Last year, I found a girl on craigslist that was offering massages, so I contacted her, brought her to my place and I got naked and she gave me a very good massage and even a happy ending. Well, sexually I am a sissy submissive bottom, that loves anal toys.
The next time we met, I always have to go and pick her up, no big deal. Before I left the house, I intentionally left out one of my dildos in the bathroom on the tub. I knew when she went in their to pee, she would be staring at it. She came out and proceeded to give me that full massage again, but did not mention the dildo at all. On the way back to her house I commented about how much I enjoy my anal fun and asked her if she ever used a strap-on or toys on anyone before.
This 24 y/o girl, said no, but she would the next time. Well that time came and after the massage, I took the lube and lubed my hole and then told her to lube the dildo and slowly push it in, all the way in, then told her to fuck me with it. She started pumping away and did this for awhile, until I finally shot my cum. On the way home, I asked her thoughts and she said she was starting to really get into it.
Somehow, I changed phone numbers and so did she and we lost contact, bummer