First Time with a Dominatrix

I always found it interesting how total strangers could get into deep conversations while seated side by side on an airplane. I guess it's a way to pass the time, realizing that they will probably never meet again. The smooth looking man seated next to the attractive woman on the other side of the aisle was describing something and I wondered if he was spinning a line or just being neighborly. I rarely had such conversations and never with a woman. I was far too shy for that, and certainly not the handsome man that I woman might want to chat up. Instead, I occupied myself by reading through my notes from the business meetings I'd had for the past two days and typing a summary into my laptop. I'd barely noticed the woman seated at the window in my row. She was reading a magazine and paying little attention to me.

As the engine noise droned on, I was surprise by the voice beside me. The woman was asking me a question and I had to ask her to repeat it. She wanted to know about my computer, saying that she was thinking of buying one and what I thought of the many models on the market. As I said, I'm not very good at small talk, but comfortable talking about things I am very familiar with. We discussed the various laptops available and where to get the best deals. I did ask her what business she was in and she'd replied that she was in business for herself. She didn't expand on what the business was and I was uncomfortable asking. I doubt if I would even have asked if it were a man I was talking to, that's my nature.

When the plane arrived at the gate, I was gathering my things from the overhead rack and juggling my computer bag. The woman thanked me for my advice and handed me a business card. I didn't have time to look at it and just tucked it into my jacket pocket. Several days later on arriving home from work, I noticed the card in my pocket and read it.

Mistress Jane -- Dominatrix

I must admit that I'd fantasized about being dominated by a woman and humiliated about my physical appearance. However, in my wildest dreams I'd never considered carrying out such a fantasy. My first impulse was to toss the card into a waste basket but for some reason I set it down on my desk. It stayed there for several days before I picked it up again. No address on the card, but the phone number was for a town a short distance away. I put the card back down and went on with the task at hand, paying my monthly bills.

It must have been about a month later that I picked the card up again. It was a Wednesday evening and I had no plans for the next few days or the week-end. I started to dial the number and then stopped. I walked around the room several times, getting up my courage and dialed again.

"Hello, you've reached the office of Mistress Jane. Please leave your name, number and a brief message. I'll get back to you."

My first impulse was to hang up, but instead I nervously gave my name and number. I also mentioned that we'd talked on the plane coming back from Chicago several weeks ago.

A few hours later the phone rang. I jumped to pick it up but decided to let the answering machine pick up instead. I heard her business like feminine voice saying she was sorry she'd missed me and asking me to please call back. Again my first instinct was to just ignore the call, but instead I quickly picked up and said hello. She was very businesslike and suggested that we should first meet at a coffee shop or bar to discuss how to proceed. I agreed and we arrange to meet the next evening after I got off work.

The day seemed to drag on forever. There was not a lot going on that week so I had to make lots of busy-work to pass the time. Five o'clock finally rolled around and I headed for the coffee shop where we'd arranged to meet. I got there 15 minutes early and after parking I had second thoughts. I started the car and pulled out of the parking lot and drove towards home. Several blocks down, I summoned my courage and slowly headed back. When I got there, I went in and saw her sitting in a booth towards the back of the room. On rubbery knees, I walked up to her, said hello and sat down.

She immediately sensed my discomfort and said that she'd guessed this was my first time meeting with a dominatrix. She assured me that she was supplying a professional service and as the customer, I had complete control over how deep an experience I wanted. I could stop at any time during our session. I was surprised at how professional and business like she appeared, not my vision of a cruel woman dressed in tight black leather with whips and chains. She asked me if I'd been with many women. I lied and said a few. When she found out that I went to the gym regularly, she asked if I showered while there and whether I was comfortable showering with other men. I was somewhat puzzled by the question, but confessed that being naked in the shower room was quite uncomfortable for me. She described several of the most common scenarios her customers requested and we established that bondage was definitely out, as was physical punishment. After a few more discussions we agreed to meet the coming Saturday night and she gave me a card with her address.

