First Meeting

The blonde stood and bid us goodbye. I waited until she was out of range and looked at the brunette. "You are Mistress Mary."

She nodded, " Exactly, my slutty little bitch. Now what did I tell you about doing exactly what any female told you to do?"

"Sorry," I said weakly.

"You will be. Now undo your pants. I want to play with my toy while you tell me all about your contact with that desk clerk. I saw part of it. Now I want details."

I knew I was in for a very interesting business trip. I just hoped I would be able to walk straight when I boarded my plane to go home.

I told Mistress Mary about my contact with the desk clerk, beginning with my check in and opening the box of toys. As I told the story, Mary slid her hand inside my briefs and gripped my penis. As I continued my story she began to rub her thumb over the tip making me squirm in my seat.

"So, she humiliated my little bitch." she stated, grinning. I nodded. She pinched the sensitive end of my penis. "You just said that Brenda insisted you show her more respect than just a nod. Do you think I will accept anything less?"

"No Ma'am. Sorry." I said gritting my teeth trying not to make a sound as she pinched harder. "You will get a little reminder lesson in a bit." Removing her hand she told me to fasten my pants. She slid out of the booth.

I followed her out of the bar and into the lobby. Once there, she paused. "Did you get two key cards? Or do you we need to ask for another?" When I told her I had two, she held out her hand. She opened her small purse and dropped the card into it.

"I have a small bag in my car. We will get it and then go upstairs. I want to get started. Maybe later I will let you treat me to supper. I am sure I will be hungry. You might even still have an appetite." She turned away, chuckling, as I followed.

Brenda noticed us and smiling, waved to Mary. Mary changed course and approached the desk. "I want to thank you for helping my boy earlier." Mary said.

"No problem at all. I loved doing it." Brenda said. "I am available if you need any assistance. Babysitter perhaps." She smiled evilly.

"Now that is an idea." Mary said. "I have an important meeting at work tomorrow that I must attend. I won't be able to get back here until 8:00 pm." Turning to me she said, "You told me you have a schedule of your meetings but I have not seen it yet. What is on for tomorrow?"

"We meet for breakfast at 7:30 and then an introduction meeting. We are supposed to be finished by noon. Several guys are going to play golf and many have tours of the area set up or were going to meet in the bar. That is what the letter said." I reported.

Brenda said she worked from 3 to 11, but she would arrange to take care of me until Mary arrived.

"I hope you did not sign up for golf or a tour." Mary said. "And you will NOT be hanging out in a bar drinking. You will report back here and report to Mistress Brenda. With your meeting taking place next door, I am sure you can be back here by 12:15. Understand?" "Yes, Ma'am," I answered.

I was officially issued a third keycard to my room. Mary handed it to Brenda and the two exchanged cell phone numbers. I then followed Mary into the garage where we retrieved her small suitcase.

"I need to go to the bathroom." Mary stated as I opened the door to my room for her. "I expect you to be naked with your hands on your head when I return.

I was posed as ordered when she got back. My only attire if you could call it attire was the packing tape belt that prevented me expelling the butt plug.

Mary walked around me inspecting me. "Just inspecting my toy, my bitch. This is the first time I have seen your whole body at once. Web cams are just not the same. She rubbed her hands over my body squeezing my ass and grabbing the rolls of fat above my hips.

"You could use a little more exercise, but all in all, you are not in too bad a shape for a man your age. Actually I should not call you a man. A real man would not be standing here with a plug up his ass and his cock hanging at half mast. A real man's cock should be standing tall, hard, ready to use on his woman. Not that I have any intention of riding your cock anyway. Your tongue is another matter. I am guessing you brought cialis or viagra, didn't you? All you old guys have a stockpile of that stuff."

I was not that old, but I had enough occasional episodes of erectile dysfunction to get some medication prescribed.

I started to confirm I had brought my bottle of ED meds when she put her hand over my mouth. "I will tell you when I want you to speak." she said.

"Yep, soft dick but look at these nipples. They look big and your chest is a little saggy. Old man titties. I can tell your testosterone is dropping. You know, instead of dick hardening meds, maybe we ought to get you some female hormones and see if we can get these little titties to grow a bit. At the very least we can get the little nips to swell up." I blushed at her humiliating monologue but knew it was a bluff. Just talk to push my submissive mind set.

