[M]y Girlfriend [F] (now ex) Pleases Her Boss’s [M] Friend [M], When She’s Not Busy Pleasing Her Boss

See my profile for prior DECADES OF PROMISCUOUS PARTNERS true stories. This is Part 8.

After being with my ex Gina for 8 years, she’d finally turned into the total slut I hoped she’d become. At this point she’d had 5 other guys cocks in her hot little mouth and 3 of those guys also fucked her. She had just started a new job in the big city, after our recent move and within the first month, she had already gotten wild with 2 guys after the company’s Christmas party. She worked at a well-known financial institution and was rubbing shoulders with well to do folks.

After the Christmas party incident where she had sex with her manager Luke and his friend, Luke invited her to party at his place. As usual, I had other commitments so she went to the party solo. She didn’t know many people there but the guys at the party were of course happy to keep her company. She was hot as hell. 5’4, 115 lbs, small but shapely tits, a tight body, cute face, long black hair and an ass men would give their first born to have a crack at. At the party, one guy caught her eye. She told me he looks like Nicolas Cage. She loves Nicolas Cage and knows that I find him annoying so she probably made a point of saying this guys looks like him, just to fuck with me. He chatted her up at the party and asked for her phone number which she happily gave. Nothing happened between them that night but that was about to change.
The following day, he got in touch with her and asked if she’d like to come by his place for a drink in a few days. She accepted and excitedly told me should will be meeting up with him. This led to a good amount of anticipation sex with her and I. We couldn’t stop fucking each other.

The day she went to meet him, she got her damn period. She wasn’t into period sex but didn’t want to cancel on him so she decided to go anyway. She got to his fancy apartment in the evening and they had a few drinks while chatting in his living room. After he got her liquored up, he made a move and big surprise, the slut that she is, she went for it. He started making out with her in the living room and they made their way to his bedroom. She told him that she has her period so she doesn’t want to have sex but she really wants to please him. He laid on the bed and she got on top, continuing the sloppy make out session which started in the living room. She took off her top and started undressing him. She worked her way down, rubbing her tits on him, her tongue sliding down his entire body and grabbed onto his hard cock which she said is about the same size as my large cock. She gave him sloppy head as she loves to do and 20 minutes later, he came down her throat. She loved swallowing so much, I’d guess by that point in her life, she had swallowed twenty gallons of cum, mostly mine. She got home to me a short while later and in no time, my load was mixing with his, in her belly.

She was eager for this guy to fuck her so the following week, just one day after her period ended, she was on her way back to his apartment. Once again, drinks were flowing and within an hour, she was back in his bedroom, completely naked and ready to finally take this guy. She said he put on a condom which I seriously doubt. We’d made an agreement a couple of years prior that any time she sleeps with a guy other than me, she would make him wear one. When my friend Jack and I tag-teamed her for the first time, she slid his dick inside her raw, while staring me in the eye. He fucked her many times after that and not once did he wear a condom. I was fairly certain nobody was using a condom with her which was concerning because of STD’s. Pregnancy wasn’t an issue since she’s on the pill. I didn’t press her too hard on the condom thing since deep down, it was a huge turn on that she would let guys bareback her.

Anyway, after “Nicolas” supposedly put on a condom, he laid between my girls spread legs. He fucked her in the missionary position initially and then put her on all 4’s. He grabbed a fistful of her hair and pulled her head back while he went deep, which she loves. She liked to be roughly dominated. After awhile, he laid on his back and she got on top. She was riding him like there’s no tomorrow and she said he was playing with her ass a lot. Squeezing her cheeks and he slid a finger deep in her asshole. When he saw how much she liked it, he worked a second finger in, eventually making his way to three fingers. This drove her wild and she had her first orgasm. He put her back in the missionary position and started throttling her, bringing her to her second orgasm. She said they kept on making out heavily as they were fucking. She could feel him starting to tense up and knew he was about to shoot his load. She told him to cum in her which made him start moaning very loudly. He went ahead and came in my girl, supposedly into the condom. She stayed just an hour longer and then headed home to me, eager to tell me what she did.

When she got in, she looked quite disheveled. Her hair was out of place as she told me all that happened. We started making out and in no time, she was naked, once again. I spread her legs, slid down and looked at her pussy which was still red, a bit split open and very wet. I started eating her out and within a few minutes she had yet another orgasm. I fucked the hell out of her for an hour and came inside her, my load likely mixing with the load of that Nicolas Cage-looking mother fucker.

She never hung out with “Nicolas” again. I can’t remember why. I think they just drifted in different directions. A few days later her manager Luke who had fucked her told her that “Nicolas” mentioned that he had also fucked her. She was getting quite the reputation. At first she was worried that Luke would be put off by it and not want to sleep with her again but of course it had the opposite effect. He wanted to see her again and soon. My next story will be about how she went to Luke’s place where he fucked her while his roommate was in the next room and how that led to another visit where she blew him and his roommate! Slut!!

Source: reddit.com/r/gonewildstories/comments/11157f2/my_girlfriend_f_now_ex_pleases_her_bosss_m_friend