Ride it Like You Stole it

Like Amber's Ambush, this is just a quick short story that caught my imagination. And, again, Like Amber, it will probably have additional chapters if you guys enjoy it. I saw a meme that read, "Ride it Like You Stole it." With my imagination, well, what else could that possibly imply?

Enjoy the 'ride'. And, as always, all standard caveats apply. Be sure to leave me a comment when you're done.

***

"I knew it! Where are the rest, you little pervert?" I had just gotten out of the shower and was walking out of the bathroom in nothing but a loose pair of shorts. Those shorts were now around my ankles, and my sister was livid.

What my sister was screaming about was the red lace trimmed thong I was wearing. It was hers. I pointed meekly at my dresser and watched in horror as she harvested my stash.

Amy went through every drawer. When she was done, she had a dozen pairs of panties, three bras, some stockings, and a garter belt in her hands. All things I had secreted from the laundry over the past few years.

"Those too." She glowered at me. I knew what she meant. When I turned to go back into the bathroom, she barked at me again. "Uh Uh. Now!"

"But Amy..." I slowly turned to face her.

"I said now. It's been driving me crazy where all this has been disappearing to and then mom commented how much she appreciated your help with the laundry, and I knew."

Taking a deep breath, I looped my thumbs in the thin band of the thong and shimmied it down my legs. I cringed as I handed her the now damp panties. My little cock was rock hard and dripping. Completely emasculated, I stood there naked and trembled until I heard Amy close the door.

Not even bothering to put my shorts back on, I curled up on my bed and cried myself to sleep.

"Hey, sweety. You going to come down for breakfast?" I knew it was my mom before she said anything, just from the way she sat on my bed. It was the way she pulled my hair back so she could see my face, and how, without judgement, she would ease my hand away from my face when I sometimes sucked my thumb when things got too hard. This was one of those times.

Amy would have jumped on me and started tickling me, well, if she weren't livid with me. My dad would have hollered "hey sport," from across the room. But my mom, always soft and gentle. She was probably the one that had come in and covered me with a blanket while I slept.

"Why am I like this?" I rolled onto my back and looked up into her eyes.

"Like what, honey?"

"Mom, you know what I mean. Amy told you; I know she did. I'm not like dad or any of the boys I went to school with. No girl will ever want me, because..." I started to tear up again. "And then there's what Amy is mad about. I don't understand it, any of it."

"Evan, you're special. You just need to find your spot. As for your sister, she was more angry that you stole her things and lied to her. If you asked, I'll bet she has some she will give you. If you want, you and I can go shopping and you can pick out some new ones that you like. Just for you."

"But boys don't..." The compassion in her eyes was so sincere. I rolled over and started crying again.

"Honey, obviously, some boys do, and to be honest, I've sort of seen this coming. The way you fold the laundry. Well, you take a little longer with some things than others. Come on, before your breakfast gets cold." She swatted me on my butt and left me there.

I washed my face and grabbed a shirt to go with the shorts I had left on the floor and followed my mom downstairs.

Amy and I sat in silence for the longest time, stuffing pancakes into our mouths and pretending not to look at each other. Despite what had happened, she was my best friend. When I thought about it, that was probably what she was most upset about. We talked about everything, and I had hidden this from her. Well, mom was right. I had stolen from her and lied about it, too.

"Amy, I'm sorry. I shouldn't have taken your things." I cast her a furtive glance.

"Me, too. I shouldn't have reacted like I did. It's just... the red ones were brand new. They're part of a set and I wanted to wear them as a surprise for Brandon. You could have just asked, you know."

"That's what mom said." It was a weak smile. "I was too embarrassed and didn't want you to think I was a pervert." I put extra emphasis on the word. Amy cringed a little. "Besides, I didn't think you'd miss them. You have like a thousand pairs. And, well, they were in the laundry."

I could feel the tension fading. I knew we were ok.

"You always wash new panties before you wear them, or do boys not do that?"

"Not my department. Mom washes, I just fold."

"You're not, you know. A pervert, that is. I was just upset."

"I know. It's just confusing. I don't even know why I do it. But when I do, it feels nice, better than nice, it feels right."

"So, do you want to?" She grinned at me. "I mean, I do have tons. Maybe we could find some you like that I won't miss."

