The Face - Painter - Cover

The Face - Painter

Copyright© 2012 by rmdexter

Chapter 8

Erotica Sex Story: Chapter 8 - A well-hung young man with a talent for shooting lots of cum tries his hand at being a male escort; while on the home-front, interesting encounters with his mother and two sisters develop.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Consensual   Heterosexual   Incest   Mother   Son   Brother   Sister   Oral Sex   Anal Sex   Masturbation   Size   Big Breasts  

9:49 ... the time slowly registered as I rolled over and looked at the alarm clock through half-closed eyes. Thoroughly exhausted and totally drained, I had slept like a baby after coming home from Margaret's. As I laid there slowly waking up I thought of what I had coming up today. Andy was coming over for lunch; I was definitely anxious to hear about that kiss he told me he'd shared with his mother. My date with my mother was later.

As I thought about her, I rolled over and my hand unconsciously went to my swollen cock. My mind wandered to that risky secretive kiss she'd given me in her rose garden and I felt my pecker lurch as I remembered the sweetness of her hot wet mouth pressing against mine. I remembered how incredibly desirable she'd looked as she quickly drew back from me after we heard my sister's voice, my mother's beautiful soft wet lips slightly open as she gasped, her huge tits heaving invitingly beneath the tight sweater she'd been wearing.

I shoved another pillow beneath my head, threw back the covers and pulled open the drawer of my bedside table. I popped the top of my ever-ready jar of Baby-Fresh Vaseline and scooped out a generous gob. I laid back against the stacked up pillows and wrapped my greasy fingers around my half-hard cock in a warm loving corridor. Between my pumping hand and stiffening prick the viscous lube quickly warmed up. Although that lengthy session with Margaret last night had been incredible, my thoughts this morning were totally centered on my sexy full-bodied mother. My hand started to pump more vigorously along the full length of over 10" of thick hard cock. I pictured my mother flashing those tremendous tits of hers at me, beautifully displayed in that scintillating white bra of hers. As I pictured kneeling over her and jerking off all over those massive tits of hers, I felt those delicious contractions take over within me. I jerked rapidly as a long white rope of cum shot high into the air before cresting and falling onto my chest. I continued to pump as rope after rope of thick milky semen spewed forth. I kept stroking as I continued to unload, my pulsing rod spewing out wad after wad until my chest and stomach were coated with a fine mess of silvery goo. As the final oozing shots slid down over my pumping hand, I finally stopped, my cum-covered hand remaining on my slowly deflating prick. As I laid there letting my breathing slowly return to normal, I thought how perfect it would be to have my mother there beside me, sensually licking up all of that warm thick cream from my body. A guy can dream, can't he? That's what makes jerking off so much fun ... plus that exquisite feeling of orgasm, of course.

Thoroughly satisfied for the moment, I reached into the lower drawer beside me and retrieved my already heavy cum-towel; the one I always used to wipe up with after jack-off sessions. I could feel that it was about time to retire this one to the garbage heap and get a replacement, the terrycloth being matted and heavy from the number of loads I'd cleaned up with it.

After wiping off all the sticky fluid from my body, I headed to the shower and gave myself a thorough cleaning, anxious to get on with the day ahead. I pulled on some shorts and a golf shirt and grabbed a quick breakfast before heading out. As I backed Sally out of the driveway, I took a quick glance over to Margaret's. I wasn't surprised to see no movement and her curtains still closed; I had fucked her good and hard repeatedly last night. She'd probably be sleeping for a few more hours yet.

I slipped on my sunglasses and put Sally into gear. The sun was out and it looked like another beautiful day in Vegas. I headed to the place where I'd gotten my hair cut for the last couple of years. Even though I had no idea what to expect on this date with my mother tonight, I felt obligated to go the extra mile and try to look my best. I'd called yesterday and made an appointment with Deanna, the girl who'd been cutting my hair for a long time now.

I'd been going to Deanna for a number of years, having been recommended to her by a friend from college. She was a few years older than me, about 32 or so, and nicely built. She was mid-height and average weight with a nice curvy body. She probably had tits that were a generous C-cup, and they looked like they would be nice and perky.

