The Face - Painter
Chapter 3

Copyright© 2012 by rmdexter

Erotica Sex Story: Chapter 3 - 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  

I hurried through my shower and quickly got dressed in a pair of shorts and a polo shirt. The session with Margaret had set me behind a little bit and I rushed around the house getting some stuff together. Not that I was complaining, the slippery hand-job Margaret had given me had been fantastic. I grabbed another pair of swim trunks, a bottle of wine from the cupboard and slipped my laptop into my shoulder bag. Taking a last look around, I picked up my keys, slipped on my sunglasses and headed out.

It was great to feel the warm sun beating down on me as I feathered Sally back and forth through traffic on the way to my mother's. Having the top down on the old Mustang was one of life's little pleasures that I absolutely loved. I pulled into our family house and parked beside Emma's car in front of the double garage. I let myself in and kicked off my flip-flops by the front door.

"Hey, anybody here?" I shouted as I made my way further into the sprawling house.

"Back here, honey," I heard my mother's voice coming from the kitchen area near the back of the house. I made my way down the hallway that lead into the rear portion of this section of the house; the walls opening into a large combination kitchen/great room. The house had ten foot ceilings throughout with a high cathedral ceiling over the great room area. The back of the house was heavily windowed to look out over the pool area and the nicely landscaped yard. My dad had put a lot of work into this house and yard and my mom hired a landscape company to keep everything in order outside. It looked great.

"There you are, sweetie," my mother said as she came out from behind the fridge door. I could only stare as she walked towards me, those wide flared hips of hers swaying seductively. My eyes looked ravenously up and down her voluptuous body, those massive tits of hers leading the way towards me. She was wearing a luscious charcoal-gray sweater that hugged her sumptuous form wonderfully. The sweater had sleeves that ended just above the elbow and a deeply scooped neckline that exposed a dick-hardening amount of her substantial cleavage. I noticed that the sweater was actually sort of a cardigan, with about five large buttons up the front. The bottom three buttons were done up with the third one anchoring the two sides together right between those huge guns of hers. Her ample bosom caused the tight sweater to pull out from either side above that; leaving the top two buttons undone. The tight ribbed material of the sweater flowed snuggly around every delicious curve of her body, accentuating that sexy hourglass figure of hers. It followed the wide fullness of her chest and then pulled in trimly at her waist before flaring out at her wide womanly hips. The bottom of the sweater fell nicely over the top of a tight white miniskirt, which followed the flow of her child-bearing hips before ending high on her thighs. My eyes followed the line of her long tanned legs downward before they ended with a smart pair of white strappy sandals that put the finishing touches on a gorgeous outfit.

"Mom, you ... you... ," I simply stared in awe as she moved in to hug me.

"There's my big boy." Her arms slipped around my neck as she pressed herself against me. She tilted her face up towards mine and as I lowered mine towards hers, she pressed her soft lips to mine in a gentle kiss. She pulled me closer to her and I felt those massive orbs pressing firmly against my own chest as the kiss seemed to last a little longer than usual before she pulled away. "I'm so glad you're here." As she kept her arms locked around my neck but drew her face back slightly from mine, the luscious scent of her perfume filled my senses like an intoxicating elixir. Oh man, she smelled as good as she looked. She looked right into my eyes with a look of pure joy, a huge smile spreading across that gorgeous face of hers. She gave me another quick peck on the lips before slipping her arms from around my neck and letting her hands slide slowly down over my muscular chest.

"Mom, you look amazing," I gushed as I looked down at her, her swirling frosty-blonde hair falling in lustrous waves about her shoulders. Once again I was struck by how much she looked like Wifey, the internet porn star.

"You don't look so bad yourself," she said as her hands gave my firm pecs a little squeeze before she let go. "I was hoping you'd like this." She stepped back and did a little pirouette so I could see the whole look. The stretchy white fabric of her miniskirt showed off her sumptuous round ass and dynamite legs exquisitely; but that top ... fuck ... it was incredible.

"Like it? I love it!" I stood and stared as she put her hands on hips and turned from side to side as she posed for me. Oh Jesus, I could feel my dick stiffening in my shorts already. "Those ... those clothes, are they new?"

