When did you realise you were a sub sissy?

[jimmynich]

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

 

[whiteasianlvr]

While I've never had your experience as a sissy, I do think a friendship with a much more assertive man, although not sexual, confirmed my orientation and desire to be under a stronger, at least mentally, man if that makes any sense.

 

[jimmynich]

While I've never had your experience as a sissy, I do think a friendship with a much more assertive man, although not sexual, confirmed my orientation and desire to be under a stronger, at least mentally, man if that makes any sense.

Yes that make sperfect sense. I am in no way sub with everyday life or with women but part of my sexual experience with men is assuming the subservient bottom sissy role which begins as soon as I slip my stockings etc on

 

[stargame]

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

Soooo amazing

 

[jimmynich]

Soooo amazing

Aw thank you .....the excitement of just ringing the tel no on sexy messages on toilet wall was wonderful....He was probably only about 30 but was so experienced and his assertiveness in a confident way plus of course his tongue lapping my ass had my legs spread wide open like I had always been fucked in the ass. I fucking loved it and still do.....
When he took me the Gemini club in Huddersfield the weekend after he instructed me to wear stockings and suspenders and tiny panties under my regular clothes as he would want to fuck me at some point and maybe his friends would.
When Jimmy introduced me to his 1st friend in the club he said somethimg like "what an amazing fuck and I was definitely but no longrr an anal virgin"
He took me back to his and fucked me all night but all nigjt in the club a couple of his mates were groping me and telling me how hard they were going to fuck me.....didnt do but the excitement ....wow

 

[Swuchrow]

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.

 

[SPARTAN047]

When I was little.

Later, when I dressed like this.
https://ibb.co/8DtMSBn

 

[jimmynich]

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.

Love this....ive worn full lingerie and wig handbag jewellery to a sex cinema but never the make up. Only red lipstick which looks great on a cock after youve sucked it.
I was so nervous in sex club..not about going in but coming out of toilets where I had changed into my slutty outfit into the cinema.
I had gone with a trans lady confident enough to arrive already dressed -- I need not have worried as in no time at all I was getting spit roasted by 2 guys with my friend also getting fucked in a busy cinema as porn was playing

 

[jimmynich]

When I was little.

Later, when I dressed like this.
https://ibb.co/8DtMSBn

I love pic!!!! I was little when I wondered as my Mum once caught me wearing her pearl necklaces to see how they felt.....another time Id try my sisters knickers on so i suppose it was destined!!!!

 

[SPARTAN047]

I love pic!!!! I was little when I wondered as my Mum once caught me wearing her pearl necklaces to see how they felt.....another time Id try my sisters knickers on so i suppose it was destined!!!!

Thanks! I used to wear rings when I was younger.

 

[SPARTAN047]

I'll be trying my newly washed sissy university bralette and panties again this weekend, and the prostate massager vibrating deep in my asshole.

 

[desertman45]

Last weekend I came with my 9" dildo shoved up my pussy .. I mean ass ..

Is it official ?

YES

 

[vbiboy]

Long before 20.

 

[2tallpaul]

When I was 20 and a big brother at a sorority house. Losing a bet I thought was impossible, I allowed my girl friend and some pledges to shave me frrom the neck down and dress me. It was all down hill from there. Somewhat a retribution for shaving the pledges during hell week.

 

[Plumbitgoodallways]

When I was little.

Later, when I dressed like this.
https://ibb.co/8DtMSBn

I see and its nice

 

[SPARTAN047]

I see and its nice

Thanks.

 

[james2346]

i realized that i was a sub after reading some stories about it. i was getting turned on.

i had some hot chats with people on here and was finally able to meet up with this one guy. it's def being on my back with the guy on top of me. that way i feel his weight and we can make out while having sex

 

[Cherylinheels]

While on all fours, my hands clenching the sheets. My FWB pumping into me. Realization came when he did.

 

[TryGuy35]

While on all fours, my hands clenching the sheets. My FWB pumping into me. Realization came when he did.

Nice visual, now your the …on your back, legs wrapped around the waist type

 

[4yourpleasureiam]

The girls let me know early on. They and the guys knew before I did

 

[tristantrotsky]

While on all fours, my hands clenching the sheets. My FWB pumping into me. Realization came when he did.

You always had such a charming way with words, Cheryl!

 

[Stacy_TG]

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

 

[SeminoleMeaghan]

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

 

[Stacy_TG]

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

Does feel wonderful and liberating, doesn’t it?

 

[SeminoleMeaghan]

Does feel wonderful and liberating, doesn’t it?

It is unbelievable. I'm still learning how to "be myself" but just being feminine and free and is the best gift I've given myself....and the boys.