"And I see you decided to keep your body hair. I only gave you the option because you begged like a bitch to let you keep you hair so you would not be embarrassed when you went to the doctor for your yearly checkup. But look how sparse it is. Hardly any in your armpits, and only a smattering on your chest, just a few tufts around your nips. And your arms and legs are almost bare! Just a few hairs here and there. Certainly not a masculine covering.. Even this little gray bush around your groin looks fairly sparse. Getting old is a bitch huh?"

"At least you still have balls in this scrotum. It will give me a good handle." she added as she gripped my whole scrotum in her hand and gave it a firm squeeze. She looked me square in the face and enjoying my blushing, asked, "So if you are not a real man anymore, what are you? What do I call you?"

"Bitch" I answered. "The FULL phrase." she ordered. "Slutty Little Bitch" I answered.

"Exactly!" she declared. "Do you like me calling you that?"

"Yes, ma'am." I replied.

"Liar! You hate it, It humiliates you. It unmans you. But you accept it because you know that is what you are, a bitch." She smiled. "And you submitted your bitch ass to me and that makes you SLUTTY."

"I will tell you now, when I release you and send your bitch ass home, you will truly understand what it means to be a woman's bitch." I shivered and Mary grinned broadly as she continued.

"I know you lost your wife last year. You live alone. No girlfriend, even if you could find one. So there is no reason why you cannot fully embrace your bitch side. I don't care if you have to go to a doctor. I don't care if you like to work in the yard without a shirt or want to go to a beach sometime. You have been telling me for months that you planned to start working out at a fitness center, but obviously you have not. So public showers or even a sauna is not a problem like you claimed before. Guess what? When you leave here, you will not have a single hair below the chin. I do not even care for this mustache you insist on growing. I won't have it around to tickle my clit while you lick my pussy so it can go also as far as I am concerned. I may decide to let you keep it if you beg enough, but if I do it will cost you."

"I think you are going to regret not removing your body hair on your own before you came. That tape is going to pull out a lot of hair when it comes off. It is going to do a number on your skin too. I gave you a little bottle of rubbing alcohol to loosen the adhesive and take the tape off, but you will do that on your own time, not mine. For now, I will just cut the tape above and below that plug. I want access to your tight little hole." Mary paused to giggle. "Well, it is probably not so tight or so little anymore after our play on line. And it certainly won't be tight when I finish working it this week."

Mary picked up the little scissors she had provided with my supplies. She directed me into the bathroom and had me lean over the side of the tub, placing my hips on the rim. This put me almost upside down, my face in the bottom of the tub. "I want better lighting so I don't cut you." she explained. "Plus if you did not do a good enough job cleansing, you can handle the cleanup easier in here."

I will not lie, taking the plug out hurt. Once Mary cut the tape, she wiggled it around a bit making me moan with the discomfort. My moan got louder when she finally pulled it out. Tossing it into the tub, she turned to wash her hands. "Clean your ass and wash the plug. I do not want to be kept waiting long, so you better hurry." she ordered.

I came out of the bathroom to find Mary wearing only her bra and panties. She was pulling a change of clothes out of her suitcase. and I saw a small makeup/ toiletry kit sitting on the table. "Is it clean?" she asked, taking the plug from me. "Yes ma'am" I replied. "Good. Lick it from tip to flange, That will be the test to see if you did a good job." I licked the plug as directed. Mary took the plug."Open!" she commanded. and when I complied she tried to stick the plug into my mouth. It was too big for more that the tip too push past my front teeth. She laughed. "Hold it there until I finish here." I had to bite down to hold it in, the smell of new latex filling my nostrils. I was glad I had been thorough washing it.

Once she had finished unpacking, she turned to me and took the plug from my mouth. "Put it with the other toys in your box."

Mary stripped off her bra and panties and tossed them onto the chair with the clothes she had worn earlier. When she turned I could see a full bush of reddish gray hair. Her breasts were medium size and did not droop much at all especially considering her age which I knew to be fifty three. I had seen her breasts only once before on cam but then the nipples had been flat. Now both were firm and stood tall. She sat back on the bed leaning against the headboard indicating I stand to one side of the bed.

