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Alyssa's First Anal

"Mr. Wright takes Alyssa's anal virginity"

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Author's Notes

"This is Chapter 5 in a series and is entirely a work of fiction."

After Daddy dropped me off back at school, I told Bobbi all about how I seduced my mother and made love to her all weekend, and then how that very morning, I seduced my father too, so that he became the second man to fuck me.

I think Bobbi spent the entire time I was talking with her jaw dropped.

When I finished, Bobbi laughed. "My God, Alyssa, you really are a little slut, fucking both your Mom and Dad, and being the instigator for it all! Wait until you tell Mr. Wright tomorrow! He's supposed to be making you a submissive slut, not one who takes sexual control of her parents!"

I giggled. "I know! But, Bobbi, it was so easy to do! This whole submissive thing might be fun to play at, but I really loved taking control of Mom and Dad!"

All while I was telling Bobbi about my weekend adventures, she was rubbing her crotch through her shorts.

"Take your clothes off, Bobbi, and do that properly. I want you naked!" I told her.

She did as she was told, and when she was nude, I went to her fully dressed, took her in my arms, and kissed her passionately, my hands roaming over her soft, naked flesh. She moaned as my fingers pinched and pulled on her nipples. I leaned down and began to suck on her nipple, and then my teeth bit down on it, and she gasped in pain, but I think it sent a rush of wetness to her cunt as well.

I pushed her down onto her bed on her tummy, and I pulled her by the hips, so her butt was in the air. I licked her cunt, and discovered how wet I had made her. Then I pulled her ass cheeks apart, and looked at her tight little virgin sphincter. I lowered my mouth to it and pushed my tongue into her butthole. She gasped and jumped.

"Oh my God, Alyssa, what are you doing? Oh, fuck, that feels nice!"

"I did this to my mom, too! She loved playing with her girlfriends when she went to school here, as you and I do! Mom told me how much she likes anal sex too. I'm hoping Mr. Wright will take my anal virginity soon!"

I went back to tonguing Bobbi's asshole. I can't get enough of her. Every part of her turns me on, even my tongue inside her butthole! I went back to licking her sopping wet pussy, but I pushed my middle finger into her ass now, and I began sliding it in and out, finger fucking her as I ate her. Bobbi had her head buried in her pillow, moaning, calling my name.

"Oh, God, Alyssa, make me cum! Tongue fuck me! Finger fuck me! OHHH FUCK!"

She bathed my face in her cum. I was coated in her cream, and I lapped up all that my tongue could reach. I pushed her onto her back and straddled her face. I ground my cunt back and forth over her mouth. Her tongue penetrated my hole, and then found my clit. She worked her tongue magic on my nub, and soon I was coating her face as she had coated mine. We collapsed in a heap, cuddling, breasts heaving.

I slipped out of her bed and got into mine. I had a big meeting with Mr. Wright tomorrow, as Bobbi did with Mr. Armstrong.

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Bobbi and I got up at 7 am. We both had our meetings at 9, so we wanted plenty of time to shower and get ready. After the shower, I put on a bra and a thong under my uniform of a plaid skirt, white blouse, and plaid tie. I kept the skirt at a decent mid-thigh length. Bobbi and I both grabbed some breakfast at the school cafeteria and headed off to our meetings. I was extra excited to tell Mr. Wright about my raunchy and incestuous weekend.

I knocked on Mr. Wright's door.

"Come in, Alyssa!"

When I stepped inside, I was thrilled to see his couch opened out into a bed again. He greeted me warmly with a hug and a kiss.

"Well, Alyssa, how are you feeling after what we did together last week?"

"Oh, Mr. Wright, last Monday was the most amazing day of my life. I can't begin to explain how happy you made me. I was so happy, I called up my mom and told her I was going to come home for the weekend. I told her a little of what we did, and I said I wanted her to tell me all about her senior year here at the school, since she didn't need to keep it a secret from me anymore."

"That's exciting, Alyssa. How did the weekend go?"

"It was so good, Sir! As soon as I got there, I changed into my bikini, and she and I sat out by the pool. I told her about what you and I did, and then she told me about her first meetings with her headmaster. She said it sounds like we are more "progressive" now than it was when she was here!"

Mr. Wright smiled and laughed a little. "Yes, we try to bring you girls along a little quicker nowadays! Go on!"

"Well, it wasn't long before I convinced her to get naked with me, so we could show each other how we played with ourselves in front of the headmaster! She didn't want to at first, but I insisted, and she followed my lead. We made each other cum as we sat by the pool. It was so exciting, actually seducing my mother. I knew then that I wanted to do the same to Daddy when he got home from his business trip Sunday morning."

