Tales of Transwomen Tops Ch. 08

His sexy stepsister had hidden one hell of a secret. Until now...

*****

My parents divorced when I was ten years old. It was the usual story of infidelity, the shock of the exposure, the fallout, the arguments, bitterness and the inevitable divorce. My parents both worked, my father full-time, my mother part-time, as she liked to be home when I left for school and home in time for when I returned.

My father worked long hours, but I wasn't really aware of the fact he was getting home later and later, and sometimes not coming home at all. Whether my mother was suspicious, or it was simply by chance she discovered it, but she was taking dinner to his office when she walked in on him fucking his secretary over the desk. Considering my father was in his early forties, my mother in her late thirties, and the girl in question barely twenty, I could only imagine the words exchanged.

But it gave my father an opportunity to show his true colours. Mum kicked him out and she filed immediately. By the time the divorce had gone through, Mum had the house, would receive spousal support, and would have received child support. Little did I realise that my father wanted nothing to do with his now ex-wife or his son. He paid an enormous lump sum of cash and then just disappeared from our lives.

"Don't worry, Mark," Mum assured me a couple of nights after I received the letter telling me he was leaving for good, "I'm confident I'll meet another man, a good man, a better man, and if he's that sort of man, he'll treat you like you're his son."

Mum met John when I was twelve years old. She was working a full-time job by then and they met at the office she now worked. She worked one of the desks and he was a regular visitor. It didn't take long for him to ask her out, and I was introduced to him around three months after their first date. I'll admit to being a little suspicious a first. Everything that happened with my father had left their scars. John didn't try and win me over immediately, understanding my own hesitancy, but he was polite and friendly, and that's what mattered.

After another three months, there was a meeting of families, as my mother and I, plus her parents, were invited to join John at his place for lunch. And that's when I met his daughter, Josie. I learned quickly it was short for Josephine, a name she quickly admitting to disliking. When asking why, her eyes darkened, muttering something about her mother.

I learned that John had gone through a bitter divorce, another victim of infidelity. Unlike our family, her mother was still in her life, but Josie wanted nothing to do with her. However, visitation was court ordered, and though she lived with her father, her mother was entitled to one night visit a week, and an entire weekend every fortnight.

Within six months, Mum admitted to me one evening that she was deeply in love with John, they were discussing living together and marriage, so how would I feel if he and Josie moved in with us. There were two spare rooms so Josie would have her own place. I think I surprised her slightly when admitting it would be nice. Josie and I were friendly, but more importantly, I'd always been an only child. She was only three months older than me, the good news being that we'd be in the same year group at school.

Moving in day was interesting as John and Mum were ever so excited. I helped Josie with things I could help carry inside. Mum had spent a few nights preparing her room, something Josie immediately thanked her for. While Mum and John spent time together, I found Josie sitting alone in her room, resting back against the headboard.

Being barely a teenager, I didn't really understand all that much. Josie smiled and patted the bed next to her. "Thanks for being so nice, Mark," she told me.

"Is it weird being here?"

"It probably will be for a few days or weeks." She paused before adding, "It's going to be weird having a boy around the house who, technically, will now be my brother."

"Well, you'll be my sister."

"Not step-sister?"

"I always wanted a sibling, whether a brother or sister."

Cuddling into my side and giving me a squeeze, I sensed she was smiling. "Never thought I'd get a brother too."

I can honestly say that, for the next few years, Josie and I rarely had a falling out. We were not entirely mature, but whenever we did have a problem, there might be the occasional tantrum though always made sure to sort any problem out between us quickly. Within six months of her moving in, she was more than just a sister, she was also my best friend. We spent a lot of time together at home, part of the same friend group, and we helped each other through any struggles we might have had.

Mum and John loved the fact their children got along so well. As my own father had walked out on me, I sat down with him within a year of marrying my mother and asked if I could call him 'Dad'. We were both emotional as we embraced, hearing him whisper that he'd be proud to call me 'son' in return. Josie wanted a hug, whispering into my ear that I was now definitely her 'brother' as much as I was her 'sister'.

