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How it Started
10/01/2025
My Cuckolding experience began in the early 70’s. The word Cuckold was unknown to me at the time but later in life it became my lifestyle.

It all started with my girlfriend named Robin. At that time I was shy and timid and she was the aggressor towards me. She was pushing me to have sex with her and I being inexperienced and shy was intimidated by it.

I wanted to have sex but I guess scared by It all. We had study hall together that was unsupervised and me and Robin plus my best friend Mark all sat together. She would always want to sit in my lap and grind on my hard dick and tease me.

She would also beg me to take the bus home with her because her mom didn’t get home from work a few hours later giving us time to have sex. My buddy Mark would tease me for not fucking her calling me a homo.

Then one day as she was asking again my buddy Mark spoke up and said if He don’t go home with her then he would gladly give her what she wanted. She asked him if he had ever had sex before and he replied no, but I have a bigger dick than Steve.

Her eyes opened a little and she asked how much bigger, looking at his crotch. It was true, I had seen his dick fully erect and it was fatter and longer than mine by a few inches.

He was a smaller guy than me and I guess you would never have expected it. She commented it doesn’t look bigger and he replied, because it’s not hard. If you want it hard then sit in my lap. Without any hesitation, she got off of my lap and sat on his.

This made me jealous instantly. She began wiggling her small ass on him and she began to say, oh my, I feel it growing. She then says, you weren’t kidding, I like your lap much better. She slipped her hand down and began squeezing him and I could see her face getting flush as she played with him.

She then asked if he would come home with her. He said he would and me getting jealous asked, what about me. She then said you are both welcome. Not wanting to lose her to my best friend, I agreed to go. That afternoon the three of us went to her house which was a couple miles away from mine and not on the same bus route.

The three of us sat together on the bus and she played with his dick the whole time ignoring me. She invited us in and led us to her bedroom where she asked us to get naked. Mark wasted no time and had his dick proudly displayed to her. She wasted no time and began playing with him as I was still undressing.

She gave me a quick look and went right back to him. She started sucking and licking him which I have never seen before and he looked at me with a huge smile on his face. My dick was really hard and begging for attention, so I began slowly stroking it patiently waiting for my turn. He began playing with her tits which were very developed for her age.

She stopped sucking him and removed her top and bra. This was our first time seeing naked tits and Mark began squeezing them as she sucked his dick. Pretty soon she stopped again and removed her pants and panties. There it was, in all its beautiful glory. Her vagina was very pink with very little blonde hair around it. I could smell the aroma from it sending my head into a spiral.

She climbed onto Marks lap and began sliding down onto his dick. She told him to let her know if he was going to cum because we had no condoms. She then slowly rode up and down on him while moaning loudly and saying how great he felt inside her. I sat there watching as she had her first orgasm. The visual of it all made me shoot my on load all over myself.

She turned to see it explode and said I guess you’re done. She went back to riding Mark as I sat with my shrinking dick. They began kissing and then he finally said he was getting close. She never stopped and he said he was cumming and she began having a huge orgasm with him. They both collapsed afterwards. We got dressed and Mark asked if he should worry about her getting pregnant. She said she thought it would be o.k. But would keep him informed later. As we left, she gave me a big kiss and thanked me for coming.

We were walking home when Mark jokingly asked how his dick tasted when she kissed me. I didn’t think about it at the time but now was embarrassed by it. About a week later she informed us she had her period but told us to bring condoms next time. We repeated this about a half dozen times and I never got to fuck but she was still my girlfriend. I guess this is how my Cuckold fetish began.

I told my wife the story many years later and she remembered Robin from school. She told me that she had a reputation as the school whore. I told her that I enjoyed watching them fuck as I jerked off. And she asked if I wanted to repeat it. I told her I did and she asked if Mark was still available. We kept in touch and he was married and lived about two hours away.

I called him and asked him if he was interested in a repeat and he jumped at the opportunity to fuck my Wife. We drove to his town and got a hotel room. We met at a bar and had a few drinks before heading back to our room. I basically sat back and watched them having sex the whole evening. I think I jerked off three different times.

Afterwards my wife was hooked and we continued to see Mark monthly until his divorce. Not because of us though. He ended up closer to our home and they began fucking several times a week. Me and my wife stopped having sex altogether saving herself for Mark. I’m not always present anymore and he has fathered two of our kids I know for sure. It’s a toss up on the first kid but I’m not tracking it.


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