Virgin Gigolo Ch. 01

"Sounds like the right approach. I think I've got several things around that I can pay you to do. Would you be interested?"

"That would be awesome."

I've never been afraid of work, even if it was dirty work, and it seemed virtually everything that Mary had for me to do was dirty. Yard work was dirty; removing overgrown plants was dirty; just mowing lawns and edging got me dirty. The preparation for painting included a lot of power sanding and preparation that got me dirty. Every time when I was approaching the end, Mary would come out, see me covered in dirt and begin laughing. "What are you, a dirt magnet?" she would laugh, and then always tell me to go take a shower before I headed home. I told her I'd wash and bring her husband's clothes the next time, and she said "That's not necessary, just wear them next time and I'll have yours cleaned and ready for you to go home in." From that time on, I was always swapping his clothes for mine or mine for his. She'd caught me a bit by surprise that first time when I was in the shower and she'd come in and taken my dirty clothes and left a clean towel but my mom would have done the same at home, and except that she was older than my mom, it sort-of seemed normal.

Sort of.

Cleaning out Robby's "man cave" as she called it, I found boxes of -- well -- crap, that he had kept rather than throw away. Most of it hadn't been moved in years, and was covered with dust. Piles of old Car and Driver, Motor Trend, Road and Track, Popular Hot Rodding, National Geographic and Arizona Highways took up a huge amount of space. Later I found copies of something called "Desert Magazine," dated from the mid 1960's through 1985. When I checked them out on-line, I found out 1985 was when they'd gone out of business, so apparently, he'd had a subscription with them. I picked up piles of these magazines and threw them out every time I was there, briefly scanning the cover pages for anything of interest, before tossing them into the trash. The amount I threw out each time basically depended on how much room was in the trashcan, and how distracted I got when I saw an article or magazine of interest. Mary had told me to go through them, and if there was anything that I wanted to take I could do so, but she just wanted them all cleaned out.

Occasionally in the Auto magazines I would find something of interest, but mostly it was just filling a trash can every time I was there. Arizona Highways had phenomenal photography and I almost couldn't bear to throw them out. I oohed and awed at all the pictures in every Arizona Highways magazine, but in the end, they went too.

It had made sense to just start at the front and move back into the room, which is what I did. I don't know how many times that I'd been in there, pulling magazine stacks, glancing through them, and carrying them out. Probably close to a dozen times before I got to the end of the front piles and realized that there were more around the corner of the L shaped room. But, once I did -- everything changed.

What initially caught my eye was that some of the magazines were a different shape. Two, in particular, were side by side and plastic covered. I wasn't sure what they were, but they were different and buried under a dozen other magazines, so I pulled the top ones off them to see what they were.

The first was the 1953 Marilyn Monroe Playboy magazine. I remember seeing Playboy at a friend's house once, an issue much newer than this which his father had, and just remembered that the girls were impossibly beautiful, impossibly sexy and my favorite masturbation fantasy from that time on. This one, however, was totally different. I didn't realize until later that this was the very first Playboy ever issued in the US, and also didn't realize at first that it was a collector's item. I should have realized it as the plastic wrap had an orange sticker with a $1500 price tag on it, but I was more interested at looking at what was inside.

The second magazine turned out to be the very first Penthouse magazine ever issued in the United States. Right from the start it was more explicit than the Playboy, probably mostly because the 1969 date was 16 years later than Playboy's first issue. This one had a gorgeous brunette on the cover wearing a sheer white blouse, with one breast totally visible through the material. This one Robby had also bought somewhere as it had a $1,950 price tag. Both magazines were in pristine physical shape, they appeared to be brand new, and they also appeared to have been there for quite some time.

I no longer had any doubt that both of these were collectors' items because they'd been bought and had price tags. I know Mary had told me I could take anything I wanted, but wasn't sure that she knew these were there. Regardless, there was no way that I was going to not look at these, and did.

Mary had stopped in while I was sorting and tossing magazines just once since I'd started, but had otherwise not bothered me at all. Now, around the corner and out of sight of the door, I did what all teenage boys do when confronted by pornography or explicit photographs. Luckily, Robby's "man cave" had an attached toilet where just a few short minutes later I had a load of cum spurting into the air, most of it going into the toilet. My legs collapsed from the intensity of my orgasm and immediately I felt guilty for having done this at Mary's house.

I wasn't quite sure what to do with these magazines, however. Mary had always been there as I headed out in the afternoons, and if she was today, there was no way I was going to be able to hide them as I left. For the meantime, I slipped them back into their plastic sheaths and stuck them back in the pile I'd found them in, and then thinking maybe I could conceal them, collected a couple of non-descript Auto magazines, and sandwiched my two "keepers" in between. I set the four magazines on the couch, where they were out of the way and hopefully wouldn't attract attention, and went back to work getting rid of the stack where they'd been.

