Just reflecting on the life I've had and how it could have been so different. My whole life I've just kept my desires hidden. Even though I have wanted to dress up since I was a young boy, I could not bring myself to disappoint my family that were very homophobic.

It was the 60's and I remember my step-father used to pull his dick out and shake it at my sisters and me. My sisters were older and could not stand him, but I was young and he was the only dad I knew. Nothing sexula ever happened, but I am sure this is what started me to be curious.

Then when I was about 8, a local 13 year old girl that evidently was already having sex, brought me to a secluded spot and showed me how differet we were between our legs. She tried to get me to have sex, but as far as I can remember either I could not have an erection or I was too embarrassed.

About a year or so later my brothe, my cousin and myself were exploring an abandoned house nearby. It still had furniture and everything, but no one lived there for some time. I opened a dresser drawer and found weird clothes, like costumes. Bras, panties, etc and some feather boas. I just thought they were womens clothes so I kept rummaging through the dresser. Then I found some polaroid snapshots that really peeked my curiousity. They were of men dressed in drag. They were dressed flamboyantly and you could tell it was men, but I was very intrigued by it. I wanted to take the pictures, but I played it off so my brother and cousin would not think I was a wierdo. We all left but for days I could not get it out of my mind. Every time we walked passed that house I wanted to go back in and even suggested it once to my brother. He said naw we already been through it, so I blew it off. Finally I went by myself back in about 3 weeks later, but someone had moved everything out. I was so disappointed.

I eventually forgot about it, but always wanted to put on my sisters slips. Never did but the urge was very strong. I am sure the crossdressing seed was planted, but I was still trying to live according to my families beliefs that a man does not do those kinds of things.

Then I guess I was about 13 and Mom let me take my little brother to a game room on the bus. We all found pinball machines and began to play them. But as I was playing, a short older man wearing a trench coat, ( he wasn't naked), of about 30 or 40 was standing really close behind me. He was complimenting me on how good I was doing. After a few minutes my game ended and I started to back away. He was so close I backed right into him. Hereached across me and put money in the slot while up against me. He told me to go ahead and play some more. I said okay. His body was against me and I could feel his bulge against my butt. He draped his trench coat so no one could see how close he was and kept grinding against my butt. I don't know why, but I was enjoying the feeling of his cock against my ass, and I pushed back also. New feelings were stirring inside me. I wanted this to go further, but knew my brothers were with me. I could not concetrate on the game from this new found excitement I was feeling. I still to this day dream about a man grinding against my butt with clothes on just to feel that big bulge on my ass. Anyway I told him I had to take my brothers hom, but I will be back. He ignored me and went to the next kid playing pinball. I got my brothers and took them home. I jumped back on a bus and went back. I went to him and said I was back, but he said I was too late. Man was I disappointed again.

I knew I wanted sex now and was still to scared to be with boys, so I went after girls. I was a good looking kid but still a little shy about girls.  I was 14 now and had a neighbor that I liked alot. She was 27 and her boyfriend was a trucker so was hardly ever there. I would help her do things around the house and we became pretty close. She had big tits and was self consious about it. We were looking through her yearbook from high school one day and I told her hot hot she was. She blushed and things began to change between us. I complimented her all the time and she enjoyed the attention, but she would not let it go further. Finally one day I pinned her against the wall and kissed her. She did say we should not do this, but I was so ready and begged her. She said I was too young and I grabbed her hand and placed it on my bulge. Does that feel too young I asked her. She dropped to her knees and pulled out my cock and gave me the best blow job of my life. She told me would could not have sex because it was not right. Needless to say I got head from her on a very regular basis and found a few more older women in the neighborhood that were single and so ready for sex. I basically was a male whore for a while I guess and started to forget about those earlier feelings about men and dressing up. I got married at 21, thinking that it was time to settle down. But it's strange becuase other women like to have sex with married men because they felt it was safe and there husbands and boyfriends would not find out. Needless to say we divorced and I played around for a while until I was 32.

