I Love Sex Stories

Gillian searched desperately for a street sign. She was on Akard, a one-way street with many stoplights. Traffic moved at a slow pace, stopping frequently. To top it off she was stuck behind a semi and couldn’t see the street signs ahead. She could see the top of the skyscrapers ahead, but where was Pacific? She moved into the right lane. A van honked behind her. She waved, glancing at the huge driver in her rearview mirror. He was mad.
This was turning out to be the worst day of her life. Suddenly she saw the sign above the street and turned. Thank God, there was less traffic. Now to find the building. Dallas was a confusion of one-way streets. It was easy to get lost. Would she ever find her way back to highway 75 in all this confusion?
Gillian took the elevator up to the 23rd floor. Her knees were shaking as she waited for the doors to open. Would she get this job? She had tried dozens of times before, but nobody wanted to hire somebody her age. She was getting desperate. The doors opened and she stepped into an empty hallway. She saw nothing significant in either direction except anonymous doorways. Gillian took the sheet of paper out of her purse and stared at the directions. Door number 27. She turned left and found the door in seconds. She turned the knob and stepped inside. A handsome man in his 40’s stood and stepped forward with a happy smile.
“Gillian?” he asked gaily.
“Yes, you must be Bill.”
“Right the first time,” he said with a heavy Texas accent. He shuffled her forward into a chair beside his desk. He pulled her chair over before her and sat with his hands in his lap, his eyes traveling over Gillian’s body. “Let me be brutally honest and come right to the point, Gillian,” he said in an intimate manner. “I’ve had seven women come thorough the door today,” he pointed at the door behind her. “They have all failed to meet my needs. Do you know why?”
“No, sir, I don’t,” Gillian said with her heart sinking. Seven?
“Because they just don’t have what I want. They are fine, up to a certain point, but they just don’t go far enough. Do you see what I mean?” he asked with his face just inches from her’s.
“N… no, I don’t understand,” Gillian said nervously.
“I’m looking for more than a secretary, more than a receptionist. I’m looking for all those and a companion. Are you willing to go that far, Gillian?” he asked, placing a hand on her knee. Her immediate reaction was anger. She wanted to slap his hand away and storm out of the office. Then she remembered how hard it was for a 48 year old woman to get a job in Dallas.
“I… I understand,” she said, swallowing convulsively.
“Good, great, Gillian. Now the first thing I want to do is see what you’ve got and how cooperative you can be. That entails taking off your clothes and putting on this suit,” he said, holding out two strips of lycra. “Consider it an audition.”
Gillian was very nervous. Her impulse was to run out of the office as fast as she could run, then find a cop. But hunger was a strong emotion. Besides, why the hell should she care, she liked to fuck as much as the next gal. Screw it, she would do this and anything else he wanted. She could always sue him for sexual harassment later.
Gillian stood and calmly undressed. Bill moved over to a nearby couch to watch. He had an eager, breathless look on his face, like a young boy with a new toy. Gillian’s suddenly stopped in the act of putting on the lycra suit. He whistled in appreciation as her full, ample breasts fell from her bra.
“How much does this job pay, and do I have the job?” she asked.
“I will certainly let you know after seeing what the next few hours bring,” he said eagerly. “Put it on,” he nodded at the plastic panties.
“No. I want some assurance that you are not going to fuck me and toss me out. How much does the job pay and do I have the job?” she insisted.
“Gillian, if you go through with this today, and any other time I feel the need for companionship, you will certainly have the job. I will start you at 25 dollars an hour. To tell you the truth I had a secretary for over three years. She would dress sexy as hell, show her panties a dozen times a day, and bend over to give me a tit shot. But the moment I tried to make a move on her she got all sanctimonious and belittled me. I had enough. I fired her. Then I was thinking, what I need is to hire exactly what I want. What I wanted was a woman close to my own age, with some experience and no husband. I wanted a woman who would bend over and drop her drawers when I told her without question. Hell, I own a multi-million dollar company, why shouldn’t I enjoy my work?”
