First Times

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Guys first time with a transwoman, her first time topping.
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JaxRhapsody
JaxRhapsody
211 Followers

"I just joined this website a few weeks ago for hookups called Sex Freaks, it's pretty cool, they claim to specialize in unique hookups, I haven't had any success anywhere else, plus it's free," Danny told his friend.

"Bruh, you my boy, but why can't you just get a regular bitch to fuck around here," Jerome asked.

"Man; I'm trying to find trans chicks... I ran across some looking at porn by accident. I wanna see what it's like."

"A fuckin tranny!? Thems dudes, bruh! What is you thinkin!?"

"Ah dunno, I wasn't lookin for shit on purpose, but I saw it. There some fine ass ones, I swear."

"Naw Danny, they got dicks, dude," Jerome waves his hands around his crotch, "like you and me."

"I just wanna try at least once, 'rome."

"If you want dick that bad, I can show you who the DL niggas are, on the block."

"I ain't in to dudes, I know for sure about that, unless we about to run a train on a chick; I can't do it."

"Remember LaShay, that shit was fun getting in to. I can call her up if you wanna smash something."

"When I saw that shit, I clicked off that shit, then I got curious and went back. I couldn't get away from it, dead ass. I've been having these urges, I can't get these chicks outta my head. Remember how you felt the first time you smashed a white chick, I gotta try it, I might lose my mind.

"Oh my god! Bruh!"

"One time, shit is eating me up, I gotta get it out of my system. I've already been talking to a chick on there, and we're meeting tonight. The pics are one thing, hell, the moment she gets naked, I might run out that mother fucker, real life ain't the internet."

"Aieght," Jerome side eyes him. "Go do it, reality about to scare yo ass, you'll see. Then none of dis shit ever happened. Deal?

"Deal, bruh."

Later that night at the restaurant.

Danny walks in with a picture of her on his phone, looking for her, finding her at a booth near a window; "Nazz, that you?"

"Oh Danny, you are cute in real life," she stands up and hugs him.

Danny stares down his nose in to her deep cleavage smashing and releasing into his chest, her breast large and firm, his hands glide from her back, down her hips upon release.

"So, you've been curious about women like me," she ask, buttering a piece of bread.

"Yeah, I ain't gonna lie; I've had this desire, I was too embarrassed to tell the whole truth."

""Well, spill," she intrigued.

"I uh... ran across porn some while back, by accident. I found myself trying less and less to avoid it, ah been havin this itch for a grip."

"So I would be your first? I mean most transwomen would be mad, but the truth is; most dudes find out we exist through porn, it's just what happens. Used to annoy the shit outta me, but I've gotten used to it, even though with trans issues coming out, more people are getting aware, dudes still be finding us through porn, though, and wanting to treat us like sex toys."

"I ain't trynna come with that kinda disrespect, my momma raised me better."

"I can tell, you read my profile and not once called me a tgirl or tranny."

"Naw, you said they were slurs and porn shit."

"Right. So, you got points on that. Another thing we didn't really talk about is; us ladies have a few different issues, than ciswomen, like gender dysphoria. Just a heads up if you finna go down this rabbit hole. Some hate an don't want nothing to do with their dicks, we do our best to appear female, so we don't get clocked."

"What's... cis...? Plus you one fine dark queen, ah can't even tell, knowin you trans," he eyes her up and down.

"Cis is people who are what they were born as. I like the way I am, I like having a dick, there are girls outside porn that think like that. Either they don't want the surgery, afraid of it, or whatever."

Just then, the waiter walked up; "you too ready to order?"

"Yes, I'd like salmon dish," Nazz replied"

"Same, with a root beer," Danny answered.

"Oh yeah, root beer."

"All right, we'll have it out, as soon as we can," he grabbed the menus and strutted away.

"So no offense, but I wouldn't be lookin if I wanted pussy, I've had that already. What about you, though, what you want?"

"Me? I wanna be myself and not have a dude ashamed to be in public, I hate having to do extra work and watch what I wear," she explained.

"Like what?"

"Like tucking this thing and making sure it don't pop out or move, or get hard, and wear stuff that can hopefully make it unnoticeable. You... you sure you want the whole experience?"

"Hell yeah," he grinned.

"You ain't my first, first. I've been disappointed by too many dudes who just wanna piece of ass and may give me a handjob. I've been wanting to use this thing for a long time. I'm not some hooker, so I don't run across dudes that bottom often. I have a real job."

"I want all of it, first off, I ain't finna miss out on nothing, he propsed.

"Oh? I like that. So you prepared to play with my dick, to suck it?"

