tagTransgender & CrossdressersPool Boy Gets Dressed Up Ch. 02

Pool Boy Gets Dressed Up Ch. 02


I would like to thank the readers for the great feedback. I hope to continue this storyline to your liking. Feel free to offer suggestions. The feedback helps.


Yesterday I was a shy, young, teenage pool boy minding his own business. Today I am dressed as a sissy slut and just finished eating my Mistress' pussy. My arms are handcuffed over my head and attached to a four poster bed.

Debra knows how to get me to spill my guts. She gets me to confess my deepest desires, even before I could figure out what they are. Debra has such a sexy and sultry voice that, just by listening to her, she can make you cum.

Debra placed her hand on my cheek, "You make such a pretty sissy slut. My turn to make one of your dreams come true baby, tell your Mistress what makes you happy, hmmm?"

I was squirming under her touch, what did she want me to confess? I blurted out one of my desires, "I'm a virgin, I want to fuck you. I want to feel my cock inside you, please Mistress?" I begged.

Debra placed her finger across my lips, "Shhhh, I said your DEEPEST desires. Besides that little cock isn't long enough to get inside my pussy, baby. No, you want your Mistress to make you really feel like the little slut you want to be, I can feel it."

As she said this she put her finger in my mouth and swirled it around on my tongue, getting it really wet. Debra bent down and started to suck my nipple through the lacy bra. At the same time I felt her wet finger probing my virgin hole. I didn't resist the penetration as I pushed back against her finger. Yes, she did know my deepest desires. I let out a deep moan as the tip of her finger entered my dark hole. "Ugh, mmmmm. Oh god YES!"

Debra released her hold on my tit, "I knew you wanted this. You need to be the fuckie, not the fucker. I know the feeling baby, let me in. I will make you feel so good. I will give you an orgasm like no other. Tell me Brandy, tell me you want this; tell me you want to be fucked." Debra's finger was slowly massaging the inside of my ass. I couldn't believe how sensitive and intense the pleasure was.

I did want more. I know I want more, and she knows it as well. "Yes! Oh Yes! Mistress please, please, fuck me. I want to be fucked. Make me cum hard Mistress."

Debra gave a low guttural laugh as she pulled her finger out of my ass. She sat up over me again and pulled off her black robe, exposing her beautiful tits, which were sticking out the top of her corset. Springing up from her crotch was a life like strapon cock. Debra grabbed hold of her cock and stroked it like the real thing. "Mistress Debra is going to fuck you Brandy. I am going to take my cock and fuck your tight little pussy. I know you will enjoy this. I will make you have the most intense orgasm of your life. You want this don't you baby? Tell me to fuck you with my cock."

My hands were cuffed over my head. I was staring up into a beautiful woman stroking a big cock, waiting for my permission to stick that big cock up my tight little virgin hole. A million things were going through my head all at once, could something that big fit? Will it hurt? What if I tell her no, will she stop and release me? Trust her, focus on trusting her I thought to myself, "Mistress Debra I want your cock in me. Fuck me with your big cock please. I want to be your sissy slut, I want to be fucked."

It was over; all my inhibitions have been released. I was dressed up like a sissy slut and begging to be fucked. I felt relieved, it was my true desire. I wanted to be taken, controlled. My body spoke volumes when my cock never really matured to a man's size. My breasts formed more as a girls would, budding and puffy, rather than a firm chest of a boy. I couldn't even grow hair on my body like a man. I now know that I want to be taken by a cock.

Debra moved forward along my torso, dragging her wet pussy up my stomach until the tip of her cock touched my lips. "Good girl, let it all out and Mistress Debra will make it all come true. Now you need to learn to suck a cock and get it nice and hard before you can get fucked by it. Take your tongue and run it over the smooth head of my cock."

I looked up, in between Debra's tits, into her lustful eyes as my tongue stretched out of my mouth searching for my first cock. I ran my tongue over the plastic phallus. It looked like a real cock, nice flaring head, long veiny shaft that was about six or seven inches long, and resting against a black studded leather harness that Debra had securely fastened around her waist.

"Ya. That's it, run your tongue all over my head, get it nice and wet. Open your mouth baby and feel and taste my cock." I opened my mouth and Debra pushed about three inches into my mouth. She pulled it out, and then pushed it back in several times, mouth fucking me.

