Secretarial Services Pt. 02

And so began my lengthy affair with my boss, handsome Mr. Holt. We still managed to accomplish a fair amount of work each day, but several times a week we took time out for extra-curricular activities. He fucked me on the desk, he fucked me on the floor, and on occasion, when I felt especially horny, I would interrupt him at his work, open up his pants, and either suck him off or climb into his lap to ride him cowgirl.

This I could do by just raising my skirt, since he insisted, after our first couple of sessions, that I wear no underpants to work, only the black nylon stockings and garter belt that he bought for me. He also required that I wear no bra and keep my blouses open far enough for my tits to be on view at all times almost to the nipples. Good thing we never had any visitors.

"I want you to be my part-time whore," he told me. I was completely sincere when I answered that I'd like nothing better.

One other thing he insisted upon was that I shave my pussy and keep it that way. A subtle touch, perhaps, but one that I found incredibly erotic.

As time passed we grew more and more daring. We'd fuck and suck each other in his car down in the underground parking lot. We even did it in the deserted stairwell, standing up. And whenever we left the building he'd want me to tease him, by walking ahead of him on the street, say, and raising my skirt or dress to flash my naked ass or pussy at him. He'd bring his camera along and have me sit on a park bench with my legs far apart and my skirt raised high enough for him to shoot my shaved crotch. He'd encourage me to flash my bare tits at him in a boutique or a shopping mall aisle. We really did take some risks and acted like two sex-crazed teenagers.

Several weeks passed by before I realized we'd never actually had sex in a bed, in a private room. And as if reading my mind he soon after invited me to a meeting he had arranged between himself and two business acquaintances of his, in a swanky west coast hotel no less. A weekend getaway in a posh hotel! I was thrilled.

Our flight was delayed somewhat, and by the time we got to our hotel we just had time for a quiet swim in the rooftop spa before bed. We had the place to ourselves, and the soft lighting and superb city views added a nice touch after a long busy week.

Mr. Holt had me wear a skimpy bikini bathing suit he'd bought for me and if we hadn't been alone I would have been too embarrassed to swim in it. The top had only enough material to cover my nipples. The bottom was a thong that left my ass completely bare and that covered my shaved pussy with a triangle maybe two inches wide.

As it happened the suit didn't stay on me long anyway. As we relaxed in the cool water, kissing and fondling each other, he untied the suit's strings and was soon behind me, reaching around to squeeze my naked tits and rub his growing hard-on up and down between my buns.

"You want to do it here?" I asked.

"No. I want us in bed together, in a beautiful hotel suite. I want tonight, and this weekend, to be special."

"But what about this?" I laughed, reaching back to squeeze his growing prick.

"It can wait. Not for long, but it can wait."

It didn't have to wait that long. Within minutes we were in our fabulous hotel room, clean and refreshed after our dip. He insisted I wear the new black garter belt and stockings he'd bought me while he posed me on the bed and took photographs. He especially liked me on my hands and knees with my ass in the air, the black garters stretched taut over my buns, my legs spread wide. He never seemed to get enough of my ass, as I was to learn beyond a doubt in the next hour or so.

First though, typical of him, he was to insist that I have my pleasure before he did. And so he laid me flat on my back, with my thighs wide open, and went down on me, licking and teasing my already moist pussy until my labia were tingling. He left my clit till last, of course, just to tease me, but by the time he touched it with the tip of his tongue I was already well on my way to a sweet climax.

He really knew how to eat pussy, and I couldn't help but wonder sometimes why his wife hadn't come to appreciate this particular service of his. Maybe her various physical ailments prevented her from doing so, and I occasionally felt a pang of sympathy for her. But not enough to stop me taking advantage myself. It's a rare man who is willing to take the time and trouble to service a woman this way with any expertise. Or at least that's been my experience. Mr. Holt was one of those men. In less than ten minutes he had me quivering and quaking with a stupendous orgasm, and once again I was spraying his poor face with jet after jet of warm cunt juice.

I think I must have entered a kind of post-orgasmic trance for a while, but the next thing I recall is him asking me to roll over and stick my ass in the air. He stuffed a pillow under my tummy and had me spread my legs as wide as I could.

"What an ass," he muttered. "What a sweet, tight, incredibly gorgeous ass."

