Balancing Work and Pleasure

Jack walked over to his colleague Ron's office to see how his interviews were going for the tech job. His cute blonde assistant smiled when she saw Jack come into the reception area. Ron's door was closed and Denise held up a finger to her lips as a signal.

"He's still interviewing," she whispered.

"How's it going so far?"

"Good he has three strong candidates. This one has been in there the longest."

"I'll just wait here until he's done."

"Are you guys going drinking tonight?"

"I don't know. I'll see what he is up to. Want to join us?"

"Not tonight, I have a date to see Motown on Broadway."

"Good for you, I hope you enjoy it. I loved it."

Jack sat in one of the chairs in the reception area by Ron's office. He checked out Denise once he sat down. She was wearing a mini-skirt that had ridden up higher than normal. She had lovely legs but Jack loved her killer ass. He still remembered the one Friday night when Denise joined him and Ron for drinks after work. They ended up in a motel and the image of him fucking her ass while she sucked Ron's cock was forever imbedded in his mind. It was a sex marathon that night with the three of them as he and Ron sampled all her holes. He thought, "Too bad she has a date tonight as I would dearly love to tap her lovely bottom." His thoughts were interrupted when Ron's door opened up and a very handsome blonde young man walked out.

"Okay Brandon, I'll be in touch. Thanks for applying for the position."

"You're welcome; I hope you see that I am qualified."

"Yes, I'll let you know," Ron repeated and then saw Jack sitting there, "Hey partner, come on in."

Jack entered Ron's office and Ron told Denise she could leave if she needed to get going. She was already gathering her things as Ron closed the office door. "Want a scotch?"

"Sure, I'll have one if you join me," Jack accepted and then asked, "How did the interviews go?"

"Good, I had three strong candidates. I like the last one best. He has some other attributes."

"Really, why does he stand out?"

"He gives great head and he has a lovely ass. That's why it took me longer with him."

"You devil, I thought he was walking gingerly when he left your office. Is he gay or bi?"

"Oh definitely gay, he's been butt fucked before but I think that I may have been his biggest."

"I bet, that's why he was walking a bit bow legged. Anyway what are your plans tonight?"

Jack sipped on the single malt scotch as Ron replied, "You know when it rains it pours. I was supposed to hook up with Kari tonight but then my wife committed us to some party of some sought. I don't even have time to have a drink with you first."

"So do you want me to take care of Kari for you?"

"Go fuck yourself." They both laughed.

Jack laughed and took another sip of scotch. "I'll probably head over to PJ's and see what's going on."

"Hey, I'm going to have that pretty gay blonde come back for another interview. This time we'll both fuck him and let him suck our dicks."

"I hope you don't see any wildlife on your way home. It's not safe for them."

"Smart ass, hey maybe I'll meet someone at this party. That would be cool."

"Nancy, will cut your balls off if you pull that in front of her."

"Well Jack, I have to take off. Happy hunting tonight"

"Thanks have a good weekend. I'll see you Monday."

Jack finished the scotch and left Ron's office. He would walk the six blocks to PJ's and check out the Friday night action.

MEET THE PLAYERS

Jack Walters headed up the Marketing and Planning division in a successful internet company. He was 30 years old and still single. He stood at 6"2" and weighed in at a fit 190 pounds. His hazel eyes and muscular physique drew chicks to him. Jack liked to snow ski and scuba dive for recreation and he was a decent golfer. He was religious about working out at the gym and usually made it there before work each day. He was not dating anyone on a serious business and he liked the chase with the ladies.

Ron Wilson was in charge of the Information Technology division and god friends with Jack. He too stayed fit and often worked out with Jack before work. Ron also was of the opinion that sex was the best cardio workout and he tried to get as much as he could. He was 36 years old, 6'0" tall and weighed 175 pounds. He had light brown hair and he had married to his wife Nancy for ten years. It was rumored that if something crawled out from under a rock that Ron would fuck it. He wasn't that bad but he was open to sex with the ladies and cute gays with nice asses.

Denise Davidson, Ron's Administrative Assistant, was a pretty 26 year old blonde. She was 5'5" with a 34-26-35 figure. She often hooked up with Ron and Jack together and she also had sex with Ron in his office from time to time. With her good looks and bubbly personality, one would never guess that she was a sexual dynamo. She had pretty much done it all with guys and other girls as well as the group scene. Her 34 B breast were perfect for her frame and she had gorgeous legs. The best asset was her derriere as she had an ass that wouldn't stop.

