I titled this story craigslist hookup because this is how long I have known the guy. We met back in the Craigslist day's originally. He is a black gentlemen, in his 50's, slightly muscular, little over 6 feet tall. A pretty good looking older guy. He calls me whenever he is feeling frisky, usually once or twice a month. We always have a good time and sometimes talk dirty to each other during our fun. He started talking about sharing me with a friend of his. I played along but after we were done, he followed back up with it and asked if I would be down. I answered of course! A week or so goes by and he messages me and tells me I should meet at his apartment tomorrow to have some fun with a friend of his. He asked me if I could wear some sexy women's underwear that I have, and the guy would like it.
The day comes and I throw on a nice pink pair of boy shorts that show off my ass nicely. The undies were a surprise for his friend. I go to my buddies apartment and meet up with a pretty average looking white guy. Good looking, but nothing crazy. We talk a few minutes until my friend (knowing how I am) tells his buddy to pull his cock out and I'll be all over it.
He takes it out and I get down on my knees and get to work. It didn't take too long and he said he wants to fuck me. Its at this point I peel off my pants and he sees my sexy undies. He really came out of his shell then. He pushes me down onto the bed and pulls my panties aside, and starts going to town eating my ass. After getting me good and wet, he flips me onto my stomach and before I can say anything he is pushing my panties aside and pushing his cock into me. He ate my ass well so I was plenty loose and wet. His cock was pretty average, but was just thick enough to fill me up good. He starts fucking me while my buddy is watching. I tell my buddy to snap a picture with the guys phone so he has something to remember :) After my buddy snapped a few pics I convinced him to come in front of the bed so I could blow him while his buddy fucked me hard in doggy style. This is my all time favorite thing to do, get fucked good and hard while sucking another cock. The only down side to this is that some guys end up coming quick from all the excitement, which is what happened here. He pounded me really hard for a good 20 or 30 seconds before he slammed deep in me and came. I of course was pushed forward on my friends cock that ended up deeper in my throat then I was ready for. I choked for a second and it took me a few seconds to get my senses back as I was overcome with everything. My buddy said he still wanted to fuck, but the other guy got dressed and peaced out.
My friend is a more passionate guy, so he went slower and really dicked me down nice and slow and deep, which is how we usually do it. He has a hard time cumming, which is good for me. It took him about 15 minutes of good fucking before he added another load to me. We cuddled a bit before I got up and cleaned up a bit.
He said that we defiantly needed to do it again, but next time he wanted me in stockings, underwear and a bra/top.

Just a spoiler for my next entry. I went back, in black stockings and a lace top/panties set. His friend was there, except it was a different friend. I'm starting to think he is whoring me out to his friends, and I'm ok with it.

Thank you again for reading about my adventures. I love feedback so dm me if you want to chat!