- Joined
- Mar 21, 2024
Seven Months Ago...
"Dammit!" My curse was quiet but heartfelt. The tight, clingy material of the dress I'd bought just this morning had crept up my thighs again.
I should've known better than to buy it on a whim. But the dress had looked so damned good on me when I'd tried it on at the shop. A low, off the shoulder top that highlighted my abundant boobs. A short hem that showed off my trim thighs. I'd stretched my neck and back into a painful pretzel to... Damn! My ass looks great!
My mom would hate it but that just made me want it more. I loved the dress so much that I shoved the clothes I'd worn into the shop into my handbag and wore the dress out of the shop. All was fine until I'd walked a block towards the subway entrance. My usual long strides had caused the hem to stretch and creep up my thighs a fraction of an inch with each step I took. I pulled the hem down and took shorter steps.
The dress behaved as long as I took short steps. But I'd forgotten on my walk from the subway to the hotel. Unconsciously my long legs had fallen into their usual long strides. By the time I remembered, the hem of the dress had hiked up to just below where the cheeks of my ass began.
I stopped on the sidewalk. Outside the entrance of the hotel were large concrete planters with flowers for decoration. I waited until the doorman's attention was focused away from my direction. Partially hidden behind a planter, I began tugging the hem down. A woman looked daggers at me as she walked past. Two men nodded at me with grins of appreciation. I nodded back and consciously shortened my stride as I entered the hotel's lobby.
Dressed as I was, I felt uneasy walking into a hotel in the middle of the day. I just knew everyone was whispering about me. Knew I was a whore meeting a guest for sex. Marla had texted me the room number, so I didn't slow my walk to the elevators. As the heels of my Christian Louboutin's made ringing sounds on the lobby's slate floor, the only notice I garnered was from the concierge. But he just smiled and looked away. He at least knew what-was-what.
In the elevator, I purposely hiked the hem of my dress up to just below indecent and gave my boobs a lift. The man who answered my knock was becoming a semi-regular of mine. Tim was my first. My first client. Barely a week after he'd fucked me in his office, he'd contacted Marla to arrange another appointment. That second time, like this time, had also been in this hotel.
As soon as the door closed behind me, Tim pressed me against a wall for a standing kiss and grope session. He smiled into our kiss when his roving hands moved up the hem of my dress to molest my ass cheeks and discovered that I wasn't wearing panties.
"What's your excuse this time," I asked.
"I'm meeting a prospective client at his office," Tim replied. Same excuse as last time. Tim's a senior partner at a large law firm. No one really questions how he spends his time as long as he keeps his billable hours high and the money flowing in. After letting him play with my tits and ass for another minute, I voiced the need to piss. Tim released me after giving my ass a final, hard squeeze.
In the month I've been a whore, I've learned that many of the clients I meet are eager, very eager, to get their cock as deep inside me as soon as possible. Discomfort and pain as dry shaft pulled and stretched dry pussy walls followed. I'd discovered that a simple expedient helped lessen the discomfort between my legs until my pussy moistened.
In the bathroom I put a large glob of a water-based lubricant on two of my fingers. Pushing, spreading and rotating my fingers as far inside me as I could moistened the first inches of my pussy. A second glob followed the first and I spread more in a film around my hole. Hopefully now my pussy wouldn't be pulled and stretched too painfully during initial penetration.
I washed my hands and pulled the hem of my dress down. After flushing the toilet for sound effects, I rejoined Tim. He had two bourbons poured and handed me one. Marla had warned me to be careful what I drank when with a client. Hell, I'd learned in high school about guarding myself from drinking anything that might have been spiked. With former high school boys or present-day clients, I only drank from beer bottles I opened or drinks I prepared.
"You're not trying to roofie me, are you," I asked before taking a sip.
"Now, Viv. Why would I need to roofie a sure thing," Tim asked as he reached under my dress to cup my pussy.
That was certainly true. I'd also learned in high school how to shotgun beer and do shots. Tossing back a shot of bourbon was no problem though it burned all the way down and exploded in my empty stomach. Tim laughed at my scrunchy facial expressions as I exhaled.
"Mmm, nice and wet already," Tim said in approval as he continued to finger my pussy.
"Just thinking about what was waiting for me got me wet," I lied, hopefully convincingly, as we exchanged another long kiss. Through the kiss I hummed a long, throaty sound of approval as Tim used a fingertip to diddle my clit.
There were some positive things about Tim that I took pleasure in. He was clean. He didn't take a shower in his aftershave. (Guys, a splash is enough, no need to use the whole bottle.) Most of all, there was no pretense on his part. He didn't try and treat me like we were on a date. To him I was a bought and paid for 'sure thing' and that's how he treated me. If he wanted to finger my pussy, he did. When he wanted to fuck me, he would. In between his wants, it was up to me to provide other 'entertainments' such as sucking his cock on demand.
Drinking wasn't the only education I received while in high school. Everything I needed to know about being a whore and satisfying men I'd learned while dating high school boys. Most clients are simple creatures, easily satisfied and even easier fooled. Give them girls ready to suck their cocks with warm, wet pussies to fuck and they're happy.
The last time Tim and I met, unhurried by work pressures, I'd learned that he loves taking his time. I was aware that I was on a clock. I had just enough time to fuck him, change clothes and still catch my regular train for home.
Wanting to move things along, I let Tim diddle my pussy for only a few more seconds before, clasping his wrist, I pulled his hand from between my legs. Moving to the mini bar, I selected two more small bottles from the refrigerator. One for my glass and one to top off Tim's drink.
"Are you trying to get me drunk, Viv?"
Setting my glass down, now it was my time to laugh as I reached to loosen his tie.
"Now, Tim. Why would I need to get a sure thing drunk?"
