Roll Play Fun With [M]y Wi[F]e: The Office Assistant [Long, but fun and hot]

The following is a role play scenario my wife and I acted out that immediately became one of my most enjoyable sex sessions ever. My “desk” was really a tray table and my living room couch, but use your imagination and enjoy…maybe even use parts of it in your next role play.

I was working feverishly in my office on a presentation with a rapidly approaching deadline when I heard a soft knock at the door.

“Come in,” I answered.

The door slowly opened and in came the office assistant, looking sexy as ever, but timid about approaching my desk even though I had called her in. She stopped by the door, letting it close behind her.

“You wanted to see me, sir?” she asked sheepishly.

“Yes,” I replied rather forcefully. “I’m under a lot of pressure to have this presentation done as soon as possible and there are some clerical tasks I need done that I’ve had on the back burner for days. If you can do them for me it’ll help me relax and focus.”

“Of course, sir. I’ll do anything you need.”

The confidence in her voice had taken a 180 as she said this. My mind couldn’t help but to go to inappropriate places because of what she said and how she said it. She seemed almost too eager to say it the way she did. It didn’t help that she was wearing a shimmery tan form-fitting sleeveless blouse that already revealed the top of her cleavage and provided a full view anytime she bent over. This was complimented with a hip-hugging black pencil skirt with a slit in the back that came down well above the middle of her thigh. Add some sensible black heels, a pair of modestly thick rimmed glasses, and a top knot pony tail with her brunette bangs hanging over her hazel eyes and she pretty much fulfilled my fantasy of whom I’d want to have a romp in the office with.

“Wonderful! I admire your enthusiasm,” I told her. “For starters, can you get me a glass of water? I’ve gotten so thirsty all of a sudden.”

“Yes, sir.” Without questioning how remedial the task was, she took my sports bottle from my desk and walked over to the cooler in the corner of my office. I couldn’t take my eyes off her ass as she sauntered over and bent over to fill it up. She didn’t have to bend over as far as she did, but why question it? I was enjoying the view.

“Here you are, sir,” she said as she slowly bent over to put the bottle on my desk, giving me a great look at her glorious cleavage pouring out of her blouse.

We happened to look into each other’s eyes at the same time for a brief second. She glanced down and noticed how low were blouse had gotten, but instead of pulling it up, she looked back up at me and smiled.

“What else can I do for you, sir?

Trying to compose myself, I quickly pointed to a stack of papers.

“It would be great if you could get these reports filed. They’ve been sitting on my desk for days and if you take care of them, I won’t have them weighing on my mind.”

“Anything you say, sir,” she obediently replied, picking up the stack of papers.

Knowing exactly what I wanted to see next, I advised, “Most of the drawers in the filing cabinet are pretty full. The one on the bottom has plenty of room though.”

Her eyes lit up. “My skirt’s a little tight to bend over comfortably. You don’t mind if I get down on my knees to do that, do you, sir?”

“I want you to be as comfortable as possible. Do whatever works best. I don’t mind,” I responded trying to hide my excitement.

I didn’t type a single word or click my mouse once while she performed this task. I was blatantly fixated on watching her as she got down on her hands and knees and organized the reports. I could have been mistaken, but I could’ve sworn she arced her back to show her off beautifully round ass for me, even swaying it side to side subtly. Her little skirt had come up just to the point where the back of her leg curved out, but I still couldn’t tell what she was wearing underneath. She didn’t look back to catch me looking, but surely she knew I couldn’t miss this show.

When she finished, she got back to her feet and adjusted her skirt while smiling an apologetic smile, although I didn’t really think she was sorry.

“How else can I be of service to you, sir?” At this point, she had added a little bit of sultriness to her voice.

I had work she could do for me at her desk, but instead I thought quickly.

“During your orientation, we never got your signature to scan so we can electronically add it to documents. Could you sign your name on this blank sheet of paper really big?”

“Anything you want, sir,” she said through her breath.

She again slowly bent over my desk to write her name. I didn’t try at all to be discrete watching her boobs jiggle as she intentionally wrote with exaggerated strokes. When she finished, she stood up straight and slid me the paper. I slid it back.

“Print too, please.”

She repeated the display for me, this time noticeably giggling a short giggle. She slid the paper back to me.

“What next, sir?” She looked at me like she was a lioness and I was a raw side of beef.

“Actually, you’ve cleared the clutter around here and I should be more relaxed, but strangely I’m still feeling stressed.”

“Oh?” she asked, turning to smile at me out of the corner of her eye.

“I know this is a professional office and this may not be totally appropriate, but do you think you could rub my shoulders? I think it would really calm me down so I can focus on this presentation.”

“It would be my pleasure, sir.”

She walked around my desk and behind my chair. I leaned forward a little and tried to act like I was working, but stopped in my tracks when her hands slid up my back and over my shoulders and neck.

