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What’s The Deal With Secretaries?

Category: Anal Sex
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Sure, go ahead and call me a square. But I’ll bet I make more money than you do. Besides, being an accountant isn’t all that bad. It’s just like taking the class in high school over and over again; you start to know what’s coming, and it gets easier all the time! Same shit, different day.

But this time I didn’t see or know what was coming. My secretary got sacked after her third DUI.

You’d never know she was a drinking lady just looking at her: 66 years old, with that sweet-ol’-grandma look that all us momma’s boys love. I made ends meet, covering the little jobs she usually did until the end of the week. Then on Monday her replacement showed up.

Her name was Pam. She was an immediately striking woman, put mildly. Her dirty-blonde hair was pulled back in a stylish and professional ponytail, which nicely accentuated her perfectly made-up eyes, lips, and lashes. Her skin was light, with many freckles, and was just slightly and naturally tanned. The straps of her short, cream-colored dress belied the thin tan-lines from her bikini. Her tits had to have been healthy D-cups, and judging by the way the hung they were 100% real-deal, and still pert and firm. Her bubble butt ass and awesome hips finished out her perfect, smooth hourglass figure, just the way I loved my women; gotta have something to grab onto, and this 5’5” beauty fit the bill perfectly.

But her last amenity should have been illegal: she wore heels that matched her dress, and a set of black, small-holed fishnet stockings. The holes stretched slightly at her calves and thighs, and I could only imagine what they looked like stretched over her ass under that short dress she wore. I had to fight to hide my massive hard-on at every moment!

She introduced herself to me when she came in that morning and got right to work; on both my papers and my sexual restraint. Whether she knew it or not I couldn’t tell at the time. She teased me all day; leaning way over the desk and showing me her cleavage, picking up things she dropped on the floor without bending her knees, and sitting with her legs side-by-side instead of crossed, so I could see her hot little panty-clad vee under her dress. Things reached a boiling point when she bent over to get in a file cabinet and the dress, stretched tight across her ass, lost its grip and rode up so far that half her ass was showing! And it was just as I imagined it would look like, if not better. I whimpered, my restraint gone. I had to have her, whatever the cost. But something told me she knew what she was doing. I cleared my throat and adjusted myself.

“Pam, will you come in here a moment?” I said out the open door I had just seen her through. She looked up and smiled innocently at me, then adjusted her dress, pulling it down a bit, and walked into my office. “Shut the door behind you, please,” I added. She obeyed, letting the latch hit with a quiet click.

“What can I do for you, sir?” she asked.

“Pam, we need to talk. About your work attire,” I said, leaning back in my chair.

“Why? What’s wrong with what I’m wearing?” she asked innocently, giving me front and back in a quick turn. I gasped again at that ass. Ohhh what a sweet ass!

“Oh no, the dress is fine,” I said, quite truthfully. “It’s those stockings, unfortunately. They just don’t look very businesslike.”

“Oh!” she said, shrugging. “Ok, I can fix that.” I jumped as she put her foot up on the front of my desk and reached under her skirt. I gasped and whimpered slightly, captivated the gaze of her beautiful green eyes, as she hooked her thumbs into the waist of the stockings and slowly peeled them down, doing a little wiggle to get them off her hips, all the while looking me in the eye with a strange little devilish smile. She pulled them off her shoes and tossed them into the corner.

“Was that all…sir?” she asked, giving me bedroom eyes to the max.

“Actually,” I began, composing myself and folding my hands cross my chest as I kicked my feet up on my desk, “Were those black panties you were wearing?”

“Mmm, yes they were,” she answered, sliding her hands down her sides and giggling a bit. I shook my head.

“Those have to go. A sexy color of underwear like that has no place in this office,” I said.

“But sir,” she acted, “My bra is black too!”

“*tsk* Gotta go, then!” I said, giving her my best “oh well” face with a shrug of my shoulders. This was going perfectly. She put on an acted dejected look.

“Yes, sir,” she said quietly. I watched with delight as she slowly peeled off the straps of her dress, exposing a strapless black bra that was holding back her big, lightly-freckled jugs. She looked me in the eye as she unclasped the bra and let it fall to the ground, her tits bouncing free. I gasped; fantastic rack! Big and round, with deep cleavage and small, light-colored nipples. Once the bra was off, she pulled her straps back up and stuffed her breasts back into her dress, which didn’t leave a thing to the imagination. The fabric was so tight that you could see her lighter flesh through it where her skin was pressed against the dress, and her nipples could easily be seen. Her tits bounced and swayed with every tiny movement she made as she next reached under her dress again, turning her back to me as she did so. I gasped and grabbed my hard shaft through my pants and she pulled down her panties all the way to her ankles, without bending her knees even a millimeter!

