“Yeah,” I said. But I still hadn’t even taken my shoes off.
“You have to come out and show me,” she said. I squirmed and wished I would have just gone to prison. Then I slowly started getting undressed. I thought about resisting—telling her that I wasn’t going to let her make a joke out of me. I couldn’t sacrifice my pride for the sake of her amusement. But I also couldn’t let her go to her father and tell him that I wasn’t participating.
I’d forgotten how strangely feminine my body looked all shaved and hairless. I found myself looking at my naked figure for a moment before slipping into the piece of lingerie on the top of the pile. It was a tight lacy number that did nothing to cover my ass—and hardly anything to cover my cock. It took a minute to shuffle my package around to actually fit in the little outfit. It had little straps dangling down, which I didn’t realize until later were for holding up stockings. I had to slip the pads from my bra into the outfit, so there weren’t just two deflated pouches on my chest.
“Any day now…” Cassandra said from the other side of the changing room door.
I took a deep breath and slipped out. I held my hands down between my legs—one wrong step and my cock would easily flop out into plain sight. Cassandra’s face lit up at the sight of me. I could see her biting down on her tongue, trying not to laugh. “That looks surprisingly great on you,” she said. And the sad part was that it was true: it really did look surprisingly great on me. It fit perfectly and it made my ass look amazing. My legs looked long and model-esque, and the thin straps made my shoulders look less defined—like the shoulders of an actual woman.
“Try on another one,” Cassandra said with bright red cheeks.
So I tried on another one: a white two piece. The bottoms did a much better job of hiding my cock, so I was less embarrassed stepping out to show off to Cassandra. It was another hit, making Cassandra’s face light up. It turned out, there wasn’t much that didn’t look surprisingly good on me—and it truly was a surprise every time. “You need to buy all of this—it would be a travesty if you didn’t own all of it,” she said to me.
“What am I going to do with it?” I asked. It’s not like I could wear it out, and it’s not like I planned on having guys over to show it off to—so what was the point?
But she insisted that I buy some—so I bought a couple items: the white two-piece and a red one-piece. The red one-piece looked especially stunning on me. I had to wait a moment to step out from the changing room in the outfit because the feeling of the tight lace against my cock gave me a raging erection.
As we left the store, Cassandra was still trying her best not to laugh. She was having too much fun, and her day of torment wasn’t over. She dragged me through the makeup store and made me sit down and have a makeup artist draw on my face. Then she dragged me through a dress shop and she made me buy a slutty cocktail dress. “You need it for formal events,” she said, as if I was going to be going to any formal events while I was stuck in the witness protection program. But I ended up buying the dress (partly because it looked so good on me, I couldn’t say no to it), and then I ended up buying about four hundred bucks worth of clothes at various other stores.
While we were leaving the mall, Cassandra started giggling. “What’s so funny?” I asked.
“You’re going to need a job soon,” she said, “if you keep spending your money like that.”
I didn’t realize until she showed me my credit card balance that I’d spent nearly a grand that afternoon. “Why did you let me buy all of this stuff?” I asked.
She laughed. “Part of being a woman is learning self control at the mall. But maxing out your credit card is a sort of right of passage as a woman,” she said. I caught her giggling again a couple of blocks later. I didn’t ask her why she was giggling this time—I just assumed it was at my expense. But I was already starting to think of a way to get back at her.
CHAPTER VI
Cassandra liked to dress me up in lingerie and tiny skirts and short dresses, but she never dressed quite so scandalous herself. In the week that I’d been living with her, the most scandalous outfit she’d put on was a knee-length dress with a slight slit up the side, showing off a bit of her hip. Even the pyjamas she wore to bed were full-length: sleeves and legs and socks.
When we got home, Cassandra said, “I’m going to take a shower.”
But I stopped her. “Wait,” I said. “I want you to try on some of the stuff I bought. I want to see how it looks on you.” I watched as her cheeks turned red and the rest of her face turned a shade of pale. She smiled and then she looked at her feet.
