“Mr. Thompson will see you now,” the attractive executive secretary to the Senior Vice President told Lesley as she waited outside his office for her two o’clock appointment. Lesley stood and smoothed her skirt before picking up her handbag and briefcase. She walked into the large office and extended her hand as Mr. Thompson, Brian, was moving towards the door to meet her.
“Lesley, so great to see you today. I hope I didn’t keep you waiting too long.”
The office door now closed behind them by Tina, the executive secretary. “Not at all, Brian. I was a few minutes early.” Brian admired how Lesley was always impressively dressed for their semi-weekly meetings. Today was a perfect example as she wore an obviously expensive dark grey business suit with skirt and white blouse. Her dark hair rested on the shoulders of her jacket. She wore ankle strap platform heels by Ferragamo.
Lesley too, admired Brian’s sense of fashion – both in style and quality. “May I get you a drink, Lesley?”
“Gin and tonic, thank you.” As he handed her the glass, he offered her a seat on the large sofa that lined one wall of his expansive office.
“How long have we been having these regular meetings? A couple years?” Brian asked as he sat down on a leather chair beside the sofa.
“Just over two years, Brian. You were one of my first regular appointments and you have been consistent. I truly appreciate your time, Brian.”
“I have a favor to ask of you. I think it’s just a small favor, but please let me know if you have any objections.” Lesley merely hinted at a smile. “Before we begin, may I take a photo of you? It’s for my wife. As you know, she is aware of our regular meetings and she would like to see the special woman who … puts up with me every other week.” Brian was now grinning at the sound of his voice.
“Of course, Brian. Should I stay seated or would you like me to stand?” Lesley was lying back on the sofa with drink in hand and her left leg crossed over her right. Very attractive and very confident.
“Just as you are should be great.” Brian pulled out his smart phone and took a photo of Lesley. He hit a few buttons on the phone and the picture was sent. “I do want to let you know I’ll be out of town for the next four weeks so we’ll have to cancel those meetings. I hope that isn’t a problem for you. Lesley waived her hand to say not at all. “Good.” Checking his watch, “Should we begin?” as he unfastened his belt.
#
Nearly two and a half years earlier, Lesley had a long and heated discussion with her husband of seven years. He had recently been forced to switch positions and take a reduction in salary. Lesley had always been a fashion monster and took immense pride in her appearance, regardless the price. Larry, her husband, always appreciated how stunning she looked but just couldn’t see how Lesley could continue to buy $700 shoes and $1,000 outfits on his new salary. The discussion grew quite tense and finally he told her, “Fine. You figure out how to afford it on my salary and you can buy it.”
His new position meant longer hours and much more stress. He really didn’t keep track of what was transpiring in Lesley’s life as she worked to afford the latest in fashion. Lesley soon contacted an old friend from college with whom she’d stayed in touch, though not frequently. The friend, Morgan, had traded her corporate job for one of a high-priced, exclusive escort. Larry had always told Lesley she had a mouth made for fucking so she thought why not see what it would earn her. Morgan was quite surprised when Lesley told her what she wanted to do to earn the money for fashion. Morgan convinced a regular customer to give Lesley an “interview” one evening.
Lesley was a bit nervous when she arrived with Morgan for the interview. Shortly after meeting him, Lesley got down on her knees and took his cock into her mouth. She walked out an hour later with $200 in her purse. All she had had to do was give him a blow job and reapply her make-up before she left his home. Now, she just needed to find her own appointments. She had always enjoyed giving oral sex anyway so she might as well get paid.
Lesley was discreet and Morgan helped out with a couple clients in the first few months. At the end of the first year, Lesley had ten regulars and about twenty other occasional clients that netted her about four grand a month. And Larry didn’t have the slightest idea.
#
Lesley pulls into the independent foreign auto shop just a little before ten a.m. on Tuesday. She checks her lipstick, cherry red like Tony likes, in the rear view mirror before turning off the key and opening her door. Her heels click on the shop floor as she makes her way to Tony’s office in the back. All the mechanics stop their work and watch as she walks past them without a glance. The secretary waves her into his office, “He’s waiting for you, Lesley.” Secretaries always know Lesley has decided so she doesn’t even try to fool them after the first few regular visits.
“Hi Tony. How are you this sunny Tuesday?”
