I’m in charge of a business function that covers several different offices, so I’m often on the road to visit the locations. I kept hearing the name of a new salesperson come up: Linda Marconi. Some of my staff at the office she worked at were becoming very involved with problems she should have been calling into a service desk for. I asked them to redirect her, but then I would hear from other employees that they continued to help her.
I was a little puzzled–these guys usually tried to avoid dealing with people as much as possible. So on my next visit, I kept one eye out to see if Linda would stop by the area where my team was assigned. By noon on my first day there, the question had been answered.
The clicking heels announced her presence and I looked up subtly to see a nice pair of legs. She was wearing a skirt that was too short for an office and four-inch heels. I already had a feeling about what her deal was before she turned to peak into my office. Once I saw the tell-tale overuse of eye makeup and low cut shirt, I knew she was experiencing what I call the “aging stewardess syndrome”: an aging woman who relied on her looks for professional success was not dealing with her decline very well. I didn’t give away that I had checked her out and continued to work.
My reaction had bothered her. Out of the corner of my eye, I saw her walk slowly back and forth across from my open door. Predictably, she dropped a pen and had to bend over to pick it up right in front of my office. She held her skirt against her while she leaned down, so she had some modesty, but she glanced back a couple times to see if I was looking. As far as she could tell, I was not. I knew how to drive this type of woman to escalation.
Once her problem was addressed by one of my underlings, she started to gather her things. I walked out and over to the guy she had been working with and asked for a status update on something he should have been working on without acknowledging Linda. When I was done talking, she introduced herself and I coldly shook her hand. I quickly returned to my office before she could start a conversation. I could feel her frustration and self-doubt growing as I walked away. It’s a gift, what can I say?
I wasn’t surprised when she showed up at my office later that day. I had stayed after the rest of my team left to finish a presentation I had to give the following morning. About 7 PM, I heard a knock on my door and finally made eye contact with Linda who gave a big smile. “Surprised you’re still here. Would you mind helping me out?”
She walked over to my desk and put her laptop down on a short filing cabinet next to my chair. She leaned over so her necklace dangled in front of well-tanned cleavage. I found myself wishing that I had a mirror on the other side because she was bending forward so far. I showed her what she needed to do on her computer to complete her work and she kept pretending to be awkward as she fumbled with the keyboard and touched my hands that were waiting for her to finish. I knew her so well–she had wrapped every man she’d run into here around her finger and now she wanted the boss. But I knew she really wanted me not to let her do that even more.
After her problem was fixed, she lingered. I turned back to my screen and was a little surprised when she picked up her laptop and then sat on the filing cabinet, heeled feet dangling above the floor. She laughed when I gave her an annoyed look. “Hey–hope you don’t mind if I hang out here for a bit. It’s creepy in this place with no one else here. Do you mind if I stay until you go?”
I looked at her directly. “Why don’t you just say what you want?”
Her eyes widened and her knees spread a bit, a subconscious answer. “Well, I’d like to keep you company. I know you’re far from home and hate to have you get lonely. You do all this travel for us–that has to be a drag?”
I gave a half-smile. “Not really. It actually suits me–I get to have my fun on the road and then be a good boy at home.”
She straightened up, thrusting her chest out slightly. “Oh?” I could see her self-doubt creeping in, but to her credit she pushed it down. “Is that something I might help you out with? Having some fun?”
I laughed. “Maybe if you were about 25 years younger, Linda. Older women just aren’t my thing.”
She look wounded. I started to get hard. “Hmm–I see. I guess girls are always looking for a daddy figure to fool around with. I don’t like to think about it, but I suppose mine does too.”
Now I perked up. “How old is your daughter?”
She smacked my arm. “Hands off, mister. She’s a freshman at college this year. Almost 19. Way too young for someone like you.”
“Sounds about right to me.” She licked her lips after I said it. “Does she look as good as I’m sure her mom did at that age?”
“She’s almost a twin. It’s actually a little creepy.” Her legs moved a bit further apart. “Would you really fool around with a girl that age?”
I nodded. “22 is pretty much my limit these days.” She slumped a little.
“So there’s nothing I could do to interest you?”
“If you can make me hard talking about your daughter, I’ll let you give me a handjob.”
“How do you want to do this?”
“Sit on my lap–that’s how I like to start with these girls.”
“Yes, sir–should I shut the door first?”
“Probably not a bad idea.” I watched her walk over to the door, suddenly full of confidence. Even if my request was unusual to her, the end result was not–her purpose was clear: make the strong man cum. That’s the only thing she ever wanted to do. She didn’t break eye contact as she walked back over and climbed into my lap as she kicked off her heels.
“What do you want to know, sir?”
“Tell me about what she’s done in your house–sexually speaking.”
