Author's Note: I am currently thinking this might go to about 8 chapters before I end the story. I have a pretty good idea of how I want the story to conclude. Something of a happy ending. I also have some ideas for what will happen in between Chapter 5 and the end, so hopefully I can post Chapter 6 within a week or two.
As always, if you have suggestions feel free to offer them.
*****
Roberts groaned in his sleep. He was riding a small sailing ship by himself. It was so warm out and there was no one else around. The waters were pure and calm and allowed the ship to pitch and roll gently in the small waves.
Suddenly, someone grabbed at his wrist and pulled his body and then gaze away from the water. To Roberts' great surprise, the hand belong to some hot guy wearing nothing but a skimpy speedo.
He was skinny and his skin was lightly tanned and looked smooth and soft. Roberts moaned and his eyes widened with shock as the scantily-clad man pulled him into an embrace and started kissing him hard.
While that was happening, two more pretty men appeared on his flanks, both wearing speedo suits as well. They all had surfer bodies. The two new arrivals tugged down his shorts and then started double-teaming his rapidly-inflating tool for a couple minutes, causing Roberts to gasp and groan around the tongue penetrating his mouth.
Then the man kissing him stopped and turned his body before bending over the boat railing. He looked back at Roberts over one shoulder and smiled with pearly teeth as he tugged his swimsuit from his hips, sending it to the deck of the ship.
He spread his cheeks with one hand, revealing a perfect, shaved asshole and winked at Roberts. Roberts grinned lustfully and wondered if he was lubed enough to slide right in. One of the guys kneeling in front of him was absolutely going to town on his dick while the other played with his balls...
Roberts opened his eyes and saw a ceiling. He was in his bedroom. The dream had seemed so real and he felt briefly depressed upon realizing that it had not been real. As he so often did with dreams, he tried to will himself back into it.
Then he moaned and felt something sucking his dick for real. It all clicked in the next second and he looked down to see Kyle kneeling between his legs and blowing him. He had almost forgotten about his current life situation in his post-dream haze.
Roberts smiled as he saw the maid head piece and Kyle's skirt-covered rear sticking up in the air behind him. This reality was better than the dream for now.
Kyle looked up and saw that Roberts was awake and smiled with his eyes. Kyle's eyes looked beautiful this morning, especially with his newly darkened and thickened eyelashes.
-----Kyle Perspective-----
Kyle groaned around his Master's cock. He had finally woken him up. He could feel himself leaking from the tip of his hard cock as it brushed against the skirt of his outfit.
Having his lips stretched open lewdly by the warm dick in front of him was just so pleasurable. It was driving him crazy. With a small motion of his tongue he licked up some precum that dribbled from his Master's cock.
The outfit had been an improvisation. Kyle really had not had anything in mind when he put the clothes on. He just saw them in his Master's kitchen when he walked in through the backyard and felt like he had to put them on. He had needed to put them on.
The stockings had gone on first, then the heels, then the skirt, top, and head piece. Once he had them all on a positive feeling surged through his body.
The panties he had been wearing he left behind on the counter because they were not part of the outfit there. It had made sense at the time to leave them.
Once he had donned the clothing, he saw that there was some lipstick and mascara where the clothes had been as well. He grabbed both and clacked carefully to the nearest bathroom in his heels.
Once inside, he had viewed his reflection in the mirror and applied the lipstick firmly around his mouth. It was a subtle red color. Kyle thought he might not even have realized he was wearing it other than the fact that it made his lips appear wet and glossy in the light.
Next the turned his attention the mascara and carefully applied it to his eyelashes until they were full. The black really stood out judging from his appearance in the mirror. Kyle left the bathroom after turning the light out and put the makeup back where he had found it.
He hadn't thought about what he was doing the entire time in the bathroom. It had just been action. Kyle had never worn makeup before but both the mascara and lip gloss had been right there with the outfit and he had put the outfit on so it just made sense to put the makeup on too since they were all clearly linked.
He snapped back to reality and focused on the delicious treat in his mouth. Using his tongue like he was licking a fat ice cream cone, he wiggled it all around his Master's shaft, eliciting another moan of pleasure from his Master.
