Betting Big

It's 1:30am, and my dick is inside a girl I have known for less than three hours. Her name is Ginger. Ginger's ass cheeks are jiggling each time I thrust in from behind. And Ginger's tongue is massaging her best friend's swollen clit. The friend's name is Alex. With Alex and Ginger splayed open in front of me -- a pleasing landscape of tawny, young flesh -- I have just had an epiphany. I have realized that the best sex -- the most satisfying fuck -- is the one you earn just by being a good person.

Maybe some backstory would help.

It's Friday night. Earlier this evening I made a bet with my brother Blake. We have a tradition of meeting for drinks at the end of each week. We work in different parts of the city and don't get to see each other often. But one of our favorite bars -- the Drunken Donkey -- is an easy drive for us both so we often meet up and catch up. And talk about women. We are both single -- him perpetually so, always playing the field, and I freshly single, after a divorce she and I both knew was inevitable. But relational status is about all my brother and I have in common. I'm a Gen-Xer and something of an old soul. I like jazz. I like to read. I like my smart phone, but I'm not married to it. Blake is eight years my junior (our parents' surprise baby) and a full-on digital native. And it was our differing perspectives on technology that put me on the path toward the menage a trois I'm currently enjoying.

At about 8pm, over bad beer, Blake asked how I was doing with the ladies, which led to me complaining about the bar scene, which led to him extolling the virtues of Tinder, which led to a vigorous debate about the value of find-an-anonymous-friend-for-a-quicky apps. Blake likes them; I'm skeptical. So Blake proposed a bet. He said he could get laid using his phone before I could get laid using my charm. Blake's phone is the latest model with the most memory, the fastest processor, the best service, and all the other bells and whistles. My charm is not the latest model and could probably use an upgrade. But I agreed to the bet. Loser has to buy drinks for a month. I drained my beer and left Blake at the Drunken Donkey, staring at his screen.

It has been seven years since I was part of the dating game. I went to a bar where I used to know every server, certain that the entire scene had passed me by. I'm 42, with a little bit of grey cropping up around my temples. I work out, but I'm a step slower on the basketball court. I realize I am not the prize I used to be. Blake's phone might beat me handily.

The bar was just how I remembered it: trendy because it didn't try to be. It drew a mixed crowd of two categories: college co-eds and office professionals drinking away a week's drudgery and enjoying the scenery provided by the first category. It was crowded, but I spotted a place at the bar where I could squeeze in. The barkeep nodded and I realized that I was in a contest of tenders. Blake's quest involved Tinder; mine a bartender. I ordered Bullit Rye, neat, and surveyed my options. Lots of pretty girls, several without obvious male attachments. At the end of the bar, there are two girls embracing. I was briefly excited by the idea of watching lezbos kiss. But then I realized it wasn't that kind of embrace. One is crying and the other is consoling.

Moving on, I spied one woman across the bar in her mid-forties, bleach-blond hair, plentiful makeup, and a low cut dress. She was showing off impressive boobs, but they look to be receiving a substantial lift from her push-up bra. I looked up from the cleavage to see that she was smiling at me. Caught me peeking. Bright red lips. Long lashes. She clearly had an agenda for the evening that included whatever it took to make herself feel sexy. And I had to admit it wa working.

"A little trashy, but I can work with trashy," I think.

On my trip around the bar, I had a twinge of guilt. Isn't this a shitty move? Trolling for trim? Was I about to take advantage of this cougar? But when I rounded the bar and saw her winking at the guy seated to her left, I realized how silly that was. If anything, the cougar was out to take advantage of me. What would it hurt to give her what she wanted --  an evening that convinced her she hasn't lost her allure -- and keep me from shelling out for Blake's beer for a month? I sat down on her right, and she lost interest in the guy to her left.

She spoke first, swinging herself around on the stool to give me her full frontal attention. "I'm Roxy."

First, I felt guilty. Now I was a little grossed out. But I can muscle through.

"Hi Roxy. I'm Tad." My name is not Tad. It's Sean. But I felt like she had already established the truth standard in this relationship and I was following her lead.

"You here alone?"

"Going on two years now," I said. It was my standard answer and I only then realized how pitiful it sounded. In a quick rescue effort, I added a question to which the answer was obvious: "You?"

