When were you first cuckolded and knew about it
When were you first cuckolded and knew about it
How old were you when you were first cuckolded (and knew it at the time)? I was 16.
Re: When were you first cuckolded and knew about it
Very first experience was at 16 and I saw my then gf fucking another guy at a party (she was cheating on me and didn't know I saw her).
My first actual cuckold experience was when my partner and I were both 17 and she fucked her 39 year old boss.
My first actual cuckold experience was when my partner and I were both 17 and she fucked her 39 year old boss.
Re: When were you first cuckolded and knew about it
When we started going out together, I think she kept fucking other guys. Didn't know at the time but these days I know what well fucked pussy feels and tastes like. First time she did with my knowledge was after we had been married 8 years. I watched the last few minutes including when he came in her. She was 31
A nicely filled wife is a happy life
Re: When were you first cuckolded and knew about it
Yeah - different girls. I split up with the cheating girl not long after- not because she cheated but because she was barking mad. When I saw her fucking, part of me was angry but I was more turned on than anything..flexxxdee wrote: ↑Fri Jun 27, 2025 12:05 amWas it different girls? Getting cucked at that age can really get you feeling conflicted.
I brought a 16 yo girl to my sisters wedding and she disappeared for an hour to suck one of the grooms friends cocks. I was hurt and turned on at the same time. Never felt that way before and I wanted more.
The other girl is my partner I've been with 35 years and I was completely aware of what was going on!
That's hot about the wedding- did she just tell you?
-
submissivedanny
- Player
- Posts: 496
- Joined: Mon Dec 07, 2015 10:13 am
Re: When were you first cuckolded and knew about it
How can you be cuckolded and not know about it? If you were cuckolded you knew and probably approved otherwise you were cheated on.
-
luvwives999
- Player
- Posts: 382
- Joined: Sun Jan 05, 2020 2:53 am
Re: When were you first cuckolded and knew about it
If you read our story about how we started in the Hotties section, you'd know we had a MMF with a good friend early in our marriage. My wife had night classes 3 nights a week, and instead of going to class she would go to my friend's apartment hoping he'd fuck her again. She came home one night 2 weeks later and admitted to me she was skipping classes to go to his apartment. She told me how there was always someone there, so nothing happened till this night, where her shirt was up, her pants were down and he was licking her pussy, when someone rang the bell and she had to scramble into the bathroom to get herself together and not get caught. I was so turned on, I told her I wanted her to keep going to his apartment so he could fuck her. That's how I found out I was being cucked, or about to be cucked.
-
lockedhappyhubby
- Trainable
- Posts: 67
- Joined: Wed Jul 20, 2022 5:59 am
Re: When were you first cuckolded and knew about it
I was 17. My high school first love cheated on me when I was out of town for a week. I knew who he was and had seen him in the locker room showers, he had a huge cock, I didn't. I was crushed hurt and cried hard. Weird thing was I couldn't stop masturbating thinking about his big cock fucking her, sliding in and out of her.
Years later my first wife cheated on me with a mutual friend of ours. I wasn't hurt so much just turned on and again masturbated a lot several times a day.
Years later my first wife cheated on me with a mutual friend of ours. I wasn't hurt so much just turned on and again masturbated a lot several times a day.
Re: When were you first cuckolded and knew about it
When I first met my wife, she had a boyfriend for awhile and I was her side piece. This went on for about 3 to 4 months before she broke up with him for me. During that time I knew she was still fucking him. There were nights when she would tell me not to call or text her. So my mind would wander and thoughts of her getting fucked went through my head. It turned me on immensely.
A few months, like I said, she broke up with him. Shortly after, I admitted to her that the thought of her getting fucked by him turned me on. Shortly after that, we met up with her first bull and I got to watch her, and the rest is history.
A few months, like I said, she broke up with him. Shortly after, I admitted to her that the thought of her getting fucked by him turned me on. Shortly after that, we met up with her first bull and I got to watch her, and the rest is history.
Married to HotfreaksHotwife.
Re: When were you first cuckolded and knew about it
-
Gentleman_jim
- Prepubescent
- Posts: 8
- Joined: Wed Jun 10, 2015 7:12 am
Re: When were you first cuckolded and knew about it
My wife and I were overseas in the military. One day my wife told me that while I was at work the day before Tom, a friend and coworker on mine, had come to the house. She said that he had been flirting were her for a few weeks but this day she fucked him.
I asked her what they did. She told me in detail what the two of them did. After several days of discussion and thought we agreed to an open relationship.
My wife continued to fuck him once or twice a week. He didn't know that I knew. He also didn't know that I seduced his wife and fucked her frequently.
I asked her what they did. She told me in detail what the two of them did. After several days of discussion and thought we agreed to an open relationship.
My wife continued to fuck him once or twice a week. He didn't know that I knew. He also didn't know that I seduced his wife and fucked her frequently.
