Tuesday, November 12th...
Tuesday started just like Monday except the chastity device I wore today was white instead of black and had no butt plug. Other than that it was exactly the same.
I started my day like the others and prepared Jess's breakfast, did a couple quick chores, and then headed off to work. I really did not have anything significant to do other than to follow up on a few issues and check on the offer that my clients made the day before. Unfortunately the seller was still mulling it over, so we were not going to get an answer for another day or two. In spite of the fact, I had a relatively uneventful morning; it went fairly quick and I decided to take a quick break for lunch.
When I returned from lunch I had a message on my voice mail from Jess. It said that she had scheduled a haircut for me at two and if that conflicted with anything to just give Kate a call and move it back a bit.
I did not have much going on and my hair was getting a bit long, so I headed to see Kate just before two. When I got there, Kate was finishing giving a perm to one of her older clients, so I took a seat in one of the waiting area chairs and picked up a magazine. I fumbled through the magazine pretending to mind my own business while Kate and the woman in her late 50's chatted.
I got a kick out of hearing them talk about the hot guys on the soaps and in some of the movies they had watched lately, but I was startled when the older woman whispered something about the "cute young man that just sat down." I continued to flip through the magazine pretending like I had not heard a thing as they finished their conversation.
A few minutes later Kate took her over to one of the chairs with the bowl that pulls down and dries your hair. After she turned it on, she motioned for me to have a seat in the barber's chair. As I was about to have a seat, Kate stopped me.
With the roar of the hair dryer in the background she said, "It is time for your inspection." She smiled, "I will let you decide how we do this. You can either take your clothes off, right here and now, and sit naked in the chair while I cut your hair. Then I will let you eat my pussy. OR you can wait to do your inspection until we are done and alone, but you have to eat the pussy of whoever walks through that door next."
I pondered the situation for a minute and decided to strip now. I figured gambling had not been my thing lately, so I better take the sure thing. Moments later, as I stood before Kate in just my white vinyl shorts, I heard the woman at the hair dryer gasp. It was obvious she had looked up from her magazine and saw me standing there half-naked as Kate inspected me. Kate just looked over and winked at her as she unlocked the device. I, on the other hand, refused to turn around and look at her. I was far too embarrassed.
Once Kate was satisfied that everything was in order, she told me to have a seat and draped the barber's sheet over me to keep the hair off. Just then the lady at the hair dryer moaned her displeasure. So Kate decided since I was not wearing any clothes to get hair on that I did not need the sheet after all, and she pulled it off. Without even looking up I could tell this made the mystery woman's day.
Initially I tried to cover myself up, but Kate ordered me to put my arms on the arm rests and relax. That was easier said than done.
Normally Kate wore simple jeans and a t-shirt to work, but today she wore a rather low-cut blouse with her jeans. So every time she stood before me she made sure I got a good look down her top to her braless tits. She also made sure to brush them against me as often as possible. It was obvious from the way her nipples stood out that she was enjoying teasing me. However, it was even more obvious that I was enjoying the teasing by the size of the erection I was sporting.
By now the woman in curlers had put down her magazine and just stared wide-eyed while Kate finished cutting my hair. Finally Kate finished and told me to stand. I had hair all over me. She grabbed a hair dryer off the counter, turned it on, and blew off all the hair.
"Nancy," Kate said, addressing the lady at the hair dryer, "what do you think?"
Nancy just sat there with her eyes wide and her mouth agape as Kate turned me to face her. I could scarcely look at her. I was so humiliated. Then Kate took it even farther.
"Nancy, would you like to see him jerk off?" Kate asked.
I could not believe she said that, but I did not have to wait long for an answer as Nancy was already nodding her head.
"Alright, Slave, get to it," Kate commanded, as she slapped my naked ass.
I slowly began to stroke my already erect member as I closed my eyes. I knew there was no way I was getting out of this so I tried to think about Kate's naked body as I stroked faster and faster. Just as I reached climax I felt something wet at the tip of my cock. I opened my eyes to see Nancy on her knees in front of me with her tongue out in anticipation. I wanted to stop, but it was too late. I had gone too far and could not stop it as come began to spurt out of my cock onto her lips and tongue. I continued to stroke until I was finished and Nancy swallowed every last drop.
