I have always been really involved in theater. I don’t act, and my specialty is costumes and make-up. I’d never considered myself feminine until I went off to University when I was 19 years old and met my new theater professor, Mr. Kean. He was a big guy, about 50 years old with black and grey hair. At 6’4’’ and over 200lbs he cut an imposing figure.
Now, I have this little thing that I’ve been doing. When I’m alone in the dressing room, which is often as I’m in charge of locking up every evening, I dress up in the girls outfits and rub one out. What’s the harm, I figured? I was always careful to never get caught. I was doing exactly this one Friday. As the last person left, I immediately went to the girls changing room and excitedly began picking things out. Okay, I have another confession. Over the summer, I bought a dildo at a sex shop, and have been routinely fucking my ass with it. I brought it with me to the dressing room that day in my backpack.
So, I put on a little dress and skirt with a pair of pink panties that I found and got out my dildo. I usually lock the door behind me, but in my excitement to get to the deed, I left it unlocked. I was a few minutes into my session, ready to cum but trying to make it last a little longer, when I got the idea of trying to cum in my own mouth. The position I ended up assuming was with my legs pointing towards the ceiling propped up against a wall and resting on my upper back and neck so that my cock was only an inch from my face and it left one hand free to push the dildo into my ass while the other hand stroked my cock. Perfect, I thought. I was really into the moment when I heard the door open. I was furiously shoving the dildo into my ass with one hand and jerking off with the other, and suddenly Mr.Kean was in the doorway, only a few feet away. I looked over at him as I came and shot a huge sticky load over my face.
So there I was, dressed in a skirt with a pair of pink panties holding my ankles together, a dildo up my exposed ass, and cum all over my face. I was stunned, and I didn’t move an inch. Suddenly Mr. Kean reached into his pocket, took out his phone, and snapped a picture.
Suddenly I was enraged,
“What the fuck?!” I said in my deepest and most intimidating voice possible as I righted myself.
I must have looked pretty funny, dressed in a skirt with makeup and cum on my face and pulling a dildo out of my ass. Mr. Kean thought so, and he laughed a little at my exclamation. Then he looked at me with a stern gaze and said “that’s no way for a slut to talk to her daddy”.
“WHAT THE FUCK?!” I said, this time the shock of what he said setting in and suddenly he slapped me. Not hard, but firmly.
“you will do what I say, or I send this picture to everyone” he said, and I knew he had me. “Now suck my cock”.
I kind of expected it at that point, and with a somewhat faked defeated groan I got on my knees in front of him.
“Good girl, I didn’t even need to tell you to kneel” Mr. Kean said. I realized he was right, and blushed a little. The idea of playing with another man’s cock had come up in my fantasies and I had kind of wanted to but I never seriously considered it. Now I would have to. I was expecting the worst when Mr. Kean unzipped himself and let his jeans fall to the floor. He was still wearing briefs and he took a step closer to me. I could see the outline of his semi-hard dick and I reached out to rub it. I gasped a bit as I felt it starting to grow under my ministrations. Now it was straining against the fabric of the briefs so I pulled the elastic down and let his cock spring out. It was magnificent. It looked like It could belong to one of those Greek statues. It was at least 8 inches long and very thick, curving slightly upward before tapering off to a circumcised mushroom head. My head was inches away from it and I was leaning forward to begin licking the shaft when Mr. Kean pulled back.
“I want you to beg for my cock” he said. In a sudden exclamation of defiance I blurted out “no” but as soon as I said it I regretted it, and looked back to his perfect cock, afraid he was going to put it away. Instead Mr. Kean barked a laugh and took out his phone again. He brought up the picture he took of me earlier and handed me the phone.
“Delete the photo, and we can pretend like this never happened, but you’ll never get to suck my cock and feel me cum in your mouth” Mr. Kean said.
I knew what I wanted, and I leaned over so Mr. Keans cock was resting on my nose and took a selfie, handing the phone back to my new daddy.
Mr. Kean’s smile broadened as he saw what I did. “May I suck daddy’s cock now?” I asked, trying to be sexy.
“Oh yeah, you’ve earned it baby” He replied.
I needed no further encouragement and immediately put the head in my mouth. It felt right, to be on my knees servicing a man, and I could feel blood rushing to my dick again. I looked up and Mr. Kean was taking another picture of me, this time with his cock in my mouth. I looked up at him as he took the picture with my mouth full of cock. I was able to get about half his cock down my throat and began bobbing my head back and forth. Suddenly Mr. Kean pushed me back forcefully so I was pushed against the wall and began thrusting in and out of my mouth.
“Just relax, and let daddy fuck your mouth” He said.
I tried to do as he said, and soon he was sliding almost all of his dick down my throat. I gagged a little, but that only made his cock slicker with saliva. Soon his balls were pressing up against my chin and my nose was buried in hair with every stroke. His strokes became more erratic and he began to grunt. I knew he was about to cum, and was still unprepared for the torrent he unleashed in my mouth. I felt his cock spurt with each thrust and I began to splutter on cum as he pulled his cock out to finish his orgasm on my face.
“good girl,” He said, “we’ll teach you how to swallow next time”.
