Tales of Transwomen Tops Ch. 04

There are advantages to having extremely rich parents, one being that though I would eventually be expected to join the family business, I'd matched their expectations through high school then into university, eventually graduating near the top of my classes, enough to please my parents. While studying, I'd started working within the family firm, getting to know how everything worked, but I'd long discussed with them that, before I went to work full-time, I wanted to have the chance to enjoy my life before I got on with my life.

I was rather surprised that my parents agreed. I guess being an only child did help. They didn't spoil me, but I was aware of our circumstances the older I grew. I didn't get everything I asked for, and my parents made sure I earned anything by doing chores or helping out at the firm once I was old enough. My father wanted me to have 'a good head on my shoulders', and my mother simply nurtured me to make sure I wasn't an arsehole.

Having finished at university in my mid-twenties, I'd agreed to take a twelve-month trip around the world before I'd return and focus on my career. My father wanted me to eventually take over but wasn't going to just hand over the reins. I needed to earn the position, and if I wasn't good enough, there were people in place who'd support me but who could easily take over should I prove a failure.

Leaving my home country, the first place I'd wanted to visit was the United States. Like most of the world, I'd grown up on a diet of American television shows and movies, and though we kept our own culture, it's fair to say that I knew quite a bit about American history and culture at the same time. It was a place I'd always wanted to visit, so with the idea of visiting Europe after that, starting in North America was the best decision.

Making my way from west to east, I'd started out in California with the idea to either drive or fly my way around, depending on the distances I needed to cover. I had a list of places I wanted to visit, and one region would be the south, having watched shows about how great the food was and how friendly and welcoming the people were.

I'd been in the States for around three months when I enjoyed a night that might end up changing everything. I was enjoying another night out on the town, though this one started with me by myself, something not too unusual as I preferred to travel alone, leaving the days to do what I wanted, before I'd make friends at a bar that evening. I'd managed to hook up with a sweet girl from time to time, always letting them know that I wouldn't be around for too long.

Nursing a second glass of beer, the bar was somewhat busy but anyone else sat at the bar had taken a seat away from me, wanting to be alone to either watch the sport on the television or just be with their thoughts. Anyone else who had entered took seats at one of the numerous tables. The waitresses were all incredibly friendly, and the two bartenders were happy to chat with me whenever they were free to talk.

"Is this seat free?" a soft voice asked, turning my head to see an absolutely gorgeous black woman smiling at me, "You're looking rather lonely, handsome. Want some company?"

I felt the smile form on my face immediately. "Sure. Take a seat. Can I get you a drink?"

She waited until she was sat next to me before replying. "I'd love a drink, baby. What's your tipple?"

"I like a good beer. What would you like?"

"Something sweet but with a good kick." Once her drink was placed down, I watched her take a sip, her eyes closing and releasing a soft moan. "Now that's a drink!"

"I'm glad you like it. I don't mind the occasional cocktail, but they tend to make me rather drunk very quickly."

"What's your accent? You're definitely not a local!"

"I'm not. I'm doing a tour of the States before heading over to Europe."

"And what brought you here?"

"Well, I've always heard and read that the south is famous for its hospitality and welcoming nature so I thought I should check it out for myself."

She offered her hand. "I'm Savannah. What's your name, baby?"

"I'm Mark. Lovely to meet you, Savannah." Pausing, I leaned closer. "Are you named after the city?"

She laughed, a melodic sound that immediately stirred some rather warm feelings inside me. I took a moment to look her up and down. She had incredibly long, smooth legs. Her body looked tight with a large bust. And her face was something carved from stone. Prominent cheekbones. Full lips. And her eyes simply sparkled. She noticed me looking at her and turned her body, one long leg cross over the other, hem of her dress riding up her thigh.

"Like what you see, baby?"

"I don't want to be too forward, Savannah."

"Don't worry about being forward, baby. And to answer your question, it's just coincidence that I'm named after the city."

We made polite conversation as we got to know each other, two strangers making a connection in a bar. I ordered her another drink, as she admitted to drinking the first one rather quickly, making sure she sipped at it. I couldn't take my eyes off her, particularly with the prominent cleavage on display and the fact her dress continued to ride a little higher. Her legs were just perfect. Never really been a leg man, but in her heels, I had a feeling she'd be quite tall.

