(This is a true story. All participants involved were consenting adults in their late 20s who enjoyed themselves very much.)
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Several years ago, I started seeing a woman who was cheating on her boyfriend. I didn't know it at first, but, after fucking for a couple weeks, she came clean. She said she'd been unhappy for some time and that she'd cheated on all her previous boyfriends. When she told me that, I knew two things. One, that I wanted her to cheat with me more. And two, that I wanted her to leave him, date me, and cheat on me. I'm a switch, and, sometimes, my fantasies get terribly complicated and vary widely. Sometimes, I want to be the bull ruining a taken woman's cheating holes. Other times…
…I want to be a humiliated, pathetic cuckold. I want to be put in my place.
So, when I say that I hoped she'd cheat on me, I meant it. I told her about my fantasies, and that I'd love it if she did it. And she did cuck me once; maybe I'll post that story another time. However, for her, and I didn't know this at the time, her thrill from cheating came from it being secret, taboo, and decidedly not consented to.
She did end up cheating, quite a bit actually. Sometimes, that turns me on, but I am much more interested in being an active party to the plans – even if it's after the fact and confessed to. That all said, she was not interested in me knowing anything, me being a cuckold, or anything open of the sort in spite of my admissions.
I had to take matters into my own hands.
Prior to that relationship, I had never been faithful in others. I cheated near-constantly in one relationship, and regret nothing. I also learned how to find people to cheat with. Finding someone to cuck me shouldn't be that hard? Right?
That search was eternal. At least, it felt that way. Sure, there was an excitement in sneaking peeks at my phone to check various apps I was on. It even made me empathize with her desire for that clandestine lust. But, sheesh did it take forever. I guess it shouldn't be surprising that not many people want to share something so private with someone perverse stranger.
Then, it happened by accident. I slipped up at work and a coworker saw my dating app on my phone. She knew I had a girlfriend, and immediately drilled me about it at a happy hour a couple days later. I was so scared she'd say something, and she sure acted like she was judging me for cheating. We'd been drinking and I spilled my guts. I told her I was cheating because I had fantasies I wanted fulfilled.
She inquired.
"I want to be made to watch."
"Watch what?"
"A couple."
"A couple? Fucking?"
I nodded.
"Why?"
"Because…" I don't remember what I said next, but I'm sure I said I wanted to be humiliated. I know I told her about wanting to be a cuckold, to almost be the object of ridicule for someone else's pleasure.
She pulled out her phone like she wasn't listening, but she most definitely had. Before I knew it, she was showing me a text exchange with her then-boyfriend (now-husband). The phrase "Bring the bitch-boy home," is gonna be stuck in my brain forever.
I texted my girlfriend that happy hour was going to go late and to figure out her own dinner plans. I was trembling with excitement. I am surprised I could drive or follow her car back to their apartment complex.
I suppose I should describe her. She was a couple years older than me. She was not my hottest coworker, but she definitely wasn't unattractive. She was slender, ran most days, and always came across as a little too into running. Her vibe was almost granola blonde who spends too much money at Whole Foods. I knew she was recently divorced, shared custody, and that she'd had an affair, but that she wasn't seeing either her ex or the former AP anymore. I knew nothing about her boyfriend.
He didn't look that different from me. He had an average build- but in slightly better shape than me, a beard like me, but was a couple inches taller than I was. His vibe wasn't too dissimilar from hers, and was very welcoming when she and I arrived.
Then he blurted out, "So, why should you get to watch me fuck my girlfriend instead of being a cheating loser who either isn't fucking his girlfriend or doesn't deserve to?" I'm paraphrasing, but it was something to that effect. It also had an effect on my cock which she noticed.
"He's already fucking hard." She was giggling. We were straight into it, for sure.
He grabbed my shoulder like I was his best friend, and said, "The safe word is purple. If we say or do anything you don't like, you say that. Got it?" I was quite familiar with the concept, but I enthusiastically nodded. "Excellent. From now on, you speak when spoke to, bitch-boy." He pointed to a cracked doorway. I could see a red light on in there. "Bedroom," he commanded. "You'll see a chair. Take a seat."
She followed me to the bedroom. When I sat down, she stood in front of me. "Is there anything absolutely off-limits?" I asked what she meant. "You're good with name calling?" I nodded. "Being denied? Begging? Humiliation? Male-male contact? Cumplay?"
I said that I didn't want to touch or be touched by him. "I don't want cum in my mouth, if that's what you're asking," I added. My girlfriend had made me taste and swallow my own cum before when we would do some humiliating play, and that I wasn't fully opposed to. "But I might be open to some limited cum-play in the future," I added.
"I should smack you for assuming there will be another time, you cheating asshole."
I said "Fuck," under my breath, which she immediately picked up on.
"You'd like that?" I nodded. Whack! My cheek was stinging and my cock was throbbing. "Open." I opened my mouth. She bent forward and spit, really, at my mouth. Some landed on my cheek and nose, but most in my mouth. She giggled, "I had no idea you were such a little bitch!" She shouted for her boyfriend. "Swallow," she commanded, and I did. "Don't wipe the rest off." When her boyfriend saw the spit on my face, he laughed too. She told him my limits and then everything really got started.
