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When I was dating my x girlfriend, when we first got together she looked to be a very shy girl. She had a very average body for a mother of 4 at 39 years old. As we got close to having sex we clicked good in that area, so I asked her about having anal sex and she said yes she loved it. So we started a great relationship and for someone that was a very shy type she was very in bed. One day we were playing in bed together and was giving me oral she inserted a finger in my rectum which surprised me because know one ever had before. She rubbed her finger in there for a while and I had a very, very intense orgasm. After a few months I realized loved anal in every position more than she did vaginal sex! It was maybe a month or two latter one day when I was lying on the bed on my stomach when she started rubbing my back, she then took the KY jelly out of the drawer, which she had done before when she was using her finger on me. This time she had a towel on the bed and was fingering my anus like she usually did, she told me too relax and played down there a while. Then she reached into the drawer and got her dildo out it was around 9” and large in circumference, I asked what she was doing and she said she wanted me to learn to do anal and it had been a big fantasy of hers, I told her I would try for her and she said I would it she knew. She lubed the large dildo and started inserting it into my anus, and did it burn, she told me just to sit still and relax, I wanted to stop but she was gentle and still wanted to play, so after a few minutes she said she had about 7 inches inside my anus. It hurt a little still but mainly I just felt very full in my ass, she was holding it still as she was rubbing my back. We played like that a while and the she asked me to roll over on my back, so I did her dildo was still in my anus, I started stroking my penis at this point and she gave me some KY for my hand. She the placed a pillow under my bottom and told me how great it look with the dildo in my anus and she was going to pump it just like a would, so she began taking short strokes, but eventually she was taking very strokes in my anus, it hurt but felt good and I finally had the most intense orgasm I ever had. Tennessee singles 50
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