Secretary's First Job

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A secretary and her Boss get to know each other.
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This is my second story I'm submitting, another short straight-to-the-point fuck session, except this one's about a boss and his secretary. Feedback is greatly appreciated, Enjoy!


I'm sitting at my desk, in a low cut blouse and short black skirt. My legs are covered in black stockings and wearing small black heels. I'm going over some emails then I get a call from you in your office. I answer it and you say "there's something I need you to take care of in here, and be quick."

I haven't known you that long, because I'm the new secretary you hired, but I find you very attractive so I tell you that I will be right in. I check my make up quickly, pull my shirt down a little, adjust my skirt then walk in to your office. It's a big room with a desk, two chairs, and a couch in the back. There is a wall window on one side overlooking the city.

"What do you need?" I ask, standing at the door.

"I don't need anything actually, I just wanted to see you on your knees"

"What do you mean?" I ask nervously, even though I've been fantasizing about being your bitch since I applied for this job.

"Well I've noticed that you've giving me some looks recently, and I want to see if you're just teasing me or you're in for the real thing."

I start blushing now, as you get up from your chair and walk over to me, with my head down, looking at my feet. "But I don't know what you're talking about," I say in voice that lets you know I actually know exactly what you mean.

"Ok, I think we've played enough games now," Right after you say this to grab my arm and pull me gently to you. Then, you whisper softly in my ear, "I want you too, let's go for it". I look at you and just stare into your eyes for a few seconds, and then you move your head closer and kiss me. It's a strong passionate kiss, and I return it. We kiss gently and you move your hands around my back and start moving then down slowly to my skirt. I put my arms around your neck and pull you in closer to my lips. Our bodies are pressed hard against each other now, and we're grinding each other whilst madly kissing. You move your tongue inside my mouth and I let you in, and start feeling it with my own tongue. Your hands are massaging my ass and feeling all over. You start squeezing a little and I love it. I lift one leg of mine and put it around yours and start grinding them together.

After sometime of us grinding and kissing, you start walking backwards and fall into your chair. You sit down and then I get on top of you. My ass is grinding into your cock through your pants as we start kissing again. We start playing with each others' tongues some more, and then you start pulling off my blouse over my head. You reveal my black lace bra underneath as you pull away from our kiss. Then, I stand up and pull down my skirt, revealing matching panties and a garter belt. I get back up on your lap and start undoing your belt and zipper. I pull your pants down just enough so your cock pops out. I grab it with one of my hands and start jacking you off. I hold my hand on your cock and stroke faster and faster. Feeling the massive thing is one of the best feelings in the world for me.

Then, I put one hand on your shoulder and lift my ass off your lap and hover it above your cock. "Fill me up, baby" I say right before I lower my ass on your cock. At first, I move down slowly until I feel you at my hole. I pull my cheeks apart a little, to let you enter in. As soon as I feel the tip enter, I start moaning. Even though it's just the tip, it still starts stretching my hole. I can feel my cheeks spreading apart as your large tool enters me. Then, I move completely down on your cock, and I am now sitting on it, with my own sticking right out of my panties. I move my ass around on your cock and then start bouncing on it a little. Every time it goes all the way inside me, I moan some more, I'm getting a little louder each time and as we pick up pace. You start moving your thighs up and down and now I'm really riding it. I let my legs relax as the bounce up and down then I put my hands on your shoulder and ride your cock as hard as I can. I bounce up and down on it, feeling it enter deep inside me. You have your hand wrapped around my cock and are stroking me gently as I impale myself on your cock repeatedly. Then we kiss again, and it's the best feeling in the world for me. I have my ass full a nice thick cock, and mine getting jacked off, and your lips on mine. It just feels amazing and we continue like this for a little bit longer.

I get up off your lap and stand up. I walk over to the couch in the back and put my hands on the back and my knees on the seat, with my ass facing out. I'm waiting for you in position, then I wink, and you come running over. You're standing behind me with cock pointed straight at my ass and with your hands on either side of my waist. You slowly move the tip inside me. Then, after a little fidgeting, you put the whole thing in me again. I move my body back and forth on your cock, trying to tell you to go faster, and then you do. Quickly, you start picking up pace and start ramming me. I'm moaning even louder now every time I feel your cock hit deep inside me. You grab on tight to my hips and pull my ass into your cock. This vigorous sex goes on for a few minutes, and then we switch positions again.

You pull out and suddenly I feel so empty. I fall back on the couch, which my legs high in the air and my hole wide open. "Come take me now!" I say as you grab my legs and hold them up while you put your cock inside me for a third time. We get a good rhythm going and we both get close to climaxing together. You put one hand around my cock and start stroking fast, as you start slamming me harder too. You start to cum inside my ass, and soon, fill me up like I've never been full before. This makes me cum too and we both climax together on the couch in your office. You keep stroking me until I go soft in your hand, and you go soft in my ass. As you pull out, I hear a "pop" and then start to feel the cum leaking out of me.

After I clean myself up, I put my clothes back on and head for the door.

"You'll do fine here," you say, as you slap my ass on the way out. I leave, walking a little funny and with a smile on my face. "

"There's more to come," I think to myself, and almost squeal with delight.

Hope you liked it! Tell me what you think. Good or bad, I'd love to read your comments. Feedback GREATLY appreciated.

Til next time, LittleBlackDress54 xx

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11 Comments
AnonymousAnonymousover 4 years ago
Thank you

I'm really glad this is very nonspecific about the boss. As a trans lesbian that would much rather be in the boss's position than the secretary, I enjoy being able to immerse myself completely in the fantasy.

cdCindy1cdCindy1almost 5 years ago
love this story

I'm a closeted sissy CD and I'd love to dress up regularly and be a sexy secretary for a well-hung boss. I would love to service my male boss every day and have him feed me his big cock and fuck my man-pussy deep and hard every day.

Please tell more stories like this one. It's so hot I came into my hand and ate it all up.

hicutloverhicutloverover 7 years ago
Wonderful

Love, love, love your stories! This one made me soooo hard and had me fantasizing of being her and riding that hard cock!

AnonymousAnonymousover 7 years ago

that was fantastic

AnonymousAnonymousalmost 9 years ago
Ok Story!

First, I want to congratulate you for submitting a good quick read. I liked how you wrote the story as the reader being the boss. The thing i didn't like about it was, the boss wasn't surprised by the extra package you had in your panties. I missed the surprise of that and the tension it can add to a cross dresser story. It's your story so I can't hold that against you although I would really enjoy holding yours if you know what i mean. Please keep the story's cumming.

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