tagTranssexuals & CrossdressersPool Boy Gets Dressed Up Ch. 03

Pool Boy Gets Dressed Up Ch. 03


Debra and I just finished some of the best sex ever. Debra had a lifelike replica of her husband's nine inch cock made, strapped it on, and fucked me silly with it. But now Debra wanted me to go out in public dressed up as Brandy. I wasn't sure about this, but looking in the mirror I did seem passable.

We reapplied my makeup and Debra picked out a nice soft brown wig that fell past my shoulders. Debra handed me a wrapped box, "Open it. It's just a little something for our special day." I opened the box and began to cry. It was a complete outfit just for me.

I pulled out the pieces one by one and held them up to me as I spun around in the three way mirror. Debra bought me a pretty light pink flowered print top, a short white straight line skirt, a white pair of tights, and a pair of black flats. "Now don't go smearing your makeup on your new clothes. I also bought you a bra with forms to give you those titties you so want and a nice pair of silky tight panties to hold back the pee wee cock of yours." I looked at Debra with more love than I have ever shown anyone in my life.

"Ok, now let's get dressed and go have a bite to eat." Debra turned and put on a similar outfit, with a red low cut blouse, a jean skirt, no bra, no panties, and a pair of "fuck me" pumps, she was hot.

"I bought you flats; didn't think you were quite ready for heels your first time out." Let's go sweetie I'm starving after that workout. I quickly slipped on my flats and jumped up to catch up with Debra.

We drove for forty-five minutes before we came to a nice mall. This mall had only high-end stores. I never have been here before but it was obvious that Debra knew her way around. She parked her Mercedes SL in a nice shaded spot and hopped out of the car. I hesitated, still not sure if I was ready. "Come on Brandy I'm starving."

I opened the car door and swung my legs out of the car, here goes nothing, "I'm coming Miss Debra."

"Out in public, Brandy, you need to just call me Debra. Remember, we are just a couple of hot chicks going out for a bite to eat, and do some shopping of course." Debra grabbed my hand and we walked through the parking lot and into the doors of the mall.

People were all over the place, and not one person stared at me. I felt my confidence building up as we strolled through the mall. We finally arrived at our destination, a sushi restaurant, my favorite. Debra ordered our meal. We ate as we watched people walk by the window. We finished our meal, Debra paid our waiter, and we left with no scene made. I now felt I was walking with me head held high.

Instead of going back to the car, Debra pulled my hand guiding me into the mall, "We have some shopping to do." Our first stop was Bloomingdales. Debra went to the young miss section and started pulling things off the rack and placing them in my arms. "Go try those on." She instructed.

I put my face close to her ear, "Debra, I can't afford this, and what if I get caught in the ladies dressing room?"

Debra looked at me with that stern look, "When Debra takes you shopping, Don pays, remember that. Besides nobody can see you in the dressing room, that's why they have doors. Now get your tight little slutty ass in there and try these on. I want you to model each one. I will be over here on the couch waiting."

I tried on, what seemed like a hundred outfits. When I was finished Debra grabbed several of them and threw her charge card at the lady, "Be a dear and have those wrapped up and sent to my house."

The total came to almost three thousand dollars. The sales lady smiled at us as she told Debra, "I will have them sent over in the morning if that is alright with you?"

Debra responded, "That will work out just fine, thank you."

Debra turned to me, "Come on Brandy, time for some bras to hold those little titties up." Debra poked my left tit and laughed as we headed to our next store.

We went to a lingerie store and bought panties, bras, and nylons. Then Debra threw in a few naughty outfits as well. Then off we went to a shoe store, where we purchased my first pair of heels. Being that I am so short any heel height would be fine. Debra picked out a four inch, open toe, sling back, with a stiletto heel. It took some doing standing up, but the salesman was very helpful and flirted with me as I fell into him trying to stand up. "Watch out there miss, you can really twist an ankle." He was very good looking and I swear his hand was on my ass longer than necessary as he righted me back up. I blushed at his remark.

Debra again threw the salesman her card and had everything sent to her home. I was exhausted, we shopped for four hours. Debra drove us home and had me call my parents to let them know I was spending the night at a friend's house and would be back the next day. No problem there, it was Saturday and my parents usually are off doing something anyway.

