Virgin Gigolo Ch. 05

~

"Brent's Tree Service?" the woman's voice said after I said hello.

"Yes," I answered, a vague feeling that I should know this voice running through my mind.

"I saw you the other day at Helen's and she said you provide wonderful... Tree and other... maintenance... services." Although she was sticking with the euphemism, there was no doubt in my mind about what she and I were talking about.

"I do," I answered, "are you in need of some... yard... maintenance?"

"If you bring the tree you had with you the other day I sure am."

"I can certainly do that. I haven't left it home yet," I answered and chuckled.

"Uhmm. I hope not. I've been thinking of that... tree... and what it could do for me ever since Helen's... party. I'm curious, how much are your services?"

"Individual service starts at $250 per hour with a two-hour minimum, but can be extended, at least until I run out of wood." I didn't know whether she caught the innuendo or not; she didn't laugh.

"Ah. And do you do clean-up? I might provide... something to eat, but I would expect the service worker to clean up from there."

"Oh definitely, not a problem. I always clean up after I eat and leave the kitchen clean."

"Oh good." I could hear a bit of heavy breathing, but she was quiet for a moment.

"Would you like me to check my calendar and see if I can fit you in?"

She giggled. "I was actually hoping that I could fit you in." It took me a second but then I realized her double entente and laughed with her.

"I will certainly give it a try."

"And you do full service?" I hesitated for a moment, not sure what it was that she was asking more than we'd already hinted at.

"Just about anything," I answered, "what have you got in mind?"

"Do you do front yards and... backyards?"

"I've never done a backyard," I answered after a few second pause, "but we can certainly give it a try." The request caught me by surprise -- just what did I feel about back-door play? Not something I had contemplated as nobody, until now, had ever brought it up. Certainly, I'd heard of anal sex, but it wasn't anything I'd ever been attracted to.

"I think that's what I really need. My husband mostly takes care of the front yard, although he hasn't given it a thorough cleaning in quite some time, I just can't get him to do the backyard at all. I, um, I'd like you to do some cleanup in front and, uh, I'd like my backyard taken care of too."

"Ah, I see. Will your husband be at home... or assisting?" I asked, wondering if he was going to be another Paul.

"Oh no. No. He won't know anything about this. Have you got any problem working on a yard at a different location?"

"What have you got in mind?"

"The Crowne Plaza, downtown? It's not far from my work and I'm thinking I can take an afternoon off." I thought she was going to say immediately, but instead we made an appointment for the following week.

~

The text just said, "Room 228."

Nobody even gave me a second look as I strode in through the door from the parking lot and walked straight to the bank of elevators, acting like I knew where I was going. Seeing the stairway just beyond, I continued and walked up the stairs, making the U-turn and hearing the "ding" of an arriving elevator at the ground floor just as I reached the second floor. Signs directed me to room 228, and I rapped on the door.

"Who is it?" The voice called out from within.

"Brent's Tree... and Room Service" I changed my response with an inward chuckle.

The door swung inward, and I stopped, shocked.

"Danny?" Robin's mother, Martha, said, obviously as shocked as I was. "Oh my God, this was a mistake."

I suppose it was bound to happen, sooner or later, that "Brent" was going to run into someone who knew Brent was really 'Danny.' But why did it have to be Robin's mom?

"I thought your voice was familiar when we talked on the phone, but I didn't realize it was you," I said.

"Oh my God, this is so embarrassing."

I stood there for another moment and when she didn't move aside, I said, "Shall I come in?" Her eyes widened, I saw her swallow, and her eyes scanned down my body as she backed up, making room for me to enter the room. I don't know how I recognized it, but in that instant realized she had made the decision that she did indeed still want to fuck me, even if she did know who I really was, even if I was her friend's teenage son.

Martha was wearing a simple pale pink, sleeveless blouse, and grey pleated skirt. Lacy decorations on her bra were visible through her semi-translucent blouse. Although partially transparent, it was still obviously business professional attire, even with the two barely visible points of her nipples. I had to wonder whether those tiny bumps of her nipples were normally visible or whether her nipples were more erect than normal. Her bra seemed to be full coverage but with the lacy material highlighting her blouse I couldn't help but wonder if it was perhaps a bit sexier than what a businesswoman would normally wear.

