This is A First Time Sex Story because some sissies have limits. They’ll dress up all girly but when it comes to certain things like sex they’re all men. They’d never be girly and fuck a guy, that’s way too kinky for them.
Usually, I let it go because it’s fun dressing them up and showing them off. I hated the way Tommy acted like he was too good to do something like that. We just had to put him in his place and show him the joys of being a true sissy. I love a First Time Sex Story.
Adam comes over and told Tommy that he was going to put on a show for us. He liked the idea of being humiliated in front of a stranger. I don’t think he was expecting what we had planned.
I picked out an outfit for him while he got naked. He put on a padded bra, a tiny red dress but no panties.
“Isn’t she a pretty girl?” Adam said, teasing him as I handed him makeup. He slicked red lipstick over his lips, flicked on some mascara and added a cute blonde wig to turn himself into Tanya.
“Oooh, now give us a twirl,” I said and watched as he spun around, his dress flying up so we could see his semi-hard dick. “Come on sexy, show us what you can do,” Adam said and Tanya did poses for us, putting her hand on her hip and fondling her fake tits while pouting her lips.
I got on the bed and gestured her to come to me and she crawled to me, her ass going up in the air as her dress fell to her hips. Adam stared at her round firm ass and virgin boy pussy as he quietly got naked behind her.
I distracted her by telling her how sexy she was and what a great First Time Sex Story this would be also a great anal sex story!
She stopped in front of me and I got on my knees, pressing them lightly down on her arms, pinning her in place. She thought it was harmless fun until Adam got behind her and popped open the bottle of lube.
“What are you doing?” she asked, looking behind her and I grabbed her chin, turning her back to me. “It’s time for you to become a woman,” I told her and pressed down harder on her arms. Putting a hand between her shoulders, I kept her low and still for Adam to lube up her boy pussy.
She tried to pull away and told us to stop as Adam shoved a finger into her tight hole and fingered her.
I told her to knock it off and it’ll feel good if she relaxed. There’s nothing better than being fucked by a big, hard dick, all girls know that. She was listening to me because she got louder as he started pushing his dick into her.
Letting go of her shoulders and pushed my hand against her mouth to shut her up as he grunted and shoved the last few inches in.
She was taking big breaths and whimpering as he began thrusting back and forth, his big dick ripping past her tight hole.
He moaned and said how tight she felt as he fucked her and it made me so wet seeing Tanya used like this.
Her body shook as Adam used her and she did a shocked noise as her prostate got hit. Adam kept going and when he came Tanya looked so freaked out.
Adam pulled out of her and she was so embarrassed and had so much Humiliation about getting fucked like a bitch. I think it was even worse for her because she liked that second of pleasure she got from her prostate. Maybe next time she’ll like it even more.