Debra and I kicked off our shoes as we walked into the house. We were walking arm in arm laughing about the salesman making a pass at me when we entered Debra's living room to find Don standing there holding a drink in his hand. Debra and I both stopped in our tracks. Without skipping a beat Debra changed the flow of the conversation, "Darling, you're home early, what a pleasant surprise." She went up to him and gave him a long tonsil washing kiss.

"I'll come home more often if two lovely ladies such as your selves were here to greet me like that. Honey, who's your pretty little friend?" Don was so suave and good looking. He had on a nice yellow polo shirt with perfectly creased black slacks. What was really attractive was the fact that he had no shoes or socks on and his feet were absolutely stunning. He had large feet, with perfectly manicured long slender toes. His feet had the same even olive complexion as the rest of his body. I stood there fantasizing about sucking on his toes.

"Brandy Sweetheart!" Debra was all but shouting at me, breaking me out of my trance. "Brandy come here and let me introduce you to my husband Don." I shyly took a step towards them.

Don reached out his hand, I thought to shake my hand, but as I extended my hand he grabbed it softly into his, turned it palm down and kissed the back of my hand. My knees went weak and I almost passed out. I could feel Don grasp my hand hard to hold my balance. "Are you ok dear? You feel like you were going to pass out."

"Oh I am sure she is fine. Brandy is Cheryl's niece from next door. Brandy came to visit but Cheryl had to leave and meet Tom to sign some papers. You know Tom, when he wants something he has to have it now. Cheryl will be back on Sunday and I told her I would be glad to entertain Brandy while she was gone. We have had a great time so far don't you think Brandy?"

I looked up at Debra, we never worked with my voice but I managed to say, "The best time ever." and ended that with a smile.

Don released my hand, but not before giving it a tender squeeze, then walked across the carpeted floor towards the bar, "I'm fixing drinks to toast our guest for the evening, that is if Brandy is old enough to drink."

Debra fell onto the couch, "I'll have a martini darling, and Brandy is old enough to have a rum and coke, if you don't call the police on her." Debra laughed off the inside joke, knowing the last time I drank rum and coke with her we ended up fucking each other.

Don, being the ever delightful and handsome bartender responded, "One Martini for My lady, and one Rum and Coke for the young lady. We are in for the night so no need for the cops." We all laughed.

I was still worried how this was going to play off. I was stuck here now since Debra told Don I was the next door neighbors visiting niece and had to now spend the night. I guess staying in such a nice house wouldn't be all bad, but in the morning Brandon is going to make an appearance unless Debra can sneak away and bring me a different set of clothes.

Don brought us our drinks and placed them on coasters on the table in front of us. Debra was lounging on the couch and I was still awkwardly standing. I guess Debra wanted to see how Don and I would interact before she finally saved me from pure embarrassment. "Come sit by me dear. Don loves his big overstuffed chair when he comes home to relax. Don, my love, what brought you home on this beautiful night?"

Don walked around his chair, with his refreshed drink, and sat down. As Don sat down he crossed his left foot over his right knee and was lightly massaging his toes with one hand as he took a sip of his drink. "I finished business early and rather than spend another night away I grabbed a flight and here I am. I thought coming home to a nice drink and a relaxing night in the spa would do me wonders."

My eyes were glued to his hand running up and down the soles of his feet. I never gave feet any thought before, but somehow, Don rubbing his feet was turning me on. I wanted to sit in front of him, massage his feet, and suck his toes. What was I thinking?

I looked up at Don's face as he smiled at me. He was watching me stare at his foot, as my face blushed a deep shade of red. Don put his foot back down on the floor, placed his drink on the table next to his chair, reached his arms over his head, and stretched his body out. As he stretched, he pointed both of his feet, clearly displaying them for my pleasure. Don's shirt lifted out of the top of his pants exposing his soft olive skinned stomach. Don then got up and announced, "I'm going to change and take that nice soak in the spa. Anybody care to join me?"

I figured this would be a good time for me and Debra to work a plan. I was mistaken as Debra chimed in, "That sounds like a wonderful idea. Brandy and I shopped for hours. My feet are killing me; they could use a good soak and a good massage. You go ahead dear while I find Brandy something to wear so she could join us as well."