"Is it more embarrassing for you? Or for me?" I questioned. "Is it more embarrassing because you wanted to hire a stranger..." I paused momentarily, and decided to get it out in the open, "for no strings attached sex and found out he's the son of your friend, or for me to find out that you, the friend of my mother, are willing to pay me for it?"

She stood silently for a moment; I could tell that she was second guessing herself. "It's OK, Martha," I said, taking another step forward to her, and reaching up two handed, fondled the collar of her blouse. I felt her recoil slightly away from me, and then she straightened up, staying where she was. "Nobody will ever know what happens in this room, whether you ask me to stay or ask me to leave." She nervously swallowed again. "So? Which will it be? Do you want me to turn around and walk out that door? If so, no one will ever know I was here." I gave it a second and said, "Or do you want me to stay?"

"Stay," she whispered.

"Good choice," I smiled, letting my fingers slide down from her collar to the top button on her silky blouse. The button easily slipped free, and taking my time I fondled the material before moving down one button. "Nice blouse," I complimented, slipped the second button, and then ran my hands sideways to her breasts, my finger rubbing gently across the barely visible nubs of her nipples. "I'll bet you'd look good in this without a bra." I couldn't tell for sure, but it looked like her nipples perked up even more to my slight caress.

"Do I... Do I need to pay you?" She stammered as my fingers found the third button.

"Normally I collect up front," I nodded, "but I know you. It's ok. We'll worry about that later." I sensed that asking her for money right now would change the dynamic, and she seemed to be somewhat reluctant to continue this, so I decided to just keep the forward motion. My hands continued down, pulling her blouse from her skirt as I reached the last visible button. Pushing the halves apart as the bottom button came free, the blouse easily slid open over her bra covered breasts, exposing them and her bare belly. I pushed the blouse aside with my wrists, gripped her waist and slid my hands up her belly to her bra and breasts, filling my hands and kneading them this time. Pushing further away from the center of her body, I used my wrists and forearms to shed her blouse.

She dropped her arms and shoulders; the blouse fell to her wrists, and I took it from her, as otherwise it would have fallen to the ground. I glanced down just long enough to ascertain how I was holding the blouse, folded it in two, and turned to step over to where I gently laid it across the arm of the chair. I stepped out of her reach as I put the blouse down and when I turned back, she hadn't moved. As I stepped back to her, her hand now came up and stroked up and across my chest and shirt. "Do you want to take my shirt off or do you want me to?" I asked, sensing her desire.

"Uhm... I want to," she said, finally relaxing a bit, as her fingers began fumbling with my polo shirt. She loosened the two buttons on the neck and then pulled it out of my pants. I lifted my arms as she pulled it up and off, tossing it to the same chair where I'd laid her blouse. "Oh my God, you've grown up!" she said, her hands running up and across my pecs, her thumbs finding and caressing my nipples.

"Happens to most of us eventually," I answered with a smile, my hands reaching for her waist and skirt. Her hands slid down my belly until her fingers found and began fumbling with my belt. I slid my hands around her waist, past the side zipper, and gripped her ass two handed and began to pull her closer. Not feeling the edge of her underwear, I stroked her hips and ass, finding the crack of her ass, my fingers rising but still feeling nothing. I ran my hands to the bottom of her skirt, lifting my hands up underneath, and found nothing but bare flesh.

Slowly sliding my hand to her sex, I still found nothing but bare skin and a hot and wet pussy. "Why, Martha! You're not wearing panties!" I said. She flinched as my finger found her clit and pressed against it.

"I soaked them... two hours ago," she said as the fingers of her one hand slipped into the front of my pants and caressed my cock head while her other hand gripped my elbow and pulled me closer.

"Two hours?" I marveled, "why is that?"

"More like four hours," she answered her fingers pulling out of my pants, her other hand coming over to grip my belt and pants to loosen them. "I was so wet I had to take them off." My belt free, a shudder ran through her body just as her hands gripped my pants to pull them open, my finger moving across her clit the cause. A pant exuded from her mouth, her grip on my pants changing to her arms encircling me, pulling me close. Realizing she was close I wiggled my fingertip back and forth across her clit -- and she almost instantly convulsed in orgasm, multiple gasps emanating from her mouth as her body shuddered.

