Tales of Transwomen Tops Ch. 08

"I've always been a girl, Mark. Dad's been my biggest supporter. He let me start living as a girl from a very early age. Mum hasn't been as understanding, yet when it all happened, she was the one who chose my name. I wasn't old enough to make the decision myself. She liked the name Josephine, and for me to have everything changed legally, that was the price. What doesn't help my relationship with her is that the newest boyfriend is both homophobic and transphobic. At least he doesn't know that I might look like a girl but obviously has a big cock. It's why I don't really talk to her anymore."

"It is rather impressive..."

"And I guess you heard everything I said?"

"I had no idea you felt that way."

"You're an idiot, Mark. I've been in love with you for a long time. I just couldn't figure out how to approach you with my secret, particularly the longer things went on." Sitting up, I almost laughed as the thick cum on her chest started to roll down her body. "I know how you feel about me. Or I did until this moment. Does me having a big cock change anything?"

"No. I've loved you for a long time too, Josie."

"Like how I've loved you?"

"Exactly the same, if I'm hearing you correctly."

"I'm guessing we're both virgins, Mark. I want you to be my first. But as you would have heard, I know you might need time to think..."

"You can fuck me if you want, Josie. I think the idea of my sister fucking me is a real turn on."

"Would you like to touch me now? My cock is all lubed up, though there's also cum too..."

Wrapping my hand around another cock for the first time was an experience in itself. Her cock was thicker than mine, definitely longer than mine, and it felt incredibly warm in my hand. As I slowly started to stroke her, I watched Josie's face, the grin that formed before she leaned forward to kiss me properly for the first time.

"I'm guessing we've both kissed people at least," I said after we broke apart.

"I've kissed a few girls. No-one at school knows I have a big cock though. Only three people now know my secret."

As I continued playing with her, I asked, "Mum knows?"

"Of course she does. Dad and I sat down with her very early on and told her the truth. Your mother assured me my secret was safe and that you would only be told by myself when I felt the time was right."

Continuing to stroke her cock, we kissed again as I moved to sit in front of her on my knees. I learned very quickly that Josie was an excellent kisser, and considering what I assumed was her sexual personality, she was always trying to take charge while kissing me. "Want to suck my cock, Mark?" she finally asked, "Not until I cum, but maybe you'd just like to try."

"Do you want to make love eventually?"

"I've been waiting for the right time, Mark. I'd do it now, if we could, but our parents will be home soon."

Kissing her again, she rested back on her elbows as I moved my position, so I was comfortable as her cock was at eye level. It looked even bigger from that position. She kept everything nice and smooth. Her balls were quite large, also hairless, like the rest of her body. Running my tongue up the shaft, there was a mixture of flavoured lube and what I assumed was her cum.

Wrapping my lips around the thick shaft earned a moan of approval, her hand immediately running over my head as she moved her hips, the tip of her cock quickly hitting the back of my throat. I was surprised I didn't gag as I'd seen enough porn to figure out what to do.

"That's it," she groaned, "Suck my cock, Mark." Gazing up into her eyes, she gazed down at me in return. "I won't cum again... You like my cock in your mouth?" I managed a nod as her fingers ran through my hair. "It'll feel even better when it's in your arse. I've dreamed about that moment for so long..."

I ended up sucking her cock for quite a while as I thoroughly enjoyed every second of it. The only reason we stopped, as I was hoping that she would eventually cum again, is we heard a car in the driveway, and we didn't particularly want to be discovered just yet. Taking my mouth from her cock, we shared one last incredibly passionate kiss before I return to my bedroom, shutting the door so Josie could get dressed.

That night, I was lying back in bed, playing with my phone, when Josie snuck in. It wasn't the first time she'd done that, but any previous time had been completely innocent. We'd sometimes lie together for a while, but she'd always return to her own bedroom to sleep. Closing the door behind her, she had me smiling rather quickly as she stripped naked, her thick cock swinging between her legs as she slid under the sheets to join me.

"I'm going to be naked more often so you get used to me and my big cock," she whispered into my ear, "But I was hoping you could finish what you started this afternoon?"

"Want me to make you cum?"

"Yes. And I'm hoping you'll swallow everything too."

