Blueeyeddevil06 thank you for being my beta.
Serena is above the age of consent, she's 18. In the USA it's 16 or 17 depending on your state. That said, sex with your Principal is illegal for a very good reason. This is fiction, please read it as such.
Principal Shields
Darien had been Principal of an all girls school for a year and a half now. He was known for being very professional and, if anything, erred on being a little cold. He knew many of the high school girls flirted with him, but he wasn't tempted in the slightest. The staff laughed at how well he was able to put them all in their place.
That was until Serena was transferred into his school her senior year. She was eighteen and looked older than that. Her body was amazing, and her breasts were straight out of a man's fantasy. He wanted. He dreamed of touching and tasting her. His fantasies were so vivid that he jerked off to the thought of her often.
Serena sat in Principle Shields' office. She was fidgeting. She was late again for school, and she was excited about it. The moment she was sent to the office she had to hold back a smile. She liked looking at him, and when he talked sternly to her, it made her stomach flip, making her so wet. She liked it when he sounded commanding. It was straight out of her fantasies.
He walked in and sighed. "Serena, you have to stop getting sent here!" His eyes bored into her. He needed her to stay away; his very thin resolve was cracking. He wanted her. His cock had a mind of its own and was getting hard.
She held back a moan and pouted, "I can't help that I'm late. I hate getting out of bed." She locked eyes with him and moaned, "I love laying in bed, I love sleeping naked, and the satin sheets feel so good on my bare skin."
He looked at her sternly, "Serena, you have to stop talking like that." His hand twitched as he felt his resolve shatter. All that had been holding it in place was him telling himself she didn't want him.
"Why?" She stood, walked over to him, and placed her hands on his chest. "Do you really want me to stop? I noticed that you watch me."
He shook his head adamantly, "No. No, I don't want you to stop." He grew even harder as he breathed in her sweet scent.
"Good." Her hand drifted down, ghosted over his abs, and then rubbed over his cock. "I want you." She stroked him through his slacks.
He moaned, "You should stop." He tried to find a scrap of resistance to her. They were in his office at school for goodness sake.
She gave him her most innocent look, "I'm not hearing that you want me to stop." She reached down in his pants and grabbed his large hard cock in her hand. She stroked him.
He snapped and reached out, grabbing her breasts. He hissed out, "I don't want you to stop. I want you so fucking much." He played with her breasts. "Your boobs feel better than I imagined. And, I've imagined them a lot." He moaned and pressed her body up against the wall, "I've wanted to do so many things to this sexy body of yours." He grabbed her ass and held it firmly. He whispered in her ear, "Tell me you'll let me fuck your sweet cunt. It's all I can think about. I'm losing my mind over you. I want to feel what it's like to bury my cock in you and hear you scream my name." He rubbed his hard cock against her leg. "Come to my apartment, I'll give you my address. Please say yes."
She nodded and said, "I'll be there." She stepped back and said, "See you tonight."
That night, he answered the door, and his already hard cock twitched at the sight of her. She was standing there in a very short skirt and a tight top that barely covered her nipples and exposed a lot of her boobs. She looked like sex.
He looked at her full of desire, and reached out with both hands and pinched her nipples, using them to pull her into his apartment. "You look so fucking sexy." He wrapped one streamer of her hair around his hand and gently pulled down on it. "Get on your knees for me." He unzipped his pants, pulled out his cock, and stroked it. "Suck it." He then thrust himself into her mouth. He held onto her hair and put his other hand on the back of her head, guiding her into a rhythm. She sucked on him and took him deep into her mouth. He then began rutting into her. He pulled out with a soft pop. "Enough, I want to cum inside of your cunt."
Serena wanted to find a way to work him up even more. She liked what she was doing, and she wanted him. She leaned forward, sucked his balls into her mouth, and hummed. She flicked her eyes up at him and saw the lust in his eyes. She then pulled back and licked her lips. "I knew you must have huge balls. You invited a student to your apartment after all."
