Love Around the World 12: London

Story Info
A capital full of gorgeous women a young man might enjoy.
13.4k words
4.57
4.8k
4

Part 12 of the 26 part series

Updated 01/30/2024
Created 11/24/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
UltimateSin
UltimateSin
5,331 Followers

A/N - Unlike my previous story in this series and in this category, if you liked my series 'Tales of Transwomen Tops', then you might just like this offering too. There are some references to same-sex (men on men) relationships.

Previous stories in this series:

Love Around the World - Andorra (Mature)

Love Around the World - Bangkok (Interracial)

Love Around the World - Colombia (Transgender)

Love Around the World - Dresden (Romance)

Love Around the World - Estonia (Group Sex)

Love Around the World - France (Anal)

Love Around the World - Guangzhou (Interracial)

Love Around the World - Hungary (Incest)

Love Around the World - India (Interracial)

Love Around the World - Japan (Mature)

Love Around the World - København (Transgender)

Australian / British standard English. There is a good chance of reading the following: lots of profanity, characters drinking, typos, and bad grammar at times.

Proofreading and editing suggestions provided by OhDave1. Any mistakes are still mine.

Comments are appreciated as always.

Feedback by email is always welcome. Enjoy chatting with anyone who likes my work.

*****

A capital full of gorgeous women a young man might enjoy.

******

Getting ready for our night out, I looked at myself in the mirror and almost laughed at the fact I was twenty-two years old and still barely needed to shave. My cheeks were still baby smooth and the light fluff of hair on my upper lip only needed removing because I found it annoying. Looking down at my chest, there was barely a hair on there and even my groin and arse were still almost as smooth as they'd ever been. I had light-coloured hair on my arms and legs, almost matching the sandy brown hair on my head.

I knew I wasn't the most masculine of men out there. I wasn't particularly tall, barely topping out at five-seven, rather slim, and hell, I think most blokes thought I was slightly effeminate. I know my arse had plenty of men appreciating it which left me feeling a little weird.

The main problem I had is that I had no idea what my sexuality was because of what I'd been doing since I turned eighteen which had me constantly questioning myself. Still deep in thought, I almost cried out in surprise when there was a thump at the bathroom door.

"You nearly finished in there, little dude?"

I blushed as Mike had called me that ever since I'd moved into the sharehouse I lived in, moving in only a couple of weeks after arriving in London. Ensuring my towel was wrapped tightly, I opened the door to see him smiling down at me from his height of six-two, his shoulders broad, toned chest and tummy, his towel loose at his hips.

"Sorry, I didn't realise I'd been so long."

Resting a hand on my shoulder, I shuddered slightly as he was one of the many reasons why I was always wondering. "You okay?" he asked.

"Yeah..."

"Excited for tonight? I know James and Steve are eager to hit a club or two."

"I swear you just like me walking in on your arms because other twinks immediately wander over and ask questions about you three."

Running his hand down my arm to my hand, he gently grasped my wrist and slid my hand underneath his towel, feeling his thick, hard cock underneath it. "We could always stay in and have fun of our own again," he offered.

My mouth watered at the prospect. Mike wasn't the first man to fuck me, but he was the first man who became a regular lover in my life. The first time he fucked me had been a week after I'd moved into the sharehouse. I was aware the three men I'd been living with were gay. I'd only been with two other men previously, both back in Australia before I'd left for London and the chance to spend time backpacking around Europe. Mike flirted with me constantly, and when I finally found the confidence to flirt back, he had me on my knees with my head buried in a pillow, his thick cock buried in my arse within an hour after that. He fucked me solidly all night, mounting me from behind before he had me on my back, my legs spread almost obscenely wide, and he seemed to really enjoy it when I was bouncing up and down on his cock. By the time I fell asleep against him, my arse was leaking plenty of cum and I knew we'd definitely be doing it again.

Neither of us was interested in a relationship. We were young, living overseas, constantly horny, and wanted to enjoy the variety that London had to offer. Didn't stop him fucking me at least once a week, and once James and Steven learned that Mike was fucking me, they were eager to start fucking me too. More than one night ended with me being fucked by the three of them, usually one of them in my arse, another with his cock in my mouth, the third waiting to fill whichever hole was emptied first. Then there were the nights I was laid back and they just rotated fucking me for hours.

