Last Minute Crossdressed Sex

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A last minute reply to my ad leads to the sex I wanted.
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Lovinhose
Lovinhose
221 Followers

I like to write and share my experiences with the world, and I prefer writing about REAL experiences, thought at some point, as in the past, when I hit a 'dry spell' and have no true story to write, I will write a piece of fantasy fiction. I am happy to say, however, that this story, while nothing special, IS TRUE, and I am happy to share it with you all. Also, and anyone who knows my writings knows this, I don't drag out the story.

I don't 'sensationalize' my stories, I tell it like it happened. Perhaps some will find my stories, and this one particularly, boring and anti-climactic, but it's how I write, as I know MOST people just want the story to get to the damn point so they can get to the 'happy ending.'

I personally hate nothing more than to be reading a long, drawn out story with my hand wrapped around my cock, waiting for the part where I blow...but the story just drags on and on and on...that's great for some, and it does, of course, highlight the skills and writing abilities of the author, however, my view is different.

If I want to showcase my writing abilities, I'll write a BOOK, which in fact I AM in the process of doing (an action-adventure-intrigue fiction novel, wish me luck). But, when I write on here, my job, as I see it, is to get you to your 'happy spot' as quick as I reasonably can without sacrificing content, and without putting you to sleep. So, here is my latest story about one of my TWO latest experiences (that story to follow). Hope you enjoy.**

******************

Craigslist again. Were it NOT for Craigslist, I don't know how the hell I'd get laid as my female persona. For anyone late to the party or unfamiliar with my writings, I am a middle-aged, white bisexual crossdresser, and I LOVE when I find a man to fuck the shit out of me! This is such a story, and it happened very recently, finally, after a way-too-long dry spell.

I was feeling very horny, as usual, and I hadn't had a good screwing in quite some time, and I was ready to climb a tree! By this time, I have been dressing completely except for my fake 42C breasts that I didn't have yet, but I DID have for my next story.

I placed another ad on Craigslist, the only successful means of hooking up that I have found in my area, albeit with very marginal, limited success. For every successful hookup I have, it takes about 30 ads to get there. But this night, I got lucky...in more ways than one...and finally got a hit, at the last minute of my 'safe window.'

My 'safe window' is from midnight or 1 am until about 3 am, as this is the time my wife is either sleeping or at work, and even though she knows I dress and like to go out for a drive while dressed, I have to play it as safe as possible as to not arouse suspicion.

It's very hard to find anyone who can 'play' within that late time frame, and most of the time I get jerked around, stiffed, blown off (no pun intended). I really hate when someone makes a commitment, then they 'fall asleep' or just blow me off after I took an hour to get ready. It's a chance I take every time, but it's worth the wait when it finally pans out. Tonight would be such a night.

I like to go out and just drive around, and when I'm done, I'll take care of myself and go home. Tonight I decided to get fully done up, except for my breasts that I didn't have yet, and my glue-on nails that I would put on later, read on, in the hopes that I would get a hit on my ad. This way I would already be ready to go.

I did my makeup, which I really do pretty good with, pulled on a pair of jet-black pantyhose over a purple pair of panties, a black slinky top, my black pencil miniskirt, wig, earrings and a pair of heels, black of course. It all came together nicely, having just shaved my legs, face and chest.

I really 'clean up nice.' I put my phone in my purse, along with my license, some cash, condoms and lipstick for any touch-ups that may be necessary, and headed out for a night on the town...alone but hoping that would change.

My ad said that I was a crossdresser, fully dressed, looking to play from 12 to 3 am, and to be LOCAL to where I lived, or VERY near, like the next village over. I got a couple replies, the usual bullshit like a link to THEIR website (like I'm gonna click on it...yeah, right), and a few one-liners, and got one that looked good. He lived right in town.

I got ready, met him at his house, and we drove to a dark part of town as he could not host, and...fail. He couldn't get it up! So, already dressed up and ready for some action, I am driving around town, hoping for some more replies, and hoping for at least one to pan out.

Almost ready to go home, as I was at the outer limit of my safe time, I got another reply that looked for real, but unfortunately, he was outside my safe zone for distance, and my time was pretty much up. I was desperate though, but still, I couldn't go that far this late. He tried his best to convince me, but I just couldn't do it, it was just too risky.

I was ready to take care of myself and go back home, when he sent me one more message. He has a family member who lives right in town who is away for whatever reason, and he has a key to the house as he was keeping an eye on things for them. He offered to come to my town if I could stay out a little later.

I agreed. Even though I was outside my safe time by this point, I would at least be only minutes from home in case time ran out and I absolutely HAD to get back home. I leave myself a cushion when my wife is working, just in case she comes home early, and I was willing to take that chance tonight.

