Tales of Transwomen Tops Ch. 03

"Sure. I can just go straight to your place as I have everything we'll need."

Shelby leaving school with me every afternoon had already set tongues wagging. I generally ignored gossip. However, any whispered comments I did hear were generally nice. There was a little jealousy from some girls, as Shelby was simply gorgeous, but I heard most people at least approved the fact Shelby and I were getting closer, even if it was happening rather quickly.

Arriving at my place, she made mention of the fact I kept the house nice and clean despite the lack of parental supervision. I retorted in a friendly manner that just because I was an eighteen-year-old male didn't immediately make me a slob. And I didn't want to live in a hovel.

"A cleaner does come once a week to do the dusting and stuff," I added, "But I clean the pool, mow the lawns and do general maintenance. Dad didn't teach me much, so I rely on online lessons."

Gathering at the table, Shelby surprised me with a tight hug. "Don't you get lonely?"

Meeting her eyes, I saw the concern, which simply made me smile for a few seconds. "I can't say I miss my parents as they've barely involved themselves in my life the past two years."

"Couldn't you have alerted the authorities?"

"Maybe, but they've always given me enough money to survive."

Studying was abandoned for a little while as she spent time cuddling me. She felt fantastic in my arms, inhaling the scent of her perfume and I guess the soap she used. Finally leaning back, both of us clearing our throats, we finally sat down next to each other at the table, opened our books, and focused on studying for a couple of hours until she had to go home.

Walking her home, I smiled at the fact she wanted to hold my hand the entire time. Stopping outside her front door, we turned to look at each other. There was no hesitation from either of us when we leaned in and kissed for the first time. Her lips were soft as her body pressed into mine. Being a couple of inches taller, it was unusual for me in that I had to move my head up to meet her lips.

Pulling back, her cheeks were slightly coloured. "Would you like to come around on the weekend? We can spend time by the pool..."

"You just want to see me as naked as possible," she retorted with humour, "But I'd love to come around. We can agree a time on Friday at the end of school."

Spending more time with Shelby, whether in class or during our breaks, my friends had certainly noticed that I was rather enamoured by her. There was some good-natured ribbing, and when I told them about her visit to my place over the weekend, there were a few comments about where they'd all meet up to have some fun.

Walking home with Shelby on Friday, I did ask her plans for that evening. "Probably enjoy a glass or two of wine, watch a movie... Keep it simple as I have no doubt that you'll keep me occupied."

Parting again, we shared another kiss, both of us smiling as she pressed her body into mine. When I rested a hand on her firm butt, she giggled, leaning back to look into my eyes. "I hope you like more than just my butt," she whispered.

"Shelby, I think my attraction is already rather obvious..."

"Thank you for making me feel so welcome, Scott. It meant the world."

"What time will you come around tomorrow?"

"How about noon?"

"Make sure you bring something to wear in the pool."

I found sleep hard to arrive that night as I thought about the possibilities of Shelby's visit the next day. She seemed as interested in me as I was in her. If I was honest, I hadn't felt such intense feelings for anyone, and I'd felt them very quickly. The last thought on my mind before I did finally drift off to sleep was if she would end up spending the night with me...

Shelby arrived a few minutes before midday the next day. Wearing a sleeveless vest and an incredibly short skirt, I glanced down her long legs to see her feet in open-toed sandals, her toenails painted quite a bright pink. Meeting her eyes, she giggled at the reaction on my face. Escorting her in, she'd brought a small bag with her, explaining she'd brought her own towel and other little things she might need for the day.

"Want to swim before we eat?" I asked her.

"I'd love to. Is there somewhere I can change?"

"You're not wearing something now?"

Grinning at me, she replied, "I'm not wearing a bra and I'm not sure you could handle seeing me in panties just yet."

"Oh really?"

Kissing my cheek, I led her towards the master bedroom. Giving me a look, I shrugged my shoulders. "Guess your parents aren't here..."

"Nope. And I don't think they'll be back for a few more weeks yet. I've been doing this long enough that I appreciate the freedom it gives me."

Giving me a smile before she closed the door, I returned to the living room and waited for her to return. Shelby returned a few minutes later, her large breasts almost completely exposed by the small bits of cloth that made up her bikini. What surprised me was the fact her breasts were incredibly perky and perhaps even a little fake.