Nothing compared to my first time back home...

*****

My first sexual experience had been back in Australia a week after I turned eighteen. There'd been a whole group of us, and most of my friends had been girls. They wanted to hit up a gay club because they didn't want to spend an entire night being hit on by obnoxious guys. I was one of only three guys, the two other guys were not bothered as I knew one of them was at least bisexual, and the other guy was gay as hell, so we happily followed them.

As the girls bought drinks and disappeared to the dancefloor, laughing to myself as I knew they were going to be hit on by women all night, I took a seat at the bar as I wasn't exactly confident at the time. Barely eighteen, a virgin, and I'd been questioning my sexuality for years. It was enough that I broke down in tears with my mother a couple of times as I just felt so confused. My father... Well, I was thankful he wasn't in the picture. I had two older sisters who loved me to bits though.

Nursing my third sweet-tasting cocktail, I felt a hand on my back as an absolutely drop-dead gorgeous woman sat down on the stool next to me. "You look sad, sweetie," she said softly, her hand continuing to caress my back.

"I'm not sad. Just very new to all of this."

"How old are you?"

"I turned eighteen last week."

She shuffled the stool a little closer as her hand moved to my thigh. "So this is your first time in a gay club?"

"Definitely. I've never been to a nightclub. The girls I'm with are all a little older than I am."

"Are you gay, sweetie?"

"I don't know, if I'm being honest. I mean, I think some guys can be hot and I do wonder what it would be like if one of them fucked me. I also like girls, but let's be honest, I'm pretty invisible when it comes to them."

"I'm a girl and you're very visible to me," she said softly, "What's your name, Honey?"

"Mark." She offered her hand, surprised at how soft her hand was though her grip was strong. She probably thought my hands were rather soft. "And you?"

"I'm Sally, sweetie. And I think you're just what I'm looking for."

I'm fairly sure my jaw dropped as I felt myself start to blush as she gently squeezed my thigh. "So you think about hot guys fucking you sometimes?"

"I really like... you know, cocks. I imagine sucking on one and then feeling one inside me. And... Well, I guess I can admit it in a place like this, but the internet is where you discover certain things and that's where I discovered transwomen. You know, they were born as males but now live as women... So many of them are so beautiful. I worry I might, you know, treat them as a fetish because they're beautiful women, and some of them I've seen have really big cocks, but then I think about what it might be like to be with a woman like that..."

"You're interested in transwomen?"

"To be honest, I'd love to meet one. I'd love to meet many of them. I'd like to understand them, and what they go through, support them, love them... I know it probably sounds like bullshit..."

"It doesn't, honey," she said, raising her other hand to my cheek, making sure I was meeting her hazel eyes, "Girls like me need to hear that from men."

"Oh..." I whispered as I hadn't given it a thought that she'd been trans.

She chuckled as she asked, "You had no idea, did you?"

"I just thought a beautiful woman totally out of my league sat down next to me."

Her hand continued to caress my cheek. "You are just far too cute for your own good. Some women are just going to gobble you up and spit you out. You'll be well used though you'd probably love it." Leaning down, she left a soft kiss on my lips. I froze as it was the first time that I'd been kissed by anyone other than my mother or sisters, and they'd long stopped kissing on the lips. She realised and pulled back. "First kiss?"

"Pathetic, I know..."

"You're a virgin?" Nodding, I gazed away as I felt even more embarrassed. What I didn't expect was her to pull me into her chest, my head resting between her rather large breasts. "Oh sweetie, it's nothing to be embarrassed about. Everyone has to go through a first time eventually." Lifting my chin with a finger, she smiled at me. "Sweetie... I'm thirty-six years old. I've lived as a woman for over twenty years."

"Wow," I said softly, "I would never... I mean, you look..." I shut up as I figured there wasn't any way I could get across what I thought without offending her.

Thankfully, she laughed lightly. "I'm guessing you were going to say you'd never have guessed I'd been assigned male at birth?"

"Yeah... You're beautiful, Sally."

Sally called over the bartender and ordered a drink for each of us. When I tried to argue, she put a finger to my lips. "You're obviously a broke student. I'm going to buy you a drink. Then we're going to go dance. Then I'm taking you home and you won't end the night a virgin. How does that sound?"

