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Hi all, Just wanted to post about our first experience cuckolding which was arousing for the both of us. My Domme was even able to reach climax from penetration alone, however the experience also left us with mixed feelings about her bull.
So it started with my Domme going on a solo date, we had already met him together and had ‘good’ vibes in the sense that he was safe, but also we weren’t sure he was the right fit. I dressed up at home and we agreed if there was enough of a ‘spark’ to be like ‘let’s try this’ then she would invite him into our house.
I did the vacuuming and mopping when she was out on her ‘date, cleaning the house up like a good gurl, my cage throbbing knowing my Domme was out on a date with her bull, chastity keys on around her neck fully visible.
Eventually I get a text message and they’re both on their way home. I greeted them at the door and called him ‘sir’ in my gurliest voice, he told me I looked pretty and seemed surprised, he said I looked exactly like my photos. I suppose this surprised him because he had seen my ‘male’ self earlier on our first ‘date’ together.
We sat down briefly, and my Domme ordered me to make her a tea so I did, she then went into our bedroom with him and he started to give her a massage. I was called in before the massage started and told to kneel at the bedside.
So I was kneeling and watching, straining in my cage as this big, masculine dominant Man was massaging my Domme I front of me listening to her moan “That feels good”, “Yes like that please”. He would make comments like “This is what a Man needs to do Olivia”, “You need to stop being such a sissy and learn to please your Domme”…..I could only mumble “Yes Sir” as a squirmed still feeling how tight my cage was.
After the massage they did start to have intercourse, he ordered me to fetch condoms and lubricant and I did so like a good gurl. He was very controlling and demanding constantly moving my Domme into different positions as she moaned loudly, my cage was so tight I kept squirming my legs and making involuntary moans as I listened. Every now and then they made a belittling comment about me not being Man enough to perform like this. At times I held my Domme’s hand and she squeezed tightly in unision with him pounding her, that made my cage super tight. I asked her if she was enjoying it and she breathlessly moaned ‘yes’.
At various points I was allowed to use a vibrator on my cage and it felt sooooo good watching and vibing, seeing a Real Man do what I could never do though I was strictly forbidden from orgasm. Eventually they climaxed and my Domme orgasmed from penetration alone, something I am unable to do for her as I lack the size, stamina and dominance for such a task, that alone felt very emasculating.
My Domme then asked me to give him a hand job and oral. I could sense he was a bit apprehensive about it, but he agreed and told me to start, so I did. I felt him getting aroused inside my mouth and hands. I assumed I was getting him ready for another round, though my Domme decided to stop saying she felt overwhelmed and we ended the session after one climax.
That’s basically how it went and what we enjoyed. We did have some negatives though which lead to mixed feelings overall.
– There was very little physical touch from the bull, when ordering the verbal was good, but he was uncomfortable with touching a Crossdresser, I would have appreciated being man-handled or spanked on the ass when being ordered to get things.
– After I gave him Oral and a handjob he said “I’ve never, ever let another Man do that to me before, you’re very lucky”……”but it wasn’t for you, I was doing it for your Domme only”. I found this a little insulting as he could just say no. The comment was unnecessary and a bit of a turn off.
– My Domme said she felt the sex was selfish, she didn’t feel like he put her first and was there mostly for his own sexual pleasure, he didn’t ask her reassuring questions or ask her how she felt, he just ordered her to change positions and she didn’t enjoy it as much as she thought she would. She still orgasmed and had fun, but didn’t want to continue after her first climax. She doesn’t regret it, but also isn’t sure she wants to continue with him.
– My Domme was a little annoyed at how fast everything moved, he really only seemed interested in fast-tracking to intercourse (despite saying otherwise when we met him), there was little conscious thought put into any sort of foreplay and little desire to act ‘dominant’ outside of barking orders.
– My Domme later told me that when they went into the room alone he started making out with her almost immediately and also taking his clothes off. She felt uncomfortable because he was supposed to start with giving her a massage first and she wanted me to be involved so she invited me into the room quickly. This mostly just reaffirmed for me that he was only really interested in quick intercourse with my Domme for his own needs and pleasure rather than either of ours.
So overall, it was an arousing experience where my Domme was able to orgasm and I definitely felt like an emasculated sissy gurl, but also there were enough negatives that we will look for someone else going forward.

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