They took their time. They made out. Squeezed each other. Made fun of me. It felt like it took forever for them to get naked. I've never had any kind of cock-envy, but when she dropped to her knees to suck his, I could have turned completely green with jealousy. He commanded me to take my clothes off and retake my seat. "Absolutely no touching unless either she or I tell you to. And if we say stop, you stop," he ordered pointing at my hard cock. It was dripping precum already. It was going to be the long night I had hoped for… That I'd been craving.
My phone, which I had set on the arm of the chair lit up. My girlfriend had texted me. I looked down at it and was about to pick it up, when my coworker noticed and took my phone away. "If you don't want to be with her now, then you don't get to talk to her now either."
Can you tell that it was incredibly hard for me not to touch my cock in that moment?
Fortunately for me, they let me touch it. Slowly. She watched as she stood up. He laid on the bed with his legs hanging off. I wasn't far from the bed; if I reached out I could have easily touched his leg. She climbed on top of him to 69. I don't remember exactly what she said, but it was something like this:
"Listen to how I moan when he licks me. I bet you have never heard a woman make sounds like this for you. Watch how I suck his cock. I'd imagine you'd like your girlfriend to suck a cock like I'm gonna suck his. You'd like to watch her do that too. You don't deserve for her to suck your cock, do you. Nod yes or no, and it better be 'No.' He's not going to cum from me sucking his cock. He is a real man, not like you. He'll cum when I want him to. So will you. Well, if I want you to."
I was floored. Had she or they done this before?!
"Stop touching yourself." She began to suck his cock. She drooled, spit on it, stroked it with her hand, she gagged. She also very vocally let him know that she liked what he was doing with his tongue and hands. I imagined he'd stuck a finger in her asshole at one point; he would later when she rode him.
I am going to gloss over much of what happened because this story is already running long. She repositioned herself to ride him while facing me next. He was largely quiet, but she verbally let me have it. She spun around and rode him cowgirl after that. That was when he stuck a finger in her ass. It gaped a little. "I bet you'd love to taste that," he said to me. He was looking me directly in the eye when he said, "You can't. Cuck."
They got off the bed, and she bent over. He stood between me and her, fucking her from behind. "I love your cock. I'd never fuck a cock like his." Size-wise, we weren't too dissimilar. His was longer by an inch or so, but mine was thicker.
"I'll never let you fuck a cheater's needy dick," he told her. "He probably likes looking at my ass right now anyway."
She implied that I wanted to suck his cock, she could see it when I was watching her suck it she claimed. While that's not my thing, which I had told her earlier, the way they said it was degrading in the right way for the moment.
While this was all going on, they would tell me to start and stop stroking my cock. There were a couple times I thought I'd cum, but it's like they could read my body language and they'd make me stop. It was the exact frustration I needed.
Finally, she stood up, "I have an idea." She came over to me and bent over the arm of the chair I was sitting in directly in front of me, across my lap practically. "Fuck me like this," she told him. "When you cum, pull out and spray it over my ass and back. Make me scream." She'd cum twice before then, and she came a third time just before he couldn't hold out any longer.
He pulled out. Thin ropes of cum shot out, maybe six in all, and the furthest shot landed just below her shoulder nearest to me. When he was finished making a mess, he tapped the head of his cock on her ass a couple times, then collapsed on the bed similar to how he'd been laying during the 69.
She must have felt cum running down her side and ass. She wiped it up with her hand and then wiped it on my bare chest. She stayed like that for a minute, spent from the fuck, like she was making me take the sights all in.
She stood up and went to the nightstand where they'd set my phone. She asked me to unlock it. She started filming me with my own phone. "Start stroking. Beg my boyfriend to let you cum. He gets to decide."
I did ask she asked. I sat there, his smeared cum drying on my chest, stroking my cock, "Please, sir, thank you for letting me come in and watch. Please let me cum." She nodded to him while keeping my phone camera pointed at me. He granted permission. Just before I exploded, she held out her other hand cupped in front of my cock. She filmed me explode into her hand. I thought my hips would shatter with how hard I came. Then she threw my cum onto me.
"You may wet a rag in the bathroom," she said pointing to the door beside their dresser. "Clean yourself up. Come up with a story for the slap mark on your face. Then get the fuck out." I cleaned myself up like she commanded. I grabbed my clothes after and dressed. "I'll see you tomorrow, bitch-boy."
He laughed after she said that, already half-asleep, "Cheating, cucky bitch-boy. See you soon. Maybe."
My girlfriend had texted me several times wondering where I was before giving up and saying that she was headed to bed. Our relationship lasted another year or so after that, and I don't believe she ever found out about it. She would cheat on me with at least three other men that I found out about. There may have been others. I still occasionally think about her cheating, and I wish she'd have let me watch or participate in some way. Either way, we wanted different things and it wasn't going to work out.
I did see that couple a handful of other times, but not for several months after the first encounter. Most came after I split up with the girlfriend. My coworker would tease me on rare occasions at work like it was an innocent inside joke she could get away with like she was toeing up to the HR line, but not crossing. If only everyone actually knew what those teases were all about.
I used to tell myself that, because I didn't touch anyone, I didn't cheat. But I'm comfortable admitting it now: I cheated to get cucked. And I loved it. And I'd do it again.
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