Overtime Ch. 1

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He works overtime with femme boss.
4.2k words
4.47
110.9k
7

Part 1 of the 2 part series

Updated 09/30/2022
Created 02/17/2002
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I work for a small business. My job is to manage a database mailing list. It's not the most exciting work, but I'm only in the office twice a month.

Well, I haven't been into the office in almost a month, because my boss has been away on vacation. So I have a lot of work for her to go over, and because they wanted me in during the afternoon, it meant staying late. When I walk into the office, my co-workers greet me, and we do the usual small talk; how have you been, anything new, etc… When I see my boss, I walk over to her. She's no model, and a bit geeky looking, but there's still something attractive about her. She was around thirty, but looked to be about twenty-six. She stands over six feet tall, and she has a slim figure that probably moves perfectly while dancing. She has light brown hair that hangs down past her shoulders, and brown eyes hidden behind sixties glasses. She usually work flashy tight pants that she would have custom made, but today she wore a black leather skirt, and a tight shirt that didn't quite cover her navel. She small breasts were easily noticeable. I was once again thankful of the casual work environment in the office.

"Hi Tasha," I said as I got closer.

She turned in her chair and smiled. "Hi Shawn," she replied in her fast tone. Her voice was deeper than most women, but still feminine.

"Got the work for you to look over," I placed the CD on her desk.

"Great, thanks." She put the CD in her computer. "Pull up a chair and we'll go over it."

"There are a lot of records there, so it will take a while."

"No problem, I was going to be staying late anyway," she said.

So I sat down and we spent the next hour going over a fraction of the work. It was going to take at least another three. After the second hour, we decided to take a break. It was already four o'clock, and some were starting to leave.

"Bye Tasha, and good luck with Jim tonight," one of the office girls said as she walked out.

"Thanks Kim. The bastard should be out by the time I get there." She replied.

I didn't say anything, but Tasha saw my curiosity. "Jim's my boyfriend," she said. "Well, ex-boyfriend to be more precise. I caught him cheating on me in our own bed, so I threw him out last week. He's supposed to get the rest of his stuff out today."

"Sorry to hear this," I said, because I didn't know what else to say.

"I'm not. I was getting tiered of him anyway." She looked back at all the work we still had to do and then back to me. "Are you hungry? Why don't we go for super or something before we continue."

I wasn't really hungry, since I had eaten before arriving, but agreed anyway. We went to a small restaurant, where we ordered a quick meal, but not one that we would be rushed to eat. While we waited we talked.

"So how have you been doing Shawn? Been a while since you were last in the office."

"I've been good, nothing too exciting. The girl I had been seeing decided to start seeing someone else, but we weren't together long."

"Sorry to hear that," she replied, giving me a grin. I couldn't help chuckling, as I took a drink from my cola.

"Where you two fucking?"

I almost chocked on my drink. "Huh?" I said in dumbfounded confusion.

Then I felt her foot rubbing against my leg. "It's obvious that Jim and me fucked, we've been living together for over a year, but what about you and your girl? Was she good? Where you good?" She grinned seductively.

"Umm… Well, we fucked a few times, and we were both good. We didn't do anything during our last few dates though."

"So you're probably horny as hell, huh? I know I am. Jim hasn't satisfied me in over a month. Probably because he was fucking some bimbo. What you need is an older, more experienced woman." Her foot had moved up to my crotch.

Our waitress chose that moment to bring us our food, and we ate it in silence. Tasha had pulled her foot back, and the seduction left her eyes and smile, leaving me to wonder if these things had even happened. I could still feel my dick stretching the fabric of my pants, trying to pop out, but maybe it was just my imagination. When the check came, Tasha picked it up and charged it to the company, and then we returned to the office. During the walk back, Tasha hooked my arm in hers, but she's done this before. We talked a bit more about work, but I just thinking back to our conversation before we ate. When we entered the building, and walked up the stairs, I stayed two steps behind her, so I could look up at her ass. Twice I saw up her skirt a bit, and I could swear she wasn't wearing any panties. My dick was stiffening again.

Inside the office, the remaining employees where starting to leave. They said their goodnights and then left Tasha and me alone. We sat back down at her cubicle, and went back to work. We worked another hour in silence, the only words spoken where the corrections she told me I had to do. It was now close to six o'clock and was starting to get dark outside because it was still winter.

