Tales of Transwomen Tops Ch. 06

Sitting at the table across from my two sisters, I was doing my best not to scowl but our lives had changed in the past few months, and I didn't like it. My father was at the head of the table, spooning cereal into his mouth while checking his phone for messages. My two sisters were chewing on toast or fruit, their noses buried in their phones too.

No idea what my mother was doing as she was now on the other side of the country with her affair partner. She'd been cheating on our father, my oldest sister the one to discover what was going on. The marriage of my parents collapsed rather quickly as she immediately told our father what was going on. Our mother didn't deny it. In fact, I remember the satisfied smirk on her face when she sat us down and told us the truth.

It meant we'd had to move as she'd timed it well. I had been eighteen for a couple of months, so she wouldn't be on the hook for any child support, and when it came to divorce, she wanted her share of the house. Dad didn't want to remain in the house either, considering his now ex-wife had fucked numerous men in the marital bed.

I understood why we'd had to move, but leaving behind all my friends, and having to start at a new school for my last year just plain sucked. My oldest sister was still studying, so simply transferred to the nearest university, while my other sister had found a new job that actually paid better than the job she'd left behind. As for my father, the company he worked for had offices everywhere, and after hearing what happened, they moved him to a new office and gave him a promotion.

Lowering his phone, he finally glanced in my direction, and I must have still been scowling. I was old enough to understand, but it still sucked. "I know you're not particularly looking forward to a new school, Steven..."

"It's already been discussed, Dad. I don't like it but there's not a lot I can do about it. Anyway, I don't blame you for any of this. I blame Mum."

"I'm glad you don't blame me, son."

Glancing at my sisters, I returned my eyes to him. "No-one at this table is to blame, Dad. Katie did the right thing in telling you what was going on."

Katie smiled at me. "Thank you, Stevie. I've always worried that you..."

"You did nothing wrong. The only one at fault is our mother. Quite frankly, I don't even really want to think about her, but it's difficult not to considering we're in our current situation. As for your original statement, Dad, I'm not particularly looking forward to starting at a new school, but things could be a lot worse for all of us."

Arriving at school in my own car was a bonus, Dad having bought it for me after moving to the new city, having spent a couple of weeks driving around, learning the important streets and the best route to and from school. Parking up in the car park, there were curious glances in my direction as I was definitely a new face. Walking into the administration part of the building, I was expected, so after filling in a bit of paperwork, I was handed my timetable of classes and what else to expect.

As it was the first day of the new school year, there'd be an assembly where all the students would congregate, the principal would give a speech, before we'd head off to the first class of the year. Each class had me introduced to a teacher, and I did end up chatting to a couple of guys who were rather friendly and ended up spending lunchtime being introduced to plenty of people. Everyone was very welcoming.

The day flew by, and my last class was English. It was at the beginning of the lesson that I was introduced to Miss Rodriguez. It was easy to figure out she was of Latin extraction, though whether that was Latin Europe or Latin America, I didn't quote know. Though friendly when I arrived, it was easy to figure out that she was respected but she didn't tolerate disrespect or dissent in her classes. Just during that first lesson, two of my classmates were warned about their behaviour in such a manner that neither made a peep.

Asked to stay at the end of the lesson, I wasn't worried as there was no rush to get home. Waiting until the room was empty, the click of her heels echoed in the silence as she walked to the door to shut it. Turning around, she pointed to an empty chair, sitting down without needing to be told. Standing in front of me, I had to arch my neck as she was tall even without her heels.

Her long dark hair hung down to her shoulders. Her eyes were a deep brown, almost a window to her soul. Her lips were full, and she wore glossy lipstick. Her blouse was tight to her body, and she had a big pair of tits. I'd heard talk during lunchtime that she wasn't the only teacher that many of the students fantasised about.

"How have you enjoyed your first day?" she asked, the question catching me by surprise.

"Better than I thought it would go. Everyone's been friendly, at least."

"Can I ask a few personal questions?"

Shrugging, I replied, "Sure."

Wheeling her chair around her desk, she sat in front of me, crossing her legs to show off the tops of her thigh-highs as her skirt rode up. The top couple of buttons of her blouse were also undone to show off a little bit of cleavage. "How tall are you, Steven?"

