Trapped Teacher

I kissed her cheek in the semi-darkness of the room and tasted the saltiness of the tear.

"This is the last time," I told her with false sincerity. "I promise I'll give you all of the photos and the negatives if you just promise to do this last party. They're expecting you to be one hot slut... are you up to it?" I waited a few seconds and saw her visibly make up her mind. "That's a good girl. Now fix that slutty make up or you'll be found out for sure. I'll send them in to you in a short time."

I went to the door, paused, and turned and addressed her in a commanding voice, "And don't think I won't be recording this with the video camera. If you are not one hundred percent the whorish slut they wanted, ready for anything but using your pussy, I will not give your blackmail back. Got it? You are to be the nastiest bitch in town."

I stared at her until she nodded her acceptance, then I turned and left the room.

As I walked out I shut the door behind me. I went down the hall and down the stairs to where the party was going on. At the bottom of the stairs I paused again and my grin broke out full force. That asshole was really going to pay for failing me in his class. Re-take senior year, fine. He is paying a lot more than me.

Backtrack one month, Friday.

Mr. Tim Gunn was my high school science teacher. He was a brand new 22 year old teacher. He could not control the class very well as he was only 5'6" tall and very thin. What with his long hair we almost never took him seriously. He was also a royal pain in the ass. He was always telling us we had to do better than we were. I was 18 years old and he treated me like I was a freshman. When he failed me for the semester and told me I would have to take biology again I was pissed. This was supposed to be my best summer ever. Just graduated and all. Now I would have to go back.

I went to the neighboring town of Chiggsville to drown my sorrows that night with my fake ID. I took along a date helper just in case I could find some girl that just might. I sat at a booth in the back and started to drink a few beers when in walked Mr. Gunn. He looked around and actually chose the booth right behind mine. An evil idea began to form in my head. 20 minutes later when he went to the bathroom I leaned around and poured the knockout drug into his beer. 15 minutes later I was walking the semi-unconscious teacher out the door with no-one the wiser.

The next morning, Saturday.

I was sitting in a chair in my parent's basement. Mr. Gunn was slowly waking up. He couldn't move too much, I had tied him to the bed and gagged him. As he became conscious he started to thrash around at first and then settled down and glared at me. I grinned back.

"Wondering what happened last night?" I asked him. He continued to glare at me. "These pictures might help you remember." I leaned over him and started to show him the pictures in order.

The first picture was of his face with only my dick resting on his lips. The second picture had my dick buried in his mouth. The next picture was of him naked on the bed with his face in my crotch. The third showed him lying like he was now on the bed but he was dressed in a woman's black bra and panties... just like he was now!

Mr. Gunn realized what he was wearing now and started to struggle again. I kept the photos out and asked him quietly, "What would happen if the principal saw these pictures?" He froze. I could see the sheer terror start to form in his eyes. "Or maybe if they got passed around the school?" He was starting to see that he was in deep shit.

I could maybe let you out of this bind, Mr. Gunn. But you see I am one horny teen and right now I only have sex on my mind. Now where could I find a woman to blow me?" I looked at him lying there in the woman's underwear. "Ahh, here's one now." I grinned sadistically at him. "I am going to ungag you now, if you scream I will spread the pictures, do you understand?" I waited until he nodded before I took the gag out of his mouth.

"I'm not going to do anything for you," he snarled at me, but I could still see the fear in his eyes.

"Yes you are, Tammy, you are going to answer to the name Tammy, for one, because I am not gay and therefore you must be a woman to blow me. And second, if you do not, you are ruined."

Mr. Gunn, excuse me, Tammy, was trapped and knew it. "You'll give me the pictures after I do this?" he asked. "I swear, Tammy," I replied.

Mr. Gunn/Tammy thought about it for a few seconds and then nodded. I quickly took off my shorts and straddled his, no excuse me, her head. My dick was as hard as it ever got. I leaned forward and set the head on her lips. She looked me in the eyes and paused.

"Open your mouth you fucking whore." I growled at her. She blinked in surprise and did just that. I pushed in and my dick sank to the hilt in her mouth. I then leaned forward and lightly touched the button on the remote on the nightstand. Tammy did not notice because she was experiencing her first blowjob from the giving end of it.