I was transferred to another city when I was 30. I did not know anyone and quit drinking so it was hard to meet anyone. For a couple of years I was alone and lonely. I began to think of those old feelings now. It was before the internet so I would pick up Penthouse forum and read some kinky stories to masturbate to. And yes they would have stories about everything so I gravitated to gay and bi stories. Loved the ones were a man had a dominat wife and made him dress up and have sex with men. I began to finger my ass and then started buying cucumbers because I was too embarrassed to buy a dildo. But after awhile I needed something else. I wanted to finally try a man and hopefully get it out of my system. They used to have free dating services through a phone number locally. You would call it and get recordings to choose gay or straight and then listen to recorded messages for people looking to hook up. I know it was dangerous to hook up with strangers, but I felt I was able to take care of myself should I get some crazy person and I have been holding this desire inside for so many years. And besides what harm would it be to just listen because I would probably chicken out anyway.I listened to a few and they sounded too feminine, I knew I wanted to be the bottom player for sure, so would not even think about those. Then it happened. The guys name was John. He was short and to the point. I don't play games. If you want to get fucked and suck cock leave me a message. Hmmm, I was tempted too leave a message, but hung up and just thought about it for a while. I kept thinking that was the kind of man I wanted. Someone to take charge and give me what I fantasize about. After an hour I called the line back. Clicked through messages until I got to his. I listened to it about 5 more times and sent him a recording. Yes I do and gave him my number. I figured I probably would not hear from him for a few days so had time to back out. Nope the phone rang within 15 minutes. He told me he does not want to waste his time. he will call me back at 8:30 with his address and number for a 9 oclock hook up. If I'm not ready or late to just forget about it. I said okay and he hung up. I paced and pretty much decided that I was stupid and just won't answer when he calls back. I tried to watch TV, eat some snacks, just anything to block it out, but I could not. I knew I wasn't going to do this, but I figured I better take a shower, just in case. After cleaning up it was about 8:15 and I said no way. I can't do this. I just won't answer and that will be it. I could not get it out of my mind. Should I? No Way! Back and forth. Then the phone rang. I put my hand on it but wasn't going to pick it up. Then I thought about how domineering he sounded and thought I better pick it up. So I did. He told me his address in a gated complex. I had to punch in his number at the gate and he would ring me in. Don;t be late. click. I grabbed my keys, but then stopped. No I can't do this. But then I told myself well I can at least drive that way just in case. I was shaking I was so nervous as I drove 15 minutes to his apartment. I got there 15 minutes early just to see the area, which was not a bad area ay all. I went to a store about a block away and got a soda, still deciding if I was going to do this. I drove to the gate and still had 5 minutes. I just sat there. I put it in reverse, then back in park. Back in reverse, back in park. At 2 minutes till I got out car and went to phone box. I took a deep breath and punched in his number. He said Hello. I said Hey, It's me. He told me which route to take in complex and were to park which was right in front of his door. I sat there for a second and he opened his door so I knew it was him. I got out and walked up. He opened door and I stepped in. He had on a short robe and I followed him into living room. He had me sit down in front of TV which was playing gay porn. He sat across from me near TV facing me. He asked a few thigs but I was so nervous and now watching th porn very jittery. He asked if I liked porn and I said yes. He opened his robe and stroked himself while I watched the porn and him also. He told me to take my clothes off, which I did as if I was in a trance following his commands. So you like dick? I said I never have, but always wanted to. Come here. I got up and walked over. Kneel and hold it. I did but man was I shaking. Lick it boy. I finally bent down and tasted cock. I closed my eyes and moaned. I could not wait and slid it in my mouth. Good boy. Watch the teeth. Suck it. And boy did I suck it. I was in heaven. I knew then that I need this in my life. It felt so natural to me. Sucking cock for an alpha male is what I was born for. I was in a whole new zone now. It was like I went into a different planet or dimension where I was a girl taking care of her man like she should. He scooted up and held my head as he started to push it in further. Of course being new, I gagged and coughed and released me so i could catch my breath. I quickly sucked it back in my mouth to assure him that I wanted this. You sure this is your first cock? I said uh huh between sucks. Yea well you are good at it. I loved the compliment and feeling his hand on my head, not to force it but to guide me in making him feel better. He pushed my head away and got up. He guided me to couch and bent me over the arm of it. I knew he was about to fuck me and I wanted it so fucking bad. But even though I used small cucumbers in my ass a few times, I had no idea about the pain I was about to feel. He lubed and fingered my ass which I took and moaned. This aint your first time. I said yes it is. I finger myself alot. I then felt him stepp in close. His cock was against my ass. God yes, I want it so bad. He pushed forward and I screamed as just the head popped in. I screamed and begged him to stop. It burns too much. I flailed around but he held me so I could not get away. Just relax. It will ease up. Tears coming down my cheeks I begged him to pull out. Calm down. Give it a minute. I tried calming down and he was right, the pain was going away. Hmmm, it was feeling kinda good. He could see my ass unclinch and told me, You see. Gonna give you a little more now, just relax. He pushed forward and I screamed again. So much pain, please stop. He stopped and let my ass get used to it again. And just as before the pain changed to pleasure. I actually was opening my ass up now. After a minute he pushed more cock in me and again the same results. I would scream and cry at so much pain and beg him to stop. But the pain would change to feeling so fucking good. After about 10 or fifteen minutes of this he was finally all the way inside me. I began to moan and movemy ass from side to side. Oh god I said. Feels so good. He would chuckle and tell me he knows. He began to fuck me now. Holding my hips with slow steady thrusts. I started moan and thought of myself as a woman then. Yes fuck me. So good. Damn. I babbled on and on as he picked up the pace. Please never stop. So good. Then I knew he wanted to cum because he grabbed my hips and began to fuck me deep and fast. I screamed and moaned. there was still some pain as he fucked me so hard, but the pleasure made up for it. God it was wild. I knew I was going to do this a lot more often now. He continued to pound my boy pussy and told me he was close where did I want his cum. I screamed in me. yes cum in me. I so wanted this to be the complete experience. I had to have his cum deep inside me. One deep thrust and wow I could feel him swell and explode. Yes I screamed. Another pump and more cum jetted inside me. God yes. I was so satisfied and happy to know all these years my dream of taking dick was so worth it. One last thrust and a growl as he held my ass hard over his cock draining the last few drops of cum inside me. God that's some good pussy boy. I smiled and said it's all yours baby. After that night, I would see John secretly 2 or 3 times a week. He used me as his personal whore and I loved it. I sucked his cock, drank his cum, rode that dick and got filled many times. Alas nothing last forever. I was transferred back home about 6 months later. Here I was now so secretly addicted to Johns cock but so far away. I had to go back to pretending I was a straight guy now and just dream about what could be. I was too scared to do anything near where I live as family and friends may find out that a sissy faggot lurks under the surface.