I have wanted to try the motel maid thing but many of the road trip motels the maids are kind of snaggletoothed and I decided that I didn't want to get lucky with any of them on the off chance that they might have been interested. I decided to just keep displaying my cock in adult theaters and ABS. This all could change if I ever come across a maid who is a hottie.

I was 14 and she was 13.

She turned and ran away. I was afraid she would tell on me, but she didn't, so I get a little bolder. One afternoon I told her I was going to my room to "play" and made sure she saw the tent in my pants as I went upstairs. I left the door slightly open, took off my pants and briefs and started pumping my dick, panting and groaning. After about 5 min. she peeked in the door. I kept pumping and said, "Come in, sis." Becky walked timidly into my room with her wide eyes glued to my pumping fist. I looked her in the eye, moaned, "Oh. Becky, I'm cumming for you," and squirted my jizz directly at her. She gasped as my cum shot out in long ropes and one squirt landed on her legs.

That is so fucking hot!

Naturist sunbathers are often seen quietly but openly playing with themselves, shyly, but hoping to be caught by someone friendly . . . .

When I was stationed in Germany with the Army my wife and I lived in private accommodation on the edge of town while waiting for an army house near the base. She and her friend were regularly flashed by a local teen lad as they took a shortcut through the woods into town. I only found out when her friend let slip about the 'wanker in the woods' At first he would just slip down his tracksuit bottoms and let his hard cock spring free the run off. This went on for a few weeks and when he saw the women just stopped and looked he began to masturbate quickly shooting a big load as younger guys tend to do. I asked her friend what my wife and her thought of it. She said they quite enjoyed their twice weekly show and used to talk about what would happen if they decided to wank him off. I never told my wife I knew about the 'wanker in the woods' and anyhow he was caught by the police when someone reported him. I wonder if the women missed him.

Oh I had fun on this one lol

I have never masturbated to intentionally get "caught". That's pretty much like flashing. I do enjoy being watched, but only if the woman watching me wants to be.
Only times I have intentionally allowed myself to be caught was by my wife, girlfriends and female friends who I was alsready having sex with and/or masturbating for/with, so I knew it was okay with them and they would be into it.
I was genuinely caught by a hotel maid once time. It was at an extended stay place that I was living at for a couple of years and the rooms were only cleaned once per week and each room had its assigned day to be cleaned. My day to be cleaned was on Wednesdays and this happened on a Thursday, plus it was a little later in the evening, so I was not expecting anyone to be coming in. I was laying on the bed with my jeans unzipped and my cock in my hand, just slowly stroking when the door flew open and a younger girl, about 18-20, who I had not seen there before, just comes right in, then sees me and backs out and pulls the door back, but not all the way, so there was still a gap of about 10 inches that anyone walking by could see right in. I barely was able to get my cock back in my pants and get them zipped and she just came right back in and apologized saying she was there to spray for regular pest control and she didn't think my room was occupied or she would have knocked first. She sprayed around the kitchen and bathroom, apologized again and left.
I think she was far more embarrassed than I was. I actually was not reaqlly embarrased like I thought I would be in a situation like that. I was more embarrased for her than I was for myself. But after she left, yes, all the scenerios played out in my head while I resumed masturbating. Thinking about her telling me to continue so she could watch, or her masturbating with me, her jacking me off or sucking me or fucking me....I thought about her being really embarrassed after she left but the more she thought about it the more turned on she would get and not being able to wait until she got home to masturbate while she was fantasizing about my cock and seeing me playing with myself and wishing she had stayed and watched and maybe fucked me.
But in reality, she just did her job and left and didn't really think about it except for one of those Hotel housekekeping war stories she would discuss with the other maids and her friends when she discusssed her job.

Not intentionally but I did get caught in a hotel apartment one Sunday morning - what else are Sunday mornings on your own for?
The maid came in, hadn't heard her, she sort of gasped and fled