Cuckolding keeps us together

Feb 03, 2022






My interview with a cuckold couple


Greg and Ann are a delightful and sexy couple living in sunny Florida and they have a secret that no one suspects of them.  They are a cuckold couple!    How they got this way and why they love it is a great story and a great lesson for us all who face challenges in our lives and wonder how we are going to get through.  


Greg and Ann are in their second marriage, have no children and have recently purchased a beautiful home in north Florida.   They both work in administrative type jobs, Greg parttime and Ann full time and it keeps them young.   They have reinvested in their health and they both look amazing after each losing a great deal of weight with improved nutritional habits and daily exercise.    Like most people in the lifestyle, they are fun, flirty and love to chat with new people.   I was invited to interview them about their choices for cuckold lifestyle and I was curious to say the least.


Greg and Ann are a May – September couple.   For those of you unfamiliar with that term, it means that Ann is significantly younger than her handsome husband and her resulting physiological “needs” are a generation younger than his.    There were some additional factors that exaggerated this divide which I will also cover.


Ann’s past first marriage to her very first boyfriend was not ideal.    During the marriage he became an alcoholic with a cheating and hygiene problem.   Ann’s reaction to his sexual demands was that it was something you did but not necessarily enjoyed.    Once the marriage finally ended, meeting up with Greg was a godsend.     He ticked all her boxes and the sex she finally got to enjoy was amazing.  She enjoyed orgasms, now loving to give, and receiving oral sex and making up for all of the lost time.   Given that her second husband, was also only her second lover, she had a lot to discover, which included eventually that she also liked sex with other men besides her husband.  Furthermore, Greg discovered that he relished the idea of watching Ann with other men.  While initially reluctant, Ann agreed to try it and while battling her guilt and religious beliefs, gradually the two began to feel more and more comfortable with this sexy addition to their already great sex lives.    Greg and Ann agreed that they were looking for a special kind of relationship where the single man would be a friend to the both and that there had to be a basis for the sex that Ann was going to be receiving from men who were not her husband.


Then came the day when it was discovered that Greg had prostate cancer.    He opted, on his doctor’s advice to have the surgical removal of the prostate gland which stopped the cancer but had the emotionally devastating side effect of rendering him totally and completely impotent.    He was no longer able to become hard enough to penetrate his wife’s pussy and further, any orgasm he had was basically ruined and not satisfying.  He referred to them as ghost orgasms.   It was a crisis in his life and hers, but there was at least, a partial solution.     While his sex life had been taken away, at least in terms of having intercourse with his wife, she still could find sexual satisfaction in the arms of the men that she had known before and new men that she could still meet.     Now Greg had become a cuckold in fantasy and in reality.  He was not able to have sex with his wife any longer.  He was now forced to be on the sidelines and he had to accept that his role would be to support his wife’s wishes to find the perfect cock for her.



Now there was even more reasons to consider inviting single men into their bedroom and for the next ten years, there were many.  It was not however something that they were both comfortable with and as a result they were quite selective.   It was frustrating at times, with the men wanting a quick encounter which they recognized as being quite common.  What they wanted though was a step by step increase in familiarity until they could be comfortable enough with the man for intercourse.   Once Ann met someone in person, after initial screening by Greg, they would if the chemistry was there, meet up for oral sex.    Ann really enjoyed pleasuring men orally and Greg enjoyed pleasuring Ann orally at the same time or afterwards.    It was great for Ann to accept the men into her mouth and enjoy her own orgasms brought on by Greg virtually at the same time.  

If the BJ experience was great, Ann would at that point agree to meet again for intercourse which she also enjoyed, but only with those men with whom she felt great comfort.  


In the perfect situation, Greg and Ann would have a single guy or two within a short drive of their town who could meet up with them on a regular basis.   Greg would enjoy very much being the loving cuckold to his beautiful wife who could continue to enjoy a full sexual life with her lover and her husband.  


With respect to humiliation, Ann’s work in the mental health field, made it difficult for her to initially taunt and tease her husband and it took a great deal of convincing and reassurance by Greg to make her comfortable with this aspect.    While he couldn’t directly participate in filling his wife’s pussy, he was at least able to be a part of the conversation of comparison which although was meant to be humiliating, was an acknowledgement of his “role” as the failed husband.