It took a minute for it all to settle. Sure, I had been stealing her panties and a few other things for a long time. But now she was offering them to me. My mom and dad knew. It would be ok. I wouldn't have to hide it from them anymore. Was that what I even wanted?

"OK." It was more of a whimper than an answer. I nodded at Amy.

It began with just panties, well, panties and some matching bras. Amy was petite, almost waifish, so with an adjustment here and there, the bras sort of fit. My favorite was a pink set that matched the red ones Amy had just bought. Tiny lacy thong and a matching balconette bra.

My little firm nipples just peeked out through the lace. Even hard, my little penis hid behind the flimsy lace of the panties. I decided to leave them on.

From there, it morphed into almost a quest to see how I looked in all kinds of her clothes. Dresses, skirts, tops, her skinny jeans, even a pair of super short shorts.

"What are you two up to in here?" My mom stuck her head in the door, probably in response to all the laughter and giggles Amy and I were sharing. There I was in a pair of shorts so short, half my cute little butt hung out. Underneath, I was wearing fishnet stockings with attached garters. Over my bra, I had on a loose fitting, short-cropped tank top that left my tummy exposed.

Somewhere along the way, Amy had added some blush, eye shadow, and bright red lipstick. Tousling my hair, I looked like her twin.

It could have been worse, but not much. I had twisted around, looking over my shoulder with a pouty look on my face and my butt sticking out while Amy took pictures of me.

"Um, hi." I was too giddy to be embarrassed. Amy burst out laughing.

"Evan, are you sure about this?"

What was the point of pretending? With Amy's help, I had discovered an entirely new truth; I had found a confidence, an aura, an energy that I'd never felt before. My diminutive stature, especially between my legs, didn't matter anymore. Where I had always felt I was a failure as a boy, I was fucking killing this girl thing.

"Well, honestly, I think the shorts might be too short and dad might have an issue with that." I gave her an impish smirk. "But, mom, look at me." I did a twirl and wrapped her in a massive hug.

"Besides, mom, you've been after me to clean out my closet forever." Amy giggled. "I think now, we may need to clean out Eve's."

"Eve?" My mom pushed me away just enough to look me in the eye.

I bit my lip and nodded. "It was Amy's idea."

"Well, OK. I have to admit you look happier than I've seen you in a long time. But only clothes until we've all let this settle in." She smiled at me and turned to leave, stopping at the door, "and you get to tell your father."

It took Amy and me two hours to get all my new clothes moved into my closet. I laughed when I realized you couldn't tell she took anything out of hers.

"Stop!" Mom shouted as we got to the front door. I had changed the shorts for a skirt that, to be honest, wasn't a lot longer, and added a pair of Converse. They looked a lot cuter on Eve than they ever had on Evan. "Where do you think you're going?"

"Mooom," Amy drew that word out, for it seemed like five minutes. "Eve needs her own makeup. We're just going to Ulta at the mall."

Mom looked at me and cocked her head to one side.

"Please? I really like this." Maybe it was the excitement on my face or the way I was bouncing up and down in anticipation.

"Just makeup. Nothing else. Got it." Mom shook her head and let out a massive sigh. We both nodded. "Ok, go. But be back before your father gets home from work." I was pretty sure everybody involved in the conversation knew Amy and I were lying.

The nice thing about having been Evan was he never spent money on anything except video games and books. What started as a quick run to Ulta, became a stop at the hair salon, and about six other stores. I only bought four outfits, but they came with six pairs of shoes. Evan probably wasn't going to get that new gaming computer he had been saving for and Eve couldn't care less.

I was going to ask Amy how she paid for all her clothes, though, because I knew she didn't get an allowance either.

This whole thing was like the first time I tried Tiramisu. I just knew it was the most delectably delicious dessert in the world. If it was on the menu, I ordered it.

Maybe it was the pink lingerie I still had on, or maybe it was that white sundress, or the deep purple bodycon micro dress. I couldn't pinpoint the exact moment, but it was in there. Maybe it was when I saw what the eyeshadow did to my eyes or felt the luxuriousness of the lipstick on my lips. I just knew there was no going back.

Dad's car was in the driveway when we got home. I left everything I bought in the car. I could sneak it into the house later. The biggie was going to be introducing dad to Eve.

"Hey Amy. Where's your brother? I need to talk to him. Who's your friend?"

