r/sissyology • • 28d ago

The psychology of arranging a hookup - How to follow through. NSFW

108 Upvotes

My advice to any sissy thinking of meeting a man (or a man thinking of meeting a sissy) is to realize the basic and near universal psychology of a hookup. Namely the moments where you'll want to back out and shouldn't.

This psychology progresses in a pattern that looks like this,

  1. The horny drive to chat with men on Grindr and arrange a hookup. This is where a sissy gleefully chats wirh men, flirts, and is quite aroused at the idea of a real encounter. The psychological state is nearly 100% positive at this point.

  2. The moment you find the right man and start actaully arranging the date itself. This is where horny chats and exchanging nude photos transition to working out the logistics of a hookup. The date, time, location, what you want to experience, and giving of an address. Usually the psychological state is 80-90% positive with just a hint of trepidation creeping in.

  3. The interhookup time. This is the critical time between arranging a hookup and meeting face to face. The period of time involved could be 15 minutes to a month away depending on how you arranged things. The psychology here is critical, this is the crux where your brain will conjure incredible doubts and think of multiple excuses not to meet. This is when your psychology is least trustful and you're most beholden to irrational fears and excuses to abandon the hookup. This interhookup time is where most people choose to flake out. They recognize their arousal is basically dead (or fleeting) and their mind has come up with half a dozen "excellent" reasons to quit.

  4. The moment of meeting. The literal knock at the door. Oddly enough this is probably where you will feel the most acute stress but feel compelled to follow through. I wouldn't worry about this part, it's a few minutes at most and once the play starts, the anxiety will instantly vanish!

  5. The play. This is where your arousal and sissy desires come roaring back! This is where you feel like you did in step 1, all those wickedly delicious sensations of being a cock slut... only now there's a man's cock in your hands!

Step 3 is the crux of the issue. This is classic stress negotiation where your self-doubt is maximized and your arousal minimized. It can feel like you're dead cold on the hookup, like all the colour and charm and hotness has drained completely out of the idea. That's just a stress response! It's your natural response to anxiety, to run away from it.

Men and sissies who have a ton of experience with hookups (50+ different hookups) still feel that arousal killing step 3 phenomenon. It never truly goes away for many people. Rather, what you gain from experience is the knowledge that it's an irrational sensation rather than your mind keying onto something true. You just acknowledge this, ignore it, and follow through with the hookup where your arousal will come roaring back.


r/sissyology • • 5h ago

Dressing for the maintenance man. Update: I did it! NSFW

63 Upvotes

As an update to my last post, I ended up wearing my leggings for the maintenance appointment!

I'll make a post with pictures so you all can see the look, but I ultimately decided on wearing a black sweatshirt, black leggings, and white socks over the leggings :)
I was so nervous going into it so I decided to just get dressed early on in the day to avoid backing out. The appointment window was from 12-4, but it kept getting delayed and delayed, which meant I just had to sit there with my anxiety for longer and longer lol.

Finally, close to 7 pm I got a text saying they would be arriving shortly. Hooked in the mirror to make any final adjustments and as I was doing that I heard a knock on my door. I knew I had to just go tor it without giving myself a chance to back out so I went for it. I opened the door and greeted the maintenance worker who was nice and professional. My front door is on the first floor and my unit is on the second, so I walked up the stairs in front of him which definitely gave him the opportunity to catch the view lol. I could tell he was making glances at my legs, but he stayed very polite and protessional which honestly put me at ease.

I stood in the bathroom with him explaining the situation and he got to work. I sat in the living room right next to the bathroom where he could see me every time he was going to his tool bag. He called me over a few times to explain things, but also a tew times just to talk casually too and make conversation. He fixed the issue (yay) and we chatted for a few minutes standing in the living room.
He went on his way and I ended up feeling very relieved.

I'm sure some of you were hoping this would be a story where I wind up on my knees or something, sadly for those of you this is a wholesome story where I was able to express some femininity and be treated totally normal.
I really respect him for being so professional and chill, and actually making conversation as well. I got to feel pretty without being judged and that alone was great. I'm definitely tempted to go out today wearing that same outfit since it felt so freeing yesterday.

