How Crossdressing Changed My Life

I began dressing very modestly about 3 years ago while I was still married. My wife was always gone for work so I had plenty of time to masturbate and that is great for me because I'd never found anyone that could make me cum as hard as I could do myself. Even after some wild fuck sessions with my wife and the women before her, I'd jack off. It was as if I had to get more out. And I was always looking for new ways and I'd try anything and did.

Once while she was away for the day I was in the middle of masturbation session. I loved getting naked then spending time around the house and watching porn online until I couldn't take it any longer then I'd jack off. This time though as I was searching for new porn to watch and I accidentally came across a CD. I didn't know it was a man at first because the pic looked just like a really hot blond and the pic was from the rear, she/he had beautiful long blonde hair and a great ass, this got my attention and when I opened it I saw she was actually a he! But I couldn't take my eyes off him and I watched the entire video as he fucked and got fucked. This was the first time I ever saw a man get fucked in the ass. But he was dressed so sexy like a woman it wasn't like watching two men. I came so hard and so much it took forever to get clean. I knew I'd found a new way to masturbate and anytime I was alone I searched for videos like that and jack off. I'd never before looked at anything like this. Before this the thought of men doing men made me sick, I hated it and thought that something must be wrong for men to want to be with other men. But I couldn't understand how I could watch this kind of thing and get so excited. I knew one thing, there was no way in hell I'd ever do that.

As I said I'm always looking for new ways to masturbate and during the time of watching this kind of thing I experimented with anal for the first time in my life. I was watching another CD video, he was getting pounded by this really big cock I wondered how it felt to have something in my ass so as I watched I slid my hand under my ass and began squeezing it first kind of slowly leading up to it I guess, then I put my finger between the cheeks and found my hole, I started touching around it I could believe how good this felt, the only thing I had for lube was spit so I wet my ass and finger as much as could and I eased my finger in, it hurt and bad but I went easy and slow and soon the pain was gone. It felt so good and I came very hard. I masturbated for a long fingering myself, I even got to where I could handle two fingers in my ass. But each time I seemed to cum harder than the last. Then I began thinking about me trying to dress in my wife clothes and do all this, it took some time for me to try it.

I wasn't sure I wanted to because I was afraid it would make me gay. Then one Saturday my wife was gone and she was going to away until the next day. Being alone made always made me very horny so that afternoon I got into her closet and got a few things. I also got her bra and pantyhose. I dressed but not looking in the mirror as I did. I was so hard and dripping cum the entire time I dressed. I put on her bra and had to find lots of padding because she had huge tits. I've always had a huge boot fetish so I wore boots, when I was finished I walked over to a full length mirror and I saw myself for the first time wearing women's clothing. I didn't use any makeup or wigs, just clothes and I loved it. I jacked off as I looked at myself, I even kissed the mirror like I was kissing myself and when I came my legs got so weak and I literally fell to my knees from cuming so hard. I knew then I'd found something special. So for the next year or so anytime I was alone I dressed in those clothes and jack off. But being married I could never expand on it, but that was okay. I was happy with that little bit of what I doing.

Then we divorced, not because of this but other things. I moved out alone in small house in the country. I really wanted to be away from everyone so I found a place that was nice but away from neighbors. In fact my nearest neighbor was over a mile away. I wanted that so I could do anything I want and never have nosy people watching. The strange thing, it took over a month before I could find the time to dress. And not having access to women's clothes meant now I had to buy them. Buying them was really weird but exciting also. I only bought a few things, no makeup or anything else. I bought two tops one gray and one pink, I bought these tight little white short shorts and a short jean skirt, I also bought a long skirt and belt to dress a little more decent I guess. I bought a pair of white pantyhose which I cut the crotch out so I could play with myself while dressed and I bought some boots which I didn't like much but I had to have boots. I also bought a 44DD bra and padding. I loved it and every time I dressed I seemed to cum harder each time, I just fell in love with it so I decided I was going to take it all the way, I needed more things but I'd felt weird when checking out so this time I ordered everything online, I ordered two wigs one blond of course and the other with long black hair, I ordered makeup which I had no idea what all to get so I bought several things and I ordered some jewelry, I ordered a few more pantyhose, (all crotch less) and bra's and to top it off I bought these really sexy thigh high boots with five inch heels. I waited until everything arrived before dressing again. I wanted the full effect.

It took over a week for everything to arrive but once it had I knew that night was going to fun. The first time I put makeup on was so exciting, I could barely get close enough to the mirror because of my cock being hard. When I finished dressing I felt so sexy, but I'd never wore heels before and that was challenging to say the least. My walk was far from sexy. And when l saw myself for the first time completely dressed I couldn't believe it was me I thought to myself I should have been born a woman because I changed to one so easily. I had planned to spend hours around the house dressed but after just an hour I was to horny, I couldn't take any longer. I came so hard it actually hurt, I was now totally hooked. But I felt embarrassed as soon as I came and I'd jump up undress and shower it was strange.