"Yeah, I decided I needed a few new things; that I needed to spark up my wardrobe a bit. This is some of the new stuff I bought."

"If the other things are like what you're wearing, I'd love to see the rest of it."

"Well, just keep your fingers crossed, and maybe you'll be lucky enough to see," she said as she kind of thrust her hip at me provocatively before giving a little giggle and stepping back to the kitchen counter.

"This is for you," I said as I reached into my bag and handed her the bottle of wine.

"Oh Connor, you didn't have to do that ... but since you did, be a dear and open it, would you? I'd love a glass." As she opened the fridge and put a few things on the counter, I pulled out the corkscrew and opened the bottle. I retrieved a couple of glasses from the cupboard and poured a glass for each of us.

"Mom, those new clothes you're wearing; that reminds me; are you wearing that new bra you were talking about earlier?"

"Maybe," she said as she gave me a teasing smile.

"I thought you promised to show me."

"I said no such thing. I think what I said was I MIGHT show you, provided you did a good job of handling the grille."

"Then when do we eat?" I asked eagerly as my eyes flicked down to her sumptuous tits.

"Oh you," she scolded with a dismissive wave of her hand. "We won't be eating for a little while yet. The girls are outside." My eyes followed hers as she nodded towards the pool. "Why don't you go out and join them?"

"What time did Emma get here?" As I looked out, I could see Zoey sitting in one of the deck chairs, her hands busy texting on her cell phone. I could see movement in the water and knew Emma was swimming laps; which she did every time she had the chance.

"She got here about a half hour ago. She's been working a lot of extra hours on that big merger her company is working on so her boss gave her the afternoon off. Actually, I think he knew she needed to work off some stress."

"That's good; she deserves a break." I sat down on one the high stools at the breakfast bar and faced my mother across the granite counter. "What was it you wanted to talk to me about, Mom?"

She looked a little nervous after I asked that and she took a sip of her wine before setting her glass down and looking at me. "Well, here's the thing ... you know how much I loved your father."

"I know, Mom. He was a great guy."

"And you how much you mean to me ... you and the girls." She paused and I wondered where she was going with this. "Well, I ... I was thinking about maybe getting back into the dating game." She looked kind of sheepish when she said this, like a little kid asking for their parent's approval; only this time it was reversed.

So this was what this was all about. As I took in my mom's words, I was at first surprised because I hadn't seen this coming at all. But as I looked at my mom, standing there nervously waiting for a response from me; the reality of her situation hit me like a tsunami wave. She was a beautiful woman, in the prime of her life, with so much to offer to another person. I knew she had loved my father dearly; when he'd still been alive, you could just see it in the way they looked at each other. But at 47, she still had a whole lifetime ahead of her. I knew she must be painfully lonely at times, missing my dad; and I knew that had to be incredibly hard on her. Now here she was, basically asking for my permission; and who was I to deny her? She didn't have to ask me but I knew she wanted my approval and she would respect my opinion, and as I looked into those deep blue eyes, my heart went out to her.

"Mom," I said slowly as I reached across the counter and took her trembling hand, "I think that's a great idea." Her eyes lit up and she squeezed my hand tightly as a beaming smile came across her face.

"You ... you really think it would be okay?"

"Sure, Mom, I really do. I know you'll always love Dad; but you're still young enough to enjoy life. And you deserve to be happy."

She came around the counter and hugged me tightly, those big round breasts of hers pressing into me warmly. "Oh Connor, thank you so much. You know your opinion means everything to me." She reached across the counter and grabbed her wine glass. "Shall we toast then? To the new me?" I could see a look of both relief and excitement in her eyes as she raised her glass.

"To the new you," I repeated as I clinked my glass on hers and we took a drink to celebrate her new outlook on life.

"So, tell me," I said as we both set our glasses on the counter and she moved back to where she'd been dealing with the food, "is there somebody?"

"What?" she replied with a confused look on her face.

"Is there somebody specific? Has some guy asked you out?"

