Divorce was fun I had time to do all kinds of fun stuff but the best part was I had time to have sex. Sex with men sex with women and sex with anything I wanted. I got divorced and the first one I hooked up with was a girl from work. Pam was a fun girl always had a lot of fun talking to her and when she found out I was getting divorced she came over to me one day and asked me if I was interested in going out. I said sure what do you have in mind and she said well I have always wanted to sit on your face and hard cock. I looked at her a little surprised. She smiled at me and moved close and grabbed my cock thru my pants and said I want this deep in my pussy and ass. I was a little shocked but also horny so I said okay now? She laughed and said no after work so I said okay and went back to doing whatever I was doing. Quitting time came around and she was next to me waiting so we both took off and she said my place or yours? I said mine so we got into my car and she left hers in the parking lot and we took off for my place. I did not live very far from work but it felt like a million miles.

We pulled into my drive and we went inside and she quickly said be right back and went down the hall to the bathroom. I sat in the chair not knowing what to but when she came back into the living room I got a good idea. She was naked except for a garter belt and nylons. Her small tits and shaved pussy visible and she also had pretty little feet and toes and her toes were red. It was funny because we had talked a lot and I had mentioned to her that I loved red toes and feet and a shaved pussy and small tits and she had it all. She smiled and said well do I meet your needs? I looked at her and she moved closer and reached for my cock and pulled my pants down and started to play with me. she smiled and said stand up and she took off all of my cloths and said okay bedroom and we walked down the hall to my bedroom and lay down on the bed. She quickly started to suck and lick on my rock hard cock and I started to play with her sweet pussy and could tell she was real horny because she was soaking wet. I picked her up and moved her around so she was sitting on my face and quickly started to lick and suck on her sweet pussy and when I found her clit she exploded filling my mouth with her juice. I licked and swallowed it all down and kept on licking her and she exploded again and again till she finally moved off my face and said I need you deep in my pussy and ass she moved around and positioned herself over my hard cock and slowly sat down on it and buried it in her wet pussy and then started to ride me deep. She rode me hard till she stopped and said next and she moved a little and sat down again but this time with my cock deep in her nice ass. She rode me deep and I was getting close and she could tell so she rode me hard and said okay fill me with your hot cum now. I could not take it anymore and finally exploded deep in her sweet ass and filled her with a huge load because this was the first sex I had in a long time. I was enjoying it so much that I kept hard so she kept on riding me. She was very well lubed now so it slid very nice and I kept fucking her ass till I exploded again and filled her ass with another load of cum. This one was smaller but still nice because I had never cum twice in that short of time. She rolled off of my cock and we lay together and just relaxed for a few minutes. Finally she got up and went into the bathroom and came back out still naked except for her nylons. She sat on the bed and smiled and said that was very nice and I said yes it was and she smiled. I looked at her and started to get horny again so I reached over and started to play with her very small tits and hard nipples and I found out that they were very sensitive and she loved it. I pushed her down on the bed and then started to lick and suck on her nipples and then started to nibble on them. She started to moan and said damn that feels so good so I kept it up and she reached down and started to play with her pussy. She quickly exploded in a nice orgasm so I kept sucking and nibbling on her sweet nipples until she finally stopped. I moved up and she smiled and said damn you are real good and I said well I have wanted to do so many things when I got divorced I have been reading and looking at books and have got a lot of ideas and could not wait to try them out. She smiled and said oh yea what else do you want to try? I smiled at her and said well and did not say anything she moved close and said come on tell me.

