Vol. 01: London - Assisting Anna

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Beautiful readhead Anna needs money. Uncle Jim can help.
3.3k words
4.09
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Part 1 of the 1 part series

Updated 06/16/2023
Created 05/24/2023
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Tails of the City Vol. 01 - London - Assisting Anna

It's like stepping out of a time machine. You come up in a small lift and the doors open and the exit gates are right there. You're stuck in a mob of tourists and they're all excited and jabbering in Italian or Spanish or whatever. They push and shove and suddenly everyone is spat out into Covent Garden, just like into a film set, and you imagine Stanley Holloway in his top hat and tails prancing around the Piazza singing "Get me to the Church on Time".

Yes, there's drinks and girls all over London, but the last time I got out at Covent Garden station there was only one girl on my mind. Anna. Her mother contacted me and said what a coincidence, Anna was in London for a few days too, would I mind meeting her, maybe show her around, keep her company? Of course, I said, and I acted all cool even though my heart nearly jumped out of my chest. I called Anna and arranged to meet her and she told me the real reason her mother had called. She was too embarrassed to call me first, and scared, I guess. I was scared too, because I wanted to help and this was an opportunity that I didn't want to fuck up. And now here I was in Covent Garden, and I'd see her in less than ten minutes.

I walked down to the market and strolled around the stalls. I spotted a necklace with a thin silver chain and a small glass pendant with rainbow stripes. Not too expensive, not too tacky. I bought it and put it in my inside jacket pocket. I checked the money was still there too.

Then it was a straight line through the Piazza, down Southampton Street to the Strand, across the road and into The Coal Hole. I walked the length of the bar. Not too many people around for early Saturday evening. I ordered a pint of Spitfire and sat at a table facing the door. I looked at my watch. She'd be here any minute if she was punctual. And she was.

A guy came in and he held the door for someone behind him. It was Anna. She said thanks, so they weren't together. Good. She wore an emerald green cocktail dress, just like I'd asked her to, and an unbuttoned long coat. Then she stood just inside the door and put a hand through her long straight red hair, suddenly unsure and nervous compared to how confident she'd looked just seconds before. God, she was beautiful. I felt my heartbeat thump and I took a quick drink. She saw me and I stood up as she walked towards me.

"Anna-"

"Jim," she said.

Oh, that quiver in her voice, the same as when we spoke the day before. The poor darling girl was terrified. I moved forward and kissed her cheek and hugged her and inhaled a wonderful perfume as I put my nose against her hair.

"You look gorgeous Anna. Here, sit down."

"Thanks. You look good too."

"Oh, I don't know. I guess I've been to the gym a lot. Let me get you a drink. What will you have?"

"White wine. Please."

I returned with the drink and sat next to her.

"Well Anna, look at you, all grown up since the last time I saw you dressed like that. How old were you, twelve?"

"Yes, I guess."

"Sorry if it's a bit weird."

"What do you mean?"

"You know, asking you to wear a green dress like the last time I saw you at that birthday party. I just thought, how will I recognise that gorgeous girl now she's a grown-up young lady of twenty? Then I thought if I got you to wear similar clothes, I'd know it was you. Just how I always remember you."

Anna looked down at her hands and blushed. "That's okay."

"I have something for you."

"Oh god Jim I'm so sorry, I just-"

"No, wait. We'll get to that. I mean I got you a gift."

She took the box and unwrapped it. "Oh Jim, thank you!"

"Not a problem. Here, let me help you. Put your hair up."

Anna lifted her hair and exposed her pale neck, all delectable and elegant, just like Audrey Hepburn. Damn, how good would it be to nibble her ear and bite that neck? The aroma of her perfume and hair made my head spin. I reached forward and the pendant fell into that delicious little crease between her small perfect boobs. My fingers traced along the freckled white skin of her neck with the barest touch as I reached back to hook the clasp. I think she even shivered. "There."

"You didn't have to do that Jim."

"It's no problem. Really. And here, I have the money. Ten thousand cash." I handed her the envelope.

Anna put the money in her lap and held her hands to her face. "Oh god Jim, I'm so embarrassed."

