A Night Out

I looked myself over in my bathroom mirror, heart racing with anticipation. My dirty blonde hair framed my face, held in place by a hairband. A tight white button-down blouse hugged my thin torso, and with the bottom part tied in a knot, showed off my flat midriff and thin waist. Down below, a short red and black plaid skirt stopped at my mid thigh, leaving a few inches of soft pale flesh visible before the black thigh-highs covered me from just above the knee all the way down to my feet. I was positively girly.

It had been boredom that started me down this path. I had been accepted into my state's biggest university after I graduated high school, but as the start of the school year approached and the emails from the school came in, I saw how restrictive the pandemic safety rules were going to be. No leaving your dorm except for class, no guests, no gatherings of more than 3 people, and so on. It was going to be more of a prison experience than a college experience.

I had decided it wasn't worth it, and that I'd be better off just taking online classes. And so here I was, nineteen years old and still living in the house I where I had spent my whole life. It was a monotonous life: wake up, go to class on Zoom, then sit around and browse the internet or play video games until it was time to go to bed and do it again tomorrow.

And so you can understand why one night, on a whim and excited by the idea of tasting the forbidden fruit, I snuck into my older sister's room to try on her clothes. Unlike me, Beth was actually off at college; she lived in an off-campus apartment and didn't have to live under draconian campus rules. I still remember my heart racing as I put on a skirt for the first time, reveling in how comfortable it was, the danger of getting caught by my parents, and, best of all, how I actually looked kind of good in it.

From that day on, I was hooked. I found myself sneaking over to Beth's room more and more, trying on skirts and booty shorts and sundresses, learning what went well together. I started to grow out my hair, and couldn't help loving how I looked in my sister's clothes. As the novelty started to wear off, I decided to take things to the next level. I thought I looked good; did other people?

I started posting pictures of myself in Beth's clothes online. They never went super viral, but I exulted in the compliments I was getting. I have always by a shy, thin, scrawny boy. I never had luck with girls. But here I was now with strangers on the internet calling me hot, encouraging me, asking for more. There were men sending me lustful messages, telling me what they wanted to do with me. The attention was thrilling beyond belief, and I found myself fantasizing about how hot it would be to actually meet up with someone, to be the object of their desire.

And so I made the Tinder account. A few pictures of myself striking sexy poses in miniskirts, booty shorts, tight dresses, with my face cropped or blurred out of all the shots. A little bio explaining that I was a crossdresser so that there wouldn't be any confusion or misunderstandings.

The thrill was even more intense than it was when I had just been posting pictures. Now it wasn't just random strangers hiding behind usernames giving me compliments or posting thirsty replies about wanting me. The thought of taking my secret hobby off the internet and into real life was quickly becoming irresistible. I was matching with actual men near me, men who might actually have sex with me in real life. And not just fat losers behind a computer screen; some of them were actually hot.

Like Chris. I had matched with him two days ago and been chatting with him since. He was 23 years old, built like a Greek statue, rock hard abs and a jawline chiseled from stone. Pictures at social events with friends and pretty girls. He was the kind of guy I was jealous of in high school, but now, instead of me wanting to be like him, he wanted me.

And in a few hours, he was going to take my virginity. I trembled with excitement as I thought about the night I was about to have, fantasizing about pressing up against his hard body, his lips on mine, and of course, what it would be like to let him penetrate me. I stepped out of my bathroom and exhaled sharply, menatlly preparing myself for what I'd have to do.

Of course, my parents still had no idea that I was dressing up in Beth's clothes, let alone that I was about to go out to hook up with a strange man from a dating app. So I was going to sneak out. It was 9:30 PM, which was right after my parents usually went to bed. I crossed my bedroom, unlocked the window, slid it open, and carefully slipped my foot out. Our house had wood siding, and it wasn't too hard to find a foothold. I managed to climb down from my second story window and into the backyard with surprisingly little difficulty.

So far, so good. It was on to the next step. I knew in advance that opening the garage door would alert my parents. I also didn't want to stand around in front of my house where my neighbors could see me dressed like this, so I had arranged with Chris to pick me up a couple streets over.