Don started up the stairs that led to his bed. I wanted to race after him and watch him change, but I knew I had to keep my feelings in check. Debra touched my should, "Brandy are you ok? Your mind seems to keep wondering and you're tuning us out. Now let's go see if we can find you a suit."

I looked at Debra, "How are we going to do that? The water might wash my makeup off, or what if my wig falls off, or worse, what if I get a hardon and Don notices?"

Debra laughed again at me, "You worry too much. Your makeup will be fine. We will apply a little adhesive to your short hair so that the wig stays on, it's not like you're going under the water and sucking his cock you know. And as far as that little thing you call a cock gets hard, well the Hubble Telescope couldn't see that." Debra laughed as she spanked my ass all the way up the stairs.

Instead of heading to her bedroom, which I was disappointed thinking I might catch a glimpse of Don naked, we turned down the hall the other way and headed towards one of the spare bedrooms. As soon as we entered the bedroom and Debra closed the door she spun me around and into her arms. Debra took me by the waist and pulled me in for a long kiss, "That was so hot. Don didn't know it was you. We can really pull this off. I will have the lights really low for a relaxing ambiance. We will put you in a nice little one piece suit. I have all sizes here for guests, I'm sure we can find you something. We will tuck that little pecker under your balls and shove it up your ass if we have to."

Debra was talking a mile a minute and all the while her hands were rummaging through the dresser drawers searching out a suit for me to wear. Debra finally came across a nice dark blue one piece bathing suit that she tossed in my direction, "Try this one on, I think we can show off that figure without exposing too much. We will enjoy the warm water and soak our feet. I am sure Don will have a couple more drinks to relax him; mixed in with the hot water and him being so tired he will be back upstairs passed out on the bed. You can sleep in this room. I will come down here and fuck while Don is down the hall. What a turn on." Debra gave me a nice kiss on the lips.

I could not figure out how I was going to get out of this without just running out the door and going home never to look back. My heart just could not fathom that. As it was, since I saw Don, my heart hadn't stopped running a mile a minute. I pulled off my clothes and let Debra apply the adhesive to my head while I pulled up the suit. It was form fitting, and after tucking my cock down and under you couldn't even see it. The suit was cut high on the waist showing off my nice legs. The sides were open, but the front was covering my muscled stomach. My nipples poked out against the material and with my wig and makeup I was sure Don couldn't tell that I was Brandon.

Debra left the room to change and told me to wait for her to come get me. It seemed like only a couple of minutes before the door flung open and Debra was running in, grabbing me by the hand, and leading me down the stairs, "Quick, Don is shaving before he comes down, that will give us enough time to jump in the water and hide under the bubbles." I thought to myself, finally, a break in this big mess.

Debra and I scurried down the stairs and out to the backyard. The spa was next to the outside bar and was already bubbling and steaming. Debra handed me some candles and a lighter, "Here light these and place them around the spa." She instructed as she ran around turning off the lights. The candles illuminated just enough to see as the twilight ours receded and darkness took over.

I slipped into the warm water as I waited for Debra and Don to join me. I was nervous as hell, that goodness I could hide my shaking hands under the water. I lay my head back against one of the pillows when I looked up to see the Greek god heading my way.

Don came down the stairs and headed for the door, leading out to the backyard. His tall body was a vision. His black hair was pulled back away from his face. His green eyes sparkled as his long dark eyelashes fluttered at me. When we locked eyes he flashed me the most perfect set of white teeth. His long bronze torso was lightly covered in a thick black coat of fur. His nipples were flat with the smallest nub in the center. His legs were long and sleek, with his flexing thighs and gams clearly outlined as he took each step. His red speedo was unable to hide the defined monster serpent that lay dormant and coiled ready to spring out and strike.

And those feet, just a small tuft of hair on the top of each foot, yet each long luscious toe was void of any hair. I stared at his foot as Don dipped it into the water to test the temperature. I watched as Don's toe flicked up at me spraying my face with a couple of drops of water. I looked up at Don, who was now looking down at me and laughing. Don turned and, to my disappointment, walked over to the edge of the pool and dove right in.