"About done for the day?" Mary asked, stopping at the door. "You've made quite a dent! I never could get Robby to throw these old things out." She stood there in the door talking to me, so I answered and turned toward her. She wasn't making any effort to interfere, but perhaps my putting the four magazines on the couch hadn't been such a good idea, as her eyes must have noticed them. "Oh! What are these? Did you find some you want to keep?" she said, striding the three steps to the couch and before I could respond, reaching down and picking up the magazines. That the middle two were covered in plastic, and hidden between two non-covered magazines, now seemed obviously a ruse to me. Whether it was to her or not, she flipped the first Car and Driver up, exposing the Penthouse magazine and the gorgeous brunette with her nearly naked boobs.

"Oh my," she glanced up at me. She smirked wryly, turned her head slightly sideways and said, "I guess you would be interested in these, wouldn't you?" She slipped the Car and Driver off the top and onto the bottom of the pile, gazing at the half nude woman now totally exposed on the cover. "She quite sexy, isn't she?" and then she flipped the Penthouse up, seeing the Marilyn Monroe Playboy beneath. "I completely forgot Robby bought these. I did tell you that you could take any that you found interesting, didn't I?" She giggled. "Here you go," she said, purposely holding them out to me, "just be careful about sticking the pages together as these are somewhat valuable, you know." She giggled again as I turned red.

I hadn't yet reached out for the magazines, and apparently the orange stickers caught her eye. "Oh, $1,500... and $1,950? I remember he told me he was buying these, probably 20 years ago now, but I'd forgotten they were worth so much. Probably worth more than that now." She lifted the Playboy, seeing the Hot Rod magazine beneath and figured out what I'd done. "Did you really want the car magazines?" she asked, looking up at me. I guess she could read it on my face, "Yeah, I thought not. Here, throw these away too," she said, handing me the four magazines again, this time as two piles of two.

I hadn't said a thing, totally mortified from the time she stepped away from the doorway. As if I wasn't uncomfortable enough, she continued to push my mortification button as if it was nothing. "Do you boys even have sex magazines these days? Probably not, you just look at sex on-line, don't you?"

That I was embarrassed had to be plainly visible to her. She stopped, apparently realizing my mortification... and paused. "It's OK, Danny. People like sex, I like sex, and I've been having it since I was in high school -- so you're no different. No need to be embarrassed. OK?"

Of course, her reassurances had no positive effect on me. Turning, she set the magazines back onto the couch. "Let's just leave these here for now, you can get them on your way out. Ok, come on, let's get your shower so you can go home." She turned and stepped back out of the room -- and I realized I'd been found out, embarrassed beyond belief, and then she'd stepped out again -- and I hadn't said a word. Sheepishly I followed her through the laundry room door where she said, "Get in your shower. I'll be back in a minute with a clean towel."

I had regularly been getting quite dirty working outside, but only mildly dirty and dusty cleaning out Robby's man cave, but from that first time when I'd gotten absolutely filthy, she'd insisted that I take a shower before leaving. My mom, although she seldom did, certainly didn't think anything of coming into the bath and collecting dirty clothes when she was washing at home, so having Mary coming in, collecting my dirty clothes, delivering new clean clothes, and a fresh towel while I was naked in the shower hadn't seemed all that unusual in the past.

Dropping my clothes into a pile so I would be sure and be in the shower when she got there, I reached over and swung the frosted shower door open, and happened to notice that the fingers of my hand weren't hidden at all when they were touching the glass. I reached my hand around where it was several inches from the glass and confirmed that the frosted glass really didn't hide much. Although I'd sort of realized she could see me through the glass, I now, for the first time, realized just how much of me she could see. In the past I'd always made sure to be facing away from the door, so she'd only seen me from the backside. She'd seen my naked back and naked butt and every time she'd stopped and made some seemingly innocent small talk, sometimes for several minutes before leaving. And just like that it popped into my head that delivering clothes and towels and talking hadn't been just being friendly -- she'd been looking at me.

My cock, which had begun to swell earlier, was now pointing at the ceiling.

I started the shower as always, immediately soaping up and washing my face, the entire time thinking that, if I was at home, I would be gripping and stroking my cock to completion. But doing that at Mary's house? Doing that when she would probably be coming in momentarily? All kinds of sexual thoughts ran through my mind while I was standing there. Remembering finding the magazines, jacking off in the toilet, Mary Jane coming in and seeing the magazines, saying that she'd been having sex since she was younger than I was, and that people like sex, she liked sex...

I'd soaped up my entire body, unable to contain my arousal. The thought that Mary would be in soon, that I had another erection that needed attention drove my thoughts -- my hand coming down to grip and stroke myself just as I would at home.

I heard the door open. "Here you go Danny, clothes and a clean towel," she needlessly said, stepping into the bath. She could have just set them down and left, but I knew she was standing. Was she looking? Somehow, I knew she was. Could she see me?