Sipping our drinks we took turns loosening and losing clothing. Since I had on only my dress, it wasn't long before I was naked except for my stilettos. Maneuvering Tim closer to the couch, I gave him a push that sat him down, bouncing his ass on the couch cushion. Tim really seems to enjoy playing with my body. While I whole-heartedly applaud any man who likes taking time to engage in long foreplay, when I'm pressed for time it's best to move things along. Leaning over I continued removing his clothes while he fondled my tits.
Tim's also a real tit lover. Which might explain why he requests me and my 34DDs. I finished my drink and straddled Tim's hips. Coat, shirt and tie were tossed to the floor while Tim took his time sucking on my nipples while his hands continued to explore my ass and pussy. Sliding two fingers up my pussy, he was pleased to find that, thanks to the motion-lotion, I was wet and ready for him.
Pushing Tim's hands away, I forced him to sit back and relax on the couch. Sliding off Tim's thighs, I went to my knees on the floor to remove his pants, briefs and shoes. Pushing his knees open, I leaned in and let Tim watch me run my tongue from his balls to the tip of his cock several times before opening my mouth to let the bulbous head slip past my lips.
Tim finished his drink and watched as I continued to stroke and suck his cock. Rising from my knees to straddle his lap, I took his glass and set it aside. Tim continued to play with my tits as I slid Tim's cock tip between my pussy lips. With the aid of the lubricant it didn't take long before we were both wet and ready.
By spreading my knees further out to the sides I lowered my pussy closer to the tip of Tim's cock. I reached between us to grasp his shaft. Placing the tip to my hole I began impaling myself on hard cock. Twerking my hips, I pulled my hand away once Tim's cock was firmly inside me. Motion lotion and my juices soon had the shaft sliding easily inside me as I rode Tim cowgirl while leaning over to dangle my nipples near his mouth.
There was a clock alarm on a table beside the bed. I glanced at it while pressing Tim's mouth hard to my breast. Tim likes to take his time, but I didn't have my usual patience for long foreplay. The last time we'd met he'd come twice. The cash gift he'd given me afterwards was very nice. If I made Tim come twice today, I was hoping to receive another nice gift. It was time to get his first release over with, so he'd have time to rest up for a second before I had to leave.
While I whole-heartedly approved of Tim's slow approach to foreplay, when it came to sex he was fast and enthusiastic. I wasn't riding his cock for very long before his hands left my tits to grasp my waist. Strong upward thrusts had me bouncing on his lap while his grip on my hips pulled me down to meet his next thrust. I put my hands on the back of the couch to either side of his head for balance. Leaning forwards just enough to run my gyrating tits over his face, I teased him by pulling back and away each time before his mouth could capture one of my nipples.
"Oh, my God... You feel so good in me. Like that... Just like that," I whispered when the angle of penetration pleased me. "Fuck me like that."
I continued teasing with my tits while voicing how good I was being fucked. This had the desired effect of making Tim approach release quickly. I think I mentioned that Tim was fast and enthusiastic? Well, I whole-heartedly approved of enthusiasm. I was much less appreciative with the fast! At least with lovers. But with clients? I liked clients who came quickly.
"Come in me, Baby. Oh, you're fucking me so good. I can feel your cock so fucking deep in my pussy. Oh, my God! Oh, my God! Oh, my God! It feels so fucking good!" I continued with my vocal foreplay as I raised the pitch and urgency in my voice.
I continued to tease Tim's seeking mouth with nipples that always seemed to bob just far enough away from his lips to avoid capture. To excite Tim more, I changed my voice to a high-pitched squeak to mimic a sexual arousal I didn't feel.
"Come in me, Baby. Fuck! It feels so good. So fucking deep... Harder...Fuck me harder... Yes! That feels so good!'
I continued to push Tim closer to his climax with words, pussy and teasing. Moving erratically, I slapped my big tits against his cheeks while twerking my hips on his thrusting cock. Only when he groaned out that he was coming and I felt his cock pulse in my pussy, filling me with his cum, did I let him capture his reward. He finished coming while sucking hard on my tit.
I stayed impaled on Tim's cock until I felt the last throbbing movement of his cock. Rising up and off Tim's dick, we both watched as a large amount of cum gushed from my pussy lips to pool on Tim's stomach. Watery cum ran off to one side to wet the couch. Thick, white cum clumped where it landed. I contracted deep cunt muscles to force as much cum from my pussy as I could until no more dripped from my pussy lips. There was a string of cum left hanging from my pussy. Reaching, I collected it on my fingers. I brought my fingers to my mouth and sucked them clean.
"Mmm, delicious," I smiled.
"Damn that was a good fuck," I congratulated Tim in a satisfied voice as I slid off his thighs. Kneeling on the floor I pushed his legs open. I pulled my hair back and out of the way so it wouldn't drag through the wet pool as I lowered my mouth to his stomach. Stomach muscles quivered as I pursed my lips to vacuum cum into my mouth.
Tim reached with his hand to help control my long hair and contentedly watched as I finished by licking up every bit of cum with my tongue until his stomach was clean of our sex.
I thought again about what a turnabout I'd achieved in such a short time. Just over a month ago I'd never let a guy come in my mouth. I'd even refuse to kiss a boy after he'd gone down on me. Now I was eating and swallowing cum from a hairy stomach. Also, just over a month ago I'd never been very vocal during sex. Now I was learning that 'talking dirty' really excited most men.
Shortly afterwards we were relaxing on the suite's bed with fresh drinks. I took very small sips from mine. I knew Tim wouldn't kiss me after I'd had his cum in my mouth. So I'd let him watch me make a large, very stiff bourbon'n'cola drink. Without being obvious, I'd made sure he could see as I swished the potent combination around in my mouth to wash all traces of his cum from between my teeth.
So the glass I was sipping from now made this my fourth or fifth, or maybe even my sixth drink in a short amount of time depending on how much bourbon I'd added to the cola. So much booze on an empty stomach is a dangerous thing. The tip of my nose was numb and I was in danger of giggling at the smallest provocation. Some girls sound delicate and... And lovely when they giggle. I just sound stupid when I giggle.
