Tales of Transwomen Tops Ch. 01

Enjoying a snack and a drink, we ended up heading towards the eastern suburbs and Bondi Beach, eventually stopping as the sun was starting to set, finding a pub that seemed rather popular. The food turned out to be excellent, and there was a friendly vibe, everyone enjoying a pleasant day and just wanting to enjoy themselves.

Returning towards the centre of the city by bus, it was the first time we broached the subject of previous relationships. She'd had a few boyfriends and even a couple of girlfriends. I noticed her watching me for a reaction. Shrugging, I told her I was open-minded about most things, and I remembered my time at university. Plenty of gays, lesbians, bisexual men and women around.

"What about trans issues?" she wondered.

The question caught me by surprise. "To be honest, I don't really give it much thought as it's never been something that's affected me. But I've always been a live and let live sort of person. Everyone has a right to be happy."

My reply seemed to be please her as she squeezed my hand and kissed my cheek again. "Knew I had a good feeling about you," she breathed into my ear, "Might have to reward you later for being a good man."

Kelli took the lead once we stepped off the bus, leading us towards Oxford Street. It was the main LGBT area of the city, though the inner-west was also known as a rather liberal, tolerant area, having change significantly after some stupid local laws had almost killed off the nightlife of the city entirely. I was a little surprised to be led by Kelli and had to ask why.

"Women sometimes feel more comfortable. I'm sure you can understand why," she said.

I did and simply walked by her side, feeling her fingers interlace with mine, glancing to see her look back at me, a smile on her face. I felt my heart beat a little faster as there was no doubting how beautiful she was. She led us towards a club, the line about two dozen deep. Thankfully, we didn't have to wait too long to get in.

"This won't put you off, will it?" she asked as the place was mostly full of gay men, though there were women around, assuming most would have been lesbians.

"Nope. We're here to have a good time. So is everyone else."

She turned me to face her and laid a kiss on me. It was our first kiss as she was certainly the aggressor, her tongue ending up in my mouth rather quickly, one of her hands ending up on my arse. Her breasts collided into my chest, which did make her stop kissing me for a moment. "Well, you're firm there," she giggled.

"Wow," I stated somewhat breathlessly.

"Wanted to do that since you stopped at my desk that night, Mike. Sometimes, just a little kindness goes a long way."

She kissed me again, moving my hands up and down her back before one ended up caressing her firm arse. She smiled while kissing me, eventually parting and heading towards the bar. We switched to spirits, a bourbon with mixer for me, a vodka and orange for her. Finishing those quickly, I found myself dragged up onto the dance floor. The music wasn't what I normally listened to, but it was easy to get into it, particularly with a beautiful woman like Kelli.

Quickly gyrating and grinding together, we could look around and see plenty of others doing the same thing. But most of my focus remained on Kelli, her eyes gazing into mine and, to be honest, I felt a little like prey in the eyes of a predator. I was left thinking she wasn't going to wait too long before we were intimate. Or she really just wanted to fuck. Either way, I probably wouldn't complain.

Moulding her body into mine, I loved the feeling of her hot breath on my neck and by my ear. "Mike, there's another reason why we're here tonight," she stated.

"What's that?"

Smiling at me, she kissed me hard again, both of her hands grabbing my arse as she almost smashed her groin against me. And that's when I felt something poking me. My eyes widened slightly as we continued to kiss, whatever was poking me getting firmer and, if I was right, larger. She finally broke the kiss and the hunger in her eyes was almost overwhelming.

Glancing down, I noticed the tent that had formed in her dress. Meeting her eyes again, there was no shame. No blush. Just that same hungry look in her eyes, with a slight curiosity.

"What do you think?" she wondered.

"Explains the trans question earlier on the bus."

"This is the part where most men will start freaking out."

Shrugging, I think I surprised her when I smiled and figured I might as well just be honest. "What do you think is one of the most popular porn categories is today?"

That made her laugh. "Ah, someone has dabbled, have they?"

Taking her hand, we walked towards the bar, ordering another drink, before heading towards a quieter area we could just sit and chat. Finding a comfortable leather couch, she curled her long legs, resting a hand on my chest, kissing me again. At least she tasted of orange rather than vodka.

