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Sweet dare


My New Career
Note: This story is based on an actual roleplay scenario I acted out with a professional dominatrix.

My situation was desperate. I had retired early (at age 46) three years ago from a well-paid position as an investment manager. I had a substantial nest egg that I was sure could take care of myself and my wife for the rest of our lives. In the investment field, we had a saying. "Bulls make money. Bears make money. But pigs get slaughtered." As it turned out, I was a pig.

I came across an investment opportunity that looked like it could provide us with a very good return. As it turned out, the person simply absconded with all of our savings.

We were destitute. To make matters worse, my wife contracted a serious form of breast cancer.

One of our neighbors, Carol, ran what seemed to be a very successful business. Although quite attractive, with a slim build on her petite 5'3" frame, she had never married.

Whenever we met her at parties, she was always seductively dressed. Her shoulder-length, strawberry blonde hair was always attractively arranged. She was personable, even "cute." I did not know anything about what her business involved. But I badly needed to find a way to bring in some income.

Embarrassed about my situation, I asked if we could meet confidentially to see if there was anything I could do to help her business. She eagerly agreed.

I was taken aback by her appearance when I arrived at her home for out meeting. I was anticipating a business conference and was dressed accordingly. She met me wearing spiked heels, a short black skirt and a white blouse--with no bra.

She leaned over, and, kissing me, invited me inside. Holding my hand, she led me into her living room. We sat opposite each other and engaged in some small talk.

Nervously, I confided to her the humiliating details of our precarious financial situation. I asked if there was anything I could do to help her business.

Carol got right to the point. "I can certainly use you," she began. Then came the bombshell. "My business is providing male companions to busy female executives," she explained. "My clients are all over the country and even international. These busy women do not have the time to devote to serious relationships. You will be well compensated. Now, I need for you to stand up."

I was very reluctant but we needed money soon and I had no other prospects. Slowly, I rose from my chair. In a tone I had never heard from her before she barked, "Okay, now strip for me." With a deep sigh, I realized I had no choice.

As my heart raced, I unbuttoned my shirt and, pulling it off, laid it on the chair. Reaching over, I took off my shoes. My hands were shaking as I undid my belt and unzipped my pants. Pulling them down and then off my legs, I placed them on the chair. Standing there in front of my neighbor in my underwear, she snapped, "Everything.

Underwear, too." Biting my lip, I pulled off my underwear and laid it also on the chair. Folding my arms in front of me to cover myself, Carol laughed and ordered, "Hands behind your back." When I did not immediately comply, she repeated, more forcefully, "Hands-behind-your back, now!" Closing my eyes so I would not have to look at her, I placed my arms behind my back.

Rising from her chair, Carol strolled over to me. Whispering, she commanded, 'Open your eyes and look at me." I did as I was told. I gasped as she reached over and began to lightly fondle my penis. "Just so you will know. I have cameras recording our little meeting. If you do not cooperate fully with me, the evidence will go to your wife. I do not think she would appreciate seeing you naked in my living room with me playing with your pecker."

Moaning as she continued to stroke me, I panicked. Near tears, I begged, "Please, Carol. Barbara does not know about our financial problems and she is very sick. Please do not do that to her."

Adopting a much more aggressive persona, she roughly grabbed my cock. Ignoring my scream, she said, "For starters, you will never address me as Carol again. You are to address me as 'mistress.' Is that clear?"

"Yes," I mumbled.

My knees buckled as she gave a hard twist to my cock and asked, "Yes--what?"

"Yes, mistress," I answered.

"Very good," she replied. "You just be a good little slave for me and Barbara need never know of our arrangement." Resuming her light teasing of my cock, she continued, "I have a few basic questions. First of all, how often do you masturbate?"

I could not believe that my neighbor was asking me something like that. Embarrassed, I answered hesitantly, "I do not know. Maybe once or twice a week."
She inquired, "How many people have you had sex with in the last six months?"

Offended, I responded sharply, "I love my wife. I could not be with anyone but her."

Carol snickered and taunted me, "Oh, trust me. You will be with many others now. And that will start with me before you leave here." Her next question was even more offensive. "Have you ever been with other men," she wanted to know.

"Absolutely not. I do not believe in that," I snapped.
Unperturbed, she shot back, as her free hand caressed my buttocks, "Well, this may then be an opportunity for you to learn some new skills."

Taking me by the hand, she led me through the living room and down a hallway. At the end of the hall was a door. Opening it, she ushered me inside. Entering behind me, she closed the door and locked it.

My heart sank. Looking around, I saw items, devices and accessories I knew to be used in BDSM activities. Leading me to the middle of the room, she positioned me on a raised pedestal. Leaving me there, she made her way over to a table, where she produced a vibrator. Returning to me, she announced, "This part will also be filmed.

