Tales of Transwomen Tops Ch. 02

"Let's head inside and make ourselves comfortable, Stevie. I'm sure you've realised you're spending the night with me."

"Sure."

While not exactly modern from the outside, as the inner west of the city was mostly terraced housing that was at least a hundred years old, the inside was modern though still maintaining a warmth with nods to the age of the place. Leading me towards the living room, she asked me to sit down while she would fix us drinks.

Returning a couple of minutes later with a glass each, I took a sip and coughed as it was a little strong. "Not getting you drunk, cutie. It's just something to help you relax," she assured me.

We took a few sips before I turned towards her, looking up and down her body. Placing a finger under my chin, she stroked my cheek and leaned down to leave a soft kiss on my lips. "Never done anything like this before," I admitted.

"It's okay, cutie. I'll take the lead. Would you like that?" Nodding, we took another sip before standing up as she wanted to see me naked. I was shaking as she helped off my shirt first. I was rather slim though hated the word scrawny. I just didn't have much muscular definition though looked after myself through diet and a little exercise. Next were my shoes, kicking those off, using a toe to get rid of my socks.

When my trousers hit the floor, pooling around the ankles, I could feel my entire body shake as I stood in front of Chanelle in just my underwear. I was hard but the tent wasn't exactly large. When Chanelle cuddled me to her body, I nearly started to cry as it was a hug of reassurance. "You're beautiful," she whispered, her fingers caressing my back, "A beautiful boy. Nothing to be ashamed of, Stevie."

Letting me go, she crouched down in front of me before resting on her knees, leaning up to kiss me again as her fingers hooked into my underwear, feeling them lower first around my butt before she ensured my cock sprang free, making sure I stepped out of them before she placed them next to us. When I felt her fingers wrap around my cock, I nearly climaxed again.

"I know it's small," I whispered, "Like the rest of me."

"So you learn how to please a woman in other ways, Stevie." Meeting her eyes, she smiled as I felt relief that she wasn't disappointed. "When I say that your cock is cute, I mean it's cute just like the rest of you."

"Thanks," I said softly, feeling my cheeks grow warm.

"Want to see me, cutie?"

"Yes!" I exclaimed excitedly. It made her laugh as she stood up in front of me. Taking off her heels again, she still towered over me. Removing her blouse first, the bra she wore was sheer, seeing her hard pink nipples behind the black fabric. Smiling as she could see where I was looking, I followed her hands down her toned body towards the top of her skirt, the zipper at the side, moving that down and lowering it to the ground.

Standing before me in just her underwear, my cock was throbbing with excitement, Chanelle stepping towards me again, my cock pressing against her. It felt so tiny against her, but I was actually naked with another woman. I was going to savour the experience for as long as possible. Taking my hands, she moved them, so I was holding a breast in each hand. I had no real idea about breast size, and I was left wondering if they were fake. They were certainly big. Very big.

"Clasp is between the cups," she whispered, "If you'd like to see my tits."

"I'd love to."

"Then undo the clasp, sweetie. I want you to see my tits too."

My hands were shaking. I was about to see a pair of breasts for the first time. Undoing the clasp, the cup moved away from each breast. I smiled at seeing her whole breast, an areola the size of a twenty-cent piece, and her nipples were hard, pointing out. Shaking the bra from her shoulders, she was now standing before me in just her panties.

"Get on your knees and take off my panties, sweetie," she told me. It sounded like an order and there was a part of me that didn't mind. I was young and inexperienced. She was an older woman who'd already said she'd take the lead.

Falling to my knees, my hands were still shaking as I rested them against her lower legs, looking up to see her smiling down at me. Running my hands up her thighs, loving how soft and smooth her skin was, I eventually made it to the fabric of her panties. "That's it, cutie," she whispered, "Take them off for me."

Lowering them down, I took my time as I reached her knees, then her calves before she lifted one foot and then the other so she was now as naked as I was. Sitting back on my knees, she leaned down to leave a soft kiss on my lips. "I have a surprise for you, cutie. Want to see it?"

"Sure."

She stood up and spread her legs slightly, and that's when an enormous, flaccid cock appeared from between her legs. I'm fairly sure I whispered 'Holy shit' at seeing such a massive cock. Meeting her eyes, she was still smiling as she offered her hand, helping me to my feet. Her hands caressed my body as she pulled me close, feeling her cock getting harder as it started to poke me.

