Sex & cuckolding in reality

I film a lot of crazy stuff. Cuckolding is one of my own personal fetishes and can be played out in many different ways.

I have recently been spending more time with a boy who I’ve known for awhile…as a friend & occasional film slave. He’s kinky & submissive…also pretty cute. He’s in his mid 20’s & I find his youth refreshing.

His sexuality is complex. The times that I’ve considered taking him as a lover his penis wouldn’t cooperate for regular sex. He worships me & is intimidated by me sexually. He gets plenty hard when I kick him in the balls or when he’s worshiping my feet but when I’ve actually tried to fuck him he’s gotten all flustered. Kinda cute.

I haven’t really cared. I have other lovers & I genuinely enjoy his company & service. I love the way he dances (often silly/goofy on purpose which I find entertaining & strangely arousing.)

Yesterday I was out with friends. A couple I’ve had a strong friendship & occasional sexual relationship with for many years. We spent the day hanging out, eating, shopping, going to the beach & flirting. Here’s a snap from yesterday:

Mistress T at the beach

Beach time with my cherished, sexy friends…

At the end of the day she went to have a tryst with a lover. He & I headed back to my place for some fun & I texted the boy to come over immediately. I decided to cuckold him. The conditions were perfect.

While we waited the fuck stud licked my pussy expertly. Mmmm…& just as I came the boy arrived. I kissed him deeply & told him today he was going to see how a real man fucks me. He watched as I licked & sucked the fuck-stud’s cock. Then I told him to suck it a little for me. I wanted him to feel how big it was in his mouth so he would understand how his cock would stretch my pussy.

I licked the shaft while the boy gently sucked the head, our lips & tongues touching.

I had moments of awe…that I’ve played these scenes out so many times in vids & here I was doing it in real life & it was just as hot, hotter even, than the vids. Reality surpassing fantasy.

I wanted that big cock inside of me & I loved the fuck stud’s technique…I was excited to get on with the fucking.

He rolled on the condom & positioned himself so the boy could see his cock entering me. He told him to watch & learn. The fuck stud is the perfect combo of assertive & dirty while still being a really caring & nice guy. He wasn’t some douche who would get off on degrading the boy if he didn’t see how much it turned the boy on.

He fucked me, slow at first, gradually increasing the intensity, depth & speed. The boy was rubbing himself through his shorts & I gave him a foot to worship as I was getting fucked.

After a thorough & truly satisfying rogering from the fuck stud…who fucks in such a manly way, physically assertive, holding me down firmly & using his rock hard cock like a weapon…while looking at me with such compassion…his eyes rolled as he pressed hard against me and came.

As he went to clean up the boy & I kissed sweetly. I wanted to feel his buttery soft young skin against me & told him to undress. I could pet him for hours he feels so good.

Warm hugs for both of us as the fuck stud left to pick up his wife from her lovers place.

The boy & I cuddled & kissed in bed. He was so nervous & overwhelmed. His cock fluctuated between hard & soft as I touched it. I know many guys reading this are rock hard & imagine that they would be rock hard 100% of the time in my presence…while others who understand reality know that often guys struggle with erectile difficulties for all kinds of reasons…none of which include not being attracted to their bed partner.

I liked the idea of having him enter me after my other lover had just stretched out my pussy with his bigger cock. I kicked him in the balls a few times & his cock grew to full attention. (I warned you, his sexuality is complex.) I rolled the condom on & we started to have sex but he quickly lost his erection. I kicked him a few more times & then straddled him, riding his cock while punching him in the balls.

I confess, this was more novel than arousing for me at this point so I told him to lick my pussy. He’s somewhat inexperienced but takes instruction well & I soon had my second delicious orgasm.

As it turns out, bizarrely, there is a sexual position that works for him & once we got going it was surprisingly hot. Probably most exciting as this was the first time we had successful intercourse. He looked so intensely passionate by candle light, so beautiful…

I certainly felt satisfied after hours of ‘play’. Sure, the sex act with the stud was more satisfying, but I got a great deal pf pleasure in a different way with the boy. He truly worships me & has other things to offer. I always enjoy my time with him.

I could have left out all this fumbling around & ended the story after I got fucked properly by the fuck stud…but I thought it was more interesting to explain the rest. Porn messes a lot of people up thinking that sex always runs smoothly. It doesn’t. Sometimes you have to have patience & get used to someone before sex works at all. If there’s chemistry it can be worth the effort.

So, what happens now? Will the boy become my cuckold because he doesn’t quite sexually satisfy me but I like him a lot anyway? Will he start to satisfy me sexually so we have great sex but have an open relationship? He’s quite likely way too young to be a serious partner, he’s more of a play thing…but is he falling too hard for me to be treated so casually?

Who knows…but if anything blog-worthy happens you’ll be sure to hear about it.

Mistress T

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14 thoughts on “Sex & cuckolding in reality

  1. Thank you . Another great blog. I have this exact problem…can get rock and cum 3-4 pr day, but when seeing a domme, I have problems maintaining an erection. It’s not that I am not attracted to the girls, but I think one of the problems is that I only jerk-off while looking at pics or video.. I also can’t have proper sex and I lose my erection because I am so used to satisfying myself with jerking off.

    • Torgeir, this is common. Some guys basically train or brainwash themselves into only being about to cum a certain way. Unless you have opportunities to practice cumming a different way there’s not much you can do about it unfortunately…that I know of?

