Falling For My Roommate Ch. 03

If there's one good thing that college taught me, it was that concentrating in class the day after getting your first blowjob is very difficult. I must've gotten aroused at least four times during my first class, and a couple during the next. It was a true pity that I wouldn't be back in my room for a few hours because, if I was, I'd definitely pleasure myself to the thought of last night. Lunch came and went uneventfully, and I finally made it out to my last lecture of the day, by which time I began to wonder what that night would bring. Would my roommate try to go even farther in bed with me, or would it be a simple good-night kiss?

When I got back to my dorm, I put down my backpack and lazily plopped down on my bed, still rather tired from the night before. Evidently I was tired enough that I fell asleep with the door ajar, and pretty soon Jesse returned from her classes. I heard the door shut calmly and the next thing I knew, I was being gently moved towards the wall as she slid into bed with me.

"You must've gotten worn out last night, eh?" I questioned, as she settled down next to me.

"Yeah, but not as worn out as you," she laughed.

"Hey, that's the first time I'd done a lot of what we did last night, so take it easy dear."

"It's quite alright. You were the first person to get me to orgasm without me having to, shall we say, intervene."

"I'm flattered. But then again, I am a girl after all. Well, ok, mostly a girl," I chuckled. After a little awkward pause, I decided to finally spill the beans on why I was so unique down there. "Ya see, I kinda baffled a few doctors when I was a baby. They saw something that looked like a little penis, so they thought, 'ooh, it's a boy,' but then they realized that I had a vagina too, and they decided that I should probably be raised as a girl. My mom was there when they were going to cut off my penis, and she told them not to. She didn't want them to do something like that, since there's always a possibility with intersex kids that they may want to be the gender other than the one they were raised with. I'm glad I'm a girl, but I'm also pretty glad my mom made them keep my cock."

"Next time you see her, tell her how awesome that decision was." With that, Jesse leaned towards me and gave me a soft kiss, and we both fell off to sleep for a couple hours, surprisingly devoid of any sexual activity.

By the time we awoke, it was getting close to sundown and it was time for us to eat something other than each other. Jesse snuck out and ate with some of her friends, which left me to eat alone, as usual. While my thoughts were still filled with the previous night, a few doubts had begun to emerge. After all, why would she eat with her friends and not invite me along? Was I just being used for sex now? Even if that was the case, it was certainly better than not having anybody to be affectionate with.

I walked back to my room and noticed that my beloved roommate was still gone, but that was ok. I knew she'd be back. I also knew that she'd probably never bring any of her friends back to our room, let alone introduce me to any of them, for fear of them finding out about us. The thought somewhat plagued me, but I did what I normally did to try and forget about it. I started reading one of my texts in true nerd fashion. In the course of an hour, I'd managed to read all I ever cared to know about influence, and had managed to get rather sleepy in the process. Since Jesse hadn't returned, I got ready for bed and read some more, still waiting on her to return.

Somewhere around midnight, she finally returned back, and finally came to bed an hour later. She seemed almost reluctant to settle into bed with me, but nonetheless she gave me a little kiss and we both drifted off to sleep.

For the next couple months, things seemed to be okay between us, but things still didn't make any sense. Not once did she ever bother trying anything beyond a kiss. That is, not until the night before we left for spring break.

While we packed for spring break, I could tell we weren't both going home. She was packing swimwear, shorts, and sandals. I was packing uber-long skirts, long-sleeved shirts, my nice comfy long coat, stockings, and boots. Needless to say, I wasn't the one going to Cancun over the break.

As she sorted through more swimsuits than any one girl should be allowed to have, she asked me a question which I never, EVER wanted to hear. "Hey Kirby, I need your advice on something... Which of these looks better?" She held up two that looked almost identical, and I arbitrarily picked the one in her left hand. She then proceeded to do something that she had never done before. She stripped naked in front of me before she put it on. Without putting a finger on me, she managed to gain my cock's full attention as it stretched my panties beneath my skirt. I didn't bother letting on that I was aroused, as I think she knew it rather well. She knew what she was doing.

She adjusted her top and twirled around in front of me, then asked me if I still thought it was the better of the two. I nodded in approval. She searched around and found a pair of sandals she was intent on wearing with it, and put them on. I was slightly baffled by why, but I soon found out. She walked over to me, almost like an exotic dancer about to give me a lap dance, and she said down on my lap. "Take it off," she said.

"Your swimsuit, or my outfit" I timidly responded.

"My swimsuit, silly."

"Alright," I said, as I reached around behind her to unfasten her top. It was almost too easy. I then untied the side strings on her bottoms and pulled them out from underneath her. All she had left on were a pair of shoes fit for a stripper (a pair I wouldn't mind having myself), yet I remained fully clothed. Realizing that this was my chance to have some fun, I leaned forward and gave her a long kiss as our bodies moved closer together. I could feel her breasts touch my shirt, and I yearned to be naked, but somehow I didn't think that's what she had in mind. She lifted up slightly and pulled my skirt up, exposing my panties which had become slightly wet. She skillfully pulled them all the way off me, past my boots, which caught them, making it more difficult for her. She eventually just flung them across the room unceremoniously. I then became really nervous. I didn't want to lose my virginity just yet, but I had a feeling I would in short order. Even that thought didn't prepare me for what was about to happen.