So all in all, I hope this story is some encouragement for any others like me who want to do something similar but may be too nervous! I feel like so many posts and comments on here are way off in sissy fantasyland that I think it's good to share the down to Earth stories as well :)


r/sissyology • • 1h ago

Is there a way of knowing if someone potentially is a sissy? NSFW

• Upvotes

Hi! Im figuring out my sexuality and femenine side and well as the title says Im not sure what I am. Is there a way to know? Or it is just time?

Is there maybe any test? Or maybe signs I could look for?


r/sissyology • • 9h ago

Sometimes I finger my ass like a pussy and my girlfriend is pushing it further NSFW

33 Upvotes

I love fingering my hole like a pussy. It started few months back when my girlfriend pegged me. Now I can't cum without thinking about cock. This is so addictive. I think she knows it now. I asked her to call my ass a pussy and she just thinks I'm so open but now I watch gay porn to cum faster.

My girlfriend also makes me suck and deap throat on her dildo. She tells me it's not gay since it's covered in her cum. I realised that I can take bigger dildo inside me compared to her. She just likes making me like this


r/sissyology • • 45m ago

Halloween Relapse… situation isn’t ideal but want to get new things NSFW

• Upvotes

My girlfriend and I have a tradition of doing a cross dress / gender bent Halloween. Started as a gag, but it’s something I look forward to.

I’m being Wanda from her Halloween wandavision look, and having the wig, dress and shoes are tempting me to go back.

I purged a ton of my stuff when my girlfriend and I moved in together because I don’t want to disrespect her. And I am sexually attracted to her, but it also turns me on to embrace the feminine side.

I’m so tempted to order a new cage and maybe a toy or two, but I don’t want to start building up a collection that I can’t hide / order for fear of being caught.

Looking for advice, or ideas of what to buy… I used to have so many shoes, a cage, dresses, wigs, even a thrusting toy… and my favorite was to use cum lube and have really messy sessions.

I think my favorite part of the fetish was listening to those feminization instructions, trying on all sorts of outfits and getting messy.


r/sissyology • • 8h ago

Getting a girl to dress you up for halloween… NSFW

20 Upvotes

Just a question I’ve been thinking of lately. I was curious if any of you have had an experience about this or even if you have any ideas just from looking in.

In my case it would be getting my girlfriend to dress me up. I struggle quite hard with dropping hints which don’t sound too obvious. But yet it’s actually my biggest dream.

I was thinking of like having an ad up of some girly costume, I think I’d need some help from you guys on which costume that is, and then even suggesting like, do you think that would suit me. Then laughing. Just to plant the seed.

I’d also love to hear about the experience anyone here has had when they did dress up as a girl. Thanks for reading!


r/sissyology • • 20m ago

Becoming her, Becoming a Woman NSFW

• Upvotes

Many of you saw my lasta AmA, where I talked about how I went on hormones and pretty much transitioned without being trans in the "typical" way. For more context, I never felt trapped in the wrong body, in fact I was quite happy being a normal cis-het dude in my day to day life. Quite successful with girls too

I will say, I always did have a fascination with femininity from a young age, which lead me to find crossdressing and eventually feminization and this community. After my last AmA, many people introduced me to the idea of maybe being trans under de gender euphoria umbrella. While this does seem to fit me better I still think I am not trans, of course I am not cis. But, there are many trans experiences which I do not connect to. I wanted to delve deeper into what I feel while transitioning and removing all masculinity from myself, even if I never loathed it and sometimes do miss it.

I am enthralled by the process of becoming a woman and the fact that I can see how my, a masculine and typical man body, each and every day resembles that of a biological woman more. It all started with the first time I did something big, shaving my body. Seeing my legs and arms resemble those of a girl was intoxicating. At first, this was enough. I would shave, wear lingerie, jerk off and then repeat it whenever I got horny. Eventually as many of you know that stops being enough, your brain chases that first high and sexual gratification again, so you push yourself forward. Painting your nails, learning to do makeup, getting a wig...