As I told all this to Mr. Wright, I was getting more and more excited. Next, I told him how I had asked Mom if she ever fucked other men besides Daddy since they had been together.

" It excited me so much when she said Daddy would arrange for men to fuck her, so he could watch and then clean her up when they were done with her. She also admitted to me how much she loved being fucked in the ass! Oh, Mr. Wright, we spent Friday evening and all day Saturday like that. I never imagined having sex with Mommy before, but I loved it. She was wary about me doing anything with Daddy, but I told her I was going to have Daddy's cock be the second one to fuck me no matter what!"

"You were taking control over your mother?"

"I guess I was a little, but I didn't care. When Daddy got home Sunday morning, I was in my skimpiest bikini, and was waiting for him."

I giggled. "Seducing Daddy was the easiest thing I ever did! In no time we were in bed together, and Daddy was fucking me while Mommy watched. Before long she joined in, and lay under me as Daddy fucked me. She licked me, and when Daddy came, some of his cum dripped onto Mommy!"

When I finally finished telling Mr. Wright everything, his demeanor changed. He appeared stern, almost angry.

He said to me, "Alyssa, I see the idea of submission is not one you are going to take to easily. Taking control of your sexual partners, whether they are your parents or not, is not something we work to instill in you girls. We are trying to teach the exact opposite! I see I have my work cut out for me. Stand up and take off your clothes and get on the bed."

I was excited and thought he would soon be fucking me, but when I was naked, he said, "Get on the bed face down and your ass in the air. Put your arms straight out in front of you!"

I did as he said, but then he told me, "Stay like that until I tell you to move!" I could hear him take a couple of pictures of me. "This is your phone. The pictures are for you to remind you what submission is!" I couldn't even see him with my face in the pillow, but I could hear that he went to his desk and sat down. I'm not sure how long I was in that position, but it seemed like forever. I didn't dare move or talk.

It was probably only ten minutes or so, but it seemed like an hour! Finally, I heard him get up and come near me. "This is some lube I am going to put on your asshole!" He rubbed the lube over my sphincter and slipped a finger inside me to lube me there as well. I was both excited and scared that he was going to fuck me in the ass, but then something else, clearly not a cock, was being pushed into my butt.

"This is a butt plug. You will leave it in place all week. You may remove it ONLY when you need to poop, and when you shower, in order to clean it. You will put it back in place as soon as you are finished with either of those two chores. Do you understand me?"

"Yes, Mr. Wright!" I said meekly.

"Get up now and put your uniform back on. We are done for today."

I was stunned. "W-we're done for today? Please, Mr. Wright, don't send me away already! I'll do ANYTHING for you. Please use me, Sir! Please fuck me!"

I started to cry. Tears dripped down my cheeks as he pulled me to my feet.

"You must learn that submission is more than just surrendering to your partner's desires. Denial is one of the hardest lessons to learn, and it is one you WILL learn. Listen to me, Alyssa. For this entire week, you are not to play with yourself. You are not to play with Bobbi, nor with anyone else. You are not to cum, or make anyone else cum. If you disobey me, I will know as soon as you set foot in this office next week. Do you understand?"

"B-b-but, Mr. Wright..."

He slapped me hard across the face.

"Do you understand me, Alyssa?"

"Y-yes, Sir! I promise!"

"Now get dressed and go back to your dorm room!"

He went back to his desk and began working. I was dismissed. Blubbering, I put my clothes back on and slipped out the door.

I cried the whole way back to the dorm. When I got to the room, Bobbi wasn't there. I was sure she was still with Mr. Armstrong. I threw myself onto the bed and cried my eyes out. I felt so frustrated and so humiliated. I wasn't sure how long I lay there before Bobbi returned.

"Alyssa, what's wrong?" she cried with alarm.

I sat up and, blubbering, told her about this awful meeting with Mr. Wright. She held me and kissed me. "Let me help make you feel better, Sweetie!"

"No, no, you can't, Bobbi! Mr. Wright made me promise not to do anything at all sexual all week, except to keep this butt plug in my ass! I can't disobey him. He said he would know instantly when he saw me next Monday if I did anything."

"How does that feel in your butt?"

"Feels kind of weird, but I guess I'll get used to it. It doesn't hurt, but he said it is there to remind me constantly what it means to be submissive."

"Well, Baby, I think you better throw yourself into your schoolwork this week to keep your mind off all this as much as you can. I promise I won't do anything to tempt you!"

I laughed a little at that, as Bobbi helped me dry my tears.

"Come on, Lys, let's grab some lunch!" She pulled me to my feet, and we headed to the cafeteria.

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The week dragged on. I did my best to focus on my schoolwork, but that damned butt plug in my ass was a constant reminder to me of how horny and frustrated I was. It was a treat to take it out in the shower. I took it out first thing, and put it back on only after I shut the water off. I wondered each time I inserted it, what a cock would feel like in there instead.

