How did the 'Sissy' experience develop for you?

How lucky both of you were, do you still think of him? Did you guys have sex?
I think of him a lot. Childhood memories. Even though I was a sissy I was good with mechanical things and had access to my uncle's tool shed. I had a bicycle I liked to work on and often went to the town dump where sometimes an old broken bicycle could be found which I took home. I would collect parts and eventually be able to construct a makeshift bicycle. This bike I gave to my friend even though he had to keep it at my house. We would go out on bike rides after exchanging clothes and pretend to be boyfriend and girlfriend. One day we were out in the country side and found this old abandoned barn so we explored it. It occurred to us how private the place was and the topic of sex came up. It probably helped that we found an old porno magazine stashed there, probably the remnants of some teen boy who once visited the barn like we were now doing. Some of the pages were stuck together,LOL. Anyway we looked thru it and found a picture of a woman giving a blowjob to this guy. Well this was our que. He asked me if I really wanted to be his girl. I knew what he meant. We were both very nervous but horny . This was the first this I ever sucked cock and after that we often returned to the barn. I started dressing more and more like a girl.
 
I havent really indulged it to a great degree yet but I may don a pair of panties for the arranged hook up in the new year. The potential excitement level is already very high because it will be with an ex of my girlfriend. He apparently has a huge cock to compare with my tiny dicklet and I get an extra kick when the other guy involved is a former lover we havent engaged with before.
My gf has suggested I wear panties before but I have so far not conceded even though the potential sph thrill is very enticing. The really major new territory is she wants to watch me suck his cock after he fucks her. I have never seriously considered taking that step but again the sph thrill of her watching me suck his massively superior cock and submitting to the 'better' man this way is a powerful enticement. The thought of Doing this while my tiny weeny is encased like a clit while wearing panties is extremely arousing so I will at least have to explore it for real.
I hope you take the leap. It will be a life awakening experience
 
IMO most people are bi,it just depend on how bi they are. I think most guys are so afraid of being "queer" they don't allow or are unable to explore their bi feelings. I was curious for a long time and after I sucked my 1st cock it was very liberating and soon I accepted I was bisexual. Works well for me, I now love cock as much as pussy, but most of the time I prefer pussy and only crave cock every 8 weeks or so. Once I suck my friends big cock I'm good for another 8 weeks.
Wow that sounds hot
 
My experience started with losing a bet to my fiancée - I had to go to biggest / busiest store in the area and look through the panties - buy some and then wear them . We both found we liked that - life took its toll and we split due to her cheating and lying to me - a real cuck opportuity missed for real maybe - who knows . Once single again I started maybe through boredom during the dark winter months to experiment with other womens things , make up , clothes , shoes , wigs etc . Got a real blast from buying all the things a man really shouldn’t buy and over time ‘Sharon ‘ was constructed with feelings of guilt , rage , excitement and adrenaline . I found I felt happiest doing just ordinary things dressed like an ordinary woman and everyone wants to be happy right . I’m sure anyone who is a cd will relate to purging there wardrobes or abstaining from dressing etc. ( and there is a difference from sissy guys who wear panties to a crossdresser ) .in fact I wanted to be honest with my girl at the time ( now my wife ) so cooked her dinner once early on in the relationship fully dressed . I have never had and still don’t have any interest in other men and the mixed emotions that all come from being interested and doing the things that a woman should and a straight man shouldn’t are still there but more in the background now as it all does make me happy inside but equally happy being a guy and have no interest in being a full time woman . My wife I think sort of grudgingly supports me in my dressing and sometimes confusingly assists and encourages it - she simply says - wanting to be a woman is inside of me ? . Would I do it again - absolutely the feeling of being fully made up and dressed up is just fantastic in every sense , however I realise as I get older IT WILL have to all end and I’m ok with that - I hope my inside viewpoint of being a crossdresser is of some use to anyone .
 
