Pool Boy Gets Dressed Up Ch. 01


Then she pulled off her bottoms and tossed them onto the chair as well. Her pussy was cleanly shaven. I have seen many pussies watching porn, but Debra's pussy was perfect. Her pussy lips were slightly swollen and at the top it almost looked like a little cock sticking out, that must be her Clitoris, just perfect.

Debra dove into the water and came up next to me. She kissed me again, and then she pushed away and started to do laps. When she reached the end of the pool she called out to me, "Come on do some laps with me."

I swam over to her and got ready to push off for some laps, "Don likes his women toned, and swimming is the perfect low impact exercise. I do 50 laps a day, are you ready?"

I was a swimmer, 50 laps? No problem. Debra never stopped and never slowed her speed until all 50 laps were completed. It was a good workout. Debra lifted herself out of the pool and dropped into the spa which was attached to the pool. I followed as I sunk into the nice warm, bubbly water. Now I was getting really relaxed and Debra made it all seem so natural.

We sat soaking for about 15 minutes when Debra lifted herself up onto the edge of the spa, leaving her legs dangling in the water. I thought that that was the signal that spa time was over, so I started to get up and get out.

Debra grabbed my shoulder, "Oh no you don't sweetie. You're not done yet. Come over here to me, we have a couple more issues to discuss."

Gliding in the water, I moved towards her. I was only able to focus on her pussy staring me in the face. I got close enough that she grabbed my head and pulled my face to her pussy, "Pussy eating lesson time, I sucked your little pecker, now it's your turn to make me feel good."

As she said this she pulled my mouth right to her pussy, and then she pulled and pushed my head side to side grinding my face all over her pussy. It was so soft and warm. Her pussy lips dragged across my lips and face. I took a deep breath so that I could smell my first pussy, it was intoxicating. "You like that do you? Now stick your tongue out and lick my pussy. Then suck on those pussy lips."

I took her instruction and pushed my tongue into her warm pussy. It felt so good, so warm and soft. I sucked in her pussy lips and used my tongue to explore the feel and taste. I must have been doing something right by the sounds of Debra's moans "Mmmm, yes that's my baby, suck those lips, get to know them. Lick up and down my snatch, push your tongue way in and move it around. That's so nice, taste my pussy juice baby."

Her hands were massaging my head, but firmly holding me in place eating her pussy. I was in heaven. I licked and sucked up and down her pussy. I felt a hard nub at the top of her pussy and really worked my tongue on that. Debra started to move around on the edge of the spa, then she started to moan louder, "Oh yes that's it keep going, I'm going to cum mmmmmm."

Debra pushed my face hard against her pussy, and held it in place as her body shook and convulsed. My nose and mouth were enveloped by her pussy lips. My tongue was darting around in the soft hot folds of her pussy. I could feel her thighs clamp down against my cheeks and start to shake. A warm flood of liquid filled my mouth. She was cumming in my mouth. It tasted nothing like my cum, but it was sweet and warm, thinner than mine. I drank it in like sweet nectar.

Debra finally released her grip and pulled me up to her and kissed me hard. She licked my face all over cleaning her juices. "Don likes his girls to clean up their messes. That was so fucking great."

I felt so proud I was able to eat my first pussy and make her cum doing it, a natural. Debra slinked back in the water and pulled me to her. "That was amazing, I needed that. Did you like eating pussy baby?"

I was elated "Oh god yes, it was the best thing I have ever done. I hope I did it right?"

Debra looked at me, "You did it just right." as she said that I felt her hand move to my hard cock, "You know you have the cutest little cocklet I've ever seen."

Then her hand went up to my nipples and started to caress them. My nipples are so sensitive, as soon as she touched them my cock jerked and my head went back to enjoy the sensation, "You love your titties played with like that don't you baby?" she cooed in my ear.

Just when I thought the subject was dropped, Debra began her questioning again, "Now tell Miss Debra what else excites you hummm? You like watching the tranny porn? I bet you picture yourself all dressed up waiting for a big hairy man to lie on top of his little pussy boy? I bet you have a nice tight pussy that is dying to have a nice cock pop that cherry? Hmmm baby, tell Miss Debra."