Re: When were you first cuckolded and knew about it
flexxxdee wrote: ↑Sat Jun 28, 2025 4:47 amsconesy73 wrote: ↑Fri Jun 27, 2025 11:02 amI'm surprised you didn't try and marry her - she sounds a keeperflexxxdee wrote: ↑Fri Jun 27, 2025 9:37 amOh it gets better. I only invited her to my sisters wedding as a ‘plus one’. She had an 18 yo old boyfriend at the time and accepted my invitation. They were fucking pretty frequently. She didn’t tell him where she went on the day of the wedding. I had feelings for her from chatting her up all year at school and thought ‘What the hell, maybe she’ll be fun’.
She told me she went off with the 22 year old because’I might not get that chance again’. True enough. So she sucked the 22 year old as I mentioned.
Then on the drive home she guided my hand to her pussy for what was my first go at finger banging a girl. She nicely helped me locate her clit — I had no idea — and I noticed her pussy was already wet. Likely from the excitement of sucking the 22 yo. So I finger banged her to climax and I felt like a God.
I assume she fucked her 18 yo boyfriend that weekend too.
That girl was so hot and slutty. I’m pretty certain she fucked around on whoever she married.🥵
Just to recap..
She was cheating on her boyfriend to be with you for the night then 'cheated' on you with the 22 year old..
Fabulous girl
Re: When were you first cuckolded and knew about it
Wife (girlfriend at that time) was very innocent and fresh 19 years old girl. She wanted to try and never came back as monogamous.
-
rogerbaulk
- Trainable
- Posts: 94
- Joined: Sun Aug 20, 2017 8:56 pm
- Location: Korea
Re: When were you first cuckolded and knew about it
I was mid-50s. My wife was mid-40s. She told me over the phone she had fucked several guys. Now she wants me to drive her to her dates and find more men for her to fuck.
Re: When were you first cuckolded and knew about it
We were 17 and 18 when we married, and both virgins. We moved into an older man's basement - Mr. Mullins, the same day we got married. I woke up the next morning, and the landlord was sitting next to our bed, and his hand was under the covers. We were naked and he was slowly finger fucking my new wife. She told me she thought it was me. Mr. Mullins told me to pull back the covers. My wife was holding his wrist. Just the tip of his finger was in her and rubbing her pussy. I removed the covers so we both were naked. I was excited when I saw her pussy was wet. Mr. Mullins talked us into letting him teach us about marriage and sex.
On his command, I held my wife's hands. Then he went to work on her pussy. He gave my wife her first orgasm. It was very large. I came without touching myself. After that he and my wife was fucking and I was jerking off only. He told us I was not allowed to fuck her until he thought I had learned enough.
On his command, I held my wife's hands. Then he went to work on her pussy. He gave my wife her first orgasm. It was very large. I came without touching myself. After that he and my wife was fucking and I was jerking off only. He told us I was not allowed to fuck her until he thought I had learned enough.
Re: When were you first cuckolded and knew about it
I was 27 when I got married. My wife was very promiscuous before we married and I knew that she was. After we married, I thought she was faithful. It wasn't long before I found out I was really wrong in thinking that. She just continued doing what she liked with other men. Some I actually knew.
When I did find out and confronted her she apologized and admitted it . We had several long talks, but came to an agreement that she could continue but had to tell me everything when she came home. She agreed and that was the beginning of some exciting times for both of us and lasted almost 12 years. I eventually got to watch her with some of her lovers and even did my part when she asked for it. I really enjoyed that period of my life. Like I mentioned it was definitely a very exciting time for us.
When I did find out and confronted her she apologized and admitted it . We had several long talks, but came to an agreement that she could continue but had to tell me everything when she came home. She agreed and that was the beginning of some exciting times for both of us and lasted almost 12 years. I eventually got to watch her with some of her lovers and even did my part when she asked for it. I really enjoyed that period of my life. Like I mentioned it was definitely a very exciting time for us.
Re: When were you first cuckolded and knew about it
This sounds amazing!AZPainter wrote: ↑Wed Jul 02, 2025 1:01 pmI was 27 when I got married. My wife was very promiscuous before we married and I knew that she was. After we married, I thought she was faithful. It wasn't long before I found out I was really wrong in thinking that. She just continued doing what she liked with other men. Some I actually knew.
When I did find out and confronted her she apologized and admitted it . We had several long talks, but came to an agreement that she could continue but had to tell me everything when she came home. She agreed and that was the beginning of some exciting times for both of us and lasted almost 12 years. I eventually got to watch her with some of her lovers and even did my part when she asked for it. I really enjoyed that period of my life. Like I mentioned it was definitely a very exciting time for us.
Are you still together?
