I was a senior in high school and just turned 18 after spring break. My schedule was very light which was nice and allowed me to be an aid for my PE teacher. Mr. Barnes despite his age, late 40's I'm guessing was in incredible shape. He had a square masculine jaw and full head of sexy light brown hair. Age had definitely been kind to this man. He was trim in the waist and had nice broad shoulders and chest. He was every girls dream at our school, both faculty and students. Mr. Barnes was not married and had no kids so this allowed him to really live up the bachelor life style. He drove a convertible Mustang which seemed to always have his set of golf clubs hanging out the back seat. I tell you what a life!
I became Mr. Barnes aid because my first three years I had been in his class. I was not the best athlete by any means. In fact I was down right terrible; I had no coordination or skills what so ever. I was tiny also, 5'4" tall and 110 lbs soaking wet. Most people just looked at me like some weird kid, with long hair and earrings. In fact I had other body piercing as well, but those were hidden from view. My nipples and belly had rings in them. Not the standard MO for a jock, but then again I wasn't one. What I did have was a huge desire to please Mr. Barnes, so I tried every class to be the best or do my best. He noticed this and finally in my senior year asked if I would be an aid for his class. I helped him out by keeping attendance running passes and anything else I could do.
It was during this time that I really got to know him and dare I say it, fall for him. I would sit and day dream all day long about how it would feel to be in his arms or to please him in any manner possible. Now I had dated girls, which was fun, but I also lusted after Men! One other thing about me is that I have been cross dressing for years now. Stealing my sister's things or buying my own. I had built up a large collection of lingerie, shoes, skirts, dresses, wigs and make up. I looked the part too when I dress, being so small with my blonde long hair and blue eyes. I made quite the sexy girl. In fact I even had pictures of my self that I kept on a jump drive. There were all sorts of pictures from tame just standing dressed in skirts and dresses wigs and make up, to hard core with me in stockings, shoes, corsets, or bras. Others with me dressed like a slut sucking on a dildo or fucking it in my ass. I felt safe as it was always with me. Well the feeling of security became my downfall. One day in my haste to get to my next class I had left the drive in Mr. Barnes' computer as I was working on grades for him at home. I must have forgotten to take it out after transferring the files.
I realized this mistake halfway through my government class. My heart began to race and I felt all the blood rush from my head. I could not concentrate on anything but. I tried to get out of class by asking to go to the rest room but that was to no avail. Mrs. Ratface as I called her was not going to budge. So there I had to sit hoping and praying that Mr. Barnes would not notice the drive and I could get it between my next classes. Finally after what seemed like fucking weeks the bell rang. My stuff already packed up I sprinted out the door down to the gym. I tore into his office and slid across the floor as my eyes burned onto the location that the jump drive was. Or should I say used to be. I stood there staring at the empty slot.
"Is everything ok Evan?" I heard the voice behind me say.
I could not move or even turn around, I knew it was Mr. Barnes and I knew he had my drive, with all my sexy pictures on it. Well sexy in my mind, but more than likely a freak show in his. Finally I spoke.
"I um, no nothing I'm ok."
Mr. Barnes walked around in front of me.
"Well you have no color, are you sure you are feeling ok?" "I can write you a pass to the nurse." "I've seen you look much better" he said with a smile.
Oh god he knows!
"No I'm fine" I said and I turned and ran out.
I went through the rest of the day not talking to anyone and to be honest I really don't remember most of it. How could I have been so stupid? What was I going to do? How could I go to class tomorrow? I didn't eat a thing at dinner and went right up to my room. My stomach was killing me and I just paced my room. I finally decided there was nothing I could do right now so maybe I could just get on my computer and chat my time away.
As I logged on to Sweet Katie I had a message to add a new person. I talked with lots of CD's and guys who like them so I thought nothing of it. What the heck I thought and clicked accept. Moments later a pop up message appeared.
Mustang1: "Hi Evan."
"What the fuck" I said out loud. "No one knows my name on here!"
Mustang1: "Evan, are you there?"
I sat staring at the screen not sure what to do. Suddenly a picture of me dressed in some black buckled high heels, thigh high stockings, and tight little boy shorts, and black bra sucking on a dildo popped up.
Mustang1: "This one is my fav!"
Oh my god I thought its Mr. Barnes. Jesus why is he fucking with me like this.
