Allison walked out of Federal Hills Blue Grotto restaurant frustrated in every sense of the word. It had been bad enough that she had been roped (and not in the fun sense) into a client meeting on a Friday night but to have had the client be fifty, fat and disgusting made the evening entirely unacceptable.
To top things off, after giving it what she had felt was a sincere effort; after all business was business and the advertising industry was as cut throat as any other, she wasn't even able to get any kind of a deal. That wasn't to say that Jabba the Hut wouldn't have played ball but probably only after she had played with his and although Allison wasn't above using what she had if it was worth it, she did have standards.
One of which was that she shouldn't need to use a GPS to find a guys cock under his stomach. The client of course seemed to think he was going to get some, point blank telling her she had to "Give a little to get a little and wouldn't it be worth it to land this account?"
At which point Allison had slipped off her heel reached up and placed her foot where she assumed his cock would be and after holding it there for a moment and enjoying the look on his face had smiled sweetly and said "Sorry Ted but your account, much like your cock isn't big enough to hold my interest."
With that Allison had put her shoe back on and strode out of the restaurant leaving Ted with both a bruised ego as well as the check. Best part was that she couldn't really get in trouble when it was your firm in the first place. Now however here she was at nine o'clock on a Friday night all dressed up with no one to appreciate it.
Then again maybe the night wasn't a total loss after all, Allison could always take out her frustration as well as have her needs catered to and by someone much more her type than the pompous ass she had just spent the last two hours with. Yes, that's exactly what she needed, someone who knew their place. Removing her cell phone from her purse Allison dialed a number and after several rings a young mans voice answered.
"Yes Mistress?" He sounded winded, better not have one of his little girlfriends over she thought.
"Why did you take so long to answer?"
"Sorry, I'm at work."
"I see and what time are you working until?"
"Eleven my Mistress." Was the reply, excitement already creeping into his voice.
"No Jeff, that's much to late. I have needs. I will be at your place at Ten o' clock"
"But Mistress, I'll get in trouble! My boss.."
"If I have to ask twice, I shall never ask again. I have a phone full of numbers of many young men who would be more than happy to service me this or any other evening. You however were my first choice, a poor one apparently."
"No Mistress! Please don't hang up! I.. I'll be there!" he was all but stammering.
"That's better. Do not be late." With that Allison hung up and approaching the valet handed him the ticket for her red 2009 BMW convertible. Maybe there was still hope for the evening.
Although she had said ten, Allison arrived at Jeff's apartment at 9:40 so she could set the tone for the evening by saying he was late. Leaving her car in the parking lot across the street so he wouldn't see it, Allison walked around to the back and let herself in the downstairs door with the key he had been more than happy to give her.
Reaching the third floor Allison took an impatient pose leaning against the railing at the top of the stair case. Jeff was twenty one years old (Which at fifteen years her junior was just how she liked them) and worked as a bus boy at the Ninety Nine restaurant at night while attending URI during the day. The three room apartment he lived in was actually in a decent neighborhood so she had no worries about waiting around.
Allison had been seeing Jeff for about three months now and had him pretty well trained. Well enough that she had actually paid last months rent for him as he had missed a few nights of work over the course of their time together and had fallen behind. Jeff had protested but she had explained to him to just enjoy the fact that a hot older woman was willing to pay him to fuck her. After all it would be a great story to tell his college buddies.
As she waited Allison removed her compact from her purse and checked herself. In a word Allison was gorgeous and if she didn't already know it there were plenty of men who would and had lined up to tell her. Standing about 5'5" she was neither too short or too tall and likewise at one hundred and twenty pounds she had curves but no where near enough to be considered chunky.
Allison had long raven black hair that she was sure behind her back the catty bitches at work said was dyed which contrasted with her very fair almost porcelain complexion. Her two best attributes in her mind however were her very full pouty lips, which despite her age gave her a slightly bratty appearance and a pair of devastatingly bright emerald green eyes which she was sure was also rumored to be fake.
Nothing on Allison however was fake, including her still very firm full breasts and perfectly manicured nails. Allison was the type of woman all men wanted and most women hated, especially when you throw in her six figure salary and position of (as) president of one of the most successful advertising firms in New England.