"Will you make love to me?" I asked softly, "I... I don't have a very big cock..."

"I bet it's as cute as you are, sweetie. Want to feel what I have to offer?"

I couldn't help nodding eagerly as she took my hand, leading it up her thigh as she spread her legs enough that I could feel her thick girlcock underneath the thin fabric of her panties. It wasn't hard though it was still thick and warm to the touch. "Oh god," I whispered.

"You like that, sweetie?" Nodding eagerly, she added, "Move my panties and get a real feel of it."

Doing as she asked, I wrapped my hand around it and felt it slowly get harder as she leaned down to kiss me again. This time I was ready, whimpering into her mouth as she didn't hesitate in sliding her tongue into my mouth. As she kissed me, I felt her girlcock getting harder and harder until it seemed it was as hard and thick as it could get. I was as hard as I could remember, and when her fingers gently caressed the small tent in my jeans, I nearly came immediately. Noticing me shudder, she broke the kiss and smiled at me.

"I think dancing might be a bad idea as I know you'll probably cum rather quickly. Would you like to come home with me, Mark? I'm going to be blunt so there's no confusion. You're going to come with me, you're going to suck my girlcock, then I'm going to spend the rest of the night fucking you. But I'm going to be ever so gentle doing it. I want to ensure your first time is memorable so that you'll want to see me again in the future."

"I'd better tell my friends I'm going."

I managed to locate a couple of them, letting them know I'd made a friend and we were going to spend time together. They put two and two together rather quickly, their smile broadening when Sally stood next to me, over six foot tall in her heels, a big set of tits and a short skirt that showed off her long legs.

Taking me by the hand, she led me outside and towards the nearest taxi rank, giving the driver an address. It was only a ten-minute drive before we pulled up outside a terraced house in the inner-west of Sydney. After paying the driver, she led me inside, explaining that she lived alone and could afford to live alone having worked her way up the corporate ladder while also being a sex worker on the side.

"Not a sex worker as in a hooker or prostitute," she explained as she handed me a glass of wine, "I have an online presence where I love to pose and do shows for people. I make a lot of money doing it. I have a big girlcock that a lot of men and women like to see me use. I've never done anything with a man or woman on camera."

"Does anyone at your work know?"

"If they do, it hasn't been mentioned. The problem is that most people are aware I'm transgender anyway, and there is more than one guy who would love nothing more than for me to fuck them. Unfortunately, there is only a certain type of man I usually go for." She finished that sentence and kissed me softly. "I love them young and very cute," she added.

We finished our glass of wine as we got to know each other. Once we placed our glasses down, she stood us up and rather eagerly got me completely naked in what felt like seconds. I immediately felt self-conscious as I had no real definition whatsoever and my cock was hard, but I'd always been embarrassed by the size. Feeling her wrap her fingers around it made me shudder.

"I'd love to see you nice and hard when you're bouncing on my girlcock later," she whispered, "There's nothing wrong with it, sweetie."

"Bet you're bigger though..."

"I am bigger, sweetie, but that's what you want, isn't it?"

I nearly cried as I nodded. I wanted nothing more than a beautiful woman with the sort of girlcock that could just fill me completely. Feeling her arms wrap around me, she kissed me again as she asked if I wanted to get her naked. Nodding again, I helped off her blouse and then her skirt, her girlcock popping out the top of her panties as I fumbled with her bra first, freeing her rather large breasts before I helped take off her panties, leaving her in just thigh-high stockings as she stepped out of her heels.

Sitting down on the couch, she had me kneel between her legs. "Play with my girlcock, baby," she said, "Get used to it. Feel how thick and warm it is. And when you feel ready, use that pretty little mouth and tongue. And if you want to be a really good boy for me, you'll swallow all of my cum."

I had no real idea what I was doing when it came to giving a blowjob, only what I'd seen in porn, but with a little instruction, I had her moaning softly as her fingers caressed my head, running through my hair as my head bobbed up and down on her girlcock. She must have been rather excited as she was warning me that she was getting close to orgasm within a few minutes.

Feeling her cum in my mouth was euphoric. I swallowed as much of her cum as possible, some of it dripped down her girlcock as I used my tongue to eagerly lick up what dribbled out of my mouth. Moving my mouth and tongue down towards her smooth balls made her coo with delight as I moved my mouth up, swirling the head of her girlcock with my tongue before I resumed blowing her.