Sweet Katie: "Who is this?"
Mustang1: "I think you already know the answer to that. Thanks for taking care of those grades by the way."
Sweet Katie: "OMG I'm so sorry I left that, I didn't mean for anyone to see it. I'm so embarrassed."
Mustang1: "Don't be, I think it is very hot. I have always fantasized about having a special girl like you. Someone to take care of my hard cock!"
Mustang1: "That is if you want too? I could just turn the drive over to the Principal and let them deal with you."
Sweet Katie: "NO, OMG NO!"
Mustang1: "Ok good girl. Oh and I like that name by the way Katie. Call me Trent."
Sweet Katie: "Ok, so what now?"
Mustang1:"Ok, this is what is going to happen. You are going to tell your parents you are sleeping over at a friend's house this weekend. I want you to pack all your sexiest clothes and bring them to school. You will put them in my office. After school tomorrow you will come home with me. Wear something sexy under your clothes tomorrow to school. Remember you are my girl now and I want you to act like it. I have to go, see you tomorrow Katie."
With that he logged off and I stared at the screen. My sick feeling suddenly turned to excitement. I had never been with a man before and it looked like now I was going to get my chance, and for an entire weekend. I ran down stairs and gave my parents the line about staying at friends this weekend. Then quickly back upstairs to pack. I got all my things together, make up and perfume, fake nails, and nail polish. Next the clothes packing. First I picked out my white thong, white stay up thigh highs and matching white silky bra. I would feel very sexy all day long in this. Then all sorts of outfits and lingerie, I knew I wanted to get a chance to wear my red corset this weekend so that was definitely in my bag. Also my white leather mini dress and a similar blue one. I had to include my tight short skirts and tight shirts. I also packed my bikini since I had no clue what he had planned. Next came all sorts of shoes, thigh high boots with 4 inch heels, high heeled oxfords, patent leather with buckles around the ankles. Once done I sat on my bed and made sure my toes were painted a nice bright red. "Oh crap my jewelry." I grabbed my box and put it in the bag. "There all done" I thought to myself. I climbed into bed as excited as a kid at Christmas time.
My alarm rang waking me from my deep sleep. I jumped into the shower and shaved my entire body smooth, not that there was much to shave having light body hair that is blonde. I even shaved all around my little cock clean. It felt so sexy to be totally smooth. With my belly and nipple rings I looked hot! I dressed in my stockings rolling them up each leg. Next I put on my thong and finally my white little bra. I felt so excited to be dressed like this going to school. I finished dressing in my guy clothes and grabbed my bags and breakfast on the go. I jumped into my car and took off to school. When I arrived I almost sprinted to Mr. Barnes office where he was sitting at his desk. I walked in with my bags.
"Can I help you Evan?"
"I ah was brining my bags in" I said with a puzzled look.
"Do you need to keep them here?"
"Um, yes please." Is he serious I was thinking to myself?
"Ok just put them over there, I'll see you next period."
I put them where he said and walked out of the office very confused. He was acting like he had no idea what I was doing. I walked to first period in a blur. The whole day was like that in fact. During my aid period he did not mention anything about this weekend or anything. I was very confused as the day came to a close. "Was he just messing with me?" I walked back to the office expecting to get my bags and head home, but when I walked in they were gone! There was a note on the computer with my name on it. There was also a bag on the desk chair. I opened the bag and found one of my outfits. Inside the bag were a short Jean skirt and tight top and a pair of heels. He also put in a black choker, rings and big hoop earrings. I opened the note which read:
"Katie, I'm sorry to be so cold to you today but you must understand my position and your own. You don't want anyone knowing your secret right? Well acting as I did ensures that you don't get too excited and get found out. I have left an outfit for you to put on here at school. Use the make up in the purse and get all sexy for me. I want you dressed when you arrive at my house. You can put your boy clothes in the bag but leave them in your car. I will be expecting you by 4 pm so hurry your cute little ass up.
P.S. I put directions to my house in your glove box"
I was immediately excited and scared. How can I get out of the school without being scene? It was nearly three so I had to hurry. I went into the office bathroom and did my makeup as requested and got dressed. I did my hair in a high ponytail, put on the jewelry and after feeling comfortable with my transformation I grabbed my clothes and keys and headed out. I passed a few people in the hall but on Friday afternoon it is pretty dead inside. I made a b line for the parking lot and got in my car. Wow was that exciting being dressed in public like that. I opened the glove box and found his directions. Pulling out of the parking lot I hit the road.
