Walking in any new school is frightening enough under normal circumstances, but it is even worse when you are a guy pretending to be a girl. Since I was a new student, I had to stop at a table outside the counselors office and pick up my schedule and information packet.
"Oh, you must be Kylie!" the counselor exclaimed, introducing herself. I smiled and said, "Hi," wandering if my voice was convincing. I had practiced this enough, even mimicking girls on TV.
"If you have any difficulty finding your way around, you be sure and stop by our office," she continued. Here, let me get somebody to show you where your first class is at. She glanced around the hallway, then loudly said, "Joel, can you come here?" A guy with brown hair and glasses looked up from his locker, then came over. He was of medium build, and looked more the studious type than the athlete.
"Joel, this is Kylie. She just moved here from California. Do you mind showing her where the Math department is at for her first period class? Are you headed that way?"
Joel glanced over, sizing me up quickly. "Sure, no problem. I'm going that way," he said, and I noticed the North Carolina accent. He had a soft, almost shy voice. "C'mon, I can help you get your locker, too, if you haven't found it yet."
"Thanks," I murmured, once again worrying about my voice. The more I used it, the easier it became.
Within minutes, I was chatting with Joel, and he became my unofficial tour guide as he showed me down the hallway. I noticed students look up at me, and when we passed some jocks standing outside the cafeteria, I felt like they were sizing me up. I stole a glance back as we went by, and one tall guy was staring at my back side- he saw me look back, and grinned sheepishly, then turned away. Maybe I was just being self conscious.
When I got to my locker, Joel offer to help me with the combination and the handle, which was sticking. He had bought into my charade as a female with no question, and I genuinely liked him so far.
"Now your class is down on the left," he directed me with his hand, "and I have the same lunch as you do, so I'll check in and make sure everything is ok. You'll find that this is a big school, but everyone is pretty friendly. Southern hospitality!"
After my first three classes, I found my way to the lunchroom. Several students had chatted with me and asked about California. No one questioned my sexuality, so I assumed I was comfortable in my new role. Once I almost messed up by going to the boy's restroom. After that, I tried to avoid bathrooms altogether. I decided that I wouldn't go during passing periods- only at times that no one was around. My PE class wasn't until second semester, so I didn't have to worry about that. I figured I would get a schedule change before then, and avoid it altogether.
Joel was waiting at the door when I went into the cafeteria and, after getting some food, we sat down. He introduced me to a few friends-male and female, and then everyone held the usual kind of conversation. Apparently there was a back-to- school dance later that week that some of them were headed to. Rachel and Brenna invited me to go with them and, since they had a car, we made plans for them to pick me up. Joel was undecided, since school dances weren't really his interest, but he said he might show up just to see everybody.
The rest of the week went reasonably well, and since my mother didn't come in until late in the evenings, I didn't have to worry about changing outfits until after I returned home. I began to wander what I should wear to the dance, but it was pretty informal so I figured a pair of jeans would probably work. When Rachel pulled up to the curb, I was watching for her and jumped in the back seat. I was relieved to see that she had dressed about the same as I had. We had both put on a little more jewelry and cosmetics than what we normally wore at school. I had also made sure to shave what little hair might have existed on my legs and underarms. My face was already smooth.
The Dance
When we walked in the school gym, a few students looked up, but most of them were pre-occupied, so we got a Coke and went to stand in the side of the dance floor to watch the students who were brave enough to get in front of their classmates. Before long the numbers increased, the lights went down, the volume went up, and everybody relaxed. A couple of times I saw a guy looking over my way that looked like a junior or senior. He had curly, dark hair and dark features- taller than me, but not too big. We made eye contact, and he looked down bashfully, then looked back up and smiled. I smiled back, then continued talking to Brenna, watching him out of the corner of my eye. I knew he was watching me, even while he chatted with some other guys.
My heart pounded as he broke away from the other guys and started moving my way. He was adorable- bright white teeth below a tanned face, with a shy, nervous look. His black curly hair was natural, and really hot.. He was dressed in jeans and a collared shirt over an olive green t-shirt. I realized that he may be coming over to see one of the other girls, but I felt my face grow warm.
"Hey, Brenna, who's your friend?" he smiled.
"Oh, hey," she said looking up. "This is Kylie. She just moved in here."
He looked at me and said, "Welcome, welcome. I'm glad ta meet ya!" with a big smile. "I'm Drew- I was Andy in elementary school, but I decided Drew sounded smarter, so I changed my name. Do you want to dance?"
"Yeah, I guess so," I replied sheepishly, "but I'm not that good." I was nearly terrified- I was a guy, parading as a girl, about to dance with a guy who would probably spit on me if he knew the truth, but he was really hot, and I loved the southern accent.
"I'm glad you're not good, 'cause now I won't feel so bad if I step on your feet," he said, reaching out for my hand.
We moved out on the floor which was playing a slower song now, and it was obvious that neither of us were very good dancers (which I think helped us relax a bit.) We talked a little bit about California, and he told me that he ran cross country and track, but avoided football and other sports because of the time it took, and that he had a job that kept him busy in an electronics store. I never noticed what a guy smelled like, until now. When you're a guy, you don't notice guy smells but, when you're parading as a perfumed girl, you pick up on this. It smelled good. I was glad I had a girdle strapped around holding my hard-on at bay, especially when he nuzzled up next to my cheek.
