Meeting His Match

As the evening wound down, I scanned the room. There were six of us in my friend Lana's apartment, three guys and three girls. All the girls were pretty, but the one I had my eye on tonight was Anna.

Anna was in her early twenties like the rest of us, with glossy chestnut hair in a high ponytail, hazel eyes, and a pretty face with a sharp jawline. She wore a dark green turtleneck and a tight pair of jeans; the outfit hugged her figure in a way that showed off an upper body well-built for a woman and some incredibly shapely legs. One of Lana's friends, I only knew her in passing, but as the hours had gone by this evening, my eyes drifted to her more and more.

It had been a pleasant few hours of red wine, tasteful banter, and storytelling, but Lana was obviously getting tired, her usual chattiness becoming subdued and yawns punctuating her sentences. One by one, guests were making polite excuses to go.

"It's been a lovely evening," said my friend Andrew, standing up from the table, "but I've got work tomorrow. Good to see all of you."

Shortly after he was out the door, Anna piped up as well.

"Yeah, I should probably head out too. Thanks for having me over." Her voice was low and pleasant, and, at least to my tipsy ears, had an almost musical quality to it.

Seeing my chance, I jumped in before Lana could even say goodbye.

"Here, I'll walk you home. It's pretty late." That was the way to do it; just offer, don't make it a question.

"Such a gentleman." There was a hint of an amused smile on Anna's face, as if there was some kind of joke I wasn't aware of.

We said our quick goodbyes to Lana, put on our coats, and stepped out into the frigid night. It was dark out, but the campus sidewalks were well-illuminated by the streetlights. Anna made a quick left turn and started us on the way back to her apartment. Not wanting an awkward silence to develop, I decided to make some light conversation.

"So, I don't think I asked, how did you meet Lana?"

"We were in the same astronomy class sophomore year. Those gen-ed requirements, you know?"

"Ugh, glad I have those out of the way. I'm a liberal arts guy, don't make me study science."

That line earned just a hint of a laugh from Anna, but that was enough to make me feel a little warmer on that cold night.

"She talks about you a lot, you know."

"Oh? What does she say? Nothing bad, I hope."

"Oh, you know. Connor, smart, funniest guy she knows, life of the party." Anna paused, looking over at me as we walked, a twinkle coming in her hazel eyes and a faint smirk on her face. "Ladies' man."

"Ladies' man?"

"Mhmm. She says you hardly ever leave an event alone."

"What can I say? It just happens."

"Oh? You seemed pretty eager to leave with me."

"Well, I wouldn't want to make a woman walk home alone at this hour."

"And they say chivalry is dead."

"Yep, that's me. Your regular knight in shining armor."

Anna giggled and turned to look at me, giving me an appraising look. She reached over and patted my arm, sending my heartrate just a bit higher.

"Well, I'm grateful to have such a big, strong man to look out for me."

I knew she was being ironic; she still had that little smirk on her face, and I definitely wasn't big or strong. I had always been slender and no more than average height. In the heels Anna was wearing, her eyes were exactly level with mine. If it hadn't been for her playful tone, I might have taken her reply for a dig at me.

"You look pretty fit yourself." I replied.

"Powerlifting will do that for you. Anyway, here we are."

We stood in the courtyard of another on-campus apartment building in front of a door that must have been Anna's. She reached into her purse and retrieved her keys while I looked at her and the door. Here was the moment of truth.

"Thanks for walking me back," said Anna as she opened her door, looking back over her shoulder at me, her eyes reflecting the lamp light. She paused for a moment, looking me up and down, thinking about something. My heart warmed as her smile got just a little bit wider.

"It was a pleasure."

"What, you're not going to try to convince me to let you in?"

"It's kind of trashy to ask outright. I was just going to let my winning smile and charming demeanor do the talking for me."

"Well well, someone's cocky."

"You're still smiling."

"Well, I suppose it wouldn't kill me to invite you in, just for a drink..."

Anna stepped inside, leaving the door open for me. I exhaled in relief and excitement as I followed her inside. It wasn't a big apartment; the front door took us straight into the kitchen, which was connected to a small living room with a faux-leather couch and a wooden coffee table. A single door at the end of the room presumably led into the one bedroom. That was good; no roommates to deal with.

"Thanks. It's cold out there. Nice place you've got here."