Or she just had the best set of tits I'd ever seen on a young woman.

Gazing down her toned body, she'd covered her bottom with a towel, her legs and feet now bare. Raising my eyes back to hers, I offered my hand and led her outside towards the pool. Diving in first, I was still under the water when Shelby must have lowered herself down as she was already floating by the time I surfaced.

Swimming towards me, she was tall enough that her feet could touch the ground by halfway. Being of similar size, we could both stand comfortably with our heads and shoulders out of the water. She was incredibly distracting but also utterly beautiful.

"Scott, I have to tell you something... Or at least..."

Before I knew it, her arms were around the back of my neck and her lips were on mine, her tongue rather eagerly trying to slide into my mouth, which I accepted without hesitation. Feeling her breasts press into my chest, I wrapped my arms around her in return, keeping my hands on her lower back. But it took me a few seconds to realise that something else was poking me below, from her groin area.

Slowly pulling back, I met her eyes before I glanced down into the water, unable to clearly see but I knew what I was feeling. Raising my eyes back to meet Shelby's, I could see the curiosity in my reaction but also the fear. I figured humour would help alleviate the tension.

"Well, I'll admit that feeling that is at least slightly unexpected..."

Managing a crooked smile, she leaned down to kiss and hug me again. "It's why we had to leave," she whispered.

"What do you mean?"

Taking my hand, she led me out of the pool towards the gazebo, providing a little shelter from the sunlight. Sitting side by side on the comfortable cushions of the wicker couch, we were angled towards each other as she held both of my hands in hers. Taking a deep breath, I could feel her nerves, leaning into kiss her cheek. "I haven't run away, Shelby, so whatever you have to tell me won't scare me." Looking down, I saw the obvious tent in her bikini bottoms. The fact it looked long and thick had me suppressing a smile.

Immediately, I knew she was well endowed. Far larger than myself and all of my friends.

"I've always been a girl, Scott. It didn't start as playing with dolls or anything. I told my mother when I was little that I was a girl. Thankfully, I had understanding parents and I've pretty much always lived as a girl. Going through primary school wasn't a real problem. I went to school in either a dress or skirt and shirt, and no-one knew any better.

High school was fine, even when going through puberty. Do I look very... masculine, Scott?"

"Hardly. You're tall, but then again, there are plenty of tall women about nowadays. But apart from the obvious bulge in your panties... I guess I should ask about your breasts?"

"Obviously fake as hell!" she replied with a smile, "As soon as I hit eighteen, my parents knew I wanted a big pair of tits." Pausing, she actually started to blush for a moment. "Do you think they suit me?"

"Hell yes. I find myself rather distracted by your cleavage whenever it's on display."

"I got the tits after the event at my previous school... So no-one knew I was trans, at least among the student population. The school administration was informed. I had some girlfriends, meant platonically, and I've always been attracted to men because I'm a woman. But I'm a woman who has a cock and I've never hated it."

"I've heard the term dysphoria but I'm not completely up to date..."

"I love masturbating, Scott. I've got a big cock and I still cum hard. And in massive loads."

I looked at her in silence for a few seconds. "Okay, I don't care what anyone thinks, that's totally hot, Shelby."

"My only boyfriend I've had didn't think that," she whispered, squeezing my hands again, "I had to tell him before we got intimate, and... Well, as I said, I have a cock and I want to use it. Understand what I mean?"

"Sure, I've seen the occasional video."

"He obviously freaked out. I think a girl having a dick was bad enough in his eyes. The fact I wanted him to bottom pretty much short circuited his brain. By the time I returned to school on Monday, everyone knew the truth and life was intolerable. People who I thought were friends turned their backs on me, but more concerning was the prospect of violence. More than one guy threatened to beat the shit out of me. My mother pulled me out of school immediately."

"I'm guessing no-one at our school knows?"

"Only you, Scott. I just want to get through this final year. If I go to university, I'm hoping that'll be a more understanding place."

"They're generally more open-minded regarding sexuality and gender, from what I've read."

We sat in silence for a few seconds before she whispered, "Scott?"

"Yeah?"

"I really like you."

Smiling, I leaned forward and kissed her cheek. "Well, I really like you, Shelby. There's a reason you're here with me this weekend and not my other friends. And I don't mean I wanted to just get you into bed. I wanted to just spend time with you first..."

