Tales of Transwomen Tops Ch. 02

A/N - Most of my other stories I've written within this category have never had the man being 'surprised' by a cock being present on a woman. Don't think that's particularly realistic, but as these stories will all be nothing but fantasy, I thought I'd do something different with this story.

Thanks for the comments and feedback regarding the first chapter.

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They often talk about 'short man syndrome'. You know the joke, sometimes stated humorously, other times stated with an edge, that some men who were not blessed with height feel rather inadequate, particularly in comparison to their taller brothers, and even against taller women, so take out their feelings of inadequacy by being aggressive pricks, usually having a chip on their shoulder against the whole world.

I wasn't one of those men. I was now twenty years old and had never enjoyed what one would call a 'growth spurt'. At only five-five, I was barely an inch taller than the average female. Add to that I didn't have to shave as body hair was something I'd never had to worry about. I was incredibly pale, barely had any muscle mass, and I'd never been called handsome. I'd been called 'cute' and 'adorable' my entire life by anyone not in my family.

And I can't not talk about my cock. I'd never measured it, but it wasn't what I'd call thick or long. I didn't think it was five inches long. Had I been with a woman? Don't make me laugh. I had plenty of girls as friends. I was considered harmless. Not boyfriend material. I'm fairly sure most at high school had considered me gay. Thankfully, I wasn't bullied too much. I think all the girls looked after me in that regard.

I was now at university, and nothing had really changed. Most girls were happy to be my friend, but the chances of landing a date were minimal. Men pretty much just ignored my presence entirely or would be friendly if they wanted something from me, as I was studying a dual major. I guess lacking confidence didn't help when it came to women, but I'd spent my entire life being looked over in more ways than one.

Living at home with my mother and three sisters probably didn't help in many ways. My father had walked out on us when I was still a kid and I'd barely seen him since. Mum had dated occasionally but most men were not interested in a single mother with four children to support. Mum eventually gave up and focused on us. As for my sisters, they were all beautiful women and loved their brother, but despite all their 'advice', I was still single and rather lonely when it came to love.

When I'd hit eighteen, I'd started heading out with some friends for a night out, enjoying a drink or two and maybe a dance. I found regular pubs rather intimidating as there were plenty of men out there who had too much to drink and would become overly aggressive. As I didn't have many male friends, I would be taken out by my other friends, and though most of them were straight, they sometimes preferred to go to gay bars so they could enjoy a night of peace, enjoying a drink and a dance without being hit on and groped all night.

"Heading out tonight?" my sister asked as I put on a shirt. Glancing at her in the doorway, she smiled at me. She was my older sister, the two others being younger. She still lived at home as Mum wasn't in any rush to kick us out of home.

"Going out with the girls as usual."

She walked in and took over buttoning up my shirt. She was a couple of inches taller, meeting her brown eyes and she smiled at me. "You'll find someone, Stevie. I promise there's a girl out there who is going to love you for you." I scoffed but otherwise remained silent as she finished buttoning up my shirt before hugging me tightly. "Mum would say the same thing," she added.

"You realise I'm twenty and still not even been kissed?"

"I can kiss you if you want."

"I'm not having my first kiss being my sister, no matter how much I love her."

She hugged me tighter. "I love you too, Stevie," she whispered, "We all love you. I hope you know that."

"I know, Amy. And thanks. I know you're trying to help me."

Grabbing what I needed for the night, I walked out into the living room where my younger sisters were getting ready to go out as well. Eighteen-year-old twins, and while I might be their brother, I knew both of them were drop dead gorgeous brunette bombshells. Both were wearing little black dresses, stockings and heels that meant they were easily towering over me.

That didn't stop them both hugging me tightly, kissing my cheek. "Very handsome, big brother," Jane stated.

"Going to break hearts tonight, big brother?" Jessica wondered. I scoffed again, both of them tightening the hug.

"Want to feel up our butts before we go?" Jane asked.

"Imagine having two girls at once as a first time, Stevie," Jessica added.

"Okay, that's all three of you now offering something rather rude."

"You don't want to hear what Mum was saying earlier," Amy joked, "Figuring she might as well just throw you on the bed and ravish you. It might make you feel better."

"Not sure she'd enjoy what I have to offer."

