A Night to Remember Ch. 01

It was 1988 and I was 25 at the time. She was 40, and my first foray into the "Sugar" life. Our start is a tale for another time, but this is the story of one of my favorite nights with her. It was truly a night to remember.

As I said, she was 40, but you'd never know it as she easily passed for late 20's or early 30's. Red hair... and I do mean RED hair. Her nickname was "Big Red", not because she was tall, as she was only 5'2", but because she kept her hair 1970's big and it was red enough to draw every eye in the room.

And her body... oh how I loved her body. 34C's with nipples that showed how she was aroused at almost anything remotely sexual, a tiny waist moving down to only slightly wider hips that all the more accentuated her breasts.

Pale skin and green eyes that I swear said "fuck me" anytime you gazed into them.

We were going out to a bar where a blues band we liked was playing. I had asked her to wear her black mini, red blouse that was slightly transparent, her black bra, and her "dancing shoes."

No, they weren't ideal for dancing, though she could kick up a tempest in them. They were shiny black pumps with a four-inch heel that today we'd call "Fuck Me Pumps."

The shoes did not lie.

The ensemble was completed by black hose, as she was a garter girl, and a black choker around her sweet neck.

You don't care what I was wearing and quite frankly, I don't remember.

We sat down, had a few drinks, then, as the band started, I handed her a small gift bag. I told her to take it to the bathroom go into a stall, then open it.

She goes to bathroom, steps into a stall, closes the door behind her and sits down on the lid. She opens the bag and inside are the following:

A note.

A vaginal egg.

A small, thin butt plug.

A pair of panties with a clit stimulator in the crotch.

And a bottle of lube.

She opens the note and it says,

"Take off your panties. Place them in the bag.

Place the vaginal egg in your pussy. Use lube as necessary.

Place the butt plug in your ass. Use lube as necessary.

Put on the panties I've provided. Make sure the stimulator is right no your clit.

Put your panties and the lube back in the bag.

Come back to our table."

She does as asked, and leaves the bathroom. As she crosses the dance floor heading back to our table she is almost overcome when I turn on all three devices at once. She stumbles just a little, then gains her composure and heads to our table with a big grin on her face.

I leave the devices on for a few minutes until the server, having seen her sit, comes to get our drink order.

I turn them off.

The server, a young blonde beauty with a ponytail asked, "what will you folks have?"

I nod to my lovely and she says, "a shot of teqEEP," as I turn on the devices. She turns her head down, closes her eyes, and lets out a long breath.

The server asks, "are you alright?"

I turn them off.

"Yes," Red replies. "Just something pinched me in my underwear."

"Maybe a stray bit of metal?" asked the server.

"Yes, a stray something..." Red giggled. "Definitely something gone astray. Anyway, I'll have a shot whatever your top shelf whiskey is and whatever beer he's having as a chaser."

I ordered the local lager (you've never heard of it, trust me) and hit the switch.

She made the face again as the server started to leave. "You should go the bathroom and fix that before it gets the best of you honey."

Red half grinned/half grimaced and looked right at me and said, "yeah, I should, but I wont."

I would always turn them off it appeared she was getting too close to cumming. I wanted her to build up, teasing and denying her throughout the evening.

When one of our favorite slow tunes came on, we got up to dance close and tight. I could feel her nipples poking me in the chest as I turned the devices on.

Periodically through our dance I would press my thigh into her crotch, crushing the clit stimulator right down on her poor, throbbing button and she would moan in my ear.

Throughout the evening I started turning on the device every time the server came over, and Red's demeaner began to change. She would look at the young blonde hungrily as she approached, compliment her, sweetly ask her name (Jenny) and then tell her what a pretty name it was.

I was clear to anyone who wasn't deaf, dumb and blind that my gal was coming on to Jenny, and the blonde wasn't shying away and even flirting back.

I came back to our table, after a trip to head, to see Red holding her blouse open and showing Jenny a look down her top.

As I sat Jenny looked away quickly but Red just said, "she was admiring my bra and I wanted to show her the lace on the cup."

Jenny was a little flushed so I chimed in, "Oh, it's quite lovely. Jenny, if you'd be a dear and head back and get us three shots of that whiskey she's been drinking."

"Three?" she questioned.

"One for each of us and don't you say no or I'll be horribly crushed," I said.

"Oh, I'm not saying no. Just making confirmation."

We continued to dance, drink, play with the buttons, flirt with Jenny and buy her drinks until about 1am. The bar closed at 2:30am but I wanted to get out before then.

As Jenny came by to settle up with us, I gave her $100 on a $40 bar bill with a note folded on top.

She opened the note, which had Red's address and phone number on it as I gave her a questioning nod. She glanced at Red and then looked back at me with a nod that was either, 'I might, I just might' or 'I'm being nice to pervy couple because they gave me a good tip.

I just said, "well, until after closing then," and we left.

In the gravel lot my little hot and bothered gal had trouble crossing in her FMP's with the toys humming away, and so held tightly to my arm. At the truck I started to help her into the cab, but instead reached around in front and once again pressed the little buzzer against her clit tightly and she bent over moaning. I held it there until I was positive she was going to cum like a house on fire... and I let go and turned them off.

She looked at me pleadingly and I just shook my head no. I had plans.

I pulled a set of thumbcuffs from my pocket and placed her hands behind her back with her thumbs locked securely. I helped her into the seat and scooted her to the center (Those of you who never had the pleasure of a vehicle with a bench seat don't know what you missed) and buckled her in.

I got in the drivers side, leaned over to her and kissed her hard as I popped the buttons on her blouse. I then pulled back and popped the shoulders of it down to her elbows, reached down the neck and did the old one hand pop on the bra clasp. Then with my other hand I exposed her tits, gave each nipple a good pincy, each soliciting a moan, and then turned on her hummers and the engine to begin the drive home.

It was short drive, but through very well lit streets to her home. At one point we pulled up next to a truck full of teenagers, a boy and two girls, who were in awe of our current situation.

Lovely Red just shrugged her shoulders at them and then moaned as I pressed the buzzer hard on her clit again.

I pressed it on her clit on and off until we reached her driveway, used the opener on the garage door and I pulled in.

NEXT CHAPTER - We begin preparations at home.