How did the 'Sissy' experience develop for you?

[maxgen373737]

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...

 

[robbiewillsucku]

In high school, I was a dom straight top who fucked the brains out of my girlfriend. Then ten years later we hooked up again and started swinging - I went from dom to switch to sub to very sub to now sub sissy-fem slut for cocks.

 

[maxgen373737]

here is what I'm wearing today...

 

[SuperSqueak]

During puberty I was washing laundry and got curious about what it would look like to put on my stepmom's clothes. When I tried it I found I was extremely excited, because I could imagine I had a girl in the mirror that I could touch and play with all I wanted. I grew out of it for a long time and kinda forgot about it. Several years later in my 20s, I ended up in a toxic marriage. After I found out she cheated on me, I started browsing Craigslist ads, which really awakened my bi side. As I looked through local ads I got more and more daring, sometimes responding but struggling to gather the nerve to go through with a meetup.

One weekend she went out of town with her family, and I had the house completely to myself for a couple of days. Temptation got the better of me, and I posted my own ad. As the night went on, I became more and more obsessed with being submissive to another man. To really embrace the idea of being a slut I put on my wife's lingerie, and my excitement amplified tenfold. I actually did find a guy to come over that night and let me suck him, though the experience wasn't great because he was too nervous to get into it much. Before he got there I had lost my nerve to wear the lingerie in front of someone else and had changed into some gym shorts. Interestingly it wasn't until after that experience that I realized I had suppressed memories of dressing when I was younger. After that I took every chance I could get with the house to myself to dress in my wife's clothes and let out my inner sissy.

I didn't actually hook up with another guy for 12 years after that, long after that marriage ended and I got married a second time to someone who accepts and encourages it. However, in the interim I still enjoyed dressing and fantasizing every chance I got.

 

[droopy1]

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.

 

[nicebiguy]

In high school, I was a dom straight top who fucked the brains out of my girlfriend. Then ten years later we hooked up again and started swinging - I went from dom to switch to sub to very sub to now sub sissy-fem slut for cocks.

Amazing how we can transition from a strait stud to a eager,sissy,cum eating, cock sucking faggot ,huh?

 

[droopy1]

Amazing how we can transition from a strait stud to a eager,sissy,cum eating, cock sucking faggot ,huh?

I think that means that we were just sissy bitches all along and in denial. It doesn't take much to wipe away that fake venier and expose us for the pathetic faggots we really are. We are only truely free when we have blistered knees and a mouth full of cum.

 

[SNJCouple]

I have always known that my gender was ambiguous and/or confusing. I struggled with it as a small child. Feeling drawn to feminine attire and more delicate things (which makes it clear to me that gender is a social construct, but that is a different post).

As a teen I was extremely delayed going into puberty and may not have had a full puberty. I struggled in locker rooms and areas where I could feel and see the differences. I was self conscious and afraid of being different. I started feeling more comfortable in circles of girls. I started experimenting with female clothing.

For me the term “sissy” became a stepping stone. It allowed me to ease into the idea of gender fluidity or being trans. I rationalized my bi sexuality and my love of the feminine as a fetish or a sexual thing.

As I have aged I have embraced who I am. I still appreciate the term “sissy” and at time when playing will use the term. I know though that for me personally my journey is more than a fetish and I have embraced my gender fluidity and possible trans status. I still struggle with some uncertainties but feel better when I can be honest about who I am.

If you have questions please let me know. Always glad to answer questions. Sorry for the rant.

 

[droopy1]

I have always known that my gender was ambiguous and/or confusing. I struggled with it as a small child. Feeling drawn to feminine attire and more delicate things (which makes it clear to me that gender is a social construct, but that is a different post).

As a teen I was extremely delayed going into puberty and may not have had a full puberty. I struggled in locker rooms and areas where I could feel and see the differences. I was self conscious and afraid of being different. I started feeling more comfortable in circles of girls. I started experimenting with female clothing.

For me the term “sissy” became a stepping stone. It allowed me to ease into the idea of gender fluidity or being trans. I rationalized my bi sexuality and my love of the feminine as a fetish or a sexual thing.

As I have aged I have embraced who I am. I still appreciate the term “sissy” and at time when playing will use the term. I know though that for me personally my journey is more than a fetish and I have embraced my gender fluidity and possible trans status. I still struggle with some uncertainties but feel better when I can be honest about who I am.

If you have questions please let me know. Always glad to answer questions. Sorry for the rant.