"Um, last time I was measured, I was around five-six."

"You keep fit?"

"Yeah. Soccer during the winter, tennis in the summer."

"Have a girlfriend?"

"Um... No."

The questions were a surprise but, considering she was hot, I didn't mind. "Virgin?" Okay, that was a question I didn't expect. Feeling my cheeks grow warm, she chuckled to herself. "I guess that's my answer. Nothing wrong with being a virgin, Steven."

"I just didn't expect a teacher to show an interest."

"It's your first day and I like to know my students. I won't be the only one with an interest in you."

"Interest?"

"Just meant by the fact you're a new face and we're all going to want to get to know you."

"What about you, Miss?"

Wheeling her chair a little closer, she smiled as one of her heels hit the floor and I felt her foot stroking my shin. "What about me, he asks? Well, I take my job very seriously, as I'm sure you've already realised. I won't tolerate any student fooling around in my class. You're here to learn and I make sure none of my students fail. I have various methods to deal with students who might need my help or inspiration. I particularly enjoy private tutoring of one or two students, taking them under my wing." She smiled as her foot continued to stroke me. "I believe you might need some of it as you might need help catching up on some topics. I've read over your previous record, and you were focusing on different things at your old school. I won't be the only teacher to suggest this."

"If you're offering to help me, Miss, I won't knock that back. I can't afford to fail anything this year as I need top marks to get into the course I want at university."

"We can discuss it further during this week." Removing her foot, she smiled as she stood up, sliding her foot back into her heeled shoe. "Can I see your timetable?"

Handing her the paper copy, it was amusing to see her eyes light up before she looked at me and smiled. "Well, you're going to have a fantastic year, Steven. Miss Anderson is a delight, and you'll love her history teacher. And Miss Bailey as your PE teacher... There's a reason every young man wants to be in her class."

"Any other teachers I should know about?"

She leaned back in her chair, stroking her chin. "Hmmm. Miss Chen is a language teacher. Everyone adores her. And Miss Nguyen teaches cooking and home economics. You might not be in either of their classes but they're great teachers to know."

"Thank you, Miss."

"You're welcome, Steven." Getting to my feet, she escorted me to the door, feeling her hand on my lower back. Before she opened it, she turned towards me. "How open minded are you, Steven?"

"How do you mean, Miss?"

"I mean in general, but say... We live in an open-minded and tolerant society. Say a new girl started this week and you found out she was born a male..."

"You mean she was trans?" Smiling and nodding, I shrugged. "It wouldn't bother me."

"Good to know, Steven. Good to know." Opening the door, she rested her hand on my shoulder. "Have a lovely afternoon and I'll see you tomorrow."

Arriving home first as expected, I knew we wouldn't see our father until much later that evening, so it was just my sisters and myself for dinner. They asked about my day, and I was ready to tell them about my last conversation with Miss Rodriguez, but then thought better of it. If she wanted to take a personal interest in me then it could only be a good thing.

She was right about Miss Anderson, though. Last lesson of the day again, I found myself being held back for a second day in a row as she asked the same questions as Miss Rodriguez the previous day, though she asked a couple of more questions about my opinion on transgirls and if I'd be attracted to them. I was almost left thinking they knew about my browser history, as like any young man, I'd been curious about certain things.

I met Miss Bailey for the first time on Wednesday, thankfully the class taking place prior to lunch. Like Miss Rodriguez and Miss Anderson, she was a tall and incredibly beautiful woman and, in her tight-fitting clothing, had a body that nearly any woman would have killed for. No wonder every red-blooded male wanted to be in her class.

By Friday, I'd met all my teachers and had even taken the advice about meeting with Miss Chen and Miss Nguyen, who were a pair of absolutely delightful women and seemed to love the fact I wanted to meet them despite neither of them teaching any of my classes. Miss Rodriguez seemed to bookend my weeks by taking my final classes on Monday and also on Friday.

Asking me to stay back again at the end of the lesson, she had me sit in front of her desk as she perched herself on the edge, and I could barely tear my eyes away from her long legs. Or her cleavage. Or her incredibly pretty face. "How have you found your first week?"

"Rather enjoyable, Miss."

"Are you still interested in some private tutoring with me?"