I was a bit surprised. She was doing a pretty good job of it. I pulled out though and sat back. "Would you be more comfortable if I untied you? Don't think you can run, I am about 70 pounds heavier than you... you'll never make it."

"Please let untie me," Mr. Gunn/Tammy asked me in a quiet submissive voice. "I won't try to run. I just want this to get over with."

I untied him and let him up. I sat with my back on the headboard and she(he) crawled in between my legs and started to blow me again. It felt great. Soon I was close. "Lay on your back, Tammy." I instructed. She did as I said.

I crawled up her chest and finished jerking myself off on her face. I grinned with delight as I shot my streams on her face.

"Now for the last thing," I said with an evil grin, "I want you to lick it off and tell me how yummy it is and then say you love being a girl."

"What? No way," Mr. Gunn said through cum covered lips.

"Do you want the photos or not?"

He was struggling with this one but could see no way out. Before he began I instructed, "Now do it like you mean it or I will have to cover your face again!"

He gave me a dirty look, thought for a second and then looked at me with a huge grin, "I love the taste of your cum!" He then licked his face and tried to get all he could.

I threw him the photos.

As he got dressed and left he never once looked at me. As he walked out I got up and went to the closet and got out the video camera I had turned on... I smiled.

Sunday afternoon.

Mr. Gunn stood at the door when I answered the knock. He just stood there. I invited him in to my parent's house and he came in and stood in the foyer. He couldn't look me in the eye. He looked around the front room and saw my friend Jerry, also a senior, laying on the couch sound asleep. I had Mr. Gunn follow me downstairs to the basement where I live.

"You said you still had one picture to give me," he said in a subdued voice. "Can I have it?"

"Have it? No. Earn it, yes."

"Listen you bastard," He said with some spark in his voice. "This is black mail. It is illegal. Do you want to go to jail?"

I looked at the stairway. "Jerry would love to see the pictures, don't you think? All I have to do is wake him up and your secret life as a cross dressing whore is out."

"I am not a cross dressing whore!" He proclaimed to me with an angry look in his eyes.

"Yes, you are," I replied sharply. "Or at least you are a whore. The cross dressing part starts now." I pointed to the bathroom. "Now get in there and follow the directions on the paper on the sink or I wake Jerry up and show him your lovely cum covered face."

I could tell he was sick with shame as he slowly walked to the bathroom and shut the door. I waited. Five minutes later I heard the shower start. I had won and I knew it now.

The note on the sink had read. You are simply my whore now. With the pictures I have and the video I made yesterday (you didn't know about that did you?) you will do as I say or I will go public and ruin you. I will soon enough give you all of the blackmail, but for now I need a bitch. I want you to become her. You will dress in these clothes and behave as my slut or else. You should try your best to be one slutty bitch because if I am displeased in any way I will make your life hell. I want you to take a few seconds and think of just how bad the rest of your life could be. Now are you willing to work this out? I thought so. In the bag on the toilet seat is the outfit I want you to be wearing when you come out. Make up too. You really must shave those hairy ass legs too. I don't want anything to make me think you are a man. Razor is in the shower. Get moving, Tammy. Remember, you are a woman now. If you do what I say for the next week, you will get everything back as soon as you change my grade to passing. But you must do everything. Now get your ass moving.

When Mr. Gunn came out about 45 minutes later no one would ever recognize him. Out of the bathroom came a slutty looking whore. Tammy (now) had done up her make up to very dark colors. The effect was very low class. She was dressed in black stockings that came just to the bottoms of her short black leather skirt. Her belly was exposed under the tight black top. Her tits were almost non-existant (of course) but I didn't care. She had even pulled her hair in front of her face a bit. I think the dear was a bit bashful.

"Come here, Tammy." I said and she dutifully walked to me in her black leather short boots. "Turn around." As she did I could find no obvious signs that she was really a man.

"You did an excellent job, Tammy." I congratulated her. "You are truly on hot slut. No one will be able to tell you are a guy from looking at you. But you have to learn how to behave as the slut you look like. When I come back downstairs you had better convince me that you really want to please me, or else." I went upstairs, woke Jerry, and came back downstairs with him.

She was sitting nervously on the couch when I came back downstairs. Her eyes got huge when she saw Jerry behind me.

