Tatum's Friend, the Bully

Pearson checked the lip gloss in the mirror. He looked perfect. Pearson knew he really didn't look like a woman, just a pudgy little man, chubbiness poking out of the hideous pink nightgown that he and Tatum had purchased through the tranny site.

But he liked this-he would go into the bedroom, and Tatum, gorgeous in her own lingerie, would make him suck her strap-on dildo, and maybe she'd fuck him in the ass, which might hurt, but was getting easier as they did it more often.

Of course, Tatum had been talking about getting bigger and bigger dildos, just so he'd learn to take it more and more.

As Tatum had decreed that they not make love until their wedding night, this sort of sex play was somewhat of a substitute, but at least it was an exciting one.

Dressing in drag was her idea, and Pearson hadn't enjoyed it at first, but he understood that if he was going to be impaled by a strap-on, he should play the part of a "little bitch."

Now, Pearson balanced on his high heels and came into the bedroom and...

Who the fuck is that?

Sitting with beautiful Tatum was a big, muscular guy. Look at those tats. Ugh.

"Who-who is this, Tatum?" Why the FUCK is he in our bedroom?

The guy looked at Pearson, sneering. "Jeez, he really is a sissy, ain't he?"

"Don't you remember Giancarlo, Pearson?" Tatum asked, smiling.

Giancarlo reached over and put his grimy fingers into Tatum's pale white cleavage.

"Giancarlo? The guy I told you about who used to bully me?"

"Aaw, we just roughhoused a little, Pearsie." Giancarlo said, before spitting tobacco on the Oriental rug.

"That's my mother's rug" Pearson said. "You'll ruin it."

"That's my mother's rug" Giancarlo and Tatum said in stereo, in a horrible falsetto.

Then they dissolved in helpless laughter. "See, that's why I hadda kick his ass now and then." Giancarlo said, shaking his head.

"Right." Tatum said, smiling. "You thought it would make him tough."

"Apparently not." Giancarlo said. "He's wearin' Seventies blue eye shadow. It's really gross. Look, rouge-"

"The modern name is blusher." Pearson said stuffily. "What the fuck is going on here, Tatum? This is our private time. And I told you, Giancarlo traumatized me."

"I know, honey, and I think this is a healthy way for you to deal with your fear."

Tatum rubbed Giancarlo's big broad chest with her small hand.

"See, if you expose your true self to Giancarlo, show him your sensitive side, here with your lip gloss and nail polish, and help him to understand that you really were a sissy, and it was just cruel of him to try to kick you into masculinity..."

"Yeah, it shows me how insensitive-" Giancarlo began laughing "Shit, Tatum, I don't think I can do this without laughing my ass off."

"Tatum, you're my fiancée." Pearson said, feeling angry tears coming into his eyes. He bunched his hands into fists, trying not to break his press-on nails.

"You told me once that you sometimes fantasized about Giancarlo taking you from behind after beating you up in the locker room and stuff." Tatum explained helpfully.

Giancarlo got up and swaggered over to Pearson, who shrank back in horror.

"So you want to get corn holed? What about sucking my dick with those pretty, painted lips."

"You should thank me for this," Tatum said, laughing. "It takes a lot for me to let my fiancée have a gay experience." She smiled.

"I know how much you like sucking on my dildos, and we really have practiced teaching you to take it in deep, and now you can make me proud."

Forty-five minutes later, Giancarlo had split and Pearson was sitting on the couch, weeping softly. His makeup was smeared and his nightie had been torn, Giancarlo had taken him hard in the mouth and the ass.

Still, Pearson's dick was stiff and he kept cringing and getting more excited as he thought of Tatum's caustic look during this horror.

And her helpless laughter as Giancarlo had rammed his cock home again and again in Pearson's tender rectum.

It had been a tender mercy that she'd stopped Giancarlo when he wanted Pearson to lick his own shit off Giancarlo's dick afterwards.

Now, Tatum came into the living room. She'd taken off her own lingerie and was resplendent in faded jeans and a little buttoned vest over her bare breasts.

Smiling, she came and sat down with Pearson, and began wiping his face a bit with some Kleenex.

"Let it all out, baby." Tatum said, trying not to giggle. "That was quite an experience, wasn't it?"

"I-I just want to make love to you." Pearson said, gasping. "Why can't that happen? I don't want to be raped by my bully."

"You weren't raped. Remember? I asked you just before it started if you wanted to stop Giancarlo's um, assault, and you shook your head, slightly. You are not a #Metoo victim."

Now, Tatum reached under Pearson's torn nightie and began playing with his cock, rubbing and tickling it. She kissed Pearson deeply and smiled.

"You know I love you, and we are going to have a great, passionate wedding night, Pearson. I promise you this. But until then, these little games are all the action you are going to get."

"But I'm so horny. I can't believe he-he-" Pearson was about to cry again.

"Well, I-I can't say I'm terribly attracted to you right now, but why don't we do this?" Tatum smiled. "You can kneel over there and jerk off, and I'll slowly unbutton my vest here, and let you have a little show. It's the least I can do."

"That's-that's it?" But the added humiliation of being forced to masturbate in front of his beautiful girl, the rejection, seemed to only make Pearson's cock even harder."

"Goodness, this wee-wee of yours feels like granite." Tatum waggled her tongue as it peeked out between her teeth. "Go on, lady boy. Get over there and pound your pud for Mama."

"But-"

"Go on, or the offer closes, and I'm going out with my girlfriends. Maybe I should have them come over and see you in your attractive dishabille here."

Weeping fresh tears, so humiliated, Pearson got up and went over and knelt on the floor. His dick was terribly stiff, but he was so tired.

"Now cry and tell me how much you love me, and I'll let you cum. But don't go too fast. I will tell you when you can cum." Tatum laughed. "Let's see how swollen that desperate little member of yours can get."

Pearson began playing with his cock, and as he rubbed it, his legs started quivering.

"Stop." Tatum said. "Put your hands on your knees."

"But-"

"Stop, or I won't unbutton my little vest here."

Pearson put his hands on his knees and Tatum unbuttoned the first button, and her boobs swelled.

It would be a long night.