My life...a sissy-cuck in the making.

Lets say highschool was not my strong years. I was a wimp then and most people new it. I was not as big as the other guys nor did I have their confidence. I hated showers after gym and I was not exactly athletically inclined. Worse part is I was tall but so thin and uncoordinated. At parties I never hooked up but all my friends did. One in fact relaxing with the girl I brought to the party.
It was during this time that I would dress and watch porn and make sex calls. I was often home alone so this was always something I could do. I even would go out at night dressed in a one peice girls bathing suit and a towel hoping to be caught by someone but it never happened.
Well one night I was in the middle of rubbing myself and watching some of my dad's porn when my younger brother came home and caught me dressed. I was so into what I was doing I did not hear him come in. Well he didnt laugh right off the bat but he sure knew what he wanted. I swear it took seconds for him to take out his cock and have it in front of my face and he had me sucking it before I knew it.

Oh, this is going to be very good... please do continue!
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Many more times throughout my life my brother has made use of my mouth. In fact he still does today.

Eventually we went our seperate ways and I eventually convinced a girl to marry me. She had been in a relationship with a rather controlling philandering man. So I guess in me she saw the opposite. we were married. had 2 kids. But my addiction to porn and dressing would be my downfall.

After being caught many times making expensive phone calls and buying porn when we didnt have much money led to her having more and more control over me. Our sex life consisted of me licking her pussy wearing lingerie and then her telling me a cuckold fantasy while i jerked off in the corner.

I was made to wear lingerie under my clothes. Always having to agree with her in public no matter what...always with the fear of being discovered.

nice addition! looking forward to more!
Wannabe - see my captions at http://www.cuckoldplace.com/27_74912_1.html

So, two years into being married. Nicole came home to catch me dressed un her clothes. In fact it was the outfit she wore the day after our wedding to brunch for the gift opening. It was white with lace...tight stiruppants with a bolero style jacket with shoulder pads. under that I was wearing lingerie i had bought for her.

She was visibly upset. Unbelieving of what she was seeing. Was very upset. I remember kneeling in the living room begging her to not be mad and not leave me. It was a long night of confessions on my part and telling her if she indulged with my crossdressing the porn addiction would stop and so would the phone sex calls.

Almost right away things changed. She became more demanding. Sex was always on her terms. Me licking her for hours. I remember in the begining her slapping my face when I wasn't licking her right. She would soon begin telling me about people we knew who turned her on. I was secretly turned on by all of this. Sometimes she would have me buy a playgirl mag or 2 and we would go through the pics and chat about it. I did everything around the house. All the cooking the cleaning diaper changing...everything.

Soon on Friday nights her friends would drop off there kids and I would babysit while she went to the local bar. I might also mention that it was almost right away that she had me wearing lingerie under my male clothes. This helped her in controlling me. Back then the fear of discovery of being a crossdresser was frightening and exciting to me all at the same time. Every Friday night consisted of me licking her pussy while she tells me who was at the bar. Who she danced with. Then she would fall arelax. This went on for years.

Keep going...

please continue this is great stuff !
Peachy

Thank you so much for sharing. I'm really enjoying the story of your life (how often can someone say that?) Your younghood and adolescence really has remisterance with my own, which I find fascinating.
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hot! I love how this is progressing.
Wannabe - see my captions at http://www.cuckoldplace.com/27_74912_1.html

After her orgasms she would turn over and go to relax. Sometimes not even a hug or kiss goodnight. And always with the instructions not to touch myself. I would lie there with a hard cock tucked away in my panties trying to relax and when I did it was a dream filled with cuck and cross-dressing fantasies.

After 5 years of marriage I was not the same permister she had married. I had shaved legs and underarms and shaved crotch. Wore more and more feminine clothes. Her fantasies became way more detailed about how she would fuck people we knew. How much more manly they were and how they probably knew how to satisfy a woman like her. I spent many hours licking her pussy. By this time she had me kissing her feet. Doing her pedicures and manicures. She made sure that any hobbies I had were feminine. Things like taking a cooking class or yoga. All things her brothers used to tease me about and I had no choice but to say I liked doing them.

Her pussy was the center of attention for me. I still remember licking it and how she always made me feel so effeminate while I did. One time we had gone to Montreal for a trade show for the company I worked with. My boss John was everything I was not. He worked out had a trophy hot girlfriend. Drove a nice car. So needless to say during the show that weekend I watched as she flrited with him all the time. The 3 of them would take off for hours leaving me to run the kiosk we had at the show.

On the Saturday night she and I went out on the town. She was looking so hot and I felt so ridiculous wearing a bra, panties and nylons under my clothes. My toenails painted a nice shade of pink. It wasnt long we found ourselves in a strip club about to watch an all male review. I was the only guy in the place. For 3 hours we stayed there and watched guy after guy get naked and her asking me all kinds of embarassing questions. Like was I hard ( I was) was that one attractive, wouldnt you like to suck that huge cock...on and on.

When we got back to the hotel room. I was between her legs licking her pussy, and then she started with how she wnated to fuck my boss and she wanted me to make it happen and how she would love to ride him....I came without touching my cock that night. When she came down from her orgasm and noticed how wet my panties were....she laughed and said ..OH well....You have been so good lately I was going to let you stick it in me tonight but I guess seeing all those cocks was just to much for you...lol.....

Now for the next 2 or 3 years things remained pretty much the same. Her dominance over me increased as did the amount of time I spent wearing womens clothes when I was home. The kids being young didnt really notice my apparel and this suited Nicole perfectly. She had gotten a new job and was moving up quick at the new company. No she wasnt relaxing with anyone yet but that would soon change.

