First Time with Jean

Literotic asexstories – First Time with Jean by JamesHunter,JamesHunter
Jean and I met at a student disco. We were both in our first term at university, though on different courses. I was surprised when she struck up a conversation with me as I was not particularly looking for female company. I was there really for a few drinks with my friends. When we talked I had the impression that she knew something about me, although I had not noticed her before and knew nothing about her. Perhaps it was through a mutual friend, I never found out.

Jean had a friendly personality, outgoing but not brash. She was medium height, her head resting comfortably on my shoulder as we danced. Her hair was reddish brown and her eyes green. She was nicely proportioned for her height, her curvy figure neither skinny nor anywhere near heavy. She had nice boobs and hips, and I thought that she was beautiful.

The evening passed pleasantly, ending with slow dances and some kissing. She was staying with some of her girlfriends that night so I did not see her home, but we agreed to meet for a drink and a meal the following night and it went from there.

I had been seeing Jean on a regular basis for several weeks before we ended up in bed. We were both virgins. She had had no experience of men beyond kissing. I had been with a couple of girls in the long summer break before I went up to university, but just got as far as some heavy petting. This was not unusual for a pair of eighteen year olds in the late nineteen seventies and I was delighted when she invited me to sleep at her place rather than go home after an evening out. She made it clear that there would be no sex, though we would share the same bed. However, hope springs eternal and I thought otherwise, anticipating at least a handjob and maybe more delights to follow.

We rode the train from the city back to the suburb where she lived. She had a room on the top floor of a large four storey house which had been converted for student accommodation. All the residents were young women, students at various colleges.

After a short walk from the train station we arrived at her place. Jean opened the door and we climbed the four flights of stairs to her room. The building was quiet and we met nobody. She explained that guests were not permitted after 11.pm; but that the rule was ignored by all and nothing ever came of it. Her room was quite small but warm and welcoming. There was a single bed, a wash basin, a desk, and a built in wardrobe on one wall. We sat down on the bed and she explained that on each floor was a shared kitchen and bathroom. Once Jean had told me all of this there was a moment’s silence which she broke by asking me if I would like a coffee. We both laughed and I said something like, “Maybe in the morning.”

I slipped my arm around her waist and kissed her. Jeans lips parted and my tongue met hers, both of us probing and exploring. We lay down on the bed and continued kissing for some time. It was the first time we had been alone, somewhere totally private, and we both quickly became flushed and heated. I had my first proper feel of her breast through her clothes. She did not object, and seemed relaxed, so I eased her blouse out from the waistband of her jeans and slipped my hand underneath. I moved my thumb over the nipple which strained at the lacy fabric of her bra and she sighed. We lay facing one another, kissing deeply. Our tongues explored one another’s mouths and our legs entwined as we ground our pelvises together. My cock was rigid, and she must have felt its hardness pushing into the top of her thigh. Previously our only intimate contact had been on the dance floor, and at first I had been embarrassed by the erection I usually got. However, whenever I pulled away she would always pull me closer again and I realised she must be aware of my cock. She never objected or even mentioned it, so I just enjoyed.

Jean was breathing hard now, but when I reached for her bra clip, she broke away and sat up, saying.

“We might as well get undressed properly. I’ll go to the bathroom and change; you can get straight into bed if you like.”

With that she picked up a small bundle and went out of the door, closing it behind her. I started to undress, and after a bit of thought decided to leave my boxers on, thinking no way would she expect me to sleep in my jeans, but stark naked might be a bit full on for the first time since she was obviously planning to be wearing something. I had a cursory wash in the basin and dried with the towel hanging beside it.

Jean reappeared in a few minutes in a rather unexciting night dress, and hopped straight into bed. This was the first time I had been in bed with a girl, and just being there was great, whatever else happened. We resumed kissing and I soon liberated a breast from the nightdress. The nipple was hard and pink, and she enjoyed me sucking and licking it. Although it was obvious that she was very aroused, every time my hand headed south it was pushed away and she studiously avoided any contact with my aching cock.

