Trying New Ways to Orgasm
As part of my chastity, my keyholder (I’m in a female lead relationship) allows me to orgasm twice a month by masturbating if I haven’t ejaculated some other way during that time. This is actually a behavior she discourages because she loves the intensity of my orgasms when she allows it after several weeks of chastity and wants to be the only source of my physical pleasure.
However, MKH is reasonable and wants me to be healthy so that she can experience those orgasms for a long time to come…so she allows me to masturbate once every two weeks on Sunday. In her mind, this is a necessity for a healthy prostate but is not meant to be enjoyed. Sometime late last year (2023) she required that I eat all of my orgasms either from her pussy or if I’m masturbating, I swallow it from a shot glass. I’ve only been averaging two orgasms a month since then, so I haven’t had a lot of chances to get used to the taste…yet.
Lately, MKH has been “feminizing” me by wearing toenail polish, lip gloss, panties and women’s clothes during the weekdays when it is just the two of us. One afternoon, MKH had me eat and suck her pussy till she came five times, usually I’d fuck her after she has had so many orgasms; she loves feeling my cock after she’s cum. But this time she asked me not to, I was bewildered. “Does this mean I don’t get to cum?” I asked. “I don’t care if you cum, but I’m not helping you,” she said as she lay back in exhaustion. I started to stroke my cock when she stopped me. “Nope, that’s not the way you masturbate…you can use no more than two fingers over your panties (which I’m required to wear at all times), but you can play with your nipples. I want you to feel what it’s like to play with yourself as a girl,” she said with authority. I sighed and did as I was told. I pulled up the nightie I was wearing to expose my thong underwear that was doing a terrible job of concealing my erection. I began to tease the head of my cock through my panties while flicking my nipples. It was an entirely different experience than what I’m used to. There were lots of build up to these crests that didn’t quite pay off but were exhilarating. I was beginning to think that I wasn’t going to cum my first time playing with myself like a woman and got a little frustrated. Finally after 15 minutes or so, my cock begin to squirt semen. It was an intense orgasm that felt elusive. MKH watched in fascination. “Don’t forget, we don’t want to waste your cum,” she purred; she captured as much of the cum as she could and fed it to me. “Holy shit, if that was half as intense for you…that must’ve been super intense,” she said, “from now on, you can only masturbate like a girl and I want to watch.” “Of course, babe.” What else was I going to say?
