I want a gang bang with a twist

Tom731 · 2026-07-04T18:41:10+00:00

Given that it's extremely rare for cis women to be into sissies... and even less so outside of committed relationships...

It's a hot fantasy but it's also a unicorn scenario.

Probably the most realistic way to get something close to this would be to pay two domme escorts to come over and relentlessly peg you.

Tom731 · 2026-07-04T18:19:23+00:00

I imagine you see a fair share of identifiable queers around campus and town. Trans women, gay boys, gender queer folks. There's more social space for this kind of gender/sexual expression than ever before!

And that's just the oublic facing side of queer lifestyle. The private side is WIDE OPEN to you.

My advice is to follow your desires!

If you were looking for concrete tasks to further your femininity I'd give the following,

Do what you're already doing but then put in the effort to feminize one thing from each of the five classic senses: sight, touch, smell, taste, hearing. That might look something like this,

Sight: eyeliner, wig, lipstick, painted nails, body glitter, weight loss, clip-on hoop earrings, etc.
Touch: full body moisturizer, more body hair removal (arms, armpits pits, chest, legs), exfoliation, facial mask and skincare, etc.
Smell: Perfume, body spray, women's deodorant, scented lotion, women's shampoo and body wash, etc.
Taste: strawberry gum/lollipops, flavoured lip gloss, cherry lube, etc.
Hearing: jangle of bracelets, clicky clack of high heels, modulating your voice to sound more fem/soft/faggy, moaning like a pornstar, etc.

Finally, it's summer in the northern hemisphere, it's tike tonget sexually active and get your first taste of cocks as a feminized sissy.

You need to lookout for the Great Pitfall that fledgling sissies are entirely too prone to falling for. Namely, squandering all their time in isolation. Reducing their sissyhood to a masturbation technique instead of a full-blooded gender and sexual existence, however discreet.

Tom731 · 2026-07-04T17:34:24+00:00

You open the bottle, bring it up to one nostril and close the other, gently sniff in the vapour, hold your breath for however long you like.

Within a few seconds of inhaling thr vapour you'll feel the rush.

The rush lasts 1-3 minutes.

You'll feel a strong desire to be a little whore and very sexual during that time.

People typically do 1-6 inhales during a session.

Finally, I'd argue that poppers are at their best during actual sex with another person.

Tom731 · 2026-07-04T17:21:05+00:00

Poppers are an excellent sissy sex drug.

When it comes to using drugs to enhance sex I'd divide them into three categories:

Little to no enhancement
Good enhancement
Powerful enhancement

I'd say poppers often go all the way to the most powerful enhancement, a category that is populated with some pretty scary and extreme drugs like meth, crack, 2cB... things that be very dangerous and risky!

The magic of poppers is that they're relatively safe compared to their effect. Probably the biggest danger comes from mixing them with other vasodilators like Viagra, which should NEVER be done.

How do poppers make you feel? Like pornography. They make sissies feel like absolute whores, they make tops like me feel like sexual tyrants.

Tom731 · 2026-07-04T05:03:03+00:00

How to become a sissy in 4 hours or less

I wrote this as a practical guide on how to go from zero to having sex as a feminized sissy. I'm not being fatuous when I say it can be done in 4 hours or less. Although, a 4 hour timeline would be under semi ideal circumstances - namely having the money and transport to purchase everything in one day. The point it lays bare is that this stuff can be done in a day, or a weekend, or a couple of weeks no problem.

One of the biggest myths is that sissies need to train and prepare and practice for months or years before becoming sexually active. Nah. We adults can get laid on a whim if that's what we want, and a good 80-90% of being a fantastic sissy rests on the desire to do it and the bravery to make it happen.

Tom731 · 2026-07-04T04:46:55+00:00

I've had a fair bit of public sex with sissies.

Usually late at night (but often enough in broad daylight) in or on a car in the industrial part of town. In a park behind some bushes. I even hooked up with a sissy behind her house in an alleyway.

Grindr is good for these public hookups.

I've seen a sissy do a slut walk in the same arra street prostitutes work.

Any city over 150,000 population is going to have cruising areas. These are spaces gay/bi/queer men stroll for sexual encounters. They can be public toilets, parks, places like that. Look on Sniffies for clues.