I was a perfect, obedient angel all week in the overwhelming hope and desire that Mr. Wright would be pleased with me come Monday. The weekend was the toughest. No class, and the anticipation of seeing Mr. Wright again on Monday was hard to bear. Bobbi went home for the weekend, which was both a good thing and a bad thing. Good, because she was a real temptation, but bad because she was also a good distraction.

Well, Monday morning finally arrived. I showered, removed the butt plug to clean it, and pushed it back into my ass when I was done. I dried my hair, got into my school uniform that I kept very modest today, with the skirt hem just above my knees. I didn't want to do anything that might upset Mr. Wright.

I was nervous as hell as I made my way across campus to the headmaster's office. I knocked softly.

"Come in, Alyssa!"

I opened the door and stepped inside. Mr. Wright came over to me and placed his hands on my shoulders. He looked deep into my eyes. I felt like he was looking into my soul!

"Alyssa, did you do anything last week that I ordered you NOT to do?"

"No, Sir, I did nothing I shouldn't have. It was hard, but I was obedient."

His gaze continued. Suddenly, his stern look vanished, and he smiled broadly.

"Yes, I can see you are telling the truth. Tell me about your week!"

"Oh, Mr. Wright, it was one of the worst weeks of my life. I felt so miserable that I had let you down, and the plug in my butt kept me in an almost constant state of agitation. I was so tempted to play with myself, but I couldn't. I couldn't bear the idea of disappointing you! I want to please you so badly. Is that what you mean by submission, Sir? I want to do whatever you desire."

"I hope you learned an important lesson this week!"

"I did, Sir. Truly, I did!"

"Good girl! Now, take off your clothes."

Oh, I was so excited he was pleased with me. I hurried to get naked. When I was nude, he said to me, "Spread your legs a little, bend over, and grab hold of your ankles."

I did as I was told. Oh, what a feeling of exposure, on display naked like this with a plug in my ass, while he was fully clothed. I relished the feeling!

He came to me and extracted the butt plug. It came out of my ass with a 'pop'! Mr. Wright then gently rubbed and caressed my ass. The feeling of his strong, warm hands stroking me filled me with joy. He was so right. I must fully learn to subjugate myself sexually!

"Stand up now, Alyssa, and lie on the bed. I have a little gift for you as a reward for your obedience."

It was only at that moment that I realized his sofa was again opened out into a bed. I lay on my back and looked at him with anticipation. He went to his desk and retrieved something. It was a vibrator.

"I was planning to give you this last week. Bobbi and the other girls all got theirs last Monday. You deserve some release after all that pent-up horniness. Use it on yourself while I watch and undress."

I spread my legs wide for him. My pussy was aching for relief. I made sure he had a perfect view of my pink, wet hole as I turned the vibrator on. Oh, God, it felt good! I locked my eyes on Mr. Wright as he undressed. The feel of the vibrations as I pushed the toy inside my cunt was indescribable!

When he pushed his boxers down, and his magnificent cock popped into view, jutting straight out and throbbing, I almost lost it. I touched the vibrator to my clit, and instantly I began to cum. I shrieked in pleasure as Mr. Wright approached me, totally naked.

He reached down and took the vibrator from my hand. "That's enough of that for now, Alyssa. I have something much better for you!"

"Are you going to use me now, Sir? I want to be a toy for your pleasure!"

"Get into that same position I had you in last week. On your tummy, ass upraised and arms extended forward."

I instantly got into position. He squirted some lube on my anus and used his fingers to massage it into me. Like last week, I was both excited and scared that he was going to fuck my ass! This time, I was allowed to move my head, and I could see he was slathering lube all over his big hard cock. I shivered in anticipation. I knew it was going to hurt, but I wanted it anyway.

"Are you going to fuck me in the ass now, Sir?"

"Yes, Alyssa. Are you scared?"

"A little, Sir! I think I need it, though! I'm your property to use as you like! My Mom told me she loves when men fuck her ass."

"I'll be as gentle as I can, but your last vestige of virginity needs to be taken from you!"

With those words, I felt the bulbous head of his cock press against my sphincter. He handed the vibrator back to me. "You can use this on your cunt to help mitigate the pain."

I turned it on and pressed it to my clit, just as he fully pushed his cock into my asshole. I cried out at the sudden, rather intense pain. He stopped to let me relax. The vibe on my clit flooded me with pleasure, as he began to slowly thrust in and out of my no longer virgin ass.

"Use me, Sir. Use me hard. I'm yours. Fuck me, please! Make me your whore!"

His tempo increased. He was really ramming my ass now. The pain of it...

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