I was 20 and still a virgin.
I had only known my then, girlfriend for a couple of months but I was madly in love and I proposed to her. She said that I had to be aware of a few things before she would answer.
She said she was bi and and that she was still sleeping with her best friend and that she'd want to be able to continue to see her and any other women she might want to make out with, in the future.
She explained how she lost her virginity to a much older, married couple and how they introduced her to the idea of thinking of sex as a fun thing to do and not to restrict oneself to just one person in a relationship. That would mean severely restricting the fun she could have in the future and also lead to useless emotions like jealousy.
She admitted she'd cheated on her previous boyfriend but that it didn't affect the way she felt about him and they'd even had a foursome with a couple he knew and it had been great fun.
She said that she would want me to have the same freedom and that as she knew I kinda liked her sister, I could go with her if I wanted.
I was taken aback by this but, thinking I'd never go with her sister and so in love with my girlfriend, that I agreed and she accepted my proposal.
I wasn't able to see her every weekend as I lived a fairly long way from her and I worked shifts so after there'd been a gap of a few weeks when I didn't see her, I suspected that she'd probably been with her best friend in that time, but it didn't bother me.
A couple of months later I did end up having a couple of unexpected trysts with her sister and I admitted them to her immediately and she surprised me by being turned on by them and encouraged me to go further with her in the future.
I felt ashamed though so when she told me she was going to a workplace party and that a married man she had a crush on, was giving her a lift, I mentioned that I wouldn't mind if she fucked him. She told me she intended to and gave me a big grin. I wasn't able to see her during the weekend of the party and this was long before the internet so on the evening of the party I could only imagine her fucking him in his car and I found I was really turned on.
I wrote to her and asked her to tell me what they did and how excited I'd felt. She got the letter a couple of days later, when she got home from work and wrote back saying how they'd fucked that night and that she'd only just sucked him off as she knelt under his desk when the office had been empty.
I didn't know about the term 'cuckold' at this time but I knew then that I was going to enjoy our marriage together.
How old were you when you became a cuckold?
-
Thebestdays1
- Pervert
- Posts: 534
- Joined: Wed Feb 15, 2023 3:02 am
Re: How old were you when you became a cuckold?
Late 20s and we were newlywed. We wanted to start a family and it developed from a cheating situation with consequences.
the long stony way: viewtopic.php?f=6&t=57837
Re: How old were you when you became a cuckold?
I was 22 and at 69 I am still married to the same woman. She is still bringing fresh loads of cum back to me. Most of our friends and coworkers know because she has fucked just about everyone of them.
Craig
Re: How old were you when you became a cuckold?
I was 21, my late wife 18 years old. But we didn't know that the expressions cuckold and HW existed.
When I went to an university I wanted to break our relationship to be free.
My GF could imagine this very well but, as she said, "that isn't a reason to finish our relationship."
It was she who phoned me that she had a wonderful day with a doctor to become.
On my question what they had done she told me she wore the daring bikini I bought for her and he played with her breasts and nipples.
"Of course I kissed him a lot to let him know I liked what he did to me."
A year later I rented three rooms with a younger brother of my best friend. One big one room for mutual use.
We were naked when he came in unexpectedly.
My GF tried to hide her nakedness but my roommate persuaded her to let him see at least her breasts.
From then on she loved to let him play with her bare breasts. Almost always she kept her eyes fixed to mine.
Two (three?) years later I played the National Student Tennis Championship.
My GF would arrive a day later by train.
I asked a very new friend to look after her at the railway station.
When they arrived at the court on which I was playing my single, they behaved like newlyweds.
They even tongue kissed when I had to switch sides.
Of course I lost my match.
Some weeks later, this friend visited us. Or, rather her...
We sat on the couch, she between the two of us.
He, with the help of my GF, took off her blouse.
He played with her breast while still covered by her bra.
He: "The bra is annoying me."
My GF: "Then take it off. Whoever says A must also do B."
He did and her breasts and nipples received the attention she appeared to want so much.
Some moments later his hand went under her panties.
She: "When you say A, you have to say B I told you already. What do you care? My BF will not kill you."
He got up to stand in front of her and took the top of her thong in his fingers.