Like most hairdressers, I never knew how her hair was going to look from one appointment to the next. She didn't go in for any real whacky styles or outrageous colors, she was just constantly experimenting. I have to admit, she knew how to make herself look good; from her hair to her makeup to her clothes, she always looked great.

We had flirted with each other over the years, but nothing had ever come of it. She usually had a boyfriend on the go that I guess subconsciously hindered me from making any further advances. Anyways, for the last couple of years, Deanna had been living with a guy who was trying to make it as professional poker player. I didn't think I could stand the uncertainty of trying to make a living like that.

"Connor, come on back," I heard Deanna say as I looked up from the magazine I'd been flipping through in the waiting area of the shop. Deanna had been at this salon/spa for about two years now, and I had followed her here. It was a little pricey, but I was always happy with the job she did for me. I could see from most of the expensive cars in the parking lot that this place catered to mostly high-end clientele.

"You're looking good," I said to her as I got up from my chair and stepped towards her. Her light brunette hair had been styled into a lush pile of attractive tight curls. They fell about her shoulders and down her back playfully, one curl after another. It just made you want to run your fingers through her hair and feel it roll through your stroking fingers. It was cute as anything. The hair style suited her. It went with her friendly brown eyes and button nose. Her cute smile always lit up her face, as it did now. Cute; that was the perfect word to describe Deanna.

As I walked towards her, I looked her over. She had on a white blouse that was cut fairly low in the front, and then pulled together with both a couple of buttons, and then a knotted bow at her midriff that showed off her flat toned stomach. I could see that if she just worn it with the tied knot alone, the shop owner may have sent her home for being a little too risqué. But even above the two buttons, I caught a glimpse of her full breasts, nicely encased in a white push-up bra that I could see the outline of through her blouse.

My eyes followed her curvy body downwards, the knotted blouse revealing her shapely hourglass figure nicely; her smooth stomach narrowing in attractively at her narrow waist. Below that she wore a faded denim miniskirt that hung from her hips, decadently revealing her smooth taut abdomen and sparkling navel piercing, similar to Zoey's. Her skin was deeply tanned, and I knew from our previous discussions that she liked to spend a lot of time outdoors on her days off. My hungry eyes looked down past the hem of her denim miniskirt to her tanned shapely legs. Her thighs appeared toned and strong as my eyes drifted lower to a pair of ornate navy cowboy boots. Man, I loved that look! She could definitely pull off the sexy cowgirl thing, that's for sure. My mind immediately started to thinking about how she'd look riding me in that outfit with me buried deep in the saddle.

"Thanks, you don't look too bad yourself," she replied with a kittenish tilt of her head as I followed her back to the shampooing area. "But I'm sure you noticed all those women scoping you out in the waiting room."

"What?" I replied, totally mystified by what she was saying as I sat down in the chair in front of the sink and slid my head back.

"Oh c'mon, are you serious? You've never noticed all those rich bitches here checking you out?"

"Uh ... no." I had to admit that I usually went in and out of there without paying much attention to anyone other than her.

"Oh yeah, I've seen them look at you as if you were the main course on the all-you-can-eat buffet. And I've heard them talk about you; and most of them would like to do more than make a meal out of you; although I'm sure you wouldn't object to that. Yeah buddy, you'd be pretty high-grade stud material if this was a horse ranch. If you were mine, I could rent you out and make a fortune off these women."

I sat there totally stunned by what she had just said. She started to wash my hair as a million confusing thoughts raced through my head. This was the second time in about a week that a woman had suggested I could make money by providing sexual favors to strange women. I had no idea if Deanna was just totally joking around or what, but it got me thinking. I had to admit that when I'd confessed to Andy about my Face-Painting endeavor; he'd scared the shit out of me by pointing out the risks involved when dealing with strangers over the internet. I had loved my initial encounter with Callie/Tanya, and more clients like that would have been fantastic. Plus, the extra money was kind of nice too. But Andy had been right; it was just too dangerous, on many levels.

But this ... this was definitely intriguing. If someone knew these potential clients, like Deanna did, that might just work out. They would know their backgrounds, and what they wanted, and they could provide that extra level of security that I knew I'd been lacking by operating on my own in the dark. I almost laughed out loud as I realized what I was thinking; that Deanna could act as my pimp. As fast as the idea had come to me, I shoved it to the back of my mind as ridiculous.

