u/FearlessWorld8387

I never thought I would cheat my boyfriend…

I’ve always been super faithful in my relationships. Never even considered cheating on anyone. But this last one was already pretty rocky. Around the time it happened, we’d just gotten back together after a break, so maybe that’s why all of this ended up happening.

To try and make him happy now that we were back on, I booked a waxing session so my ass would be completely smooth for him. I always just shaved my hole at home, but this time I wanted something longer-lasting. I looked on Instagram for a guy in my city who did male waxing, found one who seemed pretty popular, and booked him.

I showed up nervous as hell because I’d never done this before, but the waxer was really professional at first.
He was tall, dark-skinned, slim but built, covered in tattoos, with a full, well-groomed beard — that alternative look, you know? He was wearing a tank top and shorts, super casual.

He was one of those guys who keeps talking the whole time so you stay distracted and feel more comfortable. It worked. I relaxed pretty quick.

He started by waxing my cock and balls, chatting about random stuff the whole time. At one point he asked if I always preferred being smooth. I told him lately I’d been keeping it that way because my boyfriend liked me completely hairless.

He laughed and said he got it — he liked his partners smooth too, but on himself he preferred more hair. Without thinking I asked, “So even though you’re a waxer, you keep it natural?” He laughed again and said yeah, he left the bush intact and just trimmed around it.
The second he said that, my brain immediately pictured it… and of course my traitor of a dick decided that was the perfect moment to get hard.

I had nowhere to hide. I was naked right in front of him. I went bright red, but he stayed completely professional and just said it happens a lot. I nodded and waited for it to go down, but it was pretty obvious what had set me off.

Once he finished the front, he told me to lie face-down on the table so he could do my ass. Still totally professional at this point. No sign anything was about to happen, even after the earlier “accident.”

He started applying the wax, but it felt different from the front. Before he’d been quick and chatty; now he was slower. He’d spread my cheeks and take his time before I even felt the wax. He’d talk, then go quiet like he was concentrating.

This was the first time I’d ever had my ass waxed, and fuck, I was in pain. Every strip made me moan from the sting, and he’d press his hand over the spot, telling me it would feel better soon, that he was almost done. Just trying to keep me calm.

Eventually he said he was finished, and he made a joke saying he bet that it hadn’t been as bad as I’d expected. I just laughed in relief that it was over. He asked if my skin felt sensitive and I told him honestly that yes, it did. Then he offered to put some lotion on to soothe it. I said yes without thinking twice.

A few seconds later he came back with the lotion and started applying it… and that’s when it hit me what I’d just agreed to… He was literally rubbing around my hole.
By the time I realized it, his hands were already there, spreading the lotion between my cheeks and around my entrance… slow, careful, basically giving me a full massage “to calm the skin.”

There was nothing calming about it. I didn’t know what to say or do. I just stayed still, breathing deep while this hot waxer kept circling my hole, still acting like it was pure professionalism, just part of the service.

The massage kept going. Time passed and I still couldn’t bring myself to say anything, “stop, is it done yet, i think that’s enough”… nothing.

After a while I started feeling light pressure against my hole while he rubbed. I knew exactly what was about to happen and still… I couldn’t speak.

He asked if my skin felt better. I said yes, almost moaning. His voice had dropped low, almost a whisper, telling me the lotion was really good, that it left the skin soft and hydrated.

While he was saying that, the pressure got stronger… and finally my hole gave way. His finger slid in slow and I couldn’t hold it in… a deep moan came out as I felt him inside me.

The vibe had completely shifted, but he kept going like nothing had changed, still playing the professional while his finger moved in and out of my ass. All I could do was moan. The whole situation felt insane and so fucking good at the same time.

He kept saying this would leave my skin calmer and healthier, and I just agreed, clearly letting him finger me. In that moment I wasn’t thinking about anything outside that room, least of all my boyfriend.

Soon he added a second finger and started opening me up. That’s when the moaning really started. He’d ask if I was feeling better and I’d just nod, both of us still pretending this was somehow part of the service.

With two fingers inside me, he said there was something else he wanted to use to make me even more relaxed and comfortable. I just agreed. I heard him step away, opened my eyes, and came face-to-face with the huge bulge in his shorts right in front of my face.

