A man becoming a woman. It’s more difficult than it sounds!
I began dressing very modestly while I was still married to my first wife. She 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. Even with the most intense sex with any woman after it was over, I’d sneak off and masturbate and I’d cum harder and more than did with the woman I was with. I’m addicted to masturbating.
My favorite way to masturbate was getting naked then spending time around the house and watching porn online until I can’t take it any longer then I would jack off. Sometimes I can go for hours but usually, I can’t and if I cum quickly in just a short time I’m horny again and I start the process over again. I really liked my alone time and made the most of it when I had it.
I’m always looking for new ways to masturbate and I’ll try anything once. while she was away for the day, I was in the middle of my masturbation session. I was searching for new porn to watch; I accidentally came across a CD. I didn’t know it was a man at first because the pic looked just like this 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! I closed it quickly and began looking at other things, but I kept thinking about how sexy she/he looked. I didn’t know men did know a man could look so much like a woman. Soon I found it again and 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, it looked so painful I thought how the hell does it take that. But because he was dressed so sexy like a woman it wasn’t like watching two men, he looked so much like a woman that is unless I saw his cock. The man was fucking him so hard that he came out a few times and he’d just shove it back in! I squirmed in my seat thinking how painful that looked. But as I was watching I was stoking myself and before either of them came I came so hard and I don’t think I ever shot so much cum. As soon as I came, I lost interest and closed it out not watching the entire thing. About an hour later I was at again this time I made myself wait until they came before I let myself cum. When I saw how he rammed deep and hard as he came in his ass I came just as hard as I had earlier. Then the cd jacked himself off and I could believe I was watching him jack off.
After that anytime I was alone I searched for videos like that and jacked off. Before seeing this the thought of men doing men made me sick, I hated it, I thought that something must be wrong with men to want to be with other men. All this made no sense! How I could watch this kind of thing and get so excited. I was so hooked on finding and looking at CDs get fucked, but I knew there was no way in hell I’d ever be with a man.
Watching all of this kind of fucking made me curious about what it felt like to have something in my ass. I was watching another CD video, he was getting pounded so as I watched I slid my hand under my ass and began squeezing the cheeks 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 and I couldn’t 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! I pulled it out and stopped! I was thinking no way in hell could I do that. But as I continue to watch I got more and more excited and decided to try it again. I went easy and slow; I guess because I was so horny now the pain seemed less now. It took a few minutes but soon the pain was gone, and it felt very good. I came as hard as I’d ever come in my life.
Then I began thinking about trying to dress in my wife’s clothes, the thought alone made me feel weird. My first concern was it would make me gay; the other concern was feeling guilty. I think I wanted to try it just to see what it felt like to have on women’s clothes. I think I had myself talked out of it until one Saturday she was gone and was going to be away until the next day. Being alone always made me very horny so that afternoon I decided I’d at least try it, I could always strip and go back to normal. I got into her closet and got a few things. I also got her bra and pantyhose. As I dressed, I did so not look in the mirror. Mostly because I was feeling very ashamed of myself. But it wasn’t affecting my excitement because I was so hard and the pre-cum was pouring out of me the entire time I dressed. I didn’t use any makeup or wigs, just clothes, I put on her bra and had to find lots of padding because she had huge tits. I’ve always had this huge boot fetish, so I wore boots, when I was finished, I walked over to this full-length mirror and I saw myself wearing women’s clothing for the first time. I couldn’t believe how sexy I looked but the feeling of her clothes on me made me very horny! So much, I jacked off as I looked at myself, and when I came my legs became so weak and I literally fell to my knees from cuming so hard. I knew then I’d found something special.
The next year or so anytime I was alone I dressed in those clothes and jacked off. I didn’t expand on it at all, I wore the same thing every time and that was good enough to make me cum hard each time. Then we divorced, not because of this but other things. I moved out alone in a small house in the country. I 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.
