The Older Man

It's some time since I wrote the stories about my affair with a much older man. I'm married and in my twenties and Tom is a widower in his 50s. I had not recognised that I was bisexual until I met Tom but since we first got together I have enjoyed the delights of oral and anal sex and shared a fetish for briefs, especially with shirts tucked in them. We also shared a love of the same kind of music but many of our meetings were during the lunch time so we did not have much time to listen or indeed to talk!

When we first knew each other my wife was aware and encouraged me to spend the odd evening with him 'listening to music'. Suddenly out of the blue the other day she asked if I ever saw him these days. I said that we had the occasional contact and she suggested I should go over one evening -- she remembered how much I had enjoyed it! Well I'm afraid I did not need much persuading and when I messaged Tom he was also keen and named an evening in the following week.

It was really good to spend longer with him. As was our custom we stripped down to just our shirts and briefs and then sat and relaxed on his sofa, catching up on news. He had never talked much about his family though I knew he had two sons, one in Scotland and one in Canada. The eldest one was married with children and he did not get to see them very often. The younger son, Chris, lived in Canada and usually came for at least one visit a year. He explained that he would be coming over shortly for about a month. He had just split up with his long term boy friend and was in need of a change of scene and a chance to talk more with his dad rather than just an occasional Skype.

I hadn't realised that his son was gay. He had never told me, but then we hadn't really talked much about his family before. Tom said he would like me to meet him while he was here but it may be more difficult for us to arrange our usual sessions for sex. I asked him if Chris knew that he had sex with men too and he said that he had finally told him after his wife had died. I asked how he had reacted and he said he was fine with it. He suggested that perhaps that was where he had got it from!

We arranged to meet again when Chris had arrived. I was not sure about it but he seemed keen so I went along with it. I explained to my wife what was planned and then waited for Tom's message on my phone. When it arrived I was still uncertain but went along with it and turned up at his house as requested. I had taken my usual trouble with my clothing, clean white briefs and a blue buttoned shirt. I have said before that I never had been interested in guys my own age before. It was always older men that turned me on. But when I walked in the room and saw Chris standing there, that all changed.

He was just like a younger version of Tom, and was totally gorgeous. He wore a pale pink polo shirt over jeans (not tucked in, I noticed!). Tom went to get some drinks and we immediately started chatting and it was as though we'd known each other for years. When we'd had our drinks Chris said he was going to visit an old friend and he would leave us to it. There was a broad grin on his face and he obviously knew what would happen when he had gone. But he did say it would be good to get together again before he went back. I left him my mobile number.

And he was right in what he thought would happen. After our usual foreplay with our briefs and our tucked in shirts I was eager to fuck Tom and he was more than ready for it. What was scary though was that during it all I kept seeing Chris rather than Tom and pictured my cock pushing in what I knew would be his beautiful hole. I then began to feel really guilty and probably went over the top in showing my affection for Tom.

That was nothing to how I felt on my way home. I had come to terms with my affair with Tom and was still totally happy in all aspects of my marriage. Apart from a couple of mad visits to public toilets when I was away from home I had never worried about other men. Most of my work colleagues were my age or in the thirties and there was no one there that had attracted me. But now here was a guy, also in his twenties, who had sent me totally hard. Was I really gay after all, or was it possible to be happily bisexual? Of course I had no idea whether Chris was attracted to me at all, and I knew he was vulnerable from his recent break-up. But he had asked to meet up again so.... I would have to wait and see if he contacted me.

When he messaged me I immediately responded and we made a date a couple of days later. He then said that his dad was out that evening so we would have the place to ourselves. I hoped that meant what I thought it meant but determined not to be too pushy. The day arrived and I rang the door bell about three minutes late, not wanting to seem too keen. I was wearing a green polo shirt tucked into my white briefs and chinos. Chris opened the door with a big smile and ushered me in to the familiar room. He was wearing a white loose shirt over shorts.

We made small talk for a short time and then he suddenly said he was surprised I was having a relationship with this dad. He thought the age difference was rather strange. I explained all about my schoolboy crushes on teachers and that I had done nothing about it then or since until I met his dad. He said that he had noticed my underwear waistband showing last time and said he knew his dad always tucked his shirt in his briefs. Was that something that you both enjoyed, he wondered or was it just a coincidence?

I explained that his dad had started me tucking again and that it certainly was a turn on for me. He explained that his dad used to wander around the house in just his shirt and briefs when they were younger. Both he and his brother had done the same when they were young but they both stopped as they got into their teens. None of their friends seem to tuck. Then, to my amazement, he said that he'd be happy to tuck his shirt in if I would like it. I hesitated for a moment but very soon said that I'd love to see that.

So he immediately undid his shorts and dropped them to the ground revealing dark blue boxer briefs. He then carefully tucked his shirt in them and I am sure his hand lingered over his bulge longer than normal. I was getting really horny now and ever more so when he pulled his shorts up leaving the waistband of the underpants showing. He could see I was getting hard and gave me a huge smile as he came and sat down beside me. I smiled back, hardly believing my luck as he leaned over and kissed me on the lips. I responded immediately and we were then locked in a long embrace which included stroking each others' bulges. I was also feeling the back of his waistband and running my fingers round it and down inside.

'I think we had better go up to my room, don't you?' he said.

'Yes please' I replied as he took me by the hand and led me up the familiar stairs to his room. I hadn't been in there before but I barely had chance to look around before he pulled me towards the bed. He quickly removed his shorts and socks and I followed suit. And there we were -- I was with this gorgeous young guy who incredibly had his shirt tucked in his boxer briefs and was sporting an enormous hard on, as was I! It was hard to believe but I was so hungry for him that I immediately dropped to my knees and took his bulging briefs into my mouth. I licked and sucked and soon tasted precum oozing through. Then he pulled me up and did the same to me. I had to stop him or I would probably have cum there and then and I didn't want to end already.

So we kissed again and he asked if I would fuck him. He said he hadn't had sex with anyone since his partner had left and he really needed a cock in his cunt. I told his I would love to fuck him and he quickly lay back on the bed as I kneeled in front of him. He lowered his briefs and then lifted his legs round my neck giving my full access to his beautifully shaved hole. I quickly pulled my cock from the leg of my briefs, asking if he minded me keeping them on. He said it was not a problem for him and I got to work -- first with my fingers, which I spit on to help lube him up, and then slowly let my throbbing cock enter him. He knew exactly what to do to help me and in no time I was fucking hard and he was moaning and begging me to keep going. It seemed as though we fucked for ages before I knew I was going to cum. I yelled out in warning and he told me to shoot the fucking lot, which I did, straight into his beautiful mancunt.

I was completely exhausted but still waited to watch as he wanked his own cock and quickly came on to the front of his shirt. Then we both laid back in each others' arms savouring the moments of calm. After a while I realised the time and knew that I needed to get home. Very fond embraces followed with promises to repeat in the Chris had available before returning home. But as I left I was in turmoil. I had come to terms with my relationship with Tom and was able to reconcile it with my marriage. But this was something different. It was as though I had fallen in love all over again.

That night I couldn't contemplate sex with my wife and next morning I had to wank in the bathroom following all kinds of weird dreams involved Chris in the early hours. I knew I should just put it down to a great evening and make sure I did not see him again but at the same time I was desperate for the sight, the touch and the intimacy that I had had with him. A huge dilemma -- what do you think I should do?