I have been chatting with this ‘straight’ guy on a dating app for almost a year already. We would usually talk about his ‘bottom bitch’ fantasies. I am quite adventurous, and it’s been a while since I was dominant at sex. For months, we’ve been talking about meeting up and fulfilling his fantasy. But every time we set a date, something would always come up leaving us with no choice but to cancel. Until last night when all the stars lined up for us to meet.
He came in our flat looking a bit anxious. It was the first time we met face-to-face. I reassured him that no one is going to bug us, my roommate is on holiday for a few days in India. We talked a bit about the weather, work, and other awkwardly boring stuff before heading to my room.
We sat at on the foot of my bed and I asked him, “Now what?”. He said, “I am a bit stressed, would you mind giving me a massage?” I tried to keep myself from rolling my eyes and begrudgingly replied, “Okay.”
He took off his clothes, I got a little excited after seeing him wearing a g-string. He laid on his stomach on the bed as I stripped into my boxers and reached for the lotion. “I’m not a pro,” I told him. “It’s alright,” he said and then closed his eyes. I know some stuff about rubbing backs (I worked in a rehab clinic a few years back) and applied my ‘skills’ on him.
I rubbed his back, going down until I reached his butt. “Looks tasty,” I whispered while squeezing it. I ran my finger between his butt cheeks, and then reached in front to his package with my other hand. I felt something smooth over his pecker, like plastic, and asked, “Are you wearing a condom?” He looked back and said, “Yes. I don’t want to stain your sheets with my cum.” I just stared at him in disbelief, but I don’t think he noticed it since my room was dimly lit. “Do you want me to remove my underwear?” he asked. I said, “NO. I will remove it if I want to. You’re my slave tonight, remember?” I then lightly spanked his butt. He moaned.
I then proceeded to eat his hole while rubbing his engorged, wrapped-up package.
Then I climbed on top of him, rubbed my pecker between his cheeks while grabbing his chest, pinching his nipples. He looked back at me and asked, “Wait, you’re not wearing a condom?” I scoffed and said, “Really? I’m not even putting it in.” I got up and asked, “Do you want me to use the toy?” I showed him my toy, he said, “It’s too small.” He then got up and searched for his shorts. “Did you bring a toy?” I asked. He nodded and then handed me an 8-inch cucumber with a condom on it. “Have you tried to fuck yourself with this one before?” I asked, puzzled. He said yes and then laid on his belly again.
I applied lube on my fingers, inserted my index finger in his hole. I tried to be very gentle, one finger, and then two fingers, three…four… “Wow, you’re hole is huge,” I exclaimed. “Do you like it?” he asked. I didn’t answer back anymore since I got busy reaching for the lube.
I applied a good amount of it on the cucumber. “Open up,” I ordered. He spread his cheeks open, I gently inserted the tip of the cucumber in his hole, he clenched, “OPEN UP. Relax,” I said, a quarter of the cucumber was already inside. I then gently advanced it through. “Put it ALL in, please,” he begged. “No… I don’t want you to go to the ED because a cucumber’s stuck up your butt,” I plainly said. I continued on pegging him with the cucumber while rubbing his balls. Whenever I advance my hand up his cock, he would stop me.
I got bored and asked, “You’re such a trooper, do you want me to take a photo of this cucumber up your butt?”
He then immediately got up, startled, and said, “Where’s your phone? Are you taking pictures?”
I pulled out the cucumber, and told him, “Chill, man. No one’s taking pics. I just asked since I reckon this is a ‘milestone’ for you.”
He stood up, I felt something drop on my finger. I looked at the brown, sticky, matter on my finger and said,
“Shit.”
He asked me what it was? I just said, “Your shit.”
The room was dimly lit but I could swear he turned red all over. “Would you be a dear and hand me the tissue roll?” I asked. “I’m really sorry, I swear I cleaned up before coming here,” he apologized. I wiped the shit off my finger, got up and told him, “I’m really not into this stuff. I will just wash, please stay here.” I threw the cucumber in the bin and headed to the bathroom to wash my hands.
When I returned, he was already putting on his clothes, embarrassed with what just happened. I then proceed to put on my clothes, asked him if he needs to use the washroom. “Can I just wash my hands,” he asked. “Sure.” I led him to the washroom. He endlessly apologised for the incident, I just told him, “No worries. Shit happens.”
I don’t know if I’m still gonna meet up with him after this. Not because of the little ‘accident’, but mainly because he never gives me the chance to enjoy the sex too.
Source: reddit.com/r/gonewildstories/comments/7tv8m1/pegging_gone_wrong_mm
For someone that’s expanded his ass that much, he seems terrified of getting STDs, even from a cucumber. Between that and not cleaning himself out, not much of a keeper there unless he could relax.