My life of sex by a middle age man

I am writing this story for two reasons. The first of which is as I get older it is a great to walk down memory lane. For those of you reading this if you don’t know what I am talking about give it some years and you will understand. The second is to give myself an objective view of my sex life to date. I had some bad and until the last few years repressed abuse as a child and this writing is a way to take a look at how those events colored my sexual preferences and desires. The hope is as I come to understand the relationship between my past experiences and current tastes I can work on tempering some of my more destructive desires and mature my sexual feelings. (As much as I would like to deny it I think I am very much stuck with the kinks that were put in place at 10 years old. These stories will not be about that.) With those goals in mind I will try to be as honest as my memory allows. Both the act of writing this and publishing it are both very erotic for me so I am going to work very hard on keeping it honest. Being honest about some of these events may be the most erotic part for me because I think it will be the first time I have ever articulated most of this even to myself. Most of the events are by their nature erotic but often the reality is not what the fantasy would have you think. I will do my best to convey my actual reactions not the penthouse forums version.
A little back ground I am currently 39 (maybe we all starting feeling the need to look at our lives as we hit 40) happily married 11 years to my soul mate and the best wife on the planet. She does her best to make me happy sexually (and she does) but luckily for me she is strong enough emotionally to tell me no and make it stick. You will see as you read this I am very manipulative when it comes to sex and have a great talent for finding people who are easy to manipulate. I think the reason our relationship works is she is the first person who was more important to me than the sex. She is also part of the reason I want to change my focus about sex. (if that makes since) I was raised in a loving home with both parents who I am very close to and have always been very supportive. I have one younger brother. We were an upper middle class family so money was never a big issue. I got about every toy that I ever asked for including a new car when I turned 16. I am going to include that I grew up in Wilmington NC I am sure there are quite a few people that as they read this may have been involved or heard about some of the things I will talk about. Who knows you might even guess who I am. I am currently a professional (engineer) with my doctorate degree. You will notice that my spelling and grammar are not the greatest but I am not having my sectary proofread this.
Physical appearance. I am short always have been I am 5’6” and I was pretty close to that in high school. In high school I was 125 lbs. I was a wrestler all 3 years so I remember my weight. I am much heavier now at 190lbs. Since this is kind of a sex story everyone wants to know cock size. I am pretty much the same size I was in school hard to really know. Everyone always has different ways to measure this. My preferred method is the toilet paper tube method. For thickness will your hard cock fit trough the cardboard tube that toilet paper comes on. Everyone know the size of that tube so it’s a good way to compare. Mine will not fit trough but if you cut the tube down its length and wrap it around my cock, it is a little over .5 inches between the edges of the tube. For length with the tube around my cock and pushed against the pelvic bone about 4 inches sticks out the top of the tube.
As I write this I am going to start with my first real girlfriend age 14. I don’t intend for this to be child porn but these are the events that happened. She wasn’t emotional hurt by any of this in fact we reconnected (no sex just old friends talking) a few years ago and I asked her about some of this and she remembers it quite fondly. Which goes to show how stable she is. (LOL sorry about that T if you read this) I will not be talking about my abuse before that at least not anytime soon. I don’t think I am ready for that. Between the last of the abuse (abusers moved away) and first girl friend is about 2+ years. In that time other than masturbation no sex.
