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Top or Bottom?

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As curious as I had been about being fucked, I now became more so about fucking another man. Sam had taken my virginity beautifully, but insisted that he was totally a top and would not let me fuck him. That was fine, that was ok, it was his choice, his way, but it did not stop me wanting to find out just what it was like to fuck a guy.

Of course I had come near, just as I had nearly had other guys have my arse, but I had not yet gone all the way. At the gay saunas where I indulged my bisexual needs numerous guys had asked to fuck me as they had wanted me to fuck them, but I had not been ready. After all why would I be ready? I had done nothing about the urge I had felt through my thirties. I just put it to one side. As I slid rather decadently into my forties I began to think ‘why not?’ I started to think that sex is sex, the thrill is in the arousal and ejaculation and the gender causing that is irrelevant. It’s the buzz we are after.

And with that in mind I became more adventurous. I wanted to learn, to experiment, to savour new things and indulge myself more deeply in my new-found sexuality.

It’s when I first visited a gay sauna, Chariots in Shoreditch near the City of London. That was where I had a guy stroke my cock, where for the first time since my early teens I held another guy’s cock, where I was sucked and I sucked a cock and it was where I was fucked between the cheeks of my arse, but not up it.

It was also when I visited a transvestite hooker and kissed her/him as I caressed and stroked her tits and cock as she sucked me. I was excited by her underwear and stockings. The feel of them against me as we rolled around a bed in each other’s arms did something to me that was different to when I was with a woman like that. I told her that and she asked if I would like to try on some panties and stockings. Her dressing me was so exciting and she gave me my first experience of wearing ladies underwear. Also I visited gay masseurs, had a gay hooker, went to drag nights and to a couple of pubs that had gay and tranny evenings.

This account makes it seem as if I was very active, but I wasn’t really for it was spread over a five or six period. It was a period where my thinking changed completely and I accepted that sex with men and trannies could be just as exciting and satisfying as with women. It was also the time where I overcame my social conditioning and the macho thinking about sex with my own gender.

Despite coming close many times I did not go all the way until I met Sam.

We worked for the same company, a big one, where we were middle managers. One Saturday afternoon I saw him at the gay sauna. I was mortified, but it did not matter for on the Monday I got an email from him saying. ‘Perhaps we should talk?’ I agreed and that evening we did more than talk. After a drink in the pub we parked in his Porsche and we kissed and stroked each other’s cocks. I am not sure what would have happened had a car not come long. Possibly what did happen the next day at his house when he fucked me.

This ‘extra-sexuality’ activity did nothing to diminish the sex life I enjoyed with my wife of fifteen years Kelly. Although in addition to the bi stuff, I also fucked around with other women and I think Kelly had her moments with other guys, we loved each other in our own ways. A few years ago we had agreed on having an open marriage and that had worked for us, well we were still together unlike many of our friends.

As Kelly was not doing much travelling with her consultancy business and Sam’s wife had been transferred from cabin crew to a supervisory position at Heathrow, Sam and I had much less opportunity to get together. But we did, probably once or twice a month. We established a routine. We would sneak off from work, have lunch at a hotel where we had booked a room and then go up to the room. Usually I would undress first, although now and then we would kiss and caress as we undressed each other.

I was very much the subservient one in the sexual relationship, but not in our business or social ones. When we had our afternoon meetings he led the way, he directed proceedings, he was the dominant one and, of course, he fucked me, not me him.

I loved being naked whilst he was dressed and posing for him as he at first ogled me then later caressed and sometimes massaged me. He stopped me reaching out and touching him even though, still fully dressed, he would kiss, suck and lick all over my body. I really was his sex pet, almost his slave.

Had he have suggested tying me up or other BDSM I would most certainly have agreed.

It was a strange relationship. I had not experienced anything like it before. When not with him, I did not think about him or miss him although after two or three weeks I would find myself missing the sex. I would then either, go to a gay sauna and get sucked or, be wanked or if Sam was around meet up with him. It really was simply a sexual relationship with him and a sexual need that I had. With my ‘extra-marital’ women there was nearly always more than just the sex. I needed Escort bayan and usually found some form of connection and affection for them, but not with Sam.

