Some tips are just better for the giver and the waitress as well.
Being like most guys, I spend most of my time, energy, and brain function looking for pussy. Also like most guys, my schemes and plots crash and burn over 99% of the time, resulting in no pussy. A few weeks ago, with all of the odds stacked against me, I hit one out of the ballpark in the pussy department. Here's that story.
Being a single guy, I'm pretty much a regular at a local diner that serves only breakfast and lunch. Darlene is one of the waitresses there. She's a bundle of energy and friendly enough, although not over the top flirtatious like so many waitresses get with regular customers. She always wears her hair pulled back tight in a pony tail, has a cute ass, but is otherwise mostly kind of plain.
I know she is a single mom, with two school age kids who she supports with her waitress job and "occaisional" money from the "jerk", as she calls her kids' father I'd guess her to be about 35.
Recently the local TV cable played the movie about the cop who didn't have money for a tip, then left as a tip half share of a lotto ticket, then won, then honored his promise. This was the topic of conversation at the diner, with everyone throwing in their 2 cents worth.
I noticed Darlene kind of wince and grab her lower back and I asked her if her back hurt.
"Yeah," she said, "I think I did something to it. I could use one of those super spa treatments. Yep, that would fix me up."
Because the topic of the day was creative tips, I sucked up the nerve to try my luck on one with Darlene.
I was eating at a table by myself and, as Darlene refilled my coffee, I said, "Hey, instead of the normal tip, I'd be willing to give you a back massage better than a super spa treatment, guaranteed to do the job on your back."
To my shock and surprise she relied simply, "Oh God, you're on, how soon can you do it?"
"When do you get off?" I replied, fully expecting that she was putting me on.
"Uh, 10:30, if that works for you, and I don't have to come back for lunch today, " she said so matter-of-factly that I was either taken in by her kidding me or I had hit the jackpot.
"10:30 works for me too, I can do it at your place or mine, it doesn't matter to me," I said, hoping she was for real.
"Well, if you don't live too far away, and don't mind, my place is kinda' messy....," she replied.
"Okay, I'll be here for you at 10:30," I said, hopefully sealing the deal. Did I just hit the lotto?
I drove back to my place, straightened up real quick, re-made the bed with clean sheets and wondered if she was actually going through with letting me give her a massage. Darlene, baby, I'm hoping you're not just teasing...
At 10:30 I pulled into the diner parking lot as she was walking out to her car. I pulled right up beside her before she got into her car and said, "Hey, Lady, ya' want a ride somewhere?"
"Yeah, hey, do you want me to just follow you, where do you live, anyway?" she asked.
"I live just across the bridge, along the river, follow me," I said, trying very hard to appear casual, like this was just a no big deal thing.
"Alright, just drive slow so I don't lose you," she said.
Yeah, like I was going to let THAT happen.
As I'm leading her back to my place, over roads I've driven a million times, I keep checking the rear view mirror, making sure she's still there and wondering if I'm going too slow and appearing weird, but not daring to go too fast, for fear of losing her. I got increasingly excited as she kept following me, Oh my God, she is really following me all the way to my place.
I realized, as I turned into my driveway, that I was getting stiff, oh jeez, just what I needed at the wrong time to complete the impression. Here's a guy driving ten miles per hour and gets out of his car with a boner. Welcome to my house, Darlene! Would you like a fuck to go with that message?
Thankfully, the dick poking itself against my pants in greeting didn't seem to catch her attention as she looked at my house and said. "Wow, you have a really nice place."
"Thanks," I said, "come on in."
It seemed natural to offer her a tour as she was beaming her admiration of my house on the river. Every two weeks a maid service does their thing and she commented on how neat and clean the place was. I made some dumb comment like, "Yeah, the maids clean in exchange for massages."
Her comeback was something like, "Oh wow, maybe I won't be disappointed with my tip then."
As the tour concluded after my showing her every nook of the house, and lingering with the water view from the bedroom balcony, I offered her a drink and asked her what she would like.
"Whatever you recommend to go along with your spa treatment," she purred.
