Tales of Transwomen Tops Ch. 01

She slapped each cheek a little harder before she started to thrust a little harder. That earned a few groans from me as I reached under to finally start stroking myself. My cock felt so sensitive, Kelli leaning forward the same time. Resting on a forearm, she reached underneath and took over stroking my cock.

"Let me, baby. I want you to cum with my cock buried deep in your arse."

"Please," I whispered, "Keep fucking me, Kelli."

I was fairly sure she was still holding back, being my first time and all. It did hurt occasionally, particularly as she picked up the tempo of her thrusts. Her fingers caressed my cock, almost trying to milk me of my cum, her lips kissing all over my cheek, still breathing near my ear. "Cum for me, baby," she whispered into my ear, "Cum for Kelli. Cum for the girl who now owns your arse."

She wasn't wrong. I already knew this wasn't a one-time thing.

"Oh fuck!" I cried out, Kelli giggling as I exploded in her hand. Moaning and groaning, I couldn't remember a stronger orgasm in my life, Kelli continuing to pump me, which helped heighten my orgasm even more. "Oh fuck, Kelli. Keep fucking me."

"I will, baby. You made me cum earlier. I'm going to last a while fucking you now."

Relaxing as her hand moved away, I felt her reposition herself, the angle of her cock changing, as she seemed to mount me. Her breasts pressed into my back as she slowly started to drive her cock faster and deeper, really starting to fuck me. I was soon grunting as she fucked me hard, her moans joining int the cacophony of noise. The sound of her cock plunging into me was an even bigger turn on, my cock remaining rock hard as I was loving every second of it.

Turning my head, she kissed me hard, driving faster and faster, moaning together. We only broke the kiss when needing to take a breath before kissing again, her cock driving deeper. I was already of the mind that I would want this with her all the time. If our first time was this good, it was only going to get better in the future.

"Oh baby," she exclaimed, "Oh baby, going to fill you up soon."

"Fill my arse all the way up, Kelli!"

She giggled before kissing me again. "Good boy. Kelli will definitely enjoy filling your tight little arse, Mike."

Those last couple of minutes before orgasm was some of the best sex I'd ever enjoyed, Kelli slamming her big cock faster and harder with each passing half-minute. I was adamant that I felt her cock starting to throb as her orgasm hit, and I smiled as I felt a warm sensation start to fill me as she started to cum again.

"Oh yes, baby!" she cried, "Take my cum, Mike!"

"Fill me up, Kelli," I moaned, loving the feeling her cock throbbing, feeling each spurt of cum, "Fuck, that's so hot feeling you cum in me."

She kept pumping me long after her orgasm had passed, eventually stopping though leaving it buried inside me as I relaxed on the bed, and she pressed down onto my back. "How was that, baby?"

"Kelli, that was the best sex of my life!"

Remaining silent, she asked softly, "Really?"

"Really. I loved it, Kelli."

Feeling her pull out, I rolled onto my back as she leaned forward between my legs and kissed me. Wrapping my arms and legs around her, she smiled as her cock rested next to mine, eventually raising her head as we gazed at each other. Sitting back on her knees, I laid there as she applied more lube to her cock before she spread my legs wider, leaning forward to grab a pillow, placing that underneath my butt.

Pulling my legs back, she lined up her cock and slid it back inside me. Moaning softly, she didn't stop until she was buried once again. Leaning down to kiss me, we moaned in unison as she slowly started to thrust, releasing my legs as she held them in place with her upper arms.

"That's it, baby. Just enjoy it," she said softly, "Enjoy Kelli's big cock. You love me being inside you?"

"Fuck yes."

"I knew you would."

"Love being inside me?"

"I jerked off every night this week, thinking about doing this with you, Mike. Covered myself in so much cum each time."

"You take video and pictures?"

She smiled, kissing me again. "I'll send it all to you, but I plan on fucking you far more than needing to jerk off from now on."

"Sounds serious, Kelli."

She slammed her cock into me nice and hard, making me grunt but I smiled. "I don't just fuck any man, Mike. I only fuck those I really like."

"Well, I think you should keep fucking me then, Kelli."

That earned another kiss as she pushed my knees back further and really started to pump me again. Resting my hands on her back and upper back, I stroked her soft skin as I gazed down between us, my cock hard and leaking pre-cum again, watching as her cock worked my arse nice and hard, disappearing and reappearing.