"Do you like my big cock, cutie?"

"I've... Well, I've seen things before."

"Porn?"

"A little bit. Like most young men, I was curious."

Taking my hand, she led me back to the couch, sitting down first, her cock now completely hard, resting against her belly. It dwarfed my cock considerably... And it simply made her even more beautiful in my eyes. Resting a knee to either side of her body, I sat on her lap as she pulled me forward to kiss me again, her tongue quickly ending up in my mouth. Having never been kissed in such a manner, it was all very exciting, particularly when my cock rubbed against hers.

"I don't usually do that," she admitted, "But I had a feeling you wouldn't mind."

"You're beautiful, Chanelle..."

"And you're a complete sweetheart. Want to suck my tits?" I felt myself blushing as I nodded. Her fingers ran through my hair as she added, "Want to suck Mummy's big tits?"

I groaned as that just added another level. And though I'd never fantasised about my mother or sisters, I was aware that many women called their lovers 'daddy'. She was an older woman. Wanting to be called 'Mummy' was just another turn on.

Kissing again, she made me moan and whimper as her hands grabbed my arse. I was left thinking that she really wanted to fuck me. I would have to tell her that the idea only scared me because she was so big. I had a feeling she wanted to fuck me, and it wouldn't be the other way around. When I finally wrapped my lips around one of her nipples, she moaned softly as she continued to run fingers through my hair.

"That's it, cutie. Suck Mummy's tits. I bet you'd love to taste Mummy's milk, wouldn't you?" I met her eyes and groaned, loving the feeling of her nipple in my mouth. Her other hand continued to stroke my back and my butt, making me shudder as she occasionally ran fingers over my arsehole.

Moving to her other nipple, I suckled at that as she moaned again. My cock was now throbbing from the excitement, and I wondered if I was going to cum just from sucking her breasts. As I sucked her nipples, my other hand moved down between our bodies. "That's it, cutie," she whispered, "You can feel Mummy's cock if you want to."

Gently grasping another cock than my own for the first time, she moaned again as I doubled down on sucking her nipple as I ran my fingers up and down her cock, feeling slickness at the top of her cock. "Pre-cum, sweetie," she explained, "I cum a lot when I'm excited. My panties you took off will be stained from how excited I was tonight."

Taking my mouth from her nipple, I kissed her again as she pulled me close. "What do you want me to do next, Mummy?"

Her eyes lit up as she stroked my cheek with the back of her hand. "Want to taste my big cock, cutie? Maybe get down on your knees between my legs."

I surprised myself at how eagerly I nodded, sliding off her lap and kneeling between her legs. She spread her legs a little wider as I got a good look at how large and heavy her balls also were. I could barely wrap my fingers around the base of her cock, lifting it up and placing it against my cheek. "I've got a real big one, cutie," she said with humour, "I really want to see your pretty little mouth wrapped around it."

"I'll try."

"Get it nice and wet first. Lick it up and down. Get a taste of my pre-cum too. You'll love the taste of my cum."

Doing as she told me, I was surprised that I didn't feel weird that I was licking her cock. It was darker than her skin colour, quite a few veins, and as thick as my wrist, or that's how I judged it. The head was even darker, and I was wondering if she was desperate to cum. My cock was still hard, but I had calmed down a little bit.

Running my tongue up and down made her moan softly. I smiled at the sheer fact I was pleasing her. Once her cock was glistening from all my spit and saliva, I lifted myself up slightly and, with only a little hesitation, wrapped my lips around the head, feeling a small flow of pre-cum from her cock. I swallowed that down, actually liking the slightly salty taste, as I lowered my lips down as far as I could without making myself choke and gag.

"That's it, cutie," Chanelle moaned, her fingers gripping my hair, "Suck Mummy's big cock. You're going to make me cum so fast!"

I knew that eye contact was important, ensuring I was gazing up her body as I slowly bobbed my head up and down her cock. She smiled continuously, her fingers either running through my hair, down my face, or up my arm as I used one hand to stroke the large section of cock I simply couldn't get in my mouth.

Sealing my lips tighter, she moaned again as I moved faster, bobbing quicker while I used both hands to work the rest of her shaft. When her hips started to move, and her hand firmed up on the back of my head, I knew I was doing something right. "Oh Stevie... I can't believe this is your first time..."

"Watched more porn than I'd care to admit."