Deanna finished washing my hair and got me seated at her cutting station, ready to go. "I'm surprised to see you here, I didn't expect you for another week or two," she said as she ran a comb through my wet hair.

"I've got a date tonight."

"Ah, I see. Who's the lucky girl?"

"My mother, actually."

"Your mother?"

"Yeah, it's been about three years since my dad died. She thinks it's about time to get back out there in the dating world. She asked me if I'd take her out; you know, to try and shake the rust off."

"I think that's great. I really admire you for doing that for her." Little did Deanna know I was dreaming about the possibility of burying over ten hard inches deep inside my mother's gorgeous body.

"Thanks. Anyways, she wants to get all dressed up and everything, so I figured I'd better come in and let you work your magic."

"She'll be going out with the best-looking guy in Vegas when I'm done with you," she said as she picked up her scissors and went to work. I let her work in peace for a bit until she stepped around to the front of me to work on the front of my hair.

"So how are things with Brad these days?"

"I threw the lazy bastard out a couple of weeks ago."

"Really?" I asked in surprise. "I thought things were going okay?"

"They were, until I found out he'd pilfered a lot of my savings to use as his poker bankroll."

"You're kidding?"

"No ... stupid asshole. He's lucky I didn't rip his nuts off and sell them on E-bay."

"Uh ... do think you would have had any buyers?" This made her laugh as she reconsidered the strangeness of her proclamation regarding Brad's nuts.

"No," she replied with a bit of a giggle. "I guess not. Anyways, with him gone along with most of my saving, I think it's gonna tough to afford my apartment. I'm kind of done with the roommate thing at my age. I might have to start working a second job and see how that goes."

Hmmmm, now this just made things interesting all over again. Deanna needed some extra cash; and if I wanted to continue as a paid Face-Painter, I needed Deanna's help. This just might work out to be the perfect partnership. I thought this over again and again in my head as she continued to cut my hair. Finally she turned me towards the mirror to show me the finished product. It looked great, as usual.

"Deanna, you never disappoint me," I said as she brushed off my shoulders and drew away the cape. "Listen, I'm sorry to hear about what happened with Brad and him ripping you off like that. But I've been thinking; I might have a little business idea you might be interested in."

"What kind of business idea?" she replied skeptically.

"Something I think you might like. Listen, I've got to work out the details a little better, but do you think we could get together some time in the next couple of days and talk it over?"

"Sure. I'll listen. I'm not saying I'm agreeing to anything, but I'll listen to what you have to say."

"Great." As I paid my bill to the receptionist and left a generous tip at Deanna's station, she jotted down her phone number for me. I thanked her and shoved her number into my pocket as I left, this time noticing the leering views of a couple of attractive older women in the waiting room. Yeah, things might just work out for The Face-Painter yet.

On the way home I stopped at an Italian deli near my place and picked up some stuff for lunch. Andy and I liked the same things, so I got the fixins for some subs and grabbed a pre-made potato salad, plus a bag full of lemons.

There was still nothing stirring at Margaret's as I pulled into the driveway and hauled my stuff into the house. First thing I did was pull out my juicer and get to work on those lemons. I made up a big pitcher of lemonade which was kind of a simple yet delicious specialty of mine. The secret behind it compared to most lemonade recipes was to use honey; not sugar. I mixed up a big pitcher, threw in a shitload of ice cubes and some additional slices of lemon, and put the whole thing in the fridge to chill.

It was a beautiful day and I figured we'd sit outside at my little covered deck at the rear. It was still open enough to enjoy the weather, but partially covered so that the direct sun was not beating down on us. It was also far enough from any prying ears. I wanted Andy to feel secure if anything he had to say ended up being of a confidential nature. I wiped the table and chairs off and started to get some plates out of the cupboards when the doorbell rang.

"Hey, how's it goin'?" I asked as Andy strode past me.

"Good ... good. What's to eat? I'm starving!"

