Falling For My Roommate Ch. 02

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Things take an interesting turn.
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Part 2 of the 3 part series

Updated 09/22/2022
Created 05/10/2006
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Naturally, the thing I dreaded the most was the end of the semester, when the two of us would eventually go home and not see each other for a solid month. Thanksgiving break wouldn't be so bad, since that's only a week, but nonetheless it weighed on my mind as the weeks went by. About a week before Thanksgiving, I commented to Jesse, "It's gonna be hard to adjust to sleeping alone again."

She replied, "I suppose it will," with a noted lack of enthusiasm. I began wondering about this girl. Was there someone, or something, that she wasn't telling me about? Was there a reason why we only just kissed and didn't do a thing more?

Eventually, her comment faded out of my brain and I began to think happier thoughts, such as going home for a week and not having to do school work. We parted ways on Saturday with a long kiss in our room, although I had secretly hoped that she would have wanted more.

The drive home was rather uneventful, and that week was rather boring. My mom asked me if I had found a boyfriend at school, which I didn't. She was rather disappointed to hear this, but she knew just as well as I did how hard it would be to find a decent guy, especially one who would accept me for who and what I am. I refrained from telling her that I had a girlfriend, especially since I realized that the two of us were not as close as I thought.

With Thanksgiving came a two-person-size dinner, since my parents had divorced as soon as my dad had come out as being gay. This also meant that my brother Mike, who was also gay, wound up living with Dad. It was a rather bitter divorce, especially since Mike and I were moderately close and still talked to each other after the fact. I dare say she coped with it rather well. If only I could've coped that well with loneliness...

The trip back to school was one I almost didn't want to make, since I would be leaving Mom alone and would be going back to a person who I had seriously begun to doubt. When I got back to our dorm I noticed that she was already there and had begun the unpacking process. When I first saw her, I noticed that something was amiss. For one, she had her hair cut much shorter than when first we met, almost as short as most of the guys on the hall. The other thing that didn't set well was her apathy at my arrival. I didn't expect a passionate kiss there on the spot, but I did want at least a hug or something.

Since we were both somewhat tired from the trip back, we both just sat around in the room for a while before eating supper and stocking up on groceries. For once, she made her own pilgrimage to the store, which bothered me slightly. I knew that she would be going to the exact same store that I would and always asked me beforehand if I wanted to accompany her. I just chalked it up as tiredness and went on about my business, not thinking anything of it. I felt somewhat of a temptation to snoop through her things, but I decided not to violate her trust. It was a good thing, too, because within five seconds of me thinking that, she opened the door and walked in with the groceries. For the first time in a while, there was somewhat of an awkward silence in the room.

On Monday morning, she went to her early class as she always did, and I stayed in bed, as my classes were much later in the day. For some reason, I woke up as soon as she shut the door on her way out. After a few minutes, I got up and curiosity got the better of me. In one of her desk drawers, I found a photo album. I cautiously flipped through it, and found some pictures of a couple, and I stopped for some reason. The girl looked eerily familiar, and the guy was somewhat cute. Eventually, it hit me like a ton of bricks. The girl in that picture was my roommate! I never imagined her with long hair, and I never thought that she would be caught dead in a dress. This shocked me to no end. As the tears started forming, I just put the album back in her drawer and crawled back into bed for a few more minutes.

When I finally managed to get up, I was still crying somewhat, and had no idea what to do. Should I confront her about her boyfriend, or should I just shut my mouth and continue our relationship in ignorant bliss?

I decided to just let it be, rather than try to inquire about the picture, or what it meant. I had already begun to realize quite a few things I had questioned. Sooner than I thought, my questions were answered.

On the last day of fall classes, Jesse walked in and locked the door, which was something she only did when she wanted to kiss me, or when we went to bed. She immediately walked over to her desk and put down her backpack. Things didn't look too promising. "Kirby," she said, glancing over to me with a stare that could kill most mortals, "I've been holding something back from you that I probably shouldn't have." I could see it coming, just like a bomb. "I have a boyfriend at home. I felt horrible when I saw him and couldn't stop thinking about you, and I almost cried."

Amazed at her bluntness, I just held out my arms and gave her a long hug, crying onto her shoulder, not knowing what to do. "Thank you for telling me," I managed to say through my tears. It seemed like that hug lasted forever. When we finally relinquished our grip on each other, she began to explain her life.

She started off by showing me the picture of her and her boyfriend, and explained that she was afraid of being tempted to cheat on her boyfriend while at college. She confessed that she had her hair cut extremely short, to 'look like a lesbian.' Come to find out, she hadn't even thought about kissing a girl until she met me. This flattered me quite much, since almost nobody ever wanted to kiss me.

Despite the fact that I now knew that she was taken, we still continued to share the bed and kiss each other good night, but it just didn't have the same feel that it first did. Regardless, it still felt quite comforting to fall asleep in somebody's arms.

As we packed our bags for Christmas break, I couldn't help but wonder if she would tell her boyfriend about me and, if so, what would happen. I almost didn't want to think about it, but the thought still burned inside my mind.

With the new year came a new semester, and new classes, new people, and new worries. Driving back to campus, I had a rather uneasy feeling that I probably would never kiss my roommate again. I could not have imagined how wrong I was.