"Ain't never done it, but I'll try."

"Mm'kay, you gonna bottom, you said you would, you want all of it, right?"

"What if I do an you fuck me over, or it hurts and I don't like it?"

"Good questions. If you're a real man, you'll treat a lady right, have you ever took a girls virginity before, kinda the same thing. If I don't get my first, you don't get yours, and my first is part of your first. Baby, I understand how you feel, honestly, it will hurt the first time, first few times. I got everything we need to make it as easy as possible. I promise."

The waiter returns with their drinks.

"I'll make another deal with you; if I bottom like promised and everything works out like we want, I don't wanna one time thing or few times. If we click for real, I want more," he demanded.

"More?"

"Fuck yeah. I ain't seen you in da nude, but I know I ain't seen a chick as bad as you. Who the fuck wouldn't wanna show you off, a motha fucka should appreciate all a you, dick print an all."

"Really? You think you wanna date me?"

"If we click."

"And you don't care if I wear sexy clothes that show my dick... what about the stares," she asked concerned.

"Trans chicks ain't some new invention, dey can catch deez hands."

"They can catch these, too," she laughed.

Nazz thinks for a minute, excuses herself to the bathroom, to remove her underwear. She's going to test his theory, standing in front of the mirror, repositioning herself so her cock is nice and comfortable, and displayed in her snug jeans. Nazz walks back, as the waiter brings their food, Danny, and a few others notice her approach, her breast swaying, her cock swaying as her thick thighs push it side to side.

"I bet that's more comfortable," he grins.

"It is," she sat down, "it'll just take some getting used to in public."

They enjoy their dinner, chat about other things, before he follows her to her apartment.

"You sure you're ready for this," she asked, locking the door.

"Yeah," putting his arms around her and kissing her, his cock grows slightly at the embrace. He looks down at hers; "are you?"

'Trust I am, she doesn't always wake up without attention."

She leads him to the bedroom, strips off her t-shirt and bra with a bit of a sigh, he stares at her, undoing his pants.

"Now these on the other hand, get hard as fuck when I'm horny," she smirks.

"Damn them nipples are fat, like two Rollo's, dem titties look... god damn," he practically drools at the sight of her huge fake breast.

"They're a bit bigger than Rollo's," she smiles.

He sat down pulling off his shoes, Nazz approaches completely nude, he lifts his head, staring right at her uncut cock, everything shaved smooth, but a landing strip trimmed low, he could just see the head in the foreskin. He thinks to himself that he's a little bigger than that, flaccid, it might not be as bad after all.

"So do you nut, cause I seen chicks that cum but they don't nut."

"She nuts, I promise. More than any other woman, I don't even know why. Big loads, precum through anal orgasms... hopefully you have fun with it."

Never really seeing a cock before, other than his own, much less one not circumcised; rolling the skin back, to see that dark head staring back. Stroking it a little, he looks up at her.

"I ain't never sucked a dick before, but I do know what not to do," he placed it in his mouth.

Which is to make sure he keeps his teeth away, he slowly sucks to her pleasant moaning, as his lips pull and push her foreskin along her shaft, his tongue plays with the head under the skin.

"Such a tease with my dick, I love it," she purrs. "A man who appreciates uncut dick."

She starts to precum and grow in his mouth, catching him off guard, the skin now tight on het shaft, the head near his throat, dripping cum.

Pulling free, looking at the length of it and the leaking head; "damn."

"I told you I cum a lot. I can't help it."

"Not that, I wasn't expecting it to be sweet, but not that. Your dick is huge, Nazz."

"It's no bigger than yours," she points at his swelled erection."

"Well damn... mines huge, then."

"You wanna stop, or- "

'Naw, I'm good," he started sucking again.

"Fuck Danny, that's not bad," she whispers.

He sucks her sloppier and sloppier as his mouth tires, she steadies herself on his shoulders, his hands finds her ass and he digs deep, her tip gets closer and closer to the back of his throat, she spreads her legs a bit to fight her shaky knees.

"Danny, Danny... I'm going to- fuck Danny! I'm gonna..."

Her leaking cock started to pour in to a heavy stream, hitting the roof of his mouth, filling it. She pulls away as her knees try to give out. Danny slowly swallows it, smacking his lips.

"Damn, that wasn't bad, you sucked that like a real man," she looked astonished.

"That wasn't all of it, was it?"

"I have a few more in me before I'm spent, what about you?"

"Once or twice and I'm good for an hour an ready to go."

"Can you spend the night? It's been a while an I ain't in a hurry "

"Yeah."

"Cool," she replied, crawling on the bed. "That booty of yours will probably need some prep to open, lay with me."

