Just to start, this is a bi story for those not interested in it.

I was 25 at the time and traveled to NYC for business. After the work day ended I went out for dinner and some drinks where I met this sexy confident woman in her 30’s. We sat and drank and talked for a couple hours before going to a club and dancing. We hit it off, we were making out while dancing. Before parting ways I asked if she wanted to take things back to my hotel room nearby. She said no but asked for my number. I gave it to her but didn’t expect anything to come of it.

The next day during meetings I got a text explaining that she said no the night before as I had to prove myself first. I said ok, what do I need to do? I really wanted her. She proceeded to tell me that I needed to hookup with her guy friend first to prove how much I wanted her. Lucky for me, I had been with guys and trans in the past and was all for it. She didn’t know that though. So without hesitation I asked what all do we have to do? Is he at least attractive?

She then told me to go to a certain bar at a set time. Sit at the bar and he would come up to me. We would then need to talk for a bit and then we would need to go and have some fun. We would need to stroke each other, blow each other and I would need to fuck him til we both cum. No problem.

So he comes up to me at the bar. He was in his 20’s as well, fit and I got excited. We drank, talked about her and talked about what we would do til we finally go to his place and had fun. We did all that was requested, his cock was hot and his tight ass took every inch of me. (8”) After we came he texted her saying I was worth it. She gave me her location and I would then go meet her. I had one request of him, I asked if I could have some fun and use one of his plugs, she could return it to him. I put it in and left. Plug in my ass and a bit of his cum in my chest hair.

I went to her place and quickly told her I had something she would have to give back to him. My guess was based on her request she might be one for pegging and I was right. She loved that I had his plug in and brought up pegging. We were up the rest of the night. I came once with him and four times with her. Inside her twice, once she swallowed and once while she had her way with my ass.

Hopefully this was a fun story to read. Happy to chat about this experience and many others! It was the hottest night of my life