The Cock and Tail Waitress 2

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The hooker's holiday continues.
2.3k words
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Part 2 of the 6 part series

Updated 01/26/2024
Created 01/21/2024
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I knew Cindy's pussy would be sore in the morning. A lot of the cum that had flowed out of her had soaked into the seat and had started to dry. As I scrubbed the wet spot, I thought over the evening. The sight of her being gang-banged had made me super horny. Witness the speed with which I had starched my pants. I was still hot to trot. The smell of the cum-stained seat gave me a hardon. The friction between my pants and my glans had me panting as I worked. In a couple minutes, I soaked the front of my pants again. I couldn't get the vision of her being repeatedly fucked out of my mind. No sooner had my pecker become flaccid than my erection began to return.

The money had been an unexpected bonus. It had been handed to us. We hadn't asked for it. We would have to discuss what to do with it in the morning. We could upgrade our room in the next city we planned to visit, or we could add it to our house buying fund. With that extra money, we could buy a house six months sooner. The best part was we wouldn't have to share it with the IRS.

After half an hour I went back to our room. Cindy stirred as I poured the dirty water into the sink. "Where were you?" she asked sleepily.

"I was cleaning the back seat," I said. "How do you feel?"

"I feel like fucking your brains out. I'm still hotter than hell. What about you?" She noticed the wet crotch in my pants. "You've cum again, and not in me." She pouted playfully. "I'm insulted."

"I can't get the last couple hours out of my mind."

"How was your fantasy? Was it what you expected?"

"I wasn't expecting a mob, just one guy fucking you while I watched."

"But you were still turned on, weren't you?"

"Absolutely. I'm about to blow my wad again."

"Then get out of those clothes and get over here."

Cindy jumped out of bed naked and grabbed the waistband of my pants and dragged me to the bed. She shoved me on my back and unzipped my fly. My turgid member protruded though the opening. Without bothering with the slightest preliminary, she straddled my hips and guided my cock into her already wet pussy. She slowly settled down onto my lap savoring the sensation of my dick entering her. "I've been thinking about it too," she said. "You were supposed to pick me up, but I screwed up that plan."

"Maybe we can try again tomorrow night. It might work better if I go in first.

"I agree. That first guy's hand got me so hot I couldn't remember why we were there. When he touched my pussy, I had to be fucked right then. If you hadn't been there, I would have jumped his boner right there at the bar." I wiggled my butt a bit. "That feels great. Don't go too fast. I want this to last." She placed her hands on my chest and slowly rocked back and forth on my dick. "Mmm. That's how fucking should feel."

"Didn't you cum at all?"

"A couple times. Most of them weren't in me long enough to get me anywhere near the edge, let alone all the way."

"I guess we shouldn't do that again."

"It's weird, but the times I came, I was thinking about the money we were getting." She continued her rocking motion. "What should we do with it?"

"I don't know. You handle our money."

"You're the accountant. I'm just a cocktail waitress."

"With a business degree."

She playfully slapped my cheek. "You sound like my father. He only thinks about the job title."

"He knows how much you make."

"I've told him, but he doesn't believe it." She leaned over and pressed her breasts to my chest. I propped my knees up a bit and started thrusting in and out of her cunt. "I think you're trying to change the subject. Maybe we should do it again tomorrow night. I could quit working sooner if we had the extra cash." I increased my tempo as the memory of her gangbang appeared in my mind. "It feels like you like that idea." All those cocks in her earlier reappeared in my mind. "Do you think we could make ten thousand dollars on this trip?" She was tormenting me. We still had a week of our vacation left. A hundred men fucking her was possible. Eleven each day would just about do it. My cock was pumping faster and faster. My breathing was very deep and strong as my toes curled tightly. The money was unimportant. The fucking was what counted. As long as I could watch, she could have all the men she wanted. My nuts rose up, and I began firing my seed into her scalding hot hole. Her vaginal muscles held me prisoner, and she howled with excitement as waves of pure pleasure surged through her.

The drive to the next city only took two hours. Cindy wore a short, gauze sun dress and her shoes. She kept her hemline up to her waist leaving her freshly shaved pussy in view for me and anyone else who could see into the car. The upper portion of the dress was pulled down off her shoulders in the style of a peasant blouse to the point that her nipples were barely covered. When truckers pulled up beside us and stared at her, she lowered her top to expose her breasts. I wore a t-shirt and a pair of cutoffs. No underwear. The head of my stiff cock protruded out the left leg hole of my pants. Occasional light touches of her hand kept me on the verge of cumming. My leg was sticky with pre-cum when we got to the town. Because I wouldn't be able to get out of the car without my tent pole showing, I pulled into an empty alley and had her suck me off.

We had lunch and went sight-seeing. Both of us had sex on our minds. Everything we saw became a phallic or vaginal symbol. Doorways became pussies; the light poles were cocks. The banana splits we had for dessert were cocks in pussies.

We drove around to find the local watering holes and figure out the clientele each might have because we wanted someplace that attracted a lot of horny men. We decided on a sports bar similar to where she worked with a large parking lot in back.

I went in first. Cindy followed me about five minutes later. That lessened the chance of someone else hitting on her before I did. As I got out of the car, I asked her, "Are you up to this? You aren't too sore or anything?"

"I'm not a bit sore," she said. "Get going. I'm starting to get wet just thinking about this."

There was a woman sitting alone at the bar. I sat on the empty stool beside her and ordered a screwdriver. She appeared to be about forty. She had shoulder length dark brown hair and emerald eyes. Her firm boobs pressed against her tight blouse emphasizing she wasn't wearing a bra. The buttons were open down to the level of her nipples. She looked at me and smiled. I feigned a double-take. "Is something wrong?" she asked.