On Saturday evening, I found her street in a good neighborhood. Her house was small and well kept but secluded, being at the end of a short drive into the woods. As instructed I was dressed casually, wearing slacks and a pull-over shirt with short sleeves. I would not normally go out with short sleeves. I'm really skinny and don't like to expose my thin arms, but this is what she'd requested so here I was. I got out, shaking at little and rang the doorbell. After a few minutes, she answered, dressed in a professional but casual looking outfit. Well tailored slacks and a blouse accentuated her shapely figure. No jewelry or makeup and not unlike hundreds of women I'd seen at after business meeting social events. We quickly concluded our business transaction and she led me into an adjoining room.

She asked me to take off my shoes and socks and stand in the middle of the soft carpeted floor. It was a medium sized room, about 12 feet by 14 feet with two doors, the one we'd come through and one on the far side. There were drape covered windows on either end. Very little furniture, a comfortable looking sofa and several straight backed chairs. If I wanted to live out a fantasy of a dungeon with whips and chains, this certainly wasn't it.

As she started talking, her toned changed. She instructed me from now to speak to her only as Mistress Jane. All questions were to be answered with a simple, Yes Mistress or No Mistress. If asked to elaborate, I was to keep my answer short and to the point.

I said, "Ok."

She glared at me, and I said, "Ok, Mistress Jane."

She then clapped her hands loudly and the door on the far side of the room opened. A tall heavily built man walked in. He had broad shoulders and his chest bulged under a tight fitting t-shirt. He was wearing sweatpants and like me, bare foot. I suddenly felt very weak. What had I gotten myself into? Would I really be able to stop the proceedings if they started going too far? I remembered the conversation at the coffee shop. She'd stated that like any business, it thrived on repeat customers. Part of the appeal of the situations customers found themselves in was being able to deal with their fears. To me this made so much sense. I recalled my concerns showering as an adult, remembering the humiliation I'd suffered in high school and finding out it wasn't all that bad. Now I understood the shower room question at the coffee house.

"Tim, this is Dan. He's going to be helping me tonight. Dan, take Tim to the sofa."

Dan grabbed me and led me to the soft. His large hand went completely around my arm and although he wasn't in the least bit rough, I felt completely dominated by him.

Mistress Jane came over and sat on the sofa, facing me. Dan was behind me now and I could feel his presence towering over me. I was quivering but hoping that it didn't show. Mistress Jane instructed me to raise my arms above my head.

I did so, and she snapped, "How do we respond when given a command?"

I replied, "Yes, Mistress Jane," hoping she wouldn't notice the shakiness in my voice.

Suddenly Dan grabbed the sides of the shirt and pulled it off over my arms. I was too shocked to do anything but stand there with my arms up. How far was this stripping going to go? I'd fantasized about being stripped by a woman. Having a man present was never part of the scenario. Mistress Jane told me to lower my arms while she commented on my thin frame and hairless chest.

"It's a good thing you know about computers. Your certainly don't look like you could do anything a woman would expect of a man."

"Come closer and turn around. Let's see the rest of you," she commanded.

I turned around and noticed that Dan had also removed his shirt. He had a barrel-like chest with curly course black hair running from just below his neck clear down to his waist and disappearing into his sweatpants. Mistress Jane was now standing behind me and I could feel her cool hands running over my back and down my sides. This sent a cold chill through me. How far will this go? How far do I dare let this go? I wanted this and was afraid of it at the same time.

Mistress Jane turned me around so I was now facing her. She stood very close and I could feel the warmth of her body on my bare chest. I glanced down and could see her cleavage between shapely breasts.

She realized where I was looking and glared at me while snapping, "That's not where your eyes should be looking. A skinny little boy like you couldn't dream of satisfying my needs!"

"Ok, Dan. Let's get on with this flimsy specimen," she said.

I hadn't realized that Dan was directly behind me again. He reached around me, undid my belt, unzipped my slacks and lowered them down. Mistress Jane instructed me to step out of my slacks and step towards her. I remembered to say, "Yes, Mistress," and did as told. I was wearing a very tight pair of black jockey shorts, again as instructed and she viewed me intently paying close attention to the slight bulge in front. She ran her fingers over my legs, first down the outside and then slowly up the inside. A shiver went through my body as she lightly glided her fingers over the faint outline of my genitals. I could feel her fingering my penis through the fabric but dared not look down, fearing a reprimand for looking at her cleavage again.

