First Meeting

I left my small suitcase in the rental car parked in the guest arrival section of the hotel when I entered to check in. I paused in the lobby to look around to see if anybody familiar might be waiting. I was nervous. Not from the procedure of checking into a hotel in a strange city as I had done that many times in many cities. Nor did I have any concern about the series of business meetings I would be attending over the next three days although they were very important to me financially.

What made me nervous was I was about to meet a woman I had never seen in person before. She was an online dominatrix to whom I had submitted over the past year or so. She had frequently assigned small tasks for me to perform. Of course as my mistress and me her submissive, the tasks she ordered were mostly of a humiliating and often painful nature. Almost all these tasks were in the privacy of my living room on webcam. Very few were done in a public setting and even then that had been mild in comparison to what I faced now.

Now, because I planned to attend a business conference some fifty miles away from where she lived, she decided we would finally meet in person. While my day activities were scheduled, I would be fully at her disposal each night. She had instructed me she would review my meeting schedule when she arrived and any free time I had would belong to her.

I had one standing order that I was to obey from the time I arrived until I boarded the plane to go home: I was to consider any female I encountered as my superior. She had told me, "I do not care if a fifteen year old girl walks into you while texting on her phone. You WILL apologize and call her Ma'am. If you see a woman struggling with a suitcase, you will help her. And I cannot imagine this happening, but if a woman in an elevator pats you on the ass or even grabs you by the balls, you will not stop her or flinch away. As a matter of fact, I will go on to say if the person looks like a man in drag but you are not SURE there is a cock hanging between the legs, you consider the person a female and therefore your superior."

I had thought about that instruction a lot over the prior few days. Was Mistress Mary going to have a 'ringer' approach me to see how I acted? Or would she be hiding in plain sight just to observe me? I was not sure I would recognize her in person. She was usually shrouded in shadow or masked during our online sessions.

Unfortunately, the hotel lobby was busy. As I looked around, I saw several women who might be Mistress Mary who I knew to be in her early fifties. Some were dressed in business clothes but many only in casual attire like jeans. I noticed a few within easy hearing distance of the hotel check in desk.

I waited for the man in front of me to get finished with his business. As I began to step forward, I noticed a woman behind me. "Go right ahead," I said.

"You were here first." she said. I nodded and told her I was just checking in and had plenty of time. She thanked me and stepped forward. She was just returning a key card. I realized she was not Mary.

The forty or so year old clerk looked at me and asked how she could help me. I told her I was checking in and gave her my ID. She entered my information into her computer. "Oh, when I entered your name into the database, it says here we also have something waiting for you." she said. She quickly checked me in and handed me my keycards. She stepped back to a cabinet and pulled out a cardboard box. It appeared to be about a foot square and eight or nine inches tall.

"A woman dropped this off for you." she said, as she set it on the counter.

"Oh, can you describe her?" I asked hopefully. My hopes she would point out one of the women in the lobby were dashed when she said.

"Nope. Must have left it when I was at lunch. But it is obviously a woman. Look at the writing. Obviously feminine, plus the lipstick kiss mark on the tag." she giggled. "Looks like something fun!" I noticed the clerk had a few rings on her left hand but no engagement or wedding ring.

Sure enough, there was a set of lip marks on the white label where a woman had kissed it. Looking closer, the box was completely sealed in heavy packing tape, the kind with nylon string fibers. The white label with my name and the lip print was covered in clear tape. "She obviously did not want the box falling open," the clerk laughed. "This thing is going to be hard to open. You are going to have to cut this sucker open. You'll almost need a box cutter."

I knew I did not have anything sharp enough to cut that tape, not with the TSA prohibition of sharp objects on aircraft. I said as much to the clerk. The clerk said she could not let me take her scissors to my room and they might not work well anyway but she had a box cutter behind the counter. "I will help you open it." I protested saying I could do it.

"Nonsense. I have been dying to see what might be inside." she giggled. "I admit I shook it just a little. All I felt was soft thunking. So whatever is inside is solid but not hard. And the box is not that heavy."

