Painting Ms. Belding's McMansion Ch. 08

/* Note to Readers:

All characters in this story are fictitious, over 18 and consenting in their actions.

The story is told by Mike. He's just finished his second year at college and he's home for the summer, living with his parents.

Mike was introduced by his mother to the next-door neighbor Ms. Belding; she likes to be called Carol.

Carol is an attractive mid-thirties realtor who has purchased the large house with the intention of flipping it. She needs to repaint the exterior because the current pea green color has no curb appeal. She hires Mike to do the painting.

Mike is now painting Carol's house as his summer job.

Last Chapter Recap

Mike's attraction to Carol is growing rapidly. He finds himself finding trying to seduce his customer every time he gets a chance. Yesterday morning, as they were flirting, Carol challenged him to work naked if she paid him an extra $800.

Mike jumped at the challenge and agreed to work naked. As soon as he took his clothes off, Carol gave him a surprise blowjob, then she sent him outside to work.

At the end of the day, Mike again tried to seduce Carol, hoping to get a chance to fuck his attractive customer. One thing led to another and soon Mike and Carol were in a hot 69 session right out next to the pool. After satisfying each other orally, Mike was able to quickly get hard again and suggest that Carol let him fuck her.

Carol brushed off Mike's attempts and sent him home for the day.

We join Mike the next morning as he prepares to complete another day of work for Carol.

*/

The Next Morning

Before the sun was even up, I was awakened by another wild sex dream. In the dream, I was once again being used as a fuck toy for Carol's harem of saleswomen. My boxers were once again soaked in semen, thankfully the boxers contained the mess.

"What the fuck is wrong with me?" I wondered to myself, "I know I'm hot for Carol, but I'm not gay. Why am I having these lurid dreams about getting gang banged by Carol's team?"

In my mind, sex with Carol wasn't gay. Carol was just an exotic version of a hot milf. It just so happened that her smoking hot body came equipped with a big dick. But it wasn't just the dick that drew my interest. If that same dick were attached to a guy, there's no way I would suck it.

I reflected on our sex session at the end of the day yesterday. When she offered to let me fuck her if I let her fuck me first, I was ready to jump at the offer. I was willing to suck her until she was hard and then let her fuck me just so I could have the chance to see what it felt like to fuck her.

"Why am I letting this woman get into my head like this?" I wondered out loud.

I decided to clean myself up and get to work early so I could make good progress. I rinsed out my boxers and hung them over the shower rod. Then I hopped in the shower and took a quick shower. In 30 minutes, I finished my breakfast and was on the way to Carol's to start my day at work. I arrived 45 minutes earlier than normal and hoped that Carol would be O.K. with my early arrival.

Per our agreement, I left my shorts and shirt in the car and approached the house naked. I knocked on the door and then entered the house.

"Good morning?" I said quietly, wondering if Carol was even awake yet.

"Wow! Early bird looking for the worm?" I heard Carol answer from the kitchen.

I wondered if she meant the double entendre or if I was still being affected by my dream. Either way, as soon as I heard her voice, my partially hard cock grew to full attention. I was becoming addicted to showing myself off in front of Carol. I loved the attention I got from Carol, not to mention the oral sex. I was hopeful that today might start off like it did yesterday.

"I hope I'm not too early," I said as I entered the kitchen, "I wanted to get an early start, it's going to be hot again today."

Carol was in her robe at the island drinking coffee and looking intently at her laptop. She glanced up at me as I walked in; I caught her eyes immediately focusing on my crotch.

"Early is good," Carol said, "Looks like you're ready for more than painting again today."

"Yeah, I guess I'm a closet exhibitionist," I answered, "I can't wait to show up naked for you since I know how much it turns you on."

"You flatter yourself college boy," Carol laughed, "you're the one who sold yourself for an extra $800."

"Easiest eight-hundred bucks I've ever made," I answered, smiling, "I should have held out for an even thousand, you would have paid it you pervert."

"If you had half a brain, you'd be trying to learn from me, not fuck me," Carol chided, her tone growing more serious, "Do you realize that when the woman on my team sell a $2 million house they make almost 10 times what you're making to paint my house."

"What?" I asked, "how does that work."

"They make 3% on every sale which is $60,000 on a $2 million house," Carol explained, "And most of my team sells a home every month. So, they're making almost 100 times what you do."