I quietly made my way over to the fence that separated our backyard from Mrs. Johnson's. I'd have to cut across her yard and sneak past her house to get to the street where I would meet Chris. I found a handhold and a foothold in the wooden fence and quickly climbed over it, not even getting my skirt caught or any holes in the thigh highs. I was proud of that.

I started slowly tiptoeing my way across Mrs. Johnson's backyard. The light in her kitchen was on, but the blinds were closed, so her backyard was still dark. I was glad for that, but it did mean I had to be careful and watch my step.

Suddenly, the backyard became dimly illuminated. I snapped my head to the left and saw that the light in Mrs. Johnson's family room was now on, and I heard the glass back door slide open. Mrs. Johnson was standing in the doorway, a tablecloth in her hand. I was out in the open, nothing between me and her. I could hear my heart pounding in my ears as I realized the danger. Panicking, I dove behind a bush.

"Who's there?" I heard her shout. Oh shit, oh shit, oh shit. She had definitely seen me, and there's no way she hadn't heard the rustling of the bush. What was I going to do? I definitely didn't want to explain myself to her. No way I could let my secret get out, no way I could let my parents find out. That left me with one option: run.

I scrambled to my feet and made a break for the fence at the far end of her backyard. If I could make it over fast enough, hopefully she wouldn't keep chasing me.

Suddenly, I felt an impact from behind and found myself falling face first toward the ground. I was able to break my fall with my forearms before my face hit the ground. "Ah!" I exclaimed. There was someone on top of me, and I felt hands grabbing my upper arms. I hadn't been fast enough.

"Who are you, and what are you doing in my backyard?" Mrs. Johnson demanded, her voice not far from my ear. She was heavy, but not so heavy I couldn't breathe. Her grip was strong, and I was pinned between her body and the grass, her legs straddling my lower back and keeping me from getting up.

"Wait, I can explain!" I said, then realized there was nothing I wanted to do less than explain to my neighbor why I was dressed like a schoolgirl and sneaking around in her backyard.

"Cameron?" she asked, clearly recognizing my voice. Fuck. It was over. I was caught. My secret was going to get out. I gulped, and looked over my shoulder at her in the dim light.

"You had me scared for a bit there," she said, getting off me and standing up. She reached a hand down to help me up. I continued to lay there, still processing what was happening. "What are you doing in my backyard?"

I lay there for a moment, still scrambling to think of how I would explain it to her. I realized that it actually hurt to be tackled, and that I shouldn't still be on the ground. Rolling over, I reached out and took her hand. She pulled me to my feet with a surprising strength. In the dim light, I could see her eyes travel down my face and onto my outfit. My cheeks heated up; I was probably blushing so hard that I was sure she could see it even though only the outlines of our faces were visible.

"I-I" I stammered, panicking and totally unsure of what to say. How the hell was I supposed to tell her that I had taken up crossdressing and was trying to sneak out to meet up with a stranger?

"Let's go inside and get you cleaned up." She was still holding my hand, and she started leading me back toward the open sliding glass door. Defeated, I followed her without resisting. We walked into her family room, which had beige carpets, a brown microfiber couch along one wall, and an armchair across the coffee table from it. There was a TV hanging from the wall perpendicular to the side of the room with the door, but it was off.

"Have a seat." She led me to the couch, and I sat down. The room was well lit, and there was no way she couldn't see my whole outfit now. I was blushing bright red and staring at my feet, unable to meet her gaze. I could hear her sit down on the leather armchair across the coffee table from me. Steeling myself, slowly raised my eyes to look at her.

Mrs. Johnson was looking at me curiously. She was in her late thirties, but she had aged well, probably because she was in fantastic shape. Her clothes were very casual: a pair of baggy sweatpants and a loose top that had been a t-shirt but had had the sides cut out and the sleeves cut off. It left her toned, muscular arms completely exposed, and it also showed off a hint of her strong lats and the band of the sports bra she had on under the shirt. Her dark brown hair was tied in a very loose bun.

I took a deep breath, unsure of where to even begin. My heart wasn't racing quite as fast now; I was still terrified, but a sense of resignation had begun to set in. I decided that an apology was probably my best option.

"I'm really sorry, Mrs. Johnson. I shouldn't have been sneaking around in your yard. I didn't wake your kids up, did I?"