He ran his fingers over the elastic garters that were stretched so taut over my buns, snapped them playfully against my flesh a couple of times. Then he lay down and began licking up my gaping, inverted cunt, sending waves of sensation up through the entire length of my body. But then he was moving higher, scraping his tongue up the entire crack of my ass in long, slow, languorous strokes. His hands kneaded my buns gently and he licked and kissed every inch of my ass cheeks, slowly, slowly, as if he were savoring the taut, trembling flesh.

I suddenly felt his tongue on my asshole, rimming the tight puckered circle as if he wanted to poke inside. And then he was groaning softly, mashing his face between my buns and swirling his tongue around and around on my anus. I was still in a sweet post-orgasmic mode and the teasing of my asshole sent off continued sparks of pleasure deep, deep inside me.

"Oh fuck, oh fuck," I moaned into my pillow. "You know what I want you to do?"

"I know what I'm going to do, but I want you to tell me. I want you to beg me for it," he groaned.

He'd pulled his face from between my buns just long enough to say this, but then right away he was back on my ass, licking up and down the crack, poking and probing at my anus.

"Oh fuck, I can't believe I'm saying this," I wheezed. "I want your cock up my ass. I want your big hard cock to fuck me up the ass. I want you to sodomize me!"

"Beg me," he teased, taking another quick breather. "Beg me to do that to you."

"Oh fuck," I gasped. "Please do it to me. Please, please fuck me up the ass with your big stiff cock! I really want you to! I need it!"

He seemed reluctant to stop kissing and licking my asshole, but at last he knelt up, reached for a tube of lubricant on the nightstand, and began smearing gobs of the stuff up and down the crack of my ass. I felt his finger force more of the goo onto my anus and suddenly it was up my ass, making sure my inner hole was lubed. Once his finger withdrew I glanced over my shoulder and watched him smear a load of goo up and down the rock-hard column of his cock. I buried my face back in my pillow and waited.

And soon I felt the solid bulk of his cockhead scraping up and down the crack of my ass. Another second or two and it was lodged firmly onto my anus and he was applying pressure, no doubt bracing his hard-on in his fist. I braced myself also, tensing my thighs and forcing myself back onto the massive shaft of his prick.

For a few seconds nothing happened. The pressure grew against my resisting sphincter. But then suddenly something relaxed, and I felt the granite bulk of his cockhead entering my anus.

He kept up the pressure and his cock bulled deeper into me, till there must have been several inches of prick shaft buried up my ass. He paused, breathing heavily.

"You okay, baby?" he gasped.

"I'm okay," I panted, though I was unsure that I was.

I don't know if you've ever had a huge erect cock shoved up your ass, but it's the strangest sensation. It's uncomfortable, but somehow the lewdness of the situation, the outright dirtiness of it, the taboo element, give it a kind of obscene thrill. Part of you can't believe you're letting a man do this to you, but another part is excited that this is the ultimate gift you can give a man, in a way.

I'd never tried anal sex before, and I must confess I was curious about it. As inch after inch of rock-hard cock bulled up into me I did wonder momentarily what I'd gotten myself into. But then I thought what a wild, exhilarating thrill this must be for Mr. Holt. After all his years of abstinence. I was glad I was giving him this ultimate gift.

"You still okay? It's almost all the way in," he panted.

"Yes! Oh fuck, yes!" I grunted. "It just feels so strange!"

My face was mashed into the pillow. My hands clawed at the sheets. And as I felt his pubic hair against my buns I realized he was in me all the way. He'd buried that massive cock all the way up my ass.

He paused again, as if he couldn't quite believe it himself. Then he gave off a deep groan of pleasure and began fucking me, plowing his lubed cock again and again up my willing asshole. There were soft smacking sounds as his hips hit my thighs time after time.

I was being fucked up the ass. I was being sodomized. And I must confess the discomfort had given way to a kind of weird, abstract pleasure. I let myself be rammed forward into my pillow again and again. I think I began to whimper and moan. Beneath me my tits were mashed into the bed and my nipples were tingling.

And it didn't last long. He kept plowing in and out of me. At one point he gripped the rear strap of my garter belt and hauled on it so hard I thought it might snap. But he was really far gone. I think the obscenity of what he was doing to me, the incredible lewdness of it, was just too much for him to keep going for long.

