Cum Here Sissy Boi, It’s Time To Have Your Prostate Milked
Cum here sissy boi, it’s time to have your prostate milked! Sissy Boi’s are so eager to please and it doesn’t take much to get them twisted around my little finger. All they really need is a strong woman, like me to take control and it just so happens that I’m very good at the take control part. Connor is a very cute little sissy and I wanted to make him all mine, as a matter of fact, I wanted to make him my little bitch, my personal sissy faggot boi.
I picked him up at his place and took him out to dinner, you know sometimes you just gotta wine and done those little faggots. Hahaha! While eating, I told him that I had a little present for him and I had picked it out just for him. He asked what it was, but I made him wait until we went back to my place before I gave it to him. He opened the large gift bag and began taking items out of it; a short wispy dress, bra, a wig, stockings, fuck me pumps, lipstick, and eyeshadow. The only thing missing was the panties, but I told him that I needed his ass bare tonight, so forget about them and dress like a pretty princess for me.
I watched as he eagerly put everything on and helped him with the makeup because I didn’t want my little princess to look like a character out of the Rocky Horror Picture Show.
Connor looked so sexy in her new outfit and I made her do a twirl, like a ballerina! Her dress flew up and in doing so, she showed me how hard she was. I went over to her, pulled her close and kissed her, smudging her lipstick all over her pretty little face. I took her to the bed and pushed her on to her back, then went to get my strap-on. Then I made her put it on me, lube it up and then I knelt between her legs. I lubed up her hole and her tight boi pussy clenched around me.
I moved it around until she loosened up a little, then I pushed her legs up and lined up the dildo. Pushed forward, stretching her hole open, as it went inside of her and she moaned. I got it all in and began to rock my hips back and forth, the dildo sliding nearly all the way out before I shoved it back in. Her dick as twitching and pre-cum was leaking all over the head, onto her stomach. She moaned and begged me to go harder, to fuck her little boi pussy. She let out a LOUD cry, as I hit her prostate and I rammed into her again and again. I really Prostate Milked her!
Her legs tensed and she moaned non-stop as her ass moved on the dildo.
I saw her balls twitch upwards and knew she was about to lose it. I braced my hand on her leg and went in deeper, giving her prostate hard jabs. Strings of wet cum began to shoot out of her, landing on her stomach and the crumpled up underside of her dress. I kept going until there was nothing left, then ever so slowly pulled out of her.
Her legs fell on the bed and I leaned over her, cupping her face in my hand. “Did my little princess enjoy that?” I asked and she nodded breathlessly. “Good because I have another surprise for my little sissy boi Princess. Close your eyes.” I told her and went to get another bag from the closet. She kept her eyes closed, but her head moved with the sound of my footsteps, trying to figure out what I was doing by the sounds I was making. I stood by the side of the bed and said: “Open them.” She saw what I was holding and her eyes lit up like a fucking Christmas Tree in downtown New York City! This was going to be EPIC and VERY erotic! For strap-on, pegging, sissy boi phone sex, call me and I will make it WELL worth your time!