First time you were cuckolded?

Age when you were initally cuckolded.

  • Less than 18 years old

    Votes: 5 11.4%
  • 18 - 25 years old

    Votes: 10 22.7%
  • 26 - 35 years old

    Votes: 13 29.5%
  • 36 - 45 years old

    Votes: 8 18.2%
  • > 45 years old

    Votes: 8 18.2%

  • Total voters
    44
  • Poll closed .
For us we started in our early 20's. It was a typical roleplay fantasy that kinda evolved into a real instance. We discussed it. Set rules and worked out worst case scenarios before anything was done physically. Since then the lifestyle has been slow moving but moving none the less
 
When I was first going through puberty my best friend was more popular, tall, and attractive than I was... and I found out later had a huge cock. He was confident and charming and basically got any girl her wanted since we were 13. I lusted after all of them and "fell in love" with a couple over the years. All the time watching them mess around.

I started going to a local boarding school as a day student and began hooking up with this fellow student in the fall when we were 15. She told me right away she had an 18 year old boyfriend back home that she was still trying to be with.

She went home for winter break and when she came back she told me they broke up, but he fucked her in the ass right after. I didn't tell her right away but I was incredibly turned on.

A couple of months later I suddenly suggested while hanging out with that same local best friend in a coffee shop that we go back to his house and mess around. She surprisingly immediately agreed and we went.

There she sucked him off but could barely fit it in her mouth. He was so thick she couldn't open her mouth wide enough. Then finally he tried to fuck her but couldn't get more than the head inside her and she had to give him a two handed hand job instead.

That started it and we continued for 11 years together with her fucking other guys, girls, couples the whole time.

Unfortunately never black, I definitely wasn't into it. That didn't change until I turned 38 and my 20 (at the time) year old girlfriend started fucking black guys behind my back.
 
I started dating a girl when I was 20 that loved to go to clubs and have fun, very different to me that I loved to stay home with friends, listen music, etc. I loved the "party girl" look on her so I never complained about busy weekend nights and we spent most time during the day. After a few months she said she wanted to talk and in the conversation she said that she felt really confused because met me and two other guys and while I liked her the most she was unsure what to do. I loved it and said... keep dating we all! Since then always had the thrill...
 
When was the first time you were cuckolded and by who?

I think the concept of "once a cuckold, always a cuckold" holds true because for most of us it begins so early in our sexual development. I know the formal definition of a cuckold involves a married couple...but ignore that.

I was initally made a cuckold when I was 15 years old by my best friend. I had to work late, so he went to pick up my girl friend from her place and then all three of us were going to head to a party - he was single. Well, while they were waiting in the resturant parking lot they ended up fucking in the backseat of his car - he told me that she just jumped him...I never fully bought that and suspected he did a fair amount of flirting with her.

For some reason the event didn't bother me...it didn't turn me on, but we are still best friends - don't know what happened to the girl. I was cuckolded a couple of other times..and developed a over-compensating male persona until accepting my true self 4 years ago.
My ******* was cuckold husband ..i used to watch my mom with her lover ..so cuckolding was deeply rooted in my mind from my childhood...after marriage it took few years to convince my wife to sleep with other men...it took 6 months and what really worked was me and my my wife attended one of the swinger party and watched live gang bang tbat turned my wife on ..she wanted to try once but it never stopped tbere...it was like once lion taste ******* he cant stop it
 
i was engaged to a girl and she got a job out of town so we could only see each other on weekends. well we had not had sex yet, she said she wanted to wait till we got married. then one weekend she came home and said we needed to take a little vacation. on the vacation together she said she had talk to a couple of her girlfriends and they told her that we should start having sex. we got some birth control foam and we finally did it. she did ******* and i knew she was a virgin. well fast forward a few months and she was seeming distant when she would come home or when we would talk on the phone. i found out finally that after i took her cherry she had started fucking a couple guys that she worked with. we did break up but i found out from a friend the reason she let me take her virginity was that she thought since we were to get married i should be the one that broke her but that she also wanted to fuck the other guys. the guys were the ones that told her about the birth control foam. before we broke up i know they got a lot more fucking from her then i ever did. it probably would have been the same if we got married. didn't realize it then but i would end up married to her best friend and her best friend is the same way. cuckold for life i guess
 
I didn't even have sex with a girl till 32 with my tiny dick I only had sex 3 times with girls till I met my present wife at 39. I was a bitch for other guys a lot. My wife cuckolded me on our first date. I watched her have sex with a guy. I didn't fuck her. I ate her dirty pussy our first date.
 
For me, I have to say when I was 16 I had dated this girl for about 3 weeks and one night that summer, we were at a party. Well the party was great, drinks were flowing, weed was heavy, and the music was bumping. As the night crept on, I would lose her for short stints just for her to be back in sight shortly there after, no biggie it's a party, expected.

What I didn't know, was that she had been flirting with this kid Dom, all night. Anyway, I had been with a friend of mine up stairs for sometime last I got from her was she was good by to be with her friend Jessica. So after awhile I was feeling tired and was ready to go, so I walked through the house n did not see her, I happened to run into Jessica on her way out the door, I asked where she was and jess said I haven't seen her for awhile. So my curiousity began, where can she be?

So I decided to walk the house prior to going outside, no success inside, so I began to walk the grounds outside, then soon I seen this kid say as he walked passed, want to see some fucking check the back shed! So as I headed that way I saw a few people watching something, so I walked closer, as I walk closer I hear smacking sounds, followed by moans of pleasure, so crept closer and there she is on her knees taking Doms hung member, I was good sized no where near Dom, no one really knew we were together, so I was just another spectator. I hear her moan as Dom shove his hard dick deep in her pussy, she looks back at him with no care that they've amassed quite a crowd, this goes on for awhile, I'm stunned, amazed, aroused, and confused all at the same time. Here she is the girl I'm supposedly dating, getting pummeled by this other dick in front of everyone.

After awhile, I began to get soft cause I really didn't know how to feel, I mean we had only been dating 3 weeks and only had sex 2 times. So I walk away and eventually head home, but I get in bed and jerk off to the image of her getting fucked hard by this guy Dom. I wish I would have stay d to the finish to see how it ended.

We ended our relationship shortly there after, but years later we dated again and I had told her I had saw her getting fucked by Dom behind the shed at that party. She responded saying I was hoping you would, she was so horny that night she said she wished I would have joined.

That was the first time for me.
 
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