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Second Job

"I meet a prostitute again in a business meeting, five years after I paid for her."

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Author's Notes

"This story happens at the same time as Escorting Experiment, which should probably be read first. As always, if you enjoy the story, please hit the like and favourite buttons."

The London train was quiet as I headed in on a day trip for a meeting. Unlike most trips, I had company part way. My daughter Helen and her friend Kim were also on board, staying overnight with some erotic purpose in mind.

At least, that was my assumption from their whispering and giggling. I tried to concentrate on work but couldn't help glancing up from my laptop at Kim, who looked gorgeous. The girls got off at Finsbury Park, giggling together, dragging their wheelies behind them.

"For the shopping, silly," I'd been informed by my daughter when I questioned why they needed such oversized cases for an overnight stop.

I watched Kim's lovely bum wiggle as she headed towards the stairs to the Underground, astonished she regularly and enthusiastically fucked me.

I left the train at St. Pancras International, navigated through the confusing station, and out onto the square.

Thirty minutes later, I was ready after the usual nonsense of setting up laptops, connecting to screens, and, most importantly, getting coffee.

Half a dozen people from a Hong Kong-based startup crowded into the room with us, noisily setting up, gabbling away in Cantonese.

Finally, the hubbub in the crowded conference room died down. I sat quietly at the back with a couple of our engineers as they made their financial pitch. When our visitors arrived earlier, I had been immersed in laptop issues. I quickly scanned them. One of the six presented slides in a plummy accent, gesticulating enthusiastically. I smiled. Startups always felt the need for a slick front. The other five were sat in a row at the table. One other was a Westerner; the other four were Chinese and obviously Hong Kong from their informality.

Of the Chinese, a gorgeous young woman wearing a business suit caught my eye, looking familiar. I stared at her momentarily, trying to place where I'd seen the buxom woman before. I grinned to myself. Buxom didn't adequately describe her enormous boobs. Her business dress confused me for a moment until the memories flooded back.

A long time ago, during my divorce, I had felt frustrated and powerless and did something I had never done before or since: I hired an escort, the woman now sitting nearby.

As usual, I had stayed at the Langham in Kowloon. That particular evening, I wandered to a hotel on Nathan Road, where I had booked an additional, cheap room for the night, not wanting to chance it in my posh hotel. After checking in, I headed to the hotel bar, which was a notorious pick-up joint. I ordered a beer, and sure enough, I was approached by a young Chinese woman after a few minutes.

She was a pretty young thing with long black hair and dark eyes, wearing high heels and a low-cut grey and white striped dress that showed off her massive boobs.

"Hi, I'm Louise," she said.

She sounded bored, and I knew it wasn't her real name. "Brian," I replied, lying. "Pleased to meet you."

Her approach was stereotypical, "Are you looking for a good time?"

I grinned. That was my entire purpose. "Of course." I got straight to the point. "How much for the whole night?"

The girl looked surprised. She looked me up and down, her gaze lingering on my crotch, and we quickly agreed on a price.

We made a pretence at small talk, but I was impatient, even though we had the whole night ahead.

"Let's go upstairs," I suggested.

"Louise" quickly agreed. We were alone in the lift to the twelfth floor, so I pulled the girl close and groped her, roughly feeling her boobs and fingering her pussy.

The lift chimed, and the doors opened. Once inside my room, I cracked open some fizz and made more desultory small talk. The hooker fidgeted, obviously bored.

"Okay, what do you want to do?" she demanded. "How kinky are you?"

That was it, I snapped. The frustrations of the divorce were too much; I needed to be in control.

"Strip, then suck me," I ordered.

Without a word, Louise stood, reached behind herself and unzipped her dress, which fell around her ankles, leaving her standing in high heels, stockings, white panties, and no bra. I almost came right then.

She knelt in front of me, undid my trousers, and pulled them and my underpants down. My dick sprang out, almost hitting her face.

"Aren't you a big boy?" she said, suddenly more interested. She leaned forward and wrapped her massive boobs around my knob, her hands pressing them together. I started slowly fucking her tits. The end of my knob protruded from her cleavage on each upstroke.

