Overtime Ch. 2

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Boss takes the office work home.
4.2k words
4.59
55.6k
3

Part 2 of the 2 part series

Updated 09/30/2022
Created 02/17/2002
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I was walking my boss to my car after just fucking her in the office. The sun had just set, and Tasha had missed her bus, so I was going to drive her home. I could still smell the scent of sex coming from her pussy. We had both came in her underwear a few times, and she had put it back on before we left.

After helping her into my car, I got in and we left the city. Rush hour was over, but there was still a lot of traffic, so we were moving slowly. After about ten minutes, and having only traveled a little ways, Tasha showed a wicked grin. "This traffic is moving pretty slow, wouldn't you say?" she ran a finger over my leg.

"Yeah," I didn't know what she was up to, but I knew it might cause us to crash.

"There's just something about traffic that makes me so… hot." She pulled her hand back and now ran her fingers over her own legs. She kept this up for about a minute, before she moved her fingers underneath her skirt and started massaging her pussy through her dirty panties.

"Oh shit!" I shouted, almost loosing control of the car. This only seemed to make her hornier, and she plunged her fingers in beneath her panties. Leaning back in the car seat, she pumped her fingers in and out, her eyes closed and her breathing deep.

I could only take quick glimpses of her as I drove, but my dick was pushing against my pants. It felt like it would snap in half if it weren't released. But Tasha was only interested in her own crotch, as she plunged a third finger in. She let the back of her seat go as far back as it could, as she laid down. Her free hand cupped one of her breasts, as she slipped her shirt off.

"Holy fuck." I wanted to pull over to the side and jump her then, but she told me – through her gasps – to keep driving. So I did, but I had to unzip my pants and let my rock hard dick shoot out. Reflexively, unable to help herself, Tasha glanced at my erect penis. She rubbed her cunt faster, her thighs visibly trembling now, the milky flesh flushing pink like her glowing face. Tasha was panting, perspiration gleaming over her face, her soft lips slightly parted while her hips shivered, her fingers continuing to slide up and down across the damp fabric of her underwear.

"Want to know a dirty secret?" Tasha whispered between groans. "I sometimes do this on the bus ride home. I usually sit in the back, where I'm alone, and I just let my hand be bad. It's really fun when there's a hot chick sitting next to me."

My boss was bisexual. Somehow I wasn't surprised, but I was incredibly turned on.

Tasha arched her back, making her tits look bigger, and lifting her hips. Her panties were wet again, and so was her skirt.

"Not that I mind, but you better stop that, or else your going to cause me to crash."

Tasha smiled seductively at me, but pulled her fingers out from her pussy. They were dripping with cum, and she brought them to my lips. I licked them clean one at a time. When I was done, she sat straight again and straightened her skirt. She left her shirt on the back seat. Hopefully no cops would be going by. Who knows what she would do if we were pulled over, though it might be interesting to watch.

The rest of the drive went mildly, even though I had to force myself not to look at her tits. She had opened the window and the cold air blowing on them made her nipples as hard and big as my thumb.

When we arrived at her apartment, she had put her shirt back on, and directed me where to park. Then we went inside. Her apartment complex was nice, and I noticed a door leading to a pool and hot tub, but my eyes were glued to her swiveling ass. She lived on the 9th floor, so we took the elevator up. We were all alone, so when the doors closed I pulled her to me and stuck my tongue down her throat. She returned the favour, and wrapped her arms around my neck, while my hands went up underneath her skirt, and massaged her ass. My dick was still hard and was pressing against my pants, trying to get out and penetrate her cunt.

We didn't stop when the doors opened on her floor. We just backed out, hitting the wall, still kissing. We groped our way to her door and after a minute of fumbling with the key, she opened it and we fell in. The door closed itself behind us. I picked her up in my arms, and she lead me to her bed. Placing her down in the silk sheets, I started unbuttoning my pants.

"Hold on tiger," Tasha said to me. She stood up and went over to her closet. "I want do dress up for this." She smiled, took something from her closet and walked into her bathroom, closing the door part-way. "You can get us some beers from the kitchen."

