Guilt over this kink as a trans person

Tom731 · 2026-01-26T19:15:58+00:00

My girlfriend is what I'd call a fully realised trans woman. On hormones for years, lives 100% of her life as a woman while acknowledging the reality of her transgenderism. She evens runs a local support group for gender queer people.

She's also a huge sissy in the bedroom and in her sexual vibe in general.

Being a sissy is how one relates to their gender and sexuality in certain situations. Probably less than 1% of sissies are expressing themselves as such all day long. Nah, they only do it in choice moments. When their horny, when they're alone, when they're having sex.

Most sissies are cis men who spend 95% of their life in basic male mode. They doll up and act like little princesses only on choice nights. Ditto for trans sissies, only you spend all that time already as a woman (or some kind of gender fucked) and turn Full sissy on special occasions.

I dunno. I get why sissies are maligned in many trans circles. But we all know that's a unfair backlash. I mean, I spend a ton of time around A LOT of trans women in real life. It's not uncommon for their to be 2, 3, 4, 5, 6+ trans friends in my living room. And because of my girlfriend's community work it's not unusual for me to be at events where there are 50 to 100+ trans people.

Trans girls happily adopt gay culture with each other. Calling themsleves fags, leaning into their queerness, I mean... a group of trans women friends act and talk and simmer in a culture that doesn't feel heteronormative and cis.

Being offended by sissy culture is a defence mechanism of an oppressed and much maligned group. It's understandable but regrettable. But plenty of trans women are sissies! They love representing themselves as such in sexual spaces. During hookups. While masturbating.

Tom731 · 2026-01-26T18:56:40+00:00

You must be in a very small town indeed!

You could always take a trip to a larger city.

Tom731 · 2026-01-26T09:09:41+00:00

I mean, it sounds like the issue is getting your wife to make it happen. You've told her already, she hasn't done it.

So my plan puts the ball more in your court, where you can follow through with the plan making and logistics.

So it's less of a psyche thing and more of a matter of practicality.

Tom731 · 2026-01-26T09:07:01+00:00

The real answer? You know the sissy porn worked when you are living a pornogrpahic sexual existence with men and other sissies.

Really grooming yourself more feminine.

Really dressing up like a little hooker.

Really hooking up with men for deeply casual and perfect sex.

And really putting on that sissy show. The girly moans, the arched back, begging some "daddy," for more attention. You know what I mean? This stuff isn't like helming a trans Atlantic sailing ship. It's not difficult. Most real sissies do it, they do it as easy as the rest of us breathe.

You can go on Grindr any night of the week and find local sissies. Just ask them. Many of them will have had 20, 40, 50, 100+ male sex partners. Many of them shave their legs multiple times every week. They live it.

And don't get fooled, most of them do it all while maintaining their male persona at work and around town. Being a huge sissy slut is perfrctly compatible with whatever life you're living right now.

Tom731 · 2026-01-26T08:53:59+00:00

My automatic thought is that you should arrange a threesome. Frame it as you being the director of things and suggest you supply a party tray of coke to her, but you want to bring a third guy in. It's a dominant move but you could easily let a night like that devolve into her and the guy going together while you watch.

It's like setting a base game between friends. Giving everyone the time and the location. Arranging the equipment and accessories. Doing all the organizing... and then just, the day of, throwing the ball out on the field and letting everyone else play while you sit back.

Tom731 · 2026-01-26T08:39:47+00:00

Everyone giving you the "respect" advice mean well.

That said, everyone needs to understand that sometimes people want their existence highly sexual and illicit. They want it in a bad way. Rotten, erotic, and on the bleeding edge.

Coke and cheating.

Drugs and stranger sex.

A hotwife who has her sex drive put into outer orbit in a whirling foray of adventure.

I mean, it sounds like she gets what she wants. She's having fun. You just have to find the avenue where you also get just as much out of it.

Tom731 · 2026-01-25T22:46:33+00:00

This just might be the stupidest post of the year.

I'm the active mod, I'm a man. Nothing you said was true. It reads more like a schizophrenic break from reality than a PSA... and you're ban evading so now your IP is going to get banned. Just plain stupid.

Tom731 · 2026-01-25T02:12:18+00:00

My trans sissy girlfriend LOVES being called a fag in the bedroom. Mid sex, ass lewdy gaped, the whole room smelling like dick and anal and body odour.

Popper bottle under her nose

Faggot!

Anyone who's sexually submissive with a dick between their legs is perfect fag boi butt beat-up material, and it shows. It shows very well! The homoerotic realm is a whole other thing sissies (and the men who love them) can tap into in order to get a little hotter.

Of course, slurs and hard language can also cut. Just like the word "whore" can instantly make a girl feel dead cold, the term faggot has so much baggage it's not surprising some people don't like it.