"Oh," she said and gave a little laugh, "of course you would ask that. No, nobody's asked and there is nobody specific. I know that after being with your father, I guess you could say I'll have some pretty high standards for any man to meet. I'm not really in any hurry, and I guess I can be choosy, if I want." She paused for a second and I nodded in agreement to what she'd just said. She looked up at me again, a more serious expression on her face once more. "So that kind of brings me to the second thing I wanted to talk to you about." She stopped and left that hanging out there.

"Second thing?"

"Yeah ... it's been a long time since I've dated and I was wondering, do you think you could help me with that?"

"You mean like give you advice?" I asked, somewhat mystified that my mother would be asking for dating guidance from me.

"No, silly," she said with a nervous little smile and then looked intently at me once more. "I was wondering if we could go out on a date together; you know, so I can see what it's like again."

Well, this was definitely unexpected! My mother was asking me to take her on a date. As my eyes flicked down to those voluptuous tits of hers swelling over the cups of her bra, it was an easy decision for me to make. "I'd love to, Mom." The beautiful smile reappeared on her face immediately, her brilliant white teeth lighting up her face in joy. "It would be my esteemed honor to escort such a beautiful woman." I made an exaggerated gesture of a bow, extending my arm and bending from the waist. She gave a little laugh at my good-natured gesture as we each raised our glass and toasted to our date.

"So, when did you have in mind?" I asked, trying to suppress my soaring excitement at the prospect of going out with my gorgeous mother.

"What about this Saturday?" she asked, appearing to be visibly eager as well. "Are you free? Can you make it?"

"Saturday is great, I'm totally free. What would you like to do?"

"Well, I want it to be just like a real date. So is it okay if we get dressed up?" That was definitely alright with me; I was anxious to see just what she'd wear.

"Of course, I wouldn't expect anything else."

"Oh good, I've got my eye on a new dress that should be perfect. How about we go out for a nice dinner; then see a show; I haven't seen the new Cirque du Soleil show yet."

"I haven't either."

"Excellent. And then maybe after the show, we can go somewhere for a drink." She looked at me questioningly to see if that scenario was okay with me.

"That sounds perfect, Mom. Do you want me to make some reservations and pick up the tickets?"

"No silly; I'm the one who asked you out." She gave me a devilish little smile again. "I'll make the reservations and take care of the tickets. This date is all on me. You just have to pick me up, like a real gentleman would."

"You don't think I'm a real gentleman?" I gestured to her in mock despair.

"Of course not," she said with a giggle before looking at me seriously. "I think you're a perfect gentleman, Connor. That's why I'm so happy you've agreed to do this for me." I could see her eyes get slightly moist as she started to tear up.

"I'd do anything for you, Mom; anything."

"Oh thank you, sweetheart," she said as she came around the counter and hugged me once more. "You are so dear to me; I love you so much."

"I love you too, Mom."

"Okay then," she said as she gave me a quick peck on the cheek and moved back a step, "Saturday it is then. I'll call right now and make an appointment to get my hair done. Why don't you go out and visit with your sisters for a little while? I know they both love it when they get to see you. It's gonna be another hour or so before I'm ready for you to start the barbeque."

"Okay; I think I'll just put my suit on first." As my mom reached for the phone, I grabbed the suit I'd brought and went into my old room to change. It always felt both strange and yet comforting to be back in the room I'd spent most of my life in. As I thought about the upcoming "date" with my mom, I thought of all the loads of cum I'd pumped out in this room thinking about her. It brought a wry smile to my face.

My mother was still on the phone when I came back, so with one further glance at her spectacular profile, I slung my laptop bag over my shoulder, grabbed my sunglasses and my glass of wine and ventured out to the pool, closing the door behind me to keep the air-conditioning contained inside.

"Hey Zoey," I said as I put my stuff on the patio table and pulled my laptop out of its case.

My baby sister barely stopped her texting long enough to acknowledge my presence, "Hi Connor; just get here?"

"A few minutes ago; I was talking to Mom inside." I flipped open my laptop and fired it up; I had to get to work on this article or I was gonna be in deep shit. As I pulled off my polo shirt and set it beside me, I looked over at Zoey as she went back to her texting, her knees pulled up in front of her as she lay back on the deck chair. Her curly blonde hair swirled about her shoulders as she nibbled on her full bottom lip cutely while her fingers were busy manipulating those tiny buttons on her phone. "What would you do if I took that phone away from you?"