He didn’t say a word. Just kept fingering my ass with one hand while the other slowly pushed his shorts and underwear down… and his cock sprang free. Thick, heavy, probably around 8.3 inches, uncut, noticeably bigger than my boyfriend’s 6.7. And hairy… exactly as bushy as he’d described, the thing that started this whole mess.

He started stroking my head and guiding his cock toward my mouth. There was no resisting. I started sucking him like I was in a trance. The musky smell of his bush in my nose, his hand in my hair, his fingers still stretching my hole. I was on fire.

After a while of sucking him, I felt his fingers pull out. He climbed onto the table and got on top of me, cock lined up with my ass. He pressed the head against me and whispered something I really wasn’t ready for: that this would get me nice and ready for my boyfriend…

Right then I remembered my boyfriend existed… and right then he started pushing in. That thick, massive cock stretching me open in a way I hadn’t felt in a long time.

All I could do was grip the table and moan. His thrusts left me breathless, his weight on top of me. And the whole time he kept talking shit… saying my boyfriend was going to love how I looked… that he finally understood why my boyfriend liked me smooth…

Every word was both a reminder of how wrong this was and how much I was loving every second. The guilt was completely buried under how good it felt.

He fucked me slow and deep for what felt like forever. Hard, full strokes until I barely remembered where I was. He kept going until he came right against my hole. I can’t even describe how out of it I was by the end.

When he finished, he got off me, grabbed a wipe, and cleaned me up like a true professional. Then he helped me sit up and kissed me, saying he was sure my boyfriend would be happy with the result. I couldn’t even think straight, still completely gone from the fucking and now the kiss.

I got to my car completely dazed and exhausted. And of course the second I checked my phone, there were messages from my boyfriend.

There he was, asking how it went, if I’d been embarrassed, and requesting the photo of the result that I’d promised to send him.

I just texted back that I wanted to surprise him and he’d see it in person the next day when we met up. He called me a tease and said that was even better, that he couldn’t wait.

I just breathed a sigh of relief. Because if I’d sent a picture of my ass that day, there would’ve been no hiding it. He’d have seen right away that my hole wasn’t just smooth… it was completely swollen and stretched from taking another man’s cock.

reddit.com
u/FearlessWorld8387 — 2 days ago

Just joined here and I need to tell about my first time cheating

Guys, I just joined the sub and figured I’d share the first time I ever cheated on a boyfriend.

I’ve always been super faithful in my relationships. Never even considered cheating on anyone. But this last one was already pretty rocky. Around the time it happened, we’d just gotten back together after a break, so maybe that’s why all of this ended up happening.

To try and make him happy now that we were back on, I booked a waxing session so my ass would be completely smooth for him. I always just shaved my hole at home, but this time I wanted something longer-lasting. I looked on Instagram for a guy in my city who did male waxing, found one who seemed pretty popular, and booked him.

I showed up nervous as hell because I’d never done this before, but the waxer was really professional at first.
He was tall, dark-skinned, slim but built, covered in tattoos, with a full, well-groomed beard — that alternative look, you know? He was wearing a tank top and shorts, super casual.

He was one of those guys who keeps talking the whole time so you stay distracted and feel more comfortable. It worked. I relaxed pretty quick.

He started by waxing my cock and balls, chatting about random stuff the whole time. At one point he asked if I always preferred being smooth. I told him lately I’d been keeping it that way because my boyfriend liked me completely hairless.

He laughed and said he got it — he liked his partners smooth too, but on himself he preferred more hair. Without thinking I asked, “So even though you’re a waxer, you keep it natural?” He laughed again and said yeah, he left the bush intact and just trimmed around it.
The second he said that, my brain immediately pictured it… and of course my traitor of a dick decided that was the perfect moment to get hard.

I had nowhere to hide. I was naked right in front of him. I went bright red, but he stayed completely professional and just said it happens a lot. I nodded and waited for it to go down, but it was pretty obvious what had set me off.

Once he finished the front, he told me to lie face-down on the table so he could do my ass. Still totally professional at this point. No sign anything was about to happen, even after the earlier “accident.”

He started applying the wax, but it felt different from the front. Before he’d been quick and chatty; now he was slower. He’d spread my cheeks and take his time before I even felt the wax. He’d talk, then go quiet like he was concentrating.

This was the first time I’d ever had my ass waxed, and fuck, I was in pain. Every strip made me moan from the sting, and he’d press his hand over the spot, telling me it would feel better soon, that he was almost done. Just trying to keep me calm.