In a matter of seconds he was groaning loudly and falling down along my back. He kept thrusting his cock into me, and his whole body gave off a series of shudders. I knew he was coming, spewing his hot sperm deep inside my ass. I felt his hot breath against my ear as he climaxed.

His orgasm seemed to last for a long time. His thrusts grew so hard the bed began to squeak. But gradually he slowed down. His lunges grew gentler. And finally he lay quiet on top of me, his prick still embedded in my asshole.

"Amazing," he whispered in my ear. "Just fucking amazing. What a climax. What a fuck."

I lay beneath him in a kind of daze. I couldn't quite believe what I'd just done, what I'd just allowed. Anal sex. What a strange sensation. What a weird, wild, dirty thrill.

And then he was withdrawing, And if I thought having a big cock shoved up my ass was strange, how about having one withdraw! What a weird feeling of evacuation! I groaned out loud at the peculiar sensation. I couldn't help but feel my poor asshole must be gaping wide, the size of a quarter at least. Maybe that's why he knelt there behind me for so long, gazing down at me. He was probably watching his sticky semen ooze from my ass and dribble down my thighs to soil my stockings.

Eventually he lay down beside me and we kissed and cuddled and drifted into a doze. At some point we must have gotten up to shower but I can't really remember. I do recall waking up several times in that enormous bed and realizing we were finally sleeping together, spending a night in each other's arms. And as I drifted back off to sleep again I thought vaguely of the conversation we'd had after I'd first sucked him off and taken his load all over my face.

"Is there anything you won't do?" he'd asked me, or words to that effect.

"We'll see, won't we?" I'd answered.

Now that I'd let him fuck me up the ass I wondered if we'd gone as far as we could go, or if we'd maybe reached the end of the line in our sexual exploration. I didn't know it at the time, of course, but I was to have a partial answer to that question within the next twenty four hours.

The day began after breakfast with him excusing himself to go meet up with his two business acquaintances, who happened to be staying in the same hotel. We arranged to meet for lunch and a few hours of sight-seeing in the city, and before parting he handed me a wad of bills and told me to go buy some more sexy underwear from a boutique we'd noticed a block or so from the hotel.

"What sexy underwear do you have in mind?" I teased. "You don't let me wear underpants or bra anymore."

"You know. Stockings. Garter belts. The kinky stuff I love."

And so that's what I did with my morning. I bought expensive nylon stockings in several shades, mostly black, along with matching lace garter belts. I even purchased several bras that had no cups, just lace harnesses that looped around my tits but left them completely bare. I also bought some whorish make-up, inky black eye shadow and scarlet lip gloss, that I thought he might enjoy.

We spent the afternoon exploring the city, packing as much as we could into those precious few hours. We returned to the hotel exhausted but exhilarated, took another refreshing dip in the pool, and by early evening were having dinner in the hotel's rather exclusive, dimly lit restaurant, where, to my surprise, I got to meet Mr. Holt's out of town business associates.

My initial disappointment at not having Mr. Holt all to myself for a romantic meal soon evaporated in the company of these two sexy, middle-aged gentlemen. They were not only from out of town, they were from out of country, out of continent. They were from

Brazil, of all places, dark-skinned, suave men of the world, slightly graying at the temples, perfectly fluent in English and as sweet and charming as Mr. Holt himself.

They also seemed to find me as sexy and attractive as did my boss, though considering my get-up I wasn't too surprised. I'd worn a black mini-dress Mr. Holt had picked out, one so mini I swear my stocking tops and garters were on display every time I crossed my legs, and cut so low my braless tits nearly tumbled out each time I leaned forward. I'd also worn my whorish make-up, deep, dark eye shadow and garish red lipstick.

They couldn't seem to keep their eyes off me, especially my tits, though they kept the conversation light and amusing and no one tried to play footsie with me under the table. When I excused myself to use the ladies' room at one point I could feel their eyes on my black stockinged legs and trim ass. And when I returned to the table the looks they gave me didn't leave much to the imagination.

"They want to fuck you," Mr. Holt told me later as we shared an after dinner drink in the bar.

"They made that pretty obvious."

We were alone now. Marco and Tomas had retired to their rooms, but had left an invitation for us to join them up there later if we so desired.

"And how do you feel about that?" Mr. Holt went on.