It was clear that Jean did not want to take it any further for the moment, and as she had said as much before we headed back to her place I couldn’t complain too much. Maybe she just hadn’t thought of a handjob as a compromise, and, lame as it sounds, I couldn’t think of a polite way to ask her to wank me off. I really liked the girl, and it looked as though with a bit of patience things would soon go my way, so I didn’t want to upset her by being too insistent.

There is only so much kissing you can do and eventually she fell asleep, leaving me awake and frustrated. Sleep was impossible, the bed was designed for one, the room was too hot and my cock was like a length of oak, so I went over to the basin and masturbated. After a few firm strokes I shot into the porcelain and felt a lot better. I was disappointed, wondering why she had invited me into her bed if that was as far as she wanted to go. Probably just inexperience and a lack of communication, and maybe she just lost her nerve. Or perhaps I should have pushed it a little harder. However I liked her a lot and decided to be patient and stick with it.

This pattern of events was repeated over the next couple of weeks, making a little progress each time until the point where I had fingered her to her first orgasm. She would rub my cock through my boxers, and even take it out sometimes, but not make me cum. She just would not rub it hard enough or long enough. When I asked her why, especially after she had had her first orgasm, she just could not explain. I decided that this could not go on, and that something was wrong with such a one sided relationship. I didn’t want to split, so I decided to take matters out of her hands. I felt that if we could get over this bump things might normalise. I came up with a plan to cum as if by accident, and just see how she took it.

I put myself on a no masturbation regime for five days (an eternity when you’re eighteen). Next time we were together, while she was in bathroom, I masturbated until I was just on the point of orgasm. When Jean returned she got into bed as usual and we started making out. I pulled her night dress up and knelt astride her, kissing and sucking her breasts and nipples. I took my cock out of my boxers and put her hand on it. She pulled back and forth gently as usual but he movement was too slow and the pressure too little to get a result in normal circumstances. But tonight I was already primed. I raised up and knelt over her belly as a trickle of cum escaped, unnoticed by Jean. She probably would have stopped had she realised what was going on but she changed her grip, now fingers on top, thumb underneath. The tension built quickly to the point of no return and released into a sudden and intense orgasm. Powerful spasms sent thick spurts of sperm arcing through the air to land on her belly, tits, throat, face, and hair. The headboard and pillow got decorated as well.

The minute I had done it I (almost) regretted it. I hadn’t meant to make such a mess of her, but she actually took it very well. To her credit she picked up the pace and pressure and kept wanking me until the last trickle. Someone must have told her never to stop once a guy starts to cum.

She didn’t make a fuss, and as far as I remember, just said something like,

“Oh, I wasn’t expecting that. There was such a lot of it, is there much in my hair?”

And that was it. No recriminations and she was remarkably unconcerned about being covered in sperm. One of the girls who had done me before had reacted as though it was battery acid on her hand! From that time on we spent two or three nights a week together. The awful nightdress was never seen again and we slept nude. Jean still would not let me fuck her, but after that we enjoyed mutual masturbation each time we met, and would often manage to cum together.

One afternoon we decided to have a close look at one another’s genitals and talked about what felt good or not so good. I lay on my back as she checked out my cock and balls from close quarters. She squeezed my balls cautiously until I said anxiously, “That’s hard enough.” She pulled back my foreskin so that my knob popped out, then wet a finger with her saliva and gently rubbed it over the head, paying special attention to the pee hole and frenum and then the rim. It felt great. When it was my turn I gazed at the auburn curls as she spread her thighs, and moved closer. Her slit opened as she splayed wide so that I could see all she had. I got an impulse to kiss between her legs and went down on a pussy for the first time. I kissed and licked and sucked at each part of her, wanting to know what pleased her most. She seemed to love all of it and soon afterwards I got my first blowjob. It was terrible, all teeth, but I feigned great enjoyment, and anyway was more than happy to have my dick in a girls mouth. This encouraged her and she soon became very good at it, though she wouldn’t let me cum in her mouth.

I still ached to be inside her, of course, but there is a lot that two people can do together short of intercourse, and it was all new to both of us. We enjoyed the pleasure we gave to one another almost as much as our own. I think Jean tried especially hard to make me happy because of what she was holding back, and as a result I was content to wait for her. We were in love.

