As Cassandra got off the elevator at her penthouse apartment that over looked Lake Michigan she groaned a little as the strain of the day overtook her. It had been a long one, with meetings with clients starting at eight in the morning all the way to five p.m. in the afternoon, being a senior partner at one of Chicago's major law firms could at times be challenging, but most often grueling. She was about to put her key into the dead bolt lock on her door, when as if by magic it swung open and she was greeted by a pale thin young blonde boy of nineteen, who stood in front of her naked except for pair of pink silk panties. "Oh, Mistress," he gushed, "I am so glad that you're home, I missed you so much today." She stepped inside the door and while giving him a kiss on the cheek, stuck her free hand inside of his panties and asked, "Did you get everything done that I asked you to?!?" As his organ swelled in her hand, he replied excitedly, "Oh yes, I went to the market and ordered the groceries, I made an appointment for you at the beauty parlor for Saturday, and of course I shave all of my body hair, is it smooth enough for you," he asked hopefully? "We'll see," she replied a little gruffly, "now hurry up and get me a drink, I'm dead tired."
Timmy wasted no time in going over to the bar and fixing Cassandra her usual, a scotch and water! She drained half of the drink in one long swallow before returning her attention to the young boy waiting patiently at her side! She eyed his smooth pale form and felt the familiar stirring inside of her panties, how she loved his sweet warm flesh. "Show me your penis, boy," she ordered while taking a sip on her drink." "Yes, Mistress," he replied excitedly, as he quickly shoved the pink panties over his hips and down to the floor. His small penis standing fully erect and pointing straight at her, made her pussy drench itself with a flood of hot cunt juice. "You look so tense Mistress," he offered, "would you like for me to suck your vagina for you?" "Yeah," she replied, "that's a very good idea, would like to suck it for me right now?" "Oh, yes," he said enthusiastically, "I've been thinking about it all day, and hoped you'd be in the mood for it." "Well, you're in luck," she replied, "now get under my dress and suck me off." Timmy quickly scrambled to the floor, disappeared under Cassandra's dress, and immediately went straight for her dripping wet cunt. For a sixty year old, Cassandra had a massive sex drive that required at least two sessions a day to keep her from climbing the walls, and that's why it was so important that she always have a very young lover to take care of her sexual needs, as an older man would have never been able to keep up with her frenetic pace.
With her legs spread wide giving the young lad plenty of room to access her big lipped pussy, she drained the rest of her drink and just leaned back and enjoyed the cunt lapping that little Timmy was performing so admirably. "Oh, yes, panty boy," she sighed, "take good care of your Mistress' pussy, oh, my, that's it, do my clit, oh, oh, oh, right there, ooooooooh yeah." For such a young man Timmy was remarkably adept at oral servitude, and since that was one of Cassandra's favorite pastimes, he spent a great deal of his time with his mouth pressed hard against her hairy muffy. "She wasn't sure why someone her age required such a huge amount of gratification, but she once had read that people like her, the ones that were very career oriented and driven to succeed, probably used sex as one of their few natural outlets to relieve stress from the crushing responsibilities that ruled their daily lives. "Whatever the reason, for as long as she could remember sex wasn't very far from her mind. It was a constant battle between her brain and her clit over who controlled her body. Most of the time her brain prevailed, but several times a day, the power between the folds of her vagina took over her being and literally forced her to seek relief.
