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Working Late

Working Late

Series: On the Job

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An off-site meeting between a beautiful mature admin and a young new hire

(True Story) I was 27 years old when I moved to Dallas for a job and not long after had a brief sexual affair with a much older woman at work.

Gail was the first granny I ever fucked.  If you’re single in your forties you expect that to happen at some point.  But I was twenty-seven.  

I’d been in Dallas for less than a week the first time I saw Gail.  It was my first day at a new job. I’d spent eight hours in orientation before my new manager showed me my office.  A handful of people were helping me settle in, but it was the director’s administrative assistant who really stood out. 

Gail fit my idea of a Texas stereotype, even though she’d grown up in New York.  She was feisty and friendly. Her hair was honey blonde with dark roots and always up.  She dressed well and had a phenomenal body with tits that were two sizes too big for her petite frame.  She had a couple of ex-husbands and a grown daughter with a family of her own.  

I’d been with one woman who was in her early forties at that point.  Up close you could see she Gail was closer to fifty, but from twenty feet away she’d make any man stop in his tracks. There were women my own age in the office, but nobody who held my attention the same way.  

I didn’t have a work reason to talk to Gail regularly.  She sat in a little office by the director, so I couldn’t even make small talk unless I caught her at the printer or getting coffee.  She was a natural flirt with men in her age range, but it took me a while to build up a rapport.  

I’d fucked women from work in the past.  There was a thrill that came from the secret pursuit.  But Gail seemed impossible. If an older, attractive rich secretary wanted to fuck a twenty-something she could easily find one outside of work.  I still enjoyed myself by fantasizing about her all winter. The way she wore a sweater took my breath away.  

It was springtime before I finally got my shot.  I’d been at the job for six months. I reached a point where I could joke around with Gail since we had the same sense of humor.  She was getting a little flirty and not afraid to make suggestive jokes. And I was happy to take the bait.  

All winter Gail had been wearing sweaters and blazers to work.  But the week before Easter she came in dressed in a white linen bell-shaped skirt with a tight, thin pale yellow pullover.  The fabric hugged her world-class tits. It was so tight that I could see the texture of her bra. I could not get it out of my head.

A week later she wore a similar outfit.  This time the skirt was pastel green paired with white slacks and white heels.  A week later it was a peach shirt with black slacks. It didn’t matter what else she was wearing, I started looking forward to pastel pullover day.  I usually find buttons sexier, but there was something about the way those tight shirts showed off her big bouncing tits when she walked. 

I was stuck late on Friday afternoon when Gail dropped by my office.  The place had mostly cleared out for the weekend.  

“Why haven’t you left yet?” Gail asked.

“I had some things to finish.  What about you?”

“Oh, nothing for me to rush home to do.  My daughter is out of town with my grandbaby.  I broke up with the guy I was seeing a few weeks ago.  The empty house will still be there waiting for me in a few hours.”

It was pastel pullover day again.  She was wearing lavender with pale gray slacks and heels.  The air conditioner was battling the Texas heat and her nipples looked rock hard. I tried not to stare.

“How long have you been here now?” she asked.  “Will this be your first Texas summer?”

“It will, but I’ve lived in other hot climates.”

“How did you like those places compared to Dallas?”

“Dallas is definitely distinct,” I said.  “A lot of big trucks, big hair, big handbags, and big boob jobs.”

She laughed. 

“That’s true.  I think everyone got them in the eighties,” she said.  

“Oh yeah?  How about you?” I asked.

Gail flashed a sly smile.  She was used to male attention, but mostly from older guys.  She wasn’t sure how to take it from me. But she quickly recovered.  She put her hands on my desk and leaned forward.

“That’s offensive,” she said.

I started to panic.

“I’m sorry.  I shouldn’t have been so forward.”

“It’s okay to be forward, honey.  What’s offensive is to imply these aren’t natural.”

“It’s hard to judge when you’re clothed,” I said.

“How old are you?” she asked.  “I can’t flirt with you if you’re younger than my daughter.”

“I’m twenty-seven.”  

Gail seemed relieved.  And I saw the opportunity to make my move.  Just a few years earlier I had still been tentative around women. But a few years of being involved with a submissive woman had changed my demeanor and bolstered my confidence.  

I stood up and closed my office door.  

“What are you doing?” Gail asked.

“You are so fucking hot,” I said.  

Gail blushed a little.  Then she gave me a dismissive flick of the wrist.

“What are you trying to do?  You don’t need to feel sorry for me because I’m lonely today.”

I stepped closer to her.  I put my hands on her shoulders.

“Feel sorry for you?” I asked.  “I fantasize about you all the time.”

“Just stop it,” she said.  “I’m old enough to be your mother!”

