Team Spirit

Team Spirit

All characters in this story are 18 or older.

Act I: Rain Delay

High school was a hard place for a closet transsexual from a traditional family. Day in and day out, having to pretend to be someone you're not. But at the very least, after I met my friend Jessie, a few things turned around for the better.

I had a very small figure that I tried to keep as feminine as possible, keeping myself free of body hair. Though on the outside my clothes were normal, I frequently wore bras, panties, and stockings underneath. I had gotten a job as early as possible so I'd be able to buy these things in secret. I also grew my blonde hair out long to give me a more feminine appearance.

Jesse had long hair as well, brunette in color, though he'd always said he grew it long to look more like his rock and metal music idols. He was about six inches shorter than me, but his frame wasn't much bigger.

I was very shy in high school, and never really had that many friends. No one really knew I'd felt more like a girl than a boy growing up, as it was a secret I'd guarded very closely, living in a southern state and raised by traditional parents. It all changed one weekend when Jessie was spending the night.

Jessie and I met when we were sophomores, and had quickly become best friends. He was shy and relatively quiet too, but we found a common interest in baseball. He started to come over rather frequently so we could watch the games, as we had satellite and he did not.

Now at 18, we'd been best friends for two years and told each other everything. Well, nearly everything. On this particular night, the baseball game had been rained out so instead we were flipping through the channels, looking for something to watch. By complete accident, we happened to come across the Victoria's Secret Fashion Show. Immediately our eyes widened. In our various conversations we'd both admitted to being virgins, so I knew this was a turn on for him as much as it was for me.

We were both sitting on the bed, next to each other, our eyes and mouths open wide as we watched the scantily clad models saunter up and down the runway. Out of the corner of my eye, I could see a twitch in Jessie's pants. I gave a quick glance and realized he was getting hard watching the show. I couldn't really say anything though, as I was as well. We both sat in silence, watching for a few minutes longer, while I tried to gather my courage. Eventually, I managed to squeak out the words. "This is pretty hot, huh?"

Jessie nodded his head, still staring at the screen, even though my glance had shifted to him, and the growing bulge in his pants. I bit my lip, mustering my courage to continue. "Wanna...watch something a little better?" I asked.

"Like what?" Jessie asked, looking at me very briefly before returning his gaze to the fashion models.

"I've got some...y'know, adult movies. I dunno about you but seeing this has me pretty worked up. I think we've known each other long enough to be able to get some release in the same room," I blurted out, speaking quickly and nervously.

Jessie finally tore his gaze away from the TV for more than a second, staring at me inquisitively and raising a brow. "You wanna...jack off together?"

"Well I er um..." I stammered. "I kinda do it differently. I've got this soft pillow."

He laughed. I blushed and looked down, thinking he was laughing at my confession, but surprisingly, he responded, "I do the same thing. I thought it was just me."

We both had a little nervous laugh now. "Well if you want to, I've got an extra," I said, standing up from the bed.

"I don't see why not...it's not gay if we're watching the porn and not each other, right?"

"Right," I said, never really considering if it were 'gay' or not. I'd always considered myself bisexual so those kind of thoughts never really bothered me to begin with. In any case, I went to my closet, moving a few boxes aside to get to my stash. I had several adult movies, a few extremely soft pillows, and a treasure trove of women's clothes and makeup. I grabbed one of the straight porn movies and two pillows and closed the door.

I handed Jessie one of the pillows as I went to the DVD player and slid the disc in. In a matter of moments it began to play the scene. They didn't waste any time with story, as a blonde with big tits and a shapely ass immediately undressed and began to blow the guy standing in front of her.

"You can have the bed, I'll use the couch," I told Jessie, moving over to the couch that sat in the opposite corner of my room. I positioned the pillow on it and waited for Jessie to make the first move. He didn't even miss a beat, though his eyes were firmly glued to the TV, so he didn't even notice me watching. He lowered his jeans and boxers, and I caught a brief glimpse of his dick, which looked to be about the same size as mine, and just as hard. He lay down on the pillow and immediately began thrusting against it.

With him firmly distracted, I unbuttoned and lowered my jeans, pulling down the baby blue thing I was wearing with them to try and keep it hidden. I then positioned myself against the pillow as well and began to thrust against it, savoring the silky soft feeling against my hard cock.