"Why is your nut so sweet?"

"Because I'm a lady," she toys with him, "plus I eat a lot of fruits."

Danny lays on the bed next to her, quickly reminded of those huge fake tits, kissing her, rubbing a hand over both, feeling how round they are, firm, yet soft. She moans at the attention, especially Danny pressing his thumb into her large nipples that take up most of her areola. Nazz rubs her cock, making herself precum again, spreading it to him, as she rubs her thumb across the heads of their cocks. Both moaning as she strokes them together, he thrust his tongue in her mouth at the sensation. Her hand catches precum every upstroke as she twist her hand, coating them both in the sticky stuff. When the kiss is broken so they can catch breath.

"This has been so fun, you're doing surprisingly great for a first timer."

Danny finally goes for her tits, pushing his face in her cleavage, licking his way out, licking around each orb until he made it to her nipple, taking it in to his mouth, resisting the urge to bite too hard. She rolls on her back, he scoops them in his hands, pressing them together. Climbing on top of her; their cocks rub together as he sucks her nipples.

"You love those nipples don't you," she pants.

"Yo tits are perfect."

"Fuck my tits."

Don't need to tell him twice, the first piece of action his cock got so far, he scoots up, placing it right in her cleavage, Nazz smashes her tits around it, massaging it, moving her tits in every direction.

"Oh shit."

"You can't cum yet, Mr. Once or twice. I ain't even sucked it yet."

He starts ricking his hips.

"As much as I want your cum on my tits, I wanna suck the dick," she gestured him to climb off.

Danny laid on his back, she sat up and retrieved some toys and lube from her nightstand.

"What's all that," he wondered.

"Lube, a butt plug, inflatable dildo, and a small dildo. I almost forgot you needed prep, the lube has a slight numbing agent, so it doesn't hurt as bad. It's for you. The dildo is for me, I could use a bit of stretching," she explained.

Nazz laid at the foot of the bed, taking his cock in her mouth, sliding her hand between his legs, rubbing his ass. Her mouth took his whole cock in, pushing it down her throat and holding it, he moans hard. Licking the dildo, his hand sinks in her ass cheek, lifting it, slowly sticking it inside her. As she sucked him, he matched her pace with it. She pulls back, leaving the head in her mouth, pushing back down, her tongue caressing the shaft. Both bodies moving to the pleasure. Her ass seemingly trying to take the dildo out of his hand. Her finger slowly wanders between his cheeks, rubbing the tight opening. Danny shudders just before a finger slips in, pressing his g-spot.

"Damn that feels good, Nazz. I can't believe it."

She slips another finger in, his hole tightens around her. She sucks him harder, rubbing his insides to match. He feels around for her cock, pulling it to stick in his mouth, she gasp on his, his hips are working, smashing his cock in to her throat, her fingers distracting him, they rub and twist, trying to pry him open. Danny tries to swallow the precum pooling in his mouth, without taking her cock out, pounding her ass with that dildo, forcing her to cum, flooding his mouth. She pulls her fingers out, using one hand; squeezing some lube on the butt plug, slipping it inside him, he moans a little.

"Does that hurt, relax the best you can, tell me when it stops," she instructed.

"Uh-huh," he gurgled.

Rather hard to relax with her sucking his cock the way she is; clamped down with her tongue, nodding her head back and fourth. Realizing he stopped, he started fucking her again with the dildo, trying to ignore the pressure of the plug pushing against his walls, her cock starts to twitch and leak in his mouth again. Mouth too tired to suck all of her, repositioning his head, leaving the tip in, so he can lick and suck the head. Once his cock stops twitching with his breathing; Nazz gives him a minute before pulling out the butt plug, inserting two fingers back in, they slip in a little easier this time. He barely flinches, she milks him in to his first orgasm, the sensation causing slight relaxation in his muscles, his breathing slows and a moan grows. His cum starts to pour before he clenches just enough for a few small burst.

"What was that," he asked.

"I was milking you, by rubbing your g-spot," she replied, lubing up the other dildo.

"Dudes have g-spots?"

"Our prostate," she slid it in him.

"Ummm... it's not that I don't know, but don't say 'our', there's nothing masculine about you."

"Not even my dick?"

"Not the way it stays wet."

"I know, right," she gives it a few pumps to stay in.

"Damn that's tight."

"Relax baby," she licks his balls, giving the dildo a tug; "tight already."