At our ‘meetings,’ after the initial undressing and caressing of me, Sam would undress and flaunt his gorgeous cock at me. It was a beautifully shaped cock that was fairly long and thick, but not overly so. As he put it. ‘Just the right fit for your arse James’ and it was.

He would then fuck me. Usually we would only do it once for we did not have time to recover and repeat the sex, but that was enough. He would take me in a variety of positions with him usually, but me sometimes, wanking my cock so that generally we climaxed together. Now and then he would take his cock out and finish by jacking off and cumming onto my chest, face or cock. We were quite rude.

After one such session he said.

“I have someone I think you should meet James.”

“Yes, why is that,” I asked as I buttoned up my shirt?

“I think you will find him er, interesting.”

“How do you mean?”

“Well he’s intelligent, good looking and well built, in all areas,” he smiled before adding. “And he likes to be fucked.”

“Oh I see,” I said a little surprised, but also excited. “When?”

“Perhaps a drink on Tuesday after work?”


Tony was great. He had been a pilot on the airline, but had recently given that up and was working in the logistics department, which was two floors down from where I worked in marketing.

“The travelling and being away from home so much got to me,” he explained when the three of us had that drink. “And I missed the wife and kids,” he added.

He was about my age, early forties, and was around six feet and had an athletic build. He had a good head of deep brown hair and had quite piercing blue eyes. He was good looking, but not so much so that he would be described as being handsome.

“Look girls,” Sam said pushing his chair back. “I have to go, I take it I can leave the pair of you together?”

Tony and I glanced at each other and smiled.

“Yes,” we both said at the same time laughing as we did.

We had another drink and I asked him how well he knew Sam. He told me that he had known him through Sam’s wife for years, but not well.

“And you,” he asked me?

“A little like you, I have known him some time, but not very well.”

We were hedging around the topic that I certainly and him as well I suspected wanted to discuss. Sam had told me that Tony liked to be fucked and I wondered what he had told him about me?

Leaning forward so that our faces were quite close across the table, Tony looked up and right into my eyes as he said.

“I was wondering how well James?”

It seemed crazy that neither of us felt confident enough to clearly broach the burning issue.

“Pretty well now Tony.”

Smiling he casked. “Would you describe it as intimately?”

Gulping with a sort of embarrassment I mumbled. “Yes Tony, I think that’s fair. You?”

I felt his leg under the table press against mine as he said. “Me too.”

We were silent for few moments although he kept his leg pressed against mine.

“Look James I have to go soon.”

“Yes I do too.”

“Would you like to meet again?”

“Yes I would, would you?”

“Very much so,” he replied.

We got up and walked out of the pub and into the dark car park.

“Do you have any time this week?” I asked.

“What did you have in mind, afternoon, evening?”

“I’m easy.”

Smiling, he said as he moved closer to me. “And I think you will find me pretty easy too James.”

I felt very attracted to him. I wanted to grab him and kiss him, perhaps run my hands over him and certainly investigate his cock.

“I hope so Tony, maybe one afternoon this week you would give me the chance to find out?”

He closed the gap between us and put his hand on my hip. “You could find out a little right now,” he whispered pulling me to him.

“What here?”

“No in my car, it’s a Rangerover.”

“I don’t have long.”

“Nor me, but I doubt we need long do we?”


“Ok follow me in your car and I will find somewhere quiet and secluded.”

Our cars were parked near to each other and just as we almost got to them his phone rang and I listened to one side of the conversation.

“Oh right, yes I see…not for an hour or…oh ok, I can change things…right see you soon then.”

Clicking off Tony said.

“Fuck it, my wife is home early and I have to collect some stuff for her as we have guests this evening.”

“Bollocks, but never mind,” I said actually feeling a little relieved for a quick grope or fuck on the back seat of a car was not my ideal.

“I really fancied it James so I feel pissed off.”

He moved closer to me and gripped my hand. “I’ll be like this all evening thinking about you,” he said pressing my hand against him. His cock was stunningly hard.

“Feeling that Tony, I think I might as well.”

He pulled me to him Bayan escort and squashed our cocks together as his mouth found mine and we kissed. I had never kissed a guy in public before. It was hugely sexy.