It was too late. She was already making pouty lips and putting her hand on my knee. "Oh, poor thing." She scoots to the edge of her barstool, her bare knees protruding from under her dress and sliding between mine. Her hand moved up my thigh. "I'm sorry you're alone.

This was going as well as could be expected, but I was remarkably disinterested. In fact, I was a little relieved when the guy on her left whispered in her ear. Whatever he said sounded like it started with "My friend and I" but I couldn't make it out. Whatever is was, it captured all her interest. Her hand was gone. Her knees extracted from my lap. And she went full-frontal with mister-my-friend-and-I, showing me the thick-strapped back of her dress.

"Well, that's that," I thought and took a swig of whiskey. Then I noticed the two girls at the end of the bar. They weren't hugging any more; they were laughing. At me. The blond one made pouty lips in mock sympathy for me after Roxy's rejection. I flip them the bird. Then I call the bartender over and ordered them a drink.

When the drinks arrived -- cosmopolitans -- the girls raised them in a long-distance toast. Then they conferred for a moment and, to my surprise, carried their glasses in my direction. When they reached me, I was surrounded by empty seats. Roxy had decamped. They flank me and the one who made pouty lips spoke.

"That was epic," she teased, nodding behind her where Roxy was leaving with two golf-shirted men.

"She lost interest when I told her she needed a bigger bra,"I said.

"Oh, is that what happened?" she nodded in mock understanding.

"I'm Sean," I was hoping to change the subject.

"Ginger." This is the Ginger of the pouty face tease and the jiggling ass cheeks where we started this story. Ginger introduced her friend, Alex, she of quieter demeanor and soon-to-be swollen clitoris. But toasting my new friends on that barstool, I hadn't yet glimpsed either ass or clit, and had no inkling that I ever would. These girls were sweet to come over and console me, but they would move on to the rest of their night soon. And I would have to start scanning the stools for another target.

Alex had straight, dark brown hair, parted in the middle with no bangs. I thought the haircut added to a look that I wanted to describe as "vertical." Thin nose. Small mouth. Narrow frame that peeked out from one of those shirts with holes in the shoulders. Skinny waist and legs inside tight white jeans. Alex was reserved and pretty, like an antique porcelain vase one was expected to admire, but not touch.

We made small talk: established the appropriate social connections of careers, relationship status, current event awareness, and sports fandom (they both followed women's soccer). Alex and I discovered that we had attended the same local high school, and hated the same calculus teacher.

"He was crazy!" Alex laughed. "You know I once caught him trying to look up my skirt!"

"Well, he wasn't crazy for that," I winked.

"I was sixteen!"

"You're right. That's inappropriate," I retreated. "Plus, you're not Chinese."

"Right? What was with the Asian fetish!? He used to talk about Asian girls all the time. I seriously saw a bulge in his pants more than once."

Alex was reserved, but easy to talk to. She didn't look around when she talked, but kept her eyes locked on mine.

By contrast, I could hardly look at her. Not because she wasn't easy to look at. She was very pretty. But I had a mission. I was there to score -- to beat Blake -- and my best shot at that was someone a little older and a little more -- I hated to admit it -- desperate.

There was a grandma to my left. Nope.

A knot of college girls across the bar, making eyes at any dude who looked willing to buy them a drink, which was every guy in the bar. There was basically a line forming. Too young and too much competition.

I kept scanning between comments to the girls.

In contrast with Alex's appearance, Ginger went more directions than vertical. Her platinum blond hair, like her conversation, spun off in big looping curls that fell loosely out of her head and kept drawing my attention to her ample, round boobs. She was wearing a pleated skirt and a lacy top that swayed free and easy off of the shelf created by her tits. Both girls looked to be in their mid-twenties. And there was something between them they weren't telling me. After I made a comment about their waiting boyfriends, Ginger seemed to break off to another world. Alex put a hand on my shoulder and pulled me in for a conference.

"She's just been through a bad break-up," Alex said. "That's why we're out tonight. Trying to help her have a good time and forget the guy."

"Oh, I'm sorry," I said, turning to Ginger. "Her bright blue eyes were moist. "Break-ups are the worst. You start to think, 'If that person doesn't love me -- maybe doesn't even like me -- does anybody really like me?'"

Ginger grinned and exhaled, "That's exactly what it feels like."

"The worst," I repeated.