His Master was starting to buck into his mouth, and moments later Kyle felt a strong hand on the back of his head, forcing his nose into his Master's fuzzy crotch.
Seconds later, warm, delicious cum was splashing against the back of his mouth and oozing down his throat as he swallowed obediently. His Master produced such yummy cum.
----Mark Roberts Perspective-----
Roberts let out a sigh of relief as he started cumming into his neighbor's wet, willing mouth. He smiled as he saw Kyle's eyes widen in surprise and continued holding Kyle's head down firmly around his shaft as he finished cumming.
When he stopped, he removed his hand and Kyle bobbed up and down a few more times to try and clean any remaining cum before sliding his lips off. Roberts' shrinking dick popped from Kyle's mouth, leaving a trail of saliva hanging between the tip and his lips.
A quiet sigh escaped Roberts' mouth as he engaged in a full body stretch. What an amazing way to be woken up and to start the day. He could get used to this!
While Kyle had been blowing him, Roberts had closed his eyes again and imagined that the two of them were on the dream sailboat, except instead of a speedo Kyle was wearing a skimpy sky blue bikini. Fantasy Kyle had been kissing him and then blowing him and then Kyle had bent over the rail and smiled over his shoulder, lowering his swim bottoms and spreading his...
Roberts opened his eyes again and sat up slowly. If he thought about that he might get hard again. He wanted to draw out his pleasure, which would surely not happen if he ended up cumming again so soon into the day.
He grinned at Kyle. The neighbor boy had gone ahead and put on the mascara, that much was obvious. The look was hot as fuck and it accentuated his eyes which were already stunning and adorable. He was pretty sure Kyle had put the lipstick on too because his lips looked a little redder and shinier. Or maybe that was just the saliva from the blowjob.
Roberts scratched his stomach and swiveled his body to get out of bed. With both feet on the cool wood floor, he hoisted himself up. Kyle carefully extricated himself from the covers and stood up too. As Roberts looked at Kyle his mind was only thinking about two subjects:
One, Kyle made an incredible maid.
Two, maybe he ought to consider a sailboat in the future.
"Green pine cones. When you wake up, I will suggest that you become my maid. You might resist at first, but when I tell you the reasons why I think you should become my maid it will become clear to you that I'm right. Once I wear you down, you will ask me what your daily duties and your uniform will be. You will accept both without question. You will not mind being dressed up like a girly maid or wearing makeup. You will just see it as part of your uniform and not worry about how stereotypically feminine it is. You will find that cleaning and cooking for me turns you on and makes you feel good and horny. Wake up."
-----Kyle Perspective-----
"Thank you for letting me suck your dick again Master. I feel less guilty now," said Kyle sweetly. It was really so nice of him.
"No problem. By the way, would you like to become my maid?"
What? That was a very peculiar question. Kyle eyed his Master curiously.
"Uhmm, the thought hadn't crossed my mind, what makes you ask, Master?" he said.
"It just seemed like you wanted to be."
"What do you mean?"
"Well for one, you dressed up like a maid today before coming to suck my dick."
Kyle looked down at himself. Heels, stockings, a skirt and top, both black and white like a stereotypical french maid might wear. He hadn't thought about it before.
"It was just kind of a spur of the moment thing, Master," he explained. "I wasn't trying to dress like a maid."
"I think you were."
Kyle blanked out for a few moments. He blinked slowly. Had he blanked out or had it just been a second? Kyle frowned. Was his Master right? He tried to think back.
He remembered entering the house from the backyard and seeing the clothes and makeup on the counter. Right away he had decided he wanted to put it all on and dress like a slutty maid. Wait. Was that what had happened? Was he remembering wrong?
"I'm not sure..."
He felt himself spacing out again and as he snapped back to reality he chided himself for being so distracted. It was the morning though.
No, wait, he definitely remembered thinking that he wanted to look like a slutty maid. Once the thought had entered his mind he had become very turned on. He had hoped that he could turn his Master on with the outfit as well.
And there had been a quiet voice in the back of his mind whispering that maybe his Master would want him as a maid once he saw how hot Kyle looked as a slutty maid. Did that really prove that he wanted to be a maid for his Master though?
