It was three in the morning and Will was bone tired, almost too tired to climb out of his truck and climb in his comfortable bed. Finally, he crawled out of his truck, stretched, and headed inside. First order of business was to get him a Mountain Dew and then it was shower time to wash all the oil and glitter from his body. Once he accomplished both goals on his mental list, he fell into bed and was soon asleep.

After only what seemed like minutes to him but had been several hours, he was awakened by someone consistently ringing the doorbell. Knowing who it was, Will muttered, “That bitch is in so much trouble,” as he stumbled out of bed and slid on a pair of sweatpants. “I am coming, so hold on and get your damn finger off the fucking doorbell, Christy,”

Flinging open the door a few minutes later, he saw Christy standing there wearing a big smile and holding a box of doughnuts in her right hand, “Good morning, sexy. I bring a peace offering,” she said pushing past him, heading for the kitchen.

Following her to the kitchen, he saw her putting a cup of water in the microwave for instant coffee. Christy then reached into another cabinet and pulled out a big glass, which she filled with milk and put on the table.

Squinting Will looked at the clock on the wall and asked, “Do you know what time it is, Miss Sunshine?”

“Going on nine in the morning and time for sleepy heads to be out of bed,” she told him as she fixed her cup of coffee and sat down at the small table. “Are you going to sit and enjoy breakfast or just stand there and glare at me like an angry bear?”

Will sat down and reached for a doughnut saying, “Did you forget the type of work I do? I did not get into bed until around four this morning and five hours of sleep is not enough. So why you are here this early and it had better be a good reason or I am going to blister your ass.”

“I wanted to bring you breakfast,” she teased

“Spit it out. What is the real reason you are here?”

“Well,” Christy began, “you remember my friend Ann from college?”

“Ann… oh yeah, the blonde with great tits and ample junk in her trunk,” Will told her. “Yeah, I remember her but why do you ask?”

Christy snorted and said, “I want you to fuck her and show her what hot sex is like, that it is not boring, and is fun.”

Will, who had just taken a drink of milk, started to cough and spit milk everywhere at what Christy said, not believing he heard her right. She jumped up and got a dishtowel from the drawer, handing it to him to clean up his mess.

“Are you kidding me?” he asked, looking at her trying to judge by her body language to see if she was serious or not. “You want me to fuck Ann because she apparently does not like sex. Do I look like a fucking hands-on sex therapist Christy? I am a fucking stripper, not a paid escort.”

“I never said anything about paying you, Will. She thinks sex is boring, that it is not even worth the time to engage in it. It is all because of the men she has been with.”

Will shook his head and said, “I am not even going to ask how you know all these personal details. If she hates sex so much what makes you think I could get to first base or even score a homeroom?”

“Will, we have been friends since we were babies and I have seen you in action plenty of times. I know you can do this.”

“And how do you know I could give her hot passionate sex that would melt the ice and make her desire fucking?” Will asked, teasing her because he already knew the answer. He was the one to take her virginity when she turned eighteen and they had spent the weekend fucking their brains out but that was the only time.

Christy mumbled, “You know how I know, asshole. So will you do it?” She said, giving him what he called her ‘puppy dog’ eyes.

“Even if I agree, what makes you think she will?”

“Today is her birthday and I am giving you to her as her birthday present. You know it is rude to turn down gifts.”

Will just looked at Christy and shook his head, a plan formulating in his mind. “Bring her to the club tonight. I will make sure you have a front row table. This will be a birthday she will not forget,” he added, not believing he was even going along with Christy’s plan. On the other hand, Ann was a hot babe and he had at one time wanted to get in her panties but for some reason never did.

“Okay, Will, now I am getting out of here so you can go back to bed,” as she got up and walked around the table, kissing him lightly on the lips. “Thanks.”

Will turned and smacked her ass as she walked away. “I am awake now so there is no going back to bed, Christy.”

Her laughter followed her out the door as it opened and clicked shut behind her. After eating another donut and finishing his milk, Will cleaned up the kitchen and went into his bedroom yanking off the sheets and putting on another set. He then he vacuumed the bedroom and the rest of the house.

----------------

When he got to work that night he talked to his boss about what he wanted to do and to make sure that she was okay with it. When it was time for his first set he took a deep breath as he stood at the back of the stage, hoping everything did not blow up in his face. As the first notes of Shoot to Thrill by AC/DC came from the speaker Will strutted on stage. He was wearing tight black jeans that looked as if they were painted on and a maroon tee-shirt that hugged his biceps and muscular chest.

