tagGroup SexThe Bet

The Bet



Dean and I were co-workers at an Italian family restaurant. We were not friends at first. In fact, we fought like cats and dogs. Looking back, the arguments were petty and immature. And that goes for both of us.

But one day, I crossed the line. And it damned near got me fired.

One day, he was talking about his mother to a co-worker. I only caught half the conversation and didn't understand the context. About ten minutes later, I said something sarcastic to him, he said something back, and then I made a vicious comment about him being a mama's boy. He looked as though he was about to blow a gasket, but all he did was walk away steaming mad. He had to be sent home because he was so upset. Then I got royally chewed out by Chris, the assistant manager. He angrily told me that Dean's elderly mother was very sick and in a nursing home. Mainly heart disease.

"The guy's got a lot of things on his mind, so stop yanking his chain, Taylor or I'll fire you so fast you won't fucking believe it," he said.

I immediately felt terrible. I didn't know she'd been ill. If Dean would've told me, I would've apologized and backed off. I can't say I liked the guy (at least not then,) but I didn't hate him either. But I'd crossed the line and felt shitty about it.

The next day was Dean's day off. I learned that his mom died the next morning. Dean immediately took bereavement leave. Almost two weeks. During a lull in the dinner rush on his first day back, I decided to try to bury the hatchet. I asked for some time to talk to him. I approached him and apologized and told him I was sorry about his mom. He looked surprised and grateful and apologized to me. It was emotional for both of us. As he talked, I saw a side of Dean I really didn't know existed. Underneath all the pain and the distrust and the idiosyncrasies was actually a pretty decent guy. He didn't want sympathy, but it was hard not to be a little sympathetic. We never had a "Dean and Taylor moment" again. And over the next few weeks he began coming out of his shell. He was undergoing counseling for the grief and whatever else was eating at him and he became a changed man.


My car broke down. I got it towed to a local garage and I called the restaurant and asked if someone could possibly pick me up. Dean, who was working the lunch shift for the regular guy, came out. En route to the restaurant, we began talking. Even the next day, which was his day off, he offered to give me a ride to and from work. And he refused payment. Not once did he hit on me, although I did see him sneaking peeks and looking sad. I let it go.

It's probably been a while for him, I thought.

While Dean and I had made up, there was a new thorn in my side.

Bethany had been hired a month earlier. And she was getting more than a little attention from the male customers. This little blonde bitch became notorious for using her big tits and her ass as an added attraction to wring tips from male customers. I'd tried to be civil to her and tried impose some standard of professionalism. But nothing worked.

Our professional disagreement developed into a full-blown rivalry.

One day before our shifts began, we got into a fight about her behavior the night before, which I felt was more over-the-top than her usual. A group of Masons were having dinner and Bethany went into her act. She was completely unprofessional and I told her that such a display was suited for a strip club, not a family restaurant.

"At least men pay attention to me," she said. "More attention, bigger tips. You and that skinny body of yours? Puh-leeeze!" She rolled her eyes.

I hate this attitude among some women. Without surgery, I fully realize I'd probably never be classified as voluptuous (I'm in the lanlube/athletic category,) but I'm not complaining.


I decided to show Bethany a thing or two.

"Okay, Bethany. Let's make a deal. If I earn more tips tonight, you work for me on my birthday," I said.

"Deal. And if I win..." She spotted Dean arriving for work and smirked. "And if I win, you have to fuck Dean," she said quietly.

"WHAT!?" I screamed. I couldn't believe what I'd heard. Then I realized that others might eavesdrop and lowered my voice.

"Oh, you gotta be kidding me, Bethany!"

Dean and I had made peace, yes, but I didn't feel sexually attracted to him at all. He was much older for starters; probably his late thirties to my twenty-five. His mop of wavy dark brown hair was showing strands of gray here and there. He was still a little thick around the midsection despite a massive weight loss and occasional visits to the gym. He'd improved some in the looks department, but it was hard for me to decide if he could be considered handsome or not.

"Nope," she said. "You really think you're better than me, Taylor? Prove it if you've got the guts. And I have to see you do it. My brother has a spycam I can borrow. All you have to do is turn it on and hide it somewhere. It's tiny and he won't know it's there. I can hook into the feed on my laptop in my car to make sure you don't welch on the bet."

"You some sort of pervert, Bethany?" I said, still not believing this conversation was happening. "Why don't you fuck him then?"

