Raw Confessions
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Call Girl Confessions, Part 2 free porn video
Part 2 - Holly's Story
Holly; a call girl; 30 years old, five foot four inches tall, with midback-length straight blonde hair and blue eyes.
My name is Holly... Holler Holly most people call me 'cause I guess I make a lot of noise when I have sex. I just love fucking and sucking! And when I'm with a guy, I want him to know I'm having a good time too - after all if I'm not enjoying it, I won't put my heart into what I'm doing!
I'm a call girl, which means I work out of my home through a "legitimate" temp agency. The agency, which is really a temporary employment agency for short term hiring, also runs a second business using a few of us girls to fill the needs a normal secretary won't!
How it works is like this. A client, looking for someone to do more for them than typing and filing, calls the temporary agency. They, in turn, call one of us girls and tell us where and when to meet the client. The agency gets a cut for acting as the go-between, and we get the rest. It's not a bad deal - at least I don't have to walk the streets and get robbed or hassled by the police.
I wasn't always a call girl like this. I was actually the daughter of wealthy parents. They disowned me though, after they found out I had been dating a 30 year old man when I was in high school. Paul would smoke weed with me and get some beer so we could party. Usually during our partying, I would get really horny and we'd end up fucking. My parents found out because I was cutting so much class to be with him.
Actually, in looking back at it all, I think I did a lot of it because I wanted to make them mad, to make them punish me, or at least recognize I existed. You see, both my mother and father were too wrapped up in their own worlds to acknowledge that they had a daughter. My mother, in her high society women's groups... having her hoity-toity lunches and her shopping at all the high end stores. My father lived in his corporate world on the umpteenth floor of a big impressive high-rise in his corner office surrounded by other suits. They spent the day discussing financial matters, business deals, and who they were going to take over next.
Needless to say, I never fit into either world and I pretty much grew up on my own. Oh sure, I had money and a nice place to live and all that, but I didn't have the one thing all that couldn't buy. I didn't have love.
I moved in with Paul, who was the only one around to take care of me. He offered his apartment and love at first. Then, after awhile I found out the truth about him.
I was a naive 18-year-old spoiled rich girl back then. I didn't know people could be so devious and underhanded. Paul appeared to be a kind father figure, something I had been missing in my life, and so I fell hard for him. I so wanted someone to love and to love me back that I didn't see the signs until it was too late.
Paul was not who he claimed he was or who I thought he was as well. He turned out to be a controlling, egotistical, abusive tyrant of a man who kept me isolated and away from anyone unless he was right there with me. I wasn't allowed to have any friends except the ones he permitted, and even then I had to tell him everything that was said so he wouldn't think I was talking about him. He routinely went through my emails and my cell phone. He was paranoid that I was always fooling around on him (I wasn't), and plotting to leave him for someone else.
Then one day, he brought a new twist into our relationship. We had gone to this guy's apartment that Paul knew to score some weed. I don't know where Paul knew this guy from, but we went to his apartment together because he didn't want to leave me at home alone. Anyway, we get there and Paul tries the pot out to make sure it's good quality. He gives me a hit or two, just showing off for this friend. Then he goes to pay for it and comes up short of funds. Instead of buying what he can afford, he instead makes the guy another offer.
"I got half the money, but you wanna work a deal for the other half?" Paul asked him.
"What did you have in mind?" the guy said.
"Well, I'll let you fuck my girl here for the rest of the weed," he said. I looked at Paul like he had just grew a second head! I couldn't believe he had suggested something this outrageous!
"Is she any good?" he asked.
"You bet your ass! She's the best fuck in town. And she's a screamer too!" he said, joking with the guy. I was mortified! I turned beet red at his comment and stood there dumbstruck as the deal was finalized. I was going to be partial payment for the weed he wanted to get!
The dealer handed the bag of weed over to Paul and then he turned to me. He got this wicked grin on his face and I looked at him, horrified. His gaunt, pock-marked face had leathery skin and eyes larger than they should have been for his face. He had what I can only assume as a feeble excuse for a beard, although it looked more like a short haired dog with the mange. His hair was thin and falling out in small patches, and when he smiled he showed yellow, crooked, and worn teeth with a few missing here and there.
"Paul, please!" I said, turning to him. But he had made the deal and was more interested in the bag he hand in his hands than me.
