Need A Lift?

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Sexy coworker is really grateful for a ride home.
2.7k words
4.35
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Part 1 of the 4 part series

Updated 09/22/2022
Created 11/04/2001
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"Would you like a ride home?"

Cynthia was standing just inside the office door, doing up the zipper on her winter coat, as I came down the stairs on my way out to my car. She worked part time in our office as a data-entry clerk, and I knew she had no car and since she lived off the bus lines, she ended up having to do quite a bit of walking to get to and from work, her part-time wages making cabs out of the question. It was starting to get a bit cold to walk, so I thought she might appreciate the break.

She looked up from her zipper. "OK," she said. "If you don't mind. Thanks, James."

We walked out to my car in the parking lot, Cynthia a few steps ahead of me, rushing to get out of the chill. I watched her as I followed. She'd been working for us for about four years. She was in her late 40s, had divorced a couple of years before - around the same time I had - and she had two grown sons almost my own age, although you wouldn't think it to see her. She kept herself in great shape. She had long, straight black hair that reached down to her slender waist and a hard ass that said she still made it to the gym pretty regularly. Her tits were big and round, firm 38Cs, and she showed them off with the tight, form-fitting dresses she often wore to work. In the past few years I'd often fantasized about what it would be like to slide my cock between those luscious tits and to see those full lips with their bright red lipstick wrapped around it.

"Are you going to unlock the car and let us in," she said, shivering with her arms wrapped around her chest, "or are you just going to stand there all evening?"

"Huh? Oh, sorry," I said, fumbling the keys out of my pocket into the lock. Cynthia giggled and climbed into the passenger side.

"I really appreciate this," she said as I started the engine. "You're sure you don't mind?"

"No, of course not," I said. As if, I thought, my mind starting to wander again as I pulled out of the parking lot. At 32, I wasn't in as good shape as I had been in college, but I still managed to take care of myself, visiting the gym every now and then, and at six feet and 180 pounds I still had only a bit of a tummy to suggest that I earned my living sitting on my ass behind a computer monitor all day. Since the divorce a couple of years ago, I'd been doing OK with women and had had a few casual girlfriends, but I did go through long dry spells from time to time. In fact, I'd been in one for the past few months now, and the thought of Cynthia's tits popped into my head again.

She lived on the other side of town and it took us about 15 minutes to get to her place, making small talk along the way. She directed me to her apartment building. As we approached, she thanked me again for the lift.

"That was so nice of you," she said. "Would you like to come in for a cup of coffee, to warm you up?"

"Sure," I said. What, are you kidding? I parked in the lot behind her building and we walked up to her second-floor apartment.

The place was small. One room served as both living room and bedroom, with a loveseat against one wall facing a small TV and a double bed taking up the entire far end. There were two doors leading off the main room - a small kitchenette and the bathroom.

"Have a seat," she said, draping her coat over the back of a chair at the small dining table and disappearing into the kitchen. I took my coat off and put it on the chair over hers and sat down on the love seat. From the kitchen came the sounds of Cynthia making the coffee.

A few minutes later she reappeared with two steaming mugs. She set them down on the coffee-table and dashed back into the kitchen, reappearing with a bottle of Bailey's.

"All I had was instant," she said apologetically. "I hope you don't mind. I'm having mine Irish," she said, shaking the bottle. "Like some?"

"Sure." She poured a generous amount of liqueur in each mug then handed me one before settling onto the loveseat. It was a pretty cozy fit, and we tried to sit facing one another from either end while we talked. We talked for quite a while, mostly about work, and whenever our mugs started getting low, Cynthia would top them up with Bailey's. When the bottle went empty, she got a bottle of wine from the kitchen.

By now I was feeling warm and a bit flushed from the booze. After handing me a full wine glass, Cynthia sat down, this time with her back to me, leaning back against me.

"Do you mind?" she asked.

My cock started to stir. I worried she might feel it through my jeans against her back. "No, I don't mind at all."

She settled her head against my chest with a contented sigh. I wasn't sure what to do with my free hand, so I stretched my arm out along the back of the couch.