"So... You like watching chicks with dicks?" she said, humour in her tone. I knew enough to know that transwomen could be called derogatory terms.

"I won't lie, I found it hot watching them fuck women at first. It's two women, just one has a big cock."

She smiled as her hand moved lower down my body, caressing my groin. "And what about a woman with a big cock with a man?" she asked, her lips close to my ear.

"I did eventually start watching those sorts of films too."

"Men fucking women? Or women fucking the men?"

"At first, it was the men doing the fucking. But after watching a couple of movies where they fucked each other, I started watching movies when the women were the only ones doing the fucking. Eventually loved watching threesomes, two women with a man."

"Ah, so one is fucking, and the other is having her big cock sucked?"

I met her eyes, and I could see the desire in them. "Yeah..."

Placing my hand at her hip, I moved it down to her thigh. She moved so her feet were now on the floor, opening her legs enough that I could run my fingers up the silk of her stockings. "Are you going to be naughty right now, Mike?" she asked.

"I had no idea you were trans, Kelli."

"And now that you know I am?"

"Will you be relieved to hear that I'm still interested in getting to know you better?"

She leaned over and kissed me hard as my hand ended up underneath her skirt, feeling the heat from her cock as I ran my fingers over the obvious tent in her panties. She moaned into my mouth as I ended up lying back slightly. Her words said very early in our friendship about being dominant were now ringing true.

"You want to see my big cock, Mike?" she asked softly, her fingers caressing my cheek as she gazed into my eyes, "Want to perhaps live out a fantasy or two?"

"I know porn isn't real, Kelli."

Her grin made me chuckle. "We can make it as real as you want. You like watching men being fucked by women with big tits and big cocks?"

"Something so hot about watching a girl just take charge and fuck."

"Most girls like me are not like that. But we're all unique. Some of us still love to use our cocks. And some of us still love to fuck men."

"Do you want to fuck me, Kelli?"

"I'm taking you back to my place tonight, Mike. You ever had a big cock inside you?" Shaking my head, she left a soft kiss on my lips. "I promise I'll be gentle before I send you to heaven."

"I have read that receiving can be even better than fucking sometimes."

She giggled, kissing me again. "Baby, I'm going to rock your world tonight and you're going to be craving my cock all the time."

"If it's that good, maybe we could have lunch in my office?"

"Or you can visit my cubicle, get under my desk, and suck me off while I'm working?"

"So... We're going to have a lot of fun?"

"Starting tonight, Mike."

Lifting herself off me, she stood up and offered her hand. Walking back into the crowd, we ordered another drink before she wanted one last dance, this time with Kelli grinding behind me, feeling her rub her cock against me, her hands running up and down my chest. "You seem comfortable with the idea already, Mike," she murmured into my ear, biting my ear lobe, "It might be different when you're naked, bent over my bed, with my hard cock between your cheeks, ready to slide inside you for the first time."

"You're a tease, Kelli!"

"I know, baby. Want to go?" Nodding, she turned me around and kissed me. "Okay. Let's go have some fun."

It was rather late, and while public transport was still available, I ordered us a taxi to take us directly to her place. We managed to behave ourselves during the ride, though she had my hand on her thigh, ensuring it was as high up her leg as possible without feeling her up too much. Arriving outside her apartment building a little later, she practically dragged me inside and into the elevator, pushing me against the side and kissing me hard during the short journey up.

As soon as we were inside her apartment, her hands were at work, getting me naked as quickly as possible. Leading me towards her bedroom, I was down to my underwear rather quickly. Finally coming to a stop, my hands found the zipper to the back of her dress, stepping back as it slowly fell to the ground.

Her breasts were large and spectacular, her areola not large and her nipples were rock hard. Her body was toned and firm, my eyes running down towards her groin. She wore a small pair of red panties, her thick and hard cock straining against the fabric. Her thigh-high stockings looked fantastic on her long legs.

"Holy shit," I muttered, "You're fucking gorgeous."

"Want to suck my cock, baby?" Meeting her eyes, I couldn't help smiling as I nodded. "On your knees then."