The rest of the night, we stayed pretty close to each other between songs, and made a few more lame attempts on the dance floor. No one else seem to notice, or to care. As things started winding down, he asked if he could take me home. I told Rachel, and she just gave a thumbs up and said, "you behave yourself, you hear? He might not be as sweet and innocent as you think!"
Parking for the First Time
We left in his small pickup truck, which didn't have a lot of seat space, so when his hand dropped from the gear shifter to my leg, I knew he was testing me for a response. I reached down and covered his hand with mine, and pressed it into my leg. "Don't let him move into my crotch, I begged myself- he might feel it, and then I'm in big trouble."
Fortunately he didn't make any moves in that direction, but he asked if I wanted to drive around the reservoir which was the cities water supply. It was still early, so I wasn't too worried about the time.
"I want to show you a really cool view up near the damn," he said, glancing over, "if you're ok with it."
"Sure," I answered, "I'm ok with it." I hoped he would read between the lines.
When we stopped at the small parking area near the damn, it was completely deserted. There was a small nightlight not far that shined weakly on his truck. He said, "Here it is, what do you think?"
It wasn't that impressive, but I said, "Yeah, this is really cool. I'm glad we drove over here."
He turned to face me, then lifted the hand from my leg to my chin and pulled it toward him and kissed me lightly on the lips. I pressed in, and he kissed me more aggressively, and I felt the flicker of his tongue. I couldn't believe this was happening- I was literally floating on air, as I kissed back. I had kissed a few girls, and a time or two I had played around with some guys in San Francisco that were buddies staying overnight with me in middle school, but that wasn't really kissing- not like this. This was the real thing, and the more I gave in, the more aggressive he became, sliding his tongue further in my mouth.
"Mmm, you taste sooo good," he murmured in my ear, giving it a small lick, then moving back to my mouth. "Are you ok with this?" he whispered, as his hand ran down my back, "you have me so hot for you...."
Fearing exposure if he touched my breasts, I pushed back a little and said,"whew, I better catch my breath!"
Getting the message, he backed off a little and said, "sorry, you just really get me going. I've been watching you all week, since class started." He reached down and took my hand and placed it on his knee. "You are so beautiful...."
I reached up and took his face and kissed him again, then slid down to his neck and found a soft spot to gently suck on. I felt some light beard stubble, and could taste some of the cologne he was wearing.
"Oh....,"he said, as he put his hand on the back of my head, "I like that....but what I'd really like to do is to fuck you....d'you want to do it? if not, I understand....," he almost begged.
Whoa- kissing was a HUGE step, but fucking? I mean, I can't even do THAT! I had to think really fast..
"Oh, uh, I want to so much but....um, I'm having my period right now....I can't do it....but you know I want to...." I could see the disappointment in his eyes.
"Oh, Kylie, you got me going so bad.....wow....you are so hot," he moaned. "Would you give me head? I know some girls don't do it 'cause they think its gross and all, but I keep really clean."
Blow jobs I knew a little- be it, very little- about, because of messing around in 8th grade with some buddies, even if they could barely shoot a load. I reached down, and rubbed his jeans, and felt the hardness underneath, then found the zipper and snap.
"Are you really going to?" he whimpered, fumbling with his pants, and trying to help me pull them down. "Oh, this is so sweet, so very hot.....," he groaned as his cut, 6" boner broke free, and he slid his undershorts down. I could smell fresh fabric softener and a little musky odor of sweat. I held it is my hand, and glanced up at his face..
"If this is your first time, just lick it like a popsicle or a sucker, it don't taste bad," he instructed. "That sticky stuff on the end is ok, it won't hurt anything." Boy, he must have thought this was the first cock that I ever saw! And I had one of my own that was about to burst. I held it up and licked the head, tasting the pre-cum that was really flowing heavily. It didn't have a lot of taste, but it was pretty slimy. After playing with the head and licking up and down the shaft a few times, I swallowed the whole thing.
It was electrifying! He jumped and grabbed my head and said, "Ewww! Oh, that's wild, that's wild!" I reached under his balls with my other hand and pulled on them. One thing that a guy knows, is what a guy would like in a blow job. I gently tugged on his balls while I moved up and down the shaft and he squirmed and moaned.
I knew an instant before that it was about to happen- he tensed and tried to push my head off of his rod, and then the fountain of juice started shooting. I was just at the head when it started, and it went down my throat, in my mouth, and then caught my lips and even my face. Jism was going everywhere all at once. I didn't hesitate to swallow what was in my mouth, then go back for more. He must have shot for two or three minutes before he finally leaned back and dropped his arms to the side, his dick still in my mouth.
As he rubbed my hair, he said, "I am sooo sorry- I wasn't going to shoot in your mouth like that....I didn't mean too. I was trying to push you off when it happened. I hope it didn't make you sick."
I laid my head in his lap, and looked up at his embarrassed, anguished look. Then I pulled his face down and kissed him gently, but enough to smear the goo between us.
By now his cock was a soft pile of skin, and I let him pull up his own pants since he obviously felt uncomfortable.
Our ride back was quiet, but he did reach over and take my hand. I didn't know if tonight was a one time experience, or if he would ask me again. Maybe he just wanted me to get his rocks off and nothing else. I guess I would have to see.