My life as a cuckold
Posted: Wed Jun 15, 2022 4:49 am
I was asked recently, on this forum, to write my story so, finally, I have decided to give it a go. First, a little about me.
I am 67 years old and have been cuckolded by three different women over the last 48 years. In that whole time, I have experienced penetrative sex only a handful of times, something I shall explain as I go along. I have named the women Ann, Beth and Cath, for simplicity and clarity. Those are not their real names. Likewise, any men mentioned will have made up names as well. This makes it easy because I can’t remember a lot them! I may also have embellished a few details but, essentially this is all true.
Before I begin with the story of Ann, I need to explain some things. My penis is small. I accepted that a long time ago when I saw my cousin’s penis when we were both teenagers. He told me mine was very small and his was average. I then found out for sure when I went camping with a girlfriend when we 17. We were in our tent and she stripped off, ready for some sex. I did likewise and when she caught sight of my cock she laughed and said something derogatory about my lack of size.
As well as having a small penis, I also have a bit of a hair trigger when it comes to having an orgasm. This led to me experiencing my first cream pie, albeit my own. I came far too quickly one night and the girl I was with pushed my head between her legs and insisted I finish her off properly. This became a regular thing.
Girlfriends never lasted too long after those initial attempts at sex so I spent a lot of time relieving myself. Then I met Ann.
I was 19, she was 29. I thought she was beautiful and extremely sexy. We were both at the same party when I first saw her. She was wearing a mini-dress, which did not leave a lot to the imagination. We chatted and hit it off straight away. We swapped phone numbers and left the party separately.
I couldn’t wait to ring her and did a few days later. We met up for a drink then, gradually, things developed to the point where she came over to my flat to ‘stay over’.
Of course, the sex was a flop. I was way too excited and came in record time. She laughed it off and said it didn’t matter. I offered to go down on her to make up for it. She thought this was odd given I’d cum in her but she was happy for me to finish her off. Which I did more than once that night.
Moving ahead a month and my lease was about to expire and Ann suggested I move in with her. Obviously I said yes and, as soon as my lease was up, I moved into her one bed flat on the lower north shore of Sydney.
Our sex, up to this point, had mostly been me giving her oral orgasms. She occasionally gave me a hand job but, basically, I had to relieve myself. I didn’t mind. I was in love with this beautiful older woman. I was her devoted slave. Almost literally.
I was out of work at the time and she decided it was silly me looking for work when I could just look after the flat. And so I did. All the housework, the cooking, the laundry, everything. I didn’t mind. She was worth it.
Then one day, Tony knocked at the door.
Tony was Ann’s ex. He was in his early 30’s and was a ‘big shot’ in banking or law of finance or something. I can’t remember. He was also a bully which was why he was Ann’s ex. He was one of those annoying men who think they are superior to everyone else in the room. He would often smirk.
The day he knocked at the door and I let him in, changed things dramatically for me. Ann called for him to come into the lounge and told me to get them a glass of wine each. Note that I said ‘told’. She’d stopped asking me for stuff a while ago.
When I returned to the lounge room, they were sitting together on the lounge, facing me. I gave them their drinks. Ann gestured for me to sit in the armchair.
Obviously I can’t remember the exact words but this is basically the conversation:
Ann: I have decided that, while I appreciate everything you do here, our sex life is a bit lame. Which is why Tony is here.
Tony: Yes. I am here to fill in where you can’t.
Ann: As you know, I couldn’t live with Tony but I really miss the sex. It makes sense.
And so, no sooner had they pronounced this fact than Tony took Ann’s face on his hands and passionately kissed her as a prelude to an afternoon of noisy, vigorous sex in the bedroom.
I was not allowed to watch. In fact, I never saw them have sex apart from some heavy petting when Ann would take Tony’s cock out while watching a movie or just chatting or Tony would slide his hand up Ann’s skirt and start to finger her pussy.
Of course, I was always on clean up duty.
That first time, Ann called me into the bedroom eventually and pointed down at her wet crotch. I knew what I had to do and sunk down to lick her. At the time, Tony was lying on the bed next to her, his cock soft and just laying across his thigh as he watched me. He was very amused with it, wondering how on earth I could do it.
He was intrigued and, unless he had to rush off, would always watch me clean Ann up after he’d finished with her.
At wasn’t long before Tony banned me from penetrating Ann with my cock. Not that I had seen much action for a while. He told me that Ann’s cunt was his and I only allowed to use my mouth on her. Then he hit on, what he thought, was an excellent idea. He asked me if I knew what chastity was. Obviously I knew what the word meant but he explained that it was a way of controlling wankers like me. He told me we would be going shopping on the weekend.
The next Saturday saw us heading up to Oxford Street with visits to various sex shops until Tony found what he was after. Obviously, it was a male chastity belt. One that went around the waist with a tube suspended in the front for my cock and a strap that went between my legs and attached to the back of the belt.
