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  • Becoming Joey Ch. 03

Becoming Joey Ch. 03

12

Susan led me back into the guest room. She went to the dresser and opened the top drawer. The drawer was filled with panties of all different types and colors. There were French cut, bikinis, hipsters and thongs and the colors ranged from black to red to white to pink.

"I bought you your own panties. You can try different styles and different colors and see what makes you feel sexy." She reached her hand down and cradled my caged cock. "Oops, I forgot that I won't be able to tell which ones turn you on." She giggled and licked my ear.

She opened the next drawer. This drawer was full of lingerie. There were babydolls, camisoles, cheekies, and bras. Susan held a red cheeky up to me. "Oh this is perfect. So pretty, but will leave your cute ass out and ready for play."

I blushed, but felt my cock pulse once again. The next drawer held stockings and garter belts. Susan then opened the bottom drawer. "This is your toy drawer. While we're gone, I want you to get acquainted with everything in here."

There was an array of vibrators and dildos and smaller bullet shaped toys that I was to find out were butt plugs. There were several boxes of disposal enemas, as well as lube. "I didn't tell you, but Matt is out taking Dingo to the kennel. We don't want you to worry about him over the next couple of days. This is your time to explore. I've left DVDs here for you to watch." She slid her hand down my ass, pressing against me. "One more thing, I told you that you couldn't cum, but that's not exactly true. If you can cum just using your toys, you may cum as much as you want."

"But how..."

"Shh, you will learn. You will learn that your ass is your biggest erogenous zone. So many girls like you cum just from having their ass played with. It will hurt at first, which is why I want you to start with the butt plugs. We'll start with the small one and over the next couple days, you need to work up to taking the largest inside you." I stared at the large black plug, wondering how I would ever get it inside me. "In fact, let's start with the small one, right now." She picked up the small pink plug, the lube and a box of enemas.

"First thing for us girls is to make sure that we are always clean. After you go to the bathroom in the morning, you need to give yourself an enema. I'll show you how. Come on."

She led me into the bathroom. "Ok, baby, get undressed." I removed my shorts and panties. Both of us noticed that the front of the panties were covered in pre-cum. "My, this does excite you." She tugged the cage and cupped my balls. A mixture of pain and pleasure coursed through my body and I felt another small surge of pre-cum, which coated her hand. Susan released me and brought her hand to my mouth. I licked her palm and then she slowly inserted each finger into my mouth, allowing me to clean her hand. "Mmmm, that feels so good darling, how does it taste?"

"It tastes good Ma'am"

She kissed me lightly on the lips. Her tongue flicked out to catch the last remaining drop of cum. "Mmmm, it does taste good. All us girls love the taste of cum. We'll do anything for it."

Susan directed me to the shower and had me kneel inside it. "This is your first enema. It's going to feel a little strange, but soon you will love them." She opened the lube and held it over my ass. I felt the cold slickness start at the top of my crack and slowly flow down over my hole. Once, it reached my asshole, Susan gently pushed it inside with her finger. I gasped and clenched down. "Just relax baby," she said rubbing my back, "I just need to work this lube in."

I tried to relax as she withdrew and then pushed inside me again. I willed myself to stay relaxed. "That's better baby. Now, this enema is filled with a special cleaning solution. I'm going to insert this nozzle inside you and it will slowly fill you up. You will feel some pressure, but I want you to hold it as long as you can. Most days, you will only have to do this once, but sometimes, on special days, you will want to have multiple enemas."

I felt the cold nozzle press against me. I took a deep breath and let it out. As soon as I let out the breath, Susan pushed the nozzle inside me. I immediately felt my bowels filling up. I felt pressure that made me feel like I had to pee. Soon, my tummy felt bloated and Susan sensed my discomfort. "Almost done baby, just relax...there. Now when I pull out, I want you to clench really tight."

"Yes, Ma'am."

"One, two, three." She pulled the nozzle out and I clenched my ass, feeling only a small amount escape.

"Good girl, now keep yourself clenched, let it work itself around inside you." She raised me to my knees and knelt down beside me. "How does it feel?"

"Weird, but not bad."