Not a rant at all. Very interesting. I am just like you in many ways.I had a dominant mother,an aloof father and sisters both older and yonger than me. In my neighborhood most of the boys were older than me and so I was to young to hang with them. There were girls however who were my age and so I naturally hung out with them. Instead of playing touch football I played girls games like jump rope. So that might have set the stage for my trans identity. I use to steal clothes from my sisters and mother and secretly dress up and go out on my bicycle. I got a thrill out of this and the more I cross dressed, the more flamboyant or obvious I became. I loved it when people( especially girls) saw me in my flower print slacks and maybe a lacey blouse. In spite of all of this I wasn't really gay. I was highly attracted to girls.I used to say to myself,I like girls so much that I even want to be a girl. I was in love with femininity. Like you, I embraced who I was.

 

[Jeanswatcher]

I wouldnt discribe myself as a sissy so maybe i am writing on the wrong thread, i am a cuck husband who has been semi feminised. I became so as it was my wife wish and she has said she always knew i would be receptive and knew this when she was 17.

It was my wife that first collared me to her as her lover had collared her to him, hers wasnt a permanent fitting, mine was and is and locked.
It was she that presented me with my first cage, then decided it would become a virtually permanent fitment,
It was she that asked me to wear the knickers/panties she having just removed them so her lover could fuck her and she that decided from that day i would only ever wear panties. She bought me some but now we wear each others.
It was she that asked if she could paint my toe nails pink, i didnt know she meant permanently although the colours do change at repaint,
It was she that then:
Asked me to wear the suspenders she had just removed as she laid on our marital bed with her lover and then immediately decided i would wear them as a treat,
She bought me tight female jeans for indoor wear only, then took me shopping in them, then decided i would and could wear them doing my normal vanilla tasks often with suspender underneath, just as she had done for me when 16 onwards, she later added to my collection as i have too.
She bought me female brightly coloured shorts, then matching bikini bottoms for our holidays, so all my shorts are female ones,
Then she bought me female silky pink girlie patterned PJs, then added to this pair so i now only sleep in female clothing.

That ment that i wear female clothing 24/7 365 days of the year.

All these except the suspenders i wear daily, though ive worn suspenders 4 days out of the last 5! and am now under my silky PJs, locked obviously.

Am i sissy? well i would say not.

Only in later life have i orally cleaned her, she didnt like this and neither did i, but i did it as sir told me to, several times, i wouldnt have done this in my 20s.

She pissed on me as i laid on the floor, she was directed to by sir however she later siad she didnt feel comfortable pissing on her husband laid there wearing, a collar, in chastity, matching suspenders, knickers and nails. In reality i actually quite liked the humiliation, even it took me 20 years to like some humiliation. She didnt as she viewed me as her husband not her submissive cuck which is a shame.

I am a 6ft 3 masculine dominant man at home and at work, i have often had my jean clad ass felt by women and some men! who say ive a cute bottom but what they dont know is they are actually feeling is an cute bottom encased in female jeans and female knickers. My wife wouldnt say i was a sissy but has said i am a tart!

 

[droopy1]

I wouldnt discribe myself as a sissy so maybe i am writing on the wrong thread, i am a cuck husband who has been semi feminised. I became so as it was my wife wish and she has said she always knew i would be receptive and knew this when she was 17.

It was my wife that first collared me to her as her lover had collared her to him, hers wasnt a permanent fitting, mine was and is and locked.
It was she that presented me with my first cage, then decided it would become a virtually permanent fitment,
It was she that asked me to wear the knickers/panties she having just removed them so her lover could fuck her and she that decided from that day i would only ever wear panties. She bought me some but now we wear each others.
It was she that asked if she could paint my toe nails pink, i didnt know she meant permanently although the colours do change at repaint,
It was she that then:
Asked me to wear the suspenders she had just removed as she laid on our marital bed with her lover and then immediately decided i would wear them as a treat,
She bought me tight female jeans for indoor wear only, then took me shopping in them, then decided i would and could wear them doing my normal vanilla tasks often with suspender underneath, just as she had done for me when 16 onwards, she later added to my collection as i have too.
She bought me female brightly coloured shorts, then matching bikini bottoms for our holidays, so all my shorts are female ones,
Then she bought me female silky pink girlie patterned PJs, then added to this pair so i now only sleep in female clothing.

That ment that i wear female clothing 24/7 365 days of the year.

All these except the suspenders i wear daily, though ive worn suspenders 4 days out of the last 5! and am now under my silky PJs, locked obviously.

Am i sissy? well i would say not.

Only in later life have i orally cleaned her, she didnt like this and neither did i, but i did it as sir told me to, several times, i wouldnt have done this in my 20s.