Tim did most of the talking. Between playtime with my tits, he began spewing about all the shit he had to put up with from bosses at work and his wife and kids at home. Just as he had the last time we were together. All the while I listened attentively. By now I knew the names of his wife, kids and co-partners at his office. Most of Tim's venomous spew this time was about his youngest daughter who wanted to drop out of college in her senior year.
"I can't believe the money I wasted trying to give her an education. Flushed down the crapper by that ungrateful bitch," was his oft repeated lament. Tim had had more than his share of drinks, too.
Mental therapists charge shit loads of money per hour in this city. Two hours of my time was a bargain for Tim, plus I did something better for my clients than just validating parking. In truth? Giving Tim an attentive audience and the time to get all this crap out of his system maybe did more for him than my letting him put two loads of cum into me.
But cum, not psychology, is my business. I was determined to get a good gift. Glancing at the clock I knew I had to act. While Tim talked, I put my hand on his cock, slow stroking until it was semi-hard. Tim's talk of his woes ceased as I kissed my way down his stomach. I spent a few minutes sucking his cock to full hardness before I straddled his hips again.
Lifting and positioning his cocktip to where it needed to be, I impaled myself on his cock again and began riding him. I resisted when he tried to pull me down so he could suck on my nipples. Playfully, I kept fending off the hands trying to play with my tits. Leaning down to tease him, I let Tim bury his face between my tits before pulling away.
"No. Not this time you greedy boy. I did all the work last time, so you don't get my tits again until you give me what I want." I pinned Tim's wrists to the bed and leaned over to whisper my demand in his ear. "I want you to fuck me long and hard!"
Now that Tim knew how to earn his 'reward', I was squealing at how quickly he moved to put me on my back. Tim isn't a young man. Having come just a short while ago I was certain I'd be fucked for quite a long time as he strove to earn his reward for services rendered.
I spread my legs wider as he began to thrust hard. The slide of his cock filling me as his weight pressed me into the mattress felt pretty damned good. Tim had been a decent lover the last time we met and he was again today. There were long, passionate kisses as our tongues tried to enter each other's mouths as deeply as his cock penetrated my pussy.
But soon he stopped kissing me and rose above me on locked arms for some serious missionary fucking. His hard groin was pounding into my much softer pussy lips so rapidly my breaths came in gasps between grunted words as I urged him to fuck me harder.
I love it when my job is also pleasant. Tim was sweating and gasping for air when he finally pressed hard between my legs as he came. Moving my hips to grind against his groin had my clit tingling. I was pleasantly surprised at how good I felt between my thighs. I hadn't come close to achieving orgasm but everything between my legs was telling me I'd been satisfyingly fucked good and hard.
As Tim panted for breath above me on locked arms, after a few more seconds I reached up to grasp the back of his neck to guide his mouth to my tits for his deserved reward. I was content to lie still while feeling his still hard cock move inside me as he sucked on my nipples. But... alas, there's always a 'but' as Marla had once told me... But the time on the alarm clock was telling me it was close to time to go. And that's what I had to tell Tim as I pushed gently until he reluctantly rolled off me.
Tim seemed content to lay on the bed as I cleaned his cock with a hurried blow job. He seemed content to watch my boobs jiggle and sway as I slipped off the bed. Apparently, he wasn't all that content though. Sliding over the bed behind me, he gathered me up in his arms and pulled me onto his lap.
"Stay", he said. His hand pushed between my legs. Fingers pushed inside my cum wet pussy. I felt them moving, curling to capture the hard cartilage of my pubic symphysis in his grip. "Stay two more hours with me."
"I can't. Not today," I replied, twerking my hips suggestively over the fingers in my pussy while trying to convey the regret I didn't feel with my voice. I wanted nothing more than to leave though I tried not to show it. He kept asking and I kept turning him down with a made-up excuse. I mean... How many whores need to get home in time to sit and eat supper with her parents?
The fingers inside me continued to grip me so tight they hurt. My clit had received so much stimulation in the last two hours from fingers and cock that I really didn't want to be touched anymore! I put my hand on his and he finally let me pull his fingers from between my thighs. But my escape to the bathroom was not to be just yet. Tim stopped me halfway to the door and pushed me to my knees.
'Dammit! Just let me leave!' I thought. Pretending I didn't want to be doing anything else in the world, I sucked on the sticky shaft while trying very hard not to look towards the clock beside the bed. I just wanted to go home by now. Finally, after rolling his limp cock around in my mouth with my tongue until Tim was satisfied, I was able to escape into the bathroom. The things I do to earn a nice gift...
I left the door open so we could talk. I wasn't really paying much attention as Tim began saying something-something about having a plan to make a lot of money soon.
I pinned my hair up and after cleaning my face, stepped into the shower for a quick rinse. Once Tim's sweat from my tits and stomach was washed off, I detached the shower head from the wall. Opening my legs wider than my usual stance, I directed the streams of water between my legs to wash his cum from my pussy and thighs. After inserting a tampon and a quick toweling off, I slipped my dress on.
Back in the room, I let Tim watch as I repaired my makeup while we had another drink. Tim said he'd left me a gift on the table next to the couch. Putting the envelope in my handbag, I saw the lipstick I thought I'd left in the hotel room of a previous client. On a whim, I used the mirror behind the mini bar to apply a thick, red coating to my lips.
Tim's look of confusion was real as I took my time to press a red kiss emoji onto the tip of his now flaccid cock. But he certainly didn't complain and found it hilarious when, thinking quickly, I explained that only 'the best, of the best, of the best' could earn the Award of the Red Dick. Tim laughed and I giggled as, with a nod and a finger wave, I exited the room.
