Part IV: The First Time
I kept hoping that I wouldn’t wake up and this all be a dream, very gladly it wasn’t. I was sitting on my couch, watching espn, but I wasn’t really watching it, I kept reflecting, going over in my head the things that had happened, things that could happen, what was next. Well for the immediate future, she was coming here after her last class of the day. She said on the phone that she had something special in mind for tonite. Up to now we hadn’t done anything more than oral sex, and a glimpse of a threesome with her roommate. I knew that the special something had to be our first fucking, penetration sex. It would be a first for both of us. I made sure not to repeat an earlier mistake, I had purchased a large pack of condoms on my way home from campus. I heard a car pull up. I walked to the window, and saw her walking to the door, she was wearing a red shirt that had a v-neck exposing the tops of her breasts and long tight jeans. I walked to the door and opened it just before she got there, to her surprise. “Hey stranger.” I said. She playfully pushed me backward, closing the door behind her. “So what was so special you had in mind” I asked her. She responded by throwing me down on the couch, then jumping on top of me, she made a point of putting her cleavage, from her red shirt, right on my face. “I think we should broaden our horizons” she said. For a second I thought she might mean something kinky, then I realized I was right to begin with. “Like what” I said, playing dumb. “I think you know” she said, playing back at me. “Stephanie told me that I shouldn’t put off having sex. She said its stupid to pretend that we will wait years to actually have sex, it will just complicate things, and then we’ll break up and I’ll wind up having sex with someone I don’t like as much”. “Who said we were waiting?” I said. “Well I was going to make you wait” She said biting her lip. “Remind me to thank her later” I said.
…
“How does this thing work?” she said. “It has instructions on it” I said. “Ohh” she said as she turned it over. Holly now naked standing in front of me, I was sitting on the edge of my bed, naked as well. She tore it open and unrolled it. “I think you stick it in now” she said. “I think you mean, YOU stick it in now” I said playfully. “Fine” she said feigning anger. She over exaggerated her hips walking over to the bed, her breasts bouncing as she walked, nipples hard from the attention they received minutes ago on the couch. She knelt down in front of me. “Let me make sure it’s good and hard first” Holly said. She stroked my cock a few times. Then she slipped on my love glove, it was the first time I ever had a condom on. It felt kind of weird, but it didn’t seem to de-sensitize very much at all. I stood up from the bed, holding the sides of her arms and bringing her up with me, turning us around and putting her on the bed. I crawled up on top of her, holding myself just above her. I sucked on her nipples and licked her pussy a few times on my way up. We were lying face-to-face, cock-to-pussy. I just looked into her eyes. She looked back into mine, there was no fear in her eyes as I had somewhat expected. She was embracing this as much or even more than I was. I gave her a look that said ‘are you sure’, she saw my face, she leaned her head up to my ear and whispered, “fuck…me”. I was convinced. I gently thrusted forward, not looking, and missed hitting her pubic hair. She started to giggle. I smiled at her before looking down and with one hand putting my cock on her lips. I gently pushed my dick into her, it took more force than I imagined. Her tight eighteen year old pussy embraced and surrounded my eighteen year old cock. She let out a whimper, of pain or discomfort, she nodded her head, indicating that I should continue. I started to push in and out, very slowly and not very deep. I continued a slow pace for some time. Her velvety lips hugging my cock. Her nipples were now fully erect, and her breathing was very quick. She was aroused, but this was clearly not going to get her off. I started to go a little bit deeper and little bit faster, after a while I was nearly to the point that I could get it all the way in, but I had slowed down considerably at her request. I could tell she couldn’t take much more of this, it was too much pain now. I pulled out.
I laid on to her body, taking her mouth into mine, our tongues met passionately, embracing each other, our sweaty chests rubbing together. I moved down, kissing and licking her neck and massaging her breasts, until I was lips to lips, her other lips. I started to lick up and down slowly, then taking in her clit massaging and using one hand to complement my tongue on her slit, using my free hand on other various parts, as she moaned, putting her hands in my hair, and thrusting her hips upward, arching her back. “ohhhh, yes john yes” she whispered repeatedly. Her orgasm hit her like a ton of bricks. She suddenly moved her legs and arms violently like she was possessed. Screeching and screaming, as I buried my face in between her legs. It took minutes for her to calm back down, from her excited state. She was breathing incredibly rapidly. I laid down beside her, both of us staring at the ceiling, my right hand in her left. “Is it my turn now” I asked the ceiling. “I though you’d never ask” she said nearly before I had finished my sentence, suddenly leaning forward putting her mouth on my clothed cock. She started licking it. ‘it tastes like rubber” she said disappointedly. She started stroking it. She was resting her head on my stomach, her back exposed to me, all the way down to her beautiful butt. I reached my right hand down caressing her back , down her side, to her hips, ash she continued stroking my cock. “Holly, I love how beautiful your back is”. “You just like staring at my ass” she responded playfully. Then she picked her head up and put my head into her mouth sucking on it and licking all around it. “I think I could deal with this rubber thing, it keeps me from getting shot in the face again.” She said giggling. I just started to chuckle at that. She started going faster, and stroking with her right hand. Holly alternated her hand on my shaft and balls, mouth still at work. I decided to let her get a surprise, rather than alert her to the problem close at hand. I shuddered, as my balls emptied, my jizz contained in the condom. She started to giggle as her mouth was still on my mouth. She pulled her mouth away from my cock. “It tickled my tongue” she said, still stroking with her right hand. She moved back to lay next to me again. We fell asleep, exhausted.
…
I woke up in the night, realizing we had fallen asleep, I even still had the condom on, though it had nearly fallen off my shrunken member. I got out of bed, realizing that she was no longer in bed. I could hear the shower running. I snuck into the bathroom, she was showering. I snuck up to the shower curtain, I was planning on opening it and surprising her, but just as I got the shower, I heard her moaning. I stopped. It sounded like she was masturbating. I walked to the other end of the shower, knelt down, and peeked through between the curtain and the wall. Holly was laying down, pussy in the path of the falling water, her head was just below mine, her eyes were closed. Her right hand was playing with her clit, and her left hand was rubbing her all around. She was lost in ecstasy, she wouldn’t have noticed me if I had yelled. Holly was breathing very deeply. “Ohhh John, yes” She said very deeply. That made me more excited than the sight had. I sat there watching her masturbate, for several minutes. When she finally orgasmed she opened her eyes, and I instinctively moved my head back, I slowly crept out of the shower and went back to bed. I pretended to be asleep as she returned from her “cleansing” shower. She returned to bed, hugging my body tight to hers, her face to the back of my head, her chest to my back. She, thinking I was asleep, whispered into my ear, “I love you John”. I smiled, but gave no reply as we both fell back asleep.
