tagTranssexuals & CrossdressersPool Boy Gets Dressed Up Ch. 04

Pool Boy Gets Dressed Up Ch. 04


I used every skill Debra showed me in the last week to make Don happy. His cock was thicker than its replica, but more pliable. His precum tasted sweet and felt so good swirling around my mouth. I gently pulled on Don's balls forcing his cock to tighten and go further down my throat. I was very pleased with myself that I was able to take about seven inches down my throat. My goal was to press my nose into the closely trimmed little patch of hair above his cock.

Don pulled his cock out of my mouth, grabbed his cock by the shaft, and lightly caressed my face with his cock. Looking down at me, "You're very good. Let's go upstairs where we can all have a good time, shall we?"

Debra helped me up off my knees, "Come on you little cock sucker, let's get you the fucking you need. I need your tongue to take care of my pussy, you have me dripping and horny, you hot little minx."

Don hooked my arm around his and escorted me up the stairs, I felt like a girl at the prom. The three of us climbed the stairs naked and horny. Don opened the door to their bedroom and led me to the bed. As we got next to the bed Don scooped me up into his arms and walked on his hands and knees to the middle of the bed where he lay me down. I sank into the soft bedding as Don leaned in for another of his body trembling kisses.

Debra joined us on the bed, coming in from the other side of me. Soon we were all taking turns kissing one another. My hands were all over the two of them; lightly stroking Don's huge member, fingering the little nub above Debra's pussy which I know drives her wild, and alternating sucking on Don's nipples then Debra's. The entire time I felt a finger probing my soon to be fucked pussy.

Debra first pushed in her slender finger into my pussy. She continued to slowly finger fuck me, to loosen me up which was soon replaced by a much bigger finger pressing its way into my hot tunnel that I knew must be Don's. Then to my surprise, Don pulled out his finger and grabbed Debra's hand, together they put their forefingers together to form one and gently and slowly pushed it into my hot hole. "AAHHHH!!! Don't stop, please don't stop, fuck me please." I screamed as my hole stretched to accommodate their probing.

They continued to hold hands and fuck me as they both stared into my eyes. Debra spoke first, "Are you ready Brandy? You are about to cross over to another world, are you ready for a man to take your virgin pussy? Once Don fucks you the three of us will unite as one. Do you want to be our lover Brandy? Are you ready to commit to us?"

I look up into both of their faces, "Please, oh yes please. I have never been happier in my life. I want you both as lovers. Please make love to me. I know I love the both of you with all my heart."

Don kissed me on the lips and moved in between my legs. He lifted my legs up to his shoulders and placed the head of his cock at my entrance. Debra squirted lube on Don's cock and jerked it a couple of times to fully coat it with the lube. Then she inserted the bottle of lube into my hole and squeezed, I felt the rush of the liquid shooting into by pussy. Debra held on to Don's cock and guided it to my hole. This really was the three of us making love.

Debra swirled Don's cockhead around my hole before lining it up. Debra looked down at me, "Are you ready Brandy?"

I looked back at Debra, "More than you will ever know."

Don pressed forward and pushed the head of his cock into my ass. With all my training that Debra gave me, nothing prepared me for the warm sensation of a real cock penetrating me for the first time. I did remember to push out as Don pushed the first couple of inches of his cock into my waiting virgin pussy. Debra continued to hold Don's cock as he slowly fed me his cock, inch by inch. When I felt Don's full weight press against my pelvis I knew I was no longer a virgin.

I could feel the tears of happiness flow down my cheeks as I watched my lovers work together, sharing my first penetration by a real cock. Don leaned forward and started to kiss away my tears. Then I felt Debra start to kiss away my tears on the other side of my face. Debra consoled me, "There, there, it's all right now. He's all the way in. Was it everything you expected? Does Don's cock feel good inside of you?"

I lifted my head and kissed her, "Thank you. It is everything I could have imagined and so much more."

Don lifted back up and slowly pulled his cock out of my pussy, then slowly sawed his way back in, then out again. He was so slow and methodical about his movements. Making sure that his cockhead puts just the right amount of pressure in all the right places deep in my bowels. "Yes, yes, fuck me Don. Fuck me harder. Take my virgin pussy. Stretch my pussy. Fill me with your cum."

Don grinned down at me and pulled his cock nearly all the way out and slammed it back as hard as he could. "YES, that's it, harder, please fuck me harder." I screamed out in ecstasy.

