Becoming Samantha! Pt. 01

"No! No fucking way! Not a snowball's chance in hell! Are you guys all fucking crazy??!!!!" On the outside, I had to show these guys I was totally against their idea. Inside, I was tingling more than just a little bit.

Jake, Robbie, Teddy, and I had been best friends since grade school. We were now attending the same Division-III college together. The three of them were all jocks. They were good players, just not good enough to receive full ride scholarships from D-I or D-II schools. As such, they had to find financial help from any sources that were out there so they could continue to concentrate on their athletic endeavors.

When we were little, we all played on the same teams together. Football in the fall, basketball in the winter, baseball in the spring, and soccer in the summer. But when we reached high school and puberty hit our group, it missed me completely. Jake, Robbie, and Teddy all grew up and out but not me, at least physically.

Jake, the de facto leader of our group, was the biggest. He stood roughly 6' 3" tall and was the starting center on the basketball team. Fundamentally sound and an intelligent player, there was just no way a 6' 3" center was going to make it in D-I basketball. Robbie and Teddy both stood 6' tall and were the starting defensive ends on the football team. Both were on the slender side and defensive linemen who weighed just north of 200 pounds weren't going to get D-I scholarships either.

Me? I'm Sammy, the one puberty left behind. I'm only 5' 7" tall and weigh slightly over 140 pounds. I started really focusing on my academics when it became abundantly clear I wasn't even going to be a late bloomer physically. I got a three-quarter academic scholarship, so college life is a bit easier for me financially. I help the guys out with their classes and studying as much as I can. No cheating, no writing papers for them, but free tutoring and academic coaching. They're my friends after all.

"Damn it, Sammy! You could use this money too. If we win, you'd practically be on a full ride."

"Then I'll be the Wizard. No fucking way am I going dressed as Dorothy!"

Every year, the college held a costume contest at Halloween. They gave out ten room and board scholarships to the winners. There was a singles category, a doubles category, a triples category, and a foursome category. Jake, Robbie, and Teddy had decided (without any input from me) that the four of us would go dressed as the main characters from the Wizard of Oz. Jake would be The Tin Man, Robbie would be The Scarecrow, and Teddy would be The Cowardly Lion. That left me to be Dorothy.

"C'mon dude!" Robbie said. "My character might not have a brain but even I know Dorothy HAS to be a part of any costume group with a Wizard of Oz theme. That might be the name of the movie, but the Wizard is most definitely just a supporting character."

Teddy chimed in, "You're the only one of us who has any kind of chance of pulling off Dorothy. The three of us are just too damn big to be a convincing Dorothy."

"Oh, so now you're saying I'm just some femme-boy. Fuck you!"

"Don't be a dick all your life, Sammy!" Jake said. "That's NOT what Teddy was saying, and you know it! Look at me. Could I play Dorothy?" I shook my head. "Could either Robbie or Teddy play Dorothy?" I shook my head again, this time more slowly. "You're the only one of the four of us who could possibly play Dorothy. We can't do this without you. What do you say man? The Fearsome Foursome needs your help!"

The Fearsome Foursome was a goofy nickname we'd given ourselves a long time ago. I shook my head, pretending not to like the idea at all. "And you're the only one with a sister. Clare's cool: Clare could help you!"

Clare was my older sister, by two years. And Clare had been helping me for a long, long time. The guys just didn't know it. When puberty hit and I started surfing the internet for porn, I had discovered crossdressers. I just had to see what the big attraction with wearing women's clothing was, so I took a bra and panty set from Clare's dirty laundry and tried them on. My orgasm was almost immediate and was off the chart explosive. I was hooked.

Clare and I had been raised by our mother. Our father passed away when the two of us were pretty young. He'd been involved in an industrial accident and because he hadn't worn all of his PPE, the insurance company wouldn't pay out and won their case in court. Mom did her best to raise us but had to work two jobs so we could live comfortably. Clare became like a second mother to me.

Clare walked in on me one day while I was dressed up. She wasn't supposed to be home for another two hours but here she was. "Sam-Sammy? WTF? What are you doing wearing my clothes?"

I immediately burst into tears. Clare came over and hugged me to her. She was so kind, so understanding and non-judgmental. She asked me to tell her the story behind my dressing, so I did. She nodded, asking insightful questions here and there. "Do you want to keep doing this?" I nodded sheepishly. "Then let me help you. I love you little bro, but I've always wanted a little sister too. Now you can be both!"

