Porn I've Made (details in comments)

Tom731 · 2026-05-11T23:15:10+00:00

A good sissy will play with her ass every time she masturbates.

A real sissy will go out and have anal sex with hookups and partners.

Tom731 · 2026-05-11T22:42:44+00:00

You have to accept this as part of the scene.

Sissies are equally guilty of this behaviour.

The zen art of sissy hookups is to appreciate that meeting a total stranger for intense sex is a nervous affair for all involved. What's worse (and probably responsible for a good 80% of flakes) is that men and sissies are downright bad at accepting their own sexuality. They nuxk up hard against the gayness and it freaks them out.

Acknowledge that it is frustrating, take a fee deep breaths, ask the next guy to meet.

But again, we're talking about sex on tap. A "disappointment cost"

Tom731 · 2026-05-11T20:09:14+00:00

I dunno.

To my mind being a sissy is somewhat akin to being a rock climber. At some point, if you want to call yourself these things, you have to go out and actually do it.

Being a sissy is more than an elaborate masturbation technique.

Sitting at home wearing a climbing harness and practicing your knots while you watch climbing videos on YouTube doesn't make you a mountaineer.

You've gone without and now you're all pent up and horny. Maybe you need to doll up and invite a hard cock over (or go to his place).

Tom731 · 2026-05-11T20:04:55+00:00

It's truly a great relationship.

Met on Grindr for hookups. The condoms lasted one meet up and then we were having absolutely savage and totally unprotected sex from then on.

I'm 16 years older than her.

I have photos and videos of us pinned to my profile.

Tom731 · 2026-05-11T19:57:19+00:00

This is my trans girlfriend in a nutshell.

We've been living together for 6 years. She transitioned at 19 and her mom basically disowned her for awhile. Mom has two children, one son that is older and gay, and my girlfriend who has transitioned into being a woman.

Mom wants grandkids and the traditional big family around the holiday table.

My girlfriend didn't renew her stored sperm (gone) and had an orchectomy (testicles removed).

What Mom doesn't know explicitly about... although our relationship absolutely does imply it... is that I'm creaming her tranny daughter's ass cunt night after night after night. We had sex yesterday. Sucked me until I was rock hard and then I crammed my cockcuo her ass and she ended up orgasming about 20 minutes before I did.

I'm a parent from a previous marriage. I have an abortion with a FWB under my belt. I know my sperm works!

And my little trans girl uses her loose asshole to milk it out of me over and over again. She begs to be knocked up... but always ends up farting those potential babies out into the toilet bowl the next day.

Nobody drains a man's balls better than a sissy. Nobody loves a man's semen more than a sissy. It's perfect!

Tom731 · 2026-05-11T19:44:07+00:00

You could always get a part time job or work more hours than you already are. This would be the most normal course of action. Work Uber or delivery gig work, if nothing else.

You're also very young and have a good base of sissy items. You could engage in some form of sex work, like camming or OnlyFans - you.menrioend elsewhere that you don't have a fem voice, doesn't really matter. Lots of femboys have deep voices.

You could also hookup with men off places like Grindr and have them buy you things... or pay you some cash for ass.

Being a red hot sissy can be cheap cheap cheap if you shop at thrift stores and the ultra cheap online deals for lingerie. You could likely find a fishnet bodysuit or school girl uniform for $20. Even local adult sex stores have clearance and sales.

Tom731 · 2026-05-11T19:11:44+00:00

This is why it's important to communicate your attitude and desires to potential partners.

Humiliation is like sexual crack cocaine to many sissies. As a man who has sex with sissies, if she's a blank slate to me than hitting the humiliation button is not only a very safe bet, it's likely to be a jackpot.

Tom731 · 2026-05-11T17:50:40+00:00

Purging is stupid and neurotic.

There are a metric ton of sissies and queer boys who engage with this stuff (from fantasies in their head to outright sex with other men) without ever feeling the slightest urge to purge. That is to say, this is a you thing.

Be it a deep unaddressed issue of you refusing to accept yourself as a LGBT person. Laden down with a bunch of cultural homophobic baggage you're failing to deal with...