For the first time I turned in the shower, so it wasn't just my back facing the glazed glass door. I knew my erection was rock hard and pointed to the ceiling when she came in as I was gripping and stroking myself. Releasing my cock, I turned, knowing I was in profile to her, bent forward just a bit, got my hair under the shower head, and raised my hands to rub my hair. Was she looking? Could I tell if she did? I turned my head slightly in her direction, only able to see a generic form of her body, but I was closer to the glass than she was so I was pretty sure she could see me a lot better than I could see her.

Her sudden gasp, more an inhale, followed by quiet as she watched me showering said it all. No sooner did she gasp than I groaned myself, reached down and grabbing my cock again. Knowing that a quite mature woman was checking me out, watching me masturbate, was all it took to send me over the top. My cum spurted well up onto the wall, my legs all but collapsing underneath me.

Just moments after my cum painted the wall in front of me I felt the air pressure change as the door to the bath quietly closed. Looking out through the frosted glass, her body was no longer visible, and I knew that Mary was gone.

Immediately I regretted what I had just done. That 30 seconds of clarity after an orgasm struck me, and I was ashamed. Had I really just masturbated while someone was watching? While Mary was watching? And, if I was honest about it, had I really just masturbated in front of what I knew was an "old" woman, and if so -- why? She had spoken to me about the two magazines I'd found in a totally unbashful manner, had hinted that she knew I was going to masturbate looking at them later, had admitted she'd been having sex for easily twice as long as I'd been alive, and really had indicated she had no problem with any of that. Despite my regrets, my cock seemed to have a mind of its own, continuing in a semi-expanded state.

Dressed again, I stood in front of the closed bathroom door for probably two minutes before I finally got the nerve to open it, go out, and face up to Mary again. "Oh, there you are," she said as I stepped into her living room as if nothing had happened. "You'll be back on Tuesday?"

"Yeah, if that's OK," I answered.

"Oh absolutely," she responded. "I just took a glance in Robby's room and I think next weekend we'll load up all the stuff that can be given away and take it to the Goodwill. You've done a great job of clearing out all those magazines and trash. The trash can was so heavy I could barely move it to the curb on trash day. I see his two bowling balls are still in there, and I don't know if those snow skis are worth anything or not. We haven't been skiing in probably 20 years, so I'm sure they're obsolete but someone may want them. Is that Ok?"

"Yeah, that's fine."

"After that, we'll work on preparing the house for painting. A lot of woodwork that needs sanding and scraping. So, how's your bank account doing?" she asked, somewhat changing the subject, "getting money saved up?"

I thought about it for just a moment, knowing the answer was that I had nowhere near as much saved as I wanted. "Not very good, I guess. I'm thinking I might need to put off starting school for a semester and get a job that gives a constant income. I'm putting virtually everything aside, but it doesn't add up very quickly."

"Yeah, it's pretty difficult, saving money when you're really not making very much. Maybe I can come up with some other things for you to make money on."

"That would be cool," I answered, a smile jumping onto my face at the possibility, "Maybe if you know anyone else who needs help with something, tell them I'm available?"

Mary hadn't said a thing about what had happened. Surely, she had to have seen me with an erection through the frosted glass, and there couldn't have been much doubt about seeing my fist pummeling my cock. Had she seen my cock painting the shower wall with semen? Would she have been able to tell when I came? If nothing else just from the cessation of my arm motion from masturbating or the way my hips shoved forward when I spurted my cum against the wall? I didn't know, but I couldn't get her and what she might be thinking out of my mind, knowing in my heart that she had just chosen to watch me pleasure myself.

For the first time I really evaluated Mary in my head. She had to be old enough to be my mother's mother. If I was 18, and mom was 40 -- what would that make Mary, perhaps late fifties, sixty? Sixty-two? She certainly wasn't anywhere near my age, but she also wasn't a bad looking woman, but probably not much older than that. It wasn't that she looked old, it's just that she didn't any longer look young. Her hair was fairly short, well above her shoulders; her boobs were full, although not huge. I'd never seen her without a bra although I'd seen her wear some shirts that showed a bit of cleavage. Despite her age, I still found her boobs enticing to my eye.

Most days I'd seen her in pants, and she still had a bottom that nicely filled out jeans. At Robin's wedding she'd been wearing a dress, but I couldn't remember what her legs looked like. If she wasn't old enough to be my grandmother, she - almost - could have turned my head. I thought about her seeing me, and wondered what I would have thought if, somehow, I'd seen her naked in the shower? What if I'd seen her naked through the frosted glass? Would I have found her... arousing? My immediate thought was that there was no way I'd have found her as arousing as if it were Robin but, at the same time, the thought of seeing Mary naked had my cock swelling.

Thanks so much to Peter_Cleveland for his editing and suggestions to improve my writing. Especially, to correct, my penchant, for excessive, commas."