It was a bit of a drive to a nice neighborhood as I pulled in and found his house. Mr. Barnes Mustang was in the drive, golf clubs in the back seat. I pulled in and as I did the garage door opened, but there was no car in there or anyone inside. I pulled my car in and the door shut behind me. I turned off the car, opened the door and got out. When I did the inside door opened up. This was a little creepy I thought to myself but I went in anyway being driven by lust at this point.
Inside was a beautifully decorated home. Very contemporary and very clean. Not at all what I was used to living in as my family were slobs.
I called out "Hello, Trent?"
There was a note on the kitchen counter with "Katie" written on it. So I opened this one and read it.
"Katie, I'm glad you have arrived. Please make yourself comfortable in the living room. I have poured you a glass of wine and there is a movie on for you. I'm cleaning up in the shower and will be down in a moment Baby.
I went into the living room and sure enough found that glass of wine and the movie, if you could call it that. On the huge flat screen TV as a hot young girl sucking on a very hard cock! I immediately felt a rise in my thong as I looked at the screen. I sat down on the gigantic micro suede sofa and sipped the wine. It was delicious and before I knew it I had drank the whole glass. I was feeling really good and buzzed as I continued to watch the sex before me. I was mesmerized and leaned back and began to rub my sensitive nipples. My eyes were glued on the screen as I moaned like a little slut. Just then Trent walked in.
"Oh I love how my sexy girl moans."
I turned and looked. He was wearing a pair of sexy silk pajama bottoms and nothing else. I thought I was excited before, but when I looked at his perfect body I knew there was no comparison. I smiled as he walked up to me and sat down next to me.
"Do you like the video I picked out; do you want to do those things with a man Katie?"
"Yes Trent" I said as I was nodding.
"Have you ever been with a man Katie?"
"Well if you treat me like that dildo in those pictures you will be fine!"
I could see the lust in his eyes as he talked. When he finished his sentence he leaned in putting his hand on the side of my face and pulling me to him. Our lips met and I felt a rush of pleasure hit my lips. Trent's tongue pushed its way between my lip-gloss covered lips. For the first time in my life I had a man's tongue in my mouth and it was even better than I fantasized about. Trent kept his hand along my face gently stroking my soft skin. My hands went to his chest as our passion continued. I moaned into his kiss as my hands roamed over his sexy body tracing down to his waist and finding his rock hard cock. It was sticking straight up in his bottoms and felt nice with the silk. As nice as it was I had to hold it in my hands. I pulled at his waist band and wrapped my painted fingers around it. I slowly rubbed it up and down as I felt the first bit of pre cum ooze onto my hand. Oh my god this was hot, I was getting more and more excited as the kiss continued. Our kiss finally broke as Trent pulled his lips from mine.
"I want you to lick my cock baby."
I smiled and said nothing; I just bent down and without hesitation pushed it past my lips. Trent leaned back as I brought myself up to a kneeling position on the couch. My back arched in a sexy porn star pose and ass high in the air. His cock was perfect size, not too big to scare me off but definitely big enough to make me want more. It had a nice mushroom head and just seemed to pulse in my mouth. I held it in one hand as I supported myself with the other. I was pretty much acting out what I had just scene on TV. I would slide my mouth all the way down until it hit the back of my throat and slowly pull my lips and mouth back off. Then I would lick all around the head and the underside before plunging back down on it. When it was all the way in my mouth I would wiggle my tongue a bit which he seemed to like a lot. All this gave me more and more confidence as he was moaning. I too was moaning like a slut in heat. My virgin mouth sucked and licked his hard cock for all it was worth. I wanted to please him like never before. I wanted him to want this over and over again and I wanted to be the "girl" to give it to him.