-
justincassel
- Prepubescent
- Posts: 4
- Joined: Tue Feb 11, 2020 2:30 am
Re: When were you first cuckolded and knew about it
I had just started dating this ultra - horny girl back when I was 18. We basically met at a house party and within an hour she was sucking me in the basement. After that she would suck and fuck me whenever I wanted to and I felt like I was the king of this world. One night I got a text from her " are you awake? Can you pick me up ? I am drunk ", I asked her where she was. She said she was at a frat house party. I quickly drove there and text her that I was there to pick her up. She drunkenly came outside and walked to my car. She was wearing a shirt skirt with halter neck top with super low plunging neckline no bra so obviously her drunken walk was resulting in some dangling action under her top. She got in my car and hugged me. I asked her is she ok. She said yes just have a headache. On the way she told me some seniors invited her and her friends to the frat party and it was fun. I asked if any senior flirted with her. She said yes and she told them they she had a bf. I was relieved and happily drove her home. When we reached her place I asked her for a kiss. She was reluctant for the first time. I was surprised and asked her what's the matter. She said nothing and we started kissing in the car. Soon I reach out to her top and put my hands inside. She started moaning and breathing heavily. I pulled her top down exposing one of her boob and started kissing it. I noticed red spot which looked like a bite mark on her boob right above her areola. I asked what's that. She said she doesn't know could be reaction to alcohol. I got a weird feeling but I continued fondling her boobs. I could feel she not as receptive or excited as she used to be. I asked of any guys say or did anything. She got shocked and said no no no nothing happened and grabbed and started unzipping my pants. She took my cock out and put it into her mouth. I was happy again and forgot about that bite mark. She was sucking very fast and aggressively which was unlike her usual. Few minutes later she took it out of her mouth and asked me in a tired voice "Are you close? Should I continue or do you want to do something else". I was surprised again by that question. Before she used to take my cock in her mouth and only take it out once I finished inside her mouth no matter how much time it took. I was getting annoyed so I told her let's move in the backseat and fuck. She gave a "bored" nod and we moved to the backseat. Now both her boobs were hanging outside her top. Again my eyes went on the bite mark making me restless. I started fucking her hard. My cock going in and out of her pussy in cramped up missionary in the car was making me extremely horny. I would have finished any second so I decided to change positions. I turned her around and lifted her skirt. I was angling my cock to enter her from behind. Once ready I spread her cheeks to find her pussy opening. As soon as I spread her cheeks a warm bulk of cum poured out of her asshole. I was so shocked. I watched as the white bulk fluid dripped out of her asshole and formed into a thin stream running down her thigh. As as she felt the fluid on her thigh she became aware and turned around and looked at me in shock. I asked her in angry tone "WTF is this what happened at the party". She started crying and confessed. Turns out 3 frat boys room turns and fucked her in the ass in the restroom. She said she asked them to fuck her ass as she did not want me to find out. She told me the entire story in detailed which I will share if anyone is interest. This really made me feel angry but at the same time horny. I still think about that day even now. We broke up soon after but the memory stayed. I still have the same car and even today I can point to the cum stain on my car seat that dripped from her asshole that day.
Re: When were you first cuckolded and knew about it
I'd definitely love to hear more details- it sounds hot and humiliating🥵justincassel wrote: ↑Wed Jul 02, 2025 2:46 pmI had just started dating this ultra - horny girl back when I was 18. We basically met at a house party and within an hour she was sucking me in the basement. After that she would suck and fuck me whenever I wanted to and I felt like I was the king of this world. One night I got a text from her " are you awake? Can you pick me up ? I am drunk ", I asked her where she was. She said she was at a frat house party. I quickly drove there and text her that I was there to pick her up. She drunkenly came outside and walked to my car. She was wearing a shirt skirt with halter neck top with super low plunging neckline no bra so obviously her drunken walk was resulting in some dangling action under her top. She got in my car and hugged me. I asked her is she ok. She said yes just have a headache. On the way she told me some seniors invited her and her friends to the frat party and it was fun. I asked if any senior flirted with her. She said yes and she told them they she had a bf. I was relieved and happily drove her home. When we reached her place I asked her for a kiss. She was reluctant for the first time. I was surprised and asked her what's the matter. She said nothing and we started kissing in the car. Soon I reach out to her top and put my hands inside. She started moaning and breathing heavily. I pulled her top down exposing one of her boob and started kissing it. I noticed red spot which looked like a bite mark on her boob right above her areola. I asked what's that. She said she doesn't know could be reaction to alcohol. I got a weird feeling but I continued fondling her boobs. I could feel she not as receptive or excited as she used to be. I asked of any guys say or did anything. She got shocked and said no no no nothing happened and grabbed and started unzipping my pants. She took my cock out and put it into her mouth. I was happy again and forgot about that bite mark. She was sucking very fast and aggressively which was unlike her usual. Few minutes later she took it out of her mouth and asked me in a tired voice "Are you close? Should I continue or do you want to do something else". I was surprised again by that question. Before she used to take my cock in her mouth and only take it out once I finished inside her mouth no matter how much time it took. I was getting annoyed so I told her let's move in the backseat and fuck. She gave a "bored" nod and we moved to the backseat. Now both her boobs were hanging outside her top. Again my eyes went on the bite mark making me restless. I started fucking her hard. My cock going in and out of her pussy in cramped up missionary in the car was making me extremely horny. I would have finished any second so I decided to change positions. I turned her around and lifted her skirt. I was angling my cock to enter her from behind. Once ready I spread her cheeks to find her pussy opening. As soon as I spread her cheeks a warm bulk of cum poured out of her asshole. I was so shocked. I watched as the white bulk fluid dripped out of her asshole and formed into a thin stream running down her thigh. As as she felt the fluid on her thigh she became aware and turned around and looked at me in shock. I asked her in angry tone "WTF is this what happened at the party". She started crying and confessed. Turns out 3 frat boys room turns and fucked her in the ass in the restroom. She said she asked them to fuck her ass as she did not want me to find out. She told me the entire story in detailed which I will share if anyone is interest. This really made me feel angry but at the same time horny. I still think about that day even now. We broke up soon after but the memory stayed. I still have the same car and even today I can point to the cum stain on my car seat that dripped from her asshole that day.
