The Boss Ch. 02

After Mistress Janet left that first night, I couldn't sleep at all. I couldn't stop thinking about what had happened -- and how much I loved every second of it.

I got to work and settled into the "same ol' -- same ol'" humdrum. By 10:00 AM my lack of sleep was catching up with me and I was ready for a nap. Just as I was thinking about going to get a coffee, my phone rang. We have caller ID where I work and it came up with my wife's office number. Temporarily forgetting that Donna was out of town, I answered, "Hi Honey."

"Hi Honey?" Came the reply. "You're getting a little presumptuous, don't you think, slave?"

Janet! Shit!

"I'm sorry, Janet. I saw Donna's number and answered out of habit."

"Oh, now it's 'Janet'", she said caustically. "I thought you understood that you are to call me Mistress. I AM going to have to punish you, I see."

"But I'm at work. I can't talk like that at work," I objected.

"You have your own office, don't you, slave?"

"Yes, I do. But sometimes there are people in my office."

"Okay, listen -- I'm in a good mood," she said. "I'm going to let it slide this time. I'll be sympathetic to your situation. From now on, however, if you are alone when we talk -- no matter where you are -- work, home, at a restaurant, at the convenience store -- no matter where -- you are to address me properly. If there are people around, then you don't have to -- I told you that I would be discreet, and you need to trust me if this relationship is to work. But I need to trust you too, Tom, so I expect that you'll be honest."

"Yes, Mistress. I understand. Thank you for your leniency."

"You're welcome. Anyway, the reason I'm calling is because I told you we were going shopping today -- do you remember?"

"Yes, Mistress. I remember."

"Are you looking forward to it?"

"Umm..."

"I want you to always be honest with me, Tom. I will never punish you for answering a question honestly."

"Umm, okay. Well, actually, no, I'm not really looking forward to it, Mistress."

"Why not? Don't you want to be my slave-slut?"

"Yes, Mistress, I do -- I've finally accepted that I really do -- but I just don't see myself as a transvestite or cross-dresser or whatever you want to call it. I guess it just doesn't turn me on," I said.

"That's where you're wrong. You were incredibly turned on last night," she retorted.

I certainly couldn't deny it. So why did I have a problem? Was I turned on despite the cross-dressing, or because of it? I honestly didn't know.

"You're right, of course, Mistress. I was more turned on than I've ever been. I just think it was because of you, and not because of being dressed in that way," I offered.

"You may be right about that. Maybe you don't want to dress up. But the fact that you did it submissively when you didn't really want to is why it was such a turn-on for you. You got off on being ordered to do something you would never allow yourself to indulge in otherwise. There are a lot of things that'll be true for -- and we will explore many of them. I will never allow you to be hurt, Tom. Nor will you ever go home to your wife with marks on your body that you have to explain. Do you trust me?"

"Yes, Mistress. I trust you."

"Excellent. Then you will do anything I tell you to do -- even if you think you don't want to -- as long as I keep my promise not to hurt or mark you, right?"

"Yes, Mistress. You have my word."

"Good. Are you able to get away from the office for the rest of the day?"

"I guess so," I replied. "I have some sick time. I can just say I'm not feeling well and leave."

"Excellent. I'll meet you at your house. No, scratch that. You don't need nosey neighbors causing trouble. Meet me at my house. Do you know where I live?"

I told her I didn't, so she gave me directions. After making my excuse to my boss, I shot over to my new Mistress' house as fast as I could. I was nervous, though -- I really had a bit of a problem with the whole cross-dressing thing. But apparently I was very excited also, because I found myself speeding to get there.

When I arrived she let me in and I was surprised to see her in very sexy lingerie. She wore a blue demi-bra, a matching thong, white hose (the hose she wore were the type that stayed up by themselves -- she wasn't wearing a garter belt), and blue heels. She looked incredibly sexy -- truly a vision.

"I wasn't expecting you quite so soon," she said. "You made good time."

I didn't know what to say, so I said nothing.

"Well -- what do you think," she said as she twirled around. "This is more like what I had in mind for you -- not that boring stuff your wife wears."

"It's very sexy on you, Mistress. I don't think it would be on me, though."

"You might be surprised. Heather is a true artist."

"Who's Heather," I asked.

"She owns the shop where we'll be going shopping. It's a very private place and she knows me, and what I like, very well."

I must have breathed a sigh of relief, because she chuckled and said, "Don't worry, Tom, I wouldn't take you to a mall for something like this. We can't have anyone you know seeing you, can we?"

"No, Mistress. Thank you."

"I told you -- I appreciate your need for discretion. Like I said before, we need to have complete trust in each other. I will not betray that trust, Tom."