"Actually, I would recommend that you go into the master bath and relax with a hot shower while I get us something to drink and when I return I'll dry you off and start the treatment," I boldly suggested.
"Oh, that sounds great, lead the way, " she said.
In the bathroom I showed her where to get towels, hang her clothes, and offered to fill the jacuzzi tub also.
"Maybe later for the tub, the shower sounds good for now," she said.
I left her to the getting naked and wet part of the "treatment" as I brought zinfandel, glasses and ice back up to the master bedroom where Darlene was humming sweetly in the shower. This was working out!
I walked into the bathroom and held up a towel as if to offer to dry her when she was done. She motioned me to join her in the shower. I was naked and in the shower with her in a flash. We embraced and kissed for the first time with water cascading down over our bodies. Darlene felt so good naked and wrapped in my arms. She kissed back at me with spirit and she pulled us tight together. I dropped my hands to her ass and scooped her in to my hard thing that had obvious intentions about getting inside of her.
"I'm up for anything, Tom. I'm baby-proof and am in the mood for doing it all," she said just loud enough to be heard over the sound of the shower.
While it was extremely tempting to spear her right there in the shower, we managed to get dried off, she even used the hair drier and I got to see her hair flowing free and not in a pony tail.
As we approached the bed, she sat on it and looked up at me with a smile. I kind of pushed her back and helped bring her legs up high, then pulled her by the hips to the edge and knelt down and began slurping away at her honey pot. She amazed me by saying very loudly, "That's it...you like that, don't ya...tastes good, right?...slurp it all up, baby...dig that tongue in there."
The combination of tasting her sweet womanhood for the first time and the unexpected "voice over" really got all the wrinkles out of my cock. I was definitely ready to do this honey.
Darlene delighted me by being an agressive lover. She really gave my cock a working over with her mouth and hands. She seemed to know that a guy will excuse forward behavior when it's directed at his dick.
While giving my cock her lavish treatment, she paused, looked at me, and said, "I REALLY love doing this to a cock."
I shot my geyser when she had her fingers around my cock with her mouth right there cramming down on the head, with her hot breath bathing my shaft and balls and head, seemingly all at once. She laughed in a playful way when I shot off.
"Oh my, you really liked that, didn't you? I bet that Mr. Harpoon here is also going to like poking around in my twat," she said as a grin spread across her sweet face.
We fucked in jack hammer mode from the beginning. Her cunt squezed my cock at the entrance and felt hot and a bit hollow further in. It seemed to invite me to probe around with strokes from different angles. She responded to this stroking technique energetically by screaming animal grunt noises and tightly grabbing my arms and saying, "That's it..., like that...., yeah..., fuck me good."
Well into our hot fucking session, Darlene asked, "Tom, would you do me in the ass?"
Ah, my wildest dream since I began admiring her ass when I first saw her in the diner over a year ago!
She turned over on her stomach and kind of presented her ass to me and said, "Just plow me good. I love to take it really hard in the ass, you get no points for being gentle!"
Oh baby, did I plow her ass. With Darlene laying on her stomach, I climbed on top of her and squeezed her hips like a vice with my legs and banged away at her tail. I worked to full capacity to give it to her hard enough so hopefully she would say, "not THAT hard." I felt the thrill of finally being in her sweet ass with directions to NOT be gentle.
My ecstasy was interupted by a need to drop my load, which I did by jamming into her ass as hard and deep as I could and holding the final plunge as my cock spasmed out enough spurts to empty my balls and give Darlene's ass a creme filling.
I felt the pride when she expressed her appreciation for my efforts, "THAT'S how I like to have my ass done!"
Ah, sweet success.
As Darlene and I concluded our rambunctious love making session, she said, " Gee, I'm glad that you finally gave me an opening to let you know that I would like to get together with you."
"Darlene, I had no idea I had a shot with you, I didn't want to risk creating an awkward situation for you or me," I said.
"Well, I had a hunch you would be good in bed, but I had to be careful with you being a customer," she replied. "So now we don't have to waste any more time being bashful with each other, do we?"