Completely true unfabricated story
Cindy and I were business colleagues for over 20 years. In fact, we were friends as well. This past spring we were assigned to a transition event within our company that required us to be in Florida for a two week project meeting. I'm 46 yrs old, happily married with two children. Cindy is 54, married and has one older child.
We have a great relationship, get along well, and know a lot about each others lives. We also work hard, but have only once before this travelled together. The first week of our work went well, and just about every evening we'd go out to dinner together. Over the course of these evenings we began to run out of non-work related things to talk about, and our conversation eventually strayed to our spouses. Unbeknown to me Cindy was in a very similar situation as me: A good marriage, happy, content, except when it came to intimacy. I learned that she and her husband slept seperately and hadn't had intercourse in over a year. It was like she was describing my situation to a 'T'.
This led to of course us kidding each other about the joy of being in a hotel room alone for two weeks, and all the 'perks' that came with it. I saw her blushing slightly and we both knew what we were talking about. I blurted out at one point that if I didn't have to get up and work in the morning I'd be in my hotel room naked 24/7. She laughed and her eyes lit up and said 'Me TOO!'. We were both laughing and having fun, and it was her, not me, that began to make innuendos about the alone time in the room and freedom to masturbate. Finally the innuendos became more and more direct until she said, 'So where do you do it mostly? On the bed or in the shower?' I was shocked but played along, acting nonplussed, and said the bed, and I had to keep asking the maid for extra boxes of tissues. She laughed and said she liked the bed too, but preferred the shower because of the pulsating showerhead.
Now at this point we were sitting in the hotel restaraunt and I had a complete erection. Cindy's cheeks were flushed, and as I glanced down I thought I noticed that her nipples appeared to be hard and poking at her bra and white blouse. Now Cindy isn't a supermodel by any means, she's a bit husky, fairly large breasted and a full round ass. She has close cropped brown hair (colored as she told me out of a bottle) and nice green eyes framed by professional glasses. She honestly does not have a terribly attractive face but does have a cute smile. We fell silent for a minute, looking each other in the eye, no words spoken but obviously we were thinking the same thing...
She broke the silence with a simple 'Should we?' I responded with a brilliant 'I dunno'? and we both laughed. I'll spare you the details, but we debated (in whispered tones) back and forth whether we should or shouldn't be together that night. She was adamant, and I agreed 100%, that we could not have intercourse but simply use our hands on each other. She was shy and self-concious about her body, but I eased her concerns with my words, assuring her as well mine wasn't much better (I'm also husky). We finally decided what the hell, and then debated whose room we should go to the whole way up. I took charge and said mine. She went back to her room to call home and say goodnight, and I thought she'd chicken out, but five minutes later she knocked at the door and I let her in.
I took her by the hand and we sat on the edge of the bed. She looked great in her white long sleeve blouse and long, ankle length flowing purple flowery dress. I asked if I could give her a quick kiss, and before I knew it she was leaning over, her hand on my chest, and she was pressing her lips against mine. Her hand bolted down between my legs and began to stroke my cock through my slacks. I followed suit and lifted the hem of her dress halfway up her thighs and began rubbing the smooth bare skin of her thighs.
We broke and I stood in front of her, unsure of what to do next. She immediately began unbuttoning my shirt and I removed it, and her hands roamed over my hairy chest and she smiled. She unbuckled my belt, unsnapped my pants and pulled down my zipper, and yanked my pants and underwear down in one swift motion. My hard cock sprung free and as I kicked my clothes away Cindy took hold of my cock and began gently stroking it with one hand, and cupping my balls with the other, whispering a very soft 'nice' as she smiled at me.
As she masturbated me I reached down and began to unbutton her blouse. She shucked her blouse off and stood up, and we hugged, my cock pressed against the soft bulge of her stomach. I reached around and found the zipper of her dress and lowered it, and the dress billowed down and created a small silky pile at her feet. I stepped back to soak her in, nice full breasts that sagged, but her full dark areolas were visible through her white nylon bra. She wore full cut beige brief panties, also nylon, and as we hugged again my cock jumped as it slid against them. I reached behind and unsnapped her bra, and with a shrug of her shoulders and a quick tug by me it was off and on the floor. I hooked my thumbs into the waistband of her panties and gently yanked them down. I was amazed but not surprised, and completely turned on by the fact that Cindy had a full, luxurious bush of black, wirey pubic hair that spread out to form a beautiful triangle below the paunch of her belly.
I had her sit on the bed, and then pushed her shoulders so she was laying back, flat on her back, and she giggled nervously. I positioned myself next to her: I was on her left and I was propped up on my right elbow. As I leaned towards Cindy my cock snuggled and slid tight against her hip. With my left hand I began to trace her areolas which were half-dollar sized, maroon in color, and capped with rubberry extended nipples. I tweaked the nipples and gently squeezed her breasts, which elicited low moans. I looked down and saw that her right hand was between her legs and she had begun masturbating herself!
It is the ultimate fantasy and turn on for me to see a woman masturbate, so I continued to watch as I paid attention to her breasts. I encouraged her to play with herself, telling her how hot it was. Her knees bent up and her legs spread and as I looked down could see her pussy lips engorged and open, a slight dampness and pungent, erotic woman-smell emanating from them. Her hips began to buck, and as she moved closer to orgasm I removed her hand and replaced it with my own. I fingered her, slowly at first but quickly found my rythym, and as she moaned and bucked, her hand went to my cock and began to stroke it while also letting me continue to grind against her. In no time she was there, moaning deep and then letting out a shrill 'aaaahhhhhhhhhhhhhhhhhhhh' as her legs stiffened and then clamped around my hand and wrist as she trembled through a long orgasm.
As she came back to earth I gently stroked her smooth soft skin (AMAZING skin for a 54 yr old woman), and all the while she slowly continued to stroke my penis. I could tell she was spent, but she looked at me with glassy, lust-filled eyes and then stared at my cock. I knelt over her and began to masturbate as she watched, and her hand snaked around my waist and she began squeezing my ass, and encouraging me with some suprisingly dirty talk ('mmm stroke that hard cock, let me see you shoot all over me'). I groaned and wailed 'I'm cummming' as I stared down at her alabaster skin that was so nicely contrasted by her black pubic hair and dark nipples and began to ejaculate thick, long strings, about five in all (about four more than usual...!) that splashed onto her breasts and stomach, and began to slowly stream and dribble down her body, and a rather large 'puddle' formed in the spot below her stomach and the border of her bush. She laughed hard and put a finger in it and swirled it around into her pubic hair, looking at me saying, 'I think we both need a shower...'.
I hope I have time to continue this story soon. Suffice it to say during our remaining time in Florida we had some more fun, but as we were flying home had a very frank, serious talk about the fact that it was a one-time thing and must never be spoken about or happen again. We've been able to maintain our working relationship and friendship, which I know is a very rare and unusual outcome when these kinds of things happen.