"Hurry up and give him what he wants so we can get home. I wanna try this shit out for real!" he said, pushing me towards the dealer. I realized that there was nothing I could do. I hung my head and followed him into the bedroom while Paul stayed in the living room.
He shut the door and then pointed to the bed. "Get undressed," he said simply. I stood there for a moment just looking at him, my feet unable to move. "I said get undressed, you little whore... unless you want me to go out there and tell your boyfriend that you welched on the deal?" he repeated, pointing a thumb to the door behind him.
I knew that would be worse than just going through with fucking this dirtbag and getting it over with. So I slowly began to undress as he leered at me, smiling his crooked smile and licking his lips in anticipation.
I lay down on the bed and got ready to do what I needed to do. He quickly shed his clothes after watching me and climbed into bed. He crawled over the top of me and lay on top of me preparing to get what he was due.
To say that he stunk is an understatement. I don't think the guy had seen soap since puberty! He reeked of sweat, gasoline, cigarettes, beer, and a few other odors I didn't recognize. I almost puked after the first couple of whiffs of his stench. I was able to keep down my lunch though, swallowing a couple times to settle my stomach. He push my legs apart And took hold of his cock getting ready to enter me. I closed my eyes and waited for him to penetrate me and I didn't have to wait long.
I don't know whether it was the drugs that caused his cock to shrink, or if he was just naturally small, but he slid easily into me even without lubrication. My pussy had some difficulty gripping him - you see Paul was a fairly large man and I had gotten used to him, so this needle-dick barely made an impression on me. But I guess the excitement and anticipation of finally getting laid was enough, because after a bit of huffing and puffing I could feel him getting ready to cum.
"I'm gonna cum now whore! I'm gonna cum all over that pretty face!" he said then he pulled out and shot his load onto my face and tits. His cum didn't smell as it should either, having a strange acrid smell to it. After he finished the last spurt, he grabbed me by the hair and pulled me onto his tiny cock. "Suck it! Suck my cock clean, slut!" he growled.
I took him into my mouth, about gagging - and not from his size either! I licked and sucked his cock clean and then pulled back away from him. "There... you got what you wanted for the deal. Now can I go?" I asked him.
"No I think I want some pussy for dessert!" he said reaching out to grab me. I'd had all of him I could take. I grabbed a lamp off the nightstand and swung for the fences, catching the sleaze right in his hooked nose and sending him rolling backwards over the bed howling in pain. I turned and ran out of the room and past Paul in my haste to get away from the whole scene.
*
I left Paul after that. I knew that I had to find some way to support myself - I wasn't going back to him and I damn sure couldn't go back home to Mommy and Daddy! I looked in the paper and found the ad for the temp agency and decided to see if they had anything I could do. I began working as a cleaning lady, cleaning other people's houses and offices. It paid just enough to keep me in a small apartment and keep food on the table, but not much more. I struggled to get by, but at least I wasn't involved with the likes of Paul anymore. I even quit the booze and the drugs - mainly because I couldn't afford them!
I worked as a cleaning lady for about a year when one of the other girls in my cleaning crew told me of a way I could earn more money. I had been complaining about always scraping by and never seeming to have enough money - by the end of the month I was down to eating Ramen noodles for dinner! She told me to go to the office and ask for Lisa... that Lisa would show me how to make more money. The next day, I went in a little early to work to talk to this Lisa person.
"Lisa?" I said, knocking on her office door.
"Yes, come in," came the reply.
"Hi, my name is Holly, I am one of the cleaning crew," I said as I walked in and introduced myself.
"How can I help you?"
"Well, one of the other girls, Angie, said that you could help me. She said that you could show me how to make more money. I am tired of always being broke. I need to earn more money," I explained.
"I see. Close the door, Holly," she said. I closed the door and sat back down.
"I see you have been working here for almost a year now. You and Angie are good friends I take it?"
"Well we get along pretty good. I like working with her and I think she feels the same. I don't know if you'd call us good friends but we do talk and get along well."
"Well, I can show you how to make more money than you do as a cleaning woman, if you are interested. Tell you what... here is my address. Be there tonight at 7:00 pm and I will explain everything," she said.
That night, I arrived at the address Lisa had given me right on time. I rang the doorbell on a very nice split-level ranch house and presently, Lisa opened the door.
"Hi Holly, glad you decided to come. Won't you come in?" she said. Lisa led me into the living room and seated me on the sofa. "Would you like a glass of wine or something?"