“Can you make tomorrow,” he asked breaking the kiss? He slid his hand down and grabbed my dick through my trousers?

“Not really, but I will, I can’t wait.”

It was lovely to be standing in front of the full-length mirror an hour or so later. I was naked apart from a pair of black, lacy top holdups I had bought in Tesco and one of Kelly’s thongs I had taken out of the linen basket. I enjoy watching myself in her panties and seeing my cock sticking out of the elastic waist as I start to jerk off. With Tony’s face in my mind and my cock in my hand it was not long before I was spurting my cum out and onto the paper towel I had laid on the floor by my feet.


The next day at work I was a bag of nerves. I could hardly concentrate so excited was I about the afternoon. I had spoken to Tony on our mobiles to confirm it was still on and that we would have lunch then go to a hotel.

“I can get the Marriott for nothing,” I told him.

“How come?”

“That’s what being in marketing does for you. We can have lunch in the suite first.”

“Wow, how cool is that?”

I explained that I often had business meetings there so it would not be considered odd for the two of us to be in the suite or having lunch there.

“Or even,” I added. “Spend the afternoon and evening there drinking and doing what comes naturally to us.”

We both laughed as he replied. “Well I know what will come naturally to me and I hope it does to you too.”

I told him I would get there first and would text the suite number to him so he should come straight up and I would have a drink waiting for him.

I got there at around noon with the idea to do some work on my laptop, but I was too nervous to concentrate. Tony arrived at just after one and I poured him a glass of Chablis. We chatted nervously as we looked at the menus and chose our meals that I phoned down to the kitchen. The half hour or so wait was agonising. It was clear to me that we both wanted to talk about us and Sam or even get on with it, but we had to wait nervously for the food. However, once that arrived and we started on the second bottle we had both loosened up and our inhibitions had faded a little.

“You had much to do with Sam,” I asked leaning back in my chair.

Finishing his steak and placing his knife and fork neatly on the empty plate he looked at me and said.

“I assume you mean sexually?”

“Of course,” I smiled. “What else?”

“Yes silly me. Three or four times, you?”

“About the same, he gets around a bit doesn’t he?”

“He sure does how did you and he er, um work out you both had similar interests?”

“We had a threesome with that new lady pilot, the Irish one and just got it on there. You?”

I told him about meeting at the sauna. “And one thing just led to another.”

“Yes they do with Sam don’t they, we had another threesome and then just the two of us a few times.”

Finishing my wine I looked into his eyes and said. “And that has led to the two of us hasn’t it?”

“Yes, well I hope so James. It was good of him to introduce us wasn’t it?”

“Yes, why do you think he did that?”

“Well he does not like being fucked does he, just fucking. Well that’s what he told me.”

“Me too, so it’s probably the truth isn’t it?”

“Guess so. He fucked me.”

“He did me too.”

“You done that much?”

“What been fucked?”


Two or three times, Sam being the third. You?

“He was my first.”

“Wow so he took your virginity?”

“Yes he did, and it was good.”

“Yes he is a good fuck.”

I could hardly believe that we were talking this openly about our gay moments, but it seemed natural and there did not seem to be any harm in it.

“Well I don’t have anyone else to judge him against do I?”

“No James, not yet,” Tony replied reaching across the table and putting his fingertips on the back of my hand. “But you will soon.”

“Is Sam just a top?”

“Dunno, but I have found that I much prefer and have become a bottom.”

“So you have fucked then?”

“Yes a couple of times, but I think my female side is the dominant partner. I like being pampered and then shagged. What about you?”

“Tell you the truth Tony I have no fucking idea. I just love the whole man to man thing and can’t get enough.”

“So have you fucked many guys?”


“How many then?”

“Well thinking carefully and counting accurately they add up to exactly zero.”

“So Mister Versatile I will be the first then.”


“Well James we had better get on with it then hadn’t we?”

I stood up and walked round the table to stand behind him. Not knowing where the confidence came from, but knowing that I had to be the top I assumed that I should lead the way and be the slightly dominant Escort one. I put my hands on his shoulders. We had both been wearing suits with open neck shirts, his was white, mine was blue, but we had removed our jackets. I squeezed him. He sighed. I slid my fingers down his chest a little way, just to his collar bones. He lifted one of his hands and gripped the back of mine as he rested his face against my arm. That encouraged me. I slid my fingers inside his shirt and wanted to caress his breasts. But the shirt was too tight as it only had two buttons undone. He realised the problem and my heart leaped when I saw him reach up and undo more buttons.

