For those who commented on the first part of what will probably be a four part story, liked it and urged me to write more, this second part is dedicated to you…
This story began where I had met Dianna during one of the business conferences held by our company at different locations around the country. Dianna was the company’s Human Resources person who was responsible for setting up the conferences and she attended each one to make sure that everything ran smoothly. She was in her 30s, attractive, but all business and no one at any of the conferences was ever able to get to know her on any kind of personal basis. I kept at it, though, but slowly and in a gentlemanly way, and I thought that I might be breaking through the ice just a little.
But then I took a job with another company and figured I’d never see Dianna again. Soon, though, my new company sent me on a business trip to Washington, D.C., where my first company’s headquarters were and where Dianna was based. While there I took a chance and invited Dianna to dinner, and after, without much hope of success, invited her back to my motel room for a glass of after dinner wine.
Not only was Dianna willing to come and share that glass of wine with me, we had an evening of great sex. I had wanted to see her again the next night, but she explained that although she would love to come back for a repeat, she had a business dinner to attend. I walked her to her car, we exchanged phone numbers and she drove away. I was sure I’d see her again, but we’d have to work around our schedules. At the time I couldn’t tell what was in store for us.
While walking back to my hotel I went over in my mind the great time we had in bed. I remembered how my cock looked while I was fucking her from behind, how it glistened with her moisture as I stroked into her and she pushed back to me. I remembered, too, how when she was just about to cum, I rubbed my fingers across her asshole, and how that seemed to send her into a wild orgasm.
“That was an interesting reaction,” I thought to myself. “I’ll just have to check that out further.”
After the next day’s conference sessions were over, I went back to my hotel room, and had just poured myself a drink and settled into a chair when there was a knock on my door. I opened it to find a grinning Dianna there, and as she rushed into me and kicked the door closed I was not only pleasantly surprised that she had come to see me unexpectedly, but to also be able to tell from the pressure of her body against mine that she wasn’t wearing a bra. I had told her the evening before that her breasts were so beautiful that she shouldn’t ever wear a bra, and she replied that although she needed to wear one during business hours, she wouldn’t wear a bra when she was with me.
Dianna’s kiss was wet and sloppy, and if I didn’t know she had that business dinner scheduled, I’d think she was ready for more sex.
“I didn’t think I’d see you tonight,” I told her, “I thought you were going right to your dinner.”
“I had a few minutes,” she replied, “And I just wanted to come by, say hello, and thank you again for such a great time last night.”
“It was my pleasure,” I replied gallantly.
She stood there smiling, waiting for me to continue with something. I finally decided to play it safe since she was surely leaving for her dinner in a few moments, so I offered her a glass of wine from the bottle we had opened the evening before, but had barely touched. She took the wine but remained standing even after I had offered her a chair. I sat in a chair facing her, sipping on my drink.
“Did you notice?” she finally said.
“Yes,” I replied before she could continue with her sentence. “I said you shouldn’t wear a bra, and you’re not.”
“I didn’t think you noticed,” she said. She looked down at her hand which was smoothing her blouse down over her breast. I knew she had to leave shortly, but my cock started to have other ideas.
She took a sip of her wine, and unbuttoned a button on her blouse. She looked directly at me, took another sip of wine, and then undid another button. Another sip, then a third button slid open. She walked toward me, put her wine down on the table next to my chair, and opened the last button while standing directly in front of me.
“Ok,” I thought, “She doesn’t want to leave anytime soon obviously.” I stood up, my cock starting to strain again my pants, and I slipped a hand inside her blouse. Dianna didn’t have gigantic tits, but what she did have wouldn’t all fit in my hand. I caressed her breast softly, and could feel the smoothness of her skin under my fingers and the hardness of her nipple against my palm. Her eyes were closed, she was breathing slowly, and she didn’t object as I pulled her blouse out of her skirt, slid it off her arms, and tossed it away on the floor. I pulled her to me, kissed her softly, and continued to caress her breast. I had taken her nipple between my fingers, squeezing it to make it even harder, when she suddenly stepped away from me.