I won't lie I got pretty good at looking like a woman, I started posting and men would fawn over me for the first time in my life. I wasn't into them, in fact I had never looked at a man and thought he was attractive or that I wanted to be with him. However, being seen as the girl and being wanted exactly like how I had heard woman described became a new form of reaching that high. Eventually this men started to push me forward, a gift card here and there, a lingerie set, my first chastity cage, makeup, wigs, requests! A dream come true for a broke college sissy. Eventually I was finding myself getting horny and instead of looking at girls, going to talk to those same men to see them pleasure themselves to me and how they had pushed me deeper.

"You would look so good with boobs" "Let me see you go on HrT baby" "Have you ever though of transitioning" "If that ass looks like that, imagine after a year of hormones"

All those comments started to ingrain into my sub conscious, of course I had thought of them myself before. But me, a boy with a transformation and feminization fetish became obsessed with the idea of actually doing it. In a way, "forcibly feminizing" myself so that even if it was just a fetish, I would become what I had wanted to see for so long. Someone changing their body so it becomes a woman's body, starting to live as one, getting a boyfriend. All because of a kink they developed when they were younger

This took years and years, but eventually the high from dressing up fully, riding a dildo, getting compliments wasn't enough. My mind needed more, my mind needed to see my body become a woman's one. I needed to be the man that turned himself into a woman. After a little bit of therapy (which concluded with the fact that I was probably not trans) I took the plunge, I got the pills and started HrT.

It was a period of time filled with doubt, am I fucking up my life for a fetish? what if I don't like it and change my body in ways I don't really want? This was especially hard in the period where libido goes down. Letting myself be confronted with the fact that I was turning myself into a woman, while not horny was quite the challenge, as it made it feel real for the first time.

Then, the changes started to be noticeable, my breast were getting fuller, my ass and thighs heavier, and my face and skin softer. Seeing my cock shrink and become feminine while locked was the most sexually gratifying part of all. Watching my literal manhood become smaller, losing presence and starting to look like a little atrophied penis solidified the fact that yes, I am becoming a woman, there was no going back and that even if I stopped I would always be feminine in some way or the other.

Starting to be seen as a woman was quite the shock too, suddenly I was living how girls do, having a normal day to day, being called she. Seeing the world in a similar way that bio women do. Relating to them made me realize that I was in fact achieving my objective.

To conclude, I love how my body looks more womanly every month. It makes me feel like a reached the final point of this fetish and of my transformation kink. I literally did a transformation into a different body. You could say I "became" trans, because yes I do love to live as a woman knowing that I wasn't born this way, that this was the resulta of MY choices. Also, I am into men now, I find myself sexually and romantically attracted to them. Probably because of how most of my sexual experiences have been with them. Strengthening sexual connections and making them overpower the ones I was born with. Of course, I am still attracted to woman, but when I crave sex, I crave to be fucked by a man.

I'm thinking of maybe doing a YouTube series documenting my journey, the journey of becoming a woman and living as one ,as I still think I have long ways to go before I feel complete. Plus I think this is a seriously under-explored topic. Let me know if this is something people would be interested in watching. I certainly would love to make it, as this is something I would have ate up before transitioning.

Everyday I become her, everyday I become more of a woman. That's why I love this, because I started off as a man, but those days are long gone because of my choices


r/sissyology • • 6h ago

Sissy size queens. Whats your favorite way to really get yourself a deep fuck? NSFW

11 Upvotes

I have two really nice horse cocks that range from 10-14 inches are quite thick. I love riding them while sucking the other or strapping it up to my fuck machine and let it rip. That feeling of getting to / unlocking a new ridge on the cock always gets me and drives me insane. Makes me think how blessed I am to be able to feel something so massive turning me into just a cock sleeve. Best part too is that I’m locked up and lip the entire time. Add bonus if there is a vibrator involved, I’ll be leaking them.


r/sissyology • • 57m ago

Suggestions on a sissygasm instruction video? NSFW

• Upvotes

Hey I've been looking to train for a sissygasm and I was wondering how you people prepared for it. Just alone by yourself without any porn? With hard porn? With instruction videos?

