Mistaken Identity Ch. 01

Another work of fiction, hope you enjoy.

Many years ago I had a regular. I lived about 40 minutes south of him, but he lived only five minutes from where I worked. I would go to his house after work, often dressing up ahead of time in my pickup truck in the parking lot at work, then heading over for a good screwing. This spanned over a ten year period and was the highlight of my day when he could 'entertain' me.

His name was Hal, a gay man who lived alone and loved to top guys. He always played safe, and though I love bareback, in fact I prefer it, I always agreed to safe sex, especially since he was gay and was at much higher risk of carrying any STD's, though he did take really good care of himself, enough so that had he not told me his sexuality and that he was single, I would have been convinced enough to have unprotected sex with him. But, we played it safe. He never wanted to bottom, and I never wanted to top, so it worked out great.

Then the inevitable day came when he informed me that our relationship, if you could call it that, would not continue as he had found a steady man to be with and wanted to stay true to him. It was hard to grasp the concept of 'staying true' to someone of the same sex, but who was I to judge? I'm just a guy in a skirt wanting dick in my ass...and taking as much as I could get, whenever I could get it.

I had even called him a few years later, just to say hi and see if things had changed any, but they hadn't...he even had the same cell phone number, luckily, which is a rarity these days, seems like everyone changes their number every few years and so many people lose touch. Fast forward to 2020, ten years later, and I still had Hal's number in my contacts. Ten years is a long time. What did I have to lose by trying again? So I did. I called Hal again.

He answered. He STILL had the same phone number! However, he also still had the same boyfriend. But we conversed for a while and the conversation was pleasant enough. Then he made a proposition to me. Not one I would have expected, and at the time, not what I really wanted, but it was intriguing. He told me he was going away for a couple weeks, him and his boyfriend, lover, whatever you want to call him, and offered to let me use his house if I found anyone who could not host, as I could not host either. It would be free, so I wouldn't have to pay for a motel room, nor would my potential hookup, and the discretion would be unparalleled.

I gladly accepted his offer, and he told me when he was going to be gone and where the key would be. I immediately went onto this website called 'Doublelist', supposedly a 'replacement' for Craigslist, though there is really no true replacement. I have had marginal success with Doublelist, but I think that was mainly because nobody seemed to be able to host, not to mention all the nut jobs posting and answering ads. But it's really the only option without paying for a service and leaving a trail for a good lawyer to find if the wife or girlfriend ever suspected anything and had someone followed and investigated.

I was attached and couldn't take the chance. I have occasionally hosted at the house a couple times, which was a huge risk, and we usually hooked up in our camper in the driveway while she was at work. That ended abruptly when one day I had arranged for someone to come over when she came home early because her hours had been cut. A discreet message to the guy who was coming over ended what would have been a great afternoon of sex. Talk about a buzz-kill!

I wasn't about to pass up this opportunity to have access to a house and all the privacy, discretion and secrecy I could ever hope for. Nobody knew me, I wasn't from that area. A large privacy fence along the narrow driveway and the house would give ample shelter to anyone coming and going, and the fact that it would be night time would simply add to the privacy factor. I posted an ad saying I can host every night for the next two weeks, and I was looking for as many tops as I could possibly find. I also opened it up to other crossdressers too, I think that would be pretty hot!

I didn't get much interest at first. A nut job here and there, a couple of crazies asking me if I do what I clearly stated in my ad I DIDN'T do, and one that sounded like a hit but never replied back. Why do people do that? The next day, three days until Hal left his house to my sordid desires and pleasures of the flesh, I finally got a bite. I had put in my ad that I wanted to role-play. I had always had a fantasy of being forced...raped. Of course it wouldn't BE rape because I would want it, but I wouldn't tell the rapist because that would ruin the energy, I would just make sure to cooperate so as to not be harmed, just pretend to give in and promise to forget about it.

I knew what I would say to talk my way out of ending up as a statistic...'hey, I'm not going to say a thing, you really think I want to walk into a police station and say I was raped while fully dressed as a woman?' No matter, that never happened, and I figured the next best thing would be to role-play and pretend. He didn't give me his name, said it would add to the experience, and I agreed. Sitting in my office chair, my cock grew hard as a rock. I had to head to the rest room to take care of it, otherwise the rest of the day would be very uncomfortable!

