Paul had decided to go into the office on Saturday morning. It was a crummy rainy day and his gold game had been rained out. He opted to get caught up on some paperwork rather than sit at home drinking coffee. He would stop at the gym afterward to get a workout in before returning to his home. Paul showered and as he dried off he checked himself out in the mirror. At 38 years old he was in great shape. He stood 6’1″ and weighed a fit 180 pounds. His body was well toned and firm. He always kept his light brown hair cut short a habit from his Marine Corps days. He dressed in a golf shirt and slacks and donned a rain resistant windbreaker. Skipping breakfast at home he stopped at the bakery and picked up a muffin and coffee.

Paul arrived at the office building and signed in with the security guard who greeted him pleasantly. He went to his office and ate the muffin before beginning his admin work. He went through the mail that he ignored during the week tossing most of it out. He sorted through a number of documents that needed his attention and placed some in a stack to be filed by his assistant. As he created the pile for Crystal his admin assistant, he thought about her. He pictured her bent over his desk or the small conference table in his office with her dress tossed up and her panties pulled down. He thought about the many times that his cock was either in her mouth, pussy or ass.

Paul and Crystal had been having an affair for the past year. It had all started innocently enough after an office party. Paul thought it would be a one night stand and that he wouldn’t happen again but just the opposite did. They got together at least twice a week at Paul’s house and they had brought sex into the office. As he was thinking about their escapades, he suddenly wished that she was there. Just then the phone rang and it was Crystal.

“I tried you at home and there was no answer. I knew you wouldn’t be playing golf in this weather so I assumed that you might go to the office.”

“You’re right, just getting caught up on some paperwork.”

“Want some company?”

“Sure, I’ll need another hour and then I can meet you somewhere.”

“No, stay there, I’ll be over in 15 minutes.”

“Okay, see you soon.”

Paul hung up the phone and returned to his work. He wondered why Crystal wanted to come to the office but it must be because she was close to the building. She must have been out running errands to be so near. It was unusual for Crystal to be available on the weekends. Her husband must have something going on Paul figured. Minutes later she arrived and as always she was neatly dressed. Crystal was dressed in a tasteful full length light blue summer dress. It concealed her shapely body but Paul knew what was underneath.

“You look nice today, what’s up with Jerry?”

“He played cards and got drunk again and crashed at one of his buddy’s pad. I decided that I wasn’t going to stay home alone this morning.”

“You should have called me at home and we could have met somewhere.”

“I thought about it and when I did you were already gone. I was hoping to catch you here since I knew golf was rained out.”

“Well you did and it’s good to see you. We have never been together on a Saturday before.”

“I know,” Crystal replied softly as she walked up to Paul and kissed him.

He held her tight to his body as they kissed. Crystal pushed him away and slowly slid down his body until she was on her knees. She looked up at him as she unzipped his pants and reached inside and grasped his throbbing penis.

“Oh,” he moaned as he watched her struggle to pull his big dick through the fly in his pants.

When she had it out in the open, a little moan escaped her lips. She loved his large penis. While she only had three others to compare it to, it was much longer and wider than those. Crystal stared at the pulsing shaft in her hand. The slit in the head began to ooze his pre-cum juice. She moaned and opened her mouth to take the dripping head inside.

“Oh God you’re good, “Paul gasped as he watched his assistant suck him. He never grew tired of the sight of her bobbing up and down on his cock. His hips began to move back and forth as his excitement grew. He watched her cheeks suck inward when he pulled back and then bulge outward as his penis pressed toward her throat. His balls began to tighten and his hips began to move faster with his growing excitement. Paul didn’t want to cum in her mouth nor did Crystal. They wanted something else, so he pulled her willingly to her feet and led her over to the small conference table.

Paul locked his office door with the dead bolt and placed a door stop underneath. He didn’t expect to be interrupted but security had a master key and he wasn’t taking any chances. As he secured the door, Crystal leaned over the conference table awaiting his return.

“I douched my both ass and pussy this morning.”

“Are you trying to tell me something?”

“Just that I am squeaky clean in case you want to use your tongue somewhere.”

“I see. Are you telling me that you would like me to rim your sweet anus and make love to your lovely bottom?”