Debra came over with a picture and glasses of margaritas on a tray. She placed the tray on the edge of the spa and slid under the warm blanket of water next to me. "MMMMM, that feels so good. My feet were dying to get out of those shoes and this is the perfect end to a perfect day." Debra looked over at me and smiled, "Well, almost the end," as she reached over and tweaked my nipple and shot me a wink.

Don pulled himself out of the water and walked towards us. His now dripping wet red suit clung to his cock outlining the shaft and head perfectly. His balls were separated on either side of his shaft. Don slipped into the water across from me and Debra. "Oh that feels so good after a long week."

Don stretched his right foot out towards Debra, who in turned took a hold of it and began to grind her thumbs into the soles of his feet, "There, darling, does that feel good?"

Don responded with a deep moan as his left foot drifted gently across my foot, "MMMMM, that is so nice baby."

Then out of the blue Debra jerked Don's foot back causing Don to slip off the edge of his seat sending him under the water. As Don's face submerged under the bubbling water, his left foot flew out of the water and right for my face. My reflexes kicked in and I managed to dodge the flight of his foot as my hands flew up, grabbing his foot with my left hand and using my right hand to grab him by the calf. I was able to stop his momentum from continuing and began to push back against the bottom of his foot.

Debra was laughing hard and also pushing against the bottom of his other foot allowing Don's head to rise back out of the water. This all happened within seconds, but it still had the surprise effect on Don. When Don's head reappeared out of the water it was followed by a stream of squirting water from his mouth, directed at Debra and soaking her face.

Debra stopped laughing as she ran her hand over her face clearing the stream of water. I sat staring at the two of them laughing before I felt comfortable with joining in. We all continued to laugh, yet neither Debra nor I let go of Don's feet. Don looked at the two of us, "I am glad you both got a good laugh at my expense. As punishment you both have to massage my feet."

I was elated with Don's command, and started to knead the bottom of his foot. I was touching his foot; it felt so strong and manly to my touch. I didn't even notice that my other hand was bracing his calf and gently squeezing it making him think I was massaging that as well. His leg was bobbing just at the top of the water and every once in a while his torso would lift up to the water exposing his hardening cock as it floated at the surface.

Don must have been balancing on his hands in order to keep his head above water. He kept his eyes closed as I continued my massage. Debra was watching how entranced I was becoming with Don's foot before she stopped the action. "Oh Brandy he didn't mean for you to have to rub his feet, he was just joking. Now you stop it Don. Brandy is our guest and YOU should be the host and rubbing her feet."

Don gently pulled his foot from me as he sat upright. Don then dipped his hands under the water and I felt him grab my foot and pull it up into his lap. Don began to massage the top of my foot along the toes causing me to take in a deep sigh and let out a low moan, "mmmm."

My little pecker was straining in my suit. If we had to get up out of the water now my cover would for sure be blown. Don lightly stroked my leg as he pressed his thumb into the bottom of my foot. My little cock leaped against the lining of my suit as Don continued the pressure on my foot. I was about to cum from his touch and tried to pull my foot from his hands. Debra quickly calmed me down, "Relax Brandy, Don knows all the pressure points on your foot. He can make all the pain leave your body. He truly has magical fingers." Then she turned to Don, "Now stop trying to give the poor girl an orgasm. I am on to your tricks."

Don released the pressure on my foot just enough to stop my pending orgasm, but not enough to stop the erotic pulsing going on throughout my body. Like a scolded child Don played it off, "Whatever do you mean darling? I'm just being the good Host you so painfully pointed out to our guest." Don turned to me, "Brandy do you want me to stop being the gracious Host and let your foot go?"

I all but screamed at him, "NO, please don't stop."

Don looked at Debra, "See, our guest does not want me to stop massaging her foot."

Debra sat back against the wall and let her head fall back, "You're insatiable. Remember Brandy, if you cum in the water you're going to be the one having to clean the pool." Debra laughed at her inside joke. Don continued his massage and I sat back and enjoyed his touch.

Don pulled my foot closer to his crotch. He rested the heel of my foot on his lap. He gently moved my foot from side to side rubbing my heel up and down the length of his hard cock. Don continued his foot massage before asking me for my other foot, "Brandy, bring up your other foot so I can massage that one too."

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bytonyl65© 10 comments/ 91180 views/ 46 favorites

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