I've worked for many years at a small college in the Midwest, working my way up to a position of prestige in the Office of Giving. It's my job to travel around the country squeezing money from the rich and famous. I'm away from home a lot, so I haven't formed too many attachments. In spite of that, rubbing elbows with captains of industry does have its perks. While my employer may not like my methods, they appreciate the results. I get to host cocktail parties in some very interesting places and meet some very interesting people.
One example occurred last January in Syracuse, New York. I had been working the crowd when I caught a glimpse of a full figured woman in a jade green and gold sequined dress. She seemed to be doing the same thing I was, but with a little more success. I had to go looking for people, she attracted them.
When I got close enough, I asked my assistant, who she was. Jamie had no idea, so I continued to watch, fascinated, almost hypnotized by her presence. Her eyes met mine. She smiled. I smiled back, unblinking, undressing her with my eyes.
Starting with the top of her head, I took her all in. All five foot ten of her. Her shoulder length, auburn mane framed a pretty round face. Her green eyes glowed as she returned my stare. Was she undressing me as I was her? The inner halves of her collarbones moved gently as she breathed. Her ample bust, squeezed together, invited, almost dared you to stare down at the swell of her breasts. She was a large, but well proportioned woman, who, by her stature, was very self assured.
As my eyes peeled off her dress, my mind saw two large, proud mounds, jutting from her chest, crowned with large, dusty rose colored areola's, topped with gum drop sized nipples. Below was a well defined waist, soft hips, and a dark red triangle of hair, hiding her treasures. From there down, ample, but shapely legs ended in green high heels.
Snapping out of my dream state, I walked up and introduced myself, commenting on what a stunning dress she was wearing. "Hi, I'm Kathleen MacNamee. It's a pleasure to meet you." she said, adding, "Do you always stare at women like that?"
Somewhat taken aback, both at my behavior and her directness, I recovered quickly. "Only when they are as mesmerizing as you."
"Flirt!" she retorted, laughing. I spent as much of the rest of the evening with her as I could, leaving to talk to potential donors, but always drawn back to her. At one point, as I was approaching, I overheard her rejecting the advances of some rich and powerful man looking to take her to bed. "I'm terribly sorry, but I have a prior engagement." she said, as he pressed her for an answer.
We engaged in a lot of small talk, and, from what I gathered, she too had money to 'invest' in a college, but hadn't found the right one yet.
"So what can I do to get you to fund an endowment?" I asked, staring down the cleavage of that magnificent chest.
"That would depend on how good you are at begging!" she replied with a wicked smile. "Why don't we blow this pop stand, and discuss it, say, at my place?"
"But I thought you had a prior engagement."
"I do!. You! Unless, of course you're not interested."
"I'm definitely interested! But, why me?" I asked.
"The last time you were in town for a fundraiser, you took my friend Moira to bed. She raved about you, and I wanted to find out just how good you were!"
A look of surprise spread over my face. "You know Moira Sanford?" My mind instantly wandered back to the last fundraiser I held here, and the vivacious blonde that, literally, kept me 'up' all night.
"Yes, I do!" she answered back, with that wicked grin on her face. "You might say, intimately." She leaned in and whispered her address to me and slowly made her way to the door.
I spent a few more minutes schmoozing the crowd and excused myself and made my way to her home.
I knocked once. She swung open the door, pulled me inside and kicked the door closed as she wrapped her hands around my head and kissed me, passionately. Our tongues fenced for a few seconds before she took my lower lip into her mouth and gently bit it, grabbing two handfuls of my hair. My hands roamed up and down her back as my tongue swirled inside her lips and across her teeth.
She pulled away slightly, still holding my lip firmly but gently in her teeth. Staring me directly in the eyes, she said, "There are a few rules you need to know before we get started."
I arched my eyebrows quizzically in answer to her statement. She continued, "You will address me as Mistress Kathleen at all times! You will ALWAYS answer my requests in the affirmative. You will do EVERYTHING I tell you, EXACTLY as I tell you. Is that understood?"
"Yes!" I said.
She bit down firmly, without drawing blood, but getting my attention. "Yes Mistress Kathleen!"
"Yes Mistress Kathleen!" I replied.