Clare began to immediately help me. We went through her wardrobe together, selecting those clothes she no longer wore but were still somewhat fashionable. Her shoes even fit me as we were almost the same size. She began to tutor me on makeup and hair styles. I had always worn my raven-black hair longer and unkempt, with Clare's tutelage I learned how to fix my hair, so it looked more feminine and stylish when dressed.

We started to go on shopping trips together. We always drove to the next town down the interstate so there was a lesser chance of us running into anyone we knew. Those trips were invaluable for my confidence. Clare tutored me on everything: how to walk, how to talk, my mannerisms, my voice pitch and inflection.

She even helped me go on my first date dressed as Samantha. We were sitting in the food court, just resting from our shopping, sipping on tea when two cute guys approached us. I was freaking out, but Clare touched the back of my hand gently, calming me. Clare was so used to getting hit on by guys; she was gorgeous, sexy, and confident. She stared at me as if to say, "Next lesson."

I took a deep breath and just followed her lead. She was polite but non-committal. She let the guys do most of the talking so that she could get a good read on them. They were brothers and from the local high school here (our biggest rival), but they were polite and genuine. She turned down their request to get our phone numbers, but she did agree to meet them here at the mall next Saturday to go to a movie.

The week flew by; on Saturday morning my stomach was churning. "I can tell you're wound up, Samantha. If you don't want to go, we don't have to go. I'm certainly not going to push you into doing anything you aren't 100% sure about doing."

"I'm just so nervous, Clare. This is all so new. It's one thing to dress like a girl or even go out in public like a girl, but this? To go on a date as a girl? I never, ever thought about doing something like this when I first started putting on your clothes. What if he makes me? What if he finds out and punches my face in?"

"Sammie!" Clare said in her sternest big sister voice. "First of all, he's not going to 'make you.' You have the finest tutor in the world, me! Second, if he even thinks about hurting you in any way, I'm going to kick his ass. No one touches my little sister while I'm around!"

I looked at Clare and the expression on her face and started giggling. All my nerves just dissolved, and confidence flooded in where my nervousness had been. "This is a special day and I've paid for a special treat for you. We're going to the salon to get our hair and nails done. Treats on me, let's go."

There is no comparison between getting your hair cut by a men's stylist and the pampering you receive getting your hair and nails done at a women's salon. I felt like a princess. Not only did I get a manicure, but I got a pedicure too! It was heavenly. I was effervescent all the way home.

Clare ran an extremely hot tub for me with a musk scented bubble bomb. She handed me a bottle of hair remover. "Use this from head to toe. Follow the directions carefully. After you've carefully wiped away all the hair, then use a warm washcloth to make sure you've removed all the gel before getting in the tub." She handed me a mirror and my razor. "You don't have much in the way of facial hair, but shave anyway. Twice."

I did as Clare asked. I got out of the tub, as hairless as I had been since I was a newborn. Toweling dry, I called to her. She answered, "I put some musk-scented body powder on the sink. Powder yourself from head-to-toe and then come out."

This was all so new to me; I did exactly as Clare asked. Wrapped in a towel, I left the bathroom. Clare was holding what looked like a flesh-colored leotard with breasts. "Sammie, I've gone all out for your first date. This is a crossdresser's silicone, full-body prosthetic. You tuck your penis into the suit behind the vagina. The breasts are also realistic. Put it on gently."

I went back into the bathroom and put on the prosthetic, slowly and carefully. Tucking was relatively simple; the pouch construction was genius. I slid the prosthetic up over my shoulders, smoothed it out, and looked at myself in the mirror. I gasped. I almost didn't recognize myself. I realized the prosthetic had an open bottom. "Clare?" I called out to her. "You might want to ask for a refund. This thing doesn't have a backside."

Clare's musical laughter rang through the door. "It's not supposed to, silly. What if you have to go to the bathroom? What if you want to make love to your man?" she asked in a theatrically husky voice. "Come out here. I want to see how it looks."

Still wrapped in my towel, I walked out, standing nervously in front of Clare. "Well, drop the damn towel so I can see how you look." she ordered. When I hesitated, she said, "C'mon Samantha, it's not like I'm going to see Sam naked. I want to see how you look in it. I need to know what I'm going to have to work with here."