"Die!" she said emphatically as she stuck her tongue out at me and went back to what she was doing. I'm sure my mom had threatened to do that to her a thousand times already. The world revolves around their cell-phones for these girls, it seemed. Who was I to talk; although I didn't text like these teenagers, I never went anywhere without mine.

With Zoey engrossed in her texting and obviously in no mood to talk right now, I took a sip of my wine and with my sunglasses on; I was able to look over at her surreptitiously without her being aware. She had on her favorite white bikini, one of many suits she owned; it was my favorite too. I had a number of pictures of her in this suit, taken at various family get-togethers like this one. I would often bring those pictures up on my computer at home when I wanted a little ... let's call it "inspiration", during a jack-off session.

As I looked over at her, I felt a little surge go through my cock as once again I was amazed at how skillfully the little pieces of clinging material that made up that suit could contain that voluptuous curvy body of hers. The top was made up of two little triangles of material that barely encased those spectacular 34DDs of hers; the pieces of fabric held together by white spaghetti straps that tied around her back and behind her neck. I could see the hint of her budding nipples casting small shadows on the front of those clinging pieces of material. The bottom was similar, appearing to be two triangles joined together where it disappeared between her legs. It was cut very low and, like the top, the two pieces were tied together with little tiny bows at each hip. I don't know how many times I had pictured deftly plucking at one those bows and watching the bottom fall away to reveal the luscious treasure lying beneath.

Like I said earlier, Zoey was all delicious curves and mysterious valleys. Her body was lush and seemed to be just calling out for your hands to explore all the pleasure it had to offer. And as I mentioned, she had retained just that little bit of baby fat that seemed to make her all that much more innocent and alluring. She was just perfect right now; but I knew she'd have to watch herself in the next few years to make sure she didn't let herself go.

As I looked at her out of the corner of my eye, she seemed to think of something important and immediately put down her phone and almost jumped out of her chair. "Hey Connor, I forgot to show you something," she said gleefully as she stood next to her chair and faced me directly, her hands on her hips. She looked down and my eyes followed hers until they landed on shimmering stones coming from her navel. My mom had told me on the phone a couple of weeks ago that she had relented and let Zoey get her navel pierced, and now Zoey was proudly showing me how it looked. And it looked pretty fucking sexy to me, alright! I could see the little silver ball just above her navel and then a similar one at the bottom of the post right in her navel opening. Dangling from the bottom ball were two thin strands of rhinestones, one about two inches long, the second one about an inch longer. Man, did it ever look hot! As I mentioned before, I am not too keen on tattoos and what I feel are unnecessary piercings; but this one was perfect.

"Zoey, that looks great," I said sincerely as my eyes roamed up and down her plump little body; nicely tanned and seeming to just glow with youthful energy.

"So she showed you what she did to herself?" I turned as Emma's voice came from the direction of the pool. She climbed up the ladder at the end of the pool near us, water sluicing off her emerging body. I could see she had on a red Speedo, the type that fits almost all the way up to the neck and is cut extremely high on the hips; the choice of all competitive swimmers. As she grabbed her towel she'd set by the pool, my eyes were immediately drawn to the way the wet stretchy fabric formed snuggly around her 36Ds. The refreshingly cool water of the pool had caused her nipples to stiffen, their pronounced form readily apparent beneath the damp material.

"I don't know why you'd do something like that to yourself," Emma said to Zoey as she walked over to us, drying herself on the way. My eyes were drawn away from Zoey's navel piercing and zeroed in on those gorgeous long athletic legs of Emma's. With the way that bathing suit was cut, it really accentuated her tall perfect figure. The damp suit clung to all her curves like a wet loving kiss while those tanned legs seemed to go on and on forever from the high-cut leg openings.

"Well, I don't care what you think," Zoey spat back like a spoiled little kid. "I like it ... and Connor likes it too."

