Errol’s laugh is bitter. “Oh, it wasn’t a mistake. He knew what he wanted when he said he wanted to dress me up and degrade me.”
“Dress you up? What do you mean?”
His expression is guarded. “You saw the underwear I like to wear.” When I nod, he takes a heavy breath. “Well,I kind of like dressing up in other stuff like that, too. You know, lingerie, eyeliner —”
I interrupt him. “Like a feminine thing?” He nods. “You dress like that when you’re hooking up?”
His face goes red again. “Yeah, sometimes. But… I like doing it just for me, too. I mean, when I’m by myself.”
He does that just to jerk off? Just for himself?“Fuck, I don’t know why, but that sounds incredibly hot,” I confess.
Errol shoots me a look of disbelief. “I never wanted to tell anybody that, honestly. It always felt a little bit pathetic.”
“Pathetic?” My eyebrows go up. “Oh my God, no —that issexy. But I’m sorry, you were talking about something that happened?”
“Yeah. The way this guy said it sounded hot when we were chatting online, and it seemed like we were both looking for the same thing. But when we got together, it went bad. He had stuff he wanted me to wear, but it was all way too small. Like, so tight I had to squeeze into it, and it looked really awful.”
He sighs heavily. “Which was what he wanted. And then he wanted to call me, like, a pig and stuff. He wanted to make my size, my weight the focus of how he degraded me and I just —” Errol’s hair falls into his eyes as he shakes his head, but not before I catch a glimpse of the tears sparkling in them.
“Oh, no! C’mere.” I pull him against me. I’m burning mad at this stranger. How could he? Even if you didn’t know Errol like I know him, how could this douchebag have thought it would beOK to make him expose the underbelly of his self-esteem so he could eviscerate it?
It’s so fucking unfair. Errol doesn’t have a mean bone in his body. “You didn’t deserve that,” I murmur against his hair. “I wish I’d been there so I could tell you then you didn’t deserve that instead of just telling you now.”
“I didn’t think it would hurt that much,” he says. “I played along with it for as long as I could and then I told him no more, I was out. He got all pissed-off about it but I didn’t give a fuck. I put my clothes back on and got the hell out of there.”
Errol shakes his head, lips pressed into a thin line. “I have to admit, the whole hookup scene was getting tough. Just too many guys looking for subs into feminization who, as soon as they see enough of my body to realize I’m not a willowy twink, either ghost me entirely or say something nasty on their way out.”
“That’s awful!”
He shrugs, a downcast look on his face. “Even though it always made me feel shitty, I thought I didn’t let it get to me. But maybe it made me more willing to overlook red flags when it seemed like a guy might —” Errol breaks off and squirms, “likemy body instead of just tolerating it.”
He frowns and runs a hand through his hair. “I fucking hate that one asshole might’ve ruined a major kink I used to like. But after that one time, I just —it made me a little sick to think about, to be honest.And I was too afraid to try wading into it again with somebody else. Afraid that if they said the wrong thing or turned into a jerk, I’d just go to pieces on them.”
His hair now rakishly disheveled, Errol puts his hand back on his thigh. Impulsively, I grab it. I’m about to do the smartest or the dumbest thing I’ve ever done — I don’t know which.
“Listen, Errol…”
I’m taking a huge risk. If I get this wrong, I’m not just blowing up my chance at a hot, dirty fling. If I screw this up, I’msetting fire to the best, most rock-solid friendship I’ve ever had in my life.
“I want you to feel sexy. I want you to feel good. And if you want me to objectify you and degrade you, make you feel good by making you feel bad like that, I want to give youthat, too. I don’t have any experience doing this, so I can’t promise I’ll never say the wrong thing. But if I do fuck up, I don’t care if you need to give it a minute, or stop the whole —” I search for the right word, “the whole scene if you’re not feeling it anymore.”
I glance at Errol’s face but can’t tell what he’s thinking. He’s quiet for a minute more and I’m about to backpedal or apologize when he takes a deep breath.
“I like —I think I’d like that. I mean, I’d like to try again.”
“Really?”
“I just want to feel sexy, not fat.”
My best friend is going to keep breaking my heart with that. And I’ll keep telling him what he needs to hear. I pull him back into an embrace. “Youaresexy. Do you think you might like dressing up and showing off your body for me?”
Errol lets out the hottest little whimper and squirms in my arms. “Yeah,” he whispers. It emboldens me.
“What do you like? What makes you feel good to wear?”
“Material that feels nice. You know — satin, silk,” he whispers. “And things like lace and mesh that expose me even when I’m covered up.”
I have no idea why this sounds so hot, but I can’t deny the way my cock swells at his words. “If I got you pretty undies that wrapped tight around your dick, could I tease you and watch you soak them with precum?”
