Bad Virgin

by Kelli Callahan

  “You like that don’t you? You like having your asshole teased.” He pushed his finger again as I moaned.

  “Yes,” I nodded quickly and then paused when I felt a second finger next to the first one.

  The feeling was nearly as rewarding as what I felt when he was inside my pussy, but it wasn’t exactly punishment. He started working his second finger into me until it had joined the first one and my anus was stretched even wider. His saliva ran down the edge of my anus and provided more lubrication for his finger as the thrusts got faster. Two fingers hurt and stretched me so much that I was in a place between pleasure and pain. I couldn’t imagine what it would feel like when he put his cock in my tightest hole. He worked his fingers inside me until they were moving effortlessly while his tongue continued to caress the outer circle of my anus. My body was writhing against the desk, completely overwhelmed with the pleasure he was bringing. He slowed his thrusts down and I felt his tongue retreat. He put both hands on my ass and stood, pressing down on the punished flesh. The sound of his zipper echoed through the office as it was pushed down. I felt his weight against me and then his cock pressed on my anus.

  “Beg for it.” He brought his hand down hard on my ass.

  “Please...” I reached back and put my hands on my ass, pulling it apart and pushing against his cock. “Please give it to me.”

  Fear engulfed me as I begged to have my asshole fucked. I needed to be submissive to him. I needed to show him that I regretted my betrayal and my attempt at blackmail. I hoped he would see that I was doing my best to repair the damage I had done and take the punishment he thought I deserved. I would let him use my body for pleasure, even if I didn’t get what I craved most. My pussy was on fire with lust to have him inside me, but I knew my asshole was all he wanted. Giving it to him would ensure that I felt him inside my pussy again in the future—denying him his prize would put me outside his office with a door slammed in my face. The glans pressed against my anus and began to stretch it as he pushed into the saliva coated hole he had created for his pleasure. He slid a couple of inches in and I pulled my hands away, gripping the wooden desk with my nails. The pressure from being stretched gave way to pain as he pushed himself deeper.

  “This tight hole is going to make me cum so hard.” He grunted as he pulled back and pushed himself into me again.

  He kept pushing himself into me as I held onto the desk. The pain from being stretched was more intense than what I felt when he took my virginity, but it was different. His cock didn’t ignite my pleasure like it did when he was inside my pussy. He pulled back after pushing several more inches inside me and thrust a little harder. I felt a brief sensation of pleasure from being rocked against the desk, but then it faded when he started to push his cock in deeper. If the resistance was any indication of the tightness he was feeling, then I knew his gasps of excitement were authentic. He continued pulling back and thrusting, driving his dick a little further with each insertion until I finally felt his pelvis against my ass. The warmth of the spanking was still present and I could feel the heat radiating against him. He kept his cock buried deep for a few seconds, delivering softer thrusts that allowed me to finally adjust to the feeling of his cock inside my tightest hole.

  “This feels really good.” He gasped and started to pick up the pace.

  I remained bent over the desk as the speed intensified, giving him pleasure with my body even though I wasn’t feeling anything more than pressure and mild discomfort. After a few dozen thrusts, I started to feel something different. My body finally relaxed and I was no longer being stretched with every thrust. The speed of his thrusts made my ass clench against him and the faster he got, the more it started to feel good. It was a dull sensation at first with the thrusts vibrating down into my pussy, but once he was going full speed and hammering himself into my ass, I felt pleasure surging through my body. It wasn’t as powerful as feeling him inside my pussy, but the stimulation was still there and it was a slow build that teased me. I started pushing my hips back against him, trying to keep the sensation going. He could feel it as well and although he didn’t set out to make me cum, there was no way that I was going to be able to hold back if he kept it up.

  “Harder...” I moaned and started to breathe heavier. “You’re gonna make me cum!”