Sometimes now Jean would take the lead in trying new things. She had a part time job at a cosmetics concession in a big store. One morning, she had dressed in her uniform for work. It was a white dress, rather like a nurse’s uniform. Very sexy with the black stockings, if you like that sort of thing. I do, and had asked her to wear it to bed a couple of times, but no luck. She didn’t understand the attraction; it would get creased was only one of the objections. I was still in bed with a something of hangover, but I swung my legs over the side when she was ready to go, meaning to get up and see her out. Seeing I was awake came over, kissed me and knelt between my legs.

“I’ve got ten minutes before I have to go, let me get your weekend off to a good start.”

She kissed my belly and thighs while masturbating my semi erect cock, then lifted it up and started licking and sucking at my balls. This was new and very sexy, especially with the uniform. She pulled my foreskin back and sucked my cock into her mouth, moving her head back and forth while her free hand undid the buttons on the front of her dress. Underneath her breasts were restrained by a lacy bra of the type we used to call a “front loader.” Jean deftly unclipped it and leaned forwards, rubbing my cock around her cleavage and over her breasts.

“You can cum on them if you like.”

“You’ll be late for work if you have to change.”

“It’ll be Ok. Go on, I want you to.”

She put her hands either side of her tits and squeezed my cock between them, hefting up and down. I leant back on my hands and watched. It looked great, but wasn’t really working without any lubricant so she put one arm under her breasts to hold them together and went back to masturbating me.

“Go on, I want you to cum on me. Cum all over my big tits. Shoot your sperm all over me.”

She took me in her mouth again, sucking and tonguing my knob, and wanking me really fast. This always got me off quickly.

“I’m going to cum.” I gasped.

She leaned back a little and pressed the head of my cock to her cleavage. Her fist moved steadily back and forth on my penis.

“Go on love, you know you want to. Cum all over my tits.”

I groaned as I felt the familiar tightening in my groin and the first spurt of sticky opalescent fluid lobbed onto her chest.

“That’s right love, do it now, it feels so good doesn’t it? Let it all come out, I want it all over my tits.”

A couple more spurts splashed onto her chest and throat, then she tightened her grip and slowly squeezed the last drops out, spreading the mess around with my cock head.

“Did you like that? Did it feel good cumming on my tits?”

“Yes it was great, but why now when you’re just off to work and all messed up?”

“It’s not so bad. Anyway, I wanted to do something nice for you. Something different, like you did for me the first time you kissed between my legs.”

She wiped her breasts with some Kleenex.

“I know you want the whole sex thing but I’m just not ready yet. Sometimes I feel like I’m a freak for wanting to wait for a bit but I just want the first time to be when I’m completely comfortable with it.”

Jean eased her breasts back into her bra and fastened the clip. She lifted them, one in each palm, to get them comfortable and then started to button up her dress. I loved watching her dressing almost as much as undressing.

“If anyone asks me what fragrance I’m wearing today I’ll tell them its eau de semen! You don’t mind waiting a bit longer, do you?”

I kissed her.

“Of course not, we’re having plenty of fun for now.”

And we were, so I really didn’t mind too much. I knew that pretty soon she would be ready to let me in. She was already on the pill. One day we had discovered baby oil, and, lubed up, she had squeezed my cock between her closed thighs. We were in the “spoons” position and I thrust away until I came. It felt sensational, almost like the real thing, but my sperm ended up all over her pussy so we thought we had better be careful.

I never really found out what decided Jean on the particular day that the big event was to happen. I do know that she had arranged with a friend who lived in the same building that they would both loose it on the same day. The couple were Kath and Tim. I learned from Jean that they were both virgins as well and mutual masturbation was as far as they had got. The girls were close, but apart from a few times we had gone out as a foursome I hadn’t seen Tim often. One thing I did know about him was that he had a big dick. Kath had confided as much to Jean and that she was nervous about the likely pain the monster would inflict the first time. I was sceptical, and asked a question.

