as she
continued without another moment of hesitation. At first I just sat
there, my heart pounding as I looked at her pussy from as close a view as
I had ever had.
Her fingers were wet as she put one of them in her pretty pussy and then
used the others to spread the wetness over her pussy lips and clit. I
couldn't help but lick my lips in anticipation as her finger moved over
her swollen clit making her body convulse as the pleasure it created
spread out through her.
I put my hand between my legs and felt my own wet pussy, the bare skin
around it slippery from my pussy juices and moaned softly as I touch my
clit and felt a shiver go up and down my spine. For the next few minutes
I masturbated with her on her bed, the two of us next to each other but
other than the feel of her bare hips against me as I sat there, still not
touching one another.
I knew that if I didn't do something soon I would lose my courage so with
my heart beating so fast I was sure she could hear it, I took my left
hand and gently placed it on her upper leg, letting my fingers lightly
touch her inner thigh and then slowly dragging my fingertips over her
skin which was as soft and warm as I had imagined it would be. Now THAT
got her attention and she opened her eyes and stopped her masturbating.
I took note that she didn't take her hand off her pussy though which was
hopefully it was a good sign.
"Um, Kelly... what are you doing?" she asked softly, a sly grin coming to
her face.
"Shhhhhh, " I replied softly as I lifted my hand off of her, "Nothing,
don't Worry... don't let me stop you." She closed her eyes again and soon
started to finger herself again so I put my hand back on her leg again
and this time she didn't' do anything to stop me. Encouraged, I let my
hand move quicker over her silky smooth thighs, going from leg to leg but
passing north of her pussy and over her belly as I did. Jen opened her
eyes and looked at me as if seeing me for the first time.
"Kelly.. I mean really, what are you doing?" she asked but not stopping
her masturbating this time. I didn't say a word but just let my
fingertips continue to lightly trace little circles as I moved my hands
over her lower body. "Kelly, you know I have never done anything with a
girl before," she said, this time in a bit louder voice. "I'm not a
lesbian!"
"Mmmmmmm, don't worry Jen," I said, trying to reassure her, "I'm not one
either so don't worry. I love boys but it can be fun with a girl
sometimes." Her body seemed to loosen a bit and she giggled when my
fingers passed over her side just above her hips.
"That tickles!" she giggled.
I slowly moved to her stomach and made little circle around her belly
button. She giggled again and twisted just a bit as she said laughingly,
"Kelly! Stop tickling me!"
I grinned at her and slowly worked my hand down to the top of the short
line of pubic hair she kept when she shaved her pussy. "C'mon Jen, just
close your eyes and imagine it's Alex touching you."
Fortunately her incredible lust for Alex won out over any concerns about
me and she did indeed close her eyes and resumed her masturbating. Oh my
god she looked so hot! She was so small yet had such a beautiful petite
figure. Her pussy scent was so much stronger this close up and I licked
my dry lips in anticipation of tasting it for the first time. I knew
that I still had my work cut out for myself if I was going to make THAT
part of my dream come true!
I continued to slowly trace my fingers all over her body, moving from her
legs to her hips (where I she was still incredibly ticklish!) over her
tight little stomach and then at first just around her boobs which were
so petite like the rest of her naked body. My fingertips moved in ever
reduced spirals around her boobs until they were touching her pointed
nipples.
Jen gasped as I pinched them softly between my fingers, pulling on them
gently. I put my finger in my mouth to get it wet and then used it to
rub her nipples, the moisture lubricating her hard nipple under my
fingertip.
"Ohhhhhhhhh yes," she moaned softly, "That feels soooooo good."
Emboldened by her response, I worked my way back to her stomach and then
just touched the top of her hairline of her close-trimmed pussy hair.
Jen trimmed her pubic hair but didn't shave it off the way I did.
Apparently Alex liked to play with it and so she made sure there was some
for him to have fun with.
I gently lifted her hand off her pussy and place it on her breast. Her
wet fingers immediately started to knead her boobs while mine went back
to her now empty crotch. She was soaking wet from masturbating for the
past hour and probably cumming at least once or twice in that time. My
finger easily slid over her clit and I felt her tense up as I started to
play with it.
"Oh I don't know about this Kelly... I just don't know," she whispered in
a hoarse voice.
I noticed her hips were starting to move under my fingers so whatever
uneasiness she was trying to vocalize, her body was betraying her true
intent.
"Just imagine Alex's big cock forcing its way into you," I said as I
began to push one of my fingers just inside her swollen pussy.
Even though she must have been expecting it, her hand immediately flew to
her crotch on top of mine. My finger was into her pussy up to the first
joint and I held it there to see what she was going to do. After a few
seconds she pulled her hand back and went back to massaging her boob.
She opened her eyes and looked at me, her face a mixture of emotions,
lust, embarrassment and confusion all in one!
"Oh god Kelly I really don't know what to do... I want it so bad but it's
not right," she cried out as tears actually started to flow from her
eyes, "I just don't understand this, how can something so bad feel so
good?"
