Six months ago I met a great, sexy hook-up in my class. She was amazing at giving blow jobs. My first week at college was amazing. She said that it would make it worth my while if I shaved my body. And boy was it worth it. Each week was another thing I had to do, but I was rewarded with something new and incredible. Little things like, take these vitamins, don’t cut my hair, wax my eyebrows, let her try some make-up on me, etc. I never realized how pretty my face was until that day, but I washed it off and went on with my masculinity shaken but intact, nothing was permanent, and nobody knew.
Things started to escalate, she asked my to show up to college wearing panties, that is where I think I realized what her kink was, feminization. Still, nobody knew what I was wearing underneath, so I thought, what the hell. I was super nervous buying some fairly boring white ones at the store, but the cashier didn’t say anything. Pulling them on in morning was new, but they were fairly comfortable. That night she gave me a rim job for 10 minutes, I had never experienced my ass being tended to so heavily, as soon as she touched my cock I shot my load within seconds.
Next, Bra, then stockings, then getting my nails done (just clear polish on my hands, but pink on my feet). Each week cumulatively adding feminine items. Then one week she asked me to arrive at class with a chastity cage on. I bought one at the store and wore it the next day. I knew something amazing would be in-store later than night. And it was not what I expected, I took off my clothes and showed her my feminine garb with the cage on. She smiled and said “Good boy, now there will be no more touching of your cock except with my permission. Trust me, it will be worth it” I was shocked, but still trusted her.
She kept me locked up for two weeks - but she kept torturing me with anything to make me horny. At the end of the two weeks she pulled out a strap-on and fucked me in the ass. I didn’t object, I just wanted to find release, and after about 15 minutes of her fucking my ass I did surprisingly find it. It was amazing. This woman was truly a gift, even with all the feminine crap I had to put up with. She called it a Sissygasm and told me to learn to love them as this was my new release. Unfortunately the semester was coming to an end and she was going home to another city.
On our last day together she asked if I trusted her. I told her I did. She tied my arms above my head to the ceiling, and began teasing me. She did my make-up, and started placing clothes pins around my chest in circles. “I want to introduce you to someone new. I know you love your Sissygasm, and I think I know a way to keep you happy while I’m gone. Good-bye Jamie.” she kissed me and left the room.
After a few minutes in walked a man, I was totally shocked. “What are you doing here? Who are you?” I meekly asked
“Wow, you’re even more beautiful than the photos she sent. I’m your new Master. Lets take a look at that cock.”
“What?”
“Listen, I’ll be fair and let you live comfortable if you cooperate. I’m not sure what she told you, but I paid quite a bit of dough to own you. I have the pic’s I will send to everyone you know if you miss-behave. I have other ways too of making you cooperate, more drastic methods, like torture or castration. But I don’t want to be so negative, she said you were so cooperative, so I’m sure you’ll be just fine.”
My cock, finally free of the cage sprang to life instantly. Master commented “Hmm, might have to fix that, but not huge so it’s workable.” My head was spinning. “But I think maybe you like the idea of being a sissy slave, which is a big plus.”
Master returns the cage, then unzips his pants. “Time to test out your ass-pussy.”