"Come on, suck it," I ordered. Obligingly, Louise looked down. Her tongue just reached and licked off the glistening drops of pre-cum. I continued tit-fucking her for a few strokes.

"Suck me properly. Take all of it in your mouth," I ordered.

Again, Louise obeyed me, looking up at me with wide, dark eyes as she slowly swallowed my cock. I loved that she followed my every whim. When I felt myself about to come, my hands clasped her head, stopping her from pulling back. My dick shot gallons of hot spunk into her mouth. When I released her head, she looked up at me, opened her mouth so my cum dribbled out, then swallowed.

"Yummy," she said before licking my jizz from around her mouth and then sucking me clean. My colossal dick was still rock hard.

"Turn around," I ordered.

When she obeyed, I pushed her roughly to her knees. Still fully dressed, with my trousers around my ankles, I pulled her knickers aside and thrust my cock into her wet pussy. She was tight, but my rigid member still slid home easily. I pounded her hard from behind, pulling her back onto my cock. Louise was moaning, but I doubted it was real. I didn't care; that night was all about control.

Her cunt was tight enough, but I knew what would be tighter. I spat on my fingers and stuck one into her arse.

"Anal is extra," she said.

I didn't care. My wet cock pulled out of Louise's wet pussy and slowly rammed into her tight arse. Several hard thrusts later, I was balls-deep in her rectum. I fucked her tight bottom with slow, deep strokes at first, but I felt the need to punish the hooker for my wife's sins, so I brutally pounded Louise's tight arse.

That I had also sinned never crossed my mind. I didn't last long and quickly came inside the hooker's bum. When I pulled out, my cum dribbled slowly down Louise's thighs from her gaping arsehole.

"Sorry," I muttered. "I'm not usually like this".

Louise laughed. "You weren't that rough. And I loved your mammoth dick."

I got my money's worth. I fucked Louise in every imaginable position and was completely drained when we finally collapsed to sleep.

When I awoke, "Louise" was gone, taking the money I had left beside the bed.

---

My thoughts returned abruptly to the present day, realising I'd been asked a question.

"Sorry, can you repeat that? I was thinking about another problem."

The presenter drew a deep breath, obviously irritated. "Do you think it will work?"

I couldn't help glancing at the young woman - I hadn't caught a name. She was definitely the same person. She was slightly older but unmistakably "Louise."

The young woman smiled back and nodded slightly.

I turned to the presenter. I was familiar with the proposal, having recently reviewed it. The architecture was acceptable and perfectly implementable. I nodded. "Yes, it will work," I started. I outlined a few technical objections and suggested a couple of design improvements.

Memories of our Hong Kong encounter distracted me for the rest of the morning, but the meeting went well; their engineers knew their stuff. The young woman was particularly sharp. As I had recommended the day before, we would proceed with the investment. And I did glean a name: Ms. Leung.

We broke for lunch around one o'clock, the typical gruesome buffet. After browsing for a few sandwiches and a samosa, I sought out Ms. Leung. She smiled broadly when I approached.

"Hi," I said nervously. "Nice to see you again, but I didn't catch your first name." I grinned. "I just know it isn't Louise."

The woman laughed. "No, I'm Jennifer or Jenny. Whichever you prefer." She paused. "And I know you're not Brian."

"Jennifer, I think. I like that name." I shook my head. "I'm sorry I was so awful back then. I was going through a divorce."

Jennifer followed me out of the crowded conference room and into the quieter corridor.

She smiled. "Oh, you weren't that bad. You were one of my nicer ... clients." She looked down. "And I remember your mammoth dick vividly."

Jennifer glanced at my empty ring finger. "Is there a lucky girl?"

Kim and Alison flashed through my mind. I shook my head. "Divorced. My daughter is eighteen now."

The woman beamed. "I wouldn't mind reacquainting myself with that horse cock."

"Would this be a professional transaction?" I asked, unwilling to use an escort again.