Our parents were happy that we grew so close over the years. Going to the same school helped as we were in many of the same classes, meaning we could study together, bounce ideas off each other when studying, and we cheered each other on. As I said above, there were arguments and disagreements, but our relationship was always close. Going through changes in mind and body wasn't easy for anyone.

Though we were a blended family, Mum always made time for me as much as John made time for Josie. I was seventeen, around six months from turning eighteen, when Mum took me out for dinner. Nothing more than a burger, chips and ice cream to finish. Mum still liked to spoil me sometimes, even though I now worked a part-time job and had built a little nest egg of savings. Mum and John had both agreed that neither child would pay rent until we were working full-time, if we chose to remain living at home.

"Are you still going to university next year?" she asked after we'd finished dinner, now sat across from each other, nursing an ice cream sundae each.

"I've been talking to Josie, and we'd like to attend the same campus, or that's what we hope."

Mum smiled then asked, "You really love her, don't you?"

The question made me look away, my cheeks feeling rather warm. Being my stepsister, only related to me through marriage, I knew my feelings for her were not entirely wrong. Maybe a little weird, but she was also the only young woman constantly in my life. And given how close we were... "I do love her, Mum. As a sister."

"And as something more?"

I spooned ice cream into my mouth and gave the question some thought. "I wouldn't want to presume anything about our relationship. We're obviously close and get along well..."

"Mark, John won't say it in so many words, but he's so happy that you get along with his daughter. More importantly, you make her feel as loved and appreciated as much as anyone in the house. I love her like she's my own flesh and blood. I might not have birthed her, but I look at her as if she was my own. Given that her mother has basically disappeared over the past couple of years, I've loved how much she's come to rely on me too."

"I'm just glad we got along well from the start and our friendship has blossomed from that. I love how close we are. She's the first one I pretty much tell anything about my life, and I know she does the same with me."

"It's obviously how much she loves you just as much. John mentions it at least once a week. Admittedly, we were both worried when introducing you, but given you calm demeanour, and her infectious friendliness, I guess we had nothing to worry about."

Josie was the first of us to turn eighteen. The day of her actual birthday was mid-week. John took the four of us out for dinner, Josie was able to legally buy alcohol for the first time. The restaurant she chose served excellent food without breaking the bank. She had a great night and was half-cut by the time we made it home. Staggering off to bed, she stopped and hugged me tightly.

"You'll be eighteen soon enough. We should go out together the first weekend."

"Sure. Sounds great, Josie. Just you and me or with friends?"

Leaning back, she smiled at me. "Why not just you and me?"

I'll admit that question left me a little perplexed as it did sound like a bit of a date. I'll admit, I hadn't dated all that much as many girls were put off by my relationship with Josie. As for Josie, she rarely mentioned any boyfriend or girlfriend. We did discuss private matters, but relationships seemed to be a topic we just never seemed to talk about.

"I mean, if that's what you want to do."

She cuddled me, something I was used to, but for the first time, it felt different. "I think it'll be a great birthday, Mark. I promise."

Turning eighteen is usually a rite of passage in most countries as that's when a young adult can legally vote, drink and smoke. Most teenagers already have their driver's licence, whether a learner or provisional. On the morning of my birthday, I was given a few presents, but as it was a day at school, it wasn't anything particularly special until I got home. John arrived home early, told me to get changed, and took me to the pub so I could buy my first beer. Legally, at least.

I enjoyed a few beers with him before Mum and Josie arrived to join us for dinner. Mum was proud her only son was now an adult. As for Josie, she was surprisingly affectionate, particularly after we'd finished eating and had moved into the bar area, hanging on my every word and she seemed to be constantly touching me.

Arriving home later that evening, Mum and John headed off to bed straight away. Even though we had school the next day, Josie and I stayed up a little longer, as I'd bought a bottle of liquor that we could share on a weekend together. Sitting on the couch, we were both buzzed, laughing and chatting away about anything that came to mind. Eventually lapsing into silence, our eyes met, and she had this look on her face I couldn't quite pick.

