The Regional Directors' Meeting Ch. 04

Debby called me at work two days later.

"What are you doing in the office at 5:30 p.m.? I chided her. "Don't you know the corporate world closes at 4:30 on Friday?"

"Very funny, smartass," Debby retorted. "In fact, I waited to call until everybody was gone."

"Uh-oh. That sounds serious. What gives?"

"Weeell, I thought nothing of it when Margie came back from the November meeting all relaxed and cheerful," Debby said. "But when Wanda came to the office this morning acting like a new woman, I realized something was going on.

"You wouldn't know what's happening to my staff while they're in your fair city, would you? You know ... while they're staying in a hotel just six blocks from your office."

I hesitated. Dad always said a man keeps his mouth shut. Sex had always seemed to me like a private thing. If Margie and Wanda wanted Debby to know about our encounters, THEY would have to tell her. Not that she didn't already know.

"I don't know what you mean," I lied in my most innocent voice. "Maybe they're listening to Deepak Chopra tapes."

"Huh! Right! And Dr. Phil changed my life!" she jeered.

"Oh well," she added after a pause. "Now I remember one of the great things about you. You never kiss and tell."

"Maybe there's nothing to tell," I said.

"Oh, I know better," Debby said. "You see, one of my other girls had the hotel room next to Wanda's the other night. Cindy says she counted Wanda's climaxes and was quite impressed! Then Wanda mentioned you on the flight home, before clamming up when Cindy started asking questions."

"Uh-oh!" I said. "I hope Cindy won't blab. That could be tough on Wanda."

"Rest easy cowboy," Debby said. "Cindy is a very nice girl, and she promised herself she would tell only one person -- and that was me."

"That's good. I thought of trying to get Wanda to be quiet, but she was having such a nice time I didn't have the heart."

"I know," Debby giggled. "Remember that time in Aspen when the guy in the next room started pounding on the wall?"

We both laughed.

"At this rate I'll have to put you on the payroll," she said. "Your title will be something vague ... Deputy Manager for Employee Morale or something."

"Shouldn't you be telling me what an unfaithful, slut bastard I am?" I asked.

"I got used to the idea of you doing other women long ago," Debby said. "I don't own you any more than you own me. And I'd much rather think of you fucking a good friend like Margie, or a sweetie like Wanda, than boning that bitch wife of yours."

We bantered awhile longer before hanging up, but I got an email from Debby just before the March director's meeting.

"You can forget about any fun this month," she wrote. "Only two of my staff are going. One is pushing 70 and the other is Cindy, who is happily engaged and getting married in September.

"SORRY, LOSER!" she closed.

Oh well. After Margie and Wanda I already felt like the luckiest guy in the world. So I was plenty surprised when my office phone rang on the night of the March meeting and I heard a woman's voice.

It was Cindy -- the girl who was getting married in September! And she wanted to see me! Curiosity alone would have sent me to her hotel room. It was likely she was having sex with her fiance. And the sex must be good since she was marrying him. So why would she invite me to her room? Maybe she really did want to talk?

Cindy let me into her room with a smile and gave me a drink. She wore black slacks and a form-fitting green top while a matching blazer was draped over a chair. Her shoes were kicked off under the table. We drank and made small talk while looking each other over.

I was intrigued. Cindy was one of the slimmest women I had ever seen! It was as if a perfectly proportioned 5-foot-3-inch woman had been stretched up three or four inches, leaving her symmetrical in all dimensions except the vertical axis. Her face, neck, trunk, arms and legs were long without being the least bit bony.

In fact, she gave the impression of sleekness and grace from the tips of her long toes to the widow's peak on her forehead. It was a delight watching her move her long, slender hands while talking or pushing back her straight glossy brunette hair. And her snug top clearly outlined a sweet pair of champagne-glass tits in a thin bra.

Skinny model types have no appeal for me, but Cindy was nothing like that. She gave an impression of strength and coordination like an athlete.

We chatted for awhile before she came to the point, preceded by a deep breath.

"I missed the girls'-night-out last fall, but I heard a couple of Debby's stories second-hand," she said talking quickly and nervously. "Then there was last month's meeting when I had the room next to Wanda's."

Her big, hazel eyes looked at me cautiously.

"That was you wasn't it?" she asked.

"Yes, that was me."

"So ... " her voice trailed into silence and she looked away. There was a pause and I noticed her clasping her hands together tightly.

"You could tell me what you're thinking," I prompted. "But if you're uncomfortable ... " I left the sentence unfinished.

She looked up at me with a small grin.

"Actually I have a question," she said, stopping again.

I finally told her to go on, and she looked up and away.

"It's pretty personal."

"If it bothers me, I won't answer," I prodded. She looked down at the clasped hands in her lap and the silence stretched out.

"Did you ... mmm ... do her ass?" she said, still looking down.