It took over a month before I could find the time to dress. With all the moving and other things going on, the only thing I had time for was a quick jack-off sometimes before going to sleep at night. As I would jack off I’d think about how good it felt to dress and I knew as soon as things slowed down I was going to dress again.
Finally, things did slow down but now not being married meant I didn’t have access to women’s clothes this meant now I had to buy them. I didn’t know how I could do it, but I figured they’d think I was buying gifts so off I went. I got excited knowing I was going to get something to dress in. I knew nothing about sizes so guessed. Buying them was a weird feeling but exciting at the same time. I only bought a few things so it wouldn’t arouse suspicion, I didn’t buy any makeup or anything. I bought two tops, one gray and one pink, I bought these tight little white short shorts I guessed on the size with and a short jean skirt, I also bought a long skirt and belt to dress a little more decently, I guess. I bought a pair of white pantyhose, 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.
When I got home, I laid everything out on the bed. I showered and the first thing I wore was this pink top and those tight white shorts. I stuffed to bra with the padding and when I was finished, I looked in the mirror and felt the same emotion as I did the first time I dressed. This time it felt better because all these were mine and the look of my big tits in this pink top was amazing. I could have came right then but I wanted to spend some time dressed. I sat watching porn for hours, I was so horny I’d done anything to cum. It’s like teasing myself and making me want me!
Finally, I took myself to bed. I lay there playing with my big tits. I don’t know why but I could almost feel my real tits under all the padding being squeezed. I rubbed my hands all over my body feel those sexy little shorts and my legs inside the pantyhose. I slowly unzipped my shorts and put my hand in. The pantyhose were soaked with my pre-cum. For a split second, I thought I came and didn’t know. When I touched my cock, I thought I was going to die. It felt so good inside the hose, but then is when I realized I had to have crotchless hose because I had to pull everything down to grab my cock. As I stroked my cock I played with my big tits with my other hand. I brought myself to the strongest cum I’d ever had. It just kept coming out, much more than ever before. When it finally stopped, I was so weak and my head was spinning. But as soon as regained my composure I jump up and got everything off as quickly as I good. I felt so ashamed and totally embarrassed. Here I was I man’s man I was dressing like a woman, what was happening to me?
The next day brought all kinds of emotions. I don’t know why. I never felt like this when I was dressing and married. I felt like such a piece of shit. I looked at myself in the mirror and I didn’t see a woman at all. I went to work and pretended not to care but every time I had a moment, I thought about all this. But as soon as walked through the door at home I felt excited, my cock actually got hard. I wanted to dress and couldn’t wait to get dressed. As I was dressing a little voice was asking why am I doing this? But I was shaking with excitement. I did the same thing as I’d done the night before. When I came it was just as hard and as soon as I did, I jumped up, cleaned, and got undressed as quickly as I could. The same shame and guilt came over me. But loved dressing, maybe a lot more than should have, and every time I dressed, I seemed to cum harder each time, I just fell in love with it.
After about a month of dressing, I’d feel like shit afterward even though my excitement only grew. I decided I was going to take it all the way even though I was feeling like this. I needed more things to make this happen though and I’d felt weird when checking out so this time I ordered everything online, I ordered two wigs one blonde and one long black hair, I ordered makeup which I had no idea what to get so I bought several things and I ordered some jewelry, I ordered a few more pantyhose, (all crotchless this time) and bra’s and to top it off I bought these really sexy thigh high boots with five-inch heels, I was really excited about these. They arrived one at a time, but I waited until everything arrived before dressing again. I wanted the full effect.
Finally, after over a week of waiting everything was here. I laid everything out so after I showered, I could pick out what I wanted to wear. After the shower I began putting my makeup on was so exciting, I could barely get close enough to the mirror because my cock is so hard. This should have been a clue to what I am because even though I’d never put on makeup I was very good at it. That same little voice was saying what the hell are you doing putting on makeup? And I’d to admit to myself I had the shape most women would kill for naturally. Big ass, narrow waist, and long legs. The only thing missing was boobs which now I add. I’d always been teased by friends about it even women friends and it embarrassed me to no end!