She kept whispering in my ear and massaging my nipples, I was about to explode. I didn't want to admit anything, but she had me so horny with visions of me dressed in a bra and pretty panties, and a man's body, no I wanted Don's body pressing against me. Oh my god what was I thinking, no, no, stop, "Yes, yes, I want to dress like a little sissy slut, oh god." I turned my head away in shame, again.

Debra kissed my ear, "There that wasn't so bad to admit now was it sweetie. Miss Debra is here; she can make all your wishes come true here in our own little world here."

Debra pulled away, leaving me panting and almost in tears. I just confessed something out loud that I barely admitted to myself. Debra got out of the spa and told me to follow her. Like a puppy dog I did as she commanded. We went over to our chairs and Debra handed me a towel so that we could dry off. Then she grabbed my hand, both still naked, and then walked in the house. We went through the glass doors into a huge, nicely decorated, living room with plush carpet that felt wonderful on my feet. We went through a foyer to a wide open staircase leading upstairs.

She pulled me along to a set of double doors that lead into the master bedroom. Debra opened the doors to a room the size of my parent's house. Large four poster bed, couch and chairs set for conversation that faced a raised marble fireplace with glass doors that looked through into the bathroom. Debra continued to guide me through into the bathroom. The bathroom was all white marble floors with a huge Jacuzzi tub next to the fireplace. There was a large walk in shower that looked like there were at least twenty shower head nozzles attached to the walls and some attached to hand held wands, all set in beautiful stone and glass. As if you couldn't take it all in with one sweep of your eyes, one wall was mirrored so no matter where you looked you could see yourself and the entire bathroom.

Debra led me into the shower and turned it on. Debra flipped a switch on the wall and steam began to form. Debra turned to face me, "Well are you ready to play Brandy?"

I was still trying to soak it all in and answered in a stunned fashion, "I guess so Miss Debra."

"You 'guess so'? Either you're in or you're out, I don't have time to play games. I want a friend that I can truly trust, one that we can share the upmost intimate things with and I know it will stay between us. I thought I could see that in you Brandon, I thought you confessing some of your desires to me were a sign that you could trust me? Maybe I was misreading you?" Debra was firm and she hurt my feelings.

Oh my god no, I felt really bad. As usual, I was stupid in the choice of words, "Please Miss Debra, I mean, yes I am ready to play. Please trust me, I trust you with anything. I've never done anything like this before today. You make me feel like a man."

Debra looked at me shocked, "Like a man? Oh sweet baby you're nothing like a man, you have a little pecker the size of a five year old, your tits are budding like a pubescent teenage girl, and you dream of sucking a guy's cock and getting fucked. No sweetie you're more of my little girlfriend here in this house. I want to dress you all up like a little tranny slut and we can watch gay and bi porn together and suck each other's tits, won't that be fun?"

I felt slapped in the face, I thought I was going to be her male lover, and now my cock was shrinking back down to a little nub and I was starting to cry. Debra came up to me and hugged me, "Shhh, shhh, it's ok Brandy you go and cry your little eyes out. See Miss Debra loves your tongue on my clit, you make me feel wonderful, but that pathetic baby cock will never satisfy my pussy. But that's ok. There are so many other ways to make each other cum, it will blow your mind. Now come here and suck my titties like a good girl."

I wasn't even comprehending anything, I just heard her ask to have her titties sucked, so I let her push my face to her breast and she used her hand to hold her tit while I moved over to it and started to suck on her nipple like a little baby. "There, there, that's better isn't it? Yes suck Miss Debra's nipple, relax baby."

The steam and the hot water were relaxing. Our high school gym showers weren't this big and there was a large drain on the floor. Debra grabbed a bottle off one of the shelves and squirted some pink liquid soap in her hand, then she pulled me off her tit and started to rub it all over my body, it smelled like Rose petals. Then she grabbed one of the shower wands off the wall, but this had a long tube with holes on it and a valve to turn the water on and off.

Debra instructed me to get on the floor, on my hands and knees. I asked her why? "Trust me Brandy baby, when we shower we have to clean everywhere or playing sexy games is not as much fun. You'll see what I mean."