  He shifted his weight until he was directly against my ass and started to drive his cock into me so hard that the desk was tilting forward with every thrust. Papers were sent flying into the air. His nameplate hit the floor and a second later his coffee cup joined it and shattered against the tile. He didn’t seem to care. He just fucked me harder as everything on the desk got thrown off and the drawers even started to open and slam shut with the power of his thrusts. Pleasure surged through my body as he crashed into me and kept his cock driven deep. I started to feel him throb inside my ass, followed by several pulsations. He growled as he moaned and I could tell he was close. I was right there with him, hovering so close to an orgasm that I could feel my hairs standing on end. His thrusts started to get more erratic and then I felt my muscles tense. A second later they were starting to spasm as I felt the orgasm rush out of me. My anus spasmed on his cock and I felt him go deep. A torrent of cum rushed from his dick and I could feel it surging through the shaft before it was unloaded inside me. He continued to hammer his cock into me as he released all of his seed while I orgasmed. He didn’t stop until he was spent and my body finally relaxed from the intensity of my orgasm.

  “I got to cum after all.” I looked over my shoulder and smiled.

  “I guess I’m just that good.” He slowly removed his cock from my ass and wrapped his arms around me. I lifted up and we sank down into his chair tangled up in our embrace.

  “So you forgive me for trying to blackmail you?” I leaned against his shoulder as he held me tight in his arms.

  “I’ll let it go this time, but I’m not the kind of man that gives second chances.” He traced my body with his fingers. “I have to know I can trust you, otherwise this isn’t going to work at all.”

  “I know. It was stupid.” I closed my eyes and felt the afterglow of my orgasm settling into my veins.

  We stayed there together with our lips casually touching for a kiss throughout the remainder of the day as the sun went down. We didn’t need words. Our souls were connected and we were able to communicate with nothing more than a touch. There were things inside of me that I didn’t understand, feelings that had never managed to surface before that suddenly manifested. I wanted to be close to him—I didn’t want to be anywhere else. When it was finally time to go, the sting of being separated from his touch hurt more than the entire time I spent over his knee. He walked me to the door of the school and we kissed one last time before it was time for me to go. I could have stood in that doorway with his lips crushing mine until the sun came up again, but I knew my mother would lose her mind if I didn’t come home. I left the school with a smile on my face even as the heaviness in my heart ached in my chest.

  Chapter 13: Anton

  I’ve never been in love. I’ve held a lot of women that said they were, but the emotional connection was never formed with me. Bethany danced in my thoughts even when we weren’t together. My reaction to her attempted betrayal had been out of character for me, as was my decision to give her another chance. I told her I didn’t give second chances and that was true, but the reality was that I normally didn’t even give people a first chance. I kept myself guarded from things that could hurt me because it was easier that way. I opened myself up to Bethany—I gave her the power to hurt me. The way I felt after I thought she was throwing away what we were building for something as foolish as blackmail made that clear in my mind. I had no idea what it was about Bethany that brought things I thought would never exist within me to the surface and burned brighter than anything else had burned before. She was all I thought about as I finished up at the office and when I got back to Sloane’s house, she was still on my mind.

  “You wor
k later than I ever did.” My brother’s voice came from the kitchen when I walked through the front door.

  “There’s a lot to do if I’m going to give the school back to you with the walls still still standing.” I walked into the kitchen and my eyebrows raised in surprise. “You’re cooking?”

  “I’m trying to keep busy.” He flipped a hamburger in the skillet and I saw peeled potatoes that had been chopped into wedges sitting on the cutting board.

  “Need any help?” I opened the fridge and grabbed a beer.

  “You can put some plates on the table if you want.” He pointed to the cabinet where the plates were kept.

  “Sure thing.” I nodded and opened the cabinet. “You’re not drinking tonight?”

  “No, I took your advice and spoke to a psychiatrist today. She gave me some good advice.” He looked over his shoulder and smiled. “She also gave me some good drugs.”

  “I see...” I nodded and walked to the table.

  “Nothing crazy—just something to take the edge off and keep me from running to the bottle. She put things in perspective and I haven’t felt this good in—at least a year.” He finished cooking the hamburgers and moved them to a plate before he started frying the potato wedges.

  “So what did she say?” I felt my curiosity rising as I saw his jovial mood.