Personally I think instruction videos are very very hot if they are well made. Unfortunately I don't know any... Does somebody have any recommendations?

Thank you!


r/sissyology • • 3h ago

Need hookup encouragement NSFW

6 Upvotes

25M US-Basically what the title says

I’ve been at this point many times. Dressed up, caged and then flaking in the end. Then I purge..

And Im back here again after a few months. On Amazon shopping for sissy items. Except this time I want someone to talk to or chat with, as I dress up, clean up, ride my dildo, go on grindr and then ultimately meet a man to suck and get fucked.

I dont mind having girlies or daddies. Just cant do this alone anymore. Its frustrating being this drawn to cock but never having enough courage to go experience one in person.

PSA-seeking someone in US just so timezones match


r/sissyology • • 53m ago

Any one up for friendship chats 😈😅😅 NSFW

• Upvotes

Hi all need some friends up for sissy convo all things pink and purple. Gets lonely in lace and panties sometimes haha . Sissy/cd here love this realm so much fun . I need some new ideas and fits x


r/sissyology • • 4h ago

Straight guy with a sissy humiliation kink NSFW

5 Upvotes

I consider myself straight, but I’ve developed a strong sissy/crossdressing kink, especially the humiliation side of it. The biggest rush comes from imagining being seen by strangers and knowing they might judge me.

I keep going through the same cycle: I get intense urges, buy sissy clothes and chastity gear, feel excited, then get hit with guilt and throw everything away and say never again to only to buy everything again weeks later.

Nobody in my real life knows about this side of me.

Recently i once again bought sissy stuff and I’ve been planning a public sissy walk.

I’m thinking of wearing a

skirt

shirt

stockings

wig

face mask

bra

nub chastity device.

I’ve also been considering wearing a butt plug during the walk. (What do you think)

The thought of being seen by strangers is incredibly exciting but also terrifying


r/sissyology • • 10h ago

Went out dressed with another CD for the first time! NSFW

13 Upvotes

This might be a bit longer so I have provided TLDR at the end.

So I have been crossdressing since I was a child and my dream was always to go out fully dressed in public. I have done this partially like wearing lingerie underneath my boy clothes, or just wearing women's jeans - but that's about it. A few months back I connected with a CD from reddit and after chatting for sometime we decided to meet in person. Now she has gone out in public fully dressed multiple time before and I wanted to do this too.

So on the day, we decided to meet at a cockbar bar in the evening. And for the full day I decided to feminize myself. I shaved my whole body (including my clitty and boi pussy), applied scented moisturizer and did my makeup. The makeup took like sooo long, almost an hour. I'm a total amateur and wasn't too happy with the result but I went ahead anyway. Then I tucked my clitty and wore the tightest tiniest panty that I have to keep my clitty in place. Wore hip enhancing panties that gave my butt a juicy shape and women's skinny jeans. For boobs I have B cups stick on silicon breast that I used and then wore a black padded bra and finally a full sleeve black top. Finally I wore a wig with shoulder length hair and tied that into a ponytail. My look was completed and overall I looked quite feminine. Hehe. Oh also I painted my toes and wore a pair of high heels.

I called a cab and went to her hotel and was waiting outside on the footpath. And that was the mosttttt humiliation I have ever felt. There was an alcohol shop nearby and all the guys were just staring at me and I just couldn't take it. I was keeping my head down and staring at my phone the whole time and texting her to quickly come. After about 10 mins of excruciating nervousness and humiliation she finally arrived. And oh man. She was stunning. She was wearing flaired jeans, a red crop top and red hot lipstick. Sooo hottt. I was so glad she came cuz I just couldn't take the stares from the guys any longer. We quickly booked another cab and went to the cocktail bar.

Over there, the waitresses were all smiling looking at both of us. I don't know what they were thinking but they remained professional throughout. Inside the atmosphere was dimly lit and the crowd wasn't so much but I was still nervous. We ordered our drinks and once I had a few I started to feel relaxed and finally started enjoying. I even shifted to her side of the table and was laying my head on her chest while talking to her. It was like we both were two girly besties just enjoying a nice evening. I was crossing my legs like a girl, taking smaller sips and overall my mannerism was very feminine.