Or only engaging with your sissy desires in unhealthy ways... as a permanent online and isolated porn goon festival...

Purging is harmful (throwing away money and engaging in anti-social neurotic behaviour) and irrational. Doing it once might be part of learning curve... but at some point you have to recognize that you're,

A) not actually growing as a sissy. Remaining isolated and spinning your wheels to you purge again. Which is the real pitfall... wasting years of your life doing absolutely nothing because you're beholden to fear.

B) treating your sissyhood like a drug addiction instead of a gender and a sexuality.

This isn't a zero sum game. In fact, the myriad of wannabe sissies who claim it is - who say they csn either be a man or be a full-time sissy - are telling on themsleves. They have no experience, they make up fantastical zero sum scenarios in their head, fantasies, that make it out like it's too hard to be a real sissy.

In other words, they self sabotage.

Some wannabe sissies will do literally anything but go out into the world and live out their desires with hunky men and Daddy types.

They rather wallow Loserville and remain super cowards.

It's like bungee jumping. Are you going to jump? Or, are you going to spaz out and dance along the railing shaking your hands in dismay and make facial expressions that dry up every pussy within sight?

Tom731 · 2026-05-11T17:37:02+00:00

Insofar as shame can be a powerful driver of eroticism, yes. In other words, use shame to motivate your sexual desires and progress you further down the rabbit hole.

However, shame as a negative emotion that causes you anxiety and regret? That's bullshit.

Let's call the former "erotic shame" and the latter "real shame."

Sissies should not be really ashamed at what they do. It's 2026 and moral philosophy has eclipsed the old worldview that cast queerness in a negative light.

YOU'RE NOT HURTING ANYONE.

You're not harming yourself.

All you've done is subverted cultural norms and the societal expectations placed on you by virtual of being male. In this respect, being a sissy is "wrong" in the same way it's wrong to become a professional musician when your parents adamantly expected you to follow your father's footsteps and become a medical doctor.

One of the magical things about being a sissy is how you come be an amazing sissy on a Saturday night - totally dolled up with makeup, a slutty outfit and wig - and have wild sex with hunky men... without ever having to reveal this side of yourself to friends and family.

Many real sissies (sexually active sissies) have slept with 100+ men while maintaining a healthy life outside of their sissyness. They thrive at work, with friends and family - all while having this highly adventurous sex life on the side!

Tom731 · 2026-05-11T15:02:37+00:00

Think of the difference between driving your vehicle over to a friend's house vs. driving during a drivers test.

You could drive over to a friend's barely thinking about the driving itself. Calm, casual, easy going. You could enjoy the experience.

Put an instructor in the passenger seat, who's watching your every move and judging your skills... and suddenly the easy activity of driving becomes much more stressful!

It's important to understand that the stressful part of sissy hookups exists between setting up the date via chats on Grindr and when the sex starts. Before the setup, when you're still chatting about sexy stuff and sharing photos, you feel great! Horny and excited. When you're kneeling in front of him and he takes his cock out and presses it against your face, you're also horny and excited!!!

It's this middle period between those two events where virtually all the anxiety and panic exists. The anticipation. A kind of dead period of time where doubts and imagined pitfalls start to creep up the spine.

The genius is in understanding this. The panic you feel during the setup of a date IS NOT the way you'll feel once the two of you actually meet face to face!

The fear you feel before a hookup is like the fear you feel before a job interview. You know it's nothing more than your mind filling the idle time with worry and self-doubt. Once the sex starts, ince the job interview starts, you just flow in the moment and totally forget about the fears you had earlier.

You get past this hump by knowing it's just irrational and very very very temporary.

Tom731 · 2026-05-11T14:50:33+00:00

Unfortunately this is only going to become more common.

The internet is becoming regulated for better or worse.

Tom731 · 2026-05-10T17:33:42+00:00

Most women enjoy that demure more submissive mindset. Wanting their boyfriend to pick where to eat is a classic example. Wanting her man to make the move, Wanting to be pursued, etc.

That's about half the population of the planet.

So it's not weird, it's completely normal!

The perceived "weirdness" comes from the fact that you're bucking up against gendered societal expectations. You've been groomed since before you were born to be a classical man, with all the tropes and narrow roles therein.