Jane and Jessica both leaned back, looking serious. "It's not how big it is, Stevie. It's how you use it," Jane said, "Find the right position and you'll make her cum."

"And if that doesn't work, make sure your oral game is on point. Make a woman cum when eating her pussy? She'll love you forever."

"Cock size isn't everything, sweetie," Amy added, cuddling me from behind, her head resting on my shoulder, "We haven't seen you nude in a long time, but the most important thing is that you're a very sweet young man."

"We're ready if you are," Jane said, nodding that I was okay too. Amy dropped the girls off at a friend's place first, as they'd get a taxi into the city. No idea where they were going. As for me, Amy drove me to one of my friend's places, pulling up outside by the kerb.

"Have a nice night, sweetie."

"What are you doing tonight?"

Leaning over to kiss my cheek, she whispered, "I'm going to spend the night in bed being very naughty with myself."

"How are you single, Amy?" I wondered.

"I thought I had the right man. Remember Nick?" Nodding, she sighed. "We only broke up a couple of months ago. I'm not ready to start dating again. He broke my heart, Stevie." Taking my hand, she squeezed it. "If any of our teasing gets to be too much..."

I managed a smile, which made her smile in return. "I don't mind. It's a little weird, but I don't mind."

"We just want our brother to be happy and smiling too." Leaning over to hug me, she kissed my cheek again. "There's a girl or woman out there for you, Stevie. I promise. But whatever happens, I love you so much too."

"I love you, Amy."

"And you should. All little brothers should love their older sisters."

"Thanks for making me feel better."

"Have fun tonight, sweetie."

Amy waited until I was inside before she took off. I was greeted with a hug from all my friends, amused that I was the only male present. They all knew that I actually wasn't gay though I was considered harmless and not a prospective romantic partner. I guess what my sister mentioned about me just being nice helped.

We enjoyed a few drinks at the house first before we agreed to head into the city. There were enough of us that we needed two taxis to take us, sitting in the middle of one with a friend to either side. All of them were dolled up and beautiful. I didn't allow myself to feel any romantic feelings for any of them, mostly because they were good friends, and I didn't want to ruin any of the friendships I'd formed.

Stopping at a friendly pub first, the sort that had a rainbow flag outside that kept certain clientele away, the girls were all having a great time. The drinks flowed, selfies and photos were taken, and I found myself drawn into half a dozen conversations at the same time. It was times like that where I forgot about my own problems as I would find myself laughing and smiling, and all the girls were affectionate with me. I know they saw me as a brother more than anything, part of me long accepting the reality and just enjoying the attention when I had it.

Heading towards the club a couple of hours later, it was one we were regular visitors. The men on the door were large and intimidating, but they were friendly towards me considering I was surrounded by women. Gathering together once we were all inside, the first stop was the bathroom for all the girls, no doubt wanting to pee, and I knew more than one would remove their panties.

I'd seen them enjoy each other on the dance floor more than once. None of them called themselves bisexual, but on a night out, I'd seen them finger each other to orgasm on the dance floor more than once, and I knew that they would happily head home together and spend the night licking and fucking each other. Girls could do that and not be judged. Imagine a pair of guys going home to suck and fuck each other? There's definitely a double standard somewhere.

Most of the girls hit the dancefloor. Sometimes they'd drag me up, but they knew I preferred to sit by the bar, perhaps talk to other people. Some gay men would hit on me as I knew they viewed me as a 'twink', having learned some of the lingo over the years. Most were polite enough to take 'no' as an answer, but one or two would claim they could 'turn me', whatever that meant. I never mentioned I was a virgin as I figured that would just make it worse.

Sipping at my rather fruity cocktail, ensuring I didn't drink it too fast as I didn't want to get drunk, I glanced around to see plenty of people chatting, some hooking up, but everyone was there to have a good time.

"Is this seat taken?" The question took me by surprise, swinging around to see a gorgeous woman standing next to the stool to my right. Before I could open my mouth, she smiled down at me. "My feet are killing me."

Clearing my throat, I gestured to the empty stool. "It's free," I managed to reply.

Earning another warm smile, she slid onto the stool as I turned away though glanced at her to get a quick understanding. She was definitely tall. Had a large chest. Very long legs that were bare and looked very smooth, the hem of her skirt barely covering even a quarter of her thigh. The top she wore clung to her curves. Her arms were bare of clothing, one arm covered in what looked like a tattoo sleeve down to her elbow. She had another small tattoo on her right wrist that I couldn't quite make out.