We spent like 2-3 hours there and finally decided to leave. I dropped her off at her hotel and went back to my house. Overall the whole experience was so so so good. This was like a dream for me to go out as a girl and I did finally. The beginning part was full of nervousness and stressful, but the ending was full of enjoyment, satisfaction and happiness. So yeah this was my sissy achievement. I know other's over here have done so much more, but for me this was a very big step that I conquered.

TLDR

Went out fully dressed as a girl for the first time and met with another CD at a cocktail bar. At first I was really nervous and anxious but later I started to feel relaxed and enjoyed the experience.


r/sissyology • • 15h ago

Ive gotten smaller and now I'm conflicted NSFW

32 Upvotes

So I took a break from being a sissy for awhile. Mainly stop watching so much porn, got my life back together and focusing on building a life outside of such a hypersexual viewpoint.

I had to stop because my health was in shambles. I'm still working on it but I keep coming back to my sissy tendencies.

Lately, I've ran into something that has made me feel conflicted. My dick has definitely gotten smaller because of all the chastity use and anal play. It's a problem cause I still like women and want a girlfriend but now I'm maybe three inches at best. I used to be closer to six! I'm kinda ashamed but also as a sissy I like having a small cock.

Anyone else had this happen? I'm torn cause I wanna feel confident in my cock as a guy most of the time but part of me wants to be a small clittly sissy for bbc.


r/sissyology • • 2h ago

Need some help NSFW

2 Upvotes

I feel stuck , I can chat with anyone and share stuff , the moment they wanna meet with me , I feel like I don't have the courage even if I feel that I wanna be fucked or I wanna suck . Anxiety is stopping me .


r/sissyology • • 10h ago

tiered of being a man NSFW

8 Upvotes

i want to wear a small skirt that dosnt hide my buns with birght pink panty and a anal plug with thigh high fishnet sock and a red heel a black crop top with long hair i want to dance infront of men in pub i wan to shake my ass twrk for powerfull men and satisfy them i wan to kneel in front of 5 bbc and suck them and make them cum in my face

i hate being a man i dont want to be like this i want to be fucking sissy in the roads beds and let mens use me as cum dump

i want lipsticks and nailpolish not dumbells and mens shit on me i wan to ride cock infront of everyone show my sissy side and want to attract people by my feminine buty i want cock and cum all over me every day but this fucking socity sucks


r/sissyology • • 3h ago

My girlfriend is buying me panties tomorrow, but it’s complicated… NSFW

2 Upvotes

So to keep it short I’ve got a medical condition which I won’t get into down there. It’s not that serious, but it means I need more supportive underwear. I’ve worked down through every helping opportunity, my gave me until it got to the last resort my girlfriend had suggested, which was panties.

She suggested that at the start. But, not wanting to look too much like I wanted this, I tried to fake putting it off. Today I took the leap and I told her I want to try panties but that she has to keep it between us.

SHE WAS SO CHILL ABOUT IT!

She said we can go down to Primark tomorrow and pick some up. Here is where you guys come in

I think she’s thinking of Boyshorts and getting me an XL. I’m trying to route my way into girlier sets but I’d love some help on how to do that. Thank you for reading x.

Will update after!!!


r/sissyology • • 5h ago

Any suggestions for my slutty Halloween costume? NSFW

3 Upvotes

Hi :p I’ve always thought that Halloween would be a great time to really show off my sissy slut side ;) What are your favorite sissy costumes that you would recommend? 😘 Looking for something that really says “fuck me sir”


r/sissyology • • 13h ago

Lost my cage keys NSFW

13 Upvotes

I have been partially doing locktober, few days on one day off just for practical reasons. Went to go shower this morning and was going to take it off to clean and I can't find my key haha. Is this how I end up permalocked ? Not to bothered tbh I am enjoying it x


