First time with tranny story

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First time with tranny story

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We drank make-shift martinis that she concocted from the mini bar. I kept thinking about my wife to bring myself back to reality, but Elena was a living breathing babe that was flirting right then, right there.

When she leaned over to kiss me she was a little taller than me and I liked that her tongue knew exactly what it was doing. My hands were hesitant, but she placed them on her breasts and massaged them around.

She suddenly pulled away and I figured she noticed my wedding ring, but instead she asked me to wait on the balcony while she went inside.

She had a surprise. She asked me close my eyes and turn away. I did, obediently. She rubbed up against my back and I could feel something poking at my pants, against my asshole.

A dildo! I had completely forgotten about my wife at this point. I felt like I was in a porno. She reached around and unbuckled my belt, sliding my pants down.

My cock popped out, happy to escape and ready to go. The dildo was wet as it slid between my legs and up through my butt cheeks. I turned around wanting to suck her awesome tits before she initiated me.

Her cock? His cock? I froze and felt a little dizzy. I was trying to comprehend what was going on. Then I looked at her face — all woman, her legs — all woman.

That was the weird part. She was waiting for me to react, to decide what to do. My cock was still hard as a rock.

I turned back around and bent over the railing. She pulled out and came all over me. The juice ran down my legs, that were shaking.

It was unreal. Best Trans Dating Sites for I shuffle up her walkway and through the gate, hearing dogs barking as I ring the doorbell. Soon thereafter, she answers the door.

I'll call her Valerie, and dear lord, she looks absolutely amazing! She's even prettier, and more feminine in person.

She's wearing a lovely little flowery, red nighty that is mostly transparent, exposing much of her beautiful breasts. She's wearing matching red fish-net garters, and I take a closer look and see that her panties are also quite see through, exposing her penis.

My heart is about to explode out of my chest, I'm not kidding. I'm standing there wondering just what in the hell did I get myself into here.

But Valerie welcomes me inside, giving me a warm hug, although my worried self prevents me from truly embracing this beautiful creature standing before me.

Hey, I'm doing my best here! She shows me around her house a little bit, and is very inviting. I give her the flowers, and she chuckles a bit at the site of the beer and wine, saying that she doesn't drink, but she certainly appreciates the thought.

Well, it doesn't take me long to crack open the beer, and I'm actually a little thankful she doesn't drink, because I'm thinking I'm gonna have to polish this 6 pack off and rest my nerves!

We are soon in her bedroom, and I'm drinking my beer like it's going out of style, already polishing off 3 bottles in the first 20 minutes of our conversation.

Valerie is very inviting, very cool, relaxed and terrific in every way, but I just can't shake the nerves. It gets even worse when the conversation steers toward a sexual nature and my eyes keep drifting to her crotch, seeing her cock bulging out of her panties.

I think it's probably a good time to describe Valerie a little bit. She's very feminine. She has a very curvy little body, and probably stands about 5'5" tall.

She is a little Latin girl, and that only helps her femininity as it adds to her sexual ambiguity. Her breasts are probably a perfect C cup, and she has lovely curly black hair, framing her beautiful eyes and lips.

Her fingers and toes are perfectly manicured, and her smile could light up a room. Her voice is even quite feminine.

And it was all wrapped in a beautiful, honey brown skin. I sit on her loveseat, as she lounges on the bed, cracking open my 4th beer as we both light up a couple of cigarettes.

I feel my nerves easing a bit, but I'm still nowhere near ready to do anything sexual with this girl. Thank God she was so good with newbies, and could carry a conversation.

But as our chat gets a little more sexual, she tells me to please get undressed as she'd like to get a better look at me. I stand up and start unbuttoning my shirt as she looks on, continuing to chat, and then compliment me on my physique.

I can only giggle, and blush nervously. I then pull off my shoes and socks, and start unbuckling my belt. Her eyes never leave me, and my throat is dry.

My belt is unbuckled, and I unzip my pants. She then slides off the bed and resumes my old spot on the loveseat, right in front of me.

I pull my pants down, and she slowly reaches through my fly in my boxers and starts stroking my cock, looking up at me, and making sexy talk.

I feel like I'm about to have a heart attack as she takes my cock into her mouth. She sucks on my cock for a bit, and then asks me if I'm still nervous.

I reply that I am indeed still pretty nervous, and she asks me if I'd like to smoke with her. I say sure, as maybe that will help me out nerves-wise.

She reaches into her night table, and pulls out the stuff, and I notice right away that she is definitely NOT a pothead.

This is a completely different animal we're talking about here. But as I said before, I like to experiment a bit with the party favours, so I'm going into this with an open mind.

Hey, frankly, it's nothing I hadn't done before on a couple of occasions, only this time, I'd be doing it in a sexual setting, and not a social, party kind of setting.

