β–² 2 r/Sissy

On the road advice?

I'm on a extended on the road work trip. Unfortunately I'm constantly surrounded by people and don't have the time or privacy for sissy activities, has anyone else here been in similar scenarios?

What should I do till I find more privacy

reddit.com
u/Jaded_jamiecd β€” 22 hours ago
β–² 3 r/sissyology

Advice for on the road

I'm on a extended on the road work trip. Unfortunately I'm constantly surrounded by people and don't have the time or privacy for sissy activities, has anyone else here been in similar scenarios?

What should I do till I find more privacy?

reddit.com
u/Jaded_jamiecd β€” 22 hours ago
β–² 25 r/SissyConfessionBooth+1 crossposts

How many of y'all started off topping sissies? Story time/long post

Long post warning

I think perhaps it's a pretty common rabbit hole, but that's how it started for me.

once upon a time when I was a 22 year old young man a bit drunk and plenty horny, I knew a thing or two about crossdressers and sissies from porno and figured "what the hell, lets give her a go"

I downloaded Grindr met a beauty (at this time I was fit, 5 mile runs and all so it was real easy to find sissies I had a crop so to say anyway ) after this 1st time I was hooked, the next 3 years that was my only source of sex sissies all the time most every night

Till one fateful day I had a thought "she looks like she's having fun, what's so good about it"

That was the hook line and sinker ultimately, I went home with some panties I had collected and threw them on (I had tried them on before the classic stole from my mom/sister schtick so I guess it was in there at a much earlier age but buried)

It felt as all of you know amazing, I then started masturbating and gently pushing on my ass hole that's when things turned, next it was a toothbrush handle, brush handle, then on and on and the usual

Flash forward 27 I had a collection upgraded to plugs and a few toys nothing major and I eventually got the courage to ask a friend of mine about it, she is a trans woman that I had known from highschool we had a occasional hookup but good friend ultimately, I know she had a liking to top guys but always made it clear I wasn't interested.

When I finally brought it up, we had something like a 5 hour conversation she was really excited, she introduced me to maaany things, hypnos, poppers, makeup, heels, Reddit. ECT.

After the first meet she just showed me all the possibilities in the rabbit hole we did a little poppers and watch hypno, the 2nd time was a bit more, we did the same hypno pops. but this time she did none but caressed my thighs and neck while whispering sweet stuff in my ears and gently rubbing my now caged dick with some toys.

The 3rd was the whopper, we did the same, but then she asked if I wanted to suck her off, of course I agreed, after awhile of some unrefined skills, She told me to get on the bed and on all fours (more poppers πŸ˜…) and then she began to eat my ass and finger me, water a while the big show happened and I realized

"Oh wow, I just got fucked" she stayed inside my while wanding my cage, I had a very intense orgasm

On the drive home that's when I realized I just made a complete 180, I thought of all the sissies I fucked and if they thought the same thing as I'm thinking now.

The next day i was ashamed and beginning to want to throw everything out, the next week I was riding a dildo again watching hypnotube futa dildo hero πŸ˜…

I got a bit carried away on this post telling this story but I guess ultimately what I'm curious about is how many of us did this happen to or similarly I'm now 28 and yep this is something I very much love doing?

reddit.com
u/Jaded_jamiecd β€” 3 days ago
β–² 43 r/sissyology

How many of y'all started out topping sissies, story time

Long post warning

Aw jeez that's a lot of reposts and shares where is this going?

I think perhaps it's a pretty common rabbit hole, but that's how it started for me.

once upon a time when I was a 22 year old young man a bit drunk and plenty horny, I knew a thing or two about crossdressers and sissies from porno and figured "what the hell, lets give her a go"

I downloaded Grindr met a beauty (at this time I was fit, 5 mile runs and all so it was real easy to find sissies I had a crop so to say anyway ) after this 1st time I was hooked, the next 3 years that was my only source of sex sissies all the time most every night

Till one fateful day I had a thought "she looks like she's having fun, what's so good about it"

That was the hook line and sinker ultimately, I went home with some panties I had collected and threw them on (I had tried them on before the classic stole from my mom/sister schtick so I guess it was in there at a much earlier age but buried)

It felt as all of you know amazing, I then started masturbating and gently pushing on my ass hole that's when things turned, next it was a toothbrush handle, brush handle, then on and on and the usual

Flash forward 27 I had a collection upgraded to plugs and a few toys nothing major and I eventually got the courage to ask a friend of mine about it, she is a trans woman that I had known from highschool we had a occasional hookup but good friend ultimately, I know she had a liking to top guys but always made it clear I wasn't interested.

When I finally brought it up, we had something like a 5 hour conversation she was really excited, she introduced me to maaany things, hypnos, poppers, makeup, heels, Reddit. ECT.

After the first meet she just showed me all the possibilities in the rabbit hole we did a little poppers and watch hypno, the 2nd time was a bit more, we did the same hypno pops. but this time she did none but caressed my thighs and neck while whispering sweet stuff in my ears and gently rubbing my now caged dick with some toys.

The 3rd was the whopper, we did the same, but then she asked if I wanted to suck her off, of course I agreed, after awhile of some unrefined skills, She told me to get on the bed and on all fours (more poppers πŸ˜…) and then she began to eat my ass and finger me, water a while the big show happened and I realized

"Oh wow, I just got fucked" she stayed inside my while wanding my cage, I had a very intense orgasm

On the drive home that's when I realized I just made a complete 180, I thought of all the sissies I fucked and if they thought the same thing as I'm thinking now.

The next day i was ashamed and beginning to want to throw everything out, the next week I was riding a dildo again watching hypnotube futa dildo hero πŸ˜…

I got a bit carried away on this post telling this story but I guess ultimately what I'm curious about is how many of us did this happen to or similarly I'm now 28 and yep this is something I very much love doing?

reddit.com
u/Jaded_jamiecd β€” 3 days ago

I e made some AI pictures of my self to see my potential

Well like it says I made AI pictures of myself to see what I can pull off, and I'm impressed I wish I could get there and sure I can personally one day

u/Jaded_jamiecd β€” 4 days ago
β–² 0 r/sissyology

So have you ever AI'ed yourself

I've done some hyper realistic AI pictures of my self and was blown away at the potential that I have, have y'all ever done the same?

I know its a frowned upon thing but I wanted to know what I'm capable of doing with out going all the way into it 🀷🏻

reddit.com
u/Jaded_jamiecd β€” 4 days ago
β–² 2 r/Sissy

Have you ever AI'ed your self

So I've done some hyper realistic AI pictures of my self and was blown away at the potential that I have, have y'all ever done the same?

I know its a frowned upon thing but I wanted to know what I'm capable of doing with out going all the way into it 🀷🏻

reddit.com
u/Jaded_jamiecd β€” 4 days ago
β–² 8 r/sissyology

So we do this often

So we do this often

We do this often were we delete a profile and start allllll the way from the beginning it's a hard habit to break I've done it 3 times, trying to make this the last time, I understand it's something to do with PNC I suppose, but trying to fight through it this time

Good side I didn't purge still have all the clothing and goodies

reddit.com
u/Jaded_jamiecd β€” 9 days ago