Renee was helping Regina get on the large strapon. I pleaded and cried, “Regina please don’t do this I can’t watch you fuck me like this you can’t!” She approached lathering the dildo in lube, Renee and Ronnie lifted my legs up in the air exposing my cum dripping ass. “Reann, you’re a woman now, your not the guy I used to fuck, now stop being a little sissy about this and take this cock!” She said as she pressed the dildo head against my ass. This was beyond humiliating, I used to fuck her and always wanted to try anal but not like this. As she pressed harder breaking the barrier of my already loose hole she said, “Reann, remember when you wanted to try anal, well I’m about to split you in half my little sissy.” With that she pushed her weight as the dildo sank in slowly.
Renee spoke up, “Reann incase your wondering this is a 10 inch dildo that is made for prostate massages with a curved tip, it is about 2 inches in diameter right around the middle, or simply put, we don’t expect you to come in tomorrow after Regina splits you ass in half, and you’re about at the thickest part.” Right as she said that Regina withdrew the cold dildo and shoved it back in as I let out a yelp, she just kept bucking into my ass. Pounding away, verbally abusing me about what a sissy I am. “Ronnie, look what you did, his little sissy clit is dripping precum soft and flopping around while his huge tits just bounce around. You do great work I must say!”
I looked down liquid was flowing out of my cock as it danced around, I felt a wave of pleasure building up in my ass. I started to moan, what was happening to me. My moans and panting grew louder as her dildo bucked against my hips, she was fucking me like a wild woman while Ronnie and Renee cheered on. I could only look up at the faces as they stared in a trance at the huge dildo ripping my ass up. “Oh gawd, oh gawd,” I yelped out as I felt like I was about to erupt when all of a sudden my cock started to let out a stream of cum like a faucet, it pooled all over my stomach.
“There is goes, he fucking came like the little sissy slut he is, only cumming from now on with a nice firm cock up his ass!” Renee exclaimed. Regina kept fucking me for a few more minutes as I bucked around in pure ecstasy. It was too much I collapsed as she kept fucking me. I finally came too as they were all dressed and I was still naked on the couch now.
“Reann, I am sorry I guess you must have just passed out and in the heat of the moment we didn’t notice. Are your ok.” Regina asked. I nodded to them Let’s get you dressed and out of here she said. Ronnie and Renee were heading out, “Hey Reann lock up and get the fuck out, take the day off tomorrow, you’ve done enough work today.”
Regina and I went out to dinner, I was ashamed and told her the whole story. She explained how they called her out of the blue and offer $100,000 to fuck you and an extra $50,000 if I really humiliated you. I didn’t blame her for taking the deal. She felt bad but a bets a bet and she missed the old me. She did want to fuck me again, she said it gave her a lot of power, she also wanted to see a guy rail me out, perhaps my roommate, guess I know what I am doing tonight at my apartment.
The end for now!