She was breathing harder and her aroused nipples were standing straight out toward me. She looked down at the outline of my hard cock in my pants, and then looked up straight at me.
She hesitated a moment or two like that, and then said “What the hell,” as she reached up under her skirt, pulled her panties down and off, then tossed them in the direction of her blouse.
I pulled her toward me again, lowered my mouth onto her hard nipple, and slipped my hand up under her skirt. I caressed along the length of her pussy lips, and could tell that she was wet already. I slipped a finger inside her lips, then rubbing two fingers along between her hole and her clit, I sucked her nipple deep into my mouth.
“Oh,” she said, “Oh, God, that’s good,” as she pushed her pussy against my fingers.
She broke away from me then, went and sat on the edge of the bed, and then slid down until she was sitting on the floor with her legs spread and her back against the bed. I walked over to her, my hard cock pushing against my pants. She reached up and stroked along the outline of my cock, making me even harder. I undid my belt, and pulled my pants off, then my shorts. My cock was pointing straight out toward her face. I leaned over onto the bed so my cock was poised directly at her mouth. She looked at it for a few seconds as if hypnotized, then started stroking it with her hand. The precum was starting to leak out and she licked it off with her tongue before taking the head into her mouth. She worked my cock with her hand in her mouth in unison, and I could feel the urge to cum starting to build within me. When her hand dropped away and she started to suck me deeper, I moved with her rhythm, soon just fucking into her face. I felt the cum rolling along the length of my cock, and I just told her, “Here it is, Dianna, here it comes!”
She took several spurts of my cum deep into her mouth before she moved her mouth away, stroking my cock with her hand and letting the rest of the cum spurt onto her face and into her hair. When the last spurts had gone she took my softening cock back into her mouth and gently sucked the rest out of me.
“Whew,” I said, feeling weak in my knees, and as I dropped down Dianna moved up, sat just on the edge of the bed with her skirt up around her waist, then lay down so that all that I could see was a wet pussy in front of me. She was shaved except for a little patch on top, and her pussy lips pushed out, waiting for my touch.
I ran my thumb along the length of her lips and I could feel her quiver. I easily slipped a finger inside her, then two fingers as I leaned over and licked along her lips and up to her clit. My tongue took over then, licking up and down along her lips then up to her clit.
“Ohhhh,” she started to moan, “Oh, that’s good.”
She was so wet that I easily slipped a third finger into her, then a fourth. I worked my hand around so my thumb went in also, then her hand came down to mine and pushed it in further as her pussy pushed against me. She stroked hard against my hand until my hand was in her all the way to my last knuckles.
“Aaaah,” she said, “Ah, ah, ah,” in time with her strokes against my hand. I was surprised when she came, shouting “ Fuck, fuck, oh, fuck!” Her cunt spasmed around my hand, and she was so wet that I could hear a slopping sound as she forced her pussy further down along my hand.
Her breathing finally slowed and I moved up along the bed until my cock, now getting hard again, was up against her pussy. She reached down and put it into her, and to my surprise after being spread apart by my hand, I could still feel her cunt tighten around me. I fucked her slowly that way for a bit, then just lay on top of her, my cock still deep in her pussy.
“MyGod,” she said, “I have never cum that way before, with your hand, I mean, and I came so hard.”
“My pleasure,” I said. “Watching you cum like that got me hard all over again.”
“Yes, I can feel what you mean,” she said as she started to stroke up against my cock.
I let her go on for a few minutes, and then moved her around to the middle of the bed on her back. I pushed her legs up until they were almost up around her ears, and moved her hands to hold her legs like that. I put the tip of my cock at the entrance to her pussy, and then pushed deep into her at one hard stroke.
“Uhhh,” she gasped, “Uhhh, uhhh, uhhh,” all in time with my deep strokes into her. With her pussy up at that angle I was able to go deeper into her, slamming into her with stroke after stroke. She was breathing harder and moaning and I could tell that she was close to cumming.
I moved her over so her ass was up in the air, and plunged deep into her cunt from behind. I fucked her with deep strokes, and as her moans got louder, I wet my thumb with her pussy juices and forced it against the little bud of her asshole until it just popped inside. As my thumb entered her asshole, Dianna gave a muffled scream and her whole body shook as her pussy muscles went wild around my cock.