The clients need to see what kind of erection you produce. Spread your legs." I stood there, just in shock. Angrily, she snapped, "Do not defy me. Spread-your-legs. Do it!" With a sigh, I moved my legs apart. She flipped a switch on the vibrator and I grunted as she roughly shoved it against me. I did not want it to happen but I felt myself becoming aroused. As the humming device pushed into me, she intoned, "Come on. I know that you can do it. Get-it-hard-for me."

Eventually, I reached a point that I just could not hold out longer. I started to refer to her as Carol but caught myself. "Car--, I mean mistress, don't make me do this. Please. OHHH, GOOOOOD!!!" She seemed to know exactly the right moment to act. Pulling the vibrator away, she left me standing there on the pedestal, shaking and breathing hard, with a throbbing erection. Humiliating me further, she produced a tape measure and placed it against my cock, presumably as information for her clients.

Noting the measurement, she said, "Uh, hum. Very good. Now, I need for you to complete the process by making yourself cum. As you do it, you are to pretend you are with your wife. Talk to her as you orgasm for me. DO IT!!!"
I put my hands up in front of my face but knew I had to comply. Moving my hands down between my legs, I began to play with myself as the mistress watched. Stroking myself, I muttered, "OH, Barbara. OH, GOD, Barbara, I love you so much. Barbara, honey, AWWWW!!!" With that, I ejaculated onto the floor in front of me.

"Good boy," my mistress exclaimed. Taking me by the hand, she led me down from the pedestal and to a wooden device against the wall in the shape of an "X."

Positioning me against it, she took leather cuffs laying at each corner of the "X" and attached first my wrists and then my ankles to the four corners, leaving me spreadeagled and exposed. As I was restrained and helpless, she used a towel to lovingly wipe away the remaining juices from my orgasm. I could not imagine a more humiliating experience. I was wrong.

From a nearby table, she obtained a metal box with two knobs. Protruding from the box were a series of wires with adhesive patches on the ends. Attaching the patches to strategic spots around my groin, anal area and chest, she announced, "You will have to learn that your cock, in fact your body, is now my property. I can do with it as I please. Earlier, I asked you how many people you had had sex with in the last six months.

You were not truthful with me. I will not tolerate dishonesty. For that, you must be punished." With that, she twisted the knobs and electric current shot through my penis, anus and nipples. My knees buckled against the restraints, but I was helpless. "I ask you again," she intoned, how many people have you had sex with in the past six months?"

Near tears, I insisted, "I told you the truth, Car--, I mean mistress. I have been faithful to my wife."
Again she twisted the knobs. I gasped and my knees again buckled against the restraints. "I do not believe you. Tell me the truth," she insisted.

I had no choice but to make up something that I hoped would satisfy her. "Okay, um, I was with Kathy Rehring." She was another woman in our neighborhood.

"Details. I want the details," she snapped.

"Okay, um, it happened when Barbara was at the hospital. Kathy came by the house to comfort me. One thing led to another and, uh, we ended up spending the night together."
Satisfied, she said, "Good. Now, as long as you cooperate with me, your secret is safe with me. You wife need never know that you fucked her best friend while she was in the hospital." I was angry that this forced, false confession could be used as blackmail against me. But there was nothing I could do.

She then inquired, "I also asked if you had been with other men. You denied it. Are you open to experimenting with that?"

Instinctively, I blurted out, "No way. That is just disgusting to me."

Again, she twisted the knobs and the current jolted through my sensitive areas. I knew the prior answer was not acceptable. With a deep sigh, I mumbled, "Okay. Okay. I will...I will be open to, uh, that."

One more time, she twisted the knobs and the current flowed through me. As I screamed, she explained, "That is just to let you know that I own this body and I can do this to you at any time that I please." She removed the patches and replaced the box on the table.

Releasing my wrists and ankles from the cuffs, she led me to a sort of medical exam table. She patted the table, indicating for me to sit on it. When I complied, she pushed me down onto my back. She instructed me to spread my legs wide so that my feet were off the table. Leaving me there, she went over to another table and produced shaving cream and a razor.

Standing at the end of the table between my legs, she pulled my legs down so that my groin was at the end of the table. She then began to rub cream onto me and explained, "Many of our clients like to have the property shaved. Lie still while I shave you." Looking up at the ceiling, I first felt the cold sensation of the shaving cream on my pubic hair. I gasped as I felt the sharpness of the razor pull against the hair. "Lie still," she commanded again.
When she was done, she helped me up from the table. We exited the dungeon and returned to the living room, where the meeting had begun.

"Okay," she cooed lovingly, "now I need to see how well you can perform." Bending her stomach over a sofa, she looked back at me and barked, "What would your precious wife think if she saw you fucking me in the ass. Do me. Now. That is an order." I had never had sex with anyone other than Barbara in my life.

With Carol bent over, I pulled her short skirt up to her waist. She had on no underwear. I played with my cock briefly to get it harder and pushed it into her. Her fists clenched and she exclaimed, "OHH, YEAH!" I pushed myself forward and back inside of her. She shouted, "OHH, JESUS, YESSSS!" With each forward thrust, I grunted and she encouraged me. "FUCK YESSSS!! HARDER. DO ME HARDERRR!!!"