Eventually he said he was finished, and he made a joke saying he bet that it hadn’t been as bad as I’d expected. I just laughed in relief that it was over. He asked if my skin felt sensitive and I told him honestly that yes, it did. Then he offered to put some lotion on to soothe it. I said yes without thinking twice.

A few seconds later he came back with the lotion and started applying it… and that’s when it hit me what I’d just agreed to… He was literally rubbing around my hole.
By the time I realized it, his hands were already there, spreading the lotion between my cheeks and around my entrance… slow, careful, basically giving me a full massage “to calm the skin.”

There was nothing calming about it. I didn’t know what to say or do. I just stayed still, breathing deep while this hot waxer kept circling my hole, still acting like it was pure professionalism, just part of the service.

The massage kept going. Time passed and I still couldn’t bring myself to say anything, “stop, is it done yet, i think that’s enough”… nothing.

After a while I started feeling light pressure against my hole while he rubbed. I knew exactly what was about to happen and still… I couldn’t speak.

He asked if my skin felt better. I said yes, almost moaning. His voice had dropped low, almost a whisper, telling me the lotion was really good, that it left the skin soft and hydrated.

While he was saying that, the pressure got stronger… and finally my hole gave way. His finger slid in slow and I couldn’t hold it in… a deep moan came out as I felt him inside me.

The vibe had completely shifted, but he kept going like nothing had changed, still playing the professional while his finger moved in and out of my ass. All I could do was moan. The whole situation felt insane and so fucking good at the same time.

He kept saying this would leave my skin calmer and healthier, and I just agreed, clearly letting him finger me. In that moment I wasn’t thinking about anything outside that room, least of all my boyfriend.

Soon he added a second finger and started opening me up. That’s when the moaning really started. He’d ask if I was feeling better and I’d just nod, both of us still pretending this was somehow part of the service.

With two fingers inside me, he said there was something else he wanted to use to make me even more relaxed and comfortable. I just agreed. I heard him step away, opened my eyes, and came face-to-face with the huge bulge in his shorts right in front of my face.

He didn’t say a word. Just kept fingering my ass with one hand while the other slowly pushed his shorts and underwear down… and his cock sprang free. Thick, heavy, probably around 8.3 inches, uncut, noticeably bigger than my boyfriend’s 6.7. And hairy… exactly as bushy as he’d described, the thing that started this whole mess.

He started stroking my head and guiding his cock toward my mouth. There was no resisting. I started sucking him like I was in a trance. The musky smell of his bush in my nose, his hand in my hair, his fingers still stretching my hole. I was on fire.

After a while of sucking him, I felt his fingers pull out. He climbed onto the table and got on top of me, cock lined up with my ass. He pressed the head against me and whispered something I really wasn’t ready for: that this would get me nice and ready for my boyfriend…

Right then I remembered my boyfriend existed… and right then he started pushing in. That thick, massive cock stretching me open in a way I hadn’t felt in a long time.

All I could do was grip the table and moan. His thrusts left me breathless, his weight on top of me. And the whole time he kept talking shit… saying my boyfriend was going to love how I looked… that he finally understood why my boyfriend liked me smooth…

Every word was both a reminder of how wrong this was and how much I was loving every second. The guilt was completely buried under how good it felt.

He fucked me slow and deep for what felt like forever. Hard, full strokes until I barely remembered where I was. He kept going until he came right against my hole. I can’t even describe how out of it I was by the end.

When he finished, he got off me, grabbed a wipe, and cleaned me up like a true professional. Then he helped me sit up and kissed me, saying he was sure my boyfriend would be happy with the result. I couldn’t even think straight, still completely gone from the fucking and now the kiss.

I got to my car completely dazed and exhausted. And of course the second I checked my phone, there were messages from my boyfriend.

There he was, asking how it went, if I’d been embarrassed, and requesting the photo of the result that I’d promised to send him.

I just texted back that I wanted to surprise him and he’d see it in person the next day when we met up. He called me a tease and said that was even better, that he couldn’t wait.

I just breathed a sigh of relief. Because if I’d sent a picture of my ass that day, there would’ve been no hiding it. He’d have seen right away that my hole wasn’t just smooth… it was completely swollen and stretched from taking another man’s cock.

reddit.com
u/FearlessWorld8387 — 7 days ago