Boredom Forces Me to Take a Chance

The following story is fiction. Most of my stories are true, but due to a dry spell, I just wanted to put something down for the readers. This is a fantasy that just came to me while sitting around the house during this Coronavirus thing. Hope you enjoy.

***

It's been a while now since things have been normal. Restaurants are closed, 24-hour stores are closing earlier, and the streets are mostly empty. It was a Sunday night, I was sitting in my kitchen watching the new TV I had just purchased and mounted on the wall. I found a ZZ Top documentary on Netflix, having exhausted my options of things to binge-watch.

Of course, I was dressed. Well, partially. I am ALWAYS at least partially dressed. Tonight I had on a pair of suntan pantyhose, a tiger print miniskirt and a pair of flats. To this day I truly have no idea why women shun this type of clothing...it really is so much more comfortable and attractive than mens clothes. Ironically, it's mens clothes that women prefer to wear these days, while men are chastised for wearing womens clothes. I always say were it not for us crossdressers, the womens clothing and shoe manufacturers would go out of business.

The documentary was 90 minutes, and when it ended, I was not tired enough to go to bed. But man was I bored! I often take a ride late at night, between midnight and three in the morning, greatly reducing the chance of being caught while at the same time risky enough to make it exciting. But under the current circumstances, I felt I might draw unwelcome attention to myself, and though there was not any travel or driving ban, or any curfew, I still didn't want to try to explain to an overzealous cop why I was out at this time of night, having to further explain why I was dressed like I would be dressed.

So I remained home every night. Every. Night. I was going mad. I could only jerk off to porn or mental fantasies so many times. I could only eat so much. I could only play so much solitaire. Something had to change. So, I rolled the dice and decided to take a chance and do something I have never done before...go to the store, before it closed at 11 pm, fully dressed!

My local Walmart, and I believe every 24-hour store was closing at 11 pm during the pandemic in order to restock and disinfect. I never go out this early, but I figured it should be ok, while HIGHLY exciting...and risky. I'm not completely passable, so I figured I'd get 'made', but there shouldn't be too many people in the store at 10:30, which would give me plenty of time to walk the store, just looking and enjoying the sheer freedom and exhilaration of being in public dressed fully in womens clothes.

I decided to go for it. I strapped on a bra and inserted my silicon breast forms, selected a black top to compliment the tiger print skirt, applied some makeup including my favorite bright red lipstick, my long auburn wig, clip-on earrings, a necklace, ankle bracelet, and finished it off with a pair of black suede Mary Janes with a 4 inch heel. Lastly I glued on a set of fake nails that I had pre-painted bright red, then I put my debit card and drivers license in a small clutch along with my cell phone and two condoms...I always carry them just in case. It was late March so it was still cold, and I grabbed my coat, a black faux mink, and went out through the garage and out to my truck.

At 10:20, hoping that none of my neighbors are still up and looking out their windows, I walk out the front of the garage and the security light kicks on, which I knew would happen...I'm in full view of anyone who might be looking...but luckily, I saw no lights on in any nearby houses so I felt I was safe from exposure...though I can never be sure, people DO look out their windows without the lights on. In fact, it's the best way if one is going to be a nosy neighbor. So, it's a chance I take any time I leave the house, but a chance worth taking. Why leave the security lights on? Unfortunaletly they are hard-wired into the house and there is no switch for them, but that's on my to-do list in the near future.

Climbing up into my truck in 4" heels is always interesting. I have the flat running board style steps, which help greatly, but it's still challenging. Sitting on the cold leather is a shock to the back of my pantyhose covered legs, but the heated seat soon makes it comfortable. I let the truck warm up for five minutes before taking a deep breath and shifting into drive. No matter how many times I go out dressed, even when I'm not meeting anyone, it's still a heart-pounding experience and is what keeps me going. It's like a drug...I need it!

Walmart is only a five-minute drive from my house in my small town. It's pretty much all we have here, but for a grocery store and a couple fast food joints, gas stations, a couple churches and a few bars. I pull into the Walmart parking lot right at 10:30. There are about nine cars in the lot. Probably workers, maybe one or two customers? Well, maybe, I'll find out...if I have the guts to go through with this. I park close and just sit there for about ten minutes. Now I have only 20 minutes, and that's if I go NOW. Not having seen anyone else go in or come out, I take another deep breath, put my sunglasses on, shut off my truck, and exit into the cold March night air.

