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What's your biggest ever sexual regret?

  • Thread starterSwingingChris
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Hawkdoctor said:
Never becoming swingers with my wife. We’re getting too old. Never watching my wife fucked by a bbc.
It's not too late to start swinging and for her to get fucked by a BBC.
 
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Cockduh said:
It's not too late to start swinging and for her to get fucked by a BBC.
She is 5’6” 160. Was 140 when we got married so 20 pounds heavier decades later. 38D and a thick bush trimmed on the sides for tanning. If we were swingers the other guy would get good fucking. I don’t have much stamina now so the other lady would get short changed! lol
 
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My biggest regret is waiting until recently to start telling my buddy to nut inside wife. Out of respect for us he always pulled out. Not long ago he was taking wife out for a date and I told him to use her like he owned her and cum inside. When he dropped her off at home that nite she came inside a total mess amd could hardly walk. He used her real good. I kinda forgot about telling him to blow it inside until I went down on her and noticed she was soaking wet and had a salted pussy taste. I been hooked ever since and love the taste and smell of her pussy after it's been nutted in.
 
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My girlfriend and I had just got back together(now wife) we had a foursome, and I came to fast(big surprise) and watched as she got with the girl and other guy...I didn't deal with it very well at all when we were done, I felt kinda blindsided as it was all idea(promoted by the other girl)

It was amazing to watch her lick, suck and get fucked by them.
I didn't have a sit down with her after and tell her I wanted us to have an open relationship...where we tell each other everything that happened if either one of us went out.
I worked on the road traveling 9 months a year, and had felt guilty about leaving her alone, when we all have needs.
After 31 years, she still won't add anyone to our playtime, male, female, black or white...even though I have given her a total free hall pass to bring anyone she wants into bed.
 
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When it became common knowledge that my wife had cheated on me a couple of my female co-workers made passes at me, one of them actually invited me to have sex with her. I was so concerned to save my marriage that I didn't take them up on it. To this day the only woman I've had penetrative sex with is my wife.
 
I have always wanted to fuck my mother in law I've seen her naked a few times and she has caught me masterbating while I watched her bending over a few times
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.
N
 
My biggest regret is not training my Asian wife to be shared
 
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I have two big regrets. That my father had a tiny dick. And that genetics work. LOL
 
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Bad: Passing on a clear invitation to fuck my ex’s good friend after we broke up because I was already banging her other close friend.

Worse: cheating when younger. It has haunted me to this day and wasn’t ever worth it.
 
I regret waiting for years to get into sharing my wife. Shortly after we were married we started fantasising about her being fucked by lots of guys. Before long she started suggesting that we actually do it but I kept resisting. She finally did it on her own, multiple times and with two different men. She didn’t tell me until I finally agreed that we could try swinging but didn’t know who we might hook up with. She knew who would be interested because she had already been with them.
 
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Far too many to list here:

Main ones (with hindsight)

Not appreciating just how slutty my ex was (but she was bpd though)

The group sex I turned down at uni (too
Many massive drugs)

Not fucking the dirty Welsh girl at uni as much as she wanted (again….. massive drugs)


Not dealing with wife’s infidelity in an adult manner (she can sleep around but broke the “don’t fuck friends” rule).

Getting all shirty when someone else made my wife cum (she is hard work to make orgasm). Now realised that’s it’s nothing to do with me, just someone’s headspace.
 
Justspitonit said:
Far too many to list here:

Main ones (with hindsight)

Not appreciating just how slutty my ex was (but she was bpd though)

The group sex I turned down at uni (too
Many massive drugs)

Not fucking the dirty Welsh girl at uni as much as she wanted (again….. massive drugs)


Not dealing with wife’s infidelity in an adult manner (she can sleep around but broke the “don’t fuck friends” rule).

Getting all shirty when someone else made my wife cum (she is hard work to make orgasm). Now realised that’s it’s nothing to do with me, just someone’s headspace.
No, it was probably you. LOL You need to get back on those massive drugs ... viagra. LOL
 
Another regret I have , the first New Year’s Eve we were married I did not kiss my wife’s friend Libby as I watch my wife play tonsil tennis with her husband I just stood and stared as they kissed until Libby said come on you two that’s enough , when we got outside Kate said to me “ why didn’t you kiss Libby I am sure we would have finished up swapping for the night . Libby and her second husband are staying with us for a few days nearly 60 years later still regret not kissing her
 
Zima said:
Well then now is the time to break the ice, tell her that you have always regretted not kissing her 60 years ago and lay one on her and get her response
Bit nervous but may try it the worst she can do is say No and I do fancy her still
 
Kenbcolley said:
Bit nervous but may try it the worst she can do is say No and I do fancy her still
I have just given her a cuddle in the kitchen and told her what you said she said did I want to still kiss her I said most definite yes we kissed not for long but she just said we must make up for lost time , I am hopping we can grab some time alone tomorrow
 
Zima said:
Great at least now you'll never have to wonder what you had missed out on and you can think that just maybe she has always had the same feelings about you too
Just had a hour with Libby on our own , yes she was upset I did not kiss her and we had a good play with each other so I have put one of my regrets right
 
I actually have two. First one would be not agreeing to being a blowbang slut for a group of 5-6 guys. Hubby and I had just became swingers around 2003 and one of the guys in the swingers club we were part of wanted me to be their slut at a hunting camp. They would all gather at the camp at various times throughout the year to hunt and play poker. The girl that had been their slut for a few years did not want to do it anymore so they were looking for a new girl to service them. I thought about it long and hard but since we were new to the lifestyle was really nervous.

Second regret was not having my bull’s baby years ago. Was actually pregnant with his baby but had a miscarriage. That wasn’t my fault but still regret not having his baby
 
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Not taking it further when my wife's mother flaunts her massive breasts. On a number of occasions she has deliberately walked topless in front of me after her shower when my wife has been out.
 
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