Strap-on with Jan - Sex Stories

Strap-on with Jan

Several years ago I met a lady through a coworker and after a week or so of emailing back and forth we went out to dinner. After the first date we realized we were both a little on the kinky side, and enjoyed several weekends of good sex, with lots of dirty talk. One evening we were lying in bed after I’d eaten her out (to a good cum) and I asked her if she had any toys she could use while I watched. She gave me a look, then got up and pulled a cardboard box out of the closet, when I looked inside, there were several virbrators, one of which was large and purple, with a “jackrabbit” attachment that stuck out from the side and could encircle the clit, twirling around and shaking as the main part of the vibrator buzzed happily along. Further inspection revealed a black harness, with a peach colored dildo about 8” long inserted through a steel ring. When I pointed at that and asked laughingly, “Is that what I think it is?” She started laughing as well and said “Yes, it’s one of my favorites!” After a few seconds had passed, she looked at me and grinned and asked, “Want to try it?” I’d been wanting to try a strap-on for a LONG time, so I replied, “Hell Yes!” She laughed and pulled it out of the box and I got the pleasure of watching her step into the harness. My cock was already hard, but now it tried to get even harder, and a little drop of pre-cum was slowly leaking out of the tip. Once she got the harness on and adjusted, I was thrilled with how sexy she looked. Her breasts ...

... were medium sized, and while they sagged a little, they looked great on her. The dildo stuck out from her shaved crotch and pointed up at an angle that made the tip of it just about lever with her belly button. She jerked her head at the bed and instructed me to lie down on my back. I quickly hoped up on the bed and lay down, spreading my legs and she walked to the edge of the bed. She had a tube of lube with her, and applied a large dollop to her finger, then moved her hand between my legs. I spread my knees out wider for her as she carefully placed her slick finger under my balls, then slowly moved down to my butt-crack. Once there she began massaging my sphincter with her cold, slippery finger, gently pushing in and pulling back, until eventually she had her finger in all the way. She smiled and whispered, “Nice ass!” as she violated me, and I was enjoying every bit of it. After finger-fucking me for a few minutes (and smiling while she watched me begin to hump up and down on her finger, she slowly pulled it out (much to my disappointment), then squeezed some more lube onto her fingers. Putting the tube down, she wrapped her coated hand around the dildo and began to jack her hand up and down the entire length, spreading the lube all over the toy. She did pay close attention to the tip, making sure it had a generous amount of slipperiness on it. My ass was hanging just on the edge of the bed, and I had my legs up in the air and knees spread wide in anticipation of being ...