I stared at him and a slight shock swept through me.

"How do I feel about fucking two strange men I've only just met?"

"Yes."

There was a pause.

"Would I be fucking them separately, one at a time, or both together?"

I was smiling. Part of me didn't think this conversation was at all serious. I just thought Mr. Holt was teasing me.

"Both together," he said, and I suddenly knew he wasn't kidding. "They were very specific about that. And I'd be there too. You'd be taking on three men at the same time."

A lewd thrill went through me. The initial shock of having Mr. Holt proposition me in this way, in effect offering his current lover up to two horny business acquaintances for a menage a trois, a menage a quatre, whatever it was, shocked and disturbed me. How could he suggest such a thing? That was my initial reaction.

But that didn't last long. In a way, this was maybe just part of our current pattern, I thought. Sexual experimentation, sexual play. It wasn't as if Mr. Holt and I were married, or had any long-term commitment. He'd told me on several occasions that he'd never abandon his wife, and I had no illusions about our affair being a life-long deal. Did we love each other? Maybe a little. Did we feel a deep-seated affection for each other? Absolutely. Were we committed to each other forever, swearing off all other contact? Hardly.

I'd had a fair amount of wine at dinner and was now sipping a highball, but I wasn't drunk. Still, the longer the notion of a dirty evening with three men sank in, the less outlandish it sounded. And I have to confess that the longer I thought about it, the wetter I got between my legs.

"When did you all come up with this idea? When I was in the washroom?"

"Yes. They suggested the possibility while you were gone. I promised to broach the subject with you."

"How do you feel about it, that seems to be a question," I said.

"I'm a little ashamed to say that the idea excites me no end. The thought of you with three men ... I'm getting hard just imagining it."

"You wouldn't feel jealous? Possessive?"

"I don't know what I'd feel. All I know is, I want to try it. How about you?"

"Three men. At the same time. Holy fuck!"

"Was that a yes?"

I looked into his eyes.

"It wouldn't bother you to see me with other men? It would excite you?"

He took my hand and placed it on his crotch beneath the table. His cock felt hot and hard as granite through his pants.

"Does that answer your question?"

And so it was that after a brief trip back to our room to freshen up we were tapping on the door of a suite several floors above ours and were being ushered in by a grinning, welcoming Marco.

"So you decided to join us?" he said, kissing me lightly on both cheeks. "We're delighted. We couldn't wait to see you again."

Tomas came over to kiss me also. We stood by the window admiring the spectacular view while he made us something more to drink. He handed us our glasses and stared at me in frank admiration while Marco beamed at us from the sidelines.

"Mr. Holt told you why we invited you up here? You understand?" he said.

"I understand. You want me for sex."

He smiled sweetly.

"Exactly. We want you for sex. Have you ever been with more than one man before?"

I felt a little like I was applying for a job, or that I was undergoing an interview in the school principal's office. I smiled demurely.

"Never."

"And you're okay with it? It doesn't bother you?"

"It's something I'd like to try. The idea intrigues me. It excites me."

"And your boss Mr. Holt obviously agrees or he wouldn't be here either.'

Mr. Holt didn't say a word. He didn't have to. He was grinning from ear to ear, obviously anxious for things to begin.

Tomas put down his drink and took mine from my hand. He stepped in front of me and kissed me gently on the mouth. Then he hooked his fingers under the straps of my mini-dress and looped them off my shoulders. The dress drooped down, leaving me naked from the waist up.

"I've never seen such full, beautiful breasts on a girl so slender," he muttered. "You have an incredible erotic appeal, young lady. And those nipples!"

I do have amazingly erect nipples, and during this weird little interview they may have stiffened even further. Having him flick them gently with his thumbs did nothing to soften the effect, and when he dipped his head to suck one between his lips they were probably over half an inch long.

The dress slid further off my hips and to the floor, and suddenly I was standing there naked but for my stiletto heels, my stockings and garter belt.

"And a shaved pussy!" Marco murmured. "How beautiful. How perfect."

And I have kinky Mr. Holt to thank for it all, I thought, as all three men ogled me. But for him I would never have shaved my pussy, or taken to wearing garter belts and stockings. I would never have gone out in public wearing no bra or underpants. My life certainly had changed since I started working for my very naughty boss.