I counted the gift, the very nice gift, Tim had given me in the taxi. Next week was mom's birthday and I was taking the day off to spend with her. Window shopping in the mall and a lunch on my dime. Then home for birthday cake with her friends. This tip went a long way to making up for a lost day of pay.
On the walk back to the entrance to the subway, I texted Marla to report mission accomplished so my portion of the fee she charged clients for my time and body would be deposited into my account. I was surprised when she texted back that she needed me in her office ASAP. Well, that posed no problem since I was headed there anyway to change clothes.
**********
"What the hell are you wearing?" Marla didn't look happy.
"It's a new dress I bought this morning. You don't like it?"
"It fine for a party at night while you pose as arm-candy on the arm of a gay man who is still in the closet. It's completely inappropriate for the middle of the day," Marla replied. "You look like a fucking prostitute!"
"Well, duh! I am a prostitute."
"But you don't need to look like one! Go change and toss that thing in a closet until you have to attend a cocktail party at night," Marla ordered. Once I changed clothes Marla pointed at a chair and told me to sit.
"Viv, I've been patient, more than patient," Marla sighed. "Letting you fill my storage closet with your things. Letting you use my bathroom to change clothes and put on makeup. But my patience is at an end. You need to move out of my office soon! It's past time for you to have your own apartment."
"I know. I know, Marla. It's just... I can't seem to save enough money," I explained. Money seemed to flow through my fingers faster than cum through a client's dick. There was always another pair of shoes I just had to have!
"You don't have the money," Marla sounded astonished. "Viv, you're sitting on an ass that I charge clients a high price to use! A very high price of which you get a very good percentage. Really, Viv, have you no self-control?"
Marla looked at me slouching in my chair and frowned.
"Speaking of sitting, young lady, posture is the first thing a client notices."
"I thought it was my big boobs men noticed first," I countered as I sat up with my back ramrod straight.
"Tits will get you only so far, Viv," Marla volleyed back. "My clients aren't paying me top dollar for common street whores! They expect poise and sophistication in addition to sex. If all a man wants is a cock sucking whore, he can find those standing on any corner of Fifth Street. If a man wants a young lady who enjoys giving oral sex, he comes to me. It's best you begin cultivating the finer attributes along with your oral skills. "
Marla leaned back against her chair's back (With perfect posture, of course!) and tapped a manicured fingernail on her desk while considering options.
"Viv, it's your money. I can't tell you how to spend it. But I strongly suggest you put together enough money to get an apartment before you buy more clothes and shoes! I know exactly how much you're earning since I'm the one depositing the money into your bank account.
"But enough is enough so here's the deal..." Marla pointed a slim finger at me. "By next Friday you will have an apartment. Any box in my storage room past that date gets tossed. Any makeup cluttering my sink gets shit canned.
"To help you earn enough money quickly, I have a client who wants three girls this Saturday. It's a bachelor party. A car will be outside my office at noon to pick you and the other girls up. The party will last until 4am Sunday morning. Needless to say, the fee you'll receive for a sixteen-hour party with fifteen or so men should be more than enough for you to rent any apartment you find next week."
"Fifteen men!" The thought of that many men fucking me was frightening. I began trying to weasel my way out of this 'party/orgy/gangbang'.
"But, Marla, it's the weekend. I can't tell Mom I'm working..."
"Don't even try, Viv," Marla cut me off. Her slender finger was pointed at me again for emphasis. "Tell your mom you're doing a sleepover with a girl you met at an office you're working at or something. This one appointment on Saturday will earn you enough money that you can spend next week apartment hunting. I mean it, Viv. Next Friday you're out of here or all those dresses and shoes cluttering up my storage closet goes into a dumpster!"
"Not my shoes!" I was horrified. It was sinking in that Marla meant every word.
So far I had three clients scheduled between now and next Friday. More would probably be added between now and then. But I needed cash in the bank now to go apartment hunting. If it took letting fifteen men fuck me to save my shoes...
"Okay, I'll be here Saturday," I glumly nodded, surrendering to my fate. Marla smiled. She'd won but wasn't going to gloat.
"By the way, Viv, have you ever been with a woman? Have you ever wondered..."
"What? I thought you said fifteen men!"
"Fifteen or so men and two more of my girls. I'd be astonished if the client doesn't want some girl-on-girl-on-girl action at some point to entertain his guests."
"I, ahh... I thought about it a couple of times while watching porn. What it would be like. Umm, there was this one girl in high school... She didn’t make it a secret that she liked other girls," I hesitantly admitted. "But no, I've never been with a girl, you know, that way."
"This client sends a lot of money my way. I don't like the idea of sending a virgin to him," Marla said thoughtfully and then smiled as she picked up her phone. After checking her iPhone's schedule book, she auto dialed a number.
"Sandy? I have a client for you. Friday morning. 10am. Female. Two hours." Marla listened for a few moments then looked at me and smiled. "She's gorgeous and Sandy? She's a virgin. Do everything to make sure no part of her is virginal when she leaves… Thank you, Sandy. I'll text you the location later."
I listened to Marla's side of the conversation and my mouth dropped open when I realized that she was scheduling me as a client!
"10am, Friday," Marla told me in her no-nonsense voice after hanging up. "I'll text you the hotel and room number. I'll pay for Sandy and the room and deduct it from your future pay after you have an apartment. Congratulations, Ms. Olivia. You just booked your first call girl."
Dressed in my 'suburban' clothes, I stopped at the Coffee Clutch on my way to the train stop. A fruity pastry snack was just what I needed to keep my blood sugar up for the train ride home. I was nervous the entire trip. Trying to maintain my side of conversation during dinner was difficult. In my room I watched a lot of lesbian porn.
The day after tomorrow I'd have my first experience with another woman. The day after that I'd have my first gangbang. This weekend was shaping up to be... Exciting? Frightening? What word or phrase was I searching for?
