Becoming Samantha! Pt. 03

My mind started flashing back again.

The Fearsome Foursome was sitting around my living room, just shooting the breeze. The other three were kind enough not to mention the Senior Prom which would be in two days. All of them had dates, I'd gotten shot down three times and just quit asking. Jake's phone chimed, he looked at the message, and turned very pale.

"What's the matter dude? You look like you've just seen a ghost."

"It's Madeline, she was supposed to be my date to the prom."

"Supposed to be? WTF? What are you talking about?"

"She just texted me. She caught the new flu bug that's running around. It's highly contagious. She has to be in quarantine for the next week which means no way can she go to the prom this weekend." Jake looked like someone had just kicked him in the nuts. "And it's way too late to get another date, damn near everyone has already been asked." He looked at me guiltily when he realized what he'd said.

Clare had been walking through the living room when she heard this exchange. "I might be able to help you, Jake."

"What?? You mean a big-time college girl like you would go to my high school prom with me?"

"No, that's not what I mean at all. I mean my cousin is coming to visit this weekend and I might be able to talk her into going with you."

I looked at Clare strangely. She shook her head. We both knew we didn't have a cousin who was coming to visit this weekend.

"I don't want to sound like a pig, but do you have a picture of her?" Jake asked hopefully.

"I believe I might." Clare said as she scrolled through the photos on her phone. "Here's a good one of her. Her name is Samantha." Clare winked at me over Jake's shoulder as she showed him a picture of me, en femme. I couldn't believe she was doing this to me.

"Holy shit, Sam. How come you never told us you had a cousin who's this hot. She's fucking beautiful."

"I was trying to protect her by keeping her away from three dogs like you guys!" I tried to joke.

"I'll give her a quick call and see if she's interested." Clare went back to her bedroom. My phone vibrated. It was a text from Clare. "Get your ass back here."

I went to her room and said, "Are you insane? You're trying to set up one of my best friends with my female alter-ego! Are you crazy? What the fuck are you thinking?"

Clare looked hurt. "Do you trust me?"

"What, what the fuck are you talking about? What does that have to do with this?"

"Do you t-r-u-s-t me?" She spelled each letter slowly.

"Clare, you know I do. You've been an integral part of Samantha's growth. Your counsel and guidance have helped her blossom into a confident woman. Of course, I trust you. You're so much more than just my big sister, you're my BFF."

"Then hear me out. Think of this as Sammie's graduation to full womanhood. You've been on dates before; you've been with men before. If Samantha can go to prom with Jake, one of Sam's best friends, and Jake can't tell who it really is, then Samantha is the woman she's always thought she could be, Samantha is the woman she's always wanted to be. What do you say? You know I'll do everything I can to help you get ready."

I stood there silently; thinking over everything Clare had just said. "I guess I must be the crazy one. I'll do it."

We walked back out to the living room where Jake, Robbie, and Teddy were waiting. Clare smiled at Jake. "Samantha said she'll go with you to your prom. She made Sam swear you weren't some flaming asshole. Sam told her you were just half-assed, not a complete ass."

Jake looked at me for a second like he was going to kill me, then realized Clare was just teasing. "I actually lied and told her you were a good dude. I told her she'd have fun with you at prom."

Jake looked relieved. "I owe you one, bro. Big time."

Clare was having way too much fun with this. She'd once bought a floor-length black satin halter gown with a thigh high slit that she never got a chance to wear. She wanted me to wear that and pair it with the lingerie and jewelry sets that Angelo had gifted to me. Obviously, the marabou mules wouldn't do for prom. When she bought the dress, Clare had also purchased a pair of black satin stilettos with open toes and a black satin rosette with a rhinestone center on the vamp.

Clare took me to the salon the morning of the prom. I had my hair done in an updo with a smattering of hair tendrils hanging down loosely around my neck. I got both a manicure and pedicure with my nails done in a silver glitter polish with 2" gel extensions on my fingers. They looked amazing. Clare then surprised me by taking me to the massage parlor. "I want you to be as relaxed as possible, Sammie. If you've never had a full body massage before, you won't believe how heavenly it feels." We had side-by-side massages, and then Clare took me home. I was so relaxed, so loose from the massage. All my tension was gone.