Back at the flat, Tony had me strip and handed me the belt. I managed to work out how it was worn and he snapped the padlock shut. I remember the belt being remarkably uncomfortable though, with liberal doses of lube, it was bearable.
Tony said that he now controlled my orgasms. He would decide when and where. I was not to ask for release because that would merely serve to extend the time I was locked up.
Remember I was 19 years old and, like most 19 year old males, I was horny all the time. It was going to prove difficult. Still, I wanted to please Ann and was happy to whatever Tony said.
That first period of chastity lasted two weeks.
My belt was generally ignored. Ann let me out to wash every few days but that was it. She never touched me and I was straight back in after cleaning. I grew used to it though the constant erection strain was getting to me.
Then, one day, Tony came to the flat and announced I’d be allowed to cum as long as I did it there and then, in front of him, using only two fingers and within five minutes. I knew the timing was not going to problem, I felt I could explode in about two seconds. The idea of masturbating in front of another man was a bit weird though.
Still, Ann unlocked the belt and my erection bounced free. Using two fingers, I started on myself, conscious of Tony’s eyes on my action. I couldn’t look him in the face. He told me to look at him, pulling my chin up. I kept my eyes on him as he looked back down at what I was doing. As I expected, I took less than a minute.
Tony laughed as I came, spurting all over the floor. He grabbed my arm as I started squeezing myself, hoping to enjoy that final feeling of release. He shook his head and, instead, told me to clean the mess off the floor. With my mouth. If having him watch me masturbate was humiliating, it was nothing compared to how I felt licking up my mess from the floor.
Ann then took me to the bathroom where I was instructed to clean myself up before putting the belt back on.
I lived with Ann for eight years. In that time I probably had fewer than 100 orgasms. Tony would make me wait for ages then, suddenly, for no reason at all, have me cum three days in a row. And each time, I would have to clean it up. He also taught me about ruined orgasms, something he believed was all I deserved. He taught me know when to stop so my cum, just dribbled out.
Of course, during those eight years, Ann and Tony had some amazing sex. She was right, he was excellent in bed and, while it sounds a bit odd, I feel it brought us closer together.
We split up because Ann was offered a job in Western Australia. I was working by this time and couldn’t leave Sydney so we decided to go our separate ways. There followed six months living with a gay guy who believed I was gay as well. We lived for a couple in his flat until I met Beth.
Coming next – me and Beth
I am 67 years old and have been cuckolded by three different women over the last 48 years. In that whole time, I have experienced penetrative sex only a handful of times, something I shall explain as I go along. I have named the women Ann, Beth and Cath, for simplicity and clarity. Those are not their real names. Likewise, any men mentioned will have made up names as well. This makes it easy because I can’t remember a lot them! I may also have embellished a few details but, essentially this is all true.
Before I begin with the story of Ann, I need to explain some things. My penis is small. I accepted that a long time ago when I saw my cousin’s penis when we were both teenagers. He told me mine was very small and his was average. I then found out for sure when I went camping with a girlfriend when we 17. We were in our tent and she stripped off, ready for some sex. I did likewise and when she caught sight of my cock she laughed and said something derogatory about my lack of size.
As well as having a small penis, I also have a bit of a hair trigger when it comes to having an orgasm. This led to me experiencing my first cream pie, albeit my own. I came far too quickly one night and the girl I was with pushed my head between her legs and insisted I finish her off properly. This became a regular thing.
Girlfriends never lasted too long after those initial attempts at sex so I spent a lot of time relieving myself. Then I met Ann.
I was 19, she was 29. I thought she was beautiful and extremely sexy. We were both at the same party when I first saw her. She was wearing a mini-dress, which did not leave a lot to the imagination. We chatted and hit it off straight away. We swapped phone numbers and left the party separately.
I couldn’t wait to ring her and did a few days later. We met up for a drink then, gradually, things developed to the point where she came over to my flat to ‘stay over’.
Of course, the sex was a flop. I was way too excited and came in record time. She laughed it off and said it didn’t matter. I offered to go down on her to make up for it. She thought this was odd given I’d cum in her but she was happy for me to finish her off. Which I did more than once that night.
Moving ahead a month and my lease was about to expire and Ann suggested I move in with her. Obviously I said yes and, as soon as my lease was up, I moved into her one bed flat on the lower north shore of Sydney.
Our sex, up to this point, had mostly been me giving her oral orgasms. She occasionally gave me a hand job but, basically, I had to relieve myself. I didn’t mind. I was in love with this beautiful older woman. I was her devoted slave. Almost literally.
I was out of work at the time and she decided it was silly me looking for work when I could just look after the flat. And so I did. All the housework, the cooking, the laundry, everything. I didn’t mind. She was worth it.