Standing up in front of me, I wasn't really all that surprised when she reached to the side of her bikini top, undid the string, and that that fall to the ground. They were not overly fake, but they were large in proportion to her frame. Women of her stature would usually have smaller breasts. Her nipples were hard and, from how she was breathing, it was obvious she was turned on.

Moving her hands down her toned body, she then undid the strings of her bikini bottoms, letting that fall to the ground too, finally freeing her cock. Seeing it for the first time, it was coloured slightly darker than her lightly tanned skin. It was thick, long, and looked... fantastic. Yet also somewhat feminine, like the rest of her body. Stepping closer, it swayed slightly, almost as if caught in a breeze.

"What do you think?" she breathed.

"I think you're fucking sexy, Shelby."

"Do you like the fact I have a cock?"

"I had no idea, but now that it's in front of me... Yes, I like the fact you have a cock, Shelby."

"You've played with them before. Would you like to play with mine?"

"Hell yes!"

"But have you bottomed?"

"No."

"Would you like to? With me?"

Standing up, I pulled her tight and kissed her, surprising her for a second before she immediately took control. I was used to it already, as it was obvious that she was a girl who liked to have control. Feeling her cock press into mine had us both smiling. My cock was also hard and tenting in my swimming shorts, feeling one of her hands gently caress me in return.

"Should we do some skinny dipping before we head inside?"

"Will it involve more kissing and groping?" I asked.

"I hope you touch me everywhere, Scott."

Dropping my shorts, she stepped back and looked me up and down. I wasn't as endowed as she was, but I was a fit young man, and the smile that formed suggested that she did appreciate what she saw. Turning, I watched her perfect little arse disappear into the water, wasting no time in jumping into the water to join her.

Without hesitation, we were all over each other immediately, our cocks pressing into each other, and I enjoyed the fact that Shelby was the aggressor. Her hands were all over my body, but when they moved their way down to my arse, feeling her fingers spread my arse and then some fingers grazing my arsehole, I knew what was on her mind. Our relationship was going to turn physical rather quickly.

Gently grasping her cock, she moaned into my mouth. Even in the cool water, I could feel how warm it was in my hand, feeling it throbbing from excitement. Moaning into my mouth again, I slowly stroked her cock and we both smiled. I had a feeling just doing that for her was a big thing. When she shuddered as her tongue slid into my mouth, we moaned together as I tightened my grip and stroked her a little faster.

Breaking the kiss, her eyes gazed into mine, her mouth opening as another moan escaped her. "Do you want to go inside?" I asked her.

"Scott... Do you want... I mean, could you handle..." She kissed me again as I continued to stroke her, needing time to gather her thoughts. "We should definitely go inside. Your bed will be much more comfortable than in this water or anywhere next to the pool."

We moved quickly, making me laugh as she practically dragged me out of the pool and inside, towards my bedroom. Throwing me on the bed, she was quickly up and crawling towards me, her big cock swinging as she leaned down to leave a soft kiss on my lips. Leaning back enough so our eyes met, she blushed slightly as I gazed down past her big tits to her fabulous cock.

"Shelby... Are you a virgin?" When she nodded, my heart melted as she bit her bottom lip, managing to look quite innocent despite the fact we were naked in bed together. "So you've never had that big cock of yours sucked?"

Scoffing, she replied, "I wish."

"Well, why don't you lie back, and I pleasure you first?"

"You'd do that for me?"

"Hell yes!"

Leaving one hell of a kiss on my lips, she quickly laid on her back and spread her long legs, her thick cock resting against her belly, meeting her eyes and she nervously chewed on her bottom lips. She seemed to almost shake with nerves as I crawled forward so our eyes were meeting again. Leaning down to kiss her, she started to giggle as our cocks rubbed against each other.

Kissing down her body, her neck was sensitive, making her moan as I didn't waste too much time heading south, her nipples already hard and begging for my attention. Locking my lips around one of her nipples, she almost whimpered as I used my tongue to flick the hard nub again and again, using my left hand to tweak the nipple of her other breast.

Feeling her cock actually throbbing underneath me as our bodies were closed together, I continued to kiss down her body until I could feel the heat and presence of her thick cock. She was already leaking plenty of pre-cum, moving so I could wrap my hand around the base and lift it up, not wasting time by running my tongue around the thick head.