She pissed on me as i laid on the floor, she was directed to by sir however she later siad she didnt feel comfortable pissing on her husband laid there wearing, a collar, in chastity, matching suspenders, knickers and nails. In reality i actually quite liked the humiliation, even it took me 20 years to like some humiliation. She didnt as she viewed me as her husband not her submissive cuck which is a shame.

I am a 6ft 3 masculine dominant man at home and at work, i have often had my jean clad ass felt by women and some men! who say ive a cute bottom but what they dont know is they are actually feeling is an cute bottom encased in female jeans and female knickers. My wife wouldnt say i was a sissy but has said i am a tart!

We sometimes tend

I wouldnt discribe myself as a sissy so maybe i am writing on the wrong thread, i am a cuck husband who has been semi feminised. I became so as it was my wife wish and she has said she always knew i would be receptive and knew this when she was 17.

It was my wife that first collared me to her as her lover had collared her to him, hers wasnt a permanent fitting, mine was and is and locked.
It was she that presented me with my first cage, then decided it would become a virtually permanent fitment,
It was she that asked me to wear the knickers/panties she having just removed them so her lover could fuck her and she that decided from that day i would only ever wear panties. She bought me some but now we wear each others.
It was she that asked if she could paint my toe nails pink, i didnt know she meant permanently although the colours do change at repaint,
It was she that then:
Asked me to wear the suspenders she had just removed as she laid on our marital bed with her lover and then immediately decided i would wear them as a treat,
She bought me tight female jeans for indoor wear only, then took me shopping in them, then decided i would and could wear them doing my normal vanilla tasks often with suspender underneath, just as she had done for me when 16 onwards, she later added to my collection as i have too.
She bought me female brightly coloured shorts, then matching bikini bottoms for our holidays, so all my shorts are female ones,
Then she bought me female silky pink girlie patterned PJs, then added to this pair so i now only sleep in female clothing.

That ment that i wear female clothing 24/7 365 days of the year.

All these except the suspenders i wear daily, though ive worn suspenders 4 days out of the last 5! and am now under my silky PJs, locked obviously.

Am i sissy? well i would say not.

Only in later life have i orally cleaned her, she didnt like this and neither did i, but i did it as sir told me to, several times, i wouldnt have done this in my 20s.

She pissed on me as i laid on the floor, she was directed to by sir however she later siad she didnt feel comfortable pissing on her husband laid there wearing, a collar, in chastity, matching suspenders, knickers and nails. In reality i actually quite liked the humiliation, even it took me 20 years to like some humiliation. She didnt as she viewed me as her husband not her submissive cuck which is a shame.

I am a 6ft 3 masculine dominant man at home and at work, i have often had my jean clad ass felt by women and some men! who say ive a cute bottom but what they dont know is they are actually feeling is an cute bottom encased in female jeans and female knickers. My wife wouldnt say i was a sissy but has said i am a tart!

We sometimes mince words. I'm considered a sissy but I'm not gay, yet if I'm ordered to give my wifes lover a blowjob I will. I do it not because I have a genuine attraction to men, I don't have that particular drive. I do it to show my obedience to my wife and to demonstrate my lack of manhood. Thats different than being gay. To me, being a sissy means surrendering all my manhood,(if I ever had any) and being totally obedient to my wife and submissive to her lovers. I will take him in my ass because I'm too weak and submissive to stop him. She enjoys seeing my weak effeminate nature and comparing this to her lovers desireable manly traits. She enjoys her experiences with him more this way. My humiliation is her aphrodisiac. Some uses of the word sissy might refer to homosexuality but again my brand of it refers to femininity, obedience and lack of manliness( a small ineffectual penis).

 

[droopy1]

I wouldnt discribe myself as a sissy so maybe i am writing on the wrong thread, i am a cuck husband who has been semi feminised. I became so as it was my wife wish and she has said she always knew i would be receptive and knew this when she was 17.

It was my wife that first collared me to her as her lover had collared her to him, hers wasnt a permanent fitting, mine was and is and locked.
It was she that presented me with my first cage, then decided it would become a virtually permanent fitment,
It was she that asked me to wear the knickers/panties she having just removed them so her lover could fuck her and she that decided from that day i would only ever wear panties. She bought me some but now we wear each others.
It was she that asked if she could paint my toe nails pink, i didnt know she meant permanently although the colours do change at repaint,
It was she that then:
Asked me to wear the suspenders she had just removed as she laid on our marital bed with her lover and then immediately decided i would wear them as a treat,
She bought me tight female jeans for indoor wear only, then took me shopping in them, then decided i would and could wear them doing my normal vanilla tasks often with suspender underneath, just as she had done for me when 16 onwards, she later added to my collection as i have too.
She bought me female brightly coloured shorts, then matching bikini bottoms for our holidays, so all my shorts are female ones,
Then she bought me female silky pink girlie patterned PJs, then added to this pair so i now only sleep in female clothing.

