First times are always special. This is a true story. Even nearly twenty years later, I remember it all well. Being truth, it has a slow start, and you may not find it as erotic as my last submission.
There are a lot of women in my past, that I didn't treat as well as they deserved. One sticks out in my mind now and then. I had known Jenine for years; we went to the same small town high school, belonged to the same church, and even sang in the choir together for a while. I always thought she was cute I suppose, in a quiet shy sort of way. She was not what one would normally call a beauty in any sense, but she also wasn't plain.
I don't know how long it had been since I had seen her. I was out, at my favorite bar, just a college guy on the town. None of my usual drinking buddies were out that night, at least not at that bar. But there was a table with a lot of kids I had gone to school with, all of them too young to be in a bar, but it was that kind of bar. They were all probably college freshmen and sophomores, a couple years younger than I was. I remember that she was 19. There was one stranger in the crowd, a cute blonde that was rooming with one of the others. That's what initially drew me in to their group: fresh meat. Yeah, back then, I was that kind of guy. One of the boys was obviously interested in her and I didn't care; he was a dweeb. I had all the girls laughing, but that's all the further I got with the blonde. But Jenine kept on laughing, and we all got fairly well drunk. We danced, closed down the bar, and went out for food, the whole group. Somewhere along the line, Jenine and I ended up holding hands a lot, and my arm went round her slender waste. When it was time for them all to head home...most of them to mom and dad's houses or to their dorms, I kissed her goodnight. Several times. She kissed back, and quite well.
Somewhere in the following week I called her up. I knew she still lived at home. That part wasn't all that easy. Jenine had an older half sister, Sherri, who I worked with, and probably could have had with a little effort. She had had quite a crush on me at one time, and had come to a party with her best friend to be with me. Somehow, I ended up with her best friend in my bed while the party was going on. Sherri knew that I was a player, even though back then, we didn't call it that. The fact that her friend ended up knocked up didn't help matters, even though she married her boyfriend and told him it was his. Still, I knew I had a reputation around my home town, and it made me a bit nervous about picking up Jenine at her folk's house. I shouldn't have worried. Her mom loved me, and seemed thrilled that I was taking Jenine out.
I don't really recall what we did that night, dinner and movies I guess, that's really all there was to do. A few nights later, she was at my apartment. Sometime that night, she revealed to me she was a virgin. I can't say I was shocked, but I was a little surprised. Like I said, she was cute. We were making out on my couch. It was good old fashioned making out. I didn't make a play, even though my normal routine called for it, and usually succeeded. She was wearing jeans, and a buttoned shirt, with an undershirt. It was stylish at the time. The shirt got unbuttoned without any resistance. The undershirt slipped up. She had no bra on, and truthfully, she didn't need one. Tiny little perky tits, a cups, not champaign glass titties, they were martini glass. Perfect little cones that fit right in the palm of my hand. Her breath got ragged as I teased those little mounds, her body trembled. It wasn't scared tremble, it was excited tremble. She moaned and squirmed as I felt them up and sucked on them. I might have gone further, but in those days, jeans were skin tight. To go further, I was going to have to get them clear off her, and for some reason, I chose not to push it. Besides, at that point, I was already planning ahead, step by step, taking her. That was Tuesday.
I had to work on Wednesday, so I didn't see her in private again till Thursday. We caught up to each other between classes on campus, had lunch together, that sort of thing. Thursday night, she came over. We watched TV crashed back in my big bean bag chair, even better in a lot of ways than the couch. It didn't take long till a heavy make out session was in play again. Tonight, there was a change. She was wearing sweats (I would find out later, that was on purpose). As I worked my way up under her sweat shirt, meeting nothing but bare skin, she got the wiggles again, but not as much as that first time. I am guessing she had only had her tits felt up maybe a handful of times in her life before then. If I do say so myself, I was a patient and good lover, even at 21. I'm a small man, and like a chubby girl who tries harder to please a man, I knew I had to be very good at what I did to get the women. So I took time to learn, reading, studying, asking the right older women. So when I went to work on a girl's boobs, I generally made a good effort. No wham bam thankee ma'ams for me.
But those loose baggy sweatpants were just to inviting. And anyway, it fit into my plan to play with her pussy tonight. I met no resistance at all as I slowly got my hand into her pants, and into her panties. To my great joy, she was quite excited. Her virgin pussy was slippery wet to the touch, and I did a lot of touching. I spent quite a bit of time just toying with the outer lips, rubbing softly, and only occasionally letting the tip of a finger dip between the folds. I worked my way to teasing her clit, and finally, to slipping my finger into her. She was nice and tight, and if she hadn't been so wet, I doubt I could have done it. And before you ask, no, there was no hymen to pop. Based on her comments later, I take it the doctor had taken care of that. The whole time I was working, her hips were all over the place. She moaned, squirmed, kissed hard, her breathing totally ragged. Did she cum? I don't know. I would have to say she did, and several times. I kept my pace very slow, very gentle the whole time. I had never done a virgin before that I knew of. Most of the women I had been with were on the slutty side, or older. I had been with a married woman before I was 19.
At one point, I had slipped my hand back, just resting it on her mound, and come up for air, and catching a moment of the movie we were watching. She reached down and grabbed my hand thru her pants and pushed it back and asked me "Do you want to watch TV or fool around?" I teasingly told her it was a good movie...which made her laugh. She teased right back, starting to tug my hand up out of her sopping panties when I leaned over and kissed her again. She pushed my hand back. I'm guessing this was as far as she had ever been, but that petting (what we called fingerfucking in those days) wasn't totally new to her. I finally had to stop. I was getting worried that she was going to be too sore for what was forming in my mind for the next night. I also knew if I went much further, it wasn't going to be the next night; I was going to take her right then. I had a raging hard on in my jeans that I was barely keeping under control. I didn't try to get her to help with that problem. Despite her pussy juice all over my hand, there was really no doubt, she was a "good" girl, and "good" girls back then generally didn't play with yours till after the first time you took them. It was something we were used to. I suppose that's one of the reasons I went for the slutty type.
Friday night rolled around. I had cleaned up my place, made all the right preparations, including making sure the rubbers were handy in the nightstand, the lube was ready ( I had picked up the wrong box and had un-lubricated rubbers...and I had a tendency to break the damn things under normal conditions, thus leading to my daughter). When Jenine got there, we had a few drinks, and quickly wound up on the couch. Her shirt came up readily, exposing those wonderful little tits to my fingers and lips. I began to work lower. Tonight, she had jeans on again. I got them unsnapped and unzipped, but couldn't begin to work my hand inside them. In my suave, sophisticated manner I commented on that:
"You and your damn tight jeans!"
She looked up me, almost smugly and said "Well you can always take them off." Almost as soon as she said it, she gave a bit of a gulp and went a little red in the face. I stood up and very easily picked her up in my arms. Her lips came to mine and I knew, this was it, just as I had planned. I carried her into my bedroom (suave, right?).