"A glass of wine sounds nice. Thank you."
She left for a couple moments, returning with a bottle and a couple glasses. She poured the wine and sat back sipping it. I was about to ask again about the money thing when she spoke first.
"I spoke with Angie after talking with you today and she told me pretty much the same thing you said - that you and her are good coworkers and enjoy working together. She said you are friends and talk and chat a lot while you work. She also said that you have been complaining that you never seem to have enough money and by the end of the month you barely have enough money for food, much less anything else."
"Yes that's right. The end of the month is always hard," I said.
"Well, I have a way of fixing that. But what I am about to tell you can never be repeated outside of this room. If you do, you will immediately be terminated - no excuses, no second chances. Understand?"
"Yes Ma'am," I said, wondering now where this conversation was heading.
And that is when Lisa began telling me about the other side of Kirkland Temporary Services! I listened as Lisa explained that behind the front of a temporary employment agency, there was a call girl service and that select girls from the agency were picked to provide entertainment to their more affluent clients. Lisa said that several of the girls make more money in a single night than they do for two weeks of working as a cleaning lady. And if they used one of their weekend nights for the "dates", they could still do their cleaning jobs as well, doubling their money easily.
I took what she said and thought about the possibility. Most girls would probably be shocked at the idea of becoming a call girl and whoring themselves out for money. But I had already been there with Paul - and I didn't even get paid! So the idea of fucking for bucks wasn't so distasteful to me. After Lisa told me how it all worked and the money I stood to make, it didn't take me long to sign on... a girl's gotta eat, and I was getting real tired of that end of the month menu!
My first "job" came a couple days after the meeting. Lisa called me into the office after work that afternoon.
"You wanted to see me, Lisa?" I asked after knocking on her door.
"Yes, come in and shut the door, please." I did as she said, and sat down in front of her desk.
"I have a client that would like a date this Friday night. Are you up for it?" she asked me.
"Sure, what do I have to do?" I asked.
"Well, for starters, what do you have for clothes?" Lisa asked.
"Sadly, not much. Just a couple pairs of jeans, three or four tops, and my work uniform. I haven't had the money to get anything more."
"Well that won't do. The Judge likes his women to look sexy and tattered jeans aren't sexy! Here is $200.00... go shopping and get yourself something to make a man take notice of you!" she said. Lisa began telling me about the Judge and what his particular fetish was.
Judge Keeler had an obsession with secretaries - and more to the point, slutty secretaries. So I went to the local boutique to see what today's slutty secretary might wear! I found a little secretary costume that contained a bra and panties, a collar/tie neckpiece, and a tiny microskirt with garters for stockings. It was all supposed to resemble a business suit and still be sexy. I picked it up then I picked up a pair of fake glasses with the black plastic frames and a clipboard for the "realistic" look.
I met him in his office that Friday wearing my three-quarter coat so I wouldn't draw attention before I got there. I knew I had made a good first impression to him as he constantly kept admiring my costume and licking his lips as we sat and talked. We discussed my fake job application as well as what future I was looking for; I was so good at acting it out that he'd sometimes wonder if I truly was the call girl he had asked for. But I would always reassure him with a wink or a sudden compliment whenever he doubted, which made him more confident.
The role-play he had created flowed perfectly: I flirted with him, and he invited me for dinner at his house. We then spent the evening eating and drinking, playing out his fantasy to the letter, and finally we had sex together – fulfilling the final act of his play.
Judge Keeler enjoyed good foreplay, more than the actual penetration. That first night he just wanted me to give him a blow job while he used his chubby fingers to play with my pussy. His moans sounded more like bear noises; in fact he did resemble a bear. Though bald, except for the sides, his back was filled with hair. So was his ass for that matter, and his chubby form made him closer to a bear then a man. Yet he was not as strong as a bear, though the sixty year old did have his few moments of glory - it was always somewhat impressive to see him lift me up during sex.
Unfortunately his penis was not impressive, except for the resilience it had. It was smaller than average, and the girth was a bit disappointing. I was able to fit it all in my mouth with hardly any gagging, and I could easily lick around it while sucking him off.
"Ohh Holly!" he said suddenly as I sucked on his cock.
"Is he about to blow already?" I thought to myself. We hadn't been going for very long. I was just hitting my stride! "Oh well, I might as well help him then."
