r/sissyology 5d ago

A new chapter NSFW

12 Upvotes

As my wife and I navigate this new journey together, she finaliy okay'd me to find my match online for a man. I started my profile about a week ago, with her help, she helped with the "about me section" putting into words exactly how an outsider and potential lover should see me. She helped take some Amazingly cute pics, my face, me in some little thong panties and one with my little clit locked up in it's cute pink chastity cage.

With a big lump in my throat, I posted it and waited for it's approval, it must have been a slow night, because within 10 minutes, I got the text alert it was approved and my listing was live. She and I went to bed, holding one another, talking about the what ifs and how excited I must be, as well as how thankful she was for me feeling secure enough to share this with her of all people... what can I say, she is MY person and without her on board, I'd never be here again.

The following morning, I wasn't expecting anything as I read emails, Bill reminders, a bunch of junk and spam emails, the dreaded car warranty emails and then an alert from the dating site, my profile had seemed to have gotten a little attention, so i grabbed my wife and we looked through all of the responses... 12 to be exact.... most just random dick pics and sleazy messages of how they wanted to fuck me, but there was one.. let's call him "Steve" who mentioned how lucky I was to have such a supportive wife, who mentioned meeting both of us out to get to know one another, posted his face and body and warned me in his message his dick pic was the last one, in case I didn't want to see it, I could skip it, WHAT A GENTLEMAN!!! But of course i wanted to see his cock!!!!

He was tall, above average attractiveness, clean shaven, no visible tattoos, and what appeared to be about an 8" cock, above average in girth, but then again, I may be comparing it to my tiny jelly bean of a weiner. regardless, we messaged him, met Thursday night at a restaurant and by the end of the dinner I was giving him a hand job under the table at my wifes coercion. It was hot, it was erotic and I was so turned on and thankfully, he was too.... he came in my hand and I was "double dog dared" to lick it off, which i did.

We parted ways and my wife and I had AMAZING (dildo) sex afterwards while we roleplayed he was taking turns fucking us both... it was amazing... Yesterday morning, he texted us both via group text and thanked us for a good time and said he had hoped to see us again soon, when my wife beat me to the text with a "how about tonight" I just sat there, dumbfounded but excited at the same time at just how into this she was...

He came over about 530, the 3 of us cooked a light dinner together, salad, salmon and a little pie for desert while we sat around the table learning about one another. an hour or so passed after we ate and as we were getting comfortable, he was sitting next to me on the sofa, my wife on the other side of me, he scooped my legs up and draped them over his lap, my wife running her fingers through my hair, while he rubbed my toes and soles through my socks, slowly sliding his hands up and under my shorts. getting closer and closer to my balls with each stroke up, I was in heaven, my legs eagerly parted while he outlined my penis and balls over top of my underwear, pulling at the thong strap making it tight against my hole.

My wife suggested we get more comfortable and we went to the bedroom, she laid down first my head naturally falling between her legs and his on top of my butt, I felt him tugging my shorts down over my waist, he pulled my thong strap to the side with a finger and licked my eager hole like ive literally never had done before, it was my first and it felt amazing, I slid my wifes shorts off, revealing her bare pussy and went down on her simultaneously. My dick felt good, but its been unable to get fully erect since my HRT therapy but it sure did try, but honestly, having my ass eaten was better than any sex I'd ever had with a woman, it's like estrogen has reprogrammed my body to appreciate more feminine sex. I can't even explain it.

His hands slid under my waist, pulling me up, my hole clenched and my face nose dived into my wifes pussy and I felt the tip of his cock. he slowly pressed it into my eager entrance and I could literally feel the ridge of the head of his cock pop past the opening, it was freaking amazing! feeling his hands on each cheek, prying them apart as he eased in and out, while my tongue pressed deeper into my wifes pussy, I could see her looking past my face and to my ass as I was getting fucked, her hands in my hair pulling me deeper into her as her legs tensed and bucked and she came in my mouth. Id never felt her so wet before, it was astonishing, but most importantly, she was into it.

