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Well it's happening

Discussion in 'The Boudoir' started by ClubSub, Jun 21, 2017.

  1. My Mistress was out with her girlfriend Sarah, who knows about our lifestyle, and Sarah mentioned her new boyfriend is bisexual. Clearly seeing an opportunity, Mistress has decided it will be a good time for me to lose my true anal virginity - I have been taken by plenty of strapons but never actually had a guy fuck my ass. Sarah enthusiastically agreed and the boyfriend has tentatively agreed to giving the girls a show, but he wants to meet first and get to know each other.

    So Friday, Sarah and the boyfriend are meeting us for drinks and dinner. Mistress already informed me I will offer the boyfriend a blowjob in front of the girls to make him relaxed. If everyone gets along, we will all go to the shore together for the long July 4th weekend. At some point during that weekend, Mistress and Sarah will get their show. As a thankyou, Mistress and Sarah will have a threesome with the boyfriend. Clearly that weekend will be full of sex, I just hope Mistress brings the key so I can partake more than just with the boyfriend. If I am good, Mistress has told me I will get a non-ruined orgasm possible even a full orgasm from penetrative sex.
    gen72ben, locked17, Dufty and 6 others like this.
  2. Sounds like your in for a Wild Wild ride. I'm personally still a virgin but with what my Misstress has had me doing lately I think there may be a cock in my future also I'll be looking forward to your post July 4th posting. "Enjoy"
  3. Good for you. I had anal sex twice in my much younger years. Since real penises are not like the hired big ones in porn, I had no trouble with anal, giving and receiving with each of the two guys. I never did oral on a guy though. It is on my bucket list but my wife wants no part of it which is strange since she is bisexual and had had thousands of sexual encounters with women over the last 44 years of our marriage. This has nothing to do with an D/s. I just like to try new sexual things. Tried every fetish on Fetlife, and chastity was the only one I never did until now. I am heteroflexible which means that I identify as straight, am not sexually attracted to men but under the right circumstances I can have sex with men. Usually a few drinks and some hot girls encouraging and arousing me, do the trick. Of course it is not the same way I have sex with women. There is no passion, kissing, fondling, etc.. Just orgasms which feel good no matter what the source. P.S. - most guys do not cum as much as you see in porn. If it was me I would have him have sex with his wife or mine. Than when he recovers I would have oral sex while a woman's scent and taste was still on him. As they sang in Mary Poppins, a little bit of sugar makes the medicine go down. :)
  4. Thanks for the encouragement. I am not worried so much about the size of his penis, since Mistress has taken me numerous times with strap-ons. In fact, it is the manner in which I get most of my release and she has an unrealistically large strap-on she uses when she is angry. Her big black one is larger than any of her bulls. If I can take the big black strap-on, I am sure I can take whatever the boyfriend is packing.