My GF helped him remove her thong by lifting her lower body.
Now she was completely naked between two clothed men.
He sat down next to her again to immediately start playing with her pussy with his hands.
For a moment she kissed me (in thanks?) only to kiss him immediately afterwards.
She kept kissing him until she came shaking with her body.
It would be more than 40 more years before she became a real leading Lady.
Not that nothing happened in the meantime. But that is out of place here.
When I went to an university I wanted to break our relationship to be free.
My GF could imagine this very well but, as she said, "that isn't a reason to finish our relationship."
It was she who phoned me that she had a wonderful day with a doctor to become.
On my question what they had done she told me she wore the daring bikini I bought for her and he played with her breasts and nipples.
"Of course I kissed him a lot to let him know I liked what he did to me."
A year later I rented three rooms with a younger brother of my best friend. One big one room for mutual use.
We were naked when he came in unexpectedly.
My GF tried to hide her nakedness but my roommate persuaded her to let him see at least her breasts.
From then on she loved to let him play with her bare breasts. Almost always she kept her eyes fixed to mine.
Two (three?) years later I played the National Student Tennis Championship.
My GF would arrive a day later by train.
I asked a very new friend to look after her at the railway station.
When they arrived at the court on which I was playing my single, they behaved like newlyweds.
They even tongue kissed when I had to switch sides.
Of course I lost my match.
Some weeks later, this friend visited us. Or, rather her...
We sat on the couch, she between the two of us.
He, with the help of my GF, took off her blouse.
He played with her breast while still covered by her bra.
He: "The bra is annoying me."
My GF: "Then take it off. Whoever says A must also do B."
He did and her breasts and nipples received the attention she appeared to want so much.
Some moments later his hand went under her panties.
She: "When you say A, you have to say B I told you already. What do you care? My BF will not kill you."
He got up to stand in front of her and took the top of her thong in his fingers.
My GF helped him remove her thong by lifting her lower body.
Now she was completely naked between two clothed men.
He sat down next to her again to immediately start playing with her pussy with his hands.
For a moment she kissed me (in thanks?) only to kiss him immediately afterwards.
She kept kissing him until she came shaking with her body.
It would be more than 40 more years before she became a real leading Lady.
Not that nothing happened in the meantime. But that is out of place here.
Early in 2023, all my settings disappeared.
To read (and view) my contributions advanced search for author "dinoo".
We visited frequently a club. (www.kasteelwaterloo.nl)
It became "our" club.
To read (and view) my contributions advanced search for author "dinoo".
We visited frequently a club. (www.kasteelwaterloo.nl)
It became "our" club.
Re: How old were you when you became a cuckold?
I wish I knew.
At the time the events of my wife's extensive cheating and dishonesty began to sink in about 10 years ago I would've told you that somewhere around 49-50 years old I became a cuckold. In recent years I realize that it may have been happening from the time I was 16.
At 16 I met and spent much time with a young lady of 17 who I would call my first serious love interest. We were involved in little more than heavy petting and making out. I sensed there was something holding her back emotionally and questioned her about that. She confessed that since age 15 she had been involved with a married man in his early 30s who had been an advisor in an afterschool program. By the time I met her that relationship had cooled down somewhat, but they still got together occasionally. She was a good catholic girl who was extremely concerned about pregnancy, but the man had been snipped so they were indeed having sex. At 16 the feeling that I was unable to compete with a grown man for her affection was overwhelming for a while.
As I scuffled with those feelings through the Christmas holiday, I met an almost 16 year old who went to school with a friend. Our teenage romance heated up rather quickly. Many winter nights hitchhiking the 10 miles out to the house on the hill where she lived with her mother and little brother. I was a virgin but never admitted it. Many hot nights on her sofa and the bed in the basement, finger fucking her to multiple orgasms and her trying unsuccessfully to bring me off with oral. She was fantastic but I had some strange mental block that prevented me from letting go with oral. This girl was quite knowledgeable sexually for a teenager in the mid 1970s. Our relationship was fraught with headaches due to my wild nature and her roaming eyes.
