Category: Naughty Secretary Phone Sex

Naughty Secretary Phone Sex: Shemale Office Party

Naughty Secretary Phone Sex trannyA fellow tranny friend of mine got me hired on as a temp in her office. Just through the winter months, I am going to be a secretary with her in a busy medical office. Friday, we got stuck at work because a blizzard came through Pittsburgh. It was just us and this account executive that were working overtime. While we were waiting for the plow trucks to come out, we partied with some Fireball Whiskey I had stashed in my desk for just such an emergency. Pretty sure Jim was clueless about our special nature. But he was about to get a double surprise.

We all started making out, and before long, two naughty secretaries were sucking his cock. He has a decent cock too. More than enough for two tranny tongues to devour. We were swallowing his cock, playing with his balls, when my 10 inch cock starting sticking out from my skirt. I unzipped my skirt, and stood in front of him in my sexy lingerie with my hard cock. Trina did the same thing too. Standing before him were two sexy shemale secretaries.  I thought he might be upset that we concealed our identity, but he couldn’t wait to fuck us both. He didn’t want to get fucked sadly, put he pumped his big hard cock into both our asses. When he fucked my pretty tight ass, I sucked Trina’s cock and vice versa. It was so hot. I had cum running out my ass, and my mouth. Not a bad way to spend a Friday afternoon snowed in.

After a couple hours of fucking and sucking, we got word that the main road had been cleared. We decided to keep partying for a bit longer. I loved being a bottom for a change. How would you react if you discovered your sexy secretary had a 10 inch cock?

Let me see your package..

For weeks now I have been flirty with the sexy new mailman at the office. I love his dark skin. I watch as he picks up the heavy boxes and see how his sculpted muscles pop. After he leaves I rub my clit till I cum. Today  is like every other day expect I have a few boxes that need to go to my house. Jabari walks into the office like a black god. His stride is so confident and so sexy it makes me want to fuck his toes. His white smile makes my panties soaking wet. He walks up to my desk and stands right next to me and bends down and says “Its Thank a Mailman day, How are you going to thank me?” This was my chance. I turned my chair to look at him with the heat and passion in my eyes. I rubbed my thighs and pulled my skirt up just a few inches higher to catch his eye. It worked. I told him I had a few boxes that were too heavy for me and they needed to go to my home address. “Do you think you could do a home delivery for me Jabari?” He nodded and smiled. Ill meet you here after I’m off work. He adjusted his hard cock right in-front of my face as he looked down at me. I licked my lips and told him I couldn’t wait.

phone sex fetish

I was like a little girl waiting to open her gifts on Christmas morning. It was 5:30 and Jabari still didn’t show up. Maybe he was still busy. My mind was going and thinking that I didn’t hear the bell on the door go off. He found me in the supply closet. I was more than surprised to feel strong arms wrap around my waste. I saw his arms and knew it was him. He spun me around and started kissing me with his big thick lips. His mouth fallowed down my chin to my neck where he bit and sucked hard. My knees went weak and I fell to my knees. I started unzipping his pants and pulled out his massive black cock. I took as much of him down my beautiful throat as I could, there was still 4 inches that I couldn’t take. I let fuck my throat until he came. He squirted his hot cum all over my face. He smiled and bent down and kissed me. I told him I wasn’t done thanking my mailman. I started rubbing his cock to get him hard again as he was rubbing my tight ass. He pulled all my clothes off expect my thigh highs and bent me over the fax machine…

phone sex fetish

As he spit on my asshole I knew this was going to hurt so fucking good. He struggled to push his fat cock into my tight hole but finally forced it in. His cock filed up my ass. He stretched me open as he slammed his hard cock in and out of my ass. I started to rub my pussy, I was dripping wet down to my ankles. As I rubbed my clit and he fucked my perfect ass hole I started to feel a build up in my stomach. I didn’t care that his giant cock was destroying my ass. All I cared about was taking more and more of his cock. He grabbed my throat from behind and started to choke me as he slammed his big black cock into my ass. The more and more I struggled to breath the more my stomach started to go crazy. He slammed me down on the fax machine as I squirted all over us. I fell to my knees again and started to suck his cock. He loved that I went from ass to mouth so much he shot his load all over my face again.

I smiled and said thank you mailman.

Naughty Secretary Phone Sex: Sissy Training Holiday Party

I have a part time office job. I don’t have to work. I don’t even enjoy working, but this office job is unique. I am paid really good money to simply give “dicktation.” I have no real skills. But, when you can deepthroat massive cocks, you find yourself in high demand. So many women just can’t swallow a huge shaft. Since I am a total size queen and won’t get out of bed for less than 8 thick inches, many well hung corporate executives need my special skill set to get through a grueling work week. I have been the big cock blowjob secretary at an all male law office for a few years now. The smallest cock in the firm is 10 inches; so I would work for free, but I am not going to complain about a 6 figure income a year to suck real men off.

