Step One: The Introduction
She rose to her feet erratically and extended her hand it too was shaking.
"Michael?" She asked her voice nearly cracking. He smiled and it lit up the coffee house and he took her hand and gave it a few gentle pumps before letting go.
"Carol?" He asked as he directed with a gesture that they should sit. "You can relax I am here to help." He reached out and took one of her hands and began to gently rub it and waves of heat ran from her hand to the rest of her body and she found herself calm in no time at all. "There now that's better isn't it?" She could only nod. Michael looked her over discretely and made mental notes the entire time. Carol was gorgeous if you could get passed the glasses, baggy sweatshirt and sweatpants and running shoes. Her hair was up in an unflattering pigtail and what little makeup she wore was all wrong for her. Carol's red hair and green eyes were a definite good start and her firm breasts, that made even the baggy sweatshirt enticing, were a good distraction. If only her could see her ass that the sweatpants clung to so nicely but all in good time. "I am going to be your sex coach and you need to trust me, okay?"
"What exactly are you going to do?" Carol asked wondering how he looked naked and that just made her nervous all over again.
"Good question!" Michael replied smiling again. "I am going to restore your sexual confidence and make you ready to get back into the dating scene. Teach you how to make love and the basics."
"Great!" Carol half moaned, "I haven't had a cock in me in over a year." She blushed but didn't apologize. "I really need to 'learn the basics' as you put it." Michael nodded and stood up and offered her his hand.
"Time to get started." She stood up and took his hand and he led her out of the coffee house down the street and down a narrow alley. When they were well out of sight of the public he took her by her shoulders and turned her to face the brick wall.
"What are you…" his hands moved under her sweatshirt and cupped her large firm breasts and began to knead them. "…Oh gods yesssss…" His fingers found her rock hard nipples and began to tease them. She pushed her ass back against him and could feel the hard bulge in his jeans; she moved her hips up and down massaging his cock through his pants with her heart shaped ass. Michael's hands moved to her sweat pants and he pulled them down then he freed his cock. He yanked on her hips pulling her lower body away from the wall until her back was parallel with the ground. He took his iron hard dick in his hand and teased her pussy with the head. "Oh please fuck me…" she moaned softly not wanting to be overheard. Michael eased his cock into her an inch at a time; letting her feel all of it until it was buried in her very tight very wet pussy. He settled his hands on her hips and began moving his hips forward and back fucking her slowly.
"You are a dirty little whore aren't you?" He whispered in her ear his breath enticing her even more.
"Yesssssss!"
"You like your naughty tight pussy fucked like this don't you?" His teeth found her earlobe and he chewed on it as he continued to slide his cock in and out of her.
"Yesssssss!" He swatted her ass cheeks as she pushed back on him.
"You liked to be fucked hard and fast don't you?" He began to do just that ramming his hips forward and pulling her back onto his cock.
"YESSSSS!" She squeezed her already tight pussy around him and he had to fight from cumming. The wet slapping sound of their bodies echoed in the alleyway. He spat on her asshole and rubbed the spit in and then slowly eased a finger into her even tighter ass fucking both her holes at the same time. She threw back her head and her entire body shook as a powerful orgasm tore through her, a muffled scream escaped her lips and still he rammed his cock into her tight depths. He eased a second finger into her ass as her orgasm subsided. "Oh gods your fingers feel soooo good in my ass!" She moaned out as she pushed back harder and harder. "I want you to cum… fill my pussy, let me feel it paint my insides."
Michael kept fucking her his cock swelling and swelling his orgasm getting closer and closer. He yanked out his cock and without a word of encouragement she spun and dropped and took his dick into her mouth; so while one hand stroked the shaft wanting to milk him of every last drop of cum her head moved forward and back taking about half his cock into her mouth. His body shook and shook and finally with a thrust of his lips she was rewarded with pulse after pulse of hot warm sperm. She swallowed greedily and kept sucking and stroking even after the orgasm had died and she even stroked faster and sucked harder now. Sensory overload washed over him as she finally let go of him and he shuddered weak in the knees. She licked his shaft clean of her pussy juices and tucked him into his pants and zipped him up.
"Lesson one accomplished
spontaneity
." Michael said as she rose to her feet weakly and leaned up against him literally purring.
"I liked lesson one." Michael just smiled and nodded he always liked lesson one the best but time waits for no one.
"Well we need to move on to lesson two. I will meet you at your apartment bright and early tomorrow morning around nine o'clock." Carol smiled wickedly but quickly hid it.
"You could always spend the night, I have a couch you could use." Michael thought it over.
"I don't know." He said watching her body language.
"Please!" She was smiling brightly now a complete change from the moping girl in the coffee house.
"Ok I will spend the night." She clapped her hands together and together they walked out of the alley both smiling and chatting happily. For the rest of the night he fended off her sexual advances he could see she was hungry for another pounding but she had to wait.