I tried to calm her but she kept babbling on saying, "I know it's wrong
to do it with a girl but yet I want you to touch me! ...Oh Kelly I just
don't know what to do!"
I pushed my finger deeper into her and then started to stroke it in and
out of her as if it was Alex fucking her. I leaned over and took her
free nipple into my mouth and sucked on it tightly. Licking her nipple
with my tongue, I whispered to in a voice husky with lust, "Tell me what
you want Jen... Tell me what you want me to do... Please tell me."
I went back to sucking her boob as she moaned loudly. Thank God the
walls were pretty soundproof as I wouldn't want our roomies next door to
hear any of this!
Jen lifted her hips up under my hand and in a throaty voice said, "Oh god
Kelly, I want it, oh yes I want it! ...Oh god Kelly don't stop, do
anything you want to me."
She opened her eyes then and we looked directly at each other.
"Anything," she repeated softly and distinctly.
I knew she probably wasn't yet to the point where she could verbalize
exactly what she wanted but I knew from the away she said it what she
meant. I felt a twinge in my pussy as I knew I had succeeded in my quest
– Jen was mine now and all I had to do was take her. It felt so
incredible I almost didn't want to go further and spoil the sense of lust
and anticipation. I wondered if this was how my boyfriend felt when I
gave myself to him as a virgin, when I told him it was OK to fuck me and
I submitted myself to him completely? Is this how he felt when he
realized that a virgin teenager was giving herself to him and letting him
do anything he wanted to her?
All I knew was that seeing Jen lay there, waiting for me to do whatever
it was I wanted to do to her, wanting me to have my way with her, was one
of the most sensuous and erotic feelings in the world!
I got up and spread her legs wide apart with my hands. She watched me
intently, licking her lips and breathing heavily. I climbed onto the bed
with her and kneeled between her open legs, gazing at her open wet pussy
that she now was presenting to me without hesitation or shame. Leaning
down, I placed my hands on the sides of her hips and reached under to
hold up her tight little ass. Then, without breaking eye contact so as
to maintain the spell between us, I lowered my head between her legs
until I drew in a deep breath to savor the musky scent of her pussy.
Finally I worked up the nerve to plunge my face into her crotch and my
tongue searched out her clit and ran circles around it as she gasped and
arched her back. God she tasted so good! I had been wanted to taste her
for so long it seemed almost like a dream that my face was finally
pressed against her pussy for real, that the wetness I felt was her
actual pussy juice and not my vivid imagination as I masturbated. I
pushed my tongue between her pussy lips and into her pussy hole as far as
I could. She tasted so sweet and strong.
"Oh Kelly," Jen moaned, "That feels soooooo good. Please don't stop. No
matter what I say or do, don't stop!"
I pushed one finger into her pussy and went back to work on her clit with
my tongue. She was bucking against me now and gibbering like a baby,
telling me how good it felt and how much she loved it. I inserted a
second finger into her and got it good and wet and then took it out.
Then I did something I had never done to anyone before except myself, I
pressed it against her asshole and started to push it in.
"Oh no!" she yelled at me, "Don't touch me there... I can't take it,
please Kelly, no!"
Well, she was the one who said don't listen to her say NO so I didn't. I
pushed my finger further inside of her until it was to my second knuckle.
It was weird, I had never felt anyone else's asshole before and even my
own was not something I touched very often. I had always thought the
feeling would disgust me but with Jen it was anything but that. I could
feel my fingers together, one in her pussy and one in her asshole,
rubbing each other through her. My mouth was still sucking her clit when
she was ready to cum.
"Cumming!" was all she could get out but man did she ever!
Her pussy cum flowed over me and I felt her asshole pinch down on my
finger as it violated her. Her pussy cum was delicious and I lapped it
up eagerly with my tongue. God she tasted soooooo good! She finally
collapsed as her orgasm died down, exhausted from my efforts on her.
I moved up and laid next to her on my side, my breast pressed against her
side and one leg draped over hers. I ran my fingers up and down her
body, letting just my fingernails once again trace themselves over her
lightly. I let two fingers run over her breast and nipples and she
gasped as her eyes were closed and she just laid there not moving a
muscle. She didn't even have the energy to close her legs back together
again.
I would have loved to have had her lick me in return but for now this was
wonderful enough. I knew this would not be the last time we did this and
I was sure she would be returning me the favor.
Postlude
========
It took a while to get this story to print and since then events have
occurred which might be of interest so I thought I would add this before
publishing the story. Somehow we made it to class that day but as soon
as we were back Jen was hungry for more and yes indeed, she did return
the favor.
As it turned out, Thanksgiving break was soon upon us and Jen went home
where she fucked her boyfriend's brains out. Returning to school, she
wasn't nearly as horny as she had been that week just before break and
actually seemed embarrassed to even discuss it so we held off doing
anything more than masturbating for a few days. Finally I sat her down
and we discussed it. That lead to us being back in bed together and we
have been there regularly since.
I doubt we will ever be able to recreate that intensity of our first time
together but I'm happy with the way things turned out!
THE END