“Ohhh my goodness,” I gasped quietly as she revealed her private splendor to me. Her cheeks were big, round and smooth, pressed tightly together, hiding her rosebud. Her pussy was thick-lipped and meaty, shaved smooth. She slowly straightened up and tossed her panties onto the pile with the rest of her clothes.

“Good!” I said. “Now come to the office like this every day, and we won’t need to have any more of these discussions. However! To teach you a lesson for wearing such provocative clothing, I’m going to have to exact punishment.”

She acted out all her faces perfectly. “I understand, sir,” she said with head down, feet together, and hands clasped behind her back. “What is my punishment?” she asked. I scooted back my chair and beckoned to her.

“Come over here, Pam. Stand with your back to me here in back of my desk while I get ready for you. I’m going to give you a punishment you’ll always remember,” I said.

“Yes, sir,” she answered, quietly coming around and standing in front of me, arching her back slightly and sticking her ass in my direction. “Like this?” she asked.

“Perfect,” I said. I unbuckled my pants and pulled out my cock, hard and hot as a bar of newly-forged steel, throbbing in the cooler air of my office. She looked back at me over her shoulder with a cute little grin. I opened a desk drawer and retrieved a jar of Vaseline. Her mouth dropped open in a big smile as she watched me lube my cock from top to bottom with the greasy gel.

“Ooo! Sir, where do you plan on putting that thing? Are you…are you going to put it…” (Her voice fell to a whisper) “Are you going to put it in my butt?”

I nodded. “That way you’ll remember our little chat here today,” I said.

“Oo! But I’ve never done that before!” she whined in mock protest.

“All the better. Now, lift your dress and sit down,” I commanded.

“But…but…but,” she stammered, lifting her dress obediently.

“No buts!” I said. “You’re going to take it in the tush like a grown woman should do. Spread your cheeks.”

Pam complied and leaned her torso forward as she lowered her hips towards my lap. I aimed my 9 inches at her tiny little pink rosebud as it came into view. She gasped as she felt the cool, lubed head touch her pucker.

“There you are, Pam. Now keep going. I don’t want you to stop until you feel my balls on your pussy,” I said forcefully.

“O-Ok,” she stammered quietly. She continued to lower to butt down onto my cock. She was definitely a virgin! Her little hole was so tight that I had to press down on the base of my cock to keep it from bending. She groaned as her pucker started to give way, spreading and stretching around the slicked intruder. Suddenly, I popped past her guarding sphincters and the bend came out of my cock as 3 inches slipped inside all at once.

“Oo!!” she squealed.

“Keeeep going…” I said. She obeyed, her hands on her delicious ass and her tits resting on my desk as she leaned forward for balance. Riding on the smooth coating of Vaseline, my cock slid nicely into her virgin bottom with no hindrances.

“Uuunnggghh!” Pam groaned, grimacing. “Oh, sir! It’s going soooo far up my butt! I don’t think I can take it all!”

“Well, you’re going to have to, Pam,” I answered. “It’s part of your punishment! Now keep going.”

“Uhhh! Oo God! Ohhh! Ung…yes sir,” she answered, pushing her hips slowly further down.

“You’re almost there, Pam. Only 3 more inches,” I encouraged, knowing that she’d never had anything so deep before.

“Awwww gawd!” she cried. “Unnggh! It…’s so deep!”

“Then you’ll remember our little chat for the rest of the week. Two more inches…” I said.

“Ohhhhhhh!!…FUCK!!” Pam growled, letting herself go and engulfing the last 2 inches of my hard cock with a quiet slurp. “Ohhhhh gaaawwwddd…” Pam groaned through gritted teeth, my cock pushed deep into her rectum. She straightened up, the need for balance lifted, and leaned back against me. I reached around and cupped her breasts, kissing her neck.

“Good, Pam. You took it like a woman. Now, keep your legs together and lean forward on my knees. Bounce your ass up and down on my cock and don’t stop until I come up your butt. Then your punishment will be finished,” I said.