I walked out of her bedroom and took a few steps down the hallway to her kitchen. Now that I wasn't so distracted, I could see that she had a nice apartment. The kitchen was a good size for cooking, and there was a small dining room for eating, and a big living room for relaxing. She had a large pullout couch, two matching chairs and a 36" screen TV Grabbing a couple of beers from her fridge, I walked into the living room and looked around. There were some video tapes on her TV, that turned out to be porno. There were no store markings, so they must have been hers. I recognized one as being almost all lesbian. Another one involved a secretary and her boss. There were also some tapes that were marked, "Julia and Tasha, office", "Tasha and Natalia, park". Armature porn. A third one really caught my eyes, "Family day, Tasha and her sister." It wasn't Tasha's handwriting, but it sounded hot.

"We can watch that later."

I turned around and saw Tasha standing in the kitchen, looking very sexy in a black lace teddy, complete with tiny black panties and black fish-net stockings. Even her tits looked bigger in it, and her panties rode up her ass.

"Wow," I said, my jaw hanging open.

Smiling, Tasha walked over to her TV and picked up a digital camera. Setting the camera on the TV, she pointed it towards one of her chairs.She then walked over to me, and pushed me down into the chair that the camera was pointed at. She then leaned over my lap to reach her beer on the stand beside me. My right hand caressed her bare ass while she was there, and I heard her purr like a cat. After a few seconds of this, she straightened herself so that she was now sitting on my lap, and she took off my shirt, in between drinks of her beer. When my shirt was off, she kissed my chest. She kissed it again, a bit lower this time, and continued kissing downwards until she was sliding off my lap and kissing my belly. When she couldn't go down anymore, she unzipped my pants, and my dick instantly shot up. Grinning like a school girl, she pulled my pants down and threw them down the hallway. Then she took a huge gulp of beer, almost emptying the bottle and licked her lips before lowering her head onto my dick.

She took the entire shaft down, deep throating me. I leaned back in the chair, enjoying the ride and letting her do the work. This time was better then at the office. On her knees, she pushed my legs open and kept bobbing her head. I would stare down, watching her long brown hair flow over her back like silk. I ran my fingers through her hair, stroking her head as she sucked. When she looked up, she would twirl her lips around the head of my dick, and her eyes would look into mine. It was so sexy.

When she wasn't looking up at me, I would watch her ass. She kept it up in the air, and it just screamed for attention.

As I finished my beer, Tasha deep throated my dick again. It slid down her silky throat with such ease, I swear she must be a pros at this. I wonder if she has this skill on her résumé. I wouldn't be surprised. With my dick down her throat, I was ready to explode. With one hand still playing with her hair, I held her head down on my dick. She didn't need the encouragement, but when I shot the cum down her throat, I was suddenly the boss. I let her gag on it a bit before moving my hand, and she slowly slid my dick out, though keeping the head inside, licking up all the cum. When she was done, my dick was clean, but her lips where sticky.

"Come here stud and kiss me." She said. I leaned forward and gave her a deep kiss on the lips, tasting my own salty cum on her tongue. When we parted, I stood up to go get us another beer. When I came back, Tasha was now sitting in the chair, and playing with her pussy again. When she saw me staring, she smiled and said, "I just can't help myself. I'm always playing with my pussy." She reached up her free hand and took a bottle of beer before I could open it.

"Don't want me to open them?" I asked teasingly.

"I have my ways." Still keeping her eyes on mine, she raised her hips, stuck the beer bottle up her ass hole, and with a flick of her wrist, opened it. She gave a small moan of pain, but she never lost her seductive smile. I had already opened mine, so she only did the one.

After taking a long swig of her beer, she unclenched her ass cheeks, and the bottle cap fell onto the floor. Kneeling down in front of her, I rested my arms on her legs and said, "You do have many skills."

"This is just the beginning Shawn." She then spread her legs wide open, causing her panties to ride up her crotch. It was my turn now, but I didn't mind.

Grinning, I bent my head down between her thighs, and with one hand, moved aside her panties. Her pussy was already glistening, but it smelled a mix of cum and soap. She must have cleaned it while she changed. Stretching out my tongue, I first teased her pussy lips, sending shivers along her spine. When her clit popped out, I started licking and nibbling it, causing Tasha to moan in deep pleasure. When her clit became hard, I bit down on it, making her squeal, and teased it. Tasha groaned in pain, but as her pain grew, so did her clit. After a minute of this, I let go and boy was I surprised when I saw that her clit was almost as big as my thumb.

"Oh wow," Tasha said. Even she was surprised.

I played with her clit for another minute, before diving into her pussy again. Now my tongue shot inside with rapid thrusts.