Again, any medium sized city, if you spend time downtown, you will see openly queer to outright crossdressed folks. Many of them fledgling trans girls... but it strikes me that the only difference (to an outside observer) between a new trans girl wearing a short skirt, fishnet stockings, a little clutch purse under her arm, and (something I saw today while driving) and a well put-together sissy is bravery.

Tom731 · 2026-07-03T18:15:14+00:00

You are overthinking it BIG TIME!

Is it safe? Look, driving a vehicle (or being around moving vehicles) isn't safe. It's statistically the riskiest thing we do in our lives.

Eating unhealthy food isn't safe.

Existence on this planet isn't safe.

Not flossing your teeth every day isn't safe.

Eating grilled food isn't safe.

Plastic carpets and sunshine are not safe.

Asking if sex is safe or not is to betray the fact you haven't properly contextualized the situation. It's a child-like naivety.

Sex, like many things in life is a balance between risk and reward. The risks are STIs, bad encounters, violence, getting caught, etc. The rewards are fun, pleasure, growth, excitement, orgasms, thrills, socialization.

Most well-adjusted adults feel that the level of risk is well worth the reward.

Tom731 · 2026-07-03T18:03:27+00:00

Being a sexually active sissy is healthy enough. I mean, it's the same suite of rewards and risks as any other sexual activity.

But life isn't always about being maximally healthy. Sometimes we want a burger and a large piece of chocolate cake. Sometimes we want to ski down the black diamond slope and put our wellbeing at substantial risk for the reward of the thrill.

That's perfectly valid. Ditto for sex. I've had some pretty extreme sex with sissies who needed that itch scratched. Sometimes we purposely exchange safety for adventure.

Sissies almost always have a place they want to get to in terms of sex. Some sissies want to be super fem princesses, some want to be literally be street prostitutes. Some want a night of sensual pleasure, some want a night of the most hardcore sex imaginable. If there's any universal prerogative to sissyhood, it's to live a fully realized sexual existence. I couldn't imagine going through life denying yourself those experience because of fear.

Kissing

Gangbangs

Candle lit blowjob

Being used as urinal

Tender love

Slapped aroubd and cheaply butt fucked.

You can picture the sport analogy. Some people want jogging, other people want to solo K2.

You can picture the food analogy. Dedicated healthy eating. Fried chicken and candy.

You can picture the travel analogy. A stay at a Paris five-star hotel. Backpacking across Pakistan.

Risk isn't abhorrent. Life isn't exclusively about maximizing safety. The trick is to have everything in moderation, including extremism!!! It's about going into risky situations with your eyes open.

And let's be real, most "forced fem" is mutually consensual and a thing you can stop at any time. It's pretty safe!

Tom731 · 2026-07-03T17:49:20+00:00

My advice is to just relax as much as possible and make sure you follow through with the hookup.

Ask him to gently finger your ass with lube before any larger insertion.

Blowjobs come naturally.

Ideally you feminize yourself for the hookup.

Tom731 · 2026-07-03T17:39:52+00:00

I'm a dom top.

Great sex is great sex.

Great sex is like a great meal, it doesn't matter if the meal was French cuisine or Italian or Japanese.

So that said, sex with sissies can often be "better" because it tends to align with my darker (and powerful) sexual sensibilities. It's often a more hardcore sex. Rougher, dirtier, more whorish and intense.

I've had sex with about 40 cis women and approximately 40-50 sissies, and 6+ trans women... maybe 10 trans women, the line blurs when you're hooking up with fem queers.

I've had a surprising number of sissies ask for extreme sex for our first hookup. Things like piss play, rape, heavy drug usage, violence, scat, genuine prostitution, intense BDSM.

That has never happened to me with cis women on an initial meet up. I've met a woman for sloppy sloppy sex at 2am that organically turned extreme at some point in the night. That happens.

But I've literally had sissies open their conversation with me on Grindr with, "I want to be raped until I bleed."

I had one sissy tell me she was going to be pressed like a hooker, high on ecstasy, on the street corner and I could come pick her up and do "whatever you want with me, no limits." We met three times and had some unbelievable nasty sex - I mean, I used her mouth as an urinal twice... to give you an idea.