Clare immediately popped me into a hot bath with an Opium bubble bomb. I continued to luxuriate, reveling in the feel and smell of the bubble bath on my hairless body. I must have fallen asleep. An hour later Clare was banging on the door. "You're going to turn into a prune! Get out of there. There's some Opium body powder on the sink. Dust yourself from head to toe, then slip into your prosthetic and get out here. We still have a lot of work to do. Check that. I still have a lot of work to do, you just get to sit back and enjoy the fruits of my labor!" She was laughing when she said that.

I did as Clare requested. It had been a long time since being 'naked' in front of my sister had made me uncomfortable in any way. "Put all your lingerie on, including your stockings and heels. I want to give you a glamorous evening look and match the makeup to your nail polish. This is going to require some thought." I sat in the makeup chair. Clare would try a color on my upper cheekbone and then wipe it off, repeatedly shaking her head as if to say no. Eventually, she smiled at her selections and got to work.

After a long time and a lot of effort, she finished. She smiled at her handiwork. "Normally, I'd make you wait but I want you to see what I've done for you." She slowly spun the chair around so I could see myself in the mirror. I gasped. "Clare, holy shit! Clare, you're an artist! This look is way past glamorous, this look is off-the-charts ready-for-the-red-carpet!"

I looked so hot I looked like I would burst into flames. Clare had done my base makeup in neutral, more natural tones. It was my eyes and lips that jumped out at you. She had used a smoke gray / silver palette on my eyelids. The black eyebrow pencil, black eyeliner, and black mascara all contained hints of silver and sparkled just enough to let you know the silver was there.

The lipstick was off the charts insane. It was pearlescent diamond glitter gloss. My lips looked so plump and so juicy; they looked like they had liquid diamonds on them. They looked so tantalizing; I wanted to kiss myself. No, I wanted to see those lips wrapped around my cock, sucking me off. I shook my head at that crazy thought. I just beamed at Clare.

"Sometimes I even amaze myself, but I do have to admit, you're a gorgeous canvas to work with." Clare said. "Now let's finish getting you dressed."

Clare helped me into her black satin halter dress. It was almost backless and barely covered the top of my waist cincher. The bodice and waistline were ruched; the pleats were gathered just a few inches above my navel by a rhinestone rosette. The thigh high slit hung closed as long as I wasn't moving. Any movement by me at all and the slit opened up to the top of my thigh. Every time I took a step, I was flashing stocking tops held up by garter tabs. She wouldn't let me put on my own jewelry and insisted on putting it on me. I felt like such a princess.

My makeup was glistening, my jewelry was glistening, my sheer 15 denier jet-black stockings were glistening with every step I took. Clare pulled out a small bottle of Opium perfume. She spritzed it behind my ears, she spritzed it on my decolletage, she spritzed it behind my knees. She handed me a black satin clutch with a rhinestone closure. "Put your perfume in here. I've already put in everything else you'll need." I looked inside. Sure enough, there was makeup for touch-ups and a lubricated condom.

"For Jake? Now I know you're crazy!"

She just smiled knowingly and started to say, "You'd much rather have one and not need it than...."

I interrupted her. "I know, I know. '....than need one and not have it.' "

Clare smiled again, a little wickedly this time. "I'm not saying, I'm just saying." She shrugged her shoulders. Just then the doorbell rang. "Wait just inside the hallway where Jake can't see you. I'll call you when it's time." I heard voices, lots of voices. I was more than a little confused.

"Sammie, Jake is here."

I walked into the living room and gulped. Jake was not the only one here. Robbie and Teddy were here. And Robbie and Teddy's dates were here as well. The boys had decided to rent a large limousine together. Apparently, someone thought it would be a good idea to get group pictures before we left.

All eyes were on me as Clare said, "Sammie, this is Jake. He's your date tonight. This is Robbie and this is Teddy. I'm sorry guys but I don't know your dates' names." Robbie introduced his date as Becky and Teddy introduced his date as Alicia. I recognized both of the girls from school but didn't really know them very well. They waited patiently while Jake pinned my corsage to one of the straps of my dress. I pinned his boutonniere to his lapel. Of course, Clare was taking lots of pictures.

Jake finally told Clare, "We have to go, or we'll be late. Hey? Where's Sam?"

She answered. "Sam wanted me to tell you to have a great time. He said he was happy for all of you, but he just needed some alone time. I think he was taking in the latest action feature at the movie theater."

Jake nodded and held the door for me. I saw Clare grab his elbow and whisper into his ear as he was leaving. As we headed to the car, I put my hand through Jake's arm and asked, "What was that all about?"