Debra swung her leg over my head, facing Don. I looked up into her wet, puffy lipped, hot pussy. "I need my pussy eaten and we need to quiet her screams before someone calls the cops."

I looked up to see Don and Debra sharing a deep kiss before Debra lowered her pussy onto my mouth. I dove into that pussy like it was my last meal. I pushed my tongue into her pussy as deep as it would go. Her pussy was hot. Her pussy lips were swollen as I sucked on one and then the other. I then opened my mouth wide and sucked them both in. I ran my tongue up and down her clit. I could her Debra scream out, "OH YA I'M CUMMING. FUCK THIS IS SO HOT."

Debra sent a long stream of her hot sweet nectar down my throat. Bringing Debra to an orgasm always gets me off, as I felt my pussy squeeze around Don's cock harder than I thought possible as I felt my hot cum shoot onto my chest and stomach. The pressure must have been too much for Don as he cried out, "OH ya I can't believe the pressure. I'm cumming. I am going to fill your virgin little hole full of cum."

I felt Don's cock tense and swell just before his hot cum started to fill me up. The pressure of his hot cum was so intense that his cum shot out my ass and onto Don's thighs. Don slowly pulled his cock out of my ass and rolled to his back. Debra swung her leg back over my head allowing me to gaze upon the cock that just fucked me. Don's cum was dripping down the shaft of his cock.

I quickly rolled over onto my hands and knees and crawled in between Don's legs. I wanted to taste his cum. I placed a hand on his thighs and moved my face forward. I first licked up the droplets of cum dripping down his inner thighs. It was pure nectar of the gods. I savored the feeling of his thick hot cum on my tongue before it registered how good it tasted. I then moved to the head of his cock, where a big white glob was spewing out. I opened my mouth wide, as not to touch the sensitive head with my teeth, and gently enveloped my lips around his head. My tongue gently flicked the white cream into my mouth. "MMMMMMM"

I could hear Don and Debra laughing at me. I was like a child trying ice cream for the first time. Don was still hard. He showed no signs of losing his erection. Don pulled my cock from his mouth, "There is more where that came from. You will be drinking a lot of cum sweetheart, don't you worry."

Debra was now on all fours waiting for Don's cock. Don walked on his knees, lined his cock up with her pussy, and plunged it balls deep into her wet pussy. As Don's balls slapped against Debra's ass, she voiced her acceptance "OH FUCK, YES. Brandy, get under me and eat my pussy and lick Don's cock while he fucks me."

I hungrily dived under Debra, from the side. I lay beneath her on my back looking up at one of the most intimate and beautiful sites I have ever seen. Debra's pussy was glistening with her pussy juices. Her pussy was spread wide by Don's big cock. Don's balls were hanging down, almost lying on my forehead. With little effort I could lift my head and taste any and every treat that lay before me.

Don's cock slowly retreated from Debra's pussy, his shaft dripping with pussy juice, before he began his steady rhythm of fucking Debra. Don's balls waived back and forth before my eyes. Debra's juices became a frothy flow in no time. I reached out with my tongue and began to lick Debra's pussy. As Don lunged forward, bearing his cock in Debra's pussy, his balls slapped the right side of my face. I stuck out my tongue, and licked Don's shaft as it moved in and out of Debra's pussy. Debra's juices collected on my tongue as I slurped it up, relishing in the taste.

I moved my head down and caught Don's balls with my mouth. Don stopped as soon as his cock was fully embedded inside Debra's pussy. This allowed my time to enjoy cleaning Debra's juices off of Don's balls. "Oh ya Brandy suck my balls. Grab them with your teeth baby and pull on them. God, yes! That's it." I held onto Don's balls with my teeth, careful not to clamp down too tight, but tight enough to stretch his sac down as my head came back to rest on top of the bed.

I knew by stretching Don's nut sac that his cock would be pulled tight within Debra's pussy making him more sensitive. Debra must have had an equally gratifying sensation as they both rang out in unison, "Oh shit that feels so damn good. Don't stop Brandy."

I knew that they were both on the verge of cumming and I wanted to be the reason they went over the top. I wanted to make them as happy as they made me. I secured my hold on Don's sac before I moved my head towards Debra's chest, pulling Don's nut sac as far as possible. Don slammed his cock as deep as possible planting his cock inside Debra. I could see that Debra pushed back hard against Don, as her leg muscles flexed, gripping her pussy as tight around Don's cock as possible.