A married couple in their 30s lived next door to her and were good friends with her and her mother. The husband injured his back at some point and was recuperating at home that summer. I didn't realize it at the time but over the summer she had begun fucking him while his wife was at work. There were others I'm sure but honestly I had never been monogamous anyway. Predictably, due in no small part to my increasing interest in drinking and smoking weed she slowly peeled away from me and we were done by the end of the year.
Just as the book on that romance closed came New Years Eve 1976. Memorable, as it was the only time I have ever been stood up. My friends were tending bar at a racquet club party that night, so they invited me to stay and hang out with their houseguest, a petite dark brunette. 23 year old Vicki and I hit it off quite well. We fucked from about 10:30 that night until 5:30 in the morning. She was so soft, sweet and inviting. Everything felt more natural than the high school girls I'd always messed around with.
There was no romance with Vicki, just a very pleasant fwb situation. We would get together periodically over the next couple of years. A month or 2 into that I got a call early one morning from the common-law husband I'd heard about. The younger brother of the friend I met Vicki through had been teasing me about how her partner was going to kick my ass when he got out of jail. I didn't pay that mucb mind but imagine my surprise when I got a call from the jail early one morning.
Terry and Vicki had been together for several years but Terry, as he was prone to do, got in trouble with the law and was doing time. He called about 7:30 one morning. Right out of the gate he told me that Vicki had told him about me, that I was a nice guy and treated her very well. He said that he had screwed up and was now paying the price and that he had no problem with Vicki enjoying my company while he was locked up. Then he proceeded to ask me very direct, sexual questions, which I answered honestly while being completely freaked out by the situation.
Does she suck your cock?
Yes.
Have you fucked her ass?
No.
Do you usually cum inside her?
Yes.
Must've been about 6 months later I was at the home of the previously mentioned friend's parents installing some speakers in my car when Vicki and a rather large man came walking up the driveway. Realizing this must be Terry, I crawled out of the back seat of the car and went to meet my fate. As I approached them he said "You must be ___" and extended his hand. I shook his hand as he thanked me for taking good care of Vicki while he was away. He said he had some business there but invited me to go back to their apartment with them when he was done. Apparently, there was a disagreement with our mutual friend over some money Vicki had contributed to the household expenses while she stayed with the guy and his girlfriend. At any rate, I declined the invitation to join them at their apartment. A few months later I heard from Vicki again. Terry had been locked up again and she missed my company.
Being the sleazebag I was, at 19 years old I ushered one young woman out of a bad marriage and into a questionable 2 year relationship with me. Coincidentally just recently I had the chance to see her for the first time in over 40 years and to make amends for my behavior. After that relationship ended I fell madly in love with a 28 year old married woman (I was 21) who for a while I hoped would see the light and want to be with me full time. D. however was content to stay with the husband and keep a boyfriend on the side. They had been together since they were quite young and he was her rock. If they had an agreement for her to play it was never shared with me. He did tell me once that I wasn't the first and probably wouldn't be the last.
The first year she was at my place nearly every day, sometimes into the wee hours of the morning. While her body wasn't normally the type I would go for (5'6", 130 lbs, guesstimating 34C-26-38) she was absolutely gorgeous. Strawberry blonde, sparkling blue eyes, adorable in her glasses, full, sensual lips. She loved younger men and we were fucking constantly, usually with me leaving a thick load inside her to take home. After about a year, selfish tool I was, I became frustrated about not being able to live with her so I left town. That lasted just 3-4 weeks. When I returned I was staying with my parents but her and I hooked right back up, usually in the car or the seedy motels I could afford. The relationship was changing though. She was no longer willing to stay out at night and what had been about 6 days a week became 3 or 4 days a week.
I resigned myself to the fuck buddy situation and began seeing other young women. Many other young women, a few of which stand out. More about that later.
One afternoon I went to the mall to meet her at her store to go have lunch. On the bench outside the store a man asked if he could bum a cigarette and I obliged. We got to talking. Soon he was telling me about this amazing woman he'd met who worked at the store. He had just popped over there to see of she'd like to have lunch. Well sure, you see where this is going. He was a little miffed when she came out, politely told him she had plans with me and we went on our way.
