Platonic Friends and Unexpected Encounters, Part 4

Pantyhose, heels and in position (Wikimedia)

Pantyhose, heels and in position (Image: Wikimedia)

This is Part 4 of 4 of the story when two male friends decide to have a little fun in lingerie, pantyhose, heels and makeup after a casual evening at the bar.

Part 3: Curious Crossdressing

Part 2: Let’s Play Dress Up

Part 1: Two Friends, Maybe More

* * *

Sticky Wet Pantyhose

So there we are, Eve and I lying on my bed making out like two crazed, horny teenagers. I can’t really tell what was going through my mind, probably due to the numerous beers consumed earlier, but all I can say is that it feels incredibly exciting and I was more than willing to “cross the line” where I haven’t been before.

To let out a little secret, I have had an attraction to other crossdressers for quite some time now. For me, there is something so sexy about a male who can transform himself into woman (the more passable, the better of course) but, oddly, I’m not in the least bit attracted to masculine, unfeminized males. Maybe you can say that I’ve grown a fondness for chicks with dicks.

It makes total sense since, in those times when alone and throwing on a silky teddy and glossy pantyhose, I can’t stop thinking of how I would love for someone else to give me a good fuck. I mean, what better way to feel more like a woman, right?

I have even been preparing for that special moment by purchasing an eight inch dildo and a smaller, smooth profile vibrator. Both of them to, shall we say, “perform tests” on my cute little virgin ass before someone else calls it their own. Turns out, it was a smart move.

On one lonely afternoon, maybe a month ago, I decided to try them out. After cleaning my ass nice and tidy, I start out with the smaller vibrator, lube it down and begin with the first thrust gently in my “vagina.” Next came my surprise at the pain that instantly followed. Huge turn off!

Yet, I quickly learned that the following session of ass masturbation hurts less, and even less the next time until it becomes an almost necessary pleasure. I followed up with the larger dildo until I was confident that I could take on any tranny cock out there.

So now I get the chance to see.

I’m enjoying every moment of our passionate foreplay. The silkyness of the pantyhose on our tangled legs and the feeling of our lipstick smudging against one another is so incredibly intoxicating. With an instinct that I never had before, I reach down for Eve’s now rock solid cock and grab it through it’s pantyhose encasing.

As, I slide my hand so slowly up and down her nylon-covered rod, Eve releases a moan that convincingly sounds like a woman. We continue our passionate kissing while I simultaneously stroke her gently. Then I notice Eve gently pushing my head away my face and down towards her pantyhosed cock which I still have a firm hold on.

I let go, pull the pantyhose away from Eve’s member and put it in my mouth like a hot popsicle. I can’t say that I have ever given head before but I’m doing what comes naturally, sucking it as if it were my own. I must be doing a good job since Eve is girly moaning louder than before which also turns me on in the process.

To be honest, I would have thought sucking a dick would be somewhat of a chore. But turns out it is actually quite a pleasure watching your lover scream in sheer delight while it easily slides in and out of your throat. I guess I’m a natural, too, since I do not experience any gagging. I could very well get use to this.

After a few minutes of steady blowing, though, I stop well before Eve is about to come and turn over onto my back, still on the bed.

Now at the moment I have been eagerly awaiting, I whisper, “Please be gentle.”  Eve smiles in anticipation.

My silken thighs are drawn back back and legs fly up in the air. Eve casually rips an access hole in my pantyhose right the middle of my butt. “Sorry,” she says with a sly smile. I don’t know why but I ponder for a second that she just ruined a brand new pair of my favorite Oroblu pantyhose.

But then as she quickly lubes down her own excited member, all thoughts of that fade as I am overcome with an excitement so intense that I begin to tremble. At last, the fuck I’ve been waiting for.

Mounting me missionary style, she begins to penetrate, very slowly at first, carefully aware of how I am taking it. Little does she know I can take it quite well actually.

Then come the first slow thrusts. Oh, how wonderful this feels, even more so than the dildos I’ve played with before. I let out the best girly moan I could muster, loud enough for all the neighbors to hear.

“Harder,” I scream.

Eve complies, ramming my ass harder and harder with each pounding and making loud clap upon impact. The rush is so incredible, sending me into a dizzied frenzy. I moan louder and louder wishing this never stops.

But suddenly it does. Eve pulls out and grabs the sides of my thighs, placing her glistening cock right in between them, just above my own raging cock, and pushes my nyloned thighs together. She begins her thrusting again, easily gliding through the pantyhose in the thigh crack she created.

Moments later, I hear a loud moan of release as her love juice forcefully ejects onto the crotch of my pantyhose. The warm, creamy spunk feels so lovely oozing over the hose resting over my cock that I don’t bother to clean it off. I take a dab of it with my finger to have a taste. Just as I thought, pure honey.

We each share a moment of the afterglow as I prop myself up and give Eve a soft kiss as a thank-you gesture of sorts.

“My turn,” I lightly whisper. “On your hands and knees.”

Still on my bed and Eve obediently assuming the doggie-style position, I quickly rip a hole in the back seam of her black pantyhose. Then pull down the sticky wet front of my own hose and lube down my highly aroused member this time.

In it goes, nice and slow. “How nice and tight that tranny tunnel is,” I think to myself. I start to slowly thrust and moan, noticing how much better this feels than a vagina. Eve softly screams in pleasure as well, noticeably higher pitched than when she was previously in charge.

“Ahh, faster!” she screams. I comply, grabbing her butt for support and making it clap with each forceful ramming. Our moans share screams of sheer ecstasy in unison.

I reach the point of climaxing when I decide to pull out. Barely a second later, I burst all over the pantyhose covering Eve’s ass. Eve reaches back and feels my warm honey covering her butt. “Enjoyed ourselves, did we?” she quips.

Yes, indeed.

Eve collapses face down on the bed while I grab a towel and wipe her ass free of cum.

In this second post-fuck afterglow I’m having, I notice that, rather than having the urge to kick out my lover as I usually have done with girls, I want Eve to stick around. It seems as if I am falling in love with my crossdressing lover. Can this be?

“You have more pantyhose, don’t you?” she asks as if reading my mind.

I guess I’ll have to ruin a couple more pairs now.

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Posted in Erotic Stories
2 comments on “Platonic Friends and Unexpected Encounters, Part 4
  1. Charlie says:

    Oh yesss! I love the sucking and yes I feel the same way about oral, I am a natural too. I really enjoy the pleasure of being penetrated, I really wish it could last longer. I really like the cum inside me, I can sometimes feel the ejaculation inside me and if we don’t so that I love to swallow it. I am in such a horny mood right now…

  2. Sheery says:

    Nice to see you back! I guess I don’t have to ask if you enjoyed the story 😉

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