She shook her head, grinning. "I rarely do my second job anymore. I needed the money back then; Hong Kong is so expensive. Now, I only do it for the occasional thrill." She smiled lewdly. "This would be purely for pleasure - I never get to play with men as big as you."

I glanced at the time. The bulk of the afternoon was detailed financial nonsense, and we only needed to return for the wrap-up at four. "We have a few hours now?" I suggested. "Where are you staying?"

I was surprised when Jennifer named a posh hotel near Trafalgar Square. It had been on the list my daughter and Kim had considered. That would be awkward!

It was only a few stops away on the Picadilly Line. I grinned. "That's not too far. Shall we?"

Jennifer smiled and nodded. "Yes."

Thirty minutes later, after being crammed pleasantly together on the crowded Underground, we were in her hotel room.

I pulled Jennifer close, wrapped my arms around her and kissed her passionately. Her hand crept into my trousers, massaging my enormous boner.

My hands slid down her back, gently stroking her flanks before grasping her bum.

"Let's not rush," I said when we broke. "I want you to properly enjoy it this time."

Jennifer laughed. "Oh, I loved it well enough last time. Can't beat a rough anal pounding."

She slipped out of her navy jacket and hung it in the wardrobe. When she turned back to me, I slowly unbuttoned her blouse. It fell open at the front, revealing her fabulous cleavage, uplifted by a tight, white corset.

As I unfastened her long navy skirt, Jennifer unbuttoned the sleeves of her blouse and shucked it off her shoulders. The blouse fell untidily to the floor, followed by Jennifer's long skirt, which slithered down until it was bunched around her ankles.

Jennifer quickly stepped out of the skirt, leaving her wearing a corset, tights, and black high heels. She looked stunning, everything I remembered.

My hands slowly unhooked the fastenings on the front of her corset, starting from the top, where the hooks were under severe pressure, restraining her mammoth breasts. Jennifer pulled the straps of her corset off her shoulders and pulled it down, stepping out of it when it reached the floor. She kicked off her black heels as I started to pull her tights down. She sat perched on the armchair behind her, letting me pull the tights off one leg and then the other.

As each leg was freed, I lifted her dainty foot and nibbled at her toes. Soon, she just wore tiny white panties.

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When Jennifer stood and turned in a full circle, I started to strip. She smiled coquettishly. "Do you like what you see?"

She was beautiful. Everything from her dark, almond-shaped eyes to her mammoth boobs and shapely body was perfect. I could hardly wait.

I nodded. "Perfection."

She pulled off her white panties, revealing the tiny black triangle of her pubes.

I pulled her close to my naked body. My mammoth erection pressed against her flat belly as we kissed, our tongues exploring each other.

Still locked in our passionate kiss, I manoeuvred us until Jennifer's legs pressed against the bed.

We broke apart. "Lie back on the bed," I ordered.

Jennifer sat down and wiggled backwards until her feet were up on the edge of the bed, with her knees splayed wide apart.

I grinned to myself. The girl knew what I had planned. Jennifer smiled lewdly at me. "Eat me," she said before lying flat on her back.

I knelt by the bed. Jennifer's pussy was just out of my tongue's reach. She giggled when I grabbed her thighs and pulled her towards me.

My hands slid slowly up and down her slim flanks. Her skin was warm and smooth. One palm slid across her flat belly and down over her black pubes. A finger pressed between her shaved labia. She was wet.

My tongue replaced the finger, probing between her lips until it found her love bump. Jennifer sighed as my tongue played intimately with her.

"Oh, just there," she whispered.

My forefinger teased her slit below where my tongue stimulated her. It wormed inside, hooking around slowly.

"God, you're good at this," Jennifer gasped.

A second finger joined the first, and both started hooking in and out slowly. Jennifer was panting softly now.

"Keep going," she moaned. "Nearly there."

My fingers frigged her faster as my tongue played around, stimulating her clitoris. Jennifer was almost silent as she came, just panting softly. Her hips bucked under my tongue, and I felt her juices coat my invasive fingers.

When her muscles stopped quaking, Jessica sat up, her arms hugging her knees.

