[F] I wingwoman’d for my colleague [M] and hooked him up with a friend [F] after his drought. He did anal for the first time and now jokes that he owes me forever

My poor friend. I work with him and he went through a rough breakup. Anyway, after a few months, I told him he has to get back out there. I could see his confidence had seen better days. I had to do something productive.

In steps my friend, Erin. She met after work one day and said he was rather handsome. He had zero idea. So, I made she sure DM’d him, and before I knew it, they’re talking loads.

I joked I would stay out of it but secretly hoped they’d have fun. They both seemed a little shy and maybe it’d cancel things out.

After two weeks of talking, one day, he says he and Erin spent the night together. I felt like such a good wingwoman. I didn’t ask specific details, until he randomly came out with, “I did anal for the first time.”

I nearly spat my drink out. Erin was NOT the friend who I’d imagine doing anal. It came out of nowhere. We’ve spoken everything sexual and I knew she’d never had a dick between her cheeks.

The brief silence and random facial expressions from me resulted in a, “I owe you until the end of time.”

If you can’t give a good guy your ass, try to have him enjoy your friend’s ass instead. Who says you can’t make a guy feel great indirectly?

Source: reddit.com/r/gonewildstories/comments/1137f10/f_i_wingwomand_for_my_colleague_m_and_hooked_him

3 comments

  1. So, does that mean Erin is going to set you up with a guy who ends up up with his dick between your cheeks as you get ass fucked? If so, where do I sign up?

  2. My friends are terrible compared to you and yours. Had a 13 year dry spell and am now working on a 5 year dry spell. Zero wingwomen setting me up. Ugg. My friends suck.

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