“Thanks Tony,” I whispered sliding my hands down his nicely hairy chest and cupping his boobs.

“Oh James you are so very welcome,” he said softly, again holding my hands as I let them creep all over his chest.

I kissed the top of his head that he rested against my chest as I slid my hands downwards until the tips of my fingers inched into the waistband of his trousers. Of course it was too tight to push my hand down, but wonderfully and so fucking sexily Tony came to the rescue. Slipping his hand round the back of the chair he ran that up my leg until he found my full erection. He held and stroked that as he muttered.

“Unzip me James, undress me.”

They were fantastic words for me to hear for unbeknown to Tony, this was only my second real gay date. Yes I was quite experienced with gay sex, but not gay dating, Sam had been my first. I was playing a role really when I had led him by undoing his shirt, but that role was now quickly becoming a reality.

I undid his belt and with fingers that literally were shaking I slid his zip down. He took his hand away from my raging erection and between us we removed his shirt that I hung on the back of a chair. He had a great chest and I bent over his shoulder and kissed it. I ran my tongue over it and took a nipple between my teeth and gently bit him. He sighed or more purred really and reached up and cradled my head in his hand.

“Take them off James,” he whispered.

We struggled his trousers down and off and I hung those over another chair. As I did that he removed his socks and sat waiting for me in just his grey, CK Y fronts. There was an encouragingly large and beautifully shaped bulge in them.

“Oh Tony you look fabulous,” I groaned. “Sit down James,” he suddenly announced.


Smiling as he stood up he said. “Well the edge of the bed might be a good place.”

We walked into the bedroom. I was still as good as fully dressed and Tony was just wearing his underpants. I always love that sort of thing with a lover male or female; one of us clothed and the other not.

I sat down and he came and stood right in front of me his bulge less than a foot from my face. Slipping his fingers into my hair he said.

“Make me naked James let me flaunt it at you.”

What erotic words, I thought taking hold of the wide waistband of his underpants. My heart was pounding so loud as I slowly slid them down revealing his glorious, fully erect dick. It was long and thick and looked wonderfully smooth. I could see the veins in it and noticed that he was uncut. His foreskin had slid a little way down the purple glans, which looked interestingly damp.

“Oh Tony, it’s beautiful,” I groaned reaching out and holding it in both hands.

“Mmmmm like it,” he asked running his hands through my head and caressing my scalp?

“Yes it’s gorgeous,” I said kissing the tip of it.

I went to take it into my mouth, but he pulled away. “Don’t let’s fuck around too much James, I cum very easily the first time.”

“What do you want to do then,” I asked a little bemused?”

“Fuck James that’s what I want. I want to be fucked, I want you to fuck me, we can suck and lick each other after that.”

He scrambled past me and lay in the middle of the bed.

“Come on James get those clothes off you old tart.

“Hey not so much of the old if you don’t mind,” I grinned undoing and removing my shirt as I looked at Tony slowly stroking his cock.

I got rid of the rest of my clothes and climbed on the bed. “Mmmmm very nice,” he said stroking my fully bloated cock that was just about as long as his, but probably not as thick.

“Hold on a minute,” I said sliding off the bed and walking into the lounge where I had left my bag. I got the tube of lube and returned to the bedroom. “Thought we might need this.”

He smiled. “Good man, you think of everything. I think that deserves a kiss.”

Lying on our sides facing each other I wrapped my arms round him and pulled him against me. It is such a fantastic sensation to have your cock squashed against another especially when your mouth is also glued to a pair of lips. He kissed well, just as I think I do. We were both patient and creative with lots of tongue involvement and sucking on the other’s lips rather than grinding them together. As we kissed we pressed our bodies together and our hands visited all the usual places on the other guy’s body.

“If you fuck half as good as you kiss James, then this will be my lucky day.”

I was enormously aroused and knew full well that the excitement of that and what we were doing would ensure I would not last long.

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