Can I Borrow Your Boyfriend

"Ok, Ok, I got one," Josh said. I was out with my friend Melissa and her new-ish boyfriend Josh, and we were three glasses of prosecco into a late brunch. The waitress was clearly hungover and didn't give a shit, service was winding down, and we were off in a corner gossiping and talking trash. The current topic: terrible first-date icebreaker questions.

"Bunch or fold?"

"Bunch or fold what?" I asked.

"Toilet paper. Do you wad it up so it's soft, or do you fold it so you have an even surface to work with?"

I resolved to leave a good tip for our poor hungover waitress, because the volume of our laughter was visibly annoying her.

"Oh, fold. Definitely. Less wasteful, and yeah, you have an even surface."

Melissa looked at us quizzically. "Bunch, definitely."

Josh said, "I bunch too, and it never occurred to me otherwise, but someone asked me that once and I was like what the fuck else have I been not doing or not considering? What other stuff did I think was totally normal that was actually a weird thing?"

"Yeah," I said. "I actually knew someone in school who'd never eaten pickles. A Jewish girl from Long Island who'd never eaten pickles. For some reason they just weren't a thing in her house, she'd seen them at restaurants as basically inedible garnishes, and she was confused by them existing in other people's homes as actual food."

"Bizarre," Melissa replied. "But I guess that's how growing up is, right? You assume your experience is totally normal and then later you find out what's idiosyncratic or weird or unusual."

"Totally," laughed Josh. "Or things you think are very specific to your family or your culture are, in fact, pretty common and you had no idea. Like, my parents fucking loved brunch when I was growing up. Other families went to church and we'd make eggs Benedict at home on Sundays. My friends and I were grossed out because soft eggs and sauce, right? But here we are and everyone in this restaurant is paying twelve bucks for that weird thing I thought only my parents were into."

Melissa said "it's funny how tastes change – that was actually one of the get-to-know you questions on the dating app, how much your tastes have changed."

Josh laughed. "But they didn't mean if you'd learned to like olives, that was about sex."

"Ha! Yes. I mean, Josh thought I might not be adventurous enough, because I told him I'd had the same interests all along." Josh and Melissa both giggled conspiratorially. "Of course, when I was a kid and saw Aladdin, my favorite part was the princess got captured. I liked getting tied up before I knew what that even meant."

"What about you, Josh?" I asked.

"I'm not sure. It's hard to tell the difference between "I like this new thing" and "I always would have been into it and only found out about it now. But... yeah, I've definitely been into kink since I was old enough to know what that was. Not one specific role, though, just... anything involving a power exchange gets me. You?"

"There's definitely themes – I'm a sucker for anything involving someone being so horny they make terrible decisions for some reason – but I wander. Like I'll fixate on one thing for a while and get bored with it. But I also do that with non-sex interests, like that time I spent three years as a gym rat and then decided I liked drinking at brunch instead of lifting weights on weekend mornings."

We all lifted our glasses at that, and signaled for another round.

"Josh has definitely gotten me to try a few things I didn't think I'd enjoy," Melissa said. "I'd never topped before and didn't think I could. I'm terrible at it though!" We all laughed but she said "No, seriously! The first time he asked if he could come, I told him 'be my guest" instead of making him beg for it!"

Our waitress definitely deserved a substantial tip.

"You're getting better at it, though," Josh said, his voice halfway between sweet and pornographic.

"What other new stuff have you tried?" I asked, trying to match his tone.

"You first," Josh said. "I'm new to your filthy lunch bunch."

And I have to admit, I was afraid. I looked down at my mostly-empty plate and my newly-refilled glass. As much as I wanted to hear about their secrets, I was worried they'd be unwilling to tolerate mine. "OK, so... As a teenager, we had dialup and one computer and me and my friends would stay up late and look for porn. But of course this was teenagers and this was before all the tube sites. But we'd all be incredibly horny about it, and each of us would sort of sneak off to the bathroom for a minute and then come back, but it was obvious what we were doing. And eventually we all wound up jerking off together, which I thought was hotter than boobs on screen. Once, at a party, I got truth-or-dared into kissing a boy and I didn't like it at all, it was scratchy. But as an adult, I'd go on like Craigslist or hookup sites and look for guys to masturbate with."