I thought she was going to cry. I leaned forward and put my arms around her and kissed the top of her head.

"Please Anna, take the money. I know you need it. I don't want to know what for. Your mother said you need help and that's enough for me. What good is your old Uncle Jim if he can't help you out, eh?"

I'm not her real uncle, but she looked at me then and smiled and she had tears in her eyes. "Thank you so much. I don't know how I can ever repay you."

"You don't have to. That's a gift too." I lifted my pint. "Cheers."

"Cheers." She looked at me more sad than embarrassed, it seemed.

"Hey," I said, "how about we get something to eat?"

She looked at me all sad again. "Sure."

"You really sure? You don't look sure."

She looked away. Then I realised.

"It's not enough, is it?"

She looked down at the floor. She was crying now.

"Oh baby." I took her hand. "Anna, look at me."

She stared. Her eyes glistened.

"Listen to me. Let me do something. Let me give you forty thousand more."

"No."

I put a finger to her delicious red lips. "Shush. That's fifty thousand all up, and I want to give it to you and I hope it's more than enough." She closed her eyes briefly and nodded. "Good. And don't worry, you don't have to pay it back." I reached into my pocket and took out the electronic key. "Look, I'm at The Savoy hotel. It's nearby. One of the best hotels in London. I can afford it."

Anna smiled. "It's better than a two-star hotel in Notting Hill."

"Exactly. Now, gorgeous young lady, all I ask in return is that you also let me treat you to dinner. How about you come back to the hotel and we order food up to my suite? Yes, suite. Bottle of Champagne, the best of food, and celebrate how we've become acquainted again. And that your financial worries are over, thanks to Uncle Jim."

I entwined my fingers in hers. "Whatcha say, kiddo?"

Anna lifted her glass and finished the wine in one gulp. "Sure. Let's get out of here."

"Excellent." I stood up and offered her my arm.

*

Anna strolled to the window. "You must have done well for yourself. To be able to afford this room and view."

"Just got lucky," I said. "I sold my company to Microsoft. I just happened to have the right product and client base."

I walked over beside her and we surveyed the view over the Embankment and the Thames.

"You know, my first ever technology job was in a building near here, on The Strand. Some days I'd walk over Hungerford Bridge with Nicola Lombardi to the Royal Festival Hall and we'd have lunch there. Hungerford is the railway bridge over there to the right."

"Oh, was she your girlfriend?"

"No. I was only a young man and I had this foolish romantic idea that my future wife had to have long dark hair like that American actress Jennifer Connelly, and be as beautiful and sexy as her. All I needed to do was wait until she came along. Then we'd take one look at each other and that would be it. And Nicola wasn't Jennifer, though she seemed to like me. God, what a fool I was."

"Yes. Poor Nicola."

"Indeed."

There was a knock on the door. "Well, great, that's the food. I'm starving."

After dinner I topped up our Champagne glasses and went to get my laptop. I imagined Anna was hopeful I would produce the extra forty grand I'd promised her. I sat down at the desk and logged into personal banking.

"Tell me the account number you want this money deposited in to."

Anna fumbled with her phone. "Oh, yes. Hold on. Um, here." She walked over and showed me.

"This should be instantaneous. Forty thousand, confirm, there you go. No, wait, SMS verification to my phone. Yes, and yes. That's it."

Anna looked at her phone for a few seconds. Then she nodded and smiled at me. "Oh god, Jim, this is so generous."

I stood up and put my arms out. "Come here." We held each other for a long time and I rubbed my hand up and down her back. I think she cried.

I took Anna's hand and walked towards the wall to the room control screen. The blinds came down and the lights dimmed and Coldplay's The Scientist started on the sound system.

I led her into the bedroom and hugged her again at the foot of the bed. I whispered in her ear. "You really are quite beautiful Anna." I stood behind her and gently scratched along the beautiful pale skin of her bare arms. Then up to her shoulders and around the back to the zipper at the top of her dress. "Sweetie, it would mean so much to me to see you naked. Can you do that for me?"

