From drinks to cumming for each other in one evening

I'm in several groups related to exhibitionism. Before going on a trip recently, I looked for exhibitionist groups near where I was staying. Usually, the posts are all about being watched on cam or bemoaning the lack of voyeurs.

One stood out: She wanted to watch a guy masturbate for her, and seemed very up-front about it. According to her profile, she was around 50, divorced, and her pictures showed a tall woman in great shape, especially for over 30. I'm 55 myself, and know the challenge of staying fit.

So I messaged her, offering to strip & stroke while she watched, saying she could stay completely dressed if she wanted, or even bring a friend if that made her feel safe. I've masturbated for voyeurs dozens of times, mostly men, a few couples -- m/m and m/f -- and honestly don't care who watches or what their orientation is.

But I'd never masturbated for a single woman before. That never surprises me. I can't imagine a single woman saying yes to a rando online guy who wants to get naked in front of her.

But she was open to it, and we met at a bar. I wore my lucky undies, a Cocksox bikini brief, though under my loose shorts you couldn't tell. She was very friendly and open, chatting about the guys she's dated, the good sex and the bad sex, and all of this while sitting at the bar and the late-20s female bartender in earshot half the time! I was kinda blushing, but I figured it's what women chat about with other women.

She's a massage therapist and talked about how some guys want to be "draped," or have their privates covered, and some just want to be naked. I was surprised to hear her tell me how many get aroused while she's massaging them, and really surprised when she said a lot of them want to fuck her. That's crossing the line, but I could see the attraction: she's tall, buxom, long legs, in great shape. Not skinny but very well proportioned.

She was wearing a white tank top, which did nothing to hide how large her breasts were, and a lavender tennis skirt, showing some thigh. No wonder her clients couldn't help getting hard. She said she didn't mind that, which was cool. At one point she touched my leg, and I knew she was going to want to go further.

She asked about my being bi, and how I enjoyed my exhibition shows. Anyway, after we finished our drinks, she said, "So, you want to show off?" I said yes, and had her follow me in her car to my hotel.

She arrived in the lobby carrying a bag, and when we got to my room she said, "I hope you don't mind I'm going to masturbate too." I couldn't believe it! Of course I didn't, so I just took off my shirt and shorts, and there was my cock, still soft, but supported in my Cocksox. She looked at it and said, "Oh!" I smiled. She had seen pictures of me nude before, so she knew I'm no porn star, but the undies caught her attention.

I took them off, starting to get hard, and she lay back on the bed. She pulled up her skirt and pulled off her panties, and I was hard in a minute, which she noticed. "That didn't take long," she said.

"I don't usually have a woman laying back on a bed in front of me!" I replied, checking her out.

The set-up was the typical beds in a room. She had her legs draped over the side between the two, so I stood between the beds in front of her, to have a better view and to have my cock in her line of sight. She pulled a vibrator out of her bag and said, "I usually cum pretty quickly," which of course I had no problem with, and she turned it on.

I stroked, slowly, as the device, with its big soft head, vibrated on her pussy. She started moaning a bit, and her eyes were mostly closed. Careful not to cum too soon myself, I stroked very softly. With one foot on the bed, my cock was completely open for her view, but at the moment she was lost in the pleasure building between her legs, just a few feet from me.

She really was statuesque ... and those thighs looked so good that I wanted to taste them, but we had agreed to masturbation and an exhibitionist is true to his word. Soon she was getting quite noisy, which turned me on more, and then she convulsed as she came to a climax.

She had to catch her breath, and I told her how amazing it was to watch her cum. Next it was my turn. She asked if I liked toys and when I said yes, she got on her knees in front of me and stroked my cock with her vibrator. It was heaven. She went up and down with it, then applied it to my balls, then up to my head, which made me say WOW!

"Oh, I'm sorry, I know how sensitive that is!" she said. No, I want more, I told her, and she didn't hesitate.

More of the vibration on my cock, with my looking down at her kneeling, perving on her cleavage in that tank top, and I knew I wouldn't last, so I said, "I'm pretty close, where would you like to see me cum?" She wasn't sure what I meant. "I could cum on my belly, cum on the floor, or wherever you want to see it ..." Now she got the picture.

"Well, where do _you_ want to cum?" That's what 99% of voyeurs say, so I was ready for it.

I decided I'd just be honest. "Well, to tell you the truth, my favorite way is to cum on breasts."

She seemed to think for a second of two. "Well, why not?" she said, and pulled off her tank top and her bra, revealing a magnificent rack. She's well-endowed enough that she put one forearm underneath her girls to help hold them up, and I was ready to release.

I stroked another few seconds until I started exploding, releasing my load first on her right breast, then giving her more glistening goo on her left breast, pressed my cock into her firm but soft boobs. With her head bowed, she watched my cock cum the entire time. It was so hot, feeling her breasts with only my cock, spreading my cum around her big girls.

After I caught my breath, she stood up, smiled as she showed me my load on her chest, and we both relaxed again. I handed her a towel, and we chatted a bit. I was still naked, and she started putting her top on. I asked if she often watched guys masturbate, and she said yes, because her clients like to end that up. I told her how cool it was that she's seen so many guys show off for her, and that I was thrilled she had let me j/o for her.

And I really meant it -- she had the perfect personality for a show-off like me, and she was totally comfortable showing off herself. Plus, her vibrator was such fun. She said she enjoyed it too and that if I was ever in the area again, I should get in touch. I hope it happens!