Getting on my knees, she stepped forward as I raised my hands to help take off her panties. Her thick cock popped free, and I was left amazed at how thick and long it was. It was certainly larger than mine, and I was left wondering if she was hung even when flaccid. Stepping out of her panties, I found myself just looking at her cock for a couple of minutes before I finally ran my fingers up and down the shaft. It felt warm to the touch. The head was quite large and already glistening with pre-cum. The shaft was thick, and I could see plenty of veins. Her balls were also big. The entire area was shaved smooth.

"Go on, baby," she whispered, "You know you want to suck it. I want to cum down your throat later. Then I'm going to spend all night fucking you. Want that, baby? This big cock buried in your arse later?"

"I'll certainly be living out a fantasy or two by doing that."

Stroking her off at first, it felt a little weird stroking another cock at first. She moaned softly as I used my other hand to gently cup her balls, gazing up to see her smiling down at me. "That's it, baby. Work the shaft but don't forget the balls."

I didn't stroke her for too long before finally lowering my mouth and licking the tip. She giggled as I wasn't being hesitant, I was just taking my time. Running my tongue up and down the shaft, it was the taste of a feminine cock. That might sound weird to most, but she was all woman except for what was between her legs. Moving down to her balls, I made her moan as I gave them attention, continuing to stroke her at the same time.

"Baby, you're turning me on even more," she moaned.

After giving her balls plenty of attention, I moved back and wrapped my lips around her cock for the first time. She moaned again as I used my tongue at the same time, remembering tips and tricks women had used when blowing me. I had no idea how long she was, but I could use my hand to stroke the rest of her cock that I couldn't swallow yet.

When her hand ended up on the back of my head, I gazed up her body and bobbed my head up and down on her cock, feeling how warm it was in my mouth, the slightly salty taste of her pre-cum, but the lust and desire in her eyes is what turned me on even more. I felt myself wanting to please her. And I always enjoyed making my partner cum.

Gagging for the first time, she pulled back and smiled at me. "We'll get you deepthroating my cock later, baby. Just focus on what feels good for now. You're going to make me cum soon." Pulling back, I stroked her off as she leaned down to kiss me. "You like sucking my big cock, baby?"

"Fuck yes."

"Good boy. Get it back in your mouth and make me cum. And you're going to swallow it all, aren't you, baby?"

"Every drop, Kelli."

Resuming my blowjob, both her hands ended up on the back of my head as she gently thrust as my head moved faster and faster. I used my tongue as best I could while sealing my lips even tighter around her shaft. She was soon moaning louder, and I knew she was going to cum soon enough. I couldn't wait to make her orgasm.

"Oh baby, I'm so close..."

I looked up to see her eyes closed, the head of her cock hitting the back of my throat, trying not to choke and gag as I knew her orgasm was imminent. Bobbing faster and faster, pulling back now and just focusing on the first couple of inches, she gazed down and I knew she was ready to fill my mouth.

"Fuck!" she cried, her fingers gripping my head as I felt that first throb. That was followed by a warm blast of cum filling my mouth for the first time. And I learned that she came hard, and the spurts were enormous, gulping down that first one only for the second to immediately spurt.

Drinking down her cum as quickly as possible, her cock throbbed again and again, her hands holding me in place as she moaned with each spurt that filled my mouth. I moaned with her as I was completely turned on by sucking her big cock and pleasing her in such a manner.

Removing her hands, I lifted my mouth from her cock, using my tongue to clean her up, before she lowered herself down and immediately kissed me, perhaps the most passionate kiss we'd shared up to that point, her thick cock continuing to poke me. "That was wonderful, baby. Are you sure you haven't sucked cock before?"

"Nope, that was the first time."

"But seen a lot of men sucking big cocks before?"

"Yeah. Even better if he's pleasing two or three at once."

Getting to our feet, she helped take off my underwear. I'd always known I was average, but to see that she was thicker and longer didn't actually make me feel any worse. I had a feeling I wouldn't be fucking her very much in the future anyway. And there was part of me that didn't care at all. That was a moment of revelation.

"On the bed, baby. Let me get a good look at that arse of yours."

Chuckling to myself, I positioned myself on my knees before leaning forward, feeling Kelli get on behind me. Glancing back, she smiled as our eyes met as she leaned forward, running her hands down my back as her cock was pressed between my cheeks. I moaned softly, earning another giggle from Kelli. "Feels good," I murmured.

"Ever played with your arse, baby?"

"A finger or two when jerking off, but never used a dildo or anything."

