My signifcant sexual firsts
written by:
Socrates

My notable firsts

I dreamt the other day of a whole list of my ‘firsts', some of them too dangerous to repeat. The ecstasy of my first hand-holding, my first kiss, my first touch of the bare breasts of my first girl friend .... and these experiences were months apart. In those days we were meant to respect our girl friends and to assume that they were as innocent as we were.

I will never forget the joy of that first feel as I pushed into my girl friend Mary's blouse and held one of her breasts in my hand on the back row of the cinema. Her breast was so soft and so warm.

When shortly afterwards I persuaded her to undo my zip and pull my erect cock out of my trousers I was scared and excited at the same time. We used the overcoat on my lap to hide the sight of my cock being squeezed by her hand. It stayed erect throughout the whole film. Mary must have thought cocks were ramrod stiff like that all the time. I wish I had that staying power now.

We settled for that level of petting for months. We were so inexperienced and it was such a big deal to go any further. When later, a much more experienced girl picked me up in a cinema by touching her leg against mine, holding my hand and then making it clear she would welcome me touching her in a more intimate way I was in way over my head. It was so unusual to be picked up by a female in a public place. But I rose to it and quickly ticked off another first: a hand up her skirt down into her knickers and deep into her sopping wet pussy. Man that was an outstanding achievement; to score so highly so quickly with a girl I had never met before. And all of this while the friend I came to the cinema with was acting as a silent witness to my pulling success whilst pretending not to see or hear what was happening next to him. I met her by arrangement alone in that same back row a week later and we went even further. My fingers were soaked again and she also wanked my cock to completion. This was the first time a girl had masturbated me.

I still hadn't experienced cock sucking. That didn't happen until I was at college. It came shortly after a girl I was smooching with at a dance pushed her abdomen hard against me and rubbed it from side to side until she detected my hardness. Muttering to me that I had something that needed her urgent attention she took me outside and behind the dance hall, unzipped me, and knelt down in front of me. In seconds she was squeezing my ball sac and sucking my dick and I swiftly jerked and gushed into her. I couldn't believe how fast I came and that she slurped and swallowed all of my spunk without batting an eyelid. I never did figure out what pleasure she gained from this disgusting glorious act.

I met another girl at a dance the week after and when she ground her crotch into me in the slow smooching dance I waited for her invitation to go outside. But this girl was more ambitious. She told me that she had recently split up with her fella and that she was missing it! I thought I had misheard her until she invited me back to her college dorm to spend the night. I panicked. This was obviously the most experienced girl I had ever met so far and I was the most inexperienced guy she would ever meet. She scared me so much I made an excuse and fled. I was still a good catholic boy at the time and thought that the first intercourse should be with your spouse. It was too important to be offered as lightly as this young woman was doing. My respect for her vanished and I thought of her as disrespecting me. I knew nothing then of women having their own sexual needs. I thought only men could possible get that randy and need that kind of release. My first wank in a public street followed as I walked home alone to my lodging feeling very frustrated at what I had turned down. So on the way home I stopped in the shade of a wall, pulled my cock out and wanked it until I gushed on to the sidewalk.

By now my religious scruples were fading and I was fed up of being the only guy I knew of my age who had never felt a pussy grip his cock. I went to the next uni dance with the express aim of getting laid. I pulled a likely looking girl and walked her towards her bus stop after the dance. She was slim and pretty and wearing a flowered frock, and cotton panties plus, I found out later, a lacy bra. We kissed, gently at first then with more passion. My tongue explored her mouth and she did the same to me. I fondled her breast though her blouse and she moaned. My hand travelled down lower and up her skirt. Higher and higher and still she didn't stop me. I felt her mound and rubbed it gently through the cotton panties, then more urgently to provoke a reaction. She showed she enjoyed this by becoming noisier and squirming vigorously against my hand.

I moved up to her elastic and into her panties and down to her bare pussy. Her reaction was one of shock but she didn't stop me. One finger then two penetrated her. She screamed quietly but loud enough to arouse me further. I felt her explore the bump in my pants - rock hard already. She unzipped me and took it out and stroked it. Jesus man, I thought, this little girl really does want me to fuck her. I turned her around and lifted up her blouse, found her bra strap and unhooked it. Her breasts were a good size and firm. Lovely to hold and squeeze. We were down an alley and in a doorway. No-one around. Dare I? Yes. There was no stopping me. The skirt came up. The cotton panties down. I bent her away from me, lifted one of her legs, mounted her, unzipped myself and shoved my cock into her pussy. Penetrated her, fucked her, ravished her as fast as I could. She groaned but still did nothing to stop me. I was home in a cunt at last. No feeling on earth to beat it. I drove in, and up, and deeper, and more urgently. Over and over and over and over again. Animal-like. Completely selfish! She was fuck-fodder. I was getting my rocks off. Needed to so badly.