"Holy shit," I said, my cock losing its hardness as I listened in disbelief.

"Exactly," Carol said, "and all of them were horny college kids like you when I found them. Being horny is just a form of greed. Once they understood that, I helped them channel their sexual greed into financial greed."

"Can you teach me to make that kind of money, Carol?" I asked, thinking about a Lamborghini in my future verses just a chance to bang my new summer job boss."

A New Bargain Emerges

"I can teach you," Carol said, "but you must be willing to learn. I'm not sure you have the discipline even though you are fun to look at."

Carol got up from the island to get herself another cup of iced coffee. I watched as she pulled the bottom of her lightweight summer robe down to cover her bare ass as she got off the chair. My cock started to get hard again as I got a glimpse of my bosses nearly perfect ass.

"I'm willing to learn," I said, putting on my most sincere voice, "I'd love a chance to make that kind of money. I can be very disciplined."

Carol filled her glass with ice at the fridge, then poured another cup, turning to look at me after she did.

"You're the picture of discipline standing there with that raging hard on, aren't you," Carol laughed, "Besides, there's nothing in this for me, why should I do this for you?"

"How about I discount the price on the house in exchange for your training and guidance," I offered without really thinking the idea through completely.

"Don't be ridiculous, you need that money for college," Carol reasoned, "I couldn't re-trade our deal on you like that."

"I think it's a fair offer, and I'm willing to do it," I suggested, "I'm serious about learning from you."

"How about something more personal," Carol proposed, "something that's non-financial but is worth a lot to you. Something that also holds reasonable value for me."

I started to realize where Carol was headed, I was uncertain about letting this go any further, but I was really interested in learning how to make that much money. I thought back to yesterday, when I was willing to let Carol fuck me if I could fuck her afterward. I was willing to do that for free, and now I was going to learn a skill that could deliver huge future income streams.

"Can you tell me what you're thinking, boss?" I asked sheepishly, looking down a little as I did.

"I think you know what want," Carol said, smiling, "I've been watching you parade that tight ass around here for 24 hours and I'm thinking I should have it."

"So, I let you fuck me, and you teach me how to sell million-dollar homes?" I asked, looking to clarify Carol's request.

"Don't make it sound so vulgar, Mike," Carol scolded, "I'm going to take you in as my apprentice. A naked apprentice who is taking guidance from his mentor."

"Taking guidance?" I said, "is that all I'll be taking?"

"You'll be taking guidance and my cock, wherever I want to put it, whenever I want to give it to you," Carol answered, with a coy grin, "it's the same deal I've struck with many of the successful members of my team."

I stood there thinking about Carol's proposal. I enjoyed our past sexual interludes. I never considered anything we did as being "gay". I just viewed Carol as an extremely hot milf with extra equipment. However, if I agreed to this arrangement, it meant that I was O.K. with getting fucked in the ass. Being fucked in the ass is sort of the defining quality of being gay.

Then again, many straight men let their girlfriends peg them, and they aren't considered gay. If I thought about this arrangement that way, I was more comfortable with it. The key to all of this was that nobody else could ever find out. If they did, I was certain I'd be labeled as gay from that point forward.

"If I agreed to this apprenticeship, when would it start," I asked, looking sincerely at Carol.

"There's no time like the present," Carol answered, "I could mentor you right now, before you start painting."

"Well, I guess I'm already naked," I said, my voice shaking as I tacitly agreed to become Carol's apprentice.

"I think we should shake on the deal," Carol said, holding out her hand as she approached me.

As I looked down at Carol's hand, my eyes caught a large bulge in the front of her lightweight summer robe. It was clear that Carol was turned on by the new insect caught in her web. We shook hands on the deal and looked each other in the eye as we did.

"Let's get started then," Carol said, she grabbed me by the hand and led me to the bathroom down the hall near the laundry room.

We walked down a short hallway that led from the kitchen to the garage. On the right there was a door leading to the laundry room. On the left, there was a door leading to a bathroom with a shower. Carol took me to the shower and ran the water until it was lukewarm. Then, she switched the shower heads to a handheld shower head that was tube shaped.

"We need to clean you out before I mentor you," Carol said casually, "bend over, I'll show you how to do this the first time."