"Would you ever do a girl in the butt?" she asked candidly, as I sat there in quiet amazement.

"Heck yeah," I responded enthusiastically.

"Good, then I won't need that little banana," she said, tossing it aside and handing me a tube of lubricant. I immediately put a little bit on my fingers as she sat down with her butt and pussy only inches away from my cock. She began to gently stroke me as I started sliding my fingers into her butt, then slowly out. Pretty soon, she put some lube on her hand and began to prepare my cock for entrance into her back door. I had to hold onto my sheets as she slid herself down onto my cock, and I could feel her butt squeezing me tightly, making me feel like I'd burst any second.

Once my cock was all the way into her, she began to lift up, almost to the point where my cock would come out. She'd then relax and would envelop me again. It didn't take very long before I couldn't hold out any longer, and I eventually just released my cum directly into her butt. As I did, she sighed deeply and relaxed. She then bent forward and kissed me deeply with my cock still inside her.

Jesse immediately went to take a shower, and I followed suit a half hour later, as to not arouse suspicion. We went to bed quite happy, although Jesse was a wee bit sore.

The next morning, we both got up and got ready to head out, and we gave each other a long good-bye kiss and parted ways. As I was traveling home, I realized that she probably had a reason for what we did that night.

Spring break wasn't all that special, although it did give me time to relax. I had hoped to catch up with some folks I knew in high school, but alas, they didn't really want to talk to me, so I wound up spending my break shopping with my mom. It made for a pleasant week, without all the questions of what would happen once the school year is over, whether or not Jesse would still want to associate with me, and whether or not I'd ever find anyone like her again.

On the drive back, my mind was still filled with thoughts of my break and the fact that I didn't have anyone to sleep with, yet strangely didn't crave it. However, when I got off the highway and started heading towards campus, I began looking forward to having Jesse back in my bed again. For some reason, it wasn't as big of a deal to me as I had thought, but it still bugged me somewhat.

This time, instead of the romantic kiss we shared upon returning from Christmas break, it was a simple, yet sweet, kiss that didn't last very long. I knew it was more of a friendly gesture than anything, because she knew as well as I did that I was addicted to her kisses, hugs, and general cuddling that she gave me so freely. However, I felt that these things would be coming to an end along with the school year and our living together. I asked her if she wanted to live together in a dorm the next year, but she had already made plans. I was left to be assigned another random roommate, which didn't bring too much confidence in me, considering my first roommate and the troubles she brought.

The next couple weeks made me feel like I was being cheated on, because Jesse's kisses just weren't the same as they were before spring break, and she became increasingly scarce and almost didn't want to talk to me. One evening as we both crawled into bed, she and I both laid there staring at the ceiling until she broke the silence. "I have a confession to make," she uttered, her eyes fixed on some far-off point above us, "I kinda fooled around over spring break...a lot."

"How much is a lot?" I queried, trying to figure out precisely what she had done.

When I saw her begin to count, I assumed that she was counting the number of guys she had sex with, but thankfully I was wrong. "Well, there were two guys, and I had sex in some form with each one about five times, and twice with both of them," she responded. "I almost knew that I'd give into temptation over the break, and I wanted to lose my anal virginity to someone who I at least knew, so I decided on you that night. Neither of those two random guys got the satisfaction of taking my virginity, which was rather good."

I looked over to her, half in jealousy and the other half in admiration. "Well, I'm glad to see you managed to have some fun." She finally looked back at me and, as our eyes met, we exchanged a kiss before we both fell off to sleep soundly.

Spring semester exams were a rough bunch for both of us, and we scarcely got to see each other at all during that time, as Jesse pulled a few all-nighters, although where I didn't know. Somehow it seemed like only one of us were asleep at any one given time, so we didn't get to spend any appreciable time in our room together, much less in bed together. I didn't suspect anything until one day when I saw a pair of boxers underneath her bed, a bed which she almost never used. Out of morbid curiosity, I examined them and found them to be a few sizes too big for my relatively slender roommate. As I carefully put them back, I thought I knew what was going on. I figured that she had a boyfriend that she was seeing while I wasn't around, and perhaps he had been over for some fun.

On the day Jesse was moving out, I walked in and saw a guy who I'd never met before. She introduced him as her boyfriend, and I calmly, yet very awkwardly, shook his hand and introduced myself, resisting the temptation to say that I was her girlfriend, which I had somewhat considered myself to be. However, I knew that this meant that I was no longer her girlfriend, and that I should start searching for somebody else. At least I'd have a little time to grieve before I had to pack up and leave for home, but it did little to numb the pain that crept through my heart. Just when I thought I had found the right person, she was departing from my life, my bed, and my heart.