"I'm saving myself," she said proudly. "You know, that right man, right moment thing? I shudder to think how you lost your virginity, Taylor."

"As uptight as you are about sex, it would be a miracle if your cherry could ever be popped to begin with -- little girl."

"Fuck you, bitch! I'm more woman than you'll ever be."

"You haven't got a clue."

"Yours should have an open all night sign tattooed on it, Taylor!"

I'd had it with her!

"Okay, Bethany. Tell you what: You're on! If I lose, which is unlikely, maybe you'll even pick up some pointers from a real woman for whenever you do decide to have fun with that useless cooch of yours."

Although tips were a little higher, I lost by a measly fifty-three cents. I groaned during the cashout. Bethany smirked at me.

Oh, why did I do this? I thought.


We knew Dean's schedule. Both he and Bethany had every Tuesday off, and I traded shifts with another girl for that day off as well.

Then Tuesday came.

Going into my best damsel in distress act, I got Dean's phone number from work and called him under the pretext of having a computer problem and needing to complete something important. I begged him to come over to look at it because I was clueless about the thing.

"Uh... Sure, Taylor. I can be there in about a half hour or so," he said.

"Oh, great! Thank you so much!" I said. After I hung up, I activated Bethany's brother's spycam and hid it in a plant in the bedroom. I called Bethany's cell to tell her he was on his way and gave her the address of my apartment building. When she arrived, she called me and we got the aiming correct.

"I hope you rot in hell for this, Bethany," I snapped.

She hung up without a word.

Dean arrived in about the time he estimated. After several minutes of tinkering, he said, "I think all you really needed to do was reboot it and do a little maintenance."

I took a deep breath and closed my eyes as I walked up from behind and reached around and grabbed his cock through his jeans.

"Whoa! Damn... Taylor?" he said nervously as I jacked him a little.

"Did you set me up or something?" he asked.


"Yup," I said grinning. Inside, however, I was cringing. For a lot of reasons.

"I just got a little lonely," I lied. "Besides, you acted like you needed some attention, so..."


He turned around. "You serious?" he asked, still nervous.

I pulled off my top. I wasn't wearing a bra. They're more perlube than big. 32B.

"Serious as a heart attack!"

Then I remembered his mother and meekly apologized for my choice of words.

"Oh, my..." he said, taking a shalube deep breath. "God, Taylor. I love them! Beautiful."

The bulge in his jeans was growing.

"Not too small?" I asked, lifting them up and pushing them together.

"No, no... I love small breasts. You mind?"

Without waiting for an answer, he kissed both my nipples. I gasped involuntarily. He smiled, but is seemed to be more out of relief than happiness or excitement. Then I put two and two together.

"Dean, how long has it been since you were with a woman?" I asked.

"Almost ten years," he said shyly. "I've been toying with the idea of going to Nev..."

I put a finger on his lips to silence him.

"The drought ends tonight," I said.

Dean breathed deep and gave me a look of gratitude. I kissed him on the cheek. At least he smelled good. Just shampoo and soap. A pretty good sign he wasn't expecting to get laid. I sure hoped Bethany was getting off on this. I wasn't. But I'd made a deal and I prided myself on my integrity despite this being the result of a bet. Besides, it had been over a week-and-a-half for me and I'd had worse and somehow survived. I didn't feel I was exactly lying to Dean, but it bothered me that I wasn't telling the whole truth. But I sure as hell was not giving in to Bethany no matter what. What I was going to do was slightly exaggerate to try to make Dean feel a little better about himself no matter how lame he really performed.

And I wanted to rub it in Bethany's face to make her think her bet had backfired.

But instead, Dean surprised the hell out of me. We quickly undressed each other and he proceeded to make me go crazy fingering and tonguing my pussy. I came hard twice. I'd misjudged him completely! Then I thought of Bethany outside watching it all unfold.

She must be going nuts! I thought. Take that bitch!

I deep throated Dean to full erection.

"Oh, baby! Oh, baby that's nasty!" groaned Dean.

He had a really nice cock which would be perfectly suited for any girl. Not too long and not too thick. I told him to lie down on the bed. As I was about to lower my dripping wet pussy onto him, he drew me close, hugged me, kissed me on the cheek, and with tears welling in his eyes, said "Thank you, Taylor."

It was an unexpected tender moment. Then I began to feel really guilty.

"You're welcome, Dean" I whispered in his ear and guided him into me.

"Oh! Oh, damn that's so tight!" groaned Dean.