"Nobody has touched me there except my husband since before Robin was born," she said a moment later after I'd stilled my fingers and she'd finished convulsing. "Oh my God, I've wanted that all day." I heard what she said and just filed it in my memory for the moment.

Moving my finger away from her clit I realized I found no pubic hair. I ran my hand up above her pussy and then back down, finding and slipping my fingers along her labia. Several of my customers had decoratively trimmed their pubic hair; triangles, small rectangles above their clit, or landing strips, but for the most part older women were untouched in their pubes, or just closely trimmed.

"You don't have any hair," I commented, running my fingers around her sex, "Did you shave?"

"Robin waxes and she convinced me I should do it too."

"Why?"

"She said guys like to do oral more if it's bald."

"Uhmm," I acknowledged, my fingers now sliding between her labia, feeling how wet and slippery she still was. "And do you want oral?"

"I told you I did. I was hoping my husband would want to, I don't think he noticed."

"No? Why not? How could he not notice?"

"I went with Robin when she got her Brazilian last Monday. She gets one every four or 5 weeks, and she's been telling me I should do it to. I guess all the girls do it these days, don't they? My husband and I haven't had sex in about two weeks, and he hasn't gone down on me in probably 5 years. I thought if I got it done, he might want to. I don't even know if he noticed."

"He didn't notice?" I commented, "A sexy MILF like you?"

"We had sex all the time when we first got married. It's not quite like it was anymore," she answered as I pulled my hands from under her skirt and, finding the side zipper, lowered it. Almost simultaneously her skirt slid down over her hips and bottom. I held it and lowered it until she stepped out of it so that she was now totally naked except for her bra. I folded the skirt in two and laid it by her blouse before turning back to her. She immediately reached for my pants again, but I fended her off, instead gripping her arms and walking her backward the few steps to the bed.

When her legs hit the bed, she sat, and I pushed her backward until she lay back onto the bed. Sliding my hands down her body, over her breasts, I reached her hips as I dropped between her legs. Running my hands from her hips, I caressed the crease of her legs, the whole time observing her pussy, and especially her large, meaty labia. I slid my fingers in against her sex, squeezing her labia together, pooching them out, and imagining them protruding in a camel toe through tight fitting shorts or panties or a bikini bottom. "Very nice," I told her, raising my eyes to hers. "I've never seen a hairless pussy."

"Never?" she asked, her hips twinging to my caresses.

"Not totally," I answered, "most older women don't shave at all, but a few have shaved some." Letting my fingers ease the pinch of her labia I slipped a finger down and into her vagina. "Robin waxes her pussy too?"

"Yes." I couldn't help myself, wondering exactly how much my fantasy girl resembled her mother.

"Because she likes oral sex?"

"All women like oral sex."

"Is that so? And do you? Do you want me to do you with my tongue?"

"Will you shut up and eat me?"

Eating a freshly waxed pussy was totally different. No fighting pubic hair, no pubic hair coming loose and ending in my mouth. Even though I'd never seen one completely bald, I'd had several women who shaved some, and that was about like a man with a beard, it wasn't bad with the lay of the hairs, but moving the opposite direction was slightly prickly even after being freshly shaved. With Martha, her pussy was still totally smooth. I gave her everything I knew, listening to her body, tasting her pussy, her juices, and tonguing her clit, and finding her skin still slippery smooth. I had two fingers in her vagina, her hips rising to force herself harder against my tongue, when she finally bucked and quivered, grabbing my head to hold me still.

"Oh my God!" she panted, followed by another "Oh my God!" I felt her body finally relaxing underneath me, her panting slowing down.

"I take it that was ok?" I asked, leaning forward, and tonguing her clit once more. She quivered and pushed my head away.

"Oh, you have no idea. I've wanted that, I've needed that for ages. That was really nice; that might have been worth $500 by itself."

"I liked it too, your pussy is so smooth."

I stood up, still between her legs. "Take your pants off," she instructed. I'd planned on doing that anyway, but decided to tease a bit.

"Don't you want to do it?"