Nancy, Ron's wife of ten years, knew about his extra marital flings but put up with it because of her lavish lifestyle. She didn't work and she enjoyed the amenities of life. The details of Ron's activities were not important to her as he kept her happy and she also had her secret life. An attractive woman of 34 years she was in decent shape with a 35-30-35 figure. Her brown hair hung down to her shoulders and she had big beautiful brown eyes. Currently she was enjoying the services of a couple who ran a massage studio.

JACK'S FRIDAY NIGHT ADVENTURE

Jack arrived at PJ's and as usual for a Friday night it was busy. He looked around for a spot at the bar and there was none. At one of the cocktail tables he spotted a blonde woman and two guys and there was space for another person. He went over to them and asked if was alright to occupy the other space. The two guys nodded that it was okay and Jack then guessed that the woman was alone.

"Hi, I'm Jack Walters, may I buy you a drink since you let me join you?"

"Oh thanks buddy but we are leaving after this one." One of the guys replied.

"I'll have one. I'm Sherry."

Jack got the waitress attention and ordered the drinks. A quick assessment of Sherry and he guessed that she was in her mid-forties. She looked to be about 5'6" and couldn't have weighed more than 125 pounds. She was a fit with medium sized tits, a narrow waist and shapely legs. The two other guys left shortly afterward and Jack pulled up a stool. The other stool was grabbed quickly and taken to other table.

Jack and Sherry made small talk and he sensed that she was on the prowl that evening. After a few drinks Sherry sat closer to him making sure that her body rubbed against his. Sherry slid even closer to Jack and let her hand drop to his thigh. Jack was rock hard at this point and Sherry ran her hand over his thick 7+" cock in his pants.

"Oh my, we are a little excited aren't we," she whispered as she grabbed the thick dick firmly.

Not to be out done, Jack ran his hand under her miniskirt expecting to run it over her panty clad pussy. Instead he found a bare pussy that was neatly trimmed. Sherry's cunt was sopping wet and Jack inserted one of his thick fingers into her quim. Beck groaned softly and turned her head to be kissed. Jack kissed her he pulled his finger from Sherry's pussy. Sherry took Jack's hand and sucked her juices from his finger.

"Do you live in the city?" she asked in a raspy excited voice.

"Yes, on the eastside overlooking the East River."

"I live in New Jersey and I have to catch the last train home tonight. If we're going to do this we should get started."

Jack paid the tab and walked out of PJ's with Sherry. He hailed a taxi and it was a short car ride to his apartment on East 72nd Street. He entered the apartment building with Sherry and greeted the doorman and consigliore.

"Good evening Mr. Walters," they both replied.

It was not unusual for them to see Jack bring a woman back to the apartment. Jack guided Sherry to the elevator and they rode it to the 40th floor. His apartment was a tastefully furnished one bedroom overlooking the East River. It was a clear night and the view looking north was beautiful. Sherry was anxious to get going so Jack brought her into his bedroom.

Sherry went right to the bed where she undressed and sat on the side of the bed. Jack stripped off his clothes and walked toward her with his big hard dick swinging as he walked. Jack looked down at Sherry and lifted her face with his hand. Sherry smiled at him and she marveled at his confidence. Sherry took his thick cock in her hand and ran her tongue over the head of it. Then she wrapped her mouth around it and slowly moved her head up and down taking him as deep as she could without gagging herself.

Sherry was indeed an excellent cock sucker and she soon had Jack on the verge of his first cum. Sherry bobbed her head up and down on his cock pursing her lips together until she felt Jack shiver. Sherry would remove her mouth briefly to prolong his orgasm. She would lick the underside of his cock and his balls driving him wild with desire. Sherry sucked his balls into her mouth and tickled his perineum with her fingers. Sherry let her hands run over his hard abs and loins which caused Jack to tremble as a tingling sensation ran through his body.

Jack couldn't take anymore and he grabbed Sherry's head and pulled it off his cock. Jack stayed hard as he pulled his cock from Sherry's mouth. He pushed her back on the bed and slid between her legs. Jack eased his cock back into her pussy and fucked her through multiple orgasms until Sherry pleaded with him to stop and give her pussy a rest. Sherry rolled over on her stomach almost as if she was protecting her pussy from any more pounding.

As Sherry lay on her stomach Jack went to get some lotion from the bathroom. When he returned he sat on the back of her legs and she could feel his thick meat resting on her buttocks. Jack began a slow soothing massage starting at her shoulders and worked his way down her back. His strong hands mesmerized Sherry and she totally relaxed under his manipulations. Jack then massaged her legs working her calves first and gradually ascending to the back of her legs. Sherry tensed as he started to massage her ass cheeks as she knew where this was heading.