Hooking his leg around the stripper pole he began to move around it, and then he faced the audience humping the pole. Walking to the edge of the stage he crooked his finger at Ann who looked up at him in surprise and pointed to herself. He nodded his head and started to gyrate his hips, pulling his tee shirt off and tossing it at her. Christy began to push at her until Ann had no choice but to get up or be pushed to the floor by her friend.

Timidly, she made her way to the stage where Will took her by the hand and led her to a chair he had confiscated from the back of the stage. Once she was seated Will straddled her lap and began to bump and grind, almost pushing his erection that was straining his zipper in her face.

Stepping back he turned his back to her, shaking his ass at her, and then he started to slowly unzip his jeans. Turning back around, he grabbed his jeans on both sides and pulled, ripping them off and letting them drop to the stage in two pieces. This left him wearing nothing but a skimpy pair of underwear that barely was able to contain his erection.

Giving a few more gyrations, bumps, and grinds, Will leaned over and kissed her cheek, whispering in her ear, “Happy Birthday, Ann. The rest of your present will given to you later… in my bed.”

He took her by the hand and led her to the stairs. He then retrieved his clothes and went backstage. Will had made arrangements with his boss to only work that one show this evening so he quickly changed into his street clothes and headed for home. Christy was supposed to bring Ann by around eleven o’clock.

When the doorbell chimed at precisely eleven, Will had several candles lit, the bed turned down, soft music playing in the background and beer chilling in the ‘fridge along with cokes and Johnny Red. When Will opened the door he saw Ann standing there, the look on her face almost as if she was a cow being led to slaughter. At the curb, Christy gave a short toot on the horn and pulled away.

“Come on in. I promise I don’t bite… unless you ask me to,” as he leaned forward, kissing her on the cheek as she started past him. “What would you like to drink? I have beer, Johnny Red and coke, or just plain coke?”

“Johnny Red and coke sounds good but light on the liquor please,” she said as she looked around the room, taking in the candlelight and soft music.

Will disappeared in the kitchen and came out a few minutes later with two drinks in his hands. Seeing Ann still standing in the same spot he had left her in, he handed her drink and asked, “Ann, do you really want to do this or are you doing it because you don’t want to make Christy mad?”

Ann took a sip of her drink, admitting, “I want to do this but I fear it will be a big disappointment as all my other sexual encounters have been.”

“I am not like your other sexual partners Ann. I guarantee I will have you screaming out in ecstasy many times before you leave,” he reassured her as he reached out and rubbed the palm of his hand over her left breast, feeling her nipple immediately harden.

Ann took a big gulp of her drink and said, “Then let’s get this party started. I want to see if you can do what no other man has been able to do Will.”

Will loved nothing more than a challenge and he was determined to make her have mind-blowing orgasms that made her scream. Will and Ann quickly finished their drinks. He took the empty glasses and put them on the end table. Extending his hand, Ann took it and let him lead her to his bedroom.

Ann could feel her body shaking as Will began to slowly unbutton her blouse, planting kisses on each area he uncovered. Unbuttoning the last button, he pushed it off her shoulders, and down her arms, tossing it aside, leaving her standing there in a minuscule black lacy bra that barely contained her size 40 C boobs. Hefting them in his hands Will began to lick and nip at her nipples through the cups. Unclasping it at the front, it was tossed in the vicinity of her blouse.

Leaning down, Will licked her left nipple, and then her right one. Alternating he licked, sucked, and pinched each nipple, causing the crouch of her thong becoming damp. Will then moved back up kissing her throat as he reached behind her to unfastened her skirt and push it down to the floor. Sitting down on the bed, Will pulled her toward him, indicating that she should straddle his lap.

Once he had her where he wanted her, Will latched onto her right nipple, sucking hard as if were a starved baby while his right hand pinched and pulled the other one. Ann had never felt such pleasure in her life and she could feel her thong getting wetter. Soon he switched nipples, continuing alternating between her nipples until she was wiggling on his lap.

Suddenly Will stopped and indicated that she should stand up and turn her back toward him. As Ann turned around, her gorgeous ass came into view, framed by the garter belt she wore to hold up her stockings. Will could feel his cock hardening at the sight of her ample ass that was just made to be fucked. While many men were tit men Will was an ass man and nothing turned him on more than a woman with a sexy ass that demanded to be made love to.