Admittedly, while Jessie was watching the porno I'd put on, (the blonde was now bent over a desk, getting fucked from behind,) I was watching Jessie's hips thrust against the pillow. My own rhythm slowed as thoughts wandered through my head. It took a great effort not to keep going though, as turned on as I was.

Before too long, the blonde again dropped to her knees and began to suck the guy's cock, slurping up all her pussy juices in the process. Finally I sat up, placing the pillow over my lap to hide my erection.

"Hey Jessie...that looks like fun, doesn't it?" I asked, pointing to the blonde on the screen.

He stopped thrusting.

"What do you mean?" He asked suspiciously.

"How about instead of masturbating...I try...doing that, to you?"

Jessie sat up, covering his erection with the pillow as well and looking at me with a confused expression.

"I won't ever tell anyone. Come on, I bet it'd feel really nice. What do you say?"

He thought about the proposition for a moment, before muttering. "Won't that make us gay?"

I sighed and stood up, dropping the pillow and stepping out of my pants, making sure to keep the thong hidden inside them. I didn't want to reveal all my secrets too fast.

"You should stop worrying about that. If it feels good, that's all that should matter, yeah?"

"Well...I mean," he began to say, trying to come up with more. I quickly moved over to him and dropped to my knees between his. His eyes went wide as I grabbed the pillow and yanked it from his hands, tossing it where I'd dropped mine. For the first time I got a real good look at his throbbing cock, so hard it was standing up against his belly.

"Just go with it," I whispered softly, before leaning in and laying my tongue on the underside. I loved the soft feeling of it as I ran my tongue from the bottom all the way to the top. I repeated this a few times as if I were licking a lollipop and looked up to gauge his reaction. He was still staring down at me, wide-eyed.

"It feels good...doesn't it?" I asked nervously.

"Y-Yeah..." He whispered hesitantly.

I smiled and leaned forward, licking his cock once more from bottom to top. I decided to get bold and suckled his balls into my mouth, at which point I heard him give a quiet moan. After I experimented with this, I decided to push on. I opened my mouth, placing my moist lips over just the head of his cock, slowly sliding my tongue over the little slit, getting my first taste of precum. It was salty but not bad, and I savored it. As my mouth closed around him, I heard Jessie give another moan.

Hearing him enjoying it emboldened me. I slowly slid my lips down over his cock, inch by inch, taking as much of it as I could. At first I only managed to go about halfway before my gag reflex caught, but I was determined to press on.

I bobbed my head up and down, my warm, moist mouth soaking his throbbing dick with saliva as I worked it. After trying a few more times, I managed to suppress my gag reflex and finally took the whole thing into my mouth. I could feel it at the back of my throat, and I felt so full. But still I wanted more.

I began to work a little faster now, sliding my lips from the very tip of his cock all the way to his pelvis, steadily increasing my pace. Suddenly I could feel one of his hands in my hair, and I knew he'd stopped worrying about whether this was 'gay' or not and was just enjoying himself. I didn't realize just how much he was enjoying himself though as before too long, he began to buck his hips, thrusting his cock into my mouth. "Unnh...unnnh...unnnnh!" He moaned before I felt it. A very warm splash of thick, sticky spunk sprayed across my tongue.

This was my first time giving a blowjob and it caught me entirely by surprise. I enjoyed the texture and flavor though, swallowing down every last drop I could. When I realized I'd gotten it all, I slid my lips up and down his cock a few more times before finally releasing it and leaning back on my knees. I wiped my mouth and took a deep breath, looking up at Jessie wordlessly. My own cock was still rock hard, leaking precum at the thought of what I'd just done.

"Do you wanna...return the favor?" I asked hopefully as I stood up, my own rock hard dick just below his eye level.

"I...I dunno..." He said, with a nervous twinge to his voice. I sighed, and nodded my head.

"It's okay," I replied, trying my best to hide my frustration. I went back over to where I'd dropped my pillow, picked it up, placed it on the couch and returned my gaze to the TV where the guy was just about to cum all over the blonde's face. It didn't take me very long to cum against the soft fabric of the pillow as he shot his own load all over the actress.

