Carl and June's Nude Challenge! by inafantasy,inafantasy

She did not want to tell me too many details, I found out later she did not have all of them anyway. Well, the statement about not having details freaked me out. I had no choice, she was a real trouper with the one I set up for her, allowing two guys to fuck her, but she can be a nympho anyway, that’s why I hang with her, she likes sex as much as a guy.

It was set up for us to be there at 9 am, nothing about this deal was normal, I will call it strange and scary that something she came up with would be that early in broad daylight.

I dressed casually not knowing what to expect, June told me nothing other than to be clean shaved, and I knew she meant all of me, another thing to scare me. That meant someone was going to be close to me. We headed to what I found out was a rather large retirement community, one of the larger ones in Florida, and almost an hour trip by car. I tried to get more out of her but was not going to get even a clue. Of course, all I could think about is the thought of exposing myself to old ladies, or worse yet, a mixed crowd of retirees.

We got there, and the place is so big we had to use GPS navigation to find what was the Rec center, a large building with several facilities and entrances. It had a Bowling Alley, Ballroom, etc, but we were going to a smaller entrance marked activities. A large parking area for golf carts and a separate one for cars. I figured at this point I was at least expected to interact with people much older than myself and June, and while nude of course. I hoped at the very least that they were all female.

A lady met us at the door, she seemed very nice, just past MILF in looks, not a granny by my standards. I guess maybe she had just graduated to mature status. She took us to an office, to meet the woman in charge, it had a door in the hallway, and another one in her office to a room where I could hear a bunch of women talking, I was pretty scared. June was smiling the whole time, almost laughing, I was really in trouble.

Sharon, the woman in charge introduced herself, then took June to the other room telling her she could take a seat. My heart was racing, June was abandoning me with this grand, maybe great grandmother, I was feeling a lot of things. I even felt a little rage thinking that if this was a strip show for a bunch of grannies, I was going to be pissed. I wished I could have escaped but I was driven there.

Sharon the woman in charge then dropped the first bomb, she pointed to a locker and told me to go ahead and strip, and put all my clothes and valuables in there, and she would lock it up for me, no worries. Well, I still had plenty of worries, fear of the unknown. Then she took a seat at her desk and I just looked at her, as she watched me, was she just going to watch me undress?

She looked a lot like my Great Aunt Margaret! I certainly would not have wanted to strip naked in front of her. It was a stand-off, but I could tell she was not going to budge, and I had nowhere to go.

I gave in, and just started undressing, it reminded me of the first time I had to undress in front of an older nurse at the hospital, really weird and I was nervous then. I slowly took off my shirt, when I was bare-chested I was starting to get even more of her attention. I do run and keep fit, I guess to her I would look a lot better than some of the old guys I saw in their golf carts on the way in. I got down to boxers and we reached another standoff, I asked if she wanted them off now too?

Her answer was, “You don’t know exactly what you are here for, do you? I noticed your friend was having a hard time trying to keep a straight face when she brought you in here. I hope you are not going to back down, you may not get off the property alive if you disappoint the ladies sitting out there. They take this class seriously and are waiting to get started.

I asked her if I was going to have to do any kind of performance, and told her that I can’t even dance. She laughed and explained then I was just expected to be a nude model and was just going to have to stand in some poses, each for at least 10 minutes between changing to another. She added that I would get some breaks that I could come back in the office with her for.

The light bulb went on, I was going to be a male model for a bunch of seniors. She did not say, but painting, or maybe just sketching me. It did not matter, regardless of what they are doing, I was going to have to stand naked for them in some strange pose as they all stared at every part of me in detail. I figured my cock would get lots of attention like it was getting from her.

I was stuck, I mean June masturbated, not only sucked two stranger’s cocks in front of a crowd, she let them fuck her as well, it was her option though. I only had to stand naked for some grannies, I thought. I dropped the boxers and it was clear that Sharon was staring at my penis. I admit it, I am not what they call a show-er by any means, but I was looking pretty pathetic in that area. I usually am a little excited with a girl and a little stiff, what she was looking at was not my penis excited at all, almost like it was scared and wanted to hide like the rest of me did.

Sharon said, don’t worry, we have had penises with stage fright before, they are kind of cute that way but not what the girls are paying for. Just go ahead and do whatever it takes to get it ready, I can hear them getting restless. I tried fluffing my cock a little with my hand, but I had nothing to focus on. It was clear Sharon had some big breasts, and she started to unbutton her blouse as she said, “You don’t want to go out there like that, they won’t laugh in the true sense, but believe me, you will know they are laughing on the inside and by my experience, it will likely make it harder for you to get it up. Let me see if these double D’s do anything for it.”

At that point, she was in a bra that could hardly contain her breasts, and she stood there for me. It did not help much, I wanted my penis to be in at least an arc. My nerves were just not going to let it. Sharon popped off her bra, and her, what was at the very least double D’s were let free, and a little saggy. I tried to imagine my head between them, or even fucking them, but it was not working either, she was 40 or more years my senior.

She said I was going to have to go out soon, and that she noticed I liked her breasts. She rolled her desk chair in front of me and pulled her double D’s together for me. I knew what that meant, and I tried to get my limp dick in between them, she squeezed them tightly together, but it just kept falling out when I let it go.

Sharon said, “OK, no need to panic, as an older woman I have helped men with that problem before. She put one hand under my balls, and with the other, she lifted what was still looking like a tiny penis to me, just pathetic! She was prepared to do whatever was needed and put it in her mouth. Now she had something going on, I am not a bit impotent, I was just nervous, and my penis being in any woman’s warm mouth was going to help. I was starting to get some confidence.

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