As I lowered myself down to the floor, Debra squirted more gel on my back and started to rub it in. It felt so good to get a massage. Then the gel dripped down the crack of my ass and Debra's fingers stopped it right at my hole. She rubbed the gel all up and down my crack, then she pushed a finger in my hole. When I felt the intrusion my head dropped down and instead of pulling away I pushed back against her finger. "MMM, nice baby, you like that do you? This is just a little bit of pleasure, wait until you see what you will be getting later."

She continued to run her finger in and out of my ass for a few more strokes then I felt something bigger, blunt, and more rounded, pushing against my slippery hole. "Take a deep breath sweetie, then release it and push back like you want to take a shit."

I took a breath in and when I blew out through my teeth I bared down like I was taking a shit and the shower wand pushed in my ass. The soap made it really slippery and her fingering must have prepped me because there was just a slight twinge of pain before I felt my ass envelope around the device as it entered me. I bowed me head a little and groaned "Oh, mmmmmm."

I could hear Debra giggle a little, "Oh baby you haven't felt anything yet. Your little boy pussy is hot and ready for pleasure, I can tell. I think we are going unleash that sexy little slut in you." She laughed some more and gave my ass a nice comforting swat.

Now the uncomfortable part as I felt the warm water rush into my bowels. The pressure of the water as it filled me up made me groan in discomfort "UGH, I think I'm full, oh god I'm full."

Debra laughed, "We just started, we not only have to clean you out, but we have to stretch you out as well. Now hold back as long as you can, then I will pull the nozzle out and you sit on that drain hole and let it flow out."

'Really?' I thought to myself, "Miss Debra I can't go in the shower, I can make it to the toilet."

Debra swatted my ass again, but harder this time, "The hell you will, you will get one step out of the shower and make a mess all over my bathroom, besides you have to do this at least two more times so get used to it. I do this every day, it feels so good to be clean, you just wait and see."

Debra stopped the water flow, but kept the wand imbedded in my ass. I could feel the pressure build and the water leaking out around the wand and down my legs. I yelled, "I can't hold it anymore, pull it out, pull it out."

Debra placed her hand on my chest and held the wand in my ass, "Now sit up a little and scoot over to the drain. When I pull the wand out clinch your ass tight and then sit right on the hole and let loose. It's fine, don't worry any mess you make we can hose down, that is what this shower was built for."

I felt the wand pull out and I barely held the water back, as soon as my cheeks landed on the floor my bowels opened up and it felt like 10 gallons of water released out of me. Debra took another hose off the wall and sprayed me down with warm water. She lifted me up a little and washed my ass down, "Looking good, now let's do it again to finish the cleansing, then one last time to freshen up."

I didn't know what all that meant but I couldn't wait to find out. Debra repeated the first process, and this time it felt like only water came out. Then she screwed on this jar of liquid to the wand and shoved it back up my ass, "This is the freshener, a solution of herbs and perfumes to make you smell pretty and make you feel relaxed."

The liquid being sent through the wand this time felt thicker than water, like oil. It turned out to be perfumes and a little drug of some kind to relax me. Going through the rectum you don't need much to get into your blood stream and work its relaxing magic.

After our shower we dried off and moved toward a door in the bathroom. It turned out to be Debra's wardrobe room which was the size of an apartment. Debra grabbed my hand and looked at me, "Let's make your darkest dreams come true, anything you want to try on we will do it, ok?" With that she opened up a wardrobe to the most sexy bras, panties, slips, nylons, and garter belts of every possible material and color of the rainbow.

Debra grabbed my hand and guided it to touch the soft silky slips, "Feels nice doesn't it? Let's see what you would look good in?"

Debra pulled out a sexy pair of red lace panties, matching red bra, garter belt, and thigh high red nylons. She pushed me back further into the closet where there was a three sided mirror and a big, round, red, cushioned bench to sit on while getting dressed. She threw the clothes onto the bench and had me stand in the middle of the mirrors. I looked at all the mirrors and I could see my naked body, all smooth and clean. My nipples were sticking out like pert little breasts, and my pencil dick was trying to stick up like a man.

Debra held out the bra so I could put my arms through, then she turned me around and fastened the back. She spun me around again to face her and was down on her knees lifting my foot into the garter belt, then the other foot, and up it went to my waist leaving the straps dangling at my hips waiting to be attached to the nylons. Then the lacy panties, first one foot, then the other, and up my smooth legs they went. When she pulled the panties up and over my cock I felt the lace on the cheeks of my ass. I was delirious with the erotic sensations pulsing over my body.