Jack put a generous amount of lotion on her ass and lovingly kneaded her cheeks. He complimented Sherry on her beautiful ass. He slipped his hand between Sherry's ass cheeks and brushed her vagina. Jack lifted Sherry by the hips so that her ass was elevated. He poured more lotion between the cheeks of Sherry's ass and began to probe her asshole with his fingers. Soon he had two fingers sawing easily in and out of Sherry's asshole and two others in her cunt. Sherry lay there with her head on the bed turned to the side and cooed as Jack simultaneously moved his fingers in and out of her rectum and vagina. Jack pushed down on the small of Sherry's back causing her to accentuate her shapely ass even more.

Jack removed his fingers from her ass and lined up the head of his cock with her pink rosebud. Jack eased his cock into Sherry's lubricated asshole and it slid in easily all the way to the hilt. Jack stayed still for a second and then slowly pulled his cock out until only the head remained in Sherry's ass. Then he pushed all the way back in again. Sherry loved having a cock in her ass and she was pleased that he took the initiative. Jack slowly fucked Sherry in the ass watching his cock slide in and out from between her gorgeous ass cheeks. He tried to prolong his ejaculation for as long as possible as he savored every moment of his cock in her ass.

Jack stiffened and pushed his cock all the way up Sherry's ass and he held on to the globes of her ass as he fired a huge load of cum deep into her rectum. Sherry could feel the warm seed fill her ass and chills ran through her body. Jack stayed in her ass and remained hard as Sherry milked him with her anal muscles. Jack leaned over Sherry and they both flopped to the bed with Jack still buried in her bum. They lay still for a while and Sherry realized that Jack was still hard in her ass. That's what she liked about fucking guys younger than her; they could last for a long time and they could cum multiple times.

Jack moved his arms up alongside of Sherry's and braced himself on his elbows. Then he gradually started to fuck her ass again. This time Jack picked up the pace and within minutes he was pounding Sherry's ass. Sherry pushed her ass up to meet Jack's cock every time he thrust into her. The two of them established a rhythm and soon they were fucking like animals in heat. Sherry grunted every time that Jack plunged his cock deep into her ass and she urged him to fuck her hard.

"Give it to me Jack. Pound it in there. Make me feel it. Yeah that's it," the words just rolled out of Sherry's mouth.

Jack was really caught up with pounding her ass. His cock felt like it was bigger than ever and that it would explode at any moment. Sherry's thrusting of her ass up at him was driving him wild. Jack felt his orgasm building and he fucked her even faster. Then he stiffened and shot a second load in her ass. He held himself in position as he emptied his balls in her rectum. Sherry felt the warm substance enter her ass and mix with his previous cum load. She hadn't felt that full since in quite some time.

The two of them fell forward on the bed with Jack's cock still impaled in her ass. Jack rolled to his side and rolled Sherry with him so as not to crush her with his weight. As they lay there Sherry clenched and relaxed her sphincter muscles as she massaged Jack's softening cock. She felt him finally go totally soft and slip from her asshole. Streams of cum trickled out of her ass and ran over her ass cheek onto the bed sheet.

She checked the time and said, "I need to get going."

Sherry used his bathroom to clean up and then she got dressed. Jack threw on slacks and a sport shirt. He escorted Sherry back to the lobby and had the doorman hail a taxi for her. Jack paid the cab driver with instructions to take her to Penn Station and he tipped Tom the doorman. The cab pulled away and Jack decided to head over to Murphy's for a night cap. It was only 10:00 PM. Murphy's was just three blocks away and Jack knew the bar maids and waitresses as well as some of the regulars.

DENISE'S NIGHT OUT

Denise's Friday night was enjoyable but also disappointing. Her date David was a perfect gentleman. He picked her up at her apartment in a rented limo and took her to a lovely French restaurant for dinner. He instructed the driver to pick them up after the show. They had great seats and she really enjoyed the show. Afterward the driver picked them up and David invited her to his place. She readily accepted and that's when the evening went south.

David was a terrible lover. Not only was his cock below average but he came as soon as he was in her pussy. Denise tried to get him to eat her but he was having none of that. Frustrated she left the apartment and called her good friend Rachel. Denise hoped that Rachel was home so that she didn't have to go back to her apartment alone that night. She was in luck as Rachel was home and she was thrilled to hear from Denise. She told Denise to come right over. Taking a taxi she was at Rachel's building within 20 minutes.

