Virgin Gigolo Ch. 01

I suppose, had Robin not gotten married, I might not have ever become a gigolo servicing multiple MILF's. Some of them neighbors and in the neighborhood, others in parts of town where I didn't normally visit.

Robin had been my fantasy girl, well... since I'd noticed there was an enjoyable difference to girls. That she was two years older than me, and the daughter of a friend of my mother's; gorgeous, and as sexy as any girl I'd ever known -- and not at all interested in me, made no difference. Whenever our families got together, she had no choice about me being around, but it seemed we really had nothing in common. I suspected she just tolerated me, and I suspect she knew I lusted over her, but what gorgeous popular fantastically sexy girl is ever interested in a nerdy pimple faced "friend" who's two years younger? It was almost a written rule in high school; guys had girlfriends that were two years younger and the older girls had boyfriends in college.

I just knew there was no way she would ever be interested in someone like me. I'd graduated from Junior High at 5 feet 4 inches tall -- and a roly-poly 154 pounds. That I sprouted over the summer, gaining a full 8 inches, and rounding out at 6 feet tall -- only made a difference in that I actually lost weight. I entered the 9th grade a skinny, 6 foot and 135 pound bean pole. Never popular with the girls when I was "well rounded," I was now even less popular. There was no way I was playing football; I was too skinny. I had the hand-eye coordination of someone who had never played basketball before, so that sport was out, and I'd never had an opportunity for soccer or baseball -- so athletics wasn't my thing. The only thing I had going for me was that our house was three houses inside the dividing line of who got bussed to school and who didn't -- so consequently I began riding a bicycle to and from the school which was exactly 150 feet short of 3 miles. That I had to go up and down across a deep canyon, both ways, didn't hurt and gradually I began to fill out and put on muscle. By the time I was a senior I was no longer the proverbial 98-pound weakling -- but still I was known as a nerd.

Robin had been a cheerleader in high school, had multiple friends, and the popularity that ensued with being the most photogenic of them all. Her photo had graced the cover of the school annual with her golden tresses and beatific smile obvious draws to the eyes. I'm sure the pose of her, seated and leaning backwards on a large boulder, one leg bent at the knee with foot flat on the boulder while the other was stretched out straight, ensuring that at least some of your attention was focused on her very shapely legs rather than the magnificent bosom jutting from her chest (which would have otherwise totally grabbed your attention) had nothing to do with it. I'd finally taken the annual home, only to have my mother say, "Oh, Robin's on the cover? She's so pretty. Who's the guy with her?"

Guy? What guy? I looked over at the picture again, and realized that standing behind her looking at the lens, one hand resting on her naked raised knee, was the captain of the football team, and her boyfriend at the time, Adam. "Oh, so that's Adam," Mom said when I told her his name. Somehow, she'd known about Adam, but had apparently never seen him or met him. I guessed that since her mother and my mother talked all the time, she'd heard about him from Robin's mother.

Robin had so dominated the picture, at least in my mind that, to me, Adam wasn't even there. I knew that they were both seniors and that she had dated Adam for the last two years of high school. She was the popular head cheerleader, dating the popular football quarterback, and that they'd spent a lot of time in each other's beds. I knew this as her mother, Martha, had told my mother about how she'd come home unexpectedly and found them in flagrante delicto; both totally naked and fucking, with Robin on top.

I only knew this as my mother had the trouble that she didn't like to hold her phone; whenever there was no one else around she would put it on speaker. Several times over the years, I'd heard the "just a minute," as she'd answer the query of "are you on speaker?" and then I'd have to listen closely to my mother's words, as those kind of conversations invariably were the juiciest.

That day, I'd been home in my room when mom came home; she didn't even know I was home. I had easily overheard Martha telling my mother all about how she'd found them in the living room, where they had been so self-absorbed that they didn't even know they'd been caught until she'd said something. I heard her voice on the speaker more easily than my own mother's responses, but could imagine what was being said or asked. I heard her say, "Oh my god, yes. And let me tell you," she giggled, "Robin is one very lucky girl. Let's hope he doesn't spoil her, so she expects that everyone is going to be like that!" My mother's own laughter I heard quite well, followed by an unintelligible question, and a "No, I'm pretty sure they won't be permanent."