Re: When were you first cuckolded and knew about it
The closest I have come to being a cuck was with an ex Gf. Despite some very strong feelings, I broke it off.
I had previously asked her to tell me about prior sexual encounters. She would only tell me about being with a woman, while that friend was getting fucked. And then not in detail. She would never tell me about any men she was with alone. I asked her to cuck me but she wan't interested.
After we broke up she moved out of town for a new job.The morning she was leaving, she came over and told me a guy I knew was driving her to the new city. She refused to give his name. We had sex for the last time and it left me feeling jealous and unsettled, like many cucks report.
I knew the reason she did this was to try to persuade me to take her back. Later she offered a MFM with a gay priest she knew. I declined that as well.
I had previously asked her to tell me about prior sexual encounters. She would only tell me about being with a woman, while that friend was getting fucked. And then not in detail. She would never tell me about any men she was with alone. I asked her to cuck me but she wan't interested.
After we broke up she moved out of town for a new job.The morning she was leaving, she came over and told me a guy I knew was driving her to the new city. She refused to give his name. We had sex for the last time and it left me feeling jealous and unsettled, like many cucks report.
I knew the reason she did this was to try to persuade me to take her back. Later she offered a MFM with a gay priest she knew. I declined that as well.
A hotwife husband wannabe. Hoping one day my wife will spread her legs for me and let another man come in her.
Living the dream vicariously through the loving hotwives on this forum and their generous husbands.
Kik jozyxt
Living the dream vicariously through the loving hotwives on this forum and their generous husbands.
Kik jozyxt
- stubbyhubby
- Experienced
- Posts: 180
- Joined: Tue Mar 31, 2020 2:37 pm
Re: When were you first cuckolded and knew about it
I chose 19-22 because I was 20 the first time I told a girlfriend that I was OK with her fucking other guys, but when I was 18 I caught my 15-year-old girlfriend cheating and broke up with her, but we got back together a few days later. I caught her cheating again a few weeks later and we broke up for a day. I caught her a third time and we just argued really bad. After that I didn't even argue with her when I found out. So technically she cuckolded me, but at the time I didn't know what cuckolding was.
-
Thebestdays1
- Pervert
- Posts: 534
- Joined: Wed Feb 15, 2023 3:02 am
Re: When were you first cuckolded and knew about it
We were both 21 and had just returned from our honeymoon.
We had to wait about 3 weeks after the honeymoon before we could live together so she returned to her family home and went back to work for 3 weeks. One of her colleagues had fucked her on her last working day before our marriage and fucked her again when she returned to work.
She told me all the details during the honeymoon, which turned me on no end. When she fucked him again she wrote to me and gave me all the details and I read and re read that letter dozens of times.
We had to wait about 3 weeks after the honeymoon before we could live together so she returned to her family home and went back to work for 3 weeks. One of her colleagues had fucked her on her last working day before our marriage and fucked her again when she returned to work.
She told me all the details during the honeymoon, which turned me on no end. When she fucked him again she wrote to me and gave me all the details and I read and re read that letter dozens of times.
Re: When were you first cuckolded and knew about it
I'm surprised by the poll results. I thought this was a midlife fetish brought on by a search for novelty.
In my case it definitely was. Ex wife was trying to make me jealous by telling me how the men at work were propositioning her. It turned me on, and I encouraged her, told he she could fuck any man she wanted as long as she told me. Four years later, she finally gave in to one of those guys.
In my case it definitely was. Ex wife was trying to make me jealous by telling me how the men at work were propositioning her. It turned me on, and I encouraged her, told he she could fuck any man she wanted as long as she told me. Four years later, she finally gave in to one of those guys.