Stripping off myself, her fingernails raked down my chest and the smile was one of approval. Lowering my underwear, she wrapped her fingers around my cock and kissed me. "I'll jerk you off when I finally fuck you, Mark," she whispered.

Sliding off the bed, Josie moved to sit on the edge, her thick cock now hard, the tip glistening as I had a feeling that she'd worked herself up before arriving in my room. With my hand around the base of her cock, I didn't hesitate in taking her cock in my mouth again. She whimpered softly as I had my head bobbing up and down quickly. Gazing up her body, I used my free hand to either fondle her balls or give her breasts some attention. They were still quite firm after her surgery.

Moaning again, I was surprised at my lack of gag reflex, so when I felt her cock slide into my throat, she moaned even louder as her fingers gripped the back of my head tighter. "Yes, Mark!" she exclaimed, "Oh my god, it feels so good."

In all my fantasies I'd had about Josie, most of the time it had been of her with a pussy, and I'd make love to her. But with my curiosity and discovering there were women out there who had a cock, I'd also daydreamed about Josie having a big cock that I could play with. In addition to that, I'd usually thought of being the more submissive should she had a cock. Not sure why that appealed so much.

"Oh fuck... Mark..." she whimpered, "You're going to make me cum."

That was the general idea of sucking her cock but hearing that I was turning her on so much, I doubled my efforts and Josie seemed to realise that. Her fingers gripped even tighter, and I knew she was getting close. Hearing her whimper turned me on even more, and when I felt her cock start to throb in my mouth, I knew she was getting close.

"Fuck..."

Feeling that first spurt of hot cum fire into my mouth still caught me by surprise despite being aware that her orgasm was imminent. Sealing my lips tighter, her hand held me in place as my mouth was flooded with her thick cum. I swallowed what I could though each spurt seemed to be immense in volume. I did choke once but I was a trooper and wasn't going to disappoint her.

When she finally stopped spurting, I had to sit back and catch my breath. Sliding off the bed, she kissed me again, our tongues duelling playfully, as her fingers wrapped around my cock. As horny as I was, it took all of a couple of minutes before I came all over her. "Bet you feel better now too..."

"Bet my orgasm will feel even better when your cock is inside me, Josie."

Her face lit up again, hugging me tightly, feeling her still hard cock pressing against me. "I'm so happy that you love me as I am."

"I was going to love you regardless."

She was reluctant to leave the room and I was reluctant to let her go. Quickly discussing our options, I was the first to suggest that we just sit my mother and John down and explain the situation. She was silent for a couple of minutes before asking me to just wait a little while. She didn't want to keep any sort of relationship secret for too long but knew it would be a shock to both of them.

Waking up alone the next morning, I thought the previous night had been a dream until I opened my bedroom door, wandering to Josie's door, which was already open. She was awake, lying back on her bed, and the smile she gave me told me it hadn't been a dream. Getting to her feet, she skipped across the room, her body crashing against mine. The pair of us hugging wouldn't raise eyebrows. We'd always been affectionate with each other.

I think Mum knew straight away something had gone on between Josie and I as she had that look on her face I recognised. It wasn't a look stating I was in trouble. It was a look suggesting she could read me quite easily and that I had something to tell her. But Mum was also good about those sorts of things, allowing me time to approach her. She'd always done that unless she thought it was something I shouldn't keep a secret for too long. As for John, I'm not sure what he was thinking...

For the next couple of weeks, Josie and I would get together whenever we could. Most of the time, it was nothing more than a lot of making out, but that would also lead to me giving her a handjob, and I probably ended up on my knees, her cock in my mouth, at least once every couple of days. We would also sneak to each other's rooms, and she didn't take long in showing an interest in my arse.

I did enjoy it when she had me lie on the bed and she would rest on top of me, feeling her cock between my cheeks. Otherwise, I'd be lying on my back, and she'd stroke us off together. She did like to lube her fingers and play with my rosebud at the same time.

"Slide one in," I finally told her within a week of her first touching me there.

"You sure?"

"You're going to stick your cock in me eventually, Josie. Might as well get me used to having things inside me."