Debra leaned forward and kissed my cock through the lace, "You are looking so pretty Brandy." I thought she was using 'Brandy' as being short for Brandon, like calling Robert, Bobby or John, Johnny, but now I knew she was calling me Brandy as in a girl's name, and I liked it.

Debra pushed me back to the bench and sat me down. She scrunched up one of the nylons in her hand and told me to point my toes down. She then pulled up the nylon over my foot, up my calf, and all the way to my thigh. She pulled the clasps down from the garter belt and attached them to the tops of the nylons. She did the same thing to my other leg.

She quickly grabbed me by my hands and pulled me into her arms and kissed me. As she kissed me, her tongue went wild in my mouth. Her hands were feeling my ass through the lace, and then she would run a hand up and down my nylon covered thigh. She reached in between us and massaged my nipples through the lacy bra. My legs went weak and I almost lost my balance.

Debra held onto me "Go with it baby, let yourself feel the new you. You are so hot and sexy." Her naked warm body pressed against me was making me light headed; part by the drug she slipped up my ass, and part was the heightened feeling of silk and lace on my body. I was Debra's new live Barbie doll.

Debra then whisked me around the corner of the closet to a make-up table, with lights all around and a wall covered in wigs, each having its own hair style and color. Debra grabbed a brown short haired wig and pulled it over my head, with my hair so short nothing had to be hidden. She then sat me down on the make-up chair and sat right on my lap facing me. I could feel her hot pussy pressing against my cock, my lacy panties being the only thing between us.

She kissed me again, "This is making me so fucking hot. Now let's apply a little lipstick and eye shadow." She was so quick with her strokes that in less than two minutes she was spinning the chair around and hopping off of me. I looked into the mirror and I saw a, if I do say so myself, hot babe. I couldn't believe my eyes, I was totally passable.

Debra was putting on a black corset that pushed her boobs up high and her nipples were sticking out the top. She grabbed a long, black silk robe and as she slipped it on she pointed me back into the bedroom while she finished getting dressed up. I walked into the bathroom and twirled around in front of the mirror, rubbing my hands over my bra covered titties. My little budding breast seemed to fill up the little training type bra. If I had just a little more budding it would have looked like I have real breasts.

I bent over and ran my hands up and down my legs enjoying the soft nylons. Debra called out from the wardrobe, "We are going to have so much fun Brandy. Go lay on my bed sweetie, I'll be right there."

I thought to myself 'This is it. I'm going to lose my virginity. I'll finally get to put my cock in a pussy.' I know she said I couldn't please her with my little boy cock, but I want to try. I want to feel what it's like to put my cock in a nice, hot, wet pussy. I walked into the bedroom, purposely wiggling my little ass in my red panties. I was really getting into the feel of my sissy outfit.

I crawled onto the king size bed which was covered in the softest silkiest white material I have ever felt. I lay down and sank deep into the comforter. I was lying on my back looking up at a, big cliché here, mirrored ceiling. My body stood out, all dressed in red, against the white bedding. I couldn't resist as I started to play with myself. Slowly I started circling my nipples with my fingertips, gently rubbing the lacy bra against my nipples. My nipples responded to my touch by growing out and hard. The scratchy lace against my nipples made them ten times more sensitive.

I could feel a wet spot starting to form in my little red panties. I was getting into myself, starting to moan in pleasure when Debra spoke up, startling me out of my self-pleasure trance, "You keep playing with your titties like that and you're going to make a big mess in your panties." My hands darted back to my sides, and I could feel myself turn as red as my outfit, embarrassed at being caught.

Debra stood next to the bed in her black silky robe, so sexy. Debra moved onto the bed and lay next to me, "I see you like your new look, can't keep your hands off yourself you dirty little slut." as she said that she tweaked one of my nipples and made me moan and squirm under her control.

Debra smirked at me and started to rub my nipples through my bra, "MMMM, my new little sissy slut likes her titties played with doesn't she? Listen to you purr like a little kitten."

I was moaning and feeling so good. My body was on fire with lust, "Yes, yes please don't stop Miss Debra."

Report Story

bytonyl65© 21 comments/ 221180 views/ 162 favorites

Share the love

Report a Bug

3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: