Turned Into A Sissy Boi - Sex Stories

Turned Into A Sissy Boi

... spanking dressed like a sissy. Jenny did not disappoint. Her hand came down hard and fast on both cheeks. I felt my bottom starting to heat up. I also felt my cock getting hard. The more she spanked, the harder it got. “Stand up” she ordered after a few minutes. I stood there with my bobbing erection inches from her face. “Hmmm. Looks like we found something else that you like” she said as she fondled my dick. I moaned slightly as pre-cum oozed out. She pulled my panties down and had me step out of them. Then she placed me back over her lap with my cock firmly between her legs. She reached over to the nightstand and grabbed her plastic hairbrush. CRACK!!! CRACK!!! CRRACKKKK!!!! The brush stung a lot more than her hand did, but I did nothing but yelp at first. Jenny covered my whole ass with redness and soreness. The spanks were hard and steady and it felt as though my butt was on fire. But at the same time, I was ready to explode as my cock was rubbing against her bare legs. After five minutes, I was half crying in pain and half moaning in pleasure. Then it happened. I arched my back and exploded all over her legs. “I knew it! I just knew it!” Jenny exclaimed as she saw my back arch and felt my cum on her thighs. She paused spanking me while I shuddered in orgasm. After a minute, she had me get off her lap. My ass felt hot, swollen, and very, very sore. She spread her legs and ordered me to lick my cum off her legs. After that, she lay back on the bed and ordered me to ...

... eat her. She had an orgasm in a few short minutes. Sex changed for me after that night. I no longer fucked Jenny. I used my tongue and got her off orally. She kept me dressed as a sissy slut in garter belts, stockings, and all types of panties. I was required to keep my bum very clean, and to keep my body hairless. I wore the frilly lingerie under my “outside” clothes, and immediately stripped down to them when I entered Jenny’s apartment. Spankings became more and more frequent but with rare exceptions, I came each time she reddened my rump. In addition, she used several dildos and other objects to fuck my willing bottom, and I squirted each time that happened also. She began to “expose” me to different people. Once, wearing red stockings, red and white crotchless panties, and having a pink ribbon tied in a bow around my hairless balls, she made me answer the door when she ordered pizza. The pizza delivery boy just stared in shock at my outfit, and my face matched the color of my stockings. Jenny saw the whole thing and could hardly keep from laughing. I wore the same outfit a week later when she again ordered pizza. This time, an older woman delivered it. She started to laugh immediately. “Nice bow, sissy ” she said. Jenny appeared at the doorway and the delivery woman congratulated her on my outfit. As I was paying her, embarrassed as anything, I dropped one of the bills. Jenny ordered me to turn around and pick it up, which gave the woman a bird’s eye view of my recently ...