For me, as far as 'sissy', I've been fascinated with girls anatomy, dressing and their power since I was about 6 yrs old.
when playing games with kids on the street, I was either the leader, or the female side-kick.
I've dressed up in my wife's clothes when she was at work and I was home, without her knowledge.
It's pretty amazing that being a female, one has the power to say yes or no; like being a submissive, one decides whether to play or not.
also, I loved the fact the females could have multiple orgasms, just about anytime they wanted.
so, as things evolved, this slowly was brought out to my wife, and a little shocked at first, she gradually warmed up to the idea and what it meant to her; she had control over me and I was okay with that.
being a 'sissy' to me, means I can indulge myself with nice, Lacey things that are soft next to my skin.
also, when my wife and her bull see me, we all know our place, like a play on the stage; we're the actors and just enjoying the play as it develops.
In public, with friends and family, no one knows.
In private, things do get wild and a little extreme.

right now, I'm wearing a nice corset bra in leopard print, along with a chastity cock cage with a flat head piece; very comfortable. hope this helps...
Definitely a cute tush and legs!
 
i can't imagine how i would look dressed as a woman. i have seen some guys that are tall & thin & they look great. that would not be me. i, do, wear panties daily. i tried thigh highs but couldn't keep them up.

plus, i'm too old to try this, now.
 
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i can't imagine how i would look dressed as a woman. i have seen some guys that are tall & thin & they look great. that would not be me. i, do, wear panties daily. i tried thigh highs but couldn't keep them up.

plus, i'm too old to try this, now.
Same here but when I was young I could pass in public but some people still read me. It took a lot of work to get there however. As far as thigh highs you need to use suspenders with them. There is also pantyhose which may not be as sexy but still nice. I love how they feel under jeans.
 
For me, as far as 'sissy', I've been fascinated with girls anatomy, dressing and their power since I was about 6 yrs old.
when playing games with kids on the street, I was either the leader, or the female side-kick.
I've dressed up in my wife's clothes when she was at work and I was home, without her knowledge.
It's pretty amazing that being a female, one has the power to say yes or no; like being a submissive, one decides whether to play or not.
also, I loved the fact the females could have multiple orgasms, just about anytime they wanted.
so, as things evolved, this slowly was brought out to my wife, and a little shocked at first, she gradually warmed up to the idea and what it meant to her; she had control over me and I was okay with that.
being a 'sissy' to me, means I can indulge myself with nice, Lacey things that are soft next to my skin.
also, when my wife and her bull see me, we all know our place, like a play on the stage; we're the actors and just enjoying the play as it develops.
In public, with friends and family, no one knows.
In private, things do get wild and a little extreme.

right now, I'm wearing a nice corset bra in leopard print, along with a chastity cock cage with a flat head piece; very comfortable. hope this helps...
I've always fantasized about how it would feel being a woman and getting penetrated and filled with a big cock inside me and having a load of cum injected inside of me instead of the other way around. I always envy how girls only have to lay there submissively enjoying being dominated while the guy does all the work. Dressing properly as you said does set the stage for our prospective roles and I love how my wife sees me as a weak sissy while her boyfriend is the strong virile man. It turns me on so much when she teases me and tells me how good he is while I'm just her pathetic wimp.
 
I've always fantasized about how it would feel being a woman and getting penetrated and filled with a big cock inside me and having a load of cum injected inside of me instead of the other way around. I always envy how girls only have to lay there submissively enjoying being dominated while the guy does all the work. Dressing properly as you said does set the stage for our prospective roles and I love how my wife sees me as a weak sissy while her boyfriend is the strong virile man. It turns me on so much when she teases me and tells me how good he is while I'm just her pathetic wimp.
Surrendering and owning your needs and desires is very liberating, especially when you act on them.
 