My heart is pounding like never before, I feel slightly dizzy, and my vision blurs ever so slightly. Yet I proceed toward the entrance...

"Due to the recent outbreak of the Corornavirus, this store will be closing at 11 PM and reopening at 6 AM until further notice. Sorry for any inconvenience"

The doors had slid open automatically while I was reading the sign. I entered the store, never having done this before, wondering if I had made a mistake. I would never normally do anything like this in my own small town, too many people know me. But would anyone recognize me? Like I said, I'm not passable, not completely, but I do not look anything like I normally look. And with the sunglasses...well, hopefully they serve to further my disguise. I hoped.

I could hear nothing in the store but the sound of my heels on the floor. Not quite the usual 'click click'...more muffled, yet still very pronounced. Anyone could definitely tell someone was walking in the store, and it was likely a woman, or some douche in cowboy boots who thinks New York is Texas...and being 6' without heels and now 6' 4" with them, I'm certainly not incognito. No hiding for me. Damn...I'm really doing this...I'm in the fucking store, fully crossdressed from top to bottom...and it feels...funny. It's amazing, but also scary, my heart feels like it's going to bust through my chest. My mouth is dry. I'm dizzy again. I start to sweat.

Ok, I decided I had my fun, I did it, I accomplished a major goal, a milestone, and now it's time to leave.

"Attention Walmart shoppers, your Walmart store will be closing in ten minutes, please make your way to the checkouts in front to complete your purchases. We will reopen tomorrow at six A.M. As always, thank you for shopping at your local Walmart".

Shit. But is there anyone left in the store? I'm going to find out...and soon. I had made it back to the shoe department and had been browsing the womens shoes when the announcement went over the P.A. Suddenly, there they were...people. One came from the mens shoe area, two from electronics, and people were pushing carts from the grocery section. It was as if they appeared out of nowhere.

Thankfully I didn't have a purchase. I had thought about buying a new pair of flats, just to experience cashing out while dressed, not really caring if the old lady cashier (who I was sure did not know me) knew I was a guy or not. But I put the shoes back, having already had a pair just like them anyway, and started making my way to the front of the store. To safety. Should I wait and be the last one, and chance that the manager waiting to lock the doors might recognize me? Or should I hasten my retreat and get the hell out before granny starts cashing people out.

I ran for it. Almost literally, but I'm not winning any races in heels, and I certainly did NOT have the desire to need medical attention dressed in a miniskirt, nylons and heels, makeup, wig and fake tits. Briskly walking as fast as I dared, I made my way to the front doors. Almost there. And then it happened. Eye contact. A man, about my age of 50, steps out from the magazine aisle and looks right at me, then pans down to my legs, then to my beer belly. Yeah, I look more pregnant than overweight, but it's a fact, I'm overweight, but not fat. I was waiting for a laugh or a rude comment, but he merely smiled and nodded, and fell in behind me as I was walking out. BEHIND ME. No doubt staring at my legs, ass, or both the whole time.

He then comes up beside me and says "HI. Do you always go out dressed like that?"

"Uh...it's just...just a little fun."

"Yeah? I bet it is. Must be exciting." he replied.

"Well, yes, very much so. Have a good night." I just wanted to get away from this very uncomfortable situation. I had been made. Now I had to get away.

He then gently grabbed my hand and led me to his car, opening the passenger door for me to get in. For some reason, I felt no danger or risk, though my heart...man, if it could survive this, a heart attack should be the last thing I'll die from. I just stood there, looking at the open door, at the seat inside a brand new GMC Terrain, not knowing what to do. I had to ask.

"What are your intentions?" I asked him.

"I want to take you back to my place. If you don't want to, I'll understand, but I had to find out. When I saw you just a few minutes ago, you stopped my heart with those legs, and I'm not a ladies man, I don't get lucky often, so I figured, the worst you could say is no, right?" the man said.

"Sure. Yeah, I could say no. I could. I probably should. But...I'll follow you home. I'm not comfortable leaving my way home here in the parking lot..." I told him.