“That’s not really my style,” she said.
“C’mon. Just entertain me,” I said. Back when I was with the organization, some of the guys had a way of getting revenge on the girlfriends who cheated on them. When they started a relationship with someone, they would take what they called ‘insurance photos’: usually nude photos of girls that they could use later as blackmail or humiliation photos, in the case that they had a falling out with their girls.
The phone I had may not have been able to access most websites, but it had a camera. So I started Cassandra with the little cocktail dress I bought. She took it into her room and then there was a long silence. “What’s taking so long?” I asked.
“It’s just a bit short,” she said.
“Let me be the judge,” I said.
She came out a few seconds later—and she was right: it was short. But short was good. For the first time ever, I saw Cassandra’s thighs. She tried holding the skirt down while she did a little spin, but it wasn’t enough to cover her big tush—her bum was much bigger than mine. Her face was dark red. “Not great,” she said.
“I think it looks amazing,” I said. I lifted my phone and snapped a photo.
“Did you just take a photo?” she asked. Her face turned even redder.
“Yeah—so you can see yourself,” I said. “Mirrors aren’t always honest.” I showed her the photo and I watched as she let a smile slip. She liked the shot. She bit her bottom lip.
“I guess it doesn’t look so bad,” she said.
“No—it looks great. You’ve got a great ass.”
She looked at me with an unimpressed look. “Girls don’t say stuff like that,” she said.
“Sure they do—I hear them say stuff like that all the time.”
“But they don’t say it the way you just said it.” Her cheeks were still that dark shade of crimson.
Next, I had her try on the white two-piece that she made me try on in the lingerie store. She resisted a bit at first, but I could tell that she was slightly curious to see how she would look with the high-waisted lace bottoms. And to be honest, I was curious to see how she would look. I still couldn’t believe that bum that she kept covered up—it was a shame that she kept it covered, along with those perfect legs. If I were her, I would have done nothing but flaunt my body around. I wouldn’t wear jeans and sweaters all the time, and I wouldn’t sleep in full-length pyjamas.
“Ready?” she asked from the other side of her bedroom door.
“I’ve never been more ready,” I said.
The door opened slowly, and then she stepped out. And damn, did she look good. My plan was originally to embarrass her, to get back at her for toting me around the mall like her toy doll. But now, I couldn’t see any reason for her to be embarrassed. She looked good in the lingerie. I was now trying to convince myself not to throw myself at her. I wanted to feel her body. She was so amazingly curvy. Her breasts looked so soft (they were a bit too big for the white lace top) and her ass was so damned juicy. “What do you think?” she asked.
“Is it true that girls make out with each other at slumber parties?” I asked.
She laughed. “None that I’d ever been to,” she said. “And again, girls don’t say things like that to each other—and they definitely don’t look at each other the way you’re looking at me now.”
“I can’t help it. You’re sexy,”
I said.
Her whole face was that dark shade of crimson. “You aren’t being very ladylike,” she said.
“Maybe I’m a lesbian,” I said.
“Well knock it off. You’re making me uncomfortable.”
“Spin around and show me your backside,” I said. She followed the command. Then I snapped a few photos.
“Hey!” she said. She came towards me with her hand out in an attempt to snatch the phone away. “You’d better delete those photos.”
“Try to make me,” I said. She tried for a while to grab the phone from me, but she was just too slow. With a quick move, I managed to slip the phone under my skirt and into my panties. Then I raised my hands in the air. “It’s all yours if you want to grab it,” I said.
“You’re a pervert,” she said.
“I can’t help it. You’re hot,” I said. I watched as she tried not to smile. She bit her bottom lip and squirmed slightly. She liked the compliments, and I could tell that she wasn’t used to them. The guys she hung out with must have been beta-males—too afraid to compliment her. I wasn’t afraid. The girl was a fox and foxes need to be complimented.
