Trans girl's first time the night before

The night before Ramya and I walk the beach topless, our trans love interest was busy getting her own cherry popped. It's a realistic, not-so-perfect first time.

“You look good, baby. Let me get you a drink,” the tall man says in a sleazy voice.

This man is used to getting what he wants, Erin thinks. At a gay, lesbian, bi, LGBT-whatever event like this, moral depravity has reached its peak. Sex and promiscuity is rampant.

Maybe it's time I finally get laid.

“Sure,” she replies with a shy grin.

Erin has been slowly transitioning since before she was 18. Now at 19, this trip is a coming-out of sorts for her, deliberately done among strangers. She considers this trip her point at which she cracks the egg. She hasn't yet taken her new body for a test drive. So far, she is cautiously optimistic.

Erin's 5'4" frame didn't exactly make her successful with the ladies when she was a teenage boy. Not only was she short, she already was cursed with feminine features and chose to keep her hair long. All those weaknesses are now assets as a trans girl.

The men that want to fuck a short, petite and cute trans girl far outnumber the women that want to sleep with a short, feminine-looking boy. This is abundantly clear to her now. For the past few days, she's been rejecting a long list of men, women, non-binaries, sometimes she isn't even sure. Everyone seems to want to get with her.

But Erin is still caught between two worlds. These don't feel like her people. She grew up more conservative, and she never hangs out with the woke crowd. The beta male in front of her with his man bun, tattoos, and weird piercings is alien to her. But he is hot and tall underneath all the self-sabotage, a white guy, and older, maybe in his late twenties. And apparently he is into her. So he will have to do.

Erin doesn't even know if she is gay or straight or even bi. If she thinks of herself as a girl but is born a man and likes men, is she gay? Probably. She still likes girls too, though. Two worlds. Erin knows she has an identity crisis, and the people that would scream "mental illness" to a certain extent have a point. She tries to keep a level head and just explore her sexuality as her transition progresses and keep an open mind. Because one thing is certain: Erin is horny.

“Want to get out of here?” he asks. “Come on, let's fuck, baby!”

She is still getting used to these jolting requests for no-strings-attached sex from people she barely knows. Erin looks at his crotch in the thin speedo-like garment that doesn't hide his intimidating erection. She is curious. She wants to see. She is embarrassed because his request is loud enough for a few people around her to hear.

“Sorry what is your name?” she asks with a nervous laugh and a low voice.

“Rian,” he answers, thankfully matching her volume and making her feel like less of a slut to others watching.

Like all the people that have approached her on this trip, he assumes she is a slut because she is trans. But she has to admit, Rian is presenting her with exactly what she needs right now.

Erin is a virgin to both men and women. Giving and receiving. No matter which act she is supposed to be doing, she hasn't done it yet. She isn't sure what Rian's expectations are for her, but she has a feeling she is going to have to bottom for him. That is probably best. Erin's erections come less frequently now, and her penis is small anyway. Although the dwindling urge to penetrate someone is still there, she is not well-equipped to do so, especially in a pressure situation. In addition to the hormone therapy, she has taken the fateful step of clipping off her balls. She has truly "burned the boats." There is no going back now. The urges to use her penis also make her uncomfortable, because they feed her gender dysphoria as something she is trying to give up.

Rian leans down and kisses her, right there on the beach in public. He shoves his tongue into her mouth, and her body responds to his aggression, starting that fire in her loins.

“Okay, Rian, enough. Let's go somewhere private,” Erin says. Her decision is already made anyway, and she wants to get the hell out of everyone's view.

Rian's lodging situation is a suite he shares with at least two other people at the all-inclusive resort. Keeping with this whole LGBT-whatever themed, loosely organized group trip, it has a swinging vibe. One purple-haired person is in the suite when Rian escorts her to one of the rooms, leaving the door open as they make out on the bed. Erin is wondering if Rian knows she still has a penis or cares one way or another. After less than two minutes of kissing, Rian pulls her bikini bottom down, and Erin's tucked little cock plops out. She is shaved bare and looks very prepubescent and is a little self-conscious, although she knows this is an appealing look to some.