He asked, "Will you? Or will you bail on me?"

"What do you want to do when we get to your place?"

"I'd like to...I mean, I'd love to...I want to have..." the still unnamed man stammered.

"Sex? Do you want to fuck me? Is that your intention, your desire?"

"Yes. YES."

"Then...I won't bail. I will follow you. I WILL follow you home! You have no idea how badly I also want sex."

I got back into my truck, heart pounding harder than I thought possible, stomach in knots, and again breaking out into a cold sweat. I fired up my truck and followed him out of the parking lot, totally neglecting to ask him where he lived...is it 20 miles away, or nearby, or close enough to where I live to be noticed? Ah fuck, all paranoia kicking in high gear, adrenaline at maximum levels, heart on turbo mode...but I couldn't be happier at this moment, and the best was hopefully yet to come.

On the drive to his place, questions ran through my mind...could he get it up? Is he big enough? Does he have to wait a half hour for a pill to kick in? I'm going into this totally blind, I can only hope for the best and enjoy the moment, second by second. Turns out he lives just outside the village, taking only six minutes to get to his place, which was in an apartment complex. This has always been a fantasy, to come to a guys apartment, having to walk not only across a parking lot, but into a building and down a hallway where other people lived. More risky, but more exciting. Someone could always be leaving their apartment, or coming home.

The location of his unit would not disappoint my fantasy...it was at the very end of a fairly long hallway. Walking in the main door was a rush, walking down the long hallway was even more of a rush, especially since it really wasn't that late at night, just after 11 PM. We arrived at is door, apartment 8, thankfully on the lower floor (thankfully, being in 4" heels and all). Upon entering his place, he gently pushed me onto the couch that was right inside the doorway, and began caressing my nylon encased legs.

I immediately noticed my own hard on, not even having realized if I had been hard all along or just now or...I had no idea. Everything was a blur. I could have been pitching a tent from the second I left my house...or upon entering the store. Regardless, I'm fucking hard, and I can feel he is too, and his hands running up and down my pantyhose are just melting me like never before! I'm tingling all over, my excitement level is peaked, then without warning he kisses me, on the lips, then my neck, all while still caressing my legs, working his way up to my hard 'clitty.' I have honestly never, ever felt like this before! Not with any man OR woman! This could very well turn out to be the best night of my life, sexually.

While he is caressing me up and down and his tongue is in my mouth, I reached down to undo his belt and the button and zipper on his jeans. I push his pants down as far as I could, with him on one knee on the couch, and I find his beautiful, hard and large cock! YES! I have had many bad experiences where the guy was small, or couldn't get it up...usually BOTH, so it's always refreshing to find a guy who doesn't have any problems and can do the job!

He gets up off of me long enough to take off his pants the rest of the way, and his shirt. I take the opportunity to rip open the crotch of my pantyhose and pushed my panties aside as far as I could, knowing what would soon happen and wanting there to be no further delay. He sat back down on the couch next to me with his easily 9" cock sticking straight up, and I knew what he wanted. Now this is normally the time I explain that I don't do that...it's just not my thing, I had a bad experience once and I just don't...

But something pushed my head down onto that huge cock, and it wasn't him! I don't know what came over me, but in this moment I felt more like a woman than at any point in time before tonight. I couldn't take it all in, but he didn't seem to mind, and I actually think I was doing a decent job of it too, he tipped his head back and was moaning and smiling ear to ear.

"Please, don't cum in my mouth...I want you to save it for my ass!" I told him, coming up for air.

"Ok. I want to fuck you, don't worry, I'm not gonna ruin that chance," he said.

"And...uh...something I've been wanting to do forever...would you be ok if I...video record us?" I asked, forever having wanted my own porn tape of myself getting fucked.

"Ok...that might be kinda fun. Give me a copy too then?" he asked.

"Of course, but we both promise to never put it on the internet or show anyone else."

"Agreed." he said.

