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Forbidden Fruit is Sweeter

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A young man is secretly feminized by his sister's friend.
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I woke up to sunlight streaming into my room despite the closed blinds, the mattress springs groaning beneath me as I sat up. Looking at my phone, I saw that it was already almost 10:00 AM. I always had been a late riser, and being on vacation only exacerbated that habit.

My family had owned this lake house for as long as I could remember, and we came out here every summer. Even though I was now nineteen and my older sister Ella was twenty, my parents had insisted on keeping the tradition going.

Putting on a loose t-shirt and shorts that hung down almost to my knees, I walked out of my bedroom and made my way toward the living room. There was no conversation coming from down the hall, only the faint sound of heavy breathing.

I rounded the corner into the living room and saw that the only person there was Courtney, Ella's friend from college, who had joined us on this year's trip. Dressed in a tight set of blue track shorts that perfectly hugged her ass and a matching sports bra, she faced away from me, doing one-legged squats.

I couldn't help but stare. Courtney was in incredible shape, with thick legs, a shapely ass, well-defined back muscles, round and bulging shoulders, and extremely toned arms. The shape of her back leading down to her waist had an impressive v-taper before her hips broadened back out. I still didn't know exactly what ethnicity she was; she might have been part black, but only enough to give her perpetually tan skin and slightly frizzy hair, which sat in a high ponytail hanging down just past her shoulders. Transfixed, I watched her squat down practically to the floor, balancing flawlessly on just her right leg, her arms and left leg extended for balance.

After a few more reps, she stopped and glanced over her shoulder, seeing me. I hastily looked away, not wanting her to realize I had been staring at her for a solid ten seconds.

"Good morning, Ryan." Courtney said, smiling a little. The sunlight streaming in the windows highlighted her light brown eyes. Normally I struggled to make eye contact, especially with pretty girls, but I made a conscious effort to keep my eyes on hers instead of letting them wander down to her shockingly toned body. I'd always known she was fit, but I'd never seen her in so little.

"Good morning." I replied, probably later than I should have, still distracted by the sight of her in the revealing workout clothes.

"Your parents and Ella went off to town to get something your dad needed for the boat. I think they said they were going to get brunch while they were there."

"You didn't want to go with them?"

"Nah, I needed to get a workout in. Just because I'm on vacation doesn't mean I'm going to slack off."

I took that as permission to break eye contact and look down at her body. Seeing her front now, she had visible obliques and the barest outlines of a six-pack. Her breasts were on the small side of average, but they fit her frame well, and her collarbones were well-defined.

"That's impressive dedication." I replied, then paused for a moment. "And it shows." I blushed a little as I gave her that compliment.

"Thanks!" Her smile grew a bit wider, and she started to look me up and down. My heart rate picked up. I was alone in the house with her, and I had never been very good at talking to girls, especially ones as hot as Courtney. But nervous as I was, I was also excited. Truth be told, when I first heard Courtney was coming with us, the thought of seeing her in a swimsuit was the thing that had interested me most about the trip. The workout clothes weren't quite as revealing as a bikini, but I was still enjoying the sight.

We stood there looking at each other for a moment, and I realized I should say something, but I was struggling to think of what. Was I already fucking this up?

"Hey... question." Courtney finally said, breaking the awkward silence.

"What is it?"

"How much do you weigh?"

"Uh... about 140 pounds.." I had assumed she was going to ask where my parents kept the glasses or the towels or something. Why was she asking about my weight?

"Okay, perfect. Can I ask you for a quick favor?" She sounded pensive and looked like she might have flushed a little red if her skin tone were lighter. What was she so nervous about?

"Um... sure?"

"So, I'm used to working out in a gym, not at home. And there isn't really any exercise equipment or anything here... so..." She trailed off, biting her lip nervously and looking up at me. "Can I use you as a weight?

"What? You want to lift me?" I hadn't been sure what to expect, but it wasn't that. I flushed bright red and my pulse sped up even more.

"Yeah... I know it's a little weird, but I'd really appreciate it."

"Sure." Now that I'd had a moment to process her request, the thought of her tossing me around a little was extremely appealing. There was something about the idea of a woman who was stronger than me that I'd always found attractive. Hopefully Courtney didn't notice the bulge that had formed in my shorts.