So she fixes herself up as a giant cloud of smoke wafts through her room and then gets everything ready for my toke. I inhale nice and slow, and blow out an equally huge cloud.

And WHAM!!! All of a sudden I am NOT nervous anymore. All of a sudden, I'm Chatty Cathy and pulling my underwear off. I'm a sexual force and the feeling is absolutely incredible as all of my inhibitions go by the wayside.

Valerie and I chat for a bit more and she asks me if I'd like to see more of her. Of course! She pulls off her little nighty, fully exposing her gorgeous breasts.

My eyes are glued to this beautiful woman as she wiggles out of her panties, exposing her beautiful cock.

She has a little trimmed patch of pubic hair directly above her cock, but the rest of her organ is perfectly shaved from her asshole, to her balls, to her shaft.

Smooth as a baby's bottom. She resumes her spot in front of my cock, getting down on her knees this time and starts sucking on my cock as I feel myself getting hard in her mouth.

The feeling is incredible, and watching this beautiful shemale wrap her lips around my cock is about more than I can handle.

But I soon feel like I'm missing out a little bit, and I ask her if I can suck her cock. Yeah, I'm not nervous at all anymore. She stands up, and I kneel down in front of her dangling she-cock as I touch a cock other than mine, for the first time in my life.

Her cock feels so soft, and while it's much like my own, it's a completely different feeling touching someone else's cock for the first time.

I tell her this, and it only excites her that much more, knowing that I am a shemale virgin. Her cock slowly grows in my hand as I begin to stroke it up and down before finally kissing it on the head.

Her cock jumps a little bit, and she sighs as I wrap my lips around her pretty cock. Wow, I'm sucking a cock for the first time in my life, and it's absolutely wonderful.

I ask her periodically if I'm doing a good job. Hey, I know what I like when a girl is giving me head, and you'd think as a man I would know how to suck a cock, but this IS my first time.

She tells me I'm doing great as my head bobs up and down on her beefy dick. And yeah, it was a beefy cock.

As she got hard in my mouth, I could finally see just how big her dick was, and it was just the perfect size. She was probably about 7 inches long, nice and thick, and very rigid.

I'm sucking her cock for a good 10 minutes or so, and by now she's reclining lazily on the loveseat, as we gaze into each other's eyes with my hungry mouth wrapped around her cock.

We move over to the bed and get into a nice 69 position. She is lying on top of me feeding me her meat as I feel her perfect lips slide down my cock, getting hard in her mouth.

While sucking on her cock as she lies on top of me, I also get a nice view of her asshole. I instinctively move my lips and tongue to her little hole and start licking.

I feel the vibration of her heavy moan as her mouth still sucks on my cock. I ask her if she likes that, and she says yes, she loves it.

I keep licking her little asshole and tell her that I want her to fuck me. She happily agrees! As it is my first time getting fucked, I'm a tad nervous, but I'm so sexual at the moment, I long to feel her slamming into me, knowing that she'll be fucking my virgin ass.

I know she feels the same excitement knowing she'll be popping my cherry. She fidgets around in her night table again, and tells me to take another hit off of the good stuff.

I happily oblige and get another heavy rush of euphoria. Then she tells me about something called rush.

I watch her as she gets a little bottle out from her night table and tab a cloth with whatever is in the little bottle.

She says it will help relax my asshole as she's fucking me, and will also make the entire episode that much more pleasurable.

Hey, who am I to turn down more pleasure?!? She also inhales the vapours emanating from the little bottle and turns me over onto my stomach.

I feel her dab my asshole with lube as I take in my first breaths from the dabbed towel. My head is spinning and everything feels so good.

And then. I feel the head of her cock enter my virgin ass. She slowly starts fucking me doggie style and I feel her hands gripping my muscular ass as her hard cock pounds inside of my tight asshole.

She is grunting and moaning like an animal as I try to find her rhythm. Soon I'm feeling so good; I'm talking dirty and meeting her hips in perfect unison with her pounding hips.

I reach behind her and grip her ass, forcing her deeper. The feeling is just so good, I can't get enough. I'm a total sexual animal, and I can't even begin to say how good it all feels.

Her pounding is causing us to slowly move from traditional doggie to my face being forced into her pillow as she just pounds at my asshole.

The towel is close and I take another breath as I feel her also taking another breath when she says that she's getting close to cumming.

I tell her I want to see her cum and as she pulls out, I flip over and her cock explodes all over me. Her hot cum sprays on my chest, my neck and my face, a little bit hitting my lips.

The heat coming off of our bodies is extraordinary. Our bodies are damp with perspiration and the room smells of sex. She grabs a towel and wipes it down my asscrack and asshole, cleaning me up a bit as I rub her cum into my skin, taking a nice long look at us in her mirrors.

First time with tranny story

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