The Entertainment Ch. 01

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A sissy maid prepares to entertain his owners' guests.
4.4k words
4.43
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52

Part 1 of the 4 part series

Updated 10/31/2022
Created 01/11/2015
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econut
econut
421 Followers

(This series is a continuation of the story line from 'Finding My Place'. It can be read alone, but why not start from the beginning?)

*

It had been a month since the first weekend I had spent serving as a live-in maid and sex slave to Lana and Gary, an attractive, sexually dominant couple. Since then, I had been to their house serving them every weekend except one. I have always been sexually submissive and have had bisexual fantasies, so I had taken to my new role with enthusiasm. Serving them was exciting and arousing in a way I had never felt before. I spent every weekday and night thinking about them, and fantasizing about being used. I would play with the butt-plugs they gave me and jerk off multiple times a day. That is, except for this past week.

Lana and Gary had a power over me, and I would do anything they asked. When I was at their house, my dick was locked in a chastity cage, keeping me in a constant state of arousal and frustration. Sometimes Lana would tease me to the point where I would be begging to suck Gary's enormous cock or to have Lana peg me with a strap-on, or whatever else it was they wanted me to do. But the truth is, I didn't always have to be teased, I just wanted so much to please my new Master and Mistress, I would do almost anything anyway. So the previous weekend, when they told me they wanted me to wear the cock cage all week in between my visits, I couldn't say no. Lana did stroke me off as a "thank you" for agreeing, but then the cage went on and I knew it was going to be a long week.

I was a mess all week long, unable to concentrate at work, having trouble falling asleep. I kept thinking about Lana's delicious round ass, her supple body and large tits that always bounced when she walked, or about the taste of Gary's huge cock or the feeling of it sliding into my mouth or ass. With the cage on I was unable to find any release, or to even get fully hard. It only made it worse that Lana kept texting me with suggestive thoughts and sending me pictures of herself in sexual poses. One day she sent pictures of Gary fucking her to my cell phone while I was at work. Friday couldn't come soon enough. But, even though it was agonizing to be teased all weak, deep down I was enjoying the feeling of being owned.

That Friday, Lana asked if I could take off work a little early to come over. I jumped at the chance and went there straight from the office. I had shaved my whole body from the ears down the night before, as they require me to be hairless except for my head. When I got there I pulled my car into the garage as usual, then I stripped naked and inserted my butt plug into my ass. The plug and the cage were my "uniform" while I was here. My dick was already twitching with excitement and beginning to strain against the cage.

There was a note on the door of the house which informed me that nobody was home but that I was to go in and get to work on the chore list until they returned. I have to say I was disappointed not to be able to see Lana, who was always dressed in something extremely sexy to show off her amazing body. I went inside and up to the spare bedroom where I locked my clothes in a footlocker, as I did every weekend. I found the chore list on the kitchen table and I got to work cleaning the kitchen. Several hours went by. I had finished in the kitchen and had vacuumed or mopped the entire house and was beginning to dust when Lana walked in the front door.

She was wearing a pair of black slacks that were flared at the bottoms but were tight around her thighs and hugged every curve of her hips and ass. Her blouse was sensible work attire but had a few critical buttons undone at the top and seemed to be stretched tight and struggling to contain her ample breasts. Her long brown hair was pulled up and clipped in back. I'm sure she had every man at her office fantasizing about her. Turning men on seemed to be one of her favorite activities.

"Hi there," she said as she walked in flashing me a mischievous grin. She set her purse down on a table near the front door and walked over to me. She reached down and grabbed my caged junk, squeezing my balls in her hand. "How is my little pet today?" She asked.

"I'm doing great, Mistress," I said, trying to match her energy. She walked past me, looking around the house.

"You've gotten a lot done this afternoon, huh?" she said. "That's good. We're going to have company over tomorrow. I want the house to look good and clean."

Company? That made me nervous. They had said the first weekend that I was to serve any of their guests as I would them, but they had never had any. Oh well, I guess I was already a slut for them, why not add a couple more.

