The Boss Ch. 01

Last summer, my wife went away on business for about 10 days. Even though we've been married for 6 years, we don't have any children, so I found myself with quite a bit of free time alone. We had an okay sex life – a little predictable and monotonous, but hell, I knew guys that weren't getting it at all, so I counted myself lucky.

Anyway, I've always had a prolific and vivid fantasy life, but I'd never cheated on my wife – partly due to lack of opportunity, I suppose, but also partly because I felt I didn't need the hassle. Well, with so much free time with nobody around, it was only a couple of days before I started surfing the porn sites on the web.

I looked at everything – "regular" sex between couples, inter-racial, gang-bangs, BDSM – like I said my mind was full of fantasies. They all turned me on, but I found myself returning again and again to the sites with Dominant women and submissive men. I was absolutely addicted – so much so, that I even began reading erotic stories about it (actually, the stories were a bit more of a turn on than the pictures).

Even within that genre, there are numerous sub-genres from which to choose. I quickly became enthralled with stories of women who, through any number of creative devices, subjugated men in a – shall we say – less than consensual way. Almost always it was centered around blackmail of some form. Invariably, once the woman had the guy by the balls, figuratively speaking, she would escalate the humiliation of him and, quite often, involve others in his degradation.

At first, I had a difficult time understanding why this was turning me on. I was raised fairly conservatively, and I began to think of myself as some sort of pervert. Eventually, I settled on the explanation that anything taboo is, for many people, exciting and, the way I was raised, this was certainly taboo.

"Oh well," I justified to myself. "It's just a fantasy. It's not like I'm actually doing it."

Then one evening I got home from work to find Jan, my wife's boss, sitting on my front porch.

"Hi Jan. What are you doing here? You know Donna's out of town, right?"

"Of course I know, Tom. I'm the one who sent her to Chicago, remember? I'm here because Donna asked me to stop by and look at your computer. She says it seems to be running slow. Is this a bad time? I know I didn't call. I can come back when it's more convenient."

"No, no, Jan. It's always a pleasure to see you. Actually, I could use the company. I was just surprised. Donna didn't mention anything to me about you coming over, that's all."

I wasn't kidding. It is always a pleasure to see Jan. She's 54, nearly 25 years older than me, but man, is she sexy! She's about 5'6", has salt and pepper hair, which she wears shoulder length, and incredibly beautiful green eyes. At first glance, she's fairly average looking, but every time those eyes meet mine, I melt.

Obviously she doesn't have the body of a 20 year old, but there's something about a mature woman's body that's very alluring – the slight sag of her heavy breasts, the flair of her hips, the little pouch of a belly, legs that are not as thin as toothpicks, but actually have some shape – all the attributes that a young 20-something girl doesn't have.

Also, Jan always dresses nicely in some sort of business suit. I've seen her wear suits with pants, but today she was wearing a skirted suit. The skirt came a few inches above the knee and I took the opportunity to admire her legs. Her blouse, while professional, did accentuate and flatter her breasts. Yes, overall quite a nice picture. That being said, by far the most attractive thing about Jan – at least as far as I'm concerned – is her attitude. She has a very confident bearing and is completely comfortable in her own skin.

As we went into the house, she asked where the computer was.

"Wow, right down to business, huh? Aren't you hungry, or have you already eaten?" I asked.

"Actually, I am hungry," she replied. "But I don't want to tie up your entire night."

"All I was going to do was stay in and watch the tube, anyway," I said. "I don't have a lot here, though, so we'll have to either go out, or I can pick up something and bring it back here."

"Okay. Well, why don't we just get a pizza and eat here? I don't really feel like going out. I'll get started looking at your computer while we're waiting – where is it?"

I showed her to the computer and asked if she wanted anything to drink. She said she'd wait for the pizza, so I went to call in the order. Afterwards, I began walking back to the office when the phone rang. By the time I got to the office, to my surprise, Jan had answered it. Jan is always very assertive – some might say forward, or maybe even pushy – so I probably shouldn't have been surprised that she answered someone else's phone.

Anyway, judging from what I heard of her end of the conversation, the caller must've asked "Who's this?" Jan responded in quintessential "Jan fashion".

"You're calling me – who's this?"

Pause.

"Oh, hi Donna. It's me, Jan."

Pause.

