Help keep this site alive with your VIP membership and unlock exciting site features available only to our supporting members!
UPGRADE to get lifetime access to dig420's video section, the Meet Up! forums, AD FREE surfing and much, much more!
What's your biggest ever sexual regret?
- Thread starterSwingingChris
- Start date
Not capitalising on my exes secret guilt…. She used to hurt herself while talking to strangers I would have begging to be hurt…. If I’d known I would have “accidentally” slipped in her arse more often! And been honest about selling her knix to the neighbour
My ebony wife started ********* on the side and I would even take her to appointments with men, at times. During that time, I wasnt paying much attn sexually to her, and didnt mind if she escorted. Now, looking back, it is such a turn on that she escorted, got naked for mostly white men, and gave guys naked lap dances and finished them of with hand and blow jobs.
I wish I would have paid more attention back then to what she was doing because I am begging her to sleep with men for me now that we are happily married! Hopefully, we can turn the corner at some point, but I guess the good news is, I know she has it in her.
I wish I would have paid more attention back then to what she was doing because I am begging her to sleep with men for me now that we are happily married! Hopefully, we can turn the corner at some point, but I guess the good news is, I know she has it in her.
Last edited:
One night me and my ex-wife were driving in New York City by Park Ave., South and 28th St. was an open lot parking lot with a pimps hang out in their lady’s and my sexy blonde wife ask one of pimp to come over
To my car she told him through the window that she can suck a fuck better than any of his ladies and was way better looking He asked me to pull it into the lot which I did he open the door and she stepped halfway out while still sitting with her legs, spread. He’s referring to her as she pulled out his cock and suck his cock the other pimps came over and before I knew it they have her in the back seat of my Cadillac with the back doors open she was bent over the seat sucking one of guy sitting down in the backseat of the car she bent over and behind her, was other black guy fucking the shit out of her.
My regret is we didn’t have cameras back, then it happen back in 1989 summer about 2am anyways they all fucked her and 3 or 4 ass fucked her made her do ass to mouth after 3 or 4 of them, took her to the back wall of the parking lot, made her kneel on the cardboard and they begin to piss on her. To top to bottom And my surprise. She enjoy the golden shower.
The following days.
She want to talk about it.
After a few months later, she told me after work she went back a few times.
You see she works from 4pm to 12 midnight
She told me her fantasy was to be owned by pimps. She didn’t tell me because she thought I would be mad instead, I told her I loved hearing about it
To my car she told him through the window that she can suck a fuck better than any of his ladies and was way better looking He asked me to pull it into the lot which I did he open the door and she stepped halfway out while still sitting with her legs, spread. He’s referring to her as she pulled out his cock and suck his cock the other pimps came over and before I knew it they have her in the back seat of my Cadillac with the back doors open she was bent over the seat sucking one of guy sitting down in the backseat of the car she bent over and behind her, was other black guy fucking the shit out of her.
My regret is we didn’t have cameras back, then it happen back in 1989 summer about 2am anyways they all fucked her and 3 or 4 ass fucked her made her do ass to mouth after 3 or 4 of them, took her to the back wall of the parking lot, made her kneel on the cardboard and they begin to piss on her. To top to bottom And my surprise. She enjoy the golden shower.
The following days.
She want to talk about it.
After a few months later, she told me after work she went back a few times.
You see she works from 4pm to 12 midnight
She told me her fantasy was to be owned by pimps. She didn’t tell me because she thought I would be mad instead, I told her I loved hearing about it
Last edited:
My ex (attached) was cheating on me with a married man and divorced me to start a relationship with him. But I had to remain in the home for a bit. In that time span, I started fucking his ex-wife, but no relationship.
My ex would then start initiating sex with me here and there too. So I was fucking both. I come to find out, he was fucking both too. Seemed the next logical step was to start start a 4-some.
My ex started getting jealous that he was fucking his exwife—since they were in a relationship. I pointed out the hypocrisy… she got mad and I moved out the next day…
I wonder what would have happened if I didn’t move out And instead, just egged on a 4-way relationship. His exwife loved being ravished by both of us, and didn’t want to stop fucking both of us.
But since I left, my ex and him went exclusive. And my thing with his ex fizzled out.
My ex would then start initiating sex with me here and there too. So I was fucking both. I come to find out, he was fucking both too. Seemed the next logical step was to start start a 4-some.
