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First Time With a Shemale

Shemale
2008-01-17

Topic: First Time with a ShemaleI've had a couple previous stories where I go into detail about some fun I had with a celebrity's daughter, well, here's another side of my sexual personality that I like to explore every now and again, and just like with the celeb stories, this one is pretty much totally true, at least as much as I can remember anyway. . .  I'd also like to add that all of these events took place after my experiences with the celeb's daughter, and I certainly don't recommend this lifestyle for everyone, especially a few sections that I'm sure you'll figure out when you get to them, for whatever that's worth. . .
I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality.  I'd been with a few girls growing up, but nothing ridiculous.  I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we say. . .  party favors.   
I liked my share of porn, and as I had just gotten my first computer, I finally had the resources at my fingertips to do as much online porn surfing as a young man could handle.  And it was only a matter of time with all the stuff out there that I would stumble upon shemale porn.  I'd never seen anything like it.  Here were beautiful looking women, very feminine but instead of a pretty little pussy, there were these dangling cocks hanging between their legs.

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    I was utterly fixated, and I've been hooked ever since.  Don't know what it is, but there's just something about t-girls that completely fascinate me.
So I would look at the pretty shemales from time to time, jack off, and wonder what it would be like to be with one for real.  Well, this went on for a couple of years, just looking at the online stuff and continuing to date real, genetic women.  But then I entered a period where I wasn't seeing anyone regularly, and my fantasies about shemales began to become even more fixated.  
I had just joined an online site for dating, and it was a little more risque than the usual dating site, almost a bit "swingerish" in some respects.  There would be gatherings and all kinds of sexuality getting thrown around, althought to be honest, I didn't participate in much of that, though I did go on a few dates, and did manage to get lucky a few times.  Well, one night I'm perusing the chat room on the dating site, and it's the same ol' usual dialogue, until a new person logs in.  I certainly didn't recognize the name, but her quick profile read that she was a woman, so of course I immediately clicked on her name gaining access to her full profile.  
I of course click on her photo album first, and wham!  What do I see but a picture of her with a big ol' cock hanging between her legs.  Dear lord, she was a shemale!  And furthermore, she was absolutely gorgeous.  I looked around her profile, and she seemed pretty cool.  She was articulate, funny and wow, very sexual.  She also must've liked to have a good time because she mentioned that she liked to "smoke".  So I'm thinking, "great, she's a pothead".

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    Oh well, can't have everything right?  Not like I'm looking to get married anyway, so in any case. . .
I'm a little nervous to strike up a conversation with her because I know many people in the chatroom, and honestly, I didn't want to give anyone the impression that I was some kind of tranny chasing weirdo!  Hey, call me what you want, but I'm thinking most of you would understand my predicament, especially considering how new I was to the whole thing.  But eventually, we do exchange pleasantries, and I end up just writing her specifically, and having a message delivered to her profile.  To my luck, she writes me back and says that she likes my profile and is definitely interested.  Wow, my mind was blown, and all of a sudden, I started getting a little nervous that I was actually maybe gonna do something about my shemale fascination.
We go back and forth on the site's messaging system for a bit before trusting each other enough to exchange emails, and then eventually phone numbers.  I was especially hesitant because I feared she would call and one of my roomies would answer the phone, giving away this "double life" I was leading.  But thankfully, I never had any problems, and when i got a cell phone, that prevented any possible problems that may have created.  But for a number of reasons, we just never actually set a date for getting together.  I was very nervous as this would be my first time with a shemale, but after several weeks, and a good phone conversation with her, I was at ease enough, and we made a date to get together that night.
She lived about a good half hour away, which would mean I'd have to do a bit of driving.  I thought that maybe a hotel would be good, but she was a little nervous about that, and we decided to have our first meeting at her place.  
I won't lie to you, I was still very, very nervous, but I was gonna go through with it.

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    I get myself cleaned up, run down the street and pick up some beer, wine and flowers, and off I go.  The whole drive to her place, my stomach is flipping and my mind is racing.  i can't even imagine what is in store for us, and if I will be able to actually even go through with anything even when I finally do get there, but soon enough I'm pulling up in front of her house, and I see her face poke out of a window.  Whew, nervous as hell. . .
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 nightie 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.

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    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 nervous nellies.  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.

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    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 favors, so I'm going into this with an open mind.

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    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 nightie, fully exposing her gorgeous breasts.  My eyes are glued to this beautiful woman as she wiggles out of her panties, exposing her beautiful cock.  And I'm here to tell you, she has a 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.

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    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.  Perfect!
I'm sucking her cock for a good 18 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.

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    She is laying 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 lays 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 figits 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 vapors eminating 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.

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    My head is spinning and everything feels so good.  And then.  I feel the head of her cock enter my virgin ass.  Wooooooooooowwwwwwww.  The feeling is INCREDIBLE.  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.

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    The heat coming off of our bodies is extrordinary.  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.

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    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.  I think I better take care of that! 
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