I'll never forget the first time I bought my own pair of panties. I had just turned eighteen, but I would be in high school for another six months, and not knowing where to go without being seen, I decided to try to stuff them in a cart filled with groceries at a supermarket a little ways away from my house. The panties I bought were nothing special, the store didn't have much. They were just regular ones you could find in any supermarket. They were black, wide, and not at all sexy. I figured if anyone saw me, they might just think I was buying them for my mom along with the weekly groceries. Even still, I had to wear an oversized coat just to hide my erection while walking in the store. I walked back home, putting the panties in my coat pocket, and apologized for "accidentally" throwing out the receipt for the groceries. My mom lectured me on the importance of keeping a receipt, but she paid me back anyway. I had gotten away with and I felt so incredible, I even put them on under my boxers before going to bed. They weren't cute or sexy, but they were my panties.
Unfortunately for me, only a few days later, my sister Cassie came back earlier than normal from swim practice and found me, in the living room wearing one of her skirts, my mom's sweater, and a cheap Halloween store wig my sister bought last year. I hadn't even heard the door open, I was too busy feeling the softness of my wonderful, black panties.
"Oh my God, Larry, what is wrong with you?" she asked after she was finished laughing. I felt ridiculous. No longer was I a beautiful girl, but some guy, with budding facial hair, dressed up in women's clothes.
"Nothing, it's a joke. I thought it'd be funny," I told her, but my inability to talk or look her in the eye spoke volumes. I was a freak, and now I could only hope she wouldn't tell our parents.
"Just please don't tell mom and dad, I'll do anything. Anything you want, please," I begged them.
"Okay," Cassie said. "How about this? You don't ever do this shit again, and you pay for gas for the next three months, and I forget about this."
I had no job, but I still had a good amount of money saved from working on my uncle's farm the previous year. Plus, I could always get a part-time job.
"Deal," I said.
"Good," Cassie said. "Now wash my fucking skirt, give me back my wig, and take that shit off."
My sister, as cruel as she could be, was true to her word. My parents never found out, although they did admire how much I worked that summer and how little I went out. They spoke proudly to their friends about my job at a local hardware store. My dad said it reminded him of his teenage years, saving up for college. If only he knew every road trip Cassie took, every time she went out with one of her many boyfriends, all that money I'd saved for college was going to keep her quiet.
Months went by, and though I never wore my sister's clothes, sometimes I would still put on those panties of mine, but never for long, never outside my room, and never when anyone was around. Even that got old, and by the time I was about to graduate I hadn't tried them on in a month. The reason I kept them, I told myself, was to remind myself of what a freak I used to be, and how I was a totally different man. That was all well and fine until Cassie told her boyfriend Rod about me.
They had been going out for almost a year. Rod was a real jock, water polo in the fall, and swim in the spring back when he was in high school. He never gave Cassie the time of day when they were classmates, but I guess a year after they graduated they'd started hooking up, both staying in town to study at the local community college. Everyone in high school may have loved his slicked black hair, his constant tan, his muscles, and his charming personality, but I knew what Rod really was: a bully and an asshole. He was nice to my parents, and to just about everyone, but he never missed a chance to bully me. When I entered high school, he'd punch me on the shoulder when no one was looking, trip me and then pick me up to make me look weak and like he was my savior. He was such a creep, I was only too happy the day he graduated and left my life.
Now he was back and with a vengeance. He was in my house, climbing through Cassie's window just about every night. Every time he came over without fail he'd tell me to make him something to eat after he was finished with my sister. My parents weren't the most conservative, but they still had an "our house our rules" type of system, no boys after nine ("or girls" my dad had once said before my mother laughed and tried to disguise it as a cough). Even worse, they'd punish us equally if they found out, so I did what I had to. I put up with everything because I knew one day Rod would be out of my life and I'd be off in the city at a real university, far away, never to come back except for Christmas and summer.
But then, Cassie one night let it slip to her boyfriend this "funny story" about her little brother Larry. She told him everything, and I couldn't do anything to stop it. I lay wide awake, listening to their conversation through the walls, horrified. My worst enemy knew my most embarrassing secret. When he opened the door and demanded I make him something, I didn't even grumble. I nearly said, "yes sir" on my way down to the kitchen. I fried some eggs and gave them to Rod who, as usual, didn't even bother to say thank you. Sleep was a thing that didn't come easy for me most nights anyway, but with this looming over my head I dozed off for only an hour.
