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First cuckolding experiences

Discussion in 'The Boudoir' started by Aoilioa, Aug 9, 2017.

  1. So we're currently on holidays and my gf of 5 years will leave tomorrow while I stay with my family for a few days longer. Originally because of work, but now she decided to also invite her good friend over. She has done that a couple of times and there was never anything sexual but you could always sense there was something special with those two.
    She and I also agreed we would take the chastity game to become a chastity lifestyle for us, she finally discovered she really likes the control and is doing a splendid job of fulfilling my fantasies. We also just ordered a new cage (thanks to @inhershoes@inhershoes if you're reading :)). Having a rather troublesome sex life before, I love the new her and the way things have turned now.
    This was one of the reasons why I agreed to have her seduce the good friend coming over tomorrow. We discussed it a lot and came to the conclusion that it benefits our relationship, her personal sexual development and possibly fulfills the submissive fantasies that she still has despite being my mistress. We planned all the details, I helped her to put together some outfits she can wear, and we generally had a lot of fun doing all this.

    I always got turned on by her being used by other men while I wasn't allowed to cum, but this is becoming reality faster than I ever thought. It's possible that nothing much happens and the fuss was all for nothing. However, it's equally possible she gets her anal virginity taken by another man.

    I'm generally positive about the whole thing, excited and a bit scared, but we will see. Tomorrow evening I might be getting sexy selfies from my girlfriend who will then present herself to another while I will be sitting with my family and maybe have time (and allowance) to edge under the shower for a few minutes.

    The really hot part is how our relationship has developed in a relatively short time and how it will continue to do so in the future. Will my cage fit? How many orgasms will she actually allow me per year (if any)? How will our sexual encounters in the future change? Currently we have established me wearing condoms so I don't cum which makes me her living dildo or fucking machine if ou want. We still have sex sometimes but I never orgasm. I can't really tell when i was last allowed to cum inside of her (which is another extremely hot thought to me). Will she turn to other men for pleasure and excitement more often from now on?

    I will update with the experiences we make in the upcoming days. :)
    spider203 and Mash2214 like this.
  2. Congrats.
    I remember the first time I saw my ex with another man. It was so hot.
    And I remember the first time she spent the night with a female friend and came home and told me they slept together.

    My suggestion is to enjoy the ride. Be prepared for some surprises, mixed feelings, and what have you. But you should be able to get through them with the great foundation you've built!
  3. Hi, thanks for sharing. Sounds also very hot, I would love my gf to sleep with one of her female friends! :D
    So, I don't really have mixed feelings yet, we talked a lot and I'm pretty much in control of the situation. If I say stop, the thing is over. I know this is not the classic cuckolding fantasy but this is new for us and our relationship comes always first. We feel what we have is very special and we wouldn't wanna risk it if one partner doesn't feel comfortable with it any more. Sorry for being boring :/ I also feel it's more exciting if gf/mistress makes her own decisions (whether they sleep in our bed or not, if they hold hands publicly, how they have sex and where the limits are or even with whom she cuckolds me) but for the first time we decided to play it safe so I had a say in all of those things. However, the thought that that might change in the future is making my pants a bit tight ;).

    Also, I know the person she is doing it with is not a contender for me, at least in terms of the actual relationship part. In terms of sex, we will see. ;) You also should know we both had no sexual partners except each other (ever), so a few fresh experiences could bring an interesting turn. But apart from the practical part, it also fits nicely with the chaste lifestyle and I'm sure she will find many opportunities to utilize this for my humiliation and submission.
  4. I've been married to the same women for 32 years and I still do t totally understand how she thinks. Cuckolding can be a Very Dangerous thing to do. She could very easily not need you anymore. What a women really wants out of a relationship isn't the same as what we want. Good Luck. This is the one thing that my Wife and I don't do, so once again Good Luck
    sissybitch likes this.
  5. Thank you for sharing! This is good for me to hear about the experiences of others. I anticipate Mistress will be placing me in similar situations as she also has a submissive side. I applaud your courage. I like how you refer to yourself as her 'living dildo or fucking machine.' My fate is similar! My orgasms are regulated by her. :D
  6. I lost my girlfriend through cuckolding. Everyone tries to find reasons why it is good for a relationship rather than call it what it is. It is like what we do when we convince our wives of all the benefits they get if they become our keyholder. I became a bull after my girlfriend asked my friends to gangbang her and then started to date one behind my back.

    Ask any psychologist or therapist and the will all tell you to never have sex with friend. Your girlfriend already has feelings for her friend and making it sexual, usually does not end well at all. I can tell you many stories with sad endings from my Bull days which only ended 7 years ago. I cuckolded one husband for 25 years because he was afraid that his wife would cheat on him with me since she was my girlfriend for 5 years before he met her. He dealt with his fear by legitimizing his wife's sex with me. He felt that he was in control even when his wife got him to fly her out to meet me for vacation while he went off on his own.

    I am a lucky man. My wife is bi and was somewhat of a cuckquean who asked her girlfriends to have sex with me so she could watch or have sex with me afterwards. She was repressing her bisexuality, the number one reason that cucks are cucks. I finally got her to come out and we ended up inviting her girlfriend, a mutual friend of ours since childhood, into our home and our bed. I had to endure having threesomes as our regular sex for 30 years. It was difficult to watch my wife have sex with women. Yeah right. :)

    Anyway, you started off in the worst way but it is your life and you will learn like I and many cucks I knew did.
  7. Forgot to say that doing it before you get married is the way to go. If she leaves you she does not get half of your stuff as a wife would. Although I only knew one cuckold marriage that lasted long, it is possible but cuckolding is a minefield with more mines than fields. Hopefully you can avoid the problems that will pop up now and then. Good luck.
  8. Thanks for the inputs. This sounds really dangerous and pretty bad. I have given it some thorough thought and although I really don't think I know better than you, I want to give it one try. The man in question is going to go study abroad and probably move away forever in a few months so it should be safe if it's a bad experience. Also, maybe the word cuckolding is a bit over the top, we will see how far things actually go.

    And to update with the first experiences: Mistress told me it was super awkward trying to initiate something, he had to have a cold shower and didn't cum from a blowjob and apparently doesn't really know what foreplay means :D So the fantasy was hot, the reality is currently still very awkward. This should also show you we are still in our early twenties and don't have many sexual experiences yet (apart from with each other). Maybe don't think of this as cuckolding, think more of two people in college making experiences and fooling around a bit with other people. It just so happens we also wanna keep me chaste in the future because it has a positive impact on our relationship, and cuckolding and chastity are kinda in the same ball park. So there are some overlaps there. Sorry if I overhyped it in the beginning :(
    traveler likes this.