“She’s been a very active girl. I don’t know she had sex before college, but she very much liked to play with herself. We’d hear her down the hall sometimes, grinding and moaning. She liked to put a pillow between her legs–I could tell because I could smell her pussy on it when I’d change her sheets.”
She tentatively placed a hand against my zipper. “Is that the kind of thing you want to know, sir?”
“Yes. You may reach into my pants now, but don’t touch my cock directly yet. Tell me about how she likes to dress.”
I felt her aged hand rub against my cock through my boxers. “She liked to wear as little as she could get away with. She has my legs and her breasts are a little bit bigger. She is very fit, so she loved to show off her belly whenever she could. Her favorite look was classic, though–skin-tight jeans that would show off just a hint of her labia. My brother in law had to stop coming over because of those jeans. Men just couldn’t help but stare at that little spot between her legs, even though they felt bad for looking that way at someone so young. It would make me so jealous how easily she got attention.”
“I bet–just imagine how easy it is for her at college to get a cock. Strong, handsome cocks–not like the schlubs you find in an office.”
She winced for a moment. “Oh god, I know…”
I reached up under her skirt and felt her soft thighs as I moved up to her thong. I pressed the back of my fingers against her pussy–she was wet already. “Linda, are you actually getting wet from talking about your daughter with me?”
“Yes, sir. I want to show her to you. Would you like to look at here while I suck you off?”
I smiled and nodded. She grabbed her phone, unlocked it, did some tapping, and then handed it over to me. “I know you wanted a handjob, but I’m an excellent cocksucker. I actually gave my daughter some tips about how to do it right, so this would be a little like her doing it. You can look at these pictures and pretend it’s not some old slut’s mouth you’re using.”
I rubbed her pussy through the thong. “I think that’s an excellent upgrade. How did you get these?”
“We pay for her phone and she doesn’t realize all her photos are going into a shared folder. Every slutty picture and video she sends to boys are there. You can see every inch of her while I do my job. Just think about my young daughter while I suck you.”
She slid off my lap and onto her knees, pulling down my pants after unbuckling my belt. She pulled at my boxers until my cock popped out, already erect. One hand held my balls while the other started working my shaft. Then I felt her mouth on the head of my cock as I picked up her phone.
I scrolled through her phone and found one where she put on a cocksucking face–her rounded plump lips looked ready for a cock to be jammed between them. Her firm tits with hard nipples was just in frame. Her mother felt me get harder and she reached up to turn the phone to see which photo I liked. The corners of her mouth lifted in a smiling gesture as she continued to work on my dick. I put my hand on the back of her head as I thought about her daughter kneeling between my legs instead of her.
Flipping through the photos, it was clear her daughter was quite a slut. There were plenty of normal photos, but almost every weekend she was taking nude pictures and some videos. I found one where some boy had the phone as was banging her daughter from behind. Her perfect tits bounced in response to his strong thrusts and her tight asshole peaked out as her cheeks shook. I kept watching this over and over while her mom gagged on my growing head and shaft. I set up the phone on against my keyboard and pushed her head down as I began stroking my slick rod. I turned up the volume so she could hear the sounds of her daughter getting fucked and she reached down between her legs as I started to fuck her mouth.
My balls were soaked from her throat trying to accommodate my violent thrusts into her mouth. The mascara that she used generously to hide her aging skin around her eyes was running down her cheeks. The pressure was building fast and I started to pull out before I came, but she wrapped her hand slick from her wet pussy around my shaft and kept me in her mouth.
Her daughter still moaned like a girl and that innocent sounding voice imploring the boy to fill her up was finally too much. Her mouth pulled at my cock, wanting me to cum to her daughter being claimed. I obliged with thick stream of warm cum filling her mouth, her cadence never slowing as she sucked every drop out.
She pulled my wet, hard cock out of her mouth and lightly slapped her face with it. “May I finish myself, sir?” I nodded and she leaned back against my desk, furiously rubbing her clit as she listened to the looping video start up again. Sounds of slapping and wet teen pussy echoed in the office and I stayed hard as I watched her. I thought for a moment about turning her over my desk and using her again, but I decided it would be better to stretch this out. As it turned out, she didn’t take long to come herself–screaming softly into her hand that she had raised up from her wet slit. I smiled approvingly at her courtesy.
She left to clean up and returned with a wet washcloth. She cleaned up my cock and balls and then redressed me. “Will I ever get to play with you again, sir?”
“I think you know what will be required for that to happen.”
“Yes, sir. I do.”
“I’ll make sure there is an internship available for her this summer.”
“Yes, sir.”
“You will teach her what I like and then I will let you watch me use her.”
“Oh, god…of course, sir.”
“Don’t return to this office until you bring your daughter to me.”
“I wouldn’t dream of it, sir.”
Source: reddit.com/r/sexystories/comments/8wb17k/smells_like_middle_age_desperation_mf
This was fantastic.