I had a pretty good idea what kind of items were in the box and I certainly did not want this woman seeing any of them. I repeated my earlier statement that I could open it myself since she was busy. "Nonsense." she said, smiling sweetly. "Bring your butt down here to the end of the counter where it is low and we will open her right up." I looked around to see if anybody was paying an undue interest in the exchange as I followed the clerk. Once again I wondered if I was being set up.

She ordered me to hold the box at the bottom. I took it as an order especially when she took my right hand and placed it where she wanted me to hold the box. I imagined Mary was observing the whole process. She began to carefully slice the tape saying she did not want to risk damaging whatever was inside. She stuck a few fingers inside one flap so she could pull as she cut. I was hoping to pull it away before she saw the contents, but her grip was too tight and just as the last of the tape gave way she pulled the top open.

There on top was a big flesh-colored dildo. I froze, staring at it. It was at least seven inches long, a realistic model of a penis complete with balls. "Oh My!" the clerk breathed. I felt my face flush so hard I thought I was going to fall down.

The clerk looked at me and grinned. "From what you said before, you do not know what the woman who left this for you looks like?" she said. It was more a statement than a question. I shook my head, my mouth suddenly so dry I was unable to speak. "Well, this is not something you leave for a stranger. Certainly not a wife and not a girlfriend. There has to be a story here." she insisted. "Do you mind if I look to see what is underneath?"

"Please, Ma'am." I whispered hoarsely."I would rather you didn't." She grin widened, "And if I insist?" I knew better than to say anything. I was not sure I could speak anyway. I just nodded. The clerk looked around to make sure nobody could see as she reached into the box to push the dildo to one side. At least two butt plugs sat directly underneath. "Ooh, looks like a harness for the first toy and some supplies to make it easier to use these things." she said in conversational tone not even trying to keep her voice down. The clerk was now openly giggling at my humiliation.

"Looks like you are going to be a busy boy. I suspect the next time I see you around you will be walking funny. Let me guess. You don't know which woman left this but you suspected what might be in the box." I nodded. "Mistress?" she asked, smiling widely. I nodded again confused as I realized that the word mistress was the first word she might use and not girlfriend.

"Well, have fun and I expect you to come back to see me with the full story. I know your room number and how long you are staying. You do NOT want me to have to come find you, understand?" she asked with one eyebrow raised. I nodded again.

"If I see you with your Mistress I might say hello. I'll tell her what a good boy you are." she added, grinning broadly.

I tucked the box under my arm and walked outside to where I had parked my car to retrieve my suitcase.

I parked my car in the hotel garage and rode the elevator to my floor. My mouth was still dry after my encounter with the desk clerk and I needed something to drink, preferably alcoholic. But first things first.

I had noticed a folded piece of paper the clerk had pushed aside as she examined the box's contents. Reading it, I was glad the clerk had ignored it. "Bitch, Time is short. First, you are to send me a text message when you get to your room. Then you will follow the instructions that follow. When you are ready, message me again. You are being timed. I will check and compare the times you text with your check in, so DO NOT DAWDLE. When you are ready, go to the lobby. You may go into the bar. I will find you."

I dumped the box onto the bed. I found the harness the clerk had mentioned. In addition to the dildo and two butt plugs was a tube of lube and a disposable enema kit, a roll of packing tape like what was used on the box and a small bottle of rubbing alcohol.

I picked up the note."Obviously you will need to use the enema first. Hold it a while to make it effective. You might want to fill it again and rinse a couple times with plain water from the tap. Do a good job. I will have my own enema kit in my suitcase and you do NOT want me to have to use it. My nozzle is far larger than the little disposable one and I will push it in much further, not to mention the amount of solution I use."

I reread the rest of the directions while I was sitting on the toilet. "If you suck on the plug and get it well coated with your saliva, you may not need the lube. You will get a bonus if you manage that and the seal on the lube is intact. Either way, insert the smaller plug. You will notice the neck is not very narrow compared to the wide part, so it may not stay in on its own. I suggest you push it in tight or the bulge will show. You will need to use the tape I provided if you don't want to risk an accident and lose the plug in public."

