When did you realise you were a sub sissy?

[Cardinal]

Like a lot of young guys my friend and I found a lot of his dads porn magazines and without a release turned to each other and it progressed from show me yours I’ll show you mine, to touching and stroking each other to re enacting some of what we saw in the magazines. Giving each other blow jobs and eventually fucking each other. It took some time exploring and getting over the feelings of guilt and shame and not sure we ever did at that age (over 18 of course)
But one day he told me he wanted me to give him a blow job with lipstick on, so I found my mom’s reddest lipstick and put it on and gave him a blow job. He LOVED it and kept telling me to do it and I was happy to do what he told me.
That’s the first time I felt submissive and did what I was told. Probably didn’t know what a submissive was but looking back that was the first time and I enjoyed it.
Pretty fun time in my life for sure

 

[stargame]

When I was little, probably around 5 years old. I played “House” with the boy next door. I was ALWAYS the wife/mom.

That is exactly part of my story.
I got to wear the satin slip.

 

[tristantrotsky]

Like a lot of young guys my friend and I found a lot of his dads porn magazines and without a release turned to each other and it progressed from show me yours I’ll show you mine, to touching and stroking each other to re enacting some of what we saw in the magazines. Giving each other blow jobs and eventually fucking each other. It took some time exploring and getting over the feelings of guilt and shame and not sure we ever did at that age (over 18 of course)
But one day he told me he wanted me to give him a blow job with lipstick on, so I found my mom’s reddest lipstick and put it on and gave him a blow job. He LOVED it and kept telling me to do it and I was happy to do what he told me.
That’s the first time I felt submissive and did what I was told. Probably didn’t know what a submissive was but looking back that was the first time and I enjoyed it.
Pretty fun time in my life for sure

Such a sweet story. And 'over 18 of course'....?
I bet you looked so cute wearing red lipstick with his cock in your mouth!

 

[Cardinal]

Such a sweet story. And 'over 18 of course'....?
I bet you looked so cute wearing red lipstick with his cock in your mouth!

That was the point, I think he really liked it

 

[Ez247]

That is exactly part of my story.
I got to wear the satin slip.

Me too! Lol only time ever came close. I played the "Husband" he played "Wife" Naturaly things became hard and it felt good dry humping each other! we didn’t know what was going on, but we knew what we were feeling and it felt good!

 

[stargame]

Me too! Lol only time ever came close. I played the "Husband" he played "Wife" Naturaly things became hard and it felt good dry humping each other! we didn’t know what was going on, but we knew what we were feeling and it felt good!

So fun, when we played house, I was always the wife.

 

[Ez247]

So fun, when we played house, I was always the wife.

PM U would love to hear more

 

[SecretsandFantasies]

For me I was almost 20 and whilst had had mutual sucking fun usually in public toilets in Town and a bit of fun with a local lad I was mainly straight dating girls but frequenting public toilets to read the stories on wall and very occasionally have very quick fun in the closets.
When I went to next level of a) getting fucked in my little ass b) knowing my place as a sub crossdressing sissy was after I rang the number on the toilet wall saying big hard cock available for willing bottoms. This was before days of mobile phones so I rang the number and a geordie man called Jimmy gave me his address and availability and few days later off to his I went.
Not knowing anything about what "bottoming" was off i went with my heart beating out of my chest.
We sucked and rimmed which was mindblowing then as I stood up to go to the bathroom after I had cum very quickly I soon understood he was top as he pressed his as then unsatisfied cock against my ass.
I tensed up and we went back to bed....as I sucked him to completion he whispered in my ear to put the lingerie on he had in bedside cabinet and that when I come next time he was 100% going to fuck me and I would love it.
I came back midweek knowing my role and looking forward to it so much as I'd already often fingered myself and used dildos......he was so assertive from the start telling me to go upstairs....he explained and showed me what to do with shower head to douche and said he would be laying on bed and I was to put the clothes on bathroom floor on.....stockings suspenders thong mini skirt and girly top.......he said I looked like a real sissy slut and by his huge hard cock I knew he liked it.....he fucked me 2 or 3 times cumming in my ass and mouth....i fucking loved it.
Later he took me to a gay club (following week) and "introduced" me to a couple of vriends
Never ever gone back from this amazing experience

How about you

Thanks for sharing loved it….For me I was around the same age 19-20. I had only dated girls. I was still a virgin when my friend’s older brother got me really high and drunk. He just sort of took it. At first so was hesitant but fell in love with sucking his cock. I had dressed in my sister’s stuff secretly and soon I was stealing her things and wearing them with Jim.

 

[SecretsandFantasies]

Admitting that Grindr is a daily app and that I'm happier as soon as I put on that bra and panties.

So sexy

 

[stargame]

Thanks for sharing loved it….For me I was around the same age 19-20. I had only dated girls. I was still a virgin when my friend’s older brother got me really high and drunk. He just sort of took it. At first so was hesitant but fell in love with sucking his cock. I had dressed in my sister’s stuff secretly and soon I was stealing her things and wearing them with Jim.

So wonderfully
Did your friend jim enjoy you in cute panties?

 

[SecretsandFantasies]

He loved more than those. He loved when I wrapped my lips around his swollen cock and milked it to purrfection

 

[Ez247]

He loved more than those. He loved when I wrapped my lips around his swollen cock and milked it to purrfection

Great username. You R My Secret Fantasy!