So, while waiting for him to make the 20 minute drive, I went back home to put on my finishing touch of what was at that time my complete transformation, which was my fake nails, finished off with bright red nail polish.

That took about 20 minutes, so the timing was good, and when I was done and they were dry enough to head back out, I got the message that he was at the house and ready for me to come. It was only a minute drive, so it was very convenient, and luckily nobody I know lives near this house, though it was unlikely anyone would have been up at 3:30 in the morning.

I drove over and parked in the driveway in front of the barn as instructed, and entered the house from the back door. The house was next to a parking lot, with a house on the opposite side, so I was totally exposed to anyone who would have been looking in my direction, though they wouldn't have been able to tell I was a guy. That feeling was so hot, knowing that someone COULD be seeing me, in a miniskirt, heels, nylons, heels clicking along the driveway toward the door.

I find my latest one-night-lover sitting on the couch in the living room, pants off, stroking an average size cock. After some initial small talk, we head to the bedroom where he offers me a drink.

It's always nerve-wracking to meet up with a stranger for sex, especially when you're a guy dressed as a woman meeting a guy for sex. And of course, the excitement level is unparalleled! I accepted a double shot of Jack, downed it, and got down to business. He asked me to take off my pantyhose and shoes, which I did.

This also allowed me to live out another of my fantasies, which is to show up fully dressed, but to leave without wearing the nylons I came in...don't know what it is about that, but I had been wanting to do that for a while.

Maybe its a 'symbol' of having just been taken, for anyone who would be watching...they would see me go in with nylons, and come out without them. Just the THOUGHT of someone noticing that is very erotic, so I was only too happy to oblige him! He fondled me for a few minutes before moving to the bed, at which time he asked me to suck him for a while, til he got hard again.

I began working his cock in my mouth, feeling it grow with each bob of my head. Finally, hard and ready, I straddled him, my knees on either side of his chest, and grabbed his cock, lining it up with my love hole, just waiting for the feeling! Being on top is one of my favorite positions!

It was great, it felt so wonderful when the head of his cock pushed against my ass, and I slowly lowered myself down until it parted me and I was sitting on his lap, his whole cock up inside me. Up and down I rode, for about five minutes, five very short minutes, which is never long enough, all the while running my red finger nails down his chest with one hand, the other playing with his balls, my red nails providing the perfect amount of pain and pleasure.

I pulled out my own cock, a respectable average size, from under my skirt, and while riding him I stroked myself to the most amazing orgasm I have had in a very long time, as I usually don't take care of myself until I get back home or somewhere in between where I just got laid and home, either way, jerking myself off while thinking about what just happened.

But this time was different, this time I was so turned on, so hot, and so into the moment, I had to pleasure myself, and there's no better time than WHILE a hot cock is inside me. I could feel my orgasm rising, and stopped a couple times to prolong it, finally giving in to MY needs, and shooting my hot cum all over his chest, and I rode him until I could feel his cock pulsate with the orgasm he just let loose. I could feel it, as I stopped, with him all the way in me, so I could feel him fill the condom, and fill it he did.

Even though this was just a quickie, it was a wonderful feeling, a feeling like no other, of a man inside of me, fucking me, feeling great pleasure at being able to please a man like a real woman, and giving up what most women WON'T, while WEARING what most women won't wear anymore.

That amazing feeling of a cock spreading my ass, wrapping itself around the shaft, and pushing deeper inside! Unfortunately, I had to make this a quickie as I was WAY past my safe time, and after we were done, I put my shoes back on, put my nylons in my purse, and headed back home.

It was a chilly night, and the cool air on my now-bare legs felt amazing, as did I. I just had sex with another man, while dressed as a woman, and there is no better feeling in the world for me, especially to cum while his cock is inside me!! On my short drive back home, I peeled off my nails and left a trail of red along the road between my lover and my home.

Hope you enjoyed, sorry it was short and sweet, but that's really all there was to it, just a basic, no frills sexual encounter one summer night. I will be submitting my next story very soon, so keep a look out.

Thanks for reading!

Lovinhose
Lovinhose
221 Followers
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3 Comments
dacoach44dacoach44almost 4 years ago
Lovely

Kinda brief, but it shows the need we have for cock!

SuckergurlSuckergurlabout 4 years ago
Horny

Love this submission, your very right about women not wearing what we love to wear

AnonymousAnonymousalmost 7 years ago
Fucked on his own home bed

I also place ads in Craigslist looking for married men who will fuck me. I recenty was hosted by a married man who treated me like a lady, and ended penetrating my asshole very deep and seeding me with his cum. Then we slept together on his own bed...

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