Hearing the downstairs door open she dropped the mirror into her purse and glanced at her watch; 9:55 he must of driven like a maniac to get here. Jeff came around the corner and had just started up the landing and froze when he saw her leaning there.
As Allison watched two looks crossed his face: the first was an aw shit look, he knew she wouldn't be happy that she was waiting. The second one however she liked even better, it was pure lust. He looked her up and down slowly, she was still wearing the tight low cut red sweater and short black skirt with 4 inch red stiletto heels she had worn to dinner with her middle aged dog of a client, and she had to say Jeff looked much more appreciative than that louse.
"Mistress," he said softly as he came up the stairs "You look amazing."
"Resorting to compliments to mask your tardiness Jeff?" She asked "You should know better than that."
"I'm sorry Mistress! I tried but you said 10." She cocked her head at him.
"When I say 10 my dear boy that means that you should be here before that to properly greet me at your door, which speaking of are you going to let us in or shall I continue to stand here like one of your pathetic little college coeds?"
"Forgive me Mistress I was distracted by your ensemble and forgot myself." Allison rewarded this try with a small smile.
"That was much better than your first attempt, I will give you that, now shall we" Jeff unlocked the door and hit the light as they entered the apartment which was small with the typical mismatched furniture of a college student. Jeff shut the door behind them and approached her.
"May I Mistress?" he asked, leaning slightly towards her, Allison turned her head to the side and allowed him to kiss her cheek.
"Thank you Mistress" He said. She looked at him, Jeff was only slightly taller than her with dirty blond hair and brown eyes, he was usually clean shaved but tonight..
"You're scruffy!" Allison exclaimed rubbing her cheek.
"I'm sorry Mistress, I was in a hurry to get to work tonight." She shrugged.
"Its your loss as I hope you don't think you'll be putting that rough face between my thighs tonight"
"Of course not Mistress" he said putting his head down. Allison thought for a moment, she never planned things just went with what her mood was.
"You know Jeff I've had a very long day, and at the end I thought, you know what would be nice? Having my good looking young man take good care of me and if he did, why then of course in return how could I not be good to him?" She sighed.
"But here you are late, unshaven, having not even asked me what I would like this evening. Maybe I should just go home and play with myself, at least I wouldn't be disappointed that way."
"No Mistress" He said "please give me a second chance tonight."
"And why should I?" She asked enjoying the look on his face. Three weeks ago she had actually walked out on him, then told him that she had gone out and picked up another guy to play with, she hadn't of course but he had believed her.
"Because I have not had the chance to properly please you in some time and I .." He paused and said quietly "I don't want you to have to go elsewhere."
"That would bother you?" She asked
"Why is that?" She asked "You certainly don't believe that this pussy is yours, do you?"
"Of course not my mistress, I am fortunate to have what time you give me."
She nodded, "It's Good that you know that. I will tell you what Jeff, because it is late and I am in sore need of some attention I will give you a second chance tonight"
"Thank you Mistress how may I serve you this evening?"
"Well seeing as how you asked for and received a second chance I think I will leave it up to you to impress me, just know that the second I am bored or disappointed I will leave."
"Thank you Mistress may I leave the room for a moment?"
"You would leave me alone now?" She asked.
"If it pleases you, I would like to prepare a hot shower. You did say you had a long day." Allison paused to consider it.
"That's actually a very good start Jeff, be quick about it."
"Right away Mistress." As he entered the bathroom, Allison kicked her shoes off and removed her watch, tossing it on the coffee table, when Jeff came back she put her hands up over her head.
"Undress me and be sure to keep your hands to yourself while doing so." Jeff came up behind her and grabbing the bottom of her sweater gently pulled it up over her head. He then unhooked her bra and slid the straps off her shoulders, he was careful not to touch her tits with the sides of his hands as he slid it off her arms. "Good boy." She said softly.
Reaching up, Allison removed the clip from her hair and allowed her raven black hair to fall down across the porcelain skin of her back. Jeff got down to his knees and unzipped her skirt letting it fall to her feet. Allison was wearing a black lace thong and she heard Jeff take a breath as he got a look at her ass right in front of his face. The green Cat eye's tattooed on the small of her back were level with his own wide eyes.
