A true story which happened about 3 months ago.
About three months ago, I placed an ad at a erotic posting website looking for a woman who would be interested to come to my office one evening after work to take part in some masturbation fun. I wasn't looking for sex, just a friend who would like to watch or even indulge in some innocent fun. I was pleased that within a day or so, I had a response from a mature woman (45 yrs old) who emailed me, stating she was very interested (I'm 29 yrs old).
We emailed each other a few times eventually setting up a time for the following day. The plan was for her to come by my office after everybody had left. I'm often there late and alone. The next day came and went, and soon it was 6:30 and the anxiety was starting to build as I had never done this before (with a stranger). She called me when she arrived, and I gave her directions to get to my suite. Five minutes later there was a knock on the door. My heart was honestly beating out of my chest in anticipation as I opened the door. I was pleasantly surprised when I saw her standing there. She was a cute petite, mature woman with pale skin, short blonde hair, and dressed in a long black casual dress with a black jacket. We shook hands, smiled, and made a little small talk for a few minutes while we got comfortable. She told me she loved to watch and was excited to be doing this. I agreed as I sat in a chair next to her. We were in my office next to a conference table.
She said we could start whenever and asked me what I'd like to do. I asked if she wouldn't mind standing up next to me and showing me her legs and ass as those are my favorite parts of a woman's body. She kindly obliged and stood up, slowly raising her dress up to her waist. I was surprised and happy to see she wasn't wearing any panties. She put both hands on the table and slightly bent over to give me a good view of her ass. I asked her if it was okay if I massaged her ass a bit, and she said, 'Go right ahead.' I let my hands cup her ass and lightly massage her butt. It felt nice to let my hands slide around her legs and ass and feel her up. I let my hands slide between her legs a few times to feel the wetness that was beginning to build in her pussy. After a few minutes of this she turned around and gave me a nice view of her shaven pussy and ran her finger over it. She sat back down in the chair next to me with her dress still at her waist. She opened up her top and let her tits peek out. They were small but still in great shape as she lightly pinched her nipples.
She asked to see what I had, as she saw the bulge in my pants growing. I stood up next to her now and slowly started unzipping my jeans. I did it a little slow, so she could take it in and enjoy. She lightly pinched her nipple with one hand and let her other hand roam around her pussy while I did this. I pulled my jeans down to my ankles and my boxers followed, exposing my hard dick and full size. (probably around 7-8 inches fully hard). She let out a light moan of approval as I sat back down and let my hands begin slowly stroking my cock.
I masturbated slowly for her because I didn't want this to end quickly. She commented how nice my cock was and I told her how sexy she looked rubbing her clit in front of me. We sat about a foot apart in our chairs, facing each other, watching one another stroke ourselves. We played like this for the next 10 minutes or so. I stood up and continued jacking off next to her face so she could get a closer view. I leaned over and lightly sucked one of her nipples while I continued to masturbate. She leaned back in the chair enjoying every second of it.
After a few minutes more, she told me she wanted to see me cum. She opened up her top and told me to cum all over her tits. Hearing her say this was a huge turn-on and got me real close to climax. I climbed over her and the chair so that I was straddling her and my cock was a few inches from her face. We both began stroking faster and faster until I began cuming all over her tits. We both let out moans as 5 or 6 loads cum sprayed across her soft breasts. We were both nearly out of breath as we collapsed back into our chairs. We sat and laughed and cleaned up for a bit until it was time to end our little session.
We put ourselves back together, and we shook hands and she left. It was a great time and I hope to get to experience something like this again. I've masturbated with girlfriends before, but there's something about two strangers meeting and immediately letting them see you in the most private ways. It was a huge turn-on and another fantasy I can check of the list! I hope you enjoyed and would love to hear what you thought. Bye!