Jake laughed, just a little. "Clare told me I better be nice to you, or she was going to kick my ass. She said you were doing me a favor and I better act like it. She said you're her favorite cousin."

"She's my favorite cousin, too." I answered. "There aren't many better people than Clare in the world. She shows a tough exterior but inside she has a heart of gold. And I have a favor to ask. When we get into the limousine, will you please sit next to the side of my dress that has the slit in it? I really don't want to be flashing my thigh and stocking top while we're riding."

"Of course." Jake said gallantly. He helped me into the limo, we sat across from Robbie, Becky, Teddy, and Alicia. Robbie and Teddy looked slightly disappointed that Jake was blocking their view. We chatted amiably on the way to prom, but Becky and Alicia gave me an occasional glance of disapproval.

We arrived at the prom. As I scanned the room, I gave out a loud sigh. "Of course." I whispered to myself.

Jake leaned down. "What was that?"

"I said, 'Of course.' I'm talking about the colors of the other girls' dresses. They're wearing every color of the rainbow and some colors I don't even know the name of. Of course, I'm the only one here wearing a black dress. On top of that, it's cut way too low in the front and the side slit pops open showing my entire leg from ankle to thigh. I'll bet I'm the only girl here wearing garter stockings too. I'm going to kill Clare when we get home!"

"I know girls are always comparing what they're wearing, especially at a fancy event like this. I hope you'll let it go. I hope you won't give a damn what the other girls are thinking about what you're wearing. You're easily the most beautiful girl here and second place isn't even close. Every guy in this place wishes he could be me. Every guy in this place wishes he could be with you. Let it go, show me some of that Robertson family confidence. Let's have fun!"

I looked at Jake wide-eyed. This was the captain of the basketball team talking; this was an encouraging and caring pep talk just for me. It was a side of Jake I rarely saw. In spite of myself, I stood on tiptoe as I put my arms around his neck and gently kissed him on the cheek. "Thank you for that, Jake. I needed that." I stood back from him, purposely posing so the side slit on my dress was wide open, exposing all of my stocking-covered leg. I had my hands on my hips as I licked my lips and said, "I'm your party girl."

Now it was Jake's turn to stare at me wide-eyed. I don't think he expected his pep talk to have such an immediate effect on me. He smiled at the confident, sexy girl posing for him. "Then let's party!"

We had a blast. Jake and I were the center of attention, and I didn't care. Other than the Fearsome Foursome, the other kids at school had never treated Sam that way. Boys wanted to dance with me, girls were chatting with me, I felt like the queen of the prom.

At one point, I excused myself to go to the bathroom. Inside the stall, it was a little bit of an effort to extricate myself from my prosthetic, but I managed. As I was sitting there, I heard someone else come in. It was Becky and Alicia. They were talking; they were talking about me.

"Can you believe that bitch?"

"Coming to our school acting like she owns the place."

"And dressed up like a $1,000 an hour hooker?"

"The nerve."

"I never."

Becky's and Alicia's mouths were hanging open as they saw me come out of the stall and walk to the mirror.

"Actually, I bet you do. All the time. Talk about people behind their backs because you don't have the guts to say it to them in person."

Visibly agitated, they wouldn't look at me or reply. After washing and drying my hands, I touched up my makeup.

"Bitches like you used to be able to shake my confidence but that's long in my past. If you were any more jealous of me, you'd both be as green as She-Hulk."

I left the bathroom. Robbie and Teddy were both talking with Jake. I told all three of them exactly what happened. Becky and Alicia came out of the bathroom; saw the four of us talking together and just stopped. Robbie looked at Jake and said, "Why don't you take Sammie for a walk?" Then he looked at me and said, "I'm sorry, Samantha. That was really shitty of Becky and Alicia. But at least all of us found out what kind of people they really are." He and Teddy turned and walked towards where they were standing.

Jake took me by the hand and led me the other way. We didn't see the four of them for the rest of the night. I found out the next day that Robbie and Teddy had taken the girls home, went home themselves, and then sent the limousine back to the prom for Jake and me.

We enjoyed ourselves immensely. Jake was just so sweet and gentle. This was a side of him that Sam never got to see. We were having so much fun we stayed until the end of prom. We walked to the limousine hand-in-hand; my head was resting on Jake's shoulder. The driver opened the door for us. "Wait here." I told Jake. I walked the driver a little bit away from the car so I could talk to him in private. Then we went back to the car where he helped us in.