She stared into my eyes for a moment and then she said, “Don’t think I won’t.”
“Won’t what?”
“Reach and grab that phone.”
“I really don’t think you will,” I said.
She was silent for a moment. I could almost hear her heart pounding. Then she looked down and she pulled up my skirt with one hand. With the other hand she reached down, into my panties, and she went for the phone. But she didn’t quite make it before her fingers were on my cock. She stopped. Her eyes lit up for a moment and her whole body seemed to be frozen. Then she looked into my eyes again. “Are you hard?” she asked.
“Can you blame me? Look at yourself in the mirror.”
“You’re a criminal,” she said, as if she was trying to give herself a reason to let go of my cock.
“They dropped the charges, so technically I’m not a criminal.”
“But you’re… you’re in a gang,” she said.
“Not anymore.”
“Your cock is really big.”
“You haven’t even felt the whole thing,” I said.
Then, after a moment of silence, I felt her fingers curl around my girth. She pulled her hand down to my tip and then she stroked it back to my pelvis. The phone fell out of my panties, onto the floor, but she didn’t seem to notice. “It’s so big,” she said again.
“I think it should fit,” I said.
“Fit where?”
“In your pussy.”
Her face was pale now and her lips were parted. She looked scared, as if she was about to tell me that she was a virgin. She didn’t end up saying whether or not she’d ever had sex before, but I had a hunch that I was about to be her first. I reached around her and I grabbed two handfuls of that big, perfect ass. I felt a wave of relief wash over me. I wasn’t sure I could go another minute without feeling that soft bum. I squeezed and she let a little moan slip, as if she was already halfway towards her orgasm.
“I’m not a slut,” she said.
“I know—but I am,” I said. And then we kissed. Her lips were soft—every part of her was soft. I started exploring her body with my hands: feeling her sides, her thighs, her arms, and her tits. I squeezed her tits hard and then I played with her perky nipples. She moaned some more, so I bent down and sucked one of her nipples. When I finally reached down between her legs, she was already wet, already soaking through the white lacy bottoms. As soon as I touched her clit, she moaned, “Oh God.”
I lifted her up and I ran her into her bedroom. She giggled and held on tight. Her face was still dark red. As soon as she was on her bed, she reached out again and grabbed onto my cock, as if she couldn’t help herself. She needed to be holding it and feeling it and stroking it. I pushed her onto her back and then I made her suck it—and she liked it. She sucked and bobbed and salivated all over my long shaft. I gently thrust my hips, pushing my rod into the back of her throat. She gagged, but she wanted it. When I stopped thrusting, she pushed her head forward so that she could feel my tip in her throat again.
“Have you ever been fucked by a girl before?” I asked with a grin.
She shook her head. Her eyes were shining: scared and excited.
I held up her legs and I looked down at her glistening pussy. A dribble of clear fluid was running from her slit to the bed below. I pressed my cock against her tight hole. She gasped sharply and I wasn’t even inside of her yet. I ran the tip of my cock in circles around her tight hole, teasing her. She was already squirming, trying not to scream. I started pushing myself in. And for a moment, I was worried that she was too tight for my cock. Even with my cock slicked with her saliva, and her pussy dripping with warm natural lubricant, I had a hard time penetrating. But after about fifteen seconds of pushing, she suddenly opened wide and I slipped in. She groaned loudly, letting her head fall back onto her pillow—and I went straight to work.
I started thrusting quickly, putting all my force into each push. I was only able to get half of my cock into her before she looked uncomfortable, so for the first few minutes I only pleasured her with half of my cock. But I could feel her loosening up, and I could tell that she was starting to relax—so I slipped another inch into her. And then another inch, and then another. And soon enough, my pelvis was slapping her big tush. She was groaned and screaming and squirming and clutching at the bed sheets.