She was an absolute goddess. And if I judged correctly, she was definitely older than I was. Her brunette hair hung down to her shoulders. When she glanced my way, her blue eyes sparkled, her lips bright red with lipstick, her cheeks coloured slightly from either dancing or a little foundation.

Glancing me up and down, the smile broadened. "Well, aren't you a real cutie. What's your name?"

I would have normally groaned at being called cutie, but I managed to hold it back. "I'm Steven. Or Steve. Or Stevie."

She chuckled as I stumbled over a few short words, offering her hand. "Pleasure to meet you, Stevie," she stated as she took my hand, amused hers was larger than mine, and her grip was quite firm, "I'm Chanelle."

"Nice to meet you."

"Are you here alone?"

"No, I'm here with a bunch of friends. They're all out on the dancefloor right now."

"You don't want to dance with them?"

"I'm not much of a dancer, and they're all just friends. I don't mind sitting here as people are sometimes friendly enough to join me. Just like you."

"I'm here with a couple of girlfriends but I saw this cute young man at the bar all alone and just had to come over and say hello. So you're here with some girlfriends. Are you single?" Shrugging but also nodding, she rested a hand on my thigh, which near enough made me jump off the stool. "None of your girlfriends are interested?"

"They prefer tall, dark, handsome with a big cock. You know the sort of thing you usually see on online dating sites nowadays." Shrugging again, I added, "It's okay as, despite looking at me more as a brother than anything, I've had some genuine friends since primary school. What about you?"

"Free and single, which is why I'm out with my girlfriends tonight. Spend a night drinking, dancing and, if we're all lucky, end the night fucking." I almost spat my drink out, managing to swallow it though I started to cough. Chanelle giggled as she moved her hand to my back, rubbing it gently. "Sorry, sweetie. I was just being honest."

"No, it's okay. Trust me, I hear a lot of sex talk around all my friends. Heard enough stories of girls being fucked by big cocks. Threesomes. Orgies. Gangbangs. Girls happy to swallow and take facials. Girls who love anal."

"And they forget you're also a man?"

Shrugging, I sipped at my glass again. "I'm used to it. They don't mean it maliciously. Hell, I probably learn things from hearing all their stories."

Turning slightly towards her, she did the same and I offered to buy her a drink. "How old are you, sweetie?"

"Twenty."

"Oh dear! You're so young. And are you working or a student?"

"I'm doing a dual major at university."

She gently squeezed my thigh. "Then let me buy you a drink, sweetie. It's the modern age and women can buy men a drink if they want." She glanced at my glass and smiled. "And I like what you're drinking."

"It's sweet and tasty. I don't care what people think."

She stood up to get the attention, leaning forward slightly so I got a good look at her firm arse and those incredibly long legs. She must have been six foot, and with her heels, she must have been taller than most men. Even her arms looked rather strong, and her shoulders were broader than I'd seen on most women.

Sitting back down, she could see I'd been checking her out as she shuffled her stool a little closer, her hand back on my thigh, now caressing it. "So you're twenty, a student... Still live at home?"

"Yeah," I replied, a little embarrassed, "Three sisters and my mother."

"Nothing wrong with that. Are you interested in how old I am, cutie?"

"I've been told to never ask a woman her age."

"I'm thirty-six." I met her eyes as she smiled at me. "Would that be a problem for you?"

"We're just talking, Chanelle. I can talk to anyone."

Her fingers caressed my thigh as she moved her stool closer, feeling my eyes widen when I felt one of her feet start to move up and down my right leg. "Well, we're just talking for the moment, Stevie. Maybe you'd like to dance with me later?"

"Um, sure."

Sipping at our drinks, we continued to make small talk, most people ignoring us though who I assumed were her friends met my eyes occasionally, smiling back at me. There were three of them and they were all tall, gorgeous women as well. Chanelle noticed where I was looking and leaned closer to me. "I won't let them get your claws into you, cutie," she whispered, "They'd chew you up and spit you out."

"And you?"

Her fingers continued to caress my thigh as her eyes met mine. "I'm just wondering where the night will take us, Stevie."