"(Chuckle) I'm sorry, Donna. I can imagine what you thought."

Pause.

"Oh, I just got here about 10 minutes ago. In fact the computer hasn't even fully booted yet."

Pause.

"Of course. Hold on. Tom, Donna's on the phone."

"Hi Honey," I said when I picked up the extension.

"Hi. Boy, that was a surprise," my wife said. "It's pretty disconcerting to call from out of town and have another woman answer the phone. I forgot all about asking Jan to look at the computer. "

"Yeah. You also forgot to tell me she'd be coming by," I replied.

"Sorry, Honey. I guess I've had a lot on my mind lately. Do me a favor – please be as accommodating to Jan as you can. She can seem a little brusque sometimes, but she's not an asshole. In fact, she's very nice. She's just used to people doing what she says."

"Okay. I'll do whatever she wants," I said, just as Jan walked into the kitchen. She raised an eyebrow and gave a little smirk when she heard me say that.

Donna and I talked for another 15 or 20 minutes – ending only when the pizza arrived. In that time, Jan apparently had finished what she had to do with the computer. She walked out of the office carrying a CD, which she put into her pocketbook. I didn't really think too much about it at the time – I guess I figured that she'd brought it with her to do some kind of upgrade.

We were eating out on the back deck, when I noticed Jan staring at me. Neither of us had spoken for a while – we were so intent on eating – so when I saw her looking at me the way she was, I was a little taken aback. I gave her a quizzical look, but she just continued to paralyze me with those hypnotically beautiful eyes.

"Tom," she said softly.

"Yes Jan," I answered, entranced.

"I'd like a drink."

"Oh, I'm sorry," I said, embarrassed. "I've completely forgotten my manners."

"It's okay, Tom. I forgive you because I know that you're going to do whatever I want," she said with a self-satisfied smile.

I just let the comment hang in the air, not knowing how, or even whether, to respond. As I got up to get the glasses, I asked her what she'd like.

"I'm in the mood for something hard," she said.

Was it just me, or was she purposely playing with words? In my mind, I said, "I've got something hard for you," but of course I didn't say it out loud.

As if reading my mind, she quickly followed up with, "Do you have anything hard you can give me, Tom?"

Okay. It wasn't my imagination. She was definitely flirting.

"Um – we have whiskey – both scotch and blended," I stammered, trying like hell not to get trapped by my wife's boss. The last thing I needed was for Jan to tell my wife that I'd made a play for her.

"I guess blended will have to do for now – with ginger ale if you have any."

"Of course," I answered. "That's what I drink, also."

I made a drink for each of us and handed Jan hers, then sat down. As soon as I sat, she slipped her right foot out of her heeled pump and placed it in my lap.

"Give me a foot massage, Tom. I've been wearing those heels all day and my feet are killing me."

It didn't have the tone of a request for a favor. It sounded much more like a command. Without thinking, I began massaging her foot. I kneaded her arch and gently bent her toes backward and forward. I rubbed the top of her instep and let my fingers massage the tendons around her ankles.

"Mmm, you're good," she cooed.

She slipped off her other shoe and placed it on the arm of my chair.

"Do the other foot now."

Again a commanding tone. Again I followed her order.

As I moved my hands to her left foot, she didn't remove her right foot from my lap. Instead she began flexing it – very nonchalantly at first, but gradually becoming more blatant about groping my crotch with her foot. This surprised me (looking back, I don't know why – but it did), and I stopped massaging her other foot for a moment. Jan shot a look back at me and again those green eyes pierced my soul. She then moved her eyes back to her left foot, tacitly commanding my attention back there. I quickly rejoined my effort massaging her left foot, and Jan continued foot-groping my crotch with impunity.

Eventually I arrived at her ankle and I was about to stop when she said, "Keep going. Massage my calf."

I hesitated.

"Tom. You're not doing as I say," she said with a touch of irritation in her voice.

"I'm sure this isn't what Donna had in mind," I answered lamely.

"This isn't about what Donna wants," she said matter-of-factly. "This is about what I want. Ultimately, it's also about what you want."

"What do you mean?" I asked, becoming a little wary.

"I mean I could use a good submissive to please me in any way I see fit. And let's face it, Tom – you desperately want to serve me. You want that more than you've ever wanted anything in your life."

"No...really...I..."

