When I was 11 I went to a sleepover with 3 other boys. I was an outcast after most of my school had at least heard rumors of me needing diapers for my medical / bowel issues. These boys were my closer-ish friends before all that and I had even confided in them about getting daily enemas and fingers up my butt, the doctor tests I had, etc. After the rumors circulated they kept me somewhat distant, but I was excited to hopefully get back into their social graces with an invite to this sleepover.
Once it got later into the night, the conversation turned to things I had never heard of. “boners” and “jizz” and “jacking off.” They had all started rubbing themselves and caught on to the fact that I had no idea what they were talking about.
When they pressed me for times I had experienced what they described, I realized boners and jizz were what was becoming a very common result of the enemas from my mom. My shyness gave me away and they honed in to figure out what I was hiding. They convinced me to take off my diaper and rubber underwear so they could stick a finger in my butt and try to get me off. My mom had told me not to take off my diaper or rubbers under any circumstances at this sleepover knowing my accident risk, but peer pressure got the better of me. The boy whose house it was found a rubber glove and vaseline, and they had some light up toy not designed for sexual activities, but it gave off a very strong vibration they would hold to themselves.
They asked when my mom had last cleaned my butt, and sniggered when I told them it was right before I went to the sleepover. I stripped down to my converse sneakers and they had me get on my back. One boy held my feet / legs up and back, another dipped his gloved fingers in the vaseline and started rubbing my anus, and the last had my erection by the shaft and started pressing the vibrating thing to the head.
Naturally, it felt amazing. I gasped and squirmed when the boy’s finger sunk into me. They couldn’t believe the effect it was having. I had never had a finger go in and out repeatedly and it was intense. When the boy said he thought he could fit another finger in, the other two egged him on to try. It worked and I was a squirming and moaning wreck before I shot a huge load all over myself. They couldn’t believe how strong and long I came.
Well, after the boy removed his fingers a bunch of residual enema water came with it and got on the kid’s floor (It was basically clear). He was super pissed and used my clean diaper to mop it up, then mopped my cum up off me with the same diaper. I was pretty bummed and embarrassed, now probably smelling bad but still feeling the after effects of my getting off.
When I went to put on my diaper again the boy told me to wait cause he had an idea. He left and came back with a small white cardboard tube and said his sister used these for leaks from her girl parts or something. Before I could really consider it he had it in my butt and I felt something kind of soft being pushed further in me. The tube came away and there was just a string hanging from my anus. The tampon now in my butt was expanding and it made me squirmy, but he told me to get my diaper and rubbers back on fast because he’d kill me if I had another accident.
I watched in my diaper and sneakers while they rubbed themselves recollecting all that had just occurred. The tampon felt pretty big in my butt now and that was making me feel horny again. As they neared the finish line the kid whose house it was said I still owed him for crapping on his floor (slight overstatement). I asked what I could do? He said they were going to jizz on my converse sneakers and I had to rub it in. One by one they unloaded on my poor red chucks and I spread it around until there were damp spots all over.
We all passed out not long after. I remember waking up still feeling damp and sticky in too many places. My sneakers already looked crusty. My diaper was cold, full and heavy, but I learned that was because one of them poured more water down it while I was asleep.
The boys only associated with me sparingly after, more than before, but they didn’t want to risk becoming outcasts themselves. A couple months go by and I get another invite from the same boy for a sleepover at his house. Desperate for social standing I went but it was only us two. We played video games til his parents had long went to bed. He told me he had something he wanted to try if I was down. He pulled out a nudie mag with guys fucking each other. He told me he figured since my mom cleaned my butt and I obviously liked things in it… I was hesitant, but he said “cmonnn” that I still owed him for the mess I made last time and him keeping all my secrets. I caved and agreed under the pressure.
I stripped to my sneakers again and he got out the vaseline and started coating his erection. I told him to use a lot and he did. He double checked that my mom had just cleaned out my butt (she had). He had me get on all fours and he got behind me. I felt his slick erection poking at my anus while he grabbed my hips and slowly pulled me into him. After his head popped in he waited for a second before sliding the rest of the way. My gasps and moans gave away what I thought of the sensation. Feeling him pulse and twitch inside me was another level. He held the same light-up vibrating toy to my erection and I clenched on him which made him moan. He sped up when I clenched and I felt myself nearing orgasm. He kept going while I clenched on him and I jizzed hard into the towel beneath me. When I finally started to come down he was still going strong. My dick and butt were feeling pretty sensitive now and I was getting squirmy but he kept speed and wrapped one arm under me to keep me centered in front of him. He started to whimper and I thought I felt his dick spasm before he stopped. He got me off my elbows and told me to try and hold it while he went to get another tampon. I got into the best position I could to try, but when he pulled out even more residual enema water now mixed with his cum fell out onto the towel and my sneakers beneath my butt. He laughed and said “dang, you really do need that diaper.” He got the tampon into me again as I started to feel it expand. I got my diaper back on and apologized about the towel. He said it was fine, he’d just tell his mom I had an accident. I begged him not to because then she’d tell my mom, but that’s what he did. My mom said no more sleepovers after that, but that was the last one I was invited to anyways.
The other 3 boys still kept me at arms length, but would tease me some privately about what we got into for a while. Rumors spread about me being gay and liking it in the butt (which was ill perceived by kids that age at the time) and I always figured it was them trying to climb the social ladder at my expense.