With her right hand still stroking our cocks together, she slid her index finger of her left hand slowly inside my arse. It felt a little weird at first, but I surprised myself by being rather relaxed about it. Josie couldn't stop smiling as she slowly fingered me while stroking us off. Within a couple of minutes, I asked her to slide a second finger inside me and to go nice and deep.

"Someone's been reading," she whispered.

"Been watching videos of beautiful women with big cocks making love to their men."

Two fingers felt wonderful, and Josie was rather excited when I was the first to cum. She milked my cock dry before focusing on her own orgasm. Removing her fingers, she moved up my body until she was sitting on my chest, her cock almost near my mouth before she moaned and erupted. She'd given me a couple of facials, though I much preferred taking her cum in my mouth, but she must have been rather turned on as she absolutely coated my face.

Feeling her move as my eyes were closed, she ran her tongue over my face, both of us chuckling before I could finally open my eyes, my legs wide so she could lie between me, feeling her cock poking me again as it usually did.

"I love you," she whispered, kissing me softly, "I can't wait until we make love."

"Me too..."

We agreed to tell our parents about our secret relationship once we finished exams. I think we both felt guilty about all the sneaking around, so agreed to cool things during the exam period, not wanting distractions, then we'd sit down with our parents and confess, before we'd finally make love.

At least we finished all our exams feeling confident that we'd done well. Having applied for universities in our home city, we did hope to remain living at home as we continued to study. The night after our final exams, Mum and John treated us to dinner at our favourite restaurant. All four of us dressed to impress, suggesting we'd go out for drinks after dinner.

Conversation flowed easily during our meal, Josie and I swapping the occasional glance. It was only after we'd finished dessert, the four of us sipping at a coffee each, when she finally cleared her throat.

"Dad. Caroline. Mark and I have something to tell you."

"We already know, sweetheart," John stated, Mum smiling at me before turning her smile towards Josie, "You're not as subtle as you think you are." John then looked at me. "Thank you for being so accepting of my daughter, Mark. I know it's the modern world and all but there is still a lack of understanding and intolerance."

"All we want is for you to be careful," Mum added, "Mark, I've never wanted to impose but..."

"I'm still a virgin."

"So am I," Josie added, "We're going to take things slow. The only question I have is if you think it's weird?"

"Not at all," John replied, "You only met each other for the first time when you were both twelve and, though we are family, there is no shared blood. And stepsiblings falling in love probably happens far more than people would care to admit. You live together, spend a lot of time together, and you've been good friends since you first met. Falling in love with each other isn't a crime and, most importantly, you have our blessing."

"We do?" I asked in surprise, as I was expected at least some sort of argument.

"Of course," John replied with a smile, "You love my daughter, Mark. That's all any father wants for his daughter, to find a man worthy of her love. And considering you're a fine young man I know so well, neither your mother nor I will stand in your way."

"The only thing we'd ask of you is to let us get used to you being together as a couple when we're at home," Mum added, "But we have no problem with you spending the night with each other."

"Really?" Josie asked excitedly.

"You're eighteen and in a relationship. We're going to treat you like the adults you are," John replied.

Heading to a pub for a couple of drinks afterwards, our parents didn't stay for too long, Josie whispering into my ear that she wanted to go dancing before going home. John escorted Mum outside to a waiting taxi as we headed further into the city, arriving at a club we'd visited before. We stuck to water as we spent a couple of hours gyrating together. She loved to press her body against mine, though I knew she kept her cock tucked when we were out in public, so I didn't feel any erection pressing against me.

After working up a sweat, and a lot of making out and turning each other on, she whispered into my ear that she really wanted to take me home to fuck me. I'd been ready for her to do that for ages by now, so I practically dragged her out of the club, my other hand busy organising a taxi to take us home. We managed to behave ourselves when sitting together during the drive, but once we pulled up outside, I was dragged inside straight towards her bedroom.

Making sure her bedroom door was shut, we resumed making out, stripping each other naked as quickly as possible. Getting on the bed, I laid down as she spun around, groaning as she took my cock in her mouth while hers ended up down my throat in a matter of seconds. She'd blown me a few times and we'd already enjoyed more than one sixty-nine, but we both knew this was simply the entrée to what would be the main course afterwards.

