This is a true story concerning something that happened to me several years ago and I still have trouble believing that it really happened. I have always wanted to tell someone about it, but was afraid I would be found out. I have never attempted to write an erotic story before, so please bear with me.
I am presently in my mid 40's, married with three children, very straight, except for the incident I am going to try to tell you about. I was born, raised and presently live in Tennessee. Being from this region of the country, I never considered having sex with another male when I was growing up. Of course, while I was in my teen years, I would joke with the other boys about it, but none of it was serious except for one boy.
We lived in a town of about 10,000 people, but my father owned three farms outside the town. He had a man living on the largest farm who was I guess was what you might call an 'overseer'. The man had several children, and I hate to say this, but the whole family was rather crude and what would now be called a bunch of 'rednecks'. My father would sometimes drop me off at their house so I could go hunting with the man's boys. I think I was about 15 when I first found out one of the boys had a sexual interest in me. He was about 2 or 3 years older that me, big, and probably not overly bright. I had been hunting with him several times, but always one or more of his brothers was also with us. One day when my father dropped me off this guy, whose name is Ben, went with me alone. After we got down in the woods and set down to wait we started to talk, at first about girls. He wanted to know if I had ever screwed a girl and I told him I had not, but wanted to real badly. He said he had screwed several girls (probably a lie), but what he really liked to do was, in his words, 'cornhole' boys. I remember I felt really strange when he started talking about this and didn't want to talk about such things, but, at the same time, I guess I was curious. He said he had done it to all his brothers several times and I think the youngest one was only about 9 or 10 at the time. He said his older brother, who was away in the army, had done it to him and how much he liked it. He then wanted to know if we 'city boys' were doing it to each other. I told him I didn't have any friends who would consider doing such a thing. Then he said something I have never forgotten, " Have you ever been 'cornholed', I sure would like to 'cornhole' you". This really started to scare me and I told him if he didn't stop talking about this I would tell my father. He might have been stupid, but he knew what his 'place' was so he shutup and never mentioned it again. At that time some of the old Southern class system was still recognized and I am sure he thought I was much higher on the social scale than he was. I never went hunting with him alone again, but I really probably didn't have anything to worry about since I think he was actually afraid I would tell.
I never thought much about this incident for several years. I went on to college, got married and started a family. When I was 22 my father passed away and I inherited all the land he owned and the guy, Ben, who was married now, still lived on the property. I guess I was 26 or 27 when I became obsessed with anal sex due to a couple of unrelated incidences. A friend of mine had some old 'stag' movies he loaned me to watch. These were the old black and white 8mm movies that were around before VCR's. I took them home and, one night when the wife was out of the house, I watched them. They were all about the same, but one stood out. It didn't have any women, just a man and what looked like a teenage boy, and the man proceeded to fuck the boy in the ass. This just about blew my mind, but I hate to admit it I was really turned on.
At that time I had never had a complete physical exam and my wife had been bugging me for quite a while to have one. So I finally broke and made an appointment. I had never really thought much about what the doctor did to you when you got a complete physical, but I found out. After the usual x-rays and drawing of blood, etc. the doctor came in and started to look me over. He had me lower my briefs and he checked me out in front. Then he told me to turn around and bend over so he could do a rectal exam. I was never so embarrassed, because, even in my naivete, I sort of knew what he was going to do next. He asked if I had ever had a rectal exam before and I told him I had not. He then told me I would probably find it to be a little uncomfortable, but just to relax. He put some lubricant on his gloved finger and started to massage my asshole. Even in my embarrassment I have to admit it sort of felt good. He then pushed his finger in me and proceeded to probe around for quite awhile. It definitely hurt, but, at the same time, it was a turnon and I actually started to get a partial erection. This scared me because I didn't know what the doctor would think, but he seemed not to notice. When I got home I immediately had to masturbate and couldn't wait for my wife to get home so I could fuck her.
From that time on I couldn't get anal sex off my mind. First I just had to fuck my wife in the ass. This took a lot of persuasion, but see finally she gave in. I have to say my wife is a wonderful woman and I really appreciate her. She is a 'proper Southern lady' and to submit to such an act took true love on her part. At first she couldn't stand it, but endured for my sake. I just couldn't get enough and after a period of time she got where she actually asked me to do it sometimes. As much as I enjoyed my wife I knew I needed more. I hated to admit to myself, but I wanted a man to fuck me in my ass and I wanted it bad. My thoughts really bothered me and it worried me that my desires made me a 'queer' or some other weird type person. I was not turned on by men's bodies and did not want to fuck them, but I couldn't get the idea of getting fucked off my mind. I became obsessed by the thought of being 'taken' by another man to the point I actually had fantasies about being made up and dressed like a woman while I was being fucked. This went on for about a year and it was becoming such an obsession I was actually losing sleep over it. I finally resigned myself the fact I was going to have to get ass fucked or go out of my mind. Looking back on it all I realize how dangerous this could have been, but this was before the AIDS scare and I had never really given 'safe sex' much of a thought.