Chuckling, I met her eyes as she watched me suck her big cock like my life depended on it. The thought that I would make her cum thrilled me. "You loved watching women with big cocks fuck cute boys like you, didn't you?"

Smiling, it wasn't something I wouldn't normally admit to. I had always hoped my family didn't know my porn habits. I never saw much straight porn with men resembling someone like me. I knew what twinks were in gay porn. Shame I wasn't interested in men. But I'd seen plenty of transgender porn. Many sites still called them shemales or trannies, aware they were outdated or derogatory terms nowadays. Ladyboys generally referred to Asian transwomen, who were also sexy as hell.

Bobbing faster and faster, I could sense she was getting close, despite having never made a woman cum before. Her hips moved faster, and I knew she was close. Polite enough to warn me, I moved my mouth back so only the head of her cock was in my mouth as I used both hands to stroke her faster and faster.

"Oh fuck!" she exclaimed, feeling her fingers grip my hair even tighter, "Oh fuck, Stevie. Get ready, cutie. Gonna cum!"

That first spurt of hot, thick cum exploded into my mouth. I loved the feeling straight away, and I swallowed her gift immediately. More heavy spurts filled my mouth, doing my best to swallow as much as I could, but Chanelle had warned me that she came hard and heavy, and she hadn't lied. Cum eventually dribbled down my chin as I pulled back, the last couple of spurts hitting my mouth and chin.

As her climax faded, I used my tongue to clean up her cock, then a finger to clean my chin. Sitting on her knees before her, she took a moment to catch her breath before leaning forward and kissing me hard, her tongue exploring my mouth once again. While still kissing, she helped me up to sit on her lap, shuddering as her fingers wrapped around my cock again.

"Want to keep going, cutie?" she asked.

"Do you want to fuck me, Chanelle?"

Her face softened before she kissed me again, holding me tight to her body as she sat up. "I want to take you to my bedroom and spend the night with you, Stevie. And I'm hoping it's the first of many nights, if you want."

"Mummy will look after me?"

Her eyes lit up before she kissed me again. "Mummy will look after you, cutie."

Standing up, I wasn't surprised that she could easily carry me to her bedroom, turning on the light and smiling as her room was tastefully decorated, a real feminine touch. Placing me down on the edge of the bed, I wrapped my hand around her cock again, making her chuckle. Gently pushing me back, I shuffled back as she joined me on the bed, crawling towards me.

I felt tiny underneath her, left mesmerised by her big cock swinging as she reached over to her nightstand. She pulled out some lube, then offered a condom. Shaking my head, she smiled before kissing me again. "I want to feel you cum in me the first time," I admitted.

"And you still haven't cum, cutie. I promise you're going to have the best orgasm of your life while I'm inside you."

"Just be gentle," I whispered.

"I'll make sure you're ready for me."

Gesturing with a finger, I turned around to rest on my knees, leaning back as I was pressed back against Chanelle. Gently pushing me forward, I grabbed a pillow and relaxed as I felt her rub her cock between my cheeks, though that disappeared and I felt her hot breath, making me shudder.

"Well, that is just a delicious looking rosebud, cutie," she said, "So pink and virginal."

"Because it is, Chanelle!" I replied, chuckling to myself.

Groaning when I felt her tongue run over my arsehole, I gripped the sheets as Chanelle just seemed to dive in. Within a couple of minutes, I was moaning and whimpering, and the idea of her sliding her massive cock inside me only turned me on even more. Feeling her tongue disappear had me groan with disappointment as I'd enjoyed it far more than I ever thought possible.

"Ever fingered your arse, Stevie?" Shaking my head, one of her hands continued to stroke me as I glanced back to see her stroking herself. "Just try and stay relaxed. Okay?"

"Okay," I replied softly.

Feeling her pour some lube onto me, I giggled as she rubbed it against my arsehole. When her tongue returned, I moaned loudly which made her giggle. "I always used flavoured lube. I'm hoping you'll eat my arse sometime soon. It's something I love my partners to do."

"I'll do anything you want, Chanelle."

Her fingers eventually prodded me, and I couldn't help moving away at first. Gripping my hip firmly to keep me in place, she ran her fingers over my rosebud, letting me get used to the feeling, before she gently pressed a finger against me. Feeling it slowly slide inside me actually felt pretty good. Slowly thrusting into me, she gave me time to get used to it.

"That's pretty good," I finally said.

"Want another one?"