I slapped her gently on the face, which she liked, so I slapped her harder. “More,” she said. So I wrapped my fingers around her throat and I clenched. She smiled big—she liked it rough. So I grabbed her by the hips and flipped her over without restraint. I slapped her on the ass and then I started to press my cock into her asshole. She clenched at first, but she didn’t stop me. She wanted it in the ass and she wanted it hard. I slapped her ass again and then I aggressively spread her cheeks, widening her hole. I pressed my cock in. She clenched on it hard. I reached down and slipped a few fingers into her wet pussy and I fingered her while I rammed her asshole.
It was only a few seconds later before she squirted a gallon of fluid and ruined her clean bed sheets. I made her taste her squirt off of my fingers—and then I choked her again, after a few more hard spanks. “I’m going to come in your mouth,” I said.
“Please come in my mouth,” she begged.
I pulled out, flipped her over, and I shimmied forward. I grabbed her face, forcing her mouth open, and then I stuck my cock in. I made her taste her own asshole before filling her mouth with my hot load. I wiped the final drop of my cum on her chin, and then I stood up and looked down at her. Her throat was red from being choked, and her tits were red from being squeezed. When she stood up, I saw that her ass was dark red from being slapped, and her hair was a frizzy mess from being thrown around. She was probably in a bit of pain from being penetrated so aggressively—but that smile never left her face.
CHAPTER VII
It was late that night when she snuck into my bedroom and woke me up. “W—What’s going on?” I asked.
I didn’t know that I was using my male voice until she said, “Talk to me like a girl.” So I cleared my throat and I asked her again. “I’m horny,” she said. “I need you to fuck me.”
I looked over at the clock. “We just fucked like, six hours ago,” I said.
“So what?” she said. She didn’t wait for me to give her the green light. She slipped under the covers and she reached her hand up the skirt of my nightie. Then she started to massage my flaccid cock. My first assumption was that I was dreaming. I wasn’t used to hot young women sneaking into my bedroom to have sex with me—but I wasn’t about to complain. I kissed her for a few seconds, but she was more interested in my cock. She sunk down under the covers and started sucking me off. It felt nice. I slipped my hands behind my head and I relaxed. It wasn’t long before I was rock-hard.
“Talk to me,” she said.
&
nbsp; “What should I say?”
“Just say anything with your girl voice,” she said.
“You’re really good at sucking cock,” I said.
“No—talk to me like you’re a girl.”
It took me a moment to realize what she was asking. “You’re really good at eating pussy,” I said. And that did the trick. My words seemed to energize her. She sucked harder and bobbed her head faster. She even started moaning slightly. And then she moved her attention downwards, to my asshole. She started eating out my asshole.
I’d never had a girl’s tongue down there, but it actually felt kind of nice, so I didn’t stop her. Though it started feeling weird when she started pushing a finger up my asshole. “Your pussy’s so tight,” she said.
“Keep eating me out,” I said, playing along. It felt nice, but something about the act seemed off. I wasn’t sure if Cassandra was a lesbian, or if she was just into some weird kinks. She got a second finger into my asshole, and then she started pumping my butt quickly. I tensed up and clenched on her fingers, but she didn’t stop. She got her head in and she tickled the rim of my asshole as if it was my clit. I took a deep breath—once again, it took a minute or two before it started feeling nice.
And then I noticed the long black thing on the bed. My heart skipped a beat—I thought it was a snake at first. They have snakes in California, right? I nearly gasped. She must have heard my reaction, because she surfaced. “What’s wrong?” she asked. Then she saw me staring at the still creature. She grabbed it and held it up, in the ambient moonlight. It was a double-sided dildo. “This?”
“What are you going to do with that?” I asked.
“I thought we could have some fun,” she said with a big grin. She quickly pulled off her panties and then she pulled back the covers of my bed. The skirt of my nightie was pulled up, exposing my wet asshole and my throbbing erection. She got positioned in front of me, so her pussy was only a few inches away from my asshole. Then she penetrated herself with one end of the dildo. I knew right away where the other end was going to go.
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