I settled on... An unusual experience.
"Dammit!" My curse was quiet but heartfelt. The tight, clingy material of the dress I'd bought just this morning had crept up my thighs again.
I should've known better than to buy it on a whim. But the dress had looked so damned good on me when I'd tried it on at the shop. A low, off the shoulder top that highlighted my abundant boobs. A short hem that showed off my trim thighs. I'd stretched my neck and back into a painful pretzel to... Damn! My ass looks great!
My mom would hate it but that just made me want it more. I loved the dress so much that I shoved the clothes I'd worn into the shop into my handbag and wore the dress out of the shop. All was fine until I'd walked a block towards the subway entrance. My usual long strides had caused the hem to stretch and creep up my thighs a fraction of an inch with each step I took. I pulled the hem down and took shorter steps.
The dress behaved as long as I took short steps. But I'd forgotten on my walk from the subway to the hotel. Unconsciously my long legs had fallen into their usual long strides. By the time I remembered, the hem of the dress had hiked up to just below where the cheeks of my ass began.
I stopped on the sidewalk. Outside the entrance of the hotel were large concrete planters with flowers for decoration. I waited until the doorman's attention was focused away from my direction. Partially hidden behind a planter, I began tugging the hem down. A woman looked daggers at me as she walked past. Two men nodded at me with grins of appreciation. I nodded back and consciously shortened my stride as I entered the hotel's lobby.
Dressed as I was, I felt uneasy walking into a hotel in the middle of the day. I just knew everyone was whispering about me. Knew I was a whore meeting a guest for sex. Marla had texted me the room number, so I didn't slow my walk to the elevators. As the heels of my Christian Louboutin's made ringing sounds on the lobby's slate floor, the only notice I garnered was from the concierge. But he just smiled and looked away. He at least knew what-was-what.
In the elevator, I purposely hiked the hem of my dress up to just below indecent and gave my boobs a lift. The man who answered my knock was becoming a semi-regular of mine. Tim was my first. My first client. Barely a week after he'd fucked me in his office, he'd contacted Marla to arrange another appointment. That second time, like this time, had also been in this hotel.
As soon as the door closed behind me, Tim pressed me against a wall for a standing kiss and grope session. He smiled into our kiss when his roving hands moved up the hem of my dress to molest my ass cheeks and discovered that I wasn't wearing panties.
"What's your excuse this time," I asked.
"I'm meeting a prospective client at his office," Tim replied. Same excuse as last time. Tim's a senior partner at a large law firm. No one really questions how he spends his time as long as he keeps his billable hours high and the money flowing in. After letting him play with my tits and ass for another minute, I voiced the need to piss. Tim released me after giving my ass a final, hard squeeze.
In the month I've been a whore, I've learned that many of the clients I meet are eager, very eager, to get their cock as deep inside me as soon as possible. Discomfort and pain as dry shaft pulled and stretched dry pussy walls followed. I'd discovered that a simple expedient helped lessen the discomfort between my legs until my pussy moistened.
In the bathroom I put a large glob of a water-based lubricant on two of my fingers. Pushing, spreading and rotating my fingers as far inside me as I could moistened the first inches of my pussy. A second glob followed the first and I spread more in a film around my hole. Hopefully now my pussy wouldn't be pulled and stretched too painfully during initial penetration.
I washed my hands and pulled the hem of my dress down. After flushing the toilet for sound effects, I rejoined Tim. He had two bourbons poured and handed me one. Marla had warned me to be careful what I drank when with a client. Hell, I'd learned in high school about guarding myself from drinking anything that might have been spiked. With former high school boys or present-day clients, I only drank from beer bottles I opened or drinks I prepared.
"You're not trying to roofie me, are you," I asked before taking a sip.
"Now, Viv. Why would I need to roofie a sure thing," Tim asked as he reached under my dress to cup my pussy.
That was certainly true. I'd also learned in high school how to shotgun beer and do shots. Tossing back a shot of bourbon was no problem though it burned all the way down and exploded in my empty stomach. Tim laughed at my scrunchy facial expressions as I exhaled.
"Mmm, nice and wet already," Tim said in approval as he continued to finger my pussy.
"Just thinking about what was waiting for me got me wet," I lied, hopefully convincingly, as we exchanged another long kiss. Through the kiss I hummed a long, throaty sound of approval as Tim used a fingertip to diddle my clit.
There were some positive things about Tim that I took pleasure in. He was clean. He didn't take a shower in his aftershave. (Guys, a splash is enough, no need to use the whole bottle.) Most of all, there was no pretense on his part. He didn't try and treat me like we were on a date. To him I was a bought and paid for 'sure thing' and that's how he treated me. If he wanted to finger my pussy, he did. When he wanted to fuck me, he would. In between his wants, it was up to me to provide other 'entertainments' such as sucking his cock on demand.
Drinking wasn't the only education I received while in high school. Everything I needed to know about being a whore and satisfying men I'd learned while dating high school boys. Most clients are simple creatures, easily satisfied and even easier fooled. Give them girls ready to suck their cocks with warm, wet pussies to fuck and they're happy.
The last time Tim and I met, unhurried by work pressures, I'd learned that he loves taking his time. I was aware that I was on a clock. I had just enough time to fuck him, change clothes and still catch my regular train for home.
Wanting to move things along, I let Tim diddle my pussy for only a few more seconds before, clasping his wrist, I pulled his hand from between my legs. Moving to the mini bar, I selected two more small bottles from the refrigerator. One for my glass and one to top off Tim's drink.
"Are you trying to get me drunk, Viv?"
Setting my glass down, now it was my time to laugh as I reached to loosen his tie.
"Now, Tim. Why would I need to get a sure thing drunk?"