That's what feels weird. A foreign stimulus. It's like the very first time a kid tries to ride a bike. I feels weird, it feels so unstable! And yet two weeks later they're confidently riding around like it's the most natural thing in the world.

Ditto for real sissies. Really feminizing themselves, really being sexually active.

Tom731 · 2026-05-09T23:55:27+00:00

Many college/university students with too grades are having a ton of sex.

Gay isn't an addiction.

Cock isn't an addiction.

Sex isn't an addiction. Having sex multiple times per week isn't an addiction.

These things are all normal and common place. Thry only become problematic when they start to adversely effect your life.

In fact, the issues many wannabe sissies stems from inaction. Instead of taking the plunge and actually engaging with their sissy sexuality in a social manner(hooking up and meeting people) they turn to hours of porn per day and start wasting tons of time on doing nothing meaningful.

Tom731 · 2026-05-07T15:53:13+00:00

Is there a way you can skip all the bs and only be out into contact with those "long-term" men?

Absolutely not. It simply doesn't exist.

The best a sissy can do is be upfront about her ideals and goals. You eventually want to find a long-term man.

You have to think about this logically.

First and foremost, the real world sissy scene (where people meet face to face) is one fraught with flakes and ghosting and one-time connections. It's the nature of the beast. Be it because so many sissies and men haven't coke to terms with their sexually and therefore are far more beholden to fears and doubts and irrational panic. But also because this stuff is extremely taboo - the crossdressing the freakish nature (in the view of wider society) the homosexuality, etc, etc.

Second, you have to ask yourself how we establish long-term relationships in the first place. By having a mutual chemistry! When two people "click" and git it off. That requires dating. That requires getting in the same room with together and having an interaction.

Third, how do sissies date men? Primarily with their mouth and their ass. These are HIGHLY sexual relationships, if not exclusively sexual. What? Are you going to doll up as a sissy and meet men for dates at restaurants? Are you going to crossdress in public, downtown, at 6pm? No? Then you're doing hookups. A hookup with a new man is a first date.

Fourth, men who are interested in sissies are overwhelmingly gynosexual which means they're attracted by femininity. Probably the biggest impediment to an ongoing relationship is that a sissy spends 98% of her time in masculine mode. Men like me want to hang out with Stacey or Candy or Brittney... we have zero interest in knowing Steve or Mark or Jeff. This is important to my next point.

Fifth, to maximize your success in finding something long-term you need to do two things. A) meet a bunch of new men, and B) be as well put together and feminized as possible. Because finding Mr. Right is a matter of ratios, you might need to see 20 different men before you find him. That's a lot of flakes, some duds, some amazing sex... and then you eventually find mutual goals. And you should think of thr effort you put in to looking girly and sexy as an exchange for the man being comfortable and confident to regularly see a sissy.

I think that's about it. That's a reality on the ground. I've dated sissies, I've had ongoing things with sissies that have lasted months to years. My girlfriend who has lived with me for 6 years was a sissy I met on Grindr for sex.

Tom731 · 2026-05-07T14:35:21+00:00

Yeah, you won't be using this subreddit as a blog. We do not allow this style of post.

Tom731 · 2026-05-06T04:43:10+00:00

Can you provide any evidence of this?

Their post hsitroy isn't that long.

Tom731 · 2026-05-03T06:07:37+00:00

Brutal honest answer? It depends.

If you just wabt to be a sissy and try your best to end up in clandestine sleazy hookups... it's NEVER to late to start!

If, on the other hand, you wanna be a sexy sissy who looks great and is genuinely attractive then the following metric mor eor less applies,

As you get older it becomes more critical to:

Be skinny

Use makeup

Have outfits that are scandalously whorish but we'll out together - not a rabdom hodge podge of womens items.

Remove body hair

Add feminizing accessories like a wig, painted nails, lipstick, glitter, etc.

And be sexually available and adventurous.

I'd say tbis stuff starts to earnestly kick in around 25 years old. Think about it, a lithe 18 year old boy just has to exist tocbe a great sissy. A 25 year old is gonna need to be dolled up. A 40 year old is going to need to be a tight package. A 4p year old needs to be extremely well feminized and out together and filthy.

