Tales of Transwomen Tops Ch. 03

A/N - Just a warning that this will contain references to same-sex relationships between men in the early stages of the story though no actual detailed sex scenes.

*****

Being the new kid at school is always a difficult moment. Thankfully, it wasn't something I'd experienced often. I'd attended the same primary school from kindergarten to year six, and then the same high school from first form all the way to my current year, sixth form, our last year before we graduated and either headed off to university or started working for a living.

New kids had started each year from first form to around fourth form, but most parents would usually try to avoid swapping schools on their kids into the final two years, as the focus was all in preparation for the university entrance exams. One or two might have switched in time for fifth form, spending weeks being awkward as they gravitated towards the group they would feel at home with.

On the first day of sixth form, having spent a fantastic six weeks lazing about, having turned eighteen just before Christmas, there was only one new student from what I could recognise. Thankfully for her, she wasn't introduced in front of the entire year at the first assembly of the year, but there was no missing she was a new face in the crowd. The bright pink hair and her height certainly meant she stood out immediately. Dressed in the same school uniform as the rest of us, I knew she'd be feeling rather isolated and lonely for a few days to start with.

At lunchtime, I was hanging around my friends. Eight of us in total who'd known each other most of our time through primary and then secondary school. It wasn't a real surprise that the new girl was the immediate topic of conversation.

"Catch her name?" I asked.

"Think her name is Shelby," Liam replied.

"She's kinda cute," Brett suggested.

"Bloody tall though. Rare to see a girl as tall as her," Chris added.

"Big set of tits on her. Looked fake, in all honesty," Tom said.

We made small talk until Connor eventually cleared his throat. "So... Are we going to discuss what we did during the holiday?"

The rest of us shared glances, blushing and smiling, as no doubt we all remembered those six weeks rather fondly, and we now shared a bond as eight friends that very few likely did.

"Well, I don't know about the rest of you, but I don't regret anything we did," I stated, "We've all been friends for years, and you all know I've been bi-curious since hitting puberty. None of us were virgins when we started messing around. We're young, hot and horny."

There were a few chuckles before Adam cleared his throat. "All I know is that you guys sucked my cock better than any girl," he admitted.

"I had no idea receiving anal could be so pleasurable," Adam added, "I mean, I'd never do it with anyone else, but doing it with one of my mates was, well, gay but not... as gay, if you know what I mean. Still desire pussy more than anything... But I don't regret a thing we did."

"Does it end where it did or will we still fool around though?" I wondered, "Do we consider it six fun weeks and move on or...?"

"What do you want, Scott?"

I shrugged as I hadn't made a decision in my mind. "Look, I know I'll eventually settle down with a girl, but what we shared over the summer was a culmination of a lot of things we shared. We went from watching porn together and masturbating, to fooling around with each other, to changing the porn we watched and then it just went from there. I still remember the first time Adam went down on me for the first time. He had far softer lips than I imagined."

"I do like sucking your cock, Scott," he whispered.

"And I loved feeling you in my arse for the first time," Liam added, smiling at me. Out of all my friends, I'd fucked him the most. He had a tight little body, and a fantastic arse. There were no feelings of love between any of us. We were young and always horny and amazed ourselves and each other by how open minded we'd all been.

"Shame you didn't want to take any dick, Scott," Matthew stated, "Though I've got to admit that it was wonderful when you fucked me."

Chris snorted. "Please, everyone enjoyed being fucked by Scott."

Shrugging again, I smiled at them. "Hey, I would have happily bottomed for someone, but you were all quite happy to suck my dick then have me fuck you. And you had no problem taking my dick while I stroked you off until you orgasmed."

"Damn it, all this talk is turning me on," Adam moaned.

"What about you, Connor? You were the first one to bring it up," I wondered.

He blushed again. "I'd be happy to keep having fun, but I'd rather it not become well known around school. You know what many girls can be like if they learn about any young men who like to suck cock and be fucked." He paused and added quietly, "And I really liked being fucked by you guys."

"I'm happy to keep it between ourselves," I replied, "What we do as friends is no one else's business but ours."