“Uggghh! Uh! Yes, sir,” she said, leaning forward and getting in my prescribed position. She leaned forward on my knees, groaning all the way. God, her ass was heaven! Hot as a furnace and tight as a vise. I could swear I could even feel her quick little heartbeat through that hole.

Slowly, her weight on my knees, she raised her ass up my cock. I watched as the greasy length of my shaft reappeared from her tight hole, stretched snugly around my cock. She made sure it was a long stroke, like a good girl should, and didn’t stop until only my head was still in her ass. Then, she lowered her booty back down onto my cock.

“Unnnnnggghhhh….” She groaned with a mix of pain and pleasure. “God, it just slides in there so easy!” she marveled, completing a second bounce of her hips.

“That’s one of the best parts,” I concurred. I placed my hands under her delicious rear end, and helped her bounce, lifting her ass up and letting her slide back down onto my cock.

“Oooooo yeah…” I sighed. “That’s it, Pam. Take it good and deep.”

“Uhhh!” was all Pam managed to answer, her head tilted back.

“Now faster,” I encouraged, lifting her butt up with more force and pulling her back down by her hips until she got the hang of it. Then, I let go of her and laced my fingers behind my head, smiling broadly as my secretary bounced her tight virgin booty up and down, up and down…

“Oo! Oo! Oh Jesus! Uhh!” she wailed, bouncing faster and faster. I watched her meaty buttocks jiggle slightly with every bounce, my cock sliding deep into her ass, my balls hitting her pussy each time.

“How does that feel?” I asked her.

“Uh!…God! It…uhhh-huh-huh….hurts!” She cried.

“Gooood,” I said, patting her ass. “It always hurts the first time.”

“OOooOOooOOooOO…” she moaned as she bounced. God, her ass felt SO good! All that tight, slippery heat wrapped around my cock, pumping me and squeezing me, the ring of her sphincter sliding up and down, over and over! Her butt smacked down on my belly with each bounce, her big tits swinging, fantastic expressions of pain and pleasure frozen on her face. I gripped the chair as my pleasure began to mount, my balls pulling up and beginning to boil.

“Ohhhh Pam, you’re almost done!” I said.

“Ooo!” she moaned excitedly. “Does that mean you’re about to come? In my ass?” She looked back over her shoulder at me with a big smile, her butt still bouncing up and down, up and down, taking me deep, deep into her arse.

“Ohhh yes,” I nodded.

“Oo, I can’t wait!” she said, bouncing higher and faster. I watched my glistening shaft disappear up between her jiggled buttocks over and over, faster and faster, higher and higher! I spread her cheeks with my hands so I could see her anus stretched around me; she had the perfect ass for fucking. With a little luck, it wouldn’t be the last time I got to do it!

“Ohhh fuck I’m getting close,” I moaned. “Keep going!”

“Yes!…Uh!Uh!UH!!…sir!” she cried, slamming her booty down onto my cock harder and faster. I let go of her ass and watched her jiggle and flex, my cock slipping up into her hidden hole, as deep as it could go.

“Almost!” I cried through gritted teeth. I groaned and my legs tightened, my balls pulling up! “Ohhh fuck! Heeeere we go,” I said, my come jetting into her ass.

“Oo! I can feel it!” she squealed. “I can feel you coming in my ass!” Pam pushed her butt down as far as it could go and sat up straight as my cock jumped and jerked in her rectum, shooting rope after rope of hot come deep into her bowels.

“Ahhh yes…” I moaned, holding her hips. I swear it was the biggest load of my life! It must have been more than a minute that went by, during which time my cock never stopped pumping. Finally, my orgasm over, Pam slowly stood, my softening cock slipping out of her hole quickly, making her squeal. Her tight tush closed immediately, not losing a drop of semen.

“Uhh!” she groaned. “I’m going to be really sore tomorrow.” She winced and put a hand on her ass.

“You can have tomorrow off,” I offered.

“Thank you sir,” she said with a smile. “Is my punishment over?”

I considered, watching her face, then smiled back. “Well, it is for now. But if you want to continue to work here, you’ve got to respect company policy. I’m afraid your punishments will have to continue if you continue to wear such provocative clothing.”

“Yes sir,” she said, smiling devilishly and walking gingerly out the door.

Two days later, she showed up in a tube top and little cotton shorts.

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