This time, when Jesse walked in the room, she left the door open, dropped her bags and held out her arms. I suspected she wanted a hug, but instead gave me a kiss, which was a very pleasant surprise. It also surprised me that she left the door open, because she always insisted that we kiss behind closed doors, rather than in the open where others could see. After what seemed like a blissful eternity, our lips slowly parted, and she whispered to me, "My boyfriend's history now."

With my arms still around her, I finally began to understand the magnitude of this situation. As my hands slid down her arms and eventually grasped her hands in mine, one of our hallmates walked by and stopped in, evidently curious as to what we were doing. Jesse took the easy way out and said that I was helping her to cope with her break-up, which seemed laughable to me, since I knew that she was rather enthused about getting away from him. After all, why would she have, upon the first sight of me, given me that deep, passionate, wet kiss rather than telling me how heartbroken she was?

That night, we sat in an almost awkward silence, almost as if we were wondering what the other was thinking. It didn't take very long before I would out either. Jesse turned out the lights and I moved over to the side of my bed to make room for her, since these dorm beds are notoriously small. I was greeted with the now-familiar kiss on the lips that had a modest amount of tongue to it. She tried not to admit it, but she seemed rather fascinated by my tongue, as was the case with my lips. I had gotten the stud in my tongue in high school, but had only gotten the two rings in my lower lip since I came to college. I had noticed a good number of people stare at them, but none would ever accept my mental invitation to kiss me, except Jesse.

Our kiss lasted much longer than normal, and we even rested briefly, only to resume kissing for another long while. I hadn't paid much attention, but it became evident to me that Jesse was attired in a slightly different fashion tonight than she normally was. Normally she wore a t-shirt and boxer shorts that could've belonged to her boyfriend, but tonight, she had a slightly tighter shirt and her spandex pants that hugged her hips all too well. I seriously doubted that she had bothered putting any panties on beneath them, since I couldn't see any lines through her pants. Unlike Jesse, my sleepwear was the same as normal: some random t-shirt, a really long parachute skirt, and bikini bottoms, but not for long.

After a good ten minutes of kissing, Jesse began to slowly rub my stomach, her hand slowly wandering higher and higher, almost as if to tease me. I'm sure she could've told by now that I also had a ring in each nipple, identical to the rings on each side of my lip without even touching them, but soon she would know for sure. As her hand went gradually higher and higher, my nipples began to harden and so did my cock. I tried to maneuver the cock away from her a little, but she seemed to realize that I was getting aroused. I began to slowly let my hand wander up her shirt was well, my finger running circles around her navel, then proceeding slowly upward towards her breasts. Soon, her fingers were caressing my nipple rings and my hand was fully around one of her breasts, gently feeling its suppleness.

Our lips slowly parted, and we each stripped out of our shirts, only to resume kissing each other's lips briefly. Then, the temptation got the better of us and we began to kiss each other's nipples, slowly biting and tugging at them, taking turns and getting more aroused by the minute. As my hand kept rubbing her stomach, she moved somewhat closer to me, practically forcing my hand down to her waistline. As I was about to move my hand back up to her stomach, she gently pushed it back down a little bit. I nervously moved my hand down below the waist of her boxers, inching my way down very slowly. She returned the favor by slowly sliding her hand down my skirt. She didn't have as far to go as I did, seeing as how I was already quite hard and my cock was almost peeking out over my panties. Eventually, my fingers reached her moist lips, where I began to gently rub and slowly slide a finger into her, then rubbing her clit with it. By this point, she had begun to rub my cock through my bikini bottoms, but eventually she just slid her hand beneath them and began to stroke me.

I was getting more and more turned on as we eventually stopped kissing so that she could remove her boxers and I could shed my skirt and panties, leaving us both completely naked. This time, when we resumed kissing, I immediately slide two of my fingers into her, then used my index finger and my thumb to delicately pinch her clit. She then proceeded to grasp my cock and begin to stroke it again. Our lips parted yet again, except this time she laid down on me, with her face hovering above my cock and her pussy directly above my face. She then relaxed and my tongue slowly slid into her, and I could feel her lips slide down the shaft of my hard, wet, cock. I could also feel her lick her fingers, then slide a pair into my vagina, exploring around. I decided to test her kinky limits and licked one of my fingers, then rubbed a circle around her butt until I felt it begin relaxing, at which point I heard her moan slightly, then I slid it in.

I couldn't stand it much longer, and eventually, as she licked my tip with her tongue while her lips still enveloped me, I came right in her mouth. She knew just as well as I did that the fun was only part of the way over as she shifted her efforts from my cock to my pussy, as she timidly slid her tongue into me, while her fingers began to give my butt some attention. After a few minutes of me licking her deeply, I carefully positioned my tongue piercing right on her clit and began to slowly wiggle it around. It didn't take much of this before she came and I lapped up her wetness happily. This managed to get me closer and closer to orgasm until I eventually just couldn't hold it anymore and came right in her face. By this point, we were both slightly tired and rested for a moment until Jesse turned around and kissed me gently, and I could detect the taste of my own cum in her mouth.

Seeing as how I wasn't very sexually experienced, it took me quite a while to recover from what just happened. It was rather easy falling asleep that night, and somewhat surprising to wake up naked next to someone. However, pretty soon after our eyes opened, reality set in. We had to go to class. Getting up, getting dressed, and walking to class in the frigid weather was difficult enough, but what made it a little more pleasant were the thoughts of that night, a night like which I had never seen before, and didn't think I'd ever see again.

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