And that turned out to be true; she'd broken up with Adam just after they graduated, and now, here she was, the week before a mid-April Easter, sitting at the bride's spot next to her college boyfriend, Dennis, looking just as radiant, beautiful, and sexy as any girl I'd ever known. I didn't know if he was her first after Adam, or her twelfth, but she was the trophy bride and apparently from his looks, he was a trophy catch also.

I guess white is supposed to signify virginity. Although I knew she wasn't a virgin, her dress was absolutely perfect on her. The top was lace, wrapping up and over each shoulder and then barely covering part of her shoulder blades before wrapping in under her arms, leaving her naked to the waist in back. In front, the lace merged to satin cloth covering over her magnificent breasts; without a bra the two buttons of her nipples accented that material before it dipped between her breasts. The lace coming in under her arms from behind also merged with the cloth over her breasts but, when viewed from beneath her arm when she danced with her new husband Dennis, more than a little peek of her breasts was available. The lower part of the dress was the same material that covered her breasts, at least in front, and silkily covered her delectable bottom. Occasionally, as she bent a bit, it formed to the globes of her ass, without a hint of a panty line beneath. If there was ever a doubt that a wedding was essentially a public announcement that the bride and groom were now partaking of a sexual relationship -- she totally removed that doubt.

I mention this only in that, sitting at my table just one removed from the "close" family table between me and the head of the room, I had an enormous erection that was thankfully covered both by my suit and the tablecloth. It was my imagination, of course, which was the culprit. Imagining it was me lying on the living room floor with a naked Robin riding me; imagining it was me lying in our marital bed while Robin suckled my cock; imagining it was me, lifting her legs over my shoulders as my cock slipped in and out of my Robin's dripping quim, her "Oh yes! Give it to me!" urging me on.

Her dance with her new husband merged into a dance with her father, merged into a dance with her uncle and then my father, into a dance with.... After the first dance with her father I saw that a line of dancers had formed to one side, guided by her mother, and I saw that each of the dancers was being provided a safety pin where they were then pinning money to her dress, and the idea of a "dollar dance" finally took shape in my mind. I'd heard of them before, a way for people to 'give' money to the new bride and groom, and wondered if perhaps I could join. And then, as she twirled close by my table with one dancer, I was able to discern $100's and $50's, and a few $20's -- all well outside of my limited means. I could have afforded to give away maybe $10 at that time, but didn't want to appear to be a cheap skate. I suppose I could have said "Hey Dad, I need some money to dance with Robin," but that totally negated my own attempts to become totally independent -- and at the same time would have been better spent on my own, about to begin, college education that I still had no idea how I was going to pay for.

"Oh, the oven's been out of commission for quite some time," I heard a woman's voice behind me from another table intrude on my conscious, "but doesn't mean I don't still like to cook!" I'm not sure, perhaps it was the ensuing giggles and outright laughs from several other women that kind of gave away that they were talking about sex. "Oh no, I'm going to have to hire someone, I just can't take care of everything on my own anymore now that Robby's gone..." the woman stated, and after another unintelligible response from others, a laugh from her, "Well, I suppose paying for that could be an option, couldn't it?" which elicited another peal of laughter from everyone.

The changing of the music drowned out the rest of that conversation, but when I had the chance, my erection now subsided and more under control as the thoughts of dancing with my sexy friend were erased for the moment, allowed me to rise and wander to the table to obtain a drink refill. As I turned I let my eyes flow over the table behind me, realizing that the woman I'd been hearing moderately well was Mary Jane Wilson -- Mrs. Wilson was all I'd ever known her as, and remembered my mother saying that she'd recently lost her husband. The thought of anyone willing to pay for anything at this point in my life seemed to be noteworthy, and I filed it away for the moment.

"Danny? Did you dance with Robin?" my mother said, bending near to my ear as she did.

"No," I admitted, only to have to her question, "Why not?"

"I can't afford that, Mom. I don't have any money."

Just as she'd magically arrived at my elbow, without saying anything she slipped away, only to return a few moments later, slipping me a $50 bill. "Here, go dance with her."