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My first memory was when I found a pair of my sisters old slacks that she outgrew. They were so different from my boys jeans in that they had the zipper on the left hip and also little ankle zippers. They were olive green with a black paisley pattern.Inside there was a tag that said 'girls size 14'. They facinated me and thought they looked sexy. I was just discovering masturbation and started to wear them whenever I jerked off. I would wear them under my ugly boys jeans and go out on my bike to a private spot where I took off the jeans, tied them in a paper bag to my bike and went for a ride in public in my sissy slacks. It was so exciting. Later I started to wear stockings or panty hose with them. On my bike I wondered if the people I rode past noticed my nylon clad ankles with the girly leg zips. I was flying my sissy flag and it was thrilling. I my neighborhood there were no boys my age to hang with only girls. So I had a best friend Patty and 2 other girls Debbie and Peggy who I played with. I guess they considered me as "one of the girls" as I was rather feminine and had the same intrests they had. We usually played at pattys house and I was always drawn to their clothes and kind of jealous. One day the girls suggested I dress like them. I don't know how it came up but I was all for it.They were all wearing these sun suits that were popular at the time. Well patty went in her house and got one of her sun suits and brought it outside and handed it to me. She said I could change in their tool shed in the back yard. I came out in it and I was a bit embarassed but really enjoying it. The other girls were giggling but in a good way. One of them said: "Now you're a girl, just like us." We spent the day playing girls games like jump rope out on the sidewalk while the boys were in the street throwing a football back and forth. I wasn't a part of that group. Before I could go home I had to change back into my boys clothes.I hated doing that but left the sunsuit in the shed for next time. When I went to Pattys the next day It was a repeat of the day before except this time I snuck out a pair of my sisters panties that I wore under the sunsuit.
Awesome
 
Started dressing in my sisters clothes around age 10/11. She knew and privately teased me, which just made me more turned on. Around age 13/14 my best friend tols me he was gay and fancied me. I resisted at first but was really curious and tunred on. So we eventually kissed and started playing with each other. I told him about wearing sisters clothes and he wanted to see. Initallly just wore panties, but occaisionally would take a bra and skirt etc as well. he loved me sucking him off when i was dressed femme.
For years after only dressed a few times and only had a few more gay experiences at college. During first marriage dressed ni secret but once I was single again, which coincided with start off internet, I dressed a lot more and started meeting. Mostly met other cds but gradually started craving being submissive to men while dressed femme. In second marriage now, although she doens't know I dress, I crave femisation, humiliation. Work at home on my own a few days a week and dress femme all day, and gradually starting to go out wearing the odd femme item, like a blouse, or sweater, or femme jeans - things that don't attract attention immediatly but occaisionally catch someones eye who has noticed. Love the sense of realistion.

Currently in hotel wearing new lingerie
 

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Started dressing in my sisters clothes around age 10/11. She knew and privately teased me, which just made me more turned on. Around age 13/14 my best friend tols me he was gay and fancied me. I resisted at first but was really curious and tunred on. So we eventually kissed and started playing with each other. I told him about wearing sisters clothes and he wanted to see. Initallly just wore panties, but occaisionally would take a bra and skirt etc as well. he loved me sucking him off when i was dressed femme.
For years after only dressed a few times and only had a few more gay experiences at college. During first marriage dressed ni secret but once I was single again, which coincided with start off internet, I dressed a lot more and started meeting. Mostly met other cds but gradually started craving being submissive to men while dressed femme. In second marriage now, although she doens't know I dress, I crave femisation, humiliation. Work at home on my own a few days a week and dress femme all day, and gradually starting to go out wearing the odd femme item, like a blouse, or sweater, or femme jeans - things that don't attract attention immediatly but occaisionally catch someones eye who has noticed. Love the sense of realistion.

Currently in hotel wearing new lingerie
That's a lot the way I like to dress when I first started. Simply showing something as simple as nylon clad ankles and wearing jeans that were mildly femme was a big deal. I liked also like you, to see if anyone noticed. I think my mother knew I liked girls slacks better than boys, because one year for Christmas I got a pair of nice maroon colored velvet girls slacks. I loved them and was so excited to wear them to school. The crazy thing was, a girl I was friends with was wearing the same slacks that day on the school bus. She got the same pair for Christmas too. We both thought that was so cool. I was really starting to sissy out.
 