Letting go of my lip, she stood back, eyeing me up and down. "If you disobey me, you will be punished. Obedience, on the other hand will have its rewards." she said brushing her hand against my crotch.
"Yes Mistress Kathleen."
"Good! Now help me out of this snakeskin." she ordered, turning her back to me.
I went to unzip the back. "Unh Unh! No hands!"
"Yes Mistress Kathleen" I said again, leaning into her back, gripping the zipper with my teeth. I pulled downward, past her shoulders, to the small of her back where I lost the zipper. Trying to retrieve it took some doing but finally, I had the zipper back in my teeth and pulled it past her ample but shapely rump. By the time I was done, I was on my knees. The dress fell to the floor. She turned and stepped out of it. There, standing before me was a voluptuous, full figured redhead clothed only in a green bra with sheer cups, matching boy short panties with a sheer panel in front, a garter belt, sheer green stockings and green high heel pumps. My cock twitched as I took it all in!
She reached down and grabbed my tie. Using it like a leash she began walking to her bedroom. I started to rise. "No, my pet!. Stay on your hands and knees until I tell you otherwise."
I must have hesitated too long before answering, because she yanked the tie and swatted me on the ass. "Come, my pet! You need to get undressed too!" She turned and headed for the bedroom door. I followed, scurrying to keep up , staring at her undulating rump, and thinking all sorts of evil thoughts about what I would like to do to it! We stopped by her bed and she dropped my tie. "Take off your clothes!" she ordered. I swiftly complied. First the tie, the shirt, and the tee shirt, followed by the shoes, socks and the pants. It was a little awkward at first, trying to disrobe while on your hands and knees, but I managed. Then, as I sat on my haunches, not unlike a loyal dog, she produced a leather collar with a lead. Leaning over to put it on me, I got a perfect view down her cleavage! My cock twitched again. She slapped my naked ass as she said, "You naughty boy! Didn't your mother teach you to look away from temptation?"
I answered in the affirmative. She swatted my ass again, twice, harder this time. "That's for disobeying your mother!" she said, "and this is for paying me a compliment by staring at my breasts!"
I cringed, waiting for another hit or two, but was rewarded by her unsnapping her bra and freeing those proud orbs from their green prison. "You like these, don't you, my pet."
Again, I agreed, unable to take my eyes off them. They were pretty much as I imagined, large, round, firm but soft, large areolas capped by the most inviting nipples. "If you're a good boy, I might let you kiss them! But not yet! I want you to stroke your cock while you watch me undress. But don't you dare cum!."
So I sat and watched as she unsnapped the garter belt, tossing it aside. Flexing her left leg, she began to roll her stocking down, past the knee, over her calf and off her foot. Repeating the process, she then stood, clad only in her panties. Moving toward me, she stood with her crotch at face level. "Take them off!" she ordered, "but no hands!"
I grabbed the waistband with my teeth and pulled her panties off exposing a heart shaped bush pointing down to her meaty camel-toed pussy, already glistening with her juices. I breathed deeply, taking in a mixture of perfume and musk. Continuing to pull the panties down to her knees and beyond, I let them drop to the floor. Looking up, first at her luscious cunt, her belly, her breasts, my gaze finally rested on her face. She smiled down at me. "Nicely done, my pet. Do you wish to taste me?"
My eyes brightened. "Oh yes, Mistress Kathleen."
"You will! Soon! Now stand up. I wish to inspect your equipment."
I immediately stood as she lowered herself to the floor. The rose colored head of my cock was almost at eye level. She grabbed the shaft and squeezed. A drop of pre-cum formed at the slit. Her tongue swirled around it, scooping up the little gift, and moaning. She squeezed again, repeating the process, only this time surrounding the crown with her lips. Pulling off with an audible 'plop' she smiled, licked her luscious pouty lips and asked, "Do you want to cum in my mouth? Or in my cunt?"
"Both, Mistress Kathleen."
"Good answer!" she said just before sliding her lips around the shaft, engulfing more than half of me. I could feel my cockhead brush the back of her throat, as she slid up and down
my length, cupping my balls in her left hand as she stroked me with her right.