It's bad when your own father doesn't recognize you.

"Um, dad, this is Eve." She was trying so hard not to laugh.

"Hi, Eve, um, have. We. Met. Before?" It was slowly dawning on him.

"Hi, daddy." I bit my lip and cringed. "It's been an interesting day."

I don't think it's possible for a man to look more confused and surprised than my father did at that singular moment.

"Maybe we should sit down." I had long, red nails, strawberry blonde highlights in my red hair, pierced ears, and the cutest little butterfly ever hanging from my belly button.

"Talk over dinner." Mom came into the room, glaring at me and Amy. She grabbed my dad by the arm and helped him find his chair. I think we were halfway through eating before he could think straight.

Mostly, I talked to mom about what had happened all day, how it just kept escalating and getting better and better with each step. I even used the Tiramisu analogy. She laughed at that.

"So, Eve?" My dad was finally recovering from the shock of seeing his only son dressed as a very sexy young girl.

"It was Amy's idea. The name I mean. The rest I've sort of wanted for a while. I was always too embarrassed to say anything about it. That's why I started taking Amy's things."

"How long is a while?" He was trying so hard to understand. I could almost feel his angst.

"Maybe since middle school, maybe earlier."

His jaw dropped. "Evan, why didn't you come and talk to us? That's a long time to carry something like this."

"I was afraid you would laugh, that you wouldn't love me anymore. When mom woke me up this morning and wasn't mad, I knew I was wrong. I'm sorry daddy."

"Have you thought about what comes next, what this might mean to your future?"

"No" I knew he was right. I jumped way too fast, but every step felt so right. "I just knew I had to."

The four of us sat and talked for a few hours discussing all kinds of things: present, future, past. When we talked about the past, it should have been so obvious this was the path I would eventually take.

"Oh. I need to go. Brandon is going to be waiting for me." Amy jumped up from the table. And moved toward the door. "Eve, you should come, too. You could meet some people, and who knows, maybe have some fun that doesn't involve a computer."

I figured, why not? I'd already been to the mall dressed like this and the world didn't end. Besides, Amy was right. Maybe it would be fun.

It took a few minutes to get ready. Amy wanted to do something with my makeup. It looked slutty to me, but it matched hers. Besides, what did I know about makeup? She gave me some heels to wear, too. I did better walking in them than I thought I would. A few things in a small purse, and we were out the door.

I'd driven past the roadhouse a hundred times and never given it much thought. There were usually a dozen or more motorcycles parked in front, with a few dozen cars and trucks spread through the caliche parking lot. I guess it was popular. Amy didn't park in front, though. She pulled around to the back and parked next to a black Mercedes.

"Who's your friend?" A mountain of a man stepped out of the Mercedes and met us as we got out of Amy's car.

"Um, this is my brother Evan. She's a bit of a sissy and likes to be called Eve. She's here to watch, and maybe help if she wants to." Amy looked at me, her eyes begging for forgiveness.

"Amy, what is this? Why are we really here?" I wasn't too sure what I thought of being called a sissy, but, well, it was true. What choice did I have but to follow her in through the back door of the roadhouse? We ended up on some barstools toward the back by the pool tables.

It wasn't five minutes before some biker guy came up to Brandon and talked to him in whispers.

"Listen. You don't have to do anything. Just sit here next to Brandon and enjoy yourself. Eve, I know your secret. You should know mine. This is what I do." She lifted her butt off the seat and shimmied her panties down her legs, stuffing them in her purse.

I watched in awe as the biker guy bent my sister over the pool table and fucked her hard. After a few minutes, Amy got on her knees and took his cock in her mouth. When he came, she rocked back on her heels and showed him her prize before, smiling; she swallowed.

"You're a..." I hoped the look on my face displayed my confusion. Amy nodded and sat back down next to me.

"It's how I can afford all the nice things I have. Mom and dad think I'm just a waitress. You can't tell them, please."

"And you brought me here because...?"

"I wanted you to know, and to be honest, I like it a lot. I thought, maybe, you might, too." She cringed as she said it.

"You brought me here to have sex with men?" OK, now I was a little upset.

"No. Eve, it's not like that. Unless, um, you want to."

Another 'patron' showed up. I couldn't believe it. My sister laid back on the pool table and pulled her knees to her chest. Just like eating the pancakes we'd had for breakfast, she let the guy lube her and fuck her in the ass. From the look on her face, she really liked it, too.