Tony was wearing his usual clean Dickies, work boots and blue windbreaker as he stood up behind his desk. Tony is only five foot, seven inches and a bit portly but not fat. He has a mop of curly, black hair on his head and a matching set around his genitals. His office is usually pretty neat and clean but Lesley makes him keep a clean, white towel in his office for her visits. On one of her first appointments over a year ago, she ruined a pair of stockings by getting some form of grease on one knee.
His wife Maria is the love of his life, but she just won’t give him head. And on the rare occasion she does, like his birthday or their anniversary, she won’t swallow his cum. Tony always tries to make small talk, but looking at Lesley just ties his tongue in knots. So eventually, like today, he merely lays the picture of he and Maria down on his desk and pulls out the white towel. He hands it to Lesley and she inspects it to make sure it really is freshly laundered. Satisfied, she walks around behind Tony’s desk and lays the towel on the ground between his feet.
Tony had stood up and dropped his Dickies down below his knees. He pushed his boxers down with them. He sits back down with his ass near the edge of his seat. Lesley removes her blouse and places it on a hangar. She is wearing a red under-cup bra that highlights her 34B breasts and firm nipples. Every client is different and Tony likes to see her tits. Lesley rubs them for affect before slowly lowering herself to her knees on the towel.
Lesley looks up at Tony with her big, brown eyes before lowering her head over his cock. She always thinks of Tony as “chubby” when going over her appointments for the week. Even when erect, Tony is only five inches long but nearly one and a half inches in diameter. His penis really is shaped much like his body. Her lips slide over the crown in slow motion. When her tongue flicks his pee-hole, she can sense his body tensing for her touch. Her left hand cups his sac as the nails on her right hand lightly scratch at them through all his dark pubic hairs.
Her lips slide over his crown and now her teeth lightly rake the skin of his cock. It’s just a brush but he can feel her on his sensitive skin. Her lips never lose contact as she moves her mouth down his cock. Soon enough, her nose is pressing against his belly and she can feel his pubes on her skin. Lesley’s mouth begins to ride up and down his cock as her hands tease his sac.
Lesley pulls her mouth from his cock and looks up at Tony with her brown eyes. Tony is intently watching the top of her head as she fucks him with her mouth. His hands tightly grip the armrests of his desk chair. She lifts her mouth about three inches from his cock and forces a dribble of spit from her lips. Her mouth follows it down to the head of his cock and her lips slip around it once again. She takes all of Tony inside her mouth and then begins to suck her cheeks in and out. He can feel her all around his cock as she bobs up and down his hard, five-inch cock.
Lesley feels Tony’s body tense and she makes sure her mouth covers him completely. Tony lets out a little whimper as he thrusts his cock into her mouth and cums. It’s warm and wet and fills her mouth. Her tongue pushes his cum around her mouth and his cock before swallowing. She licks him clean as she lifts her mouth from his throbbing cock.
Lesley stands up and reaches for her purse. She opens a small bottle of water and takes a drink. Without Tony noticing, she swishes the water around inside her mouth to remove any traces of his cum. She puts the water back in her purse and pulls out her cherry red lipstick and mirror. She reapplies it to her lips. Tony hands her four fifty dollar bills and she slides them into the purse with her lipstick and mirror. Lesley puts her blouse back on as Tony stuffs the towel into his desk drawer. “Thanks Tony. See you next month.”
As she starts her car, Lesley puts a big piece of sweet bubblegum into her mouth. She’s learned it’s the only thing that will get the taste of cum out of her mouth. She blows a bubble as she heads to the mall.
#
Lesley parks her car outside the large office building just after one p.m. on Thursday. She grabs her briefcase, though it’s nearly empty, from the backseat and closes the door. She checks in with the receptionist and takes a seat as she watches CNBC on the video monitors and the closing stock ticker scroll across the bottom of the screen. Just before 1:30, a tall, thin red-haired man about 30 years old opens the glass doors that separate the lobby from the offices. “Hello Lesley, how are you?” She stands and shakes his hand.
“Wonderful John. How did we do today?” She asks as he shows her through the glass doors.
“Well, the market was up across the board so we probably made money.” It was really just banter as he led her to his office. Closing the door behind him, he flipped the lock so they wouldn’t be disturbed. John is an every other Thursday client. He’s single and tells her he dates occasionally but never anyone too seriously. The television on the wall is tuned to CNBC and the drone of the after-market announcers plays off to the side.
“I have a couple stock ideas for you, if you’re interested.”