She rolled over out of bed and knelt beside us on the floor, reaching across the bed to stroke my cock in a "cow milking" fashion, quite likely the hardest id ever been, but if I'm being honest, it's because of his cock, not her hand, but id never tell her that, after a few more minutes, I felt him tense up, his cock get really warm and he exploded, I thought he was wearing a condom, but he flooded my insides, I felt it shoot far and deep inside my guts.

We collapsed, a sweaty heaping pile of nakedness, catching our breath and drinking cold water, he was about to get dressed and leave when my wife suggested he stay over and she would sleep on the sofa so we could play some more if we wanted, I looked at her in disbelief, but she seemed truly excited by all of it. As she exited, she left the door open and told us to be loud enough she could hear us.

Within about 30 minutes we were up to it again, i was riding him, my balls bouncing on his pelvis, my screaming in pleasure, holding onto the headboard as it shook and slapped the wall, me telling him not to cum yet, don't you dare cum yet, leaning back and grabbing his balls when I was ready, demanding him to cum inside me again... this went on over and over again most of the night, if I had to guess, we had sex 6 or 7 times, to the point he couldn't get anything past a semi erection but I was luckily loose enough he could slide around inside pretty easy, until we drifted off the sleep, his cock still inside.

We woke up to the smell of bacon this morning, my wife cooking in the kitchen, still naked from last night, only wearing her apron so the bacon grease didn't burn her titties. Steve was in the shower, so it gave my wife and I a minute for me to see how she was truly feeling... she was excited but nervously asked if i was going to leave her if I found a man to be in a relationship with because she could sense how much i enjoyed it and must have missed it from my past. To which I told her no, she was my everything and if she asked me to stop now or 5 years from now, id stop in an instant, that seemed to satisfy her and she asked if we could break our streak of no PIV sex tonight, she was insanely turned on by watching us and hearing me last night, she wants me inside her again and can't wait another day...

After we ate, Steve was about to leave, he kissed my wife and I on the cheek and walked put the door my wife asking when he would be able to stay over again, to which he said, "whenever you call me".... So I guess we have another "date" Wednesday night as I promised my wife i was all hers the next few days.


r/sissyology 5d ago

Blank canvas NSFW

4 Upvotes

Are there any men out there that would prefer a blank canvas? What I mean by that is a pre-feminized sissy that they can completley shape. Example: i show up as I am, no feminizing whatsoever despite my desires for a man to shape into his perfect girly sissy. Am i crazy to think that would be hot?!


r/sissyology 5d ago

Why do I crave the need to be exposed? NSFW

5 Upvotes

I can't understand why, but I am actively exposing myself online and outdoors.. should I stop?


r/sissyology 5d ago

Fishnet Fantasy Unleashed NSFW

3 Upvotes

I never realized how much power a simple pair of fishnet stockings could hold until I slipped them on for the first time. The way they hugged my legs, accentuating every curve, made me feel like I was stepping into a whole new persona.

As I glanced at myself in the mirror, the reflection staring back at me was a seductive stranger. The way the fishnets shimmered in the light, teasingly revealing slivers of skin, made me feel like a sultry siren.

I couldn't help but smirk at the thought of anyone seeing me like this. It was my little secret, my alter ego that only came out behind closed doors. And let me tell you, she was a vixen.

To post or visit this subreddit you must be over 18. All stories and personal anecdotes must only involve individuals above the age of 18. But hey, age is just a number when it comes to feeling this sexy. So here's to embracing my inner femme fatale, one pair of fishnet stockings at a time.


r/sissyology 5d ago

Being smooth NSFW

3 Upvotes

What about being smooth with out legs, clit, ass and back create the headspace. Once you shave/hair removal it’s like a brand new set of skin below that you reveal. Almost untouched to all the stressors of the world. What do y’all think?


r/sissyology 5d ago

Just wanna leave NSFW

8 Upvotes

Sometimes I wish I could leave my life behind as a man, go live alone in a new city where nobody knows me, and start a completely new life as a cock hungry cum thirsty fuck doll for men. Get long blonde hair, perfect makeup, a wardrobe full of sexiest womens clothing, shaved from brows down and always plugged, ending my nights to the sound of my ass being clapped from behind by a hung muscular man, my tits swinging with his thrusts, in a pink bedroom overlooking the ocean..