    I am more nervous about the idea of another man fucking me. I consider myself heterosexual - not interested in men at all. I do not want to be with men, but I am a fully submissive cuckold to my Mistress. If she orders me to do something, it is my duty to her to comply. In fact, Mistress knows I am not interested in men which is why she enjoys making me suck her lovers and now have someone fuck me. She gets off sexually though humiliating me. While the bulls help please her sexual urges, she is never wetter than when she watches me suck other men. Yes, I know that it is not truly forced since I willfully submit to her. But, I cannot disappoint her so I gladly follow her orders against my own judgement.
    gen72ben, Ronn, Xtudo3002 and 3 others like this.
  5. Congrats
    You're talking a step few do.
    Just remember to relax. And speak up if it hurts. Make sure he goes slow until he's in.
    After that enjoy losing your virginity.
    My first time was with a friend. My ex directed and his wife was watching. I'll never forget it and always know it was more incredible than I thought.
    So please let us know. And careful as you know what they say
    Ronn likes this.
  6. I envy you the experience.
  7. Use good lube and you will really enjoy it.
  8. I hope it works out for you. I personally don't cuckolding is good for a relationship having your Mistress be serviced by someone else in my opinion can lead to problems but that's just me. But you shouldn't be doing things against your judgement at least not on a regular bases. It's a delicate balancing act when you incorporate other people into you sexual life. It tests your relationship and commitment to each other. I know that when other women came into our situation it was a test at first for us. Good Luck if this is what you want than Enjoy It.
    sissybitch and lockit like this.
  9. ma'ats live by a different code than mistresses do. no sex with any xy but our own puck is allowed( breaking this rule has severe consequences). on the other hand we can have sex with other xxs and we can order our puck to service or be serviced by another puck. being a small group that limits who can participate. since it is ordered my puck has no emotional attachment to the other puck but he says it is awkward when they meet in town. more disturbing to him is that it is ordered for our entertainment. what you will endure and/or enjoy will be witnessed by two others. how would you feel if there were 20 or 30 people you see all the time watching and commenting for days or weeks later. puck says to this day that is the worst part.
    set your mind to obey and it will not be too bad. if you find you like it she may have found something to deny you as well.
  10. Hope everything goes well and you have a great time. Enjoy!
  11. I have to say that I feel very much like you do in terms of heterosexuality. I have never given another man head, but I do have fantasies about it. I have the very same fantasy as you are about live to. I hope it works out for you the way you want it to. Good luck, Keep us informed how it goes!
  12. The first time my Lady directed me to pleasure another male (orally) was a defining moment in O/our relationship. That is when She assumed ultimate control. It changed the relationship, for the good, forever. She assumed ownership and I truly felt owned.
    tomf_22033 likes this.
  13. Too funny
    It got me thinking about my first time
    I was very homophobic but I enjoyed cross dressing and BDSM. I met a crossdresser at a BDSM club and we talked. Well I was invited over to get help with my dressing. We had fun dressing me and improving my walking in heals and stuff. When we were finished he asked if I'd like a blow job. Being homophobic I freaked out inside.i did however politely decline. Thankfully, he was cool and told me about how he was told a mouth feels the same and it's the skill of the sucker that's what matters.
    Well to make a long story short this must have gotten into my subconscious somehow as we decided to play dress up again. This time when we were done, before I knew it we were in 69 and not only was my cock being sucked on my a crossdresser, I was sucking my first cock.
    To make the story even more interesting, I spent the next few months thinking about this. Part of me confused, part of me liking it, and part of me feeling a bit sick.
    It was it wasn't until I met a Fem Dom couple and played with them where I sucked his cock that I felt good. I then knew I was no longer homophobic, and was in fact bi courious. Later I even felt comfortable accepting that I'm bisexual and actually enjoy male/male sex be it oral or anal.
    My point of this is this is a journey. We change and evolve so enjoy life. You may be surprised what happens if you can relax, ignore social stigmas and do try new things.
    Ronn, Xtudo3002 and Switch Alpha like this.
  14. So how did it go?
    tomf_22033 likes this.
  15. Overall, it was one of the best weekends of my life. It was a long sex filled weekend. Only I never got out of chastity. Mistress, Sarah and the boyfriend took turns fucking my ass. Furthermore, Mistress and Sarah both had me go down on them constantly. Finally, Mistress and Sarah shared the boyfriend numerous times, so the number of blowjobs I had to perform was limited. In total I think I only gave him three.

    While I never got out of chastity during the weekend, when we got home Mistress kissed me, told me she loved me, and said I was perfect all weekend. I didn’t actually get my reward for a few more days; but as any submissive cuckold knows, my true reward was the love from her eyes when she thanked me.

    As far as a guy fucking my ass, the experience was not as bad as I was picturing all week. When I could not see the boyfriend, I imagined it was Mistress or one of her friends with a strap-on. Since I love when Mistress shares me with her friends, I just kept thinking about those times. Plus, the girls seemed to really enjoy the show and kept me super excited which was both fun and painful – my chastity cage is rather small. Mistress hasn't stopped talking about how much fun she had, so I believe a similar weekend will be in our future. We actually are meeting Sarah and the boyfriend for drinks this week, so I don’t know if Mistress already has a plan in her mind.
  16. When imagination flies one can never know where it will go, generally picturing the worst case, which is not bad, since the mind goes more aware when the right time arrive.
    Congratulations to you and your very excited partner, now you are mastered in taking a real dick inside. Sure you will go for more, and the more skilled you are most rewarding anal sex is.

    Isnt this a real love? I envy your happiness and the adventurous KH of yours.
    ClubSub and tomf_22033 like this.
  17. What an interesting and amazing story. What happened after you guys enjoyed drinks together?