“Of course I’m interested. What hard-working girl doesn’t want to make a few bucks in the market?” She smiled as she opened her briefcase and pulled out a pen and pad of paper. The only two things in it. John told her a couple of his current favorite selections and she scribbled down pertinent notes. At one point, she stood and slipped off her jacket and hung it in the corner. While he concluded his salient points about the second stock, Lesley unbuttoned her blouse. By the time she unhooked her bra and sat nude from the waist up, John had stopped talking about stocks.
Lesley likes John and his boyish innocence She wishes he would find a steady girlfriend and tells him so about once a month. Her fingers caress her nipples as she sits across the desk from him. John reaches down and unzips his fly. He pulls out his cock and begins to lightly stroke it as Lesley tells him some inane story about shopping for handbags at the mall on Tuesday. It’s really just a game of foreplay for them. Finally he stands up and walks around his desk to where she is sitting. Lesley unfastens his belt and pulls his pants down below his knees.
She gives him a look as her fingers slip inside his bikini briefs. “A new style John. Are these for me?” She grins as she looks up at him. He gives her a goofy look that so endears him to her. It’s like sucking my baby brother she thinks. His penis is already stiff. He’s seven inches long but a bit thinner than average. Lesley leans forward and kisses the crown lightly. She tastes a drop of his precum. Her touch is gentle and her hands lightly caress his small ass cheeks. Her lips kiss down his shaft. She lowers her head and opens her mouth to take his balls inside of her lips. She licks and sucks on them as she feels John shift from one leg to the other.
Lesley opens her mouth and slides over John’s cock. Her mouth feels warm and inviting to him. She slides up and down a few strokes before she begins to lightly hum. It’s really no fair, but she does it anyway. Before five minutes have even passed since he walked in front of her. He cums in her mouth. Lesley sucks on his cock, her tongue moving over his skin. John puts his hand on her shoulder for support and cums again. He pulls out and shuffles his feet backward. He pulls up his briefs and slacks and fastens his belt.
Lesley opens her purse and takes her bottle of water. Still with her tits exposed to John, she takes a couple drinks of the water. His cum really doesn’t have much taste but it’s a routine for her. Finally she puts on her bra and blouse and puts away her notepad and pen. John hands her two one-hundred dollar bills and she slides them in her purse. She slips on her jacket and John shows her to the lobby. “I’ll do some research on those stocks you suggested. Thanks, John.”
#
Four weeks later, Lesley rode the elevator to the thirty-fourth floor. She stopped into the ladies room to have one last look – perfect. “Hello Tina. Glad to have Brian back in the office?”
“It really didn’t change much. Most of his travels were business and with the time difference, I usually had an inbox full by the time I arrived. But it is very nice to have him back.” She motioned to the sofa, “He should be with you in a few minutes. He’s been running a little late all day.” Lesley took a seat.
Ten minutes later, Tina looked at Lesley. “He’ll see you now.” She walked into the large office and extended her hand as Brian met her. Appearances, it’s always about appearances for the client.
“Lesley, so great to see you today. I’m sorry about the wait – I hope it wasn’t too long.” She brushed it aside as he motioned for her to the sofa.
“Tell me about your trip to Europe. Was it successful?” She reached out to take the gin and tonic he offered to her and took a sip.
“It was wonderful. Very successful meetings and even a few days of R&R here and there with my lovely Rachel, his wife. In fact, we brought this home for you.” Lesley was surprised as this had never happened previously. She had received extra cash at times, but never a gift-wrapped present. She took another sip from her drink.
“Brian, you shouldn’t have done this but thank you,” as she started to open the wrapping paper.
“I should tell you that it was Rachel’s idea and she picked it out personally.” Lesley looked at him quizzically. “She says you’ve been wonderful for me … and her. For the pleasure you bring to me, you deserved a special gift. She would never let me do the things I do to you, but then you know that from our conversations.” Lesley saw the Gucci markings on the box and knew they had been in Italy. She could feel her heart race as she opened the box and looked inside of it. She knew exactly what is was – a top handle bag that cost nearly $6,000 on the website!
“Oh Brian … this is way too much!”
“Don’t be silly Lesley. Like I told you, Rachel picked it out for you with her appreciation and admiration.”
“Thank you. And please tell your lovely wife thank you for me.” Lesley drank the last of her drink and sat it on the table. She put the bag in the box and closed the lid. “Now Brian, I think I need to show you my appreciation. What did you have in mind for us today?”