I couldn't help but stare a bit as Anna stepped out of her heels and shrugged out of her coat, once again letting me see her in that form-fitting turtleneck. Her breasts weren't large, but they fit her frame perfectly. Plus, she had a very nice ass. This was going to be an amazing night if I played my cards right.

"Wine?" she asked, heading into the kitchen and getting out a bottle and a set of glasses before I could answer.

"I'd love some." I enjoyed the view as she bent over just a little bit in front of the kitchen counter, her tight jeans hugging her thick legs and full rear.

"Go ahead and take a seat, I'll bring it to you."

I made my way over to the couch and sat down. Soon, Anna walked over to join me, two glasses of red wine in her hands. She set them down on the coffee table and took a seat on the couch, not at the opposite end, but also not as close to me as I would have liked. I picked my glass up off the table and took a sip.

"It's delightful. You have good taste."

"In wine, or the kind of guys I invite home?"

"Both." I said, smiling at her, pleased to hear some indication she hadn't just let me in out of politeness.

"So, how does this normally go?" Anna asked, her eyes staring directly into mine.

"What do you mean 'this'?"

"Oh, you know. This thing where you chat a girl up, go back home with her? You've got quite the reputation."

"I was planning to just see where the night takes us." I sipped again.

"I hear a lot of nights have taken you a lot of places."

"A gentleman doesn't kiss and tell."

"You'd be surprised by how many girls do, though. I've heard a lot about you."

I actually wasn't all that surprised. Truth be told, my reputation made it easier to get laid. Once you make it with a few girls and they start gossiping about you, a mystique builds up around you, and then other girls start to think of sleeping with you as a way of proving they can compete with the others.

"Hopefully nothing too bad."

Anna's eyes were searching me now, sizing me up, seeming to pierce into me. It actually made me a little uncomfortable, and I looked away.

"Nothing horrible. Some complaints that you don't want more than a hookup. That you just kind of disappear if you're not interested."

"Hey, sometimes it just doesn't work out. There isn't always chemistry."

"No judgment from me." Her stare became a little less intense, and her playful smile started to form on her face again. "I can see how you get around though."

"How's that?" I asked, my ears prickling. Call me vain, but I always appreciate compliments.

"You're funny. And you have that pretty boy thing going. Like you could be a pop star or something."

"Thanks." I blushed. "You're a looker yourself." I let my eyes ostentatiously make their way down to her chest and legs, then back up." Just then, my phone buzzed in my pocket. I was holding the wine glass with the base touching my leg, and it picked up the vibration, letting Anna hear it.

"In high demand, are we?"

"So it seems."

"Who is it? Someone I know?" There was a spark in her eyes, a smile on her face, and a tone of eager, playful curiosity in her voice.

Wanting to keep the good mood going, I reached into my pocket and pulled out my phone to check. Anna scooted closer to me on the couch, her leg brushing against mine. Now that I looked down, her legs were thicker than mine.

"Do you know Cassandra?" I asked, checking the text to see who it was from. Anna was looking over my shoulder.

"What's her last name?"

"It's... uh..."

"You don't even know?" She looked ready to burst out laughing. "If I look through your phone, how many girls' numbers am I going to see?"

I opened my mouth to speak, but before I could say anything, she reached over and snatched my phone from my hands.

"Hey!" I said, reaching out to grab it back. Anna scooted back, giggling, and held it away from me as I scrambled for my phone, unable to touch it. I followed her to the other end of the couch and reached over her. My fingertips brushed it, but then I felt her arm around my waist as she pulled us both off the couch and onto the floor.

I landed on top of her, but that didn't last for long. Laughing, Anna rolled us over, climbing onto me. I wriggled and tried to wrestle free, grabbing at my phone too, but soon I could feel my back pressed against the floor and her thick thighs straddling my waist. I'd known she was in good shape, but now I realized just how strong she was as she pinned me to the floor, my phone in her right hand, her left hand grabbing my wrist.

"Alright, let's take a look... Wait, the phone got locked while we were wrestling." Anna stared at the phone screen for a second. "Oh, fingerprint to unlock. Cool." I only struggled a little as she pressed my finger to the screen, unlocking it.

Sighing, I realized I was beaten and stopped struggling. There was no way I was going to be able to get out from under her or get my phone back. Honestly, it felt nice to have her weight on top of me, not to mention the way her legs, which I'd been admiring all night, were wrapped around me. With just a little embarrassment, I noticed I was starting to get hard.