Trent grabbed my ponytail and began to guide my head as my mouth was running up and down his shaft. I felt his cock begin to get bigger and his body tense up. Suddenly he held my head still as I felt the first bit of cum shoot into my mouth. It hit the back of my throat and mixed around in my mouth. I was surprised that I liked the taste and began to swallow it. Rope after rope of cum flooded my mouth and I kept swallowing it down. Little bits escaped out of the corners of my mouth as his cock stopped its convulsions. Trent let go of my hair and fell back into the sofa. I held his cock and began to gently lick around it cleaning up any last bits of cum I may have missed. I was so turned on and wanted more. Pulling is cock from my mouth I looked up at him and licked my lips. He smiled back at me and just stared at me for a long moment.
He finally broke the silence and said "I'm so glad I found that drive on my desk. I have never ever had a blow job that good in my life, and I have had lots of girlfriends, Real girls!"
I couldn't help but smile knowing that I made him happy. I scooted myself up and snuggled into him.
"That was so hot" I told him. "I love sucking cock!"
"Well good baby, cause you are going to be sucking a lot this weekend and for a long time to come. Now why don't you get up and give me a little strip tease and show me how you look?"
I stood up as he grabbed the remote and put on some sexy music. He leaned back as I stepped back and did my best impression of a stripper. It was probably really awkward looking but Trent did not let on. I slowly took off my shirt wiggling as I did to the music. Then I reached behind me and pulled the zipper of my skirt letting it fall to the floor. I stood there for the first time in my life in white thigh highs, thong and bra in front of another person and I loved it. My little cock was bent but hard in my panties. I slowly ground to the music in front of my new man. Being as sexy as I could I turned facing away from him and bent in half, before slowly pulling myself back up while rubbing my hands up my stocking covered legs. I turned and rubbed my hands over my belly ring and up to my chest and into my hair. I looked and noticed his cock was getting hard again.
"Can I take care of that for you stud" I said in a breathy girl's voice.
His response was to stand up and take my hand.
Trent led me to the bedroom where he picked me up and carried me to the bed. He set me down and stood back up. Placing both hands on the waist band of his bottoms he removed them before climbing onto the bed. As he did he started at my feet kissing his way up my body.
"You have such a beautiful body Katie. I want you in every way."
With that he went back to kissing me along my legs and up my pelvis. He concentrated a bit on my hip bones which I would not have guessed would be an erogenous zone, but oh my god it was. His journey continued up kissing my belly button and playing with my belly ring before moving on. He nuzzled himself into my bar and started licking my nipples. Wow did that feel good. This man had an amazing tongue and I was feeling its benefits. He then moved onto my neck licking and sucking as he did until he found my ear.
His hot breath on me he whispered every so lightly "I want to fuck you Katie."
My boy clit jumped as he said this. I loved to ride my dildo and always wondered what the real thing would feel like. I was about to find out.
I looked into his eyes and nodded to him that I wanted it too. Trent reached for the night stand and pulled out a bottle of lube. He rolled me onto my belly and pulled my thong to the side and began to massage the cool lube into my boy pussy. One by one he pushed fingers into me slowly fucking me with them. It felt so much better than any dildo ever did. I was moaning like a girl at this point and wanted the real thing now, but Trent kept things slow. He was now fucking me with four fingers and I was on my hands and knees pushing myself onto him.
Satisfied he had me nice and loosened up he put some more lube on his cock and then some on my ass. He pushed my legs apart slightly and brought his hard rod up to my virgin hole. As he pushed his cock into me he held my hip with one hand and gently stoked my back with the other. The head popped into my hole and he held still a moment allowing me to get adjusted to its size. He then began to push little by little into me. Jesus this felt so fucking good and I moaned even louder to let him know. His cock was now all the way in my boy pussy and his legs pressed against mine. Trent then slowly pulled it back out till just his head was inside of me. Each time he would push in and pull out he would increase his tempo. The whole time he was fucking me I felt the tenderness of his touch as he wanted this to be as enjoyable for me as it was for him. Trent was now holding my hips as he was burying his cock deep inside me. Sliding it in and out as I was on my knees, I was now Trent's slut and I loved it. Trent's cock continuing to pound my virgin ass. I was feeling my first cock and I knew it would not be my last. I was now hooked and was a true cock whore after just one blow job and one fuck. I was moaning and calling his name as he fucked, cock sliding in and out. Occasionally he would change pace or pull his cock all the way out before plunging it back in. He slid his cock in and pulled me up off my hands and held my chest and rubbed my nipples as he ground his cock into me. Licking my neck and pulling my mouth to him to kiss. He was hot and loved his new toy.