When I finished the makeup, I went to the bedroom and began dressing I wore my big tits with the tight gray sweater. I wore this jean skirt along with a pair of crotchless pantyhose. Now I had clear access to everything, I didn’t have to remove anything. I decided I wanted to be blonde, so I wore the blonde wigs. I sat down to put my boots on and pulling them up was so exciting then zipping them up was almost more than I could stand. I could feel the pre-cum soaking my legs. When I stood up I felt tall and sexy. And having never worn heels before walking was challenging, to say the least, my walk was far from sexy. But when l saw myself for the first time completely dressed, wig and makeup I couldn’t believe it was me, but I saw what people had teased me about, my body is like a woman! It even has an hourglass shape to it. Why haven’t I seen this before?
I’d planned to spend hours around the house dressed but after just an hour or less I was much too excited to make it any further, I couldn’t take any longer. When I laid down my long blonde hair felt so good. I began like always playing with big tits but it wasn’t long before I had my hand in my skirt and I didn’t last long. I came so hard it actually hurt. But just like before felt so ashamed, as soon as I came, I jumped up undressed, and showered.
The next day the guilt was far worse. I guess because I had taken it further. I told myself several times during the day I wasn’t going to dress ever again. But as soon as I walked through the door I felt this overwhelming urge that I couldn’t control. After being home just a few minutes, I was in the process of getting dressed. This became the “normal” process of things.
I began looking for new ways to make myself cum and I remembered how fingering myself made me cum hard. That night while I was masturbating, I began fingering myself. It felt so good, it took a few minutes to get over the pain though. But it was well worth the pain for me. I began fingering myself every time. I loved it and I should have realized I liked it a lot more than should have liked it.
I loved fingering myself but just like everything else I wanted more. I wondered what it would feel like to have a dildo in me, so online I went to order one, I needed a very small one and the smallest I could find was 5” with a suction cup. The night I used for the first time was the most painful thing I had ever experienced, I couldn’t take it and had to stop. I nearly gave up on it and only tried occasionally. But one night after putting on these beautiful fake nails I’d bought I became very excited. As I was masturbating, I began trying to get it in again this time for some reason I was able to take it. It took some time and patience, but I did and when the pain left the feeling of complete pleasure took over and it made me cum so hard. Once again, I felt so ashamed and cleaned up quickly. And as strange as this sounds, I still didn’t want anything to do with another man, it still turned my stomach. So, nothing about those feeling had changed and I didn’t expect them to.
Over the next few 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. The pain at first was always very bad but I knew now that when the pain left it felt so good that going through the pain was worth it. But I always felt so guilty.
A big turning point came one day when I decided to shave my entire body. I’m naturally hairy so this was quite the undertaking, I’ve always kept the hair trimmed around my cock but never shaved my body. The shame and guilt were something I’d come to grips with knowing it was going to be there no matter what I did. In preparation for my shaving, I’d 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. I could not get over how different I looked, I thought I really do look like a woman now even without dressing. I am not a fat man (or girl or whatever I am) but I’ve always had what I’d call big tits for a man and with no hair to hide them I see I have tits of my own, and with no hair, they looked almost as good as any woman I’d ever seen. I played with them squeezing them together and cupping them in my hands as I put the lotion on. My body felt so smooth and soft, it felt as good as any woman I had ever touched. I got dressed and when I was done, I felt as if something inside me was 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 woman-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 like this before I was in bed and masturbating. I rubbed my body under my clothes, and it felt so wonderfully strange, 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 see myself in bra only and smooth skin was wonderful. When I started sliding the dildo in, I noticed it didn’t seem to hurt as much. I didn’t think it was because I was used to it now, it was because of this new heightened aroused feeling I had. As I began riding it, I had this thought come to me out of the blue, I started fantasizing this was a man fucking me! I began fantasizing about me on my back being the woman and how good he felt in me. I came so hard I shook, it seemed harder than ever. When I stopped cuming I felt completely exhausted, but I jumped up and undressed quicker than normal.