"Good, we need to keep it in there a little while. Tell me when it starts to hurt." She pulled me towards her. "Here this will keep you occupied while we wait." She pulled me to her breast and slipped one nipple out of her shirt. "Nurse on me baby." I took the thick nipple between my lips and as she held me tight to her chest, I began to nurse, softly sucking the nipple into my mouth and running my tongue all over it. It was so soothing and I felt so close to her.

Somehow, she had picked me out and understood me. Understood that I needed this and that I would never be happy as just a man. I felt the doubt and stress leave my body and began to quietly cry against her. She held me tighter, even knowing what the tears were about. "I know, baby, it feels so right to become who you are supposed to be. We will always be here for you to help you, to guide you, to teach you. You are safe now."

Her nipple tasted salty with my tears, but I didn't want to let know. She stroked my head and whispered "Good girl."

As my tears dried, I felt an ache building in my tummy. "Ma'am?"

"Is it time?"

"Yes Ma'am."

Ok, let's get you up on the toilet. Hold tight until we get you up there." She helped me up and sat me on the toilet. Before another word could be said, I expelled the solution. Susan rubbed my back, "That's it, just let it go. Make sure it's all out." She handed me toilet paper to clean myself. I did and flushed the toilet.

"Good, now bend over and put your hands on the sink." I did as she moved around behind me. "Oh my God, you have such a lovely ass. I would kill for an ass like yours." She ran her hands over me, sliding her fingers back and forth across my hole. I felt more lube and then her finger pushing inside me again. It went in easier this time and before long she added a second. Each time her fingers went inside me, I felt a spark of pleasure and soon I was pushing back each time she pushed into me. "God, you are such a little slut. Matt is going to love you."

She pulled out of me and held the pink plug in front of my face. "Get it wet for me baby." I opened my mouth and eagerly took the plug inside. I rolled my tongue around it, making sure it was wet all around. "Good," she said, pulling it out. "Remember to stay relaxed, it will be a little pressure at first and then a little pain, but once it is inside it will push against your prostate every time you move and you'll love it. You'll never want to be without it."

I stayed relaxed, felt the pressure and the pain and finally the relief as the plug was buried deep inside me. "Keep this one in until tonight, but before you go to sleep, I want you to put the next biggest one in."

"Yes, Ma'am."

"Okay, get dressed. I have two more things to show you." She led me back to the guest bedroom and opened the closet. There were sundresses, skirts and blouses, although with a French maid outfit and a cheerleader outfit.

"There are times you will want to be dressed demurely, but still sexy, for going out in the daytime and there will be times that you want to dress to please your man."

"Please my man?"

"Come on now, Joey, you're not stupid, you know where this is heading. You are going to be a very hot young girl, every man's fantasy, no matter his age. There will be young men and middle aged men and even old men that are going to want you for themselves. You need to know how to dress to bring out the best in each of them...Now this one" she held up the cheerleader outfit, "This is a favorite of Matt's. Think about how you would feel wearing this on Wednesday evening when we come home, knowing that you are doing it to turn Matt on. Close your eyes and picture it."

I closed my eyes. I felt Susan behind me, pressing her tits to my back and her pussy to my ass. I pictured walking down the stairs and answering the door when they came home. I pictured Matt taking me in his arms, his hands on my ass as he pulls me into him. In my mind, I can feel his cock harden against and I know that I have done this to him. His hand lifts my face and I gaze into his eyes. He softly kisses me, then more urgently, sliding his tongue into my mouth. "Mmmm," I moan, as Susan continues to caress me.

"Yes, I know, it turns you on. Well, that is what I want. When we get home on Wednesday, I want you dressed in this outfit and then..." She paused, "Well then, we'll just see where the night takes us."

I melt against her, "Yes Ma'am."

"Good girl. One more thing. Come with me."

She led me into the guest bathroom. She showed me the makeup she had purchased as well as a long blonde wig and a short page cut brunette wig. "I have favorited some YouTube videos on makeup. You will need to spend a lot of time on this. It is a fine line between looking sexy, or slutty or just foolish. Bring the laptop up her and practice."

"Now for the wigs, you have two to choose from. We will work on growing out your own hair, but the beautiful thing about wigs is that with one change you can be a completely different woman. For Wednesday, I'd suggest the brunette page cut. Now you stay in here and look through your makeup. I have to finish packing. Matt will be home soon and we'll be off."

