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What's your biggest ever sexual regret?

  • Thread starterSwingingChris
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  • #101
I guess that one of my regrets must be turning down the chance of same sex play when I was 14 years old. Back then and for many later years I was basically a homophobe and derided those who had same sex play.

At that time I was having a male friend sleep over and share my bed. That friend Melvin woke me during the night and he was slowly wanking my erect and hard cock. I instantly slapped his hand away and he slept the rest of the night on the floor. I’d so love to re engage with Melvin, apologise and hopefully show him what I’ve since learned.

If only I’d have known then that many (probably the majority) of males are bi sexual and they can and do enjoy sex with both sexes. I now appreciate and love sex with both males and females and wonder in fact whether the wonderful joy of having my man pussie filled with a lovers hot cum eclipses the best female sex? Yes I now prefer sex with males!
 
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  • #102
Not saying yes to an ex gf when she said she wanted me to watch her get fucked by another guy. Biggest regret of my life so far
 
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  • #103
Not going bare from the beginning, when we started out we always insisted on condoms till one meet with well hung guy that didn’t fit him. It was a game changer, after that meet the condoms were thrown in the bin.
 
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  • #104
Hubbytells said:
Not going bare from the beginning, when we started out we always insisted on condoms till one meet with well hung guy that didn’t fit him. It was a game changer, after that meet the condoms were thrown in the bin.
hubby and I used a condom the first time we had sex when we were 18. I had to get it out after if came off inside.

Have never used one since.
 
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  • #105
When we were in college, my now wife and I, had a friend with an adventurous girlfriend. We’d send snapchats back and forth as couples while we each had sex or had a sexual act done. They wanted to full swap with us, never ended up doing it. Years later, me and him are still friends and we’ve actually had him join us but his gf is long gone
 
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  • #106
I'd say playing with close people like friends and family never again in my new relationship.
 
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  • #108
Not setting up a MFF when I was in Thailand for military training bc I was being faithful to my wife who I later divorced for cheating on me.
 
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  • #109
Shepardwronged said:
Not setting up a MFF when I was in Thailand for military training bc I was being faithful to my wife who I later divorced for cheating on me.
Just reminds of a time when a very hot milf neighbor was very eager that I fuck her, and I was faithful to my cheater wife.
 
  • #110
My EX-wife and I met at the start of 11th grade of high school. I got her cherry by Christmas and we were fucking several times every day, almost every chance we got. She was gorgeous and wore a 34DD cup bra, If you ever saw the porn actress Samantha 38g, imagine the same woman with 30 pounds less weight. 5-7, big boobs, blonde. Even in high school, I had fantasies of watching her fuck other guys, She was incredibly hot looking

We married after fucking for 3 years. I was away at college, she lived at home with her parents. 2 years later, child #1. Then I graduated and entered the work force traveling a lot for the next 7 years and 3 more kids. I began to suspect that she was finding other men while I was away and perhaps #4 is not my child. I suspected that a business acquaintance, an automobile dealer, was fucking her, fathering #4.

At our age 28, we moved to Panama and began living together as a family, with me working odd hours, never away from home more than 13 hours. Sex with her was fantastic and frequent. The next 5 years were great, life, job, career all in blossom.

At age 34, I took a different job requiring that we all move to my next work area 5000 miles away. The Ex had gained weight, now looking almost exactly like Samantha 38g, but still super hot. She entered a weight loss program and recovered her former figure. She was so spectacular looking that the weight loss program made her their star Representative. She traveled with a male counterpart to promote the program and they became lovers.

To reciprocate, I found other women too, but keeping in mind the need to provide for my family, I did not demand that she stop fucking him. My career was soaring, and as long as she kept me sexually satisfied, I did not force change.

3 years later, I returned to Panama for a big pay increase and moved my family back the same 5000 miles. Then she started going out while I was at work and was fucking other guys.

I was away on business for 5 days and when I got back home, my wife admitted that she had been kissing a co-worker of mine named Freddy. at the Yacht Club He was single and lived alone near our apartment.

I did not respond well to exploit the situation. I should have asked if he touched her tits and if so, did he fuck her. My long time wish to watch her with other guys was lost for the time. But she started to spend a lot of time on the phone with somebody (Freddy)?

Then about a week later, One night, right after dinner, I went to bed early because I had a callout for work at 3 AM. She came to bed with me and we fucked, so that I would sleep soundly. About 11 PM, I was awake and sitting on the end of the bed looking out the window. I saw my wife, with her distinct super busty figure in a tight black sweater, black pants and HIGH HEELS in front of the house, scurrying down the street towards Freddy's apartment.

I followed.

Silently, I entered the back door of his apartment unit into his kitchen. Through the crack in the kitchen door I could look into his living room. He was sitting on a sofa wearing an open bathrobe.

She was standing in front of him, heels and all, holding a drink and doing a sexy dance routine. She pulled her tight black sweater up and over her head making her massive breasts bounce up and down in her bra. Then she shrugged off her bra and her huge breasts burst out. She continued dancing, but I could not stand it any more and burst into the living room.

When she saw me, she cursed me with every foul name and demanded that I get the hell out.

The guy sat there cool.

Again, I had another one time great opportunity. I could have told them to go ahead with their fuck. But no, I was not prepared mentally yet.

She got dressed again, her hoped for fuck with him was not going to happen. As I calmed down, I asked him if he wanted her on a permanent basis, and if so, I would divorce her.

