Why would a sissy boy only wanna  suck cock? That’s laughable in my opinion. If you’re willing to suck off a juicy big cock, you may as well dip into the pleasures of having your man pussy fucked hard and good by a big strap on before you let a meaty cock take the plunge!

Honestly, I think if you are a sissy boy you miss out on all the fun. I have a sissy boy just like that once upon a time. Always refused cock anywhere but his mouth. I decided enough was enough, and if he wanted me to keep dressing him up and feeding him cum, he would need to be a bit more open to anal play!

I went over to Josh’s house with a new sexy outfit and my shiny new black strap on. I laid out his new garments and showed him how I was going to dress him up like the little tramp he was. He fingered the silky fabric and smiled with pleasure. Once he saw the large strap on he was full of apprehension. He picked it up and asked why I brought it along. I told him to get dressed and do up his make up and come back when ready.

He did look tempting when he walked back into his room. Sleek stockings, push up bra, and the panties…well they had a nice large opening in the ass area. His chest was waxed smooth and makeup looked flawless. He could easily pass as a female. In his daily life he was a high powered attorney though. Not a single person would suspect he sucked dick on the reg.

I asked him how bad he was craving cum that night. He assumed the position and waited for one of my beefy black friends to enter the room. I stood in the room wearing thigh high latex stockings and fuck me heels. I wore a matching pair of latex booty shorts and bra. I was quite a sight for him. I was fitting my dildo on while I spoke to him. “Waiting for something Bethany? A nice cock to suck off?” “Well yes Mistress, that what we usually do.” He said. “Well here’s the thing, I have several cocks the need servicing by a sexy sissy boy but, if you want to play with them, you have to take my strap on in that virgin man pussy off yours!”

Once I said that 5 men filed into the room with cocks swaying between their legs. Oh how my sissy’s mouth salivated! He looked towards me and started to beg. “Please mistress, you know I only like to suck and swallow. I don’t think I will like it.” “Lay on the bed and spread your legs open like a good little whore. Open up your mouth, you have allot of cock to satisfy. I promise you will enjoy this!”

He begrudgingly laid on the bed and did as I instructed. I lubed up his opening and prepped his little man pussy for my big cock. I could hear his sucking and groaning as he worked the men in the room. Two cocks in his mouth, two in his hands and one jacking off waiting his turn…

Wanna find out what happens next? Read more of my sex stories until part 2 comes out.

Alyson

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