"I just want to see that cock that I've been thinking about since Helen's party." I released my pants, letting them just fall to the floor, now standing naked between Martha's legs. "He's gorgeous. Bring that up here," she said, gripping my cock and pulling me towards her. Moving outside her legs, I crawled onto the bed beside her, her hand immediately going back to my erection.

"Does anyone else know that "Brent" is Danny?" she asked, her hand pulling me to the bed beside her.

"Just one," I said.

"Who's that?"

I shook my head no. "I don't kiss and tell, even if I don't kiss."

"You don't kiss?"

"Something I started from the beginning. Kissing is about love; this is about sex."

"Hmmm," she responded. "You've got quite a reputation for making women happy, you know?" I shrugged a shoulder. Every woman that I'd been with had said something like "you come highly recommended," or similar. I kind of assumed I was leaving women happy, but nobody had ever said that specifically.

"How does this work?" she asked. Did I understand you guarantee at least two orgasms?"

"I don't guarantee anything," I answered with a smile, "although generally it's no problem to have at least two orgasms. I'm here for you, so whatever gets you off..."

"And you cum too?"

"Of course. I guess I'm about like most guys. I cum pretty fast the first time, but after that, I can usually control an orgasm until after you've cum. Some women cum quite fast, at least one woman likes about two hours of oral and foreplay before she cums just once. My tongue can get a little tired working on her." I smiled, letting her know I wasn't complaining. "So, what's your desire, Martha?"

She didn't answer for a moment, her hand holding, squeezing, and slowly stroking my erection. "I want you to do what my husband won't."

"Hmm," I said, "your husband won't do something for you? And what is that?" I knew what she'd hinted at with our original phone call, I'd just eaten her to a magnificent orgasm, but I wasn't going to go there unless she asked for it.

"Will you... I want you to fuck me in the ass." She started to ask, and changed to telling me what she wanted.

"You've done it before and you like it, or is it something you want to try?"

She sighed. "We all like what we like, don't we?" I nodded. "I started doing anal before I started vaginal sex. My boyfriend wanted to fuck, I said no, and he kept pushing. My older sister was the one that told me I should let him take my ass instead. She gave me lube and condoms, and told me how to get ready, and said the trick was to push out, like I was taking a poop, when he was trying to get in. The next time when he was pushing me to fuck, I told him if he wanted, he could fuck my ass. We did it, with lots of lube it really wasn't bad at all, actually it was quite nice. When he was fingering my clit at the same time, I had a nice orgasm. Over time I found I really liked when he fucked my ass, even after I started having vaginal sex. Normal sex was good, but the orgasms when someone was taking my behind... they could be... phenomenal. The only lover of mine who's never done my ass is my husband."

"You'll have to guide me; I've never done it before."

Martha just looked at me for a moment, her tongue slipping between her lips, when suddenly she shook her head and said "Fuck!"

"What?" I said, surprised at her outburst.

"What am I going to tell your Mother?"

I shook my head in surprise, thought about it calmly for a moment, and then said, "You'll tell her nothing of course. What you do, and what I do, has nothing to do with her, any more than what you and your husband do has nothing to do with her. Like I said, there is one other woman who knows who I really am and also knows my mother. I've seen her once while my mother was there, and we'll do the same thing. You'll treat me like you've always treated me in public, and I'll treat you the same. You're just my mother's friend whom I'm only barely acquainted with." I slipped up onto the bed beside her, pushed her onto her back from her side, and straddled her. "But for right now," I said, reaching up to her bra, pushing it up and over her breasts, "I want to play with your nipples." I filled my hands with both breasts, my thumb and finger coming together to roll her nipples between them.

"Oh, you are something else," she giggled, and sat up, forcing me back momentarily. Reaching behind herself she unhooked her bra and pulled it off until she was now as naked as I was.

I smiled at her, reaching for her breasts once again.

When she pushed me backward and off her legs, I rolled to the side, and she turned, bent her face to my crotch, and took my cock in her mouth. She bobbed and twisted, sucked, and licked, for several minutes, the tingling increasing in my cock the entire time. "I've always loved sucking cock," she said when she pulled away, holding my cock upright, "but I can do that, or get fucked, at home with my husband."

I rolled back and off the bed, grabbed my pants and pulled one of the condoms out of my pocket. "Do you want to put it on?" I asked, after I'd torn open the foil and pulled it out.