With that, he walked out. I jerked off again, attempted to clean up, and went home. The next week I was cast to a girls role. Mr. Kean said I was perfect for the role, and that was that. Later that week, I found a note in my locker telling me to get a wax for all my hair waist down. My body was already almost hairless, but I liked the idea. It hurt like hell getting waxed, but damn did I ever look sexy in the mirror afterwards. On Monday, we were rehearsing a scene in the play during which I have a long speaking part. Mr. Kean kept telling me that I needed to make my voice go higher, but I just couldn’t do it. After a few tries, he finally told me to stay after class today for some private voice lessons. My cock immediately sprung up and I have to admit I was excited to show off my newly hairless body. I also couldn’t stop picturing his big meaty member. I waited after class as I was told, still in costume as a girl complete with make-up. I walked up to Mr. Keans office and knocked tentatively.
“Come in” said a voice from inside.
I did, and walked into Mr. Keans office. I had never been here before. There were some posters for various productions and plays, some signed and others not. Directly in front of me was a large mahogany desk. I remember thinking that desk certainly wasn’t bought on the schools budget. Mr. Kean sat behind it in an armchair with a hungry look in his eye. He was wearing a white button-up shirt and black pants. I walked closer and he began to talk
“I’ve seen that you’re not completely committed to this role”, he said. I began to protest but he waved me off and I fell silent.
“Right now, I’m going to teach you how much of a girly little slut you are”.
If I wasn’t completely hard before, I sure was now. I nodded at him and was about to talk again when he cut me off “come over here and take a seat”, he said, patting his knee. I began to do as I was told and walked over to him, turning around and sitting on his thigh. Immediately, I felt arms around my waist pull me in closer to him. I couldn’t help but notice the bulge pressing between my cheeks and I began to gyrate my hips a little bit. Mr. Kean softly moaned and began pulling up my dress around my waist. Next, he pulled my little rock hard cock out of my panties and fit one large fist over my whole erection and began to quickly vibrate his fist back and forth, sending waves of my pleasure through my body.
“You like it when daddy rubs your little clit, don’t you?” he whispered in my ear. I mumbled that I loved it. Soon, I could feel myself getting ready to cum and I yelped, saying “I’m gonna cum daddy!” in a voice that was so high I hardly recognized it as my own.
“cum for daddy” I heard him say as I blasted my load into his hand.
“Take your panties off, and get my cock out” He said as I was panting and recovering from my orgasm
I did as he was told, standing up to slide out of my panties and next kneeling inbetween his legs. I unbuckled his pants and pulled them around his waist, revealing the same style of briefs that he was wearing before and that glorious cock straining to be free. I obliged it and pulled down the elastic, once again in awe in front of such a massive and perfectly shaped cock. I immediately reached forward with my mouth to begin my work but I had only managed to get the tip in when I felt his strong arms reach under my armpits and lift me onto his lap, facing him.
“I’m going to teach you how to really be a good girl” he said.
I felt his right hand reach around me and begin rubbing my hole with something wet and a little sticky. I realized he was lubing my hole with my own cum. The realization made my cock grow hard again and I leaned a little further into Mr.Kean, allowing his probing hand better access to my hole. My growing cock was not lost on him.
“You like it when Daddy plays with your little pussy, don’t you?”
“Mmhmm” I moaned in response.
Suddenly he hoisted me a little higher and positioned his cock at the entrance to my asshole. I was excited and terrified. Slowly he began to push against me. I could feel his hard member, both strong and firm, but also soft pushing slowly into me. I gasped a little as the head slipped past my ring. He smiled and gave my ass a playful slap, the vibrations feeling fantastic in my ass. Now I was the one applying pressure as I slowly sank deeper onto his cock. It felt strange, but also wonderful to be this full. The last few inches started to hurt and instead of taking the whole thing I began to bounce up and down slowly. The feeling was indescribable and I was lost in my lust and pleasure, still bouncing up and down on ¾ of his huge cock. I felt his arms on my shoulders applying pressure and pushing me deeper on each down stroke. It hurt a little, but it also felt incredibly good to be so full and going deeper on each bounce. I was lost in the sensation when suddenly his hands pushed me down harder than before and I squealed a little in pain as I slid down the last inch of his cock all at once. Mr.Kean smiled at me.
“Now you sound like a good little slut. I knew you could do it” He said. I felt myself blush a little. He reached out and moved aside my little dick, still hard as a rock, to show that I was completely impaled on his cock. I felt proud, and I started my rhythmic bouncing again. Soon I felt my orgasm beginning to build. No one was touching my cock, but the feeling of sliding up and down Mr. Keans big pole was going to make me cum.
“I’m going to cum!” I gasped.
“Go ahead. Use my big cock to cum” He replied.
With his permission, I started bucking more erratically and pushing my ass down hard. My orgasm was like a wave breaking. I don’t know how long it lasted but it was easily the longest orgasm I’ve ever had. I moaned and collapsed onto Mr. Keans chest.
“Damn girl, that was sexy,” He said, “but you got cum all over my shirt” he added as he looked down and I saw that it was true.
“I’m sorry” I managed to say, still out of breath.
“I’m going to fuck you hard for that” He growled.
With that, he lifted me up again and laid me face up onto his desk, with my feet over his shoulders. His cock never left me, and now it started to thrust in and out.
I honestly thought I was going to cum again when his strokes became stronger and his grunts louder.
“Take it slut” he growled, and I needed to steady myself with my hands so he didn’t fuck me right off the desk!
I felt his cock inflate in my ass and with a momentuous thrust he unloaded inside me. He kept his cock inside my ass for a beautiful few moments. Slowly, he pulled out and I felt the emptiness as his cock flopped out, still covered in cum. I turned around, got down on my knees, and began to lick his still enormous cock clean. Suddenly, I felt it twitch. Was he getting hard again? The thought caused my own cock to twitch, and I began bobbing my head back and forth on his member in earnest…