"Well, you're too sexy to resist. I tried so hard. I masterbated so many times trying to control myself. And, every time it wasn't satisfying enough. Now, it's time for you to satisfy me." He pulled her up off her knees. He then slid his hand up her skirt. "I'm going to fuck you and make you come back begging me for more." He slid his fingers under her panties and thrust his fingers into her tight, wet pussy. He moaned, "You're going to feel so damn tight on my cock. He pulled his fingers out, pinched her clit, and heard her moan. "Follow me. I'm going to fuck you now."
"Yes, Mr. Shields."
"You better call me Darien. Mr. Shields is a bit much to scream out during sex." He led her into his room and pulled off her shirt. He then played with her breasts. "This bra looks so sexy on you." He pinched her nipples and rolled them in his fingers. He released her and then unhooked her bra. "Lay on my bed." She did, and he pulled off her skirt and panties. "You are so damn hot. I want you so much." He removed his pants the rest of the way and took off his shirt. "Spread those sexy long legs for me."
She scooted back more onto the bed, spread her legs for him, and he thrust deep inside of her. He felt a barrier tear. "You're a virgin?"
"Was. Now fuck me." She wanted him to get over it. She was nervous that it would bother him.
"I… you should have said something. I would have been more gentle." He wanted her, but he didn't want to hurt her.
She rolled her eyes, "Fuck me, now. I'm okay."
He began thrusting long slow strokes of his cock into her. He watched her face as he took her. He reveled in how much pleasure shone there. "Are you on the pill?"
She moaned, "Yes."
"Good. You feel so good. I don't want to put on a condom. I like fucking you like this and feeling you on my bare cock." He thrust once hard into her and then went back to his slow and steady rhythm. "I like seeing my cock glisten with your juices. Flex your inner muscles." He let out a guttural moan, "Good girl. That feels so damn good. You're so fucking tight." He sped up the pace the smallest bit. "I'm going to have so much fun with you. Does this feel good?"
"So good," she moaned out.
"Your tight cunt feels like a vice on my cock." He started thrusting harder. He moaned, "So good. You have such a pretty cunt and your boobs are so big." He grabbed her breasts and pinched her nipples. "You're a naughty girl, aren't you? You just love being sent to the Principal's office, don't you? You like it when I lust after you. How images of your perfect body tortured me." He thrust into her harder. "You like coming to my office and finding out your punishment from me. I fantasized about being able to spank you. I would love that."
She moaned, "I do like it. I purposely get in trouble to be sent to you. When you talk sternly to me, it gets me so hot. I also unbutton a few buttons on my shirt on my way to your office. I'm so naughty, I think you do need to spank me."
"Fuck, Serena," he thrust into her harder now. "Are you up for punishments? We'll have a safe word."
"Yes, punish me!" She then moaned loudly. "But first, fuck me harder, dammit."
Darien thrust into her harder and flicked her clit. He felt his release building and pounded his cock into her pussy. He heard his balls slapping against her and moaned. He then lost himself in blinding pleasure. He did hear her yell out his name in passion. They both collapsed on his bed.
He looked at her. "Serena, you're not going anywhere right now. You stay in my bed. I'll need a bit of time, and then we'll go for another round. I'm going to love fucking you again. You feel too good to let you out of my bed, yet."
She looked at him with vulnerability in her eyes. "What are we?"
"Exclusive. I don't want you fucking any boys. I want you only in my bed. Also, if I'm bold enough, in my office."
"You won't see anyone else? Even for dates?"
"I won't even meet up one on one with a female friend if that makes you feel more comfortable with continuing to have sex with me. We'll be truly exclusive, I promise. Do you promise too? You won't need any boys. I'll keep you satisfied."
"Yes, I'll promise that we're exclusive."
"We need to work out our schedules. We have to be careful and plan ahead. I can't get caught."
"I can come by tomorrow. Is seven okay?"
"Yes, that works for me. Will I see you in my office tomorrow?"
She smirked, "That will be a surprise."
Darien stood and got a washcloth. "I'm going to get us cleaned up." He wiped off the blood from her. "I love looking at your body." He then sighed, "You should have told me you were a virgin. I would have been more careful with you."
"I was afraid you'd turn me down if I told you."