-
SheLikesWhenIWatch
- Player
- Posts: 406
- Joined: Sat Sep 05, 2020 11:58 am
Re: When were you first cuckolded and knew about it
We started fantasizing about it together at (her) 25 and (me) 29.
It took ten years for her to feel comfortable enough to actually do it. She was 35. I was 39.
It was a full year of them fucking in private, without me present. After a full year, I had sort of a mini-tantrum that I was being left out, so they invited me into the bedroom to watch. We agreed that it wouldn’t be a one-off, and that I’d be allowed to watch regularly. That agreement evolved into a once-a-month (more or less) arrangement.
She cucked me in absentia, then, at 35/39 (our ages). And she cucked me in-person at 36/40.
There has never been anything like watching my beautiful wife slip her boyfriend’s cock into her excited, wet slit for the first time…and then watching her lean back so I could see him sliding into her. (She knew I wanted to see EVERYTHING, and she finally indulged me.) It was one of the most important moments of our marriage, to be completely honest.
She rode him. Switched to reverse cowgirl and rode him some more. He came in her, and I shall never forget watching his softening dick slip out of her, only to be followed by a gob of his pearly white cum.
I was officially (and proudly) cucked that day……but…..
What they discovered is that they actually LIKED fucking for an audience (me). My wife fell in love with cucking me right away. She LOVED the once-a-month threesomes, sort of showing me how she can make another man (her boyfriend) cum. I was (and still am) elated to have finally been cucked. Over the next six months or so, we got more comfortable with each experience. She wanted me close. She wanted me to hold her hand while he fucked her. She eventually wanted me to tell her I love her and give her a loving kiss as he was exploding inside of her. We all began to feel more comfortable during our threesomes, and I eventually felt comfortable enough to pull out my own dick and masturbate for her as he fucked her. She ALWAYS wanted me to be no more than an arm’s length away so she could pull me in for kisses or nipple-licking, maybe tonguing the knob of my dick, while her boyfriend went to town on her pussy.
We were sort of surprised when her boyfriend eventually admitted that he, too, liked watching me masturbate while fucking her. “It gives me a sense of power I’ve never felt before…fucking her in front of you and seeing you sort of submissively jerking off as she moans on my dick.” He admitted that he hadn’t expected that it would turn him on, but it did. He liked showing me how to properly fuck my wife, and she loved it, asking me from time to time if I was paying attention.
For a long time, I operated under a different username here, on OHW. It was a username that might have actually revealed our true identities. (My username had a significant part of my real last name. A savvy reader might have been able to figure out who we are. In fact, I think it happened, but that’s another story.) So, after several years of monthly cucking sessions in which I was expected to jerk-off (and cum) in front of/around him and my lovely wife while he absolutely feasted on and plundered her pussy, I abandoned my previous username here, on OHW, and created THIS username, SheLikesWhenIWatch.
But over 16+ years of him being in our lives, she sort of outgrew him. It didn’t seem to have that spark that it all had when we were in our mid- and late-30s.
She decided it had come full circle. She wanted to end it, but still remain friends with him.
I was bummed. (It absolutely NEVER gets old…watching the woman you love cum on another man’s cock…and then watching him cum in her, on her, down her throat, etc. I could watch them monthly for another 10,000 years and still never tire of it.) She brought it to an end. (It was hard on him, too. He had fallen for her, too. It’s easy to see why. She’s just a lovely person.) I feel bad for the fellow. He’s a good guy.
It’s up to her, though.
But to my surprise, she had been eye-balling a fellow at work. He wanted her in the worst way. (Despite her age…50s, by this time…she’s so fortunate to have Asian genes, and she rocks a body that most people would say places her in her mid- to late-30s. Petite and fit. She’s so lucky in that way! I can’t say I’ve aged as well.) He had been saying things to his immediate co-workers that, if turned in, would have had HR firing him. Luckily, no one turned him in. Word of his carnal desires eventually reached her. She surprised me when she said she wanted to meet him after work one day. (I remember thinking, “What the fuck is happening? Are we doing this again?”) (“…Yes!” she’d reply!)
She waited until they were alone and confronted him on his “foul desires.” He was embarrassed that the rumor mill had delivered his most carnal desires, but he didn’t apologize. He went all in and said he’d do it in a heartbeat if she ever gave him the chance. He told her she was gorgeous, and that it would be a privilege to be with such a hot girl as her.
Instead of castigating him there, on the spot, she gave him hope. She wanted to go get a bite after work.
As any guy in similar circumstances would, he took that moment as a green light. He basically told her he wanted to ravage her body, fuck her lights out, and she invited him out for “a bite” after work. They saw each other after work often for about two months. She’d come home and tell me everything.
We talked. I asked her if she wanted to do this again. She said she was having fun…and finally, “Yes. I wanna have some more fun. I wanna do this. I want to give him a thrill, too.”
So…Initially, he thought he had a cheating wife on his hands. He was thinking she’d be sneaking out on her husband
But she didn’t want to keep secrets from him from the get-go, so she told him that I’m VERY aware of everything that’s happening, and that I approve.