"Love the view, baby?"

"Oh yeah. Never thought I'd see a big cock on a beautiful woman sliding inside me."

"Can't wait to cum in you again, baby."

"Fuck me for as long as you want, Kelli."

She giggled, leaning down to kiss me again. "Might have to invite you over more often."

"Or you can come to mine and fuck me in my bed too."

We both went quiet as she focused on fucking me and I just savoured the feeling of her cock plunging deep. I was tempted to stroke myself, but she must have read my mind, whispering that she wanted me to cum without touching myself, adding that we'd figure it out together so I'd cum hands-free more often than not. I loved the sound of that, my body being so turned on from her fucking me that I'd just cum.

Realising I was getting rather desperate for orgasm, she eventually relented and stroked me off, giggling as I came within a minute. My legs ended up over her shoulders as she started to fuck me harder, both of us smiling as we both wanted her to cum in me again. Leaning down to kiss me, I was amazed at how flexible I was proving to be.

"Fuck me," I whimpered, "Keep fucking me."

"I will, baby. But don't you worry your sweet little arse, we're going to be doing this a lot more in our time together. I love to fuck and you're exactly what I was looking for."

"I had no idea I was looking for a girl like you, Kelli."

"Thank you, baby. Now get ready as I really need to cum in you again."

Feeling her cock throbbing as she deposited another load had me smiling at her, gazing into her gorgeous eyes as she groaned softly, needing to kiss me hard as she pumped away until she finally had to stop and relax, releasing my legs so I could wrap those around her. She giggled, suggesting I was enjoying the feeling of her cock inside me far too much.

She wasn't wrong, to be honest.

Pulling out, she sat back on her knees again and I licked my lips as her cock was glistening with cum and lube, and I'd seen more than one video of a man happily sucking a cock that had just been inside him. She read my eyes and leaned down to kiss me. "You want to suck my cock again, don't you? And after it's just spent so long in your arse? Naughty boy."

We were in desperate need of a shower, Kelli dragging me to her modern bathroom, washing each other up and down. Kelli did warn me that I would likely wake up with a dull ache in the morning though assured her I actually felt pretty damned good considering it was my first time. Returning to her bed once we'd dried off, we changed one of the sheets as there was quite a large cum stain, before we cuddled together. To my amusement, I ended up spooning back against her.

"I'm obviously not your typical woman in my ways, Mike," she said, her hard nipples pressing into my back, feeling her rub her cock against my cheeks, "And I might just want to wake you up by sliding my cock inside you again in the morning."

"Quite the alarm."

I think we fell asleep at roughly the same time. It had been a long day and night, and I was exhausted. Waking up in the morning, I wasn't surprised that Kelli was poking me in the back. Turning around, she didn't wake up at first as I gently stroked her cock. I only knew she was awake when she giggled while I was pleasing her with my mouth, throwing the sheet back before she rolled onto her back.

Gazing up her body, she smiled as I bobbed my mouth up and down. "Someone wants a morning treat," she stated.

I got my treat rather quickly, taking the first couple of spurts in my mouth before I'm sure I surprised her by taking a couple of spurts on my face, using my mouth to then clean up her cock. Moving up to straddle her lap, I leaned down and kissed her, Kelli using a finger to clean my face and feed me her cum before she grabbed the lube and applied some to her cock then my arse.

Lifting myself up, I pressed the head of her cock against me and, though I hadn't been prepared, I managed to take the head inside me without it hurting too much, slowing sliding down the rest of her length, savouring the feeling of her big cock being back inside me.

"Love watching a man enjoy my cock so much," she said softly.

Once she was buried, I slowly rode her, my face no doubt lighting up as she felt as deep as ever inside me. Stroking myself at the same time, I erupted all over her chest within a few minutes, earning another chuckle as she suggested I must have been rather excited. Leaning forward to kiss her, I felt her hands end up on my arse as she started to fuck me while I continued to ride her big cock.

"Fuck yeah," she groaned, "Going to pound your arse then we'll have breakfast."

I definitely surprised her by eventually rolling off her and got on my knees, leaning forward. She moved ever so quickly, sliding her cock deep and mounting me, immediately fucking me nice and hard. "Think he knows what he really likes. A girl with a big cock buried in his arse," she grunted, hands on my shoulders as she fucked me hard and fast.