"What was all that about?" Jake asked.

"I just told the driver he could take his time getting us back to my house."

Jake looked at me with a raised eyebrow but didn't push it. He clumsily put his arm around me to pull me closer to him. He didn't need to do that. I turned and climbed into his lap facing him. My legs were straddling his; the slit in my gown was wide open and my stocking-covered leg was exposed ankle to thigh.

"Samantha! Wh-What are you doing?"

"I think you know exactly what I'm doing." I replied as I reached behind my neck and unclasped the halter of my dress. My naked breasts were soon exposed to him.

"Samantha, I promised Clare I would be nice to you! She's more than a little crazy. She REALLY will kick my ass. Please, stop!"

I reached behind me to unzip my gown, letting it fall past my hips. I had to shimmy and shake to get out of it, but I never left Jake's lap. "You're asking me to stop, but this throbbing bulge in the front of your pants wants me to keep going."

I leaned in and kissed him hard, thrusting my tongue inside his mouth. At first, he didn't return my kiss, but I was insistent. I began to lick and nibble his neck, ears, and lips. This time when I thrust my tongue into his mouth, he returned my kiss with a frenzy. He was pulling me to him, one hand was squeezing my ass cheeks, the other hand was stroking my stockings.

"Oooooohhhhh, yes Jake! Mmmmmm, baby, that feels so good." I was grinding my ass against his cock, and I could feel him start trembling. "No, baby. Not like that. You're going to cum in my ass. It's my time of month and I don't want to make a mess, but I have to have you somewhere inside me."

I stopped and climbed off of him so I could unbelt, unbuckle, and unzip his pants. Together we pushed his pants and underwear down around his ankles. I reached for my purse and found the lubricated condom. Tearing it open, I carefully rolled it down the length of his pulsating erection. Then climbing back into his lap, I reached behind me and guided him to my rosebud.

I sat back quickly, engulfing his shaft all the way down to his lap. "Jake, shit, oh Jake, oh damn, you feel so good inside me. Mmmmmm, baby, this is so good."

I started squeezing my ass muscles and rotating around his hardness; he started moaning immediately. "Nnnnnngggggghhhhhh, oh Sammie, oh Sammie baby! Your ass is so tight, so wonderful. Fuck me, Sammie, fuck me good!"

I began to ride Jake's cock, slow, then fast, then slow again. All the while I continued to milk him with my ass muscles while I rotated my hips around his cock. Suddenly he reached down, grabbed me by the hips and began using my ass to jerk off with. He would pull me up until just his prick was inside me, then jam me all the way down to his lap while he thrust up inside me. I shuddered. Jake was starting to hit my P-spot with every thrust.

"F-fu-fuck meeeeee! Oh-stop-no-don't-stop-oh-stop-oh-no-don't-stop-oh-stop-oh-no-don't-stop! FUCKMEFUCKMEFUCKME!!!!" I was screaming as I collapsed against his chest in the throes of multiple orgasms. I lost complete control of myself from the sensation of his prick rubbing my P-spot again and again.

Somewhere through my orgasmic fog, I could feel Jake's raging member explode inside the condom wrapped around his cock buried in my ass. "Yes, Sammie, yes, Sammie, YES! Pussy good, so good, cum, cum, cumming for you, cumming for my beautiful Sammie!"

I could feel Jake erupting again and again through the thin sheath of the condom. I would have had cum running down both of my legs had I let him take me bareback. With a final shudder, Jake collapsed against the back of the limousine seat. We both just sat there in each other's arms as we came down from our orgasmic highs.

"Sammie, Sammie, oh my beautiful Sammie!" Jake cooed into my ear. He was nuzzling me and caressing me as he continued to tell me how good I had made him feel. There was a tapping on the privacy screen. The driver was letting us know we were pulling up to my house. Jake and I hurriedly got dressed. I checked my makeup and touched it up.

We got out of the limo and walked to my door hand-in-hand. Jake pulled me to him and kissed me deeply, passionately. Both of us were completely surprised when my mother opened the door. "Jake, I'm happy to see that you're following my daughter's advice and being nice to my niece. Of course, my definition of 'being nice' and my daughter's definition of 'being nice' might be slightly different." She smiled to take any sting out of her words. I already knew Jake was her favorite of the Fearsome Foursome.