How I became a sissy.
I started out like any other person by wearing my sisters panties when I was around twelve years old. The more I wore them the more I wanted them. Silky smooth panties that felt so good and gave my cock a stiffey. I had only two pair but that was all I needed at the time. We lived on a farm so going into the corn field where no one could see you was the place to get naked and were only panties. Walking around in a large corn field where it is over your head is like a huge maze. Try finding where you left you clothes, some times became a game which would turn into a challenge. Once it took me two hours to find them.
Eventually I obtained another one or two articles of clothing. I continued to play by my self in this manner until I became seventeen when I started dating. I quit dressing all together in female clothing at that point. I had girls to be with and it took my mind away from cross dressing as I explored the female body. This was until I graduated from school and obtained my first job. Which after six months took me on the road.
When I was on the road for my job I found found adult book stores and would frequent them any chance I could. I became obsessed with adult magazines and found the adult world of Transsexuals. This was the best sex pictures which I could never get enough of. I thought the shemale was the most beautifullest body I had ever seen and still do to this day. A female with a cock, I so wanted to be with one of these girls. I just adored them.
I eventually married a girl from my home town at age twenty one. I confided in her I was a cross dresser after we were married. She accepted it but was not really into it. Sometimes she would buy me panties or point out something for me to buy. But that was the extent of it. I still frequented adult book stores where I would sometimes were my panties under my jeans. I remember I suck my first cock in and adult book store and many more over time.
I now started working in a factory and became restless of the same day to day grind. While sex was good with my wife, it never progressed any farther than just that "sex". I started meeting other girls at my job which would flirt with me. One in particular showed way more interest than any other. Her and I ended up having an affair which lasted six months until I became careless and was caught. That ended my marriage and I didn't blame my wife, she was in every right and I would have done the same thing if it were me.
I ended up with no one by time the divorce was over with. I did have a small collection of female clothing which I started to wear again. Even though I dated several women I still dressed in privet. I had dated two women over a period of five years when I met my third girlfriend. She dressed with more reveling clothing and I was turned on by that. I told her I cross dressed and she thought it was neat when I did. With her help I was passable in public which and we would both go out of town together with me dressed being cross dressed. I would look forward to these weekend dates but they came with a coast. She wanted to sleep with other guys and relished having me as her cuckold. This was the trade off for letting me be a cross dresser.
I agreed to it, so when we went out of town with me dressed as a girl and her looking for a Man it always ended up her getting laid while I watched. We would get a room for the weekend with two beds. This way she could spend the night in her lovers bed while I slept in the next bed. Our relationship lasted for five years in which four and a half of them I was a cuckold in the relation ship. On occasions I would be allowed to have sex with her after her lover. I became addicted to sloppy seconds and found them to be the pinnacle of sex. After some years she became tired of coming home to a cross dresser. Eventually she found herself a "Real Man" it all ended.
My next girlfriend I met in an add for singles. She lived three hours away in the next state. The first night she came to visit she took off her shirt and we slept together. She was very attractive and she knew it. Not wanting to end up dating for a long tome and then getting dumped because of my cross dressing, I told her about it at our third meeting while out having a few drinks. Once back to my place she insisted in seeing my collection of clothing. She didn't believe I was a cross dresser but she admitted having a friend in the past who was one. Once I showed her my some what large collection of clothing she had me try on articles of clothing she would pick out. He comment was, "They all looked like slutty outfits". I told her I likes the slutty look as she smiled.
After a couple of months she moved in with me. She took charge after about six months of living with me. She sat me down and told me since I was a cross dresser and if I wanted to continue to cross dress than I had to shave my pubic area, under my arm pits and my legs. The rest of my body was already hairless. Once I came home from work and showered, I was expected to cross dress every night. This was the new normal for me doing these on a daily basis. Three months into this I was sat down for another talking to. She told me since I was doing so well, she would fix my hair and makeup and take me to the city dressed as a girl. Over the next year once a month I went out cross dressed wearing slutty outfits.
Then came the next talking. I was asked if I was a sissy? I told her I was a cross dresser not a sissy! I was informed I was indeed a sissy and I needed to accept it. This is when she started to humiliate me, every so often she would degrade me. Little did I know she was conditioning me. She would say things like, "No Man would dress like that"! or she would say, "you are nothing but a little sissy aren't you"? She kept pointing out on a regular basis I had a "small penis". She sat me down after four months of this for another "Talking to".
