tagTransgender & CrossdressersPool Boy Gets Dressed Up Ch. 05

Pool Boy Gets Dressed Up Ch. 05


"WOW. WOW. WOW. Just give me a minute to grab a baseball bat so that I can keep the onlookers from getting too close. I am going take you beauties out on the town. Let's go celebrate our new union. And just to warn you two, when we get home I will expect one hell of night of earth shaking, ball draining, cum drenching S-E-X." The last word he spelled out slowly.

Don hooked both his arms out to us as we slid our arms through his loops and continued to walk out the door, in one fluid motion. We were already acting as one.

We strolled out to Don's car, the two of them towering next to me. I felt like a child going out with her parents, and probably looked like it too. Don opened the car door and held my hand as I stepped into the backseat. Don then opened the front door for Debra. Don was such the gentlemen. We drove out to the same mall that Debra and I had gone the day before. I was totally comfortable there since we spent the day there without incident.

Don escorted us to a very nice restaurant where we dined on food I couldn't even pronounce, but it was very good. After dinner Debra took control and led the way through various stores. As she was loading my arms full of outfits to try on she mentioned to Don, "We have to get Brandy a whole new wardrobe for England, don't you think?"

Don laughed and clapped his hands together, "My darling I couldn't agree more. And with that I am going to the smoke shop and buy a couple of cigars while you girls flatten out my credit card." We all laughed as Don scurried out of the female clothing store.

Debra called out at him, "Just for that I am buying me some things as well." Debra looked back at me with her beautiful smile and winked. "Let's teach him a lesson and buy out the store." We both laughed.

We had a truck load of boxes being sent back to Don and Debra's house, and Debra didn't seem to be slowing down. Debra literally grabbed me by the hand and pulled me from one store to the next. We finally ended up at the same shoe store that had the gorgeous flirty salesman. As luck would have it he was on duty again.

"Good evening ladies, how may I assist you?" My mouth dropped open as I stared into Sam's (as his name tag stated) beautiful sea blue eyes and the longest black eyelashes I have ever seen.

Debra taking charge as usual, jumped right in, "Good evening Sam. My husband ditched us so we are going to punish him by earning you a great big commission." Debra turned to me with a grin, "Close your mouth and wipe your drool Brandy we have shoes to try on." Debra laughed as she pushed me towards the chairs so we can be fitted for shoes.

Sam laughed along with Debra, and I just blushed. I sat down on one of the chairs as Debra walked up and down the wall filled with shoes on display. Debra was grabbing an armful of shoes. Sam pulled up a low bench with an angled foot rest readying to measure my foot, again.

Debra called out to Sam, "Get her foot measurements and then I want to see her try on all of these."

Sam smiled, showing the whitest teeth, "Anything you want Debra. Will we be sending these to your home as well?"

"Sam you know me so well." Debra chimed back as she had at least a dozen shoes for me to try on.

I kept telling myself to stop staring at Sam but I just couldn't take my eyes off of his slicked back black hair, blue eyes, perfectly sculpted jaw, and those blue eyes again. As he spoke I watched his Adam's apple jiggle up and down his lightly bronzed neck. I watched his hand as it moved down and grabbed my foot. Even his hands were perfect. Long tanned fingers, perfectly manicured nails, and a dark black tuft of hair protruding out the cuff on his shirt.

I shook my head back to reality as Sam lifted my foot onto the measuring device. Sam slipped off my black flat then looked up into my eyes, "Would you mind if I slipped off your stocking and put on a nylon stocking so you can try on the shoes?"

I nodded to Sam and just about came in my panties as his hand ran up my calf. He slipped his fingers in the top of my stocking and slowly guided it down to my ankle. I lifted my foot and he slipped of my stocking. His hands were touching my skin the entire time. I could feel myself leak precum and my cock strained against my panties.

Sam scrunched up a nylon in his hand and slipped it over my toes. The palm of his hand glided against the sole of my foot and then continued up my calf. I bit my lip to keep from moaning out loud.

Debra broke my pending orgasm as she dangled a pair of shoes in Sam's face, "Can we see her in this pair first Sam?"

Sam was still holding my calf, and actually I felt him squeezing it just slightly, "Of course, let me go grab some shoes out of the back. I will be right back."

As Sam disappeared through the door to the backroom, Debra sat next to me, "Oh he wants you almost as bad as you want him." Debra emphasized her point by grabbing ahold of my cock through my skirt.