"What about the disk. You threatened to blackmail me. How is that trust?"

"Oh, Tom, is that what you're worried about? That was just to give you an excuse to do what you wanted to do anyway. I would never really blackmail you with that."

With that, she went to her pocketbook and retrieved the disk and handed it to me.

"Here. Do what you want with it. I'm not going to use it. It's just that I knew that you wanted to submit to me -- perhaps more than anything you've ever wanted. But you were holding back, trying to be 'good'. That was just my way of nudging you. I don't need it any more. You're here to stay now, aren't you Tom?"

"Yes, Mistress. I am."

"Good. Let's go to Heather's."

Heather was an extremely beautiful woman. She was about 6'1" in heels. She had curly red hair, perfectly painted nails, and was wearing a very tight green sheath-type dress. I don't know what it's really called -- basically a 'little black number', but in green.

"Well, well, Janet," she said. "You have quite a handsome guy here. Is he a new slave of yours?"

"Yes. This is Tom. He's a bit apprehensive about this, so be gentle with him," she said, chuckling.

"Of course. You know me, sweetie. You won't know him in an hour."

"No, Heather. Not the full treatment -- just lingerie. I actually like him as a man. This is just an exercise in obedience. I don't want him feminized."

"Oh well. It's probably just as well," Heather said. "He is a very masculine man, I can see your attraction."

Then to me, she said, "Okay, Tom, start getting undressed so we can try on a few items."

I looked at Janet.

"Mistress?"

"Get undressed, Tom. That's why we're here."

I undressed to my briefs and stood there while Heather caressed my chest and teased my nipples. After a minute or so of that, she slid her other hand down the back of my briefs and gave my ass a gentle squeeze. Again I looked at Janet, but she was just watching with a smile on her face.

"Almost there, Tom," Heather said. "But I think you'd look silly with a thong over your briefs. Take them off."

I bent as I removed my underwear. As I stood back up, my cock was in plain view -- in all its rampant glory.

"Mmm. Janet, you are one lucky woman," Heather said as she stroked my hard cock. "I'm jealous."

Then she handed me a red, lacey thong. She didn't need to say anything -- I knew what was expected and put it on. Heather reached into it and arranged my cock so that it was pointed up, flat against my belly. Then she handed me a red bra -- also lacey. After a minute or two of clumsy attempts to put it on, she helped me with it.

"Well, Janet, what do you think?" Heather asked.

"Nice. But something looks out of place." Another chuckle.

"Yeah. I see what you mean. Are you sure he didn't want to do this?"

"That's what he said. Although he does look pretty excited, don't you think?" Janet asked.

"He certainly does -- too much so. It just won't do."

"Well, you're the expert," Janet said with a smirk. "You do whatever you think is necessary."

Heather got down on her knees in front of me and started removing the thong.

"The first thing we need to do is get it off him before he stretches it out."

She brought the thong all the way down and I stepped out of it when she tapped me on the ankle.

"Now," she said. "We have to do something about that big dick. It's just going to continue getting in the way -- plus it's distracting."

"Yes. I see how it keeps drawing your attention," Janet said. "Why don't you satisfy your curiosity and take care of it, Heather. Make it so it's not quite so ...um...prominent."

"I think that would be best, Janet. Come here, Tom."

With that, she took hold of my cock, led me to a chair, and told me to sit down. Then she kneeled down again and, took my entire cock into her hot mouth. She moved her head up and down three or four times, moaning the whole time.

Releasing my cock from her vacuum-like mouth, she said, "Mmm, Janet, that is one heavenly piece of meat."

Then she went back to sucking me off like crazy. This woman obviously loved sucking cock. She was damn good, too. I grabbed her head and started guiding her up and down my length, when suddenly Janet slapped me across the face.

"Who do you think you are, slave? You're not in control here. You're my slave, and you will act like a slave. If I decide I want you to service someone else, you will do it -- but the reason you're doing it is for their pleasure, not yours."

"I'm sorry, Mistress."

"Apologize to Heather, not me."

"I'm sorry, Heather."

"I'll make sure that doesn't happen again," Janet said.

She pulled a pair of handcuffs out of her pocketbook and weaved them through a spindle on the chair and fastened them to me. Then, from Heather's inventory, she got a pair of stockings and used them like ropes to tie my legs to the legs of the chair. While she did this, Heather just watched her. Now, Heather looked to Janet for approval to continue.

"There you go, Heather. I'm so sorry about that," Janet said. "Please continue. Enjoy yourself. I wish there was some way I could make it up to you -- like I said, he's new to this."