Debra came first as her head shot up in the air and her torso came slamming down by my head, "I'm cumming, shit, shit, shit, my god..mmmmmmmm!"

The pressure was too much for Don, as his fingers, that were gripping Debra's waist, turned white. I watched the underside of his balls pulse as I knew he was shooting a load deep inside Debra. Don blurted out incoherent grunts as he came, "Oh Fuck! I'm cumming.nnngggg! Ahh! MMMM!"

As I watched their bodies relax I released the hold I had on Don's nut sac, hoping that I didn't puncture him. Don's cock slowly slipped out of Debra's pussy. I quickly scooted back down under them just in time to be rewarded by a gush of Don's cream flooding from Debra's pussy. I opened my mouth, not wanting to lose a drop, and planted it at the opening of Debra's pussy. I lapped up the cum before letting my head fall back and pulling Don's cock into my mouth.

Don's cock was still dripping with his thick cream, and his cock was just soft enough to allow me to engulf its entire girth. Don's balls were resting on my forehead and I was able to look up to see, for the first time, Don's pink rosebud. What a site. So many things to explore, I thought to myself.

I licked every bit of fresh cum from Don's cock head and all of Debra's pussy juice off of his shaft and balls before Don pulled his cock out of my mouth, becoming too sensitive. Debra took my vacant mouth as an invitation as she lowered her dripping pussy onto my face, "All good cum sluts clean their messes. Eat me Brandy. Lick all of Don's cum out of my pussy. Make me cum baby, use that tongue like you know how."

I wrapped my arms around Debra's torso to hold on for I knew I was going to do my best to send this woman into an orgasm orbit. I ran my tongue up the entire length of her pussy before I sucked on her pussy lips. I know how much Debra loves her pussy lips sucked on as I rim the insides of her pussy. "Yes! That's it baby use that tongue. God suck my pussy harder baby. Eat Don's cum. Suck it out of me. I'm going to cum hard. Brandy, oh, yes, fuuucckkk!"

Debra's back arched up, trying to pull away, but my arms locked on tight holding her back so that I could continue to eat her through her orgasm. Floods of Don's juices mixed with Debra's sweet nectar rushed out of Debra's hot pussy. I could feel their cum dripping down the sides of my face. I shook my head back and forth while flicking my tongue deep inside her pussy. I could feel Debra's body flex and tighten as she shoved her face into a pillow to muffle her screams of pleasure.

Debra rolled off of me, not being able to take it anymore. Don sat back against the headboard as Debra snuggled under his left shoulder. I felt that the climax was over and my services were no longer needed. How do I get out of this awkward moment? Then Debra reached out her left hand, and Don raised his right, both beckoning me to join them.

"Come here baby, come cuddle with us." Don's voice was so soothing to my ears. I crawled under his arm as he wrapped it around me and pulled me to his chest. The smell of sex was intoxicating. I lightly caressed Don's cock as he rubbed my back. Debra reached over and cupped her hand on my face. I looked up at her as she leaned down and kissed me on the lips.

I fell into a deep sleep, as we all must have, because when I awoke I could see that a couple of hours had past and Don and Debra were still asleep. We all started to stir; it was dark outside and looked to be the middle of the night. Nobody was expecting me tonight anyway so I just cuddled in with my lovers and enjoyed the body heat. We all drifted off to sleep until the morning light woke us.

Don pulled me and Debra into him and kissed the tops of our heads, "Morning ladies. I hope you both had as good a night sleep as I did? I can't remember the last time I had such a well fucked night sleep."

Debra stretched her body out, kissed me on the cheek and Don on his lips, "Morning loves. I think we all could use a shower. Why don't you two go ahead and get started while I run down and put on a pot of coffee?"

I was delighted to spend more time with Don's naked body. Don gave my ass a nice little love slap, "Come on sleepy head, let's get that pretty little bottom of yours into the shower?" I lifted myself up off of Don's chest and moved off of the bed. By the looks of the bedding, I would say that it would have to go out to the cleaners as well.

Don and I slumbered to the shower while Debra left the bedroom to make the coffee. I wondered if this was a one-time fling. Was the spontaneity over? Was Don going to be upset with what happened? Again, I was overthinking everything, but the happiness I felt I wanted to hang on to it for as long as I could.

