First Times: Jenine

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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 illegal bahis 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, illegal bahis siteleri 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?).

I had to have her help getting the jeans off. To this day, I can’t peel skin tight jeans off a woman. There is some magic spell involved in it. In just her panties, she helped me off with my shirt, and then started to help me off with my jeans, only she lost her nerve a bit. In nothing but my briefs I gentled her down on to my bed. I had saved my best trick to this moment, as I began to nibble on her thighs. I teased her pussy softly thru her panties before easing them off her, bit by bit. She had brown pubes, straight and sparse, and a bit long, but not nasty. Her labes wear a dusky dark color, full and inviting. All in all, she had a very pretty pussy and I told her so. This made her giggle and she said that she really didn’t know that much about it. I told her I had seen a few, and hers was pretty. Normally, that was a line, but in her case, it was true.

I leaned in close, and caught a deep taste of her scent. It was heavenly. Strong, and sweet, the way I like it. A woman should taste like a woman, not like flowers. I began to lick. I have always been proud of my licking, and I was giving her some of my best. Her fine little ass was bouncing all over the bed; her fingers were curled into my hair and pulling. I added fingers to my tongue, driving her even higher. I sucked softly on her little clit while I slid my hands up her sides and played wither rock hard nipples. She was not quite screaming. I slipped my hands down, under her legs, under her knees pushing them up, rolling her up into a ball. This was my secret trick at the time. My tongue darted into her asscrack and danced around her little bung. This really drove her wild, after the initial shock of the act. Then, rocking her back and forth, my tongue danced from hole to hole, back and forth, and up around her clit. I finally let her legs back down, spread wide open and returned to concentrating on her clit. I kept at it for more than a half hour, teasing and pleasing, till I knew it was time. Rising up to stand by the bed, I slipped my briefs off, exposing my rock hard cock. I could feel her eyes on it, and I enjoyed her stare. To this day, I am sure it was the first real live grown penis she had seen hard. I reached for a rubber and opened the package. I tried to get her to roll it on, but she was to shy about it, so I rolled it on, slowly, feeling her watching. I slipped between her thighs, just laying there, kissing her and holding her close.

“Are you sure you are ready to do this honey?” I asked, giving her the chance to back out. She nodded and quietly, whispering, told me she was.

“I’m going to go real easy. You tell me if it hurts, ok?”

“Don’t worry about it baby, it will be ok.” She whispered to me.

I took her. Slowly, painfully slowly, canlı bahis siteleri savoring the tight feel as her wet pussy closed round me. I didn’t need any of the lube. I pushed in barely, then slipped away and then back in, then away, each time pushing a little further, a little deeper. Her eyes were glazed over, she was biting her lip, her arms were round me, pulling me closer. I was about half way in, working so slow, bit by bit when I asked her if it hurt.

“No, no, it doesn’t hurt!” she wasn’t whispering now. I eased back up, till only the very tip of my cock was in her, and then slowly, steadily pushed all the way into her. Her eyes went wide, she gasped and moaned, and her arms tightened round me.

“Hurt?” I asked.

“God no!” she answered.

“Like it?”


I began to fuck her, slow and easy. She picked up the rhythm after a bit, and her hips moved with me clumsy and jerky. Her legs were wrapping round me, her nails clawing at my back. I slid my hand under her beautiful little ass, and began to tickle her rose with a finger, then gradually eased the finger inside her. It was no problem; her juices were running down her ass making it as slippery as her tiny pussy. When my fingertip invaded her ass, her bucking grew even wilder. My cock was throbbing inside her. She was intensely tight. I was working the finger in and out in the opposite time from my cock, then in time with it. I was nibbling on her neck, whispering in her ears, “Oh baby, this feels so good!”

I gradually increased the pace, all the time telling her to tell me if it hurt, or if she was sore. Her only answer was to fuck back harder, and she cried out “oh baby BABY baby!”

After a while, I began to feel the pressure deep down inside my balls. Trying to be gentle, I was loosing, pounding harder into her. I could hear the wet slurping sound her pussy was making gripping my cock each time it plunged in and out. My body strained and flexed, and I felt the hot cum boiling up from my balls, and pumping out into the rubber. With a long deep hard shudder, orgasm took me, and I lost track of the world for a moment. As I floated back, I slipped out of her, being careful to hold onto the rubber. I cuddled her close in one arm as I groped for a smoke, kissing her first. She snuggled in close and we talked, her giggling now and then, me chuckling. I confessed to her, that I had been planning this all week. She confessed back, that she had to, except she planned it for Saturday night instead of Friday. I asked her the big question. She didn’t know.

“How can you not know?” I asked, “I know you have to know what one feels like.”

“I’m just not sure” she replied back, which made me chuckle again.

“Are you going to tell me, you have never given yourself an orgasm?”

She laughed shyly, and said “No, of course not, but that’s not the same, and it’s never felt like this. And besides, I’m the one who is new at this, remember?” She squeezed me tight, “Besides, even if I didn’t, it still felt great.”

We kept talking for a while, with the occasional loving kiss. When the time came, I pulled her hand to me. She did hold me softly, giving it a few shy strokes before her hand slipped away. The second time, taking her, I was more sure of myself. It was long slow strong steady fucking. Her legs opened wide for me, wrapped round me. I watched her eyes, and when I saw her wince a few times, I knew it was time to quit. I slowed down, and just wiggled round deep in her. She said “Honey, I’m getting a little sore now, ok?” I assured her it was ok as I slid slowly out of her, kissing her all over. She told me she was sorry she couldn’t go on, that she wanted to, and how she wanted to please me.

“You have pleased me baby, very much. I just want to make you feel good”

“You did make me feel good baby, so good.”

There would be more with Jenine over the next few weeks. But, I began to feel trapped by her. Here she was, the first “good girl” I had been with in years, and I was growing tired of her. I wish I hadn’t let it end.

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