Heather went from kneeling upright to being on her hands and knees and glanced over her shoulder toward her own ass, then she looked back at Janet.

"Oh, of course," Janet cooed. "You love having your ass filled, don't you? Would you like me to play with your ass and prepare you while you continue sucking Tom?"

"Mmm, that sounds very nice," Heather replied. Then she enthusiastically resumed sucking me.

Janet got down behind Heather and started rimming her asshole. When Janet's tongue pushed into her ass, Heather moaned loudly, sending a pleasing vibration through my engulfed cock. Janet continued rimming Heather and Heather continued moaning, which continued sending vibrations down to the root of my cock -- my balls tingled -- I swear the bones in my pelvis were vibrating. I began to moan.

"Don't you dare cum," Janet warned. "Heather wants her ass fucked and you'd better not embarrass me again by coming before that happens."

Janet sidled up alongside heather and, dipping her fingers in some lube that she had ready on the table, she slowly inserted two fingers into Heather's ass. Fortunately for me (I didn't want to cum, after all), this drew Heather's attention away from my cock and back to her own pleasure. She threw her head back and cried out in a throaty voice, "Oh yes, Janet. That feels so good."

Janet continued driving two fingers in and out of Heather's ass, while with her other hand she began caressing the rest of her body -- the cheeks of her ass, her breasts, up and down her back -- then, after a few minutes of that, she added another finger, driving three fingers in and out of Heather's hot little ass. This resulted in another cry of approval from Heather.

"Oh Janet, you do that so good, baby, but I'm ready for the real thing. I want that hard cock in my ass."

She stood up and grabbed my cock.

"Good. He's still hard."

Of course I was still hard. True, she had stopped sucking me for a while, but I was still watching the show the two of them put on. I'd have to be dead to not be hard. Anyway, this is when Heather straddled me and, with her back to me, slowly descended onto my hard, throbbing cock, taking the entire thing in her ass. When she bottomed out, she stayed there for a minute to get accustomed to it, then, after about a minute, she began grinding her ass. She did this for a little while, and then she began a slow up and down motion. At first, she only went up an inch or two before coming back down, but after a few strokes, she really started going all the way up and down. Her hot, tight ass felt incredible around my dick.

"Mistress, I don't know how long I can hold out. I feel like I'm going to cum," I said, almost in a panic.

With that announcement, Heather got off my dick and got back on her knees.

"In my mouth," was all she said before plunging straight down onto my cock.

I didn't last more than three or four seconds before I started coming. My cock spasmed five or six times and Heather just kept her mouth on me and took in every hot, sticky drop. Then, when she knew that my cock was completely spent, she stood up and straddled me again -- this time facing me -- and pressed her mouth to mine and kissed me. Janet stood behind me and pressed the edges of her hands down along my jaw, forcing my mouth to open. Heather pushed her tongue in and my cum began flowing into my own mouth. She continued kissing me very passionately -- just the kiss by itself was hot as hell -- she really knew how to kiss.

When Heather broke the kiss, I noticed that Janet had brought another chair alongside mine and was sitting in it.

"That was quite a turn-on to watch, Heather. Did you enjoy yourself?" Janet asked.

"Um-hmm!" was Heather's emphatic reply.

"Are you ready to finish?" Janet asked.

"Yes. Absolutely," Heather responded.

I thought they were talking about continuing with the dress-up party. Imagine my surprise when Heather walked over to Janet, pulled up her green dress and presented Janet with a solid looking cock. And no, it wasn't a strap-on. It was the real deal. Where "she" was hiding it, I have no idea, because it was of significant proportion.

Janet started devouring this gift with gusto. She apparently loved Heather's cock. I couldn't blame her -- it was quite a cock. There are all kinds of styles of sucking cock. On Heather, Janet used one that involved a lot of slurping sounds. Saliva coated and dripped off Heather's cock with every out stroke. The sight and sounds of this had me getting hard all over again.

I guess Heather was pretty worked up also, because she only lasted a few minutes before Janet's expert mouth had her on the verge of orgasm. At the point of no return, Janet stopped sucking and, with a gentle tug of her hand, directed Heather's cock over to me. Being restrained, I was at their mercy, but honestly, it didn't matter. I was so horny I didn't care what happened.

Of course what happened was Heather stood in front of me, Janet stood behind her and jerked off her amazing cock until it spewed a huge load all over my face. Afterward, Janet and Heather cleaned my face with their tongues and shared the creamy profits with each other in a long, sexy kiss.

When we'd all calmed down again, Janet said that the thong and bra set was perfect and paid Heather. Then she released me and brought me home -- to her home.