Last night had gone perfectly, Tabitha had played her role just as I had asked. Driving the borrowed Yukon, doing all the talking in her fake male voice and relieving my pent up sexual energy while we were teasing Tana.
After we drove away from the restaurant she pulled over as planned. I pushed Tana out under a street light and told her to strip. Once she was naked I dropped the hood back over her head and put the hand cuffs back on then forced her into the storage area.
We pulled her back out in the alley and Tab whispered."Go home, maybe he'll use you again sometime."
I waited almost a week, Tana was still working at the other location so I was easily able to avoid her.
One of the things I had learned during our dates was that she really liked the humiliation aspect, almost as much as the loss of control and the physical side.
She had also let on that flashing and exhibitionism was a big turn on, that's the main reason she dressed so slutty when going out to a club.
Tabitha and I had spent hours on the phone, first off so I could learn as much about Tana as I could and then planning the last adventure.
Tabitha had informed me that Tana's favorite band was doing a concert at a outdoor venue on the upcoming Saturday night. I sold a few things and got tickets, then redid the schedule so that we would both have the night free.
"I'll pick you up at 7:00 Saturday night, why don't you wear that black skirt, thigh highs, garter belt and a tank. I'll leave the shoes up to you." I texted.
"Yes Sir!" was the text I got back.
Not more than three minutes later my phone rang. "Bill? Tabitha here, I heard you are planning something. Need any help?"
"No, just taking her to that concert you mentioned."
"Oh" disappointment in her voice"
I chuckled into the phone.
Then "OH!" as she started to catch on.
"Yeah it's in a park or something right? Outside, dark, thousands of people."
Now she had the idea.
"Please, please where exactly are you going to be, I have a ticket I just have to see this."
I had been on Google Earth looking at the site, still not knowing exactly how it was going to be set up for the concert I wasn't sure where the best place was going to be.
"Tell you what, I'm picking her up at 7:00 we are going to stop at that roadside place for a bite on the way. Get there before 7:30 and find a spot where you can see the entrance and just follow us. I'm going to shoot for a place where we can see the drummer you said she has the hots for. Looking at their videos on YouTube he is usually on the right side of the stage."
I must have tried on fifty pairs of pants at the thrift store, finally finding a pair that fit well but were loose enough that I could get my cock out and not have them around my ankles.
Saturday morning I stopped by the adult toy store, I had called the number on the back of the receipt. I was easily able to pick out Jane by the blue strands in her hair.
Walking up to the counter I introduced myself. "Hi, I'm Bill we spoke on the phone."
She looked me up and down. "You're with the hot little slut that came in last week?" She asked with a look of astonishment.
Okay I guess I really don't look the part, neatly trimmed hair, blue jeans and white tennis shoes with a red polo shirt. I looked like what I was, a regular college guy, maybe a jock, which I had been until I got hurt and decided a degree was what I really wanted.
"Okay what can I do for you?" she asked.
"One thing for sure and another if you are interested. I need one of those butt plugs with the flashing LEDs in the base."
"Well that's easy enough." She said as she led the way down one of the aisles.
There were five different sizes and I grabbed the second to largest.
Where we were standing there were no customers or employees close so I explained the second thing to her.
She thought about it for a while then asked. "Let me see it?"
Looking around I undid my belt, and popped open the buttons on my fly, reaching in I pulled out my soft dick.
"Impressive." she said before agreeing to help.
I paid for the plug and a replacement set of batteries and handed her a ticket to the concert.
If I thought I had been excited before our restaurant adventure, tonight I was almost bursting.
I arrived at Tana's fifteen minutes early, I tried the door and it was open so I just walked in, I could hear her in the bedroom singing along softly to the band we would be seeing in a few hours.
I pushed the door open and she shrieked and jumped from the small chair in front of her makeup table. My eyes scanned her up and down, she was only partially dressed, black pumps with three inch heels, black seamed stockings, and a black garter belt. I stepped close and took her by the neck pushing her back towards the bed. I spun her around and bent her over. She had the emerald jeweled plug in her perfect ass. Grabbing it I tugged, pulling it part way out and started to fuck her with it. After fifty or so strokes I pulled it free and reaching around offered it to her lips.
Tana opened her mouth and accepted my gift. Her ass was still slightly open and I was very tempted to stick my now hard cock in, but that would wait. I had the new plug in a baggie in my pocket, I took it out and with a bit of pressure forced it in, her nether ring stretched and she let out a groan as it slipped into place, her asshole snapping closed.
I had had my hand around her throat the entire time and I roughly pulled her up and kissed her lips hard, squeezing just a bit to remind her who she belonged to.
She quickly finished her makeup and before dressing she put my collar around her neck partially obscuring the marks from my fingers. She then slipped on her skirt and a shimmering silver open backed tank with a plunging neckline that just barley covered her tits. As usual her nipples were like little rocks and could be clearly seen through the thin material.
"You need to keep your door locked, anyone could have come in."
I sat on the edge of the bed and pulled her to me, I nodded at her and she positioned herself over my knees pulling her skirt up.
"Count"
Running my calloused hand over her firm ass and pushing on the base of the plug before giving her a swat.
"One Master."
I aimed the next two for the base of her cheeks just above her thighs where the red hand prints would still be covered by the short skirt.
"Two, three Master, thank you."
I wanted to let her know I was really displeased about her leaving the door unlocked, so the next two landed dead in the middle of each cheek, harder than I have ever done before. My hand stung from the blows.
Holding back her tears "Four, five Master. Thank you for correcting my mistake."
I caressed the deep red marks on her butt before helping her up, she adjusted her skirt and checked in the mirror to see if the base of the plug was visible. It was, but just barely, she tried to pull the hem down more but I reached out and took her wrist stopping her.
"I think that will do!" I said firmly.
It was only a ten minute drive to the park, so we had plenty of time to stop by a roadside taco stand and grab a bite on the way.
I told Tana my order and gave her some cash, leaning against the hood of my truck watching her go up to the window. There were a few other people around sitting at tables eating or waiting for their orders.
For her to get to the window she had to walk between the tables, people's eyes at just the right height to see the plug in her ass. A younger woman about our age did a double take and then whispered to her male friend, he looked right at Tana's butt as she stood waiting her turn to order, not six feet from him. He nudged the guy sitting next to him with his elbow and pointed at Tana.