Later that night…
Carol tiptoed from her bedroom into the living room her heart was tripping in her chest beating so loud surely it would wake up the sleeping figure of Michael. She got to the couch with its fold out bed gliding on sock clad feet. She looked down at the sleeping figure of Michael and she smiled hungrily licking her lips as she knelt down by his midsection. All she could think of was his hard cock in her mouth. Slowly she peeled away the blanket covering him and she revealed him in all his glory, he slept in the nude! Carol reached down and took his soft member into her hand and he moaned in his sleep. She started stroking him and quicker than she would have thought it began to grow getting harder and harder. She lowered her head, opened her mouth and took just the head into her warm wet mouth. Michael moaned louder in his sleep.
"…oh God yes…" She sucked and swirled her tongue around the head and his hips moved a little. His moaning got a little louder as inch by inch she took more of him into her mouth. With her free hand she slid two fingers into her already soaked pussy and bit-by-bit her head moved faster her fingers keeping perfect time. She moaned around his dick sending more sensations to his dreaming brain. She took a firm grip on his cock and then she took it out of her mouth and lapped at it as if it were an ice cream cone before standing up, moving onto the bed above him. Slowly Carol squatted bringing her pussy closer and closer to iron hard cock savoring the moment. She felt the head touch her lips and she wiggled and the tip slid into her. Now she moved slower still her eyes fluttered shut as he began to fill her up; his long thick cock stretching her until with a purr he was hilted in her. She began to move up and down a little at first just a few inches up and down. But soon half his thick member was moving and out of her. Carol began to pant as she felt a mind-blowing orgasm building and building getting too big for her body to contain. Her eyes snapped open and she looked down and Michael was moaning loudly in his sleep.
"Oh God yes! Fuck me you dirty little whore take that cock in your fucking ass!" He grunted with each of her down strokes. Suddenly her orgasm was upon her and she had to bite her hand to keep from screaming. She sat down his cock fully buried in her and she just sat there and squeezed him with her pussy muscles. Each time he moaned and muttered a curse. "Mmmm your ass is so fucking tight you filthy slut!" Carol had never done anal before but the more he moaned the more she wanted to at least try it. She stood up then kneeled next to him then with a mix of spit and her pussy juices she eased a finger into her ass.
'That's not so bad she thought.' She fingered her ass while she licked and sucked on Michael's cock to keep it nice and hard for her. When she was ready to she added a second finger and finally a third. 'That ought to about do it.' Once more she stood up and turned away from Michael and began to squat until the head of his cock met her sphincter and with a deep breath out she lowered herself slowly until the head 'popped' in. With a few quick breaths she relaxed and lowered herself the rest of the way. She waited until her ass got adjusted to having an eight-inch cock in it before moving. Carol rocked forward and back fucking herself in the ass with Michael's dick. Despite her reservations she began to like the sensation and then she reached between her legs finding her clit and the dual sensations were amazing. Michael's cock began to thicken and swell signally a powerful orgasm and she kept a quick pace and loved the extra stretching her ass received from his dick. His moaning got softer and his body shuddered and with perfect timing she sat down on his cock as it exploded sending a torrent of cum into her very tight ass. Each pulse of his orgasm risked pushing her over the edge but not quite. While his cock was still hard she started moving again and rubbed her clit faster and faster and soon her hips were once more moving forward and back and she rocked and rocked. The sensation started in her toes and moved quickly all over her body and she knew this orgasm was stronger than the one in the alley. But she forced herself to keep a slow pace to eek out every possible moment of pleasure from the sleeping man.
It hit her mid stride and her body felt like jello as all her strength was tore from her by the orgasm. She dropped down impaling herself on his cock and a second orgasm blurred into the first and Carol nearly fainted. When she could open her eyes she looked back and saw Michael lying there with an angelic smile on his sleeping face. She eased off of him and using her mouth she cleaned him then covered him up. Once more she snuck away on stealthy feet to return to her own bed. Her eyes slowly closed seeing the clock on her end table that read 4:04 a.m. she smiled and drifted off to sleep.
"BUZZZZZZZZZ!!" The alarm wailed at bright and early hour of eight a.m.
"Oh fuck off!" Carol moaned hitting the snooze button.
"Morning Sunshine!" Michael beamed down at her holding a cup of coffee for her wearing nothing but his smile and a semi hard cock. Carol's head escaped the covers and took in the scene. Her eyes drifted between coffee and cock. She sat up and took the coffee from him and absently stroked his cock while she sipped her coffee.
"You are in a good mood." Carol said watching his member get harder and harder.
"Had the most amazing dreams last night." Carol sets her coffee cup down and takes his cock in her hand and starts to stroke while her mouth licks and sucks the tip. She takes the head in her mouth sucking; he cheeks caving in, and then slowly inch-by-inch it disappears into her throat. Michael sets a hand on either side of her head and starts fucking her mouth.
"I dreamt of fucking you in the ass, is that crazy or what?" Carol sucked harder her tongue swirling around the shaft as his hips thrust forward. "Oh you like me talking dirty while you suck my cock!" He grabbed her by the hair now "I was swatting you on the ass as I watched my dick sink into you slowly but oh so good. I was calling you a dirty slut and I could really feel my cock in your ass." Carol lightly raked his shaft with her teeth. "So are you a dirty little slut?" Her answer was to deep throat him and hold him there. "Mmmm you are a fucking little whore!" Michael pulled his cock out of her mouth and made eye contact. "Do you want to swallow my cum or wear it?"