"Yeah, well Connor's never been known to have good taste," Emma said as she looked at me with a playful smile while she wrapped some of her long brunette hair in the towel and rubbed it dry.

"What's that supposed to mean?" I asked indignantly.

"What about that girl you dated in high-school, Chantal what's-er-name?"

"Chantal Simmons? What was wrong with her?"

"Kind of a skank, don't you think?"

Chantal actually was kind of skank, but man, she could suck cock like nobody's business. Anywhere, anytime, she loved to get her mouth filled. "A skank? Are you kidding me; she was very sweet," I replied, all the time knowing Emma was right; about Chantal anyways.

"Sweet my ass." My sister shook her head as if to say that if I couldn't see it like she did; this part of the conversation was over. That was the lawyer in her coming out; presenting the facts as she knew them; then shaking her head in dismay if the guilty party was too ignorant to see through their own stupidity. Her attitude brought a smile to my face as I watched her rubbing the towel down those long tanned legs of hers. "Well, I'm gonna go in and get out of this wet suit."

"Grab yourself a glass of wine on your way back," I said as I gestured towards my glass on the table. My eyes followed the sensual sway of that perfect ass of hers as she walked towards the house, her hips moving from side to side and up and down in a perfect rhythm. The way that damp suit cupped her firm rear end was spectacular; the muscled yet nicely round cheeks drawing my eyes like a magnet.

"So Connor, you really do like it, don't you?" Zoey asked with her full lower lip pouting out; now wanting the attention back on her, as usual.

"I think it looks absolutely perfect," I replied with emphasis, watching the happiness appear on her face as I did.

"Do you ... do you think it looks ... you know ... sexy?" she asked with a naughty glint in her eye.

"Yes it does, it looks very sexy ... very grown up," I said with a gentle nod of my head. I could see her looking more pleased with herself, especially after I added that "very grown up" part.

"Do you think I look fat?" That question seemed to come right out of the blue as she kind of turned her back towards me and looked back at me over her shoulder, her hands still on her hips. Oh man, what a fucking pose she had presented to me; her curly blonde hair falling teasingly over one eye, those huge round tits thrusting out before her, and that plump beach-ball like bum pointing directly towards me. I almost gulped in surprise as my eyes roamed over that lush touchable body of hers.

"No, not at all. Why do you say that?" I asked in mock surprise, knowing girls at that age worried about their weight constantly.

"Well, I just overheard some girls at school talking about me. One of them called me a 'fat cow' and one said something else that was pretty mean."

"I don't think you're a fat cow at all. I think you're beautiful. The girl that said that is probably just jealous."

"That's what Jenna said." I knew Jenna was her best friend and would stick up for Zoey through thick and thin.

"And Jenna's exactly right." My curiosity about what else she said got the better of me though. "So what did the other girl say?"

"She said the only reason I got an 'A' in English class was that I was always flaunting my big boobs and fat ass at Mr. Dexter." She kind of turned and showed me that lush plump ass of hers as she said this, as if to give me a good look in order to give my judgement on the "fat ass" comment.

"Fat ass?" I exclaimed as if even the thought of it was an inconceivable notion; although like I said, Zoey's cute bum was perfectly full, round and soft right now; but verging on going over the edge if she didn't watch it. "I think your little bum is nice and cute, just like the rest of you. Now your big boobs, I think we both know there's nothing you can do about that." I paused as both of us looked at that tremendous chest of hers, so round and full with a dark line of cleavage that you just wanted to stick your tongue into. "So, were you flaunting them at this Mr. Dexter?"

"Of course not!" she said indignantly; but I knew my little sister better than that.

"So if I called the cops and they gave you a lie-detector test about that, you'd pass?" This made her laugh and her girlish giggle lit up both our faces.

"Well, maybe I did a little," she confessed with mock innocence, "but that's only because Mr. Dexter makes me sit in the first row and well, I think he likes to look too." I wondered about this guy Dexter; wondering if he was some kind of perv teacher or just a regular guy. Knowing the way Zoey dressed and her raw sexual allure; I figured he was just a normal guy who liked to put the eye candy up front in the first row. I was pretty sure I'd do the same thing if I was her teacher. It would be great to look over every day and see those full round tits of hers staring back at me; or catching a glimpse of those plump creamy thighs of hers beneath the short skirts I knew she loved to wear.