(I was REALLY hoping I’d get to watch her cumming on another dick soon.)
He was freaked out, at first.
He realized that he was headed for her pussy at some point, but he just couldn’t reconcile the idea that her husband might want to watch (…and masturbate?) while he fucked her. I, after all, have known for all those years that…SheLikesWhenIWatch. Surely, she’d want me to hold her hand, tell her I love her, and kiss her while he pumps her full of his cum.
She asked me to take a back seat for the time being. He was REALLY having a hard time that “some other guy is gonna be looking at my junk.” She didn’t have the heart to tell him that we had been doing exactly that monthly for more than 15 years, and that it’s really no big deal….even though it is.
She has never told him about her first boyfriend. (And it’s not my place to tell him, either.)
So, I’ve been sitting in the back seat for more than two years, now. Like boyfriend #1, he too has fallen for her. It’s so easy. Her girlish charm and energy is so addictive.
They fuck often. She has occasionally come home from his place and planted her pussy on my face. It’s not the same, but it’s not bad, either. (She has come to LOVE the reclamation sex. She gives me the blow-by-blow as I get some sloppy seconds. She’s clearly thinking of him when she cums with me, though. I LOVE IT!!! She just LOVES her new cock.)
At first, I was upset about not being included. (It NEVER gets old!) But over time, I imagined how it would have happened in reality…the awkwardness, the idea of watching another guy masturbate while you’re fucking his wife, etc…and that’s when I felt myself “evolving.” I have finally come to a place where I am not feeling the need to watch. I’ve seen (literally) EVERYTHING with her first boyfriend…up close, far away, eating her out moments after he came in her, cummy kisses (snowballing), kissing her as she came on another man’s cock, kissing her and telling her how much I love her as he filled her cunt, sloppy seconds, etc. (Can’t speak highly enough about sloppy seconds, btw. The BEST lays I have ever had in my life! Heavenly!)
If she was choosing to play this one without me, I would just have to live with it.
That’s good, because she has REALLY been having fun bouncing on his dick…and he’s STILL freaked out that another man might look at his junk while he fucks.
They have made some sex clips on their phones, and she has shown me.
Frankly, I don’t see what he’s worried about. He has a handsome dick. I can see why she’s having so much fun. He should actually be kinda proud! He’s well put together. (Certainly better than me!)
So……It’s a different kind of cucking for these last 2+ years. She has occasionally come home freshly fucked, but more often than not, she’s just looking forward to reliving the feeling of his superior cock as she gets reclamation sex from me. (And I’m more than happy help her scratch that itch!)
I’m having a good time. He’s obviously having a good time. But most importantly, she’s having a GREAT time!
(I’m stuck with this username. I didn’t think we’d evolve beyond it!)
It took ten years for her to feel comfortable enough to actually do it. She was 35. I was 39.
It was a full year of them fucking in private, without me present. After a full year, I had sort of a mini-tantrum that I was being left out, so they invited me into the bedroom to watch. We agreed that it wouldn’t be a one-off, and that I’d be allowed to watch regularly. That agreement evolved into a once-a-month (more or less) arrangement.
She cucked me in absentia, then, at 35/39 (our ages). And she cucked me in-person at 36/40.
There has never been anything like watching my beautiful wife slip her boyfriend’s cock into her excited, wet slit for the first time…and then watching her lean back so I could see him sliding into her. (She knew I wanted to see EVERYTHING, and she finally indulged me.) It was one of the most important moments of our marriage, to be completely honest.
She rode him. Switched to reverse cowgirl and rode him some more. He came in her, and I shall never forget watching his softening dick slip out of her, only to be followed by a gob of his pearly white cum.
I was officially (and proudly) cucked that day……but…..
What they discovered is that they actually LIKED fucking for an audience (me). My wife fell in love with cucking me right away. She LOVED the once-a-month threesomes, sort of showing me how she can make another man (her boyfriend) cum. I was (and still am) elated to have finally been cucked. Over the next six months or so, we got more comfortable with each experience. She wanted me close. She wanted me to hold her hand while he fucked her. She eventually wanted me to tell her I love her and give her a loving kiss as he was exploding inside of her. We all began to feel more comfortable during our threesomes, and I eventually felt comfortable enough to pull out my own dick and masturbate for her as he fucked her. She ALWAYS wanted me to be no more than an arm’s length away so she could pull me in for kisses or nipple-licking, maybe tonguing the knob of my dick, while her boyfriend went to town on her pussy.
We were sort of surprised when her boyfriend eventually admitted that he, too, liked watching me masturbate while fucking her. “It gives me a sense of power I’ve never felt before…fucking her in front of you and seeing you sort of submissively jerking off as she moans on my dick.” He admitted that he hadn’t expected that it would turn him on, but it did. He liked showing me how to properly fuck my wife, and she loved it, asking me from time to time if I was paying attention.