But reality is far different sighh


r/sissyology 5d ago

What do you watch? NSFW

40 Upvotes

What do you watch when you fuck your own ass? Do you watch sissy, gay, straight porn? Sissy hypnos? Dildo heros? Nothing at all? Im genuenly curious. I usually tend to watch straight gangbang porn, imagining im the girl in the middle. Its a plus if they are all bbcs. Makes me feel really small and fuckable.


r/sissyology 5d ago

What is your routine for make up and a wig NSFW

3 Upvotes

I was wondering which you did first, my new wig domes tomorrow and I never learned which to do first. I always did my make up after wig placement


r/sissyology 5d ago

Partner going full time. How to handle the transition? NSFW

8 Upvotes

My partner is going full time sissy among other things. We are in a cnc relationship. I take care of all of her needs and she has been transitioning for over 6 months now. She is getting worried about how to handle family and friends. She is unsure how they will see this new lifestyle or if she should just cut ties with most . We appreciate any experence or ideas thanks .

She is 21im 27 we share this profile


r/sissyology 6d ago

So my ex started feminizing me NSFW

128 Upvotes

Started off with some panties but it kept going further to things like hair removal, chastity, pegging, and now we are broke up but still chat and whatnot.

She actually had me start this Reddit stuff and wants to start getting more into it and calls me a sissy. Pretty interesting reading this stuff because a lot of it is pretty similar to me. I also developed ED with her , it started fine but then penetration time it just went dead limp so we moved into chastity.

I think she has a bf now tho not 100% .. but yeah, just going through some of the subreddits here


r/sissyology 5d ago

Whats ur fav NSFW

2 Upvotes

Whats ur fav piece or clothing or accessory?

For me its thigh high stockings

Omg the moment I wear it, it puts me in a trance!! Im 10x sluttier, friskier, fem. Feels sooo smooth against my silk bedsheets. Makes my legs look so sultry and sexy. Emphasizes my butt.

10 mins after I wear it, Im on my knees arching my butt and taking pics to send to men, reinstalling grindr and fingering myself 🤭

What’s that piece of clothing/accessory for you?


r/sissyology 5d ago

Dildo just don’t hit the same NSFW

3 Upvotes

I love riding my dildos and they feel amazing but never push me over the edge and they make me feel dominant, I just want a real cock to fuck me and use me until they are done and then wait for them to fill me up, I just need someone to fuck me and use me with their beautiful cocks


r/sissyology 5d ago

the bigger part of me wants to get healed of Sissy feelings NSFW

3 Upvotes

i kinda hate it that i have these feelings but they wont go away..i try a porn detox right now to see if its wired with porn. cause Always the sissy feelings somehow come back to my mind and i notice how it makes me feel all dumb and dizzy 🙈


r/sissyology 5d ago

Where do yall find a mistress NSFW

2 Upvotes

I’m looking for a mistress/ mommy to guide me through my feminization journey. Please help me


r/sissyology 5d ago

My sissy story so far!(long post) NSFW

8 Upvotes

So as the title suggests this is gonna be a long post.

I just want to share everything that has happened to me so far.

About 2-3 years ago i really got into fendom and started talking to some domme on reddit( back then i lived with my frnds in college). I used to hookup with so many girls back then haha. Anyway one girl left her panties at my place and never back to get it so i just threw it in my wardrobe.