"I'll be right back," Tasha suddenly said. "I just have to pee."

She walked out of the office, leaving me alone. I used this moment to stand up and stretch. I bent down to adjust my shoes, and I noticed something unusual under her desk. A large raw hind bone. One knot was cut off at the end, and smoothed round, making it look like a giant cock. It was also sticky at that end, and smelled like pussy. I realized that I was holding Tasha's dildo. I suddenly remembered seeing this before.

It was right after I had started working here. I was working late again, and I had left after everyone else, except Tasha. I had gotten outside the building before I realized that I had forgotten a disk in the office. So I went back up to get it, and that's when I saw Tasha at her desk. Her flashy pants where lying on the floor, and her silky panties where lying around one ankle. She was sitting in her chair, her legs spread wide, and she was shoving something big into her pussy. I couldn't see exactly what it was, because she had her back to me, but her cries of pleasure told me that it was working.

I just stood at the open door, watching. I wanted to whip out my dick and jack off, but I didn't want to get caught and risk loosing my job. I must have been standing there for fifteen minutes before she saw me. She had stopped playing with her self, and had pulled out her toy —the very bone I now held — and she started sucking it like a Popsicle. That's when she had turned around and saw me at the door. I had quickly jumped back, out into the hallway, but I still saw her smile. When I was back in the office the next day, it was as if nothing had happened.

"I see you found my nasty secret again," I heard behind me.

I dropped the bone and turned around to see Tasha standing over me. I was at eye level with her exposed belly. If I looked up, I could see up her shirt, and if I looked down, I'd be staring at her crotch, that was probably still damp from her pee. My dick got hard again.

I couldn't keep staring at her navel all night, so I looked up into her eyes, catching a glimpse of her breasts for a second.

"It's okay Shawn. I was actually hopping you would. Ever since you caught me that night, I'd been fantasizing about you. About us." She sat back down in her seat, but she didn't cross her legs this time. Instead, she picked up the bone I had dropped, and ran her tongue over its head, her eyes staying locked on my eyes the whole time. "That's why I wore a skirt today. Because I wanted it to be easier to shove this in once you were gone. I wanted to pretend it was your massive cock."

She chose that moment to spread her legs open as wide as they could go, stretching her skirt and exposing her shaved pussy. "Holy fuck," I said.

Then Tasha slid the bone down her body, and brought it to touch her pussy lips. "It was very cold walking outside without any panties today." She said as she teased her cunt (and my dick.) "But it was worth it. The cold tingled against my exposed flesh, but knowing that you were right beside me, staring at my ass." She became excited and shoved the bone into herself. She cried out in both pain and pleasure, but relaxed into her chair as she started pumping it. "Only Julia saw me do this before, but she's gone now." Julia had been fired over a month ago. I didn't know why, I was out of the office, and I never asked.

My dick was killing me as it pressed against my pants, starting to bend with no more room to grow. Tasha must have seen my bulge, because she stopped pushing the bone in and leaned forward. As her hips moved, the bone was pushed further in by the chair. When she could reach me, she slowly unzipped my pants, freeing my cock. "That's better," she said. But she wasn't completely happy, so she pulled my pants and shorts off completely, letting them lie on the floor. "No fair me having all the fun, and you getting all the entertainment." She leaned back into her chair, and continued manually pumping the bone. Now that my cock was free, my hand went straight to it and started jacking off.

"There you go Shawn. But you need more." Leaving the bone buried in her pussy, she took her purse and from it removed a pair of white, silk panties. "Here, jerk off into these. I wore them when I went into the bathroom, and came in them twice." I took her panties and my fingers became sticky. They were soaked with her cum. I didn't realize she was in there that long.

Tasha licked her fingers clean and returned to fucking the bone, though her eyes where open now and watching me. There wasn't much to fuck in her panties. She has a small, tight ass, so she only needed small panties, but I wrapped them around my huge cock, sighing when I felt her warm cum spread from them onto my dick. I slid it up and down my shaft slowly at first, covering my entire length with her cream, before going faster. Within minutes, all her cum had evaporated from the friction, but I didn't care. When you can't fuck some real pussy, there's nothing better then a chick's silk pantie. And when it belongs to someone you know, it's even better.