"Don't try to deny it, Tom. Just look at how hard your cock is."

Just hearing Jan say the word cock got me even harder.

"Well, of course..."

"Tom, Tom, Tom. Don't even think of saying that the only reason you're hard is because I've been touching you. I know better, and so do you. You're hard – probably harder than you've ever been – because you're getting the sense that I'm beginning to dominate you."

I just hung my head.

"You want me to dominate you, don't you Tom?"

I remained silent.

She moved so fast, she was a blur. The next thing I knew, she had her hand on my crotch and began squeezing – hard.

"Tom, I asked you a question. Answer me," she demanded.

"Ow, Janet, you're hurting me."

"Yes, and I can squeeze much harder than this, Tom. When I ask you a question, you answer me. Do you understand?"

"Yes. Please let go. I'll answer you," I begged.

She let go and I sighed, an instant relief settling on me.

"Speak Tom. I'm not a patient woman. Tell me what I already know – that you want to be dominated by me."

"Well, I do want to be dominated – and you are an incredibly sexy woman – but no, I can't cheat on Donna."

"Then why don't you ask, or better yet beg, Donna to do it?"

"I can't. She would never do it"

"How do you know?"

"I just know. All she ever wants is straight missionary sex – and then only when I initiate it. She thinks everything else is too kinky. She would never even try to seduce me, never mind control me. Are you kidding me? Seriously, if she knew I even had these thoughts, she'd see me as weird and I'd have real problems getting sex from her at all."

"Hmm," Janet began. "It seems that you have a conundrum. Well I, for one, think it's wrong for you to hide who you are and not be allowed to express your sexuality. I'm going to do you a favor, Tom. I'm going to allow you to serve me. Don't worry, I know you're right about Donna – she's much too...um... demure, to ever initiate anything – and I suspect that you're right – if she ever found out about your, shall we say "unconventional", desires, your marriage would be over. I can tell that just by working with her. No, Donna will never find out. I'll be very discreet. Let's start off slow. Come here and give me a back rub."

"I'm sorry, Janet, but I just can't," I said, looking at the floor.

"Okay, Tom. Just this once I'll ask nicely. Please do me a favor and go get my pocketbook on the kitchen counter."

"Um, okay," I replied, slightly confused. Why didn't she just pick it up on the way out?

I retrieved her pocketbook and brought it to her. I remained standing after I handed it to her.

"Please sit down, Tom – I'm not leaving. I just wanted to show you something," she said with a smile as she removed the CD from her pocketbook. "You don't know much about computers, do you?" She asked rhetorically.

"No, not really. I just use it occasionally. I'm certainly no expert. But I figure I don't have to be a mechanic to know how to drive a car, either."

"I suppose that's true," she said. "But ignorance of how your computer works can get you into trouble."

"What do you mean?" I asked, suddenly nervous.

"Well, for example, your computer retains every web site you ever visit. This CD I'm holding has all the ones you've been visiting the last few days." She just let that hang in the air for a moment, then she continued. "Now, if you think you have nothing to hide – if you think that Donna would be totally okay with the sites you've been visiting lately – then you don't have to serve me. However, if you'd rather not have her find out, then I suggest you do exactly as I say, because if you don't, I promise you that she'll see what you've been up to. I hope I've made myself clear, Tom."

"Yes, you have."

"Hmm, I see you have a lot to learn. Tom, when you address me, or respond to me, you will address me as Mistress. Now let's try that again...I hope I've made myself clear."

"Yes, Mistress. You have."

"Excellent. Now we can begin. A back-rub isn't going to cut it now, though, Tom. I think you need to prove to me how devout you are. Come here – on your hands and knees."

I got onto my knees and crawled over to her. As I got to where she was, she opened her legs and raised her skirt. I started moving my head closer and stuck out my tongue, but she slapped me in the face and then grabbed me by the hair and turned my face up to look her in the face.

"Did I say you would get to taste me?"

"No, Mistress."

"Of course not, slave. You haven't earned that privilege yet. Oh, your face is going into my crotch all right, but you better not stick out your tongue unless I tell you to."

"I'm sorry, Mistress," I found myself saying.

Her only response was to pull my face into her crotch hard – controlling me by pulling my hair this way and that, according to her whim. After several minutes of this, she stood and commanded me to get undressed. Once I was nude, she instructed me to find some of Donna's lingerie and put it on.