"Oh baby, you're so eager to suck me..."

"I've dreamed about doing this to someone for so long," I admitted, "But the fact it's someone as beautiful as you, Sally..."

Standing up, she offered her hand and practically dragged me to her bedroom. Pushing me up onto the bed, I remained how I was positioned with my arse in the air as she spread my cheeks and didn't hesitate in using her tongue on my arse. The noises that escaped me had me blushing as I had little idea about eating arse. And I loved it from the first moment her tongue touched me.

Her tongue was followed by some fingers once she'd lubed me up. I'd fingered myself a few times while masturbating but nothing compared to having two of her fingers inside me while she leaned forward, leaving kisses up my back before her head rested on my shoulder.

"Three fingers, baby, then I'm going to slide my big girlcock inside your tight little arse," she murmured into my ear, "I'll be gentle. Just relax and try not to clench too much."

"I'll try."

Once she had me ready, I was surprised when she rolled me over onto my back, and spread my legs as wide as possible as I watched her long, thick girlcock bobbing up and down as she lubed it up and pressed it against me. I gasped as she pushed forward, whimpering as I felt it ever so slowly start to spread me wider so I could accept it into my body. I tried not to clench but did it more than once, Sally leaning down to kiss me softly, not stopping as I knew once it was inside, it would feel wonderful.

"Oh god!" I cried out once the head slipped inside me, and she didn't stop, my hands were on her back and I knew my fingers were digging into her. "Oh god!" I whimpered as I felt inch after inch of that thick girlcock descend deep.

"Good boy," she whispered, kissing my cheek, "Very good boy. You love my big girlcock now?" she asked once her entire length was inside me. Managing to nod, she kissed my cheek again as I blinked back the tears. Not from pain but from being so happy in that moment. It was everything I wanted.

Feeling her start to move, I couldn't believe the sounds I was making. The moans. The groans. The grunts. The whimpers of pleasure and delight. She made the same noises but was very complimentary. She called me cute. She said I was a sweetheart. She marvelled at how tight my little arse was. She suggested that she was going to keep me around and just spend all day fucking me. That thought turned me on to no end.

"Don't touch yourself until you're bouncing on me later," she said, "Though I can see you're so hard right now, sweetie."

"Please don't stop," I practically blubbered, "It feels so good."

"I know it does, baby. I'm so glad I'm your first. And this won't be our only time if you'd like."

"I'd love to see you again, Sally."

"Good boy. You'll love my big girlcock as often as you can."

Having already made her cum, she must have made love to me for an hour before I finally felt her girlcock pulsing as spurt after spurt of hot thick cum flooded my bowels, I wrapped my limbs around her and pretty much burst into tears. She cuddled me in return, whispering very sweet and affectionate words into my ears. I felt like a wimp for crying. She told me there was nothing wrong with feeling emotional after your first time making love.

"That's what it was, baby," she whispered, "We just made love."

I didn't want her to pull out as the feeling of her girlcock inside me was already addictive, but she needed to relax for a few minutes having cum twice in a short space of time. Lying on our sides, she let me run my hands all over her body. Playing with her breasts made her chuckle, and I eventually ended up with one of her nipples in my mouth, surprised they were still so sensitive. My hand eventually ended up caressing her girlcock back to life and that's when she laid on her back and had me straddle her.

Sliding down her girlcock, I'm sure my eyes rolled back into my head from the pleasure as her hands ended up at my hips to help me balance. "Stroke that cute cock of yours, baby. I want to see you shoot all over me!"

As I moved on her girlcock, marvelling at the new sensations flowing through my body, I slowly stroked my cock at the same time. I barely lasted a few minutes before I had a toe-curling orgasm, the sort which had me nearly passing out, needing to rest on a forearm as I sucked in some deep breaths, her chest now coated in my cum.

And that's when she started to fuck me, her hands on my arse as she cuddled me. She eventually had me roll off and onto my knees as she got behind me, sliding her girlcock deep inside me and leaning forward, pretty much mounting me immediately, grunting as she started to thrust faster and faster.

"Oh god," I groaned as I barely kept my arse in the air, "Oh god, Sally..."

UltimateSin
UltimateSin
5,331 Followers