That ment that i wear female clothing 24/7 365 days of the year.

All these except the suspenders i wear daily, though ive worn suspenders 4 days out of the last 5! and am now under my silky PJs, locked obviously.

Am i sissy? well i would say not.

Only in later life have i orally cleaned her, she didnt like this and neither did i, but i did it as sir told me to, several times, i wouldnt have done this in my 20s.

She pissed on me as i laid on the floor, she was directed to by sir however she later siad she didnt feel comfortable pissing on her husband laid there wearing, a collar, in chastity, matching suspenders, knickers and nails. In reality i actually quite liked the humiliation, even it took me 20 years to like some humiliation. She didnt as she viewed me as her husband not her submissive cuck which is a shame.

I am a 6ft 3 masculine dominant man at home and at work, i have often had my jean clad ass felt by women and some men! who say ive a cute bottom but what they dont know is they are actually feeling is an cute bottom encased in female jeans and female knickers. My wife wouldnt say i was a sissy but has said i am a tart!

It seems to me like you are describing a sissy. She didn't view you as her submissive cuck yet she cross dressed you,collared you and pissed on you and made you eat his cum out of her pussy. You wear womans clothes 24/7/365 even in public and call your wifes lover "sir" while he fucks her with no resistance from you. How can it be said that you are not a submissive cuck and a sissy? What then does someone have to do to be a submissive cuck or a sissy.

 

[theGherkin]

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.

 

[nicebiguy]

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 think putting you in a pink cock cage while you suck and clean his big pussy smelling, cum covered,big manly cock is something to consider, Might as well go all the way. Do you jerk off thinking of serving and sucking a real mans big cock?

 

[droopy1]

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.

Do it. It will be the best sexual experience of your life. You will become the tiny dicked sissy that everyone knows you are. I remember my arrival into sissy hood and how sexy I felt. You will wear panties every day after this because you will have accepted yourself for who you really are.

 

[BlackMilfman JJ]

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.

One of my white friends grew up with a divorced single mom and 3 older sisters, so he was pretty much a sissy from the time he was born. Just comes natural to him.

 

[nicebiguy]

One of my white friends grew up with a divorced single mom and 3 older sisters, so he was pretty much a sissy from the time he was born. Just comes natural to him.

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.

 

[BlackMilfman JJ]

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.

You are so right.

 

[droopy1]

One of my white friends grew up with a divorced single mom and 3 older sisters, so he was pretty much a sissy from the time he was born. Just comes natural to him.

Absolutely. A lot of boys who had older sisters back in the day had to wear their sisters hand-me downs if the family had no money. I had a friend in this situation. His mom would cut up a dress that his sis outgrew and make pants out of the material. Sure they were pants but they had flower prints or were pink and lacey. Try as she may to make them more boyish it just didn't work. He also had to wear all these girls shirts and blouses. He got bullied a lot but was a good fighter, he had to be. Emotionally I was was a sissy so a few times I offered to swap clothes with him for the day. I was happy to get off my boys clothes and don these feminine things. He felt the same way. So we would pal around this way all day. He was good at protecting me from bullies and we kind of pretended I was his girlfriend secretly. That's another story. At the end of the day we had to switch back cuz we couldn't explain things. He moved away one day. It was a sad parting but I gathered together some of my clothes he could take with him. He could maybe hide them from his mom or say he found them. This was because she was a proud woman and would not accept charity ,my mom tried and was refused.

 

[nicebiguy]

Absolutely. A lot of boys who had older sisters back in the day had to wear their sisters hand-me downs if the family had no money. I had a friend in this situation. His mom would cut up a dress that his sis outgrew and make pants out of the material. Sure they were pants but they had flower prints or were pink and lacey. Try as she may to make them more boyish it just didn't work. He also had to wear all these girls shirts and blouses. He got bullied a lot but was a good fighter, he had to be. Emotionally I was was a sissy so a few times I offered to swap clothes with him for the day. I was happy to get off my boys clothes and don these feminine things. He felt the same way. So we would pal around this way all day. He was good at protecting me from bullies and we kind of pretended I was his girlfriend secretly. That's another story. At the end of the day we had to switch back cuz we couldn't explain things. He moved away one day. It was a sad parting but I gathered together some of my clothes he could take with him. He could maybe hide them from his mom or say he found them. This was because she was a proud woman and would not accept charity ,my mom tried and was refused.

How lucky both of you were, do you still think of him? Did you guys have sex?