I reluctantly did as Clare instructed, still holding onto the towel with the fingers of one hand like it was a security blanket. Clare smiled that reassuring smile and walked slowly all around me. She did a close-up inspection of the breasts and even knelt down to get the same close-up of the silicone vagina. She stood up and smiled again.

"Damn, they weren't kidding when they advertised this as lifelike. And please don't take this the wrong way, it's a complement. You have a great ass already; you don't need any help back there."

We both laughed out loud. Honestly, it's something I'd already heard from the rest of the Fearsome Foursome although we were all pretty drunk at the time. None of us ever mentioned that conversation again!

Clare produced a navy-blue satin and lace, bra and thong set. "Slip into these while I get the rest of your outfit. I slid the thong up my legs, when the crack nestled into my ass, I shivered. I'd never worn thong panties before. Clipping the bra in front of me, I turned it around and slid the straps over my shoulders. The breasts nestled nicely into the half cups of the bra, showing some impressive decolletage!

Clare came back and handed me the rest of my clothing. "Go back into the bathroom and get dressed while I get dressed out here."

I did exactly what she asked, it was very clear to me that Clare had planned this day out carefully. I opened the pack of pantyhose and slid them up my legs. They were also navy-blue with the slightest hint of a silver shimmer that caught the light every time I took a step. I slid a figure hugging, denim mini-skirt up my legs; it had a frayed hem and came to mid-thigh. The fraying was sure to draw anyone's attention to where my legs disappeared under the skirt.

Clare had matched that with a navy-blue and gold tiger striped satin blouse with cap sleeves. It was form fitting and had a deep v-neck. Finally, she had given me a pair of denim, open toe stilettos with 3 1/2" heels. I had worn much higher heels before; I'm guessing Clare wanted me to be comfortable. When I finished getting dressed, I looked in the full-length mirror and gasped. Even without makeup, a sexy young lady was looking back at me!

Clare heard me gasp and asked, "Is everything OK?"

"Oh Clare, yes, I look amazing. Your fashion sense is impeccable."

"Well, then don't hide in there, come out and show me!"

I confidently strode out into Clare's room, knowing I looked as good as I felt. Clare smiled broadly and walked over to give me a big hug. "You're beautiful. That young man is going to be on cloud nine when he sees you today. Now, let's do your makeup and put on your jewelry to complete this package!"

I had gotten my nails done in a pink chrome color and Clare set about matching my makeup to my nails. She brushed on pastel pink glitter eye shadow, both above and a little below my eyes. She used jet-black eyebrow pencil and volumizing mascara to make my crystal blue eyes really pop. She put just a hint of blush on my cheeks and finished everything off by brushing hot pink lip gloss onto my lips.

I started to turn around so I could look at myself in the mirror. Clare firmly but gently held my shoulder. "Not yet baby girl. Let me get the jewelry set I picked out for you and put that on first." She clipped 14k gold, 2" hoop earrings onto my ears. "Depending on how far you want to take this, you might want to think about getting your ears pierced at some point in time. No worries for today, these look great on you."

"Hold your hair up." I did as she asked, and she clipped a gold mesh choker around my neck. She placed a gold cuff bracelet on one wrist, and multiple gold bangle bracelets on the other wrist. She put gold rings on the pinky and index fingers of my left hand, and middle and ring fingers of my right hand. She knelt in front of me and gently clipped a gold ankle bracelet around my right ankle. It said, "Sammie."

Clare stood up and helped me to my feet. "Now you can look, baby girl." She held onto my shoulders while she helped spin me around.

"Oh-oh-oh! Is-is-is that REALLY me??!!!!" I asked incredulously. I had never, ever looked like this in my life. There was a gorgeous, sexy, confident woman staring back at me.

Clare gave me a little kiss on the cheek. "Yes, Sammie. It's you. This is the woman who's been hiding inside you all this time." She gave me a playful swat on the butt. "Now get out of here and let me finish getting ready."

I couldn't sit down; I was on an adrenaline rush. I walked around the kitchen, the sound of my stiletto heels click-clacking off the tile floor. Clare finally came in and she looked beautiful as always but had dressed down a little. She was wearing a knee length skirt with a baggy sweater and flat sandals. "I've deliberately dressed down a bit. This is your day, your first date. I want all eyes on you, baby sister!"