So T and I started dating in jr high school. She was a heavy set girl, nice and curvy. I was the second guy that she went out with. She had, had sex with the first guy but apparently he came in like 5 seconds and it had led to a huge pregnancy scare. She we made out several times usually ending up with me fingering her and jerking off. I really liked fingering her she would get so wet her inner thighs would get slick. I could get my hand up to my last knuckle of my thumb inside her. She would lay on her back with me between her legs I would finger her pushing as much as I could in her. Then as she would cum (didn’t know that what it was back then) she would get wetter and I would switch hands and jerk off. Her wetness on my cock would drive me crazy. The most intense time I was about to cum and was really pushing hard and her vagina just popped and my whole hand went in. I freaked and started to pull my hand back out. She grabbed my arm and just held me in place. She wouldn’t talk or move she just held my arm with both hands. After a bit she relaxed a bit and let me pull my hand back out. She was sweating and still wasn’t talking. Needless to say I lost my hard on. I thought I had really hurt her. There was some blood on my hand and I didn’t know what had happened. We were at her parent’s house and after laying there a while she said she needed to get a shower and I had to go. I walked to my house that was in the next neighborhood trough the woods. It was several days before we were alone again and I was afraid that I had lost my only outlet for sex. We talked for a long time and finally came around to the fact that she had really liked what we did but was afraid of what I would think. I admitted that I was afraid I had hurt her but I lied to her and told her I had cum during it. So fisting became our regular thing. Our normal thing was heavy petting and then fingers till she came a few times with her on her back then she would get on her knees with her head on the ground. She would hold her cheeks apart and I would fist her changing hands to jerk off till I shot off. Our first time actually having intercourse we started out the same way but after she started cumming I laid over her and started rubbing my cock on her labia. She said no but I just kept asking to get a little closer in. Telling her the whole time I wouldn’t go in her. Ok I lied. And eventually I slipped in. At that point she stopped asking me to stop and we went at it. I pulled out just before I came and shot off across her stomach. After we both freaked about her getting pregnant. The rest of that month we didn’t have any sex till she got her period. Slowly we worked back into sex and included intercourse. We kept saying we were going to use condoms but it never seemed to work. After we were dating a while her mom and dad got divorced. T went to live with her mom in a trailer that was farther away for our neighborhood. That really sucked. I started riding the bus to her place after school and my parents would pick me up latter. Her trailer was really small her bedroom was the front end of it and her mom had her room in the back where the bath room was. T’s bedroom had a huge bay window that was floor to ceiling. The room couldn’t have been more than 8 by 10 and her bed was on the floor with no bed frame. It was a twin size bed and one side was against the wall and the other was midway across the window. This plays an important role. As it turns out one of our favorite positions was her with her knees on the floor and her laying across the bed. This put her ass from the side right in the window. She had curtains and kept them close. We would get off the bus and run to her bed room and fuck before her mom got home. So I was behind her going at it when I noticed the curtains were open enough for anyone outside to see. There was a pickup truck stopped right there and a guy was look in. As soon as I saw him I pulled out and came over her ass. The pickup drove on by the time I looked back up. I didn’t mention it to T but I couldn’t get it out of my head and ended up jerking off to the memory several times that night. It turned out to be her neighbor. He was an older man ( LOL I would say in his 30’s that was old then) that lived there alone. Every day I would try to get the curtains open without T realizing it and hoped he would see again. It didn’t happen. Then a few weeks later we had just finished and gone to the back room to the bathroom. I got out and T went in. I was standing there waiting for her to come out. I was in her mom’s room and noticed the guy next door was looking in through the window. As T came out of the bathroom I grabbed her and started kissing her. She was turned away from the window so she couldn’t see. It was not that strange for us to have sex a few times in a row (ah to be that young again) I got her shorts pulled down so he could see her ass. I realized he was jerking off but you couldn’t see since his window was too high on the wall. But you could tell from his movements. I got her bent over the bed and started fisting her. I made her hold her cheeks apart so he could see. It was such a trill to show her off like this. I came jerking off standing beside her. The guy moved away from the window as soon as she started to move. After that I tried to get her to go to her mom’s room every time I could and every time he would pop up to watch. He always kept where she couldn’t see. Eventually he was outside one day when my parents dropped me off to stay over with her on a Sunday. Her mom and her were not back from church yet so I was just standing around and he came out to sit on his porch. We said hi in that guy nod way. I didn’t know what to say. Eventually I got up the nerve and asked if he liked the show. He laughed and said he did very much. We talked for a little and he made a big deal out of making fun of her for being fat and asked me if she was like fucking a mayonnaise jar. At first I as getting pissed but as he talked I got a hard on. It was such a turn on to expose her and have him laugh at her. It was still kind of wearied and after that I stopped showing her to him.