“So how many cocks has Kath seen?”

“Three, her two brothers and Tim’s.”

“Well, how many of them were hard?”

“Only Tim’s of course! Anyway, don’t worry about it; I’m quite happy with yours.”

“Well, if you’ve only seen one, and so has Kath, you’ve no way of knowing whose is big, small or average. You can’t tell by looking at limp ones. Look at mine, if I’m warm and relaxed it looks big; if I’m cold it shrinks right down. I could be the guy with the big dick for all you know!”

Tim’s alleged huge dick became a bit of a running joke – if one of us, say, saw salami hanging in a shop we would make a remark like, “Hey, does Tim know some shops got his cock hanging in the window.” Ok, you probably had to be there, but you get the idea.

The story seemed to have been substantiated when the big day arrived because we had no problems whilst Tim couldn’t manage to get it in, to put it delicately. In fact it was a couple of weeks before he managed to penetrate her properly. Jean told me everything that Kath confided to her. I assume now that the opposite applied, though it didn’t occur to me at the time. Funnily enough, a year or so later we would find out the truth of the matter by accident, really having forgotten about it by then.

Anyway, when the day came it was a surprise to me as Jean had said nothing. It was a Saturday. We had arranged to meet Kath and Tim for a lunchtime drink in a pub close to where the girls lived. Jean looked nice, as always, in stretch jeans and a silk blouse. She seemed to be in a happy mood and was a little excitable. Kath was a bit more subdued, and Tim was just Tim. We had a couple of drinks and something to eat and then walked back to the house, two couples hand in hand. We left Kath and Tim on the third floor and continued up to Jeans room.

Once in the room we kissed and lay down on the bed, starting to help one another out of our clothes. We had not seen one another for several days, so our caresses quickly became urgent. When all the buttons were undone and the easy garments removed we jumped up and took the rest off. Jean left her panties until last, grinning at me and wriggling her hips as she took them down. They hung on one foot and she kicked them into a corner with a flourish. We stood facing one another, and I admired her perky breasts, the pink nipples contrasting with her creamy skin. My gaze dropped to the curly triangle between her thighs.

“See something you like?”

“Not like. Love.” I replied.

She gave me a twirl then walked to the bed, giving my erection a friendly tug as she passed me.

“That’s easy to see.”

Jean lay on the bed, with her buttocks on the edge and legs spread, feet on the floor. I knew what she wanted as this was her favourite position for me to go down on her. I knelt between her legs and kissed her thighs and pussy. She spread wider, cupped my head in her hands and pulled me closer. I started to lick at her lips and around her clit, probing at the entrance with my tongue from time to time. She was very wet. Sometimes she liked to cum like this before turning her attention to me, but this time she stopped me.

“Come up here, your turn now.”

I got onto the bed, but had being enjoying what I was doing to her, so knelt over her to let her lick my cock and balls for a moment, then went down into the sixty nine position. As I pushed my tongue back into her slit, I felt Jean pull back my foreskin and take my cock head into her mouth. She held my cock in her hand but did all the work with her tongue, now probing at the underside and slit and now swirling all around the knob.

We enjoyed this for a few minutes, and then I withdrew from her mouth and turned around to lie beside her. I reached for the baby oil on the bedside table, but she swung her leg over and knelt astride me, saying.

“We won’t need that today. I’m wet enough for what I want.”

She ground her slippery pussy back and forth on my swollen cock.

“Let’s make sure you are as well.”

She moved down and sucked at my knob, covering it with saliva and then went back to her original position. She raised one leg a little and rubbed the purple bulb of my cock back and forth along her slit, using her other hand to spread the lips a little.

“What do you think, shall we put it in?” She asked.

I answered her by pushing my hips up.

“Oh Yes!”

But she was already pushing down on me. She still had my cock in her hand and moved it around to find the entrance, pushing down some more when it was in the right place. It started to go in bit by bit as she moved up and down, going in a little more each time. My knob slipped past the tightness of the entrance and then gradually all the way in. When her pubis was against mine she stopped where she was, kneeling on me, and we looked into one another’s eyes smiling at our achievement.