Now with me wearing makeup and wigs I started looking for new ways to make myself cum I remembered how fingering myself made me cum hard so I began fingering myself every time. I loved it and I kind of knew I liked it a lot more than should but I wasn't going to stop. Fingering myself was working but I wanted more. So online I went and I ordered a toy, I needed a very small one and the smallest I could find was 5". The night I used for the first time was the most painful thing I'd ever experienced, I couldn't take it and had to stop, it took me a few nights before I could actually get it in and once I did the pain was horrific. The first time I got it all in I just laid there thinking if it was going to be this hard to do I might not like it but after my ass relaxed it felt better than good and it always made me cum very hard. But as strange as this sounds, with all this still fucking myself with the dildo it didn't make me want a man. I never entertained the idea of being with a man. Nothing about those feeling had changed as odd as that sounds. Over the next two weeks I fucked myself with that dildo nearly every night, every time I did it took several minutes to get in and a few more before I could actually fuck it, but it was great but still I'd feel guilty even though I seemed to cum harder each time.

The big turning point came one day when I decided to shave my entire my body. I'm naturally hairy but I've always kept the hair trimmed around my cock but never shaved my body. It took a long time to get myself shaven and in preparation of this I bought some sweet smelling women's lotion to put on when I was done. As I looked in the mirror at my new body and rubbing the lotion on I got incredibly excited. My body felt so smooth and soft, it felt as good as any woman I'd ever touched. The pre-cum was dripping out of me by the tons. I got dressed and when I was done I could feel something inside me changing, the way the clothes now felt against my skin was unbelievable, I didn't want to admit it but I was beginning to feel so lady like. I really wasn't ready for that feeling at all but this was all too exciting and I couldn't stop now. It only took about an hour of being dressed before I was in bed and masturbating. I rubbed my body under my clothes and it felt so wonderful, then I took my blouse off so I could feel it I left my bra and padding on so I could feel the cleavage, and seeing myself in bra only and smooth skin was great. When I started sliding the dildo in I noticed it didn't seem to hurt as much, I was to excited to hurt I guess. As I began riding my dildo out of the blue I started fantasizing this was man fucking me. I began fantasizing about me on my back being the woman and telling him how good he felt in me. I came so hard I shook, it seemed harder than ever, and now I was really worried. I didn't know why I had this thought. It caught me completely by surprise. I jumped up and undressed quickly.

I spent the entire next day worried. I considered stopping dressing because I thought it was turning me gay. I struggled with it all day. That night I wanted to try it again and see if I had those same thoughts. I dressed and during the time I was fucking myself it happened again, it was like I couldn't stop it from getting in my mind. Now I was really worried. I didn't even dress for a while. I went back to masturbating the old way. It wasn't near as good but I didn't want to be gay. But because the old way wasn't as satisfying to me now it wasn't long before I dressed again. But every time I masturbated I had this fantasy. I thought about it for a few days. I even tried looking at gay porn but couldn't. But it was pulling me in even though I wasn't sure about it so I gave in and decided I'd try it once. I set my own personal boundaries. The first thing, I didn't want anyone I knew finding out I dressed like this, so in my ad I said nobody without a face pic first. I also knew I didn't ever want to be kissed by a man and I for sure didn't want to touch or suck another cock. I didn't even want them talking to me. I just wanted to try to be fucked and see if I liked it so I could say I tried it. I wasn't sure I could handle a man fucking me or even go through with it. I also didn't want someone with a huge cock, I could barely handle my little skinny 5"er. If much bigger than this, I wouldn't be able to take it so I asked for full stats.

After about four days of no takers I began to worry if I could get this. I knew there would be no way I could go out dressed and find a man. I decided I'd try adding pix to the ad, I put pix with my big tits in the ad and things changed quick. I had so many men emailing I could barely keep up with it, and the things they were saying, wow! I couldn't believe the things I was reading were about me, I'd never looked at myself even dressed as wanted like this and now I was hearing how sexy I was and how bad they wanted me, they were telling me all the things they wanted to do to me and wanting my lips on their cock. I was asked if I really was a man and if my tits were real, all this made me feel special but strange and powerful, hearing things said about me like this especially coming from men was odd to say the least. I realized what women went through and why they didn't give out their pussy if they didn't want to. There was always someone that would fuck them when they were ready so why settle, be picky. I couldn't believe I was actually liking what I was hearing from men, after all I thought men being with men was nasty. I was told all the time "I'll be there" and then never show. I rejected several based on their cock size, over the next week or so I began to think that even with the pix it wasn't going to happen. Night after night nobody came, not that it was bad but I'd masturbate and wonder what it felt like.