"You think I wouldn't have been willing to take your virginity?" He laughed, tossed the wet rag in the sink, and came back. "It wouldn't have stopped me for a second. I don't think you understand how much I lust after you." He pinched her nipple. "All I needed was to know you were willing. Once I did, I had zero desire to control myself around you. Tomorrow, if you show up at my office, I'm going to tell you in detail what your punishment will be for the evening. You'll also get to approve it."
"I may even add something to it. You do seem rather tame to me." She smirked.
"How the hell am I tame? I just took the virginity of a student, and I'm not even remotely sorry."
"Spankings. I think we can be more creative than that. Do you have a paddle?" He shook his head no. She smiled and said, "I'll pick one up on the way over tomorrow. I think I know exactly the one I want you to spank me with."
"You already have a paddle picked out? How? You were a virgin." He was puzzled.
"I like pleasure in pain. I like pinching my own nipples, hard. I also stop by the sex toy shop. I have a vibrator I bought there." She smirked, "I named it Darien. While I was there, I browsed through the other things, and it looked exciting."
His gaze darkened, and he stroked her stomach, "You're a very naughty girl. You look so incredibly innocent, but you're not." He ran his hand over her breasts. "It's exciting." He pinched her nipples. "Spread your legs for me again. Now, I'm going to taste you." Without a word, he buried his head between her legs and sucked her clit. She bucked her hips, and he put his hands on them pinning her down. "Stay still." He then began sucking on her again. She whimpered and moaned.
"That feels so good. Please, don't stop." She writhed under his minstations. He fucked her with his tongue and used his teeth on her clit. He quickly had her screaming his name.
"See, screaming 'Darien' works better. Plus, it's what I thought of you screaming out when I jerked off." He wiped off his mouth and kissed her, hard. "You taste delicious. Don't you think so?"
She moaned. "Kiss me again, and I'll tell you."
He kissed her and thrust his tongue into her mouth. She moaned. When he pulled back, she was panting and nodded. "That was so good. You're so good with your tongue."
He rubbed his hardening cock against her leg. "Touch me and finish getting me hard. I want to have sex again."
She reached down, took him in her hand, and stroked his cock. "Does this feel good? You need to teach me."
He changed the angle and grip very slightly. "There. Shit, that's perfect. Feel how hard I am?" She nodded, and he pulled her hand off of him. "I'm plenty hard now." He smacked her thigh, "Spread 'em." He then thrust into her.
She matched his rhythm as he pounded into her from the start. She moaned and said, "I like it rough. That feels so fucking good when you do that. Harder!"
He pounded into her and watched her boobs bounce. "Fuck, you're perfect. I love your boobs and hearing you like it hard." He snapped his hips into hers, and he heard them slapping together. Pretty soon they were both coming, and he was screaming out her name.
He collapsed next to her and tried to catch his breath. "What kind of hobbies do you have?"
It struck her odd when he asked her about her hobbies. She asked, "Besides being late?"
He chuckled, "Yes, besides that."
"I like to hang out with my friends at the arcade and play video games. I used to take gymnastics."
His eyes darkened. "You did? I didn't know that."
"You're suddenly trying to think of sexual positions."
"Yes, but that's not why I asked."
"What are your hobbies?"
"I love to read… that's mainly it. Gosh, that sounds boring."
"I think having sex with one of your students makes you officially not boring. Plus, I rate that sex incredible. Not dull at all." She smiled at him, "It's actually very exciting that we get to do that again tomorrow."
He grabbed her breast. "I couldn't agree more about tomorrow." He pinched her nipple. "Your boobs are so perky and big. I liked the shirt you wore to my place today." He kissed her breasts.
Serena groaned. "I hate this, but I have to go. My parents are expecting me." She leaned down and kissed his pecs. "You're hot."
Darien nodded. "See you tomorrow."
The next day, Serena smirked when she was sent to the Principal's office. She sat outside of it and was called in by a very stern looking Mr. Shields.
He closed the door and smirked, "You just couldn't stay out of trouble, could you?"
"No, Mr. Shields. I was promised that I would hear what my punishment was going to be tonight." She moaned and unbuttoned a few extra buttons.
