Virgin Gigolo Ch. 02

It was a fairly large, nondescript, brown cardboard box.

Stuck out of sight in the forward corner of the closet, I'd about emptied everything else out. Bowling balls and skis, an old wooden baseball bat, brown with age, all had been moved out to the garage to be loaded into her car. I started to move it, found it was heavier than I anticipated, and pulled it open to see what was in it before taking it out to the garage or the trash.

Inside there were three large loose-leaf binders, and another batch of magazines. This time the magazines were stacked so I could only see the top one, but there was no difficulty seeing what it was. "Penthouse Forum" was blazoned in large red letters across the top. A sultry blond in red, with breasts almost exposed, festooned the cover with multiple sub headlines. Beneath that top magazine were multiple other magazines and paperback books titled variously "Letters," "Penthouse Letters," "The Best of Penthouse Letters," etc.

I'd never seen or heard of these magazines before, but opening and reading the first page of the top issue -- I was immediately enthralled and knew there was no way these were going to the trash. This was pure masturbation fantasy material! The only problem I could see was how to get them out and get them home, and where would I keep them once I got them there?

I really didn't have time, but found myself hooked, unable to stop, and found myself reading several short stories before I put the magazines back into the box, and fished out one of the loose-leaf binders to see what they were. No sooner did I open the cover than I knew why they were there.

The very first picture was a Polaroid, taken with one of those old self-developing cameras that I think have been obsolete, or virtually so, for at least 25 years or more. The full color picture, the first in the book, was Mary. She couldn't have been much older than me at the time, maybe 20 or 22? That would have made it something like 1980. There were only a few of these Polaroids before the camera had obviously been upgraded, and at the same time the pictures upgraded to high-quality photo paper.

The first picture of Mary was in the mountains surrounded by trees, and all she had on was a pair of tight-fitting short shorts. Her legs were bare... and so were her breasts. Naked from the waist up, she was leaning back against a big boulder supporting herself with her arms, obviously showing off her naked breasts and her near naked body. She was looking right at the camera with a proud, smirky, smile on her face. This wasn't a voyeur picture surreptitiously caught -- she was posing, I suppose for her husband.

I could see why he had this one at the front of the book, it was almost something that could be shared. Mary was absolutely drop-dead gorgeous and, I presume, newly married. Never in my wildest thoughts of her had I ever pictured her like this, but now that I had, I couldn't help but wonder what she would look like nearly naked today. And then I turned the page -- and found out.

The rest of the pictures weren't nearly as demure, and some (most?) were downright pornographic. Mary posing in lingerie. Mary posing naked. Mary looking right at the camera and masturbating, her finger obviously rubbing her clit. A close-up of a pussy, female fingers with bright red fingernail polish the only color other than flesh delving through her pubic hair and touching her clit, where in another I could see her fingers had red nail polish confirming it was her. Mary's backside, at least I presumed so, as she was on her hands and knees with a cock sliding in and out of her, her butt naturally spread open with a cute pucker showing.

Neither of the two people in that pic were identifiable, but there were multiple others where either she, or Robby, were identifiable. Mary sucking a cock, presumably Robby's, in multiple pictures: Just the head, deep in her throat, her tongue running up the outside, cum decorating her face or lips or drooling from them. One of his cock head ejaculating, a glob of semen suspended in air about to land on her face with Mary's hand around the shaft, her tongue against the frenulum. Multiple pictures of the top of Robby's head between her legs, or his tongue extending to touch her clit -- almost all of those obviously taken by Mary herself from her viewpoint. I recognized their kitchen table in one instance, the same table they still had, Mary lying back totally naked, Robby's cock visible as it slid into her.

The pictures ranged from what I guessed at nearly 40 years old to the latest that were probably no more than a year or two. Although Mary had aged over time, for the first time I found myself admiring the naked female body of someone who was closer in age to my grandmother than me.

"I didn't intend for you to see those," Mary's voice quietly said from behind me. Immediately I slammed the cover closed, although it bounced back open to the first picture. "I didn't remember Robby had those down here."

Once again, I was mortified. I had a rock-hard erection in my pants, and it was because of this woman who had quietly walked up behind me. I'm sure she hadn't 'snuck' up on me, but I'd been so engrossed I just didn't hear her.