I had to wonder why I bothered. I don't know as Robin doesn't like me, but I definitely got no feeling of anything other than "this is the dweeb of a son of my parents friends" after I pinned a $50 bill to her dress and stood to slip my arms around her. I wanted to hold her close, to feel her hot body against mine; maybe the feel of those gorgeous breasts pressed against my chest, my hand against her bare back, her giggling at the hard rocket in my pants pressing against her belly as my hand slipped onto her gorgeous bottom -- nobody else in the room noticing, of course ...

Instead I got a hand on the shoulder, the other in her hand and a quick spin around the floor, before she spun me off to take on another, with barely a "Thank You."

Slightly deflated, although I'd known, in reality, that's how it was going to be, I slipped back into my chair. A few minutes later, the solo dance of Robin with anyone willing to pay finally finished and others had begun dancing, I felt a touch to my shoulder and turning, heard "Will you dance with me, Danny?"

"Oh, of course, Mrs. Wilson," I said as I recognized the woman that had momentarily caught my attention previously.

"Please, you're old enough you can call me Mary."

"I don't know... Mary... it feels funny to call you that." She laughed.

"What are you now, 18?" Our small talk extended through the entire dance and unlike with Robin, Mary didn't hesitate to hold me close. She was almost as tall as I was, a slower song started just as she stepped into my arms, and when my hand went to her back, her breasts rested softly against my chest. Her arms started behind my neck, but as we moved slightly around the floor, she slipped them onto my back, pulling me in against her. If it had been Robin holding me close like that, her breasts rubbing against my chest like that, I'm sure I would have sprung an intrusion between us. But with Mary, I was able to control such a physical response.

I knew she was older than my parents. who were in their 40's, so she had to be in her late 50's, maybe early 60's? But Mary really didn't look that old to me, which is unusual for me to say, as in my eyes, anything over 28 was "OLD." I smiled to myself as this went through my mind as back when I'd been 12, anything over 14 was "old" and under 12 was "young." By the time I was 15 or 16, anything over 20 or 22 was old, and under 12 was young. And now, at 18 -- I was unconsciously rating any woman over 28 as "old" -- and my lower limit had finally raised so that anything under 13 or 14 was "young." I wondered momentarily if that escalation of the upper limit would continue faster than the lower limit.

"Fond of Robin, are you?" Mary said virtually into my ear.

"What?" I said, pretending to not understand her question, and then totally negated that idea by saying, "Why do you say that?"

"I saw you. You seemed so eager to go up and dance with her, and then she didn't exactly... well, it wasn't a very friendly dance, was it?"

"Uh-uh," I grunted in reply, embarrassed by having been understood so perfectly by this older woman.

"She is really pretty though."

"Yeah. She's always known it, too."

"Outer beauty fades but what is inside blossoms with time." The song came to an end and stepping back from each other she let her hand stroke down mine, our fingers momentarily catching and squeezing as she said "Thank you, Danny. That was nice."

"You're welcome Mrs... Mary," I corrected myself. We walked back to our tables, where I took my glass and headed again to the drink table for a refill.

~

When I went out to get into my car to leave, I saw Mary standing by a car next to mine talking with a woman that I didn't know. Just as I arrived at mine, she bid the other woman goodbye and turned to get into her car. "Uhm... Mrs... uhmm, I mean Mary -- I overheard you saying earlier you have some work you need to hire someone to help with? If it's something I could do? I need to earn money for college, so if you wanted, I'd be willing..."

"Really?" She said, stopping and turning toward me. "What kind of work are you willing to do, Danny?"

"Almost anything that pays money," I laughed, "the more it pays the better. School's going to be really expensive and the more I can earn, the less I'll have to borrow." I'd applied for multiple jobs already, all of them entry-level, minimum wage jobs, and to date had heard nothing in reply to any of them.

"Are you sure you don't mean you need money to spend on your girlfriend?" Her laugh was a tease, but it hit close to home. I grimaced.

"That would be nice but, I uh, I don't have a girlfriend."

"A good-looking boy like you doesn't have a girlfriend?" I shrugged, embarrassed. "I'm sorry, that's really none of my business is it? So, what can you do?"

