Never Judge a Book by its Cover or A Wolf in Sheep's ClothingSubmitted by: Lickitgood
Rachel was a magnificent woman who was 15 years younger than my 40. When I originally hired her as my executive assistant, I was immediately drawn to the beauty and confidence she demonstrated on a regular basis. I found myself daydreaming about her, assured that a women like her would never be interested in a man like me. Rachel stands 5' 11" in her bare feet. She has beautiful long blond hair with ringlet curls, blue eyes and a smile that stops me in my tracks.
She always dresses very professionally in suits that showed off her long legs and enough cleavage to tease the lucky soul that caught a glimpse and let him or her know that she was very well endowed. She was the kind of woman that knew she turned heads and deep down loved the feeling of power it gave her. I very quickly became dependant upon the high quality of work she always demonstrated. She organized my office, my computer, my life.
Fooling myself that I could shove the genie back into the bottle I decided that I had to try and ask Rachel out. What genie you ask? While I'm quite good at hiding it in public, I'm quite the submissive in private. My sexual tastes are more exotic than most: bondage, forced oral sex, prolonged sessions, feminization, role reversal and most importantly chastity. Nothing quite stimulates me more than dreaming about having a beautiful woman dominate me, take control and do as she pleases. Up until now, my 40 years have only been filled with dreams of this desire and no fulfillment. Sure I have purchased several 'toys' and have even on occasion practiced some self-chastity with a belt I purchased, but it always ended the same way with me being frustrated that I could not find somebody to share these fantasies with. I finally reached a point in my life where I felt I had to ignore these desires and act "normal" if I ever wanted to share my life with somebody as sweet and beautiful as Rachel.
Unbelievably shocked, I stood before Rachel in my office when she said yes to my invitation to dinner. She flashed a smile and turned on her 4" heels, which made her 5" taller than me, and walked away. As she reached the door to my office she turned and said, "Would 7:00 tonight be alright?" Embarrassed that I was so excited she said yes, that I forgot to tell her a date and time, I croaked out a feeble, "yes" as she smiled again and resumed her work at her desk outside my office. I vowed there and then, that I would cast my submissive tendencies away and act as normally as I could with Rachel. I spent the rest of that Friday afternoon trying to do work, but found myself drifting off thinking about the good fortune I had that afternoon. At 5:00 Rachel came into my office and handed me a piece of paper saying, "This is my address. See you at 7:00." Again I felt foolish for not thinking to ask where I should pick her up.
At 5:30 I left my 27th floor office and raced home. I took extra care to hide all of my 'toys' just incase we ended up back at my house. I changed into casual attire and hopped into my Porsche. At exactly 7:00 I pulled up to Rachel's house. I knocked on the door and when it opened the vision was stunning. There stood Rachel in what must have been 6" heels in a very tasteful yet short dress exposing most of her long legs and showing off her ample breasts. I looked up into her beautiful blue eyes and asked if she was ready to go. We headed out to the beach to a very quiet little Italian restaurant I frequent. It's right on the water and very romantic. We sat there eating and making small talk. After dinner was cleared Rachel took a more serious tone asking why I was not married at 40. Not wanting to divulge my secrets, I simply said, "I have not found the right woman yet."
"Come now Steve, there must be more to it than that."
Nervously I said, "No."
"It's ok Steve, you can tell me anything."
Tempted, but not taking the bait, I said, "There is nothing to tell."
"Really Steve, if you can't be open with me, I don't know if we should go out again."
I was so torn. On the one hand I was scared that she would not want to go out with me again and on the other hand I was scared to let my secrets out for fear of scaring her away.
"Steve, I seemed to have dropped my phone under the table. Would you be a dear and pick it up for me?"
As I crawled under the table I got a great look at her legs which were right in front of me. I lost track of time staring at her legs.
When I returned to my seat Rachel asked with a giggle, "Did you enjoy the view down there?"
My mouth suddenly felt as if it were stuffed with cotton. Then she put her hand on my thigh and said, "It's ok Steve, I know."
"Know what" I asked.
"Steve, I'm in your office and on your computer at work all the time and I know what web pages you like to frequent."
Fear gripped me and I was unable to say anything.
Very sweetly Rachel said, "Steve, I know you have very special needs and I think I can help. From what I can tell you have a very submissive personality. I on the other hand love to be dominant. If you let go of your fear and are open with me, I think we can make each other very happy." Then she reached into her purse and pulled out a bag. She handed it to me. "If you want to finally live out your fantasies and overcome your fear go into the bathroom and follow the instructions inside. Remember though, if you go through with this, there will be no turning back and I will have complete control." Then she handed me a cup of ice and some butter in a napkin and told me, "You will need these".
Stunned and not knowing what to do, I walked to the bathroom. As I closed the stall and sat down, I opened the bag and found the instructions. "Dear Steve, I know you are submissive and would like nothing more than to please and serve a beautiful woman like myself. If I'm correct you will put on this chastity belt and butt plug and hand me the key when you return. Steve if you agree to put this on, you will be in my control and we will play by my rules. Think carefully before making this life decision. There is no turning back and you will be made to do things you never have done before. If you agree put the belt and plug on and when you return to the table refer to me only as Ma'am for the rest of the evening."
