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First Time Being Watched

Posted by: Author: Age: 48 Posted on: 2 comments
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This story is about the first time I openly masturbated in front of a woman and admitted to her that I was doing so because because it turned me on to do it.


This is my first submission, and while I am becoming more comfortable admitting how I feel about masturbation, and my natural exhibitionism that revolves around it, it is still a big step for me to write this on a public forum, even though I am “anonymous” here. This story is about the first time I openly masturbated in front of a woman and admitted to her that I was doing so because because it turned me on to do it. Something that was entirely different than the few times I had masturbated in front of my aunt, which is another story entirely.

The first time I masturbated for a woman after openly admitting to her that I would get off on being watched occurred when I was 27 years old. I was in Corpus Christi taking a continuing education course, and staying at a friend’s place. He was out of town and left me the key to his place, but no transportation. I wound up riding his bike all over town to run errands.

I had a Friday off and was getting totally horny, so I rode over to the local papershop to pick-up a couple of porno mags. It was mid-morning and the place was empty except for the woman working the counter. She was overweight and to be honest, not great looking, but did say hello and remarked it was awful hot to be riding around on a bike. I smiled and was a little embarrassed as I went over to the rack of mags. Now at this point I guess I should admit that in addition to having a long time desire to be watched while I masturbate, I have also always had a fetish for “natural” women, as in unshaved pussy and even armpits. I guess that’s probably because the first pictures I ever stroked to were of the unshaved woman in the book “The Joy of Sex” from a long time ago. Because of this fetish, I usually liked to get a good look through the stroke books to find photos of hairier women. Even back then, the trend towards less pussy hair had already started, but I was still occasionally able to find photos of amateurs, and the (very) rare full photo spread of a woman with hairy pits. Now I know that most guys have the opposite reaction, but I wanted to include that fact as my “fetish” has a small place in this story.

After a few minutes of perusing the magazines I looked up and noticed she was watching me. Sometimes in these stores, I had learned, they got mad if you looked and didn’t buy, so I nervously told her not to worry I was going to buy one. She surprised me by saying I should take my time and find what I liked. After a while I found one with an an amateur section that included an older woman with hairy pits. That was enough for me and I nervously brought it to the counter to pay. I knew my erection was sort of visible since I was wearing running shorts, so I tried to hide it by standing close to the counter. “Find something you like?” she asked pleasantly, as if I was just purchasing a drink.

“Um, yes” I replied. Then getting a little braver, “Thanks for you know, being understanding and letting me really look through them.”

“Of course Hon, those magazines are plenny ‘spensive. I get you wanna’ make sure you find one that does the trick for ya’. Most guys come in here, they look at one or two then get ‘barrassed and buy and run!” She laughed. “Seemed like you were more choosy and not as ‘barrassed. Also not too satisfied with the selection, so I’m glad you found yourself something that will help you out when ya’ get on home.”

My heart was pounding! “Um, yeah, not really much of what I you know I like, but I did find one with a pic or two you know. So um, well thanks for being you know, like understanding.”

She smiled sweetly at me and looked around as if to make sure we were alone, “I do understand honey, and maybe if you tell me what you’re looking for I can point you in the right direction, you aren’t the only one likes to look at pictures in a book.”

Now I was totally shocked, excited and embarrassed. I blushed and she laughed. “Now don’t get all ‘barrassed on me. Nobody here but you and me to hear ‘bout this.” So I nervously told her about liking hairy women. She thought for a moment and suggested I should go to a book store she knew that sold old European magazines. She gave directions, and I went off on my bike with a very big hard on and a smile on my face.

Her suggestion did me right and I found what I was looking for and excitedly headed home planning to enjoy my hot new photos of women I liked looking at while having a nice long stroke session. The papershop wasn’t far off the route home, and on a whim, I headed back to thank the woman for her tip. To be honest, I also wanted another thrill talking about masturbation with her. I made up my mind I wouldn’t hide my erection from sticking up a bit if we were alone again. The thought of her really being able to see I was going to be masturbating to the magazines was terribly exciting to me.

It was a hot day and uphill most of the way back so I was pretty winded and sweaty when I got to the shop. I had my shirt off and stood sweating outside trying to get my breath back. A car left the lot and the woman came out and smiled at me. “You’re back” she said “You should come in and cool off. I told you it was too hot for ridin’ that bike.” Don’t worry about the shirt.” I could see she was eying me, which made me feel both very good and even hornier. I was not a six pack abs kind of guy, but at the time I was fit, and knew I wasn’t bad looking. I walked in and my cock was already semi hard. I bought a drink, and as I was drinking it I said “I um, I want to thank you for being so understanding and helping me out.”

She smiled her sweet smile, “Not a problem hon? I’m Candy by the way.”

“Billy” We shook hands.

“So you had good luck finding some photos y’all liked?”

That did it.. My cock was back at full rise, and I saw her eyes widen as it became obvious through my shorts. This time I made no attempt to hide it. “Yeah, I found some I really like, that I think I will really, um, you know enjoy looking at.”

“I’ll bet” she said still stealing glances at my crotch.

I got my guts up and looked at her and asked if she would like a photo or two of me as my way of thanking her. She said of course. I then added “Candy, you understand, I was um, I mean you know, a photo or two of me like um, using the magazines I bought.”