Ann was very candid in her description of her journey towards cuckolding her husband.  I asked her some pointed questions and she answered them straight on.   Here they are.


  1.  You and "Greg" started inviting single guys to be with you before he had his surgery and became completely impotent.   What led to that decision?   Over time, we discovered that I enjoyed looking at other guys cocks on the computer. That evolved to discussions of how much I enjoyed sucking "Greg"'s cock, and then at some point it evolved to the decision to try sucking others.  (this was over a long period of time...years)  What was your motivation to do that given that Greg was so much better than your ex?  For clarification: "Better" may not be the right word.  I never enjoyed sex with my ex.  I did, however, enjoy sex with "Greg".  Yes, the ex, had a bigger one (probably average to slightly below average), but that didn't mean I felt he was better at sex. In my opinion, there's a lot more to it than just size.  But to answer your question... after I sucked my first couple cocks, it became more obvious that "Greg"'s was definitely much smaller than an average one.  And I liked the ones that weren't "tiny" a lot more.  So, I guess that's what lead to it. 
  1. Now that he is impotent, can he manage to put his soft cock into your pussy at all?  No, it is too small to stay in.  Does he manually stimulate you?   Yes, mostly it's oral sex.  If so, how often? Every week or two?  I suck his little dick about once a week?
  2. When you were involved with single guys on the regular, how often did you have intercourse? I didn't like keeping track, but probably 25% or less of the guys.  I honestly don't like to think about the number.  It makes me feel a little trashy.  lol  But at my most active time, maybe once every month or two? We were always very busy with our regular lives. I was getting the feeling that you only did BJ"s but then you said that you had been with quite a few guys over the years.  I was confused as to the past and current frequency of intercourse with these guys.  There was a period (10 years ago?) where I was pretty active and most of it was bjs.  That stopped and it went for years where I didn't do anything.  Now (the last couple years) we are looking to get back into it.  (covid slowed the search a bit too)
  3. You said you didn't care about Penis size with the single guys and that you were petite. When you were with Greg, how big was his erect penis and how big do you like to see a cock now? His erect penis at its best was 6 inches, but VERY thin (MAYBE almost 1 inch wide at the most, guessing...) and that was at its BEST. Usually it was more like 5 inches.   I like a nice sized cock, but if I had to pick, I prefer girth over length.  But if they are extremely (freakishly) large, I want nothing of it, I don't think it will even fit!  LOLOL 
  4. Do you have any regular guys now that can come over and have sex with you? No, it's been a few years!  Darn it!
  5. How did losing weight affect the ability of you to attract single guys?  I wasn't looking for guys around the time I lost the majority of the weight.  It's been off (mostly) for the past 5 years and we weren't looking most of that time.  But now that we started looking again, it doesn't seem to make it any easier.  lol  (never really thought about that, until now...interesting)  But...again, it may just be because we live in a small town.  (We prefer that person to be close to us, due to our busy schedules, and living in a small town gives us much less options
  6. What kind of sex do you like? Slow and gentle to medium.  Slow and gentle, medium, a bit rough and poundy?   
  7. Are you into any kind of kink?  Spanking, pegging, bondage, discipline, humiliation, etc  Yes, with "Greg" I am into a lot of these things.  With Greg's tiny and inactive dick, we have found fun ways to keep US active.  I have recently made him wear a cock cage and that's fun.  Just to make him more submissive to me.  He has a key and I have a key to it.  But he is pretty obedient about wearing it unless I tell him to take it off.   He and I also a little bit of whipping of his dick, humiliation, etc.   None of that seems appropriate with someone else.  The guys with "real dicks" don't deserve that kind of reactions from me.  They deserve to get my admiration. 😉  If you are asking if "I" am into those things being done to me with another guy....not really.  I do prefer to be submissive with the other guy.  I enjoy pleasing the guy, so if they were INTO a little bit of spanking, I might get into that IF it turned them on.  But not to the extreme.

Greg and Ann, thanks for sharing your story!

Sue has more information on her website.