"Not much we can do about it now," she said, seemingly not as mortified by my seeing her having sex as I was about her finding me seeing her sex pictures. "Have you looked at them all?" She asked, indicating with her hands at the other two binders. I shook my head no, afraid to speak.

"Well, nothing we can do about that now," she repeated and held out her hands. "Why don't you give those binders to me?" The one I'd had open was on top, I passed it on to her and then pulled the other two out and stacked them on top. She just stood there for a moment before she nodded once more at the box of magazines. "You'll probably like those, though. They always had pretty good masturbation stories. Robby and I used to read them together." She giggled and turned around and headed for the door. "Come in and see me when you're done."

I wasn't sure how I was going to take all those magazines home, but I knew there was no way I wanted to just throw them away, at least until I'd had a chance to read them. It was only a few blocks to our house so I'd been walking or riding a bicycle to get here, but I knew I could come up with an excuse to borrow my parents' car and get them home that way. I could hide them outside until they left and then sneak them into my room... I had a plan in seconds, and then pushed the box back into the hidden corner it had been in until some later time when I could retrieve it.

As it was, there wasn't much left to dispose of, but now, afraid to face Mary and what she was going to say, I finished moving everything else out and then dallied as much as I could before I had to swallow my pride and moved back into the main part of her house. I found Mary in the kitchen, offending binders on the table, the first binder that I'd opened also open, with the picture of her hot pants wearing, nearly naked, former self front and center.

Hearing me come in, she stepped over to the counter where there was a two-liter bottle of Coca-Cola with two glasses already poured and picked them up. Turning back, she stepped up to the table and handed me one glass. and then pulling out a chair to sit, said, "Have a seat, Danny." I did as she bid.

"Mary, I uh..." I stammered, seeing that she'd opened the binder with the nearly naked picture of her leaning on the rock and not having a clue what to say.

"Nothing for you to say. My husband and I both loved sex, and he loved to document it... document me, and our activities." She flipped a page, another sexy picture coming up. "Hmm. I really was a hottie back then, wasn't I?" she said, motioning toward the binder. She flipped another page, and then another -- coming to rest on a picture of her with a cock in her mouth, her eyes on the camera.

"I used to question why he always wanted more. Did you look at them all?" she asked, closing the binder she had opened and with her hand waved in the general direction of the other binders.

"No." I practically whispered; my mouth so dry I could barely speak.

"Hmm. Kind of funny, you're the only one other than my husband and me who's ever looked at them. You didn't hear me, did you?"

"When?" I asked, not understanding her question.

"When I found you looking at them. You were so engrossed you didn't even hear me come in." I shook my head no, she picked up her soda and took a sip. "At first, I was... embarrassed. Those were my husband's and my personal pictures; they weren't intended to be seen by anyone else. And then, watching you looking at them, seeing which ones you paused longer on... which ones you liked..." she paused, "it kind of..." She didn't finish the thought. "That first picture..." she said, flipping back to the one in the mountains, "that's always been one of my favorites. It was the first time I let him take pictures of me naked... and I really liked the result. I always thought he made me look better than I was. At first when he wanted to take pictures of us... having sex... I wouldn't let him... but now, looking back, I'm glad I did. Great memories." I didn't know what to say, so said nothing.

"Have you got a girlfriend?" she asked.

"Uhm..." I hesitated. Was there any reason I couldn't say I didn't? "No."

"Really? I'm surprised, a good-looking guy like you? But you've had girlfriends?"

"Never anything serious," I answered, trying to put an 'it's no big deal" spin on my answer although the reality was, I thought it was a big deal.

"Are you... gay?"

"What? No! I like girls... it's just that..." I had to think about what I wanted to say, "it hasn't happened yet." She nodded.

"It will. I didn't have a boyfriend until late in high school, but then," she giggled, "I guess I made up for lost time."

"How's that?" I asked, not understanding her reference.

"I guess I really shouldn't be telling you this," she said, pausing momentarily, and then continued, "but once I was introduced to sex, I found that I really liked it. Until Robby died, I don't think a week has gone by in my life where I didn't have sex at least three or four times."