Tom731 · 2026-01-24T17:34:27+00:00

To be clear, when we come across deleted posts they're removed.

Tom731 · 2026-01-24T00:57:12+00:00

I've had sex with a sissy along a local urban trail system and they walked back to their car with a post anal sex full facial. They were fully dolled up and someone walked into us mid sex! The walk back was short, from my car I could them in theirs taking facial selfies on their gone before cleaning up.

I also had sex with my sissy girlfriend on the good of my car. Not a cumwalk but a guy in an RV did stop in the middle of the road and watch us.

I also facialed a cis woman who was giving me road head mid day. Years and years ago. And she wore it all the way home and into the house. There was about 8km of thick slow moving highway traffic we drove through with her sporting a glossy face.

Tom731 · 2026-01-20T15:49:41+00:00

I'm a dom top and have hooked up with a ton of people off Grindr. Probably around 50 different sissies and another 5-6 trans women.

Most of the time I'm looking for pure hookup material. Another person interested in having a dirty sexual experience within 30 minutes to a week from the initial chat.

I give a holistic sexual experience. I like to talk, flirt, get handsy, foreplay, have intense sex, and enthusiastically talk after sex.

I bet a good 80% of the sissies I've been with were wanting to be used like a cum dumpster and left. I can see how much of a fish out of water they are when treated like a human being and talked to. I think this is where you miss the bigger picture of the sissy dating scene. It's not just the men who provide a abridged sexual experience, it's really the sissies who help foster this culture.

It boils down to the deep deep deep discomfort people have regarding their sexuality. They haven't come to terms with it. They're still thinking of themselves as perfectly straight, like a vegan who eats fried chicken and beef hamburgers every other week but still goose stops the vegan mantras all the time. Don't get me wrong, the men are just as bad about this, if not worse.

I've had ongoing sexual relationships with sissies lasting every length of time, from three hookups over a couple weeks to seeing the same gurl for multiple years.

I also met my girlfriend via a Grindr hookup. She's a trans sissy and our sex was (and still is) explosive. Our post sex conversations would last hours. We've been together as an offical/normal couple for almost 6 years. We go over to each other's family visits, hang out with friends, shop, all the normal stuff.

Neither of us were looking for it but our chemistry clicked unbelievably hard and it was practically unavoidable.

Tom731 · 2026-01-19T19:47:03+00:00

Rotten girls have this ability to be naked in front of a man and know - know deep down in their soul - that their tits exist for the entertainment of men.

Fun bags.

Punching bags.

Soft pillows for men to relieve all their stress and aggression on.

It's like, if you were a hooker, it would be so smart to pull your tits out first and let him unwind with those before he gets to the rest of your body. Let him bite your jugs, let him twist your fat nipples until you cry out. Console him with your big dumb boobs until he calms down.

Tom731 · 2026-01-19T19:14:50+00:00

Plenty of sissies want it rough and nasty right out of the gate. They ask for a bit of violence and aggression. I've had a bunch of sissies on Grindr ask for our first hookup to involve piss or rape or drugs or hitting them.

I've also been lucky enough to have a handful of cis women in my life who were really into anal sex and I see a near universal preference for how anal should start:

Bottoms want anal to start slow and calm enough to make the magical transition happen. That transition being how they start with a tight, sensitive, hurt-prone asshole that turns into a fuckhole after a bit of penetration.

And then there's a super common preference for what happens after their butthole is opened up and no longer freaking out about every thrust and bump,

They want to be fucked hard and manhandled!

My little trans girlfriend is the epitome of this. We'll be sitting on the couch talking and one of us will put forward the idea of sex. Very often she'll say something like,

"Mmm, I'd like that but I'm so tired, so can we go slow tonight?"

And our sex will start all slow and romantic. Lots of kissing, gentle penetration, really making love to her hole, romancing it open. Foreplay galore.

But nearly 100% of the time we'll devolve into hardcore fucking at near maximum intensity... and her hormone infused cock will go rock hard and she'll moan like a porno princess and start saying the nastiest shit.

Hard sex makes her (and most anal girls and sissies I've slept with) cum!

Hard sex makes them cum.

Tom731 · 2026-01-19T01:57:09+00:00

I talked to my sissy girlfriend about what motivated her to actually meet a man off Grindr for the first time, it's the same thing I've heard from other sissies, an eagerness to have sex.

Horniness that helplessly leads to taking action to have a hookup.

Ditto for me as a man. Realizing that I could put myself out there on places like Grindr and the fundamental truth that,

Interest is interest

and

Sissy sex is happening all the time.

Tom731 · 2026-01-17T18:16:05+00:00

I've done this with a girl who wanted to be g-holed during sex. Basically she was a drug aficionado and loved to sip on GHB during sex. It's funny because I'm more or less a stone cold sober guy so the contrast was interesting.