Lana was already letting her hair down and unbuttoning her blouse. She took her top off and threw it over the couch, followed by her bra. Then she bent down to take off her high heels. My whole body shuddered as I watched her bend over away from me. My cock twitched uselessly. After kicking off her heels she undid her belt and slid her pants off. "Ahhh, that feels better," she said smiling at me. She was now wearing only a thong and I knew that wouldn't last long.

She turned toward me and smiled her devilish smile. She strode over to me seductively and put her arms around my neck. The smell of her perfume was intoxicating. "How was your week?" she asked. "Did you enjoy my texts?"

"Yes, Mistress," I said, telling the truth. She played with my earlobe with her fingers for a few seconds, sending a shiver down my spine.

"Good," she said. "I just wanted to make sure you didn't forget about us." She winked. As if I could possibly forget with my cock locked up in a cage. She began to run her hands down my chest, playing with my nipples and tracing her finger all the way down to the base of my emasculated member. "I wanted you to be excited for this weekend. We're going to have a lot of fun." She began to kiss my neck, letting her hair fall over my naked chest. She began to squat down, running her lips down my body. She knew just how to turn me on. She took one of my balls into her mouth and began to suck on it. My balls were super sensitive from me being constantly aroused all week and being unable to empty them. She began to suck on the other one while running her hands up the back of my legs and taking a firm grasp on my butt cheeks. The feeling of her mouth on my testicles was amazing. My dick was twitching and turning red from pressing against the cage. She continued for a few minutes then stood back up slowly and grabbed my hand.

"Now, how about a massage?" she asked while leading me towards the workout room where the massage table stood. She stopped before the table and shimmied out of her panties. Then she climbed up onto the table. The massage was a standard part of our weekend routine. She enjoyed getting them, and she knew how much it turned me on to give her one, rubbing my hands all over her body. Before long she turned over on her back so I could rub her boobs and pleasure her with my tongue. I ate her out for some time, bringing her to several orgasms. Then she flipped back over and beckoned me to keep going. I started to lick her ass while rubbing her cheeks. I ran my tongue up and down her crack, stabbing it into her hole, all the while kneading her butt cheeks with my hands. I think I love eating her ass almost as much as she loves having me eat it. We continued in this way for quite a while, with me tonguing her asshole and crack while she just lay there, enjoying the sensation. Then after a while, it was time to get up. She told me to get back to work on whatever I was doing. I resumed dusting, while she went upstairs to take a shower.

I had finished dusting and had begun cleaning the upstairs hall bathroom when Gary came home. He was dressed in carpenter pants and a t-shirt. He said "Hey" to me and then went into the master bed room. Lana was just getting out of the shower. When she saw Gary she sat him down on the bed, undid his fly, and began to go down on him.

"Mmmm..." he moaned. "To what do I owe this pleasure?"

She swallowed his stiffening cock and bobbed up and down. "I just wanted to taste your beautiful cock," she said. She swallowed it again and stroked the base. "Before you go and shove it up the maid's ass." She wrapped her mouth around him and swirled her tongue around the tip.

Gary moaned again and ran his fingers through her silky hair. "Well, I'd much rather shove it inside of you." He grabbed her shoulders and pulled her up off of her knees. He lay back on the bed as she climbed on top of him. She straddled him and lowered herself onto his massive shaft. Her head rolled back and she gave a low moan as the head of his cock slipped past her labia. Gary put his hands back behind his head and enjoyed the ride as Lana lowered herself onto him, taking inch after inch of his manhood into her. When he was buried to the hilt she steadied herself with her hands and began rocking back and forth and up and down. She rode him faster and faster, settling into a steady rhythm. Her boobs bounced each time and her ass cheeks were slapping against his thighs. As she began to edge closer to orgasm, her moans began to grow louder. Soon she was screaming with pleasure as she pushed herself up and then dropped herself back down, letting gravity push his cock deep into her.

At this point I could hear her screams emanating from upstairs and could hear the bedsprings squeaking. I had just begun dusting the desk and tables in the small home office room. I began to think about how I would likely be called up to clean her with my tongue once they were finished. That had become one of my regular duties, and I had actually come to enjoy it.