I put a finger under her chin and tilted her head.  She had beautiful brown eyes.

“Then maybe you could teach me a thing or two?”

She stared at me silently. When she spoke her tone was softer.

“It seems like you already know a lot,” she said.  “You’re very direct. It’s refreshing. Most men aren’t these days.”

“I stare at your body all the time.”

“I know,” she said.  “I’ve seen you.”

“And what did you think?”

“I didn’t really think about it,” she said.  “I’m used to men staring. Although it’s not as common with men your age anymore.”

I brushed my lips over hers.  She didn’t resist.

"This is so wrong," Gail said. "I have a daughter your age."

I didn't have a response.  I kissed her again. Gail seemed to melt in my hands.  She wanted me to keep going.

"I've been dreaming about that body for months, Gail."

I gave her shirt a tug.  It came untucked from her pants.  I put my hand on her bare stomach.  It was smooth and flat I worked my way up to her tits.  She had on a lacy pink bra.  

“We aren’t doing this,” she said.  

She pushed my hand away and pulled her top down.  

“Come on, Gail.  You know you’re curious.”

“Of course I am,” she said.  “I haven’t been with a young man in a long time.  But you’re not going to bend me over your desk and use me.”

“Would you like to go out for a drink?  Dinner?”

“No.  What if someone sees us?  How do I explain getting a drink with someone half my age who works with me?”

“Who cares?” I asked.

“I do,” she said.  “I’m a grandmother.  People talk.”

“So I want this.  And you want this.  But it’s not going to happen?” I asked.

“YOU want this,” she said.  “I’ve never thought about it before today.  And maybe I want it now. But we don’t always get what we want.”

“We are adults.  And it’s harmless fun.  There is no reason you can’t get exactly what you want right now.”

She stood quietly.  I seized the opportunity to kiss her again. She wrapped an arm about my waist.  We kissed and embraced. My tongue parted her lips.

“Fuck,” she said.  “Fuck you. This isn’t fair.”

“We don’t have to go out,” I said.  “We can fuck right here.”

“I’m fifty years old,” she said.  “I’m not getting fired for having sex at work.”

She pulled away and grabbed a notepad and a pen from my desk.  She scribbled an address and phone number.  

“Seven o’clock,” she said.  “Don’t be late or I might change my mind.”

She straightened her clothes and left my office in a hurry.  

I showed up at her place ten minutes early.  She answered the door in a loose white shirt, a frilly white skirt, and cowgirl boots.  It was a very in-style look for Dallas in 2005.  

“Are you going to keep those boots on while I fuck you?” I asked.

She gave me a perplexed smile.

“I can’t believe how direct you are,” she said.  “Men are never like this with me.”

“Do you invite a lot of men over just to fuck?”

“Of course not.  I’ve never done this.  It’s been thirty years since I slept with a man I wasn’t dating or married to.”

“That streak ends tonight,” I said.

“Well then don’t make me wait.  I don’t want to get cold feet.”

I grabbed her hand and pulled her close.  We kissed passionately. I guided her toward the sofa and spun her around.  Then I bent her over the back and lifted her skirt. She was wearing silky pink panties that matched the bra I’d seen earlier.  I pulled them down around her knees. Her pussy was hiding in a thick black bush.

I quickly dropped my jeans around my ankles.  My cock was swollen. I buried it in her wet pussy.

“Oh my god,” Gail moaned.  “Fuck me hard. I haven’t been fucked hard in years.”

I grabbed her blonde hair and pulled.  She arched her back and slammed herself onto my cock.  I wanted to cum quick and then take my time during round two.

“Fuck me harder,” she pleaded.  “Fuck me.”

I slapped her surprisingly firm ass.  I drove into her again and again. Her big titties bounced wildly under her shirt.  

“You like being fucked by a younger man?” I asked.

“Yes,” she moaned.  

“You like being the sexy secretary getting fucked by your younger coworker?”

“Yes.  Yes,” she moaned.  

She kept asking me to fuck her harder.  I was happy to oblige. My thighs were getting tight from driving into her.  I was close to cumming when Gail lost control. She wailed like a banshee. I felt her pussy squeezing my cock.  I gave a few more thrusts and pulled out at the last second. I shot my load all over her bare ass cheeks.

Gail stood up and let her skirt fall back down.  She kicked her panties off.  

“I hope you don’t think you’re sneaking out the door now,” she said.

“I hope you’re not throwing me out,” I answered.

She offered me a glass of wine.  I pulled my pants up and followed her to the kitchen. As she poured the wine I wrapped an arm around her waist and stood behind her.  I swept her hair to the side and kissed her long neck.

“Already?” she asked.  “You ARE young.”

“Not quite,” I answered.  “But it won’t take long.”

