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Anal with my niece
Maybe this should go under Cheating since I was dating someone at the time. When I told him what happened he broke up with me.
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I'm gay and my niece has always been able to ask me anything. She told me her boyfriend had been bugging her about doing anal, and she has always hated it because it hurt. She wanted to know how I could stand it.
So I took her to my favorite "toy store" and showed her butt plugs, anal beads, and a few different sized toys that are designed to slowly stretch you out. She showed me a dildo that was as big as her boyfriend so we bought a bag of toys so she could work her way up to that and went back to my place.
We were drinking wine and I was laying out the toys and lube explaining to her what she needed to do. She pulled off her pants and said she wanted to start right now. So I had her kneel over the edge of the sofa, lubed up the smallest and inserted it. She said that one didn't hurt and wanted to keep going. I suggested we take it slowly and give her ass time to stretch out. So we spent all afternoon and all night drinking wine, eating Tapas and getting silly. We got naked together, not for the first time mind you, and she even was putting some inside me. We were having a great time.
Then she told me she thought she was ready to try the boyfriend sized one but it was still too big. She told me she wished I wasn't gay because then I could fuck her and maybe she would stretch out more. I told her an ass is an ass. She lubed up really good and I slipped it in. Her ass felt so damn nice, plus I kinda got off on playing with her titties. She said it felt pretty good, more intense than regular sex. After I shot my wad we were finally able to get the big one in, just get it in.
Then my boyfriend broke up with me. I was devastated and called her. Not to complain and whine but to let her know I didn't blame her and I will always love her as my best friend. She came over immediately and helped me pack my things and moved me in with her. That night we got drunk together and had anal. She even used a strap-on on me.
Cool Story Bro, Cooler if True.
Hope the hurt heals nicely.
I wondered how it would feel if I jacked off while something was in my ass, so I bought one of those vibrating dildos shaped like a penis. It was about 10 inches long & I could just get my fingers around its girth.
I could only get it half-way in bec it was painful & the vibrations didn't really transmit pleasurable sensations.
After 2 weeks I washed & disinfected it thoroughly, put it in its original box & dropped it into a Salvation Army bin. I hope some old lady sorting through the donations will set it aside for herself and find a use for it.
I give my wife anal and she likes it. I get her to finger my ass in the shower but I still don't get any really erotic feelings even when she probes at different angles. Maybe more practice?
At least your ass isn't in a sorry state. I hope the rest of your life catches up to it :)
Yall need Jesus.