"That's a good slut, get it wet. Let's see how much you can take." With that she started pushing her cock farther down my throat. Each stroke went down a bit more each time. I could feel my eyes begin to water as I started choking for air.

"Breathe baby. When I pull my cock out of your mouth take a breath. Relax your throat, let my cock slide down. We will work on your gag reflex. That's better. You are taking six inches of cock in your mouth. You're such a cock slut. Your little pussy is probably hot and ready to be fucked." I looked up and over the cock in my mouth as nodded to her. I was quite proud of being such a good cocksucker my first time.

I couldn't believe I was sucking a cock, though a plastic one. The size of Debra's cock was so different compared to my little pecker. I now understand how pathetic my cock really is, it couldn't possibly satisfy anyone. You need a real man sized cock, like the one filling my mouth.

Debra pulled out her cock, "That was a good first cock sucking lesson. You need to make your man happy so he fucks you really good. And you are going to do just fine."

Debra slipped her cock out of my mouth and moved back down over my body, dragging her cock down my torso. I felt the heat of her pussy when she reached my cock. She started to grind her pussy against my cock. I lifted my hips up in attempt to feel the heat of her pussy and stroke my little cock.

Debra looked at me, "I know that little thing is somewhere in your panties." She laughed as she ground back against my pelvis.

Debra moved down my legs, grabbed hold of my panties, just like she did with my speedo earlier, and then she pulled them down and off in one quick motion. She then grabbed my legs, lifted them over her shoulders, and dove into my hot little hole. I felt her tongue penetrate me. It was so hot and wet I wanted to scream out in pleasure. She kept at it, tongue fucking me, getting me really wet. My puny little cock was staring down at me with a big drop of cum ready to fall.

Debra rocked my ass forward, forcing my cock to be just inches from my mouth. The drop of cum dripped off the tip of my cock and I opened my mouth just in time for it to land on my tongue. Fresh from the tap always tastes the best. Debra then pushed two fingers in my ass. "Oh, yes, yes, that feels so good Mistress." I whined.

"That's it baby take it, open that tight little hole for your Mistress. You're getting nice and loose, almost ready." Debra poured some liquid on my ass and her fingers continued to slip in and out of my ass with no pain at all.

Debra lowered my legs as she moved up to lay her body on top of mine. Our cocks pressed into each other. Her cock was so much bigger than mine. Debra kissed me on the lips as she moved to my right ear. Debra lightly bit my earlobe and darted her tongue around the edge, "Are you ready baby; ready to get the best fucking of your life? Let me hear you say it? Tell me how much you want my cock inside you. Tell me your all mine; you are my fucking little cock sucking slut!" Debra continued to grind our cocks together as she taunted me into confession.

I raised my legs up and wrapped them around Debra's waist. Her cock slid down and pressed against my virgin hole. I looked at Debra, and with a panted breath, "Yes Mistress, I am yours. Fuck your little cock sucking slut. Show me how to take a real cock."

I felt the head of Debra's cock push gently into my ass. This was so much bigger than her fingers. It felt like a baseball bat was trying to push its way in. "Remember baby; push out when I push in. Let me fuck you with my cock baby." Just as she instructed me I felt the firm pressure of her cock slipping into me. I pushed out against the intrusion. The pain shot through me and Debra bit down on my ear sending another sensation through my body.

"Take it slut, feel my cock enter you. Relax, and enjoy being fucked by a cock. You want this, you watched movies of boys taking a cock, and you know you want it." Debra urged me on as she pushed more and more of her cock deep inside me.

I felt Debra's weight resting on my legs and knew she was all the way in. I felt so full and so stretched. The pain was subsiding. I wiggled my ass a bit to allow my pussy lips to wrap around her cock. "Ya, that's it slut wiggle that hot little ass of yours. You control the feeling. Grind that slutty pussy of yours against my cock. Tell me when you're ready to be fucked."

I pushed back against Debra's cock. I moved my hips back and forth, feeling the big head press against my insides. My ass was on fire, not in pain, but in sheer pleasure. This is what I was built for, to be fucked by a big cock. The feelings were over whelming, I wanted to be fucked so badly. "Yes Mistress, please fuck me. Fuck me hard. Please fuck me I need your cock."

"That's the little slut I knew was in there waiting to come out." With that Debra pulled her cock out, just until the head held my ass open, then she slowly pushed every inch of her cock back into my ass. Slowly she fucked me letting me feel her cock glide in and out; breaking my pussy in slowly so that I could take and want more.