I was left wondering if we'd keep hooking up in the future. Don't get me wrong, I had no romantic interest in any of my friends. But I was comfortable enough to fool around with them sometimes. Those six weeks of summer had been eye opening for all of us, surprised at how quickly we were comfortable in doing things with each other that would have led most to call us some rather derogatory names.

But at heart, I still wanted to find a girl to date and fall in love with, eventually marry and start a family, growing old together in the future. While I was waiting to find this girl, it wasn't going to stop me having some fun, and if it meant sinking my cock in the arse of one of my friends on occasion, I was going to enjoy it.

The new girl, Shelby, ended up being in four of my six classes. Being the new girl and a little shy, I noticed she would take an empty desk near the back in a corner. The first few times, I left her alone as she looked almost painfully shy and a little awkward. But there was no missing that she was also utterly gorgeous. Whenever she glanced my ways, I was met by a pair of utterly gorgeous green eyes. Adding those to her pink hair, obviously not her real colour, and I couldn't help but think she was just absolutely beautiful. I was left wondering if she realised...

It actually took me nearly all week just to work up the courage to talk to her. I'd seen her walking around alone during the first four days, so finally just plucked up the courage to approach her during recess on Friday, as she was sitting by herself at one of the long tables. Sitting down opposite her, she lifted her face to mine, noticing the immediate colouring of her cheeks.

"Hello," I stated.

"Hi," she replied, her voice soft, almost breathy.

"I'm Scott. And I know your name is Shelby. Nice to finally talk to you."

She blushed a little more, curling some hair behind her left ear. "I know who you are. I've seen you sitting with your friends by the playing field."

"How are you finding our school so far?"

"Everyone's been really nice but I'm still finding my feet."

"Little unfair to start at a new school in your last year."

Shrugging, she managed a tight grin. "It might seem like that but there's a good reason why." Before I could open my mouth, she shook her head. "I don't know you well enough yet, Scott."

"Would you like to get to know me well enough?"

The warm smile was a surprise, though I didn't miss the fidgeting of her hands at the same time. Then her green eyes met my blue and the smile broadened. "I'd like to make some friends while I'm here. I left so much behind moving schools. Left a lot of people behind that I'd known for years, since I was a little kid."

"Most of my friends I've known since I was five so I could certainly understand what it would mean to leave good friends behind. But you have plenty of time to make some new friends."

The bell for the end of recess rang and I knew she was in my next class. Offering to walk with her, that same smile formed and we kept on talking until we were sat side by side, waiting for our teacher to arrive. As we listened and took notes, we shared glances the entire time, and I knew I was smiling at her in return.

At lunchtime, I invited Shelby to join me and my friends though she smiled, stating she needed to do some studying as the curriculum we'd focused on was different to what she'd been doing, so she needed time in the library to catch up. My friends asked where I was during recess. Of course, letting them know I'd been talking to Shelby led to plenty of good natured ribbing.

"Interested in her?" Brett asked.

"She's gorgeous and already proven how smart she is. But I don't know her that well yet. Let's not get over excited."

"Plans for the weekend?" Adam wondered.

"You guys are free to come over as usual," I replied, "Parents won't be home as usual, so I'll have the run of the house. Fridge full of beer, pool is always clean, and I'm sure I can find us some good porn to watch."

Later that afternoon, I was home alone, watching some porn on the big screen television in the living room when the doorbell rang. I was ready to put on some shorts when I thought I'd check who was at the door. Grinning to myself, I opened it to find Connor waiting for me, an almost needy look in his eyes. Within a couple of minutes, he was on the floor between my legs, eager to please me, before he moved up to straddle my lap, cock buried in his arse as he slowly rode me, stroking himself off until he enjoyed an orgasm.

"Want to stay the night? The rest of them will be coming over in the morning."

"Another weekend of group sex?" he asked softly.

"Is that what you want, Connor?"

"I want to meet a girl but I can't help really loving the feeling of something in my arse. It's a little addictive."

"You're bisexual, Connor. There's nothing wrong with it. And if a girl is going to judge you for it, then she's not the one for you."