When I came inside of her, she turned around and looked up at me. "Now, kiss me and tell me that you love me." I gave her a light kiss and said, in a low monotone, that I loved her. She slapped me across the face. "NO," she insisted. "Give me a passionate kiss and tell me that you love only me. And you better make me believe it or we go back to the dungeon for more training."

With a deep sigh, I put my hand on the back of her neck. Pulling her to me, I reached down and pushed my tongue into her mouth. We "necked" briefly. I then told her, "Car--, mistress, I love you so much. You are a very special woman."

"Very good," she replied. "Now, there is one more project for today. I anticipated some of the clients that may be most appropriate for you. They will be arriving for a 'meet and greet' soon. When each one arrives, I will have you greet them at the door. ls that understood?"
Looking away, I replied, "Yes, mistress." I then moved to pick up my clothes. She wanted to know what I thought I was doing. I told her I was going to get dressed for the party.

She exploded, "You will do no such thing. You will greet our guests as you are." Now lovingly reaching up and stroking my cheek, "Do you want to return to the back room for some more electrical treatments? Do you want me to send photos and film of our time together to your wife?"
Dejectedly, I responded, "No, mistress. I want to please you and will do as you say." With that, the doorbell rang.

She motioned for me to answer it. My heart raced as I opened the door. Standing there were two young women. It did not seem to phase them in the least that they had been met at the door by a naked stranger. I forced myself to be pleasant. "Hello," I began. "I suppose you are here for the party."

"Got that right," one of them giggled as they brushed by me and greeted Carol as a long lost friend. In all, there were a half-dozen clients that had been invited to meet me. No one found it the least bit odd that this nude, male stranger was in their midst. All the guests were women except for one man. His presence was especially troubling and brought to mind the questions as to my willingness to engage in sexual activity with men.

I stayed in the background as much as I could. At one point, she motioned for me to come and stand next to where she was sitting, talking to some of the guests. When I was next to her, she lightly fondled my penis and proceeded to explain her charges to 'have' me for various periods of time.
Two of the women proceeded to attempt to negotiate the price with Carol. As Carol fingered me, and I stood there silently, they haggled as if discussing the purchase of a car. They appeared to reach an understanding. Apparently, Carol closed a few deals for me there on the spot.

Then, as the meeting was breaking up, the lone male guest came over to where I was still standing next to Carol. Putting his arm around me, he inquired of her, "You say he has no experience in being with other men."
"That's right," she replied. "But he is willing and eager to learn. And I thought of you as the perfect teacher He would be excited about that, wouldn't you?" She looked at me and glared.

Staring at the floor, I bit my lip and said, unenthusiastically, "Yes, mistress."

Clapping his hands, the guest shot back, "Fine. Has anyone taken him for next Friday?" Carol shook her head in the negative. "Good. I can pick him up here about 6:00. Our usual financial arrangement?"

Carol smiled. "Of course," she replied. As the guests departed, I was expected to see each of them to do the door. I had also been instructed to give each of them a passionate kiss and tell them how much I looked forward to spending time with them. This included the male guest. As I kissed him and told him I looked forward to being with him, he smiled and, grabbing my penis, whispered, "I am looking forward to it, too."

When the last guest was gone, Carol motioned for me to sit back down in the chair where our meeting had begun. "Okay," she began. "Your first assignment is tomorrow with Kim. You will be gone for four days. She is going to a convention in Las Vegas and is taking you with her. You will need to tell Barbara that you will be gone for that period. I do not care what you tell her. Just make her believe it.

Remember what will happen otherwise. Her total fee for that four day package is @25,000. Your share is half of that. She will pick you up here at 2:00 to go to the airport. You are to be here, packed and ready to go. And I better not hear any complaints at all from her. She is paying good money for you. And if she regrets it, trust me, you will regret it. Do I make myself clear?" I was just stunned at how this day had gone. More insistent, she repeated, "DO-I_MAKE_MYSELF-CLEAR?"

'Yes, mistress," I replied.

"Good," she snapped. "Now, get dressed. Be back here tomorrow afternoon. And remember. Tell your wife whatever you want. But make a believer of her. That's it for today. I will see you tomorrow." With that, Carol headed back toward the hallway.

Silently, I got dressed. I was still shaking as I headed down the driveway to the car. This was nothing but prostitution. We needed the money. But how could I do this to Barbara. If she found out, especially if she learned that the reason I had turned to this was because I had foolishly lost all of our savings, how could she ever have any respect for me again.

But if I did not do it, we faced imminent foreclosure on our home. I would have to swallow my pride and go through with it. I hoped that this woman I was going to Las Vegas with would treat me well. And I started contemplating what story I could tell Barbara.
Poster: Tim