"Thank you so much! Okay, let's see..." Courtney looked around the living room, trying to find a suitable spot for whatever it was she wanted to try. Her eyes settled on the couch near the middle of the living room and she walked over to it, sitting down on the rug with her back against the couch and her legs straight outward. I followed her, unsure of what she wanted.

"Okay, I want to do some hip thrusts. Normally I do these with a barbell on my lap, but, uh... today it's going to be you."

"You want me to sit on your lap?" My ears were burning hot now, and my underwear got tighter at the front. Why did this turn me on so much?

"I don't bite." She gave me a little grin and eased her hips forward so that only her upper back was pressing against the couch, then spread her arms out on top of the cushions for stability. Bending her knees, she placed the soles of her feet flat on the floor.

Heart racing, I stepped forward and climbed down onto Courtney's lap, facing away from her, my feet on either side of hers. She stifled a giggle as I settled into position, my back leaning against her torso. Her skin was soft, but the muscles underneath were hard. Then I felt her hands grabbing my hips, and it was my turn to try not to giggle. I'd always been ticklish.

"Ready?" She asked from behind me.

"Yeah."

I felt myself being lifted as she pushed her hips up in a smooth motion, leaving only my feet on the ground before she settled back down to the bottom of the motion.

"Here, try to keep your legs wrapped around mine so your feet aren't on the floor."

I obeyed, putting my legs over hers to keep my feet off the ground. The incline of my legs made the hem of the shorts drop toward my hips, making it obvious how much thicker and stronger her legs were than mine.

She repeated her hip thrust, lifting me again, my entire body supported by her this time. Breathing with each rep, she repeated the motion over and over and over again slowly, her hips and my body rising up and down. I knew she was strong, but I was amazed how she finished ten reps of effortlessly lifting my entire weight with just her hips before she started to get tired. Even then, she managed another five reps with a little more effort. As her motions became more wobbly, I grabbed the undersides of her thighs for stability, feeling the hard muscle and the soft skin beneath my hands.

Courtney finished her last rep and settled back to the floor, breathing heavily. With my back pressed against her, I could feel her chest rising and falling. We lingered there for a moment, my hands on her thighs and her hands on my waist as I sat on her lap. Her fingers suddenly squeezed at my hips and waist, making me gasp. Courtney gave out a little giggle at that.

"That was... a good set. Mind getting me a glass of water?" she asked.

"Yeah, of course." I said, reluctantly pulling myself off Courtney's lap and standing up. The house had an open floor plan, so I could still see her leaning back against the couch from the kitchen. I stole another glance at her as I filled the glass at the sink, and her eyes caught mine. Like I had earlier, I turned my head away quickly, not wanting to be caught staring. That seemed to amuse her.

"It's okay to look at me. I spend a lot of time working out. You think I don't like showing off?"

I blushed, but I appreciated the permission. I kept my eyes on Courtney as I made my way back over with the glass of water.

"Just trying not to be creepy." I explained, sitting down on the floor next to her and handing her the glass of water. She chugged the entire glass eagerly.

"Don't worry about it. You're too pretty to be creepy."

My whole face flushed hot at that. It felt good to get a compliment from her, but being called pretty felt a little emasculating. But maybe that was part of what made it feel so exciting.

"You're really cute when you get flustered like that." Courtney said with a slightly mischievous smile.

"Th-thanks." I managed to reply, my mouth dry. "You're..." What was I supposed to say back? I was supposed to give her a compliment back, right? "You're really strong."

Really? That was the best my brain could manage? This girl was calling me pretty and cute, and "strong" was what I could come up with to flirt back?

Courtney seemed to enjoy hearing it, though. She grinned broadly and flexed her triceps for me as she slid her arms off the couch and put her hand on the floor between us. The muscle had a very impressive and well-defined v shape.

"You did seem to like holding onto my legs during those hip thrusts..." she said, wiggling her muscular legs at me.

"I didn't want to fall off." I couldn't keep my eyes off her body, glancing between those toned arms and statuesque legs. "But yeah, it did feel nice." I admitted.

"I liked it too." Courtney smiled and paused for a moment. "You can touch me some more if you want to."