Every year they throw a wicked wild holiday party. They hire male strippers, bring in a celebrity chef and bartender for catering, even hire a few pretty whores to help entertain the guests. Besides the whores and myself, it is an all male, all well hung party. No sissies or tiny dick losers allowed. Well this year’s party was the kinkiest ever. Somehow, two tiny dick losers snuck in. I guess they had huge wallets and thought that would make up for having clit sticks. My bosses recognized that I am too hot as were the hired whores to service anyone with less than 8 inches. No amount of money will make me lower my standards.

Being the mean size queen I am, I suggested we sissify the girls who failed to measure up. I love humiliating tiny dick losers, especially ones who do not know their place. The rented whores joined me. We got them all prettied up and made them suck off the male strippers. Dressed them like pretty sissy Santa sluts.  Even had them bend over and take it in the ass by the real men. I  put on my big red strap on and fucked them like the  sissies they were. The strippers enjoyed humiliating  the sissy fairy fags too because they thought they were better than the rest of us simply because they had money. At this office holiday party, big cock was the only thing that mattered. Last year’s party I was sucking big dick and getting fucked. I did enjoy some of the hot hung strippers, but I spent most of the party training the new sissies to suck cock and take it in their back door pussies like good sluts. Even made them  drink cumnog! Got to get sissies hooked on cum early on in their training.

Even though the office Christmas party was different this year, it was still wicked kinky fun. Only thing I enjoy as much as a big hard cock in my holes, is putting tiny dick losers in their place!

Office Holiday Party Circle Jerk

My office holiday party this year got WILD! My boss had these Latin studs serving us drinks. Well we all had one too many drinks and before long a few of us girls thought we were at a Chippendale’s show instead of an office party. We were shoving money in their pants, chanting “Show us your cocks.” Sure enough, they whipped them out. They started a circle jerk. Some of guys in the office joined in. Seeing those big cocks being stroked made my cunt wet.  I often have black studs standing around me circle jerking on my face, but this was first time I saw a bunch of guys jacking off in front of a mixed group of people who were all clothed.

Normally, I am the biggest office slut. But more than one co-worker was on their knees in front of them hoping to get a face full of jizz before me. Guys and girls too. I work with some greedy cum whores.  I joined in on the party fun. I figured out of all of them, I was likely the only one with real circle jerk experience. I didn’t need to be drunk to get wild with some cum filled cock and balls. I showed them how to be true cum sluts. I instructed them to take off all their clothes, lay down on the floor and let the cum flow over their faces and bodies. I am a black bukkake gal, so I was egging those Latin Lotharios on.  Telling them to shoot their jizz all over our faces.

The holiday office party turned into an office orgy. Turns out our hired help went both ways. They fucked the girls and a couple willing guys too. I never knew my co-workers got freaky. Made me feel good to know I was not the only huge cock loving cum dumpster in the place. I went into the kitchen got some glasses and had the boys circle jerk their loads right in the cups so we could all toast to the best office holiday party ever.

My Raise

Yesterday I was running late for work. I get there an hour late. My fucking boss was all over my ass, pulled me into one of the rooms to give me my performance appraisal.  First he said I have been doing great but I needed to prove my development in a few areas. My daughters watched with excitement as he walked over to me pulled up my shirt and starting playing with my nipples.  His hands fondled them and groped them like he was feeling the ripeness of a melon. His hands eagerly moved down my body grabbing my hips and pulling them to his groin. He pushes me to my knees and demanded me to be beg about keeping my job and if I didn’t do what he expected of me he was going to whore out my little girls. I pleaded to only focus on me but his insistence, drove my desires. The urge to taste cum overwhelmed me and I start fondling my tits and push my panties aside and slide a finger it my dripping wet pussy. He demands I take a hold of his cock, I do as I’m told. I start sucking his big 10inch cock and start deep throating it, he rams in my mouth. I gagged because of how deep it went. My little girls sat back absorbing mommy’s techniques thinking how they could improve. My boss watched them gazing at me and pushed me away and demands that they come over and finish the job. Oh boy did they, it didn’t take much for my girls licking and stroking him that he shot his load all over their faces. They laughed and giggled at the excitement they caused him and took their fingers to clean their face.  After my boss composed himself he walked over and slapped my ass and said good job, you got your raise.

