Jacob was caring with Michael. I think he really fell in love with him.That all changed after about six months when Jacob stabbed another inmate and was sent to another jail. Michael then got another cellmate. His name was Big Bob. Big Bob was ripped and had a temper on him. Michael would show him what he could do with his mouth. Bob liked the blowjobs, but he wanted to have sex with Michael. He was a little rough with him. I think he got off on that kind of a thing. Michael knew that Bob wanted his ass. He accepted that he’d get fucked. He just didn’t know when or where it would happen.Michael had laundry duty and Bob and his crew entered the room. He told Michael he wanted his ass. Michael was okay with it. Bob’s crew looked out for the guards. Michael took his jumpsuit off and assumed the position. Bob slid on a condom and squeezed some lube onto Michael’s asshole. He slowly entered Michael’s asshole. He was extremely tight, and it took many tries before slamming his dick up. I gradually got her to express her self and we started slowly together into the lifestyle, and it's been an amazing time with so much more in our future. This story, however, focuses on one particular "first" for us: my wife's first time fucking another man in front of me.It was just over 2 years ago. My wife had already watched me with many other women (one of her biggest turn-ons, more on that later) and we had a few threesomes with women, but now she and I were finally ready to have her experience another man.Together we decided that we would find someone online, a stranger with no attachment, for this experience. Once we created a Tinder profile for her it wasn't long before we had to start sorting through dozens of guys. We finally settled on one who seemed chill and wouldn't get attached, and he knew the situation: he'd be with a married woman and I'd be there to watch. We also had a few ground rules: light rough play was ok but nothing extreme (since we just met him), no anal,.
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