The rest of our friends all arrived by lunchtime the next day. We spent the day by the pool, drinking, fooling around the pool, or taking in the sun, in addition to sucking cock and fucking. A lot of fucking. Cum ended up everywhere, particularly once we moved inside and the living room echoed to the sounds of eight young men enjoying the company of each other. If we'd filmed it, we'd probably make a lot of money. We were fit young men but all of us were average in the cock department. None of us was swinging a ten-inch cock, as round as a baseball bat, and capable of dumping monster loads into each other.

Returning to school on Monday morning, we were all in good moods as it had been a fun weekend. Shelby was in my first class of the day, and I found myself sitting next to her again, asking about her weekend. She admitted to being slightly lonely as she was now so far away from old friends and most of her family but added again that it was for a good reason.

"Want to have lunch with me later?" I wondered.

She looked thoughtful before smiling at me. "I'd like that, Scott. We're in the same class before lunch so we can walk together."

I noticed later while walking next to her that she was actually an inch or two taller than me. The last time I'd been measured, I was around five-ten, so she must have been six foot at a minimum. That was very tall for a young woman of eighteen. Sitting across from each other with our lunchboxes of food, we conversed about nothing in particular, mostly about our classes and what we hoped to achieve during our last year at school.

Asking where she lived, I was pleased to learn she only lived a couple of streets away from me. And that led to an immediate offer for her to study at my place, particularly as she needed help catching on certain subjects that she hadn't studied. The offer made her smile. "No other reason, Scott?"

"Not at the moment. I'd like to be your friend though, Shelby."

The smile that formed near enough made my heart stop. "I'd like that too," she said softly, "You've made me feel very welcome. Thank you."

"I know I've been lucky to be at the same primary school then secondary school, with the same friends. I can only guess at how difficult changing has been."

"In more ways than one," she stated, somewhat cryptically, though I didn't really get the reference. Then she met my eyes and smiled again. "Are your friends as nice as you?"

"Sure. Wouldn't hang out with them if they weren't."

Standing up, I escorted her out to where my friends were kicking a ball around. Noticing she was stood rather close to me, I didn't miss their reactions as I'd known them long enough to see the signs of interest, giving me looks that told me they knew exactly what I was thinking at the same time. Shelby leaned a little closer, glancing to see she was blushing, as the seven approached us. I made introductions and we chatted a little bit before lunch ended, not realising how long I'd spent talking to Shelby in the canteen.

At the end of the day, she met me at the front of the school and asked if I'd like to walk her home. I was finding her incredibly easy to talk to and the walk to her house seemed to fly by. Stopping outside her house, I gave it the once over and was impressed. It was a nice house.

"Doesn't come with a pool though," she stated.

"We have one at my place. Add to that I'm an only child and I rarely see my parents..."

"Why's that?"

Shrugging, I admitted I didn't actually know. "They do their own thing. Were interested in what I was doing until I was about sixteen. Now they're off doing whatever, leave me enough money to buy myself food and get myself about. In fact, they leave more than enough money. I think they mix travelling and working."

"Sounds rather lonely."

Smiling, I shook my head. "I've taken advantage, I guess. Friends can visit whenever they want. And as long as I don't burn the place down, or have the police showing up regularly, they come home for a few days, we pass like ships in the night, then they disappear again. They usually just say they're off for a few weeks, even a few months. They leave contact information, but now that I'm eighteen, I guess they believe their job is now over. At least they haven't cut me off or kicked me out."

"Damn, don't you get lonely?"

Shrugging, I replied, "Nah. To be honest, I've never been close to my father. I was close to my mother but I have a feeling I put a dampener on their lives. The sooner they were done raising me, the better."

To my surprise, Shelby stepped closer and hugged me. "If you're ever feeling lonely, just give me a call. I'll come over and visit."

Hugging her back, it felt nice. I can't remember the last time I'd hugged either of my parents. I had no problem hugging my mates, but that was difficult. Hugging Shelby in that moment felt wonderful. "I might just take you up on that offer."

