The Older Man Pt. 04

For a few days after I had fucked Tom, my wonderful 50 something friend, I was caught up in a whole range of thoughts and emotions.

Should I go ahead and let him fuck me too, or should I draw the line? If I let him would it mean that I really was gay and had been pretending to myself through my 3 years of marriage and before?

I continued to feel guilty about Lisa, my wife, but I kept remembering that Tom had enjoyed a limited amount of sex with men all through his marriage until his wife had died. As far as he could tell she did not know about it and he did not think it had harmed their relationship. I had also seen on the internet that many men identified themselves as bisexual. So perhaps that was what I was.

The strange thing was that I still did not really have any interest in other men apart from Tom. Ok so I had had an encounter with an old guy in a public toilet but that was just anonymous sex. I did feel differently about Tom. He fulfilled my childhood and teen dreams about an older man (in those days it was mainly my school teachers) and when we kissed and held each other it was something really special.

Eventually I realised that I could not go on thinking in this way and I needed to concentrate on work and on my marriage which I was still determined was what I wanted. Then a rather odd thing happened. I think I have mentioned before that I had started tucking my shirt in my briefs, something that I had done in my school days but that I had stopped as I got older. For some reason it made me horny and once I found that Tom thought the same I decided I wanted to enjoy those feelings again.

I thought I had managed to conceal this from Lisa but one day she came into the bedroom just as I was putting my trousers on. She said that she had noticed my waistband showing a few times.She wondered why I had suddenly started tucking my shirt in like that but she hadn't said anything about it. I said something about keeping some of my shirts neater and to my amazement she said that I should carry on doing it as she thought it looked rather sexy.

I couldn't believe it and didn't know what to say but simply told her that I had got to like it too so would carry on doing it. That night instead of taking my shirt off first I took my trousers off and walked around the bedroom in my shirt and briefs as I was sorting clothes out for the next day. The problem was that I could feel myself getting hard and I was about to finish undressing when Lisa said:

"Come on over here, sexy, let me have a look at those bulging briefs!"

What could I do but go over to her as she laid down on the bed. I stood in front of her and she stroked me and ran her hands around inside the waistband. Then she suddenly pulled my cock out of the leg of the briefs, opened her nightdress and rubbed it against her breasts. We had had various types of foreplay in the past and had done something similar but somehow for me it was fantastic to do it with my shirt tucked in my briefs. We went on to fuck and, instead of getting naked as we usually did she stopped me taking my clothes off. She also said she would keep her panties on and that seemed to move the whole thing on to a new level for both of us. We had a great time.

The next day I was replaying all of this in the car going to work and knew more than ever that I loved Lisa and wanted to stay with her and start that family we had talked about. But then I began to think about Tom. We were due to meet in a couple of days and I nearly called him there and then to cancel. But something stopped me. The more I thought about it I knew that I still wanted to see him too and to my surprise I also knew that I wanted him to fuck me. I decided to do nothing to prepare myself but just to put myself in Tom's hands.

So on the due date I was ringing his door bell full of nervous excitement. I was taken aback when he opened the door to see him in a dressing gown half open revealing his shirt and boxer briefs underneath.

"Wow!" I said, "Somebody's keen."

"I've really missed you," he replied, "and I can't wait to take those trousers off and have my wicked way with you."

This old fashioned expression made me remember the age gap between us but it just made me want him even more. We hurried up to the bedroom and stood by the bed kissing and stroking each other. He quickly undid my belt and undid my trousers and let them drop to the floor. Then he carefully removed my shoes and socks and pulled my trousers off. By now I was getting hard in my white briefs and he pushed his face against them licking and sucking the length of my cock and my balls through the fabric.

I pulled him up quickly worrying that I would cum far too soon, and I took off his dressing gown and returned the favour. His briefs were damp with precum so I could tell he had been 'getting ready' before I arrived. Then he made me stand up and looked me in the eye before saying simply:

"Well?"

I leant over and kissed him on the lips before saying "Yes please, fuck me Tom."

After all my agonising I did not hesitate and let him take me over to the bed. He made my lie on my back just as he had done last time we met and I understood that he liked that position. I had hoped he would choose that as I wanted to look at him rather than have him behind me. He said we would take it slowly but added that it would hurt at first. But he assured me it would be worth it and I wouldn't look back once I had experienced the full joy of a cock inside me.

So we began and he used gel on first one finger and later two to ease his way into my tight but hungry hole. By the time two fingers had gone in part of the way I began to experience the pain he had talked about but he said, confidently, that he thought I was ready. He gently tugged on his cock and then slid the condom over it. He applied more gel to my hole and also to the condom and then started to push his cock gently in. Very soon I felt an almost excruciating pain and was ready to tell him to stop when he pulled out. He must have sensed how I was feeling. He assured me it would get better and once again began to enter me. This time he was even more gentle and as he pushed in further the pain came again but somehow was not so bad. As most of you will know, I'm sure, it wasn't long before I passed the point when pain was overtaken by pleasure and soon I was crying out:

"Oh yes, fuck me Tom, just keep fucking me."

And he did. As he fucked me I pulled my cock out of my briefs and started wanking furiously until I couldn't stop myself shooting all over the outside of my briefs and the front of my shirt. He then reached down with his finger and took some my cum and put it in his mouth. Then he leant over and kissed me, pushing his cum-filled tongue in my mouth. I was still in total ecstasy and was waiting for him to cum inside me. But he had another idea. I remembered the first time we had sucked each other he had pulled out of my mouth and shot his load on my face. He asked if he could do it again. He said that he really liked seeing himself cum and even more if we could share the cum together afterwards.

I think I would have been happy to do anything Tom asked me so of course I said yes. He quickly removed the condom and moved up so that his cock was over my face. I found myself opening my mouth ready to receive him, and after just a few strokes of his cock he spurted great dollops of his beautiful creamy spunk on to my face. I took some in my mouth and savoured it and then, when he had finished and I had licked him clean, we kissed and licked each other and shared it.

When I finally lay back and started to come back to reality I realised I needed to get back to work very soon. My briefs and shirt still had cum on them but Tom assured me I could borrow a pair of his briefs and he would sponge my shirt clean. He asked me to look in the drawer and choose something to wear and I found a pair of black CK briefs which were similar to some I had. I hoped that Lisa wouldn't notice!

And so I dressed and was ready to leave. I told him that I had had a wonderful time and could not wait to see him again. We made a provisional date and I kissed him and left him, still in his own cum-stained shirt and briefs.

Would I ever tell Lisa about all this or would I live this separate life whilst remaining a devoted husband and hopefully father? I couldn't have answered that at that moment but all I knew was that I had started something I couldn't imagine finishing.