I bent over and felt Carol place the nozzle against my hole. She pressed slowly until the wet head was about 2 inches inside my ass. Then she turned up the flow and I felt my intestines fill with the lukewarm water.

"Oh my God," I said, "this feels strange as hell."

"Stay calm," Carol said, "after a while, you'll be so used to this, you might find it pleasurable."

After a few seconds, Carol told me to hold the water in and walk to the toilet.

"Hold it in as long as you can," Carol said, "when you can't hold it any longer, let it go and then repeat this process two more times. I'll wait for you by the pool."

Carol left me in the bathroom to continue using the water dildo to flush my ass. I felt like I had fallen into a weird fetish porno scene. I was so far out of my element; I was amazed that I could even do this to myself. I was just going through the motions, trying to get this process behind me as fast as possible.

As I walked back through the kitchen on the way to the pool, I was shocked by how hard my cock was, especially after what I had just finished doing. I couldn't tell if it was because of the kinky stuff I just did to myself, or if it was because I knew that Carol was waiting by the pool to "mentor" me.

The Apprentice Gets Mentored in Public

As I walked out of the kitchen patio doors and on to the pool deck, I saw Carol waiting for me in one of the pool chaise lounges. She was naked except for sunglasses; her 8-inch cock fully erect, pointing skyward. The morning shadows were long across the pool and yard. It was still early morning, and the heat was just coming up. Carol turned to see me approaching and smiled.

"I'm going to make you such a good apprentice," Carol said smiling, "when we're done this summer, I hope you'll consider joining our team. You have great potential Mike."

I didn't know how to answer her so I sat down in one of the pool chairs and waited for my instructions.

"How would you like me to start?" I asked, my voice somewhat hesitant and shaky.

"I like that you're sporting a hard-on," Carol said, "I think you like it when Momma has her big dick out on display. Why don't you suck Momma's big cock so it's nice and wet when you beg for it in the tight little virgin ass of yours."

"I'm not going to beg for it," I said, defiantly, "I'm not gay."

"Of course you're not gay," Carol replied, "I'm your hot milf boss, it's not like you're giving it up for a man. You can't tell me you haven't let your girlfriend peg your ass in a moment of lust."

"Not yet," I answered, watching as Carol's cock throbbed, lifting off her stomach to match the rhythm of her pulse.

"You're going to love being Momma's apprentice, Mike," Carol said, "Now don't keep me waiting and take me in your mouth so I can start mentoring you."

"Promise me you're going to teach me how to sell million-dollar homes," I said, looking Carol in the eye, "I need to know that if I do this, you'll keep your word."

"If you live up to your end of the bargain, I will live up to mine," Carol said, in a serious tone, "Do you think I would have such a loyal team if I didn't live up to my word and create meaningful change in their lives."

"O.K.," I replied, "I'm willing to go all-in here and learn everything I can from you.

"Good boy," Carol said in a comforting voice, "Now why don't you get over here and make Momma feel good."

I got off my chair and moved to my knees next to Carol's chaise lounge. Even though I was nervous about giving up my anal virginity to her, I was incredibly turned on looking at her naked body out in the open in her backyard.

I started by working on her D-cup breasts. I worshipped them like she was a queen. I kissed, licked, and sucked her right nipple. I listened to her breathing and gauged her reaction to ensure I was getting the reaction I wanted. I loved sucking on her perfect tits.

"Mmmm, I think my apprentice loves Momma's bit tits," Carol whispered, "tell me if you do, baby."

"I love your tits, Carol," I said, my lips wet from suckling, "they are so pert and perfect."

"Please, baby, call me Momma when I'm mentoring you," Carol moaned, reacting to my ongoing breast worship.

"I love Momma's tits," I groaned, incredibly turned on by Carol's role play.

"Baby, look how hard you've made Momma's cock," Carol sighed, "don't you want to have me in your mouth?"

I continued to suck on Carol's breast for a few seconds and then took her less than subtle hint on what she wanted next. I slowly kissed my way down her long flat stomach until I was face to face with her raging hard on.

"Do you want me to suck your cock for you, Momma?" I asked, doing my part to continue the role play.

"Oh yes, baby, please nurse from Momma's big cock before I make you my apprentice," Carol whispered in a guttural tone.