Realising I was hesitating, she gently took my wrist and placed my hand on her thigh. Noticing as I was shaking with nerves, her other hand caressed my cheek before she leaned down and left a very soft kiss on my lips. "Nervous?" Managing to nod, she then asked softly, "Virgin?"

"Yeah," I whispered.

"Like how smooth my skin is, cutie?" Smiling and nodding, I ran my fingers down to her knee then back up to her skirt. "My legs are always nice and smooth. Got to look after your skin. Your hands are incredibly soft. Look after yourself?"

"I'm not exactly equipped for manual labour."

Finishing her drink, she dropped her feet to the ground and stood up, offering her hand. Without a word, she gently pulled me towards the dancefloor. I noticed a few of my friends paired up, grinding against each other. I knew where the night was going to end for most of them. I heard the stories during the week. But I noticed a few eyes glance my way as I stepped into the crowd with Chanelle, who turned towards me, and I finally realised how much taller than me she was.

To her credit, she kicked off her heels, so she wasn't so much taller than I was. Hooking her arms around the back of my neck, she pulled me tight to her body, my head resting in the valley between her big breasts. "That's it, cutie. Just sway to the music," she said, one of her hands stroking my back, and it didn't take long until one of her hands reached my arse, giving it a gentle squeeze.

Pulling me tighter to her body, I inhaled her fragrance and smiled. She was beautiful and she smelled delightful. Then I felt my cock start to get hard and I tried to pull back. "Don't worry, cutie. If you get hard, I'll take it as a compliment..."

"I'm not that big," I muttered.

Lifting my chin with a finger, she smiled before leaving another soft kiss on my lips. "I don't care, cutie. All I know is that I want to share this dance with you right now. So you're cute little butt is staying here with me. Got it?"

"Okay."

"Good boy. Now put your head back between my tits and just enjoy the moment."

I did just that, closing my eyes and enjoying how her hands moved over my body. I had my hands on her back, eventually finding the courage to move one down to her arse. It was firm but more than enough to give a good squeeze. It made her chuckle, feeling a hand move to the back of my head to stroke my hair. We actually danced through a couple of numbers before she spun me around so I was resting back against her. Feeling her hands move over my chest did make me feel a little awkward.

Eventually returning to our stools, I could see some of the girls looking at me. Though there was surprise, nearly all of them smiled when they met my eyes. Sitting down again, she ordered another drink for each of us, my hand ending up on her thigh again as she turned rubbed my lower leg and moved her hand up towards my groin. I could feel my cock was still rock hard.

Then she ran her fingers over the small tent in my trousers and I nearly climaxed. Noticing me shudder, she leaned down to kiss my cheek first. "Nearly cum?" Managing to nod, she kissed my cheek again. "Are you attracted to me, Stevie?"

"God yes."

"Want to come home with me?"

I didn't know how to answer that. I would have thought it was all some sort of joke, but when I met her eyes, I knew she was being completely serious with me. "You want me to go home with you?"

"Definitely, cutie. And I'd like to take you right now. Go say goodbye to your friends, I'll do the same with mine, and then I'll take you home to my place."

I could barely stand as I was so full of nerves, managing to find most of the girls, letting them know I was going home with Chanelle. To say they were excited for me wouldn't be an understatement. "She's gorgeous," one of them stated.

"And she looks mature. No-one better to learn from," another friend added.

"Just make sure you enjoy yourself but remember, make her cum!" another suggested.

I knew I was blushing as I returned to Chanelle, who was busy saying goodbye to her friends. She quickly introduced me, finding myself hugged by a trio of tall, buxom women, each getting a good grip of my arse at the same time, calling me cute and other pet names which didn't bother me at all. In fact, it made me feel rather good.

Taking my hand, Chanelle practically dragged me outside, flagging down a passing taxi. Getting in the back, she directed the driver to an address in the inner west. We behaved while we were driven to her place, slightly surprised that it turned out to be a little terraced place. After paying the driver, she led me towards the front door.

That's when she kissed me properly for the first time, finding my back pressed against the door as she slid her tongue into my mouth, whimpering as she was taller and stronger than me. I have no idea how long that first kiss lasted, but when she finally pulled back, there was a look in her eyes that made me gulp.