"Do you like looking into my pretty green eyes Jeff?"
"Oh yes." He breathed. Jeff put his hands up to remove her thong.
"I'll take that off thank you." She said and hooking her fingers through the sides. She slowly slid the thong off, bending over in Jeff's face in the process. From this angle her pussy was inches from his nose.
Allison stood up and turned around so that he could see her pussy from the front now. She loved the look of absolute desire on his face as he took in her body. He was still fully clothed and it turned her on to be totally naked in front of him. His eyes wandered up from her pussy to her large firm tits with their light pink nipples, the silver barbel in her naval gleamed as it caught the light of the lamp.
"Do you like my body Jeff?"
"My Mistress is perfect in every way." He whispered his eyes glazed over with lust. She could sense him struggling to not reach out and touch her.
"I am aren't I? Far better than that skinny girlfriend of yours."
"Far better." He agreed
And far better than you deserve."
"That goes without saying Mistress."
"Good answer, shall we go to the shower?" She asked as she turned and walked to the bathroom knowing he was following close behind, unable to take his eyes off her. They entered the bathroom which had filled up completely with steam.
"Fix the water please." She told him and waited while he adjusted the temperature, the hot air was making her sweat and also was making her a little drowsy.
"The water's perfect my Mistress" He pronounced.
"We'll see." She said and stepped in as he held the curtain aside for her. He was right the water was just fine.
"May I wash you my Mistress?" He asked; she nodded
"Yes. As long as you wash and do not fondle" Jeff stripped down to his boxers, when he went to remove those Allison spoke.
"Leave those on I do not want your cock touching me in the shower. After all it is for my benefit not yours."
"Yes Mistress." Jeff entered the shower behind her and grabbing a bottle off the shelf, poured some into the soft sponge he had picked up and began slowly rubbing it across her shoulders and back, Allison smelled Raspberry.
"That smells nice Jeff."
"Thank you Mistress its my favorite on you." Allison leaned backwards into him and he reached around and began washing her stomach slowly making his way up to her tits. He paused with one hand just under her right tit.
"May I Mistress?"
"Yes but just to wash." Jeff gently lifted her tit with his hand so he could wash underneath, as he did Allison put her arm up behind her and behind his head leaning her head against his. She actually liked the scruff but why tell him that. He switched to her left and she lifted that arm and went to the other side.
"This is really nice Jeff!" She cooed happily and gave him a small kiss on the neck.
"Thank you." He replied with a small smile and dropping to his knees began going up and down her legs.
"Hold on." She said and turning to face him put her right foot up on his shoulder. After washing the top of her foot he continued up her leg, his eyes were fixated on her pussy. Allison switched legs, when he finished, he hesitated.
"Go ahead." Allison said softly as she spoke she reached down and spread herself open. Jeff gently rubbed the sponge up and down across her slit which was wet from more than just the shower. Allison let him do it several times, it felt incredible, but she wasn't ready to cum just yet.
"Enough." She told him. Jeff stood up and took a bottle of shampoo from the shelf.
"May I wash your hair Mistress?"
"Yes. I would like that." Jeff took his time lathering her hair running his fingers through it massaging her scalp. He was doing an excellent job tonight she had to admit. When he had rinsed her hair Allison turned to face him.
"Now wash yourself my dear, you smell like food."
"Of course Mistress." He began soaping himself up as Allison watched she resisted the urge to do it for him. Rub his shoulders and chest feel his muscles beneath his skin, Jeff was not a large man but he worked out and his young body was lean and hard, which speaking of hard.
"You may remove your shorts now and clean yourself." Jeff stripped than began washing himself, his cock was standing at full attention.
"Stroke your cock for me." She whispered he began sliding his soapy hand up and down the length of his shaft. It looked incredible, after a moment she stopped him.
"That's enough. I wouldn't want you wasting it in the shower, now turn off the water please." Jeff obeyed then stepping out of the shower held up a towel.
"May I?" Allison stepped out and turned her back to him he began to dry her off.
"Easy!" She snapped "You do not rub me dry like a dog you pat me dry gently."