"Relax, it's okay." She said, her voice calm. She didn't look mad at me. "It's a weekend, my kids are with my ex. I'm just surprised is all."

Surprised at what? That I was sneaking through her yard at night? Or because I was dressed like a girl?

"It's not what it looks like." I replied, staring down at my lap. I realized my legs were open and my lace panties must be showing, so I hurriedly closed my knees together.

"What it looks like?" she asked, repeating my words back as a question.

"I was just..." I had no idea how to finish that sentence. How the hell was I supposed to explain this? "I was..." This was bad. I had been so caught up in my excitement for tonight that I hadn't though about the things that could go wrong. And now it was all coming down around me.

"Hey, hey, it's okay. There's nothing to be afraid of. I'm not going to tell anyone." I looked up cautiously.

"Not even my parents?"

"Not even your parents. Look, I was your age once. I used to sneak out on my parents too."

I was still in disbelief, but not a feeling of relief was starting to creep in. Maybe this wasn't going to turn my life upside down after all. Maybe this was going to be an incident I would be embarrassed to remember, but nothing worse than that. Maybe I was just going to have to talk a bit to Mrs. Johnson and go back home, my parents none the wiser.

"Let me get you a glass of water." She said, standing up and walking over to the kitchen. I could see the back of her toned shoulder strain a little as she reached up into a cabinet to grab a glass, then fill it with water at the sink. She walked back over and sat down on the couch a couple feet from me, setting the glass on the coffee table. I suddenly realized I was very thirsty and picked up the glass. I chugged the cool water quickly and set the half-empty glass back down, my fear and anxiety calming down.

"So, if you don't mind my asking, why were you sneaking around in my backyard?" asked Mrs. Johnson. I blushed again, but at least now that she was sitting next to me and not across from me, it was much easier not to look at her.

"I was..." I hesitated for a moment. But I could tell I wasn't going to get out of this without an explanation. "Do you promise not to tell anyone? Not even my parents." I looked over at Mrs. Johnson.

"I promise. Your secret is safe with me." she said, her green eyes staring back directly into mine. I took a deep breath and looked straight ahead at the sliding glass door we had walked in through. It was easier to continue if I didn't have to match her gaze.

"I was going out to meet someone." I finally said. My thoughts went back to Chris. A lot of the excitement had been the risk of getting caught, but now that I actually was caught, I was finding that it wasn't fun at all. Maybe this hadn't been such a good idea. Maybe Mrs. Johnson wasn't going to tell my parents, but I couldn't stop thinking about their disappointment and disgust if they did find out.

"What kind of someone?"

"A..." I stopped again, completely unsure what to say because I really didn't want to tell the truth. "A friend."

Mrs. Johnson giggled. I indignantly turned to look at her, and found her smiling an annoyingly knowing smirk at me, her eyes twinkling.

"What?" I asked, a hint of stress in my voice.

"A friend you couldn't tell your parents about?" She asked. Her smirk became even wider, and a hint of mischief entered her eyes. "A friend you dressed up in a sexy schoolgirl costume for?"

The self-consciousness that had begun to recede came back even stronger and hit me like a truck. My cheeks were burning hot, and I knew I was bright red. I couldn't even think of a reply to that. Mrs. Johnson giggled again.

"Hey, I wasn't an innocent little angel at your age either." She paused. "So, what kind of friend?"

"A guy." I practically whispered, unable to bring myself to look at Mrs. Johnson.

"What's his name?"

"Chris."

"Where did you meet Chris?"

"On an app." I said. I looked over and saw her smirk dampen.

"Do you meet guys from apps often? This is the first time I've caught you in my yard."

"No," I said, feeling a little defensive. "This is the first time."

Now she wasn't smirking; she had a look of concern on her face. For some reason, it worried me.

"How do you know he's who he claims he is?"

"I've been talking to him for days now."

"Oh, that settles it. How do you know he's not going to hurt you? How do you know he doesn't have any diseases?"

"Look, I'm nineteen years old. I'm supposed to be off at college right now. I'm supposed to be living my life, and I'm trapped at home like a kid. I don't need a lecture! I can make my own decisions!" My own outburst shocked me. I couldn't believe I'd gone from being unable to even look at Mrs. Johnson to practically yelling at her in the space of a few minutes. I nervously looked away, realizing she could still tell my parents about this whole thing.

