Sweet November

Monday, November 11th....

I woke up with the alarm at 5:00 a.m., just like normal. I took a shower and groomed myself for work before heading to grab my "Monday" panties. When I opened the drawer it was empty. I turned around to see Jess sitting up on the bed with a devilish grin.

"You are going to wear something different this week," she told me, and pulled out a pair of black vinyl shorts from under her pillow. "Now, come here. I am going to help you put this on. This will ensure that you behave yourself this week."

As I walked over to her I realized they were more than just shorts. They were a chastity device.

She leaned over and positioned it for me to step in as she slid them up my legs. Then she grabbed my soft cock and balls and slid them into a cage. The cage consisted of a three-inch leather strap which held seven o-rings that got progressively smaller and encased my penis. Then there were two other straps underneath. One wrapped around the base of my balls and the other separated them. All three straps met at one large o-ring at the base of my cock and were locked shut with a tiny padlock.

Then she turned me around to pull up the back, but first she squirted a little lube on my asshole. Then she pushed a 3" butt plug into my ass and pulled the shorts up the rest of the way. Finally she locked two more tiny padlocks, one on each side of the shorts, ensuring that I could not remove the plug or cage without a key.

"You will be inspected at least once a day by a key bearer. At that time, if everything is as it should be, you will be allowed to pleasure them and masturbate for them. If, somehow, things are not in order, you will be severely punished. When you get home you will come straight inside without changing, and I will inspect you again. Then you will receive 10 spankings, just because I can, and I will determine your next reward." Then I was told to finish getting ready and make her breakfast.

When I brought her breakfast to her, she told me that we were going to have fun tonight, so I should get home early if possible. Then I grabbed my things and headed off to work.

I had a busy day ahead of me so I wanted to get as much done as possible as quickly as possible. I had a realtors' meeting right off the bat, to go over some new listing. Then Helen was supposed to be in around one to finish the paperwork on her house. After that I needed to get in contact with the other couple from last week so that we could put together a proposal on the house the wanted to make an offer on. On top of all that, I had a hundred other little things that were going to envelope my day.

With all my busyness the first half of the day went pretty fast. I had just finished eating the lunch I picked up when I saw Helen walking towards the door. I opened the door for her and greeted her with a smile. She looked just as beautiful today as the first time I met her.

"I assume everything is ready, right?" she asked, as she stepped inside.

I assured her it was and then directed her to the private conference area we often used when signing papers for real estate. I pulled the door closed behind us to ensure our privacy as I do with all my clients. Then I retrieved the appropriate paperwork from my briefcase and placed them before her to review. I went over each piece in summary and reminded her that they had all been approved by her lawyer. Then I showed her his initials on each form.

I was taken back a little as she worked through the paper work so quickly and professionally. It was as if nothing had happened the previous week. Soon enough, she had signed her last piece and handed me a check for the full amount. I informed her that I would get the deed to her as soon as the previous lien holders received their portion of the check.

"I trust you," she said bluntly. "Now it's time for your inspection."

I looked at her in utter shock, as she pulled a key from her purse. "But how did you..." I stuttered.

"I'll explain later," Helen interrupted. "Now let's see how you've done so far."

Not knowing what else to do, I dropped my pants and revealed my chastity device to her. She reached out with her key and unlocked the two side locks and then the one that locked the cage. Then she pulled the plug from my ass and slid the whole thing down to the floor and told me to step out.

I did as I was told, although I was still perplexed by the whole thing. Then she hiked up her skirt and said, "I believe you owe me something."

My confusion turned to arousal as gladly knelt in front of her and pulled her lacey red panties off. Then I dove right in with the enthusiasm of a sixteen year old. She tasted so good that I wanted to take my time, but fear of being discovered caused me to rush a little more than I intended. Nevertheless, I gave her a "mind blowing orgasm", as she put it.

When I stood, I had a raging hard-on. Helen reached into her purse and pulled out a little tube of lotion and squirted some on my cock and rubbed it on. Then she stopped. "You can take it from here," she said as she released it, gesturing for me to finish the job.

It was kind of humiliating masturbating in front of a beautiful woman. Until yesterday, I had never done it with anyone else in the room. But these were the rules and I was going to play by them. Helen helped me out a little by talking dirty to me and telling me how bad she wanted to see my "giant monster squirt". I shot my load in a fairly short period of time.

As I started to put my device back on Helen offered to help. This did not really surprise me until she pulled the lube from her purse and squirted on the plug and pushed it back in my ass. She also knew how to work the cage even better than Jess did.

While I finished getting dressed, Helen said. "I told you I would 'explain later', so you should probably have a seat. This may take a little while."

Helen went on to tell me that only bits and pieces about what I knew about her were true. She was in fact a widow and her husband was a prick with a ton of money, but that was about where it ended.

I was floored by what I found out in the next hour and a half of conversation with Helen. I found out that Helen ran a company that sold and serviced S&M equipment to the general public in a discreet way. Her company actually constructed and furnished the room in the house she bought. She had not seen it on line. Her company also gave seminars on how to be a dominatrix. Amber was one of her managers that distributed her product and gave instruction to others.

