• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Swallowing My First Shemale

Swallowing My First Shemale

It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me.

I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous girls on all the websites, but I'm still so nervous about taking that big first step into taking a shemale cock inside me. It's pretty weird that I'm so enthralled with videos of guys getting fucked hard or being force fed a big, hard shemale cock, but when I get the chance to do it, I chicken out.

Here I sit, again, jerking off to videos of other guys doing what I wish I could do. How do I make that jump from bystander to player? I know I can just call any one of the local shemales I've seen in the past and just set it up, but how do I get past the mental block in my head?

I know it's just an irrational fear of the unknown, but still, it's a fear that I haven't conquered. Well, as it's been said, the only thing we have to fear is fear itself.

If I don't just go and do it, it'll never happen, and the truth is that I really want it to happen.

I want a shemale to take control of me and make me swallow her cum.

On screen, it looks like the most erotic thing I've ever seen, and I want to live it. I'm shaking just thinking about it, but I want this so bad.

I make the call.

The girl I've seen a few times the past couple months answers and we set up a meet, and like usual, I call when I park and she answers immediately when I knock.

She's beautiful. She's Hispanic, about 5'-5" with dark eyes, long, straight dark hair and a body built for sin, with perfect 36Cs, flat stomach with a hint of abs, nice curvy hips and an ass that just begs to be bitten.

She's wearing a black bra and panties and a see trough white teddy, and she's the sexiest thing I've ever seen.

She speaks with an accent and says she's missed me, and I want to believe her, but I'm shaking, I'm so nervous, because this isn't like the other visits when we stroked each other and she blew me and I was on my way.

No, this time will be different, shaky hands be damned.

She leads me into her bedroom like usual, and some kissing begins before we get to the bed. She starts undoing my pants and I'm already rock hard, and she feels it, looks up at me and smiles and kisses me.

"Oh, you're so big already," she says in her sexy accent, as she's rubbing my cock through my pants, and I reach around and rub both my hands all over her perfect ass.

"Yes, baby, you get me that way."

She grabs me by my underwear and pulls me onto the bed on top of her and we kiss, and her tongue and lips are so soft and wet, and I begin shaking even more.

"Why you so nervous, baby?"

I was hoping she wouldn't notice.

I want to tell her why I'm nervous but I choke up and can't speak the words, and she kisses me again, and tells me I need to relax and enjoy, then she rolls me over, to begin our usual routine of her stroking me then giving me head.

She pulls my pants all the way off, and I'm rigid like a steel beam and she starts with light stroking, and my God, it feels so good!

"Baby..." I mutter, then choke up again. I want to tell her I want to suck her cock this time, but my mouth freezes up.

Geez, if my mouth can't even say it, how will it do it?

I can't back out, I'll hate myself. She's the girl I want to be the one, I have to do this and I have to do it today!

She's taken off her teddy and bra, and her tits hang just a bit but are so beautifully shaped and her nipples, just wow, they're as hard as my cock and the size of the tip of my pinky.

I lean in and suck on her left tit a little and she leans back and cups my head, she groans a little bit and tells me it feels nice.

Her nipple feels so good in my mouth, it makes me wonder how a cock would feel, and I wrap my arms around her waist, taking more of her tit in my mouth.

We're lying facing each other on our sides now, me a bit lower than her with her tit in my mouth and I can feel her cock getting hard against my stomach.

I pull her close to me and press her cock against me, sliding my hands to her waist and inside the waistband of her panties.

I'm shaking so hard, I'm scared she'll think I'm having a seizure, but this is it, this has to be it, I cannot stop now, I've got to make this happen.

My heart is racing, but if I can keep my nerve and just work my way down I can do this, I can kiss my way down her stomach to her cock.

"Easy baby, enjoy, it's good, baby," she says in her broken English, and I'm hoping that means she's reading what I want, so I turn her on her back and start sucking her other tit now, laying on top of her, stroking her sides and hips, still grabbing at the sides of her panties.

Oh my God, I'm shaking, I'm so so nervous. I've watched a hundred videos of guys sucking shemale cocks, dreaming of doing it myself, and here I am, inches away from it.

I work my mouth to her cleavage, lick her other nipple one more time, and I start kissing her under her tits and her stomach from one side to the other, stalling because I'm so horny but still so scared.

Is this real? Am I about have a shemale cock in my mouth? I can't believe what's happening.

I slowly kiss my way down her stomach, her panties still on, and she begins to groan a bit, and she pushes her hard cock up against my chest now.

I've never been so terrified and so anxious at the same time, my heart is going all out now.

I drag my lips across the smooth skin of her stomach to the waist of her panties, and I glance down at her and she's rock hard. This is it, it's really happening. I feel like I'm about to black out, I'm delirious.

She's moaning a bit, and I know what she's expecting. I can't back out now. She presses her cock up at me again, only this time, it's against my chin.

I respond by lowering my head further and feeling her rock hard cock against my face through her panties, and I slide my face back and forth against it and up and down its' length.

It feels soooo good!

I grab her panties at the hips and slide them down, and the moment they go far enough, her cock stands straight up, harder than I ever dreamed.

Oh, my God, it's right by my face! It's inches from my mouth!

I thought I was shaking before, that was nothing.