After working myself down all the way and using my muscles and slowly grinding on him for a few minutes, I felt Dean thicken a little inside me. And it felt wonderful. He looked happier than I'd ever seen him. He soon took control and fucked me silly. For a guy who hadn't been with a woman in a decade, Dean's lovemaking skills were sharp save for a few minor fumbles, and he damn sure knew his way around a woman's body. He ended up giving me another huge orgasm. I screamed and convulsed when it hit. After I quit convulsing enough to do it, I blew him to orgasm while I fingered myself. He groaned loudly and shot an enormous gooey load right in my mouth. It was a miracle I got it all.

Dean fell back onto the bed and exhaled.

"Incredible! You're incredible, Taylor," he smiled as he cooled off. "Whew! Thank you."

He sat up, took my hand and kissed it.

Dean? A romantic? I thought. Who would've guessed?

I could not help but cry. He wiped them away.

"Hey! Hey, what's that?" he said softly. "Taylor, you're too beautiful to do that. Then he cocked an eyebrow and said, "So stop, huh, before you get me going."

I snickered. Dean recharged quicker than I expected. In the meantime, we held each other and talked. A short time later, he was ready to go again. His cock began to harden.

"Damn! You on Viagra or something?" I joked.

He reached around and cupped my breasts and kissed me under the ear.

"Nope," he said. "Don't need it."

I giggled. Despite all my initial reservations, I'd ended up loving every damned second of it. Losing to Bethany was a blessing in disguise. But I'd satisfied our bet. The next one was strictly for us. I wasn't sure whether this was a only a one night stand or it would lead to something serious, but I loved it.

If the people at work learned what we were up to, they'd probably faint dead away.

I started going down on Dean again, but a knock at the door interrupted us. I rolled my eyes and wondered who the hell it could be. Dean groaned and threw up his hands in exasperation.

"Oh, you gotta be kidding me!" he said.

Then it hit me.


Bethany? Nah... Couldn't be! Did she see it all?

I quickly put on a robe and walked to the living room, closing the bedroom door behind me. I opened the door and a flushed Bethany walked in uninvited.

"Bethany, what the fuck are you doing?" I whispered through clenched teeth.

"I can't help myself," she said breathing heavily. I was confused. She walked toward the bedroom.

"Just don't tell him about the bet!" I whispered. "I mean it! I'll do whatever you want. Just shut up about it."

"The bet?" Bethany looked over her shoulder and scoffed. "That's ancient history,"

She smirked as she boldly opened the bedroom door and walked in.

"Bethany!" I whispered loudly through my teeth as I ran after her.

"Bethany! What the hell?" I heard Dean yelling.

"Dean!? Oh, goodness I thought this was the bathroom! Oh, goodness! I caught you two at a bad time. Oh, I am soooo sorry! "

"It's alright," said Dean. "Why are you out this way? You live on the other side of town don't you?"

"Oh, I... uh... I was just in the neighborhood and I realized I've been a real bitch to Taylor and wanted to make it up to her," she said as she squirmed and tried to straighten out a non-existent wrinkle in her skirt.

"Okay," said Dean. "I can understand that." But he was confused.

"Oh, damn!" said Bethany as she squirmed again. "While I'm here, I don't suppose you guys wouldn't mind company?"

She smiled nervously and squirmed yet again.

"Bethany?" I said. "Are you...?"

"Dammit! Yes!" she cried. "Look!"

She hiked up her skirt and pulled her panties aside. Her tighty whities were soaked and her little peach fuzz pussy was glistening. I thought she was going to pass out. I was speechless.

"I couldn't help it," she said shyly.

"Wow... Bethany!" Dean said, gulping in disbelief. "I don't know... Are you sure about this?"

"Yes," she nodded shakily as she began undressing. Soon she was completely nude.

Oh my God, she was really going to do this!

I couldn't help but stare at Bethany's curvy body with my mouth open. Whatever I may have thought about her personally, I had to admit one thing: she was damn sexy! I suddenly wondered if she was recording all this and worried that it would be up on the Internet. And I couldn't do anything about it!

Bethany kissed Dean full on the lips and jumped into bed and straddled his shocked face. He spread her open.

"Whoa!" he said, seeing her hymen. "Bethany, are you absolutely positive...?"

She nodded. "Positive."

"Okay," he said in an uncertain voice and began going to town on Bethany's virgin pussy. She was moaning like a madwoman in seconds.

