First time with a shemale stories

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First time with a shemale stories

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Does that mean I'm a frustrated homosexual? I don't think so. However sometime during my life i began to wonder what it would be like to suck another guys cock and be penetrated.

Guys don't turn me on, I tried fantasizing but the reality of hairy blokes just left me cold. About 2 years ago I began looking at Transexual porn and realised that I was attracted to the male genitals when surrounded by the female form.

It was at that point that a seed of an idea formed. There I was in a backlane somewhere in the suburban areas of a UK city looking down a path to the entrance to some slightly salubrious looking flats which fronted a tired row of commercial property.

Prior to this I had been considering how I might do this thing. How to keep it secret and what might go wrong. After extensive research i found a Transexual Escort that was far enough away that it was unlikely I would be seen, but close enough that any meeting could be fitted into a day.

I was very tense as I rang the number from my mobile, seated in my car prior to an early business meeting.

My throat was dry and I was shaking. The phone was answered and the person on the other end sounded mature and very female.

She gave me direction and we set a time for later that day. I even took cash out of my credit account so that it was all very untraceable.

The whole business meeting I felt like a nervous wreck, my mind rnning over the reality of what I was about to do and my concentration on the meeting at an all time low.

Wow, sucking a cock and getting penetrated in my virgin arsehole for the first time. I had struggled to find the address and when I did eventually park up, the row of shops looked very forbidding, seedy and slightly run down.

The path to the flats lead to a slightly open door and I was told to enter and go straight through to the door directly ahead of the enterance.

I knocked and was ushered in to a small apartment. My date was taller than me. She was slim, white with long blond hair and was wearing black knickers and a bra.

I didn't dare stare at her so just asked if I could use the toilet first. When I emerged she showed me into a small bedroom which was lit with a red light.

She asked for the money first and I fumbled the cash from my pocket. She told me to take my clothes off.

I had expected this because it's a way to ensure that prostitutes are not going to get incriminated and prosecuted by the law.

I undressed without any formality and piled my clothes up on the chair next to the single bed. The room was very warm and felt quite secluded and intimate.

She asked me to get on the bed and lie face down while she gave me a massage to help me relax. I felt her weight on my buttocks and the warmth of her thighs around my waist.

There was a squeezing sound from a bottle and massage oil was dribbled onto my back. The oil was very heady and having her hands work over my body was incredibly sensual, really hot as her hands glided over my buttocks and moved close to my groin.

I was happy just lying there and relaxing as she talked to me about what I wanted to do with her. I was half expecting her to say that she wouldn't let me suck her cock, or penetrate me, but she said it would be fine.

She lifted off me slightly and asked me to turn over and lie on my back. She sat back down and began to massage my chest. After a short while she stopped and asked me to put my hands on her.

She laughed and said that it was what i had paid for after all. I didn't waste any time and tugged her panties down and exposed her limp cock.

She was shaved and that big purple cock head protruded from the wrinkly foreskin. This was the first time I had been so close to another cock and I filled my mouth full of that delicious fruit.

My hand delved inside her skimpy black panties and cupped her soft, warm balls. God they were big, mine felt more like chestnuts and hers were big ripe plums.

Her cock began to grow in my mouth as I sucked and liked the head and shaft. She asked me to be careful with my teeth and I tried my best as her cock swelled to fill my mouth forcing my jaws wide.

At this point she got off me and took that amazing rod from my lips. She was fully erect and from my position her cock looked about nine inches long and I was wondering how the hell I was going to get that monster inside me.

She took off her panties and bra and lay down beside me. I couldn't keep my eyes off that giant between her legs. The head looked like it was about to explode, the skin was tight and smooth and the shaft slightly curved, milky white and veined.

I started again. Engulfing that swollen head with my lips and letting my tongue run along the piss slit and along the back of the head.

I wanted to take it all in, to savour every moment. I was suprised at just how slippery a cock head actually is, not at all like plain skin it is more of a membrane and it has a taste.

In this case I knew it was the taste of a male, not unpleasant and quite arousing because I felt very submissive without being threatened in any way.

I licked her massive balls, I just couldn't get over the size of them and felt a kid of privilige that I was being allowed to hold another persons tender, vunerable parts in my hand.

My tongue picked up the slight coarsness of her closely shaved scrotum, another turn on, and suprisingly I wished she had a full compliment of pubic hair for me to nuzzle into.

I really wanted her to cum in my mouth, but I worried about the possibility of picking something up not so bad if you are single. She asked me if I wanted to be sucked by her.

I nodded and she twisted her body until she could swallow me. I wasn't really up for having my own cock sucked. I was about to leave but she came out greeted me while I am in my car and told me to come and fallow her into her apartment.

Her apartment is really small and by the looks of it she lives by her self. I laugh a bit because there is porn on when I enter the living room and we talk about ps3 and how she knows how to fix them.

When I first saw her with my eyes I realized she is really tall and she is beautiful and the pics she sent me do no justice, she looked way better in person and even better than her porn videos.

We talked and she told me, she was a porn star for a while for she-male strokers and she told me stories how men with there wives would recognize her at the stores.

