Jayme's Emasculation

"Get on my bed, on all fours." She ordered. "I want this to be special for you."

He did as he was told and crawled onto the middle of the bed and waited for her. He felt the bed creak as she got on behind him, one of her hands resting on his hip. "Get ready sweety." She remarks as she pulls aside the string covering his ass and pushed something long and thin into his ass. He gasped at the sudden intrusion but wondered for a second why it felt soo small compared to the massive cock she was wearing. "Just getting you all lubed up, don't worry hun." And with those words she starts squeezing the bottle attached to the nozzle, shooting lube into his ass.

"Take a deep breath and relax." She says, giving him a slap on his ass. "Just let it slide right on in, I know all you femboys are just sluts for being fucked in the ass, so this should be amazing for you." He was about to protest when he felt the thick bulbous head of her strapon push against his tight hole. The feeling was overwhelming as it strained against his hole for a second and slipped in. He moaned and lowered his face into the bed. "Good girl." She says as she slides in the thick rubber cock. Getting about halfway in before pulling out and pushing back in, getting a little more in with each thrust. Gently working the entire length of her cock inside him.

All of Jayme's confusion about tonight has just melted away with her first thrust, he had never expected to enjoy any kind of anal play, never once had he touched himself sexually back there. But this was heaven. At first it hurt a tiny bit but the pressure of such a large toy entering him had hit pleasure centers he did not know existed. With each thrust she rubbed against a spot that sent jolts of pleasure to his shrunken clit, already overwhelmed with the feeling of rubbing the sensitive tip against the soft material of his new thong. It felt like he was cumming nonstop, leaking into his thong leaving a damp spot he could see when he looked down at her legs.

After a short time, Cassie was able to get her entire toy into her newly made femboy's ass, slapping her balls against the smooth skin where Jayme's should have been, she picked up the pace. Fucking him with the huge toy and slapping his ass. Telling him what a good little slut he was, begging to come over and give her his balls like a good femboy. Jayme was overwhelmed by the feelings and could not believe his ears when he heard himself beg for her to fuck him harder.

"Fuck me! Fuck me harder! Make me your little femboy slut!" He cried out as his 3rd orgasm washed over him, the wet spot in his thong now dripping onto her bed. She laughed and started to slow down before coming to a stop, balls deep in Jayme.

She gave him a playful slap on the ass and then pulled out. Jayme gasping for air, let out a loud moan as the tip slid out. "You can use my shower for a rinse if you want to, ill find you another cute pair of panties to wear home."

"That's a good idea." Jayme gasped. Standing up on wobbly legs, holding the bed for support while he gained his balance. The bathroom was joined to her bedroom, so he did not have far to go. Thankfully.

While he was in the shower, he thought he could hear Cassie talking to someone on the phone, laughing, but he was not sure. So, he decided not to worry about it. He quickly rinsed and got out, drying himself off he walked back into her room. She handed him a skimpy pair of yellow panties with bows on the hips of the waistbands.

"You can keep those ones, I got them for you yesterday!" She said beaming a huge smile at him.

"Thanks, you sure you don't want them back or anything?" Jayme answered while pulling them on.

"Nah, I figure they are a good trade. Since I get to keep your balls and all that." She laughed. Jayme could not help but join her in a good laugh at that last remark.

He grabbed his jeans and noticed his boxers were missing. While he was pulling them on and looking around, she told him that she threw them out, since he wont need boy underwear anymore. He finished getting dressed and she walked him to the front door. Gave him a kiss on the cheek and just as he was walking away from her house she called out.

"Oh, don't forget to tell Tara I said hi and thanks!"

He was left wondering thanks for what as he walked home. Each step rubbing the soft fabric of his panties against his little clit. He was loving the new sensations. He got home in no time at all, not paying attention to his walk, instead just basking in how amazing his night was. He got in and his mom was sitting on the couch waiting for him.

"I hear you had one hell of a night, come tell me all about it! Ill grab you a glass of wine and we can chat!"

Oh no. Jayme realized that it was Cassie messaging his mom the entire time and likely it has her that she called while he was rinsing. He had no choice though, so he sat next to his mom, took the offered glass of rose wine and took a big gulp...