I rushed over to Clare and hugged her. "You're the best, the most amazing big sister any girl could ever have. I love you."

Clare hugged me back and smiled. "I love you, too, Sammie. Now let's go knock those brothers out!" She gave me a navy-blue, leather over the shoulder purse with a long gold chain. I looked inside and there was some makeup for touch-ups and a lubricated condom. "What's this for?" I asked as I held it up with a puzzled look on my face.

"A girl always needs to be prepared. You'd much rather have one and not need it than need one and not have it."

Still confused, I put it back in my purse.

We got to the mall in plenty of time; Clare drove. "We're going to have to teach you how to drive in heels sometime, it's definitely different!"

The brothers were waiting for us just outside of the theatre. They had already purchased tickets and we went inside. That particular movie had been out for a while, the theater was empty except for the four of us. They led us to the back rows. I was with the younger brother, Jay; we sat in the last row on one end. Clare was with the older brother, Derrick; they sat in the third to last row on the other end. Jay and Derrick were both cute; Jay was definitely nervous.

Jay and I were chatting, just making small talk, when the lights began to dim, and the movie began. We were still the only four people in the theater. After a few minutes, Jay pulled the old stretching routine and sure enough, when he pulled his arms down, one of them went around my shoulders. "What the heck," I thought and rested my head on his shoulder. He started stroking my hair and running his fingertips up my spine. That sent a jolt through me, and I turned to look at him.

He misunderstood my actions and leaned in to kiss me. I put my finger against his lips and said, "You're moving pretty fast. I think you're cute but slow down just a little bit. The movie has barely started."

He mumbled an apology and started to pull his arm from around my shoulders, but I grabbed his hand to keep it there. "I didn't say I didn't like it, I just asked you to slow down a little." I smiled and gave him a quick kiss on the cheek to let him know I wasn't angry.

Neither one of us paid much attention to the movie as we continued to talk quietly, getting to know one another. Jay was actually pretty shy; I'm guessing his older brother had coached him a little bit on how to 'make a move' on me. Now that he was relaxing and being himself, I found him that much more attractive. "What the hell is going on with me?" I thought to myself. "No one has ever been this closely attracted to Sam before, but Jay can't resist Sammie. I shouldn't but I like the way this feels."

"Jay?" I whispered. When he turned to face me, I offered him my lips and kissed him. He seemed momentarily surprised but then kissed me back hungrily. I put my arms around his neck and held his face to mine. I thrust my tongue past his lips and eagerly explored the inside of his mouth. His tongue danced with mine; we were making out with no inhibitions at all.

His hand cupped my breast and I moaned for him. Even though I couldn't feel anything he didn't know that. When his hand dropped down to my leg and he began to caress my nylon-encased thigh, I moaned again, this time for real! "Oh, Jay, that feels so good. Your touch is amazing."

He continued to stroke my thigh and I was getting turned on. I couldn't get an erection inside the pouch of my prosthetic, but I could definitely feel myself getting damp with pre-cum. Without thinking, I reached down and began to stroke the front of his pants where his erection was already in progress. Within moments, there was a raging hard-on underneath the ministrations of my fingertips.

"Sammie," he groaned. "That's so hot, I'm so turned on by you." I began to lick his neck and tongue his ear as I continued to rub his crotch. "Take it out Sammie, please take it out." I unbuckled his pants and unzipped his fly.

His hard-on poked out and was in my hand, my painted nails wrapped around his shaft. I began to stroke him as if I was stroking my own cock. The first drop of pre-cum dribbled onto the back of my hand. "What the fuck am I doing?" I thought. I stopped for a moment but then reached for my purse.

"Sammie, please don't tease me like this. Your touch is magical."

I kissed Jay again. "I promise not to be a tease, but we don't want a big mess everywhere." I whispered. I fumbled around inside my purse with one hand and found the condom Clare had put in there. Now I knew exactly what she had meant when she said, 'You'd much rather have one and not need it than need one and not have it.'

I got the package open and rolled the condom onto Jay's throbbing member. Even though the condom was lubricated, I spit into the palm of my hand before stroking him again. Jay's eyes were closed, and his head was back. He was under my complete control. He wanted me, he wanted to be with me. No one had ever felt that way about Sam before. It was intoxicating to be this wanted by another person.