A brief sidebar if I may. Seems crazy, but when it comes to sex with her the thing I think about the most from those days 40+ years ago are the blowjobs in the parking lot at McDonalds or wherever during those lunch hour dates.
Well, this relationship took a long time to die. We went on for a total of about 4 years. Toward the end, one night knowing her husband and daughter were out of town I invited myself over to her house. One thing led to another and soon we were making out in her marital bed. I moved down to lick her deliciously sweet pussy. She resisted a little, which was very strange. She loved oral so much. I persisted and had been kissing, licking and sucking her for just a moment when it occurred to me that she tasted quite different than usual. By the time she came a few minutes later I was sure someone else had been there earlier that day. I wondered if it was the guy from the store. It neither turned me on or grossed me out. I would come to realize that this was my first experience cleaning a woman up down there.
D and I ran into each other about 2 years after our thing finally ended. I was living with the young woman who would eventually become my wife by then. We had sex once but whatever magic had been there before was gone, for both of us I think. Some years later I was able to make an amends to her too. From what I gather from the newspaper at some point she and her husband did finally get divorced, and he passed away from a heart attack a couple of years later. I've run into her a few times since and it's been brief, but cordial.
I'll leave it there for now, and if there's any interest will pick it back up and work my way to when I was profoundly cuckolded by my wife.
At the time the events of my wife's extensive cheating and dishonesty began to sink in about 10 years ago I would've told you that somewhere around 49-50 years old I became a cuckold. In recent years I realize that it may have been happening from the time I was 16.
At 16 I met and spent much time with a young lady of 17 who I would call my first serious love interest. We were involved in little more than heavy petting and making out. I sensed there was something holding her back emotionally and questioned her about that. She confessed that since age 15 she had been involved with a married man in his early 30s who had been an advisor in an afterschool program. By the time I met her that relationship had cooled down somewhat, but they still got together occasionally. She was a good catholic girl who was extremely concerned about pregnancy, but the man had been snipped so they were indeed having sex. At 16 the feeling that I was unable to compete with a grown man for her affection was overwhelming for a while.
As I scuffled with those feelings through the Christmas holiday, I met an almost 16 year old who went to school with a friend. Our teenage romance heated up rather quickly. Many winter nights hitchhiking the 10 miles out to the house on the hill where she lived with her mother and little brother. I was a virgin but never admitted it. Many hot nights on her sofa and the bed in the basement, finger fucking her to multiple orgasms and her trying unsuccessfully to bring me off with oral. She was fantastic but I had some strange mental block that prevented me from letting go with oral. This girl was quite knowledgeable sexually for a teenager in the mid 1970s. Our relationship was fraught with headaches due to my wild nature and her roaming eyes.
A married couple in their 30s lived next door to her and were good friends with her and her mother. The husband injured his back at some point and was recuperating at home that summer. I didn't realize it at the time but over the summer she had begun fucking him while his wife was at work. There were others I'm sure but honestly I had never been monogamous anyway. Predictably, due in no small part to my increasing interest in drinking and smoking weed she slowly peeled away from me and we were done by the end of the year.
Just as the book on that romance closed came New Years Eve 1976. Memorable, as it was the only time I have ever been stood up. My friends were tending bar at a racquet club party that night, so they invited me to stay and hang out with their houseguest, a petite dark brunette. 23 year old Vicki and I hit it off quite well. We fucked from about 10:30 that night until 5:30 in the morning. She was so soft, sweet and inviting. Everything felt more natural than the high school girls I'd always messed around with.
There was no romance with Vicki, just a very pleasant fwb situation. We would get together periodically over the next couple of years. A month or 2 into that I got a call early one morning from the common-law husband I'd heard about. The younger brother of the friend I met Vicki through had been teasing me about how her partner was going to kick my ass when he got out of jail. I didn't pay that mucb mind but imagine my surprise when I got a call from the jail early one morning.
Terry and Vicki had been together for several years but Terry, as he was prone to do, got in trouble with the law and was doing time. He called about 7:30 one morning. Right out of the gate he told me that Vicki had told him about me, that I was a nice guy and treated her very well. He said that he had screwed up and was now paying the price and that he had no problem with Vicki enjoying my company while he was locked up. Then he proceeded to ask me very direct, sexual questions, which I answered honestly while being completely freaked out by the situation.