"As long as it isn't..."

"It won't be a problem, Steven. And it won't just be with me. Miss Anderson has suggested she would also like to help. And Miss Bailey is a good friend, so she'll probably join us too. This weekend might be a little too early, but how about we start at the end of next week? You can come around on Saturday morning and we can spend all day ensuring you're all caught up as soon as possible."

"Thank you, Miss. I appreciate the fact you're all willing to help."

"It won't just be working. I have a pool if you'd like to join us for a swim. And we'll happily provide lunch too."

Her eyes sparkled when I smiled at her. "I can only say thank you again, Miss."

"You're very welcome." Placing her feet down, she gestured for me to follow her to the door. Before opening it, she turned back to me and placed a hand on my shoulder. "Make sure you mention this to your father. We don't want any secrets."

"I'll tell him though I'm sure my sisters will insinuate certain things. Hell, most of my new friends will probably be suggestive."

Running her fingers up and down my arm, she leaned in slightly closer. "And is that such a bad thing, Stevie? The new student in school attracting more than one teacher to him? You would be considered an instant legend. The sort of student they'd still be talking about in twenty years."

"Now you're just teasing me, Miss."

"While I am, we all agree that you're rather cute, Steven." I felt my cheeks grow warm, but I didn't expect her fingers to gently caress me at the same time. "You're a delightful young man, Steven. I'm glad you're in my class."

"I'm glad you're my teacher, Miss."

She took a deep breath and stepped back to open the door. "Have a lovely weekend, Steven."

"I will, Miss. You have a great weekend too."

I didn't actually tell anyone about what I would be doing the next weekend. I'd wait until next Friday. Instead, my sisters did show some interest in how my first week had progressed, pleased to hear that I wasn't an outcast and that I'd already made some friends. My father arrived home at a reasonable time, and we shared a beer together as we ate some take-out. He was doing his best to support his kids, but with the hours he was working, even I knew he was burning the candle at both ends.

The next week was much the same as the first, though I wasn't asked to stay back. Instead, I may not have had much experience with the opposite sex, but I was left convinced by the end of the week that Miss Rodriguez and Miss Anderson were, quite frankly, flirting with me and seemed to be interested. I had no real idea why though I did enjoy the attention.

"Come around about 10am tomorrow, Steven," Miss Rodriguez told me at the end of our final lesson on Friday.

"Yes, Miss."

"Although I guess you will need my address. Hand me your phone and I'll put all my details in there. You'll be the only student to have my phone number. I trust you won't be too inappropriate with it."

"I'll be good, Miss."

Telling my sisters and eventually my father about what I'd be doing the next day, I was surprised that none of them made any real jokes. In fact, my oldest sister suggested it was rather sweet that my teachers were taking such an interest in trying to help me catch up, while my other sister admitted to being a little jealous that none of her teachers had ever shown such an interest in her studies.

I was up early and that's when I was teased as showered and shaved, my sisters asking if I was going to study or if I was going out on a date. I showered every morning, though I guess I didn't want to make a bad impression. I wore my school uniform five days a week and wasn't going to just show up in a pair of grubby shorts and t-shirt.

Arriving outside a rather gorgeous house in a suburb not far from where I lived, I felt some butterflies as I approached the front door. Miss Rodriguez opened the door seconds after I'd pressed the doorbell, greeting me with a warm smile before leaning down to kiss my cheek. Feeling myself blush, she took my hand and led me inside, Miss Anderson rising from her position on the couch to kiss my cheek too. Miss Rodriguez and Anderson wore gorgeous sundresses, showing off toned legs and tanned, toned arms. Miss Bailey wore a tank top with a very tight and small pair of shorts.

"Want a drink before we start, Stevie?"

"I'll have another wine, Josie," Miss Anderson replied, wiggling her empty glass in her direction.

"Courtney?"

Miss Bailey sculled whatever was in her glass. "I won't say no, though is this a study session or something else?" Her words were for Miss Rodriguez, but her eyes were only looking at me.

"Behave, Courtney. At least for now... Stevie, drink?"

"Um, as I'm here to study..."

Miss Rodriguez caressed my cheek. "That's true, sweetie... I mean Stevie, but you should also relax too. Have a sweet tooth? I don't have beer but there's wine and plenty of liquor to make cocktails."