“Nice,” Rian says, then leans down and takes her entire little nub into his mouth!

She gasps. This feels really good, and it looks hot to see him doing this for her.

But Erin knows her cock isn't going to get hard. She is barely up to a semi, and that's about as far as she might get. She is confused and tries to silence her mind and her doubts. Does he notice she doesn't have her testicles? Is he expecting her to climax? What is his goal?

“Rian, I'm not sure I'll get...”

Before she can finish that thought, her thin cock plops out of his mouth. Rian grins and shoves down his speedo, revealing a completely-shaved, rather large erection. He spreads her legs, pushing her knees back, forcing her bum upward until he can see her butthole. He leans down, and Erin has the very weird sensation of the man's tongue licking all around the her dainty starfish. He stays there a minute, coating her in saliva, pushing with the tip, but not quite entering her bum. Erin is self-conscious and wishes he'd stop. She hasn't had a chance to clean off after the beach, but apparently he doesn't care.

He stops anyway for her and gets to his knees, kneeling between her legs.

“Are you going to fuck me?” she asks meekly.

“Yeah, baby, here get it wet for me,” he says as he moves to her front, just long enough to shove his penis in her face. She doesn't hesitate, opening her mouth to take him in for her first taste of a man, tasting the musky scent mixed with salty sweat from the beach. It isn't horrible. She bobs her head twice and drools all over it. He pulls out, grins down at her, then pecks her lips before moving back between her legs.

Erin is scared to death. She suddenly definitely does not want to do this, but she is too embarrassed to stop him. “Do we need protection? Condom?”

Rian dismisses her concern, and Erin is too weak to insist. “I'm clean, baby.”

His first push is too high. Erin has never played with her anus, but she knows, she can tell. She wills herself to be brave, she grips behind her knees and holds her legs apart and back. Get it over with.

His second push is perfectly aligned, right on the center of her starfish, but he can't breach. He pushes harder, but it doesn't hurt because it isn't opening her, it is just pushing the surrounding tissue in. The suite-mate appears at the door, purple hair and all. They/them's eyes meet Erin's for a second, then the person turns away.

Rian tries to penetrate again, but he is a little high again this time. “Damn, girl.” He chuckles and reaches over to the bedside table, finds lube, and squirts it on his cock.

“Yeah, you might need that. I'm tight,” Erin says, as if she has any clue. She wants to tell him she's a virgin, but she is embarrassed, plus he probably wouldn't believe her anyway. Again, everyone assumes trans girl = slut.

Rian is against her backdoor again, and this time she knows she will be successfully impaled. The lube makes a difference. He is on-target, and her muscles engage inside this time, blocking him, the tip beginning to open her, the crown of his cock still outside. She remembers something she read, she concentrates, bears down, pushes out to let him in...

“Ow! Fuck!” Erin groans in surprise as her muscles grip the thick head, spread around it, spasming in pain but now unable to stop his progress.

Rian grins and pushes in, ignoring Erin's bracing hand on his belly that is trying to slow him. Inch after inch of thick cock slides into the petite girl's virgin ass until it hurts again deep in her where her insides turn, at her limit. Rian grinds, squeezing in that last half inch, rearranging her body to meet his needs, and his pubic bone nudges the deflated scrotum where her balls used to be. Her face grimaces in pain even as Rian's creepy smile and look of intense lust show on his face.

It hurts way more than she thought it would. Despite the overwhelming pain, Erin sees the look of pleasure on Rian's face and has half a second of pride knowing she lost her virginity finally. Then the moment passes, and Rian pulls his cock back, hurting her stretched anus, then pushes in and begins to fuck her in and out.

“Wait,” she groans. “Rian, it hurts too much, please stop.”

Pump. Pump. Two more strokes.

“No, baby. I got in in finally, we're going to finish.”

“Rian...” she starts, then her voice and objections fade even as tears stream down her face. She is too weak to stop him, and she does not think it is her place to deny him.