Sipping our drinks we took turns loosening and losing clothing. Since I had on only my dress, it wasn't long before I was naked except for my stilettos. Maneuvering Tim closer to the couch, I gave him a push that sat him down, bouncing his ass on the couch cushion. Tim really seems to enjoy playing with my body. While I whole-heartedly applaud any man who likes taking time to engage in long foreplay, when I'm pressed for time it's best to move things along. Leaning over I continued removing his clothes while he fondled my tits.
Tim's also a real tit lover. Which might explain why he requests me and my 34DDs. I finished my drink and straddled Tim's hips. Coat, shirt and tie were tossed to the floor while Tim took his time sucking on my nipples while his hands continued to explore my ass and pussy. Sliding two fingers up my pussy, he was pleased to find that, thanks to the motion-lotion, I was wet and ready for him.
Pushing Tim's hands away, I forced him to sit back and relax on the couch. Sliding off Tim's thighs, I went to my knees on the floor to remove his pants, briefs and shoes. Pushing his knees open, I leaned in and let Tim watch me run my tongue from his balls to the tip of his cock several times before opening my mouth to let the bulbous head slip past my lips.
Tim finished his drink and watched as I continued to stroke and suck his cock. Rising from my knees to straddle his lap, I took his glass and set it aside. Tim continued to play with my tits as I slid Tim's cock tip between my pussy lips. With the aid of the lubricant it didn't take long before we were both wet and ready.
By spreading my knees further out to the sides I lowered my pussy closer to the tip of Tim's cock. I reached between us to grasp his shaft. Placing the tip to my hole I began impaling myself on hard cock. Twerking my hips, I pulled my hand away once Tim's cock was firmly inside me. Motion lotion and my juices soon had the shaft sliding easily inside me as I rode Tim cowgirl while leaning over to dangle my nipples near his mouth.
There was a clock alarm on a table beside the bed. I glanced at it while pressing Tim's mouth hard to my breast. Tim likes to take his time, but I didn't have my usual patience for long foreplay. The last time we'd met he'd come twice. The cash gift he'd given me afterwards was very nice. If I made Tim come twice today, I was hoping to receive another nice gift. It was time to get his first release over with, so he'd have time to rest up for a second before I had to leave.
While I whole-heartedly approved of Tim's slow approach to foreplay, when it came to sex he was fast and enthusiastic. I wasn't riding his cock for very long before his hands left my tits to grasp my waist. Strong upward thrusts had me bouncing on his lap while his grip on my hips pulled me down to meet his next thrust. I put my hands on the back of the couch to either side of his head for balance. Leaning forwards just enough to run my gyrating tits over his face, I teased him by pulling back and away each time before his mouth could capture one of my nipples.
"Oh, my God... You feel so good in me. Like that... Just like that," I whispered when the angle of penetration pleased me. "Fuck me like that."
I continued teasing with my tits while voicing how good I was being fucked. This had the desired effect of making Tim approach release quickly. I think I mentioned that Tim was fast and enthusiastic? Well, I whole-heartedly approved of enthusiasm. I was much less appreciative with the fast! At least with lovers. But with clients? I liked clients who came quickly.
"Come in me, Baby. Oh, you're fucking me so good. I can feel your cock so fucking deep in my pussy. Oh, my God! Oh, my God! Oh, my God! It feels so fucking good!" I continued with my vocal foreplay as I raised the pitch and urgency in my voice.
I continued to tease Tim's seeking mouth with nipples that always seemed to bob just far enough away from his lips to avoid capture. To excite Tim more, I changed my voice to a high-pitched squeak to mimic a sexual arousal I didn't feel.
"Come in me, Baby. Fuck! It feels so good. So fucking deep... Harder...Fuck me harder... Yes! That feels so good!'
I continued to push Tim closer to his climax with words, pussy and teasing. Moving erratically, I slapped my big tits against his cheeks while twerking my hips on his thrusting cock. Only when he groaned out that he was coming and I felt his cock pulse in my pussy, filling me with his cum, did I let him capture his reward. He finished coming while sucking hard on my tit.
I stayed impaled on Tim's cock until I felt the last throbbing movement of his cock. Rising up and off Tim's dick, we both watched as a large amount of cum gushed from my pussy lips to pool on Tim's stomach. Watery cum ran off to one side to wet the couch. Thick, white cum clumped where it landed. I contracted deep cunt muscles to force as much cum from my pussy as I could until no more dripped from my pussy lips. There was a string of cum left hanging from my pussy. Reaching, I collected it on my fingers. I brought my fingers to my mouth and sucked them clean.
"Mmm, delicious," I smiled.
"Damn that was a good fuck," I congratulated Tim in a satisfied voice as I slid off his thighs. Kneeling on the floor I pushed his legs open. I pulled my hair back and out of the way so it wouldn't drag through the wet pool as I lowered my mouth to his stomach. Stomach muscles quivered as I pursed my lips to vacuum cum into my mouth.
Tim reached with his hand to help control my long hair and contentedly watched as I finished by licking up every bit of cum with my tongue until his stomach was clean of our sex.
I thought again about what a turnabout I'd achieved in such a short time. Just over a month ago I'd never let a guy come in my mouth. I'd even refuse to kiss a boy after he'd gone down on me. Now I was eating and swallowing cum from a hairy stomach. Also, just over a month ago I'd never been very vocal during sex. Now I was learning that 'talking dirty' really excited most men.
Shortly afterwards we were relaxing on the suite's bed with fresh drinks. I took very small sips from mine. I knew Tim wouldn't kiss me after I'd had his cum in my mouth. So I'd let him watch me make a large, very stiff bourbon'n'cola drink. Without being obvious, I'd made sure he could see as I swished the potent combination around in my mouth to wash all traces of his cum from between my teeth.
So the glass I was sipping from now made this my fourth or fifth, or maybe even my sixth drink in a short amount of time depending on how much bourbon I'd added to the cola. So much booze on an empty stomach is a dangerous thing. The tip of my nose was numb and I was in danger of giggling at the smallest provocation. Some girls sound delicate and... And lovely when they giggle. I just sound stupid when I giggle.