Soon, Lana's screams took on a higher pitch and I knew she was starting to cum. Gary put his hands on her hips and began thrusting up into her. He was beginning to get close too. She leaned forward and rocked her hips back onto Gary's cock as the orgasm washed over her. After a couple minutes, her high pitched screams began to turn to a deep animal growl as she rode the wave of pleasure back down to earth. Then, without warning she stopped rocking back and instead dismounted and stood up. "Ahh, I needed that," she sighed.

"Wait, I haven't finished yet," protested Gary.

"I just showered," said Lana, with feigned innocence. "I don't want to have to clean up a mess."

"So you want me to finish myself off?" asked Gary, frustrated.

"Why don't you ask the help?" said Lana with a grin, then spun around and walked back into the bathroom and closed the door behind her.

Gary got up and strode down the hall and down the stairs, stroking his cock as he walked. He walked into the office where I was wiping the dust off of an end table. I had barely realized he was there before he put his hands on my shoulders and firmly but gently pushed me down and bent me over the arm of a small loveseat. Without a word, he kept one hand on my back pushing me down while reaching with the other and pulling the plug out of my ass. It hurt being pulled out so fast. Then he grabbed my hips and, in one motion, shoved his cock into my ass and plunged it in to the hilt. It slid in easily because I kept myself lubed all the time I was here.

He started fucking me hard and fast. I was shocked from being forced like that. I felt like he was just treating me like an object, or a toy. That's all I was here. I was just a toy to be used for Gary and Lana's pleasure. It felt so dirty and degrading as he fucked me. The humiliation of it excited me. I surrendered myself to him as I felt his huge cock filling my insides and stretching my hole. Before long he began to grunt and thrust harder, then I felt a gush of warm liquid inside my ass as he climaxed. When he pulled out, he immediately shoved the plug back in trapping his cum inside. Without being told I turned around and sank to my knees. I took his softening cock into my mouth and began to suck it clean. I could smell and taste a mixture of Gary's cum, Lana's juices, and my ass. I squeezed the last few drops out him and then sat back.

"Thanks, slut" said Gary. "You've got Lana to thank for that." Then he walked back out, a little slower this time with a little more swagger. I returned to my chores.

The rest of the night was fairly uneventful. I did the dishes and folded laundry while Lana and Gary mostly kept to themselves. They seemed to be discussing their plans for the next day when a couple of their friends were coming over. They didn't seem to want to tell me very much despite, or possibly because of my obvious curiosity. Lana did tell me that Steve and Tracy, friends of theirs from the neighborhood, knew all about me were eager to play. She reminded me that I should be prepared to do anything they want me to do. A couple times she referred to me as "the entertainment" and then said that I was going to love the special outfit that she had picked out for me.

That evening Lana called me up to my room. She told me to get on the bed and bend over. She pulled the plug out of my ass. I could feel my ass gaping open. She picked up an even bigger plug, this one well over 2" wide at the base, and began lubing it up. She pressed it against my already well stretched ass hole and slowly shoved it in. It felt as thick as Gary's monster cock, but thankfully not as long or I wouldn't be able to walk around. As usual whenever I get a larger plug for the first time, I began to feel like I had to take a huge dump. The feeling usually wears off after a while, but it is always uncomfortable at first.

"You're going to get plenty of use tomorrow so I want you to be good and loose," Lana said in a caring voice. "I wouldn't want you to be in any pain. I know how much you enjoy getting fucked in the ass." I couldn't help thinking that she genuinely cared about me.

When it was in she sat down on the bed and told me to eat her out. "I need another good orgasm before bedtime," she said. "Don't you just love a nice big orgasm before you go to sleep?" She was running her hands through my hair as I lapped at her slit. "I always feel so much more relaxed afterwards, don't you?"

"Yes, Mistress, I love orgasms before bed," I said and then ran my tongue back over her moistened clit. Of course I love coming before bed. I usually jerked off every night, especially since I had started seeing them. She was just rubbing in the fact that I hadn't been able to for the last week. And since I knew how much she loved to tease me, I probably wasn't going to get to tonight. She had me lick her to two loud, apparently very satisfying climaxes. Then she went on about how much she enjoyed them and how much better she felt now, extolling the joys of orgasm just to frustrate me even more.