"I can't take it anymore, please Mistress fuck me harder. I want to be fucked hard." Debra pulled her cock all the way and then slammed her cock all the way back in until her pelvis slammed hard against my thighs. "Yes, that's it, yes, fuck your little slut Mistress, fuck her good."

Debra started to slam her cock in me harder and harder. She was relentless. The sweat began to drip off of her forehead as she continued to plunge into my hole. "Take it bitch. You want a cock in you; well here is what it feels like. You like cock don't you baby? You want a real man to fuck you now, huh slut? You need more cock. I bet you want to suck a real cock now, don't you?"

My head slapped back and forth against the pillows. I bucked up to meet every thrust Debra gave me. My little cock was soft and flopping all around, spewing strings of pre cum all over my stomach. "Look at you leaking cum all over. I bet you're thinking of sucking cock aren't you slut? Dreaming of having a big man take you and treat you like his little slut? Ya, you want a man to shoot his hot cum in your mouth and fill your little pussy with his juices."

We both couldn't hold back any longer. Debra screamed out first, "Oh god, yes I'm cumming. AAHHH!!" When Debra started her orgasm by ass actually had an orgasm. Not my cock, but I felt my ass actually spasm. Cum seeped out of my cock and onto my chest and stomach. My cock was soft and not giving me the pleasure that I was feeling deep in my bowels.

"I'm having an orgasm in my pussy. AHHHH!! YES! I want a real cock Mistress. I want to feel a man cumming inside. I want to suck his juice from his cock. OHHHH! My...god.." My body shook uncontrollably until Debra finally fell on top of me in a pile of sweat and cum. She grabbed my face and we kissed until our bodies calmed down.

"Holy shit that was wild and hot." Debra stated as she gently pulled her cock out of my ass. She then jumped off the bed, stepped over to the nightstand, and pulled out a bottle of cream.

As she spread the cool cream on my gaping hole she said, "This will help get you back to normal and keep you from burning. Was that the best orgasm ever?"

"Oh yes Mistress, you are so right, I am a cock slut. Thank you for opening me up and making me confess my desires." Debra came around to the top of the bed and kissed me on the lips as she unlocked the hand cuffs.

We went back into the shower and cleaned up. When we were done I asked Debra, "I hope I could still be your pool boy?"

Debra embraced me, "Of course silly. You think that this changes anything? No sweetheart I want you around for a long time. Don is gone, again, for the rest of the week. Finish your job as fast as you can and come over so we can play some more. I have a lot more to teach you." With that she kissed me on the head and walked back to the pool where I left my stupid boy clothes.

I finished my six hour a day job in half the time. I was at Debra's house by noon each day. Debra taught me how to deep throat her seven inch dildo without gagging. I was accustomed to being fucked, and wanted more each time. My oral skills on Debra's pussy seemed to be pretty good by the sounds of her orgasm. But the week came to an end and Don would be back from his business trip.

Debra sensed my melancholy mood on our last day together. We lay in bed spooning, with Debra behind me firmly embedded in my ass. I was slowly grinding my ass back against her cock trying to enjoy every last second I could. "What's that matter baby?" Debra whispered in my ear.

"Our week is over, Don will be back tomorrow and I won't be able to come and play. I don't want to think about not getting fucked, eating your pussy, or being able to dress up." I was almost in tears.

"Is that all that's bothering you. No worries my little slut." As she said this she tweaked my nipples and shoved her cock deeper in my ass, causing me to just about have another orgasm.

"Don comes and goes all the time. He will be here for a couple of days, and then off he goes again for days at a time. You just give me a call on the days you aren't cleaning our pool and I will let you know if you can come over. I want you just as much as you want me. I love fucking my little tranny slut."

The following week I stopped by Debra and Don's place to do my routine pool check. Debra was home walking around in absolutely nothing. "I was expecting you today Brandy. Don is not here so I thought you can hurry with the pool chores and scurry your tight little ass up to my bathroom and get ready for some play time."

I was elated, "Yes Mistress. Thank you. I will be done here in no time." I quickly cleaned the pool and tested the chemical balance. Within the hour I was scurrying up the stairs, pulling my shirt and shorts off as I fumbled my way to the bathroom. Debra was on the phone, talking, and walking around the bedroom when I cleared the door. She was wearing a see through negligée that in no-way was designed to conceal anything. Debra waved me through to the bathroom, and held her hand over the receiver as she told me to go ahead and get started in the shower without her.