I played with his balls with my hand while sucking his cock all the way down to his crotch. His pubic hair tickled my nostrils, and smelled of dry semen. I could feel his sacks vibrating and soon a spurt of hot cum shot out of his pee-slit, and hit the back of my throat. I swallowed the small amount he had fired, since he apparently found it very satisfying to see. He held my head tight and huffed and moaned at the same time he was coming - until the last drop of sperm had left his body.
I could feel his cock turning soft as it exited my mouth. A single thread of cum and saliva attached itself between my mouth and his cock, forming a bridge, while it exited.
"I am sorry Holly, I did it again. I could not help it, I had to come," he sat down on the bed sweating and breathing heavily, while I cleaned my mouth with a tissue.
"It's ok dear, it was fun as long as it lasted," I liked how he apologized for cumming too quickly; I found it cute and sweet that he cared.
"Next time, next time I promise you won't be disappointed," he said to me while his breathing became more controlled.
I smiled to him and said, "I am not disappointed," it was important to me that my clients believed themselves the best, so I often lied. I kissed him on the forehead and walked towards the bathroom, readying myself to leave.
Closing the bathroom door behind me, I began to inspect myself on the mirror, checking to see what make-up needed to be refreshed. My eyelashes remained mostly untouched except for a small curve on the one of my right eye, which I fixed immediately. My bright red lips had lost some of their color, so I used my lipstick to renovate the color a bit. Though my makeup usually got a bit damaged during sex, it was always my hair that suffered the most. The length of my hair did not help me either, as it made it easier for my clients to grab it during intercourse, thus leaving me to fix it again at the end of it all.
I used a comb to carefully brush my hair back into place, which was not entirely easy. I then washed my mouth with water and some mouth wash, which I had brought along; cleaning out the semen that had remained inside of me. Finally I got dressed in my costume, which was the only clothes I had brought at that time (I have since learned to carry a bigger purse with something to throw on inside for that trip back home!). Once dressed, I came back in the bedroom and Judge Keeler paid for my services.
With a promise to come see him again soon, I kissed him sweetly on the forehead, leaving him with a red lipstick kiss on his bald head and a smile on his lips. I slipped on my coat and went downstairs to the cab I had called, and headed home.
Holly; a call girl; 30 years old, five foot four inches tall, with midback-length straight blonde hair and blue eyes.
My name is Holly... Holler Holly most people call me 'cause I guess I make a lot of noise when I have sex. I just love fucking and sucking! And when I'm with a guy, I want him to know I'm having a good time too - after all if I'm not enjoying it, I won't put my heart into what I'm doing!
I'm a call girl, which means I work out of my home through a "legitimate" temp agency. The agency, which is really a temporary employment agency for short term hiring, also runs a second business using a few of us girls to fill the needs a normal secretary won't!
How it works is like this. A client, looking for someone to do more for them than typing and filing, calls the temporary agency. They, in turn, call one of us girls and tell us where and when to meet the client. The agency gets a cut for acting as the go-between, and we get the rest. It's not a bad deal - at least I don't have to walk the streets and get robbed or hassled by the police.
I wasn't always a call girl like this. I was actually the daughter of wealthy parents. They disowned me though, after they found out I had been dating a 30 year old man when I was in high school. Paul would smoke weed with me and get some beer so we could party. Usually during our partying, I would get really horny and we'd end up fucking. My parents found out because I was cutting so much class to be with him.
Actually, in looking back at it all, I think I did a lot of it because I wanted to make them mad, to make them punish me, or at least recognize I existed. You see, both my mother and father were too wrapped up in their own worlds to acknowledge that they had a daughter. My mother, in her high society women's groups... having her hoity-toity lunches and her shopping at all the high end stores. My father lived in his corporate world on the umpteenth floor of a big impressive high-rise in his corner office surrounded by other suits. They spent the day discussing financial matters, business deals, and who they were going to take over next.
Needless to say, I never fit into either world and I pretty much grew up on my own. Oh sure, I had money and a nice place to live and all that, but I didn't have the one thing all that couldn't buy. I didn't have love.
I moved in with Paul, who was the only one around to take care of me. He offered his apartment and love at first. Then, after awhile I found out the truth about him.
I was a naive 18-year-old spoiled rich girl back then. I didn't know people could be so devious and underhanded. Paul appeared to be a kind father figure, something I had been missing in my life, and so I fell hard for him. I so wanted someone to love and to love me back that I didn't see the signs until it was too late.