Tim did most of the talking. Between playtime with my tits, he began spewing about all the shit he had to put up with from bosses at work and his wife and kids at home. Just as he had the last time we were together. All the while I listened attentively. By now I knew the names of his wife, kids and co-partners at his office. Most of Tim's venomous spew this time was about his youngest daughter who wanted to drop out of college in her senior year.
"I can't believe the money I wasted trying to give her an education. Flushed down the crapper by that ungrateful bitch," was his oft repeated lament. Tim had had more than his share of drinks, too.
Mental therapists charge shit loads of money per hour in this city. Two hours of my time was a bargain for Tim, plus I did something better for my clients than just validating parking. In truth? Giving Tim an attentive audience and the time to get all this crap out of his system maybe did more for him than my letting him put two loads of cum into me.
But cum, not psychology, is my business. I was determined to get a good gift. Glancing at the clock I knew I had to act. While Tim talked, I put my hand on his cock, slow stroking until it was semi-hard. Tim's talk of his woes ceased as I kissed my way down his stomach. I spent a few minutes sucking his cock to full hardness before I straddled his hips again.
Lifting and positioning his cocktip to where it needed to be, I impaled myself on his cock again and began riding him. I resisted when he tried to pull me down so he could suck on my nipples. Playfully, I kept fending off the hands trying to play with my tits. Leaning down to tease him, I let Tim bury his face between my tits before pulling away.
"No. Not this time you greedy boy. I did all the work last time, so you don't get my tits again until you give me what I want." I pinned Tim's wrists to the bed and leaned over to whisper my demand in his ear. "I want you to fuck me long and hard!"
Now that Tim knew how to earn his 'reward', I was squealing at how quickly he moved to put me on my back. Tim isn't a young man. Having come just a short while ago I was certain I'd be fucked for quite a long time as he strove to earn his reward for services rendered.
I spread my legs wider as he began to thrust hard. The slide of his cock filling me as his weight pressed me into the mattress felt pretty damned good. Tim had been a decent lover the last time we met and he was again today. There were long, passionate kisses as our tongues tried to enter each other's mouths as deeply as his cock penetrated my pussy.
But soon he stopped kissing me and rose above me on locked arms for some serious missionary fucking. His hard groin was pounding into my much softer pussy lips so rapidly my breaths came in gasps between grunted words as I urged him to fuck me harder.
I love it when my job is also pleasant. Tim was sweating and gasping for air when he finally pressed hard between my legs as he came. Moving my hips to grind against his groin had my clit tingling. I was pleasantly surprised at how good I felt between my thighs. I hadn't come close to achieving orgasm but everything between my legs was telling me I'd been satisfyingly fucked good and hard.
As Tim panted for breath above me on locked arms, after a few more seconds I reached up to grasp the back of his neck to guide his mouth to my tits for his deserved reward. I was content to lie still while feeling his still hard cock move inside me as he sucked on my nipples. But... alas, there's always a 'but' as Marla had once told me... But the time on the alarm clock was telling me it was close to time to go. And that's what I had to tell Tim as I pushed gently until he reluctantly rolled off me.
Tim seemed content to lay on the bed as I cleaned his cock with a hurried blow job. He seemed content to watch my boobs jiggle and sway as I slipped off the bed. Apparently, he wasn't all that content though. Sliding over the bed behind me, he gathered me up in his arms and pulled me onto his lap.
"Stay", he said. His hand pushed between my legs. Fingers pushed inside my cum wet pussy. I felt them moving, curling to capture the hard cartilage of my pubic symphysis in his grip. "Stay two more hours with me."
"I can't. Not today," I replied, twerking my hips suggestively over the fingers in my pussy while trying to convey the regret I didn't feel with my voice. I wanted nothing more than to leave though I tried not to show it. He kept asking and I kept turning him down with a made-up excuse. I mean... How many whores need to get home in time to sit and eat supper with her parents?
The fingers inside me continued to grip me so tight they hurt. My clit had received so much stimulation in the last two hours from fingers and cock that I really didn't want to be touched anymore! I put my hand on his and he finally let me pull his fingers from between my thighs. But my escape to the bathroom was not to be just yet. Tim stopped me halfway to the door and pushed me to my knees.
'Dammit! Just let me leave!' I thought. Pretending I didn't want to be doing anything else in the world, I sucked on the sticky shaft while trying very hard not to look towards the clock beside the bed. I just wanted to go home by now. Finally, after rolling his limp cock around in my mouth with my tongue until Tim was satisfied, I was able to escape into the bathroom. The things I do to earn a nice gift...
I left the door open so we could talk. I wasn't really paying much attention as Tim began saying something-something about having a plan to make a lot of money soon.
I pinned my hair up and after cleaning my face, stepped into the shower for a quick rinse. Once Tim's sweat from my tits and stomach was washed off, I detached the shower head from the wall. Opening my legs wider than my usual stance, I directed the streams of water between my legs to wash his cum from my pussy and thighs. After inserting a tampon and a quick toweling off, I slipped my dress on.
Back in the room, I let Tim watch as I repaired my makeup while we had another drink. Tim said he'd left me a gift on the table next to the couch. Putting the envelope in my handbag, I saw the lipstick I thought I'd left in the hotel room of a previous client. On a whim, I used the mirror behind the mini bar to apply a thick, red coating to my lips.
Tim's look of confusion was real as I took my time to press a red kiss emoji onto the tip of his now flaccid cock. But he certainly didn't complain and found it hilarious when, thinking quickly, I explained that only 'the best, of the best, of the best' could earn the Award of the Red Dick. Tim laughed and I giggled as, with a nod and a finger wave, I exited the room.