She was so easy to talk to though, with a heavy undercurrent of flirting, and I had a feeling she was as attracted to me as I was to her. "How long are you in the city for?" she finally asked.

"I only arrived this morning. I usually stay somewhere for three to four days at most. I'm not in any rush."

"Want some company while you're here, baby?" she asked, her hand immediately ending up on my thigh, meeting her eyes as she dazzled me with a gorgeous smile, "Maybe you'd like a friend or two while you're here?"

"Are you propositioning me, Savannah?" I asked in a teasing manner.

"A girl won't get what she wants if she doesn't ask. You're cute, baby, and I'd just love to take you home with me. I guess you have a place to stay though?"

"Yeah, found me a rather nice hotel to stay for a few nights."

Her hand moved further up my thigh, swallowing down the mouthful of beer. I'd met some forward women before, but Savannah was something else entirely. "Would you like some company tonight, baby? Maybe you don't want an empty place next to you in bed."

Placing the glass down on the bar, I turned towards her, taken by surprise when she leaned forward and kissed me. My god, it was one of the best kisses of my life to that moment, her tongue immediately sliding into mine as she shuffled her stool closer, her hand moving to cup my groin as I wrapped an arm around her, getting a good feel of her arse.

"Mmmm. Grab and squeeze it, baby," she purred, "Might have to get a good grab of your arse in return though." She kissed me again, surprised at how aggressive and in control she was. "Ever been with a black girl before, Mark?"

"No."

"Ever wanted to be with one?"

"Well, I mean..."

She giggled as I stumbled over my words. "Nothing wrong with wanting to be with a black girl, an Asian, a Latina, or any other girl." She kissed me again before kissing up my cheek towards my ears. "I love a white man every so often. Maybe I can invite a girlfriend later and you can enjoy yourself an Oreo."

I leaned back and laughed as she giggled again. "You're serious?"

"I can get a good sense of someone within seconds, baby. And I reckon that you're a real sweetheart." Feeling my cheeks grow warm at such a compliment, she kissed me again. "Would you like my company the rest of the night, baby?"

"Yeah... I really would."

"Good answer because we're not just going to have a great night, Mark. You're going to love your time here so much that you won't want to leave."

Sliding off our stools, it was in that moment I realised how much taller than she was. I never reached six foot while going through puberty, though I still made it to around five-ten. More than big enough to handle yourself on a rugby field. In her heels, Savannah seemed to tower over me, though in fact was probably only four or five inches and most of that might have been the heels. Taking my hand, she led me outside and flagged down a taxi.

Giving the driver the name of the hotel I was staying in, Savannah spent the entire trip all over me, her kisses intense and passionate, her hands all over my body. Her being in control actually turned me on a little bit, as every other woman I'd been with had expected me to take the lead the entire time. Savannah clearly knew what she wanted and was going to get it.

Pulling up outside the hotel, I paid the driver before I led Savannah by the hand through the lobby towards the elevators. "One last drink, baby?" she asked, looking at the bar.

"Sure."

Leading her towards the stools, we sat down, and she shuffled hers closer. Ordering us a cocktail each, she took my hand and placed it on the inside of her thigh, enjoying how soft and smooth her skin was. Her eyes sparkled with mischief as she took my wrist and ensured my hand disappeared underneath her dress.

"You can explore me, baby," she whispered, "I'm being forward because I always know what I want. I walked into that bar, saw you immediately and smiled to myself. Bet you have no idea how cute you really are, do you?" I felt myself blushing again as she leaned forward to kiss me. "I know you've never had a black girl before. I'm sure you're wondering if we're always this forward?"

"Nothing wrong with being confident, Savannah."

She moved her hand higher I could feel the heat from her crotch on my fingertips. "I know I'm sexy, baby. I know a man like you... Well, I'm here with you now having spent only a couple of hours getting to know each other..."

"I was attracted immediately too."

Another warm mile led to another intense kiss, her fingers on the back of my head as she moaned softly as my fingers trailed ever higher. "You can touch me, baby," she whispered, meeting my eyes as I finally grazed what felt like the thin cloth of her panties. But it wasn't a warm pussy I felt, as I'd done this more than once and usually felt damp panties.