Every Command

   The way you made me writhe under you last night was exquisite. I was thinking about it all night last night, and all day today at work. I just could not get the way your nice, hard, thick cock stretched my tight cunt to the very limit… oh lord have mercy I’m wet and desperate just from the memory of it! The way you took charge of me was exquisite, and you had me begging for that wonderful, thick cock within seconds of those first harsh, commanding words. I know that my subservience was pleasing to you; I could see that your cock was straining to be freed from your jeans as I obeyed your every command. When you commanded it, I bent over the arm of your couch and spread my legs as wide as they would go. When you told me to stay silent, I tried my very hardest to hold in my moans and whimpers as you brutalized my clit. My favorite part of the evening was when you forced me on my knees and forced that perfect cock down my throat. I can’t wait for you to call on me again, because you know I’ll obey your every command no matter what.  

Books can’t teach you this Part 3

   Thick. That’s the only thing I could think about when Vince grabbed my head and forced himself into my waiting mouth. His cock was HUGE and think and every time he forced it to the back of my throat I felt my dripping pussy quiver. If his cock felt this good in my mouth and down my throat, I could only imagine how amazing it would feel buried deep inside my tight, dripping cunt. I glanced up at Vince and saw that while pleasure was obvious on his face, he seemed cool, calm and collected. 

   As if on cue, he looked me straight in he eye and started to mock me about how desperate I must be to have his thick, hard cock deep inside my dripping pussy. All i could do is nod and moan. He grabbed me by my hair and pulled me up. He ordered me to bend over the table at the end of the books shelves and wasted no time holding my head down against the table and holding my arms behind my back. The instant his cock thrust into me I was writhing. He was stretching me to my limits, and I could already feel an intense orgasm fast approaching. In moments it was over. I felt pleasure overtake me… my cunt squeezed around Vince’s cock and he burst inside me. It wasn’t until I came down from my high that I realized Vince had already taken his leave. I hope to see him again soon, the things he can teach me can’t be learned from books…

Books can’t teach you this Part 2

   Here I am. Backed up against a bookshelf in a public library with a mans hand working me into a stupor. He was smirking at me, just watching every little reaction on my face as his skilled fingers worked themselves into my dripping core. I tipped my head back and allowed the please to overtake me. The fact that this was happening in such a public place only heightened the intense pleasure I was feeling. Suddenly, Vince’s magic fingers were gone, leaving my dripping cunt feeling empty. He leaned down and hissed into my ear that if I wanted to cum, I would need to prove I was worthy of it.

   Vince gently yet firmly placed his hand on the top of my head and pushed me down until I was kneeling in front of him, my face directly in front of the bulge in his pants. He looked down at me with a pleased expression and told me that I should keep my hands behind my back if I wanted to feel that sweet, sweet release. He unzipped his pants and drew his massive cock out. He smirked and pressed the tip of it right to my lips and gave me a simple command. Suck. I needed to do a good job if I wanted to him to let me cum too…

Books can’t teach you this! Part 1

Everyone needs to escape for a bit… wether that escape is a vacation or a good book it doesn’t matter, as long as it does what it needs to do. While I was at the library yesterday searching for the next big thrill to allow me to escape from my humdrum reality, I noticed a quite handsome young man lurking a few feet away. Every few minutes he would steal a glance at me and shoot me a suggestive look. It took me a few minutes but I finally realized why this guy looks so familiar… he’s a client at the law firm I work at… Mr. Vincent Hammond. Finally he could see the revaluation on my face and sauntered over to me, a smirk playing on his lips. We spoke for a few minutes before he suddenly grabbed my shoulders and forced me up against the rows of books. His voice suddenly turned dark, and I realized that the hands that had once been on my shoulders were now bunching my skirt up around my hips. Oh god, 5 minutes and this man had my panties soaked! My night just got much more interesting…

Anytime, Anyplace, Any Position

I wait until after five o’clock, so we can have all the privacy we need.  I get up from my desk and pass a crowd of co-workers waiting for the elevator.  I make my way to your office, sashaying my hips in anticipation of what we’re about to do.  I stand in your doorway and wait for you to notice me.  The scent of my perfume makes its way to you, and you look up at me.  The sexy smile creeping across your face tells me that you know why I’m here.  I step in, close the door and draw the blinds.  When I turn around, you’re right there.  You unbutton my blouse to set free my lovely tits.  I unzip your pants and free your steel rod.  Your Johnson is in my mouth before you can take another breath.  You want me bad, and I’m already wet for you.  We make our way to your desk.  Your strong arms grab my hips, and you pull me on top of you, as you lay back on the desk.  You love the up-close view of my big, brown bubble butt.  I ride you until I cum.  You hold me to you, get up and put me on my knees, never breaking the connection of your thick cock and my juicy twat.  You ram that big pipe in me fast and hard, making my ass jiggle and dance for you.  I cream all over your cock again.  You grab my legs and rotate me, swirling my pussy on your pole until I’m facing you.  You pull me to the edge of the desk, throw one leg across your shoulder, grab my tits, and penetrate me until you’re balls deep.  I gush my juices all over you, and you fill my chocolate puff with your cream.  What a way to end the day!