He declined, so I took her home and demanded that she stop running around on me. She so promised.

Two days later,
An Asian neighbor lady told my Second daughter that she had been seeing my wife with Freddy at a downtown hotel during the day. She was a Bingo Gambling fanatic and the game at the hotel was high stakes Bingo. She revealed that to my 11 year old daughter and my daughter told me. My daughter must have understood what she was telling me.

I had a friend in the local phone (Wired) exchange and put a tap on our phone and listened to all the calls. Amid all the chattering of our 4 kids on the phone, I learned more about her affair with "her friend:"

I discovered that she was fucking other guys from the local army base too. One evening, while heading home, I saw my fancy Sportscar parked behind a GI bar. I went into the bar and saw her at a table with 4 GIs.

She introduced me as her husband to her 4 friends,.

I should have asked, "Which one of you or are all of you are going home with us tonight?"

The 4 GIs disappeared like roaches out the door and into the night.

Then about 2 months later my phone taps revealed that my wife had stopped fucking Freddy, but there were others guys.

At that point there was no longer any reason to not openly share my wife. To be honest I had a girlfriend by then too.

Her sluttish behavior was getting embarrassing. Our long time maid/housekeeper suddenly quit. My wife's scandalous activities disgusted her. She stayed because she loved our kids.

A female family member who was visiting with us suddenly returned home. Never did say why.

One afternoon, the wife and I were in bed after fucking and she asked me if I would be interested if another woman wanted to be a 3 some with us.

I only half listened and never found out who she had in mind. Another regret.
 
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  • #111
Regcuckcouple said:
Not having sex with my ex mother in law when I had the chance. Much older but when she stood and watched me dry off after the shower I’m sure she would have.
My biggest regret is my mother in law never giving me the opportunity,I made plenty attempts at body contact whilst sitting next to her, my arm against her breat etc, leg against leg, but never got any encouragment.

Had I gotten the slightest encouragment I'd have been like a rat up a drainpipe:p
 
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  • #112
A few years after our return from Africa, my wife mentioned to me in passing that she had had the opportunity to cheat on me there. She never specified whether she had done so or declined the offer. Out of fear, cowardice, and pride, I did not want to continue this conversation or bring it up again later.
Today, I deeply regret it and I like to imagine that in the end, she took advantage of it, at least once. I also remember the men in our expatriate circle at the time. Who could it have been? My boss? One of my colleagues? A friend? Someone who didn't necessarily like me? An African? A stranger (to me) but whom she would have met under what circumstances?
 
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  • #113
Sandy Row said:
My biggest regret is my mother in law never giving me the opportunity,I made plenty attempts at body contact whilst sitting next to her, my arm against her breat etc, leg against leg, but never got any encouragment.

Had I gotten the slightest encouragment I'd have been like a rat up a drainpipe:p
One of my great regrets too! My mother in law was much sexier and much more beautiful than my fiancé. When my fiancé was studying in another town, her mother used me like her private driver. I loved it as it gave me the opportunity to stare at her sexy thick white thighs as she sat next to me. She almost ways wore minis and sandals. I jerked to her thousands of times those years! There were a few occasions when I'm sure she wouldn't mind if I kissed her, but I was too timid. I saw her in revealing night gowns many times. I still regret I didn't go for her.
 
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  • #114
Rooscuck said:
... I saw her in revealing night gowns many times. I still regret I didn't go for her.
There is nothing sexier (to me) than a wife in a gown that is transparent.
I think it is so hot to see a lady who is totally covered, yet ******* at the same time.

Even the wives who wear the thin cotton "granny gowns" that show through when backlit are a huge turn on.

And it instantly creates the question in your mind; is it accidental or does she not realize, or is she trying to seduce you?
 
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  • #115
Nazareth said:
There is nothing sexier (to me) than a wife in a gown that is transparent.
I think it is so hot to see a lady who is totally covered, yet ******* at the same time.

Even the wives who wear the thin cotton "granny gowns" that show through when backlit are a huge turn on.

And it instantly creates the question in your mind; is it accidental or does she not realize, or is she trying to seduce you?
She has to be teasing! Why would she wear that in front of of your wife’s husband? Seems highly inappropriate
 
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  • #117
When I was in middle school, had a friend jacking off inches from my face, I was in the floor he was on the edge of the bed. I know he wanted me to suck it, but we were both scared to say it, so he came in his hand. I’ve craved his cock ever since.
 
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  • #118
Nazareth said:
There is nothing sexier (to me) than a wife in a gown that is transparent.
I think it is so hot to see a lady who is totally covered, yet ******* at the same time.

Even the wives who wear the thin cotton "granny gowns" that show through when backlit are a huge turn on.

And it instantly creates the question in your mind; is it accidental or does she not realize, or is she trying to seduce you?
So true...those curves...and I like them to have their panties on but no bra.
 
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  • #119
Roghubs said:
When I was in middle school, had a friend jacking off inches from my face, I was in the floor he was on the edge of the bed. I know he wanted me to suck it, but we were both scared to say it, so he came in his hand. I’ve craved his cock ever since.
I remember jacking off with friends in high school no touching. I so wish now I had got on my knees and sucked their cocks.
 
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  • #120
seems like every girl friend I had and my wife I shared with my friends...but back in high school I stayed the night at one of my best friends house, his parents were gone...he asked if I wanted to just sleep in the same bed and I said no....and ended up sleeping in the guest room.
 
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