Now I was really worried! I didn’t know why I had this thought. It caught me completely by surprise. I spent the entire next day worried. 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 could not stop it from getting in my mind. This scared me so bad I stopped dressing, I didn’t like what I was becoming. I went back to masturbating the old way. It was not near as good but at that time it was better than fantasizing about a man fucking me.
But because the old way wasn’t as satisfying to me now, it wasn’t long before I dressed again, every time I dressed, I had this fantasy. The guilt was overwhelming. I tested myself by looking at gay porn but it still disgusted me, I sort of felt better. But every time I masturbated, I would fantasize about being the woman in a relationship and a man fucking me. The fantasy became increasingly more vivid each time until I could almost see him on top of me.
After getting dressed one night even though I was not sure I could do it I gave in and decided I’d try it once. I sat down and wrote out my own personal boundaries. The first thing, I did not want anyone I knew finding out I dressed like this, that would have been the most humiliating thing in the world so in my ad I said nobody without a face pic first. Second, I never want to be kissed by a man and I for sure didn’t want to touch or suck a cock. I did not even want them talking to me. I just wanted to try and be fucked and see if I liked it. But my biggest limit was I didn’t want someone with a huge cock, I could barely handle my little skinny five incher and If it was much bigger than this, I wouldn’t be able to take it so I asked for full stats. And I put in it that this would be my first time ever being with a man. When I finished writing the ad and reread it, I thought this sounds like somebody that doesn’t want to do this, and that was true in a very big sense, I wanted to do it…. but not really. It seemed I had to prove to myself I hate it then I could move on and continue my normal ways if that was what I was doing.
For days of no response from anyone I began to think it might not happen, maybe nobody wanted a cd. Maybe this dressing style of life turned men off, that I was a freak or worse. This only added to my shame but when I was alone and dressed, I felt so sexy and alive.
I knew there would be no way I could go out dressed and find a man. I couldn’t see myself walking up to a man in a bar me all dressed and looking sexy and asking him if he’d like to fuck me. I had to think of something else if this was going to work. I decided I’d try adding pictures to my ad, I put pictures with my body dressed showing my huge tits, making sure my face could not be seen. Just a few minutes after posting them to my ad and from there things changed quickly. I had so many emails 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 as wanted like this by anyone. 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 strangely special and powerful. Hearing things said about me like this especially coming from men was odd and shameful. I couldn’t believe it, but I was actually liking hearing this even though it was from men. 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. I rejected many based on cock size alone I knew there was no way I could take much so anything big was out of the question and most were. At least most said they were, and a few provided pictures.
I found a few in the emails I felt I could take. Six was a common size and I felt I could take that. And from the pictures they didn’t look thick so we made plans and I was told all the time “I will be there” and then never show. Over the next week or so I began to think that even with the pictures it wasn’t going to happen. Night after night nobody came, I became frustrated. But the more I would get all worked up to try my first time seemed the more I wanted it. I’d masturbate and use my fantasy and wonder what it felt like. Not that was a problem and in a strange way I was relieved I couldn’t find anyone to fuck me. It was like I was proving to myself I could fuck myself and be satisfied so why even try. But that didn’t stop me either, but I continued answering emails every night. I was like Dr. Jekyll and Mr. Hyde.