 

[Ez247]

I wonder if I should have known I could be this, even at a very young age based on nothing at all sexual. Because we all hear that the left v right hemisphere in the brain uses a different means of information processing - left is analytical and the right more emotive/creative. Yet I was a little scientist then mathematician but...also if there's any skill I would call "natural" for me? It's music - not just playing but the whole thing - my piano teacher had me whizzing (not urinating but progressing rapidly through...) through college music theory books at the ripe age of 10. And I self-taught other instruments including guitar and sax and I would say piano, guitar and sax use very different body movements and skills on that dimension, but they are all subsumed under a similar concept and symbolic system (music theory). Of course, I also know that cognitive psychologists (read: idiots) see deep-level similarities between music and math. (P.S. I was a cog psych...so simmer down!). My point is my brain has always been located inside my skull. I mean, it's always been both analytic and artistic. So I probably should have known even at age 7 someday I'd love cock. Yet I had no clue.

I love the way you explained that. Very interesting..

 

[panty_chap]

It was relatively recently fo rme. During the lockdown I suppose.

I've been into panties for ages, since before I really even knew what a fetish was. But back then I had zero interest in anything other than women. Dominent women, sure, but guys didn't even occur to me.

I've never wondered if I was gay. Was never confused about anything in high school or college. It was always women who were invovled in my life and fantasies.

Then came chat rooms. Turns out those femdoms were usually men, and the conversation ended soon after figuring it out. Until I decide it was only fantasy... who cares who's writing the replies.

But... then I realized I kind of liked the taboo of that. One thing led to another and soon my chats, and fantasies, involved men. But I still didn't think I was a sissy.

No, the sissy part started to evolve much later. I got inovled with a cyberdom, and he started leading me down a path. "Sissy" became a more common theme... but it was all fantasy, chat room stuff. Not my real life. But then during lockdown I went down the rabbit hole. I was shaving everything below my waist, and liking it. I was being directed to stories and lists and training about becoming a sissy, and realizing I already did some of this stuff in real life. And had been for years.

On my online profiles I had been listing myself as straight. My cyberdom finally pointed out that couldn't really be true. I had to agree and changed it to hetro flexible. And then it became too hard to deny anymore. This wasn't just a fantasy I played with online. I really was a sissy. I fit the descriptions I was seeing. I was going to the health club and changing into panties after my workout. I was being trained to eat cum. I didn' tlike it but I'd do it on command. I was being trained to only get pleasure from anal stimulation. That... that I liked. A lot. I had a vibrator I was instructed to use and found that even after it was removed I enjoyed the feeling of it having been there. I would leak precum just from the vibrator being inserted. Dripping wet panties when using it. I LOVED the feeling of the precum, ad found the wet spots to be wonderfully humiliating, physocal proof that I enjoyed being pentrated. I couldn't deny it.

I am a reluctant sissy who would be horrified to admit it in person to someone, but know that I have that side of me. Put me in lingerie, take control, and I feel duty bound to serve and entertain.

So yeah, I realised it was true around sometime around 2021. I don't particularly enjoy that it's me, but that only adds to the thrill when it comes right down to it.

 

[Subsy]

My early days consisted of humiliation and degradation from family, church, teachers, other students etc. They were trying to convince me that I was all wrong.
Leaving home to live on the street was my day of liberation. Being instructed to act the whore was my salvation.

 

[kimjohnsoncd]

In my 20s. My top was 50s and a coworker. I had sucked him and bottomed for him but the feeling didn’t happen until he hired an Asian nail lady to come to his place. She shaved my body, made me up with make up and wig, manicure and pedicure. He then had me dress in a lingerie set and lay in bed and wait for him. As he kissed me and we made eye contact, he was penetrating me and said “you are mine now”. This was when realized I was a sub sissy. I was his gurl for more than two years before I moved for work.

I had a very similar experience. I was just into my 30's. The relationship lasted about the same amount of time. He moved for work. It progressed to the point that I stayed dressed and most people probably thought I was a girl. We'd go out on dates and I lived more at his place than mine. It was exciting and incredible in many ways. Heartbreaking when he left.

 

[BobbieSue420]

the first time a let a boy fuck me in this position i knew i was a sub sissy...View attachment 2546536

 

[neon_noodle]

the first time a let a boy fuck me in this position i knew i was a sub sissy...View attachment 2546536

Great position for a Sissy. Bent over, tight ass up and offered to her man's cock.

 

[SecretsandFantasies]

the first time a let a boy fuck me in this position i knew i was a sub sissy...View attachment 2546536

Arch that back

 

[BobbieSue420]

mmmmm arching my back as he drives his cock far up in me is a uncontrollable reaction , the same way my tight hole squeezes his cock as to not let it out. mmmmm .. just a sissy at heart I guess...View attachment 2546542

 

[neon_noodle]

mmmmm arching my back as he drives his cock far up in me is a uncontrollable reaction , the same way my tight hole squeezes his cock as to not let it out. mmmmm .. just a sissy at heart I guess...View attachment 2546542

A good Sissy like you locks her man's cock into her ass, not letting it out until he's moaned and shot off his cumload deep inside you.

 

[SecretsandFantasies]

mmmmm arching my back as he drives his cock far up in me is a uncontrollable reaction , the same way my tight hole squeezes his cock as to not let it out. mmmmm .. just a sissy at heart I guess...View attachment 2546542

Fuck yes you are. A limp wristed girlie one.

 

[neon_noodle]

The best kind.

She's look even better dressed up in my wife's hottest outfits, bent over in the bed, ready to be the wife for the weekend.

 

[tristantrotsky]

mmmmm arching my back as he drives his cock far up in me is a uncontrollable reaction , the same way my tight hole squeezes his cock as to not let it out. mmmmm .. just a sissy at heart I guess...View attachment 2546542

You are such a romantic at heart...

 

[tristantrotsky]

the first time a let a boy fuck me in this position i knew i was a sub sissy...View attachment 2546536

That moment of recognising and accepting your true nature is such a precious thing, congratulations BobbieSue, I'm so happy for you