"My god girl calm down or your cum will be dripping right down your leg. He is gorgeous isn't he? I think we all come here just to have him look up our skirts. He is such a flirt, but I have yet to hear of anyone that has been able to take him home. I think he may like what you have for him." I felt my cheeks flush read again as Debra squeezed my cock.

It just occurred to me what Debra was saying, "Oh my god, did he just look up my skirt and figure out I wasn't a girl? Can we go now Debra, please?"

"Honey, he saw your cock the last time we were here. I am telling you he likes cock. I bet Sam will fuck you good and hard. He is a dreamy Persian god that anybody would love to have. But sweetie, I can tell he wants your pussy over any cougar that comes in here." Debra reached under my skirt and tugged my panties down and off.

I never thought of stopping Debra from doing anything, even stripping me of my panties in a public place, so I just lifted my ass and let her pull them off. "Now let's see if his reaction changes. Brandy we are here until I am satisfied that you have enough shoes for all your new outfits. And that Sam wants to fuck you. You know you would suck his cock if given the chance, maybe I just gave you the chance." Debra winked again at me as she patted my hard cock.

Debra grabbed up my panties and noticed how wet they were, "Look how wet you got these? Oh you want him bad, you're such a little cock slut." Debra laughed at me and I just smiled back.

Sam came out the door balancing about six boxes of shoes. He sat back down and opened the top box. Sam pulled out a silver pair of ankle strap shoes with a single strap. He bent down and pulled up my foot to slip the first shoe on. One hand firmly held my calf, as the heel of my foot rested in the palm of his other hand. I watched his expression as he raised my foot, parting my legs, and exposing my hairless cock. I was not disappointed, and it appeared that neither was Sam, as his eyes locked onto my cock and I could feel the palm of his hand begin to sweat against my heel.

Sam released his grip on my calf reached down grabbed the shoe and slowly slipped it over my foot. The shoe slipped onto my foot like butter. Sam carefully wrapped the strap around my ankle and fastened it. As he guided my foot back to the floor his body leaned forward towards my crotch. He held his face in place as he pulled my other foot up to fit the other shoe. His eyes never left my cock. Sam put on my other shoe and placed my foot back on the ground.

Sam stood up and both Debra and I noticed his thick cock pressing down his leg. Sam held out his hand for me so that he could help me stand. I took Sam's hand and lifted myself up to a standing position. My small cock was hard enough to poke my skirt out just enough so that you could tell I was a guy. Thank goodness it was nearly closing time and the area we were in was void of customers.

Sam continued to hold my hand as I took a few wobbly steps around on the four inch heels. Though I was not used to heels, I was able to hold my own without looking too ridiculous. Sam spun me around in a pirouette before I sat back down on the chair. We all giggled as my skirt lifted just enough to air out my cock, but not high enough to show the world. As I sat back down my skirt was riding a little higher than before so Sam had a really good eye shot under my skirt.

We repeated the routine through various colors of peep toes, platform, pumps, slides, stacked heels, and my favorite, stiletto's. Debra excused herself to check out some jewelry and handbags while Sam and I finished our shoe show. Sam looked at me, "I have one more pair for you to try on, would you mind giving me a hand, the box is kind of high and nobody is left in my department to hold the ladder?"

"Why Sam, if I wasn't so shy I could swear you were trying to get me in the backroom alone. Of course I will come and give you a hand." I twirled my hair and batted my eyelashes is the most flirty pose I could muster.

Sam extended his hand and I graciously accepted it as he just about lifted me into his arms. All of those looks, and muscle too, this guy made my head spin. We walked through the back door and it no sooner shut before Sam spun me into his arms, bent over, and gently pushed his lips to mine. I wrapped one arm around his waist and the other moved up and combed my fingers through his thick hair. My lips parted and his tongue swirled its way into my mouth.

I could feel his monster cock pressing against my stomach. We separated and Sam looked at me, "I have always dreamed of a beautiful girl like you coming into my life. What is your relationship with Debra and her husband?"

I was a little caught off guard with the question, everything was moving fast with Debra and Don, but Debra was encouraging me to play with Sam. "I love Debra and Don. I don't think they would mind if I had a relationship with you."

Sam kissed me again, "I would like the opportunity to date you Brandy. You seem to be everything I have ever wanted, everything I have needed."