I took off the robe and climbed onto the bed and began deep throating Dean again. I could not resist reaching over and grabbing Bethany's beautiful ass and licking her right above the crack. It's a major erogenous zone for me and apparently it was one of hers, too. She stiffened and moaned. Her smell was incredible. She went nuts when she orgasmed a minute later. Dean lapped up as much as he could.

"Alright, Dean," she said panting. She backed up on her knees and straddled his cock and put the head right against her hymen. "Make me a woman!" she commanded and looked right at me.

"Oh God!" moaned Dean, as he kneaded her ass and fondled and kissed her tits. She moaned loudly. "I don't fucking believe this is happening!" he said deliriously.

"Hold on," I said. By now, my juices were literally running down my leg. I ran into the bathroom and grabbed a towel. However turned on I was, I still didn't want blood on the mattress. The big bloodstain on my old mattress at home was a reminder of the night my cherry was popped. I lied to my parents and said I'd had a nosebleed during the weekend they were gone. I straddled his face and then leaned over and kissed Bethany deeply and felt her beautiful tits. She looked stunned, but offered no resistance and even began to feel my tits with one tiny hand while stroking Dean's engorged cock with the other and rubbing it on her pussy.

"Damn, girl!" Dean said. "I don't know who's more excited!" and he began lapping at my clit and fingering me. After the orgasm, I got off him.

"You ready, Bethany?" asked Dean.

She nodded with tears welling in her eyes.

"I'll try to do this as easy as I can, but..."

Bethany nodded again.

Dean lined it up and grabbed her hips. She gritted her teeth and closed her eyes. Dean thrust upwards sharply.

"Owww...! Oh fuck! Oh fuck!" she cried. "It hurts!"

"It won't hurt long," said Dean, stroking her hair to comfort her.

Tears flowed and a trickle of blood leaked out. Dean pulled out and I cleaned them up.

"Okay, the worst is over," he said. "Try not to contract. Just relax and let me do the work, alright?"

She nodded.

Dean re-entered her pussy, causing another loud whimper. Bethany groaned as he slowly buried his cock to the hilt in her. After a minute to get Bethany used to the feeling of having a cock all the way in her, Dean began to slowly fuck her. Soon the whimpers turned to moans and panting and a smile began appearing on her pretty face. Dean went faster and Bethany began to really enjoy herself.

I'd been with several women and could probably call myself almost bisexual. But riding her first cock, Bethany looked prettier than all of them combined. When Bethany finally experienced a real orgasm, she grunted and screamed. She had another soon afterward. But the real surprise was yet to come.

Bethany dismounted Dean, got on her knees, and stuck her ass up in the air and said, "Take it all!"

"God, Bethany, are you...?" Dean said. His eyes were as wide as saucers.

"Do it!" she yelled as she fingered her tiny asshole.

I opened the nightstand drawer and handed Dean a tube of lube. He looked at me in shock.

"I like anal," I said simply.

In fact, I'd planned to ask Dean to do it to me. I remembered the first time I took a cock in my ass and envied Bethany. And I admired her courage. It took over four years for me to have the nerve to take the anal plunge. Now I love it. After lubing her and then himself and working it with a finger, Dean told her to spread her ass wide with her hands and put the head of his cock against her virgin asshole and pushed slowly.

"Ooooh! Owww!" Bethany said. Her face was a mix of pain and pleasure. I diddled her clit as Dean's cock slowly went in deep.

"Oh, fuuuck that's tight!" he groaned.

Bethany simultaneously moaned and whimpered and growled every step of the way. When it was buried in her, I thought I even saw a hint of a smile. After a good ten minutes of plowing her back door, Dean shook his head.

"Oh God, Oh I can't hold back," he groaned and pulled out. He turned Bethany around, stuck his cock right in front of her pretty face, told her to open her mouth, and began pumping. Dean groaned loudly and let it loose. The cumshot was huge. She managed to swallow most of it and wiped up what missed her mouth with her fingers and licked them clean.

Damn! I swallowed that much?

Afterward, Bethany fell back smiling from ear to ear. She was almost giddy. I could not believe a bet over tips had led to this. But I didn't care either. I showed Bethany some womanly attention while Dean watched and recharged. Her pussy was amazing and she did an admirable job on me. It didn't take long for Dean to get hard again and he even fucked my ass while I ate Bethany out. The night ended with both Bethany and I taking turns blowing Dean to his third orgasm of the night. Bethany took to sucking cock like a fish takes to water.

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