Gillian thought for a moment and nodded. She managed to put on the lycra blouse and was about to snap the crotch on a unique contraption to form a pair of panties, but he stopped her.
“Wait, turn around and show me your butt,” he whispered.
She licked her lips nervously, but did as he asked. She knew her ass was not her best asset, but it was cute for a woman her age.
“Climb up on the desk and bend over. My God, look at that,” he said breathlessly. She could hear him moving closer. He knelt behind her and ran a hand over her unblemished rounded cheeks. She felt him sniffing her pussy and resisted the urge to giggle. “That is the most beautiful ass I’ve ever seen,” he said before kissing her right butt cheek. She shivered under the warm contact.
“Would you let me fuck you in the rectum, Gillian?” he asked in a whisper.
“Yes,” she said simply. She was shuddering in excitement. She felt like she was in high school with the first boy who had fucked her. She had lost her virginity in the back of a 1968 Cougar. She was now about to lose her anal virginity on the 23rd floor of an office building in downtown Dallas.
As Bill’s tongue touched Gillian’s puckered asshole she squealed and shot forward on the desk. He pursued her, pressing his puckered lips between the cheeks of her ass and rimming her delectable asshole. She felt fire spreading from her rectum outward. She mashed her tits in her hands, with her face pressed against the cold shiny surface of the desk.
“Roll over,” he whispered after giving her butt one final kiss. Gillian decided that what had occurred so far had made the trip from New Orleans worthwhile all by itself. This was becoming very exciting.
She rolled over on her back and noticed that Bill was now naked. He had a short fat cock. At the moment it was standing at attention, just inches from her asshole. Bill smiled, spit into his hand and rubbed the end of his cock. The movement made a slick wet sound. She felt so excited that she shook visibly.
Bill held one of her legs in the air with his left hand, and guided his thick cock toward her anus with the right. He was moaning with each breath. She could see that he was as nervous as she was. His cock touched her rectum and she cried out. He smiled and looked down at his cock as the head pressed against her ass. He applied more pressure and she could feel it spreading the ring of her asshole with great pressure. She whimpered slightly, but pressed her anus back toward him. He gave a few shuddering thrusts toward her ass and the head suddenly slid inside. Gillian screamed and grabbed at his cock. But he had stopped and was simply waiting for her anus to stretched to accommodate him.
Gillian felt like a wine bottle had been shoved up her rectum. She wondered if she was bleeding. What if she needed stitches? How could she ever show up at the hospital and explain what had happened? Gillian was suddenly aware that his cock was sliding further inside her. She whimpered fearfully, but there was less pain. Her asshole had miraculously stretched. It seemed hours, but was only a few minutes until Bill began plunging in and out of her butt while he breathed harshly above her.
Bill reached out and mashed her firm breast in his hand, as he pumped steadily into her anus. His cock was sliding smoothly well up into her anus now. She felt a fire building deep down inside her. The fire was spreading to her loins.
The fire was building in her ass, but she needed relief in her pussy. She started to reach for her pussy, but he slapped her hand away.
“Wait,” he whispered in a grunt. She felt like crying, but she had to obey him. He fucked her for several more minutes, then paused.
“On your knees,” he commanded. She turned and knelt on the cold desk with her head down. He climbed up on the desk behind her and shoved his fat cock inside her gaping asshole. She screamed and tried to jerk away, but he grabbed her butt and held it in a firm grip. In a moment she no longer wanted to pull away. His cock in her rectum felt heavenly. But she needed relief and being fucked in the ass would not give it too her. Was it a test?
“Oh fuck,” Bill moaned above her. “You have such a sweet little backside,” he said as his hips hit her ass with a loud smacking sound. She realized that her knees were beginning to hurt. At first she could ignore the pain because of the pleasure emanating from her asshole. But soon it became too much to bear.
