Karen and I had been “friends with benefits” for quite some time. She was about ten years older than I was, and was wealthy beyond my imagination. I loved visiting her large pre-war apartment overlooking Central Park West, and our weekends of sexual exploration were intoxicating. Karen was a former dancer who maintained her lithe and sexy body even into her late 30’s, and I was a young grad student who was still at the age that without an ounce of nutritional planning and just a minimal amount of strength training would still manage to have the physique of an Abercrombie and Fitch model.
Karen loved admiring my toned body as I’d wander through the hallways of her spacious apartment on the weekends, clad in nothing but my Daniel Alexander Thong underwear and a stainless steel chastity cage locked around my cock underneath the thong. Karen would keep the key hidden somewhere and would never unlock me until the end of the weekend, if at all. We had an understanding. I would show up on Friday evening and remove my clothes, handing them to her. I’d only wear my thong and chastity cage, which remained locked around my cock all the time. I’d spend the entire weekend pleasuring Karen, cooking for her, serving her, giving massages, and whatever else she desired. If she invited her girlfriends over, I’d do the same for them too.
Just in case I needed to remove the chastity cage during the week when I was away from Karen, I could always text her and she would remotely unlock the iKeyp Pro WiFi Safe in my apartment via the remote controlled app, but only if she deemed the unlocking necessary. If I wanted to be unlocked while I joined friends out on the town, she usually declined the request as it wasn’t urgent enough and because there would always be a chance I might meet a woman my age who wanted to get intimate, which would possibly result in me having an orgasm. Karen wanted me to always be ready for her. If I was going to have a one night stand, I’d have to keep my chastity cage on and risk the ridicule of my partner. If a potential partner was still open to an encounter with a guy wearing a chastity cage, I had no way to remove it and would still be denied relief. If I needed to remove the cage for a doctor appointment or for travel, that was a different matter.
In exchange, I got to experience a whole other world with Karen. She would bring me to dinners at Michelin Star restaurants, gallery openings, and I’d sometimes accompany her on trips, traveling first class to exotic locations. I never learned how she acquired such great wealth, but I was happy to enjoy it, and I was very happy to “pay my way”.
One weekend, Karen came to me with a request. After I arrived at her apartment and removed my clothes, I sat next to her in my thong underwear and chastity cage, gently massaging her feet as she liked.
She spoke. “I want to do something special for three of my closest friends. Amber, Rachel, and Sarah have been having a really tough time finding good men to date and they’re really disappointed with the current state of the dating market. They’ll be coming by tomorrow evening and I want you to show them a good time. You’ll serve them drinks, let them admire your body, and flirt with them a bit. Once they’re relaxed, I want you to take each of them, one at a time, into my meditation room and satisfy their desires. I know that each of them has either fantasies or sexual desires they want fulfilled. I assure you it’s nothing that you’d be uncomfortable with. Just trust me, and go make them satisfied and happy.”
Having seen her friends, I knew they were all quite attractive and in good shape. They were even quite sexy. I had a feeling that this experience would be fun. My thoughts were interrupted by Karen, who had removed her panties from under her miniskirt and was laying spread-eagle on the sofa. I knew what that meant.
I immediately got on my knees before her and began gently kissing the inside of her thighs as she began to moan. When I licked her pussy, she was even wetter than usual, and gave a slight shudder as my tongue came in contact with her clit. “I can’t wait to have you service my friends tomorrow…we’re gonna have a great time” she said. She was clearly growing incredibly excited just thinking about the upcoming evening. I was inspired to lick with more passion.
It was at that moment that I noticed that the lights were still on in the apartment, and the curtains were pulled back from all the windows. I couldn’t see outside, but anyone with a set of binoculars could easily see us. Karen always found this arousing, and loved for me to walk around clad only in my thong knowing full well that her neighbors likely watched us from time to time. I always found this slightly humiliating, but I think that made me enjoy it even more. I continued licking.
By now, my face was wet with the juices from her pussy, and her hips were moving involuntarily. I could feel my cock pushing against the inside of the chastity cage. I desperately wanted to get off too, but part of me really enjoyed being captive to Karen. I slid two fingers inside of her wet pussy as I continued to lick, and this was what put her over the edge. Karen let out a loud sustained scream as her muscles contracted into her orgasm. I held my tongue against her clit and gently applied pressure with my fingers as she rode several waves of her orgasm. I could even feel a little bit of pre-cum drip out into my chastity cage as she came through her final wave.
Once she came down from her orgasm, I climbed up on the sofa and held her as she liked for me to do. She was still breathing heavily and looked quite satisfied. We laid there together for some time, my fingers gently stroking her curly dark brown hair.
The moment was interrupted by her voice, “There are some leftovers in the kitchen if you’re hungry. I’m thoroughly exhausted. I’m going to sleep. Come join me in bed when you’re ready.”
With that, she got up, ran her hand over my ass for a few moments, smiled, and walked to the bedroom, leaving me on the sofa alone. After shutting off the lights, I got up and admired the view out the window. It was such a beautiful view, and I could see clear across Central Park over to the high rises along Park Avenue. I felt like a prisoner inside a palace, and it turned me on immensely. I turned around and walked over to join Karen in bed.
I lay awake next to her for some time thinking about tomorrow evening. I couldn’t wait, though I was a bit nervous, not knowing what her friends would want to do with me. I was suddenly wondering what I got myself into. But I also reminded myself that I was always at Karen’s mercy, and she never abused her power or put me into any situation I couldn’t or wouldn’t accept. Even when she brought me to Fire Island that one time and had me walking around the beach in my thong swimsuit with my chastity cage poking through, I was incredibly self-conscious and a bit embarrassed at first, but I came to love the attention, and I even enjoyed being ogled and fondled by all of the other men. And Karen loved it too. She truly got off on seeing me so powerless, so much so that she couldn’t even wait for me to go down on her. I was astonished to look over and see her masturbating in the corner of the room as she watched me being fondled by three (or was it four?) other men.
I would trust her judgment and would lean into the situation in the moment. We had a safe word, but I didn’t want to use it for fear that she’d grow tired of our arrangement. I was determined to do whatever was asked or demanded of me.
Continue reading Male Chastity Servant Part 2…
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