Jess and the others had attended one of the seminars at a lingerie and adult toy show a few months back and had really gotten excited about the possibilities, but Jess was not sure how to spring it on me. Helen had suggested the bet as the best way to break the ice. Helen and Jess had also been communicating via e-mail on a regular basis for hints and guidance. That was also how Jess knew all the details of what happened last week minutes after I got home. Helen emailed her from her laptop with all the info.

It took a while for it all to sink in, but it actually made a lot of sense. I was also intrigued by the amount of work Jess put into this. That really turned me on. Unfortunately the cage restricted too much excitement.

Finally Helen said she needed to get going and that she looked forward to seeing me again. I confirmed the feeling was mutual and got back to work as she headed out the door.

I talked to the couple from last week and we put together an offer. Then I got it over to the listing realtor to review with his client and let my customers know it might take a day or two, but I was confident we would work this all out. Finally, I tied up a couple loose ends and headed home.

When I got home I went straight in, just as I had been told. Jess told me to strip down to my 'shorts' for inspection. I immediately did as I was told while she pulled a key from her pocket. As she inspected me, she asked how everything went with Helen.

I told her it went well and smiled. She smiled back with understanding.

Once she was happy that the device was still firmly in place she unlocked all three locks and released me. "Bend over and grab your ankles," she ordered and I obeyed.

"Count them out," Jess commanded, as she struck my ass with her bare hand.

"One, two, three, four..." I called out following each slap, all the way up to ten.

"Good slave. Now put that back on and the clothes on the bed and I will take you to your reward," she told me, pointing to some jeans and a pullover on the bed.

As quickly as I could, I got dressed and met Jess in the family room. Then she told me to get in the car, she was going to drive. On the way to our destination we stopped and got some fast food to eat and continued quickly on our way. Jess said nothing the whole ride. She did not even ask me what I wanted to eat; she just ordered for me.

Finally we pulled into the parking lot of a Wal-mart across town. I was a little confused simply because we had one only a couple minutes from our house.

"Okay, we're here. Time for your reward," she chimed.

We got out of the car and headed inside. I had no idea what to expect. Jess led me up and down aisle after aisle looking around for who-knew-what. I was completely confused. We had been in grocery, toys, hardware, and now we were in girls clothing. I could not figure out what she could be looking for that could possibly be my reward.

Finally she stopped. "She's perfect," Jess proclaimed, as she pointed to a woman, pushing a cart, obviously shopping for her daughter standing by her side.

"I want you to go tell that woman that you would love to eat her pussy," she told me.

"You're kidding, right?" I said.

"No, slave, I'm not kidding." Jess said forcibly, reminding me of my status. "She looks like she could use it. Now go whisper to her, so her kids can't hear, that you would love to eat her pussy. And that your wife would be happy to watch her kids while you do."

I could not believe what I was about to do. I stepped slowly toward her wondering how hard she would smack me and how fast security was going to drag me out. As I got closer I understood why Jess said 'she could use it'. This woman looked to be in her late 20s, with a two-year-old little boy in her cart and a six- or seven-year-old little girl standing next to her.

She had a pretty face, but wore no make up to cover the slight bags under her pretty blue eyes. Her dirty blonde hair was pulled back in a pony tail and she wore simple hoop earrings. She was about 5'6" tall with an average build. It was pretty hard to tell much else with the loose fitting sweat pants and shirt she wore with her jacket. It was obvious she was tired from probably just getting off work.

As I approached her I called out, "Excuse me, can I ask you something?"

She looked around a bit to make sure I was talking to her. "I guess..." came her puzzled reply.

I looked back at Jess and saw her watching closely. Then I leaned in and spoke softly, "You look like a lovely woman, and you look like you could use a little fun right now, and I would love to eat your pussy. My wife is right over there and she says she would be happy to watch your kids for you while we're gone. So what do you say?" I paused, waiting for it all to sink in. I had said it all so quickly as I directed her attention to my wife standing 30-35 feet away.

"Are you serious?" she said, in disbelief.

"Completely and it would be my pleasure," I responded. "Besides, I am told I am quite good."

She stepped back and looked at me inquisitively and then looked over at my wife. "Wait here," she said, as she took her cart and kids and walked towards Jess.

I stood there and watched as they conversed for several minutes. At one point I saw her hand Jess a piece of paper and some money. Then they continued their conversation several more minutes before I saw the woman talk to both of her kids and then walk away leaving her cart and kids with my wife.

Jess walked over to me with a huge grin on her face. Jess told me, "Her name is Stacy and she will meet you at the front door in a couple minutes. Here is a key to room 227 for the hotel across the street. I will pick you back up at the golden arches in a couple hours."

"Did you just pimp me out?" I asked. "I saw her give you some cash."

"No," she laughed, "that was to finish her shopping with. She gave me her shopping list. I told her I would finish it for her and take her kids to McD's."