Carol's role play had me more turned on than I could remember being in recent history. I couldn't help but reach down and stroke my hard cock. I wasn't even concerned that we were doing this out in the open, under a blue sky, as the sun was starting to heat up the air around us.

I took Carol's cock into my mouth and immediately felt Carol's hands on my head. At the same time, Carol's hips raised off the lounger so she could drive more of her 8-inch cock into my mouth.

"I love your big cock, Momma," I said, surprising myself with my confession, "it's so powerful and strong."

"I know you do, baby," Carol groaned, "I knew from the first day that you were going to make a great apprentice."

I had moved from worshipping Carol's tits to worshipping her big cock. I couldn't believe how turned on and devious I felt naked on my knees sucking the older woman's cock. She seemed to have me in her spell now. I was becoming a willing participant in her unique approach to mentoring.

"That's it baby, take more of me into your mouth," Carol groaned, "By the end of the summer you'll easily take all of me down your throat."

I worked more of Carol's hard cock into my mouth while I cupped her large, hairless balls in my hand. I was really turned on by giving my new boss pleasure. I wanted to be the best apprentice she'd ever had.

"Momma can't wait to have you like this every day," Carol groaned, "I love your hot, tight, college boy body."

"I love our body too, Momma," I said, pulling off Carol's cock briefly, "You're so fucking hot."

"Get Momma's cock nice and wet, baby," Carol said softly, "I am so ready to take all of you."

I went as deeply as I could on Carol's big cock. Her cock head hit the back of my throat and I pushed hard until it popped into my throat. I chocked a bit but relaxed and tried to take more. My mouth filled with saliva that spilled out all over Carol's big pink cock.

"Oh baby, I felt myself go into your throat," Carol growled, pushing down on my head, "do it again baby, take Momma into your throat."

Motivated by Carol's challenge, I dove back down on her cock. This time I tried to yawn as she approached my throat, and she popped in more easily. As she felt herself enter my throat, I felt the pressure on my head increase exponentially. Simultaneously, she lifted her hips off the chair driving her cock hard into my gullet.

"Do it, baby, let Momma's big cock into your throat," Carol commanded, "I want to see your nose right up against Momma's shaved pubic bone."

My participation was no longer voluntary, I was now being face fucked by my milf boss. I was shocked by how much I liked it. I was so fucking turned on I was pretty sure I was going to blow my wad right there on the pool deck. Carol sat up, still holding my head with both hands. Then, I felt her swing her hips around so she could stand up from the chair. I watched as my statuesque boss stood with her legs spread to face fuck me in her own back yard.

It was so hot looking up from her crotch, across her long flat stomach, over her big tits to see her looking down at me intently watching her victim give up his throat to her cock.

"Just a little more, baby," Carol coached, "Another two inches and you will have all of Momma's cock in your throat. You are doing so good, baby, you're making me proud."

I loved Carol's dirty talk; it made me hot as hell. I wanted to prove to her I was a worthy apprentice and take her balls deep right now. I pushed off Carol's tan thighs so I could talk and looked up at Carol.

"Help me take it all right now, Momma," I begged, "I want to feel you all the way down my throat."

"Good boy," Carol laughed, "Look how wet you're making Momma's dick, I'm so ready to fuck you now. Let's start with that throat and then I'm going to bury myself in that tight college boy ass!"

I relaxed my throat and gave myself to my milf boss. I was hers now; naked on my knees letting her use my throat to pleasure her big phallus. She worked my head like a boxer works a speed bag, punching her cock into my throat a little deeper each time. My throat was making obscene sloshing noises and I loved it.

"Almost there, baby," Carol grunted, "just a few more strokes and I'll be balls deep in your throat."

"Gawk, gawk, gawk," I heard my throat squawk as Carol fucked my skull.

In a final thrust, my nose was pressed against Carol's smooth pubic bone. She had done it; she had helped me reach my first goal. I stopped jacking my cock because I didn't want to cum too soon. I couldn't believe how turned on I was by Carol's rough treatment. Maybe those dreams of being gangbanged by her entire team were trying to show me some subconscious desire I had. At this point, I was thrilled to have my hot milf customer using me for her pleasure. Carol held me tight against her smooth pubes, looking down on me with a sexy grin.