I sorted through the makeup, amazed at the different shades and colors, especially the lipsticks and eyeshadows. I leaned over the sink and felt the plug move in me. I relaxed my muscles and felt it start to slide out. I immediately reached around and pushed it back in, eliciting a gasp from my throat. I did it again, loosened, then pushed, feeling it push against my prostate each time. The front of my shorts were visibly damp. When I finally looked up in the mirror, I saw Susan smiling at me.

"Are you enjoying yourself?"

I nodded.

"Pussy control is very important. Being able to feel as you constrict against a cock, tighten yourself to make him cum in you, or be able to open up and let him fuck you hard. I think you are ready for the next bigger one. Go get it and the lube and meet me downstairs."

I scampered off to my room. I noticed that my overnight bag was no longer there, but didn't give it a lot of thought. My mind was on getting the buttplug.

I heard voices as I came down the stairs. I turned the corner into the kitchen and saw Susan standing by the kitchen table. Matt was seated at the table. They both turned and watched me walk into the room. I felt my hips moving a little more on their own accord.

"Here she is. Did you bring it?"

I nodded.

"Well aren't you going to say hello to Matt?"

"Hi Mr. Williams."

"Hi Joey, I hear you've been quite busy today."

I blushed, "Yes, Sir."

"Come on now. We are going to have to get going. Let's get you set up with the bigger plug." She held out her hand. I placed the plug and the lube in her hand. "Take off your shorts and bend over. Put your hands on the chair and stick your ass out."

I hesitated, having not been naked in front of Matt, which earned me a swift, sharp spank on my ass. "Now, young lady, you will obey me!"

I quickly pulled my shorts off and assumed the position.

"Good, now push out like you were before."

I pushed and felt my ass spread. The plug fell to the floor. "When we're done, you need to clean that with hot soapy water." I nodded. Once again, I felt the lube being drizzled down my ass and a finger playing with my hole as the lube reached it. This finger was meatier, rougher. I looked up and saw Susan standing to the side and I knew that Matt's finger was about to enter me. I clenched involuntarily. Matt rubbed my ass softly. "Just relax baby girl, it will go in much easier."

I willed myself to relax. Matt's finger pushed inside me. I gasped then moaned as he began to pump it back and forth, working the lube into me. "Should I go for two, honey?" I shook my head, but realized that he wasn't talking to me. Soon, I felt a second finger being pushed in beside the first. Susan brought her face to mine. She smiled at me and stroked my head. "Relax, you know you want this, open up for Matt."

Matt thrust his fingers in and out several more times. When he withdrew, I felt empty. I watched as Susan lubed the larger plug. It wasn't much longer, but was definitely thicker. She handed it to Matt. Matt probed my ass with the plug. Pushing it in slowly and watching my hole gape a bit, before withdrawing and watching me close up. Each time it went a little further. The pain was almost unbearable as he reached the widest portion of the plug. Susan stared into my eyes, wiped a tear from my face and simply said, "Take it."

I relaxed and Matt pushed and suddenly the plug was firmly embedded in my ass. I let out a gasp and sank to my knees. Matt helped me up and sat me in the chair. The plug pushed into me deeper. He wiped a tear from my eye. "Good girl," he said and kissed my forehead.

"Ok, I think we have everything. I've left money on the counter. The fridge is stocked. Help yourself to any alcohol. I will text you occasionally during our trip. When I text, I expect you to take a picture of yourself as you are at that moment and send it to me. I think you know what I am looking for, so don't disappoint me."

I walked to the door with them. Susan turned and hugged me. "I can't wait for this trip to be over."

Matt then took me in his arms. I felt his hand on my ass pulling me into him and yes, I felt it. I felt his cock, much bigger than my own, pushing against my tummy. Matt released me, smiled at me and they were out the door.

I immediately sat back down at the kitchen table, pushing the plug deeper into my ass again. I moaned and ran my fingers across my balls that the outside of the cage. Soaking wet. I spent the next four days trying all types of lingerie. I was never naked, except when I showered. I began to get in the practice of giving myself an enema at the beginning of a shower and by the end, I was ready to expel.

Although, I'm not very hairy, I took the opportunity to shave all the hair off my body. My armpits, legs and crotch were now smooth. I practiced with the makeup relentlessly and by Monday felt that I had a pretty good handle on it. I loved how I looked with foundation, concealer, a light brush of eyeshadow and a soft pink lipstick. I worked my way up to the largest plug, 6" long and probably 2" wide.