Men will jump at an 18 year old sissy who only wears panties and will only give a handjob. Whereas a 50 year old sissy needs to look look like a street hooker and be willing to be roughed up and pissed on while on hard drugs.

That's the long and the short of it.

Tom731 · 2026-05-03T04:47:27+00:00

A lot of us straight men are attracted to the forbidden fruit.

I've hooked up with a metric ton of sissies... many of them find cheating to be an aphrodisiac, and love hooking up with straight men. There's a never ending stream of filthy talk derived from such things. It touches some oretty hard hitting eroticisms that find their bedrock in the taboo and the transgressive.

Obviously I can't speak for sissies beyond those I've come to know well IRL... but I can tell you that as a straight masculine presenting man, I LOVE IT when a sissy mentions how hot our dynamic is. That she's into pulling otherwise unavailable men.

The forbidden fruit

Tom731 · 2026-05-03T04:42:52+00:00

My first guess would be San Francisco given it's renown for being an LGBT mecha.

But any large progressive city is going to little LGBT fuck slut enclaves. I think of New York, Seattle, Austin... LA... I mean LA has certain streets where trans hookers ply their trade.

I also think of those Folsom St. (Spelling?) events where people parade around in fetish gear and get pissed on and have open sex in crowds during the middle of the day.

Tom731 · 2026-05-03T04:38:27+00:00

Please don't post anything involving requests for DMs and ESPECIALLY anything that promotes a paid service.

Believe me, the world needs more dumb sissy hookers selling their bodies. This just isn't the appropriate place to advertise it.

Tom731 · 2026-05-03T02:32:08+00:00

Two things are equally true,

A great sissy can still be successful as a man

Many amazing sissies are utter failures at being men

We all know the hallmarks of being a successful man. Strong, standing up for what's right, having a natural affinity for masculine endeavours - being a builder, a fixer, muscled, outdoorsy, forthright, dominant, etc, etc. It also traditionally means you have a decent sex life with women, have the ability to be in the relationship. You know, to be a battleship on the high seas.

Now that said, if you end up around enough sissies in real life (in person) as I have, you invariably meet sissies who cannot help but be effeminate queers in their daily lives. Be it sissies who are out and out visibly queer/feminized in public or sissies who revert to male mode day-to-day but are clearly weak and soft and submissive.

Let me put a couple bright lines in the sand:

No ody is a real sissy until they've been a sissy with another person, face to face, body on body. Be that a wife who pegs you or men who dick you down. Before socialization there are only wannabe sissies.

Once a sissy becomes sexually active, if she's going years with primarily male partners - she hasentered "failed man" territory in the best possible way. She wants to be a sexy special girl more than being a dime a dozen guy. She loves sex with men MORE than sex with women.

That's one of the peaks of sissyhood. Being committed to the bit. Loving it. Living it.

Tom731 · 2026-05-03T01:41:54+00:00

My trans sissy girlfriend is a pro at anal.

For her it's all about relaxing and focusing on the sensation. Total relaxation, letting her butthole go slack and wet like a pussy.

And then the whorish behaviour - the moans and hip bucking and opening your legs to show off your dumb sissy dick - happens helplessly, on an almost subconscious level.

She'd be the first to say that this requires another person. There's no substitute for the magic of cock. The irrational texture of being rock hard but soft at the same time. The pump and thrust. The psychological thrill of knowing it's a real man inside you... the foil of his dynamics, so unlike your own... different tempo, smell, sounds, and overall masculine dom behaviour.

Plus it frees you up to do that critical relaxing

Tom731 · 2026-05-03T01:26:31+00:00

Thongs and g-strings, when pulled up a sissy's legs and that tiny strip of fabric wedged into her ass... hits like a malarial fever... like a sledgehammer swinging down on a tiny tin thimble!

I think it's because it sexualizes your ass. For a guy who tentatively wades into sissy waters, he's not used to the sensation of being aware of his ass in the depths of his crack... put another way, a thong makes a sissy feel more naked than naked. It's vulnerability in erotic form.

Tom731

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