Then one night after another no show I’d given up again and was ready to fuck myself when I get an email asking if I was still looking. He answered right back to my “yes I am”, he said send me your address and I’ll be right there. To this day I don’t know why I broke my own rule and gave it to him without asking for a face pix or cock size. I guess thought he’d not show anyway. But about 30 minutes later I heard a car pull in, and I got really nervous. I thought this may be someone I know, I peeked out of the window to make sure I didn’t know him, I didn’t recognize him, so I let him in. We stood silently at first, me too scared to say anything and he looked like he made a mistake and was ready to leave. But then he spoke, he startled telling me how sexy I looked. He said he couldn’t believe I actually looked like my pictures even better. My cock got hard quickly, and I was soaking my pantyhose. 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 thought he was about to kiss me! I turned my head away quickly. I only touch his arms which to be honest felt strange. They were big and firm, not like a woman’s soft arms. This made me realize for a moment I was touching a man in a way I never thought I would. He asked if I want to go to bed, I could only nod yes and off we went.
I laid in bed and watched as he undressed not saying a word and so nervous, I could feel myself shaking. But then he pulled his shorts off and I see the biggest cock I’d ever seen in my life! It wasn’t hard but it was huge and hanging there. I realized then I shouldn’t have broken that rule for sure. I can still remember to this day my exact words because for one I spoke which I had no intention of doing and embarrassed myself. I said, “How big are you?” Even under my makeup, I’m certain my face was red. He grinned and said ten inches. I didn’t measure it, but I don’t think there was any doubt he was at least that big! 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’ll be gentle”. For some reason, I wanted to touch it and I reached out a took it in my hand (another broken rule). The first thing I noticed was how thick and heavy it was. I played with it like I do my own and I could feel it growing in my hand. Then for some reason, the urge to suck it came over me so I took it in my mouth, it was like I couldn’t stop myself from doing things. The first thing I noticed was the taste of his the pre-cum, it was sweet and salty. I’d never even tasted my own, so this was a surprise. It was so big I couldn’t take much of it, it stretched my mouth so wide it hurt, I began sucking him and before long he was going crazy. He accused me over and over of this not being my first time doing this. Knowing I was this good and making him so horny made me feel special for some reason. I also became very motivated to get him off. I thought if I did he wouldn’t want to fuck me. I wasn’t going to let him cum in my mouth though. 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 put it back in my mouth. He pushed me away again and said it’s time you lost your cherry. I said, really, I cannot take something that big in me I barely can take my little dildo. He grinned and pushed me back on the bed. He had one hand under my skirt playing with my balls. He asked are you going to let me fuck you? I said no, he said, “you really want me to be your first because I’m gentle and others will hurt you”. I said, “I don’t think I can”, he said, “let me try”. With the way he was playing with me he’d made me so horny, I couldn’t stop. I gave in, I said if you’ll be very easy with me and stop if I say so. 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 couldn’t get in me. I didn’t think it was going to work. I said just let me suck you off instead. He told me to relax we had all night. He kept trying, I thought he’d lose his hard-on and give up, but he didn’t. He was telling me how I could help by pushing out. I tried but the fear of the pain would make me tight again. Then suddenly it happened! I felt the worse pain of my life, it was the head of his cock sliding in, I let out this loud scream followed by “get it out”! He said just wait it’ll stop hurting. I laid very still, the slightest movement hurt, he didn’t either. I was breathing hard and trying to relax. Several minutes past and the pain eased and he pushed more in me. I screamed again like a little girl tell him to stop and he did. Now I had several inches of his cock in me, and it was hurting so bad. I begged him, please let me get you off my hands I can’t take much more. All he would say was the pain will go away and you’ll love this. Finally, after a lot of patience, he got all of it in me and just held it there. He was telling me to relax and breathe, that was impossible to do with something so big in me. As I lay there neither of us was speaking and it seemed time stopped, I began thinking how this was me, lying there on my back legs straight up and a man had his cock in me! I couldn’t believe I was letting this happen, I felt ashamed but I didn’t want to stop. Soon the pain eased like he said it would. He