CD Gets Fucked while House-Sitting

This is a true story that happened recently. I also recently submitted a four-part, runaway-imagination complete fiction story, hope you enjoyed. For anyone not familiar with me or my stories, here's a brief background.

I'm middle age, white, a little overweight (hidden well with the right garments), and a married bisexual crossdresser who LOVES getting screwed and wearing women's clothes. My legwear preference, which you'll see in all my stories, fiction or non-fiction, is pantyhose. I LOVE pantyhose (and tights)! I'm not into stockings. I love the total coverage, the tight feeling, and you can always rip the crotch out for easy access!

I also clearly disclose whether my story is true or fiction. This one, as I said, is true, but it was literally a quickie, so there's really not much material to write about, though I'll try my best. It definitely has a 'happy ENDing!'

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I was house-sitting for a friend while he was on vacation. The house was empty, save for a table and four very comfy chairs. It had been renovated and listed for sale, so it was all new, but empty. He asked if I would keep an eye on things, take calls from realtors if they called, and go make sure everything was ok and nobody lobbed a rock through a window etc.

He gave me a key, and said I could do whatever I wanted while he was gone. I could 'hang out' or whatever. He knew I was studying for a certification, and mentioned it would be a nice, quiet place to get away. Immediately I formed a plan, seeing this as a golden opportunity unlike any other I've had in a very long time. I already knew what I wanted to wear, and I couldn't wait until late at night when I could leave home, go to this empty house, change into my female persona, and enjoy some 'me' time.

I love dressing fully, and I mean fully, wig, makeup, nails and all the clothes. It's an exhilarating feeling. I had just bought some purple patterned pantyhose on clearance as well as a beautiful pink bustier with black lace. I would wear that under a shiny black 3/4 sleeve top, and a very tight, sexy, ribbed black tube skirt. I would of course finish off the ensemble with bright red nails to match the hooker-red lipstick I would apply, and a pair of patent black Mary Jane's with a 4" heel. I was already hard just thinking about it.

I got everything together, making sure I had what I needed, including a spare pair of hose (always have a spare, I hate runs), my makeup, lube, and the rest of the outfit that I couldn't easily wear under my man clothes. With that all done, all I had to do was wait...for two days! That's like two MONTHS for my level of excitement and anticipation. I wasn't simply planning on dressing up and prancing around an empty house at night...I wasn't planning on being the only one to enjoy what I would be wearing!

With plenty of time to plan and wait, I crafted an ad on Craigslist. Now, Craigslist has been a curse as well as a blessing. More of a curse though. The number of nut jobs, game players and fucktards you come across is crazy! For every 20 attempts, I'll be lucky to get laid once. So when it actually happens, it's pretty intense, filled with excitement, nerves, fear, apprehension, joy...you know, you shoot some bricks and the day can't come fast enough!

I do prefer the married guys, they have as much to lose as I do, and they just want what they don't get at home...sex or BJ's. Crossdressers are not clingy, picky or judgemental. Guys know we will let them do what their wives won't... take it in the ass, wear lingerie, short skirts, and nylons, and we don't need a new car, jewelry, money or an expensive dinner. Guys know we're not gold diggers! You can fuck us with nothing expected in return. Quick in, quick out, just like a pit stop.

But FINDING someone who'll actually NOT chicken out is a monumental feat in itself. But this time might be different...this time, I have an advantage. My ads always state that 'you must host' or we could meet somewhere dark. Well, nobody can ever host, as they're in the same situation I am...we're married and don't think it would be a particularly good idea to bring home a sex partner...especially another guy, and most people are afraid of doing anything outdoors. Hey...I'M the guy wearing a skirt, nylons, heels and a wig...and YOU'RE afraid? Anyway, that's how it goes.

However, having a place to host, in this case the empty house, while not glamorous, gives me a much better chance than I would otherwise have had. So as you might imagine, I got quite a few more replies than usual...of course, that means nothing if they're all flakes who just want dirty talk and pictures to get them off.

I eliminated most of the replies...even with a place to play I still attracted all the areas morons...and narrowed it down to two that seemed promising. Seemed. I had given a number to text, from an app I have that provides a regular phone number within your area code but uses Wi-Fi or data, so I can change it when I need to and it can't be traced...or worse, recognized by anyone who knows me. As unlikely as it would be for someone I know to be browsing the 't4m' Craigslist personals, I still exercise the utmost discretion and safety to the fullest extent possible.

One of the 'finalists' was only available that night, which was not possible, so now I was down to one. I was hoping this would pan out...I'd hate to miss out on this opportunity. I only had a few days. So this last prospect sounded really serious. He just needed 20 minutes notice to get there, and promised he would show up. Believe it when I see it, but nonetheless, I was pumped, excited, nervous, scared...all the normal emotions I always feel when arranging a hookup with a complete stranger. I'm TRYING to find a regular, and hoping it's just a matter of time before I find him.