You see Nicole had made it so that every Thursday night I would have to tell her another secret I had or had to share some experience with her of what I was like before she met me. By the 8th year of our marriage she knew everything about me. The dressing, my activities with my brother...which by the way she thouroughly enjoyed...she laughed often about this.

Well one Saturday I was in the house cleaning the washroom doing laundry, the usual household chores I did on Saturday while she sat on the deck in the backyard. Shortly after lunch my brother showed up for a visit. Something he occasionally did when he had the kids. Now, our relationship since I had gotten married was pretty normal. He was still the dominant one but he did not exert his influence on me like he did when we were younger. This day would prove to be different.

oooh, nice, I like the cliffhanger entries! Leaving us wanting MORE!
Wannabe - see my captions at http://www.cuckoldplace.com/27_74912_1.html

I was in the house watching the kids. Yes both our 2 and my brothers 2 kids. While she and him were outside having takes. I knew there was something up when my brother had just walked into the house and went out to see her, knowing I wouldn't say anything. 3 hours later they came back in and with a wicked smile Nicole told me she was going to the bedroom with my brother and that I should make sure they not get disturbed. My brother was laughing and grinning never saying a word just grinning and laughing. I felt a knot in my stomach like nothing before. I was speechless. Couldn't move. Just stood there as they went upstairs. I don't know why but I got the kids settled, and then sat on the bottom step trying to hear. Afraid to go up the stairs and have them hear me. They stayed up there for 2 hours. And yes I did hear some screams and moans from both of them. My brother came downstairs and told me Nicole wanted to see me and he would watch the kids. Well when I got to the room there she was spread her hand over her pussy. She asked me if I knew what she was thinking and I nodded yes. without her even saying a word I got on my knees and started cleaning her pussy. It was swollen, red and oh so full and covered with cum. her hand on the back of my head, practically humping my face she came...and then slapped me told me to go and wash up and get the kids ready we were going to my parents for supper.

OMG! So the FIRST time she cuckolds you was with your BROTHER!!?? WOW!
Wannabe - see my captions at http://www.cuckoldplace.com/27_74912_1.html

To say the drive to my parents place was awkward would be a huge under-statement. I didn't know what to feel. I was shocked at her boldness, but yet it turned me on. Her casual demeanor like what had happened only a few short minutes ago was normal. I was floored, speechless for most of the drive as I sat there. I spent most of the drive there trying to hide my erection. I didn't know how she would react if she knew I was that turned on. But yes I was. Some of you will know exactly what I felt. That anger and jealousy and being turned on and humiliated all at the same time. Knowing that every minute that went by was her securing her role as my complete superior. Just before getting there she finally said something. She said what happened today would happen again. Maybe with my brother, maybe with someone else but it would happen again.

VERY well done sir!

So the visit to my parents was as usual an embarrassing time for me as Nicole always acted and talked in a way that it was obvious who was in control. When we got there for example, I carried all the baby stuff in. Took care of all diaper changing needs while we visited and she insisted that I always clean up after supper. If I even hesitated in any thing she told me to do or didn't agree with her right away she would give me that look that meant she would have no problem pointing out to everyone that I was wearing lingerie under my clothes.

This particular Saturday night my lady's co-worker ( a teacher) was also there and he was openly gay. A situation that greatly amused Nicole as she would tease about how Marcel would use me if he knew I was the little sissy she knew I was.

That night when we got home she had me play with my penis while she kept telling me all the sexual things I could do with Marcel. Like how big was his cock. Did I look at his crotch. he had a nice package from what she would say. Then she laughed when I shot my load in my hand. After she had orgasmed from me licking her pussy she informed me that her ex-bf ( a guy she lived with for 4 years ) was coming to visit the following weekend.

Incredible stuff!!!
Wannabe - see my captions at http://www.cuckoldplace.com/27_74912_1.html

Now, before I get on to the weekend her bf Mario came to visit. I will explain some of our day to day routine we had during the week. We both worked at this point as both kids were now in school full time and we had my parents to babysit for us whenever we needed them to. I worked nights and she worked days.
It would go something like this. Sunday night at 11 pm I would leave for work. In the morning she would get the kids off to school and then she would leave for work. I finished usually before noon sometimes later. When I got home I would do any housework that needed doing and get supper ready. Get the kids at the bus stop and then wait for Nicole to get home. Then we would have supper. Afterwards i cleaned while she went to watch tv or play with the kids. After this I would bathe the kids and put them to bed and then get a nap myself. Then at 11 oclock the whole thing would start again.

Like a good submissive... very nice.
Wannabe - see my captions at http://www.cuckoldplace.com/27_74912_1.html

Please post pics of your wife.....
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Well it was Thursday night and I was getting ready to go to work. Nicole was in a very happy, giggly mood but I could tell it was not directed at me. She had taken tomorrow's shift off. Her ex-boyfriend Darren was going to be arriving around noon on Friday. That night I left the house wearing pink lace panties, nylons, a push up bra that matched it all and she insisted to spray me with her perfume before I left. The whole night I worked all I kept thinking about was her ex-bf arriving and that he would be in my home by the time I finished my shift. I was both looking forward to meeting him and dreading it all at the same time.

In short....I was a mess....

That Friday when I walked into the house and saw them sitting in the living room...nothing sexual was going on but it was the way they were laughing and chatting....I swear it was intense. I was no sooner in the door then she instructed me that Darren's bags were still out in his car. I knew better and for some reamister just turned around and went out to his car and got his stuff. Only when I had brought everything in did she finally introduce me to him and then shooed me off to the kitchen to get the dishes done and finish my work and then we were all going to go out for supper as soon as the kids got home from school. At one time while we were alone she told me that we would introduce Darren as Uncle Darren to the kids. To make things easy as he would be staying here for 1 week.

keep writing, its great that you share it with us