Danny rolls her on her back, sitting on his knees taking a deep breath, feeling that dildo knotted tightly in him. Stroking her cock, spitting on the dildo, twisting it in and out until it's mostly wet. Nazz pinches and tugs on her big nipples in joy, moaning the word fuck. An idea crosses his head; slowly pulling it out if her, rubbing it's shaft along her tip, spreading her cum on it, stroking her quickly. Sticking it back in her, he thought if it weren't for the balls on it, it might have slipped all the way inside.

"Oh fuck Danny," she massages her own tits.

A smile on his face as she starts working her hips once the dildo and his hand are synchronized. Her leaking cum lubing his hand, taking his tongue; lapping up the access, before taking her back in his mouth sucking on the tip, swirling his tongue on the tip. Pulling off so she could relube his hand.

"Unnngh... daddy," she came.

Her shot arched as she lifted her hips, hitting her chest, second on shoots and splatters on her sternum and stomach, running down his hand. He stops to lick her cum from her stomach, stopping to circle her navel.

"Ooo daddy," she heaves.

Danny's tongue travels, dragging up and down her stomach, lips sucking and kissing, her breath shallows the closer his mouth gets to her tits. Nazz reaches for the pump, giving it a few more squeezes, he grunts and shakes when the device opens his anus, pushing his walls open and reaches deeper. He continues his licking.

"How you feel?"

"Kinda like I gotta shit, for real," he whispers.

"Yeah. You sure you wanna keep going?"

"Ain't no goin back, I need this," he moves towards her tits, the dildo rubs his prostate a little bit. "Oh shit."

"What's up," she sat up, concerned.

"It's kinda touching that spot you was talkin about."

"I'm still messy," she smiled

His lips moved, licking under her tits, finding her surgery scars, from under one tit, to the next. Every time he reaches across her body to her left tit, that dildo rubs his prostate, the less it hurts, the more he moves his back. Mouth sucking her skin clean, she catches his cock bounce, knowing his prostate is being hit. Danny climbs on her completely, licking the tops of her tits, she raises a leg for him to push against. When he does so, unknowingly, lost in her tit, pushes the dildo in to him, her hands feel the muscles in his thighs, peeking at him from over her tit, licking up to her nipple.

"You're a king among light-skinned brothas," she muses.

He sits up enough to squeeze a tit in his hands as he sucks hard on her nipple to her pleasing coos, all while rubbing his butt on her leg.

"How big is this thing," he pulls off, breathing hard

"Well... deflated; about the size of this one," she pulled the one out her ass, "about eight pumps later, maybe a inch bigger around, an inch or so longer."

"That's what, like five inches," still rubbing on her leg, pointing to the one on the bed.

"I guess. Not as big as us, does it still hurt?"

"Naw, I think I could almost nut with it "

"So can I get my first, now?"

"I think I'm ready, how do we do it?"

"Watch out, first I gotta see this!"

He moved over and Nazz crawled behind him, inspecting his ass, tugging on the dildo making him flinch before releasing the air, pulling it out slowly; his hole was gaped open just enough for two fingers to slide in.

"You're nice and open," she pulled her fingers out, reaching for regular lube.

"So how you want me?"

"It's your first time with a lady like me, pick."

"Yeah but it's your first time topping, so ladies first."

"I want... just like this, dudes seem to love doggystyle," she lubed herself.

Positioning her tip, slowly sticking it in, rubbing her hands over his ass, pushing in balls deep.

"Oh my god, this feels so fucking good," she exclaims. "Shit, my bad, you good?"

"Yeah just don't rip my ass."

She eases back out almost to her head and pushes back in, taking her time, breathing, watching her cock go in and out of his ass, fascinated. His grunts turn to shallow breathing paced with her strokes, the feeling of her pulling out and in. She pulls all the way out and his hole is opened a bit more, she watches it breath before rubbing her cum around the opening and sticking back in. Laying on him, she humps, wrapping her arms around his body, kissing parts of his back she can reach. Her cock massaging his insides.

"I think this is the fastest I've ever came."

He slides his legs down under her, so they lay flat together, her tits pressed in to his back. She starts to pull herself by his shoulders, working her hips, stroking out her orgasm.

"Fuck yes, thank you daddy! Unnng," she cried through her orgasm, still stroking.

"Don't stop, shits feelin too good," he begged.

"I don't want to. Trust me, baby."

She continues working her hips, pulling out so far, pushing back in to him. He starts to grip at the bed and clench up. His breathing is harder, so is hers. He tries to push back in to her, clenching every time she starts to pull out. Nazz braces herself up, he starts grunting and clenching hard as he orgasms, she cums with him, pushing her cock as deep as it'll go, spraying his walls again.

JaxRhapsody
JaxRhapsody
211 Followers
12