"I'm sorry my Mistress" He began to pat her softly.
"That's better. Remember, I am much softer than you." Jeff finished, then quickly dried himself.
"May I take you to my bed Mistress?"
"You've been good so far, so yes." She began to walk out in front of him but he stopped her.
"Mistress you should not have to walk across the floor after you have just been cleaned."
"You do have a point there, and what would you do about it?" She asked
"May I?" She nodded. Putting his left arm around her waist he bent down put his other arm under her knees and effortlessly lifted her up and carried her into his bedroom.
"Oooh" She cooed "This is a very nice touch Jeff." She turned her head into his chest and began tonguing his nipple. She could feel him shudder.
"Thank you Mistress" He breathed. He turned sideways to get through his door then gently laid her on his bed.
"Would my Mistress like to roll over so that I may rub her back?"
"I'll allow it." She said rolling over onto her stomach. Jeff took a moment to light a couple of candles then grabbed a tube of lotion from the nightstand. For the next twenty minutes Jeff massaged her from the bottom of her feet up to her neck, his hands were strong and firm and he was taking his time. Allison lied there thinking she should be pampered like this everyday. It felt so good she could have fallen asleep, well almost, she was also getting quite wet.
"I'd like to roll over now." She said softly he moved to the side and she lazily rolled onto her back and smiled at him.
"You are being a very good boy tonight Jeff I'm glad I gave you a chance." As she spoke Allison stretched out watching as his eyes devoured her lush body.
"Thank you." He was positively beaming at this point.
"How do my tits look Jeff" She asked stretching her arms over her head, Allison had very pale pink nipples which on her alabaster skin were almost invisible, she knew Jeff loved them.
"Lean over and tongue them, just a minute each." Jeff eagerly leaned over and obeyed, Allison watched his tongue flicking over her nipples and began breathing heavier.
"Okay stop," She paused then asked smiling sweetly at him, "Do you have my favorite toy?" Jeff leaned over to the nightstand and removed a silver bullet vibrator from the drawer. Allison put her hand out and he handed her the remote. Slowly spreading her legs and loving the look on his face as she exposed her pussy to him she reached down and opened herself.
"Kneel between my legs!" As he did he took the vibrator and placed it on her clit. Allison switched it on low, she did not want to cum quickly.
"Now place the tip of your cock at my pussy, do not put it in." Jeff obeyed Allison could feel him throbbing right at the edge of her pussy. She raised her legs and put her feet on his chest.
"Now ease in an inch." She said, he did and groaned quietly. She turned the control a bit more.
"A little deeper." Once again he eased in a little more she could feel him twitching inside of her. She clenched her muscles around his cock he moaned.
"Your little girlfriends can't do that can they?"
"No mistress." He breathed
"All the way in slowly." Very deliberately he pushed himself all the way, an inch at a time. He was not large but my god was he hard, Allison thought.
"Back out just as slow." She turned the vibrator a bit more.
"Now give me three hard pumps." She whispered then "Oh yes!" She breathed as he slammed her three times then stopped.
"Mmmm," She groaned. "You like that don't you?"
"Of course Mistress, its a privilege to feel your pussy."
"That(')s right and the best part is how nice and soft I am. Not at all like those bony skanks you fuck sometimes."
"Their young girls Mistress, you're an amazing woman."
"That's a very good answer Jeff as a matter of fact you've been very good tonight I think there may be a reward for you if you make me cum nice and hard"
"Your cumming will be my reward Mistress." Damn, Allison thought, he is on tonight.
"That's right, it is, isn't it? Now put it all the way in." He did.
"That's right. Push that vibrator into my clit. Oh yes," She moaned as she turned the bullet all the way up.
"In and out but slow," Jeff began gently pumping her pulling his cock out only about halfway each stroke. Every time he pushed in he would grind the bullet into her clit. Jeff actually had a good rhythm going and Allison licked her fingers and began playing with her nipples. Once again the look on his face was as much fun as actually doing it.
"Oh that's sooo nice" She whispered as she got closer, she pushed her feet against his chest, loving the way her bright red toes looked on his tanned chest and how it forced him to strain to stay inside of her Allison could see the muscles in his arms bulge.