Watching her walk towards her front door, she glanced back and waved. Waving back, I waited until she was inside before I finished walking home. We did the same thing for the rest of the week, spending time together at lunchtime either together or with my friends. It seemed very few girls were keen to become her friends, though I'd always known they were rather cliquey.

Asking what she was doing on the weekend, I was disappointed to hear that she'd be visiting family so wouldn't be around. She seemed to notice my disappointment, giving me another hug, which I found myself enjoying immensely every time she did. "Maybe I could visit you next weekend? Check out this pool of yours?"

"You're welcome anytime you want to visit."

"I might just take you up on that."

Arriving home by myself, I invited a couple of friends over for the night, and we ended up having a little fun. The others arrived on Saturday for our usual weekend of sex and debauchery. It was amusing that it was continuing even though we were back at school. If anyone at school found out what we were doing with each other... But when I had my cock buried in the arse of a friend, I didn't really care about anything else.

Shelby was excited to see me when I picked her up on the way to school on Monday morning, telling me about catching up with her aunts, uncles and cousins at a family gathering. I gave her vague details about my weekend, the fact I had some friends over during the weekend. We hadn't really talked much about our personal lives, though we both confessed to being single.

It took her a few days to muster up the courage to ask about my love life during our walk home. Maybe I looked somewhat satisfied. I knew some women could react negatively when hearing a man was bisexual. There wasn't exactly a double standard, but I'd read enough horror stories of men admitting to being bisexual and for their partners to just assume they were covering up being gay.

"Are you fooling around with anyone, Scott?"

"Fooling around, yes. But no actual feelings are involved. Purely physical sort of thing." Pausing, I quickly added, "I'm looking for the right girl to fall in love with."

"Who with?"

"Well, to be honest, I'm bisexual, Shelby."

That made her stop and stare at me. "Really?"

Smiling at her, I nodded. "You know who I'm sleeping with rather well. We're mostly all busy fucking each other when the mood hits. Summer holidays was a hell of a lot of fun. They helped keep my balls empty the entire time."

"No!" she squealed, making me laugh. "Your friends?"

"Yeah, we're all open-minded young men. I reckon one or two of my friends is actually gay. Won't tell you who. But we enjoyed the summer and we've continued meeting up and having fun."

"Wow..." she whispered. Then she stopped and hugged me tightly. "Thank you for being honest with me."

"Shelby, if I were to meet the right girl..."

She leaned back and met my eyes, and she immediately read my insinuation. The smile that formed made my heart flutter a little bit. "Do you think you've met the right girl?"

"I'm not sure just yet because we haven't known each other that long. But I'm finding that I enjoy spending time with her."

She hugged me again. "I'll see you tomorrow morning, Scott."

"See you, Shelby."

I found myself thinking about her whenever I wasn't around her. I'd had a couple of girlfriends before, but I was starting to experience feelings for her very quickly that I hadn't really felt before. Walking to and from school every day gave us around twenty minutes to ourselves, talking about anything and everything that was on our mind. But while I was happy to talk about anything, I did notice she was rather closed off about her past. No mention of previous relationships, and anything about her previous school was quickly shut down.

Noticing my reaction when she reacted badly to one question that I asked over lunch a few days later, she leaned over to take my hand, squeezing it affectionately. "I'm not comfortable talking about it yet, Scott," she said softly, "But if there's anyone I will tell, it's you." She squeezed my hand again. "The most important thing is that I trust you already, Scott."

Biting the bullet, I squeezed her hand in return. "Well, I like you already too, Shelby."

That same smile I'd seen a few times appeared, and we held hands for the rest of the lunch break, chatting away and not even bothering heading out to join my friends. I found her rather captivating and those feelings I was starting to experience grew stronger with each passing day. I was quite sure it was a healthy dose of lust. I was eighteen and perpetually horny, but I also knew I was feeling more than just wanting to be intimate. I just wanted to be in her company and wanted much more than that.

"Want to come around to mine this afternoon to study?" I offered on a Wednesday, about three weeks after she'd started, "I know you're still catching up on certain things."