She lets her legs fall to mattress. With Rian solidly inside her, she doesn't need to spread herself open anymore to facilitate the coupling.

“Uh! Oggh! Fuck!” she groans with each pump.

Her small penis that has risen to a modest semi is gone now, replaced by a thin noodle an inch long, as small as she's ever seen it. Rian playfully flicks it with his finger, apparently turned on by her submission or at least unbothered.

Another person appears in the doorway, no purple hair this time. He is short but massively overweight, blocking the light behind him that is shining in her eyes. “Take it easy on her, bro,” he says.

“She's okay.” Rian gives a quick, irritated look back, then turns to Erin again and begins kissing her. His tongue probes into her mouth, and it is not meant for either of their pleasure, rather it is muffling her objections, her squeals.

Erin sucks his tongue, distracting from the pain in her butthole. In addition to her natural tightness from being short and petite and never having stretched her anus before, she is a true anal virgin. She has not yet learned how to stop her muscles from involuntarily clenching up, desperately trying to expel the phallic intruder. It still hurts, only slightly less than when she was deflowered. At least he isn't able to penetrate as deeply with her legs on the bed versus drawn back, so that sharp pain at the end of his range isn't there. His length isn't the problem anymore, just his cruel girth.

The virgin's natural tightness and clenching spasms have the opposite effect on Rian. She is giving him the ride of his life. No way he is going to let this whiny, trans slut deny him his release!

Erin finally gets his tongue out of her mouth and turns her head to the side. “Rian... please... stop,” she whispers in resignation. “Uh!” Air explodes out of her as he puts his full weight on her now, making it hard to breathe.

“Okay. Almost done, baby,” he whispers in her ear.

“Fine. Whatever,” she mutters.

The next three pumps are full range, with his cock completely departing her body. Unlike his first successful penetration, her lover easily re-opens the stretched, lubed hole each time since it does not close completely. But it hurts Erin more as her opening is forced each time. Mercifully, on this next pump, Rian holds himself deep inside her.

And then, suddenly, she feels his body clench, he groans, and she knows his release has arrived. Rian is going to come inside her.

The tight seal her anus forms with his cock enables her to sense his ejaculation as he twitches, even as she cannot feel the fluids that defile her. This stranger, this man she just meets, is pumping his seed into her violated bum. She closes her eyes in shame, knowing she'll be left to wonder if he is really clean as he says, knowing if he cared about her, he would have pulled out. She is just glad the ordeal is over.

“Arggh!” He groans as he grinds his cock into her all the way, finishing his ejaculation. “Fuck, that was good. Nice. Very good. Tight,” he says, smiling at his lover.

“Okay. Yeah that was great. Get off,” Erin groans, and she feels his softening cock plop out. He rolls over to his back next to her.

Erin fights to catch her breath. The sting in her butt fades to about half of what it is, but she is left sore. Rian has damaged her sensitive channel. It's just anal sex, but Erin feels like she has endured a true deflowering. One day, with experience, her butt will open easier and stay relaxed, even gaping after a torrid fuck like this. But now, after her virgin fuck, her butt clenches tight after its thorough drilling, holding in Rian's copious load.

“Oh my God...” Erin says. She chuckles, then winces as her laugh triggers a pain inside her where her guts have been rearranged. At least her first time is over.

They both stare at the ceiling for a few minutes then Rian says, “I guess you want to go clean up, right? This was fun, thanks.”

It isn't a question. Erin gets the hint and puts her bikini back on. The only thing she has to cover up with is the hotel towel she brought from the beach. She doesn't bother tucking her tiny penis. She leaves the suite as quickly as possible, ignoring the sleazy grins from the two people in the suite's living area that have seen them fucking. As the door is closing behind her, the overweight guy yells out. “Come back tomorrow, I want a turn!”

Erin grins despite herself. It is a traumatic experience. It hurts. He uses her. Her butthole aches, and she worries she won't be able to hold the load in until she reaches her own room. But it is behind her, and she is proud of herself.