With that Sam knelt in front of me and lifted my skirt and pushed his face into my hard cock. He rubbed his face all over my cock and balls before he engulfed my little dick all the way into his mouth. I reached down and grabbed his head with both hands and ran my fingers through his thick black hair. Sam reached both hands around me and grabbed my ass cheeks. He kneaded my cheeks before he spread them and placed the tip of his finger against my pussy. "Oh yes Sam do it, finger my pussy. You are so hot baby. Is this what you need baby, a nice cock in your mouth and a tight boy pussy to fuck?"

Sam answered me by shoving his finger deep into my pussy and deep throating my cock. My little cock barely reached the back of Sam's throat, which allowed Sam to tongue my balls at the same time. I was in heaven and about to shoot my load. I wasn't sure if Sam was ready for that but it felt so damn good. "Oh Sam you are such a good cock sucker. Oh tongue my little ball sack baby. MMMMM. Oh Sam you're going to make me cum."

Sam held me tighter and used his finger that was fucking my pussy to hold me against his face. Sam wanted my cum and I think he likes dirty talk too. I looked down into Sam's eyes as he sucked my cock, "You may be a ladies man on the outside, but baby I know you're a lady wanting a man on the inside. My little boy needs my cum. That's it cock sucker drain my balls. Suck my juice out. Here it comes baby. Ready to feel my hot cum shoot in your cock sucking mouth?"

Sam starting sucking me for all he was worth. He started to moan into my cock and he now had two fingers fucking my pussy with lightning speed. My balls tightened up, my pussy clinched tight around Sam's fingers. I could feel the head of my cock swell. I grabbed onto Sam's head and started to slam fuck his mouth hard, "That's it baby fuck my pussy hard. This is what you want isn't it my little bitch? You like being face fucked by a cock don't you? Well here it comes baby, drink my load. AAAGGGHHH!!!" I screamed out and shot my load down Sam's throat.

Sam did not want to let my cock go, but it was becoming too sensitive as I pulled away from him. I know the feeling of just exposing your deepest desires with someone, so I grabbed Sam's head and pulled him to me for a cum sharing kiss. I pushed my tongue into Sam's mouth and searched my cum out. I felt Sam relax and give into my kiss as he pulled me closer to him.

I reached down to Sam's cock and found that he had cum. As Sam and I kissed I could feel tears dripping against my cheek. I pulled away and looked into Sam's watery eyes, "Oh baby don't worry your secret is safe with me. If I can't keep a secret nobody can." With that I kissed Sam lightly on his lips.

"Brandy, I never...I mean I dreamt about this, but never thought it possible. This was my first time, please don't tell anybody. I just couldn't stop myself. You were all woman and man at the same time. What do we do now?" Sam pleaded with me.

"Sammy don't you worry I will figure out a way to play with you." I handed Sammy my pool boy business card with my cell number on it. "Call me so that I can get your cell number and we can chat some more. Don't worry baby, I think I know what you need. I will see about getting your deepest desires taken care of and I can guarantee that nobody will ever find out."

Sam lifted me into his arms and kissed me with such passion that he took my breath away. I straightened my outfit out, walked out the door, and back into the store.

Debra was sitting waiting for me. "Well, well, well, you look like the cat that swallowed the cock. What have you been up to slut? And where is Sam, sleeping in the back?" Debra's smirk on her face told me that she wasn't mad.

As I got closer to Debra and told her, "Let's just say that Sam has to sneak over to Men's wear and grab a new pair of pants, his are kind of wet. I told him to put everything on your tab and send it to your house. But not before he applies his employee discount." I winked at Debra as I said this.

Debra put her arm around me and started to laugh as we went to find Don, "You are such the little whore. I love that about you. And listen to you, 'put it on the tab and send it home'. Brandy we are going to have a marvelous friendship."

We walked through the mall looking for Don. I was still free balling with all the people around and so unaware that it made me stay partially erect. I loved it. We found Don sitting in a real man's chair smoking a big sweet smelling cigar. Debra and I took a seat on each of the arms of Don's chair. Don put his cigar in his mouth and placed a hand on both of our thighs. "Hello my beauties are we maxed out on my credit card or do we have enough for some dessert?"

Debra and I leaned over and kissed Don on each cheek as we all laughed. We left the mall and got back into Don's car. The car doors no sooner closed before Debra whirled around in her seat, "Ok Brandy, spill the beans what happened in the backroom?" Debra was like a school girl awaiting the latest gossip.

Don had a surprised look, "What did I miss while I was smoking my cigar?"

