Jen is my Junior year roomie and cute as a button. She has a boyfriend with whom she is definitely no prude buy has 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!
It was the start of my 3rd 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 w had 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 16 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 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 her way which me sleeping with something on instead of nude as I have been since I was 12. 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. Her 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-time 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. Needless to say, she missed Alex ‒ a lot, and it wasn’t his glowing smile she was missing already! As the weeks went by I could tell she was missing him 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 but she didn’t say anything and in fact the next night I noticed 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 incestuous 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 her 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.
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.
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 then 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!” “Mmmmmm, 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 you 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 finger tips moved in ever reduced spirals around her boobs until they were touching her pointed nipples. She 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 soooo 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 it’s 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. Then I plunged my face into her cunt 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 sooooooo 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 sooooooo 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.
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