r/sissyology • • 15h ago

I do think these so called paid dommes have ruined the femdom kink so much NSFW

16 Upvotes

Like sissy femdom/feminization has been my top kink and it's really interesting as both the gender gets in opposing roles and as a sissy it sounds amazing but those paid mistresses have stormed every sub there is for femdom

i hate how ignorant they are all they care about is there so called paid sessions they don't gaf about dressing someone up or anything they will just give those basic tasks that almost everyone already knows and there is no connection or anything

it's just pure money making i believe there are women who are genuinely into this as I was with one for some time ,and now as I'm looking for another one it's so hard as they are here only for money and do not really care about kinks and all and every femdom sub is filled with their corny posts with weird titles


r/sissyology • • 3m ago

First experience with another guy at a kink event! NSFW

• Upvotes

Yesterday I went to my first ever kink event for Locktober, it was amazing! I was unsure about going but I’m so glad I did. At first I was pretty nervous and anxious but I quickly felt more comfortable as people came up to say hi and were super approachable.

I got complimented and called cute by a few different guys. I was afraid my outfit wasn’t attractive but having tops and bottoms compliment was insanely hot.

Last night was also my first playing and kissing with another guy!!! He was also in chastity and was soooo cute. After we first talked he said “I hope I see you later” and my heart was racing from excitement.

When we met up later on we talked for a bit before he started playing with my balls, a first for me. Then after feeling his for a bit he asked if he would kiss me and without second thought I said “Of course.” It only lasted for a minute or two but making out with eachother while feeling each others cages and balls was an experience I will never forget. I wish I saw him again that night so I could’ve kissed his balls and cage:(.

I’m so glad I ending up going to this event, it’s given me so much more confidence in myself. I think this was the push I need to finally have the courage to meet up with someone!!!

Also shoutout KINK3D, they have the best cages and people❤️


r/sissyology • • 7h ago

SO looking forward to a sissy vacation NSFW

3 Upvotes

Hey all!

On and off sissy here! While I am long past purging and have completely accepted my sissy side, I am unfortunately not in a housing situation I can be a sissy whenever I want.

BUT!

I have some time off in early December and have decided part of that will involve just getting out of town and getting a decent hotel room for a few days.

Plan to bring enough stuff to doll up for most of that time.

Also, knowing I've got about 7 weeks, it has motivated my diet and training! Gotta look good in those sissy outfits!

And for me, being in sissy mode is so RELAXING. An escape (in a non sexual sense) from life. The thought of just being able to be dressed, with makeup on and a cage, playing my Switch for hours.

But also, really hoping to fulfill one of my fantasies.

Kinda mild all things considered, but I've got this fantasy of meeting up with two separate guys. I've had my share of hookups before, but never two separate men in one day.

Just the thought of having one man come over pound me, leave, and immediately getting back on Grindr to find his replacement is just so hot to me!

Can't wait! Counting down the days!


r/sissyology • • 4h ago

Started from being dominant with Women to being fucked and the sluts of Women is the hottest thing for me NSFW

2 Upvotes

Reversed the classic NSFW Straight Relationship into having the Woman being the Alpha Male role and the Man being her Sissy Slut as a relationship for me sounds incredible for me, it's my goal kinda


r/sissyology • • 5h ago

Post Purge Advice NSFW

2 Upvotes

I recently purged my sissy toys and gear and I’m pent up. I want to approach an online femdom for a video/chat session with disappearing media. Specifics I’m looking for: 

  • She directs me to lock in a chastity cage 
  • Instructs me to fuck a dildo 
  • Makes me cum and eat it

I need to stay fully anonymous: no face, legs covered.  Looking for advice on: 

  1. Best way to approach/post to find someone reliable 
  2. Precautions for privacy
  3. Any recommended platforms

Not looking for the session in this post — just solid advice first. Thanks


r/sissyology • • 8h ago

Whats in your experience the best way to start being a sissy? NSFW

3 Upvotes

Rn now I live with my parents where is impossible to do nothing. The Next step should be pay a rent but probably Will need to have roommates to be affordable. And I dont think my cravings Will resist waiting untill I have my own House and probably a girl friend. What would you do? What has worked for you?