She laughed at me calling me a phatic sperm slurper. Then telling me to go look at myself in the mirror. She stood behind me and pointed out how I was dress in lingerie. How girly I looked with such a small cocklit no one would ever consider dating me again. During this discussion she told me I needed to be castrated. I asked her why did I need to be castrated? She told me, I did not need my balls any more since I would no longer be having intercourse. I started to actually cry hearing this. I told her no I didn't want to be castrated. Well you need to be castrated! I asked at this point if I could have breasts then? She looked at me and asked why did I want breasts? I told her if I was going to have to be castrated than I wanted breasts. I will need to think bout it, was her answer as she left the room while I continued to cry silently.
Now I felt like the sissy which she had always been saying I was. I went to the bed room and laid there crying for the next ten minutes. She came in the bed room asking if I needed to be put in diapers? I asked what she meant? Well if your going to cry like a baby I will have to start making you wear diapers. No, no, I don't want to be put in diapers. Then be a big girl and come out to the living room, which I did and sat down. After a few minutes she asked, do you know your a sissy? I told her Yes, I know I am. Well as a sissy there are certain things a sissy doesn't do and other things a sissy should do. I asked what were the things she was referring to. I was informed I should have my little penis locked up. I should never plan on having intercourse ever again. She would need a Real Man to have sex with. I would need to get used to that and accept it. You will always dress like the fem sissy you are. Then she asked if I was interested in men at all? I was surprised by what she asked and told her no I was not interested in men.
Over time she kept reminding me what a phatic sissy I was and how she needed a Big Cock. Then she started saying things like, I know you would like to be with a Man. I knew she was testing me but I refused to say I was interested. But over months of similar constant programming, she had me admit I wanted a Big Cock to suck on. She smiled from ear to ear and told me I could masturbate and eat my commies if I wanted to. You know darn good and well that is just what I did as she watched. When she told me all sissies like cock and she knew of a Big Cock for me to suck, I shot my cum into my hand and ate it. Her disgusting look at me, I knew it pleased her seeing me eat it. She told me her old lover had a Big Cock and she would call him to come and spend a night or two with us.
The next day I could here her talking to some one on the phone and I knew it was some one she was planning to have sex with by what she was saying. I picked up on of the extensions phones and listened in. She stopped talking and asked who was on the line? I told her it was me. She said, Dale don't worry he is the one who wants to suck your cock. Will you let his suck your cock. I don't know the voice on the other end answered. I hung up and let then talk. When I seen her next I asked if he was coming to visit. She told me he was hesitant about having a sissy suck his cock. He is a manly, man and wants me to come and visit him she said.
She went to see him three weeks later but according to her they never met up as he had to leave to go some place due to his work or so she said. I asked her if she would keep me if I was castrated and had tits? What do you mean she asked? If I do as you want and get breasts will I get to stay with you? What happen if I meet someone and live with a guy she asked. I asked if I would get to stay with them as her sissy? What about the guy she asked? I had been so brain washed by her I answered, I will suck his cock when ever he wants me to. Hmm, I will need to think about it she answered.
Three weeks later she told me she could not stay with a sissy faggot like myself and she needed to find a Real Man with a Big Cock. She no longer had any need for a faggot like me. Than what about me I asked? Well you will need to go find a Man of your own. You want to be a girl and now is the time for you to find a Man of your own she said. Continuing she added, you know you want a Mans Cock to Suck. You will have the opportunity now to date some one.
She left and I never seen her again. I said in the beginning I had suck a few cocks but had never told her. I often wondered if it would have made any difference had I told her about it. I thought about everything she had said. I did look good as a girl and was passable. I actually did go out with a couple of guys who I slept with. One particular guy was a Cuban whom took an interest in me. He had a Big Cock which I always wanted to suck. He was a mouth full and when he wanted to have intercourse with me I told him I had never had such a big cock in me before. I was afraid he would rip me with his size. He assured me he would go slow as he sat in a big arm chair with me on my knees licking and sucking on His Man Cock.
Looking up at him I kissed his Cock as he told me to come and sit on his it facing him. Once I straddled him I lowered myself down slowly as it entered me I gasped, he told me to relax and sit down on it. I managed to plant myself on his cock and I put my head on his shoulder panting. You okay he asked? Yes, I answered while nuzzled into his neck like a lover. He slowly fucked me and I responded by humping his Big Cock while he masturbated my little cock in rhythm to my humping his Cock. When he climaxed I did also and started to shake uncontrollably. He asked again if I was all right? I told him yes, that was the best sex I had ever had. He took me to bed and fucked me again the next morning. I kissed him good by and he told me to come back again giving me his phone number.
I had to really make a decision if I was going to continue to be a sissy cock sucker or turn my life around. Even though it was the best sex I had ever had I never did go back. I would be lying if I said, I never thought about it. But in the end I decided to try and be some kind of a man again. I still cross dress and I relate to myself as a sissy on internet dating sites. I have been with more men but I do date females also.
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