Oh fuck. TMI.

Despite that Mary, by my estimation, was an old lady, as I've said, old enough to be my grandmother, I found my cock expanding in my pants. I'd had my eyes opened in the last few weeks, finding the first issue of Playboy and the corresponding first issue of Penthouse; finding pictures of Mary made by her husband from maybe forty years before when she was about my age, sexual story magazines where some, or all, were really hot, and Mary admitting she and her husband used to read them together and she'd been very sexually active, right up until her husband died. I couldn't picture my parents having sex, let alone someone their parents age, but here she was admitting that she had, until recently, been sexually active and liked it.

I found myself once again assessing this woman, and seeing her in a different light. She still had boobs that seemed to fill out her blouse quite well. I'd seen cartoons of old ladies with boobs that hung to their knees, but she didn't seem to be like that. I wondered what her boobs looked like -- would they still be as nice as they were in the mountain picture? And that she'd caught me looking at her pictures, and hadn't screamed or grabbed them away -- she'd just let me look at them.

I was glad I was sitting down.

"Ok, so where do we stand?" Mary asked, totally changing the subject. "You've got Robby's room all cleaned out?"

"Uh... Just about," I answered.

"What's left?"

"Just that... uh, last box of those magazines. I, uh, was going to take them home."

"Ah," she said nodding her head, "and probably not anything you want your mother to see you bringing in?" I blushed, feeling the heat radiating from my face. "Ok, no big deal, you can leave those there until you can take them away. Take them home a few at a time if you want. So, are we ready to get busy on preparation for painting?" I nodded, and she stood up, "Ok, so let's go look at what there is to do."

I knew as we reviewed what she wanted done that I was going to be busy for quite some time. The outside paint had deteriorated a lot, I knew it was going to take days and days of hot, sweaty, dirty preparation work. She showed me where she wanted me to start and then suggested we just start fresh the next time. She showed me where everything I needed was, told me to let her know if I needed something else and she'd get it, and told me I could just get started by myself on Saturday as she had a morning appointment elsewhere.

~

As expected, she wasn't home when I got there on Saturday but she'd shown me where the key was, and I let myself in. The door to the back was through the kitchen so I collected the tools and went out back, and realizing I needed an extension cord for the power sander went back for that. I hadn't particularly been looking, but as I stepped back into the kitchen, I spotted the three binders of photos that I'd only partially looked at before, on the counter, where she hadn't put them away. It only took me a second to know I was going to look at them again and forgot about the extension cord.

The binder that I'd looked at before happened to be the one with the oldest pictures, where Mary was the youngest, starting with what Mary had confessed was the first topless picture Robby had ever taken of her. I hadn't even finished that binder, but now did. As I'd noticed before, the earliest photos were more just nudes, but by the end of the binder included some sex acts, particularly of Mary sucking Robby's cock which seemed to be a favorite theme.

I realized the next binder must have been out of order as Mary was much older. Sliding it aside I opened the third and found pictures of her older than in the first but younger than the second.

The binders were almost like a history of their vacations and sexual activities; Mary topless on a beach surrounded by white sand and palm trees; another at some type of resort, a waiter with a tray of drinks with umbrellas bending to hand a drink to a topless Mary, Robby's photo perfectly catching the waiters eyes glancing sideways at Mary. And of course, multiple pictures of Robby and Mary having sex or Mary in lingerie. I didn't dally long perusing the photos, my cock getting harder and harder, before I found one of Mary looking into the lens, sucking Robby's cock that was the final straw and I had to take care of myself. Dropping my pants, I gripped my cock and jacked off -- semen spurting into the air and all over the kitchen floor.

Immediately mortified at my own actions, I grabbed paper towels from beside the sink and wiped up semen that seemingly had gone everywhere. I washed my hands, replaced the binders in order, and took the messy paper towels with me and put them outside in the trash can. I left the outside door open with the screen door closed so fresh air could enter the kitchen, and by the time I came back from putting the paper towels in the outside trash, I could no longer smell my semen, but double checked -- making sure I'd left no evidence of my indoor activities, finished fetching the extension cord, and got busy.