“Oh, sir, your shoulders feel so strong. I could rub you for a loooooooong time. Does it feel okay?”

“Yeah,” I moaned out. “It’s exactly what I needed.”

“Okay, good. I want to do a good job at anything I do for you, sir.”

“Why don’t you take a look at the new performance evaluation I’ve been working on,” I said, bringing up a different presentation on my screen.

She stopped and leaned in to get a closer look, pressing into my shoulder with her soft chest.

“Oh no, keep rubbing,” I instructed, in spite of how great her boobs felt against me. “It feels too good for you to stop. I’m starting to relax a little.”

She picked up right where she left off, going in circles with her palms on my lower back while gripping my sides with her fingers.

I continued, “For the last two months, performance around here has decreased dramatically and this evaluation is supposed to help us understand the reasons for the decline, although I have a pretty good idea of what’s causing it. How long have you been working here?”

She answered, “Two months, sir.”

“I’m not surprised as it plays into my theory. Do you hear how the other women of the office talk about you?” I asked.

“I have,” she retorted with a hint of disgust. “They say I dress inappropriately, that my tops are too low and too tight and that my skirts are too short and too tight.”

“Have you noticed how the men stop and look at you each time you walk by or each time they walk by your desk?”

“I really only look to see if one man is looking…sir.”

I pressed on. “Do you think your clothes are unprofessional?”

“I feel good in what I wear and I like the attention a certain co-worker gives me,” she justified.

“Shouldn’t we all feel good as much as possible?” I asked. “If it feels good, do it. Right?”

“You make me feel good, sir. Do I make you feel good?”

“This massage is making me feel good. But back to my theory. I think ever since you came aboard, everyone’s been too worried about what you’re doing rather than focusing on his or her own work. What do you think about that?”

“To that I say we’re all adults. They need to get over themselves,” she said with swagger.

“Exactly. While I think my theory rings true, it isn’t your problem. You’ve been a great asset to me. Very motivating. I want to show you what your performance looks like using my new template. Would you like to see?” I asked, knowing she’d say yes.

“Of course, sir. I’ve wondered for two months now what you think of me.”

I showed her the first slide. “On a scale of 1 to 10 for the question of ‘does employee do good work?’ I’ve given you a 10 so far.”

“Thank you, sir!” she said with authentic enthusiasm. “I do my best everyday to give you what you want.”

“Now the following questions go into the criteria surrounding why I truly hired you,” I said as I brought up the next slide.

I looked up and saw her smiling big at what she saw on my screen.

I lowered my voice a bit. “You’ll see here I’ve given you another 10 for the question ‘do employee’s tits look sexy in her top?’

She responded, “I put a lot of focus on this question just for you, sir.”

Next slide, “And here, please note you get another 10 for ‘does employee’s ass look hot in a skirt?’

She spoke with a whisper in my ear as her hands went from rubbing my shoulders to rubbing my chest. “I had a feeling you liked pencil skirts. That’s why I wear them all the time.”

“And here,” I said switching to the next slide, “here you’ve got another 10 for ‘crushability.’ Can you tell I have a major crush on you?”

“I’ve hoped and dreamed for the last two months that you did, sir.”

To the next slide, I said, “and the next 10 goes for the category of ‘fuckability.’ Are you aware of how badly I want to fuck you?”

“I’m aware of how badly I’ve wanted to fuck you for the last two months, sir. I’m getting so wet knowing you feel the same way.”

Insisting I finish what I’d prepared before taking her right then and there, I told her, “Two more. The question for ‘does employee give good backrubs?’ is blank. But now that I know you give the best backrubs, I can give you a 10 just by typing “10” into this field. Pretty impressive?”

“Oh yes, sir. You impress me in every way.”

I tried to change to a serious tone for the last question. “For the last question, ‘does employee relax her boss?’ I would currently have to give you a low score.”

“Oh no, sir. I thought you said you liked my backrubs,” she said slightly panicked.

“Oh, your backrubs are the best, but I’m still very amped up. Think about what kind of tension I must be feeling and what you could do to relieve that.”

Her face turned a slight shade of pink. “I know just what to do for you, sir.”

We both darted our faces toward each other, feverishly making out while she continued to rub her hands over my chest as I reached behind me, sliding my hands under her blouse and up her warm, smooth back. I started to get up. She pushed downward on my shoulders and guided me right back down.

“I’m here to help you relax, sir. Sit, breath slowly, and watch me,” she breathed while kissing my neck.

“You better lock the door,” I warned.

“Oh, sir, I locked it when I first walked in,” she said slyly.

She swiveled my chair toward her and unbuttoned her blouse, throwing it toward my coat rack. I marveled at her perfect breasts heaving out of her black strapless bra. She then turned around and unzipped her skirt, slowly bending at the waist and pulling it down to reveal a tiny matching thong. She began to turn around, but I stopped her.