My ex started getting jealous that he was fucking his exwife—since they were in a relationship. I pointed out the hypocrisy… she got mad and I moved out the next day…
I wonder what would have happened if I didn’t move out And instead, just egged on a 4-way relationship. His exwife loved being ravished by both of us, and didn’t want to stop fucking both of us.
But since I left, my ex and him went exclusive. And my thing with his ex fizzled out.
Last edited:
I went out with a woman for 9 years but we took a year break in the middle. When we got back together she confessed she had cheated on me at the end of our first period together. She told me she had fucked half a dozen guys in the last 6 months we were together. One of these she left me for. She told me that she had come home on numerous occassions after fucking someone with their cum still in her pussy. She told me that there were times she had sat next to me to watch TV and cum dribbled from her pussy. There were also times she came home from a fuck and got straight into bed with me. She told me there was even a time that I had cuddled her, got hard and fucked her and I said how wet her pussy was and she now confessed it wasnt because she was excited, but because less than an hour earlier a guy had cum in her.
She also said that after she left the guy she had left me for she had gone a bit mad and had fucked a fair few guys. She told me in detail about some of them.
She noticed how hard I would get when we talked about her exploits when she cheated on me and we had great sex. I told her that in the future, if she wanted to fuck other guys she should just tell me ... and I would love to watch her. She never did and then had another affair and left me for the guy. That was back in 2005 and they are married now.
I regret I could never get her to fuck other guys while I could watch her
She also said that after she left the guy she had left me for she had gone a bit mad and had fucked a fair few guys. She told me in detail about some of them.
She noticed how hard I would get when we talked about her exploits when she cheated on me and we had great sex. I told her that in the future, if she wanted to fuck other guys she should just tell me ... and I would love to watch her. She never did and then had another affair and left me for the guy. That was back in 2005 and they are married now.
I regret I could never get her to fuck other guys while I could watch her
What a body she has!! Fuck!!devontallguy said:I went out with a woman for 9 years but we took a year break in the middle. When we got back together she confessed she had cheated on me at the end of our first period together. She told me she had fucked half a dozen guys in the last 6 months we were together. One of these she left me for. She told me that she had come home on numerous occassions after fucking someone with their cum still in her pussy. She told me that there were times she had sat next to me to watch TV and cum dribbled from her pussy. There were also times she came home from a fuck and got straight into bed with me. She told me there was even a time that I had cuddled her, got hard and fucked her and I said how wet her pussy was and she now confessed it wasnt because she was excited, but because less than an hour earlier a guy had cum in her.
She also said that after she left the guy she had left me for she had gone a bit mad and had fucked a fair few guys. She told me in detail about some of them.
She noticed how hard I would get when we talked about her exploits when she cheated on me and we had great sex. I told her that in the future, if she wanted to fuck other guys she should just tell me ... and I would love to watch her. She never did and then had another affair and left me for the guy. That was back in 2005 and they are married now.
I regret I could never get her to fuck other guys while I could watch her
devontallguy said:
devontallguy said:I went out with a woman for 9 years but we took a year break in the middle. When we got back together she confessed she had cheated on me at the end of our first period together. She told me she had fucked half a dozen guys in the last 6 months we were together. One of these she left me for. She told me that she had come home on numerous occassions after fucking someone with their cum still in her pussy. She told me that there were times she had sat next to me to watch TV and cum dribbled from her pussy. There were also times she came home from a fuck and got straight into bed with me. She told me there was even a time that I had cuddled her, got hard and fucked her and I said how wet her pussy was and she now confessed it wasnt because she was excited, but because less than an hour earlier a guy had cum in her.
She also said that after she left the guy she had left me for she had gone a bit mad and had fucked a fair few guys. She told me in detail about some of them.
She noticed how hard I would get when we talked about her exploits when she cheated on me and we had great sex. I told her that in the future, if she wanted to fuck other guys she should just tell me ... and I would love to watch her. She never did and then had another affair and left me for the guy. That was back in 2005 and they are married now.
I regret I could never get her to fuck other guys while I could watch her
Late 80s when we 1st got together she had very loose sexual morals and I didn't, I won out and we became exclusive. As time went by I became looser and she became tighter until I wanted her to go back to having sex with others and she didn't want to. Finally she did become a hotwife.Took 30 years, I regret not following her loose morals, 30 years of missed sexual activity with a willing woman.
