Unbelievable, never thought it would happen. But it really did, about 3 months ago.
About three months back I was sent on a business trip to one of our satellite offices in Florida, and was accompanied by the head of our IT group. Cindy and I had known each other through work for about 15 years, and had travelled together before. This was just an overnight excursion, down and back, pretty simple work. We arrived around 5:00 and checked into our rooms (right next to each other at the Hilton Gardens Inn) and arranged to meet in the lobby for dinner at 7:00.
Once we got to the lobby, we both realized we were pretty wiped out from travelling and decided just to eat in the hotel restaurant. Cindy and I had lots to talk about, and inquired about our respective families. I'm married with two kids, and Cindy has met them and my wife several times. Cindy, on the other hand, at 51 years old was divorced about two years ago after only three years of marriage, and hadn't been married previously and has no children. She's a nice gal, very motherly and average looking. Typical 'soccer mom' look. She's about 5'3', a bit chunky at about 160lbs, short brown hair, nice eyes, pleasant face. I've never really gotten a good feel for what her body looks like as her clothes are typically pretty loose fitting (as she's told me, she's self conscious about her weight).
So dinner was great, lots of chatter, good food and drink, and as the evening wore on we surprisingly were really 'connecting'. We decided to stop at the bar for a night cap on the way upstairs, and we were laughing about people at work and just silly stuff in general. We talked about who was dating who, who was boffing who at lunch, etc. when she commented about how SHE wished she was getting some at lunch, and laughed. Cindy proceeded to make a comment about getting tired of 'taking care of herself', said with a wink and a bit of blush. I took advantage of her comment and shared with her that despite being married 14 yrs and loving my wife, our sex life was non-existent and that I also had to take matters into my own hands regularly. She looked at me with a surprised and wide-eyes expression and said 'Really?'
I told her yes, it's no big deal since 'doing it' allows me to really explore my fantasies and get aroused by all different things. 'Me too!' she said, and I knew this was beginning to head some place interesting. I pressed her about what kind of things, and this time she REALLY blushed and I told her it's OK, we're both adults. She proceeded to say she had fantasies involving both voyeurism and exhibitionism, group sex, and even being with other women. Wow, I kidded her, you REALLY do have a lot of kinky fantasies and patted her on the knee.
Then she pressed me, and I explained that I shared some of those same interests, even telling her I had fantasized about masturbating with another guy. She was fascinated, and pressed me for details, and I gave her a few (quietly since there were other people around). A bit later we fell silent for a bit, awkwardly, but she broke it by leaning over and whispering to me something to the effect of 'I have an idea, and I don't want to freak you out, but I'm REALLY turned on right now. Would you consider letting me watch you masturbate, and you could watch me. No touching or intercourse, just, just watching.'
I had a semi-erection before this, and when she said that, I went instantly hard. 'Sounds like fun' I smiled at her, and with that we headed to the elevator and upstairs. 'Your place or mine' I kidded her, and since my room was closest, we went in there. She told me how nervous she was, and asked me repeatedly if I was ok with it. She was VERY worried about what I would think of her body, telling me that she's fat and I wouldn't be turned on watching an 'old broad' like her play with herself. I assured her I found her sexy and that I don't have a perfect body either. I said, 'If it would make you more comfortable, I'll strip first and then you can do what you want whenever your ready.'
With that she sat on the chair next to the bed. She was wearing a long flowing nylon print skirt with a matching button down top, and didn't have on stockings or pantyhose (which I noticed on the way to the room). I stood at the foot of the bed, and removed my shoes/socks, shirt and then pants. I was shaking slightly, but so turned on, which she noticed and joked about when she saw the tent in my boxers. No turning back at that point and I simply slid them down and kicked them aside, and put my hands on my hips and laughed 'Ta-DA!'. Cindy laughed too, nervously, but after at first averting her eyes they became glued to my cock.
