Intro to Cuckoldry

literotica
literotica
8 Min Read

It actually started with him telling me that he’d slept with guys in the past and that he’d like to do it again. As he’d only seen him act dominant sexually, I really liked the idea of seeing him submit to another man. Initially, he was uncomfortable with me being there in person, but as I got to know the guy he was messing around with (A handsome, closeted bi man in his mid-fifties) I started receiving pics of my boyfriend sucking his cock or bent over a couch, cheeks spread, asshole open from being freshly fucked. This, I later learned, was my boyfriend’s idea, even though they were from the man’s phone. Then, as I was home alone one night my bf claimed to be working, I got a text with a website, username, and password. I logged on and a live stream from a webcam appeared. The bedroom it featured was only empty for a second before I saw my boyfriend walk in from a door across the room, naked and wet, he hopped onto the bed.

The man entered with a towel wrapped around his waist and as he passed the camera, he threw it off, revealing a flaccid penis bigger than any I’d seen in real life. I could tell he’d known I’d be impressed with his cock by the way he smiled into the camera. As he approached the bed, my boyfriend eagerly crawled towards him, opened his mouth and looked up at him with doe- eyes as the man fed his cock to my boyfriend. A few minutes later the man looked at the camera, winked, and like he weighed nothing, flipped my boyfriend onto his back and around so his ass hung off the bed. Finally, I could see the man’s hard cock unobstructed. It was bigger than I’d imagined it would get, with its foreskin pulled back exposing a head like an apple. I could only see it for a second before he grabbed it with one hand, pushing my bf’s legs above his head with the other, and expertly fitting it into my boyfriend’s asshole.

Later that night I got a text from the man saying “Hope you liked the show, no need for … to know”. This started us chatting behind my bf’s back. Mostly about the two of them fucking and whatever. Each time he’d text, I’d picture his massive cock. After about a month, I got a picture message from him. It was of his soft cock. The message read “need some help here”. I couldn’t believe it, we’d never talked about anything sexual that didn’t involve my boyfriend. I was at work at the time so I went to the bathroom and sent him an upskirt. Before the message was completely uploaded and sent he texted “whoops meant to send that to your bf”. It was too late and I didn’t care. We agreed to meet at his place so I told my boss I felt sick and left. I took a cab and was at his house in ten minutes. Immediately after he let me through his front door, he asks me to strip. Which I gladly did. I stood there, bare and blushing as he inspected me like you would a car. He squeezed and palmed my boobs and ass firmly. He then stuck a finger in my mouth to wet it, before putting it in my pussy. I was so wet it slid in easily. So there I was, naked in the doorway this man’s house as he fingers me, and I hear a creak behind me.

“Woops, guess we forgot to shut the door,” he says.

I couldn’t believe it, he lived on a moderately busy street, I’d guess that six to ten people had seen what was going on in the past 5 minutes. I rushed to shut it while he laughed.

“Put that skirt and top back on, I’m expecting someone”.

I did as he said even though I felt a complete lack of control. I left my panties and bra off as he said, He made me feel so comfortable. He sat me down on his couch and he sat across from me in a chair, his legs spread confidently wide. Bashfully, I asked him if I could see his penis. He undid his jeans and pulled them down but left his tight boxers. I knew what he wanted so I walked over and pulled them down. His half-hard cock looked bigger than I’d remembered. I pulled the foreskin back to reveal it’s huge head.

“That a girl,” he said as he pulled my head towards it. I complied and began to suck, enjoying the feeling of it growing in my mouth. I didn’t even hear the door open, only nearing footsteps before a voice I didn’t recognize, greeted my host. I pulled away for a second, embarrassed before he grabbed my head again and put my mouth back on his cock.

“Don’t worry, this is just Mark?” he said, as I felt the other man lift my skirt, exposing everything to him.

“Cute girl. Who is it?” Asked Mark.

“A friend” he replied.

Minutes later, they had me on my back on a massage table, Mark in front fucking my throat, while my host gently fucked my pussy.

We went for half an hour or so before my host stopped us.

“We’d better get downstairs,” he said to Mark Knowingly.

We got dressed, again, me without bra our panties, and went downstairs. We chatted for a bit before the doorbell rang, it was my boyfriend. The host explained that I’d shown up minutes before and had been invited by him for dinner. We all sat down and chatted for a bit, then the host asked my bf to look at his computer because it seemed to be acting funny. Add he did, the host asks in front of my bf if I’d like a tour of the house. I agreed and followed him and Mark as my bf stayed at the computer. Upstairs, I’m ushered into the bedroom where both men have me suck their cocks, the host eagerly eyeing the door. He then hosted me from my knees to the bed and began fucking me harder than I’d ever been before. I think it was my yelping, despite Mark trying to silence it by fucking my throat, that got my boyfriend’s attention, who walked in while I lay there, mouth and pussy filled with cock.

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