"See Jerry," I said while looking Tammy in the eyes, "I did too hire a hooker for us. She just loves to give blowjobs, don't you?" Jerry looked at her and I could read the fear and humiliation in Mr. Gunn's eyes. He looked at me and cleared his throat. "Yes," came the quiet feminine voice.

"How much?" I asked.

"I love to suck dick." Tammy replied.

"More or I blow the news, whore." I growled at her. Jerry looked at me confused for a moment. Tammy looked horrified. She quickly started to babble. "I would love to suck your dick, sir. Please let me later tonight. I want to so bad."

I smiled at her and she visibly relaxed. "That's better, Tammy. But I have a better idea. Why don't you suck off Jerry? He looks like he could go for some of you, you hottie!"

Jerry pulled off his pants in a hurry. "You love that idea don't you?" I asked her. She took a deep breath and got to her knees and crawled between his legs. I watched with glee as Mr. Gunn, that asshole, started to give one of his former student head while dressed as a hooker!

He looked at me as he did it. "I bet you love this don't you Tammy?" I asked looking at her, "You probably want to moan about what a good time you are having. Go ahead, and let it out." Tammy took the hint and started to moan and hum as she slurped on Jerry's hog. Jerry's breathing got faster as he neared his climax.

"I'm going to cum!" Jerry shouted as he arched his back. Tammy pulled back to avoid it and instead it shot all over her face. I leaned in close and hissed to her. "Never pull away again, you will act like you love this or I will beat you and ruin you!"

She looked at me with terrified eyes, "Yes sir. Never again."

Jerry calmed down and looked at us. "Are you going to fuck her now?"

Tammy looked shocked.

"I sure am!" I told my excited friend. "I paid for the first time in her ass. She's on the rag, you see." Tammy started to back away while still on her knees.

"Come here whore." She stopped, looked at Jerry grinning at her, and did. "Do you want me to fuck your ass like a champ?"

"Yes, sir. Please do me. But please be gentle."

I moved the ottoman in front of her and bent her over it.

I pulled her panties to the side so I could have access to Mr. Gunn's virgin ass. I reached on the ground in front of the couch and grabbed the Vaseline. I got a big glob of it and slid it into Mr. Gunn's asshole. I leaned over him and set the tip of my dick at the top of his ass crack.

"Well, whore? What do you want me to do?"

"Please put it in me, sir," came Mr. Gunn's feminine sounding response. I slid the tip of my dick slowly down the crack and held it at her opening. "Now?" I asked. "Now," She replied.

I slowly worked my dick deep in my playacting prostitute. She was taking me like a champ. Jerry was grinning like an idiot.

"You should see her face, dude." He told me. "Her face is all scrunched up. I think you really are her first back there." He started to pull on his hardening dick.

"How does this feel, Tammy?" I asked her as I slowly increased the tempo of my fucking.

"It only hurts a little, sir. Maybe it will feel good in a minute."

"Oh no, Tammy. I think you had better start loving it now!" I said as I started to slam into her ass with a vengeance. "Well?"

"It feels really good sir," Mr. Gunn growled out in a deeply feminine voice. "Please keep it up." Jerry was grinning and looking from me to my "hooker". I knew Gunn had to be trying to look like a girl getting laid to try to fool Jerry. I loved the feeling of power I got from this. I really started to slam into my unwilling sex slave.

"Do you love it now, bitch?"

The moaning from her was getting noticeably louder. Jerry was grinning from ear to ear, "Look at her face, dude, "She is loving this."

I began to notice that Gunn/Tammy was now arching her back and pushing back to meet my thrusts. I'll be damned, she did like this.

I was about ready to blow my load so I pulled out and slapped her ass. "Turn around whore and finish me off in your mouth."

Tammy spun around and took me all the way in in one deep gulp. She was practically frantic as she began to blow me. I was grinning like an idiot. I loved it. This was the best head I had ever gotten. "You are turned on aren't you?" Tammy could only keep going but I knew she was.

"Here it comes!" I shot off deep in her mouth. She never let up until I was limp in her mouth.

I leaned back satisfied and then high fived Jerry. Tammy had sat back on the floor with a dazed look on her face. I looked across the room at Jerry, "Why don't you come over tomorrow night, Jerry," I asked. "I think I might hire her again!"

I loved the look in Mr. Gunn's eyes at that!