As soon as she entered the apartment, Rachel pushed Denise back against the door and pressed her knee into the pretty blonde as she pinned her against the door. Rachel's hands were all over Denise as she started kissing her passionately on the lips. Rachel's kisses were so wonderful and eager as her hands cupped Denise's face, Rachel kissed her over and over. Denise reveled in the thrill of all the emotions and adrenalin coursing through her body. Rachel nibbled on Denise's lower lip gently and Denise gushed with exhilaration as their tongues intertwined. Rachel shoved her tongue deep into Denise's mouth causing her knees to almost buckle under her with the excitement of the moment. As Rachel's wet hot tongue explored Denise's mouth her hands roamed all over her body. Rachel explored inside Denise's blouse, up her skirt and stroked the exposed skin of her thighs above her nylons. Denise murmured into Rachel's mouth as her friend's caresses sent shivers through her body as Rachel seductively stroked her breasts and thighs. Denise's desire intensified as Rachel stroked her pussy through her damp panties.

She dropped to her knees and raised Denise's skirt pushing it up to her waist. Then she hooked her fingers into Denise's panty and slowly peeled it down her thighs and off her legs. Rachel then held the panty to her nose and inhaled the sweet smell of Denise's sex. Next Rachel steered Denise back against foyer table and helped raise her up until she was sitting on the table. Rachel smiled wickedly at Denise as she pushed up her skirt and then dropped slowly in front of her. As Rachel spread her legs Denise couldn't conceal a moan and she had to stifle her gasps with the back of her hand. Denise could feel Rachel's hot breath on her sopping wet pussy. Denise then started to place delicate kisses upon Denise's naked thighs and the sensation of her wet lips on Denise's skin sent waves of excitement through her. Rachel ran a fingertip down Denise's slit causing her to groan with pleasure as Rachel's fingers honed in on Denise's engorged clit.

As Rachel inhaled the sweet odor of Denise's pussy her tongue darted out for an exploratory lick and then she lapped excitedly at Denise's quim. Rachel began to lick her from her little puckered asshole to her clit. She then pulled Denise's pussy lips open and exposed her pink pussy as her tongue darted in and out of Denise's now dripping cunt. Denise felt as if she were being fucked with a little cock as Rachel stiffened her tongue. Using her thumb Rachel rubbed Denise's clit and she also dipped her fingers into the soaking wet pussy. Rachel then took one very wet finger and slid it into Denise's tight asshole. Oh how good it felt to Denise to have something in her ass again. Rachel sucked Denise's clit into her hot mouth and slid her fingers into her pussy and one into her ass. Denise groaned with the pleasure of the raw sex and her love of anal sex betrayed her. Soon the intensity in Denise's ass, pussy and clit built up to the boiling point and she came noisily with her juices spilling from her and into Rachel's waiting mouth.

"Oh Denise, I am so glad you called. I missed you and it is so good to be with you again. Come with me."

Rachel hurriedly took Denise by the hand and led her to the bedroom. Once in the room they frantically removed the rest of their clothes. Denise knew it was her turn to pleasure Rachel. Rachel stood by the bed as Denise moved behind her and placed gentle kisses all over her body. She started at Rachel's shoulders and worked her way slowly down to her buttocks. Denise was enthralled with Rachel's body with her firmness and smooth skin. Denise began to lick and kiss Rachel's hips planting kisses all over her sensitive body. Denise couldn't resist sinking her teeth into Rachel's firm ass cheeks causing her to shiver and gasp in surprise. Denise turned Rachel toward her and then kissed the inside of her thighs and worked steadily toward her pussy. Denise kissed the area around Rachel's pussy and inhaled the sweet aroma produced by her arousal.

Denise loved the smell of Rachel's pussy and she was desperate to taste her. Denise flicked out her tongue and tasted her pussy. Denise was pleased to find that Rachel tasted as sweet as she smelled. She began by probing Rachel's pussy gently with her tongue and then found herself diving into the luscious pussy. Rachel fell back onto her bed and Denise moved to a sitting position between her legs. Denise then began to lick her clit and loved the way it swelled under her tender touch. Remembering her lesbian experiences, Denise enveloped Rachel's clit with her mouth and swirled her tongue around it emitting squeals of delight from Rachel letting Denise know that she was driving her crazy. Denise started to lick Rachel's pussy again tasting her sweetness. She ate her, licked her and probed Rachel's sweet hole with her tongue and then slipped a finger into Rachel's dripping pussy and finger fucked her while she sucked and nibbled her swollen clit.