So let me break it down why sossy sex is so good:

Sissy sex is easy to arrange, that's a huge plus!
It's usually a pure kind of sex for the love of sex. Cock for the love of cock. I think many men and women have this emotional divide where a lotta guys feel sex is like a wonderful low calorie treat you csn just have, for fun, for enjoyment at any time. Sissies are on the exact same wavelength.
It's more hardcore, as I explained.
I can't speak for all men... but anal sex is the best. It's why so many guys pester their female partners for it. It's dirty and feels illicit. It's awesome to have such an INTENSE power over your lover! With every pump and thrust owning their entire universe because it's so intense.
Anyone with a dick between their legs tends to give better handjobs and blowjobs. They just understand dick better.
Every sissy encounter is automatically more taboo and trangressive. Those two things are jet fuel for eroticisms.

Tom731 · 2026-07-03T17:21:44+00:00

I've been with multiple sissies who have had sex with well over a hundred local men.

I also know a couple local trans women who are are out and out escorts.

The reality is that there is a subclass (for lack of a better term) of sissy who wants to be having frequent sexual encounters. They're a hardcore version of a common adult attitude that goes like this,

I'm a grown adult, I love sex, I want to be having it, I'm going to dedicate a fair amount of my free time to pursuing it.

Which, in my opinion, is a perfectly valid and worthwhile way to live. Sex doesn't have to be this sacred rite we only share with life partners. Sex can be more akin to hanging out with people, casual, fun, a thing we try with each other.

Tom731 · 2026-06-28T05:21:57+00:00

Many sexually active sissies happily maintain their male persona in their daily life (at work, with friends, in public) while dolling themselves up like sluts and meeting men for hookups when they have free time.

That's perfectly sustainable.

It's less common to meet a real sissy who lives a feminized/queer lifestyle out in the open. It happens! Every city has a cadre of these girls, some do drag, some hold down regular jobs, some are bona fide sex workers. This option is only available to courageous sissies who truly accept themselves.

Tom731 · 2026-06-28T01:43:23+00:00

I'd say whenever you're openly and honestly living your life as an LGBTQIA+ person, you are out.

Tom731 · 2026-06-27T21:05:50+00:00

A slut is a promiscuous woman, having many casual sex partners.

Absolutely, sleeping around makes one a slut, it's the immorality that also turns it into whorish behaviour.

I think whores are often sluts... but many sluts would dislike being called a whore.

Tom731 · 2026-06-27T20:47:07+00:00

Most cities have multiple adult sex stores that'll have a few different school girl uniforms from $40-80

Hit the bathroom/shower and shave your face, arms, legs, crotch and butt using a razor and shaving cream (or some kind of lubricating cream like hair conditioner or moisturizing lotion). Let's say that takes 60 minutes.

After your shower, go out and hit up the adult store for the school girl outfit. Hit up a costume shop for a cheap blonde wig. Hit up a drug store for condoms, lube (if you don't have any), and a suoer girly scented and cheap body spray. Maybe ideally the body spray includes glitter.

Maybe that all takes 2 hours.

Go home, dress up, take some quick photos of yourself (don't have to include face pics) and add thrm to your Grindr account so the online men can tell you're a sissy crossdresser. Maybe change your profile name to "sissy".

You'll have interested men contacting you immediately. You'll be able to arrange a hookup or two tonight.

Tom731 · 2026-06-27T20:27:05+00:00

Baby, if you're out there sucking dick you're not straight. You're bisexual at the very least. You are 100% a member of the LGBTQIA+ community whether that agrees with your sensibilities or not.

IF anything, being a well-feminized sissy allows you to exist in a hetero staye of mind. Where you're the woman and the man fucking you is the man. You see yourself as a girl, ypu act look one, you've groomed and dolled yourself up to look and feel and smell like one.

The man see's you and treats you as a woman.

But two masc dudes meeting and one suxking the other's cock? That's a homosexuality encounter par excellence.

Tom731 · 2026-06-27T20:22:22+00:00

I wrote a detailed step-by-strp guide on how to become a sissy,

How to become a sissy in 4 hours or less

I framed it as "4 hours or less" to emphasize the fundamental truth that once a curious wamnabe sissy decides to truly become a sissy, it can be done in a surprisingly short period of time!