“It’s been four weeks and I’ve missed this greatly. I may be a bit rough with you today. So please remove your lovely blouse and let me remove your bra.” As Lesley stood up, Brian handed her a hangar. She slipped her jacket on the sofa while she slowly unbuttoned her blouse for him to watch. She put it on the hangar and then draped the jacket over it. She walked to the closet and hung it up before returning to him. He had removed his dress shirt and slacks and now stood in just his underwear. Brian is just passed fifty, but in excellent condition with the body of a running back.
Lesley walked up to him and he unhooked her bra between her tits. He slid it off her shoulders. His hands lightly brushed her nipples and she bit her lip lightly. “You may want to remove your expensive skirt. I’d hate for anything to spill on it.” She had only done this a couple times previously for Brian and only when he had asked. This was a liberty she would allow no other client to take.
She turned away from him and said over her shoulder, “Would you be so kind as to help me with the zipper?” Brian slid it down and watched as it fell to the floor. Lesley was wearing a black thong bikini with matching garter and dark stockings. When she bent over to step out of her skirt, Brian marveled at her firm, sexy ass. Still wearing four-inch heels, she walked over to the closet and hung the skirt with her blouse and jacket. She smiled as she walked back to him.
Brian pinched her left nipple and pulled her close to him. He put his lips to her ear and spoke lightly, “You have the sexiest fucking mouth I have ever seen, Lesley. I’m going to use it this afternoon. I fucked Rachel’s cunt and I fucked Rachel’s ass in Europe but I’m going to fuck your mouth today.” With that, he released her nipple and shoved her to the floor. Lesley quickly reached up and pulled down his underwear over his semi-erect cock. She always marveled at his cock, even though she saw it twice a month. When fully erect, it was nearly nine-inches long and more than two inches wide. It is the only cock she services that really causes her to strain – he’s just so damned big in every way.
He grabbed the back of her head and pressed her face to his cock, even as he was stepping out of his underwear. Lesley opened her mouth and took the crown inside. Her tongue licked all around it as she tried to coat it with her saliva. He allowed her just a moment before he pushed her mouth down farther on his cock. She had the first five inches of him before he started thrusting his hips in and out of her mouth. She pressed her tongue to the bottom of her mouth as she tried to open as wide as possible for him. His cock was now ramrod stiff as he fucked her mouth.
Moments passed and she was now taking his entire cock in her mouth. He pressed her head down on his cock and she felt her nose against his pubic mound. Her mouth was filling with her own spit and when he pulled his cock from her mouth in one motion, thick strands of her spit linked his cock to her mouth. He looked down and smiled. He started deep-throating her with his cock and sounds of her spit in her throat filled the air around them. Lesley could feel herself gagging on his cock and all the fluid in her mouth. When he would pull his cock free of her lips, she would do her best to dribble it out past her lips before he would shove his cock back inside of her.
Brian buried his cock in her mouth and reached down at pinched her nose. Lesley had never had this done and could feel herself starting to hyper-ventilate. She was sucking and blowing with her cheeks but no air was filling her lungs. Finally, Brian released her nostrils and pulled his cock from her mouth. She was gasping for air as spit ran down her chin and tits. “My God Lesley. You are one sexy cocksucker!”
He grabbed her by the hair and angled her face upwards. Brian took his cock in his hand and stroked it. Lesley opened her mouth to receive him. But this time, Brian pressed the head of his cock against her cheek and shot a stream of cum that hit her cheek and eye. It was a healthy wad but he wasn’t finished. He took his cock and smeared his cum all over her beautiful face. He even gave her a couple slaps with his cock on her cheek. He then pressed his cock to her lips and she slowly opened them. He forced his cock in her mouth once again and began fucking.
It didn’t take long for him to near orgasm the second time. He pulled out of her mouth and said, “Squeeze those sexy titties for me, Lesley.” She quickly pressed them together and he shot his load of cum onto her tits. He splashed on both tits before walking away from her. “My washroom is this way.” Brian extended a hand and helped her to her feet. She crossed the room with her face and tits covered in his cum. Brian grabbed a towel and wiped off his cock before returning to his office.
Lesley took a few minutes to wash her face and breasts. Brian usually wanted her to swallow his cum but not today. She walked to the closet and got dressed. When she went to collect her present, five one hundred dollar bills were on the box. She looked at him, “I figure I owed you a little extra today.” Her jaw ached and she still felt like she was trying to catch her breath so she agreed that he did, even if he had bought her such an expensive gift.
“Thank you Brian and don’t forget to thank Mrs. Thompson for me.” Lesley smiled at Tina as she walked past her with her Gucci bag in the box. Shoes, Lesley thought to herself, I need a new pair of shoes …