My pulse spiked and I hesitated for a moment, but I decided I definitely wanted to. Tentatively, I reached over and ran a finger down the hard muscle of her tricep. She gave me an encouraging look, so I scooted closer and placed a hand on the muscle of her thigh. She straightened the leg out, flexing the muscle and letting me feel just how thick and strong it was.

"You have an amazing body." I said, marveling at her. She beamed with pride, then put on that mischievous grin again.

"I bet yours is pretty nice too."

I blushed again, this time in shame. I was slender and scrawny, not at all athletic. In school, I had always been the last kid picked for the team.

"Yeah, I don't know about that. I'm sure you're stronger than me. I don't even work out."

"That suits your vibe, though."

"My vibe?"

"You know. Cute, shy, demure."

My face heated up at that, and I'm sure that I turned as red as a tomato. Cute? Shy? Demure? I didn't have a lot of experience with women, but these didn't seem like the compliments they normally give men.

"I don't think I've ever seen anyone blush so red," said Courtney with a giggle. She paused for a moment, staring at me with those brown eyes. "Can I kiss you?"

The words hit me like a hammer. My heart pounded like a drum.

"Yes." I replied almost instantly. I expected her to lean in slowly and give me a peck on the lips.

Instead, Courtney launched herself at me, practically tackling me onto the rug, pinning me to the floor. She slipped her waist between my legs and pressed down on me with her whole weight, trapping me underneath her as her lips locked onto mine and her tongue thrust into my mouth. I breathed through my nose as she kissed me with animal passion, and I jumped with shock as she reached a hand down the leg of my shorts and groped my ass.

After ten or fifteen seconds of that, she finally broke away from the kiss and looked down at me with a grin. The way she was pressed on top of me, my legs around her waist, there was no way she couldn't feel my raging erection. She bucked her hips, grinding against it.

"So..." she finally said, "when do I get to see that body?"

Courtney reached down to the hem of the t-shirt and started lifting it up. I moved to sit up, still a little dazed from how fast this was happening, and Courtney climbed off of me, letting me up. I pulled the t-shirt off and saw her standing in front of me, reaching a hand down to help me up. I looked up at her for a moment, admiring the view from her feet, before taking it and standing up. Without letting go of my hand, she started leading me back to the bedroom she shared with Ella. My heart raced.

Courtney pulled us into the bedroom and shut the door.

"Don't forget the shorts," she said.

I unzipped them and dropped them to the floor, leaving me there in nothing but my white briefs. There was a mirror on the wall, and I couldn't help but note the contrast between us. We were exactly the same height, but she had dark tan skin and a toned, powerful, muscular physique compared to my pale skin and slender body. I felt emasculated, but somehow that just turned me on more.

"I don't know why you were so ashamed of your body," said Courtney, looking me up and down with a smile.

"T-thanks," I said, blushing again, but feeling better about that knowing she thought it was cute. "I didn't think you'd like it."

"But it's so nice and... supple. I think you just need to find some clothes that fit you better." She stepped into the closet, looking for something. I watched her with puzzlement, but she returned a moment later with one of Ella's floral pattern sundresses and a pair of panties.

"Uh, Courtney?" I asked, staring at the dress.

"Ryan?"

"You... you want me to put that on?"

"Why else would I have gotten it out?"

I gulped, unsure of what to do. Why would she want me to put on a dress?

"If it makes you feel more comfortable," she said, "I'll look the other way while you change into it."

I tried to stammer out an answer but was at a total loss for words. Courtney tossed me the dress and the panties, then turned her back toward the door and away from me and the mirror. I hesitated. Putting on my sister's dress would be humiliating. But it was awfully hard to say no to Courtney. I took one glance at her toned body and then down at the dress.

The decision didn't take long to make. I dropped the briefs and stepped into the panties, which wasn't easy with my erection. Then I slipped the dress on over my head and turned to inspect myself in the mirror. It actually fit me quite well, the spaghetti straps sitting on my slender shoulders and showing off my delicate upper body and well-defined collarbones, the midsection hugging my thin waist, and the hem stopping mid-thigh, revealing my thin legs. My thin blonde body hair was barely visible. I took a deep breath.

"Courtney? You can turn around now."

She turned around and opened her eyes, and I saw her face light up as she took in the sight of me. Her eyes twinkled and she grinned the broadest grin I'd ever seen from her.