After a while she asks me what turns me on? Know this is my very first time sucking on a cock at all and especially at this size its huge.

I lick the head gently like ice cream hoping to get that cream filling at the center. Then I finally put it in my mouth and I am moaning with so much excitement.

I am kissing her cock, smelling it, rubbing it and trying to take as much as I can in my mouth. I can tell she is getting really Horney.

She asks me did you bring the condoms? I reply no because I become scared and she looks at me, with so much disappointment.

She puts lube on her finger and goes in me it felt so good entering my tight little boy pussy and then puts some lube on her cock before entering me.

Now this cock was way better than that guys cock before. I felt so much and she was way better in every way.

She is really making my ass stretch to its limits. After going in slowly she finally all the way in me.

Then here comes the best anal sex I have ever had in my life. She pounds me at a long slow pace at first it feels so good I can feel it through my whole body.

Office Workload Ch. Lily An accident leads to a very pleasant surprise. Sex Adventures with Alisha Ch. Permanent Slavery Journey Ch. Caught with Consequences Ch.

Alex's Fateful Feminization Pt. Chains Willing Ch. A Big Surprise! A weekend get away to share kinky truths and a big surprise.

The Houseguest A daughter's friend packs a surprise that tempts her mother. Expectations be Damned Ch. Surprises incoming. Ginger and Cinnamon Cinnamon puts spice into Ginger's life.

Goth-night Getdown Guy meets girl at a goth night and have sex. Shower Curtain Glory Hole Quarantined guys find a solution.

A Mother's Duty Ch. What could go wrong? Welcome to Paradise Pt. Rosa's Mask Ch. The Meeting Employee experiences three-way her with boss and new client.

The Brown Bag A futa Captain kills time at a backwater space port. Special Delivery A Courier provides some premium service for a special client.

Jasmine's Magic Fluid Transsexual woman has magic powers. Journey to Trans Submission Ch. Who Wanna Be a Bimbo?

Face Down Ass Up Leslie takes control and lets me feel all of her. Red Rose Rose's romantic adventure reaches new heights of threesome!

X-change: Lockdown Two guys trapped in the lockdown get help with a pill. Bayonetta's Abuse Ch. The Lab Rat Pt. My First Ladyboy Experience How a massage opened more than my mind.

Save Some Punch for Me Pt. The Theater My first taste. Master is Going to Cum Now Imagine a website that caters for all your dreams Second Life Two students are kidnapped and then auctioned as sex-slaves.

Becoming Joey Ch. Fucked by Hope Guy gets fucked and playfully dominated by his t-girlfriend. Caught Red Handed Pt. Rescuer A hermaphrodite mage saves a knight.

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.

That's one of the nice things about her bedroom, she has several large mirrors throughout the room and we can look around and see ourselves fucking and sucking in every position, and from every angle.

Very sexy I must say. And now it's my turn. I lay down on the bed as her head dives between my legs, sucking on my cock, getting me nice and hard again.

Doesn't take long, and I long to fuck her sweet ass. Her ass really is a thing of beauty. She's got that latin blood if you know what I mean, and I tell ya, her ass is a true blessing.

Nice and round, and very feminine. Total J-Lo ass and perfectly smooth. We lube up her ass and dab the towels a bit more from her little bottle of rush, freshening it up.

We're on her bed, and she gets on her hands and knees, her asshole ready to be fucked. I take a nice look at us in the mirrors and the scene is truly amazing.

Looking down at her asshole, I squirt a healthy amount of lube all over her hole and on my cock before insertion. I slowly slip my cock into her pretty little asshole and the feeling is amazing.

I've never had anal sex before, so this too is a brand new experience for me. I inhale heartily from the dabbed towel and my brain catches fever turning every sensation into sheer pleasure.

And boy, it doesn't take long before I have to cum. I'm watching her head sway, and her hair bouncing up and down. Her ass meets my every thrust and it isn't gonna be long.

I hunker over her and start fondling her breasts and sucking on her neck as I feel my hot cum boiling in my balls. I tell her I'm about to cum and she actually pushes her ass harder against my cock, preventing me from pulling out.

I feel my body quake as I heave into a tremendous orgasm. My cock explodes into her ass, pumping stream after stream of cum deep inside her hole.

Wow, my head and body are spinning. Our bodies are covered in perspiration and my cock finally slips free from her little asshole, a long string of cum dangling all the while, still keeping us connected.

She turns over and we kiss passionately, our tongues lapping at each other's still hungry mouths before she dismounts from the bed and makes a quick trip to the bathroom for a little cleaning up.

I follow her into the bathroom when she is finished and clean myself up a bit as well. Soon we're both back in her bedroom, blowing some more smoke and talking the night away before another nice session of sucking and fucking.

She cums all over my face and I leave a very, very happy young man. It won't be our last time together, and she even goes so far as to tell me that I was one of her most incredible sexual experiences ever.

Trust me, the feeling was definitely mutual. I'd love to share more experiences, and trust me, there are plenty, if anyone is interested, but I think this is good stopping point for this first shemale experience.

Hope everyone enjoys it, and now, I've got to jack off. Because reliving this experience has left me with quite a spot of precum on the front of my boxers.

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