"Helps when the girl is also fucking hot," I groaned in reply, "And she sure knows how to fuck!"

No idea how long she fucked me until I felt her filling me up again, collapsing on my back once her cock had stopped throbbing. Lying flat on the bed, she continued to slightly move, earning soft moans from me as her cock remained hard, leaving soft little kisses on my cheeks and neck. "You hungry, baby? For something other than my cock and cum."

"Yeah, I could do with some food."

We eventually agreed to head out for breakfast, enjoying another shower together, though I ended up on my knees as I wanted her cock in my mouth again. I didn't make her cum as she wanted to be aroused through breakfast. Getting dressed, she put on a pair of jeans and a t-shirt, putting her hair in a ponytail, she looked fantastic. I had to wear the same clothes as the night before. We found a little place not far away that sold food all day, and there was no doubt that we shared an attraction but were both already thinking of perhaps something more than just sex.

After we ate, we walked to the nearest train station as I needed to get home. It was the first time that Kelli wasn't the happy, smiling, bubbly herself. When I hugged her, she held me ever so tightly in return. "I loved last night," she whispered, "Will you want to do it again?"

"Kelli, I'm already thinking about how often we'll be seeing other outside of work this week." Leaning back, I caressed her cheek as her bottom lip trembled. It was the first real sign of vulnerability. "Opening your heart up isn't easy for anyone," I said softly, "But I guess it's harder for a girl like you sometimes?"

"I really like you already, Mike."

"Feeling is mutual, Kelli." Taking her hand, I squeezed it. "I really want to see where this goes."

"See you at work tomorrow?"

"I'm going to call you tonight just so I can hear your voice again."

That earned me a kiss. One hell of a kiss. Passionate but her eyes now reflected another emotion that I knew I was feeling already. There were no rules about the heart and falling in love. We hugged and kissed until my train was about to arrive. I didn't check my phone on the way home, only checking it once I was inside, sitting back on my lounge.

I wasn't surprised to see a few messages already, opening a couple of pictures, her cock appearing o my screen, with a message stating on each that she was already missing me. Following that was a video of her jerking off, figuring she must have been doing it for a while, as she came rather quickly, making me smile when she moaned my name more than once.

Walking into work the next day, I wasn't one of the first to arrive. Kelli was already there, stopping by her desk. Her eyes lit up when she sensed my presence. Asking her to join me, no-one paid us much attention as we walked into my office. Closing the door, I made sure the blinds were shut but the windows provided a great view of the city.

That first kiss was something else, surprised she wasn't immediately poking me, though I'd done a little research, figuring she probably tucked herself while at work. "I'd love to bend you over this desk right now and leave a load of cum in you," she breathed into my ear.

Checking my watch, we had twenty minutes. "How about you take a seat in my chair and I suck you off?"

"Oh baby, you're so good to me already."

She wore a blouse, skirt, stockings and heels. Removing her skirt showed off where the thigh-highs ended, pulling down her panties to free her already growing cock. I played with it until it was at full length and thickness, my mouth watering at the idea of having it inside me again. "Fuck, I love your cock already," I groaned as I ran my tongue up it.

"Suck me, baby," she groaned, pulling my head down as her cock slid in my mouth, "Going to give you a nice load to enjoy rather quickly. And I think we should incorporate fucking into our lunchtime from now on."

My head was quickly bobbing up and down on her cock as she relaxed back, happy to watch me work. She undid her blouse and played with her tits as I ran my hands up and down her legs before gently playing with her balls. She loved that, moaning softly, and when her hips did start to move, I already knew she was getting close.

I savoured every spurt of cum that erupted from the head of her cock, making her smile as I made sure I gulped it all down. Once her cock stopped throbbing, I sat back as she leaned forward to kiss me. "Now that's a wonderful way to start the day, baby," she said softly.

"I could wake you like that whenever we sleep together."

She giggled, kissing me again. "We'd never get to work as I'd just want to spend the rest of the day fucking you."

"I'm owed a lot of sick days... And as I'm management, I could state you're assisting me."

Standing up, she tucked her cock away, put her skirt back on, and we shared another kiss. "Come to my office for lunch," I stated, "I'll order in some food."

"Let me know when you want me here, baby."