She didn't say anything for a few seconds. Then she nodded.

I eased the zipper down and reached under to her gorgeous young titties. Anna inhaled sharply when I cupped her boobs and rubbed my palms over the nipples. Then back around to pull the zipper all the way down and ease the beautiful green dress over her shoulders and down so she could step out of it. She only had heels and silky white panties on now. It was so fucking sexy.

I took the phone out of my pocket. "God Anna, this means so much to me. Can I take some photos?"

"Okay. As long as you don't have my face in them."

"Sure. Can I tell you what to do. I mean, to pose for me?"

"If you like."

"Good girl. I like poses that don't show your face anyway. Can you take your underwear off?"

I got the phone ready as Anna slipped out of the panties. I snapped one from behind. I admired the long straight red hair down her back, her little white bum, and her sexy slim legs in those heels.

"Now from the front. Neck down."

Anna turned in my direction but looked towards the wall. I moaned at the sight of her trimmed dark red bush and took another photo.

"Now can you get on the bed for me? Yes, on your hands and knees." Another snap. "And lie on your tummy. Legs spread slightly. And lift your hair up, show me your neck." Snap. "Good girl. Now Anna, can you get on your hands and knees again? And can you lean forward on your elbows and push your bum in the air. Yes, honey, arch your back like that with your legs spread a little. Oh god yes!" Snap, snap, snap. The sight of Anna's exposed pussy and tight little anus made me hard. This was so much better than my wildest expectations.

"I want to get naked honey."

"Can you dim the lights some more?"

"Sure."

I got back to the bed and undressed and reached for Anna's hand as she looked back at me over her shoulder.

"Just stand beside me for a little."

Anna got off the bed and I faced her and put my hand up to her cheek. Delicate strokes with the backs of my fingers.

"So beautiful."

I leaned forward and kissed the delicious red lips and put my hands on her waist and reached back to feel her lovely little bum cheeks.

"Now, lie down again, on your back."

Accompanied by the smallest push from me on her chest, Anna eased back on the bed. I pulled her legs apart and kissed the inside of a thigh, all the way down to her pussy. Oh god, that aroma. I resisted the temptation to dive in and turned my attention to the other leg. I kissed on the inside of the knee, then further kisses all the way down that beautifully smooth white skin, to the ultimate goal.

Then it was mine. I pressed my nose, then my whole face, into that inviting bush and inhaled. What a combination. Woman, girl, young pussy, pee even, but that turned me on too. All those wonderful aromas mixed together in a gorgeous pale, slim, red-haired girl.

Then my lips on her lower lips, to kiss and lick and stroke. I parted the sweet folds with my fingers. What a delicious wet sound. I leaned forward to taste the exposed pinkness.

"You're so sexy Anna. God, you taste so good."

I licked in long strokes, top to bottom. My saliva and Anna's lubrication combined to create a delicious slippery mound that my tongue explored and probed.

Time to get a little kinky. I lifted Anna's legs up and pushed them back to expose her even more. And there it was in front of me, the tight rosebud of her anus. I used my tongue to explore the edges, to let her know what was coming, and to make her anticipate if I would do such a thing. I imagined she wouldn't believe I would do that, it would be far too naughty, wouldn't it? Yes, let her think that. That's when I pressed my tongue right into the sphincter.

"Aaaaahhhhhh!"

She lifted her back at the unexpectedness of the sensation but that didn't stop me. I probed with my tongue, put it right in there and the nastiness of it turned me on even more.

Then back to her pussy and up to the clit and another arch of her back. I put my finger in my mouth as I flicked my tongue over the clit and felt her try to move away because the sensation was so good. I removed the finger all coated in saliva as I continued the clit licking with my tongue, and placed the finger back down at the rosebud. Then the slight push into her rectum, combined with the sensation on her clit, all became too much for Anna.

"Noooooooooo."

Another arch of her back as she tried to get away. That must have been a real strong orgasm for her.

"Of fuck yes. Good girl, come as hard as you like."

Anna looked like she was having convulsions on the bed. I was impressed with my ability to make her come so hard.