Debra laughed, "That is what I am trying to find out. Seems Brandy was smoking on a cigar too."

I laughed, "I did not as a matter of fact. And a lady doesn't kiss and tell."

"Bullshit, a woman always kisses and tells. What happened?" Debra giggled out.

I was having a blast with this, "You're right they do. Well you're not going to believe this but it turns out that Sam is not the womanizer he portrays himself to be. In fact, Sam prefers to be Sammy and likes the illusion of a woman but the cock of a man."

Debra and Don both laughed out, "NO. You're kidding right?" Debra wanted more detail, "That good looking Persian god likes dick? I don't believe you? I thought flashing your dick was a joke, I didn't think he would take the bait. I guess I am better than I thought with my gadar."

I filled them in with the details, "Oh ya, he took one look up my dress and he wanted it bad. We went in the backroom and he couldn't kiss me fast enough. Then he went down on me faster than, well, faster than I went down on Don." We were all laughing hysterically now.

I continued with my story, "It gets better. Once Sammy nestled his face into my crotch he started to finger my pussy. I thought he would fuck me but as I prodded him I had a hunch and went with it. I started calling him a cocksucker and dominated him a bit. The guy ate it up and my cock too."

Debra was breathing heavy, "No, really. He not only likes cock but he is a sub like you?"

"You bet he is. I told him he is a girl on the inside and wants a big cock to fuck him. I hit the mark, because as soon as I discovered his true desires the guy shot his load in his pants. I never even touched him. He came with my cock in his mouth and me talking dirty to him."

I could see Debra's mind turning as she turned to Don, "I think we may have a toy to play with and, if I'm not mistaken, I think Brandy wants to be in charge of this one?"

I jumped on this, "Can I? I like being submissive with you two and you both can fuck me tell the end of time, but something about turning Sammy into a sissy cock sucking tramp that really turns me on. I want to get him to the point of begging for Don's cock and then have Don come in and fuck Sammy right into the cock sucking whore he wants to be."

We drove home and we all tore off our clothes as we ran up to the master shower to prepare for bed. Debra and Don showered up as I douched, not wanting to waste a second of time. We dried off and Don and Debra headed to bed. I had a little makeup to reapply. A girl's gotta look her best for her lovers. I slipped on a nice pink baby doll with matching panties and walked into the bedroom.

As I walked into the bedroom I could see there was going to be no foreplay tonight. Don was lying on his back naked, hardon sticking straight up in the air. Debra was sitting on Don's face facing the headboard. Debra was holding onto the top of the headboard and grinding her pussy into Don's face, "Come on eat me baby. I am so fucking horny. That's it move that tongue. OHHHH! YES! Bite my pussy lips. Stretch them with your teeth baby."

I crawled on the bed between Don's legs. He must have sensed my on the bed because his legs spread giving me access to his cock. I ran my tongue up his shaft and licked his dripping precum. I moved back down to his balls and started washing his balls with my tongue. His balls smelled so good and I could tell that Debra had her pussy on his pole. "You like my little treat I left for your Brandy? I came fast when I sat on Don's cock, make sure you clean all my juices up."

"Yes mistress. I am licking his balls now. I think you may have dripped down to his ass crack too." I said as I ran my tongue over his hairy hole.

Don moaned into Debra's pussy. I pulled my panties off and moved over Don's dripping cock. I was facing Debra's back and held her hips for support. I squatted down grabbing Don's cock and pointing it to my waiting pussy. I wiggled my ass to accommodate his head and to allow its entrance. Once Don's head broke through my pussy, I plunged myself all the way down his shaft. Don's cock filled me all the way up.

I grabbed ahold of Debra's hips and pulled her ass to my face, "Yes, Brandy, eat my ass while Don eats my pussy." I pushed my tongue deep into Debra's dark hole. Debra moved back down to rest her pussy on Don's face, then leaned forward opening her ass up for me to devour.

Don and I worked Debra over orally. Don continued to gyrate his hips, grinding his cock into my pussy. I lifted up off of Don's cock and slammed back down in between eating Debra's ass out. Debra was ready to cum and so was Don.

Don began to pump his cock into me faster and faster. Debra was pushing back against both of our tongues, "Oh yes that's it. OH YES! FUCK!" Debra screamed out and went stiff as she filled Don's mouth with her cum juice.

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bytonyl65© 18 comments/ 82390 views/ 49 favorites

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