Back at my desk in the office, I replied to another of his emails, and we set up a date and time. It would be Friday night at 8 pm. I told my significant other that I would be going out with some of the guys from the office for drinks, which she was OK with as she worked the night shift. Perfect. There's just something calming about when your S.O. Is working even if you're far away...less chance of inquiring phone calls and messages, she'll be at work doing her job, thinking I'm out with some guys, none the wiser that some guy's cock will be filling my ass and doing me good.

The mystery man said he would bring a pair of handcuffs. That had always been a huge fantasy as well! Being raped while tied up or handcuffed. This was shaping up to be an amazing hookup in the making. The days until Friday night dragged on like never before. I tried keeping busy to try making the day go by faster, but to no avail. Luckily I'm the owner of this small company so I don't have answer to anyone. Tick, tock. Ever so slowly the hours went by. At home, alone in bed at night, I would close my eyes and fantasize about how Friday night would go, hands cuffed behind my back, laying on the bed, getting fucked, feeling the weight of another man on top of me having his way with me.

Our plan was he would leave the key for the handcuffs on the table in the kitchen, and I would have to unlock myself, a risk yes, but one that peaked my desire, my sheer excitement. I simply could not wait for this night to come. I had my outfit already planned out and packed in my truck, and I would head over right after work and get ready. I would leave about 4 pm, which would give me almost 4 hours to get ready. I would do my makeup, nails, wig, and a sexy, slutty outfit.

Finally, the time came. We had emailed a couple times just to confirm he was still coming, and he assured me he was. Of course, you don't really know until they actually show up, and I've been stood up and blown off more than once. In fact, it's happened too many times. Well, even once is too many times, but you get what I'm saying, it's probably happened to everyone at some point. I left the office at 4:00 pm on the dot, set the alarm, and drove the five minutes to Hal's house.

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The house where Hal lived is a small, modest ranch, built around the 70's, tastefully landscaped without being overdone, the window awnings painted burgundy, the whole house built with red brick, back when they actually used brick all the way around, before the cheap vinyl siding craze that hasn't lost any momentum. Pretty sad to see even million-dollar homes with a beautiful stone front, yet finished off with vinyl siding the rest of the way around. The driveway was just wide enough for my truck without folding the mirrors in, and I pulled all the way through, parking in front of the single-car garage behind the house at the end of the driveway.

I found the key where Hal said it would be, grabbed my small travel bag with all my stuff, and let myself in. It was just as I had remembered it. Very tasteful, clean, neat, not a thing out of place. Hal certainly was not your typical bachelor. It was a three bedroom, one bath home. He only asked that I used the guest room, the same room he always fucked me in. It had a twin bed, a desk, a dresser, and some pictures on the walls. The lamp on the desk cast a pleasant, almost romantic glow across the room. Perfect ambiance I thought, and just as it had always been all those times before. Although our flings were 'quickies', there was nothing like the feeling of when I laid on my belly and he penetrated me from atop, using his legs to move mine together, feeling his cock fill my willing hole, until I could feel the pulsations of his cock as he had his ejaculation.

I really missed our hookups, but I was determined to take full advantage of these next two weeks. I would just tell my woman that I would be working late or something...I'd figure something out. Would be nice if she would be up to participating, but I know that's not going to happen. Sometimes I really wish I was single. But you take the bad with the good I guess.

I had already shaved my armpits, chest, legs and face this morning, but I ran the razor over my face one more time just to remove any stubble that appeared throughout the day, the '5 o' clock shadow.' With that done, I leaned in front of the mirror to apply my makeup, afterwhich I undressed completely down to my black, lace-trimmed panties which were going to be part of my outfit for tonight. I emailed Mr. No Name again, and he once again assured me he was coming. He said he might be there a little early, if that was OK, and I told him it would be fine, just not TOO early, I needed time to finish getting ready.