Timmy's tongue now working the head of her clit, was whipping her pussy into a blinding fury, that quickly was approaching the critical mass needed to bring her to climax. "I'm very close," little boy," she panted, "do my clit hard, now, that's it, do it for your Mistress." He just loved bringing her to orgasm, just the knowledge that he could make her so happy was enough to give him an incredibly hard cock. All at once all of the muscles in her cunt contracted at the same time, as the blood rushed to engorge her genitals in a massive orgasm that she thought might stop her heart. After a few moments in which she regained her senses, she gently pulled Timmy out from under her skirt and asked softly, "Did you enjoy sucking my pussy, boy?" With his face still shiny from her juices, he replied with a smile, "Oh yes, Mistress, you taste so sweet to me." Taking his rock hard pecker into her hand, she continued with another question, "Tell, boy, did you masturbate today?" With the color rising in his cheeks and hi head down, he answered softly, "I-I didn't want to, Mistress, but I couldn't help myself, I'm sorry, it won't happen again." "Timmy, Timmy, Timmy," she said in rebuke, "how many times have I told you never to touch yourself unless I give you permission?!?" "I don't know," he said sadly, "but quite a few I guess." With her hand now rapidly jerking his little four inch erection she scolded, "What am I going to do wit you, boy, you ignore my orders and make me sorry I brought you into my house." Tears now filled his eyes as he realized how disappointed she was in him, and he said in almost a wail, "P-please don't make me leave, Mistress, I'll try to do better, honest I will, please give me another chance." Cassandra could feel Timmy's nut bag tightening, which of course was a precursor to his ejaculation, so as she usually did, she leaned over and took the little member into her warm mouth and let the young boy fill her mouth with his sperm. For such a slightly built young man he had an unusually large amount of ejaculate, and Cassandra had a hard time swallowing all of it, as some of it trickled out of the corners of her mouth. "Now that is how you are supposed to do it," she said with a reprimand in her voice, "Mistress always gets to drink her panty boy's sperm, is that understood?" "Yes, Mistress," he said with a smile, sensing that she was over her anger." "All right now," she went on, "scoot into the bathroom and draw me a hot bath, I'll be in shortly, and remember, keep your hands off your penis."
Timmy helped Cassandra remove her robe before helping her climb into the giant four person whirl pool spa! "Oh man, that feels so good," she sighed while lying down and letting the hot water soothe her tired bones, while Timmy stood expectantly next to the tub, praying that his Mistress would allow him to join her in the hot bubbling water. Deciding to make him wait a bit, Cassandra asked casually while cupping her huge fat boobs, "so tell me panty boy, what were you thinking about when you masturbated today?" Again with the red rising in his face he replied softly, "You, ma'am, I was thinking about........." "Come on," she interrupted, "tell me boy, what was it?" "Uh, I was thinking about your bottom, ma'am." "So, you were thinking about my fat ass, huh," she rejoined?!?" "Yes, Mistress," he said in a small voice! "So," she spat, "you think my ass is fat do you?" "Oh no," he said in a pleading voice, "I-I didn't mean that, I just meant that......" "Oh shut up," she said coldly, "now I can see what you think of me, just as a fat old broad who you have to fuck once in awhile in trade for a nice place to stay." Tears began forming in his eyes, and seconds later he was crying like a two year old. "What are you crying about," she snapped?" "I-I love you, Mistress," he sobbed, "h-how could you think those bad things about me, look at my penis, isn't it always hard for you, I-I could never keep it up for someone I didn't care for." She looked at him with a frown on her face that slowly changed to a smile and replied softly, "Okay, little panty boy, come in here and suck on my tits for her."
Almost joyously he leaped into the spa, while urgently searching out one of Cassandra's big hard nipples. "Whoa, little boy," she said gently, "take it easy, that's a good panty boy, mmmmmm, good boy, suck my nipple for me." Since she was a big woman, and out weighed him by at least sixty pounds, he looked like a rag doll as she cradled him to her chest and nursed him like a baby. "You do such a good job of sucking your Mistress," she cooed to him softly, "now mama needs something else from her little panty boy?!?" He lifted his mouth from her nipple and said, "Anything Mistress, I am here to serve you." "That's a good little boy," she replied, my legs are spread for her panty boy's little cock, will you please fuck me now, little boy?" Sliding over her wet body with ease, his little erection quickly found her opening and easily entered her big hairy muff. "Oh, little panty boy," she said with a sigh, "you have such a nice little penis, and mama is so glad she has a little boy like you to fuck her when she needs it, and she needs it every day." Resting his cheek in the valley between her breasts, his little ass pounded his pecker in and out of the large lips that guarded the entrance to her luscious pussy. "Are you close to shooting your sperm," she whispered in his ear?!?" "O-oh, yes," he panted, "I-I'm almost there, I'm sorry, but I can't hold it back, I'm so excited I can't help myself." Normally she might have reprimanded him for cumming too quickly, but tonight, she was happy to let him have his climax in a more out of control way! "Oh, oh, I'm cumming, Mistress," he moaned while plunging in and out of her at a frightening speed. "That's good little panty boy," she said while caressing his cheek, "cum in my vagina, fill my pussy with your sperm, little boy." "H-here it cums," he moaned, "I'm giving you all of my sperm, it's my gift to my Mistress, ohhhhhhhhhh, god, I'm shooting it nowwwwwwwwwwww." Even though she wasn't even trying to cum, just hearing her little panty boy getting so excited had caused her vagina to involuntarily spasm and wrench another orgasm from her now very alert little clitoris.