"Hey, hey, hey" she said in a soothing voice, scooting a little closer to me. "I'm not trying to stifle you or make your decisions for you. I was doing things like this at your age too. I just want you to be safe"

I looked at her a little suspiciously. She continued.

"You're still a virgin, aren't you?"

"Yes." I admitted, blushing.

"Listen: your first time shouldn't be with some random guy off the internet that you've never even met and might not even be who he says he is. It should be special, with someone you can trust, someone who won't hurt you." She looked deeply into my eyes. "Like me."

My breath caught in my throat, and my heart started to race. Mrs. Johnson took my hand and leaned in, pressing her lips softly against mine. I panicked; I had never kissed anyone before, and didn't know what to do. She held her lips there for a moment as I sat petrified, then pulled back and smiled at me.

"How about you come upstairs with me?" she asked, standing up and reaching a hand down to help me up. I paused a moment and looked up at her, admiring her toned arms and her sharp jawline. I grabbed her hand and let her pull me to my feet once again. My heart was pounding so loud I could hear it as she led me to the stairs.

"Ladies first," she said playfully, placing her hand on the small of my back and nudging me toward the stairs. I started my way up the stairs and could hear her footsteps behind me. I got to the top of the stairs and turned around to look at her, not sure of where to go next. She stepped right up to me, placing her hands on the wall on either side of me, pressing her hard body up against me. She was a couple inches shorter than me, but the confident way she carried herself and my own nervousness certainly didn't make me feel taller than her.

"Your ass looks great in that skirt," said Mrs. Johnson, leaning in and kissing me on the neck. I shuddered and exhaled sharply, shocked at her advance. I could feel the panties tightening as I grew rock hard, and the way she was pressed up against me, she knew it too. She pulled back from my neck and smiled up at me wickedly. Grabbing my hand once again, she led me down the hall and opened the door to the master bedroom.

Mrs. Johnson pulled me into the bedroom and closed the door behind us. She was grinning broadly as she reached down to the hem of her shirt and pulled it off over her head. Her body was absolutely stunning; six pack abs and defined obliques, muscular shoulders, tight and toned arms, and yet with her breasts in the sports bra and her relatively thin waist, she still looked feminine.

She saw me staring at her and smiled. I looked away, still shy even though I was now extremely aroused. She giggled.

"You don't have to look away."

I turned back toward her, looking at her tanned, towned, incredibly fit body. She must have seen the look on my face, and her smirk reappeared. Slowly, hesitatingly, I reached out toward her and ran my hand down the front of her muscular shoulder. She didn't draw back from my touch at all, and I put my left hand on her too, feeling up her muscular shoulders and upper back. I could feel the hard, powerful muscle under a layer of soft skin. I continued to run my hands down her sides.

Trembling, I knelt at her feet. I was awestruck at the strength and beauty of her body, and kneeling just felt right. Leaning in, I planted a few kisses on her abs and rested my cheek against the hard muscle. My chest was up against her legs, and even through my own blouse and her sweatpants, I could feel how thick her thighs were.

I looked up at Mrs. Johnson, who was smiling down at me. Slowly, I began fumbling with the drawstrings of her sweatpants, then pulled them down. I wasn't disappointed. Her thighs were strong and bulging with muscle, and I leaned down to kiss them. She giggled as I planted kisses on her thighs over and over, my arms wrapped around her waist.

She stepped out of the sweatpants, which made me pull back from her legs. Grabbing my upper arm, she gently pulled me to my feet.

"You seem excited." she said, staring up into my eyes.

"Yes" was all I could manage. She smiled and gave me a gentle push toward her queen-size bed. Obediently, I walked over to the bed and lay down on it. She looked down at me a for moment.

"I love your outfit," said Mrs. Johnson, climbing on top of me and straddling my waist with her thick, powerful thighs. She leaned down and hungrily kissed my neck. I threw my head back in pleasure, feeling her lips on my neck and her hands running down my sides. Her full weight on top of me was comforting but not crushing, and she leaned up, pressing her lips to mine once again. I jumped a bit in shock as I felt her tongue enter my mouth. She rocked her hips and forth, teasing my erection through the skirt and the panties.