I should have seen it coming. Something about what had transpired during the past few weeks should have tipped me off but it did not. It all started that night after the Tigers had beaten the Yankees in the ALCS. It was a Sunday night...
I liked going to Freddy's Pizza because they had great food, cold drinks, and nice scenery. And by scenery I meant all the young ladies who worked there. Freddy's was a rather good-sized restaurant with a long bar in the front and a truckload of seating in the back. They were always packed to the gills as it was a very popular family place. People would congregate there after church or for birthdays or to watch a big game while having a nice meal.
Freddy was one of those places that girls might fight to work at as they got their feet wet late in high school. The pay was probably nothing special but the place was clean and well kept. Customers tipped well and there weren't any trouble-makers; Freddy's seemed to have the pick of the litter. Frankly, this was the real reason I enjoyed going there.
I'd usually go there maybe a few nights a week. I'd get some drinks, chat with the bartenders and other patrons while watching a game on their rather large HD television. Then I'd get some food to go and eat later when I got home. But I'd make sure to put on a nice buzz and not get caught staring at the hired help. As this was absolutely a family place, I didn't want to get a reputation as a pervert.
The staff was very well trained to be nice to their guests. They'd make a point to chat with the regulars and were always pleasant. Their uniforms were the standard black stretch pants with a Freddy's shirt (usually red or green). They didn't flatter their figures but I don't imagine they were supposed to. The result was a pool of similar looking cuties, all between 16 and 22 years old. There were others who fell outside this mold, but not many.
One particular waitress I was working on was Chriss. When I say I was 'working' on Chriss it was simply a matter of being nice, tipping well, trying to make her laugh with a stupid joke, and quietly fantasizing about what kind of panties she might be wearing. She would respond by being nice and pouring me drinks until I went home. As I was 35 and she was 19, it seemed to be closest I'd ever get.
Chriss stood out because she seemed to be the queen bee of the gaggle. She was neither pretty nor ugly. She was about 5'6" with small breasts. Her hair was short and very blond and her skin was milky white. Her nose was board-straight and her eyes were just a tad bit too close together. The entire package was maybe 4 on a 10 scale and there were certainly other more attractive little girls there. But she was still fun to flirt with.
So it all began on that Sunday night after I'd gone up to Freddy's for some drinks and takeout. Chriss was bartending and she had my drink ready almost before I sat down.
"Hey there gorgeous" I said as usual. I made it a point to always say things like this so it wouldn't stand out when I really meant it. I'd experienced this down south and always liked it when the ladies called me 'darlin' or 'sugar'.
"Hi Mr. Johnson!" Chriss beamed, placing my drinks in front of me. "Did you want a menu?"
"No thanks. I'll probably get something to go later. How's your Sunday going?"
"Oh, it's going good. We did some shopping yesterday and bought a bunch of cool stuff."
"Oh yeah, like what?" I asked.
"Oh, well... uh, stuff." She smiled with a somewhat guilty look on her face. "Maybe I'll tell you later if you're good." She replied, looking around to make sure nobody else overheard. Although the restaurant was always full, the bar usually wasn't. And, at that point in time, there was only myself and another couple at the other end of the bar.
I don't quite know what happened or why tonight was any different than any other night, but something seemed strange. Chriss was feeding me drinks a bit more quickly than usual. In addition, she was actually being flirtatious. She seemed to be bending over a bit more than usual, specifically when I had a nice view. And she seemed to be talking about me to her flock. She would be talking with one of her minions and then they'd both look over in my direction. Something was going on.
After several drinks I ordered my food to go. I got the small pizza with a side salad to eat while I watched Fox's Sunday night lineup. In this regard, I was anything but creative. I ordered one last drink and asked Chriss to cash me out.
"Aww! Leaving so soon?" Chriss almost pouted. "But I've been so busy we haven't had a chance to talk. And you haven't told me any jokes yet."
I was a bit buzzed and couldn't put any smooth lines together, not to mention I couldn't remember any good jokes. So I just shrugged and smiled; no excuses.
"Um, Mr. Johnson?" She looked at me with her head down a bit. The phrase 'puppy-dog' eyes came to mind until she slowly and subtly licked her lips. "Mr. Johnson?"
"Yeah, Chriss, what's up?"
"Mr. Johnson? Would you do something for me if I asked?"
"Well, sure I would. Like what?" I asked, assuming it was something simple and innocent like bumming her a smoke or helping her change a tire or something. I should have just said no but I couldn't see that many moves ahead.
"I can't tell you. But will you promise to if I ask?" she said as if it were actually very serious.
"C'mon sweetie. You know I'll help you in any way that I can."