I put on a black lace bra and inserted my D-cup silicon breast forms that I had finally ordered from Amazon, having wanted a pair for many years but never having, or wanting to spend the money for them, they're not cheap. I followed the bra and breast forms with a stretch 'pencil' mini-dress, oh how it hugged every curve, what curves I had, and looked amazing over my fake tits. It came down to mid-thigh, showing plenty of leg with the added help of the six-inch slit up both sides or the skirt. I topped it all off with my shoulder-length auburn wig, clip on earrings and a necklace.

Grabbing the 4" heel Mary Janes I would strap on my feet, I went into the guest room, sat on the bed, and pulled on a pair of black sheer pantyhose, then I slid my pantyhose encased feet into the shoes, buckled the straps, and finished the whole outfit with a gold ankle bracelet on my left ankle. I stood up in front of the full mirror attached to the dresser, and what I saw took my breath away. For a guy, damn, I looked pretty hot! I started to get hard again, now that I was all ready for this, and had three hours to wait! Oh shit, my nails! I completely forgot about my nails!

This would take up a few more minutes. I grabbed my package of glue-on nails and glued on a set, filing them smooth so as not to put a run in my pantyhose. I had brought a jar of bright red nail polish and applied it to one hand, waved it around for about five minutes, then did the other hand, repeating the process. Once that was done, I was finally, truly complete. I looked myself over to make sure I hadn't forgotten anything else, and realized I never lubed myself. Fuck. It always hurts with my nails on. Good job asshole, forget one of the most important things BEFORE putting little daggers on my fingertips!

I thought of a better way though. I had a dildo in my bag, so I put a glob of lube on the tip and pushed it in my hole, slowly filling my void that would soon be filled with the real thing, lubing myself while at the same time enjoying the pleasure from it, killing a little more time. A look at the clock showed it was only 6:00 pm! What the fuck! I would have to wait TWO HOURS? No way, I just couldn't. Well, I suppose I COULD, but that would be torture. I thought about pleasuring myself to orgasm, as I would be ready again long before he arrived, but it would be best for him to come early.

I sent him another message, telling him I was ready now, so he could come as soon as he could. He replied back 7 painstaking minutes later saying he wasn't sure if he could get here earlier than 7:00, but he would try. We agreed he would just walk in, pretend to be robbing the joint, surprising me in the guest room, overpowering me, cuffing me and doing what we agreed upon, then he would fuck the shit out of me and leave the handcuff key on the table. He said they were real cuffs but he got them at a truckstop for $10 so he wasn't worried about leaving them behind if it would heighten the experience for me. Plus, hopefully we'd do this again and he could have them back. Though I had to wonder why a truckstop would sell handcuffs...

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I decided to hold off cumming, as he could arrive at any moment, but the wait was brutal. I was so turned on by how I looked in the mirror and took some pictures of myself for future posts. I really outdid myself this time, getting ready in record time and how well of a job I did. I almost looked passable, hard for someone who is a bit overweight and 6' tall without the 4" heels. Just then there was a knock on the door. I got in position, pretending to go about my business in the room, when there was another knock. Ok, perhaps he's not comfortable just walking into someone else's house? A third knock.

I went through the kitchen, my heels clacking on the bare hardwood floor, and down the three steps to the side door. I opened the door and standing outside was a man about 40 ish, maybe 6'4", a little chubby but not fat, with brown eyes and graying hair. When he saw me his eyes did something...hard to explain, but I saw something in them, something that made me uneasy for a moment. Then he smiled and started to come in the house. I led mystery man up into the kitchen, when from behind he inserted a ball-gag, pushing me against the counter top, securing the strap behind my head, then grabbing my wrists and pulling them forcefully behind my back. He then zip-tied my wrists together, tighter than I would have wanted but not enough to cut off circulation. I wondered why he was deviating from the plan, but I guess he just wanted to make it as real for me as possible. Maybe he forgot the cuffs.

With my hands secured behind my back, he forcefully pushed me against the kitchen table, knocking over the chair that had been resting against it on the other side, and pushed my upper body down onto the tabletop. He told me to shut the fuck up and not make a sound, and if I didn't put up a struggle, he would cut me loose when he was done and leave when he got what he came for. He yanked up the bottom of my dress up and yanked my pantyhose and panties down to just below my ass. He stuck a finger in my hole, snickering when he felt I was already lubed, then he wiped his finger on my thigh, I could feel a wet spot through my nylons.

