Turned Into A Sissy Boi - Sex Stories

Turned Into A Sissy Boi

... yours. I have a special treat for you tonight.” “I can’t wait!” During that enema, Jenny played with my cock and balls and I came dangerously close to having an orgasm several times. She knew just when to back off though. She also gave me several smacks on my presented posterior telling me what a cute ass I had. With a final smack, she told me to use the toilet. Afterwards, she wrapped her hand around my penis and led me into the bedroom. She had me get on my knees with my face on the bed. My ass was positioned towards her. She told me to spread my legs a bit, and she started to slide a lubricated finger in and out of ass. I started to moan, and she chuckled. “That feels good, doesn’t it?” she asked playfully. :”Mmmm Hmmm” I moaned in response. “Then this should really feel good,” she laughed. I felt something press up against my hole. In another second, I felt this large object being pushed into me. “What the hell are you doing”, I said as I started to get up? I got a sharp slap on my ass. “Lie back down!” Jenny ordered. I did as I was told, and felt more and more of something being shoved up my ass. “Tonight, I’m the one who’s going to do the fucking” Jenny announced. “I’m going to fuck your ass with a strap-on, so you may as well try and enjoy it.” “But….” “Exactly! Your butt! The butt I’m currently fucking! I want to see if I can make you shoot your load by butt-fucking you! Now just kneel there like a good boy and enjoy.” I did as I was told as Jenny slowly pushed the ...

... dildo into me. She then drew it out just as slowly. The next in and out motions were just a bit faster. It took her a minute or two before she got into a nice rhythm. When the strap-on first entered my butt, my cock began to soften. However, as she started to fuck me, it grew stiff again, and I had to admit that I was really enjoying it. I began to push my ass back against her. I started to moan again. “That’s it baby. It feels good when I fuck your ass, huh? You like it when I fuck your ass, don’t you?” I really did! The soft plastic cock moving in and out of my bottom felt strange yet wonderful. Jenny was plowing my butt harder and faster now. My dick was hard as a rock. “Cum for me baby! Cum for me baby! Shoot like a good boy!” Jenny repeated this over and over and started smack my ass cheeks while thrusting the strap-on in and out of my willing butt. I finally reached the point of no return and let out a load groan as I came all over the bed. Jenny buried the strap-on deep in my ass and held it there while I shuddered in orgasm. She briefly pulled out and unbuckled it, then shoved it back into my ass. She told me to stay where I was. She grabbed a paper towel and wiped up my sperm. Then since I was at the bottom of the bed, she lay down in front of me, legs spread wide. I didn’t need to be told what to do. I started eating her out with my dildo-filled butt sticking up in the air. Sex for the next few weeks consisted of me getting my rump reamed in all sorts of positions ...