"That was wonderful." She laughed. "None of the punters ever did that to me."

Jennifer stared at my engorged dick, shaking her head. "I should offer to return the favour, but I hate giving head. It's the first thing every punter demands, and I'm sick of it."

I looked her up and down and laughed. "I don't think I need any help getting erect."

Her mammoth tits were pressed between her wide-spread knees, and her shaved slit oozed where her thighs met.

She had, by far, the most enormous tits of anyone I'd fucked. "Just ride me, cowgirl, so I can watch your puppies bounce."

She grinned. "All you boys ask for that. Anything so I can feel your monster inside me."

I lay on my back, propped up by the pillows. Jennifer turned and knelt astride me, expertly positioning herself above my rampant weapon. She grinned at me as she started to lower herself. "I'm looking forward to being split open."

My glans pressed between her fat, shaved lips. She gasped when it entered her. "You're even bigger than I remember. Fantastic."

Her wide, dark eyes were glued to me as she let her weight drive my fat boner into her tight, wet cunt.

Her face was blissful when her bum finally rested on my thighs. "Every inch of your monster is stretching me to bursting," she said softly. "I could never forget this feeling." She leered at me. "So delightfully full!"

Jennifer lifted herself slowly. My dick inched out of her tight, moist grotto until only my tip was inside. She sighed as her weight forced me back inside her incredible pussy. "Fabulous," she said.

Her hands reached forward and pressed against my chest. I stared up at her ecstatic face as her hips rocked, expertly driving my steely sword repeatedly deep into her wet twat.

I reached around her waist, gently grasping her firm bum as she slowly rode me. Once my dick slid smoothly in and out as her cunt stretched to accommodate my girth, Jennifer sped up, rising and falling quickly, driving me balls-deep with every fabulous thrust. Her enormous chest rose and fell magnificently as she impaled herself on my unbending erection.

"That feels incredible," she sighed. "Pound me. Make me come."

I needed no further prompting. My hands slid up the warm skin of Jennifer's back, wrapping around her torso. I pulled her close so her fabulous chest pressed against me, and her face was inches from mine.

My hips drove my rigid pole deep into her wet minge, as hard and fast as I could manage. Her face contorted with pleasure, and she panted softly. After a few more thrusts, my efforts were rewarded. I felt her body quiver and shake as she climaxed quietly again. Her cunt rippled around my engorged member, driving me over the edge. My rampant dick slammed into her, spewing gallons of spunk into her fabulous snatch, as she quivered above me. Balls-deep in her pussy, my hips thrust upwards hard, ejecting more jizz from my dick.

Our mutual passion ebbed away, and Jennifer slumped against me with my rigid dick deep inside her. "Thank you," she murmured. "No one else has ever made me feel like that." She kissed me passionately.

We rested like that in the warm afterglow of sex for a few minutes. Suddenly, Jennifer giggled. "That's one hole satisfied." She pushed herself upright so she sat astride me. Her magnificent boobs were flushed. "Now, you'd better satisfy my bum."

I laughed. "What position does madam require?"

Jennifer didn't hesitate. "Doggy. You can go so deep and hard that way."

She grinned. "I'd better get some lube."

I watched her walk into the small bathroom, admiring her slender hips and firm arse. When she returned carrying a bottle, I looked her up and down, marvelling at her voluptuous figure and beautiful face.

Jennifer giggled as she handed me the bottle. "Better make sure I'm well-oiled for your monster."

She climbed naked onto the bed and got onto all fours. She lifted her bum into the air and lowered herself so her face was pressed against the duvet.

She giggled when I squeezed oil into the top of her bum crack. "That's cold," she complained.

I cackled lewdly. "I'll soon warm your arse up."

The lube ran down between her flushed buttocks, coating her perfect starfish and oozing into her shaved slit.

My fingers started with her pussy, massaging her meat flaps and pressing briefly inside her wet cunt. Then, my forefinger and middle finger pushed into her two tight, oily orifices. They moved in and out briefly, working the lube into her bum.