"The worst," Ginger confirmed. She gave me a quick hug, but then looked away, pretending to be interested in something to her right, but I knew she was hiding tears, regaining her composure.

Behind me, I felt Alex put her weight against my back and her lips to my left ear. "Thank you. That was sweet."

Sweet, maybe. But temporary. These girls would move on any minute and I would need to find another companion or risk looking like of the other lonely losers bellied up to this bar.

To the right, there was another cougar. She was my best bet. Early forties. Red hair. Dressed modestly and drinking white wine. She kept looking at her watch and the front door. While Ginger and Alex chatted, I crafted a mental plan. In the short moments after the cougar gave up on her date and before she left in disgust, I would swoop in with a fresh glass of wine and a winning smile.

My plan in place, I was content to bide my time between two beauties. Ginger seemed to brighten after the hug. Alex smiled more. We started to make up stories for each of the people at the bar.

...a corporate drone bored of life, dreading the drive home to his nagging wife and screaming kids.

...a college hottie without a clue except that her firm physique buys drinks. She learned that in high school, we imagined together. At a party where she lost her virginity and her good sense.

...a divorcee (this was my cougar target) who was nervous about getting back into dating, but even more nervous about spending the rest of her life alone.

"Look how short those skirts are," Ginger said absentmindedly. I looked around at the hemlines I could see before I realized Ginger was looking up. There was women's tennis on the TVs above the bar. A tiny, athletic Russian with pigtails was beating a tiny, athletic Norwegian with a pony tail. Both my girls were staring up at the screens, mouths and slender necks open. I assumed the skirt comment was the prelude to a women's rights rant. I took a sip of the Bullit and tried to think of how to agree but not sound like I was pandering.

"Sexy as hell," Ginger breathed.

I literally spit whiskey onto the bar. I started to choke and Alex slapped my back in a motherly instinct against asphyxiation.

Ginger smiled. "You're surprised I think short skirts are sexy?"

"I just didn't expect you to say that."

"That's the whole point of women's tennis, isn't it? Toned legs and short skirts? That's why people watch this. You can't tell me any of the guys in this bar care a rat's ass about the actual tennis."

"Yeah, you're probably right," I said.

There was a close-up of the Russian, and, without taking her eyes off the screen, Alex said, "We would tear that bitch up."

I spit again.

Ginger said, "Yeah we would." And the two fist-bumped across my chest in a show of unexpected, lustful solidarity.

The tennis match went to commercial and Alex announced that she needed to visit the ladies' room. As they both rose to leave, I raised my glass slightly and told them I enjoyed the chat. Ginger gave me another hug and said, "Hang in there, Tiger."

I watched them walk away because the view was fantastic. Then I mentally raised my glass to their lovely young backsides and assumed I would never see them again.

The cougar drained her glass and motioned to the bartender. She was tabbing out, which meant it was almost go-time. I popped in an Altoid and asked the bartender to pour me a glass of what she was having. But when I turned to get up, I saw Alex coming toward me.

"Hey," I said, surprised. "Forget something?"

Alex stood close, between my knees. She smelled terrific. I couldn't believe I was worried about the cougar leaving when this fox was right in front of me. "Look," she said. "Ginger and I are going to get a drink down the street. Some place quieter. You want to join us?"

I hesitated. These girls were amazing. Way out of my league. The cougar was slipping away. But I couldn't say no.

"Another drink?" I stalled. "Haven't had enough yet?"

"I never get enough," Alex winked.

The cougar got up. "Um, sure," I said. "Where?" thinking I could still intercept the cougar while not pissing off the girls.

"Its called the Lizard Lounge," Alex said. I realized the cougar was crossing the room, but I couldn't look away from Alex because she wouldn't look away from me. Her eyes were locked onto mine, as if she was trying to communicate something through them. I wasn't picking up the signal; distracted by my escaping prey. Without breaking the connection, Alex slipped a business card into my shirt pocket and patted it against my chest. "Here's my cell number. See you soon." I watched her figure sway gracefully toward the door, only steps behind my best shot at winning the bet.

"Shit!" I whispered.

My phone buzzed. A text from Blake: "I'm talking dirty to a chick in Jonesboro."

"Jonesboro is an hour away from you. Are you really chasing tail that far?"

"Oh, like you're texting me from a centerfold's love den. Have you even met a real female yet?"