Somehow, I managed to concentrate on my work the entire morning, getting into the usual flow. I did find myself thinking about Kelli from time to time but only brief moments. I was busy reading over a report when there was a knock at the door, glancing up to see Kelli in the doorway. She was holding a bag of food in her hand, I guess taking care of the lunch situation.

Closing and locking the door, we ate lunch first, a light meal that wouldn't be too heavy in our stomachs. We didn't eat too quickly, though the glances we shared across the desk suggested we had other things on our mind. As soon as we finished, she walked around the desk as I stood up, our mouths colliding as she worked quickly on my belt then my trousers.

As soon as they were around my ankles, she bent me over my desk as I heard her skirt hit the floor. Grabbing her handbag, I felt the application of lube before I looked back to see her crouching down, her tongue quickly getting to work. That was followed by a couple of fingers, sitting up and leaning forward to kiss me as she didn't waste time getting me nice and ready for her.

"You ready, baby? Ready for my big cock to slide inside you? Ready for me to fuck you in your office?"

"Fuck me, Kelli."

We groaned together as she didn't take long burying her thick cock nice and deep, hands at my hips, thrusting away quickly. We had to keep the noise down but it's rather difficult keeping quiet when you're being fucked nice and hard by a beautiful woman. She leaned forward, resting a hand to either side of me, as she started to drive her cock harder and harder.

"Oh fuck yes," I whimpered, hearing her chuckle as I couldn't get enough of her, "Nail me, Kelli."

"Oh baby... You feel so good around my cock."

She fucked me for around ten minutes before pulling out, turning me around so I could sit on the desk, arse hanging off the edge as she slid inside, legs over her shoulders, slamming my arse harder and harder. When I climaxed all over my shirt, I groaned loudly, Kelli leaning forward, kissing me to keep me as quiet as possible.

"Cum in me," I moaned, "Fill me up and I'll carry around your cum the rest of the day."

"You're so sweet to me, baby."

She fucked me for as long as she could before I felt that already familiar warm sensation as she came inside me. Kissing each other again, I rested my hands on her shoulders as she continued to pump away into me. "I love your cock," I moaned, "How am I this addicted to it already?"

"Because it's attached to me, baby," she replied, continuing to drive nice and deep.

We only stopped because I looked at the time and realised the lunch break was nearly over. Pulling out, she surprised me by taking a toy out of her handbag. I recognised it immediately and smiled. "You want me to wear one for you?"

"Do you want to, baby? Keep you nice and ready for my big cock all the time."

"I'll wear it for you, Kelli."

That earned another kiss before I felt her gently slide the toy inside me. When she saw me smile, she giggled as she knew I was already enjoying it. Quickly getting dressed, we wiped down everywhere required before I walked her to the door. Sharing a last, soft kiss, there was a look in her eyes I'd already seen. I'm sure I looked at her in return the same way.

"Want to come around for dinner tomorrow night?"

"I'd love to. Should I bring a bag?"

"You'll be coming to work with me the next morning, so I'd definitely bring a bag."

We didn't fuck at lunchtime the next day, heading downstairs to the diner we were already calling our own. I wouldn't call it romantic though we leaned closer, holding each other's hand. I was still captivated by how beautiful she was. The waitress tried not to interrupt us too often though had already mentioned that we made a cute couple.

Leaving the office later that day, she enjoyed the walk from the train station to my apartment. After giving her a brief tour, I took her out to the balcony after grabbing the bottle of wine I'd had chilling in the fridge. Enjoying a make-out session, I eventually led her to the kitchen so I could finish cooking dinner I'd started preparing earlier that morning.

The moans she made while eating made me smile as she seemed to enjoy what I'd cooked, finishing up by serving a simple cheesecake, that I hadn't actually done myself. Adjourning to the living room after starting the dishwasher, we enjoyed another glass of wine before I slid onto the floor between her legs.

"You love being in that position, don't you, baby?"

"I'm more than just living out a fantasy now, Kelli. I'm infatuated with a beautiful woman."

She remained silent before whispering, "That woman is already falling in love with someone too."

Leaning down to kiss me, it quickly developed into the removing of each other's clothes as I finally got my lips around one of her hard nipples as I straddled her lap, her hands caressing my back and my arse, smiling as I felt her fingers pressing at the base of the plug I was wearing. She loved the attention to her breasts, slowing moving down her firm body, kissing over her cock and down to her balls, sucking on each of those.