I didn't last too long, as horny as I was, so I ended up on my knees on the floor with Josie on the edge of the bed, slowly making love to her cock with my mouth. I'd already promised her that I would suck her cock whenever she wanted as I just loved pleasing her and making her happy. Gazing up into her eyes, she smiled lovingly down at me, and I finally earned a tasty load to swallow down.

Making out and waiting until we were both hard again, we whispered our love for each other more than once, unable to stop smiling at each other. Now that our parents knew the truth, we knew we'd have to tell all our friends. Most probably wouldn't be surprised. Hell, more than one had already insinuated that we were already fooling around.

"Going to lube you up, Mark," she told me, "Are you ready for me?"

"Been ready for this from the first time we fooled around, Josie."

She had to get me ready first, surprising me when I ended up on my knees with my head on a pillow, as she used her tongue on me. It wasn't the first time she'd eaten my arse, as she loved to use her fingers and tongue on me while stroking me off. As much as I loved to make her cum, she loved to make me orgasm in return. She was a very generous lover.

It didn't take her too long to get me ready, and being honest, I finally wanted to feel her inside me. Turning over onto my back, she made sure I was comfortable, my legs spread nice and wide so she could easily fit between them. We were both lubed completely so she was going to slide inside me easily but we both knew the first time wasn't going to be entirely painless either.

"I'll be as gentle as I can," she said softly, pressing the head of her cock against me.

"It's fine, Josie. We've both been looking forward to this for weeks."

Leaning down to kiss me, we whimpered together as the head of her cock ever so slowly started to slide inside me. The head of her cock was quite large, so it took a little time for just that to gently force its way inside me, moaning into her mouth once it finally popped inside me. Josie broke the kiss and smiled, her lower lip trembling slightly as I caressed her cheek, gazing down between our bodies to watch her slide the rest of her big cock inside me.

Once the entire length was buried a couple of minutes later, we kissed again as I moved my hands to her back, stroking her smooth skin. "I can't believe I'm finally inside you," she whispered, "How does it feel?"

"Fucking wonderful, Josie. Ever since I walked in on you that afternoon, I've also dreamed of this moment."

"I love you so much."

"This is it, Josie. We were both virgins until this moment, and I know right now, I want no-one else."

Slowly thrusting into me, I stroked my cock at the same time, keeping it nice and slow and timing it with each of her thrusts. When she moved her hands to rest underneath my knees, she pushed my legs back and started to thrust a little faster. Stopping to lube up again, just to be safe, she was soon thrusting away quicker, and I'd never felt such bliss in my life. Watching my stepsister sliding her cock inside me every couple of seconds was nothing short of fantastic, and from gazing at her face, I knew she was loving it too.

My legs ended up over her shoulders as she leaned forward and really started to drive her cock home. "Fuck yes!" I moaned softly.

"Your arse is mine, Mark. You love my big cock?"

"Fuck yes, Josie. Your cock was just made for me."

"Like your arse was made for mine."

It certainly was as I'd stopped stroking my cock, but I still came hard while she was busy fucking me. Feeling me squeeze her cock with my arse excited her even further as she started to pump my arse even more, now eager to enjoy her own orgasm. Those last few minutes were difficult as I wasn't used to be fucked yet, but I wasn't going to stop her from enjoying her own orgasm, and despite some lingering pain, feeling her cock thrusting into me far outweighed any small amount of pain.

"Fuck... Gonna cum, baby," she groaned before I felt her cock start to throb and a warm sensation in my arse. Her cock throbbed over and over again as she filled me to the brim before releasing my legs and collapsing on top of me, moving my legs so I could wrap my limbs around her body.

"Okay, we're doing that all the time," I whispered, making her chuckle as she cuddled me in return.

"I'm glad you're okay with this."

"Why wouldn't I be? I'm with the woman I'm madly in love with, and I can say, hand on heart, that I absolutely love the feeling of her big cock inside me."

Lifting her head, she kissed me hard. "You're right about one thing, Mark. We're definitely doing this all the time."

Feeling her pull out was disappointing, snuggling together as I ended up as the little spoon. Though we could have definitely kept going, we had been out for a long night together and, as soon as we both yawned, we knew the fun was over, but there was no rush to just fuck each other senseless. We had the rest of our lives together.