Will dropped to his knees behind her and squeezed her ass. He leaned forward, kissing each cheek before he started to nip her at her ass, leaving several hickeys. Moving her thong aside, he swept his tongue up the crack of her ass, causing her to shiver.

“Strip for me, Ann,” he said sitting back on his heels as he reached into the bedside table for some lube.

Ann slowly unfastened her stockings from her garter belt, rolling them down her leg, one at a time, and then removed her garter belt and thong. She turned around, standing before him naked, her nipples hard little peaks. When she looked at Will, he had removed his sweatpants and was sitting on the bed naked with a tube of lube in his hand.

“I… ah… never…” she started saying only to be interrupted by Will.

“I love anal virgins,” he whispered

Pulling her toward him on the bed, he had her spread her legs as he leaned forward to kiss his way up one thigh and down the other while his hands squeezed her ass, loving the way it felt in his hands. He could not wait to take her anal virginity but first, he had other plans.

Putting some lube on his finger he began to put just the fingertip in her anus while his tongue licked her outer lips. Ann braced herself by putting her hands on his shoulders as his tongue dipped inside her pussy, his finger sliding farther into her little-puckered hole.

Will continued to lick her sex slit while he gently finger fucked her, making sure he did not go past the first knuckle on his index finger. His tongue flicked over her clit, causing her to inhale quickly at the strange sensation. Then he moved back to the middle of her sex slit, tongue fucking her as he fucked her ass with his finger. 

Will listened to the change in her breathing as he started to taste her juices on his tongue. He was not ready to let her cum yet.  Pulling his finger out and backing up on the bed, he patted the bed, indicating he wanted her to lie down beside him.

As soon as she lay down, he moved down toward her feet.  Will spread her legs apart blowing hot air on her exposed pussy.  Then he spread her pussy lips and continued to blow gently, this time on her clit for several minutes. Soon Ann found herself wiggling on the bed, her body feeling like it was on fire.

He began to nibble on her pussy lips as the tip of his thumb grazed her clit, causing her to squeal in pleasure. Sliding two fingers deep inside, he moved over to suck on her clit, sending her reeling toward the edge, and then he stopped and started to flick his tongue over it while finger fucking her.

Ann reached down and grabbed him by the hair, moaning as she pulled him closer to her pussy. Will continued his assault on her clit until she screamed and clamped her thighs together, trapping his head between her legs, his face lapping up her juices as her body trembled and shook, stars flashing behind her eyes as Ann achieved her first orgasm. Finally, she relaxed her thighs and Will moved back and then up to kiss her, his tongue slipping between her lips.

As his tongue plunged into her mouth she could taste her juices on it as Will kissed her hard and deep, tongue plundering her mouth. While he kissed her he started to rub his cock against her wet pussy.

“Touch me, Ann, guide me inside of you,” Will instructed. “I want to fuck you.”

Ann reached down and touched his cock, slowly guiding him to the entrance of her pussy. Will then pulled her legs over his shoulders, driving himself deep in her pussy, almost bending her in half. As he pistoned slowly in and out Will made love to her mouth, and then her neck. Slowly, he began to fuck her harder and faster, making the bed rock with his hard deep thrusts. He listed to her breathing and when she was almost to the edge, he stopped and pulled out.

“On your knees, ass in the air,” he ordered stroking his cock.

Ann did as he told her, being rewarded with a smack on the ass as he drove his cock into her pussy. Grabbing the lube from where he had dropped it on the bed, he put some on her little-puckered hole and his index finger.  Slowly he slid his finger into her ass, this time all the way into the last knuckle.

“Reach back and rub your clit while I fuck you,” Will said.

Soon he was fucking her hard in both places, his free hand squeezing her ass.

“Oh fuck,” Ann moaned as she felt her body start to tingle, all nerve endings on fire, her pussy squeezing his cock like a vice grip.

Suddenly, Ann screamed as her juices covered his cock and ran down her thigh. Will pumped her harder, moaning loudly as he shot jet streams of cum deep inside her. Ann slumped down on the bed, Will on top of her. He pulled his finger out and started planting little kisses on her neck and shoulders, his cock slowly deflating inside of her.

“That is round one. As soon as I rest it we will have round two,” he said as he rolled off her, pulling her in his arms, kissing her gently.