"I told you before you left home that I would not REQUIRE you to remove your body hair and left it up to you. I am curious to see if you took the hint." I had not. My body hair was intact. The way nature had grown it. "I want the tape used in the following manner. A long strip from your belly to one side of your scrotum and underneath into your buttcrack to hold the plug. Then up the back. Repeat with another strip on the other side of your scrotum following the same path up your butt. Then wrap tape around your hips to hold it all in place. I want a belt of sorts at the level of the top of your bush if you still have one. Two passes of tape. Use the tiny scissors I gave you to trim the tape. Neatness counts."

Examining the plugs I saw neither was small. One was slightly smaller in diameter than the other at first glance then I measured with my fingers. I could not get my index finger and thumb to touch around the wide part on the first. The second was larger than the circle formed with my thumb and middle finger. I knew I would need the lube.

Even heavily lubed, it hurt going in. I had to work it in and out to slowly stretch my anus. I got to the widest part and had to stop several times. Finally I gritted my teeth and it popped inside. I washed my butt to remove the excess lube. I knew it would prevent the tape sticking and I certainly did not want to risk the plug popping out in public. As it was, my ass spasmed painfully several times almost dropping me to my knees while I taped myself up..

Once dressed, I examined myself in the mirror and could not see a discernible bulge. It felt like I had a log up my ass, though. Walking was difficult and I know I was walking a little bowlegged. The tape did not help. It pulled my hair unmercifully.

I quickly sent the message saying I was leaving my room and a description of my clothing: tan cargo shorts and dark brown tshirt. I had also changed clothes. I hoped the baggy clothing would hide any bulge the plug might make. I knew my jeans would not. I got onto an empty elevator but when four women entered the next floor down I moved quietly to the back. "Relax," I told myself. "Every woman is not in on your humiliation."

Every woman might not have been but I knew there was at least two. Sure enough the desk clerk I had met earlier saw me when I entered the lobby. She grinned and waved.

I walked across the lobby and stopped at the entrance to the bar. I turned to look around the lobby. It was still busy. I noticed a disproportionate number of women milling around. Usually two thirds of the people in a hotel lobby are men especially in a hotel that does not have a lot of families. Here, three quarters of the people I saw seemed to be women.

None of the women appeared to be watching me or even looking my way. I pulled my phone out of my pocket and sent a text message. I had hoped to hear a notification on somebody's phone. It seemed like half the women were busy on their phones anyway, texting or whatever.

I jumped when I felt a hand on my arm. I turned to see the desk clerk, smiling widely. "Hello Mr. Wilson or should I call you John? Or maybe Johnny Boy with an i."

I stuttered and said, "Hello." She grinned even more widely and said in a low voice. "I watched you walk across the lobby. You seemed to be having a little trouble. Are you full?" I nodded.

"Excuse me?" she asked sharply, reprimanding me."Where are your manners?"

"Sorry Ma'am." I replied meekly. "Yes I am full."

"Better. Good manners are important. Now describe to me in detail what you did in your room" she ordered, with an evil glint."I expect detail."

"Please, Ma'am" I begged. "We are standing almost in the door to the bar. Somebody might overhear."

She grinned and took me about ten feet to one side. She positioned me so I was facing the lobby she stepped close placing her body against mine and offered her ear. As I began, I felt her hand reach behind me. She pressed on the plug and I almost jumped. "It doesn't move much." she whispered. "Your hungry little ass must be really gripping it." "Tape," I said simply and quickly told her about the set of instructions.

"I love it!" she grinned. I asked her why she was messing with me and wasn't she worried about taking time away from the desk.

"Nope. The hotel manager is my brother in law and he knows I'll bust his balls if he bitches at me. As for why I am doing it, the answer is simple. I CAN. I like doing shit like this. It is fun. I just rarely have an unexpected subbie drop into my hands here at work. This is only the second time."

"May I go, Ma'am? I am waiting for my mistress. She said I could go to the bar. She might be inside waiting."

"I was hoping she would see us and come over." the clerk whispered softly into my ear. "Sure you can go. Believe me, I will be seeing you around and I expect you to show me the utmost respect. Ma'am in public and Mistress Brenda in private." I nodded.