Now I really had a problem. I did not know where I could find a man to take care of my problem. I knew a couple of guys everyone said were gay, but they both were definitely on the feminine side and what I was looking for was a real man. After a lot of thought I remembered the guy, Ben, and our teenage chat. Ben now worked for me so I did see him at least once a month. I thought long and hard about this before I made up my mind. The more I thought about it the more it seemed he was just right. Although he was definitely a crude clod he was also definitely very manly in an animal sort of way. Also, since he lived on my property and worked for me I felt like I had a hold on him and I could trust him to keep his mouth shut.
Very soon after I had made up my mind he came to the house to settle up for some crops. I always believed he liked coming to my house just to look at my wife. Anyway, after we finished with the finances I followed him out to his truck. I was nervous, but I asked him if he still fucked other guys in the ass. It definitely took him back, but he finally was able to say he had not done it in a long time, but still would like to if he ever got a chance. Then he asked why did I want to know. I said I just remembered the time years ago that he told me he wanted to 'cornhole' me. That really made him nervous and he said he was just a kid then and he was sorry. He was very polite and always called me, "Mr. Tom". I then told him if he ever said anything about what I was about to tell him I would kick him off my property. He nervousness made me braver. I then told him he could be honest and asked him if he still wanted to fuck me. It took awhile but he finally managed to say he would. I then told him I was still a virgin, but lately I had thought a lot about it and had made up my mind I wanted to experience taking it up the ass and not only I wanted but wanted it the worst sort of way. I could tell he wasn't sure I was serious, so I assured him I was very serious. He then started to loosen up a bit and asked me when and where did I want to do it. I knew I had reached the point of no return so I asked him what he thought about me coming down to the farm the following Saturday mourning. He said that would be great and then he left.
After he had gone reality set in about what I had just done. The next couple of days were pure hell. I was so nervous I could hardly sleep or eat, but Saturday finally came and, although it has been almost 18 years now, I can remember that day like it was yesterday.
I would like to say I had always worked out and ran ever since I was in high school and in those days I was a pretty nice looking guy. Looking back on it now I guess I had the kind of ass a guy would like the fuck because it was definitely firm and muscular. After we had breakfast my wife had to run some errands, so as soon as she left I gave myself a very thorough enema. I not only did this for sanitary reasons, but I was honestly afraid I might not be able to control my bowels with all that thrusting going on in my ass. I showered, got dressed and set out on my journey. I figured he would have some sort of lubricant, but I took a tube of KY with me just to be safe.
It is almost 10 miles from my house to the farm and I almost lost my nerve before I got there. I had always considered myself to be all man and I had still had some misgivings about letting another man fuck me in my ass, but I didn't chicken out. He was setting on the porch when I drove up and he met me at the car. He had a strange sort of grin on his face and said he really didn't think I would show up. He said he thought his wife would be gone, but she was still at home so we would have to go down to a barn that was about a quarter of a mile behind the house. Anyway, that was really much better since no one would bother us back there. I agreed and he got in the car. I noticed he already had a pretty large lump in his pants and that both scared and thrilled me at the same time.
Neither one of us said a word while I drove back to the barn. When we got to the barn he said we should climb up in the hayloft because it would be very private up there. So we did. It was a fairly common hayloft with a lot of loose hay lying around with lots of bales stacked up in the back. He then told me that he couldn't believe this was happening and how much he wanted to fuck me. I knew that the moment of truth had arrived and there was no turning back now even if I wanted to. He also asked me if I knew it would probably hurt quite a bit the first time. I told I did, but I wasn't going to whimper or whine and if I did I didn't want him to stop. I had wanted this for quite a while and now that it was about to happen I wanted to be fucked good. He really smiled then and assured me he was going to do a good job and when he was finished I would know I had really been fucked. He said he had always wanted to fuck a city boy's ass and my ass was the one he had wanted most of all. I figured he had a lot of experience so I asked him what position he wanted me to get into and he said it would probably be best if I got down on my knees and laid me head on a bale of hay. I asked if he had brought some lubricant and he just laughed and said he was well prepared. So we both took off our pants and briefs and I got my first look at his cock. I am fairly well endowed, but his was not only longer but quite a bit thicker and he was so turned on it was sticking almost straight up. I knew then for sure I was in for a rough time, but part of the 'thrill' of my fantasies was really being 'taken' by another man. I guess to know I was surrendering my body like a woman was what I had wanted and now I was going to get it.