Her eyes suddenly got huge and she licked her lips. She reached her hand out and grabbed my arm squeezing it painfully tightly “Billy”, that is surely something I would like to see.” Just then a customer walked in and she quickly went behind the counter while looking at me and said “Sir, I told you ya’ got to put a shirt on!” She winked as the customer, an older woman got a look at me and I saw her eyes get wider as she noticed my obvious erection. I tried to act nonchalant as I put the shirt on and went back down the aisle and picked out a roll of film. Her hand was shaking just a little as she rang it up. So was mine!

As I left, I noticed that on my receipt she had written “See you at about 4:00”, so I knew when I had to be back. My friend had what was a top of the line camera from back then. You have to understand that this was a long time before digital photography, so Polaroid cameras were about the only way to take dirty photos back then. I had already checked out the camera out and realized it had a self timer. The thought of masturbating in front of that camera and showing the photos to Candy had me so horny I was afraid I’d come in my pants before I even got started.

When I got home I quickly stowed the bike in the hallway, grabbed the camera and set myself up in the living room. I stripped and opened my purchases. I masturbated briefly while looking at the pictures I most liked, then began to take the photos. Each one made me hornier and braver in front of the camera until finally I got the nerve up to do something I did occasionally but wasn’t sure I really wanted her to see, nevertheless I arranged myself, practiced a couple of times, and then started the camera’s timer and hurriedly got into position for the photo. After the flash I hurriedly got up and watched it as it came in. What I saw of myself really turned me on, more than I expected it could or would,

I knew I had to stop. I carefully put the photos into an order I liked, and placed them in an envelope I labeled “Candy”. At the last minute I put that last “Special” photo of myself on top of the envelope, not sure if I had the guts to show her. I took a cold shower to calm down, and tried to take a nap while I waited for 4:00 to come so I could deliver my package.

Finally, it was almost 4:00. I grabbed the envelope and the last photo, which I put in my pocket, and rolled down the hill to the store. There were quite a few people in the store and when I stepped in I saw Candy and another woman behind the counter. After a little bit I was able to get Candy’s attention and nervously handed her the envelope and said “Here’s the information I promised you.”

She grinned and surprised me by answering that I should follow her back to the office to help explain it to her. I was really excited that I would get to see her looking at he photos of me actually masturbating. I followed her into a cramped office off of the store room in back. There was a small desk and a chair on one end of the office. She closed the door, then stood next to me and nervously opened the envelope and looked at the first picture. It was of me standing nude in front of the camera holding a sign that said “Thanks Candy”. She looked at me and put her arm around me. “You’re welcome” she murmured. The next photo I was masturbating and she looked at it then at me and back at it before saying “Wow. You really are…doing it. Wow I have never…wow.”

“So um, you like them?” I asked dumbly, in reality just wanting to hear from her lips that she did.

“Like them, My lord boy, you can thank me like this any time you want. Boy you was really enjoyin’ yesself too weren’t you. Your cock is dang hard there son.”

Finally she got to the last one and looked up at me. “These are so hot. Thank you Billy. I mean that.”

I took a deep breath and got up the guts to show her the last one. I said “Candy, I’m sort of embarrassed to show this to you ‘cause it’s a little different than the rest, but I wanted you to see it ‘cause I really, um I liked so much how open you were with me about all this and I wanted…well anyway, here it is.”

I handed it to her and tensed, hoping she would like it. I am going to be honest about what it was here. The photo was of me on my back, my legs spread as I curled myself over so that I could put my hard cock into my own mouth. I was rewarded with a gasp and obvious delight. “This one is…wow that’s amazing Billy. I always wondered how guys did that, or if they even could. Wow, I really like these Billy. This is great. Why were you ‘barrassed ‘bout this? I mean I seen you jerking off in all the photos. But this is the best way you do it here.”

“So you aren’t…you don’t think it’s weird?”

She looked at me “What that you like to give yourself a blow job?.”

My face reddened from embarrassment, and I nodded.

“I think it’s hot” She said. “Way hot. Now is there some way I can repay you for these pictures?”

I took a deep breath and dove in head first.”Yeah Candy there is. I have …a fantasy. I‘ve always wanted to do…to do what you saw in those photos, in front of a woman. In person”

“You want a woman to watch you masturbate honey?”

“I do Candy. Very much.”

She reached out and very gently ran a hand over my hard cock through my shorts.“You want me to be that woman?”

“I want you to watch me masturbate Candy. May I?”

She looked at me again, you sure that's all you want?

I nodded, "I'd really like it a lot" I said.

She sort of sighed, and then nodded herself “I’d like that honey. I’d like that very much.”

I stepped back and trembling took of my shirt and then dropped my shorts. I hadn’t worn underwear so aside for my flip flops, I was nude. I haltingly touched myself and then began to stroke. She smiled and watched and encouraged as I quickly built to orgasm and finally came spurting all over myself. She thanked me, and offered tissues to help me clean myself up. I exited the store room and tried to be unobtrusive as I headed out of the store.

I went back in a couple more times after that but she was never there. I fantasized endlessly about that encounter, and still wonder if she has the photos anymore, or ever thinks about the horny young guy who just wanted her to watch him masturbate.



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