I was shocked, excited and scared all at the same time. This could be a dream come true fulfilling my fantasies with a women like Rachel. I pulled out the belt and examined it. It was a finely crafted stainless steel belt that went around my waist and through my legs. It all joined together in the front where a plate covered my groin area. My penis would be bent back and pulled through a tube. I would be forced to pee sitting down. Then there was the butt plug. It attached to the stainless strap that would be pulled from the back side of the belt to the front under my scrotum. I looked at the devise and knew there was no way for me to get it on because I was as hard as I have ever been. Nonetheless I placed the belt around my waist and joined the two ends in the front. With a click the first lock was engaged. It was a tight fit. Next I took the plug and realized what the butter was for. I coated it and then attached it to the 2" thick stainless belt that was to be pulled through my legs. I lined up the plug and very painfully inserted it into my virgin ass. I then pulled the stainless strap up and tried to get my penis in the tube attached to that strap. The tube was too small to get my engorged penis into. I then took some ice and held it on my penis until it became flaccid. I quickly pulled my penis through the tube and pulled the stainless strap up to meet the front of the belt. This also drove the plug deeper into my ass. It joined where the other two parts of the belt came together and click lock number 2 was engaged. Then I took the front plate and pushed it in until I heard a 3rd click. There I was standing there with metal underwear on and no way to even touch my penis let alone make it hard. I looked in the bag again and found a gold key and a pair of pink woman's underwear. I figured I was supposed to put them on which I did. I pulled my pants up and walked very gingerly back to the table. I sat down next to a smiling Rachel. I handed her the key, and said, "Rachel I can't believe I'm doing this, but here is the key."
With a stone cold look she asked, "What did you call me?" Before I could fix my error Rachel reached into her purse and pushed something that sent a shock to my groin.
Smiling Rachel informed me that she held a remote that could administer shocks through the belt. "I will be using this to train you Steven."
"Yes Ma'am" I quickly responded not wanting another shock and wondering what I got myself into.
"See, it's working already! Now Steve, I know all about your desires. I've been tracking everything you read on the web for a long time. I plan on letting you live out your fantasies and more while you please me and serve as my slave. I plan on taking you way beyond anything you have dreamed of. And remember, you have nobody else to blame but yourself. You chose to put the belt on. I seemed to have dropped my phone again. Please be a dear and pick it up. While you are down there on your hands and knee staring at my legs again, I expect you to kiss my feet for the honor."
As she moved her hand towards her purse again, I quickly ducked under the table, found her phone and kissed her beautiful feet. I was thankful that the tablecloth went almost to the floor so nobody could really see me. She pulled her foot from my mouth and used it to tab the front of my belt signaling me to come back up. I quickly returned to my seat.
"Do you like me feet Steven?"
The waiter came and asked if we would like dessert. Rachel said, "No thank you. Stephen would you like dessert?"
Knowing I had to answer her properly in front of the waiter or get shocked left me no choice. "No thank you Ma'am." The waiter raised an eyebrow and left the check. I quickly paid. As we got up to leave Rachel whispered into my ear, "I expect you to heel whenever we are out in public."
"Yes Ma'am" I couldn't believe the change in her, or was she always like this? I walked behind her to her left. Being a tall woman she took long strides as we walked to the front of the restaurant. It was difficult keeping up with her with the plug seated firmly up my ass. As we got to the car Rachel stated that she will drive. "Yes Ma'am." About a mile up the coast she pulled over on a dark shoulder and told me to take off all of my clothes accept my underwear. I complied and handed her everything. She left them by the side of the road and drove off.
"We are going to your house Steve." She had been there many times to drop off papers so she knew where she was going. About a mile from my house she pulled over again. "Get out Steve!"
"Ma'am please, somebody might see me." She moved her hand towards her purse. I got out quickly.
"You have 15 minutes to get home. If you are not there on time, you will be punished." She took off. Barefoot and essentially naked I tried to run and stay out of site. With the plug up my ass, I could not run very fast. I was about halfway there, but I used 10 minutes. I ran as fast as I could and luckily nobody saw me. I made it to the front door but having no keys I was forced to knock. She buzzed me in and there before me stood my goddess dressed in a black leather bustier, a tiny black mini-skirt and thigh high black leather boots with 6" heels.
"You are late Steve!" I could not believe how my sweet beautiful assistant had turned into this goddess bitch who now had complete control of my life. "I let your maid have the night off. I hope you don't mind."
"I'm sorry Ma'am. I tried my hardest." I felt so small next to her yet I was so turned on. I couldn't believe I was groveling for mercy from the person who was my assistant, but now my mistress. I could feel my penis trying to get hard to no avail. She sat on the couch and perched her feet up on the coffee table. In a lustful pose she spread her legs to reveal her moist pussy.
"Get to work," was her only command. I got on my hands and knees between her legs and started to lick her blond pussy.
Page last updated 06-Sep-16 by: Altairboy@aol.com