"When you have a beautiful build like you do Zoey, all men like to look; you should know that by now."

"All men?" she asked quizzically as she looked at me and swayed slowly from side to side, those massive tits wobbling gently. "Even you, Connor?" She had a devilish look in her eye as she provocatively tilted her head to one side. When she said that and with the slow teasing swaying of her upper body, my eyes couldn't help but flick down to those heavy round orbs. I could feel the sweat break out on my forehead as my gaze took in those round voluptuous tits, enticingly accentuated by her tiny white bikini. As I lifted my eyes back to hers, she was staring at me intently, as if she could read my very thoughts. I could feel the blood rushing to my face, like a little kid being caught red-handed. Fortunately, I was saved from having to answer as I heard Emma's voice as she emerged from the house.

"So Connor, did Mom talk to you?" The tenseness of the moment was broken by the intrusion and I saw Zoey sit back down in her deck chair and pick up her phone as I turned towards Emma.

"About what?" I asked as I watched Emma approach. Jesus, she looked fucking hot! She had changed out of her actual 'swimsuit" into a jet black bikini; once again, with Emma in a black one, and Zoey in a white, they were like night and day. Her toned body looked great in the suit; her lithe form athletically sculpted and nicely tanned, those large breasts of hers being perfectly shaped. She was carrying her briefcase in one hand and a glass of the wine I'd brought in the other. She put her stuff down at the table next to me and took a seat.

"I thought Mom was going to talk to you?" It was like we were feeling each other out; wondering if the other was talking about the dating thing; or something else entirely.

"Well, we talked about something earlier when I got here," I said kind of noncommittally; as if it was no big deal.

Emma pause for a second before finally broaching the subject, "Did she mention about the dating thing?" she asked delicately, just in case my mom hadn't mentioned it yet.

"Yeah, she did." I could see the relaxed expression on her face now that we were both on the same wavelength.

"So, what did you say?"

"I told her I think it's a great idea."

"Oh good," Emma said with relief. "She was so worried about what you would think. I know if you hadn't liked the idea of her dating, she wouldn't do it."

"Really?" I asked incredulously.

"Oh God, no. I don't know why, dear brother, but our mother thinks the world rises and sets around you. Your opinion means everything to her."

I was shocked but thrilled by what Emma had just said; that my mother valued my opinion that highly. I let my sister know what I thought, "She's still a young, beautiful woman; she deserves to be happy."

"I'm glad you feel that way. It will make it so much easier for her to get back out there if she knows you feel like that. I think she's been waiting long enough."

"No kidding," Zoey's voice reached our ears and we both looked over at her, her fingers pausing momentarily from texting on her phone. She looked over at us and you could see the concerned look on her face as she talked about our mother. "We all know ... and she knows, that she can never replace Dad; but you guys aren't here all the time; you don't see how lonely she is sometimes."

"That's why it will do her some good to get out there, meet some new people," Emma said; both Zoey and I nodding our heads in agreement.

"How would you guys like a snack," our mother's voice ended the conversation as she came out of the patio door, a tray in her hands. Jesus, she looked so fucking hot in that new outfit, the cardigan and the structured bra I knew was lying beneath cupping and lifting her massive breasts until they seemed to threaten to spill over the top of the plunging neckline.

"Here you go, some veggies and dip," she said as she set the tray down on the table between Emma and me. "I've got some more stuff to do inside. Connor, I'll let you know when to start the grille. You two have some work to do, right?" Emma and I both nodded as I turned to my laptop while Emma reached into her briefcase and pulled out a couple of files.

For the next hour or so, I worked on refining my article while Emma read through her files and occasionally jotted down some notes on a legal pad. Zoey went into the house briefly and fetched a school book and finally put her phone away before starting to do some studying. I knew that as much as she loved to socialize and pretend to dislike school, she got excellent grades. Emma and I had both done well, and Zoey seemed to be following right along. I knew that was why my mother gave her a little leeway every now and then; like with this navel piercing thing.

 
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