At that moment I couldn't care less who she was and what she looked like. The only part of her that mattered was her cunt. I wanted to impregnate her. I might have been a danger to her through not wearing a condom, but she was too far gone to protest. I rammed into her whilst squeezing her breasts hard, and soon I came. Streams and streams of it. I grunted, groaned, moaned and spurted deep into her. Then it was over and I shrank out of her, feeling ashamed at my selfishness but massively elated at the same time. I'd done it, got rid of my virginity, joined a higher league. Then reality hit me. No condom. What have I done?

It's OK, she said, reading my mind. I'm on the pill. I wanted you to do it. I needed it as much as you did. I needed to know what really rough no-holds-barred fucking was like. You've done your job. Broken me in to this kind of sex. Treated me like dirt. But now I don't want to see you again. Next time I need someone less selfish, who doesn't just see me as a whore. Some one who will think of my pleasure not just his own. And will treat me as a human being not an animal.

She kissed me on the cheek. Pulled up her knickers. Fastened her blouse. Pulled down and straightened her skirt and ran for her bus. I never did saw her again. But she taught me a lesson I will always remember. I never again did that to anyone. Never treated anyone as just a spunk-basket!

The rest of my college career is a blur. Suffice to say that by my final year I was neither religious nor inexperienced any more. In the term before my graduation I met the woman who became my wife, the love of my life, and we are still together 25 years later. I knew after just ten minutes with her, that she was the one. We were engaged within a month, and married shortly after we graduated. We then both went on to train as teachers. With marriage I discovered the difference between rough selfish sex and mutual unselfish loving. The first is just an animal need. Any warm body (within reason) will do. The second is terrifyingly spiritual, in a non-religious sense, and only one body at a time will do. Making love is completely different from having horny anonymous egocentric aggressive sex with lots of different women in turn. It takes years to get right and the effort to make it work is well worth the effort.

This intense and completely loyal loving monogamous feeling lasted for 20 years or so and included the raising of three gorgeous children ..... but then my beloved gradually contracted a persistent illness that needed strong medication, the side effects of which included the destruction of her libido. Devastated, I returned at first to the masturbation that had sustained me in my young virginal religious days. Then I broached the problem with her and hinted at my selfish need of a warm responsive body at times. She was very understanding but very sensible in her response. She had read of another couple solving this by the husband visiting a massage parlour and paying for relief. She could cope with that, she said. But she told me she would be less happy if I had full blown affairs. That would be harder for her to bear. But if I did go down that path she didn't want to know about it or when it was likely to happen. And that is how my extra-marital second sex life began.

First I discovered on-line chat groups and became quite skilled at chatting up and arousing women on-line and sometimes on the phone. Many of them said they found my voice very sexy, I was funny, made them laugh and had a good way with words. I had many a glorious wank as the woman on the other end of the line did the same thing to herself.

But it wasn't enough and the temptation of the chat lines became more irresistible. Some of the women seemed as needy as me and eager for some excitement on the side. So I made arrangements to travel to my first adulterous liaison with Elaine, who lived over 50 miles away. Elaine was recently separated and said she understood my predicament. Phone and on-line sex with her was good, but left us both wanting more. So she let me travel to her flat early one morning after telling my wife I was going to work. When I arrived I found her in her dressing gown wearing underneath what I had asked her to wear, her sexiest, skimpiest matching underwear. I opened her gown and ogled her lilac lacy bra and skimpy matching thong. I gripped her buttocks and pulled her against me. My cock swelled up as I pushed it against her. The feeling between us was instant, the lust from the phone sex cane alive in no time so I removed her dressing gown and led her to her bedroom and she climbed under her duvet. I stripped off quickly, condommed myself (my first condom for almost 20 years) and climbed in beside her. Her smooth softness and warmth excited me so much I was trembling. I had to take a grip on myself and slow down. This was not like in my college days. This woman was not just fuck - fodder. She was a pleasant, sociable, presentable grown woman, more friendly and far better looking than I had feared she might be, but she was also lonely and vulnerable. I determined to treat her with respect, as a woman, a person, someone's daughter, a lady with feelings, to be wooed and charmed, seduced with style, not roughly taken. We lay together holding each other, our flesh touching along our whole length. She cuddled against me. I gripped her close and tight. I held her buttocks and squeezed them. She must have felt my hard cock and adjusted her position so that it was close to the mound between the top of her legs. I felt her heat. I ached to possess her, to push into her, to enjoy her, to fuck her, but I held back and rested my hand on one cup of her lacy bra and squeezed that breast as I moved over to nuzzle against and kiss the other breast, searching for and finding a nipple to nibble and playfully bit it. After a while I moved my hand to between her legs, asked her to spread them wider for me and cupped her mons with my palm. I pushed her thong to one side so that I could thrust a finger gently between her lips. She reached over and wrapped her fingers around my shaft and I moaned and made some joke about being hers for as long as she held my cock. I said that if she led me around the house holding on to me in that way I would not be able to refuse her anything. Whoever controls a man's cock controls the man, I told her. She laughed and moved her hands to my ball sac and squeezed that instead. This provoked me into pushing two fingers into her very wet pussy. We spent a long while mutually masturbating each other. It was bliss. I never wanted to stop enjoying and being enjoyed in turn. She returned to holding my cock and she tugged me into moving to and fro against her. I pushed my fingers deeper into her and she squirmed and moaned louder. I kept them inside her and when I pressed my thumb against her clit she screamed and rocked enthusiastically from side to side against me. I spread her juices on the outside of her gash and increased my pace. She slackened her grip on my cock and concentrated upon her own pleasure. I increased my manipulation of her pussy and she bucked against me for what seemed ages, then slowed and relaxed and calmed and quieted herself. We had only been together for about 15 minutes and already I had made her cum. I was proud of myself. Maybe I would make a good middle-aged stud.