The funny thing about her and I was it was a relationship like no other. We had been friends for years while at work and nothing sexual had ever crossed our minds but we could talk about anything together. She had told me about some of her boyfriends and how good or bad they were in bed and I had got to know a lot about her sex wise because of our talks. I had slowly started to tell her about my now ex wife and how she would not give me sex for months at a time and would go out to the bar with friends while I watched our son and would not come home till 2am. I also started to tell her about what I liked and disliked like red toes shaved pussy small tits and stuff. Well when it got time to tell her about this it felt right so I told her how I had been looking at books and magazines and had started to be interested in cross dressing and strap on play. She looked at me and said really and I said well I figure I love nylons and garter belts etc on women well why not on me? and well strap on play is just another part of cross-dressing kind of like giving yourself completely to your women. She smiled and said well I must say that would be kind of interesting and the idea of fucking you in the ass and mouth sounds like a lot of fun. I looked at her and smiled and she said okay lets go and I said lets go? She said yup it is almost the weekend let go to the store and find the stuff so we can have fun this weekend. I got up and we took off for the lingerie store close by my house and we went inside and looked around. A nice cute girl maybe 22 came over and asked if she could help us and I said not yet just looking. I was not about to ask her yes could you point out what area the strap on cock were in I want one deep in my ass and while you are at it can you find some nylons and garter belts that will fit me. We looked around a little and finally Pam said be right back and she went up to the girl and talked to her for about 5 minutes. They both came over to me smiling and the girl said well the strap on cock are this way and we have many outfits that will fit you what color do you want? I did not say anything and finally Pam said lets try red I think he will look nice in red. I smiled and said okay and we went over to the area that had the nylons and stuff and she picked out a nice garter belt, sheer panties and a nice pair of red nylons. She said I think this should fit but why not go and try it on in the back. I smiled and said okay and walked in the back room and into the dressing room they had and closed the curtain. I started to take off my stuff and then looked at the outfit and had no idea how to put it on or hook the nylons when just then the girl opened the curtains and said I figured I better come and help you put the stuff on. I tried to cover up my now hardening cock but she said stand up so I did and she started to put on the garter belt then said okay sit and I did and she opened up the package and took out the nylons and started to put them on my legs. She looked at me and said you know you really should do your toes like my boyfriend. I looked at her and she said yes my boyfriend dresses all the time for me I love it but he also shaves completely and has his toes red. I looked at my feet and just then Pam walked in and she said yes good idea lets do them red for him and we can shave him later. She took off the nylons and went into the store and came back with a bottle of red nail polish and slowly did my toes. I must say they looked real sexy in red. She waited for a short time until they had dried and then put on my red nylons and hooked them to the garter belt and said okay stand up. I stood up and she put on a nice sexy red and black baby doll and said okay check yourself out. I looked in the mirror and liked what I saw she said okay now to complete the look and she gave me a pair of sexy sheer panties and I put them on to cover my hard cock. I loved the look and so did Pam. The salesgirl checked me out and said damn you look nice maybe I will come over one day and bring my boyfriend with me and I can watch him and you sucking and fucking each other while you are both dressed like sissies. She said okay now we need to look for a nice strap on cock so she and the salesgirl went out on the floor and soon came back with two boxes one about 5” and the other 6”. The salesgirl said start slow and get him use to it first a little at a time use enema first to clean him out then slowly stick it in and when he is use to it fuck him slow then hard and finally pound his ass. I thanked the salesgirl and gave her my number and told her to call me one day and we could get together with her and her boyfriend and play I would love to get fucked in the ass by a man.. I kept on the outfit and put my pants and shirt over the stuff and put on my shoes over the nylons and we paid for the stuff and we went to my house and she sucked my cock while I was wearing the outfit. We went to work the next day Friday and finally the weekend started. I went home and Pam followed me home and we decided that we would start with the strap on so I went and took a shower and then she came in and with the electric razor and blade she shaved my cock and balls and also did my legs so I was nice and smooth. She checked me out and said forgot something so she got out the razor and cream and also did my chest and belly so now I was completely smooth and I must say I looked nice. She said okay now lets get you clean inside also so she got out the enema and we mixed up some soap and water and I used that till I was nice and clean inside also. She had put my outfit on the bed so when I came out I went and put it on and while I was dressing she came into the bedroom and she was dressed in the new strap on and I saw it and got hard quickly I checked her out and she said lets see if this fits sissy.

We went and I bent over the bed and she got behind me and put some lube on her cock and she slowly started to work it in my virgin ass. She went slow and after a few minutes she had all of her cock in my ass so now she started to work it in and out slowly. I was getting use to it and enjoying it and finally told her okay now pound my ass master. This is all she needed to hear, and she started to really pound my ass deep and hard and I was loving it. She said okay now get up and lay down on your back on the bed so I got up and lay down and she moved between my legs and picked them up and slowly worked her cock in my ass and then started to pound me again but this time she was also playing with my rock hard cock. we kept this up all weekend and finally stopped only because we had to get some sleep and go to work. We continued this off and on for almost a month. I finally started to go to the sex club and park and found that I really loved real cocks also and would get fucked by them most weekends. My little salesgirl did get hold of me and she did bring her boyfriend out on Saturday night and him and I fucked each other while she watched us and played with her vibrator. She finally could not take it anymore and took off her cloth’s and sat on my face while her boyfriend fucked my ass deep. She had a real nice body but her pussy was covered with hair but I ate it and made her cum a bunch while her boyfriend filled my ass with a nice load of his hot cum. This was a fun time in my life