The next day everyone had plans except for me, as usual. Cassie was out with Rod again, and my parents were taking the weekend to go visit some wineries. I thought about calling one of my friends up, but I was still too scared from last night. I could only imagine who Rod would tell, and how soon it would be before the whole town knew I was a sissy little girl boy. My few friends would leave me and join the rest. I'd be a pariah, and those that went to the same university would make sure every girl I talked to found out too. Like every time I've ever had stress, I went to my Playstation to take my mind off it. I was halfway through a campaign when the doorbell rang. I paused and figuring it was a delivery for someone else in my family, opened the door without bothering to check who it was. It wasn't a delivery though, in fact, it was Rod. "You and me gotta talk about some things," he said and walked in. "Close the door already."
"Where's Cassie?" I asked him.
"Shit, like I know. She's pissed at me for something, just fucks off and takes the car. You know how I got here? I had to take a bus."
This had happened before. They'd fight every few months, I knew where Cassie was, she'd be back late. Every time they fought, she'd go smoke some weed and watch movies all day. That was what she liked to call "some me time." I didn't tell Rod that though, I didn't want to help him. Even if I hated my sister, she was still family, and I respected that.
"Anyway," Rod said. "I didn't really come here for her. I came here because somebody told me something about you, you shit." He grinned, he was a little shorter than me, but you could barely tell with my skinny frame and his giant arms. I slouched a little, wondering what he was going to ask of me. I imagined all my savings for college gone. Or maybe I'd get lucky and he would only want me to write some history paper for him. I heard that was the only subject he had any trouble with, his own little Achilles' heel, not that he'd get the reference.
"What?" I asked him.
"Your sister," he said and walked toward me, "told me something very interesting last night. Is it true?"
"What?" I asked again.
"Don't fuck around man, is it true you like wearing her skirts?"
My heart raced. "No," I said, but I could tell he wouldn't believe me.
"Bullshit. She told me how she caught you with it on. Man, you must be a real fucking freak to want to do that shit."
"I'm not, I...she's lying. Just some bullshit," I said feebly.
"Really? Then why don't we check your sock drawer? She told me that's where you keep your fucking panties."
"Okay, look-" I said, but he cut me off.
"Look at that, little Larry is a real freak," Rod said. "Shit, even for me that's nuts. I mean, the things your sister does to me in bed is one thing, but the real freak in the family," he paused to point at me, "is you."
"I'm not a freak," I said. "It was a onetime thing, I swear, just to see, you know I was in drama and we might be doing an all-male cast and-"
"Just shut the fuck up Larry," Rod said with a big grin. "Now, here's what you're going to do if you don't want everyone to know."
I tried to swallow but my mouth was completely dry. "What do you want from me?" I asked him. "I'll do anything, just please don't tell."
"Put it on," Rod said.
I thought I misheard him. "What?" I asked.
"I said, put it on, the same skirt," he said. "Put it on now before I call up a few friends of mine, friends who know their way around Photoshop."
I couldn't believe it. Why would he want to see me in it? He was dating my sister, a young woman that even I had to admit was good-looking. "Why?" I asked him.
"You don't need to know, just do it," he commanded me.
"Yes sir," I said pausing a little. I couldn't believe I just said that. Even more terrifying was I could feel my penis growing harder at the thought. Before Rod saw a full erection in my pants I ran upstairs to my sister's room and put her skirt on. I was about to run back downstairs when I got a look at myself in the mirror. I looked like an idiot. I couldn't face Rod with a T-shirt, skirt, and ankle socks on. The skirt barely went over my boxers. I knew I had to make the look complete. I raced to my room, changed into the black panties, went to my parents' bedroom to grab the sweater, and went back to Cassie's room to grab her wig. I checked myself out one last time; now I looked presentable. There was no denying I was a guy, but I looked like a pretty guy at least.
"What's taking so long?" Rod yelled from downstairs.
"Just a second sir," I replied and again felt my penis twitch at the thought of following his orders. I hated the guy, everything about him made me cringe before today, but now all I wanted was to make sure all his commands were followed. I came back downstairs, being careful to sway my hips as I walked down the stairs.
"Well look at that, Larry," Rod said smiling. "You clean up nice. Say cheese." Before I could react he took a picture with his phone and looked at it. "Now I think I got everything. Jesus man, I only wanted to see the skirt. What did you think was gonna happen?"