Started dressing in my sisters clothes around age 10/11. She knew and privately teased me, which just made me more turned on. Around age 13/14 my best friend tols me he was gay and fancied me. I resisted at first but was really curious and tunred on. So we eventually kissed and started playing with each other. I told him about wearing sisters clothes and he wanted to see. Initallly just wore panties, but occaisionally would take a bra and skirt etc as well. he loved me sucking him off when i was dressed femme.
For years after only dressed a few times and only had a few more gay experiences at college. During first marriage dressed ni secret but once I was single again, which coincided with start off internet, I dressed a lot more and started meeting. Mostly met other cds but gradually started craving being submissive to men while dressed femme. In second marriage now, although she doens't know I dress, I crave femisation, humiliation. Work at home on my own a few days a week and dress femme all day, and gradually starting to go out wearing the odd femme item, like a blouse, or sweater, or femme jeans - things that don't attract attention immediatly but occaisionally catch someones eye who has noticed. Love the sense of realistion.

Currently in hotel wearing new lingerie
Do you plan on trying to bring wife into it or telling her?
 
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That's a lot the way I like to dress when I first started. Simply showing something as simple as nylon clad ankles and wearing jeans that were mildly femme was a big deal. I liked also like you, to see if anyone noticed. I think my mother knew I liked girls slacks better than boys, because one year for Christmas I got a pair of nice maroon colored velvet girls slacks. I loved them and was so excited to wear them to school. The crazy thing was, a girl I was friends with was wearing the same slacks that day on the school bus. She got the same pair for Christmas too. We both thought that was so cool. I was really starting to sissy out.
The nylon clad ankles are great - done that plenty of times!

My sister knowing about me dressing was such a turn on - she'd tease me so much, sometimes leaving her panties in my bed where mum could find them. She'd ask me about them the next day, said I got hard in them and and wanked my tiny cock. I'd jusy get hard all over again!
 
The nylon clad ankles are great - done that plenty of times!

My sister knowing about me dressing was such a turn on - she'd tease me so much, sometimes leaving her panties in my bed where mum could find them. She'd ask me about them the next day, said I got hard in them and and wanked my tiny cock. I'd jusy get hard all over again!
I used to wear my sisters panties a lot to school. I loved doing that and nobody knew. It was my little secret. One day the teacher announced for all the boys to report to the nurses office. To my shock I realized it was the day of our annual physical exams. We walked in all as a group and each of us had a chair. The nurse told us to strip down to our under pants and neatly fold our clothes and put them under out chairs. So there I was sitting in front of all the boys in my class wearing pink nylon panties with white lace trim. The news spread fast and I got the reputation of being a sissy. After that I had nothing to lose so I got up the nerve to buy several panties at a store and wore them every day. The girls didn't believe it so one day a group of them gathered round and panced me in the school yard. Actually I loved the humiliation and just stood there in my embarrassment while the girls all pointed and laughed at me.
 
I just love even the slightest chance to be femme outside so as it is dark in the morning and around 5 here in Scotland just now I love to put on lipstick - some are bold shades too for my drive to work in the mornings and home again - have also worn it when out on my motorbike and couple of times eyeshadow too - my wife checks me before we go out and it’s just bliss to kiss with both of us wearing it . Always have make up wipes in my pocket as you never know
 
I just love even the slightest chance to be femme outside so as it is dark in the morning and around 5 here in Scotland just now I love to put on lipstick - some are bold shades too for my drive to work in the mornings and home again - have also worn it when out on my motorbike and couple of times eyeshadow too - my wife checks me before we go out and it’s just bliss to kiss with both of us wearing it . Always have make up wipes in my pocket as you never know
Have you ever forgot you were wearing it or forget to wipe it off and go somewhere where you shouldn't. I once forgot to take off my earrings one time.
 
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