"Let's see... yeah, a whole lot of girl names -- just first names, mind you -- in your contact list. Quite the Snapchat message history too..."

My cheeks were getting hot. Between being overpowered by a woman, having her invade my privacy like this, and somehow being aroused by it, I was feeling embarrassed.

"Damn, Connor. I knew you got around, but if a girl slept around half as much as you did, she'd get called a slut."

I tried to come up with an answer, but it's hard to be witty when you're pinned to the floor and being interrogated about your sexual history. Anna looked down into my eyes, and her amused smile became just a little warmer. She set my phone down to the side and let go of my hand. There was a moment of silence. My erection was not going away. She shifted her hips, and I realized there was no way she didn't notice it.

"Hey, it's okay, I'm just messing with you. I do like you, you know."

"You're... different from the other girls, I'll give you that." I exhaled, wriggling a little, the thin carpet not terribly comfortable beneath me. "I like you too." I said after a moment.

"Mmm, I could tell." Anna playfully shifted her hips back and forth, grinding on me, and I became quite aware that our clothes were the only thing between my erection and her. Encouraged, I let my hands drift down onto her thighs, feeling the hard muscle underneath her tight jeans.

"These legs certainly help"

Anna reached down and stroked my cheek, then let her hand continue down my neck, over my chest, and across my shoulder and arm.

"You really are cute." Her voice was even lower than usual, sultry and smooth in a way that sent my heart fluttering.

Hands trembling, I gripped the hem of her turtleneck and started to lift it up. Anna smiled wickedly and reached down, pulling it off over her head, revealing her magnificently sculpted torso and arms, only her breasts covered by a tan bra. With her toned arms stretched over her head, I could see the outlines of six-pack abs. She was undeniably muscular, but her waist was appreciably narrower than her shoulders or hips, forming an hourglass figure. I admired her body breathlessly for a moment before speaking.

"Damn. That's... impressive."

"Like what you see?"

"I've never seen a body like yours before. So muscular without seeming masculine." I slid my hands up her hips to her sides, feeling the contours of her obliques and then running my fingers over her abs. Anna's face became a self-satisfied smirk, obviously enjoying my admiration.

"Well, if muscles were masculine, that would make me more of a man than you, wouldn't it?"

My cheeks burned hot with the playful dig, but it would be impossible to argue without seeming insecure. Doubly impossible since she'd easily overpowered me and pinned me.

"As much as I like it... down here, maybe the bedroom would be more comfortable."

"Oh?" She arched an eyebrow. "Are you offering to make me girl number fifty?"

"Forty one." I corrected her, trying to match her playfulness.

"Oh, well in that case, how could I refuse?" Anna squeezed her thighs together and ground on me one last time before climbing off me. I almost regretted not being pinned down with her thighs around me anymore. Standing up, she reached down to help me off the floor. I took her hand and, even though I could see how muscular she was, was still surprised by her strength as she pulled me up.

"Let's get moving," Anna said. I felt a sharp smack on my ass and gave her a startled look, which only made her giggle. She started off toward the bedroom, her hips swaying and the outlines of her back muscles shifting invitingly, and I followed her, my heart racing. I loved it when a woman took the lead like this.

"Yes ma'am." I replied, trying to sound a little sarcastic but actually just sounding eager. Oh well, it was past time to drop the coy act anyway.

"I like the sound of that."

Anna opened the bedroom door and ushered me inside. I immediately took the invitation to enter. She had a full-size bed against one wall, and a full-length mirror on the wall perpendicular to it. There wasn't much time to look around before she followed me in, shutting the door behind us. Standing just behind me, I could feel her grabbing at the hem of my t-shirt.

"Glad I'm not the only eager one." I said, reaching down to pull it off over my head.

"I just want to see what the other forty girls got so excited about."

"Honestly, after seeing how toned you are, I feel kind of unimpressive by comparison." I stepped further into the room to look at myself in the full-length mirror. I wasn't fat, but I wasn't muscular either. My body was slender and smooth, with my blonde body hair barely visible. It was really my face, with symmetrical and delicate but only slightly masculine features, that got me success with girls.

"Nah, the twink look is in right now." Anna stepped up beside and behind me by a couple steps. The contrast between her muscular body and my thin one was obvious. She was shamelessly checking me out. "Don't forget the pants too." She added playfully.

