I met Wendy through an add I posted on Craigslist looking for a friend with benefits. She was newly separated from her husband, but still having sex with him while looking for someone else to transition to. She and I hit it off and soon we were chatting non-stop and had decided to meet. Our first meet up was actually just hanging out and cruising around town. More probably could have happened but were both too nervous to make the first move. Funny/scary moment of the night, she and I were walking around the downtown area and ran into some friends of my wife and I. I introduced Wendy as a friend and chatted for a bit before moving on.
After that first night we both agreed we were interested in more, and would have been willing that night. So we agreed to meet up again with full intention of having some fun. I made up an excuse to leave the house one evening and drove straight to Wendy’s place. I got there and we sat in the couch watching TV for a little while before we started making out. We made out for a while, hands exploring each other’s bodies. I was groping at her tits as she was rubbing my cock through my jeans.
She was wearing a dress and before long her dress was on the floor along with my shirt. She wasn’t wearing a bra so her breasts were exposed and my hands and mouth were soon playing with her nipples. My hand eventually made it’s way into her thong panties and I was amazed at just how wet her pussy was. She was undoing my belt and working her way toward my cock. She fished it out and slid to her knees on the floor and began to give me head. She sucked my cock for a bit and then suggested to me that we should move to her bedroom.
I followed her to her room, watching her ass wiggle and getting turned on by seeing her walking in just the skimpy panties. We get to her room and I take my pants and underwear off and lay down naked on her bed. She crawls up beside me on her hands and knees and begins sucking my cock again. Her mouth felt so good and I loved watching this woman that I barely knew bobbing her head up and down my shaft.
She continued for a bit but then stopped. She had her fuck me eyes going as she sat up and I watched her role the thing down her thighs and eventually kicking them off. I remember watching and thinking we’re about to have sex. As she tossed her panties aside I told her I had condoms in the back pocket of my jeans. She glanced at them laying on the floor and leaned down and started kissing me, throwing her leg over me so she was straddling me. We were making out and grinding against each other and then she reached down and grabbed my cock, lined me up and slid down onto me. The feeling of her bare pussy gliding down my uncovered cock was incredible, and I remember thinking I’m going raw with a woman I just recently met via craigslist!
She was riding me, hands on my chest as I played with her tits and another hand rubbing her clit. It didn’t take her long before she was cumming and she had me really close. I told her I was about to cum, assuming she would have me pull out, but she didn’t stop, she just kept fucking me and soon I was unloading into her pussy.
She collapsed beside me and we had some after sex chat. After some while of chatting we began kissing again, my hands were exploring and soon I was hard and made my way between her legs and posted my dick back inside of her. I always love additional rounds of sex. I’m able to last much longer and fuck harder. I had my way with Wendy’s pussy and ended up spilling a second load of cum into her pussy. We chatted a bit more before I got dressed and headed back home to my wife.
Source: reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf