Hello, my name is Jack. I am an old man now. Penny, the nice volunteer lady at the Home said I need to record my happiest memories before I begin to forget and I need to include my 'happy place' so that I can be reminded when things get bad. I'm wondering what she is going to think when she reads this, she doesn't look the sort of person who would enjoy it. Maybe you will?
I'm a quiet man whose adult life started conventionally enough. A lovely young woman, Caroline, took a very shy young me under her wing at university. Earlier, I had been to an all boys school and girls had become a terrifying mystery.
If a girl talked to me I would turn red, if I danced with one I would get an embarrassing hard on and if ever I got to kissing I had been known to cum in my pants. Some of the boys in my class were similarly awkward but I think I suffered the most. It certainly wasn't the done thing to talk to anyone about it, although the answer was simple enough, I was then and I remain now, simply over sexed. I prefer the term mucky though.
Life became more bearable when I got to university, I had a room of my own and I could wank endlessly without fear of interruption. This took the pressure off and meant I could at least talk sensibly to a member of the opposite sex.
Caroline was the first, she was lovely.
She was small, 5 foot 2 and lithe.
Always happy and smiling, she was neat and well groomed with shiny straight brown hair cut in a bob, lively brown eyes and creamy soft skin. She had a way of tucking her hair behind an ear with her hand that I found very endearing.
She had perky little breasts with pink nipples and pussy that was a neat slit topped with a perfect triangle of pubes.
I'm getting ahead of myself here. It was a good while before I got to see anything of those.
And a good thing too. My first university experiences with girls had been rare, drunken, embarrassing ordeals in the dark that had only made me even more nervous of the opposite sex.
Caroline became a friend first. I chatted with her comfortably from the start. I try my hardest not to ogle women but from the back there was something about Caroline's line of hair, her shoulders and her hips that was captivating and I would often have to stop myself staring. Soon we started to seek out one anothers company and eventually came a party, it seemed obvious we should go together and we did.
A massive bout of masterbating before hand made sure I didn't get an enormous hard on and spoil the evening.
It worked. I didn't get an uncomfortable stiffy until the end when we were slow dancing and kissing.
Not enough is written about kissing. How gently sucking lips, touching tongues and the full on feeling around another's mouth with your tongue. It's a lovely experience and a fascinating game of trust about how far to go and when. I was seriously turned on by Caroline happily probing my mouth. By way of explaining why I was not embarrassed by my cock just yet, a description of me. I'm 6 foot, Caroline's 5'2". Leaning over to kiss meant no body contact below the waist. I also wore tight underwear and had my cock pointing up to begin with to keep everything under as much control as possible.
So for the rest of me, as much as Caroline effortlessly managed neat I'm hopelessly scruffy. My hair is straight but sticks up at all angles, I can never look pressed, I'm always creased and rumpled. I like to say I have a slim build but back then I was plain skinny. People say I have the general look of a little boy lost. I had taken advantage of the move to university to grow a beard so I looked more like a lost young man, which I was.
We walked home arm in arm, kissed at her door but that was as far as I was getting. Studies all week then the weekend, a little bit further each time we met. Squeeze of bottom, squeeze of boob. Hand up under her shirt, no bra, glorious.
I was savoring the slow pace, I was dealing with it all without making a sticky mess at least until I got home when I had to fire off a huge wank.
Inevitably the big day had to come. Caroline had had two serious boyfriends before and I had admitted to her I was clueless and had only a basic grasp of what I was supposed to do. In retrospect that must have been completely obvious to Caroline.
It's very sexy when someone does a hot breathy whisper in your ear. I'm not sure anyone has ever beaten Caroline's 'I'm on the pill now, you'd better come in.' Long years of waiting and here it is was. We tumbled through the door. Frantically trying to throw off our clothes before we hit the bed. Caroline's lithe naked body under my hands was unimaginably sensuous, her muscles rippled as she moved. All in the dark, Caroline was never one for the lights on, which made all my other senses heightened.
This might never happen again if I messed up so I took advantage of the situation and went exploring. I kissed down her neck, her shoulders, down to her breasts, she was making all the right sort of noises from my limited knowledge so I continued. After probably over indulging on sucking her nipples I decided to head south. This was necessary to stop my by now explosive cock touching anything that might make it go off. A brief interlude sucking her belly button allowed me to get my hand around and touch Caroline's pussy. I moved my thumb gently up and down and her flesh seemed to part for me. I moved my thumb up again and felt a little hard bit, that got a reaction, must have found her clitoris. This was going well, better than I expected. Further south then, small kisses past the pubes, the smell, the warmth, I was in heaven and then the juices, I said I was mucky didn't I? I put my mouth over her clitoris and worked it with my tongue then pushed my thumb into the entrance of her vagina. I thought it would be a good idea lick upwards and gently roll my thumb around her entrance, one lick to one circle. I was really enjoying doing this when I was hoiked up by my ears.
The time had come.
As a six foot man with a 5 foot 2 woman my masturbatory fantasies had over looked an obvious problem. My large cock. Big cocks are supposed to be a good thing. Women are meant to get lustful at the mere sight of one. In the dark, after my third attempt to battering ram my way into the poor woman the panic in me started to rise. I froze somewhere between, if my cock gets stimulated any more it's going to go off before this has really started and, I'm getting so embarrassed my erection is going to flag.
I was saved by Caroline's clipped instruction, "Get over onto your back."
Relieved someone who knew what they were doing was taking charge I happily complied.
A little hand grappled with my cock to get it lined up. I didn't get the "Oh my god that's a big one" or similar abandoned cry porn would have you believe, just a quiet "Ooh fuck."
Caroline's fingers couldn't touch when they grabbed around my cock. I suppose I've got to give some vital statistics. The circumference is 6 inches. I never quite get length measurements, if I measure looking down, belly button side, it is 8 inches. From the bottom, ball bag side it measures 10, but it's difficult to say where it really starts. If you measure all the way down to the to the bottom of my balls it becomes a very frightening prospect to be confronted by.
Let's settle for 9 inches. Fortunately as it was dark Caroline wasn't able to see how veiny and knobbly it is.
This was it, Caroline pushed down. It is still the best bit for me pushing inside someone else, those first couple of inches, all the stimulation and psychology that got you to that point.
Presumably this is where as a man you loose your virginity, a momentous occasion for me.
My whole body had gone completely rigid at this point, a supersensitive rock hard cock combined with a petrifying fear of premature ejaculation.
Caroline moved slowly down my cock and uttered a small "ow". We'd found our limit.
In the literature men are always slamming their hard cocks in and women are screaming for more. This was never going to happen for me, I realised I was going to have to be very careful with what was quite a dangerous weapon.
Caroline got her measure and started earnestly moving up and down
I remained rigid in every respect.
Far sooner than really appropriate the inevitable happened and my testicles exploded. It actually felt as if I had shot them out of the top of my cock. This repeated over and over again. I've never matched the enormity of that ejaculation. It was if a lifetime of cum came out in one go. All that wanking had been for nothing.
Caroline seemed pleased her efforts had come to end, she popped herself off the end of my cock and made a beeline for the toilet depositing some blobs of cum down my leg on the way. I could hear lots of plops, and wiping before the toilet flushed.
The longer it took the more awful I imagined her reaction was going to be, I got to the stage where I imagined she was going to tell me I was a disgusting animal and demanded I leave.
What a relief when she climbed into the bed gave me a kiss and simply lay on top of me and went to sleep.