I got down on my knees and leaned over the nearest bale of hay. He got up behind me and told me what a nice ass I had and how much he would going to enjoy fucking it and I was going to like it too after I had gotten used to it. Then he said I had come to the right person to give my 'cherry' to because he had done a lot of ass fucking and was good at it. He then put his hands on my buns and started to squeeze, massage and spread them apart. I was still a little uptight but I was trying to relax. I knew he was looking at my asshole and this along with all the other attention he was giving my ass started to relax me and I started to feel an erection coming on. Next I heard what sounded like him unsrewing a jar or bottle and then I felt a glob of cold lubricant being put between my cheeks. He then began to rub it around and into my rectal opening. He took quite a while which was a blessing, because as much I had wanted it I also didn't want to suffer any lasting injury. He probably also knew he didn't want to chance tearing his landlord's asshole. Next came his finger and after a short time it started to really hurt because he started to use two fingers. He said I was really tight but that would all change in a little while. He probably did this for a couple of minutes but it seemed to be a long time. By this time I really had a very hard erection. Then I felt him pull out his fingers and I felt what I knew to be the head of his cock pressing against my asshole. Then he started to really appIy pressure and I felt the head of his cock slowly stretching me and starting to go in. It hurt like hell and I still remember how my opening burned like it was on fire, but I also knew once it had worked its way in it wouldn't hurt as much. At that time I started to question my sanity about ever doing something so stupid, but I finally felt a sudden relaxation and I started to feel his cock slide into me. Even though I had made up my mind not moan or groan, the sudden realization of his big cock was actually going deep into my ass made me gasp. I never looked back during any of the act, but just looked down at the bale of hay and clenched my teeth. He pulled backed a little and pushed forward again. After he did this three or four times he managed to get all the way in because I could feel his pubic hairs rubbing against my ass cheeks. Along with the burning I now had very full sensation. I would have thought he was going to kill me if I didn't know that my little wife took almost as much into her tight little ass many times and she never had seemed to suffer any lasting damage. I am sure Ben wanted me to suffer some, because I know he thought I looked down on him, but I have to give him credit where credit is due. He probably did as a good a job of taking my virginity as could be expected. He started with real slow, short strokes and slowly increased the rate and length of thrusts. It really didn't last very long before I felt him shooting his hot cum into my insides. He sort of leaned over on my back and started to catch his breath. I had lost my erection with all the pain of his entering me and all thoughts of lust had left me. I was somewhat disappointed and ashamed of myself.
I was ready to leave, but Ben had other ideas. He never had pulled his cock out of my ass and although he had just cum it did not seem like it was getting any softer or smaller. He said my ass was so tight he couldn't help it but he came before he wanted to. He also said he would be ready again in a few minutes and he would last a lot longer next time and it would be better for me since the worst was over. I really had had all I wanted, but I figured that, if I had come this far, I could go a little farther. Anyway by this time my asshole was sort of numb.
After he had rested a few minutes he started to slowly move inside me again which quickly increased to some fairly hard strokes. I still continued to look down at the hay bale as he continued to fuck me. Although there was still some pain, the original lust that drove me to this started to return and along with that my erection. I can't be sure, but I feel certain he fucked me pretty hard for 15 or more minutes. Finally he came and just about collapsed on top of me. After he lay there for a minute or so he pulled his dick out of my ass which did not immediately close up because I felt cold air up inside me after his withdrawal. I sort of stumbled to my feet and I felt somewhat dizzy, but my cock was hard as a rock. Ben told me to turn around and face him and took my cock in his mouth. I didn't expect this, but I really needed it and it wasn't long before I came in his mouth.
After we sort of cleaned up and put our pants back on, Ben asked me how I liked it. I told him I had mixed emotions and now that my curiosity was cured I didn't know if I wanted to do it anymore. He said he hoped I would let him fuck me again sometimes, because he had never fucked such a hard and tight ass. I should try it a few more times just to give it a fair chance to see if I liked it. I told him I would think about it and I left. All the way home I felt like I was in a daze, like I was somewhere else. When I got home my wife wanted to know what was wrong with me. I told I didn't feel well and wanted to take a hot shower. In the shower I gingerly washed my asshole. I was definitely sore and stretched and I was worried I might be bleeding, so when I got out of the shower I squatted over a mirror to check out the situation. I was red and enflamed but no bleeding was evident. I think it took at least two weeks before rectum started to feel normal again and it never has been as tight as it was before he fucked me.
I did think I needed to give it a honest chance to see if I really liked it, especially since I had gone through the worst part of the 'break-in' process, so I returned to the farm 3 other times over the next 5 or 6 months to get thoroughly fucked. It did get better and it was a real turnon at times, but it never lived up to my fantasies.
Well, I hope I didn't do too bad a job. I haven't been fucked in the ass since then, but I do think about once in a while and I may have to have it again sometimes.