I scooted up onto the bed and began to stroke myself, ever so slowly, looking at her. I told her it had been a very, very long time since I masturbated in front of anyone, and it was incredibly arousing for me. She commented that my cock was 'so nice' and she was surprised how hard I was (I'm about 7' cut, pretty average). I thanked her, and continued to stroke. She very cautiously put her hand in her lap, and then began to rub herself through her clothes. I asked her if I could see what was under her skirt, and she smiled and complied, hiking it up until her panties were exposed. No thong or sexy lacy bikini panties for Cindy; they were closer to granny-panties, not quite a girdle but very full white nylon panties. I groaned when I saw them, and she kept her skirt up, and began to rub herself thru her panties.
After a few minutes of this, she stood up without any prompting from me and let her skirt drop to the floor, and then began unbuttoning her blouse. She told me again not to be disappointed by her body, but I pointed to my hard cock and said, 'Does it look like I'm disappointed' and that helped ease her concerns. She shrugged off her blouse, and immediately reached around to unsnap her bra, and it was off in no time. Her breasts weren't huge, but they were full and sagged slightly, and were capped by thick, maroon areolae and nipples that were erect. She squeezed her breasts momentarily, and I told her she was sexy. Without ceremony she rolled her panties down her legs and stood before me. She did indeed have a belly, not a big one but it was there, and didn't bother me at all. Her pussy looked like heaven; covered with a thick and wide mat of brown pubic hair, speckled with a tiny bit of grey, and it was obvious she was already very wet.
I patted the bed next to me, and as she walked around to get on, I eyed her ass. It was white, plump, a bit of cellulite but still very, very nice. She laid next to me and her hand went between her legs, which were still mostly closed, but not for long. As her middle finger found her slit, her legs parted and now she was moaning, quite loud in fact, and I got up on one elbow to look at her as I stroked my cock. Her left leg and my right were touching, and my cock was a mere few inches from her hip.
I encouraged her with some dirty talk, telling her how nice her 'tits' looked and to play with her 'pussy' and mmmmm you're nice and wet. She giggled between moans and told me she liked dirty talk, so I continued, trying not to cum yet myself, and in a matter of no time I could tell SHE was going to cum. Her moans became louder, her hips were bucking fast, she was squeezing her nipples with the fingers of her left hand, and suddenly she arched her back and her legs clamped around her hand and wrist and she was quite literally convulsing in orgasm. It was SUCH a turn on to watch. As she came back to earth, I gently kissed her shoulder, the first time (other than our legs touching) that we had come in contact with each other.
Cindy surprised me when she quickly put her head and hands on my chest. I could easily smell the scent of her pussy and it was AMAZING. She kissed my chest and her hand wandered down towards my cock. She looked at me and simply said 'OK?' and I nodded, and her hand was on my cock and balls. She was wonderful, slowly manipulating them and alternating between slow and fast strokes for the better part of 20 minutes. She changed positions about halfway through, and I began to massage her ass and play with her breasts. Eventually she had her ass in such away that I could finger her pussy from behind, and I found her to be SOAKING wet, and her clitoris was standing out like a little dick. I mean it was really big, and meaty, and I began to flick and diddle it while she stroked me. She came before me, collapsing this time on my abdomen (and cock) as she did, her tits enveloping my cock. I groaned and began to jack myself as she lifted up slightly, and mumbled and grunted that I was going to cum, and I did, and Cindy leaned over me as stream after stream of cum plopped up onto her chest, lower neck, and breasts. It was an amazing, amazing orgasm.
We were both spent, and I got a wash cloth and helped her clean up. I got her key and opened the door between our rooms so she didn't have to get dressed, and before she eased into her room she gave me a kiss on the cheek and thanked me. The next morning at breakfast I was a little freaked out, but Cindy was SO cool and said it's our little secret, no one will know, and she didn't want it to change our relationship at work. Everything has been fine since, but I would LOVE to hook up with her again.