Kissing my cheek, her soft lips definitely made me blush. "I'm glad you're in my life, Mark. Best thing my father ever did was meet your mother. She's been great but you've been nothing short of wonderful."

"Shucks. You're going to make me cry, Josie."

She laughed and gave me a gentle shove. "I'm being serious here, Mark. You've seen me on my worst days, but sometimes all I've needed was a kind word from you, and my world be alright again. I'll never be able to thank you enough for that."

That weekend, we headed out together for the first time. She was dressed to impress as always while even I made an attempt at looking semi-decent. Mum and John didn't see anything wrong with us wanting to go out together. Our first stop in the city was to get something to eat, agreeing we wanted nothing more than a burger and a beer. What followed was nothing short of a pub crawl, taking in various establishments that were within walking distance, Josie not struggling in her heels, even after enjoying a few drinks.

We ended up in a club, of course, Josie proving she could dance incredibly well. I wasn't much of a dancer but having her pressed against me stirred some feelings in me that I knew I should probably keep suppressed. I knew she wasn't actually my sister, there was no blood shared, but we had been in a close relationship for the past few years. Turning that into something else might cause problems, and even though she was sending me signals, I knew I could be misinterpreting.

Making it home safely sometime early the next morning, we staggered inside, heading straight our bedrooms. Before heading into hers, she turned and hugged me tightly again, another soft kiss on my cheek. "Thank you for tonight, Mark. It's been a lot of fun," she whispered into my ear.

"You're welcome, Josie. I love you."

She leaned back and smiled. "I love you too."

Staggering into her room, she turned and smiled again before she slowly closed the door. Walking into my bedroom, I realised I probably hadn't told her I loved her very often, though we both knew that we loved each other. It felt nice to tell her and for it to just feel right.

We still had a couple of months left before graduating, with one more holiday break. A couple of weeks before said break, Mum and John sat me down and explained that Josie would be heading into hospital. They wouldn't tell me why, that it was something I'd need to talk to her about, but they just wanted me to be aware, that she wasn't sick or in any danger, but they couldn't tell me exactly what.

Sitting with Josie that same evening, relaxing back against the headboard of her bed, I broached the subject rather quickly. She could hear the concern in my tone and immediately sat up on her knees, gazing into my eyes.

"I have tiny tits, Mark," she stated bluntly.

I'll be honest right here. I knew she had tiny tits. I'd never seen her naked, but I was a young man who helped with chores around the house, in addition to working part-time, much like Josie did. I didn't check out my mother's underwear. I wasn't a weirdo. But I had shown a passing interest in Josie's underwear, merely out of curiosity, and I knew that her cup size was much smaller than my mother.

"So is that what Mum and John were talking about?"

"I've been saving money like crazy since the first day I started working at fifteen, Mark. And Dad promised to match every dollar I saved with two dollars of his own." She took a deep breath before taking both of my hands in hers. "I'm having surgery, Mark. I want a big pair of tits!" Her enthusiasm made me chuckle. "Does that make me shallow?"

"Of course it doesn't, Josie. If it makes you happy, that's all that matters. You've never mentioned any concerns about having a smaller chest though."

"They're not going to be huge, but big enough for... um... Well, I'll just be happy to finally have some cleavage to show off."

"How big?" I had to ask.

"I'm probably going to go up to a D-cup at most. I think they'll suit my frame."

"You'll be okay afterwards?"

"Nothing more than a little bed rest and taking it easy as my body recovers."

She went into hospital within a fortnight, and I was surprised that she'd told all our friends at school that she was going under the knife. I'd been told the actual operation itself would only take a couple of hours, but her recovery would be in the region of around six weeks. Mum and John had both asked me to help out. They didn't have to ask.

Josie came home the day after her operation, clearly in a lot of pain but she still managed a smile, and the new breasts were obvious. Whether she went with the smaller C or larger D option, she'd probably tell me later, but whatever size they were, the difference was obvious, and they completely suited her.

