A Sissy Boy is Made

Fearing that he himself might be sent away less than satisfied Gregory quickly stammered, "Ohhhh yes ... yes I can satisfy you."

"I doubt it, you lit' wimp., but give it your best shot. Come up here and give Miss Fellows all you got. Fuck my brains out with that little thing." She told him in a voice dripping with sarcasm.

Jaclyn's degrading words heightened his arousal as his tiny man tool stiffened further. Excitedly, he jumped on her and slid his teenie cock all the way in, and began eagerly pumping her pussy as best he could.

Jaclyn giggled out loud, "You're tickling me, baby doll." "Come on, is that all you got sweetie?" she teased him, only turning him on more. "Fuck me, you bitch, fuck me like you mean it," Jaclyn urged.

Gregory pumped harder and tried futility to go deeper. His masterful performance was laughable, as it was only about a minute and a half before he unloaded his steamy hot cum inside her accepting pussy. He collapsed on top of her in complete exhausted satisfaction.

Jaclyn patted him on his head as he lay panting on her chest, and in a comforting voice she said, "That's OK baby, Miss Fellows didn't expect anything more than that. You tried your best."

Once again Gregory wasn't embarrassed by her condescension; He was turned on by it. They lay there for a few more minutes before Jaclyn sent him on his way in a taxi. The taillights of the taxi hadn't even disappeared from view before she was on the phone calling a real man to come over and fuck her right.

That was the first of only 16 times that Gregory has been allowed to fuck Jaclyn to date. The next time he was allowed pussy access was their wedding night, then each year after that on their anniversary.

The day after their first sexual encounter Gregory found himself in Jaclyn's office fearing he was going to be scolded, or worse, fired. To his surprise, he ended up under her desk eating her pussy for more than an hour as she conducted business on the phone.