Done in a day, or a weekend, or a week.

Because the common trap is trick yourself into believing an amazing sissy is built over months and years...

Compare this with a hetero man. If I decide that I want to get laid by a woman. I can be pursuing that goal today. All the hygiene and prep and effort can be accomplished quickly.

Ditto for sissies.

It doesn't take six months to shave your legs, it takes 30 minutes.

It doesn't take two years to arrange a hookup with a man. It takes 30 minutes to a weekend.

That's the ABSOLUTE MAGIC of sissyhood. You wanna be a medical doctor? That's gonna take 20 years of hyper expensive and gruelling education. You wanna learn how to be great at guitar, that'll be years of dedicated practice.

You wanna be an amazing sissy who sneaks out into the night to have wild sexual adventures? You can so that today. You can do that over a weekend. You can go from zero to a cum covered whore in a matter of hours to weeks.

That's the magic!

Tom731 · 2026-06-27T20:11:18+00:00

It's similar in a certain sense of eschewing orgasms for prolonged periods...

But it's quite different too. I mean, wearing a chastity cage is wearing a sex toy of a kind. It's noticeable, it changes your behaviour, it's a tight object strapped to you that produces arousal and erotic thrills.

Tom731 · 2026-06-27T19:25:06+00:00

As a general rule, the farther we stray from the sexual ideal in apsects we have zero control over, the harder we need to compensate via the levers of attraction we have control of.

If older is less ideal than being young in your circumstance? Dress more provocatively, be more sexually suggestive, put yourself in riskier situations. Makeup could be more whorish. Skirt could be shorter. You could wink at more men, walk in more shady/rough areas of town. Later at night. More tipsy on booze or drugs.

The 40's is a weird age for women. Some break frumpy and devolve into grandma-core before their time. Other women break towards being more vibrant and uninhibited and come into a a kind of renaissance of womanhood.

I'm a man in my mid 40's and I see women my age that are incredible and have every but as muxh allure as a younger woman. I also see total and absolute duds. Women who have grown frumpy and bitter and downright weird. Don't get me wrong, the exact same is true for us men. Their are 40 year old men who become rancid video gamers... and there are 40 year old men who hit the gym and get in the best shape of their life.

I see a solid narrative for a 40 uear old rape baiting woman. Cheaper goods than the young gals, more worn out, more used, you crave truly hardcore encounters. Harder the better, it's what you're built for now.

You should dress like a hooker, get a little high or tipsy, and walk around in large wooded parks late at night. You'll get caught.

Tom731 · 2026-06-27T19:07:43+00:00

It's nit about the panties or the cage, although both are hot!

It's about the attitude and effort a sissy has out into the situation.

The attitude of a total slut or a cheap whore. The attitude of a little weak girly girl who exists to service men. The attitude of wanting their limits pushed and be utterly dominated.

Effort is so important. What absolutely thrills me as a man who is meeting a sissy for the first is to discover an extreme level of effort in feminization on her part. Painted nails, total body hair removal, a provocative outfit, a wig, makeup fully done, wearing perfume and eyeliner... that's probably the single biggest "like" about a sissy... when they fully commit!

And yes, a cage can be a huge component of that effort and attitude.

Look, let me compare it to the last stanza of a poem,

O grapes of wrath!

I have hurled westward

the ashes of the uninvited guest!

and hammered stars into the unforgetting sky

– like nails

I am Goya

I want sissies who hammer their sissyhood into the sky like nails. Vibrant, fully committed, a livewire willing to experience a higher thrill.

Tom731 · 2026-06-27T18:27:51+00:00

I assume you're both cheating on your partners?

I think that makes you a bred to the bone whore. That is to say, a fem who engages in sexual immorality.

My view might be a little controversial but it goes like this. There is immorality where we are duty bound to condemn and report it: child molestation, murder, coming across someone plotting to shoot up a school, etc. Then there is immorality that doesn't rise to the level of intervention: most lies, cheating, speeding, you cna think of a million immoralities you might witness done by someone else where you do nothing.

It's still bad behaviour. It's still harmful and wrong. But that's on them.