"No, we just covered the basics," I said, my pulse beginning to thud. Another silence fell, her face was flushed pink.

"Have you ever?"

"Yes, I have," I said, "several times."

"So ... you like it?"

"I do."

"Was it good ... for the girl."

"Well, with one girl it was her first time. She changed her mind pretty quick, so we stopped."

"But the other girls liked it?"

"One girl, actually. She didn't want it all the time. But every month or six weeks she'd whisper in my ear and we'd do it again."

A long silence followed, then Cindy took another deep breath and stared out the window at the twinkling skyline.

"I saw this movie once ... it was the hottest I ever saw," she explained. "The guy was very sexy and the girl was even better. As a couple they really turned me on ... the seductive way she moved ... the forceful way he responded. They had amazing chemistry.

"Anyway, in one scene the girl was naked, lying face down on a bed. The guy was on top of her ... he was humping her. You really couldn't see anything except their faces and bare shoulders, but my God! It looked so real ... so animal!

"I sat there squirming in my seat. I knew if I touched myself I would come and my date would hear me. I couldn't wait to get rid of the guy, go home and rub myself all I wanted.

"For a couple of years I replayed that scene in my head whenever I wanted to get turned on," Cindy said. "But after awhile it began to puzzle me. So I bought the video and watched it again.

"The position ... the angle ... was all wrong! There was no way he could get into her pussy in that position! And I realized ... he was fucking her ASS!

"Sure, they were faking it ... but they were ASS-fucking right there in front of the world ... in an R-rated movie! And I could tell the actors were turned on! They were into it!

"I ... I was stunned when I figured that out. But the next thing I did was shove both hands in my pants. I rubbed my spot a few times, then just pushed a little against my asshole. I came like mad, flopping off the couch to the floor! I even passed out a little ... .

"I went went online that day and bought my first dildo. Two actually. One for my pussy and a little one for my ass. I spent the next weekend watching that video and coming and coming. I could come right now just thinking about it.

"That was great. But after awhile I got tired of watching the movie and I wanted to be IN the movie! But when I asked him, my boyfriend was turned off. Backdoor sex doesn't appeal to him at all. So I dropped the subject. Now he's my fiance and we're getting married soon."

She paused and took another deep breath.

"So I mentioned anal again and his reaction told me all I need to know. Ron will never change his mind. I'm going to spend the rest of my life never knowing what it feels like ... the one thing that makes me crazy just thinking about it."

"So now you know why I asked you here ..." her voice trailed off, but she glanced quickly at my face before looking away again.

"Cindy I would be happy to show you what it's like," I said, "but you've fantasized about it so long ... the real thing can't possibly match your imagination. You'll probably be disappointed."

"I know that's possible, but I have to know," she sighed. "I have to know what it feels like before I can forget about it forever. It's the dirtiest, wildest sex I can imagine and I have to KNOW!"

I was pretty hot myself by that time, while realizing I had to use extreme care. It's one thing to imagine butt sex, when your mind controls every move and sensation. But it's another to attempt with a flesh-and-blood partner. The real thing requires patience and control, especially the first time.

"So, lights on or lights off," I asked.

"Definitely off!" she said, grinning. "I may be helplessly horny, but I'm not crazy enough to let a strange man see me naked!"

So I turned off the lights and saw her silhouetted by the dim glow of the city coming through the window.

"Can I ask you one favor for tonight?" she said tentatively.

"Sure."

"Two, actually," Cindy continued, breathing quickly. "Don't ... put your dick in my pussy and ... and don't kiss me on the mouth. I think I can live with my conscience as long as that's saved for Ron and nobody else."

"Okay, sounds reasonable. How about we start with a shower so we're clean and comfortable," I suggested.

Cindy agreed and we fumbled our way into the darkened bathroom and shed our clothes, laughing when we bumped each other. Luckily one of the power outlets had a tiny amber light on it, or the blackness would have been complete. She started the shower, waited for it to warm and we carefully felt our way into the tub.

"Why don't you wash me?" I said, hoping to relax and divert her with the task. Without replying, she sprayed me with the shower head, then started soaping my chest. She started quickly at my neck, then slowed to feel her way along my shoulders and down across my chest to my ribs.

Cindy washed down my front, while I washed my face and hair. She came to my dick and stroked its soapy length.

"Maybe I should look for somebody smaller," she said, smiling up at me in the dim light.

"But that's not what you want, is it?" I asked, guessing her thoughts. "You decided to do this when you knew you were coming to the meeting. And you don't care how big I am."

She seemed to blush in the dim light, and studied my swollen dick in her hands.

"You're right. I don't care how big you are, but I'm glad you're not a horsecock. My fantasies are about pleasure, not pain."

I massaged shampoo into her hair, washed her neck and moved my hands down the silky smoothness of her shoulders. Her breasts were small enough that I couldn't really cup them, so I pressed them gently against her ribcage and soaped them with circular motions. Her small nipples grew into hard little pebbles and she held herself motionless, sighing contentedly.