"And I found a jerkoff forum on Reddit, where guys share porn they're looking at, and it feels sort of like doing it together without actually having to meet up in person. And some of it I wasn't into, but some of it I was surprised I liked. I found a video of a guy coming just from being pegged, without touching his cock, and it blew my mind. And I kept looking for that. And there was this huge current of gender bending to a lot of it– some just men bottoming, but also trans women and some men crossdressing and calling themselves sissies. And the sissy stuff, the guys wanting to be humiliated and feminized... for some reason that really stuck with me. I never thought I'd get into that, but just watching that... eruption, you know?"

I was still staring at my glass, blushing, and hard as a rock.

Josh's eyes were gleaming. "Oh, handsfree orgasms are the best!"

Melissa looked surprised. "You can do that?"

He nodded. "It's the best – and I'm usually still horny after and want to keep going, too." Nodding to me, he asked "Can you?"

"Ha! No, although I'll admit I've had fun trying. I don't much feel like a sissy but I think it'd be pretty hot to have a femboy to play with sometime. Are you into that kind of stuff?"

Josh and Melissa looked at each other. This conversation was definitely crossing some lines we'd never crossed even in the years of our tell-all gossipy friendship. "Yeah, I definitely like dressing up as a girl. I know there's something fucked up about it, too, that whole 'being feminine is humiliating and weak and bad' aspect of it. And it's not the only thing I like, I'm pretty versatile. But if I'm bottoming, I don't just want to be tied up, I want to be objectified. And it's been there for a long time, probably since junior high."

"My first crush on a boy, my first real sexual experience, was a lacrosse teammate. We were the same age, but he definitely hit puberty way earlier than I did. Like, you know how high school is – he was taller and more grown-looking than the rest of us. Even since JV sports, he was clearly the star. Everyone looked up to him. And we were changing in the locker room after practice, and you know how teenage boys are, like, super shy in the locker room. He wasn't. And I looked, and he had nothing to be shy about. And he saw me looking. And then I sort of was just slow getting my stuff together and everyone else had left, and he comes up to me and says 'you like what you see?'

"I denied it, of course, but it had to be obvious. And he says 'show me yours.' I didn't want to, but he said it was only fair. And I did, and he pulls his cock out and mine is smaller – it's grown plenty since then, thank you – and he gets up really close to me, I'm like frozen with fear and lust, and he pulls his dick out and holds it next to mine and says 'look how different they are' and puts his hand around both of them at the same time. And then he says 'you can suck on it,' and puts his hand on my shoulder, and pushes me down, and I do."

"He never reciprocated. He just used me. And I loved it. And he'd call or text and have me come over after class, or he'd come to my house, we'd tell our parents we were doing homework – and we were, mostly, but halfway through he'd want a break and I'd have to suck him off again. I couldn't ask for it. He'd always initiate. And I maybe that love of the uneven power dynamic, of one person giving and one person taking, had been waiting to be discovered. And maybe I'd learned to like it from such an intense formative experience. But I'll play either side of it, to different degrees, any time."

"So do you dress up a lot? Do you have, like, a wardrobe?"

"Not a ton, I have a few outfits, some stockings."

Melissa interjected, "He's better at makeup than I am. I asked him to put my eyeliner on for me the other day and it was fucking perfect. I think I'm learning to enjoy topping – seriously, last night was fantastic, babe – but it doesn't feel natural."

"How so?" I asked.

"Like, what kink has always been for me is handing the reins over to someone I trust, letting them take charge. I like being controlled but I don't want to be humiliated, I don't want to serve – I want to be able to let go. But Josh says he wants to serve me, he wants me to humiliate him. I'm like, what, do my dishes? Dishes aren't sexy."

"If you made me do it naked, and ordered me to do it, it'd be sexy," said Josh.

"Nah, I don't think I can handle that, at least not yet."

"Shit," I said. "My apartment's filthy. Can I borrow your boyfriend?"

We all laughed, but the seed had been planted. A week or two later, Melissa texted me to ask if I'd been serious about borrowing Josh. I told her my apartment didn't actually need cleaning but I'd be happy to boss her boyfriend around. And that's how I wound up standing awkwardly in his kitchen on a Saturday morning, trying to figure out what to say.