"Oh, Mistress," he sighed while nestling against her breasts, "I love you so much, I hope I have pleased you." Guiding one of her nipples back into his mouth she replied softly, "You have pleased me greatly little panty boy, now suck my nipple and take a nap."
"Timmy, dear" Cassandra said while reading morning paper at the breakfast table, "I have a convention in New Orleans and I'm leaving right after work for the airport, so I'll have the cabby swing by here and pick up my bags." "I've laid out all the clothes I'm going to need, but I want you to get them all packed and ready to go, understand?" "How long are you going to be gone," the crest fallen young man asked sadly?!? "Five days for sure," she replied while trying to keep from laughing, "why do you ask?!?" "Oh," he replied disappointedly, "it's just that I'm going to miss you, that's all." "Why will you miss me," she asked teasingly? "Well, if you're going to be gone for five days...............," he replied while letting his voice trail off. Cassandra lowered the paper, looked into his sad eyes, and then slid two round trip airline tickets across the table at him and said, "I don't know why, because you're coming with me." The look of shear joy on her panty boy's face was enough to break her heart, so she didn't even protest when he raced around the table and gave her a big hug and kiss and exclaimed, "Oh, Mistress, I so happy, thank you for taking me." She chuckled a bit, and then in her stern mistress voice ordered, "Well," you just make sure you've got everything packed an ready to go by five o'clock, got it?"
When they were finally situated in their first class seat on the plane, Timmy leaned over to Cassandra and whispered, "I'm wearing something special just for the occasion, I hope you will approve." Cassandra arched her brow a bit and asked softly, "I'm very intrigued, what is it, tell me right now." Lowering his voice even more he said, "I went shopping on Oak Street today, at that new lingerie shop, and I picked up a pair of while lace crotchless panties." He then added, "When I get an erection it sticks right out of the front, I can't wait to show you." Cassandra moaned softly to herself while picturing Timmy's little hardon poking out from the feminine under garment, and naturally, she immediately became quite wet. Now in a hoarse voice she asked, "You didn't masturbate did you, you know what will happen if you did?" "Oh no," he replied quickly, "I got hard cuz of the silk, I promise you I didn't jerk it at all." "She looked into his innocent eyes and said softly, "When we get to our room, the first thing you're going to do is suck my vagina, you've got me just dripping." A broad grin spread across his face and he answered, "Oh thank you, Mistress, I can hardly wait."
The bell captain placed their bags next to the queen sized bed, thanked Cassandra for his five dollar tip, and closed the door on his way out. Once they were alone, she ordered, "Okay, panty boy, take off your clothes except for your new panties." "Yes, Mistress," he replied, while quickly shucking everything but the tiny silk panties that clung to his cute little ass. "Very nice," she said under her breath, "your penis looks darling sticking out of the opening, now, come over here and help me with my things." With both of them helping, Cassandra soon stood naked next to her little panty boy servant, and as was usually her habit, she took him into her arms and gave him a crushing kiss on the mouth while feeling him up all over. Her huge breasts were just about at his mouth level, so she easily fed a hard nipple into his mouth while her hand slipped between them and she softly fisted his tiny pecker. "Hmmmmmmm," she hummed, "you know just how to take care of your Mistress, don't you panty boy?!?" "Oh, yes," he replied softly, "and it's a privilege and an honor to take care of my Mistress's needs." "Remember what I said on the plane," she asked softly? "Of course I do, Mistress," he responded, "would Madame care to have her vagina tongued?" "Jesus this nineteen year old kid was good," she said to herself, while leading him over to the bed and spreading her legs, "so very fucking good."