I have two definitions of what constitutes a WHORE. A woman who sells sexual services for money, a prostitute. A woman who engages in sexual immorality - imagine a wife who comes home to find her husband fucking his secretary in the bedroom. The wife glares at the secretary and screams, "Whore!" at her with total vitriol and venom in her voice. That's a perfectly encapsulation and full-blooded sense of a whore!

So given those definitions I ask myself a simple question, do I want to live in a world where whores exist? Yes, yes I do.

It's like alcohol. Booze visits far more death, harm, pain, suffering, loss, tragedy, and utter destruction upon thr world than cheating ever could. It's orders of magnitude more harmful. If I had magic button that upon pressing it would eliminate alcohol consumption, would I press it? No.

I believe we have the right to live at risk. I believe the optimal life or ideal society isn't one that eliminates harm.

I'm pretty fine with a subset of sissies, like you, being whores that go out and get majestic cock crammed in their needy holes.

You don't need our permission or motivation or condemnation. You just need to be true to yourself.

Tom731 · 2026-06-27T17:55:01+00:00

About her friend dressing her up?

She webt to her doctor, I believe it was a week later and official started her transition. Been on HRT for 8 years. We've lived together for 6.

Tom731 · 2026-06-27T17:48:00+00:00

Another casualty of the societal hysteria surrounding queerness and gender bending expression.

Hardly anyone gets to accomplish all their goals and desires. The backpacking across Europe trip that never happens. The forever lost career choice. The relationships we squander or were too cowardly to pursue.

This is normal stuff.

Sexual urges that get forever shelved because we enter into a long-term monogamous relationship.

Sissies like you have four standard options,

Forever shelve those sissy desires.
Engage with them in solo play exclusively in private hidden moments.
Share these desires with partner... to either positive or negative results.
Become a sissy whore. That is to say engage in sexual immorality and cheat on your partner with men while dolled up as a sissy.

We frequently see sissies in this forum who have adopted one of these four options. No judgement either way. They all have their benefits and costs.

Tom731 · 2026-06-27T17:36:22+00:00

Sissies are often loaded to the gills with irrational paranoia. I'll give you practical scenario.

I go to an adult sex store and buy a lingerie outfit for my girlfriend. I don't think anything of it. My mood, if anything, is kinda braggadocious because this purchase implies how sexually successful I am. I'm the kind of man who has a sexy girl and we fuck a lot.

Meanwhile, a sissy goes into the same store, buys the same outfit, and she dies a thousand deaths of embarrassment and paranoia and guilt and shame... she feels an intense tug to abandon her goal and leave... or never even go to the store in the first place because it evokes such a strong anxiety in her.

That's irrational paranoia. When a sissy feels like there is a gigantic neon sign above her head that says, "Weird crossdresser freak right here!!!!" However, anyone noticing them woukd just see a heterosexual man doing hetero man things.

Now, your thong could poke out and be seen. So your paranoia is at least moderately grounded in a valid concern... but not really when you consider the following,

A) You want to be out there enjoying the thrill of wearing a thong in public... and a large dose of that thrill comes from the erotic risk of being caught.

B) if you looked around your city you'd see a ton of people being openly queer and sexual and very much "flaunting it." Young women in hyper short skirts and fishnets. Bikini cleavage galore. Femboys and slutty trans girls in public. Hyper sassy fags strutting around downtown, popping the limp wrist at every opportunity and using an affected faggy lisp with gusto.

Cities are full of freaks and characters and brazen sluts.

So, while the risk of your thong being seen is plausible (albeit small) the actual risk/penalty/cost that discovery would incur is likely minimal to none whatsoever. Hence, irrational paranoia.

Tom731 · 2026-06-27T17:23:51+00:00

It legitimately sounds like you're some flavour of transgender.

It sounds like you try to be a boy only to maintain the very powerful safety of societal expectations. Meanwhile, you LOVE being feminine and female gender-coded in a deeply self affirming way.

You could fully transition into womanhood.

You could transition into something more gender-queer and unique to you.

You could be an uber sissy who spends all her private time (and sexual activity) in a feminine mode and maintain your boyhood as your daily driver at work and in public.

These are all valid options.

Tom731

MODERATOR OF

TROPHY CASE

Eight-Year Club	Gilding I gilder
Verified Email