"Thanks Mr. J.! I think your pizza's up, I'll go get it." Chriss said seeming very happy as she skipped back into the kitchen to get my food.
It seemed like a very long time and she finally came back with my bags of goodies. "There's a little something extra in there for you. I hope you like them." Chriss said as she handed me the bags and I got up to leave. "I'm here again next Sunday! I hope you can make it." She smiled at me as I headed out and if I weren't a bit buzzed I would have sworn she actually winked at me before returning to her duties.
It was Tuesday before I finally remembered and found her 'something extra'. I had saved the salad and she had slipped another bag into that one along with a note.
Mr. Johnson, I really hope you can help but please don't tell anybody if you can't. I want you to come back next Sunday and do me a favor. As I told you, we went shopping and got some fun stuff. I've always thought you were handsome and really think I might want to spend some time getting to know you. If you like me too, you can let me know by doing what I ask.
In the bag are a couple of things. First are the panties I'm wearing as I'm writing this. They're nothing special but they got so wet as I was thinking about this that I couldn't wear them any longer. I hope you enjoy them as I got some new, pretty ones at the store yesterday; maybe you'll get a peek soon. The second is a special toy. I want you to put it in your butt and hold it there when you come in next week. If things go well, you should be really excited. And I'll be excited too just thinking about it.
I really hope to see you again on Sunday!
Please!!!
Chriss
"Holy shit" I thought as I opened the bag. Sure enough, there was a pair of basic white cotton panties. I picked them up, examining them closely, smelling them. They definitely had that unique odor and I completely took them in. I could almost see her bending over, imagining that these very panties had been covering up her 19 year old ass. I was at a loss. Then I found the other item in her bag of tricks.
I've seen butt plugs before, but never for my own use. I had a rather kinky girlfriend a while back and she had a variety of toys. I'm no prude but this was a bit of a stretch; I wasn't quite sure I wanted to have a pink-plastic tube up my ass. But if this could lead to having sex with Chriss, then it might be worth the risk.
+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++
Sunday rolled around and, after masturbating several times with Chriss's panties on my face, I had decided to go for it. I shaved and showered and put on some cologne as I got ready for Freddy's. I was trying to figure out what she was going to do as I drove into the parking lot. Maybe she had one in her too? Maybe she was going to need a 'ride home'? I was concerned that I didn't know what was going to happen but, as she had predicted, having a plug up my butt had the desired effect; I was semi-hard and quite excited as I found a seat at the somewhat crowded bar.
"Hi Mr. J." Chriss said as she poured my drink. She had a somewhat evil look in her eye as she almost ignored me. Granted, the bar was full of people and she was busy waiting on them all. I patiently sat there, squirming just a bit, as I threw back my drink and presented the glass on the line for another.
Chriss finally made her way back to my end of the bar and poured me another. She definitely had a look in her eye; I think she was trying to figure out if I had done what she asked. It was too crowded to actually talk to her about it but she gave me an inquisitive look as if to ask the question. I responded with the same look as if to say 'maybe I did, maybe not'. This would turn out to be a mistake on my part as she reached into her pocket and pulled something out. She held it in her hand as if it were nothing; nobody there made any notice of her subtle actions.
She placed a small pink box on the back counter as she addressed other customers. I couldn't quite see what it was but it looked eerily similar in color to the object in my ass. It almost looked like the button you use to unlock your car but a little cheaper looking. I had a bad feeling about things as she returned, typed something in the cash register, and picked up the item. Her back was still turned to me when it hit me; the button was a remote control for the toy in my ass and it started buzzing.
My eyes went wide and my cock instantly jumped as the stimulation in my anus did it's job. It went on and off several times before she looked over her shoulder at me. She had received her answer as I simply gripped the bar, trying to maintain some control and not fall off my chair. She smiled in a very wicked way; I was in her complete control now; there was little I could do.
"So did you like the salad Mr. Johnson?" She asked as she put the button back in her pocket. I regained control and said, "Yeah, it was okay." She had her hand in her pocket and buzzed me again. "It was really good, actually, Chriss. I liked it very much."
"That's good. I'm glad you enjoyed it. This drink is on the house." Chriss poured me another stiff one to go along with the stiff one in my pants.
For the next hour or so Chriss acted as if nothing were going on. She'd occasionally give me a buzz when I wasn't expecting it. But, otherwise, she acted as if nothing was out of the ordinary. After a while, the bar got less and less crowded and she started to flirt a bit more. At one point, she bent down to re-stock some beers and I could clearly see she was wearing a thong. It must be one of the items she had procured last weekend and it added to my excitement. A little while later, the bar had almost emptied and she came over to chat.