could tell by the way I was breathing the pain was gone. He asked me if I was ready, I said I think so but just go slow and he began slowly fucking me. It hurt at first, it made me feel like I was going to piss or shit myself. But as the pain left it started feeling really good, I couldn’t believe how good this felt. I looked at his face while he fucked me and seen he was loving this, knowing I felt this good to him made me feel like a woman and this wasn’t a feeling I’d expected to have. He went very slow, pulling nearly out and slowly going back deep. This was far better than I ever dreamed it to be. The sensations I was feeling were nothing like I’d ever felt. And one of the strangest, maybe surprise more like it was I felt like I going to cum several times as he slowly went back in me. I thought my god what is he doing to me down there! I also found myself thinking how good it would feel for him to cum inside me. I don’t know why but I never thought about this aspect of it. Where would he cum. But now I wondered how it would feel to have it in me. I tried to wait until he came because I knew if I came, I’d lose interest and make him stop. I made the mistake of grabbing my cock and stroking it. I came so quickly and so hard I saw stars, I shot cum all the way up to my face. Just as I finished cuming he pulled out fast shot his cum all over my hand and cock. As soon as we were done, I was ready for him to leave so I didn’t talk much. He asked me if it was good and I told him yes, I didn’t want to tell him I loved it. Thank god he dressed and left quickly. As soon as he was, I got out of those clothes as fast as could and cleaned up. Even though while I was on my back with him deep in me and loved it, now I felt dirty and ashamed I’d let my life evolve to this.
After I got cleaned up and back into my “normal self” I felt so weird, I thought about his facial expressions as he fucked me and my liking knowing I felt this good for him. But to be honest the feeling of me about to cum by just being fucked was the biggest surprise. I didn’t even know it was possible to cum like that. Does this mean I’m more woman than a man? All of these were not feelings I’d expected I’d have. I thought I’m really gay! I love being fucked and I really liked sucking his cock. It took forever to fall asleep that night. I could feel my hole throbbing; it’s never been stretched like that. The next day at work it was still throbbing trying to get back normal. This made me both excited and repulsed. More than once I was in the restroom nearly in tears thinking what the hell am I doing. I must be gay because I liked it so much.
I put it to a test, I’d try looking at other men and think about them as sexy and what it’d be like to be fucked by him, I couldn’t stand it, it was just as repulsive as before maybe even more. I felt much better about myself and for the next several days 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 needed to try and figure all this out. I thought about quitting in fact I didn’t dress at all, didn’t even masturbate.
Then about two weeks later I decided I would only dress for myself and never be with another man again, by now I was over the soreness and really horny. After getting dressed and looking at my emails and porn and I found myself looking at men again and thinking how sexy he looked or what it’d feel like to be fucked by that cock. I was so confused, I kept thinking how insane this is and why was I thinking like this again. Then it occurred to me! When I dress I think like a woman. When dressed I look at men as sexy and my woman side wants them. I liked seeing a big hard cock and thinking about letting it fuck me. It was as if the weight of the world had been lifted off me. I jumped right into the email and now my responses to emails were different now. I was talking like a woman might if she was going to let a man fuck her. I was asking them what they’d do to me and how they liked my big tits. I was telling them I’d suck their cock better than they’d ever had. I watched men fuck other men and got so horny I went and got my dildo and sat on it while I watched others get fucked. I jacked off and came very hard. But just like always as soon as I came I jumped, undressed, and showered. I still couldn’t handle the thought of me being dressed after I came. Even though just a short time later I could have done it again I wouldn’t let myself do that. That would be like crossing a line I shouldn’t, so I’d just go to sleep and start the whole process over the next night.
It took some time to come to grips with this new way of thinking or being if you will, I even began liking this feeling. It allowed me to be totally free and do anything I wanted. I could be this normal macho man during the day and be a complete slut at night and do whatever I wanted. I didn’t have boundaries society puts on us. I could be open and completely crazy if I wanted. A complete opposite of my normal self. But what I didn’t realize was this was going to engulf the man side of me and later…. well, there’s a lot more to this story…a lot!!!!