“Let me just bask for a second,” I said as I groped her curvy ass and gave it a sharp spank, which brought out a giggle from her.

She turn around, dropped to her knees, and began undoing my tie and unbuttoning my shirt. She showered my neck, shoulders, and chest with wet kisses before undoing my belt and pulling down my pants and underwear.

“Oh, SIR!” she exclaimed at the sight of my fully erect cock. She proceeded to run her tongue up and down my shaft before bobbing her head from my cock’s head all the way to the base without any trouble.

“I can’t believe this is happening,” I moaned. “Your mouth feels even better than I imagined.”

She looked up and smiled through her eyes, but continued sucking away. She came up for a break and gave my cock a few jacks before my desire to return the favor overcame me. I grabbed her around her top knot and gently pulled her to her feet and spun her around.

“Hands on the desk,” I ordered.

She did as she was told and I slowly pulled her little thong off. The aroma was intoxicating. After another loud spank (the office was pretty much sound proof), I took her by the waist and sat her up on the desk. This time I dropped to my knees and attacked the entire length of her pussy with the whole flat part of my tongue, savoring the flavor with every lap. I then put a focus on her clit with my lips and tongue while carefully sliding a finger in her to put pressure on her g-spot.

After several minutes, she moaned out, “You’re going to make me cum, sir. But I want to cum with you inside me.”

At this, I sat back on the chair and she jumped right on me, riding my cock while I unhooked her bra, buried my face between her boobs, and squeezed her ass over and over.

“I know it’s a little cliché,” she managed to say, “but I’ve always wanted to be bent over a desk. I’ve wanted you to do it to me since I first saw you.”

Without hesitation, we got out of the chair. I turned her around, put one hand over her tummy and the other around her top knot and gently pushed her down over the length of the desk. My cock glided right back into her as I held her hips and pushed inward, consciously intending to rub my mushroom shaped head over her g-spot. She started thrusting back toward me faster, to which I was happy to oblige by taking the hint and pumping away.

She voiced her pleasure with every thrust.

“I think I should only work with you on projects from now on, sir. I want to spend as much time as possible in your office just you and me.”

I agreed while fucking her as deep as I could, the ecstasy mounting as I watched her ass wave forward with every piston. “I think I need to have you be my personal assistant. There’s so much you could do for me that I’d only want you to do.”

She must’ve liked this suggestion as she replied with, “Oh yes, sir, I want that too. I’m gonna cum, sir. Hold it in as deep as you can!”

I did as she requested as she moaned with every convulsion. I took it all in as her pussy contracted around my throbbing cock.

After her breathing calmed, she asked, “Is my score for relaxing you improving, sir?”

“You’re almost to a 10. I just need you to make one more thing happen for me.”

“Tell me what to do, sir. You know I’ll do anything you ask.”

I didn’t need to tell her. I turned her around and laid her on my desk on her back. I held her legs up high and told her to put her hands over her head. I slid my cock right back in her and went in and out while watching her perky breasts bounce forward and back.

“Tell me how my cock feels inside you,” I commanded.

“Your cock feel so full and thick inside me, sir. My pussy can feel everything. It makes me want to feel your hot cum all over me.”

I pulled out and told her to stroke my cock hard as I aimed over her tummy.

“Tell me to cum for you.”

“Cum for me,” she said.

“Say it again, but call me sir this time.”

“Cum for me, sir.”

This put me past the point of no return as I let myself go and exploded my cum over her tummy with the first few shots landing on or between her boobs. I nodded to let her know I was done, to which she dropped to her knees and slowly deep throated me, the perfect “after care” treatment.

As we put our clothes back on, I told her, “after this big presentation is behind me, they’re sending me on a business trip. I think I’ll need your help to keep my schedule organized and handle my day to day operations. Simply put, you should go with me.”

“That would be a most efficient use of time, sir. There could be a lot of late nights and extra hours to put in. Could be very stressful. You’ll need someone who knows how to help you relax.”

I sent her back to her desk with one last spank on her ass, but not before I made sure she saw me enter a final and most deserved 10 into her evaluation.

Source: reddit.com/r/gonewildstories/comments/8t7890/roll_play_fun_with_my_wife_the_office_assistant

2 comments

  1. If I remember right, one night she asked me about my fantasies we could actually bring to life and “office sex” was one I mentioned. Then in the car one day she read me a post from this subreddit about an intern who got her boss’s attention that we both really enjoyed. She mentioned she had an outfit she thought I’d like, causing me to spend a day at work planning a scenario I thought she’d enjoy. That night I hastily threw together a rudimentary PowerPoint bar graph as my “performance evaluation.” I put on my snuggest slacks and button up collared shirt and tie on, approached her where she was working and told her she needed to change. She went to change and I set up an “office” in the living room.

    And that’s where the story begins…

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