After having lived with Cassandra for six months now, and knowing every nook and cranny of her smooth shaven cunt, Timmy spent the first ten minutes or so just licking and sucking her outer lips. Although he hadn't had much experience with other women, he was sure that his Mistress had vaginal lips that bulged out much much farther than on a normal woman, and he absolutely loved seeing her pussy encased in expensive panties that showed he vulva bulging plumply through the shiny thin material. He really couldn't help himself, and although he loved his Mistress dearly, he was also having a very real love affair with the lips of her vagina, so consequently, he would spend a great deal of time making sure that they were thoroughly washed with his devoted tongue. "Oh, Timmy," she moaned, "you love mama's vagina don't you, dear?!?" "Oh yes, Mistress," he said between pants, "especially your lovely vulva, I love it so." "I know you do, dear," she said with a sigh, "but mama needs to have her clitty taken care of now, so be a good little panty boy and suck mama's clit for her, please?" Sorry to have to give up sucking her lips, he took his fingers and gently pulled them apart, exposing her very erect little clit to his still hungry mouth.
"Oh, Mistress," he whispered, "your clitoris is all hard and erect, I think it needs some attention." "Mmmmmm," she hummed, "suck mama's clit like a good little boy, make her have a nice hard orgasm, okay?" And of course he did, taking her little member directly between his lips, he flicked the tiny head with his tongue until her whole body was awash in a soothing climax that swept away the days tensions and frustrations right out of her. "Was it good for you Mistress," he asked hopefully?!? While caressing his cheek with her hand, she smiled at him and sighed, "It was very good, Timmy, you sucked mama's vagina just the way she likes it, and she is very proud of her little panty boy." "Oh thank you, Mistress," he replied happily, "I so want to make you happy," while he snuggling his face against her wet vulva. "So tired," she mumbled, and the two of them fell off in fitful sleeps, she lying there with her legs spread wide, and him with his cheek nestled up against her very distended cunt.
Two hours later a knock on the door roused the two sleeping lovers, and a voice on the other side yelled, "Hey, Cass, it's me, Emily, is anybody in there?" Cassandra woke Timmy up and ordered, "A friend of mine is at the door, answer it and let her in, please." "Yes, Mistress," he replied while putting on his trousers, "right away." "Timmy," she said sternly, "did I tell you to put on your pants, leave them off and answer the door in your panties, right now." A very embarrassed Timmy mumbled, "Yes, Mistress," as he walked over and opened up the door. "Come in please," he said courteously, "Mistress is right over there." Emily swept into the room, and after giving Timmy the once over offered loudly, "My god, Cass, he's fucking adorable, where in the hell did you find him?" "Thanks, Ems," Cassandra replied, "in Chicago, I've had him for six months or so, and he seems to be working just fine." Emily looked back at the now red cheeked Timmy and went on, "And such a pretty pair of panties that let his little erection poke through, how very nice, and by the way, how's his mouth?" "That's the best part," she replied quickly, "just look at my vagina, licked clean as a whistle."
"Uh, Cass," Emily asked slowly, do you think I could, you know?" "Do what, Emily," Cassandra casually, "you have to be a little more specific in your request, after all, I'm not a mind reader?" "Well," Emily replied softly, "he is erect, and I haven't sucked a pretty little cock like that in years, so if you don't mind..........?!?" "Timmy," Cassandra said sharply, "I want you to let Miss Emily suck your penis, it's okay, I'm allowing it, so if she wants you to ejaculate in her mouth, you can go right ahead." "Y-yes Mistress," he stammered, as this was a totally new experience for him. Mistress had never allowed anyone other than herself to use him sexually since he had moved in with her, and to say that he was nervous would be an understatement. He padded over to Emily, who had since sat down on the floor, and stood quietly in front of her as she opened her mouth and sucked in his cute little erection. Cassandra watched with bemused fascination while her little panty boy stood there and allowed a perfect stranger to suck his hard little penis. "Timmy," she asked, "is Emily a good cocksucker?" "V-very good, Mistress," he gasped as she had his whole member all the way inside of her hungry mouth. Now deciding to have a little fun with him she asked, "Is she as good as I am?" "Oh, Mistress," he moaned "I-I don't know, she's different, but very good." "Oh, I see," Cassandra replied, "how is she different?" "I don't know," he said with a moan, "s-she just is, ohhhhhhhhhhhhhhh, I'm cumming in her mouth." And he did too, a spurting load of hot cum jettisoned from the end of his tiny dick and filled Emily's mouth with hot burning cum.
"So, Ems," Cassandra asked, "how was my little panty boy, did he come nice and hard for you?" Without directly answering the question Emily asked, "Didn't you say he was good at sucking cunt," as she slipped off her panties? Cassandra just rolled her eyes and said, "You're going to be a very busy boy for the next five days, Timmy, a very busy boy.
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