After she went off to her room, I lay in my bed for a long time, unable to sleep. I was frustrated from being denied orgasms for so long, and I was excited and nervous about serving another couple the next day. A million different scenarios played through my mind. Eventually I drifted off.

I woke up to the alarm as usual, and then went to the bathroom to clean up. I started by removing my plug to give myself an enema. I felt the cool air hit the inside of my gaping ass. After squeezing the water in, I stood up to turn the shower on to let the water heat up. I felt a little trickle of water running down my leg. I squeezed my muscles as hard as I could but I still felt a few drops leaking out. I got back on my knees and stuck my butt in the air to keep it from spilling out. My ass was getting so stretched out that I could barely even close it! A few minutes later I released the water into the toilet and got in the shower. When I got out, I slipped the plug back in, with less effort than Lana had used the night before. By now, having something in my ass was starting to feel natural, almost comfortable.

After getting cleaned up, I went to the bedroom and woke Gary up with a blowjob. After he blew his load down my throat, he went to make breakfast. Lana, who was dressed this morning in a pair of skin tight running shorts and a sports bra, was pulling a shoebox out of the closet. She came over and handed it to me. "Here you go, try these on," she said. "These are part of the outfit you'll be wearing tonight."

Inside the box was a pair of black high-heel boots. The heels were an inch or so wide and about 3 inches long. The tops came up to mid-calf and had a thin zipper up the side. I held one up wide-eyed. I had never worn heels before.

"Go ahead, let's see how they look," said Lana, smiling.

Reluctantly, I bent down and slipped my left foot into a shoe. It felt like a pretty snug fit. The zipper was a little tight around my calf but once zipped, it fit like a glove. A little tight in the toes but otherwise it felt alright. I slipped the other one on my foot and zipped it up.

"On your feet," said Lana. She grabbed my hands and pulled me up. "Now walk around a bit."

I took a step and almost fell flat on my face as my ankle rolled to the side. Lana caught my arm. The next step was better but I still felt clumsy. At least the heels had a little width to them. Lana had probably anticipated my lack of experience. I took a few more steps around the room. Lana walked over to the closet and slipped on her own pair of heels. "Here, walk like this," she said and began to walk around keeping her back straight and swaying her hips. She made it look so easy. I followed her, doing my best to imitate for a few minutes. Then she kicked her heels off and announced that she was going to go work out. I was to make the beds and make sure the dishes were done and the house was clean before the guests came over in the afternoon. And I was to wear the heels all day. "I want you to get some practice," said Lana. "I don't want you falling on your face in front of the guests.

All morning I did my chores while trying not to stumble. Wearing the heels made my ass stick out, making me feel more vulnerable and exposed. The swaying of my hips also made the plug in my ass move differently, rubbing more against my prostate. It was actually kind of pleasurable once I got used to it. Although, after a few hours, my feet began to hurt. By lunchtime I had gotten the hang of it and was feeling much more confident in them.

That afternoon, Lana decided to tease me extra hard. She tied me to a chair and took my cock cage off. My dick sprang to life immediately. She proceeded to stroke me and suck me for almost an hour, bringing me to the edge of an orgasm and then denying me. She would sit in my lap and grind her beautiful ass into me. I was practically in tears from the frustration. I had been locked up all week, unable to cum, and my balls were aching for release. When I got close to cumming, she would squeeze them and the pain would drive away the orgasm. Finally, she dropped a soaking, ice cold towel in my lap and left it there until my dick shriveled up, then she slipped the cage back on. Before she untied me, however, she told me that if I did a good job pleasing their guests that I would be allowed to cum. I was determined to earn that pleasure.

After lunch, Lana dragged me upstairs to the bedroom telling me it was time to get dressed for the party. She took the plug out of my ass, telling me that she wanted my ass to be easily accessible to my guests. It felt empty after the large plug was removed. Then she walked me over to the bed where a small black dress was laid out. We stopped in front of it. "What do you think?" asked Lana. The skirt looked very short and the whole thing looked like it would be really tight on her generous curves.

"I think it would look stunning on you, Mistress," I said.

Oh you silly, it's not for me," she snickered. I looked at her and gulped. "It's for you," she finished with a grin. "Now slip it on and let's see."

econut
econut
421 Followers
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