"In fact, I have met three. And just let one get away."

"Are they 80? Fat? Blind? All three?"

"Hey, you didn't say I had to bed a looker."

"Just as long as it's not a hooker."

+++

Alex and Ginger were already half a drink in when I got to the Lizard Lounge. I didn't see them at first, and figured they had pranked me. But then I spotted them in a corner booth in the back.

"We weren't sure you'd show," Alex said when I scooted in next to her. It seemed that she had become the pair's spokesperson now.

"Sorry. Had to return a message."

The waitress stopped by, wearing a tight, short skirt, high heels, thigh-high stockings, and a bra. It wasn't until then that I realized the Lizard Lounge had a distinctively sexual vibe. All the waitresses were dressed this way. There were male waiters too, wearing tight pants and bow ties, nothing else. The music and the light were very low. I ordered another Bullit.

Ginger scooted out of the far end of the booth and walked around the table. Then she scooted in on my left side. Alex came in close on the right. She found my eyes again and spoke steadily, as if conveying a state secret. "I'm glad you came." I felt Ginger's fingers in my hair. "Here's the thing: Ginger and I have a mission tonight and we think you can help. We came out to party, and to help Ginger feel better. I think that's something all three of us want, isn't it? To help Ginger feel good?"

Without looking away from Alex's alluring eyes, I reached back and put a hand on Ginger's thigh. If I was reading this wrong, I was about to step way over a line, and probably get myself slapped. But if I was reading it right, this could be one hell of a night. It was worth a shot. I moved my hand under Ginger's skirt while I said, "I think we should do whatever it takes to make Ginger feel good." Then turning to Ginger, I continued. "Very, very good."

I kissed Ginger gingerly, lolling my tongue lightly against hers for a long, seductive moment. She sighed when I pulled away, and her chest heaved.

Alex said, "Do you know what revenge porn is?"

"Yes," my head was spinning.

"We want to make a revenge porno with you. Tonight."

"Ummm."

"But you need to know that we're going to film it and put it on the internet."

"Yep. Got that. And why me?"

"You're cute. And sweet. And..."

"Old?"

"Mature. How old are you?"

"Forty-two," I decided not to lie. Ginger giggled. And I said, "Outside the range?"

"Not for me," Ginger said. "I'm 31. But Alex is 26. She's a little young for you."

In reply, Alex put a hand on my thigh, just below my crotch. It felt warm and promising. Then she leaned in put her lips to my ear for the second time. "I'll make you feel like a teenager again."

+++

We rode in their car, Ginger and I making out in the back seat. Alex had the key so I assumed it was her apartment. Maybe they lived together? The place was decorated in dark wood and beige furniture, surprisingly masculine. While Alex turned on a few lamps and lit a few candles, Ginger made a round of drinks and then said she was going to change. I couldn't wait to see what she put on next.

Once she was out of the room, Alex started setting up a camera on a tripod. She told me to stand by the couch so she could make sure it was in frame. And I took the opportunity to clear something with her. "Look, is Ginger good with this? I mean, breakups are tough. I don't want to be a rebound one night stand that she regrets later."

Alex cocked her head to the side as if confused. "We talked about that a lot. She assures me that she is sooo ready for this. And that even if she regrets it later, she wants it now. But you should know that this is almost definitely a one night stand. I hope you weren't thinking this was leading to marriage."

I laughed, realizing how silly my comment sounded. "Right. Of course. I just don't want to hurt anybody."

Alex stepped out from behind the camera and came to me in front of the couch. She pressed herself against me. "Are you just laying it on thick or are you really this sweet?"

I kissed her hard, put my hand on her skinny, firm butt. "I think you should taste me and see how sweet I am."

I door opened. "Save some for me." It was Ginger's voice. She was walking slowly toward us, swaying her hips and licking her top lip. She was dressed for her big night. She wore a black leather bustier that hugged her hourglass waist. It looked like a ribbed, carved pedestal for her chest, which was two perfectly-sculpted globes of amber flesh tipped with pert, erect nipples just slightly north of center. Her slender legs were encased in thigh-high leather boots with steep heels and zippers up the back. She wore nothing between the boots and the bustier, and I caught my first glimpse of her hairless pussy. The candlelight lit her tanned body softly. She strutted, blew a kiss, and then turned a circle to show off her outfit.