The look on her face was priceless. She looked as though she had just drunk from the fountain of youth and she was going to live for ever. I had never seen a woman her age with a smile so big, but I could not help but be embarrassed as the humiliation rushed over my body.
Kate waited just a minute before she grabbed me and pushed me into one of the tanning bed rooms. Then she slammed the door and left me there to recover.
I sat naked in a plastic chair for at least fifteen minutes before she finally returned. "I had to finish her hair," Kate said, as she pulled the door closed behind her and began to pull off her jeans.
"You know I have never gotten a bigger tip from anyone in my life than that woman just gave me," she commented, as she pushed me to the floor and straddled my face. "Now it's my turn to get off. I am so horny from watching you. Don't you dare make me wait."
Another second did not even pass before I raised my head to her delicious pussy. She obviously had been turned on because she was soaking wet. I wanted so badly to take my time, but by the way she was bucking up and down I could tell I better make it quick. I darted my tongue in and out of her sweet hole a few more times before I stopped at her clit and finished the job. She rode my face even harder as she reached the pinnacle of her climax and shook violently. Then she fell back on top of me panting heavily.
She quickly pulled her jeans back on and rushed back into the salon. Then she threw my clothes back at me so that I could get dressed and return to work. By now it was almost four and I had to get back to the office to make a couple calls before I could go home. So I paid Kate quickly for the haircut and ran out the door.
When I got back to the office it was a relative ghost town. There was no one in sight. This allowed me the time I needed to get a few things done that I needed to get done without the possibility of interruption. Just as I was finishing up, my phone rang. It was Jess telling me to stop and get something for myself to eat on the way home because she was not going to give me any time to get any later.
I hung up the phone, grabbed my things and headed out the door. I drove through a fast food place close to my office so I would still have time to eat as I drove. Thanks to a decent-sized train holding me up, I did not have to scarf it down. By the time the final train car passed, I had finished my supper and drove quickly home.
As instructed, I parked and walked right in to Jess for inspection. Once she gave me permission, I stripped down to my chastity device, and she proceeded to check me over. After that she unlocked it and pulled it down to my ankles, sat down on the couch, and then pulled my naked body across her lap. Then she reached up underneath me and grabbed my cock and balls and secured them firmly between her legs. Then I watched as she reached down between the cushions of the couch and pulled out a twelve inch leather strap with a wooden handle on the end. Without ever saying a word she landed swat after swat on my taught ass until ten had been given and my ass began to burn a little.
"You didn't count," she complained boldly.
I began to object that I had not been instructed to, but then thought better of it. "Sorry, Mistress, please forgive me," I begged.
"Ten more swats ought to be enough to remind you to count out your spankings," she jeered, as once again she pulled harshly on my now-erect member in order to keep it in place.
"One," I called out as she planted the first swat on my bottom. I followed each additional swat accordingly until a grand total of twenty made my ass burn.
Finally she released my raging erection and let me stand. "Now get dressed. I have another surprise for you," she said nonchalantly, as she pointed to my chastity device and the jeans and sweater she already had prepared for me.
I walked over and put on the sweater, but was unable to get my shorts back on due to my aroused state. Jess noticed and walked towards me and then grabbed my cock firmly and pulled me by it to the patio door. Before I knew what was going on, she had thrown me outside wearing just a sweater in the middle of November.
"You can come back in when 'that' is gone," she said in anger, gesturing towards my erection. "And don't even think of jerking off." Then she slammed the door.
The only good thing about it was that it was already getting pretty dark out, so I do not think anyone saw me, and the cold caused my erection to dwindle rather quickly. Unfortunately Jess had disappeared from sight and left me outside several minutes longer than necessary to get the desired effect.
Finally when she returned, she grabbed my arm and pulled me back in. "I don't have time for this," she announced harshly, as she took it upon herself to put my bondage back on.
She was not gentle about it in the least bit. She forced my cock and balls into their cage and locked them tight as though they were a rabid dog she was taking to the pound, never to be heard from again. I winced several times as she locked it in place; then she tossed me my jeans and told me to hurry up as she opened the door to the garage and got in the car. I quickly pulled up my pants, slipped on my shoes, and then joined her in the car.
She drove for several minutes without saying a word. Occasionally I would look over to see a smirk on her face. It was obvious to me she was pleased with the devious idea she had running through her mind.