I found some panties and a basic bra, put them on, and walked back out to the deck where Janet was waiting. She walked around me checking me out and giving me a pinch on my ass. Then she stood in front of me again and gently caressed my cock through the smooth fabric of my panties.

"Not the sexiest stuff in the world," she remarked. "But I guess it'll have to do for tonight. Tomorrow I'll accompany you shopping so we can get you some appropriately slutty attire. Because that's what you are, isn't it, Tom? My slut!"

"Yes, Mistress."

"Good. Very good," she purred. "Now get back on your knees and remove my panties."

I hit my knees immediately – both because I truly wanted to submit to her, and also because I especially wanted to taste her pussy. It appeared that time was here. I slid her panties over her nice firm ass and down her gorgeous legs. She stepped out of them and then got on her knees on the chair – facing the back of the chair with her luscious ass pointing right at me.

I was hard as a rock with pre-cum dribbling down my shaft and soaking my panties. God, I was actually going to get the chance to lick and suck that wet, delicious pussy.

"Come closer, Tom. Now you can stick out that tongue of yours..." she said as she pulled her ass cheeks apart. "And use it on my ass. I want you to rim my asshole really well, Tom. If you're good enough, then I'll reward you by letting you taste my pussy – but you have to prove yourself first. You don't get the pussy until you prove how good you are with your mouth and tongue."

"Yes, Mistress," I replied and settled in for what turned out to be about a half hour of rimming her beautiful asshole.

Actually, I wasn't looking forward to it. Just the thought of my tongue up her asshole kind of turned me off. I was only willing to do it because she had commanded it – and I was hers, no doubt about it. A strange thing happened, though. I started getting into it when I heard her moans and felt her pressing her ass harder into my face. Her moans were legitimate – she had no reason to fake it, she was in charge – and just knowing that I was bringing her that much pleasure made me happy – and hornier than I'd ever been in my life. My cock was positively throbbing now, and my panties were soaked through with the river of pre-cum practically pouring out of my cock.

Finally, she'd apparently had enough because she turned around and sat on the chair.

"Oh, Tom, that was just lovely," she said. "Come and get your reward."

She spread her legs and beckoned me forward. She gently caressed my hair as I tentatively moved my face toward her drenched pussy.

"Come on, Tom. Don't be shy. I'm not even going to manipulate your head. You proved your ability to bring pleasure with your mouth. I know you want to please me. I'm going to just let you do it your way."

So I went down on her and I honestly don't know who enjoyed it more. Certainly she enjoyed it – at the risk of sounding immodest, I'm quite good at it – but the reason I'm so good at it is because I love doing it – and I never enjoyed it more than with Janet. I loved the way her body responded, and besides, she was absolutely delicious. I brought her to two orgasms and then she was satisfied and let me stop. As much as I love it, after 40 or 45 minutes my jaw and tongue were sore and exhausted.

"Mmm, that was wonderful, Tom – truly. I'm so impressed, I'm going to allow you to cum. Why don't you roll over on your back and relax?"

I did as she instructed and she pulled my panties down and off. She pushed my legs up toward my chest and told me to hold them there. Then she ran the fingers of her right hand over my cock and gathered a fair amount of my pre-cum onto them and then stuck her fingers into my mouth and ordered me to clean them off. After I did so, she took my panties into her left hand and, using them as a type of glove, started stroking my painfully hard cock with the silky material.

As she was stroking me, she gathered more of my juice onto the fingers of her right hand and then pushed two fingers right up my asshole. I grunted at the unexpectedness of it. It didn't really hurt, I guess, so much as it just surprised me. She began working her fingers in and out patiently and I actually started enjoying it. My initial grunt turned into a long moan.

"You like that, don't you, my good little slut?"

"Oh, yes, Mistress. Very much."

"Good. I'm glad. Are you close to coming?"

"Yes, Mistress. Very close."

"Okay, you have permission to cum whenever you're ready."

After she said that, she began stroking my cock faster and harder with my silky panties. Then, all of a sudden, she rammed three fingers up my ass hard and I came, and came, and came – completely filling the panties with my sticky ecstasy.

I hope you liked this story. Chapter two will follow as soon as I can find the time – hopefully soon. As always, your comments are welcome and helpful.