I spun her around.  We stood face-to-face.  She looked her age, but I found the lines on her face made her more attractive.  We kissed.  

“You know I want to see them,” I said.

“Every man does,” she answered.  “They’re not as perky as girls your age.”

“I bet they’re magnificent.”

She grabbed both glasses of wine and led me to the bedroom.  

“Will you undress for me?” I asked.

“Yes.  But you don’t get to sit there in your clothes and just watch.”

“We can take turns,” I suggested.

“Fun idea.”

We stood at the foot of her bed.

“Shoes and socks,” she said. “Men look ridiculous if they undress and still have their socks on.

I sat down and untied my shoes.  I took them off followed by my socks.

“Take off your skirt, Gail.” 

She smiled and stood in front of me and slid it down to her ankles. She kicked it across the room.  Her shirt was still too long for me to get a good look at her pussy.  

“Your turn,” she said.  “Shirt.”

I stood back up and unbuttoned my shirt slowly.  Gail let out a mocking catcall.  

“Take off your top,” I said.

She made a show of unbuttoning her white shirt.  My cock was getting hard again. She let it hang open for a second.  Her big tits were stuffed into that lacy pink bra that I’d seen earlier.

“Jeans,” she said.

I unbuckled and unzipped.  I pulled my jeans down to the floor and stepped out of them.  There was a bulge in my boxer-briefs.

“Take off that bra,” I told her. It was the only thing left except her cowgirl boots.

She reached behind her back and opened the clasp.  Her big, bell-shaped titties spilled out. I was worried they would disappoint. But I was wrong.  

I dropped my shorts quickly.  My cock was almost at full attention.  I took Gail’s hand and pulled her to the edge of the bed to sit down.  I dropped to my knees in front of her and spread her legs.  

“What are you doing?” she asked.  

I kissed my way up her inner thigh.

“Oh no.  Oh my. Nobody has done that for me in ages,” she said.

I buried my face in her pussy.  I wasn’t in the mood to tease. I was overwhelmed with desire for her.  And I wanted her to cum for me again. I put two fingers in her cunt. I licked her clit.  Gail ran her fingers through my hair. I feverishly lapped at her pussy until she couldn’t take it anymore.  She squeezed my head between her thighs as she came.

She saw my rock hard cock when I stood up.  She started to lie back on the bed.

“I want you on top,” I said. “I want to watch those tits.”

She nodded.  I got into bed with her. She straddled me.  My cock easily slipped back inside her pussy.  

Gail knew how to put on a show.  She arched her back and stuck out her tits.  I could see my glistening cock sliding in and out of her pussy.  She put one hand on her clit and used her other to tease her nipples.  She moaned my name.  

The visual was stunning.  Her big tits jiggled as she rode my cock.

“You’re amazing,” I said.

She just smiled.  She kept a nice slow tempo.  She didn’t bounce off my cock like an inexperienced woman. She knew just how to ride.  She would go up and down the shaft and then stop and focus just on the head.  

“Do you like how I fuck?” she asked.  “Do the young girls fuck you like this?”

“No,” I panted.  

I had to concentrate to avoid cumming.  

She worked her clitoris with discipline  There was no rush. She was slowly building to an orgasm and taking her time on my cock.  

“I’m close,” she moaned.  “I want you to cum in me, okay?”

“Fuck yes,” I moaned.

“Oh. Ohhh,” she wailed.  “I’m going to cum. I want you to cum with me.”

She moved faster on my dick.  

“So close,” she said.  “Five. Four.”

I started to thrust up into her.  I grabbed her hips for leverage. My cock was trembling.

“Three.  Two.”

I lost control.  My dick spasmed inside her hot pussy.  

Gail worked her clit faster.  She came just a few seconds after me.  My cum filled her up at the same time.

She leaned forward and kissed me.  She rested on top of me until my dick got flaccid and came out of her.  

“Fuck, I needed this,” she said.  “It beats the hell out of going to Blockbuster and drinking wine alone.”

I stroked her back and ran my fingers through her hair. 

“Did it live up to your fantasy?” she asked.

“You exceeded it in every way,” I answered.

“I’m glad.  It’s good we both got something out of it. Will you stay here for a bit and hold me?  I feel a bit emotional now.”

“I’ll stay all night if you’ll let me.”

She seemed surprised. 

“I didn’t think you’d want that,” she said.  

“I don’t want to go anywhere,” I responded.

“Because you just want to fuck me again?”  

“No,” I said.  “We don’t have to.  It won’t change my mind.  But we definitely can.”

“I think I’d like that,” she said.

She started kissing her way down my body.  My cock wasn’t ready again. But it wouldn’t take long once she started using her mouth.

I knew the evening was just getting started.  




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