After this we both silently got into our PJs and went to sleep for the night. I let him remain on the bed while I slept on the couch.

Act II: Batting Practice

I awoke before Jessie did on Saturday morning. I yawned and stretched, crawling off the couch. I slipped out of my bedroom and went to the kitchen, finding my parents already having breakfast.

"We're going up to visit my sister for the day, dear, so you and Jessie have the house to yourselves. Try not to make a mess, alright?" My mother said as I retrieved the orange juice from the fridge to pour myself a glass.

"Will do, mom," I replied, hugging both my parents before they departed. I stood, sipping my orange juice, thinking. Before long I heard the familiar sound of the family car driving away and then it hit me. Jessie and I would be alone all day. My aunt lived two hours away, so accounting for the trip there and the time they'd be staying, I realized my parents wouldn't be home until very late tonight. Regardless of Jessie's apprehension the following night, I made a decision.

I finished my orange juice and went back to my room. Jessie was still fast asleep on my bed, so I crept to my closet and accessed my secret stash, removing a large duffle bag that I kept various clothes and supplies in. I snuck back out of the bedroom and into the bathroom, placing the bag on the sink.

I stripped out of my PJs and opened the bag, gazing at my collection of women's clothing and makeup. I chose my undergarments first, picking out a hot pink satin thong and bra set. I slid the thong up my legs until I could feel the soft material encase my cock, which gave a little twitch. I then put on the matching bra, clasping it in the back. Digging around in the bag, I removed the soft gel breast inserts I'd bought and slid them in the cups of the bra, giving me the appearance of having pert, perky 36C breasts.

The next thing I grabbed where my white thigh high stockings. They were silky soft and opaque, with a pattern of lace around the top 4 inches or so. I sat on the edge of the tub and slowly slid each one up my legs, savoring the feeling of the material. They were by far my favorite thing about dressing like a woman. I'd always found stockings sexy, whether they be on me or someone else.

Next was makeup. I wanted everything to match, so I found my makeup kit within the duffle bag, set it on top, and unzipped it. I retrieved my sparkly pink nail polish and applied it to my fingernails carefully. After giving them a few minutes to dry I stood up and looked in the mirror to apply matching lip gloss. I then finished it off with a little blush, mascara, eyeliner, and shadow. After this I styled my hair, curling it just slightly at the ends so it better framed my dolled up, feminine face.

Finally, I pulled out a sheer, see-thru white camisole that just barely went down below the panties. To top the entire thing off, I pulled out a pair of sexy, strappy 3-inch pink heels and slid them on, then spritzed myself with warm vanilla sugar bodyspray.

I observed myself in the mirror and smiled, feeling more natural than when I dressed in my normal clothes. With my sensual outfit, painted nails and face, and long blonde hair, I looked like a sexy schoolgirl who just needed some relief.

Satisfied with my appearance, I left the bathroom and returned to my bedroom. I sauntered over to the bed and sat down on the edge of it, gently running my fingertips up and down Jessie's arm. It didn't take him long to stir and open his eyes. When he did, he quickly sat up and gasped. I smiled sweetly at him. For a long time, neither of us said a word.

"What...what are you wearing?" He finally managed to squeak out.

"Well," I said in the most feminine voice I could muster, which I had to admit was pretty convincing, as I'd been practicing and honing it for years. "You were so concerned about what we were doing being gay that I thought maybe, if I looked like this...you'd come around."

Again there was an awkward silence, though I could see his eyes examining my form top to bottom. I also noticed a twitch in his PJ bottoms, and was immediately sure he liked the outfit. Finally he managed to find his voice again.

"But...so you...had all this...just lying around?"

I bit my lip, looking down for a moment before raising my gaze to meet his. "We've always told each other everything Jessie so I'm going to come clean. I'm a transsexual. I feel I was born in the wrong body, and looking like this, I feel way more comfortable than I ever do dressing normally. I still mostly like girls but...I do have to admit, I enjoyed blowing you last night."

Again with the awkward silence. I bit my lip again, nervously awaiting his response. I could see his cock had gone from a twitch to growing firm now through the PJ bottoms.