I took the key card from her and headed for the front door still not sure what was going on. Moments later Stacy walked up and we headed for the parking lot. She had gone to get a bottle of wine. I figured she needed it to set a tone or for courage. I just knew I was under orders.

When we got to the room she poured us both a glass. It was obvious she was still unsure. The wine was cheap, but after a glass-and-a-half she must have been feeling it, as she loosened up a bit.

"Well, you gonna eat my pussy or what?" she asked, in a tone that made it sound like I owed it to her.

I drank my last gulp of wine and proceeded in her direction. I pulled off her sweatshirt and pants to reveal her bra and panties. They really were not anything special. In fact they did not even match. Her bra was white and lacey and held her nice C-cup tits. She wore aqua-colored bikinis, obvious that she expected nothing like this to happen to her today. She was just a few pounds overweight but she carried it well.

As I reached out to remove her panties she stopped. "I showed you mine, now you show me yours," she insisted.

I thought about telling her it was a waste of time, but I figured it would take longer to explain than to just show her. So I took off my pants to reveal my bondage to her.

"Wow," she said. "I've never seen anything like that. No wonder you've gotten so good with your tongue." She got off of the bed and walked around me as she checked it out. She even pulled on the locks and the cage a bit to test it out. Finally she lay back down on the bed, and pulled off her panties. "Let's see if you really are as good as you say."

I climbed up between her legs to her moderately thick bush. It seemed as if she hadn't trimmed it in quite some time. Although, I was surprised to find how soft and smooth her legs were as I ran my hands up them to her pussy. I pulled her lips open with my fingers and explored her with my tongue. It took only a few minutes to bring her to orgasm. As I began to pull away she threw her legs around me.

"That was amazing!" she said between breaths. "You're gonna have to do that again." Then she pulled her surprisingly strong legs against my back and drew me in for round two.

This time I knew it was not going to be quite so easy, so I started out slow and steady and worked my way up to a quicker pace. After several minutes of lapping slowly at her pussy I found her clit once more, wrapped my lips around it, and began to hum. In no time at all she began moaning and writhing on the bed as started her climb to another climax.

I was surprised to find that I was starting to get aroused while licking this complete strangers pussy, and my cock was trying to rise in spite of the cage. The muscle of my member was no challenge for the metal of the cage as my cock struggled in futility to get hard. I now found my self experiencing a new sensation as my arousal grew, but my cock could not.

Nevertheless, I continued licking, sucking, and massaging her pussy until she screamed out in another orgasm. Finally she released me and rolled over on her side. Her eyes seemed to be a bit glazed over as she lay there, breathing heavily, with an enormous smile on her face.

After a couple minutes had passed I heard her say, "We aren't supposed to meet your wife for another forty five minutes. How 'bout we see what else that mouth of yours is good for?"

As I looked up I saw she was reaching behind her back to unhook her bra to free her C-cup tits. They sagged just a bit, I assume from child birth and breast feeding, but all-in-all they were nice and round with large, dark pink nipples. I crawled up the bed towards her as she lay back down. I took her breasts in my hands and began to caress and fondle them as I flicked her left nipple with my tongue. It quickly spring to life and grew to a length as big as I had ever seen.

As I continued to lick and suck on her left one, I rolled her right nipple between my fingers until it was equally erect. Then I proceeded to alternate between each one. I licked, sucked, pinched, fondled, and squeezed her breasts for quite some time. I could tell by the way she was rolling her head from side to side that she was enjoying herself, but eventually she wanted more and I felt my head being pushed down to her snatch once again.

I could not believe how turned on I was by this whole ordeal. The restriction on my cock was such a tease. The idea of propositioning a total stranger had been humiliating, but erotic all at the same time. All these thoughts hit me at the same time as I dove into her pussy once again. This time I was so aroused that I felt like a caged animal being set free to devour her. I licked and sucked her like as though I had not seen a pussy in ages. My intensity flung her over the edge quickly, thanks to her already heightened arousal, but I hung on for more and took her to the top two more times before I finally let her go.

"Holy Crap!" she exclaimed. "You are an animal." I sat back on the edge of the bed and watched her tits rise and fall with every heavy breath she took.

Shortly thereafter we were getting dressed and she grabbed my ass. "Thank you," she said. "I haven't had that much fun since before my husband passed away last spring. You made me feel alive again."

I just smiled as she kissed my cheek and we finished getting dressed. Then we headed back to the car to meet back up with Jess and her kids. When we arrived Jess was sitting there watching the kids as they played on the indoor playground. Stacy had a smile from ear to ear as her kids rushed to greet her when we walked through the door. Jess and I took that opportunity to sneak out and head home.

Jess did not say a word the whole drive home. She just sat there with a look of contentment on her face. I do not know if it was the kids that put that look there or her attempt to humiliate me. I did not bother to ask.

When we got home we both went right to bed without saying much of anything. She did remove my chastity device and let me sleep naked in my usual spot. That did present some bit of a problem as I soon found myself with an erection as I recalled the day's events. Luckily I was able to fall asleep before giving in to the temptation of pleasuring myself and did not have to face my Diva's wrath.