I held her against me. It felt so good. She pushed me on to my back and climbed up on to me, lowering her vulva on to my turgid rod and gripped me tightly. I'd given another woman an orgasm and was now penetrating her with my penis. My first adultery was taking place. It had been ages since I had had full sex even with my wife and 25 years since having sex with any other woman but my wife and it was exciting. This seduction had taken me months of telephone calls and typing to arrange. I wanted physical coupling with this lady more than anything else in the world at that moment. This new attractive lover, who fancied me, found me sexy and lusted after me, wanted sexual pleasure as much as I did. And she didn't want it with just any man. She wanted it with me!

I turned her over so that I was on top of her and pushed deep into her .... slowly at first then with a frantic urgency that she matched. We went at it like rabbits. No one had ever fucked me back with such intensity, such urgency, such desire. I found this so overwhelmingly sexy it made me speed up and power drive into her. My cock had never been harder, never wanted a cunt as much. You are beautiful I whispered into her ear as I nuzzled close against her. You too she replied. Please fuck me again! I need fucking so very badly. I want you Jack. I want you to fuck me over and over and over again. I turned her over on to her front and placed a pillow under her tummy and sat astride her as I rogered her again and again and then some more. Finally I exploded into the condom in her pussy and we both collapsed into a deep sleep. The deed was accomplished. I'd fucked the gorgeous woman who lusted after me, in place of my wife who loved me but couldn't lust after me any longer.

Later, I don't know how much later, I was woken from the deep sleep that followed our love-making by another first. I thought I was dreaming at first. Someone was sucking my cock and squeezing my balls. Man, if this has never happened to you, please try to arrange for it as soon as you can. It is unbelievably sexy. You think you are having a sexy dream then you suddenly become aware it is real. You are stiff and hard as hell and being squeezed in a gentle suction vice. A bit like a milking machine sucking a cow's teat. In no time at all I jerked, screamed out aloud and flooded her mouth. She swallowed at all like a pro.

I had one more session with Elaine two months later. I'd managed to get back from working away a day earlier than I told my wife and was able to have supper and a sleep over with Elaine. The loving was just as spectacular as the first time and I was thoroughly hooked on this woman. Thinking of her dominated all my thinking time. On my drive back home after this overnight stay Elaine texted me that she had never enjoyed sex so much for decades and my heart sang, I was so pleased with myself. But pride comes before a fall, as the sage said and disaster turned out to be very close.

Our annual family holiday took me away to the far east for three weeks and I had no contact at all with Elaine in that time. In those days phoning from that distance was a non starter. By the time I returned she wasn't answering my phone calls for a while. Then she phoned me and told me she had met someone else, a younger man, one who lived much closer to her and was happy to leave his wife and move in with her, etc....

The shock and pain was awful. I was devastated. This was another first. Unbelievably, no-one had ever dumped me before and I hated it. Ridiculously, I remember thinking nothing could hurt me so much. It took ages to get over it, and there was no-one I could tell who could console me. But, realistically, it also convinced me that my wife had been right. Affairs were dangerous. Massage parlours were safer. No serious working girl was going to want me to fall for her and you had a choice of lady every time. There were no strings in between visits. It was a perfect solution.

I found a superb massage parlour at which I became a regular and have written about my experiences there in two other stories.

One detail I left out in those stories - another dangerous first. The other week I had my first anal. Not me in a woman. I can't get my prick that stiff enough anymore. No, it was my current favourite massage parlour lady fulfilling my request that she should dildo me. It was something I had always been curious about. I enjoyed it for a while but then she suddenly pulled out of me without warning and for about two seconds I felt something I never want to experience again. I was lying in bed being held by a beautiful woman and I shat on to her. I screamed an apology because I couldn't stop the ‘shit' coming out but she just laughed. It wasn't me shitting, even though that is what it felt like. Think about it! It was the dildo coming out. But I learned never to ask for that service again.

My marriage is still strong. I am always incredibly careful not to frighten the horses. My wife may suspect but so far has never found out about either the chat lines (which shortly afterwards were taken down because of a leak of people's details) or the adulterous affair. She knows about and accepts that I go to a massage parlour but not when I go. She knows that I masturbate a lot and she sometimes helps me to get started and lets me go my computer to finish myself off by making use of the video clips on You Porn. It makes her feel less guilty about me, she says. And less worried about losing me, of course.