Darien noticed her bra, "Pink lace, very nice. As for your punishment." He pulled out some cash and handed it to her. "Buy a paddle. Whatever's left will go towards future purchases. They all stay at my place. We can't have your parents finding out." He reached out and pinched her nipple. "I plan on spanking you with the paddle. I'll make you count them out."
She moaned. "I'm loving it. How many?"
"How bad have you been?"
"So bad. You have no idea. I want you to spank me and then make me suck your cock. I liked it when you grabbed my hair and forced me on my knees last night. Just thinking about it gets me so turned on." She looked around. "What's the chance I can suck on your cock in here? I bet you're so hard right now."
"Fuck. Yes, it's so hard. Everyone thinks you're so sweet and innocent. Get over here quickly," He rolled his chair back and waited for her. "Be a good girl and take me deep down your throat."
She sank down on her knees under his desk as he unzipped his pants and pulled out his turgid cock. She slid it in her mouth and sucked on him. He held the back of her head as he rutted into her mouth. He tugged her hair as he thrust into her. He came hard against the back of her throat. She swallowed, looked up at him, and smirked.
"You look like sex right now." He reached down, grabbed her breasts, and rolled her nipples in between his fingers. He then released her.
She stood, buttoned up her shirt, wiped her lips, fixed her lipstick, and straightened her hair. "Better?"
"Yes." He looked down. "I have your pink lipstick on my cock. That's so damn hot." He zipped his pants back up and straightened his shirt.
"You might want to open a window. It smells like sex in here." She said.
Darien opened his window. He then whispered, "I'm going to leave your ass pink tonight. You're so naughty."
"You're the bad boy. I only did what you told me to." She smirked and stood. "I'll tell them you gave me a warning. After all, the real punishment comes later. After you spank me, I think you need to take me from behind." She then walked out his door and closed it.
She showed up that night right on time. Serena handed him the paddle. "It looks sturdy enough."
"You really want me to use this on you?"
"If you don't want to, then that's okay."
He shook his head then went and sat on his couch. "Ms. Tsukino, you have been tardy yet again today. Come over here. It's time for your punishment. Bend over my knee, and show me your bare ass. I'm going to paddle it."
Serena did as he asked. She purposely wore her school clothes to his apartment that night. She pulled off her panties, flipped up her skirt, and bared her ass to him. She was bent over his knees. "I've been so bad. How many spankings?"
"We'll see. Count them."
He lightly paddles her ass. "One," she said. He paddled her a bit harder. "Two." He made the next a bit harder. "Three." He paddled her a bit harder, and she let out a lusty moan. "Four."
"You like it that hard?" His cock twitched.
"Yes!" He paddled her again. She moaned out, "Five." He did it again. "Six." Again. "Seven." He paddled her one more time harder. She moaned loudly, "Eight!"
He set the paddle down and looked at her pink ass. He then ran his fingers over her pussy. "Fuck! You're so wet. You really liked that, didn't you?" His eyes were blown wide in shock.
"Yes, I did. It was so hot."
He flicked her clit, and he felt her body react. He buried two fingers inside of her completely and fucked her with them. He then scissored them. "Serena, I'm going to play with your pussy as you're bent over my knees."
She rocked into his fingers to create more friction. "You have no idea how worked up I've been since I gave you a blowjob in your office. I want you."
"Serena, I'm going to give it to you. Right now, you look so wanton. I love seeing you like this." He thrust his fingers into her tight channel harder. "All the people in the office today were talking about how kind you were and that they wished you would just show up to school on time. They called you a sweetheart." He let out a dark chuckle. "The whole time I knew I had that sweetheart's lipstick on my cock. Shit, I loved it. Knowing that you had just been on your knees for me. I knew that you had money in your pocket to buy a paddle that I would get to spank you with. And now, look at you. You're bent over my knees with a pink ass and my fingers buried in you. I really like this addition to your punishment." He flicked her clit.
She moaned. "How do you want me? I want you so badly. Please fuck me so hard."
"Get up, strip, and get on your hands and knees on my bed." He thrust his fingers into her again. "I'm going to take you from behind." He kissed her pink backside.
She got up and stripped with his fingers still inside of her.