For a long time, I operated under a different username here, on OHW. It was a username that might have actually revealed our true identities. (My username had a significant part of my real last name. A savvy reader might have been able to figure out who we are. In fact, I think it happened, but that’s another story.) So, after several years of monthly cucking sessions in which I was expected to jerk-off (and cum) in front of/around him and my lovely wife while he absolutely feasted on and plundered her pussy, I abandoned my previous username here, on OHW, and created THIS username, SheLikesWhenIWatch.
But over 16+ years of him being in our lives, she sort of outgrew him. It didn’t seem to have that spark that it all had when we were in our mid- and late-30s.
She decided it had come full circle. She wanted to end it, but still remain friends with him.
I was bummed. (It absolutely NEVER gets old…watching the woman you love cum on another man’s cock…and then watching him cum in her, on her, down her throat, etc. I could watch them monthly for another 10,000 years and still never tire of it.) She brought it to an end. (It was hard on him, too. He had fallen for her, too. It’s easy to see why. She’s just a lovely person.) I feel bad for the fellow. He’s a good guy.
It’s up to her, though.
But to my surprise, she had been eye-balling a fellow at work. He wanted her in the worst way. (Despite her age…50s, by this time…she’s so fortunate to have Asian genes, and she rocks a body that most people would say places her in her mid- to late-30s. Petite and fit. She’s so lucky in that way! I can’t say I’ve aged as well.) He had been saying things to his immediate co-workers that, if turned in, would have had HR firing him. Luckily, no one turned him in. Word of his carnal desires eventually reached her. She surprised me when she said she wanted to meet him after work one day. (I remember thinking, “What the fuck is happening? Are we doing this again?”) (“…Yes!” she’d reply!)
She waited until they were alone and confronted him on his “foul desires.” He was embarrassed that the rumor mill had delivered his most carnal desires, but he didn’t apologize. He went all in and said he’d do it in a heartbeat if she ever gave him the chance. He told her she was gorgeous, and that it would be a privilege to be with such a hot girl as her.
Instead of castigating him there, on the spot, she gave him hope. She wanted to go get a bite after work.
As any guy in similar circumstances would, he took that moment as a green light. He basically told her he wanted to ravage her body, fuck her lights out, and she invited him out for “a bite” after work. They saw each other after work often for about two months. She’d come home and tell me everything.
We talked. I asked her if she wanted to do this again. She said she was having fun…and finally, “Yes. I wanna have some more fun. I wanna do this. I want to give him a thrill, too.”
So…Initially, he thought he had a cheating wife on his hands. He was thinking she’d be sneaking out on her husband
But she didn’t want to keep secrets from him from the get-go, so she told him that I’m VERY aware of everything that’s happening, and that I approve.
(I was REALLY hoping I’d get to watch her cumming on another dick soon.)
He was freaked out, at first.
He realized that he was headed for her pussy at some point, but he just couldn’t reconcile the idea that her husband might want to watch (…and masturbate?) while he fucked her. I, after all, have known for all those years that…SheLikesWhenIWatch. Surely, she’d want me to hold her hand, tell her I love her, and kiss her while he pumps her full of his cum.
She asked me to take a back seat for the time being. He was REALLY having a hard time that “some other guy is gonna be looking at my junk.” She didn’t have the heart to tell him that we had been doing exactly that monthly for more than 15 years, and that it’s really no big deal….even though it is.
She has never told him about her first boyfriend. (And it’s not my place to tell him, either.)
So, I’ve been sitting in the back seat for more than two years, now. Like boyfriend #1, he too has fallen for her. It’s so easy. Her girlish charm and energy is so addictive.
They fuck often. She has occasionally come home from his place and planted her pussy on my face. It’s not the same, but it’s not bad, either. (She has come to LOVE the reclamation sex. She gives me the blow-by-blow as I get some sloppy seconds. She’s clearly thinking of him when she cums with me, though. I LOVE IT!!! She just LOVES her new cock.)
At first, I was upset about not being included. (It NEVER gets old!) But over time, I imagined how it would have happened in reality…the awkwardness, the idea of watching another guy masturbate while you’re fucking his wife, etc…and that’s when I felt myself “evolving.” I have finally come to a place where I am not feeling the need to watch. I’ve seen (literally) EVERYTHING with her first boyfriend…up close, far away, eating her out moments after he came in her, cummy kisses (snowballing), kissing her as she came on another man’s cock, kissing her and telling her how much I love her as he filled her cunt, sloppy seconds, etc. (Can’t speak highly enough about sloppy seconds, btw. The BEST lays I have ever had in my life! Heavenly!)
If she was choosing to play this one without me, I would just have to live with it.
That’s good, because she has REALLY been having fun bouncing on his dick…and he’s STILL freaked out that another man might look at his junk while he fucks.
They have made some sex clips on their phones, and she has shown me.