Then I pulled her to me and washed her back, delighting in the way my hands slid down her spine to her smoothly indented waist. Cindy's hands washed my balls and went underneath them all the way to my ass, washing carefully. My hands cupped her full, rounded buttocks, gripping them to pull her against me. My fingers rubbed gently down the crack of her ass then brushed over her puckered little hole, making her stiffen and gasp.

Next I knelt in front of her and washed her feet, carefully lifting them to get her soles and between her toes. She put her hands on my shoulders to keep her balance while I lifted one foot to wash, then the other. The 'V' between her thighs was inches from my face, a neatly trimmed bush covering the sweet treasure beneath. I massaged and washed my way up one long slender leg, then up the other all the way to her butt.

Then we rinsed, helping each other turn round under the warm spray, hands caressing gently, before turning off the shower. The dimly lit room was filled with warmth and moisture.

"Wait a sec," I said, and opened the shower curtain enough to put one foot on the floor and reach for a small bottle of hotel lotion on the counter opposite the tub. Back in the shower I emptied half the lotion into one hand and knelt again to massage Cindy's legs, smoothing the lotion up from her ankles all the way to her butt, first one leg then the other ... taking my time. Her hands rested on my wet hair.

Then I emptied the rest of the lotion into my hands and reached around to massage her butt, leaning my head against her flat belly. I could feel the warmth rising from her crotch. I heard Cindy give a long sigh as my hands squeezed her butt cheeks then started spreading lotion down her back channel.

Finally I found her puckered little hole and my slippery fingers stroked carefully over it, spreading lotion, but not penetrating the tight ring of muscle. Now she was crooning softly as my fingertips rimmed her butthole.

Turning my head I suddenly pressed my open mouth to Cindy's pussy and my tongue delved down through her coarse pubes until I found the top of her slit. I parted her pussy lips with my tongue-tip and slid down a short way before finding a firm little bump cradled in folds of flesh. I licked her lightly and she jerked, her fingers digging into my hair.

"Ohmygod!" she cried, jerking each time my tongue slid slowly across her clit. I found the opening of her vagina and gradually pushed my thumb inside, finding her warm and slippery. She was gasping and panting continuously now, her hands pressing my head into her crotch and her legs quivering slightly.

"Mmm, mmm, mmmmm!" she hummed between gasps.

I centered the tip of a middle finger in Cindy's asshole and waited a couple of seconds to give her fair warning. Then I slid it quickly into her ass up to the second knuckle. In fact, my second knuckle stopped right in the tight ring of muscle at her entrance. The muscle trying involuntarily to close on my invading digit.

She came.

Oh boy did she come! She gave a short, high-pitched yelp when she felt my finger thrust into her ... followed by a series of low grunts and hip thrusts that nearly knocked me to the bottom of the tub. I expected her reaction, but it was still hard keeping my tongue on her clit, my thumb buried in her pussy and my finger in her ass.

So I threw gasoline on the fire by starting to thrust my finger in and out of her asshole in short, quick strokes. But I had time for only two strokes before Cindy gave a short scream and her legs collapsed. Her beautiful butt hit the tub at the same time that she pulled the shower curtain down with a loud ripping sound.

I couldn't keep my tongue in her pussy in the new configuration, but my thumb stayed inside her and my middle finger was driven even deeper up her ass. So I continued to finger-fuck her ass with short, quick strokes while her cries filled the room.

"AAAH! AAAAH! OHMYGOD! AAAH! AAAH! AAH! AAAAH!"

Cindy's arms were behind her, braced so she could thrust her hips repeatedly against my invading fingers. Her mouth was open wide to gasp for air and her eyes stared intently, fixed on my hands where they disappeared into her body.

"AAAAAAAAUGGHHH!" she groaned hoarsely. "FUCK ME, FUCK ME, FUCKMYASSSSSS! OH YES, YEESSSSS!"

Finally her climax ended and she laid back in the tub, spasming occasionally, with her eyes closed. Her hands reached forward to hold my hands motionless. She could tolerate no more stimulation of her tender asshole and dripping pussy. I slowly slid my fingers out of her and helped her out of the tub onto shaky legs.

Drying her with a big towel, I led Cindy out of the bathroom and laid her on the bed. I covered her with a blanket, wrapped a towel around her wet hair and lay down beside her. It was several minutes before she gathered enough strength to speak.

"My god that was intense," she whispered. "I had no idea just being fingered by someone would send me to the moon."

She opened her pretty eyes and looked into my face.

"I still ... I want you in my ass. I thought I was ready ... now I KNOW I'm ready. And I know it's going to be wonderful."

Her eyes drifted closed and her breathing became deep and steady.

"But ... just let me rest ... I have to recover ... just a little."

So I let her rest.