I felt something hard instead. Something I wouldn't expect on a beautiful woman, at least most of the time, but I knew enough about the world nowadays to know things were not always what they seemed at first appearances. "You're not freaking out, baby," she whispered, sounding happy about the situation.

"Why would I freak out?"

"Because you're feeling my big cock instead of a wet pussy."

Smiling as I met her eyes, I ran my fingers over the obvious bulge in her panties. Savannah bit her bottom lip as I caressed it a few times before she kissed me hard. I had a feeling I'd done exactly the right thing and it made her feel good. "Want to see it, baby? Want to see my big black cock?" she whispered into my ear.

"Yes."

"You do?" she asked, hearing the pleasure in her tone.

"I've often wondered what it would be like meeting a girl like you, Savannah."

When she hugged me, I knew I'd learned another thing about her. Though outwardly confident, she was a woman that also needed acceptance. "Take me upstairs, baby. Take me upstairs so I can rock your world all night."

Quickly finishing our drinks, I took her by the hand and led her towards the elevator. I'd paid for one of the suites near the top of the building, escorting her towards the door and leading her into the living quarters. "Oh my god, baby!" she exclaimed, releasing my hand as she walked around, her mouth agape, "How can you afford..." She stopped as she opened the double doors to the bedroom, looking in silence before she turned around and walked back towards me, no doubt noticing the smile on my face as I loved her reactions. "I'm just some girl you met in a bar and you're..."

"A young man already infatuated by the beautiful woman he met tonight."

"You mean that, don't you?"

"I wouldn't have invited you back if I didn't feel some connection, Savannah."

Still smiling at me, Savannah reached behind her back to undo the zip of her dress, keeping my eyes on hers though I noticed the dress slip over her breasts and eventually pool around her ankles. Gazing down her body, the sheer black bra barely covered her large breasts, and her darker nipples were easily prominent. Gazing down her toned body, she wore a small pair of black panties, her big cock tenting almost obscenely. Her legs were bare, the dress pooled around her heels.

"Like what you see, baby?" Nodding mutely, she smiled as she kicked the dress away, slowly striding towards me, "On your knees, baby. Savannah will look after you tonight."

Doing as she said, I remained silent as she stood before me, gently leaning down to grasp my chin. "Fuck, you're beautiful," I murmured.

"Thank you, baby. I love to hear cute men like yourself tell me that. I don't hear it often enough." Pausing to leave a soft kiss on my lips, she added softly, "Savannah likes to be in charge. Understand what I mean?" Gulping, I nodded as she added, "And I love to fuck. Have you ever taken a big cock before, baby?"

"No," I whispered.

"But you're thinking about me fucking you right now, aren't you? Lying on your back, your legs spread wide, while Savannah slides her big black cock inside you. You're imagining it right now, aren't you?"

Nodding, she kissed me softly again. "I had no idea," I admitted.

"Of course you didn't," she smiled, "Though I'd only surprise men I know I can trust. And I had a good feeling about you, baby. Want me naked?"

"God yes!"

"Just the reaction I wanted, baby. I'm going to look after you all night." She paused before adding, "And if you keep being a good boy, I'll have to introduce you to my friends."

"Are they like you?"

"They are, baby. Could you handle that?"

"I've never had a threesome."

Leaning down to kiss me, she moved her lips to my ear. "How about three girls at once, baby?"

"Wow..."

"Wow indeed, baby. I'll have to take your picture and let them see how cute you are."

Taking my hand, she led me towards the bedroom. Kissing me again, she smiled while kissing her as I eagerly took off her bra, revealing a pair of big breasts, dark nipples hard. She didn't need to ask as I latched onto one immediately, her fingers caressing the back of my head as I moved from one nipple to the next, enjoying the sounds she made.

Her hands moved to the front of my t-shirt, helping me take that off before I was back at her nipples, her hands moving down to the belt of my jeans, managing to kick off my shoes in time for my jeans to pool around my ankles, leaving me standing in just my underwear. Her nipples were now coated in my saliva, and remembering her request about being on my knees, I left a trail of soft kisses, running my hands down her back towards her firm, thick arse as I ended up on my knees again, nuzzling against the bulge in her panties.

"Take them off, baby," she murmured, "Get a good look at my big cock."