For the first couple of weeks, Josie couldn't really do all that much. I helped out where I could, bringing homework with me from school and we'd spend each afternoon studying. I knew she was still in a little pain. When it came to cleaning, she tried to look after herself, but Mum would occasionally have to go I and help.

She recovered quicker than anyone expected and was back at school and work after a month. She'd always been a confident young woman, but it was amazing how different she was now that she had a big set of tits on her chest. Her wardrobe changed overnight, with plenty of low-cut tops, and for some reason, she had no problem showing off the multitude of new bras she had, and the matching lingerie she'd bought for herself too. No modelling shows but it didn't take too much imagination...

"Mark?" she asked one afternoon when we were sitting in the living room after school, "Do you think I'm pretty?"

Dangerous question if ever I'd heard one. I mean, no-one would have considered her anything short of gorgeous. I was left thinking someone might have been teasing her. God knows why as I knew nearly every guy at school was now obsessed with her enhanced chest. "I think you're gorgeous, Josie. I thought that would have been obvious by now," I replied.

"Did you think that before I got my new tits?"

I met her eyes. "Give me some credit here, Josie. Your new tits were something for you. The men of the world are simply an added beneficiary of your new chest. But if you want complete honesty, I've always thought you were pretty, Josie."

Her face lit up before she wrapped me in a hug. "Thank you, Mark."

"Someone been teasing you or something?"

"No. I just wanted to know."

Life continued as it normally did. Mum and John were still working hard but gave Josie and I plenty of space. We were also working part-time in addition to studying, and when not studying or working, we generally spent most of our free time together, sometimes only as a pair, sometimes as part of our larger friend group.

It was perhaps a month before exams that things changed between us. Two out of the five days of the week, she would have the last block of lessons after lunch free, so she'd head home to get on with studying, and I'd arrive home a couple of hours later. I'd usually find her in the living room or her bedroom, head buried in a book.

Walking into the house after driving home from school, there was no sign of Josie in the living room or sitting at the table near the kitchen. Assuming she'd be in her bedroom, I dumped my bag in my bedroom first before heading to her door. It was wide open, and I was ready to just stroll in like I always did. But what I saw on the bed brought me to a halt.

A trail of clothing led from the doorway to the bed. On the bed was Josie, completely naked. Her new breasts were spectacular. It was the first time I'd seen them without being covered by at least a bra. But as I gazed down her body, it was what rested between her legs that had my eyes widening in surprise, as she was busy stroking an enormous cock. Far larger than mine. Her eyes were closed as she fisted it.

"Suck my cock, Mark," she moaned, "Wrap those lips around it and take it all the way to your throat."

She was thinking about me while masturbating? I'd surprised myself by not yelling out but watching her masturbate was simply mesmerising. I thought I should clear my throat or something, but if I saw my reflection, I probably stood there with my jaw wide open.

"I bet you'd love it when I finally fuck you," she groaned, her hand moving faster on her cock, "I'd love to cum deep inside you. You'll want nothing but my cock after I've been inside you that first time."

Okay, I have to be honest about one thing here. She must have seen my browsing history, because I was a young man and curious about certain things, and one thing I'd been curious about for quite a while were transwomen who loved to pleasure men, just like she was mentioning. As I watched her hand move faster and faster, I heard her breathing change, her moans grow louder as she was quite obviously reaching climax.

Cum fired from her cock all over her chest. It was an enormous load, over half a dozen thick ropes of cum firing from her cock. Once her cock stopped firing, she licked her hand cleaned and chuckled to herself. Opening her eyes, she turned her head and looked straight at me, not surprised to see me standing there.

"I wanted you to get home and find me, Mark," she admitted, "I needed you to know the truth."

"I had no idea..."

"Come closer, Mark. Sit on the edge of the bed."

Doing as she asked, I couldn't help looking up and down her body again. I'd always thought she was gorgeous, but I'd never seen her completely nude. We'd always been careful around each other, knowing we were only siblings due to the marriage of our parents, and we didn't want to disrespect each other.