I knew the routine as I gave myself an enema and ran the shaver over my body to remove any possible stubble. I finished my shower and was rinsing the last of the perfumed soap off my body when Debra popped her head in the shower, "Almost done sweetie? I'm dying to show you a couple of new tricks, and I bought a new toy." Debra gave me a wicked wink as she left the shower.

I was so excited that my limp little dick started to drip cum already. I quickly got out of the shower and dried off. I met up with Debra in the wardrobe ready for my transformation to Brandy. I liked being Brandy more than Brandon. Brandy wore sexy clothes that felt great on my body and gave me confidence. Brandy was more submissive but a sexual slut at the same time. Brandon was an insecure introvert that had no sex or friends.

Today I donned a sexy red wig that flowed down past my shoulders. Even the hair cascading over my shoulders was turning me on. I was getting pretty good at applying my own makeup by now, but Debra still left the final touches for her to do. Debra handed me a white corset to put on. I stepped into the corset and Debra cinched it up in the back. It was so tight I could barely breathe, but turning around to the mirror, by breasts actually looked full and stood out like real tits. I lifted my hands to my breasts and gave them a squeeze. I couldn't believe how good they looked.

Debra hugged me from behind and put her hands over mine as she whispered in my ear, "You look absolutely beautiful. Except for that little thing hanging between your legs, these tits make you totally passable as a sexy, hot, pretty little girl." Debra squeezed my breasts and kissed me on the cheek.

I thought 'A pretty little girl' yes, that is what makes me feel good. I looked at myself in the mirror, my hair and makeup were perfect; soft face with no stubble what so ever; even my Adams apple was barely noticeable. The corset showed off my perky little breasts and curvy body, and my swimmers legs showed smooth and tone. I was pretty hot, except for that puny little cock sticking out between my legs. At least it is so small that it hides well in the sheerest of panties. My boy pussy is as sensitive as any real pussy, at least for me. I love the orgasms that come from being fucked by Mistress Debra; they are intense and earth shaking.

Debra pushed me out of the wardrobe, "That's all we are wearing today, now go on and wait for me on the bed, I will be right along." With that she gave my bare ass a nice slap as I shimmied out the door.

I lay on the bed looking up at the mirrors, admiring myself, when Debra walked into the room wearing a new strapon, and nothing else. This cock was at least nine inches long and three inches wide. It looked so real, right down to the balls that seemed to actually have movement. Debra grabbed her cock and pointed it at me, "Do you like my new cock? It finally arrived yesterday and I have been dying to have you over ever since. Don left this morning for a trip and the only thing I could think about was fucking you with this baby. It has a soft latex coating that feels so real, my balls are actually soft and they hang just the like real thing." As she said this she cradled her balls in her hand as if weighing them.

Debra walked over to the bed and stood at the end, "Come here slut, suck my cock and get me ready to fuck your pussy." My mouth was watering and my ass was twitching with excitement. I wanted this cock real bad. I crawled on all fours, towards Debra, like a lioness to its prey. My mouth was, watering, anticipating the feel of that cock sliding down my throat.

I took a hold of her cock, feeling the weight and girth of this monster. My eyes were transfixed on it as I felt it up and down the shaft. It actually had pliable skin that moved when I jacked it up and down. In a daze I spoke more to myself than to Debra, "It's so life like, it feels just like a real cock."

I moved my hand down to the balls, and rolled them around my hand. This was the closest thing to a real cock I could have ever imagined. It was a thousand times better than my little nub. I could see why Debra, or any woman, could never be pleased by my pathetic dick, when there are cocks like this out there. It felt so natural to be holding a cock in my hand.

I leaned over and rubbed the soft head over my face. I slowly ran my tongue over the head and shaft. I wasn't even thinking about Debra, I was just making love to this cock. I was in another world, just me and this cock. I had been practicing cock sucking on a smaller dildo, but this was different. I opened my mouth and moved my head over the cock. I swallowed about four inches as I felt the head pushing at the back of my throat. I moved my tongue along the shaft as I felt the skin move back and forth. It wasn't solid and stiff like the other dildos.

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bytonyl65© 17 comments/ 155375 views/ 75 favorites

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