I never knew when Susan would text me and I'd have to send a picture. I think her favorite was when I was lying on the bed with a 7" vibrator buried in my ass. She kept telling me how they couldn't wait to get home to me. On Tuesday, I was dressed demurely, wearing boy shorts, with a matching bra that I had stuffed with stockings. I wore a cute yellow sundress and because I was practicing walking in heels, a pair of sandals with 2" heels. Of course, I had the plug in.

When the doorbell rang, my first instinct was to ignore it. When it rang the second time, I looked myself in the mirror and without thinking further went to the door to open it.

"Excuse me, Miss. I'm sorry to trouble you, but I have been working with your neighbors down the street on their home security system and they mentioned that you might be interested in upgrading your own."

The man was in his mid thirties, slightly overweight and slightly balding, but cute in a way.

I tried a soft feminine voice, "My parents aren't home right now. You may have to come back later."

"This is exactly why you need an upgrade, leaving a beautiful girl like you home alone. You never know what could happen."

I knew what I wanted to happen. I pictured myself inviting him in, coyly touching his arm, before letting my hand brush against the front of his pants. At that touch, he would pick me up and set me on the kitchen table, hungrily kissing me as he pushed me back and pulled my panties down. He would laugh when he saw my little caged cock, then lift me off the table and place me on my knees in front of him. I'd watch as he quickly unzipped his pants and pushed them to his ankles. I would see his cock, thick and veiny, pulsing in his underwear, then he'd tell me to take them off.

I shook myself out of the fantasy. The man looked at me oddly. "I'm sorry. You'll have to come back. They won't be available until Thursday."

"Alright, I'll just leave you my card. Please let them know I called."

"I will." I quickly shut the door. I couldn't believe it. I passed. He had no idea. My confidence soared. I couldn't wait for Susan and Matt to arrive home.

I slept fitfully Tuesday night. Excitement, nervousness, horniness all kept me tossing and turning. I woke early on Wednesday to a text from Susan. "Joey, we will be home at 3pm. I expect you to be made up and dressed. You decide what would be appropriate to wear. Stay in your bedroom when we arrive. I will come get you shortly."

I gave myself 2 enemas that morning, then replaced the large plug. I shaved my body, making sure that I was smooth. I found some perfume that Susan had left and strategically applied it. I dressed in the cheerleader outfit, not padding my small bra. I fixed the page boy wig on my head, then went to work on my makeup. Finally, I was satisfied that I looked as sexy as I could. I looked at the clock, amazed that it was already 2:30.

I went into my bedroom and started a DVD. It was one I had watched often over the past few days. A threesome, a transsexual and a married couple. I heard the garage door open, my stomach began doing flips. Finally, I heard footsteps on the stairs and a soft knock at my door.

"Come in." I sat up on the bed as the door opened and Susan entered. She rushed to me and pulled me into a hug. "Joey, you are so beautiful. You are beyond our wildest dreams." She kissed my forehead, then tilting my face up with her finger, softly kissed my lips. "I'm so happy to see you. Come with me."

I heard water running, but was surprised when we entered the master bedroom that it was empty. She led me into the bathroom and began stripping. "I don't want you to shower and mess up all your work. I'm just going to jump in quickly to get rid of this travel grime."

She bent over in front of me to remove her panties, giving me a view of her pink puffy lips and tight pale asshole. She stood, removing her bra. Her breasts were round and firm and her nipples, the same color as her pussy, were hardening in the cool air. The necklace with the key hung between them. She turned on the shower and waited for it to heat up. She lifted my skirt and tugged at my caged cock. "Did you leave it on the whole time?"

"Yes, Ma'am."

"Good. If you're good girl, it will come off tonight."

"Yes, Ma'am"

I watched her shower through the opaque glass, wishing I were running my soapy hands across her body. She finished. I held a towel out for her and wrapped her in it as she exited the shower. She quickly dried, explaining, "Matt is waiting for us downstairs."

She slid a loose tank top on. I could see her tits swaying through the arm holes. The shirt came down to the middle of her ass. She didn't put any panties on.

"Joey, are you ready?"

I nodded.

"When we get downstairs, I want you to obey Matt and me. We will do nothing to hurt you and I promise you, you will feel better than you ever have before."

12
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