After what seemed to be an eternity but was probably only 20 seconds, I heard his zipper come down, and a few seconds later I felt the head of his large cock pressing against my anus. He felt a little bigger than he described, which is an added bonus! What a wonderful feeling this was! I definitely struck gold with this guy, I was loving how he went off script to create the fantasy I had always wanted! It wasn't long before his large member entered me and he pushed all the way inside, then he removed it fully, and did it again, quite forcefully. He proceeded to fuck me pretty rough, exactly how I would imagine it would be had I really been forced.

With his height over mine, with me in 4" heels, his tool was at the perfect height to fuck the shit out of me, which was exactly what he was doing! He was being very rough, and I was loving every minute of it! We would definitely have to do this again! I'll say one thing, he also had stamina! There didn't seem to be any end in sight. I was actually starting to get sore and feel some pain, but I wouldn't ask him to stop, even if I could, which I could do nothing but moan and make noises with the ball-gag in my mouth and secured behind my head. My own cock was throbbing in the confines of the front of my panties and pantyhose, only the back having been yanked down. I started to feel something happening, which I was familiar with the feeling, but only when jerking myself off, I had never cum without touching it before, but I felt like it may actually happen this time. After what seemed to be 20 minutes, it finally happen...I did indeed cum without touching myself! At that moment, I felt like a real woman! I had never felt this way before. I had an orgasm just by getting fucked.

My hands secured behind my back, an anonymous cock in my ass balls-deep, I blew my own load all over the inside of my black lace panties. I could feel what felt like a large load start making its way down between my balls and my inner thigh, continuing down my leg until being slowed from further advance by my pantyhose, though I could feel it slowly making its way further down once working its way through the thin nylon material of the hosiery. I had never, ever cum that hard in my life! I don't know how MUCH I came, but it felt like it was the biggest load I had ever shot.

He was still behind me, pumping away. This was playing into another fantasy, one where I was tied up AFTER I blew my load, and fucked good and hard. I always wanted to do that. I know most guys lose interest after they cum, and I'll admit I do as well to a certain extent, but I still want to get fucked even after I cum. So here we are, I came, I'm spent, I feel exhausted, my knees are weak and I'm shaking in what I assume is extasy! I can feel a layer of sweat form between my silicon breasts and my chest, probably brought on by the friction between them and the table. My heels 'clack' on the hardwood floor of the kitchen every time he pulls back after a thrust or pushing into me, and what I feel, sense, hear...is driving me wild. I actually feel myself getting horny again! My surroundings have taken over my thoughts, my world, my very being.

Having no idea how long he has been in me, he finally cums, and cums hard. With a guttural grunt, he pushes in one last time, and empties into me! I could feel his hot cum filling my cavity, I could feel his throbbing cock pulse through my anal ring with every shot of cum he was emptying into me. This was a magical experience, one I would never forget, and one I would always want to repeat. We would have to keep in touch, for sure. Maybe he could do this every night for the next two weeks...but right now I was in no position to ask questions.

When he pulled out, I felt empty. I had grown accustomed to him being inside me, and I could have lived like that for the rest of my life were it possible. He yanked me up straight, and I felt a twinge of pain in my back. I thought that was a bit rough, but it's part of the fantasy. I'll fine tune things for next time, hopefully there will be a next time, I absolutely HAD to have this again! I'll just leave it up to him to do what he wants like he did this time, rather than try to script something that he didn't even follow this time, but which also made it that much more enjoyable!

He then led me into the bedroom straight off the kitchen, the guest room where we were SUPPOSED to have done the deed. He cut my hands loose from behind my back, pushed me down on the bed, and zip-tied my wrists together again, this time in front of me, securing me to the iron headboard of the bed. He left the room for a minute, and I could hear a drawer opening. He returned with a butter knife, putting it in one of my hands. He left me like that, gag and all, and I heard him go down the three steps, and out the door, closing it behind him. I heard a car start and drive away.