"You're such a sweet guy," she said. "My husband would never do this. You know," she raised her arm back above her head and softly stroked my cheek with her arm, "just sit like this and cuddle."

"Yeah," I said, not really sure what I was agreeing with. Her hand was still stroking my cheek, her fingertips gently brushing against my lips. Tentatively, I brought my arm down from the back of the couch and touched her cheek, tracing the line of her jaw and chin with my fingers. She smiled and sighed. I brushed my fingers over her lips and her tongue slithered out, gently touching the tip of my middle finger before sucking it into her mouth.

I moaned softly and she released my finger, turning her face up toward mine. Her face was flushed and her eyes were half-closed. I lowered my mouth to hers and kissed her, softly at first, then more urgently as her lips parted and her tongue snaked out, seeking out mine. I rubbed my hand over her cheek and into her hair, combing it out, until she took my hand in hers and placed it on her right breast. Through the fabric of her blouse and bra, her nipple was rock-hard, and she groaned into my mouth as I started to knead her tit.

We broke our lip lock just long enough to set the wine glasses on the table, then I stretched out on the couch and she lay full-length on top of me. I sucked the soft skin of her neck into my mouth and found her earlobe, running my tongue over it as I sucked, and I pulled her blouse from her slacks and ran my hands over the bare skin of her back.

"Ohh, yeah," she said as my hands found the strap of her bra and undid the clasp. She raised herself off me and stuck her tongue into my mouth as my hands moved to the front and undid the buttons on the blouse. With her shirt open, I pushed up her loosened bra and ran my hands over her big, hard tits, the nipples the size of pencil erasers. I lifted my head off the couch and took her right nipple in my mouth, sucking hard, flicking it with my tongue and gently nibbling with my teeth.

"Argh!" she said, wrapping her hand behind my head and pulling me into her chest. Then she pulled away and kissed me hard on the mouth. "Let's move to the bed," she said, her tongue snaking into my ear.

She got up and walked the few feet across the room to the bed and sat back. I followed and took off her blouse and black-lace bra and went back to work on her tits with my mouth as I undid her pants. I pulled them down and laying back, she lifted her ass from the bed to let me get them off. Underneath, she wore a black lace thong, the thin strip of fabric disappearing into the crack of her luscious ass, with the black hairs of her bush peeking out from the edges of the triangle of fabric in front. I leaned down and ran my tongue up the inside of her thigh to her pussy lips, which were also wrapped around the thin strip of fabric.

"Get undressed," she hissed. I stood and took off my sweater. Cynthia slid off the bed onto her knees on the floor in front of me and tugged feverishly at my belt buckle, then pulled down my pants and boxers, freeing my cock, which stood straight out from my body. Cynthia moaned and cupped my balls with one hand as she ran her tongue around the tip of my cock, poking into the peehole. I shuddered as she took the head into her mouth, still running her tongue around it, then with one sudden movement she took all seven inches into her mouth and I felt the tightness of her throat squeezing the head.

"Ohh, ahh!" I moaned, wrapping my fingers in the long black hair at the back of her head as she started to bob back and forth on my cock. Cynthia was moaning too as she sucked me, and I could feel her saliva running down the shaft to soak my balls. Every now and then, when her mouth reached bottom, she'd pause in her bobbing long enough to snake her tongue out from around a mouthful of cock and run it over my balls. Then on an upstroke, she'd let my cock slip from between her lips and, looking up at me with her round brown eyes, she licked underneath my shaft as she rubbed my glistening cock all over her cheeks, taking first one ball then the other into her mouth and sucking gently, before deep-throating me again and bobbing up and down, faster and faster, as one hand rubbed my soaked balls and the other squeezed my ass.

It took only a few minutes before I felt my orgasm start to stir in my balls. "I'm gonna cum," I breathed hoarsely. Cynthia moved her head faster, sucking harder and making slurping noises as she moved back and forth on my cock. With a cry, I grabbed her hair as the first shot of my hot cum erupted into her mouth.

"Mmmm!" Cynthia moaned, letting the second shot hit the back of her throat before replacing her mouth with her hand, jerking me off as she held my cock aimed at her open mouth. I came on her tongue, and a few spurts hit her cheek, then she took me into her mouth again and pressed her tongue against the underside of my shaft, running it up and down to squeeze out the last of my cum.