I looked at Andy, dressed in an old pair of jeans and a t-shirt. This was the kind of thing he'd usually put on the day after a party or late-night out. I was surprised that since he had left the restaurant last night pretty early, he looked as rough as he did. I figured he'd probably gotten to bed at a reasonable hour after talking to his mom for a while. "You okay?" I asked as I closed the door and made my way to the kitchen.

"Yeah ... yeah. I just haven't had anything to eat yet."

This was so un-Andy-like, I was kind of thrown off a bit. I looked at the clock before turning back to him. "It's almost 12:30 ... and you haven't eaten yet? And you look like you've been put through the ringer. What's going on?"

He looked at me with a bit of a devilish smile on his face and gave me a big shrug of his shoulders. "Can I just have something to eat first? Or is this a game of twenty questions?"

"Sure, alright. There's buns, cold meat and stuff there," I said as I pointed to the stuff I'd set out on a big tray. "And I've got some potato salad too. Here're some plates and glasses." I grabbed a couple of big glasses from the cupboard and stuck them on the tray next to the plates. "It's so nice out; I figured we'd eat outside."

"That's great." Andy grabbed the tray as I retrieved the pitcher of lemonade from the fridge. We got everything outside and I poured a couple of glasses while Andy quickly started making his sandwich. I passed him his glass and he nearly drained it in one gulp.

"Jesus, I love that," he said with an audible sigh as he pushed his glass over to me for more. I refilled it and passed it back to him before loading up my own plate. "Man, this really hits the spot," he said as he wolfed down a few bites and jammed a couple of forkfuls of potato salad into his mouth.

"Easy there, buddy," I said with a laugh. "You look like a starving dog, afraid somebody's gonna try and take your food away from you."

"Sorry." He purposefully set his half-eaten sandwich down and sat back in his chair. When he finished his mouthful, he took a much slower drink this time. "Hey, thanks for making this. I can't believe how hungry I am."

"What the hell have you been doing that's made you so hungry?"

"Aaaaah," he replied, that conniving smile on his face once more. "Wouldn't you like to know?"

"Dammit right I'd like to know; that's why I asked, dickhead."

"Alright ... alright," he answered with a chuckle as he picked up his napkin and wiped his mouth. He set his napkin down and looked at me intently, a contented smile on his face, and yet a serious concerned look in his eyes as well. "We've been through a lot together, right?"

"Too much, I'd say. Hanging out with a scumbag like you has its challenges," I said, cracking wise. I gave him a big grin and a quizzical shake of my head as I kind of questioned why he'd ask this; I always thought it was pretty obvious to both of us.

"I'm serious, Connor." When he used my name, I knew it was serious.

"Yeah, okay. Sorry." I wiped the grin off my face and just waited for him to continue.

He looked around, and it seemed to me he wanted to make sure we were alone, which we were. He turned back to me and looked directly into my eyes as he spoke. "I need you to promise me that what I'm gonna say to you, you'll take to your grave. I mean it."

"Of course, Andy. You know that's the way things are between us," I replied with a wave of my hand that showed I wouldn't consider anything otherwise.

"Good." He waited briefly before continuing. "Remember what we started talking about last night before I had to leave?"

"About our mothers?"

"Yeah, and I think we both could tell from what we said how each of us feels about them, right?" I simply nodded in acknowledgment of the fact that we both suffered from a severe case of the hots for our respective mothers; something that until we'd started talking about yesterday, neither one of us would have ever confessed to anyone. He paused for a second and nodded back at me before continuing. "I guess the reason why I'm so hungry and look like shit today is that I've been up all night fucking mine."

The enormity of his words slammed into me like a massive tsunami, leaving me in shock and struggling for air as I gasped noticeably. I could feel my blood pounding in my chest as I just sat and stared open-mouthed at the calm expression on his face; totally awestruck by what he had just said. As I sat dumbstruck; a million thoughts racing through my mind at the speed of light, Andy reached forward and calmly took another bite of his sandwich.

"I ... I heard you right, didn't I?" I finally croaked out, my voice tremulous at best.

"I think you did, yes."

"You were up all night fucking your own mother?" I needed to hear him say it, just one more time at least.

"Yes."

I looked at him, sitting there so calmly while thousands of questions flew back and forth in my brain. I think I was just as surprised as him by the one I blurted out next. "How was it?"