“Only is you want to,” Crystal replied in a shaky voice.

Crystal moaned as she was bent over with her ass in the air. She knew what was coming and her heart began to pound in her chest. Paul raised her dress and draped over her back and knelt behind her taking in her beauty. Crystal was an attractive 35 year old woman. She had an athletic figure with small breasts, flat belly, shapely legs and a marvelous ass. She was 5’5″ tall and weighed a very fit 130 pounds. A gasp escaped Paul’s lips as he stared at her panty-covered ass. She was wearing his favorite pantyhose and panties. The crotch less pantyhose had side panels that attached to the waist band creating a frame fir her gorgeous ass. The silk panties barely covered her cheeks. There was a beautiful contrast of her light blue panties, white cheeks and brown hose.

Slowly Paul began to pull the panties down, revealing the divide between her soft white buttocks inch by inch. He left the panties at her thighs and leaned forward and kissed first one soft cheek and then the other. Crystal groaned as his lips left a trail of wetness, moving slowly across her soft cheeks. Paul smiled as goose bumps appeared on her smooth skin. Crystal was excited and ready for anything. She knew where this was heading and she trembled in anticipation but first she needed something else.

“Fuck my pussy first, I am so hot,” she pleaded in a whisper.

Paul removed her panties and turned her around. He lifted her onto the conference table and she raised her knees to her chest exposing her lovely blonde pussy. Paul leaned in and kissed her inner thighs working his way toward her treasure dripping with desire. As unfastened his pants and drooped them along with his underwear to his knees.

“Oh, I’m ready,” Crystal called out as she gasped his head and pulled it away from her pussy.

Paul moved between her legs and his 7+” thick cock looked ominous around her twitching pussy. He aimed his shaft at her opening and slowly eased it into her womb. Crystal gasped loudly with the penetration that she experienced so many times. He moved slowly and steadily between her legs thrusting into her and keeping his cock in constant contact with her clit. Crystal was going wild and she knew that she would cum quickly. She felt the orgasm building and then she climaxed covering her mouth with the crook if her arm to muffle her cries of ecstasy.

“Oh, hold me,” she called out after her intense orgasm.

Paul pulled her up and held her as tremor ran through her body. He waited until the calm after the storm before his eased his cock out of her. Crystal lay back down on the table but not for long. Paul stepped back, lifted her off the table and turned her around. Once again he bent her over the table, flipped her dress back up and went back to work in her lovely bottom. He smiled as he watched his beautiful assistant squirm in front of him. He loved to tease her. He would sometimes take an hour or more making love to her bottom. He loved the slow and sensual seduction.

“Oh God, Paul,” Crystal moaned. “Please!”

Paul gently nibbled the soft flesh. He stood back slightly and paused to take in the view. Her firm buttocks were perfect. His hands trembled as he reached out and caressed the soft skin. He again saw goose bumps rise on her cheeks and then run down the back of her thighs. Slowly, he opened her cheeks. Both of them moaned as Crystal’s tiny rose was exposed. He stared in amazement. He loved looking at her puckered little hole. Crystal couldn’t stop her hips from squirming as she felt his adoring eyes centered on her private place. Suddenly, she could feel his breath on her pulsing hole.

Paul’s lips were so close that he could almost taste her. His tongue came out and he touched the little hole. He circled his tongue around the hole in a teasing fashion. When Crystal pushed her bottom back, he pulled away teasing her. Next he moved his tongue to the top of her buttocks before sliding it down one cheek and then the other, leaving a trail of his saliva.

Crystal was growing impatient. “Oh please don’t tease me any longer!” she moaned as she felt Paul begin to lick her again. This time, his tongue started at the top of her crack and moved slowly downward, edging closer and closer. The excitement in the office grew when Paul’s tongue moved between the cheeks. Finally his tongue touched the tiny hole.

“Yesss!” Crystal groaned and pushed her ass back toward his tongue again.

Paul stiffened his tongue and pressed forward. Crystal screamed and her body began to shake. Paul had done this to her countless times but every time seemed like the first. She felt his wide tongue separating her sphincter and slipping into her body. She moaned as she felt his tongue begin to move in and out of her slowly stretching hole. He could lick his wonderful assistant’s ass for hours, but not today because he was too excited. When he pulled his tongue from her anus, it made a little pop as it shut.

