Our first and only cuckold experience

This story is absolutely true and honest. It might seem uneventful to those who have fully embraced the lifestyle but it was the greatest night of my life and its the first time I’ve shared it.

My wife and I just turned 50. We first started dating when we were in out early 20’s. I have a statistically average penis at 6.5″ but have always been very insecure about its size. In the 7th grade I started a conversation with my father about puberty. I was hoping to ask him when he thought I might get pubic hair. It was difficult to talk about because I felt very underdeveloped compared to most of my peers. I can remember the conversation almost verbatim because it had such impact on me.

“Dad, can I talk to you about something?”
“Sure, what is it”
“Sometimes I get a little embarrassed in the locker room after gym.”
“Is it because your penis is so small?”

I had not considered that possibility until that moment. I was just concerned about pubic hair. But not a day has gone by since then without me wishing for a larger penis. Not one day.

I, of course, reached puberty late but otherwise uneventfully. I was relatively successful with girls in High School and had sex for the first time at the age of 17. Alcohol was usually involved and I never worried about my size during sex. I was convinced that my flaccid penis was very small but that my erection was normal. I had convinced myself that I was good at sex. Similarly, through college, I had very frequent sex. Usually one night stands.

Toward the end of college I had a serious girlfriend and snooped in her diary. We had had a brief break-up and she described having sex with someone else. Again, the words will be with me forever. “Its felt soooo good.” Now, she didn’t say it was because his penis was bigger but I wasn’t sure what else it could be.

At about that time, I bought a copy of Penthouse Forum and there was a cuckold story (the word cuckold was not used). It described a wife who went skinny dipping with her husband and his friend who a very large cock that “hung like sweet rope” over his thigh when he laid down in the sun. I masturbated furiously to that story for years.

I met my wife right after college. She had just ended a relationship with a football player. She didn’t think much of him as a person but as she and I grew closer and more intimate, we began to talk about her previous partners. To be fair, I aksed. I know she enjoyed sex with me and it was frequent but she told me, eventually, that he had a very thick cock “a little longer than yours” and that that was the best sex she had ever had. She would go into great detail and she could make me cum in a matter of seconds with these stories.

Over time she became more and more frank about the disappointment she felt when she first felt my penis. I have never made her orgasm with intercourse but I touch her well and I have a few stories from college that always make her cum. I would describe a few threesomes I had with college friends (who she knew) and various girls and I would exaggerate my friends’ size during the stories. I could also make her cum in seconds with the right description.

We began to talk very specifically about certain friends of ours and she be flirtatious but never crossed any lines. We talked about her having sex with a colleague of hers at work. She did a lot of flirting with him (let him peek down her shirt, danced with him, etc) but, again, never anything really inappropriate.

About 5 years ago, we left out children with a close family friend and turned my 1-day work conference weekend in NY into a long weekend. This was our first weekend away from the kids who were about 10 and 12 at the time. We had spoken about trying to meet up with someone get a massage and she eventually consented to “meet” someone but there would be no guarantees about anything other than that. I knew this was a rare opportunity for us and I was determined to make my fantasies a reality.

I placed an ad on craigslist describing how much my wife missed her college boyfriend’s thick cock and made contact with someone.

This was his response cut and pasted from his email reply:

“Your idea sounds like a lot of fun. I’d love to give your wife a massage (and more, if that’s what she wants). I’m a white male, 30 years old, good looking and VERY thick (let me know if you wanna see that pic). She will definitely not be disappointed, and I’d be more than happy to let her check 😉 I also give a great massage with a nice combination of swedish and sensual techniques. I’m fine with you watching, but please know that I’m 100% straight. My basic pic is attached. Let me know if she wants to see a more interesting pic. Hopefully we can all have a good time. ”

After a few messages back and forth, he sent a picture of his cock which was every bit as thick as he claimed. We met for drinks at a club in NY and I was immediately uneasy about how quickly he took charge. He kissed her hello and put his arm around her and generally excluded me from the conversation. I bought them drinks and tried to remain calm. Then we all agreed to go back to out hotel room.

They made out in the cab on the way back and he touched her small breasts. I really couldn’t believe this was happening in front of me. It was so disrespectful and I was so jealous and hard. Such a strange confluence of feelings.

They were standing at the foot of the bed and I was sitting in a chair, out of the way. He wasted no timed pulling out his cock which was really very thick and ridiculously hard. They slowed down a bit and moved to the bed where he started to massage my wife right in front of me. This lasted for about 10 or 15minutes when he asked if he should put a condom on. She answered, “I’m not sure.” I said, “put a condom on.” I knew she was excited and I knew she would go through with it.

He grabbed a condom from his jeans pocket and, again, I remember his precise comment directed at both me and my wife. “This is a Magnum. Have you sen this before?” His hands were slippery from the massage oil and he held the condom out to me expecting that I would open it for him. I regret not being more submissive in a lot of ways but this was the first. I declined to open it for him. I wish I had and I wish I had been to told to put it on him.

He finally got the condom on and began to fuck her from behind while she was lying flat on her belly. That is our favorite position because, as she says, “it makes it seem like your penis is bigger.” His must have felt huge. She didn’t scream and she didn’t have an orgasm but I will never forget her deep guttural grunts. I had never heard her make a sound like that with me. He fucked her like a man for what seemed like a long time to me. He came and then I got naked. They both saw my smallish penis and a fucked her from behind and came in about 3 minutes. She was wetter than I had ever made her and she felt loose. He was standing at the bedside with his cock hanging near her face and said with a disbelieving laugh, “Did you just cum?”

He left shortly after and I laid on the sweaty sheets next to my wife hardly able to believe that we had finally crossed this line. I asked her the next morning very seriously if she wished my penis was like his and she stated that yes, she did.

There was something very final about this having happened. The boyfriend stories were probably true but I had not seen them with my own eyes. I had not heard her grunt. She had not been able to so clearly compare a large thick cock to my little penis.

Though she has had hundreds of orgasms with me touching her and talking about the details of that night, we haven’t really had the chance to repeat it. I’m not sure she would but I am quite sure I would. And I have committed to the idea of being completely submissive if I am ever luck enough to have this opportunity again. I will make sure I put on the condom. I would like to lay underneath her while she is fucked doggy style. I have no interest in eating a cream-pie but I would encourage her to go bareback.

Maybe when the kids are older, we’ll do this again.