"What about her?" Another guy showed up and motioned at me when he talked to Brandon.

"She's new, and a sissy. Maybe later."

"I'll wait." He fucking licked his lips when he looked at me. I couldn't believe Brandon said what he did.

"Fuck, I love it when they do that." Amy smiled as she sat down next to me again after a quick trip to the ladies' room.

"But he was in your, well, your bottom." I was back to confused.

"And it feels amazing. Almost better than regular sex sometimes. It would feel even better for you."

"Amy, I... This is a lot. I can't believe you're a, well a prostitute. How many guys do you have sex with?"

"Depends. I think tonight it might be a lot."

"Define 'a lot.'" I had to admit that I was getting curious. I'd seen the look on her face. She wasn't kidding. She liked it. It felt as good as she said it did.

"Maybe three or four an hour. Sometimes there's even a line." She looked almost giddy at the thought as she said it.

"And it doesn't hurt? I mean back there like you just did."

"It did a little at first, but then it just felt so full. It's hard to describe. Now it just feels amazing."

It was weird, me and Amy sitting there on those barstools talking about the intricacies of having sex, the mechanics, the technique. I just listened, asking a few questions for clarification as Amy told me everything about being a prostitute, or, as Amy referred to herself, a cum slut.

Brandon actually worked for Amy. He got a percentage for handling the money and making sure no one got out of line. I guess it was lucrative.

Another patron. Amy got on her knees as he pulled his cock from his pants. He was bigger, or thicker, than the others, but not porn star obscene. I watched, mesmerized, as Amy did the things she had described to me.

When she stopped and looked at me, reaching out with her hand. It was like someone had hypnotized me or something. I got up and went to join her. Dropping to my knees, I reached out and took it in my hand, stroking gently while Amy played with the head.

"Kiss his balls." She whispered. "They're nice and warm."

They were warm and felt good against my lips. I licked them, one, then the other. His musk filled my head. I felt a strange, queasy feeling in my groin. The man moaned when I took one of his balls in my mouth and sucked on it.

"Now, lick the shaft." Amy was whispering in my ear. Our lips glided up his cock in unison. I was doing it. We were doing it together. It was so wrong, so taboo, but it felt so right.

"Now you." Amy kissed me and smiled. I took the swollen beast in my mouth and teased it with my tongue, stroking it with my hand as I did. Amy's whispers guided me, telling me what to do. The man's moans reinforced all of it.

Instinctively, I went back to his balls, licking and slurping them both, before kissing and caressing my way back to his glans. Bobbing furiously, I stroked what wouldn't fit in my mouth.

When his hands grabbed the sides of my head, I knew there was no choice. Submitting to my fate, I relaxed and let him fill my mouth with his hot seed. Stroking him as he softened, I made sure I got all of it. Before I could swallow, Amy grabbed my face and kissed me violently, driving her tongue into my mouth, sucking the slimy juice into hers. Back and forth, we fought over the growing froth.

"Let me see." The man asked. It was almost a demand. I sucked the snowball from Amy. Smiling at the stranger, I opened my mouth and played with it while he smiled down at me. He nodded. I swallowed. Amy was right. What little male ego I had dissolved.

"Well?" Amy smiled at me as we sat back down. I fixed my lipstick just like she did.

"Yeah. I think I see why you like it. At first it felt dirty, but when he moaned. I felt sort of powerful. I was in control, not him. Even when he put his hands on my head. It was still me in control. When he came in my mouth, it wasn't disgusting like I thought it would be. I was like, I did that. I made that happen. Then you kissed me, and shit, Amy." I laughed.

We took turns until a small group came over. It sort of just happened. There were six of them. I did the blow jobs and if someone wanted to fuck, Amy took care of that. I sucked more than one of them a second time after they'd fucked Amy.

"Extra for the sissy to clean her up." The leader of the pack was talking to Brandon but looking at me.

"Her choice." Brandon cocked his head at me. I moved over and took my first taste of my sister's pussy. Thick streams of semen flowed into my mouth as Amy flexed and rocked her sex into my face. I lapped and sucked and did everything I could to not miss a drop. I knew I was finished when Amy moaned, and her body trembled. Her hands grabbed my hair and held me there while her thighs squeezed my face.