"Yes, oh god yes. Eat my pussy!" she cried. She then closed her legs, trapping my head between her thighs.

I was surprised and stopped licking for a second, but when I realized she wouldn't let me go until I satisfied her, I figured I'd better oblige her. With my face squashed into her cunt, all I could do was munch away. As my lips sucked her, my tongue kept massaging the inside. I couldn't hear Tasha's cries, but I felt them through her thighs. Her cries weren't the only things I could feel. As I munched away, Tasha's body shook with multiple orgasms. I could feel her shiver through her thighs, and with each shiver, my face was sprayed with droplets of cum from her cunt.

Finding it hard to breath, I moved my hands out from between her inner thighs and I slid them underneath her to grab her ass cheeks. Tasha moaned a bit more from this new attention, but when I spread her cheeks open and shoved two fingers up her hole, she almost jumped out of the chair, taking my head with her. When she settled back down, she once again had my head in a vice, and was now squirming in ecstasy. "Oh god, yes. Pump my ass!"

She started pumping her hips, my face going deeper into her cunt, and her ass moving up and down my fingers. When I stuck a third finger in her tight hole, that was as much as she could take. Crushing my head between her thighs, she leaned back in the chair and shook with a huge orgasm. A tidal wave of cum covered my face. When it finally ended, she released my head, and settled down. I pulled back from her wet cunt, letting her panties fall back into place. They were already starting to absorb her cum. I then pulled my fingers out of her ass with a wet sucking sound. I was happy to see that they weren't covered in shit, though they stunk of it. It didn't matter to Tasha though, because after she licked her own cum off of my face, she took my fingers into her mouth and started sucking them too, her eyes never leaving mine.

"You are so nasty." I said through a grin.

"You haven't seen anything yet, tiger." She let my fingers go and looked back to her bedroom. Taking the hint, I picked her up and carried her in my arms to her bedroom, after making sure she had picked up her camera, and our beers.

Her bedroom was of good size. She had a double bed at the end of the room that was covered in rumpled sheets and different outfits including other pieces of lingerie. Also in the room was a good computer desk, complete with a PC, files and papers, and a whopper of a dildo. It was black rubber and must have been a good 12" long, and 3" thick. Beside the desk was a hamper covered in more discarded clothing and lingerie, and another, smaller, dildo. There were pictures of both naked men and women posted on her walls, and a large mirror over her bed. And sitting on her nightstand was a half-empty bottle of wine, a porno magazine and a flesh colored vibrator, complete with a clit stimulator.

"How long have you been single again?" I asked her as I dropped her on the bed.

She landed with a grunt, but looked up at me with a feral grin. "I've had those for a while. He just couldn't keep up with them."

Tasha sat up on her knees, her back towards me, and leaned against my chest. I ran my fingers over her breasts and down her chest before pulling away. When I did, she slid forward to lay on her hands and knees, sticking her tight ass in my face. I bent forward and plant a kiss on her panties, before sliding them down. When they fell to her ankles, I positioned myself behind her and teased her cunt lips with the tip of my dick head. Tasha moaned in pleasure, but when I moved my dick to her asshole and shoved it in, she screamed in pain and surprise. She grabbed her bed sheets with a death grip and rode out the pain as her tight ass stretched to accommodate the size of my dick.

"Oh, you bastard," she said between grinding teeth. "Oh, god, oh god, oh god."

"You don't take it up here a lot, eh?"

"It's… been a… while."

Tasha had stopped crying out as she became used to the intrusion, and now she was moaning and groaning as I pumped inside her.

"Oh god, I'm cumming." My right hand slid down her thighs to touch her pussy. It was sticky with her honey. Her ass tightened again as she shook with an orgasm. It was so intense, that her arms fell from underneath her, and she buried her face in a pillow as she cried out.

When she was finished, I pulled out of her ass and turned her over, so she was lying on her back. "I want to try something I saw on the web." Before she could reply, I bent her legs back. Understanding what I wanted, Tasha bent her legs back so they were around her shoulders. Her hips were lifted because of this, and her pussy lay open bellow me.

Standing over her, I crouched down and stuck my dick down into her cunt. Tasha moaned in pleasure as she felt me enter, and smiled as we stared into each other's eyes. Not wanting this to get to mushy, I started pumping into Tasha a lot harder. Her eyes slammed shut as she groaned.