The idea of showing her to people still turned me on and I eventually talked to her about fucking a friend of mine. We talked about it for weeks but it never happened. Eventually she asked about having a girl friend of her’s join us. I agreed without hesitation. My idea was that she would watch me fuck T. The friend’s name was Tara and she was something of a slut. She was this very thin small girl with huge brown eyes and short cropped hair. We went her trailer; she lived right down the road from T and her mom worked nights as a nurse. We got there and played around for hours not really sex more touching, kissing, and tickling with lots of really nervous laughing. It turned out they kissed more than I kissed either of them. We end up nude in her bed room floor. Tara started stroking me and kissing her way down T’s body. She ended up eating T out and both of them seamed to really love it. I found out years later it was not their first time together. When T started cumming she changed positions Tara laid on her back and T sat on her face. T tucked Tara’s arms under her legs and trapped them there. Tara kept on eating her. T got me around between Tara’s legs and I didn’t need any direction from there. I started pumping her. T pushed me back and grabbed my cock. She rubbed me up and down Tara’s pussy with one hand and held her leg back with the other one. She put my cock against Tara’s asshole. She looked me in the eye and said “do it” I looked at her and she mouthed “she loves it” So as T pulled Tara’s other leg back I pushed in. Tara bucked hard and I thought she was cumming so I kept going. T held her there and sat hard on her face. I couldn’t believe how tight she was and didn’t last long. I pulled out and came across her stomach. When I pulled out my cock was red with blood. T rolled to the side laughing. Tara curled up in a ball crying. I wasn’t sure what was going on or what to do. T pulled me down to her and started kissing me. She told me that it was ok and I think she spent more time reassuring me then worrying about Tara. After a little time she took Tara by the hair and pulled her head to my cock. Tara started sucking my cock. I got hard after a little while. I couldn’t believe what was going on. After I got hard T got Tara up on her knees and got behind me holding my cock. She guided me back into Tara’s ass. I took the hint and started fucking her again. I lasted longer this time. The whole time Tara cried but she stayed right there and didn’t try to move. After T got me to leave saying she needed to get Tara cleaned up. After that Tara never really talked to me and T never asked to do it again. It was a very confusing time for me I didn’t understand what had happened but I knew I liked it.
When I caught back up with T a few years ago she admitted that it had been Tara’s first time doing anal. Turns out Tara was the first to fist T (her hand was just smaller) and they had played around before. Turns out that Tara stole T’s first boy friend and it was about getting even with her.
Latter T and I got into playing around with bondage. She had convinced me at the time that Tara had really like the anal. So one evening I had T tied up and tried anal on her. First time she put her face in a pillow and screamed the whole time. We talked about it latter and the next time I went a lot slower and eventually T got where she really liked anal. She liked that I could cum in her without pulling out. T was also where I started getting into spanking. I would have her kneel at the side of her bed with her upper body across the bed. She would put the leg farthest from me up on the bed with her leg out strait. She had this little thin red leather belt. It was like 2 round tubes of soft leather stitched together. It was about a half inch wide. She kept it tucked under the corner of her bed. I would swing the belt so it followed the crack of her ass and the tip would whip around and land on her labia. I found if I started very lightly and worked up to hitting harder she would actually cum from it. I really loved the sounds she would make kind of a half whimper half cry but I also loved how it made her pussy feel. I can’t really explain what was different but it was like she was softer and tighter after being whipped like that. I have never been with another person who liked being hit that hard. We always had to do it when everyone was gone because the belt made a lot of noise. If we were at her trailer and her mom left the belt would magically appear in her hand. I so loved making her beg for the belt.
Eventually T’s mom met another guy and she moved with T to another town. We broke up
There are a lot more adventures with T and 2 more serious girlfriends and a few short term girls friends to go if it sounds interesting to anyone. Any comments on how to write it out better would be gladly accepted.

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