Today’s story is a showstopper. It also highlights a shadowy area of intrigue for some of us…what men get up to when left to their own devices. We have all heard the tales about boy’s boarding schools and whilst I am not accusing every man I ever met of being secretly gay, I do think that most men are a lot less hung up on the idea of ‘being gay’ than they let on. I also think its got nothing to do with being gay and everything to do with making the most of whatever opportunities come your way.
Some years ago I took a detour into restaurant management. The restaurant was populated by the gayest (and loveliest) collection of male waiting staff you have ever encountered. The kitchen was where the straight guys hid. Big, beefy macho men who could take the punishing pace and crippling heat of a Saturday night restaurant service. Well, you might think that east is east, west is west and never the twain shall meet but that wasn’t the case in the restaurant that I worked in. It wasn’t just that we were the culinary equivalent of the United Nations, i.e. all departments loved to party together regardless of our differing roles, genders, sexualities and religions. No, there was partying of quite a different kind going on between some of the straightest, manliest chefs I have ever encountered and some of the most homosexual waiters. Strictly behind closed kitchen doors you understand. I only know all this because I had the ‘ears’ of the gay waiting staff. This wasn’t a one off either, it happened a lot.
I remember being surprised at the time but I am not now. Men understand each other. They understand each other’s needs and to that end, they can make simple physical transactions with each other that have fewer emotional repercussions than their heterosexual equivalents. Women are hardwired to involve feelings. Sometimes it’s easier to leave us out of the equation.
‘I prefer the company of and sex with women but enjoy the frisson of possible discovery involved in homosexual activity. I don't regard myself as a gay man; I'm not sure where I stand on the sexual continuum. I suppose I am about 10% gay and 90% straight.’
So says today's story teller. Sexual orientation is not a black and white matter and it never has been. Today’s story teller is totally down with that.
‘I am a 68yr old man, born in the UK where I still live.
I was educated at public school and this seems to have bred into me a subsequent tolerance of the breadth of sexual desire. I was 16 or 17 when I lost my virginity. I was at boarding-school and living in one of seven houses, where we ate, slept and entertained ourselves. Among the staff was a young woman who was employed as a maid in the kitchen and the dining-room. She was a pleasant, friendly lass, well-built with large breasts and bottom.
I think it was in May 1959, the summer term and I walked through from the boys' end of the house, past the kitchen towards the cellars where the craft and other rooms were. What I had intended to do there, I haven't a clue.
As I approached the door to the cellar steps, I bumped into Jesse. I cannot remember from this distance in time what was said nor how it was that we came to be kissing. I can remember that she had full lips and that when ours met I lost all sense of place and time. I think it was at that point that I stuck my hand up under her overall and into her pants.
We made a tacit decision to go down to the cellar, where we shut ourselves into a vegetable store room. We continued kissing and I put my hand inside her bra to feel a breast which was large and soft. She took off her pants and lay down on the floor; I'm not sure if I took down my shorts (yes, it was that kind of school!) or simply unleashed my erection from the fly. I lay down on top of her and my cock entered her very easily. She was soft, wet and roomy but unlike anything I had ever felt in my life - blissful. However much I was enjoying it, the sensation did not, sadly, affect the enthusiasm of a young man's first time and the excitement ensured that the performance was all too brief. I had just relaxed on top of Jesse, when we heard familiar footsteps coming down the stairs.
My housemaster! His steel-tipped heels clicked their way along the stone-flagged passage outside our door. Jesse and I did not breathe. Our already-raised heart rates must have doubled as we lay, terror-stricken. The footsteps continued and on into the craft-room next door. They did not stay there long before retracing their way back up the stairs. Silently praising providence that he had not wanted a vegetable, we gave him a decent time to return to his quarters, hastily adjusted our clothes and went back upstairs. I kissed Jesse good-bye and, knees trembling, went back to daily life. Jesse will always have a warm place in my heart and I shall be for ever grateful to her for the pleasure I had in giving her my virginity.
During my time at prep and public school, being a male with a very healthy sexual appetite, I did become involved with other boys in mutual masturbation but never experienced anal sex. I was in my 40s in the mid-1980s before I started to explore an interest in sex with men. I had read stories of the infamous New York bath-houses and learned that there was a Turkish bath and sauna in the neighbouring city. On my first visit it became clear that it was a hot-bed of homoerotic activity. There was a steam-room, and three sauna areas of varying temperatures from mild to very hot. In those days, men would walk around naked and sexual activity was common almost anywhere. I had a number of pleasant experiences there and met someone with whom I shared other sexual moments over a good number of years.
However, my experience of anal sex took place in a well-know male 'cruising ground' in woods north of the city. One way of soliciting attention is to single out a likely candidate (and they're quite obvious), to stop and have a pee, making your intentions clear by displaying your cock to the subject. On this occasion, a short, bald well-built man responded by producing his cock but remarking that he knew a better place to go and suggesting I follow him. We returned to our cars and drove a mile or so to another area of the woods where I followed him into the trees for a distance until we were sheltered from gaze. I asked him what he liked (a stock phrase of the male cruiser), to which he replied that he liked to be fucked. I was happy to oblige.
We dropped our trousers and I gave his cock a cursory fondle before turning him round. He had a muscular bum, smooth and lightly covered with dark hair. He gave me a condom, which I put on and he bent over to receive me. I place my cock at the entrance to his anus and pushed, a bit too sharply, because he complained. I took more time and let him absorb my cock until I was fully inside him and started to slide in and out. His passage was tight and smooth and felt wonderful and the condom ensured that I could enjoy a decent ride before shooting my load. As is usual in these circumstances, we parted with a mutual pat on the backside.
Having fucked a man, I developed a curiosity as to what it felt like to be fucked. One evening, some years later, I was cruising in woods nearer home, where I met a man who was similarly inclined. We withdrew to a secluded spot, where we got out our cocks and indulged in mutual stroking, sucking, bottom-stroking and hole-fingering. He asked if I was up to be fucked. I had another look at his cock which was uncut (my favourite!) and, although not small, was, I hoped, of an acceptable size, so I agreed. He put on a condom and I anointed his cock and my anus with KY and bent over to receive him. His cock felt large as it entered and its passage through my sphincter while uncomfortable, was not unduly painful.
He shafted me enthusiastically for a few minutes before he came. It did not feel 'natural', which of course it isn't and it did not feel, judging by this experience, to be a past-time I wanted to pursue, although I have succumbed occasionally since. I am now a subscriber to the Julian Clary philosophy that it is better to give than to receive, though, in fact, having recently received a clean sexual bill of health, I now abstain from anal sex and fellatio but I do not resist the occasional 'feel'. I don't know if you are aware of the seemingly huge number of men who seek out this kind of experience before returning to their partners but it appears to be prevalent wherever one goes.
So there you are, dear Kate, three virginitie for the price of one. I am glad I was not the subject of the rogering administered by the female banker's dildo to her husband.’