I struggled not to grab her head and force more of me in her mouth, swaying my hips, watching intently as my spit slickened manhood churned in her face. She pulled off again, telling me how good it felt to have a cock in her mouth. Still frigging me she lowered her face to my balls and after licking each one thoroughly, took my left testicle into her mouth and sucked. Rolling her tongue around the delicate orb, she gently pulled, stretching the sac before letting it loose and caressing the other one in like fashion.
Another groan escaped my lips as she licked her way up the shaft, re-swallowing the head. My brain was on overload and I was dangerously close to cumming. "Gonna cum soon, Mistress!" I croaked, while humping her round, pretty face.
Pulling her mouth off my stiff prick, she said, "Good! I want to taste you!" Laying my cock on her tongue, she stared into my eyes as she stroked me with her left hand while scratching the skin behind my nuts with her right. "Cum for me now, my pet!"
I grunted loudly as I felt her finger invade my ass. I felt my sperm travel up my cockshaft. Forcing my eyes to stay open, I watched as it spurted across her tongue as she milked it with her hand. When she had coaxed all of the warm fluid from my cock, she kissed the head, smiled and stood up.
She grabbed my head and planted a wet, spermy kiss on my lips, forcing them open with her tongue. As my own essence flowed back into my mouth, I responded in kind and we spent the next minute swapping my seed, smearing it all over our lips.
In the throes of our passionate kiss, I had let her turn us around. She gently , but firmly pushed me backward onto the bed, climbed on top and positioned her freshening pussy directly over my face. "Eat me!" she said as she lowered herself.
My response was muffled by the soft, warm lips of her pussy as it settled onto my nose and mouth. The bridge of my nose rubbed against her now prominent clit as my cum coated tongue sliced upward into the cleft of her pussy. Rolling her hips, she wiped her musky cream all over, rocking and moaning as I tongue fucked her. She was careful not to cut off my ability to breathe, but restricted the movement of my head as I continued to assault her velvet smooth cunt.
I was able to reach around her thighs and caress her clit as I continued stabbing my tongue into the soft folds of her sex. I could feel as much as hear her coo as she moved ever closer to an orgasm. I felt one hand close over my cock and the other grabbing my hair as she steadied herself, riding my face.
"Oh! God! Yes! Yes!." she screamed as her cunt poured its contents over my lips and tongue. Her legs quivered as the orgasm racked her body. I didn't stop flicking her clit and she continued to writhe until she couldn't take any more and slid off, laying beside me panting and clutching her pussy. "Jesus! That was incredible!" she gasped, quickly recovering. Looking up at me with a smile on her face, she said, "Well. Are you going to fuck me or not?"
I did not answer her in the affirmative. I rolled her onto her stomach, grabbed her hips, pulled her ample apple-shaped ass into the air and effortlessly entered her sopping pussy. I thought momentarily of entering her slowly, drawing out the sweet agony for both of us. My animal instincts won out and I slammed into her velvet cunt, making her breasts jiggle and sway each time my hips and balls came in contact. She started rolling her ass with each jarring thrust, grunting her pleasure at my assault. I leaned over biting her shoulder, cupping her pendulous breasts, kneading them as I sawed in and out, in and out, slapping her ass with my hips. She grabbed my left hand, tearing it from her nipple and pushing it down to her soaking crotch. "Make me cum again! Please?" she pleaded.
I strummed her clit with all four fingers, grunting with pleasure and exertion as we fucked like dogs in heat. She began to tense again, babbling almost incoherently as she approached yet another orgasm. Wanting to feel her clasping cunt milking me again, I kept slamming, pinching and strumming. She buried her face in the pillow and started to scream as her pussy let loose a torrent of musk, soaking the sheets. Her clutching pussy drove me to the edge and I howled as my cock exploded deep inside her.
She collapsed, trapping my hand on her breast, my fingers on her clit, and my cock sliding slowly out of her as it shrank. We lay there intertwined for several minutes before she let me loose, except for the hand on her breast. She curled up holding me tight to her.
"Get a good nights sleep." she whispered, "Your going to need all your strength for tomorrow! And the size of my donation will depend on your behavior and performance."
“Yes Mistress Kathleen.”
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