"Jesus!" I said, collapsing to my knees in front of her. I kissed her, pushing my tongue between her lips, tasting my cum in her mouth, licking it off her chin before kissing her again, feeding it back to her as Cynthia continued to gently stroke my now-softening cock with her hand. I reached down between her legs and felt the fabric of the thong was soaked.

"Get up on the bed," I hissed. She climbed up and lay on her back. I pulled off the thong, spread her legs and dived right between them, burying my tongue between her swollen pussy lips.

"Ohh!" she cried as my tongue flicked across her clit. I sucked her button into my mouth hard and pushed first one, then two fingers into her wet slit, rubbing hard and fast against the front of her hole. Her hips came up off the mattress and fucked back against my face.

"Oh my god!" she cried. "Ohh, god, James, I'm cumming, I'm cumming, ohhh . . ." Her pussy gushed against my face and hand, her juices running down into her crack. As she came down from her orgasm, I kept right on eating her and finger-fucking her hole.

"Move up here," she moaned. "I want your cock in my mouth." I shifted on the bed so that my crotch was in front of her face and, lying on our sides, I lifted her leg in the air to give me better access as she took my now-semi-hard cock in her mouth.

I continued sucking her clit as I moved a wet finger from her pussy to her asshole. Her pucker was soaked from my saliva and the juice from her cum, so I managed to slip a finger in easily.

Cynthia moaned and sucked hard on my cock. "Fuck me, James," she panted, releasing my cock. "Please fuck me. I want your cock in me."

She rolled onto her back and I climbed between her legs. My cock slipped easily into her pussy and we kissed deeply as I pushed all the way into her, pausing for a few moments to savour the warmth of her tight pussy around my cock and her juices running down my balls.

I fucked her with hard, deep strokes, then pulled out. "Turn around," I breathed, and Cynthia rolled over onto her hands and knees. I pushed my cock back into her pussy and she pressed back against me. I grabbed the cheeks of her perfect ass and squeezed them hard, then pressed a thumb against the pucker of her asshole. The tip of my thumb pushed in and the whole thumb easily followed. Cynthia was grunting as I fucked into her. She looked back over her shoulder and shook her long, black hair from her face.


"Fuck me in the ass, baby," she said, her eyes glazed over with lust. "Put your cock in my ass. I know you want to."

I pulled out of her pussy and pressed the head of my cock to her asshole, which was so wet from her juices that I slid right in. I stopped when the tip broke past the sphincter, to give Cynthia a chance to get used to it, but she pushed back against me with a frustrated, lustful wail until I was buried to the hilt. She lowered her head to the mattress and I started pumping in and out of her ass.

"Oh god," I moaned. "Your asshole is so tight."

"Fuck my ass, baby," she groaned. "You fuck my ass so good. Split me open. Ohh, god, your cock feels so good in my ass."

I fucked her hard for a few more minutes, then pulled out and rolled her over onto her back. Raising her legs until her ankles were at the sides of her head, I positioned myself and pushed my cock back into her asshole. As I started pumping hard again, Cynthia reached down and started to furiously rub her clit. When I leaned down and took a nipple in my mouth, she started to wail.

"Oh yeah! Ohh, oh oh! I'm cumming! Oh, fuck me hard, fuck my ass hard baby, I'm cumming!" Her asshole squeezed my cock tightly as I continued to pump through her orgasm. I could feel the tingle start in my balls.

"I'm gonna cum," I panted.

"Cum in my mouth, baby," Cynthia hissed. "I want to taste you. I want to suck your cum."

I fucked her ass hard for another minute, then pulled out. Cynthia quickly moved into position to take my cock into her mouth and as she squeezed my balls, I unloaded in her mouth. She didn't swallow - she held my cum in her mouth and let it coat my cock as she moved back and forth on it. When I was done shooting, looking up at me with a smile, she swallowed what was in her mouth, then licked my cock clean.

We collapsed together in a tangle of limbs, Cynthia smiling as she lay her head on my chest.

"So," I said, "do you think you'll need a ride home again tomorrow?"

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