She then said, almost in a whisper, "Do you enjoy this Tim?"

I then looked down and could see her fingers in front of my jockeys, emphasizing the smallness of my package.

In a trembling voice, I replied, "Yes Mistress Jane."

"Do you want to take Dan's sweat pants off?" she asked.

"No, Mistress Jane," I replied.

"Dan, little Timmy here isn't interested in you. Do you want to show us how much of a man you are?" she asked, looking away from me and towards Dan.

"Yes, Mistress," he replied.

"You heard him," she said. "Go over there and take Dan's pants off."

"Yes, Mistress Jane," I replied and walked slowly over to Dan.

The cord that secured his sweat pants hung down the front and I fumbled as I tried to loosen it. I could feel the heat radiating from his body and I was puzzled by the feeling of excitement coupled with fright that came over me. I finally got the cord untied and moved to the side as I loosened the top of his pants. I was trying to avoid looking directly at him when I pulled them down but couldn't help but notice the enormous bulge he was sporting. I could vaguely make out the shape of a thick penis even with his loose fitting shorts.

"Which one of the Seven Deadly Sins are you thinking of right now," she asked Dan.

I was surprised by the question, but obviously Dan had heard it before and he replied that he felt Pride. She then asked me what sin I was thinking of. I hesitated, trying to remember the seven and finally replied, Envy.

"You don't feel Lust?" Mistress Jane asked.

"No, Mistress," I replied although there was a hint of hesitation in my voice. Hopefully she didn't notice it.

Mistress Jane then said, "Well now, I already know why Dan feels Pride and I'm pretty sure I know why Tim feels Envy. I could tell one of you to demonstrate your position but rather than do that, I'm going to give you a contest. The loser then has to do what I say. The contest is simple; I'm going to show a 'Frame Game' picture. The one who guesses first is the winner. "

I'm pretty good at Frame Games, but not knowing what the loser has to do left me with a no-win feeling. If I lost, would she have Dan show off by lowering his shorts or would she have him strip me? If I won, what would I do? I had always fantasized a dominatrix scenario with the mistress stripping me and commenting. Now there was a man in the mix. My mind went back several years to the time I started going to the gym as an adult. While initially very frightened showering in public, I'd gotten more comfortable after a time. However, any time I was in the shower with a particularly well endowed man my boyhood experiences came back to me and I always felt very vulnerable. Had he seen me? What were his thoughts? Was he amused? Was he contemptuous? At the same time, I was very uncomfortable about having to strip him. The feeling I got taking his sweat pants down was confusing.

Mistress Jane put up the picture.

INTR4IGUE

"Foreign Intrigue," I blurted out almost instantly.

"Excellent!" cried Mistress Jane. "Dan, you're the loser. I want Jim to go over there and strip you."

I hesitated, but went over and started to kneel behind Dan.

"That won't do," cried Mistress Jane. "I want you in front of him and I want you to look directly at him. See what he's so proud of. See what it is you envy."

I was already on my knees so felt doubly humbled having to crawl around in front of Dan. He was looking down at me, an amused and somewhat smug look on his face. I started to pull Dan's shorts down and Mistress Jane commanded:

"Go slowly now. Just lower them a little bit. Tell me what you see."

I lowered his shorts a few inches below his navel and said, "I see a very hairy stomach. The hair is black and very course."

"Excellent," exclaimed Mistress Jane. "Now lower them a few more inches. Slowly."

I lowered his shorts until the base of his penis started to show. I was fascinated with what I saw and surprisingly excited at the same time.

"He has a very thick cock," I called out, no longer waiting for the command. I then lowered the shorts a few more inches. Was his cock starting to move? It looked like it might be. My emotions were becoming confused. I know I look at other men while in the shower, but they often look at me. I wondered if I might actually be gay but had convinced myself that it was something all men did. I finally pulled Dan's shorts all the way down, now mesmerized by the long thick shaft barely inches in front of me.

"Don't keep it all to yourself," Mistress Jane called out. "I want to know what you're looking at and how you feel."