"There you go," she said to me. "But I think you need a bit more incentive." Then she took off her shirt, letting her small round breasts hang out. She was wearing no bras, but what really caught my attention were the rings hanging from her erect nipples. Both her tits where pierced. "A little something from my school years," she said as she fondled her breasts.

"Holy fuck," I said again, as I started jerking faster. I was leaning forward a bit to increase the pleasure I felt.

"I got them when I started stripping and doing amateur porn."

"Fuck!" I said loudly. I could feel my orgasm coming.

"You should see my clit ring." She moved the bone down a bit, and that's when I saw her little pink piece of flesh, only it wasn't so little, and it had a gold ring through it.

That was all I could take. The combination of her soiled panties, her playful pussy, her pierced boobs and clit, plus the fact the she's my boss I couldn't hold it anymore. My load exploded into her panties. The white material became soiled with my cum, quickly turning from white to yellow. My stomach muscles contracted in pain from the bad angle, but I rode it out.

"Oh, yeah!" Tasha also cried out. After seeing me ruin her panties, she came herself. I could see cum dribble from her pussy and down the length of the bone.

"Oh wow." I said, watching her layback in her chair. She had a satisfied expression on her face, but her eyes were still hungry. I must have looked the same.

"I'm not done with you yet," She said to me. She slowly pulled the bone out of her pussy, and ran it between her tits, covering them and her chest with warm cum. Then she handed it to me and said, "I like to keep this clean, so it doesn't get nasty and I'm forced to throw it out." I understood what she meant, and I started licking it. I didn't like the taste of raw hind, but it was masked by the salty taste of her juices. It didn't take my long to clean it, and when I was done, she took off my shirt and let it fall with the rest of our clothes. We were now both completely naked, sitting across from each other.

I still had her panties hanging from my dick, and Tasha took them, her fingers slowly sliding along my still erect shaft. Standing up, she slipped them back on, her eyes closing and her mouth sighing as she felt my cum touch her pussy lips. "I want to wear these for a while." I had no complaint. She looked incredible in them. Because of all the sum, they were almost see through. When I tried to stand up to take her in my arms, she pushed me back down and knelt down in front of me. Grabbing my dick with one hand, she pumped out the rest of the cum from it and then licked it with the tip of her tongue. "Oh wow," I said again.

When she finished cleaning my cock, she stuck the whole thing into her mouth. I sat back and enjoyed the ride. Tasha swallowed the entire length of my shaft, and I moaned as it went down her throat. She was obviously experienced at this. As she went up and down my dick, she would look up at me. I loved it when my dates would do that. I always found it more intense looking into their eyes as they sucked me off. She would occasionally stop and jack my dick off a bit, before going back to swallowing. When she wasn't looking up at me, I would stare hungrily at her ass. She had it stuck up in the air, and her panties made it look more appealing.

When she saw me looking at her ass, she said, "You know what? With these wet panties, it' getting really cold up there." She stood up, took my hand, and led me to the lounge, where there is a couch. She pushed me down onto the couch, and then climbed on top of me. She turned around so her tight ass was in my face, and she went back to sucking my dick. I pushed aside her panties, exposing her dripping cunt, and pushed my face into it. My tongue went deep inside, and she gasped in pleasure.

"You do learn fast," she said.

To thank her for the compliment, I took two fingers and dipped them into her dripping cunt. She arched her back, and I felt my dick slide down her throat. I kept pumping my fingers while she sucked, and when they got soaked, I'd pull out and stick my tongue back in. I just couldn't believe that I was 69'ing my boss. I spread her pussy lips open with both hands now, and continued licking up her wetty goodness. As I buried my face into her cunt, I slipped my fingers over her ass, and under her panties. Tasha moaned in pleasure, but didn't stop. I was getting ready to cum right in her mouth and I wanted her to do the same to me. My fingers continued their exploration by slipping between her cheeks and into the tight little hole they found. Now Tasha did gasp at the sudden and unexpected intrusion, and she took my cock further in her mouth, sucking on it like a Hoover vacuum. I wanted to continue surprising her, so I moved away from her cunt, and brushed her ass hole with my tongue. I had never gone down on an ass before, but I found her smell intoxicating, and I knew her ass was clean, because I felt nothing inside. Pulling the hole open a bit more, I stuck my tongue deep inside.