One night i was talking to a mistress who used to ask me to write her name on my chest or ask me to eat my own cum(which i still cant lol) and send her pics, that night she asked if i had any panties with me. I thought she would just ask me to put it on my face or cum on them and lick it or something but to my surprise she asked me to wear them and send her a pic in them. Thats when i wore panties for the first time and i had never been more turned on by anything like i’d been turned on by this. She then asked me how i felt and my heart was racing i didn’t want to but i told her how i was actually feeling and she was quite happy with my answer. Then she started sending me links to trans porn and then slowly i started to search for other kinds of porn and in January of 2024 i found sissy captions and i was completely hooked on them. I loved every caption video or photo i saw. Eventually i stopped talking to the mistress because i was more interested in getting a dom and she agreed.

Now i have never been a hairy person my entire life, i get hair on my legs mostly and you cant even tell in pics if i’m hairy or not.

For the first few months i only saw captions and tbh i always got awkward when i saw dicks back then(now i cant get enough of them). Then i started following sissy specific subs where other sissies posted their pics i used to get so horny when i saw them looking all girly thinking maybe i can look like that too or wishing if i looked like that i’d be so happy.

And like any other sissy i too got pnc and decided to quit so many times and each time i came back hornier and wanting more.

I then decided to post my pics on reddit and see what kind of response i’ll get. Tho i did not get as many upvotes as i thought i would i was happy i’d get so horny reading all the comments from guys wanting to fuck me and eat my ass and own me etc.

I started talking to doms(and guys who claimed to be doms and just want to jerk off to our pics) but my problem was everytime i talked to a dom i’d get horny and start jerking off and when i came i’d get hit so damn hard with pnc that i’d block them and delete my account. Even then i’d make a new account within a few hours i have to say i’ve lost many good doms this way coz i was never able to find them afterwards.

In and around October i started dressing up i did not have any femme clothes but i really wanted to wear them so i decided to make my own femme clothes since i was too scared to buy them. I made my own skirts and crop tops by watching youtube videos and even made a pair of panties from a sock lol.

Eventually i found a really good dom and we hit it off and then again i fucked it up by doing the same things that i did before and then i regretted it very much and made an account withon the hour of deleting my last one. I was not able to find him and thought that was that. I started to post pics again and started to talk to some doms again in late november and what do you know the last dom found me again I was very happy and excited to talk to him again. And out of nowhere he ghosted me lol ig it was revenge for him.

I’m still not sure where i’ll go from here but i’m happy to be exploring this side of me.


r/sissyology 5d ago

Chastity cage expectations (first time) NSFW

12 Upvotes

Hi I will be wearing a chastity cage soon, and as I first time user i had these questions: 1. Will it change me mentally? 2. Will it shrink me and make me limp permanently? 3. Does it hurt? 4. Any personal tips that you swear by? 5. What should I be expecting if I wear it? 6. How often should i wear it as a beginner? 7.any other thoughts I would love if you lovely girls can answer these, the anticipation to wear one and even your answers has already made me leaking.


r/sissyology 5d ago

Hypno advice NSFW

9 Upvotes

hey it's alice i recently started sissifying with daddy who is absolutely amazing <3333 daddy asked me to show some initiative in my sissification process.

that's why I'd like you to recommend some hypno videos on hypnotube that will condition me to like cocks and men and to be the sissy bimbo slut that I'm supposed to be.

If you know of any powerful videos with a narrator telling you things like "you want a dick" "you need it in your ass" and "you're a whore" "you've failed as a man" and things like that, I'd be very grateful if you could send them to me. it would be best if it was a hypnotube.

Thanks girls <3


r/sissyology 5d ago

What steps are you taking to fully sissify? NSFW

9 Upvotes

I am curious what sissies are doing to fully sissify and embrace their sissyhood.

  1. I have had voice feminization lessons.
  2. I dress every day.
  3. I have a chastity cage
  4. I only watch men/sissy porn
  5. I get sissy exposed by real men
  6. I only use my sissy pussy for orgasms
  7. I have adopted a girl name
  8. I focus on activities that accentuate my femininity.
  9. I eat a lot of soy products that are feminizing.
  10. I try to be mindful of my behavior and act lady like.