Frankly, I don’t see what he’s worried about. He has a handsome dick. I can see why she’s having so much fun. He should actually be kinda proud! He’s well put together. (Certainly better than me!)
So……It’s a different kind of cucking for these last 2+ years. She has occasionally come home freshly fucked, but more often than not, she’s just looking forward to reliving the feeling of his superior cock as she gets reclamation sex from me. (And I’m more than happy help her scratch that itch!)
I’m having a good time. He’s obviously having a good time. But most importantly, she’s having a GREAT time!
(I’m stuck with this username. I didn’t think we’d evolve beyond it!)
Re: When were you first cuckolded and knew about it
I had a girlfriend in college, who was only my second sexual partner. It was in college, and I was attending a major university with tons of beautiful coeds around. I stupidly fantasized that I could play the field and have experience with having sex with lots of other girls. I told my girlfriend that I would like to end our arrangement as steady boyfriend and girlfriend, and play the field. Her feelings were hurt, and she said that she had no interest in sleeping with other people. She said that I should see other girls, if that's what I really wanted.
I started asking other girls out and going on some dates, none of which ended up with sex. When word got out that we were taking a break for each other, she had some guys approach her pretty quickly, and one who hooked up with her within the first week.
I asked my girlfriend to spend Friday night with me, and she told me she couldn't because she had a first date with this new guy. I went out riding on my motorcycle feeling in a panic, that I was losing her. Somehow my motorcycle route that summer evening, took me by her house a few times. Eventually I saw his car in her driveway, when they returned from their date. I could see their silhouettes against the window shade in her living room, where they were sitting on the couch. I could watch the silhouettes of them making out.
Then I saw their silhouettes move in the direction of her bedroom, and the living room lights went out.
I crawled on my hands and knees around the corner, under her bedroom window. I could hear them having sex. She made sounds of pleasure I had never heard from her before, when we did it. She was sort of screaming, "Oh my God! Oh my God! Oh my God! shit, yes! Yes! There'd be a quieter moment, and then that would start up all over again. I think I counted five different orgasms she had.
I crawled away, and rolled my motorcycle down the street before starting it. I couldn't sleep all night. I masturbated so many times, that I made my penis sore and raw. I was up with the sun, and went out riding on my motorcycle. I coasted by her house, and his car was still in her driveway. It was there until late in the morning. I think they had more sex, and then she made him breakfast.
I hadn't had any luck finding anyone else to have sex with, and I was desperate to get back with my girlfriend. As soon as I saw that his car was gone from her house, I dropped by. She told me a bit about her date, and I begged her to get back together with me, and to return to our steady dating arrangement we had previously. She told me that I had hurt her, and she wasn't willing to go steady with me again. She said she liked the new guy, and wanted to see where that relationship went. She agreed that we could go out, but she wanted to keep things open, to play the field, which had originally been my idea. I tried to get her to have sex with me, but she said she was tired from her date. I begged her to have sex with me, wanting to reclaim her as my girlfriend, but she eventually asked me to leave because she was tired and wanted to take a nap.
We started going on dinner dates and movie dates, but she always had some excuse of why she didn't want to have sex with me. She continued to see him often. I just sort of ended up in the "friend zone", without her actually saying that. I took many late night cruises on my motorcycle, somehow always finding myself going down her street and passing her house. His car was often in her driveway, sometimes for an entire weekend. When his car finally left, I would drop by begging her to have sex with me. She finally told me that I was no longer allowed to just drop by, that I needed to call her first, to see if it was convenient for me to come over.
The other guy eventually graduated from his school program, and took a job out of town. She started having sex with me again, occasionally, but every few weeks she drove to see him in the town where he lived. On other weekends he would drive down to see her, and she would spend the whole weekend with him exclusively. She would let me spend the night with her, when he was back in his town. She rarely let me have sex with her, but would give me a sympathy handjob.
My girlfriend worked as a server in a restaurant. There was a young girl who worked there, who was just out of high school, and had a reputation of liking to sleep around with different guys. My girlfriend introduced me to her and suggested that she would probably have sex with me. That girl had sex with me that Saturday, while my girlfriend had the other guy visiting , from out of town, for the weekend. I found out later, that my girlfriend asked the other girl to give me a sympathy fuck, as a favor to her, because she felt sorry for me, and wanted me occupied while the other guy was visiting for the weekend. My girlfriend agreed to give the other girl a couple of her shifts, in return for giving me the sympathy fuck. I tried to get with the other girl for more, but she told me it was a one-time thing that she did as a favor for my girlfriend, and to get the extra shift, to earn more money.
The long distance relationship eventually became too much for my girlfriend and they ended that relationship. I got more frequent sex after that, for a little while. My girlfriend continued to refuse to return to a steady dating arrangement. She had occasional dates with other guys. Finally she met one, and again became exclusive with him, shutting me out sexually. She eventually married that guy.