Suddenly, Crystal felt empty and her anus pulsed, as if it had a mind of its own. Paul went to his desk and took out a bottle of lotion and paper towels. He returned to her and thoroughly lubricated her anus and his stiff cock. He brought his now throbbing erection to the divide between her cheeks and rested at the top of her crack. He added saliva to his lotion covered cock which provided the necessary lubricant.

The head touched the puckered rose and they both groaned. Crystal was going mad with desire now. She had to have it inside her. She pushed her hips up and back in desperation. Paul let the head touch the hole again as he pulled the cheeks even further apart. He centered the large head on her anus and pushed forward, gradually increasing the pressure. The tight sphincter resisted for a second before it opened up to receive him.

“Oh my!” Crystal moaned as the impossibly large head opened her hole. She concentrated, trying to relax. She knew that the head was always the toughest part. She held her breath and bit her lip. With a final push from her hips and Paul’s, the crown slipped inside and air rushed from her lungs. The stretched muscles of her sphincter gripped the head below the mushroom head, trapping it in a warm vise.

“This is so good doll!” Paul moaned as he felt her anal canal open to welcome him. Slowly he slid in, inch by inch, pausing occasionally to let her adjust until finally, his swollen testicles touched her dripping vagina. He stopped moving as he always did, allowing for Crystal to get used to the length and width of his large tool. The office was now silent but for their heavy breathing. By then he pants and underwear had dropped to his ankles. It seemed like an eternity for both of them before he started to move. Finally when he felt she was ready he slowly but steadily moved in and out.

“Fuck me! Fuck me! Fuck my ass!” Crystal cried out is a raspy whisper.

Paul smiled at her urging and began to move his hips faster. It was always like this; once she loosened up he didn’t have to be gentle any longer. He pulled his hips back to where only the cock head remained in her and then pushed forward sliding all the way into her with one thrust.

Crystal cried out with incredible pleasure. She could feel every inch of his hot shaft as it slid past the sensitive nerve endings deep in her canal. Paul gradually began to move more rapidly until he was pounding into his assistant’s tight ass without reservation. The table rocked beneath the two of them and the room filled with the slapping sound of skin against skin.

“Oh Crystal, I’m going to cum,” Paul moaned in warning.

“Yes, yes, yes, cum in me, cum in my ass!” Crystal begged as a strong climax overtook her. She could feel her anal canal pulsing and squeezing Paul’s long shaft. Each of her contractions brought a return throb from his hot shaft. Suddenly, Paul grunted in pleasure and began to pump his thick sperm deep into Crystal’s waiting hole. It felt like his balls were going to explode from the release of the building pressure.

Crystal could feel it as always. She loved the feel of the hot cum pouring into her canal. It was almost as if a soothing balm was being pumped into her ravaged hole. She gasped for breath until her climax began to wane.

Finally, Paul fell across his insatiable assistant. Each convulsion made her sphincter squeeze a little more of his dwindling release into her hole. He sighed as the last drop was pulled into her already overflowing hole. He kissed her neck tenderly and whispered, “I love your ass.”

Crystal let out a big sigh in response. Gradually, Paul’s penis lost its stiffness and slipped out of his assistant’s bottom. He stood up and smiled down at her still trembling form. A trickle of his sperm dribbled from her hole and ran down her leg. Paul took the paper towels and caught his seed as it oozed out her anus.

“Oh Paul, that got me so hot, I need to cum again. Eat my pussy, please eat my pussy.”

Paul turned Crystal back to him and lifted her back up on the table. She raised and parted her legs giving him full access to her pussy and he dove right in. Paul was a very accomplished cunt lapper, not that Crystal needed much at that moment. Within minutes she was cumming and drenching his face with her love juices. Crystal held his face lovingly against her quim as his tongued danced around her swollen clit. Her orgasm was intense and she again he to muffle her cries of joy in her arm.

They parted slowly and Paul looked at his lovely assistant sprawled out on the conference table. It was an erotic sight as she was still dressed except for her panties with her lower body framed by the pantyhose. Crystal cleaned her body the best she could with the paper towels before making her way to the ladies room. Paul cleaned up the office while she was gone and straightened his own clothes.

