This is a true story of how i became cuckolded to my fiance and the man who came to train, dominate & own her over ten years. I hope you enjoy reading.
I have always been very nervous and submissive around women, especially very attractive ones. I have only had sex with 2 women, first when i was 19 and unfortunately after 15 minutes of trying to stay hard and keep the condom on, i climaxed as i entered her. She looked quite disgusted or humiliated and i began to realise my fears were correct, i was small and weak sexually and would struggle to please a woman.
The second girl was my best friend, i had knows her a couple of years, i was 24 and she was 19. I had asked her out many times and she had resisted saying it wouldnt work. After a series of “bad” boyfriends she agreed to become my girlfriend. In the time i had known her she had, had sex with 11 men from our local bar, all people i knew and more that i did not. While i was basically still a virgin. I had overheard guys who had been with her saying things about her sexually, how good she was in bed, how dirty she was, how she loved this guys big dick and told him she was a “size queen” I knew her huge experience would show me up as less than capable sexually but i hoped things would be ok.
Within weeks of getting together i had failed to stay hard and fallen out of condoms so many times she asked me if i had a problem. One time she got very upset saying she was not used to anyone struggling to get hard or stay hard. She got very upset when she dressed up in lingerie and heels and hair and makeup done, she posed for photos, very explicitly showing and exposing everything for me.
I later found out she had been advised to do it by her friend to help me get “so turned on i wont be able not to get hard”. As i put on the condom and tried to enter her i began to feel myself going soft, she realised and the look in her eye followed by tears forming sent me panicing into softness sliding out, leaving the condom in her pussy hanging out. At that point i suddenly shot my entire cum load all over her thighs, stocking tops and pussy. She began to get dressed and walked out saying she needed more than this and couldnt have a boyfriend who couldnt fuck her.
After 3 months she came to me and confessed she had cheated, three times with two different men. First she had gone home with an older guy from our local after telling him how frustrated she was, the second was a younger guy we met at a party, he had slipped her his number and she had gone to meet him the following night having sex 3 or 4 times before coming home. The third time was once again with the first man, the older man in his 40’s she had initially confessed her frustrations too. I was not happy that she had been lying to me since the end of the first week of our relationship, but i told her i understood and didnt blame her at all. She was more upset than i was, i told her if thats what she needed to be happy and remain with me then that was ok with me.
Her reaction was not good, she said she was not some slut, she said if i wanted to remain with her she would not do it again. I asked her why she went back to the older man, remebering the romours she liked big dicks. She said she didnt know, i asked if it was because he was very “big”, she went really red and said “you dont really want to know” she looked quite uneasy but i said its ok i understand. She said “honestly, yes, hes pretty big, really long. At that point i went bright red and she said “i told you not to ask babe”. I was slightly jealous at that point seeing her eye light up talking about his size. I asked her how long was he, compared to me. She shook her head and said “your about four inches he must be nine at least, and thick like a redbull can”. four inches i thought to myself, she thinks im four inches and hes nine. I had never felt so unmasculine before and really aware of my small size and appearence to her.
At that point she noticed i was hard, hard enough to show through my clothing. She was shocked and felt it, she looked confused but said “we cant waste this” she took me up to the bedroom and stripped of maying on the bed, i was right behind her still hard. She put a condom on me and then stopped like she remebered something. She said to me “i forgot to tell you, neither of the men used condoms with me” I was shocked as she was always so insistant on me wearing condoms, and extra thick ones. As she said it she pulled my condomed cock into her very wet pussy. I then entered her fully for the first time, not going soft. She let out a pleasurable moan and smiled at me, we had sex for about 15 minutes before i came. As i climaxed she orgasmed rubbing her clit a little.
All the time i was having sex with her i was hearing her words “your about four inches, he must be nine” and imagining her being fucked by the men without condoms, and now i am here in a condom having sex with her. I flt a mix of humiliation and turn on, i was somewhat cunfused but i stayed hard for the whole time, knowing the men myself i could not get images of her with them out of my head.
At this point neither of us knew what cuckolding was but we were soon to find out. After a few weeks i was once again confronted with my girlfriend amditting she had been unfaithful again with yet another new man. Once again i said it was ok and i understood. She then confessed that my penis was too small to stimulate her and she really disliked sex with me in the penetrative way. She said she was sorry and she wanted to stay together but couldnt go on. I once again told her to find a discreet lover or lovers so she was not so frustrated.
Eventually she agreed and once again went back to the older man with the nine inch cock asking him to be her discreet lover. She came home very happy, having not only had sex but learned what cuckolding was. She eagerly told me about it, about hotwives, about chastity, emasculation. The older man turned out was already cuckolding two other couples. As things moved forward we both learned a lot online and on forums. By that point we had got engaged and the older man was having sex with my fiance every week soemtimes twice a week or over the weekend.
My fiance then came to me telling me that she loved seeing me turning from a normal man into a submissive and almost sexless apart from weekly hand relief on a sunday night. She expressed her desire to feminise me, which i loved as i had always dressed secretly, she said she wanted to stop having any sexual contact with me, and she wanted to put me in a chastity device whenever i was not in her company. She seemed massivly turned on by this idea, more than i had seen before, eager, bright eyed, excited and figity almost like she wanted to masturbate right there and then. She then did exactly that masturbated in front of me telling me to look but not touch, as she climaxed after about 30 seconds she let out a squeel turning into “i want to you to be pussy free for life”. She climaxed hard and squeeked “and maybe gay” she rolled into a second orgasm. After a minute of her climaxing and coming down she looked at me and said “agreed?” i just said “yes agreed” i couldnt believe what i had said but i was blown away by how hard she came, unlike anything i had seen from her before.
After some embarrassment and pretending we hadnt just had that conversation, later that night when she was turned on again she asked, “will you really go pussy free, forever, if i ask you” i got very humiliated and didnt answer, she got a little embarrassed again, i said “i will if it turns you on”, “it would” she said. We went to bed at that point. The last thing she said to me that nght was “we will have to find you an extra short chastity cage soon wont we babe” i replied with a simple “yes” She left things with “we will order one online tomorrow” I felt her rubbing her clit as she spooned with me, she had a shuddering orgasm and soon fell of to sleep. I went to sleep wondering what i had agreed to and still not fully realising the humiliation and emasculation was actually what was turning me on enough to agree.
To be continued in Phase 2: ❤️ Cuckold Emasculation ❤️