I counted the gift, the very nice gift, Tim had given me in the taxi. Next week was mom's birthday and I was taking the day off to spend with her. Window shopping in the mall and a lunch on my dime. Then home for birthday cake with her friends. This tip went a long way to making up for a lost day of pay.
On the walk back to the entrance to the subway, I texted Marla to report mission accomplished so my portion of the fee she charged clients for my time and body would be deposited into my account. I was surprised when she texted back that she needed me in her office ASAP. Well, that posed no problem since I was headed there anyway to change clothes.
**********
"What the hell are you wearing?" Marla didn't look happy.
"It's a new dress I bought this morning. You don't like it?"
"It fine for a party at night while you pose as arm-candy on the arm of a gay man who is still in the closet. It's completely inappropriate for the middle of the day," Marla replied. "You look like a fucking prostitute!"
"Well, duh! I am a prostitute."
"But you don't need to look like one! Go change and toss that thing in a closet until you have to attend a cocktail party at night," Marla ordered. Once I changed clothes Marla pointed at a chair and told me to sit.
"Viv, I've been patient, more than patient," Marla sighed. "Letting you fill my storage closet with your things. Letting you use my bathroom to change clothes and put on makeup. But my patience is at an end. You need to move out of my office soon! It's past time for you to have your own apartment."
"I know. I know, Marla. It's just... I can't seem to save enough money," I explained. Money seemed to flow through my fingers faster than cum through a client's dick. There was always another pair of shoes I just had to have!
"You don't have the money," Marla sounded astonished. "Viv, you're sitting on an ass that I charge clients a high price to use! A very high price of which you get a very good percentage. Really, Viv, have you no self-control?"
Marla looked at me slouching in my chair and frowned.
"Speaking of sitting, young lady, posture is the first thing a client notices."
"I thought it was my big boobs men noticed first," I countered as I sat up with my back ramrod straight.
"Tits will get you only so far, Viv," Marla volleyed back. "My clients aren't paying me top dollar for common street whores! They expect poise and sophistication in addition to sex. If all a man wants is a cock sucking whore, he can find those standing on any corner of Fifth Street. If a man wants a young lady who enjoys giving oral sex, he comes to me. It's best you begin cultivating the finer attributes along with your oral skills. "
Marla leaned back against her chair's back (With perfect posture, of course!) and tapped a manicured fingernail on her desk while considering options.
"Viv, it's your money. I can't tell you how to spend it. But I strongly suggest you put together enough money to get an apartment before you buy more clothes and shoes! I know exactly how much you're earning since I'm the one depositing the money into your bank account.
"But enough is enough so here's the deal..." Marla pointed a slim finger at me. "By next Friday you will have an apartment. Any box in my storage room past that date gets tossed. Any makeup cluttering my sink gets shit canned.
"To help you earn enough money quickly, I have a client who wants three girls this Saturday. It's a bachelor party. A car will be outside my office at noon to pick you and the other girls up. The party will last until 4am Sunday morning. Needless to say, the fee you'll receive for a sixteen-hour party with fifteen or so men should be more than enough for you to rent any apartment you find next week."
"Fifteen men!" The thought of that many men fucking me was frightening. I began trying to weasel my way out of this 'party/orgy/gangbang'.
"But, Marla, it's the weekend. I can't tell Mom I'm working..."
"Don't even try, Viv," Marla cut me off. Her slender finger was pointed at me again for emphasis. "Tell your mom you're doing a sleepover with a girl you met at an office you're working at or something. This one appointment on Saturday will earn you enough money that you can spend next week apartment hunting. I mean it, Viv. Next Friday you're out of here or all those dresses and shoes cluttering up my storage closet goes into a dumpster!"
"Not my shoes!" I was horrified. It was sinking in that Marla meant every word.
So far I had three clients scheduled between now and next Friday. More would probably be added between now and then. But I needed cash in the bank now to go apartment hunting. If it took letting fifteen men fuck me to save my shoes...
"Okay, I'll be here Saturday," I glumly nodded, surrendering to my fate. Marla smiled. She'd won but wasn't going to gloat.
"By the way, Viv, have you ever been with a woman? Have you ever wondered..."
"What? I thought you said fifteen men!"
"Fifteen or so men and two more of my girls. I'd be astonished if the client doesn't want some girl-on-girl-on-girl action at some point to entertain his guests."
"I, ahh... I thought about it a couple of times while watching porn. What it would be like. Umm, there was this one girl in high school... She didn’t make it a secret that she liked other girls," I hesitantly admitted. "But no, I've never been with a girl, you know, that way."
"This client sends a lot of money my way. I don't like the idea of sending a virgin to him," Marla said thoughtfully and then smiled as she picked up her phone. After checking her iPhone's schedule book, she auto dialed a number.
"Sandy? I have a client for you. Friday morning. 10am. Female. Two hours." Marla listened for a few moments then looked at me and smiled. "She's gorgeous and Sandy? She's a virgin. Do everything to make sure no part of her is virginal when she leaves… Thank you, Sandy. I'll text you the location later."
I listened to Marla's side of the conversation and my mouth dropped open when I realized that she was scheduling me as a client!
"10am, Friday," Marla told me in her no-nonsense voice after hanging up. "I'll text you the hotel and room number. I'll pay for Sandy and the room and deduct it from your future pay after you have an apartment. Congratulations, Ms. Olivia. You just booked your first call girl."
Dressed in my 'suburban' clothes, I stopped at the Coffee Clutch on my way to the train stop. A fruity pastry snack was just what I needed to keep my blood sugar up for the train ride home. I was nervous the entire trip. Trying to maintain my side of conversation during dinner was difficult. In my room I watched a lot of lesbian porn.
The day after tomorrow I'd have my first experience with another woman. The day after that I'd have my first gangbang. This weekend was shaping up to be... Exciting? Frightening? What word or phrase was I searching for?
I settled on... An unusual experience.
