A gay story: The Older Man Pt. 03 It’s a while since I wrote about my meetings with Tom, a 50 something widower who shared my particular tastes in music but also got me so horny that I just wanted to spend more time with him. The trouble was that I was 25 and happily married to a beautiful woman! The last story finished up with a wonderful session of 69 at the culmination of which Tom swallowed my explosion of cum but, because of my nervousness, he came over my face and then kissed and licked my as we shared his cream. The other thing we had in common was our strange liking for tucking shirts in underpants. Mine started at school from looking at a teacher who quite often displayed his waistband in the classroom. My interest always seemed to be in older men, never in boys of my own age, and none of us tucked our shirts in anyway. To my amazement I found that Tom not only tucked his shirt in his briefs but also was turned on by it like me.
At our last meeting we had agreed to meet up again in a couple of weeks. Once again I was very concerned about my wife but had been encouraged when Tom said he had had occasional sex with men during his marriage and that his wife had never appeared to find out. Nevertheless I did not want to hurt her and knew that I needed to take great care. I felt I could trust Tom which was the most important thing. So I texted him and we decided to meet at a lunchtime rather than take up a whole evening.
I was away working for a couple of days after we had made the arrangement and stayed in a Travelodge. During the evening I lay in my bedroom in just my shirt and briefs and had a great wank thinking about what Tom and I had done and what we might do next time. When I had finished work the next day I was walking back to my car and passed a public toilet. I remembered Tom had said he had some encounters with men in them and I suddenly had the urge to go in and see what it was like. I was in a town well away from home so didn’t really know anyone. I didn’t expect anyone would be in there anyway, and certainly not for what I was looking for.
The toilet had two cubicles and three urinals and they were all empty when I went in. I nearly turned round and went out again but eventually stood at the urinal next to the far wall and took out my cock. I managed to piss a little but was just finishing when an older guy, must have been in his 60s, came in and stood at the third stall leaving a space between us. I knew I could not piss any more so I just held on to my cock and looked down at it but watched what the guy was doing out of the corner of my eye. He unzipped and pulled his cock out of his jeans and pissed. But when he had finished he made no effort to put his cock away and gently started to stroke it. This of course started to get me hard and I just couldn’t help doing the same. After a few moments he turned and smiled and I smiled back as he stepped back a short distance to give me a better look at his uncut cock, about 5 inches long.
By this time I was too horny to stop, though I still kept listening and glancing at the entrance anxious that someone might come in. I stepped back a bit too and the guy said that it looked nice. As he spoke he moved beside me and rubbed himself harder. Then he reached out and took my cock in his other hand and began to work it gently. It was already wet with precum. After a short while he bent forwards and began to suck me. It was too much and it seemed that in no time at all I was telling him that I was going to cum. He carried on sucking and took the lot in his mouth. He had carried on wanking while he sucked me and, as I reached over to hold his cock, he suddenly tensed and with a couple of thrusts he shot his load into the urinal. After that he quickly put his cock away — sadly I couldn’t see his underwear — and zipped up and left.
“Thanks son,” he said as he walked out, “see you again I hope.”
I had to stand for a minute to think about what had just happened. Then I quickly put my cock back in my briefs, zipped up and walked back to my car. For some reason I wondered if I should tell Tom about it but wasn’t sure at that point.
A few days later I was due for my next visit to Tom’s house. As I said before it was lunchtime so I reckoned I could spare about an hour out of work time. He was ready and waiting when I got there and didn’t make small talk. He simply asked if I would like to go up to his bedroom. I agreed of course and followed him up the stairs. It was a large room with a king size bed in the middle of the far wall. He led me over to the bed and then reached out and undid my trousers and let them drop to the floor. I hurriedly kicked off my shoes and pulled my socks and trousers off. He sat down on the bed in front of me and began kissing my white Sloggi briefs, stroking the waistband and reaching inside where my pink shirt was tucked in.
Then I stopped him and pulled him up returning the favour until he too was in his shirt and briefs. This time he was in a white shirt and red briefs with a Boss waistband. His bulge seems to show up even better and I was quickly down on him and enjoying feeling the shape of his cock through the fabric. Then it was his turn to pull me up and led me on to the bed where we lay together and kissed. As we paused for breath he whispered that he wanted me to fuck him, but hastily said that he quite understood if I didn’t want to. But of course I wanted to and had been thinking about it a lot since we had last met.
I said that I had never fucked a man or a woman in their ass but he was very encouraging and told me to take my time. He said he usually liked to keep his briefs on when being fucked but, as it was my first time, he would take them off to make it easier for me. He hoped I would keep mine on though, as well as my shirt. I had no problem with this. My shirt was fully tucked in my briefs and would not get in the way so I pulled my hard and wet cock out of the leg of the briefs as he reached over to the locker by the bed. He produced a condom and a tube of jelly and proceeded to get me ready.
Then he lay on his back and lifted his legs, indicating to me to get in between them. Still nervous about not being able to do it right and disappointing him I moved into position. He suggested using my finger first so I slid my first finger in. It went in very easily and I realised that his hole had had more than a little action in the relatively near past. I wondered if he used a dildo or something or whether he had a regular session with someone. But these thoughts quickly passed and I put a second finger in and gently found the spot that made him moan.
I rubbed him for a few moments and then he said,
“Time to fuck me now, Will”
And so I slowly positioned myself and pushed my sheathed cock to the entrance. Then I just went for it and in no time I was pushing in and out. It was an amazing feeling, somehow so different from fucking my wife’s cunt, and I knew that I probably wouldn’t be long before I came. As I fucked him Tom had taken his cock in his hand and was gently wanking. As I got more intense we both increased the moaning and he started wanking faster.
Incredibly as I shouted “Oh fuck, yes” released spurts of cum he too let go and shot a huge load on to his shirt.
I seemed to carry on filling him for ages and finally pulled out and removed the condom. Almost immediately Tom sat up and started licking my cock clean. I did the same for him and then we lay back and kissed, sharing our creamy cum. We then both lay quietly for a few minutes in each other’s arms until I suddenly looked at my watch and realised I needed to get back to work.
We didn’t talk much except for me to check that I had been OK and for him to assure me I had done brilliantly. I told him it had been a great experience and we agreed to meet again soon to ‘explore more opportunities’. I guess I knew what he had in mind and I needed to time to think, and probably wank, about the prospect. Then we both dressed and I kissed him again and hurried back to my car and then to the office.
For the next few days I kept thinking what we had done and what we might do. Should I prepare myself with my fingers or something else? I was scared and excited in equal proportions about actually being fucked but I knew that I had to go on with this.
I’ll let you know what happened!