Strap-on Sex with My Sissy

I Love When My Sissy Pretends

To be a man. It gives me such pleasure to laugh at him when he is wearing men’s clothing. We all know that costume is a front! What he wants, is strap-on sex with me, or the real thing. If you’ve ever done a call with me then you know how ready I am to oblige a sissy with my cock. My sissy goes by the name “Sam”, and she likes it when I dress her up and then use her until she is cock drunk and sore.

Tonight, I picked out my favorite piece of lingerie. A sweet white bra and pantie set. Sam’s favorite roleplay was being the shy virgin girl who discovers she loves strap-on sex. Of course, I would wear something more masculine, and commanding, make Sam feel like I was a man about to take her virginity by force. You know how it goes at first, I’m sweet, “Come on baby, you know you like me and want what I have” I’d coo in her ear. She would play the blushing girl and refuse me.

This Was All Part of Strap-on Sex

Eventually, my hands would become too free, and would grab at her bare knees. Sam would push my hands away and act horrified that I was politely forcing myself on her. By this point, I would become frustrated and take from her what she wasn’t giving me freely. I’d leave my pants buttoned but would unzip and pull my strap out.

“Get the fuck on your knees, and suck my cock, bitch!” I’d command. She wouldn’t even have an opportunity to refuse. I would overpower her and stuff my 8-inch cock deep into her throat. “Oh, please Mistress, Hailey, I can’t take anymore” Sam would beg. Of course, I knew she wanted me to escalate things. I could hear her pussy throbbing while I pumped my cock in and out of her drooling mouth. She was obsessed with anal phone sex, and that’s how we got started.

She Loved Strap-on Sex More Than Anything

And she was embarrassed to admit it and felt less guilty when I “made” her take my cock. “Good slut. Now, lay on your back and let me see that pretty little pussy of yours”. Sam pretended to be full of fear and said “Please! I’m a virgin, I’ve never had sex before!” the look of fear was almost believable. “Shhh, I’ll be the judge of that. Stop talking, and roll onto your back, whore”. Sam did as she was told

I put a generous amount of lube on my cock. Sam tries to wiggle away as I touch and tear at her panties. She won’t stop moving, so I pin her down reach between us, and yank her panties to the side. Immediately, she started bucking her hips trying to throw me off. “Oh no sweetheart, you’re in for a long night of strap-on sex. That hole is going to be mighty sore by the time I’m done”.

I Slid All 8-Inches Deep into Sam

She let out a loud moan. “Fucking, whore! I knew you couldn’t resist. Wrap your legs around me and take my cock!” I took her by the hips and began a hard deep fuck journey into her pussy. It took all of 2-minutes before she was begging to cum. Of course, I wasn’t so generous…not yet. “You wanna cum? Aww, that’s so cute. How bad do you wanna cum?” I taughtened.

“I’ll do anything, Mistress! Please!” She said. “Admit you’re a whore and you love strap-on sex, and you can’t get enough of sissy boy sex toys“.

Call Hailey 1-888-823-9243