“My knees hurt,” she whispered, hoping he would not become angry. He pulled out of her rectum wordlessly and pushed her to the edge of the desk. He laid on the desk face up and waited. She quickly crawled over his prone body and started to lower her pussy over his cock.
“Not yet,” he cautioned her with the shake of a finger and a smile. He repositioned her plump ass until her asshole touched his cock. He pulled her down roughly, impaling her anus on his cock. He moaned, feeling an orgasm begin deep down in his balls. He knew it wouldn’t be long.
“My pussy is starving for attention,” she begged as she bounced on his fat little cock.
“Not yet,” he said with a twisted face. “I have never fucked an ass before. I want to cum in your butt,” he nearly shouted, feeling his orgasm give a few false starts as the heat built in his balls. “NOT YET!” he screamed again louder. “NOW!” he cried. Gillian felt his hot cum spurting up into her rectum. It was a good feeling, hot and somehow satisfying. She felt the pressure build in her as a huge ball of cum collected inside it. She again reached for her pussy, but he grabbed her hand and pulled it away. She sat motionless in defeat, watching the emotions twist his once handsome face into a withered mask. Slowly he relaxed and slumped down on the desk. He turned and pulled open a drawer. He pulled out a box of kleenex and a huge oddly shaped dildo. He handed the dildo to Gillian and pulled a handful of kleenex out for himself. He held them around his cock and lifted her. She pulled off his cock. He handed her the box of kleenex and sat up on the edge of the desk.
As Gillian cleaned her tortured butt with the kleenex, Bill wiped his cock and sat in the desk chair with a satisfied grin.
“Now,” he said quietly. “I’ve only seen a woman fuck herself with a dildo once in my entire life. It was the most erotic thing I have ever seen. Now that I’ve made you hot, make yourself cum.”
Gillian hurriedly turned on the vibrator and laid on the desk. Fully aware of his lustful eyes on her, she slid the vibrator up inside her pussy with a squeal of delight. The dildo had two heads, one large head for her pussy, and a smaller one for her ass, or to stimulate her clit. She chose to insert the smaller head into her anus, increasing the fire he had already started there. She pulled the dildo up inside herself with sure, brutal strokes. The vibrations seemed to fill her ass and travel up her spine. She used her left hand to reach down and stimulate her clit. She was in heaven. She felt very hot and sexy under his adoring, lustful eyes. She had never felt so wanted in her entire life.
She arched up off the desk with her pussy in the air. She jerked the dildo down inside her moist hole, crying with each stroke. The fire was unbearable. Her entire body was on fire. Even her neck tingled. She hunched against the dildo harder, feeling her loins glowing with the beginning of a horrendous orgasm. She knew it would be devastating and all-consuming. She feared the impending orgasm, but craved it at the same time.
“Oh fuck,” she gasped. Her eyes flew wide with horror. Bill moved closer to the desk so he wouldn’t miss a thing. He looked down in his lap in surprise and found his cock again had a raging hardon. This was one hot little bitch, and she was all his.
“Oh yes!” Gillian yelled. She grunted several times, stiffened with a frightened glance toward Bill, then screamed as the orgasm began throbbing in her loins. She felt her pussy muscles clenching and unclenching around the dildo. She threw here head back and trashed from side to side. She swore and grunted as she withered on the desk, then suddenly sat up and grabbed for the dildo. She jerked it out of her sensitive pussy and fell back in exhaustion. Eventually she twisted the base and turned it off.
“My God,” Bill said reverently. “That is the sexist fucking thing I’ve ever seen. You are hired, Gillian,” he said, leaning forward and kissing her breast. She shivered at the contact. She rolled over slowly. He slapped her butt cheek and jumped to his feet.
“Get dressed,” I’m hungry. “Well take the rest of the day off to celebrate,” he said as he pulled his clothes on.
“I’m going to love working here,” Gillian said as she slowly began to dress.