"I just thought that-" I tried to say.
"No, you don't need to think anymore. That's not one of Cassie's sweaters, is it? Looks too, I don't know, grown-up for her."
"It's not," I whispered, my short life flashing before my eyes, my mind racing, trying to find any way out of this situation.
"What? I can't hear you speak up when you talk to me," Rod demanded.
I raised my voice, and said, "no it's my mother's. The wig is Cassie's and," I stopped short of telling me what I had on underneath. What the hell was I thinking? He only asked about the sweater and already I wanted to tell him everything.
"Alright, well whatever," he said and looked back at his phone. "Goddamnit, this picture's no good."
"I'm sorry," I told him. "We can take another one if you like." Jesus, I was another person now, I could only watch myself like I was outside of my own body yelling "No stupid! Stop!" and helpless to do anything.
"No, that's not the problem," he said. "The quality's not so great so-," he laughed. "You look like a fucking girl here Larry."
I blushed. "Oh, well, I kinda feel like one," I said. It was true, but my penis, already as hard as it could get, begged to differ.
"Come here, I want to see you up close," Rod commanded, and I obliged. "Good, that's good Larry. Well tell me, under that skirt, what are you wearing?"
"My panties, I bought them at a supermarket a few months back." Again I gave him more information than he wanted, but he ignored the extra bits.
"Panties? Shit, you really are a girl. Well, Larry, you might look a little like a girl, but can you suck like one too?" Rod asked me as he pulled the zipper of his jeans down.
I could only stare in amazement as I saw his cock bulge through his boxer shorts. It was big, even while flaccid, so much bigger than mine. The sight of it intimidated me. Even under those boxers, I could tell it would be difficult to satisfy. At the same time, the same voice telling me to get out of this had been replaced by another, one more feminine, sweet and loving. "Go to him," it said. "Make him happy."
I got on my knees as he pulled down his shorts. It came out, not fully erect yet, but still big and slapped me on the face. "Sorry about that," Rod said. "But this guy's been needing to get drained all day. Your sister teased and teased, but he's gotta get some release."
Before I could tell him I was alright with it, he grabbed the back of my wig and pulled me in closer. I could smell the sweat, the irresistible warmth comforted me as I wrapped my lips around his cock. I had no idea what I was doing, I'd never even touched another man's...thing, but I'd seen videos. I'd always thought I'd be the one on the receiving end when it was my time, but my own smaller erect penis told me it was okay. I wanted to make Rod cum as fast as possible. He grunted a little. "Woah, not the teeth," he warned.
I nodded, his cock still inside me, and tried to avoid any contact with my teeth. I licked all over and tried to not gag. I barely could, he kept pulling me ever closer to the base. I grabbed his ass for support, as my face went red and breathing no longer became an option I tried as hard as I could to reach his crotch. It was no use, I wasn't there yet and Rod mercifully released me, letting me take a quick breath. My spit flew out everywhere as I sputtered and coughed. Then, not wanting to keep him waiting, I went back for more until I could hear him moaning. I didn't know why, but I remembered how every time he and Cassie were in her bedroom I never heard him moan. Sometimes I'd hear my sister do it, but never Rod. I tried to smile, but his cock was twitching and I was desperately trying to not get my teeth on him. At last, his moans turned to grunts and without a word of warning from him, hot cum filled my mouth. It tasted so salty, so warm, not the greatest thing I'd ever tasted to be sure, but what it represented made the taste all the sweeter.
"Woah, easy," Rod said. My head was on autopilot, still going up and down, even as Rod was trying to push me off him. When he released me, I swallowed, and not knowing exactly why I opened my mouth to show him.
"Good, didn't even have to ask. Good girl Larry," Rod said smiling.
For some reason, that hurt more than anything he'd done to me so far. I looked down a little sad, not knowing exactly why.
"What's the matter? You didn't like it? he asked me, his voice more gentle than I'd ever heard it.
"I loved it, but please don't call me Larry again," I said, confident.
"Fine, what should I call you?" he asked as he put his pants back on.
"Please Rod, when I'm, you know, dressed like this, call me Lexi."
"Lexi? Alright, yeah, I like it. Sexy Lexi," he said grinning. "Well, see ya, Lexi," he waved goodbye nonchalantly, and was out the door in seconds, leaving me there, still on my knees, my penis stretching my black panties out and the taste of Rod still left in my mouth.