Then one night after a man didn't show like he said he would I was preparing to do myself when an email popped in asking if I was still looking. I figured like all the others he was nothing. But he answered right back to "yes I am" and he said send me your address and I'll be right there, I don't know why but I broke my own rule and gave it to him without asking for a face pix or cock size. I guess I didn't think he'd show anyway. But about 30 minutes later I heard a car pull in. I peeked out of the window to make sure I didn't know him, so I let him in. He started telling me how sexy I looked, he even said I was hotter than his girlfriend which I doubted. My cock was hard and dripping cum. He moved closer and wrapped his arms around me and pulled me tight as he squeezed my ass. This sent chills up my spine and now we were face to face, he was getting closer and closer, I knew he was about to kiss me, I don't know why but I did nothing to stop him, my rule was never to do this but the way his lips felt on mine made me feel different. All the thoughts of this being a man kissing didn't matter.

After what seemed like an hour of him kissing me we went to the bedroom where we continued to kiss he began pulling his jeans and shorts off and then I see the biggest cock I'd ever seen, I realized then I shouldn't have broken that rule. I still remember to this day my exact words because I got so embarrassed. I set on the bed and just looked at it, saying "My god your huge! How big are you?" Even under heavy makeup I'm sure my face was red. He grinned and said 10" I shook my head and said there is NO WAY I can take that in me. He walked over closer to me and said "yes you can". I knew I couldn't, and for some reason I wanted to touch and suck it (another broken rule). I began playing with it. I thought how warm it felt and heavy it was. I played with like I do my own and when I was ready I took in mouth. The first thing I noticed was the taste of his the pre-cum, it was sweet and salty. It was so big I couldn't take much of it, it stretched my mouth so wide it hurt, but I began sucking him and before long he was going crazy. He accused me of this not being my first time doing this, I'd had women suck mine using their tongue in such way it drives you crazy, so I was doing it to him!

Knowing I was this good and making him so horny made me feel special for some reason. I was also very motivated to get him off because he wouldn't want to fuck me then. But just about the time I thought he was about to explode he pushed me away saying I had to stop or he was going to cum. I said I want you to and took it back in but he pushed me away again and said it's time you lost your cherry. I said, really I cannot take it, I told him I barely can take my little 5"er. He grinned and pushed me back on the bed crawling on top me and kissing me again. He had one hand under my skirt playing with my balls. He stopped kissing me and asked are you going to let me fuck you? I said no, and he'd start kissing me again. Finally, I was so horny when he asked again I said yes, I said as long as you'll be very easy with me I'll let you try. He said not to worry. He raised my legs and lubed us up and he began trying to put his monster in me. He tried and tried but it didn't seem it was going to happen; he was too big. I said just let me suck you off instead. He told me to relax and everything would work. He kept trying and I thought he'd lose his hard on and give up, but he didn't.

Then I felt the worse pain of my life, it was the head of his cock sliding in, I let out a loud scream with get it out! He said just wait it'll stop hurting. I laid there feeling like his arm was in me. The pain did ease and he pushed more in me, every time I'd scream and tell him to stop. Finally after a lot of patience he got all 10" in me and just held it there. He was telling to me relax and breath, but that's very difficult with a thick 10" cock in your ass. But soon I had very little pain and he began slowly fucking me. It hurt at first, it made me feel like I was going to shit myself or something, but as the pain left and that feeling went away I couldn't believe how good this felt. I looked at his face while he fucked me and seen he was loving this and knowing I felt this good to him made me feel like a woman and this wasn't a feeling I'd expected to have, and I found myself thinking how good it would feel for him to cum inside me. I tried to wait until he came but I made the mistake of grabbing my cock and stroking it. I came so quickly and so hard I seen stars and cum shot all the way up to my face, I hadn't done that since I was in my 20's. Just as I finished cuming he pulled out really fast shot his cum all over my hand and cock. He was great.

After he left I started feeling weird. I got to thinking about how I let him kiss me. I thought about his facial expressions as he fucked me and my liking knowing my pussy was good for him. These were not something I'd expected I'd have, I figured I'd either like it or not but nothing else. I thought I'm really gay! I loved being fucked and I really liked sucking his cock. For the next several days I thought about this. I didn't answer any emails and didn't even dress. I couldn't have let anyone fuck me anyway, I was too sore, but I tried to figure all this out. The next day while sitting at work I could feel my hole throbbing trying to get back normal. This made me both excited and repulsed. I tried looked at other men when I wasn't dressed and try to think about them as sexy and what it'd be like to be fucked by him, but I couldn't, it was too repulsive.

Then about a week later I dressed again, by now I was over the soreness and really horny, I'd planned on just doing myself. After getting dressed and looking at my emails I found myself thinking about men as sexy and how good it'd feel to be fucked by that cock. Then it occurred to me, when I dress I think like woman. It took some time but I came to grips with it and even began liking this feeling. It allowed me to be totally free and do anything I wanted. I even began making a list of all the things I wanted to do. I wanted to watch a man's face as he came inside me. I wanted to taste cum for the first time. The list was long with all the things I wanted to do. And I did all of them and more. I also developed fetishes for things I didn't even know you could have, I learned most of them by doing things for men.