"Now that's what I'm talking about!" She walked toward me, then around me, inspecting me from behind. I stood still, watching her in the mirror as she shamelessly checked out my ass. Now that I looked, there was a nice shelf at my backside. Courtney reached down and smacked it playfully.

I yelped in shock but couldn't stop myself from giggling. There was something about being in the dress, seeing myself looking so girly, that made me want to play into the role.

"You like it?" I asked, fishing for a compliment.

"That's not a strong enough word." Courtney looked me up and down again. "Fuck! You look better in that dress than Ella does."

"Thank you." I blushed, enjoying her obvious enthusiasm for the way I looked in the dress. We looked into each other's eyes again and she stepped forward, closing the distance between us. Grabbing my waist, she pulled me in against her toned body and kissed me passionately again. Less caught by surprise this time, I kissed back.

Courtney reached down and groped my ass again, making me gasp in shock but press up against her harder. She grinned excitedly and gave me a shove back onto the bed. I lay on the bed, looking up at her eagerly, but she didn't climb on top of me. Instead, she crossed the room to her suitcase and fished for something in it.

"Courtney?" I asked, confused.

"Stay right there." She hooked her hand into the waistband of her track shorts and pulled them down along with the panties, stepping out of them. Seeing her naked except for her bra, I marveled at her glute muscles and thick thighs. Next, she grabbed that thing from her suitcase and started stepping into its harness. What the hell was that?

"Courtney? What's that?"

She turned around, revealing a five inch strapon and grinning at me.

"Is that... why do you have that in your suitcase?" I asked, alarmed. My heart was racing now, pounding in my ears.

"Well, I knew you'd be on this trip, soI brought it in case we got a moment alone." She pulled something else out of her suitcase, a bottle of liquid, and starting squirting some of it on the strapon. Lube.

"Wait, what? You've been planning this?" I sat up on the bed and watched her as she approached me, smiling like a predator and swaying her hips sensually. I was ashamed to realize the sight somehow turned me on even more despite my fear.

"Mhmm. I've been itching to fuck you since we came up here yesterday. You haven't noticed me eyeing you up this whole time?"

Courtney stopped right in front of me, leaving me eye level with her abs. I looked up at her, grinning down at me with a wicked look in her brown eyes. I searched my memory of the drive up here and the first day at the lake house. I'd been stealing glances at Courtney the whole time, but now that she mentioned it, she had seemed to catch me doing that an awful lot. Like she'd been watching me too.

"I-" I stammered, trying to think of what to say but coming up blank.

"The way you look when you get nervous turns me on so much. There's just something about you that makes me want to... mmm!" She squeezed her eyes shut for a moment. I noticed she was trembling with anticipation.

When I first realized I was alone in the house with her, I had been nervous. Now I realized I was alone with her and she was aching to peg me, and somehow the nervousness had been joined by excitement. Part of me wanted to man up and tell her no, to keep my dignity intact. But an even bigger part of me wanted to give in to this beautiful, muscular goddess of a woman.

"I-I've just never done this before." I managed to say. Telling her no was beyond me.

"Never done what?"

"I've never... done anything really. Never even had sex. Definitely never been pegged. I'm still a virgin."

Courtney's expression grew warmer and gentler, but her eyes didn't leave me. She put a hand on my shoulder, sliding a finger under the strapon of the sundress. My heart raced at her touch.

"Well, you don't need to be afraid. I'm going to make your first time special. Don't worry, I'll be gentle." Her voice was calm and soothing, but there was still an edge of excitement to it.

"Yes, please. I'd like that."

"You liked being on my lap for those hip thrusts, right?"

"Mhmm." I nodded.

Courtney sat down on the floor, her back against the bed like it had been against the couch earlier, the strapon pointing up. She looked up at me and patted her thigh.

"Get on my lap. Straddle me and face me this time."

I obeyed, placing my feet on either side of her hips and sitting down toward her lap. She put her hands on my hips to guide me, lowering me toward the strapon. Reaching up the dress, she slid the panties to the side. I felt the tip of the strapon between my cheeks and shivered. Courtney slowly guided me down, the strapon reaching all the way to the hole and then penetrating it. I gasped as I felt it begin to stretch me.

12


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