"Now for a couple ground rules. I will not waste our time going over the obvious. You will do what I say, when I say it. You know that. BUT you will also obey anybody else I allow into our circle.. Of course all activity will be within your limits. Nod if you understand." I nodded. "I may stretch your old limits a bit though before you go home." she laughed.

"In this room you will be nude at all times. And this means ALL times. You will strip immediately upon entry taking time only to set down whatever you are carrying. You will not even walk across the room clothed. You will put a change of clothes next to the door. You may only get dressed immediately before leaving. Your limit is five feet from the door. If you get dressed to leave and realize you left your watch on the nightstand, you will strip bare before you cross the room to retrieve it. Understood?"

"Yes ma'am," I said as I nodded again.

"The penalty for disobedience is harsh. The first time, I will give you five swipes across the ass with the acrylic rod I have in my suitcase. Then you will walk nude to one end of the hallway, turn and go to the far end and then return. Your hands will be at your side at all times carrying only your keycard. The second time you violate the nudity rule, I will lead you on your trip with a leash attached to your scrotum after striping your ass."

"Now, what happens if the maid comes to clean the room?" she asked, smiling.

"Please, don't make be naked in front of a maid." I begged.

Mary smiled and said, "You may get dressed quickly before letting her in and you may leave. BUT, if you stay in this room you WILL be nude. And no loitering in the hall outside either. You go to the lobby and wait. You may put your clothes by the door later. For now, you have more important things to do."

She scootched down in the bed then raised and spread her knees ."Get busy." she ordered patting her mound.

I brought her to three orgasms before she let me take a break. I laid on my back to one side, hands on my head as ordered. Finally Mary stretched. "Does my little bitch think he deserves to cum?" she asked.

"If you think so, ma'am." I said unsure of my answer and expecting to be denied.

Mary got out of bed. "Go get a towel. I do not want a mess on my sheets. You will lick up anything you produce, of course, but I don't want a wet spot I might touch during the night." When I returned Mary was fastening the dildo harness around her hips. After seeing it in the box I expected it would be used on my ass sooner or later. I had just hoped to wait a day or so. I was sore from the plug. "Oh shit!" I muttered.

"You better not. I just might make you lick that up too." she offered. I stood watching as she finished strapping the dildo in place and testing the fit by fisting the dildo and acting like she was a male masturbating. She centered a pillow at the end of the bed spreading the towel over it..

I expected her to tell me to bend over, but she surprised me when she ordered me onto my back. "My back?" I questioned. "Yep. For this first time, I want to look into your eyes as I ream your little hole. I want to see the humiliation on your face as I make you my bitch. Ass on the pillow and pull your knees up to your shoulders and hold your legs up.."

It took a bit of positioning to get me placed where Mary was satisfied. She added two more pillows so my bottom was elevated. I watched as she smeared lube on the dildo. It was larger than any of the ones I owned. Its entire girth was probably close to the size of the larger butt plug at the widest. 'Does my bitch want a little lube in his pussy?" she asked grinning.

"Yes ma'am" I answered.

"Then ask nicely." she ordered. She told me what to say and had me repeat it several times as she applied the lube to my hole with two fingers.

"Please Mistress. Please lube my pussy so you can fuck it and make me the slutty little bitch that I am. Please Mistress. Please lube my pussy so you can fuck it and make me the slutty little bitch that I am."

"Hold onto those legs." she warned and I felt her press the tip of the dildo against my anus. I saw her wipe hands on a towel and grab my hips. 'Let's see how well your training at home and that plug earlier got you ready for this." she said with a smile and pressed forward.

At first, nothing happened. The pressure was intense."I began to beg, "No! Wait! Let's try something smaller.." Then I hollered at the burning pain as the tip popped inside. It felt like I was being ripped in two.

My eyes teared as I heard Mary say gleefully, "There we are! We are in!" She pulled back slightly then pressed forward again. Each push of the dildo brought fresh pain. I almost lost my grip on my right leg. Mary warned me against letting go.

"In a day or two I might let you wrap your legs around me when I fuck you like the whore I am going to turn you into, " she laughed." But for now let me do the work and you just enjoy it."