My biggest fantasy is to find a regular who is SO regular (and lives alone and lives really close to me, like walking distance), where I could keep a closet full of clothes and shoes at his place, and a drawer full of makeup in the bathroom. I guess I'm looking for a 'double life.' So far, this is still just a fantasy. Back to reality...

We agreed on a time, and he wanted me waiting inside the door, on all fours, where he would come in, drop to his knees, whip it out, and slip it in. I wouldn't even see what he looked like, which is fine. He wouldn't see my face, I wouldn't see his, we would simply both enjoy the great, spontaneous sex we both needed so badly. The next two days dragged on and on...

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The day had finally arrived. I had been jerking off to the scene in my head for the last 48 hours, and finally the day, or more accurately, the night, was finally here. At about 11 pm I began putting on as much as I could under my outer clothes. My new purple pantyhose were pulled on first over a pair of purple nylon panties. Then my bustier, for now without the fake breasts that will be inserted shortly, and this gorgeous, tight black tube-type miniskirt. Oh how it conformed to my hips and hugged my legs!

The rest of my stuff...makeup, wig, fake tits, shoes etc...went in my gym bag. I threw the bag in my car and drove the short distance to the empty house. Letting myself in with the key my friend had given me, I locked the door behind me and went upstairs to the bathroom. To this day I still don't know why I didn't use the one downstairs, but I didn't, which really doesn't matter anyway.

In the bathroom I removed my outer clothes, inserted my fake 44C's into the cups, pulled on my top, and applied my makeup. Not really much use for the makeup as he wouldn't even see my face, but I felt so damn sexy and hot being FULLY made up from head to toe. After my foundation, bronzer and blush, I applied my eye shadow, eye liner, and hooker red lipstick.

I then put on my wig, clipped on a pair of dangly earrings, and slipped into my Mary Jane's, my purple legs looking hot as they maneuvered into the shoes. Looking at myself in the mirror, I thought how much of a shame it is that I have to keep this hidden. I would so love to go out like this any time I wanted, day, night, to a mall, Walmart, around town...but obviously, that's not reality.

I get a text from him, not even knowing his name so I don't even know what to call him. He asked if I was there. I told him I was, I was ready too. And horny as fuck!! He said he was leaving his house now, which would put him about a half hour later than what we had set up, already being ten minutes late. I have hours, so it's not a huge deal, but I hate waiting around for someone. Then of course I start to think he's just playing games, it's happened before...I'd be all ready, fully done up, guy said he was on his way, never hear from him again. Some people just like playing games.

My phone is almost dead, so I'm hoping it lasts long enough to continue communicating with him, that is IF he's really coming. About 20 minutes later he texts me again...he's pulling in the long driveway, and asked if I was on all fours inside the side entrance. I said yes, quickly put my phone down, and moved into position, my heels clicking on the tiled floors. I walked down the three stairs, took a deep breath, unlocked the door, saw his headlights turn off, and dropped down to the floor. I pulled my panties and hose down just below my ass, which I had generously lubricated in the bathroom, leaned on the stairs, and waited.

A few seconds later, the side door opened, then closed a second after that. I could hear his heavy breathing. I heard the sound of nylon sweatpants being pulled down, and him rubbing himself to a hard on. The anticipation and my excitement level has peaked. He finally knelt down behind me, and lifted my skirt rather hastily.

He found my entrance and pushed, my hole stretching so willingly to allow all of him to fill my void, then he proceeded to fuck the shit out of me! It felt wonderful! Very smooth, his cock the perfect size, and though I would have preferred he last an hour, that wasn't to be. I heard his breaths get shorter and more urgent, then heard the telltale exhale, much like a pronounced sigh, signaling that I've been injected with another man's cum. He pulled out quickly, pulled up his pants, and left. Never a spoken word between us.

I knelt there for a minute, relishing in the euphoria that enveloped me at that moment. Nothing, and I mean NOTHING is as satisfying and fulfilling to a crossdresser than being fucked by another man...no toys, porn or fantasies can come close to the real experience.

I came to my feet and walked into the downstairs bathroom, jerked myself off, and went back upstairs to change back. I used makeup removing wipes on my face and packed everything away in my bag. When I was finished, I left, locking the door behind me, a wet spot formed in my panties and pantyhose that I still had on under my jeans, got in my car and went to the McDonald's drive thru. Tonight was a long time coming. And I enjoyed every short minute of it.

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To all crossdressers who want to do this but are apprehensive, scared or in denial, I say go for it! You truly don't know what you're missing! You have but ONE life to live...don't look back with regret.