When I was 24, I was 100% closeted. I was in a relationship for about 6 months with a girl (22) and enjoyed having sex with her. We were out day drinking for St. Patty’s day, and met up with a couple of her friends, who both happened to be lesbians. After drinking all day, we went back to her apartment and fucked for a while. Out of no where, she told me she had hooked up with both of her friends we had met up with earlier when they were in high school and college. I was shocked, but also extremely turned on. I don’t know what took over me, probably the alcohol, but I decided to tell her that I really enjoyed hooking in with guys, specifically older men. I told her I had been with a few before but not since her and I had started dating. She was in complete shock but told me that it really turned her on. She asked if I wanted to hook up with a guy now which definitely caught me off guard. I told her I would if she wanted me to, and she told me she didn’t want to stand in my way.

I grabbed my phone and downloaded Grindr and logged in. She told me she wanted to pick someone out for me, so I gave her my phone. We set my age to 50 because that’s what I preferred in men. She went through messaging quite a few guys, she lived right outside of Cleveland so there were plenty to choose from. After messaging with a few for about an hour, with a little bit of my input of course, she picked the one she wanted me to hookup with.

He was 59, a little over 6ft, a bit of a belly, and a really nice cock and balls covered in a little bit of gray hair. She picked the perfect one. She asked where we should meet, and I was in no condition to drive. She was nervous about a random guy coming to her apartment, which is totally understandable. She messaged the guy and asked him if he knew anywhere to meet. He offered to cover the cost of an Uber for me, so we were all set.

My heart was racing as I kissed her bye and walked down to the Uber. After about a 20 minute drive I was dropped off in his driveway. I knocked on the door and was let inside. He offered me a drink but I said no because I was already pretty buzzed. He sat down in the couch and I sat next to him. He said “so, your girlfriend put you up to this?” I said “yea it was her idea.” He laughed and said “well get to it then” and I dropped down off the couch to my knees and positioned myself right in front of him. I pulled down his shorts and started sucking his cock. I switched back and forth between his cock and his balls, licking and sucking them both. After a few minutes I could feel him already getting close. So I pulled my mouth off and just slowly stroked his cock for awhile. After a few minutes he was getting impatient and told me to start sucking him again. I did as I was told and not 60 seconds later he was shooting a load in my mouth.

I kept him in my mouth until I started feeling him go soft. I pulled back and smiled. He said “I’ll order another Uber if you want to go wait outside” and he stood up and walked into what I was assuming was the bathroom and shut the door behind him. I was extremely confused, and a little disappointed. I stood up and walked out the door. After waiting outside for at least 30 minutes I began to realize he definitely didn’t call an Uber. So I ordered one for myself and waited. When I got in the Uber I texted my girlfriend to let her know I was heading back already and explained what happened. She didn’t respond so I figured she must’ve fell asleep. Boy was I wrong. When I got back to her place I walked in to see her 69ing with one of her friends we were just out with. I smiled and let her have her fun, went to her bedroom, jerked off, and fell asleep.

After that, she was always asking to find older men for me to hookup with. She even downloaded Grindr on her phone and logged into my account. We’d be out having a few drinks and she’d smile and say “I found someone for you and he’s on his way here now.” Or just chilling on the couch watching shows and she’d tell me to prep my ass in the shower tonight because she found another guy for me. She was basically my pimp.

Then one night she was in the shower and I was browsing Grindr. Up popped a profile about 100 feet away. I clicked on it and discovered my girlfriend had already been messaging this guy a few days before. I read back through and learned a few things. He’s 65, retired and divorced, kinda heavy set, he has an extremely nice cock, and… he just moved into the same apartment complex as her! She was telling him about me, and told him that she wanted me to be a regular cock slut for him, and that she could even convince me to wear a pair of her panties for him!

And she was right. This man ended up fucking me two or three nights a week, some times multiple times in one day. And yes, most of the time I was wearing one of her thongs. There were multiple occasions where I would go over to his apartment, suck his cock and let him fuck me for hours, and go back home without even telling my girlfriend I was there.

Her and I dated for another 8 months or so, and this went on the entire time. She must’ve found over 50 or 60 guys around Cleveland for me to hookup with. Damn was that fun.