I am a cuckold and my wife and I are glad of it. Knowing that things that happen to us when we are younger can have an influence in forming us what we are later in life, I decided to look back to my younger years to see if there were experiences that help me become a cuckold and I believe there were.
The first one I can recall was when I had just turned 18, I was in the basement of one of our neighborhoods hottest girls house watching from the stairs as she and an older boy were laying on a couch kissing.
I do recall getting a rather nice hard on as their lips worked together and their legs intertwined. The girl was wearing a white blouse, checkered skirt and knee-high socks.
My eyes went between their mouths and her legs, especially the bare part between the lower edge of her skirt and the top of her socks, as she moved against his body. I think it is safe to say that they were dry humping each other. And I think it is also safe to say that this is when I became a leg man.
Sorry to say I did not watch for long before I left. But the memory is still with me.
A few months later I got myself a very pretty girl friend, Amy. We did a lot of kissing and feeling, but nothing more. A neighbor of hers was a member of a local band that we would go and watch perform. One day he was in a car wreck and the poor guy broke both his arms and was hospitalized.
Amy never let on she knew him very well, so I was surprised when she said we needed to go see him at the hospital. He was in a 2-bed room but without anyone in the second bed. It was just the 3 of us sitting and talking for a while. A couple of days later she said we needed to go see him again.
After sitting and chatting for a while Amy told me to go stand by the door and let her know if anyone was coming towards the room. I recall it being a strange request but did so anyway. While standing at the door, with my back to the room, I heard some giggling then quiet. I turned to see what was happening and saw Amy leaning on the bed with her arms under the sheet. The sheet at his mid-section was moving up and down. Their eyes were locked onto each other's and no words or sounds were being made.
There was no doubt she was jacking him off. I forgot about my duties and just stared at her hands moving under the sheet. It did not take long for him to come and when he did Amy stood up, gave him a kiss on his forehead and said "See ya later" as she grabbed my hand and we left his room.
Before I could say anything to her she told me to be quite and let's get to the car. Once in the car we had one of our hottest make out session right in the parking lot in broad daylight. I took her hands and moved them to my crotch more than once and each time she refused, telling me no she couldn't. Needless to say I got mad and we left.
Two days later she told me she needed to go back to the hospital and see him again. For some unknown reason, I took her. Again, after a short visit she told me to go stand guard at the door and again she reached under the sheet and jacked him off. And again, I stood by the door and watched.
However, this time when she remover her hands from under the sheet she licked his cum off her fingers. Then she kissed his forehead and said "Later" and we left.
When we got to the car and before I could say or do anything she turned and gave me one heck of hot French kiss and at the same time she grabbed my cock through my pants. Feeling how hard I was, her kiss and grip became stronger.
Breaking our kiss, she asked me if I could taste his cum on her tongue. When I told her yes she tightened her hand around my dick and I came.
She let go of my dick, sat back in the seat and laughed saying she loved it. And then said take her home.
She refused any attempt I made to see her again after that day. I never saw her again.
A short while later I met a girl by the name of Ann. She was the same age as me, tall and thin and sweet, or so I thought. She had a mean streak in her that took a while for me to see. She let it be known pretty much right away that she was also dating other guys, so don't get any ideas that she was mine alone.
Her game was to use the newest guy to tease one or more of the other guys she had been dating. She did this by being with the newest guy when one of the older, time wise, ones showed up.
By "being with" I mean kissing, feeling and as it turned out also fucking.
Of course, me being the latest new one I thought it was very cool to be making out with Ann when one of her other guys came over. Oh, a couple of times there were almost fights but fists never flew. I think now that Ann enjoyed the confrontations.
Well it did not take long for me to become one of the "old guys" One evening as I entered her yard I could hear activity on the back porch. As I looked through the screen door I could see a bare bottom going up and down between a spread pair of female legs. I first thought it was Ann's older sister being fucked. But as I heard the girl moan I realized it was Ann.
I was dumbfounded, but, I should not have been, I knew what she was like. So, I just stood there and watched. I soon was stroking myself through my pants as I watch them fuck. The guy was so hot for her he did not last very long. Right after he came in her she pushed him off her and told him she did not cum and perhaps Mike, that's me, who has been watching could finish her off.
The gal knew that I had been standing there watching them the whole time. Of course, she did, she had planned this to happen.
Being a horny 19-year-old, I took her up on her invitation. I dropped my pants, while she was not the first girl I had fucked, it was the first time I entered a freshly fucked pussy. I must say it felt wonderful. Hot, willing and wet. We went at it for close to 5 minutes. She acted as though she came, I know I did. When we were done the other guy was standing next to us with a nice hard on. He told me to move away for he was going to fuck her again.
Ann said that sounded nice and I could leave, she won't be needing me anymore.
About a week later Ann called me and asked if I was available to come over to their house the next night. Thinking I was going to get with Ann again I said yes.
When I got there her older sister, Terry, met me at the door and said that Ann was busy right now but follow me. I followed Terry to the garage and she lead me to a window at the rear of the building. Standing behind me she directed me to look across the lawn. There I could see Ann on her knees giving some guy a blow job.
Reaching around my waist Terry took hold of my cock through my pants. She stroked me as I grew hard while she asked if I liked watching her sister suck a cock. My growing dick gave her the answer. Terry told me to unzip and once I did she had my bare cock out and was stroking me while telling me to keep my eyes on that cock being worked on by Ann.
She asked me if Ann ever gave me a blow job. When I answered to the affirmative, she was told me to think how good Ann's mouth must feel around his dick. She told me I should think about how good her tongue felt licking the underside of my dick and how good it must be feeling to him. She said too bad it is his dick that was enjoying that feeling and not mine. Just about that time he was grabbed the back of Ann's head and Terry said I think he is about to cum down her throat, oh there he goes. Right then I shot my wad against the garage wall.
As the guy's dick slid out of Ann's mouth she turned her head and while licking her lips she looked right at the window where I was and smiled. Terry said it appears I enjoyed the show and ushered me to the door and said good bye.
I never saw either of them again.
Sometime later a few of us guys went over to Canada where there were bars with totally nude dancers. Back then the legal drinking age in Canada was 18. While sitting at a side table at one of the bars I found myself drawn to one of the dancers. There was no way I had any intention of trying to hook up with her, I just found her inviting and very pleasant to look at.