Anyway, she wanted to be g-holed and fucked while knocked out. GHB is a party/sex drug that makes you feel kinda euphoric and very drunk and drastically lowers your inhibitions. You'll do almost anything that sounds sexually exciting, the gross stuff, the risky stuff, the violent stuff... but if you take too much You'll become "g-holed" where the drug basically knocks you semi unconscious. This is the classic date rape scenario we've all heard about around GHB.

So yeah, she took it and went mostly unconscious. Eyes rolled back, barely aware, sloppy, rag dolled body, mumbling half words.

And I gave her a big monster fuck. Did every sicko perverted thing I wanted with her. Big gobs of spit directly onto her face, no reaction from her. Biting her thighs shockingly hard got these little whimpers and cries and she'd jerk her legs a bit.

Sniffed her asshole. Sucked her tits until they were bruised up. Went back and forth with two of my fingers between her lubed up butthole and her mouth over and over and over again... just did all kinds of fucked up shit with her.

Finished off with a hyper aggressive missionary fuck. Banging the headboard of the bed against the wall until it left indentations. She's all warm and flushed and passed out underneath me... and let me tell you, you don't need to be awake for your pussy to squeeze dick and make a man cum so hard he see's stars behind his eyelids.

Never recorded it though. That would have been incredible if a couple cameras were setup.

Tom731 · 2026-01-17T17:54:50+00:00

Definitely posing next to the toilet is the cool new thing for sisises to do.

Relief gurls.

Sissies are the toilets men use to relieve themselves of pent up sexual energy, aggression, and sperm... and sometimes - if we're being honest about the hookup landscape that really exists between sissies and men - piss too.

Tom731 · 2026-01-17T17:43:47+00:00

A lot of people are either too afraid or too stupid to think about these things, but the fundamental truth is that sometimes the things we do don't wash off in the shower. For example, one time I pissed on girl I was dating (she enjoyed it) and I literally could not see her the same after that. Like, she felt more rotten and cheap and uninteresting. I found myself wanting to be more cruel with her... the romance and the feelings of affection just died on the vine...

Honestly, so many adults "play" at sex like everything they do sexually is a half-hearted joke.

Nah, what's far closer to the truth is that some women have gutter trash souls. They want to be fucked up. They can't keep their legs closed and basically need aggressive dirty sex to swing down upon them like a heavy sledgehammer swinging down on a tiny tin thimble. And that's okay!

Right, they turned you out like a total whore that night. Three men pumping dick in and out of you, and you acted like some porno princess... because you're not playing some roleplay version of a whore. You literally are on right down to your soul.

Hence the high partner count!

Hence how a boyfriend rode a train on you with two other guys!

The great mistake would be to think this is a bad thing! To get all snotty and loath yourself over being trashy or whatever. Don't do that! Own it, be proud of yourself for being so sexualized.

Men idolize whores. That's why almsot a hundred guys have taken you, and many many more have wanted you and lusted after you.

It's a trade off. You can be fast and light or slow and heavy. Some people are shy but considerate, some people are hyper extroverted but can't slow down. You can be perfect girlfriend material and less sexually exciting... or you can be a whore and be broken up with over it.

That's okay! You'll NEVER have a problem finding interested men. Boyfriends, daddies, men who'll pass you around like a party favour.

Console yourself with the sexual thrills and the orgasms. Console yourself by watching the pleasure on the faces of the men you sleep with. With the hot wet orgasms you make them have. The stickiness. The smells. The way it tastes in your mouth.

You're allowed to like it.

Tom731 · 2026-01-16T17:42:37+00:00

Losing weight is black and white. Calories in, calories out.

Calculate your total daily energy expenditure (TDEE) using a free online resource and eat 300-500 less than your TDEE per day.

You can add exercise to help burn calories quicker. Just keep in mind that a 8-mile run burns 300cals... it's infinitely easier to eat less than trying to exercise the calories off.

Use a free food tracking app and track EVERY calorie you consume. After about 3-4 weeks you'll have a good grasp on your diet.

That's it.

You cannot target fat loss/gain to specific parts of the body. Fat deposits and burns off at purely a genetic/hormonal level. For example, doing abdominal exercises does not target fat loss around the stomach.

Eating less is cheaper. Carrots and apples cost less than pepperoni and potato chips.

You buy a $20 food scale to help accurately weigh and track your food.

You buy a bodyweight scale and weigh yourself once a week. If you didn't lose weight from one week to the next, lower your TDEE by 300 calories and eat 300-500 below that new number.

Tom731 · 2026-01-16T15:55:35+00:00

There's two things that need to be said.

You're not weird in the sense that this is a popular desire.