I slide her panties down her legs, and her skin is like silk all the way down, and at her feet, I look back up, and there it is again in all its' beautiful glory - eight inches of thick, hard, shemale cock.

I slide my hands up her inner thighs, and like she knows what I'm thinking, she opens her legs a bit, exposing her balls to me, cock still standing rigid.

I'm completely hypnotized and don't take my eyes off it as I kiss my way up her inner thighs, anticipating my first lick of shemale cock.

I reach up and just glide my open hand up the shaft from balls to head and down again, and she moans.

"Ah, baby, very nice, good, baby..."

I work my way back up her legs and finally, after three years of fantasizing, watching others, dreaming about it, I was going to swallow a shemale cock.

This is a dream, and it's about to come true.

I stroke my hand slowly up and down her shaft and put my face right up near it, I'm an inch away from my dream.

I stick out my tongue and get my first ever taste of shemale cock, and lick it from balls up to the bottom of the head and she groans, thrusting her hips up to my mouth.

"Oh yes, baby, that's so good, yes..."

I'm in Heaven, I'm in another world, it;s the sweetest thing I've ever tasted.

I slide my tongue all the way down again an then up again.

This time though, I pick my head up a bit, and looking down on her beautiful cock, purse my lips and wrap them around the head, and I'm about to explode!

I've got a shemale cock in my mouth! FINALLY!

I slide my mouth down around the head and swirl my tongue around it and I can't hold back anymore - I slide my mouth all the way down her shaft, and she groans out loud, thrusting into my mouth.

She's all the way deep in my mouth now, and I just sit still, savoring her delicious cock, licking my tongue all around the shaft while she's groaning.

I can't believe how hard she is!

I finally slide my mouth back up and lick around the head again, then cup her balls softly with my hand and slide my mouth all the way down her eight inches again.

Her moans tell me she's enjoying it, and I'm euphoric.

I start sucking on her shaft while I have her whole cock in my mouth, and I'm sliding my tongue around it, and I start sliding my mouth up and down her cock, just a few inches, just a little bit, I don't want her to cum too soon.

I feel the head of her cock push against the back of my mouth and gag a bit, and have to pull back to take a breath.

She's got one of the prettiest cocks I've ever seen on a shemale, and it's in my mouth. This is surreal.

I take a breath and wrap my lips around her cock again, just the head this time, and suck on it softly, teasing her a bit.

I can almost feel a pulse in her cock, it's throbbing and I have to have it in my mouth all the way again.

I can't believe it, but I need her cock in my mouth. It's as great as I imagined.

"Papi, suck it," she tells me, and I obey. She's pulled her knees up and spread her legs nice and wide now, and she's a vision like I've never seen, perfect, smooth olive skin, cleanly shaven, and big, thick, beautiful, hard cock standing straight up like a steel beam.

Her pose is so inviting, I need to put my face between her legs.

I wrap my mouth on her cock again, only this time, I give a bit tighter grip with my lips, and I begin a rhythmic slide up and down her cock, and it takes only a minute for her to begin thrusting up into my mouth to my rhythm.

Her cock is delicious and I don't want this to end, but I know she can't hold out too long.

This is why I'm here. this is what I've wanted for three years - the cum load in my mouth, and I'm about to get it.

Here come the shakes again.

What will it taste like? How big will it be? Will I gag?

Here I am having the most erotic experience of my life and I'm asking myself questions.

I tell myself just shut up and keep sucking, you'll find out soon enough.

She's pushing up off the bed stronger now, and I'm matching my sucking to her hips now.

I'm so - fucking - hard!!

She groans and grabs the back of my head with both hands now, and I'm sucking for all I'm worth.

Her hands tighten into fistfuls of my hair and her moaning is getting louder.

She's fucking my mouth now, and I'm absolute glory!

I can feel the throbbing in her cock, like her cum is churning, about to let go.

Her cock is thrusting in and out of my mouth like a ramrod now and I'm keeping my lips tight on her cock, never letting up.

"Papi, I cumming Papi! Papi! CUMMING!!"

Then she pushed up a foot off the bed, forcing my head deeper than ever before.

"UHHHHHHHH!!"

Her load exploded out of her cock like a bullet, filling my mouth and still holding my head down, forced me to swallow it all.

It was huge, and I had to gulp twice to take it all, then she thrusts again, shooting a smaller shot in my mouth, still holding my head down on her cock.

I couldn't believe what was happening. My mouth made a beautiful shemale cum and I was swallowing it.

She finished off with a few smaller thrusts, and my mouth never lifted off her cock.

She convulsed on the bed one or two more times, but still, I refused to let her cock out of my mouth.

"Oh Papi, you suck so good, baby."

Her cock still in my mouth, I look up to see her lay her head back, close her eyes and breathe.

I didn't want it to end though, and I laid there for a few minutes, feeling her cock go a bit soft in my mouth, when I finally let go.

"Was that good, baby," I asked.

"Oh Papi, yes, that was so good, you suck good, baby, you suck my cock good."

I leaned back and just stared at her cock for a minute, still not soft, and licked it up and down a few times just because I loved it so much.

I finally made my dream come true, and it was so much more than I ever imagined it would be.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Swallowing My First Shemale

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 240 milliseconds