I got up and found a coffee cup that I used to lean my phone up against, aimed it at the couch where we were, and hit record. This was another ultimate fantasy of mine, and I could not believe it was coming true! I went back to my new found cock and continued working it, and after my jaw started to hurt and most of my bright red lipstick was on his shaft, I asked if he was ready for the main event. He had some lube in his bedroom, which was a good thing because I did not have any with me, just lubricated condoms and I only use them if the the guy insists...yeah, I know it's not safe, but it's not great sex unless there is cum leaking from your ass for a while afterward. Hey, do what you will, don't judge, I love that shot of hot cum in my ass! There's nothing like it!

I lube up my hole real good, and put a liberal amount on his shaft, further smearing the red lipstick I left behind. He leaned me against the back of the couch and pressed the tip of that beautiful cock against my tight, willing and waiting anus, slowly advancing, slow and gentle which I appreciated as it had been a while since I last took a real cock and even then it wasn't this big. But it felt so damn good! Further and further, slowly pushing in more and more, my ass hole stretching beyond what it was used to, but not beyond what it can happily handle.

Finally, after what seemed like ten minutes but was actually more like 20 seconds, his cock popped in past the rim and he was all the way in, and I was in a euphoric heaven! Slowly he retracted almost all the way, then back in, back and forth, slowly, making love to me not like a teenager with raging hormones, but rather like two middle aged people actually enjoying the experience, cherishing the moment, making it last. With his hands now fondling my silicon breasts, he continued making love to me, stopping now and then to keep from cumming. He wanted this to last as long as possible, as did I. The last fuck I had lasted 20 seconds, that was it! 20 friggin SECONDS. I enjoyed getting fucked of course, but damn, make it last.

After about 15 glorious minutes, he pulled out and asked me to lay on my back. He then gently, ever so gently, placed my legs on his shoulders and slowly reentered me, the different angle making my own cock twitch and start getting hard once again, having lost the erection once he had entered my prostate before. Slowly, in and out, my cock getting harder with each gentle push, feeling as if I were on the verge of an anal orgasm...I had never had one before but I would feel complete if I had one during sex, just like a woman orgasms when she is getting laid...I wanted the same experience...I wanted to cum without touching it.

He leaned into me more, bending my legs further than they had ever been before, a little painful but in a pleasurable way, and resumed kissing me passionately...lips, neck, lips...all the while gently pushing in and pulling out of my ass. I was fucking ecstatic, this was indeed the best sex I have ever had in my life, woman or man. I could feel my own cock so badly wanting to blow its load, feeling right on the edge, but not quite able to. I usually end up taking care of myself when I get home after being fucked, I normally don't even have an erection when I'm playing the woman, but I wanted this to be different...I wanted to cum, without touching it, without it being touched! This time felt different. I wanted this time bo BE different.

"Fuck me. Fuck me hard. Fuck me HARD! I wanna cum!" I pled.

Without questioning my command and without missing a beat, our lips once again locked in a passionate embrace, he began to pick up the pace and started to fuck me. The love making had come to an end, now he was fucking me senseless...and I was loving every fucking thrust! My cock was harder than it had ever been, it was so hard it was painful, it actually hurt, and I swore it grew another inch from its normal meager 6"...and I could feel something getting ready to happen.

"Try not to cum...hold off as long as you can" I told him. I wanted what I wanted before he was done.

He continued to fuck me for a long time, I was impressed, and extremely pleased with his stamina! This guy certainly was no 20-second marvel, was no 'minute-man,' and I loved that. I was finally getting what I really wanted, a nice LONG sex session, a true appreciation of one another, not just animal hookup sex, though that's what this really was in the end. And, a great video to forever cherish. After another couple minutes it happened...I fucking came all over in between his bare stomach and my miniskirt and pantyhose...my cock went off like a rocket! I almost passed out, I had NEVER cum that hard in my life, ever! That was the absolute best orgasm I had ever had. I felt light-headed.

He asked me if I wanted him to stop for a while, understanding that when someone cums, they often lose the desire to continue, but I told him to keep going, as gentle or as hard as he wanted for as long as he could, I was loving every minute of this man and I didn't want it to stop! His stamina did not disappoint, he continued for another ten minutes before having me lay on my stomach, reentering me for a third time from behind and atop me. His thrusts pushed me into the cushions of the couch, and went on for another 20 minutes...in which time I had become hard again!