"No," I replied. "You remind me of someone I used to be in love with."

"That's different. Considering I'm probably fifteen years older than you, it's not very probable."

"I would have said no more than five, and this was about five years ago. Your hair style is the same; I'd guess you use the same apple-scented shampoo. You're the same height and weight. But it was the eyes that got me. You must have a sister somewhere." I had used a similar line of bull when I first met Cindy. It worked then, and I had a feeling it would work again.

"You're very sweet. Unfortunately I'm an only child. My father died when I was an infant. Mom never remarried; never even had a boyfriend that I know about. I see you're married." She tapped my wedding band.

"I see you are too."

"Touché. My husband's out of town on business. I got lonely and decided to find some company. What about you?"

"We're on vacation. Any children?"

"I can't have any. I had a female operation when I was seventeen. They took out the cradle but left the playpen."

"That's sad."

"I thought so at first, then I realized without kids the playpen could get a lot more use. Where's your wife?"

"Shopping. I understand it's a girl thing. She's meeting me here later."

"It looks like we both could use some company. There's a very dark booth in the back. Why don't we wait for her there?"

"Okay." We picked up our drinks, and I followed her to the corner booth. The table was not very close to the seat which was long enough to take a nap on without propping your feet up. Her skirt rode up as she sat down, but she made no attempt to rearrange her clothing.

She placed her had gently on my cheek and drew my lips to hers. Our first kisses were very light; contact was minimal. My arms encircled her shoulders so she couldn't pull away. Her hand went to my lap and inner thigh as I held her mouth to mine. My cock strained against my pants as she stroked it through the fabric. Her legs parted as I ran my fingertips up her thigh to her uncovered love nest. With an expert hand, she unzipped my fly and freed my aching shaft.

I opened her blouse completely and caressed her breasts pausing briefly to gently twirl her nipples between my fingers. I kissed her neck and breastbone before moving to her nipples. They stood up as my tongue slowly left a damp trail around each one. She lifted her skirt to her waist and laid back on the bench seat. Her labia were already swollen and had parted in anticipation. Her clit protruded from under its hood inviting me to suck on it, an invitation I did not hesitate to accept. I hummed a low note as I worked on her clit. Her thighs instantly locked my head in position as her body trembled violently. I stopped humming until her orgasm ended, then began again. Once more my head was clamped between her legs. This time I did not stop humming, but continued until I was out of breath. When she released my skull, she grabbed me under the arms and pulled me up on top of her. I hooked my arms under her legs drawing them up to her chest exposing her pussy to my rampant manhood. I entered her with ease and drove my cock all the way into her on the first stroke. If anyone was watching, they had a clear view of my meat going in and out of her. As she began moaning, I pressed my mouth to hers to keep everyone in the place from hearing her. My ass bounced like a rabbit's until my loins tightened up. My pecker jerked inside her as my jism shot into her tunnel. Her pussy contracted milking every drop from me.

We laid on the bench until we caught our breaths. "Where did you learn that humming trick?" she gasped. "That was fantastic."

"We pros never give away our secrets," I said.

"You're a gigolo? I should have known. What do I owe you? Fifty?" I didn't respond. "Seventy-five? A hundred? That's my top offer."

"That will do," I said trying to be casual. She picked up her purse and dug out a hundred-dollar bill while I zipped up my pants. As I put the money in my pocket, I said, "You should consider the life. You'd make a fortune." I gave her one last kiss and went to the men's room.

Cindy came through the front door as I left the rest room. I went to her and hugged her. "What took you so long?" I whispered.

"I got an offer outside I couldn't refuse," she whispered. "He said he always pays two hundred. How could I say no?"

"Couldn't you have come in and gotten me first? You could have been badly hurt."

"I wasn't." She sniffed at my face. "You smell like you've been eating pussy."

Why is it that pussy juice defies soap and water? "You are not the only one who gets offers."

Cindy stared at me in amazement. "Some woman paid you to fuck her?"

"Is that so incredible?"

"No. We're supposed to be doing your fantasy which is watching me get screwed. I guess it's okay. If I can have a bunch of strangers, you should be entitled to some too." Her voice didn't sound like she was convinced by her own logic.

We found an empty table in the middle of the room and sat down. "Are you okay?" I asked her.

"Yeah. I didn't expect you to get lucky, let alone get paid. The idea never entered my mind." I put my arms around her and kissed her. When our lips parted, I glanced around. Several men were watching us. "Okay, give me the money so it looks like I'm a whore." I took out my wallet and pulled out the five twenties I had for that purpose. After fanning them and counting them, I handed them to her, and she put them into her purse.

We went outside, got into the back seat of our car, and started putting on the show that we had done the previous night. As before a crowd formed around the car as we ate, sucked, and fucked. I remembered to shoot my cum on her tummy. After I pulled my pants back on, I assumed my roles of doorkeeper and money collector.

This time we both cleaned the cum puddle off the back seat before spending the rest of the night fucking ourselves silly.

When we got home, we had twelve thousand dollars in our pockets. Surprisingly she wasn't sore from all the fucking she had done.

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  • COMMENTS
3 Comments
GuyfromShadesGuyfromShadesabout 2 months ago

Thanks for your writing.

MorevinilaMorevinila4 months ago

Story line fun but lacking some narration of juicy bits to earn a 5.

AmbulAmbul4 months ago

Fascinating story of how a couple got into whoring the wife in the backseat of a car. Cindy, with her very large tits and hot body has no problem attracting men but really gets off on the money she is paid for being fucked. And now her husband, who turns out to be a first class pussy eater, has made money too. What next for this enterprising couple?

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