Paul was not who he claimed he was or who I thought he was as well. He turned out to be a controlling, egotistical, abusive tyrant of a man who kept me isolated and away from anyone unless he was right there with me. I wasn't allowed to have any friends except the ones he permitted, and even then I had to tell him everything that was said so he wouldn't think I was talking about him. He routinely went through my emails and my cell phone. He was paranoid that I was always fooling around on him (I wasn't), and plotting to leave him for someone else.
Then one day, he brought a new twist into our relationship. We had gone to this guy's apartment that Paul knew to score some weed. I don't know where Paul knew this guy from, but we went to his apartment together because he didn't want to leave me at home alone. Anyway, we get there and Paul tries the pot out to make sure it's good quality. He gives me a hit or two, just showing off for this friend. Then he goes to pay for it and comes up short of funds. Instead of buying what he can afford, he instead makes the guy another offer.
"I got half the money, but you wanna work a deal for the other half?" Paul asked him.
"What did you have in mind?" the guy said.
"Well, I'll let you fuck my girl here for the rest of the weed," he said. I looked at Paul like he had just grew a second head! I couldn't believe he had suggested something this outrageous!
"Is she any good?" he asked.
"You bet your ass! She's the best fuck in town. And she's a screamer too!" he said, joking with the guy. I was mortified! I turned beet red at his comment and stood there dumbstruck as the deal was finalized. I was going to be partial payment for the weed he wanted to get!
The dealer handed the bag of weed over to Paul and then he turned to me. He got this wicked grin on his face and I looked at him, horrified. His gaunt, pock-marked face had leathery skin and eyes larger than they should have been for his face. He had what I can only assume as a feeble excuse for a beard, although it looked more like a short haired dog with the mange. His hair was thin and falling out in small patches, and when he smiled he showed yellow, crooked, and worn teeth with a few missing here and there.
"Paul, please!" I said, turning to him. But he had made the deal and was more interested in the bag he hand in his hands than me.
"Hurry up and give him what he wants so we can get home. I wanna try this shit out for real!" he said, pushing me towards the dealer. I realized that there was nothing I could do. I hung my head and followed him into the bedroom while Paul stayed in the living room.
He shut the door and then pointed to the bed. "Get undressed," he said simply. I stood there for a moment just looking at him, my feet unable to move. "I said get undressed, you little whore... unless you want me to go out there and tell your boyfriend that you welched on the deal?" he repeated, pointing a thumb to the door behind him.
I knew that would be worse than just going through with fucking this dirtbag and getting it over with. So I slowly began to undress as he leered at me, smiling his crooked smile and licking his lips in anticipation.
I lay down on the bed and got ready to do what I needed to do. He quickly shed his clothes after watching me and climbed into bed. He crawled over the top of me and lay on top of me preparing to get what he was due.
To say that he stunk is an understatement. I don't think the guy had seen soap since puberty! He reeked of sweat, gasoline, cigarettes, beer, and a few other odors I didn't recognize. I almost puked after the first couple of whiffs of his stench. I was able to keep down my lunch though, swallowing a couple times to settle my stomach. He push my legs apart And took hold of his cock getting ready to enter me. I closed my eyes and waited for him to penetrate me and I didn't have to wait long.
I don't know whether it was the drugs that caused his cock to shrink, or if he was just naturally small, but he slid easily into me even without lubrication. My pussy had some difficulty gripping him - you see Paul was a fairly large man and I had gotten used to him, so this needle-dick barely made an impression on me. But I guess the excitement and anticipation of finally getting laid was enough, because after a bit of huffing and puffing I could feel him getting ready to cum.
"I'm gonna cum now whore! I'm gonna cum all over that pretty face!" he said then he pulled out and shot his load onto my face and tits. His cum didn't smell as it should either, having a strange acrid smell to it. After he finished the last spurt, he grabbed me by the hair and pulled me onto his tiny cock. "Suck it! Suck my cock clean, slut!" he growled.
I took him into my mouth, about gagging - and not from his size either! I licked and sucked his cock clean and then pulled back away from him. "There... you got what you wanted for the deal. Now can I go?" I asked him.