He said, "You're so sexy. I like seeing myself buried inside of you." He pulled his fingers out and licked them.
Serena went and got on his bed on her hands and knees.
"You remembered to take the pill today?"
"Yes."
He slid his hard cock inside of her. "Good." He grabbed her ass. "I like this view." He reached around with both hands and grabbed her nipples. "I'm not going to be gentle."
"Good. Now fuck me already!"
He thrust into her and played with her clit. She moaned and arched her back. He grabbed a shoulder for leverage and took her. Hard. She moaned out her pleasure. Their bodies slapped together, and she shouted out her orgasm as his orgasm raced through him. He came deep inside of her.
They both laid on the bed. He wrapped his arms around her and pulled the sheets over them. "That was incredible," he said.
She just nodded and made an unintelligible sound.
He gave her a cocky grin. "It was that good?"
"Yes," she breathed out.
He continued to hold her. "Please tell me you're available tomorrow."
"It's Friday. I should make plans with my friends. We're trying to hide this."
"Can't you make any time for me?" He pinched her nipples, hard.
She moaned and said, "Since you asked so nicely, yes. How about ten o'clock? I'll tell them I'm tired and leave early."
"What time will you have to leave though?"
"My parents are gone. I don't have a curfew that will be enforced."
He smiled, "So, late night play time at my place."
"Yes." She shifted to get up.
"Where are you going?"
"We already had sex. I just assumed you wanted me to leave." She looked confused.
"Give me some time, and we'll go again." He grabbed her ass. "You're just too good to let go yet."
She nodded and settled back into his arms. "Just let me know when you're ready."
He looked at her funny. "Don't you want it?"
She rolled her eyes, "Of course I do. I showed up here after all. I don't have to come."
"What aren't you saying?"
"I just don't know the protocol for having sex with your hot Principal. Forgive me if I get it wrong sometimes."
"With a body like this," he ran his hands over her. "It's hard to get anything wrong."
She smiled, "Good to know."
He looked at her and huffed, "So, I don't play video games. A lot of guys my age do. I just don't know what to do with them. If I bought a console and some controllers, would you teach me? I would like a new hobby."
"Yes. I would be happy to. I love all video games."
"Thanks."
She laid there in his arms and felt a bit lost. It felt tender to her. She worried that being so soft hearted would make this mean too much to her. She reminded herself that he was just waiting on his cock until he could fuck her again. He really liked her body. Then she would be dressed and on her way back home.
Another incredible orgasm and an agreed upon safe word later, and she was dressing and getting ready to head out. She left the paddle by his bed.
The next night at ten, she showed up. He let her in, she took off her shoes, and then her shirt. "So, where do you want me?" She then removed her shorts. "I remembered to take my pill."
He seemed a bit lost. "Is there something you want to do?"
"I want to ride you."
Two orgasms later, she was dressing and getting ready to head home. "When should I come over next?"
"Tomorrow afternoon?"
"I'll be here at one. Is that okay?"
"Yes."
She left after that. He rubbed his hand through his hair. He didn't know how to make her stay longer, but he wanted to figure it out. He decided he would buy a gaming system tomorrow morning.
The next day at one, she showed up, and Darien smiled and held up two gaming controllers. "Care to teach me?"
"I'd love to!" She beamed.
She absolutely kicked his ass at the game. He was laughing so hard when they stopped. "I'm just terrible."
"You just need practice. You'll get good at it." She smiled at him. "It was fun beating you."
Darien chuckled, "I'll just have to show you how I can come out on top."
"Please do." She gave him a sultry look. "I want you cuming on top."
He picked her up and pinched her ass. "Time for a different kind of play." He set her on his bed and pulled off all of her clothes. He smiled at her body. "I can't resist any bit of you. Now, I want to bury myself inside of you."
She spread her legs wide. "Get naked, and get inside of me. I want you so much right now."
"Can I tie up your wrists? We do have a safe word."
"Yes." She held her wrists over her head, and he tied her up with a silk necktie.
"This is so hot!"
He thrust inside of her. "I can't get over how tight you are! It feels so good." He then began taking her. He could tell she was loving it. Her nipples were hard and flushed. She was also moaning. "You have no idea how good you look like this."