I grabbed my crotch and leered, "You like what you see?" We both laughed, breaking the tension, but also setting the tone. I stood close to him and wordlessly started unbuttoning his jeans, then mine, and we held our cocks against each other. He wasn't lying about having grown since his youth. We were nicely matched, his skin fairer than mine, but we fit together, a substantial handful of twitching maleness. I kissed him, scratchy though it was, and then pushed him slowly to his knees so he could taste me.

Soon, though, I stopped him. We had work to do. "I brought you something to wear today, and I want you to do makeup to coordinate with it. And then you're coming to my house and I'm making you do some laundry, and then I'm making you come. Sound good?"

"Yeah."

"You mean 'Yes sir.'"

"Yes Sir."

"OK, now, strip."

The blinds were open, and Josh looked out the window to see if anyone was home next door. They weren't. So he stripped and I pulled out the clothes I wanted him to wear. It wasn't much: a pink double-A-cup bra and matching lace thong, and a steel butt plug with a matching pink gem on the base.

First, the plug. I bent him across the kitchen counter, his cock pressing a droplet of pre-cum against the cabinets, as I put lubricant on his pink asshole, slid a finger inside and felt the snug heat of his body. He gasped as the cold steel plug touched him, his anus winking at me as I teased it, pressed the toy in and felt it yield, then become acquisitive as the widest part of the plug went inside him and pulled the glimmering pink flared base level with his skin. The thong would hold it in more, but it wasn't going anywhere regardless.

Pink on pink on his fair pink skin, and despite the cock straining grotesquely against the front of the thong, he looked even more feminine than I had imagined. So I sat him down to do his makeup, a demure lip, some eyeshadow, nothing too time consuming. We did, after all, have some chores to do. He had a crop-top and some shorts that completed the look, or at least made it complete enough to leave the house in, as long as nobody saw him.

At my house I stripped him back to the lingerie and told him to start folding my laundry, while I sat on the couch, unbuttoned my jeans, and interrupted him again and again to come service me for a minute or two. Yes sir. No sir. Mfffrmc.

When the laundry was folded, I ordered him to take off the thong and bend over the dining room table. His hips fit right at the edge of it, his pointing at the floor, and I pulled his hands behind his back, pressing his face into the tabletop. I wrapped the thong around his wrists and tied them, then wriggled the plug still back and forth in his ass to hear him whimper.

"Do you like this?"

"Yes" he whispered.

"Yes what?"

"Yes sir."

"Do you need more?"

"Yes sir."

I slid it out and added more lube before stepping over to the sideboard where I'd hidden a surprise – a curved steel prostate massager. Facedown on the table he couldn't have seen it, but the intake of breath when it touched him was delightfully familiar. He wriggled I held it firm against his hole until he relaxed and then slid it in, sliding it slowly and firmly across his interior topography. He was fully hard, and a glistening droplet of fluid held at the tip of his cock. I caressed it lightly as he shivered and whimpered.

"Do you like having your hole owned like this?"

"Yes sir."

"Do you want me to keep pushing you like this?"

"Yes sir."

The fluid dripping from his cock was white now, as though I were milking the semen right out of him.

"Do you need it?"

"Yes sir. I need it. I need it sir. Oh god."

His voice was high-pitched, begging. I pressed harder, rhythmically, against his prostate. His cock swung in the air, untouched and leaking prolifically.

"Oh god, I need it. I'm gonna come. Oh god. Sir, may I come?"

"Not yet. Not yet. How bad do you need it?"

"Bad! Sir I need it!"

"What'll you do for permission to come?"

"Anything. Oh god, I need it."

"Come for me."

His moan of response was beautiful as he twitched beneath my hands and came, dropping more semen onto the floor. The house was definitely not as clean as when he'd started "cleaning" it.

I untied his hands and helped him up, and asked him how he felt.

"Instatiable."

"Good."

His asshole was slick with lube and stretched, ready for my cock, but I didn't slide it in immediately.

"Get on your hands and knees. Ass in the air."

He knelt down and I pressed his head toward the ground, near the pool of semen he'd left.

"Clean it up for me."

He shivered, blushed deeply, and began to lick up his own mess.

"How's it taste, femboy?"

"It's good, sir."

And that's when I finally let him have my cock. It didn't take long before I came, and when I pulled out, his asshole was dripping with come and lubricant.

He was going to need more fucking.