"No I think I want some pussy for dessert!" he said reaching out to grab me. I'd had all of him I could take. I grabbed a lamp off the nightstand and swung for the fences, catching the sleaze right in his hooked nose and sending him rolling backwards over the bed howling in pain. I turned and ran out of the room and past Paul in my haste to get away from the whole scene.
*
I left Paul after that. I knew that I had to find some way to support myself - I wasn't going back to him and I damn sure couldn't go back home to Mommy and Daddy! I looked in the paper and found the ad for the temp agency and decided to see if they had anything I could do. I began working as a cleaning lady, cleaning other people's houses and offices. It paid just enough to keep me in a small apartment and keep food on the table, but not much more. I struggled to get by, but at least I wasn't involved with the likes of Paul anymore. I even quit the booze and the drugs - mainly because I couldn't afford them!
I worked as a cleaning lady for about a year when one of the other girls in my cleaning crew told me of a way I could earn more money. I had been complaining about always scraping by and never seeming to have enough money - by the end of the month I was down to eating Ramen noodles for dinner! She told me to go to the office and ask for Lisa... that Lisa would show me how to make more money. The next day, I went in a little early to work to talk to this Lisa person.
"Lisa?" I said, knocking on her office door.
"Yes, come in," came the reply.
"Hi, my name is Holly, I am one of the cleaning crew," I said as I walked in and introduced myself.
"How can I help you?"
"Well, one of the other girls, Angie, said that you could help me. She said that you could show me how to make more money. I am tired of always being broke. I need to earn more money," I explained.
"I see. Close the door, Holly," she said. I closed the door and sat back down.
"I see you have been working here for almost a year now. You and Angie are good friends I take it?"
"Well we get along pretty good. I like working with her and I think she feels the same. I don't know if you'd call us good friends but we do talk and get along well."
"Well, I can show you how to make more money than you do as a cleaning woman, if you are interested. Tell you what... here is my address. Be there tonight at 7:00 pm and I will explain everything," she said.
That night, I arrived at the address Lisa had given me right on time. I rang the doorbell on a very nice split-level ranch house and presently, Lisa opened the door.
"Hi Holly, glad you decided to come. Won't you come in?" she said. Lisa led me into the living room and seated me on the sofa. "Would you like a glass of wine or something?"
"A glass of wine sounds nice. Thank you."
She left for a couple moments, returning with a bottle and a couple glasses. She poured the wine and sat back sipping it. I was about to ask again about the money thing when she spoke first.
"I spoke with Angie after talking with you today and she told me pretty much the same thing you said - that you and her are good coworkers and enjoy working together. She said you are friends and talk and chat a lot while you work. She also said that you have been complaining that you never seem to have enough money and by the end of the month you barely have enough money for food, much less anything else."
"Yes that's right. The end of the month is always hard," I said.
"Well, I have a way of fixing that. But what I am about to tell you can never be repeated outside of this room. If you do, you will immediately be terminated - no excuses, no second chances. Understand?"
"Yes Ma'am," I said, wondering now where this conversation was heading.
And that is when Lisa began telling me about the other side of Kirkland Temporary Services! I listened as Lisa explained that behind the front of a temporary employment agency, there was a call girl service and that select girls from the agency were picked to provide entertainment to their more affluent clients. Lisa said that several of the girls make more money in a single night than they do for two weeks of working as a cleaning lady. And if they used one of their weekend nights for the "dates", they could still do their cleaning jobs as well, doubling their money easily.
I took what she said and thought about the possibility. Most girls would probably be shocked at the idea of becoming a call girl and whoring themselves out for money. But I had already been there with Paul - and I didn't even get paid! So the idea of fucking for bucks wasn't so distasteful to me. After Lisa told me how it all worked and the money I stood to make, it didn't take me long to sign on... a girl's gotta eat, and I was getting real tired of that end of the month menu!
My first "job" came a couple days after the meeting. Lisa called me into the office after work that afternoon.
"You wanted to see me, Lisa?" I asked after knocking on her door.
"Yes, come in and shut the door, please." I did as she said, and sat down in front of her desk.
"I have a client that would like a date this Friday night. Are you up for it?" she asked me.
"Sure, what do I have to do?" I asked.
"Well, for starters, what do you have for clothes?" Lisa asked.
"Sadly, not much. Just a couple pairs of jeans, three or four tops, and my work uniform. I haven't had the money to get anything more."