Then one day, Tony knocked at the door.
Tony was Ann’s ex. He was in his early 30’s and was a ‘big shot’ in banking or law of finance or something. I can’t remember. He was also a bully which was why he was Ann’s ex. He was one of those annoying men who think they are superior to everyone else in the room. He would often smirk.
The day he knocked at the door and I let him in, changed things dramatically for me. Ann called for him to come into the lounge and told me to get them a glass of wine each. Note that I said ‘told’. She’d stopped asking me for stuff a while ago.
When I returned to the lounge room, they were sitting together on the lounge, facing me. I gave them their drinks. Ann gestured for me to sit in the armchair.
Obviously I can’t remember the exact words but this is basically the conversation:
Ann: I have decided that, while I appreciate everything you do here, our sex life is a bit lame. Which is why Tony is here.
Tony: Yes. I am here to fill in where you can’t.
Ann: As you know, I couldn’t live with Tony but I really miss the sex. It makes sense.
And so, no sooner had they pronounced this fact than Tony took Ann’s face on his hands and passionately kissed her as a prelude to an afternoon of noisy, vigorous sex in the bedroom.
I was not allowed to watch. In fact, I never saw them have sex apart from some heavy petting when Ann would take Tony’s cock out while watching a movie or just chatting or Tony would slide his hand up Ann’s skirt and start to finger her pussy.
Of course, I was always on clean up duty.
That first time, Ann called me into the bedroom eventually and pointed down at her wet crotch. I knew what I had to do and sunk down to lick her. At the time, Tony was lying on the bed next to her, his cock soft and just laying across his thigh as he watched me. He was very amused with it, wondering how on earth I could do it.
He was intrigued and, unless he had to rush off, would always watch me clean Ann up after he’d finished with her.
At wasn’t long before Tony banned me from penetrating Ann with my cock. Not that I had seen much action for a while. He told me that Ann’s cunt was his and I only allowed to use my mouth on her. Then he hit on, what he thought, was an excellent idea. He asked me if I knew what chastity was. Obviously I knew what the word meant but he explained that it was a way of controlling wankers like me. He told me we would be going shopping on the weekend.
The next Saturday saw us heading up to Oxford Street with visits to various sex shops until Tony found what he was after. Obviously, it was a male chastity belt. One that went around the waist with a tube suspended in the front for my cock and a strap that went between my legs and attached to the back of the belt.
Back at the flat, Tony had me strip and handed me the belt. I managed to work out how it was worn and he snapped the padlock shut. I remember the belt being remarkably uncomfortable though, with liberal doses of lube, it was bearable.
Tony said that he now controlled my orgasms. He would decide when and where. I was not to ask for release because that would merely serve to extend the time I was locked up.
Remember I was 19 years old and, like most 19 year old males, I was horny all the time. It was going to prove difficult. Still, I wanted to please Ann and was happy to whatever Tony said.
That first period of chastity lasted two weeks.
My belt was generally ignored. Ann let me out to wash every few days but that was it. She never touched me and I was straight back in after cleaning. I grew used to it though the constant erection strain was getting to me.
Then, one day, Tony came to the flat and announced I’d be allowed to cum as long as I did it there and then, in front of him, using only two fingers and within five minutes. I knew the timing was not going to problem, I felt I could explode in about two seconds. The idea of masturbating in front of another man was a bit weird though.
Still, Ann unlocked the belt and my erection bounced free. Using two fingers, I started on myself, conscious of Tony’s eyes on my action. I couldn’t look him in the face. He told me to look at him, pulling my chin up. I kept my eyes on him as he looked back down at what I was doing. As I expected, I took less than a minute.
Tony laughed as I came, spurting all over the floor. He grabbed my arm as I started squeezing myself, hoping to enjoy that final feeling of release. He shook his head and, instead, told me to clean the mess off the floor. With my mouth. If having him watch me masturbate was humiliating, it was nothing compared to how I felt licking up my mess from the floor.
Ann then took me to the bathroom where I was instructed to clean myself up before putting the belt back on.
I lived with Ann for eight years. In that time I probably had fewer than 100 orgasms. Tony would make me wait for ages then, suddenly, for no reason at all, have me cum three days in a row. And each time, I would have to clean it up. He also taught me about ruined orgasms, something he believed was all I deserved. He taught me know when to stop so my cum, just dribbled out.
Of course, during those eight years, Ann and Tony had some amazing sex. She was right, he was excellent in bed and, while it sounds a bit odd, I feel it brought us closer together.
We split up because Ann was offered a job in Western Australia. I was working by this time and couldn’t leave Sydney so we decided to go our separate ways. There followed six months living with a gay guy who believed I was gay as well. We lived for a couple in his flat until I met Beth.
Coming next – me and Beth