My wife went out of town a couple weekends ago, so I decided to go all out and have some fun. It was the perfect time to live out some of my nastiest, most twisted sex fantasies, and I knew I could do it with some help from Grindr. It would be my dream weekend.
I knew right away that cross-dressing was going to be involved. It had been years since I'd worn lingerie. Just the thought of doing it again made my dick hard. Wearing slutty undies always made sex hotter and more depraved. It was like telling the world I wanted to be used like a whore.
A day before my wife left, I swung into a Victoria's Secret in the mall on my way home from work. Foot traffic was light, even for a Wednesday afternoon. My heart thumped as I tried to creep into the store unnoticed. Inside, it was just me, a couple other customers and a clerk at the register. Picking out lingerie for myself is a huge rush for me. Here I am, this average-looking guy in a basic blue button-down shirt and khaki pants, secretly buying women's undies for myself.
It didn't take long for my stealth mode to get blown. Out of nowhere appeared a blonde saleswoman with big tits, obviously wearing a push-up bra under her flimsy, white blouse. She sneaked up from behind while I perused a rack of lacy, black merchandise.
"Anything I can help you find?" she asked sweetly.
I swallowed hard.
"Uh, no, I think I know what I want," I said.
"OK, just let me know if you need anything," she said with a flirty smile.
I nodded nervously and went back to my hunt. It didn't take me long to find a bra, 36c, the same size my stepmother wore back when I used to raid her panty drawer. Then I found some matching boy-short panties, thigh-high stockings and a garter belt. On the way to the register, I plucked some body spray off the shelf.
The clerk at the register either thought I was buying for someone else or acted like she did.
"Oh, she is going to love these," the clerk said as she folded the panties. "Would you like a gift receipt?"
I played along.
"Yes, please," I said.
I paid in cash and hustled out of the store, making a beeline to the parking lot. When I got to my car, I popped the trunk and peeled back the carpet covering the spare tire. I stuffed the striped pink bag and its contents in an indentation next to the tire and replaced the carpet.
The next day, an Uber picked up my wife shortly after 8 a.m. to take her to the airport. As soon as she was gone, I opened my laptop and sent my boss an email saying I needed to take a sick day. In a sense, it wasn't a lie. What I was about to do was pretty sick. I didn't want to wait for the weekend for two reasons. First, I was horny as hell and wanted to start fucking. Second, I love fucking married guys, and weekdays are the best time to find them on Grindr. It's easier for a lot of us to slip away from work unnoticed for an hour than trying to make up an excuse to tell the wife to step out on a weekend.
I hustled out to my car and headed for the grocery store around the corner. I bought a 12-pack of IPA beers, 8.2% alcohol content. The old-lady clerk must've wondered what a clean-cut guy like me was doing buying beer- and only beer- first thing in the morning. But I didn't give a fuck.
After the grocery store, I drove to the Walgreens across the street. My car screeched to a halt near the front door, and I hustled inside. A blast of warm air greeted me when the automatic door swung open. I headed for the makeup aisle and quickly picked out some cherry-red lipstick, dark gray eyeshadow, black eyeliner and heavy mascara. I didn't want anyone I knew to see me, so I didn't linger. Thankfully, no one was in line at the register, and I was back in the car within a couple minutes.
I was in such a hurry to get home and start looking for a hookup, I nearly took out the mailbox as I squealed into the driveway. As soon as I was parked, I grabbed the beer and makeup and popped the trunk. I found my stash of lingerie under the carpet right where I'd left it. My hands were full of goodies as I clambered up the steps to the front door of the house.
Once inside, I bolted for the bedroom and dropped my packages on the bed. The first order of business was to catch a little bit of a buzz. I cracked open a beer and guzzled half of it to get started. Then I downloaded Grindr to my phone and logged in. I did a quick check to see if any of my regulars or top prospects were hunting. Nothing was doing at the moment, but I had a good feeling.
I set up my laptop on the bed and navigated to a compilation of bukkake videos. I wanted some inspiration while changing clothes, and nothing gets me going like videos of women being used like whores. I dumped the contents of the Victoria's Secret bag on the white comforter. Moans poured out of the computer's speakers as I tore the tags off the bra, panties and garter belt. I pulled off my collared shirt and slid down my cargo shorts and boxers.
I've done enough cross-dressing to know how to put on lingerie. For me, the bra always goes on first. I like the feel of it too much to wait. My fingers trembled as I fastened the two hooks at the front of my chest and then slid the cups around to the front. Threading my arms through the straps was a cinch, and then I shoved as much flesh as I could into the cups to make my tits look as big as possible. I was nowhere near filling them out, but the garment's firm squeeze felt very naughty.
Next I tore open the thigh-high stockings package and sat on the edge of the bed. I rolled the stockings up my legs one at a time. The sexy fishnet pattern hugged my skin ever so tightly. The garter belt, the toughest part of putting on the outfit, came next. Getting it around my waist was no problem, but I fumbled with the clasps that connect the garters to stockings for a while. Eventually I secured them. Then I slid on the panties. I know boy shorts usually don't go with garter belts, but I like them because I can fit my cock and balls in them. I arranged my prick so that it was pointing up toward my belly. Every time I moved the lacy fabric rubbed against the sensitive underside of my dick.