Tasha's eyes opened wide and she shouted out, "Oh FUCK YEAH!" then went back down onto my dick, sucking it hungrily.

Her asshole tasted terrible, but the whole idea of this was so hot that I didn't care. Tasha was now almost choking on my massive cock, engorged because of the excitement. I took my tongue out of her ass and stuck it back into her pussy. Tasha moaned and looked up from dick. She turned her head to face me, her hand pumping my cock, and said, "I want to taste you. I want to feel your cum slide down my throat." She returned to my dick and went back to sucking, now with a purpose. She was no longer teasing it and massaging it; she wanted the creamy centre.

Her hips moving with her excitement, she pushed her pussy into my face and sucked furiously on my cock. I couldn't take anymore and obliged her hunger. With my cock down her throat, I unleashed a wave of warm juice. She took a bit of my cock out of her mouth, to better savour the taste on her lips and tongue, but she kept her eyes closed and her ass moving. I felt her pussy clamp down on my fingers and the tip of my tongue, and tasted her own orgasm.

When I was spent, she sat up on my chest, her pantied pussy slowly sliding down my face as she slid her hips forward, her back still to me, and ran her fingers along my dick. She was cleaning off the few spots of cum she had missed with her tongue, and was licking them off her fingers. When she was done, she looked over her shoulders at me and smiled down.

I smiled back as I ran my fingers up along her spine, sending shivers through her skin. She ground her sticky pussy into my chest while I tickled her, and my cock was rock hard once again. Seeing this, she swivelled herself so that she was now facing me, and slid her hips down, so her pussy was aligned with my cock. Then she lifted her hips, and slid her panties off. She tossed them at me, where they landed on my face. I had a sticky coating of cum on my face when I took them off, and she laughed with girlish mischief. I took a big sniff from her panties, almost melting from the aroma, and then put them on the floor. Hanging over my hard cock, she positioned my dick underneath her, and slowly slid down the length of my shaft. She had the entire length inside her and was now leaning forward, thrusting her hips up and down, back and forth, like she was riding a horse. It was incredible watching her. My boss was riding me like a stallion. Her petite tits bounced wildly with her movements, and I slid my hands up along her chest to grab them, and she smiled. Her eyes opened up to slits as she looked seductively down at me, and then she increased her pace. She started whispering, "Up and down, back and forth, faster, faster. Up and down, back and forth, faster, faster." It was like she was remembering lessons taught to her.

I just smiled and continued massaging her tits, twisting her nipples between my fingers. They stuck out almost an inch and were rock hard. I pinched one, and she gasp in pain. Giving me an evil smirk, she twisted her hips the slightest bit in revenge. My dick twisted along with her and I groaned from the pain.

Not to be outdone, I suddenly sat up, pulling her down when my hips went back, but keeping her in a sitting position. She was still bouncing speedily on my dick, but now I was adding my own hard thrusts into her, moving in sync with her. Her surprise disappeared with her purrs of pleasure, and she wrapped her arms around me in a lovers embrace and kissed me passionately. I returned the kiss, my tongue moving into her mouth and massaging hers, while my arms wrapped around her waist, my hands sliding down to cup her ass. Her breasts were crushed into my chest, and if anyone saw us, they would have thought we were one person.

We kept this up for five minutes before Tasha broke our embrace and leaned back. "Oh fuck, I'm going to cum." I knew that she had already had cum, having felt her pussy clench my dick, but this must have been a big one, because I couldn't move my dick. Her pussy muscle had clenched so tightly on my cock it was stuck. Sweat covered both of us like a blanket, and Tasha looked like she was glowing. "Cum with me Shawn," she panted. "I want to feel you cum as I do."

I had no problem with this because I was about to cum too, thanks to the pressure on my dick. Tasha fell back into our embrace, and we held each other as we simultaneously came. "Ughhhh!!!" Tasha moaned. "Yesss, oh god yesss!" It lasted about two minutes, both of us shaking from the intensity. When it was finished, we both collapsed back down onto the couch. Tasha lay on top of me, her eyes closed and her breathing soft. She looked like she was asleep, but then she opened her eyes to slits, and smiled.

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