Despite that I was trying to concentrate on sanding and cleaning woodwork to prepare for painting, my mind kept going over and over the photos of Mary. Mary naked, Mary in lingerie, Mary masturbating, Mary sucking cock, and a multitude of Mary having sex with Robby in multiple different positions. The very last picture in the third book was of Mary, totally nude and sitting on Robby's cock in what I knew was called a cowgirl position. Both hands were up, a breast in each hand, her fingers tweaking her own nipples, a happy smile on her face. I didn't know when that picture had been taken, but was certain it hadn't been all that long ago. She wasn't the 20-year-old newlywed in that picture, but was the older woman that she was now, obviously still enjoying herself.

I heard Mary's laughter over the noise of the sander and stopped what I was doing which was standing on the ladder sanding and grinding on the eaves. "Oh hi!" I said, flipping the safety goggles up as they were also coated with powdered paint and made it difficult to see very far.

"Oh my," Mary laughed aloud again, "you look like a raccoon!" I glanced down to see that I was covered with paint dust and dirt. Apparently, my eyes, clean behind the googles, made me look like a raccoon. "You're definitely going to need a shower today. Why don't you come down and I'll get us a drink? Soda or iced tea?"

By the time I got my hands and face washed at the hose she had two sodas sitting on the patio table. "It's going to take a long time," I said, pointing at the eaves. "They're in really bad shape."

"I know. I had several contractors make estimates, but not a one of them had proper preparation included. They all just wanted to knock down anything that was really loose and just spray over it."

"Yeah, my dad taught me about preparation and if you don't do that properly, it always looks like you just painted over the top and then in a few years it will begin to peel again."

Back to work, surprisingly Mary came out to help. While I was on the ladder, she began sanding around windows, kicking up nearly as much dust as I was. When she again called me down to get a rest and drink, I had to laugh at her as she also had "raccoon eyes". "Looks like you're going to need a shower too."

"Yeah, probably," she answered. I took a drink of soda.

"Danny?"

"Yeah?"

"I uhm..." she hesitantly started. I'd never heard her hesitate like this before, and just waited. "You're earning money for college; would you be interested in something that pays a bit more than sanding eaves and painting walls?"

"Of course!" I answered without hesitation, only then realizing she hadn't said what it was. "What have you got in mind?" I asked somewhat hesitantly. I'd previously told her I was up for almost anything that earned money, so why her hesitation?

"Did you enjoy finishing looking at my pictures?"

I gulped. I had no doubt she was talking about the binders that she'd left on the kitchen counter -- but how had she known? Without waiting for my answer, she smiled and continued, "It's OK, I figured you would, I didn't mind you seeing me."

"I um... how did you..." I stammered.

"You put them back in chronological order, but I'd put the second oldest on the bottom."

Damn. Immediately I remembered that had been the case. That's why I'd double checked after I'd cleaned up -- something had seemed it might be different than I'd found it, but hadn't realized what. She'd set me up.

"So, how would you like to earn $250 dollars an hour?"

"What?" I asked, now totally befuddled at the seeming change of subject. She asked about money, she asked about her pictures, and now was back to money, talking about ten times what she was paying me. What was she getting at?

"$250 dollars an hour. Not every time you're over here, but at least once a week, maybe more?"

"Oh wow! That would be fantastic!" I answered, my mind immediately multiplying to a thousand a month, $12 thousand in the year, minimum, and maybe more. "What do you want me to do?"

She was looking right at me, later I realized it was to judge my reaction. "Did you masturbate to my pictures? Like you did with those magazines the other day?" I know my face gave me away -- she had me dead to rights. "I was pretty sure you had." She let me stew in my own embarrassment for a moment before she continued. "So, you did find me sexy, huh? Not bad for an old lady?" She paused. "What was it that Rose said in the movie Titanic? I was quite a dish, wasn't I?" She paused again, obviously a bit reluctant to continue. "I'm not going to beat around the bush," she said, beating around the bush, "I'm just going to ask you. You're a pretty sexy young man, I've seen you naked in the shower. You've seen me naked in my pictures. I love sex and I need sex, and you do too. I'll pay you $250 to have sex with me. At least once a week, more on occasion. No strings attached, I just need sex and you need money and I'm willing to pay you for it."