He leaned back and took a drink before setting his glass down, then looked directly at me once more. A massive grin slowly spread across his face as he replied, "Absolutely incredible; even better than I thought it would be all those times I fantasized and jerked off thinking about her."

Oh man, I was expecting a hot little story about some kiss they'd shared, but nothing like this. "How ... how long have you been fucking her?"

"Well, that actually just happened last night for the first time. But there've been some other things along the way that have lead up to this."

"Like ... like what?" I asked, my curiosity level climbing to stratospheric levels.

"Pour me some more lemonade and I'll tell you." I poured him another glass and as we finished our lunch and sat back in our chairs, Andy told me his story...

For the next few hours I sat mesmerized as Andy told me his amazing story. I barely said a word as he continued to speak, his voice weaving a tale of forbidden lust that echoed my own similar fantasies; only for him, they had become wonderfully real. I refilled his glass a number of times, not wanting his voice to fail on him during his lengthy narrative.

As I listened, riveted by his illicit tale, envy rose up in me, and yet at the same time, I was sincerely thrilled for my good friend. I couldn't believe how hot his story got as he told it. It started off with a flickering ember; then a few sparks ignited a rising flame that grew in intensity until the raging heat enveloped and swept away both he and his mother. Fuck, I couldn't believe it. There was so much he told me. Here I was thinking my best friend for so many years could never surprise me again, but boy, was I so very wrong. I always thought that there was much more to Andy than meets the eye, and the way her had managed to seduce his gorgeous busty mom shows how right I had always been. His story is a lengthy one ... too long to tell here, but well worth the read. I suggest to any followers of my story to check it out if you like hot mom/son stories. I talked Andy into posting it. It is under the title, "Educating Mom--Andy's Story". Trust me, you won't be disappointed. It took me some time to convince Andy to share it with all of you from his perspective, and trust me; you should definitely give it a try when he posts it.

"And so, that brings us to the point where I show up on your doorstep, looking like I've been 'put through the ringer'; I think that's the expression you used. I guess now, you know why." Andy sat back in his chair and took another lengthy drink, I'm sure his throat was parched from talking for so long.

"That is incredible," I said as I just sat and looked at him. I felt a big grin start to spread across my face. "You lucky bastard; I am so jealous!"

We shared a chuckle before he pointed at me with an accusatory finger. "Hey, just wait. If things go well on this date with your mother tonight, maybe you'll have a similar story to tell me. And promise me, if something happens, you will tell me, right?"

After what he had told me, if something did happen, how could I not? "Of course, after what you've just told me, I'd feel too guilty not to." I paused for a second as he nodded his head in agreement. After listening to what I'd just said about feeling guilty, I felt a few little pangs shoot through me at what I'd already failed to mention. "There is something I probably should have told you last night, but you kind of ran out of the restaurant in a hurry."

"What's that?" I could see his own curiosity was piqued now. Neither Andy nor I are the kind of guys who 'kiss and tell', but we trust each other to keep the information we reveal to each other secret. We know no one else we didn't want to would learn about our affairs through either of us.

"You know Margaret next door, right?"

"Yes?" he replied questioningly as he sat forward in his chair with a mischievous glint in his eye. Obviously, thoughts of the sexy Margaret were putting his senses on high alert. I proceeded to tell him what had happened with Margaret over the past couple of days. I never mentioned a word about Zoey; there were some things I just knew I couldn't tell him, not at this point anyways. He listened attentively, and I noticed that he refilled my glass a couple of times, just as I'd done for him.

When I finished and sat back, he just looked at me, an incredulous look on his face this time; which I'm sure mirrored the one that had been on my face just a short time ago. "Jesus, what a hot story," he said as he let out a low whistle of admiration. "So she ... she's as hot as she looks."

I took my index finger, touched the tip to my lips and then placed it on my other forearm. "SSSSSSSSSS," I hissed, making a hot sizzling sound. This brought a big chuckle from Andy and I joined in as well. Sharing our recent good fortune with each other seemed to bring us closer together once more; I could see it in his eyes, and I'm sure he could see it in mine.