Finally she announced she was fully buried. I had no doubt. I felt the dildo all the way to my belly button as she pressed her groin against my ass cheeks. I could barely see. I had tears in my eyes from the pain and humiliation. "Comfy?" she asked. I shook my head and groaned, "It hurts" I cried, as my ass spasmed from being stretched.

"It will get better." she said and began to move the dildo in and out in long slow strokes. After a few moments she began to pick up the pace.

It did NOT get much better. The intense sharp burning merely subsided to an ache. Mary paused, the dildo fully embedded. "It looks like my little slut is enjoying his fucking." she proclaimed, pointing at the pool of semen on my belly. I had not even realized I had ejaculated from the dildo stimulating my prostate. She stuck a finger into the jiz and had me suck it off.

She began to wiggle the dildo side to side. I moaned at the fresh pain. "I am going to open you up even more. I will keep doing it until you eat all your cum." she said. She began to transfer the cum from my stomach to my mouth one fingerfull at a time. I sucked her fingers clean as I whimpered. Finally she was satisfied it was gone. She pulled the dildo back slowly and I thought she was going to remove it. I was mistaken. She slammed it home again.

"Please, no more!" I begged, crying out at the sudden intrusion. "I have had enough." Mary paused only long enough to reach forward and pinch both nipples. She squeezed, twisted and pulled them as she began to fuck me hard again.

"YOU do not decide when you have had enough. That is up to me." she said. She maintained her grip on my nipples as she slammed into me repeatedly. I was crying in earnest now. Finally she stopped. She told me later she only pounded my butt another twenty times, but it felt like much more.

She stepped back and began to remove the harness. Handing it to me, she told me to go wash it and return. As I stood, I noticed she had not even broken a sweat at the exertion.

I limped to the bathroom to do as I was ordered. I looked into the mirror. My chest had red streaks and my nipples looked as bruised as they felt.

Upon my return, I found Mary almost dressed. She took the strapon and held it to my face. I knew what she expected. I licked it without a word. "Get dressed. It is still early. I want to go out and get a bite to eat. Plus I want a word with Brenda before she gets off shift. You don't have a problem with her looking after you when I am away do you?"

I opened my mouth. What I wanted to do was beg her to leave Brenda out of our business. What I said was, "No, Ma'am, you are the boss."

"Indeed, I am." she said

As she put the strapon into the box, I carried my clothes to the door and began to put them on. I had my underwear on and one leg in my cargo shorts before I realized I had left my wallet, watch and key card on the dresser. I pulled off my clothes and went to get them, stark naked. "Good boy." Mary said. "I was wondering if you would remember the rules."

Mary told me she would be in the lobby. I had five minutes to get down there. She grinned and kissed me on the cheek. "You have been a good little bitch so far." Then without hesitating or waiting for me to step aside or cover she opened the door and stepped out into the hallway.

I was relieved there was no one in the hall or at least directly in front of the door. I jumped to one side when Mary opened the door and walked out. I waited for the door to close on its own. It moved part way and then stopped. One of my shoes was blocking it open. Apparently Mary had kicked the shoe in place to hold it open. I felt myself blush at just the potential embarrassment of being seen nude.

I dressed quickly and headed downstairs. Mary and Brenda sat together at one end of the registration desk. Mary snapped her fingers and pointed to a spot several feet to one side. I took my place and strained to hear what they were saying.

All I could discern were snippets. "Sounds good. I will let you handle that." "I will not tolerate a bit of disobedience." several chuckles and I could see them grinning."I am sure he will obey. Just take..." "What do you think about..." " bent but not broken..." more laughing.

Finally, Mary beckoned me over. "I have decided to share you with Brenda. Whenever I am not actively using you, she can. And we might decide to use you together. You will obey her like you would me. Understand?"

Reluctantly, and with a dry mouth, I replied nervously. "Yes ma'am. I understand." Brenda sat, smiling broadly.

Mary and I went to a cafe around the corner from the hotel. I could barely eat. Mary insisted I eat it all. "You need the energy. Between Brenda and I, you will learn to be an obedient little bitch." she said with a smile. "I am very happy to have a resource like that just fall into my lap. I thought I might have to leave you to your own devices for long periods of time while I am away. We can't have that, can we?"