We had a short discussion and the majority of stuff that she needed done was strictly manual labor: lifting, cleaning, sorting through her husband Robby's "stuff" and throwing it out or sending it for recycling. Before we parted, I'd agreed to come over to her house the following Tuesday and in the meantime, she'd start putting together a list for me to tackle.

~

As it was, there was a lot to do. It took a week of afternoons and Saturday just to get the yard cleaned up. Everything had overgrown since her husband had died. Just mowing the yard was enough to fill the trash cans with green waste, but when I started trimming bushes, I found large bags that I transferred the grass to and then started refilling the cans with thorny brush. It had to be chopped into quite small pieces to fit in, chopping it up took almost as long as cutting it down. I filled the cans and bags that first day, but luckily the trash collection came two days later, so when I returned on Friday to continue chopping brush into smaller pieces, I had empty cans again.

That first few days, I managed to stay comparatively clean. Mowing, trimming, sweeping -- I got hot and sweaty but not all that physically dirty.

Friday was a different matter. All the "easy" stuff had been done and now I was climbing in under things that hadn't been trimmed in years. I was raking piles of leaves and kicking up clouds of dust and dirt. When the end of the day came and I knocked on the door to tell Mary I was done, she opened the door and just started laughing.

"Did you clean things up, or are you just wearing all the dirt?" she laughed. "Just look at yourself, you can't go home like that."

I looked down at myself, finding, as she was saying, that everything was filthy. My pants, shirt, shoes, arms -- everything was brown or black with dirt and I could feel the dirt on my face and neck. "Ok, come in here," she said, holding the door open. "Take your shoes off here, and I'll be right back. I'm sure some of Robby's clothes will fit you, and you can use the front shower here before you go home." I sat to take my shoes off, and by the time she came back, she had jeans and a tee-shirt and led me to the front bath. "Get undressed and I'll put your things in the wash," she told me, and then stepped out and pulled the door shut.

No sooner had I climbed in the shower than I heard a laugh and "My goodness! Even your underwear is filthy! Well, I guess we know you weren't sloughing off out there, were you? I brought you a clean towel." I hadn't heard the door open, hadn't expected Mary to come in, but glancing over my shoulder through the frosted glass of the door I could see the shape of her body on the far side of the small bathroom and realized that she had to be able to see me as well. I knew from past experience that the closer to the frosted glass that you are, the more visible you are, and I was thankful that I was facing away from the door as I was much closer to the glass than she was.

I got out of the shower and when I reached for the clothes she'd brought, I realized all she'd brought was a shirt and pants. No underwear, no socks. I hesitated momentarily, realizing that if I asked for some underwear, it would be her husband Robby's. Sure, it would have been washed and clean, but something in my head cringed about wearing someone else's underwear. I slipped the pants on, going commando, and wondered later if Mary realized she'd dressed me that way.

The "every day" of that first week became a Tuesday/Saturday duo from then on. The following Tuesday I returned and mowed the lawn again, moving on to the back yard where other bushes needed trimming. By the end of the second week, the outside was almost back in shape.

"Have you ever done any painting, Danny?" she asked after complimenting me on the great job I'd done on the yards.

"A little. Worked with Dad at our house a time or two."

"What's the most important part about a good paint job?" she asked, and I could sense she had her own thoughts about it.

"Uhm..." I hesitated, even though I knew my answer. "Besides quality paint? It's got to be the prep job. That's the part that most people miss. Sure, a fresh coat of paint looks good now, but it will rapidly deteriorate if the surface isn't properly prepared." It was easy to parrot my dad's teachings, I'd heard it with every paint job we'd ever done. Painting is about 90 percent preparation and 10% actual painting." Her nod of approval confirmed she agreed.

"Would you be interested in doing some painting for me?"

"Of course. Anything that makes me some money."

"Hmm. I've got to sort through Robby's "man-room," he's got a ton of stuff that needs to be thrown out. Would you be interested in helping with that too?"

"Like I said, anything to make money!"

"Anything?" she asked with a smirk on her face. Something about the smirk, the accent on that single word implying a hidden innuendo...

"I need a lot of money and I'm not sure where I'm going to get it," I explained. "I've applied for student loans, but I've read so much about people who get in over their head and sometimes never get out. I'm hoping to earn most of what I need and keep my head above water."