I probably surprised her with my eager nod. "Please," I whispered.

Adding a second finger felt even better, keeping my eye on Chanelle as she leaned forward to kiss me on the cheek, driving her fingers a little deeper. When I moaned loudly, she giggled before kissing my again. Asking if I wanted a third, I met her eyes and almost begged for it. Taking a third caught my breath as I felt completely stretched out though aware her big cock would feel even bigger.

"Good boy," she cooed, "Mummy will look after you."

She gently fingered me for a few more minutes before she decided I was ready for her. Removing her fingers, she picked me up, making me nearly squeal before resting me on my back, spreading my legs as she placed a pillow under my butt. Watching her lube up her cock filled me with even more excitement. It perhaps wasn't the way I imagined losing my virginity, but now that I was in the moment, I couldn't think of a better way.

Watching her lube up was exciting, knowing she would be inside me within a couple of minutes. Once she looked ready, she spread my legs wide and lifted my arse slightly. Feeling her cock press against me, she leaned forward and kissed me softly.

"Ready for Mummy's big cock, cutie?"

"Yes, Mummy. I can't wait to feel you inside me."

"I'm going to make you cum quite quickly, cutie."

"Okay."

She kept kissing me as I felt her press her thick cock against me. When she ever so slowly started to slide inside me, feeling my arsehole get wider and wider to accept her, I dug my fingers into her back as I won't lie. It still hurt a little bit. She realised and broke the kiss, stroking my cheek. "It's okay, cutie," she whispered, "I won't hurt you too much."

"Slow... Just let me get used to it."

"I will but you're so deliciously tight, cutie."

When the head of her cock popped inside me, I could stop the moan that escaped me, squeezing her cock a few times as I got used to having something so large inside me. Giving me time to get used to it, she started to slide more of her length into me, wondering where it could go considering I was small compared to her, and her cock was simply enormous.

We groaned together as she continued to slide her length inside me, Chanelle the first to smile when her entire length had disappeared inside me. Keeping my legs back, she ever so slowly pulled back and slid forward, making love to me as our mouths met, moaning together as she slowly picked up the tempo of her thrusts.

"Fuck," I whimpered, "Holy shit..."

"You okay, cutie?"

"Fuck me, Mummy!"

She laughed, kissing me again. "I'll change the angle slightly and you're going to cum so hard, cutie. You ready?"

"God yes. I really want to cum with your cock inside me, Mummy."

Lifting herself up slightly, my legs ended up wrapping around her upper arms, as she started to fuck me a little faster. I'd never felt it before but knew she was now hitting my prostate. It felt fantastic, moaning with every thrust, her eyes watching mine as I knew I was on the verge of orgasm. She leaned down to kiss me, holding her tight as I felt my cock just erupt. Squeezing her cock with my arsehole, she kept thrusting as the orgasm tore through my body. I whimpered and moaned as I felt my cock throbbing away, spurt after spurt of cum covering me.

"Mummy..." I whimpered.

"I promised I'd look after you, cutie. Mummy made you cum hard."

"Oh my god... It feels so good, Mummy."

She kept thrusting into me. Fuck, it just got better and better. Now that I'd orgasmed, I could just focus on the feeling of her thick cock sliding inside me. I looked down between our bodies to see it disappear and reappear. Moving my eyes back to hers, she smiled as my legs moved from her upper arms to her shoulders.

Lifting my arse even more, she started to drive into me faster though, while there was a dull ache, it wasn't as painful as some of the stories I'd read about men being fucked for the first time. Chanelle had applied plenty of lube and had taken time to look after me.

"Love your tight little arse, cutie," she groaned, "And I'm about to fill you up with loads of hot cum."

"Fill me up, Mummy."

She did just that within a couple of minutes, feeling her thick cock throbbing away in my tight arse, a new warm sensation as she continued to thrust as I was sure I felt every spurt of her big cock. When she eventually stopped thrusting, she gazed into my eyes before kissing me softly, releasing my legs so I could wrap them around her waist, my fingers digging into her back as she continued to gently thrust into me.

"Is it always this good?" I wondered.

"It gets so much better once you'll be capable of really being fucked hard."

Feeling her pull out had me groaning with disappointment as I'd already grown to enjoy feeling her inside me. Lying down next to me, I turned onto my side and cuddled into her, making her chuckle as I latched onto one of her breasts again while my other hand started to stroke her still thick, hard cock.