To celebrate the completion of the outfit, I chugged the rest of the beer and cracked open another. Almost as if on cue, my phone buzzed. Married DL had messaged me on Grindr. Adrenaline surged through my veins as I read his words: "Hey, can you host?"
"Yeah," I wrote back. "Wife is out of town, and I'm cross-dressing today."
"Hot af!" he replied. "I am too. When can you meet?"
"Now."
"Leaving in 5."
Married DL and I had fucked twice before. I'm sure we would have hooked up more, if we'd had a place to do it. I didn't know much about him, except that he worked in a bank a couple miles from my house and liked secret, gay sex as much as I did. His wife had no idea. Neither did mine.
I polished off my beer and opened another. The mix of bukkake videos ended, and I cued up another one. Then I grabbed the Walgreens bag off the bed and went into the bathroom. I dug through the contents until I found the lipstick. My hands shook as I cracked open the plastic wrapped around the case. I twisted the tube and pressed the tapered top of the lipstick against my upper lip. It went on smooth and shiny, and I instantly felt like a slut. Then I did the lower lip and blew myself a kiss in the mirror. With the eye shadow, eyeliner and mascara, I did my best to give myself a sultry, porno star look. I was nowhere close to passing as a woman, but it was enough for me to just be wearing the makeup. I felt dirtier.
I finished off my third beer while watching two cum-covered sluts make out, licking each other's faces. I was just cracking open my fourth when I heard Married DL's Mercedes pull into the driveway. He followed the pavement behind the house and parked under the big oak tree. My heart thudded in my chest as I skittered to the back door. He didn't even have to knock. I just opened the door and stood behind it so no one from the outside could see me.
Married DL walked in and turned to face me as I closed the door. He took a look at my outfit and nodded approvingly.
"I feel like such a slut," I said.
"I do, too," he said.
Married DL started peeling off his button-down blue shirt and khaki panties. Underneath he was wearing his wife's pink bra and panties. His cock was pitching a major tent in the satin. My prick was doing the same thing in my lace. I poked my cock into his.
"Let's fuck," I said.
"Definitely," he said.
He followed me down the hall to the bedroom. Moans and shrieks from the laptop speakers filled the room. A blonde girl who looked barely 18 was getting fucked missionary style and facialiIzed at the same time by a group of guys.
Married DL pulled down his panties and kicked them to the side. He spread his legs and bent over, bracing his forearms on the comforter. He had a nice, pert ass for a guy his age.
"Let's cheat on our wives," he said.
"Fuck yeah," I said. "Today I'm gonna show you how I fuck her."
I peeled off my boyshort panties. The garter belt and stockings made for a sexy frame to my rock-hard cock. I got some KY Jelly out of the nightstand drawer and squirted some on my fingertips. It was fun to watch the hairs rise on Married DL's ass as soon as the cool lube touched his asshole. I shoved my middle finger inside him one knuckle deep and wiggled it around to get him good and greasy. Every cell in my body wanted to fuck him. I pulled out my finger and slid my dick between his cheeks. The head pushed against his hole without entering. I felt Married DL's muscles tighten.
"We're gonna cheat on our wives again," I said.
"I know," Married DL said breathlessly. "Fuck me instead of your wife. I wanna be your bitch."
I pushed my cock inside him. Married DL arched his back as the first bolt of pleasure and pain shuddered through him. I pulled back just a little and then pushed back in, this time deeper. It felt so good to be going bareback with another married guy.
My hips started rocking a little faster and wider. As my prick went deeper into Married DL's hole, his soft moans started intermingling with the sounds of dirty group sex coming from my laptop speakers.
"This is how I fuck my wife," I said. "You like it?"
"Oh fuck yeah," Married DL said. "I want you to cum in me."
"I'd rather fuck you than fuck my wife," I said.
"Cum in me!" he said.
I started fucking him full throttle, my balls slapping off his ass. The pressure built in my cock. I held back as long as I could, but the force building inside me became too much. That first spurt of cum was like the Hoover Dam exploding. I let my balls empty into his butthole.
"Oh fuck that's goooood," he moaned.
When I pulled out, my body filled with shame. But I wanted to go deeper into this time. I got down on my knees and opened wide. Married DL grabbed me by the back of the head and shoved his prick into between my lips. He shot his load instantly, his salty cum filling my mouth. When he pulled out, I swallowed.
I felt like a whore and loved it.
Married DL quickly scrambled back out to the living room to slide on his boxers and pants. Neither of us said a word. I just cracked open a beer and drank while waiting for him to finish dressing. After he buttoned up, I walked him to the door, and we exchanged quick goodbyes.
I listened to his wheels crackle on the driveway while I stood silently in the living room, sipping my beer. I was still wearing the bra, garter belt and stockings. And I wasn't ready to take them off.
I went back into the bedroom to grab my phone and check Grindr. Sure enough, it was a message from Panties1. Yes, indeed, it was certainly turning into my dream weekend."
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