[MT] Breaking in a stranger’s boyfriend

Early this year I messaged a younger trans guy who was looking to start hooking up with people. His partner had “a slutty phase” and wanted him to have the same experience, but he was anxious about meeting a stranger, so he was planning to have her come to watch and encourage him.

Moreover, he was essentially a virgin and wanted to be eased into having sex at all. I’d done this for others before, and actually helped another redditor with their first time a couple months ago, so I was eager for the opportunity. Plus, I’d get to help out a trans couple, which is who I prefer (DMs welcome! 👀)

We exchanged face pics after a couple messages and really hit it off. I’m really into twinks, and he’s really into physically larger guys. Since there was potential, we started exchanging porn clips to figure out what kind of sex he was interested in having. It was an interesting combination of gentle and caring, and violent or even taboo.

He’d mentioned filming was a kink, so at some point I sent video of me roughly fucking one of my FWBs. He responded:

“I wish that was me…”

We started discussing logistics and set a date for the end of the month. We agreed that she’d be there and help hand him over to me to be broken in, and to keep him calm and safe. He wanted a scene that started out gentle but escalated as he got more comfortable.

“You’re going to look so hot with a thick cock gaping your boypussy and a sturdy hand around your little throat…”

He was into it, to say the least! We exchanged more porn and talked about sex toys, STIs and protection, costumes, and more. We also talked about why he was looking now, and why on Reddit. We did talk about CNC and group play but I was clear we shouldn’t do that for his first-ever time.

The conversation went well enough that we moved the date up, to about two weeks from when we first started talking. He also decided that he felt safe coming down by himself, and that we’d film for his girlfriend instead.

He drove down to my place and I let him in – I’m a solidly built >6′ gender nonconforming goth, and he’s a skinny 5′ stoner/emo boy, so I towered over him. Our original plan was to hang out and watch some anime to see if we were feeling it, but within minutes of sitting down he was all over me. I actually got pushed into the corner of the couch with him grinding on top of me!

I have housemates, so once it got a bit too X-rated, I literally grabbed him (to his delighted squeals), carried him to my room, and threw him into my bed. We made out for a bit but I called pause so I could set up the cameras.

Before anything else, I had him film an intro about what he was looking for and to say hi to his girlfriend. Then we started really slow, totally clothed, with him laying back on the bed. I put my weight to use to pin him and kissed him all over, working my hands under his clothes.

Once he was a little warmed up I straddled him and we started taking off some layers. Soon I slid down his skinny jeans down his skinny legs, revealing lacy black underwear. I kissed my way back up his legs and gently kissed his cock through the fabric, then moved my mouth along his hipbones, slowly and gently.

…until I grabbed his hips and hoisted his thighs over my shoulders, lifting his whole ass off the bed. I rolled his underwear down to expose his neatly trimmed pussy and gave it another gentle kiss, then shoved his legs together and forced his ass up into the air.

I held him up in the air like that while I sucked and licked. He’d never had anyone go down on his cock and started gasping immediately at the sensation of my tongue. I kept him lifted up and went down on him for about ten minutes in that position. He came at least three times, with my hand on his throat towards the end.

After the last orgasm I gave him a kiss tasting of himself while he wrapped his legs around my bare back. I sat back upright, then pulled him into my lap and worked on taking off the rest of his clothes. He ground his nude body against my black jeans and I leaned in to whisper to him:

“You’re gonna suck my cock, then I’m going to fuck you raw, and then I’m going to cum inside of your cunt. Is that what you want?”

“Yes, please…”

I lay back on the pillows while he unbelted my jeans, then straddled me. He slid down and kissed my chest the whole way while I stroked his hair. My jeans got pulled off first, and then my underwear – he gasped when my cock flopped out and immediately leaned in to give it a loving kiss, then to take it into his mouth.

I desperately wanted to take his virgin boypussy, so he only went down on me for a few minutes before I pulled him upwards to straddle me again, grabbing his ass and brushing against his clit from behind. I asked if he was ready, and he responded by grabbing my shaft and lining it up to slide against his thick labia.

I sucked on his nipples while he slid along my shaft, getting it slick. When I was as wet as him, I grabbed his wrist forcefully and placed his hand back onto my bare cock. He eagerly moved it into position and sat back, working the head into himself.

Even that took a minute to adjust, and he just gently rocked back and forth with it only partly inside of him. He leaned in for a kiss and I started helping gently, pushing my own hips upwards to go a bit deeper. As he started to ride me, I gave his soft ass a deep squeeze and told him: “This is what your cunt is made for.”

Once he’d gotten used to having a cock inside him, I pulled him down to lay his chest against mine, so I could kiss his neck and whisper instructions into his ear. I pulled out, then grabbed him and moved him to lay on his belly on the edge of the bed with me on my knees behind him.

I pulled him up by his hair to face the camera, and per my instructions, he started talking to the camera:

“Hi, [girlfriend]!”

“I feel like such a slut, I’m a whore!”

“I love you, [girlfriend]!”

Meanwhile I fucked him bareback from behind, and started being a bit rougher. I fingered his mouth while I thrust, roughly grabbed his chest, and even used my arm to choke him. But I was still gentle and made sure to kiss him all over too.

We stayed in that position a while and worked up to enough speed to make the bed creak. When I felt he was ready, I sat upright and pulled him into my lap forcefully. I grabbed his chest roughly from behind, choked him, and slapped his engorged cock. After some more teasing I fucked my way back into him, making him bounce up and down in my lap while I held him from behind.

He was quite tight, and when I slipped out he turned to face me and got back on while holding on to me. I grabbed him, lifting him most of the way off the bed into a squat and holding him tight to my chest while he rode me and milked my bare cock.

At this point I was getting close, so I threw him onto his back and pinned his thighs against his chest. I put my whole weight against him, slid my dick back into his cunt, and whispered in his ear that I was going to fill him and make him mine.

“Please, please, please give it to me, please, please”

Who can say no to that? My whole body tensed to thrust deeper and faster until I fucked a week-long load of cum deep inside his unprotected boycunt, claiming it as mine.

After I came I stayed inside of him and leaned down to kiss him gently, still gently rocking my hips. I kept my half-hard cock filling his cunt for another minute or two until I pulled out. He stayed on his back and kept his legs raised up – not a drop spilled out. And he had the biggest smile on his face the whole time.

We cuddled a while afterwards, listened to music, and even napped a bit. But he enjoyed his first time enough that I fucked him three more times that date. I only sent him home after a second deep creampie.

We’ve since hooked up a few more times and plan to keep doing so; and I made sure he looked into birth control and STI testing. And I know his girlfriend is okay with me using his holes this way because she gets to watch every video. Now that’s a success story!

Source: reddit.com/r/gonewildstories/comments/tcu723/mt_breaking_in_a_strangers_boyfriend