"Okay, I'll have something."

"Good boy. Now keep Miss Anderson and Miss Bailey company while I make us some drinks."

Finding myself between the two statuesque beauties, even when sat down, I felt a little intimidated with all the skin and cleavage on display. Both turned slightly in my direction, smiling at me as we made small talk. I was still quite new to them, so they asked general questions about my life. I was actually rather forward in asking one or two personal questions in return, surprised to learn their first names, as I knew most teachers preferred students not to know.

Miss Rodriguez returned with a tray of drinks, sitting between me and Miss Anderson, surprised when she immediately rested a soft hand on my thigh. "Thank you for coming today, sweetie..."

There was no correction to my name this time, simply meeting her eyes and smiling. "Well, I'll accept any offer to help as I know I'm behind regarding certain things."

"Finish your drink, then we'll head into my office to study. If you'd like, we'll have some lunch then spend a couple of hours by the pool this afternoon. Could you handle seeing three of your teachers in bikinis or two-piece swimsuits?"

"I don't think that will be a problem, Miss."

"Good boy. Now, that's for later. Follow me to my office."

Standing up, I followed her down a hallway, passing by what looked like a guest room, the bathroom and what must have been her bedroom further on. Her office was already set up for us to sit side by side at her desk, dropping my bag and taking out my laptop. Sitting next to her, she rolled her chair as close as possible, her legs and arms often bumping into mine as we worked through a few things I needed to catch up on. Miss Anderson joined us an hour later to offer her assistance, rather turned on when I found myself pressed between the pair of them.

A couple of hours flew by. Miss Rodriguez eventually cleared her throat and locked her screen. "Time for another drink, lunch, then we should head outside to relax. We don't have to do everything today, Stevie. Moving school at this time isn't the best thing but we'll get you caught up as soon as we can."

"If you don't come here, you can always come to mine for more one-to-one tutoring," Miss Anderson added, resting her hand on my thigh, meeting her eyes, "I love helping those students who prove as dedicated to learning as I am to teaching."

"Thank you, Miss."

"Want to come and join your three teachers in relaxing, sweetie?" Miss Rodriguez asked.

"Sure."

"Let Courtney know we'll be out in a couple of minutes, Natasha."

Miss Anderson returned a grin before she left, closing the door behind her. Getting to my feet, Miss Rodriguez did the same, though she almost made me help when gently grasping my wrist and pulling me closer to her. "Do you think I'm attractive, sweetie?" she asked softly.

"Miss?"

"We're outside of class, sweetie. Call me Josie. And the question remains."

"I think you're beautiful, Miss."

"Good answer. And Natasha?" Nodding, she added, "And Miss Bailey?"

"You're all beautiful, Miss."

Caressing my cheek made me blush, her soft fingers running from next to my ear towards my chin, grasping it and moving my head, lifting it so my eyes could meet hers. She returned an utterly gorgeous smile. "You're going to love what you see by the pool a little later, sweetie," she added, "All your teenage dreams might just come true." Gulping, she smiled before leaning down to kiss my cheek, her hot breath in my ear making me shudder. "Even better news is that our school would have no problem. You're eighteen and an adult. And if you wanted to fool around with three of your very fit teachers..."

In a daze, she took my hand and led me towards the kitchen, where Miss Anderson and Miss Bailey were preparing food and drinks. Noticing the look on my face, Miss Anderson turned her eyes to Miss Rodriguez. "What did you tell him, Josie?"

"Just that he's going to have a lot of fun with us, Tash."

"So we're sharing him?" Courtney wondered, the question having me looking between all three of them.

"We're not going to just leap into everything straight away and scare the poor boy. We'll ease him in slowly, but the idea would eventually be for the three of us, plus Becca and Emily to also have fun with him. And if he's really interested, all five of us could be with him at once."

"Can't remember the last time I was in a gangbang," Miss Anderson stated wistfully.

I nearly spat my drink out, coughing a few times as Miss Rodriguez gently patted my back. "Sorry, sweetie. The sex talk started far earlier than anticipated."

"I'm going to put my bikini on," Miss Bailey stated, "Want a free show, Stevie?"