Suddenly she jammed the plug hard enough to almost raise me onto my toes. Despite the tape, the plug moved sideways and jolted my lower intestines. The shock drove up my spine. "Do you need a lesson in respect?" she asked a smile, her face a bare inch from my own. "No Ma'am." I moaned.

"Go." she ordered.

"Thank you, Ma'am." I said. She smiled and nodded.

I paused at the bar entrance to look around the lobby one last time. Nobody seemed to be paying any particular interest. I knew nobody had observed my contact with the clerk.

The hotel bar was designed to be a quiet getaway at the end of a business day. Tall tables, most with four chairs. Booths around the walls Subdued lighting but not too dark you could not read a paper. Just inside the bar, I saw a pair of women leaning close examining what looked like a document.

I walked around slowly looking for a place to sit. I also wanted to give my mistress the chance to see me if she was there. Almost every table was occupied, the great majority by only women. Several women glanced in my direction, but none of their gazes lingered long enough for me to make eye contact.

I had walked two full rounds through the bar and was starting my third, when a woman sitting in a booth stopped me. "You need a place to sit. You are getting a lot of exercise running laps."

She slid quickly out of the booth and stood in front of me. In the light I could not tell if she had the reddish hair with grey highlights I was looking for or if her hair was brown. I judged her height at five four or so, several inches shorter than me. I am not a good judge of age but suspected she might be late forties or early fifties. "Sit with us."she said, pleasantly.

The seated woman was a blonde. She looked at the brunette and giggled. "Sit down. I insist." the brunette indicated the seat she had just vacated and took my arm and pulled gently to get me moving. I slid into the booth. Turning to the blonde, the darker haired woman said, "See? You need to practice what the seminars teach. Be assertive."

"They meant business dealings not grabbing up a guy in a bar." the blonde said laughing.

"My sister here is attending a conference on empowering women and how they need to be assertive." the brunette explained. Turning to the blonde, she said "It is for any contact, business or social. You said that earlier."

"He looked like he was looking for someone." the blonde protested.

The brunette countered, "Well, when she comes in, he can get up and join her. It is a woman you are looking for, right?" she inquired. I nodded.

"I knew it. There are only a few men in the place and you did not look closely at any of them. You checked out all the women, though, as you walked around." She grinned at me.

The waitress came and we ordered drinks. I reached for my wallet. "Nope. Thank you, but Sis here promised to pay for the drinks if I came to visit. Her conference has their final meeting this afternoon. Then she has to rush to catch her flight. This is the first time I managed to get here."

I explained I had meetings for the next few days. We made small talk about where we lived and what we did while we waited for our drinks.

I was starting to relax, but just as I took my first sip of beer, the brunette put her hand on my knee and rubbed straight up the bare skin of my thigh until the shorts stopped her progress. I almost choked on my beer. I turned my head. She had a small smile on her lips but her face was non-reactive otherwise. She kept her hand on the bare skin of my mid-thigh as she sipped her own drink.

After a few seconds, she removed her hand. My relief was short lived, A slight shift in position, she placed her hand directly on my crotch and gave me my package a little squeeze. Her facial expression gave no indication of what she was doing below the table. Seated to the outside, she blocked me in the booth. I could have stopped her but there was no way I would unless I wanted to risk creating a scene.

The brunette kept up a running commentary. "You see, sis, You need to take charge more. I like men like our friend here. He is so polite, accepting our hospitality and even offering to buy us drinks."

The blonde had ordered another round, stating she had just enough time for one more drink before she had to leave. I shifted slightly and the brunette took advantage by sliding her left hand under the edge of my pant leg, her fingers lightly tapping a cadence on my bare skin. Once again I tried to carefully move her hand. She was having none of it and responded by pushing her hand up my thigh and held it there.

I looked at her face. She raised one eyebrow and grinned. All doubts were gone now. I moved my leg to loosen up my pant leg and grant her full access. She nodded. A second later I barely stifled a yelp. She had pinched my inner thigh. Hard. She looked at her sister as she followed the first pinch with two more.