Does she suck your cock?
Yes.
Have you fucked her ass?
No.
Do you usually cum inside her?
Yes.
Must've been about 6 months later I was at the home of the previously mentioned friend's parents installing some speakers in my car when Vicki and a rather large man came walking up the driveway. Realizing this must be Terry, I crawled out of the back seat of the car and went to meet my fate. As I approached them he said "You must be ___" and extended his hand. I shook his hand as he thanked me for taking good care of Vicki while he was away. He said he had some business there but invited me to go back to their apartment with them when he was done. Apparently, there was a disagreement with our mutual friend over some money Vicki had contributed to the household expenses while she stayed with the guy and his girlfriend. At any rate, I declined the invitation to join them at their apartment. A few months later I heard from Vicki again. Terry had been locked up again and she missed my company.
Being the sleazebag I was, at 19 years old I ushered one young woman out of a bad marriage and into a questionable 2 year relationship with me. Coincidentally just recently I had the chance to see her for the first time in over 40 years and to make amends for my behavior. After that relationship ended I fell madly in love with a 28 year old married woman (I was 21) who for a while I hoped would see the light and want to be with me full time. D. however was content to stay with the husband and keep a boyfriend on the side. They had been together since they were quite young and he was her rock. If they had an agreement for her to play it was never shared with me. He did tell me once that I wasn't the first and probably wouldn't be the last.
The first year she was at my place nearly every day, sometimes into the wee hours of the morning. While her body wasn't normally the type I would go for (5'6", 130 lbs, guesstimating 34C-26-38) she was absolutely gorgeous. Strawberry blonde, sparkling blue eyes, adorable in her glasses, full, sensual lips. She loved younger men and we were fucking constantly, usually with me leaving a thick load inside her to take home. After about a year, selfish tool I was, I became frustrated about not being able to live with her so I left town. That lasted just 3-4 weeks. When I returned I was staying with my parents but her and I hooked right back up, usually in the car or the seedy motels I could afford. The relationship was changing though. She was no longer willing to stay out at night and what had been about 6 days a week became 3 or 4 days a week.
I resigned myself to the fuck buddy situation and began seeing other young women. Many other young women, a few of which stand out. More about that later.
One afternoon I went to the mall to meet her at her store to go have lunch. On the bench outside the store a man asked if he could bum a cigarette and I obliged. We got to talking. Soon he was telling me about this amazing woman he'd met who worked at the store. He had just popped over there to see of she'd like to have lunch. Well sure, you see where this is going. He was a little miffed when she came out, politely told him she had plans with me and we went on our way.
A brief sidebar if I may. Seems crazy, but when it comes to sex with her the thing I think about the most from those days 40+ years ago are the blowjobs in the parking lot at McDonalds or wherever during those lunch hour dates.
Well, this relationship took a long time to die. We went on for a total of about 4 years. Toward the end, one night knowing her husband and daughter were out of town I invited myself over to her house. One thing led to another and soon we were making out in her marital bed. I moved down to lick her deliciously sweet pussy. She resisted a little, which was very strange. She loved oral so much. I persisted and had been kissing, licking and sucking her for just a moment when it occurred to me that she tasted quite different than usual. By the time she came a few minutes later I was sure someone else had been there earlier that day. I wondered if it was the guy from the store. It neither turned me on or grossed me out. I would come to realize that this was my first experience cleaning a woman up down there.
D and I ran into each other about 2 years after our thing finally ended. I was living with the young woman who would eventually become my wife by then. We had sex once but whatever magic had been there before was gone, for both of us I think. Some years later I was able to make an amends to her too. From what I gather from the newspaper at some point she and her husband did finally get divorced, and he passed away from a heart attack a couple of years later. I've run into her a few times since and it's been brief, but cordial.
I'll leave it there for now, and if there's any interest will pick it back up and work my way to when I was profoundly cuckolded by my wife.
Re: How old were you when you became a cuckold?
I began sharing her when we were 33.
Hubby of Hotwife from late summer '88 to late winter '93. A fun 4 1/2 year run.