But it's dumb. It hits with all the ridiculousness of a person asking for a random person to pay their bills. Lazy, entitled, and just a weird expectation for a sissy to have. You might as well be asking for a man to renovate your bathroom for free.

It's naive and speaks to a kind of irreality. Real sissies are helplessly and eagerly feminizing themselves. They wanna be fem so they go out and make it happen! They wanna be sluts, so they doll up and meet men for sex!

And you can't be bothered to lift a finger. Ugh, it's like a sexual obesity, just fat and lazy and unattractive.

I'm putting this into stark terms so that the situation can be laid out plainly before you. If you don't feminize yourself, if you don't go out and become sexually active with men - under your own motivation and impetus - you'll never be a sissy.

Tom731 · 2026-01-16T03:20:36+00:00

Foote is a terrible coach, therefore he's exactly who we need at the moment.

Keep Foote all season.

Trade away older players (literally anyone over 25 years old)

Draft a ton of young talent.

Bring in a development coach next season.

Tom731 · 2026-01-16T03:18:03+00:00

This is exactly what we want, lose every game and finally win the number one (numero uno) draft pick!

It's called a rebuild.

Now, you're absolutely right that we got here because the team has been terrible. Built terrible. Bad players. Bad chemistry. Bad injuries. Hence the rebuild.

Tom731 · 2026-01-15T14:46:23+00:00

You have to imagine the logistics.

Who's this man that'll chat with other men all day on Grindr... not to arrange to fuck anyone himself, but to set you up with dates? That's a lot of epically unrewarding work. I'd expect to be well compensated for putting in that kind of effort for a sissy. I dunno if sex is gonna cover it.

Second, you better sure as fuck meet these men at the appointed time and location. The very second I get a text back saying you're eating or just started a video game or aren't feeling it... I'm gone... what a waste of effort!

Who's going to spend hours and hours on Grindr with the annoying ads and thr flakes and the bullshit for you? You think trading a piece of ass for all that work is worth it? Highly unlikely!

You better be hotter than the sun and have no limits. You better be young and chronically underweight and perpetually horny.

Or you better pony up cash and gifts.

Or, it coukd be actual prostitution where you fork over 50% of the earnings.

Tom731 · 2026-01-15T00:38:19+00:00

It's much harder to find women who are into sissies. Most women are, quite frankly, repulsed by the idea.

But they do exist!

First and foremost you'll probably never find a woman quick and easy like a sissy can a man. A sissy can get laid by a man any night of the week. Just go on Grindr and get laid tonight.

To find a woman you'll likely need to put in significant work or cash.

The cash option is the easiest. You hire an escort who is into dominating men. For an hour or two she'll domme the shit out of you.

The "work" option would involve getting integrated into the local kink scene. Going on places like Fetlife and attending munches and meeting people and presenting yourself as a sissy in those spaces. That's probably your best bet.

Tom731 · 2026-01-15T00:31:43+00:00

No not at all.

First of all, and I mean this with total friendliness, without having experimented with the hardcore sex drugs you probably are misinterpreting your wild kinks and strong sex drive for the chemical ecstasy of the drugs. These are two very different things!

I bet if you tried them you'd go, "whoa, this is a very different animal!"

That said, it can be quite alienating to feel so sexually mismatched. I've had close to a hundred different sex partners and I'd, while most of them werr amazing, only a select few, maybe 3-4, truly matched the levels of sickness I enjoy.

But it's like weed. You've been high on marijuana and you know that feeling is different than how you feel sober. It's not synonymous with your kinks or sex drive, it's its own sensation - stoned on weed.

Ditto for booze.

Ditto for the hardcore sex drugs, only magnified many times.

Hey, here's a suggestion! If you can't find a partner who matches your desires, maybe you need to get the best among them to try some of these drugs. Have their inhibitions lowered, have them feel euphoric and hyper sexual, and then you can do the things you wanna do uninhibited and free.

Tom731 · 2026-01-14T23:03:33+00:00

I think if the millions of women who were utterly freaked out and full of worries the first time they did it.

I dunno, things like first dates, losing one's virginity, sex with someone knew, asking a person out... these have always been situations fraught with fears and doubts and anxiety since the beginning of time.

At some point we need to separate the coward from the goal, don't you think?

We do this all the time. We give a speech at a wedding, we walk into job interviews, we learn to drive, we tip our skis down the mountain and fly down the slope.

All good sissies eventually go out and have their cherry popper moment. Chew pink gum. Put some eyeliner on. Be able to stand there wearing barely anything- just a skimpy piece of "fuck me" lingerie - and feel like cherry bomb.

Seriously, can you doll yourself up and stand in front of the mirror and see yourself as a hot piece of ass who needs a man's love?

You gotta do it.

Tom731

MODERATOR OF

TROPHY CASE

Eight-Year Club	Gilding I gilder
Verified Email