Fingers in the thin band of her panties, I eased them over her cock and helped push them down her legs. Putting those with her bra, I leaned back slightly to get a good look at the first cock I'd seen other than my own outside of perhaps a changing room. It was long. It was thick. The head was exposed and already glistening with pre-cum. Slightly curved to the left. The scent of her was intoxicating. She had a pair of large balls underneath. The skin of her cock was slightly darker than her otherwise mocha coloured skin.

"Want to taste me, baby?" she asked, wrapping her fingers around the base, "Want to wrap your lips around my cock and make me cum?"

"It's beautiful," I replied, running my fingers up her thighs, "I had no idea a cock could look so good."

"Thank you, baby."

Leaning forward, I ran my tongue over the thick head of her cock, tasting another person's cum for the first time. It actually wasn't that bad, taking the base of her cock and running my tongue up and down the thick shaft. It was the sort of cock I'd probably see in porn. Admittedly, I'd seen a little trans porn over the years and often found it rather erotic and the women involved more beautiful than I expected.

Her cock was soon glistening from my spit, gazing up her firm, gorgeous body to see her looking down at me, eyes filled with lust, and I knew she was eager for much more than just a blowjob. Wrapping my lips around her cock earned a groan of appreciation, one hand immediately moving to the back of my head, as I slowly took a couple of inches into my mouth.

"That's it, baby," she cooed, "Suck my big black cock." Gazing up to meet her eyes, she smiled at me. "I'll keep mentioning that too, baby. It's going to look so good sliding into your arse later. Do you love the sound of that?" Nodding eagerly, surprising myself at how much I liked the idea, her fingers moved to my cheek. "I'll look after you tonight, baby. But I'll make sure you're cared for by my friends on other nights too."

Taking as much of her cock in my mouth as I could before I gagged, she let me get comfortable as I enjoyed sucking her cock. Never thought I'd think such a thing but hearing her moan excited me, and I could feel my cock was hard at the same time. Quickly getting into some sort of rhythm, she gave me a couple of pointers, including using my tongue on the sensitive underside, and had me circle the head of her cock as I used my hands to either fondle her balls or stroke the part of her cock I couldn't yet swallow.

Having watched enough porn to have an idea, I soon had my mouth, tongue and hands working together, and I found myself wanting nothing more than to make this beautiful woman cum. Her eyes continued to watch me; her gaze intense as she started to move her hips. I continued to choke and gag, wanting to take as much of her cock as possible, but she told me not to worry. I was going to make her cum, and we'd work on deepthroating later.

"Oh baby," she finally cried softly, "You sure you haven't sucked a girl's big cock before?" Shaking my head as I continued to pleasure her, she chuckled. "Guess you just feel the need to please me then."

Removing my mouth, I stroked her quickly as I licked the head of more pre-cum. "I just want to make you cum, Savannah."

"Get your mouth back to work, baby. I'm going to fill your mouth soon enough."

Swallowing as much of her cock as possible, she thrust as I bobbed, timing it right so I didn't gag or choke too often, though I think she found that a bit of a turn on, and I wanted to learn how to deepthroat, the idea of taking her entire length, pressing my nose into her as it disappeared entirely, was a real turn on. Gazing up her body, I could see she was getting close to orgasm, her fingers gripping my hair tighter.

"Oh baby," she moaned, "You're far too good at this already."

I moaned around her cock, humming for vibration, having just doing that alone could help. Fondling her balls, I caressed them and used my hand to stroke her cock at the same time, doing everything I could think of to make her cum.

"You want my cum, baby?" she groaned, "You going to swallow every drop like a good boy?" Moaning around her cock, I'm sure my eyes would have reflected a desperation to please. "Here it comes, baby. Get ready!"

Pulling back so just the head of her cock was in my mouth, I stroked her and waited until I felt that first spurt. When she erupted, I knew it was going to warm, surprised at how thick and creamy it was, swallowing it down and smiling as her taste was rather pleasant. She moaned softly with each spurt, and I was left rather amazed at how much she did cum, spurt after spurt erupting from her cock, feeling as if half a pint of cum was nestling in my stomach by the time she was done.

Removing my mouth, I cleaned up her cock with my tongue before sitting back on my knees, smiling up at her. She was immediately on her knees in front of me, kissing me passionately, her cock pressing into me. "Thank you, baby," she said, "That was wonderful."