[B4T] Femboy's First Pride Festival

All Users and Characters 18+. Please read whole post.

This had been a year of firsts for Ash. Growing up in an ultra rich household, he never thought he'd be living on his own, but after his family caught him dressing like a girl, they kicked him out. So first place of his own, check.

He had a small (well small in terms of a billionaire) nest egg, but he knew first hand that money isn't forever, so he needed something to rely on. So First Job, Check.

And now, he was attending his first Pride Festival. Figuring he should not be afraid to celebrate his lifestyle and sexuality. But around a bunch of horny men, this femboy virgin was about to check one last "first" off his list.

Character: Ash is a male, dressing as a femboy. He is Bi with a male preference, though he is also a "never been kissed" virgin. He's explored his body with a small dildo and prostate toys, achieving anal orgasm, but he's never been with a man. He was once part of an old school traditional rich family (New York billionaires), but recently was cut off as his sexuality and lifestyle preferences were outed for him. He did manage to use connections to score a decent job and he has a few million stashed away just in case, so he's not gonna starve. He's outgoing and easy to approach, but a bit naive about sex and dating, but when he ultimately begins to experience sex, I imagine him embracing his inner slut.

Outfit/Appearance:

Ash is 5'6, long brown hair that goes down to his chin with dyed Pink ends. His eyes are blue. He is wearing a lilac shirt with a pair of tight jeans that show off his bubble butt. A few rips in his jeans reveal the fishnets he is wearing under them. A pair of sneakers are on his feet. His nails are painted black and he has a spiked bracelet on his left wrist. His cock is four and a half inches and slim.

Set Ups:

Here are the ideas of have how Ash finds himself losing his virginity. These are not set in stone, and I'm open to changing any of them.

Best Friend:

You are Ash's best friend. Maybe you're a childhood buddy from back when Ash was rich, maybe you're a new addition in his life but instantly you two became bros. However you met, you have no problem coming to Ash's aide, and he's no issue being there for you. So when he asked you to attend the Pride Festival with you, you of course agreed. That was until he confessed why. Ash was nervous about being hit on, and wanted you to go as his boyfriend. That meant holding hands, kisses on cheeks, things like that. Maybe your straight, maybe closeted, or out and proud, whatever it is, you never thought of Ash as anything more than a friend. But you agreed. Putting on your best Pride Wear, (<--the password) you attended with Ash, exploring the Festival. The music, the dancing, even visiting the erotic areas. Somewhere the kisses on the cheek became kisses on lips, which became making out. Somewhere arm around shoulder became arm around waist, became hand firmly gripping your best friend's ass. Somewhere dancing in front of the main stage became dancing against each other in a sweaty rave, became grinding on each other. Somewhere doing a friend a favor became guiding him on his first blow job, became fucking his virgin ass as he begs for more...

Father/Son:

When Ash was being kicked out, it was mainly the Matriarchs of the family doing the kicking out, his mother and grandmother. Ash never thought much of it, until he saw his father at the Festival. Dressed in way that CLEARLY stated he was looking for a male partner. Ash confronts him and he confesses he's been cheating on Ash's mom with other men for months. And worse, Mom knows. Dad pulls Ash aside and they have a heart to heart, dad apologizing for not standing up for Ash. At some point he complaints Ash on how cute he looks as a femboy. From there things get sexual between the two...

Brothers:

Roughly same idea up top, only this time Ash runs into one of his (married?) older brothers.

The Alleyway:

Ash, exploring everything, finds himself in an alleyway filled with men having sex. What will he find there?

• Two men jerking off together who decide to seduce Ash and Spit roast him
• A man tied up, naked, writing on his chest saying "free cum," letting Ash practice giving a blow job.
• A Gang of men who decide Ash is their next target (Non con: They force him, Dub Con: threats of violence, Con: They seduce him)
• Etc

The BDSM Tent:

Ash has to check out the kinky areas too! What will he find there?

• Spanking/Impact Play: Ash meets a man giving demonstrations on spanking, flogging, whipping. Ash is curious and the man offers to do some over the clothes Impact Play on the femboy. Ash finds himself moaning and begging for more and is convinced to undress and give the man access to his body. Each strike turns Ash into more and more of a moaning mess and offers no resistance when the man begins to finger his virgin ass and finally pushing his lube cock in the smaller male.
• Bondage: Ash is convinced to give a bondage device a try, left in it for a while as random men come up and use his state to take advantage of his body. Ash could also be gagged so no one knows the boy is begging them to stop if you want it dark.

Come with your own ideas too!

Kinks: Anal (receiving), Anal Virginity, Oral (giving and receiving), Public/semipublic sex, Consensual, Non-Con, Non Con to Con, Bondage, spanking/impact play, hair pulling, kissing, sex toys, leash/collar, dirty talk, humiliation, dominant/sub, mpreg, incest, bloodplay, pain play, choking, gangbangs, free use, threesomes, tattoos, marking, Cheating(YC having a partner they are cheating on with Ash)

Limits: Watersports, Scat, Heavy Gore, Death, smellplay.

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