Obliging, I unzipped my jeans and stepped out of them. Like my torso, my legs were thin, slender, and without much body hair. With my pants off, the erection in my briefs was now obvious.

"Ta-da" I said, watching for her reaction in the mirror. Anna giggled.

"You have a nice butt. Nice waist too." She giggled some more. "You know... you would actually look good in lingerie." I flushed bright red at the suggestion.

"W-what?" She'd been taking little digs at my masculinity, but this was far even for her.

I jumped a little as she stepped up behind me and ran her hands down my sides, emphasizing the slight inward curve of my waist and then pinching my ass.

"I'm serious. You have the right shape for it. Here, I think I have a set that suits you."

Anna stepped away from me and rifled through her dresser on the wall behind us. My heart rate picked up as I realized she wasn't just teasing me. I turned to watch her, and within seconds she turned back around, extending a hand to me with a lacy purple bundle in it.

"You... want me to put on lingerie?"

"Yes." She was looking directly into my eyes, a serious expression on her face. I let out a nervous chuckle, but she stayed stone-faced, eyeing me intently.

"That's..." What would I even say to a request like that? "That's a little... unusual."

"You did say I was different from the other girls." She pressed the bundle into my hand, maintaining eye contact.

"I..." I couldn't handle her hazel-eyed stare and looked down, taking in the sight of her muscled body. There really was something hot about how strong she was, how able to overpower me she had been, and now I was realizing she had the personality to match. "With you watching?"

Anna's smile returned, noticing my objection had changed from wearing it at all to putting it on while being watched. Taking her victory, she simply turned around and faced the other way. Realizing it was too late to object now that I'd suggested I'd put it on if she looked away, I hesitantly unrolled the bundle. It was a pair of lacy purple panties and a sheer purple negligee, transparent except for the bra portion.

With trembling fingers and a pounding heart, I stepped out of my briefs and into the panties. I was still erect, the taboo of what I was now doing somehow making me even harder, and there was a visible tent in the panties. Staring at Anna's muscular back, I slipped the negligee on over my head. The bottom of it stopped just short of the panties, and the transparent fabric left my whole midriff visible. The fabric was smooth and soft on my skin, and actually quite comfortable.

"So, uh... what do you think?"

Anna turned around and looked me up and down, a grin spreading on her face and a wicked gleam in her eyes. After a moment, she bit her lip and nodded.

"From ladies' man to ladyboy. It's a good look for you."

My cheeks were hot and my ears were burning. I was humiliated, but it did nothing to dampen my arousal. Gently, Anna put her hand on my hip and turned me around so I could see myself in the mirror. The contrast between us had been sharp when I was in my underwear, and it was even sharper now that I was in her underwear. She was sleek, strong, and toned, even if she was a few inches shorter than me. I was delicate, dainty, and fragile. My pretty, pale face flushed bright red.

"Um, thanks. I'm... glad you like it." I kept my eyes on Anna in the mirror, her hand still on my hip, fingers pressed against my skin. "So... what now?"

"Be honest with me, Connor. You came here to hook up with me, right?"

"I..." In the lingerie, I felt vulnerable, exposed, unable to hide. "Yes."

"Well, then. Let's hook up."

Anna spun me toward her, got up on her tiptoes, and kissed me on the lips. Taken aback at first, I quickly recovered, closing my eyes and kissing her back passionately. We wrapped our arms around each other, and I felt myself soft skin and hard muscle pressed against me through the transparent fabric of the negligee. I ran my hands down her back, enjoying the sensation of her skin, and let them come to a rest on her round, voluptuous ass. With my eyes closed and my hands on her, I forgot for a moment that she had made me wear lingerie.

Reaching around in front of her and opening my eyes, I started to unbutton her jeans. She disengaged from the kiss and looked up at me, studying my face, but didn't stop me. I unzipped her jeans and grabbed the waistline, pulling them down, letting me finally see the massive, impressively muscled thighs that had been wrapped around my waist just a few minutes ago.

Anna stepped out of the jeans and looked up at me, biting her lip invitingly the way I'd seen so many other girls do. Grabbing her ass, I pulled her up against me, my erection pressing against her abdomen through the lace negligee, and kissed her again. She kissed back for a moment, then disengaged again, looking up at me again with wicked hazel eyes.