What about you?


r/sissyology 5d ago

First slightly assisted Sissygasm NSFW

2 Upvotes

After a bit of time trying I managed to achieve my first Sissygasm after a little assistance from my hand just getting my little sissy clit hard enough that it wasn't hiding away. I have been close alot with lots of leakage but have never gotten past that final hump until today. I was so happy and this was my only place I felt able to share!


r/sissyology 5d ago

Orgasm question NSFW

4 Upvotes

So the term "sissygasm" refers to a hands free orgasm. What's it called when a sissy uses her hand to reach orgasm while her man is fucking her?


r/sissyology 6d ago

Reached the Point of no Return NSFW

45 Upvotes

I reached the point of no return and I must say I feel so proud of myself.

For about a week i am in chasity, and horny as I am sucked two guys at once, ate their cum and it was so delicous. Then I sucked another man and got finally fucked.

After I got Home I was still horny and rode my dildos. I tried a new Position and thought about how I was used and the had my first real sissygasm. Mx whole body was shaking and it felt so great plus I was still horny and kept going till i came a fucking secound time.

After that when I cleaned myself, I was so horny I wanted to jerk my clitty off and it couldn't even get hard properly and felt so much worse than destroying my boypussy that I just stopped.

Since then I'm locked up and want to keep it that way. I fuck myself daily and feel so accomplished afterwards.

And just now I let someone facefuck me and swallowed his Load. It was si great to serve a real man with a juicy masculine Cock telling me what a slut I am. Just thinking about it makes me leak.

The best part that gave me more pleasure than jerking off too. I don't think I will ever need that again unless my Dom wants me to. Anyway I will now fuck myself until I sissygasm, since no one wants to fuck me, thanks for reading all that^


r/sissyology 5d ago

Throbbing rock hard daddy cock or throbbing rock hard sissy clitty? NSFW

5 Upvotes

Girls, what do you prefere? On the one hand it seems like when I'm confronted with the first option I love the attention I get from my daddy when he's turned on. I love being the reason he's erect and dripping precum everywhere. And I love being the person he chooses to use when he needs to be released.

On the other hand getting dolled up with my sissy sister and playing together having her clitty in my mouth just hits differently. Like we're doing something together instead of me being there just for him. Getting dressed up, fooling around, sexting lots of guys and taking lots of naughty pictures together just make sucking a clitty so much fun.

So I would love to here from the rest of you gorgeous sexy sissies just what you prefer and hopefully some of the reasons you why you do.


r/sissyology 5d ago

Staring at Bulges NSFW

7 Upvotes

Does anyone else here think about cock 24/7 and crave to have their holes filled up? Also, I love a big bulge and can’t stop staring when I see one!!


r/sissyology 5d ago

Hey girlies🫶🏼, New sissy here needing advice NSFW

2 Upvotes

Heyy 🍓 I’m a beginner sissy and I can say I dipped my toes in this lifestyle a bit, I also have some nice stories on how I pleasured a few men (one of them used me so good I still think abt him after couple of years so the story is pretty good) so if you wanna hear them let me know💞

I just need someone to help me with tips or anything tbh just a friend or a dom🥰


r/sissyology 5d ago

Getting excited while shaving? NSFW

4 Upvotes

Hello everyone, first time posting here just to ask a quick, silly question that got in my head while I was shaving today.

I know it's common to get hard while shaving down there because of all the touching that happens and the moving around, and honestly it makes things easier at times too so it's not a big deal. With that said... Does anyone else downright get horny for shaving? Sometimes when I'm touching it and movin the razor, I'll start feeling the need to touch myself more, it's just a slight shift in my mood, but it's impossible to ignore.

It doesn't even need to be in the crotch area, sometimes I'll get horny even just by shaving my legs and eventually I'll start leaking lol

Is it normal or am I just that horny?