After another squirt of oil, my fingers concentrated on her sphincter. Jennifer moaned as they stretched it wider with one, two, and finally three fingers.

She squealed and giggled when I slapped her buttocks. "Are you ready?" I asked.

"Split me open with that monster," she replied, laughing.

I positioned myself behind her, running my glans up and down her bum crack. My dick nudged teasingly at her pussy, pushing slightly inside. Then, it moved up until my tip pressed against her back door.

Jennifer gasped when my hips pushed forward, driving my glans slowly into her tight bottom.

"God, you're huge." She giggled. "You might split me open yet."

My hips pressed forward again, forcing me deeper into her warm, tight backside, with her sphincter resisting all the way.

Jennifer gasped and moaned as I repeatedly pulled back before driving ever deeper. When my groin pressed against her backside, I ran my hands gently over her lovely bum cheeks. "That's it. That's all I've got."

She laughed. "All? So deep and so hard! Like there's a fat steel rod is rammed in my arse."

My hips pulled back, sliding my monstrous dick slowly out until only the tip remained in her bum. My hips drove forward once more, ramming my rampant cock entirely into her rectum in a very slow, hard thrust.

Several repeated later, my engorged weapon slid smoothly in and out, though against much resistance.

"That feels wonderful," Jennifer sighed. "I can feel every inch of your monster distending me."

I changed position slightly, so I was almost above her and could slam my mammoth dick even further into her rectum.

Jennifer gasped. "Ever so deep. So full!"

I increased my pace until my rampant cock hammered into her as hard and fast as I could manage.

My unbending pole hammered into her arsehole for what seemed a blissful eternity. Unlike before, when she climaxed silently, Jennifer now gasped and moaned loudly as I slammed into her backside.

I felt her shudder beneath me, her soft flesh shivering under my hands as she peaked again. Her sphincter clamped painfully hard around my dick. "Split me open. Destroy me," she yelled.

Her arse clamping rhythmically around my engorged weapon drove me over the edge. My hips slammed against her buttocks as my cock erupted into her back passage. Finally, my balls were drained, and Jennifer's orgasm ebbed away.

My hands stroked her flushed body as I paused with my dick balls-deep in her derriere. After a few seconds, I pulled out. Her starfish gaped wide open, and then cum dribbled out as her bum-hole slowly closed.

Jennifer exhaled a long, satisfied sigh. "I never have anal orgasms like that! I hardly needed to finger myself."

She reached behind herself and fingered her bum hole. "That will be sore tomorrow," she giggled. "But it was worth it."

Jennifer turned so she knelt on the bed facing me. Her small hand ran over the bedspread, and she smiled. "The staff will have fun gossiping about that wet patch."

There was a large, discoloured patch. Not just wet with sweat but mixed with lube and spunk. I laughed and reached out a hand to Jennifer. "Let's go and clean up."

She took my hand, and I helped her up. We stood under the hot shower, soaping each other for ages, gently exploring each other's bodies.

Finally, we dried each other and got dressed.

"God, I loved that," I said. "You are incredible."

Jennifer massaged my dick, smiling. "And you are enormous. Better than any punter." She looked at me with wide eyes. "We must do this again."

I laughed. "I can't wait. The sooner, the better."

Jessica just nodded with a massive grin on her face.

When I checked the time, it was gone three. "We'd better get back."

As we hurried through reception, I spotted Helen and Kim sitting at a table, giggling together, surrounded by bags. I tried not to think about what they'd get up to that evening and desperately hoped they hadn't spotted us.

We tried not to look at each other through the boring wrap-up, only glancing at each other occasionally. Finally, the meeting was done.

We met in the corridor. Jennifer looked crestfallen. "I wanted you to stay the night," she said, "but we're on the late plane home. Apparently, something has gone wrong, and we've been summoned. You know how it is."

I was disappointed, but it was probably for the best, given that I didn't want Helen, let alone Kim, to see us together. "I'm in Hong Kong in a few weeks, so see you then?" I asked hopefully.

Jennifer grinned. "Definitely. My sore bottom will have recovered by then."

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Written by grendel54321
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