"Well that won't do. The Judge likes his women to look sexy and tattered jeans aren't sexy! Here is $200.00... go shopping and get yourself something to make a man take notice of you!" she said. Lisa began telling me about the Judge and what his particular fetish was.
Judge Keeler had an obsession with secretaries - and more to the point, slutty secretaries. So I went to the local boutique to see what today's slutty secretary might wear! I found a little secretary costume that contained a bra and panties, a collar/tie neckpiece, and a tiny microskirt with garters for stockings. It was all supposed to resemble a business suit and still be sexy. I picked it up then I picked up a pair of fake glasses with the black plastic frames and a clipboard for the "realistic" look.
I met him in his office that Friday wearing my three-quarter coat so I wouldn't draw attention before I got there. I knew I had made a good first impression to him as he constantly kept admiring my costume and licking his lips as we sat and talked. We discussed my fake job application as well as what future I was looking for; I was so good at acting it out that he'd sometimes wonder if I truly was the call girl he had asked for. But I would always reassure him with a wink or a sudden compliment whenever he doubted, which made him more confident.
The role-play he had created flowed perfectly: I flirted with him, and he invited me for dinner at his house. We then spent the evening eating and drinking, playing out his fantasy to the letter, and finally we had sex together – fulfilling the final act of his play.
Judge Keeler enjoyed good foreplay, more than the actual penetration. That first night he just wanted me to give him a blow job while he used his chubby fingers to play with my pussy. His moans sounded more like bear noises; in fact he did resemble a bear. Though bald, except for the sides, his back was filled with hair. So was his ass for that matter, and his chubby form made him closer to a bear then a man. Yet he was not as strong as a bear, though the sixty year old did have his few moments of glory - it was always somewhat impressive to see him lift me up during sex.
Unfortunately his penis was not impressive, except for the resilience it had. It was smaller than average, and the girth was a bit disappointing. I was able to fit it all in my mouth with hardly any gagging, and I could easily lick around it while sucking him off.
"Ohh Holly!" he said suddenly as I sucked on his cock.
"Is he about to blow already?" I thought to myself. We hadn't been going for very long. I was just hitting my stride! "Oh well, I might as well help him then."
I played with his balls with my hand while sucking his cock all the way down to his crotch. His pubic hair tickled my nostrils, and smelled of dry semen. I could feel his sacks vibrating and soon a spurt of hot cum shot out of his pee-slit, and hit the back of my throat. I swallowed the small amount he had fired, since he apparently found it very satisfying to see. He held my head tight and huffed and moaned at the same time he was coming - until the last drop of sperm had left his body.
I could feel his cock turning soft as it exited my mouth. A single thread of cum and saliva attached itself between my mouth and his cock, forming a bridge, while it exited.
"I am sorry Holly, I did it again. I could not help it, I had to come," he sat down on the bed sweating and breathing heavily, while I cleaned my mouth with a tissue.
"It's ok dear, it was fun as long as it lasted," I liked how he apologized for cumming too quickly; I found it cute and sweet that he cared.
"Next time, next time I promise you won't be disappointed," he said to me while his breathing became more controlled.
I smiled to him and said, "I am not disappointed," it was important to me that my clients believed themselves the best, so I often lied. I kissed him on the forehead and walked towards the bathroom, readying myself to leave.
Closing the bathroom door behind me, I began to inspect myself on the mirror, checking to see what make-up needed to be refreshed. My eyelashes remained mostly untouched except for a small curve on the one of my right eye, which I fixed immediately. My bright red lips had lost some of their color, so I used my lipstick to renovate the color a bit. Though my makeup usually got a bit damaged during sex, it was always my hair that suffered the most. The length of my hair did not help me either, as it made it easier for my clients to grab it during intercourse, thus leaving me to fix it again at the end of it all.
I used a comb to carefully brush my hair back into place, which was not entirely easy. I then washed my mouth with water and some mouth wash, which I had brought along; cleaning out the semen that had remained inside of me. Finally I got dressed in my costume, which was the only clothes I had brought at that time (I have since learned to carry a bigger purse with something to throw on inside for that trip back home!). Once dressed, I came back in the bedroom and Judge Keeler paid for my services.
With a promise to come see him again soon, I kissed him sweetly on the forehead, leaving him with a red lipstick kiss on his bald head and a smile on his lips. I slipped on my coat and went downstairs to the cab I had called, and headed home.
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