"So never had your arse eaten?" Shaking my head, she chuckled again. "I'm going to get you ready for me, baby. You're going to love having your arsehole licked."

Leaning back, she spread my cheeks, making note of the fact that I was relatively hairless myself. I'd never been a particularly hairy man. My chest had always been rather sparse, I kept my groin area smooth, and had never really worried about my arse. She squeezed and playfully slapped my cheeks before spreading them again and I felt her wet tongue gently playing with my rosebud.

"Holy shit," I cried softly as she immediately started to work me, "Oh my god!"

"Good, baby?"

"I had no idea."

Getting me into a better position, she really started to lick my arse as I felt another hand wrap around my cock. That made me moan as I was feeling incredibly sensitive, no doubt leaking plenty of pre-cum. When I felt her tongue work its way inside me, I moaned even louder. Fairly sure I even whimpered, the sort of sound I never thought I'd make.

When her tongue disappeared, I opened my eyes to see her leaning over the bed, opening a drawer and grabbing what I assumed was lube. I'd had anal sex with a previous girlfriend and knew what was required. Her tongue quickly returned though only for a couple of minutes before I felt the cool liquid poured onto me.

Kissing up my back, her fingers circled my arsehole, almost sensing her smile as I ever so slightly pushed back against them. "Good boy," she whispered into my ear, "First my fingers, then my big cock. Is that what you want, baby?"

"Yes, Kelli," I whispered back.

She paused a moment before adding, "I really like you already, Mike. I hope you love what we do tonight. I hope you'll want this again and again."

I tried not to clench when she worked her first finger inside me. I moaned softly again as her lips kissed my cheek, her cock positioned underneath me, resting against mine. Slowly fingering me felt rather nice, to be honest. She could feel I was comfortable and slid a second one inside me. Earned a louder moan, turning my head so I could kiss her properly.

"You want my cock, don't you, baby?"

"Soon... I like this right now."

Thrusting her fingers into me a little harder earned a few moans and a groan. When a third finger slid inside me, I started to move back against her fingers as she thrust them even faster. "Oh fuck," I groaned.

"That's it, baby. You're nearly ready for me."

"Feels so good..."

She kept fucking me with her fingers for a few more minutes, her lips against my neck, feeling her nibble into my skin as she breathed against my ear, talking dirty about all the things she'd love to do with me in the future. Sensing I was now ready for her, she sat back and removed her fingers, keeping my eyes on her as she lubed up her cock.

Getting into position, she teased me by rubbing her cock against and between my cheeks. Meeting her eyes, she smiled as I felt her press the head of her cock against me. Nodding firmly, I felt my arsehole slowly start to spread as the thick head of her lubed-up cock started to slide inside me. I thought it was going to hurt far more than I did, but that's why she'd licked and fingers me first.

Running her free hand up and down my back, she pushed my lower body a little closer to the bed as the head of her cock slid inside me. Moaning softly, she leaned forward to leave a soft kiss on my shoulder as she started to slide a little more of her cock inside me.

"Fucking hell," I moaned softly.

"You're loving it, aren't you, baby?"

"I had no idea it would feel so good."

Kelli took her time sinking her thick cock. There was a little discomfort as it was something I hadn't had before, but it was amazing how quickly it felt really good at the same time. I let her maintain control, but when I felt her body press against my butt, I knew I'd taken her entire length. "Oh fuck," I whimpered.

Yes, whimpered.

She started to slowly thrust, feeling her pull back, only the head of her cock remaining inside me, before she slid forward again, my cock throbbing as her cock seemed to be massaging my prostate. I hadn't even considered my own orgasm just yet. Sitting back, I felt her hands at my hips as she started to thrust a little faster.

"Fuck, baby. You're so tight. Been a long time since I had a nice virgin arse to fuck."

I could barely get a word out as she thrust a little quicker. The sensations flowing through my body were unlike any I'd felt before. The tingles around my arse had me thinking I was going to cum. My cock continued to throb. I was fairly sure I was absolutely leaking pre-cum. Kelli occasionally slapped one of my cheeks, which made us both chuckle. I knew the position I was in would be seen as completely submissive.

Again, I didn't really care as I was already enjoying it far too much.

"Fuck me," I moaned, "Fuck me, Kelli."