Don entered the enormous shower and turned on the water and steam. Don reached out his hands and helped me pull off my wig. The glue stuck a bit to my hair but seemed to have pulled off without much of a battle. Don threw the wig out of the shower and onto one of the sink counters. Don reached over and grabbed a bottle of perfumed bath soap and poured some in his hand, "Come here sweetheart, let me bathe you."

I rinsed my body under the warm water before stepping over to Don. My knees went weak as Don's soapy hands explored every inch and crevice of my body. His hands were like a million little electric needles touching my body. I was getting a hardon, what little there is of it. Don pulled me to his chest as he ran his hands up and down my back, "Feel good baby. Do you like when I touch you all over?"

I pushed my face into Don's chest, "Oh yes. You and Debra have made me so happy."

"The first time Debra and I saw you cleaning our pool we both knew you were the one to complete our little family. Debra and I both have a very specific appetite for sex. You not only fulfill our dreams of sex, but we have both become very fond of you, if you know what I mean?"

I was afraid to presume the wrong thing and look like a fool, when I felt Debra's body sandwich me in between the two of them. "What Don is saying Brandy, is we both do love you. You have turned out to be a great girlfriend and companion for me. We would like to make a proposition for you. Let's get cleaned up and go out to the pool, have a cup of coffee, and talk."

I couldn't imagine what they wanted to talk to me about, but right now I didn't care I was naked with my two favorite naked people. We lathered each other up and rinsed the soap off. Don gave me my enemas and cleaned me out. He was always gentle and never forced anything on me. We dried off and went straight downstairs. No clothes were worn.

Debra brought in a tray with our coffee and some Danish as we all sat at the table by the pool. Debra was first to begin. Placing a soft hand on my knee, "Brandy dear, I know how much you prefer being Brandy over Brandon. I can see how your eyes light up when you slip into a pretty outfit and get your face all made up." I agreed, but still bowed my head in embarrassment.

"Don and I would like to make you an offer to come live with us as Brandy. Don't get me wrong, it's not that we want you just to be a sex toy, we want you to come live here as part of our family. We both love you like our own and we want you to be who you really are. Of course that would mean you would learn about our businesses, how they operate, and how we operate in business. We would travel the world. While here at home, you would have your own room filled with beautiful clothes."

I sat stunned as Don picked up where Debra left off, "Last night was fantastic. I felt a true emotional connection with you Brandy. Not like I feel with Debra, but our love goes beyond that. We know we can have you in our hearts and bed. Having you and Debra as part of my life would make me the happiest man on earth."

I gave Don a funny look and giggled, "Here I thought I was the happiest man on earth." We all started to laugh. "When do you want my answer?"

Don and Debra looked at each other with almost hurt feelings, "Well, anytime you feel comfortable. And if you don't want to be with us we would understand." Debra actually had tears in her eyes worried about how I would answer.

I stood up, walked over to Don, swung my leg over his lap, and sat down on his soft cock, "Good, because I couldn't wait another second to tell you that I would love to be part of your family." With that I gave Don a big kiss as I ground my little ass against his now hardening cock. Debra came up next to me and added her mouth to our kiss as we all hugged and kissed each other.

Debra broke the kiss first, "We are so delighted. We have so much to prepare for. First we have to explain to your parents that you want to be Brandy and move in here."

"NO!" I screamed out, "They would never understand. Can't we think of something else?"

Debra patted my back, "Calm down baby. I prefer honesty, but we can start off with telling them that you have obtained an internship with Don's company and that you would be staying here in between flying around the world as our intern. You don't start school until September anyway, so that will buy us a couple of months to ease into this. We can call it a trial run for all of us. How does that sound?"

At the same time Don and I both said, "Perfect."

The doorbell rang and Debra looked at the two of us, "Stay here, I'll go get the door." Debra grabbed a terrycloth wrap and put it on as she headed for the front door. I stayed on Don's lap, started to kiss his neck, and grind my ass against his raging hardon.

The sound of Debra's voice broke us up from making out. "Is this how it's going to be every time I leave you two alone? Brandy you are such a little cock slut," she said with a wicked little grin on her face. Debra also had an arm fool of boxes and a couple of bags dangling from her fingers. "Guess what arrived? Part of Brandy's new wardrobe."

I jumped off of Don's lap, kissed him on the lips, and ran to Debra like a child on Christmas morning. Debra turned and headed back towards the stairs, "Come on Brandy, we have a lot of work to do." Debra and I went upstairs to one of the spare bedrooms, which is just as beautifully furnished as the rest of the house. Debra emptied her arms and hands onto the bed.

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