"Tied up, moaning in pleasure?"
"Yes, and naked. I can't get enough of your body."
He thrust into her and played with her breasts. He loved them. He changed angles and hit her g-spot. They both came, and he wrapped his arms around her. He kissed the top of her head. "Want to kick my ass again at the game? I want to have you again before you leave." He untied her.
"Sounds wonderful to me. Video games and hot sex. Great day!"
She destroyed him again, and then they came together again.
Later that night, he practiced his game. He wanted to get better.
A week and a half later, he was reading an article online and laughed. He turned to tell Serena and grew pensive. She wasn't there. He tried to figure out what he was feeling. He realized he really missed talking to her. She had a family night, and she wasn't able to come.
The next day at school, he was cranky. That was until the sixth hour when Serena showed up at his office door.
She walked into his office, closed the door, and sat down. "I'm sorry I couldn't get away last night. I hope you aren't mad at me."
"What?"
"We didn't have sex. Are you upset with me? I wanted to apologize. I can come over tonight, and I'm up for anything you want to do." She looked sheepish.
"Serena, I understand you have a life. I'm not mad."
"Oh, good! I can still come tonight at seven."
"I'd like that."
She smiled. "I'm glad our deal is still on. It is, right?"
"I haven't gotten together with any woman."
She breathed out a sigh of relief. "Good."
He looked confused, "I promised that we're exclusive."
"I know. I just… never mind."
"Everything is fine. Come over tonight. I've been practicing my video game. I don't think I'll lose as badly this time."
"I'll be there!"
Darien felt uncomfortable. He didn't know what he did to make her feel like he would end things with her so easily. He didn't want to. Not at all.
He thought for a moment. He realized he wanted way more than just sex from her. He then thought about how he had been holding her, talking, and playing video games with her. He had wanted more from the beginning.
Serena showed up at his apartment in a tight pink dress. He opened the door and said, "Serena, you are so damn hot. I want you." He pulled her in and pressed her against the wall. "I want to fuck you in this dress." He pulled off her panties and bent her over the back of the couch. He pulled out his hard cock and buried it inside of her. "I like your wet pussy. It feels so good." He drove himself into her until they both came.
She smiled at him over her shoulder. "So, the dress worked like I wanted it to."
He sat on the couch and pulled her into his arms. "If you mean it drove me wild, then yes. It worked."
"Good." She sighed. "We need to be more careful at school. I can't get sent to your office again for a while. Ms. Moore is getting weird around me. She also wants you."
Darien rolled his eyes, "I know. She's asked me out several times in the last two weeks."
She grew pensive, "Oh."
"Don't say 'oh.' You know we're exclusive. I would have said no even if we weren't. She's not my type."
Serena laughed bitterly, "Hot and easy? I think she's both."
"Serena, don't. That's not how I see you."
She gave a dark chuckle, "I'm a good fuck. I know just how you see me."
"No, you're wrong." He was aggravated with her.
She smirked, "I'm not a good fuck?"
"You are, but that's not all you are." He sighed. "Give yourself some credit."
"I did. I said I was good."
"Serena."
"I'm also good at video games."
"You're more than all of that."
A tear leaked down her cheek. "You need to stop. I've been trying so hard, but I can't do this anymore." She stood and wrapped her arms around her stomach. "I'm not capable of separating sex and my heart. I… I'm so sorry. Please forgive me, but I fell in love with you. Don't worry. I'll leave, and I won't bother you again." She turned and looked for her shoes through her tears.
He grabbed her arm. "Look at me!" She turned with tears in her eyes. "I love you too."
"Wha…?"
"I miss you when you're gone. Not just the sex. I just noticed that I turn to you to say things all the time when you're not here. I love having you around. I've been trying to figure out how to tell you I want more from you. Please stop leaving right after sex everytime damn time. I want to spend time with you talking and holding you."
"Darien, really?" She smiled at him, and her tears dried.
"Really. I don't ever want to let you go."
Six months after she graduated, they faked the start of a romance between them. Four months after that, he asked her to marry him. They eloped by the end of the following week.