"Urgh, ohhh, yeah. Harder."

"You're the boss." I started going into her faster. Getting an idea, I slowed down as I climbed onto her bed, kneeling over her. On her bed, I was able to bounce, my dick now plunging into her with more force.

"Yeah, that's it. Oh my god, that's good." She cried out as another orgasm shook through her. While she was shaking, she let go of her legs, and they rested on my shoulders. Grabbing them, I used them for leverage as I pumped her harder.

"Oh god, YESSS!!!" Her pussy crushed my dick as a huge climax went through her.

I couldn't take anymore and I also came inside of her. "Oh yeah," I cried out.

I came for about one minute, but Tasha continued for more than five. It was intense. When she finished, I got off of Tasha and she then stood up. I moved over to where she was laying, and layed down myself. Then Tasha stood over me, and positioned her cunt over my dick. When she was ready, she slowly kneeled down to slide over my dick. Her pussy was still tight, though really slick. My dick slid in easily, right down to my balls. Leaning back, Tasha untied her lingerie and let it fall to the floor. She now sat over me, wearing only her fish-net stockings. Her small breasts bounced along with her movements.

I slid my hands up her chest to grasp her breasts as she ground her pussy onto my dick. Tasha started thrusting her hips back and forth, as if she were riding a horse. I could feel my dick going deeper and deeper inside of her.

"Yee haw!" she shouted. With one hand she was holding onto the blanket bellow us like it was a harness and her other hand was waving around over her head, as if she held a cowboy hat.

My fingers tweaked her nipples before moving down her chest and stomach to firmly grasp her ass. Squeezing tight, I helped balance her and she rode me even harder now. My dick got harder inside of her, and I must have found her G-Spot, because all of a sudden, she stopped ridding and just started grinding down into me, trying to shove my dick further in.

"Yeah, right there. Yes. Yes! YESSS!" Her pussy crunched down on my cock, and she arched her back, sticking her tits out in the air, as she had her biggest orgasm of the night.

I was also ready to have one, but I tried to hold out. The feeling was intense. My dick felt like it was a dam that about to explode, but waves of pleasure kept flooding through me hat I didn't want it to stop. My fingers dug themselves into her ass cheeks as I rode out her orgasm. But because I wouldn't release, my dick just kept getting bigger, much to Tasha's enjoyment. It was so big now, that I could swear that the only way I could pull out of her was to shoot my load. To help control it, my fingers spread her ass cheeks open, and I stuck two fingers from each hand inside her asshole, which had been closing shut from lack of attention. Tasha wasn't ready for this, and her orgasm intensified.

"Oh fuck Shawn, cum inside me. Now. I want to feel you cum at the same time as I do. Shoot it deep inside me. Don't worry, I'm on the pill."

Unable to hold it anymore, I did as my boss ordered, and just exploded inside her. It was incredible. I went light headed, and my right leg started shaking uncontrollably, much like a rabbit or a dog when you scratch it in the right place. My fingers were shoved further up her ass as I pulled her hips down so hard my balls were getting shoved up her cunt.

"God yes. FUCK. Fuck. FUCK!!!!!" Tasha cried out. Her long brown hair had fallen over her face during her wild ride.

But neither of us where done yet. After I finished cumming, my dick was still hard, and now extremely sensitive. Tasha was also still active. Instead of both of us being tiered, we actually had more energy. We started fucking harder. Both of us were now grunting like animals in heat. Our naked bodies where glowing with sweat. Tasha fell down over me, holding herself inches above me by her elbows. Because she was a few inches taller than me, her boobs were close to my face, so I leaned up a bit to suck on one of them. Tasha closed her eyes and continued groaning. We both increased our pace, going at each other like wild animals.

"Fuck me Shawn. Yes, harder, harder. Stick that big cock of yours up my pussy."

I changed our position so that we were both lying on the bed sideways. I was behind her, and I lifted one of her legs up high, so I could fuck her cunt.

"Oh god, yes. More. Harder."

I reached over her and groped around her nightstand. After a few seconds I found her vibrator and took it. Tasha had her eyes closed, so she didn't see me bring it behind her, but she sure felt it when I stuck it between her ass cheeks and shoved it up her open ass hole.

"Ohhh FUCK!!!" She shouted, but I felt her climax again. And she really shook when I turned it on max. "Ugggghhhh." All she could do was moan as her cunt muscles crushed my dick.

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