Crystal returned with a smile on her face and asked teasingly, “How was your Saturday morning?”

“The best ever, I have never had a Saturday start off like this one.”

“So are we still on for the trip?”

“We are, all the arrangements have been made. Is Jerry still going on his trip?”

“Yes, thank God. I am really looking forward to spending a week with you in the Caribbean.”

“I am too. It will be the first time that we will spend a night together, in fact six of them.”

“I should get going. See you Monday,” Crystal said and then kissed Paul on the cheek.

Crystal left the office and Paul got another cup of coffee and finished up his admin work. He locked up the office and headed to the deli for lunch. After lunch he worked out at the gym before returning home. The rest of the afternoon he watched gold on TV and read the paper. He thought about the upcoming trip to a couple’s resort with Crystal. It should be quite a vacation. He liked all-inclusive resorts as they were hassle free.

THE VACATION

Two weeks later Paul and Crystal were on the plane on the way to the Caribbean resort. Crystal was excited because the resort had a nude beach and she had always wanted to sunbathe nude. On the flight down they reminisced about some of their experiences before they hooked up and the first time they made it. Paul shared some of his affairs when he traveled particularly about one girl named Bonnie.

“She had the perfect body and there wasn’t anything she wouldn’t do. I particularly liked her curvy ass and fucking her on all fours. One time I looked over at the mirror and saw us. Bonnie was on all fours in her bed with her luscious tits hanging down while I fucked her in her incredible ass. It was an incredibly erotic sight. What about you? When was your first anal sex?”

“Well believe this or not, you are only the fourth guy I’ve had sex with and you are the only one since I got married. The first time is when I worked in Washington, D.C. I worked as a secretary in a government office. One Friday night we all went out for drinks and I ended up with two guys in their apartment. Before I knew it we were all naked and I was on all fours sucking one guy’s cock while the second one fucked me in the ass.”

“Was that your first time anal?”

“Yes but they took turns with me all night. I sucked both guys off twice and both guys fucked my ass twice. On Saturday they were back at me but I made them take care of my pussy too. There was always one of them in my ass though whether the other cock was in my mouth or pussy. They made me stay with them all weekend and by the time I left, my ass was really broken in and stretched out.”

“Wow that was some weekend. I heard that in D.C. a lot of girls are on the make.”

“Yeah, most of them power hungry. They like being with people of power, it’s a turn on for them.”

“So how did you meet Jerry?”

“He worked for a search firm and he found me my first job in Chicago. We hit it off, dated and then got married. The first five years were fine but then he started drinking heavy and using. He hung out with guys that were into drugs, that’s when our marriage went downhill. We hadn’t had sex for nearly a year when you and I hooked up.”

“Did you and Jerry have anal sex?”

“A couple of times but he didn’t get into it even though I always cleaned myself first.”

“His loss, you have a beautiful ass and I loved fucking it.”

“I know and you will have unlimited access to it this week.”

Just then the flight attendant announced that the plane was on the final approach and to fasten seat belts. Crystal hugged his arm and cuddled up to him as she was excited about a week in the Caribbean. They both looked out the plane’s window and saw the deep blue sea. It was absolutely beautiful and Paul was looking forward to a great vacation and a week of great sex with Crystal.

After the landed they went through customs and reclaimed their luggage. Next they took the shuttle to the resort and Crystal was surprised by the third world appearance of the island. Paul told her that the money the resorts made went to the corporations and the government, unfortunately very little of it made its way back to the island residents. The shuttle ride was about 45 minutes before they arrived at the resort.

Crystal, Paul and three other couples got off the bus and retrieved their luggage. They were ushered into the main lobby where they checked in and were given a map of the resort and the itinerary for the week. Crystal and Paul were shown to their room by a very polite resort employee. Paul learned the man’s name was William and he tipped him for bringing the luggage to the room.

“I thought that you weren’t supposed to tip,” Crystal stated.

“You don’t have to, but a dollar here and there goes a long way and we will get great service in return. We have an hour before dinner. Let’s walk around and get familiar with the grounds and then eat.”