"You look just like a chick," he said, a bit of apprehension still in his voice. "If I saw you and didn't know any better I'd think you were one."

Finally I leaned in close to him, placing a hand on his thigh, and whispering a mere inch away from his ear, letting my hot breath wash over him. "I am one, Jessie. Call me Angie."

"Angie?" He asked, still sounding unsure.

I bit his earlobe, flicking my tongue across it before moving down to gently kiss his neck. He instinctively tilted his head the other way, giving me more access, but didn't say anything. I slowly made my way across his cheek, kissing gently the entire time, before I finally came to his lips. His eyes were wide open now, and I could tell he was still nervous about what this meant for him. But for me, it was do or die time.

I closed my eyes and pressed my soft, sparkly lips to his. He did nothing for the first few seconds but then eventually began to kiss me back. I could feel his lips part and for the first time our tongues met. They danced across each other, intertwining as our lips pressed firmly together. As we made out, I placed one hand in his lap, rubbing his cock through the PJ bottoms.

He moaned into the kiss and so did I. We both found ourselves totally lost in the passion of the moment. The kiss went on for what seemed like ages before I finally pulled back to catch my breath, my hand still on his crotch.

"You smell so good, Angie," he whispered, my proximity making it easy for him to catch the scent of the vanilla bodyspray.

"And you feel so hard," I whispered back in the most sultry voice I could muster. "I want your cock again."

I pushed him back on the bed and grabbed the hem of his PJs, pulling them down his legs and off, letting them fall to the floor. He did the same with his shirt, so that he now lay there completely naked. I began to plant a soft trail of kisses from his knee up to his thigh, every now and again glancing up to look at him. He was watching me intently now. I knew my outfit had done the trick, making me look enough like a real woman that he was having no trouble believing he was with one.

As I finally reached his crotch, I kissed all around his rock hard cock, mere centimeters away from it to tease him, to make him as rigid as he could possibly be. At the same time I moved my stocking-clad leg up and down his, sure that he enjoyed the feeling of the material as I did.

I couldn't hold back any longer. I wrapped my lips around his cock and slid them all the way down, loving the feeling of his thick member filling my mouth once more. My pink, glossy, glittery lips did their work, sliding up and down his shaft, making it shine with saliva in the process. I reached one hand up and began to fondle his balls at the same time.

He couldn't hold in his moaning. He raised both hands and ran his fingers through my hair, which bobbed alongside my head as I slid my mouth up and down his cock.

"This is so hot," I heard him whisper, as he began to thrust his hips up instinctively. I could tell he was getting close already, seeing this hot blonde in stockings and heels blow him so perfectly. But before he could, I stopped, releasing his member and licking my lips.

"Why'd you stop?" He pouted.

I moved up and kissed him again, and found no hesitation this time. He parted his lips, letting my tongue again meet his. I found this surprising, as I knew he'd be able to taste his precum on me. I brought my leg up further as were kissing, letting the soft material of the stockings rub across his cock now, while at the same time being careful not to let him get off just quite yet.

Once we'd broken the kiss, I lay next to him and smiled sweetly. "If you want to cum this time, you're going to have to return the favor first."

I slid the camisole up to expose the pink satin thong, which was stretched taut now, my hard cock aching to be set free. There was a moment here where I thought again that he'd want to go no further, but to my surprise he rolled on top of me and kissed me again. I moaned as his body melted into mine, again rubbing my stockinged leg against his bare skin. I could feel one of his hands squeezing my fake breasts, and although it was just an insert, he seemed to enjoy doing it all the same.

He lifted his head, taking a deep breath and sliding down my body. "You're so hot, Angie," he whispered, reaching my panty-clad cock. He pulled it aside, allowing it to spring free. There was already precum leaking from the tip, as I was more turned on than I'd ever been in my life.

He wrapped his fingers around it and began to pump up and down, slowly at first. I moaned, feeling for the first time a hand other than my own on it. He continued this for a few moments, before finally growing bold enough to go further. I watched excitedly as he leaned his head down. I could feel the end of his silky brown hair tickle my thighs as he wrapped his lips around the head of my cock. I couldn't help but moan again, and raised a hand to run my fingers through his hair.