“Aaghh,” she screamed into the pillow as she slammed back against my cock and my thumb, then she slowly sagged down onto the bed.
I got up from the bed and went into the bathroom where I had earlier noticed a small plastic container of some super slick lotion that the hotel had put there along with soap and shampoo. Back on the bed, I moved Dianna back up onto her knees. I put a generous amount of the lotion on my cock, and then rubbed some on my fingers and around her asshole. I slid a finger into her ass and stroked her. As she loosened up I slid another slick finger into her ass, and pushed them into her all the way up to my knuckles. She started to push back against my fingers and we soon had a rhythm going.
“Oh, God,” she said in a quivering voice as I removed my fingers from her and touched the head of my cock to her asshole. She pushed back against me a little, urging me on. I pushed the head of my dick hard against her asshole, and it seemed as though she pulled me right in. I could feel her muscle tight around my cock, just under the head, and I held it there until Dianna pushed back against me again, and I slid in further. I stroked into her slowly, deeper each time, and relished the feel of that muscle tight along the length of my dick as I stroked in and out until I was completely buried in her ass.
I held there for a moment, and then moved almost all the way out until just the tip of my dick was in her. I held that position for just a moment or two, and then pushed hard into her ass all in one stroke.
“Unnngh,” said Dianna as her breath came out of her in a gasp. I moved back out again, then started to stroke back in, but Dianna pushed back against me, pushing my cock deep into her. We both moved apart, and then back again until we were fucking each other hard. I looked down on a few of the out strokes and was amazed that my cock was burying itself into this woman’s ass, this woman who had been so unapproachable just a few weeks ago.
Dianna pushed against me harder and harder, and felt her beginning to tremble as she started to cum again. She sagged down onto the bed as her cum rippled through her, but I just lay down on her soft ass cheeks, and continued to stroke into her.
After a few moments of this mutual ass fucking I could feel the cum building up along the length of my cock again. Dianna must have felt it too, because I could hear almost a chant coming from her in time to my strokes.
“Don’t come in me, don’t come in me, don’t come in me,” she said at each of my strokes, and I realized that she was afraid she would be leaking my cum from her ass all night when she finally showed up at the business dinner she was originally supposed to go to.
So although I’d like nothing more than to fill this attractive woman’s ass with my cum, I reluctantly pulled out of her and rolled to the side. Dianna immediately moved around and took my cock in her mouth, and with her mouth and her hand she almost immediately had me pumping my cum down her throat. After a moment or two, when I finally stopped spurting into her mouth, Dianna took a few more long strokes along my softening cock, and then crawled up next to me.
“I never thought all this would be happening with you,” she said, “and I won’t pretend that I’ve never been fucked in the ass before.”
“I think I could tell that,” I replied, “but you certainly know how to enjoy it.”
“Well, it’s been a long time,” she said, “a very long time, maybe ten years ago or more.”
“Why did you wait so long?” I asked.
“Oh, the few guys that I had the time to date never seemed to be interested, but I was hoping that maybe you would be. When you touched my ass last night, I was thinking maybe, but then you didn’t go any further and I was a little disappointed.”
“Well, I’ll try not to disappoint you that way in the future,” I said. “Speaking of the future,” I continued, “will you be coming by tomorrow evening?”
“I don’t know, but for the more immediate future, I’ve got to get dressed and see if I can still make part of the dinner I was supposed to go to before you got me off track,” she laughed as she got up and headed for the bathroom.
In a few minutes she was back out, but I was still on the bed.
“Don’t get up for me, I can let myself out,” she chided me with a grin, then leaned over and sucked my soft cock in her mouth for a few strokes, then finished dressing.
She headed for the door, then called over her shoulder on her way out, “I’ll call you, ok?”
“Ok,” I answered as I noticed a small drop of my earlier cum that she still had in her hair. The other women at the dinner would probably know what that drop was, but I wondered what the men would think.
I smiled to myself, very sure that I’d see Dianna soon again, but I couldn’t imagine what that future would hold.