  2. Not near as intense as your experience Ms T, but a number of years ago I was kind of cuckolded by the woman I have married, it was when we were dating and it has permanently left a mark if you will. She is a tall red head, almost fitness model, even in NY (we are here in BC) she turns heads. She was an admitted size queen even when we dated, I am average in size. A friend of hers from work was dating a guy who apparently is hung like a yeti, and knows it, I never did like the guy, big muscular alpha dude. She had implied to me from time to time that they had sparks between them out at the bar in the past but once she made a joke or two about how big his cock was I was obviously dismayed and she didn’t really bring it up again.
    Then one night we were out, she was looking hot, hot come from work in skirt boots black nylons, I have a foot fetish and had been thinking and aching to worship her feet all day which adds some subtext to this. Anyway, we were getting set to leave a bar and I was chatting with some friends, I heard him call her name, she walked over to speak with him, I was watching from the corner of my eye as they were laughing and talking, her touching his arm from time to time for just a second or two too long. So then I walk over, they kind of stop talking, she looks at me, not maliciously, but overtly says ‘have you paid the bill?’ and I replied know, but on our way out, and she says, ‘i’ll catch up’…so I am fucking pissed at this point but, like a selfish little subbie I don’t want to have a fight and not get to bury my face in those sweaty black nylons when we get home….so we go to one more place for a couple of drinks, not much is being said if anything…she looks distant which worries me to the point of taking away my anger, I try to start conversation but she is disengaged…finally we get home, I ask if she wants to meet downstairs for a glass of wine and a quick foot massage which is usually a prelude to sex, she agrees so I am relieved…but as soon as I got downstairs things were different than ususal. Her boots were propped up on the couch, I tried to hand her a glass, she just put it down on the table, I went undo the zipper on her boot but instead she grabbed a tuft of my hair and dragged it down between her legs and started to squeeze, I thought she wanted me to go down on her but I could even get her pantyhose off she was just squeezing and bucking and moaning, writhing to an orgasm then pushed me away, I knew what was happening who she was thinking about, but couldn’t help but ask, even though I was emotionally torn in doing so, ‘so what are you so wired up, god you are soaking’, she said ‘what the fuck do you think, did you see who I was talking to, fucking huge cock and she started to squeeze her legs together again, but by this time I had a boot off and was sucking on that sweaty reinforced toe, never ever have or was I so conflicted emotionally, basically the woman I love telling me she came over another guy and me tonguing her foot like a dog in the meantime…I said ‘you know people think he’s an arrogant prick and it just got her going more, mmmmm I know fuck then she started demanding that I say his name…as she brought herself to another orgasm, ‘SAY HIS FUCKING NAME MMMMM and she went off again…” I know this sounds like a wanker story but I think there is commonality in this story and yours in your statement about real life versus fantasy. I can watch as many of your wonderful clips as I might buy, hundreds, but nothing will ever have the lasting effect of something real and in the flesh like this. We are still together, 3 kids too, haha just like a Hollywood movie…if this was boring apologies, I realize its a little self induldegent sounding…

    • Mark, you really should have encouraged her to fuck him. If an opportunity like this comes up again put your insecurities on the back-burner & put her needs before yours. If he was an arrogant prick it’s unlikely it would have been anything more than a one-night or brief fling. Extra marital activities don’t have to end a marriage…there are many scenario’s including cheating & consensual swinging where marriages stay intact or are strengthened by it.
      Just communicate honestly & with compassion.
      You only live once.

  3. Thanks for responding Ms T, but I would worried she wouldn’t want to have sex with me anymore after riding that big python. If she came twice just after a conversation with him imagine how mind blowing the sex would be? On the other hand, just recently as we continue to explore the femdom dynamic in our relationship, she told me that during her conversation with him that night, he basically told her he could make her happy, asked her how serious we were, and reminded her of the asset he had in his pants and she ended up home with me and I am the guy she married. You’re awesome Ms T as usual….

  4. Talk about Sunday fun day!!
    When a person is sexually liberated they are able to derive pleasure from several different sources. Awww that sweet little cuck might be on the way down the rabbit hole.. interested to see where this goes.

  5. Mistress,

    i absolutely love your honesty. You come across far more ‘real’ than so many other distant contacts. Thank you for all you say!

    (P.S. Cuckoldry does excite me — sharing ‘the main man’)

  6. This is beautiful and reminds me so much of my first sexual encounter with my then slave, now husband. He was also a bit, shall I say, shocked, and so completely overwhelmed with nervousness when I opened up to him about my desire for him, he could not perform either. It took a few times. He would tremble uncontrollably and could not keep his giant member hard, I wondered if he had a problem! Now, he pleases me immensely, regularly, and has become a master at having his head, and cock, between my legs. We’re so very happy together, and love with slave who would have never thought he had a chance, is totally possible, with time. It sounds like you’re lookin

  7. Just discovered Your blog. You are quite amazing. So open and honest as I wish I was. I am a sissy and live a double life. I didn’t know I was a sissy until my thirties and it has grown and grown since then as these things do. I am married and have high profile job. Las year I told my Wife, Z, that I wanted Her to dominate me and She jumped at it. We had played a bit in our early years together. She has really embraced it while I have been unable to let go and tell Z I am a sissy and need to be cuckolded. I know I don’t sexually satisfy Her and I think She would jump at it but I am procrastinating endlessly. She has also told me often She would love to see man on man sex which as a sissy cuckold would be amazing. Just thought I would tell you briefly my situation and compliment You on Your courage. You are gorgeous too btw!

  8. Amazing story (sorry reality)…….enjoyed reading each word …. eagerlii waiting to know what will happen next…. i am saving your blog on my bookmark list… please do let your blog readers know what happens next ….thanks !

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