"Oh fuck!" Shelby exclaimed softly.

Gripping the base of her cock, I made sure I was smiling as I met her eyes. "I haven't even started, gorgeous..."

"You really mean that, don't you?"

"Shelby, after today, you're going to be my girlfriend. Or I hope you will be."

"I'd love that, Scott."

Smiling again, I made her moan as I wrapped my lips around her cock and slowly lowered my mouth around it. I'd taken around half her length in my mouth before it hit my throat. Feeling her cock throbbing away, I knew she wasn't going to last long. I hadn't lasted all that long when receiving my first blowjob.

Bobbing up and down on her cock, I kept looking up into her eyes, her eyes wide and expressive, perhaps still a little surprised she was receiving her first blowjob. Her thick cock was hitting the back of my throat. I'd been able to deepthroat smaller cocks so was wondering if I could do it for her.

"Oh fuck!" she cried softly, "I'm close already..."

"I'll swallow, gorgeous," I told her, "Just cum when you need to."

Bobbing faster, I loved the feeling of her big cock in my mouth. Her natural scent made my own cock even harder. I could taste her pre-cum flowing and was surprised at how much nicer she tasted than anyone else, male or female, I'd been down on previously. I gave up trying to deepthroat her, but knew it would be something I'd definitely try for later, focusing on the sensitive parts of her cock, enjoying the sounds of excitement that escaped her and the continuous throbbing of her cock as her excitement continued to grow.

"Gonna cum!" she warned me. Within a couple of seconds, I felt that first warm spray of cum flood into my mouth, Shelby moaning even louder, as I quickly swallowed that, only for the next spurt to erupt from her cock. Each eruption I swallowed, moaning at the taste of her as her cock must have easily throbbed more than half a dozen times before she finally had nothing left.

Pulling my mouth away, I immediately leaned up to kiss her, and in that kiss, I knew how much we already cared for each other, her fingers caressing the back of my head as her tongue slid into my mouth. Smiling as I continued to gently stroke her cock, which barely softened at all, I finally broke the kiss so I could just gaze at her pretty face for a few seconds.

"Like it?" I wondered.

"I loved it," she whispered, "Do you want to keep going?"

"Shelby, there's lube on the nightstand next to the bed, and while I've never had a real cock up my arse, I've done plenty of experimenting." Gently squeezing her cock, I added, "But if you want to make love to me..."

"More than anything," she replied, chuckling at how shy she was admitting it, "I'd really like to get you ready for me."

"Oh?"

Nodding eagerly, she smiled. "You have a tight little arse, Scott. I'd like to play with it before I fuck it."

I hadn't been fucked before though I'd had my arsehole licked a few times and always enjoyed the feeling. And I'd had fingers up my arse plenty of times when jerking off. Positioning ourselves, me on my knees and my head on a pillow with Shelby sitting on her knees behind me, she gave each cheek a playful slap before spreading me wide and not hesitating in using her tongue on me.

Moaning softly, she chuckled as her tongue tickled me. "Oh fuck yes," I moaned softly, "Love feeling a tongue back there."

"And fingers?" she wondered as her tongue worked my rosebud.

"Yeah, love to jam two up me when I jerk off."

Shelby remained silent as her tongue continued to lick me, getting me nice and ready before I felt her move away and the application of lube, rubbing it all over my arsehole before she started to poke and prod me. Glancing back, she smiled as I felt her index finger slowly slide inside me. Smiling as it felt nice to feel someone else's finger inside me, she buried it quickly, making me groan as she chuckled at my reaction.

Taking her time as she thrust in and out, I quickly asked her for a second finger. That earned a slightly louder groan, using her other hand to start stroking my cock at the same time. "I want to cum with you inside me," I murmured, "It's why I wasn't worried about a blowjob."

"Will you cum when we make love?"

"Shelby, I'm going to cum so hard when you're finally inside me..."

She fingered me a little faster and harder, learning how my body reacted and enjoying the noises I was making. When she slid a third finger inside me, I knew that was simply to get me ready for her big cock, as that was going to be bigger that her three fingers. Leaning forward, feeling her soft lips up my back, her fingers were soon fucking me and I couldn't believe how good just her fingers felt inside me.