"Well," he said as put his hands flat on the patio table and stood up, "after listening to that story, I've gotta go home and see what I can do to keep up with you."

"You left your mom there?"

"Yeah, she was still sleeping when I left, with my cum all over her and leaking out of her. After last night, she'll probably still be asleep when I get back."

"Oh, and I'm sure a dutiful son like you will just rush back and make sure you give her more of what you think she needs, right?" I said with a playful smile on my face.

"Of course," he replied holding his hands up innocently, "as her son, I think it's my job to fulFILL all her needs." I noticed he specifically emphasized the 'fill' part of 'fulfill'. "Besides, when she wakes up, she's gonna need to be fed, and I know exactly what's gonna satisfy that hunger."

"Oh, I bet you do." He helped me gather up the dishes and we carried the stuff inside. I filled the dishwasher as Andy headed toward the door.

"So," he said as he turned to me, one hand on the doorknob, "are we good?"

"Couldn't be better," I replied as I gave him a comforting nod. "Andy, I'm really happy for you."

He paused and just looked at me, a warm smile on his face. "Thanks, that means a lot. And hey, tonight?" He raised his eyebrows for a second questioningly as he brought both hands up and I watched as he crossed the index fingers and middle fingers of each hand and showed them to me. I knew what he meant; he was wishing me good luck on my date with my mother. He knew from what we'd shared over the past twenty-four hours how much I wanted her. But right now, I could only dream it would go as well with her as things had gone between him and his mother.

"Me too," I replied, holding up my own crossed fingers. He slapped my arm good-naturedly and left.

I checked the clock and realized I didn't have a lot of time before I was due to pick up my mother. I stripped off my clothes, took a long hot shower and shaved, nice and close. I wanted to look my absolute best for this date. I combed my hair, brushed my teeth and then went into my bedroom to get dressed.

I pulled out what I had decided on, starting with a nice pair of black fitted boxers. An open-necked black dress shirt was next, followed by a slim-fitting charcoal gray Hugo Boss suit I'd bought a short time back. My mother had only seen me in it once before and I knew she loved it. I finished dressing and completed the whole outfit with a pair of black Steve Madden slip-ons that were my favorites. I'd had many compliments from women on those dress shoes and I loved them. Not only did they look great, but they were incredibly comfortable too. Putting everything together, I stepped in front of the mirror and looked myself up and down. "Not bad," I thought to myself as I made a couple of final adjustments to the collar and cuffs of the shirt. Knowing my mother had wanted me to get dressed up for the occasion; I looked once more in the mirror and thought she would approve. It set my mind to wondering what she was going to be wearing. I was almost licking my lips in anticipation.

I slipped my wallet into the inside pocket of the jacket along with my cell phone. Grabbing my keys, I checked my hair one last time and headed out, the weather still perfect as the sun slowly started to drift towards the horizon. I fired up Sally and headed out, a million thoughts racing through my mind. I felt as nervous as I'd been on my first date in high school. I think it was a combination of two things primarily; excitement at actually going out with just about the most beautiful sexy woman I could think of, and nervousness as I had absolutely no idea how this date was going to go, or what to expect. All the other dates I'd been on, well, I always had a feeling of what to expect, how I would react, how the girls or women would react to me ... but here ... I had no idea what to expect from my mother. I kept wondering if I had read too much into that secretive kiss she'd given me the other day out by her pool; or the steamy little episode as we fed each other whipped cream from our fingers. Fuck ... that had been hot! Just thinking about it had my cock starting to rise in my pants, and that was the last thing I wanted right now; to arrive at her door with an embarrassing bulge in my shorts.

I turned on the radio in an effort to occupy my mind as I maneuvered my way through traffic. I hit the selection for the all-sports station and concentrated on listening to the scores. It seemed to work as I felt my stiffening cock slowly start to recede. "Good boy," I said with a quick glance down to my crotch as I made my way the final few blocks to my mother's house. As I pulled into the driveway, I noticed my Aunt Julia's BMW parked in front of the garage.

"Well hello, handsome." I heard as I climbed out of my car and closed the door behind me.

"Aunt Julia," I said as I saw my mother's younger sister closing the front door of the house. "What are you doing here?"

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