"He has a very long thick penis," I said. "He's so much bigger than me. I'm not even close to that big when erect."

Mistress Jane asked, "How do you feel looking at him like that?"

I replied, "I've never dared look so closely at a man before. I'm not sure what I feel. I guess I'm a little frightened and intimidated. Excited too."

"Ok, that's enough of that," Mistress Jane said. Come over here, Tim and let's continue our session. Dan, do you want to see what Tim has been hiding? He thinks you're very big. Let's see how much bigger you are."

I knew this next moment was going to happen but was dreading it. While I wanted her to see me and comment, did I really want Dan's opinion? I guess in a way I did.

Dan came over, knelt in front of me and slowly removed my shorts. While I'd been excited looking at Dan, I was still frightened by the mixed emotions and I was as retracted as I'd been the first time I dared shower in public. My penis, short at the best of times was barely visible, pulled into my light sandy pubic hair. My testicles were drawn up close to my body and almost non-existent.

Dan didn't need to be told what to do and started commenting. "He's got one of the smallest penises I've ever seen. It can't be more than an inch long and really thin. The head is almost lost in the loose skin although he's circumcised. His testicles are the size of little grapes. His girlfriends must be very disappointed."

"Well Tim, are your girlfriends disappointed?" the dominatrix asked.

I stammered, trying to think of a good answer. I've never had any complaints didn't seem like the right reply.

"You've never been with a woman have you?" Mistress Jane called out. "You lied to me didn't you Tim? Dan, we've got a virgin here. Maybe he doesn't like girls. He certainly can't take his eyes off you. Ok, let's play another game. This time I'll tell you what the winner gets to do. He gets to be given a hand job. Or if Tim wins maybe it's just a finger job," she giggled.

It was a Frame Game again, but my head was so confused with the mixed emotions I was feeling that Dan finally came up with the answer. I wanted to run but at the same time I was mesmerized by Dan's huge cock and intrigued by how big it might get. It was quite wrinkled now so I knew it would grow appreciably. I kneeled in front of Dan and gingerly held his penis and raised it to a level position. I couldn't believe how heavy it was. I could barely get my hand around it and it felt hot to the touch. I began to stroke slowly and could feel it starting to thicken and stiffen. The head became swollen and a bright purple color. His scrotum jerked sporadically as it started to draw up, one of his egg sized testicles hanging down lower that the other. I could now hold his penis in two hands, a huge contrast to mine while masturbating when it barely filled one of my small hands. I could see a drop of moisture gathering at the tip and realized that his cock could stand pointing slightly upward without my support.

"I think Dan would like you to lick him," said the dominatrix.

She had little reason to command it. Now I wanted desperately to get my eyes as close to his member as I could. I licked and rubbed my face against that monster shaft and scrotum, all the time not noticing that I was now fully erect myself.

My erection was not lost on Mistress Jane and she commanded, "Dan, you've been getting enough attention. Tim needs some attention too."

Dan leaned down and pulled me to my feet. He knelt in front of me and started to finger my cock. I was surprised at how good it felt. He held the tip of my penis between his index finger and thumb and slowly stroked the shaft along the top and bottom with the index finger of his other hand. When he tickled my scrotum my penis twitched excitedly. He then stood behind me and passed his penis between my legs. It stuck out well beyond my pitiful organ. We then stood side by side facing Mistress Jane and stroked each other to an almost simultaneous orgasm. Jane made us each clean the other off with our tongues. I almost had a second orgasm as Dan engulfed my penis in his mouth and messaged it forcefully with his tongue.

Dan and I were both instructed to sit on the couch while Mistress Jane went to get some coffee, tea and cake. We relaxed and she asked me how I liked the session. I found out that Dan had been one of her early customers and occasionally helped out if the session with her male or female customers called for it. I was surprised at how relaxed I now was. Maybe it was just coming down from the high emotion of the previous several hours. I think partly it was the comfort I felt in dealing with my body appearance. I did envy Dan his big cock, now relaxed and hanging between his legs and resting on the couch. At the same time, I was oddly proud of my penis, now a thin withered worm lying on my leg.