Now it was my turn. I took Anna's delicate hand and placed it on my hard cock. "Sweet girl, look how hard you make me. And down under. Feel how full my balls are? I have so much cum for you. I've dreamed about putting this cock inside you. Now, just lie back and let me put it in."

"No. Um, I mean, don't you want to do it from behind? Wouldn't you like that?"

"Yes, good girl. I would."

Anna got on her hands and knees on the bed again. I spat on my fingers and coated my knob in preparation for the sweet pussy. I rubbed it up and down the slit and leaned forward and placed a hand on her shoulder. A slight push forward and then I was inside.

"Nnnnnnnnnn."

"Oh fuck!" Oh my god, such a grip. I had to force my way into her pussy, but when I did it was the hottest, tightest, sweetest sensation my cock had ever experienced.

I eased my hands back down to Anna's waist and held on as I started the gentle fuck. I built the tempo slowly to savour how she squeezed my cock like she was trying to force me out. The speed increased and I began to piston. Each thrust was accompanied by Anna's grunt and I felt that if I continued, I'd probably come too quickly. But goddammit, that's what I wanted right now, and it would probably make Anna come again too.

I hammered away inside her. I looked down and could make out her little rosebud as I fucked away like a madman. When I spat on my thumb and placed it on her anus, I felt my orgasm approach.

"Ahhhhhh."

Anna's moan of pleasure set me off. I gripped her waist, my eyes rolled up in my head, and spurts of hot cum sprayed up inside the beautiful girl.

"Fuuuccckkk!"

I shivered inside Anna. Completely filled her with my cum. Then I was spent and eased myself down on to the bed to lie on my back and stare at the ceiling as I gasped.

I looked over to Anna who was still on all fours but I couldn't see her because her head was down and her hair covered her face.

After a few seconds she slid off the bed and said "I need to take a shower."

"Sure, go ahead. I'll just recover here. Wow."

As my heart and breathing started to come back to normal I realised it was still early and we'd probably have time for more sex later. How fucking good was this?

I figured I could have a short snooze and then ask Anna what she wanted to do next.

*

It was very quiet when I woke.

I sat up and looked around and saw no sign of Anna. I picked up my phone and realised I'd been asleep for two hours. I walked around the suite. Nothing of Anna or her clothes. Maybe she'd gone to the bar? I checked my phone for messages. Zero. Did she have somewhere to go? She never said anything.

This was strange. As I dressed, I saw the necklace on one of the bedside tables. I picked it up and stared. How terrible that she'd forgotten it. If she did need to be somewhere, it would have been nice if she'd told me. But at least now I had an excuse to call her to give the necklace back.

And then, of course, the penny dropped. I remembered the way she'd shivered when I put the necklace on her. The way she'd looked away when I took photos. Her shivers of revulsion that were not orgasms. The way she wanted to do it doggy, and after when she put her head down, so she didn't have to look in my face. And now she was gone.

I walked into the living room and pressed the button to open the blinds. It was dark and the lights twinkled on the Thames. I looked down over the river and back towards Hungerford Bridge. Life went on as normal. Boats went up and down the river. People crossed back and forth over the bridge. I glanced at my laptop. I remembered how someone had told me that these days if you have a LinkedIn account it's possible to find just about anyone you've ever worked with.

I wonder whatever happened to Nicola Lombardi?

*

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ColinPiperColinPiperabout 2 months agoAuthor

Thanks for the comments. As there is a series planned, and there's money involved, Jim and Anna will meet again in Vol. 02. This time in Amsterdam's Red Light District, where Anna's little white bum will be the centre of attention for Jim and a cute little Asian whore. Lekker.

AnonymousAnonymous4 months ago

no anal,but still .....

SwewxxxSwewxxx5 months ago

This one claims a continuation.

She will need him again.

Next time no excuses for no rear endings. I only hope it's her first time back there.

ColinPiperColinPiper11 months agoAuthor

Yes, a story where the main character is an asshole is not a world we want to live in all the time, but such is life. Thanks.

AnonymousAnonymous11 months ago

Misogynistic Bastard!....5 Stars!!!

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