  “I’m setting unrealistic expectations and I need to realize that I can’t change the world. I can only control what goes on in my sandbox.” He pushed the potato wedges around in the skillet. “If I’m not happy with what I’m doing, I need to find something that makes me happy.”

  “So what is going to make you happy?” I picked up the plate with the hamburger patties and grabbed the buns from the top of the fridge.

  “I don’t know yet, but I aim to find it. Maybe it isn’t Grantham University. Maybe it isn’t teaching at all.” He shrugged and started salting the potato wedges.

  “Does that mean you’re ready to go back to Grantham?” I wasn’t ready to leave, but he seemed to be in a much different place than when I first took over for him.

  “No.” He shook his head back and forth quickly. “What you’re doing is a blessing. I don’t know what the future holds for me, but I know I need time to figure it out.”

  Sloane finally finished cooking and we sat down to eat. There was definitely something different about him. Either the medication was taking him to a new realm of happy or he was genuinely at peace after meeting with the psychiatrist. I never dreamed that he would have such a drastic turnaround so quickly. I figured he would need intense therapy just to get him out of his funk. If the miracle of medicine was that good, then I might need to see a psychiatrist the next time I got in a foul mood. Fortunately, that wasn’t the case for me. I was walking on a cloud of bliss after my time with Bethany. We devoured our dinner then walked into the living room. I continued drinking beer while he sipped water. He actually stayed up pretty late, just talking about the old days and some of the things we did when we were kids. It was the first time we had actually sat down and had a conversation like that in a long time. Even before I caused us to be estranged by having sex with his wife, we weren’t really close—not like brothers should be. We were more like strangers bonded together by a common bloodline than family.

  THE WEEK FELT LIKE torture. I couldn’t have Bethany in my arms and it was like a part of me was missing. We had casual glances—sometimes a warm, wet kiss filled with our passion when I could pull her away from the crowd in the hallway—but life was in the way of what we both desired. I couldn’t really bring her to my brother’s house, the moment was never right after school with other teachers hanging around, and she was actually making an effort with class. A few times I watched her in the library, smiling as she got frustrated with an assignment or tried to figure out what she was reading in her textbook. She was like forbidden fruit and while I would have wore our relationship with a badge of honor if I could have, I knew it would have destroyed my brother’s career to even tell anyone about it. Someone knew, though—Mr. Matthews had been silent, but he knew the truth. He was a loose end and I didn’t like it. After several days passed, I was convinced he was going to let it go, even if he did shoot me an angry glare every time I saw him. My mind was too full of Bethany to really delve into the the possibility of what he could do if he decided to tell the wrong person about what he saw.

  “Tonight...” Bethany’s lips lingered against mine in my office.

  “Yes.” I nodded quickly. “I turned in a detention form. It’s Friday night so none of the teachers really want to do it. I told Mrs. Smith I would handle it and she practically did a back flip.”

  “She’s ninety years old...” Bethany grinned and her eyes sparkled as she started to laugh.

  “She’s agile for her age. She was just overcome with joy.” I shrugged and laughed, pulling Bethany close again.

  Her lips were like crimson-coated fire against mine. I would have devoured them and pulled her into my office to feel her naked body against mine in an instant if I could have found a way to make it work. When I heard my secretary walk in, I had to pull away quickly and pretend like I was scolding her. My secretary gave me an understanding nod—thinking Bethany was in trouble again. Bethany left and I spent the afternoon doing paperwork. When I first arrived, my days were filled with a line of students in need of punishment, but the lines had gotten so sparse it was almost boring. I did what I could and passed the rest to the Assistant Principal. The technicalities were a little over my head and the budget might as well have been Greek, but I was getting better with it as the days went by. The day ended and I was anxiously awaiting Bethany’s arrival, but I heard footsteps that were too hard to belong to her. I looked up to see Mr. Matthews entering my office. He didn’t wait for an invitation and I could see by his body language that he was walking with a purpose.

  “Mr. Thorne.” He gave me a nod and took a seat across from me.

  “What I can do for you, Mr. Matthews?” I leaned back in my chair and looked across my desk at him.

  “I’ve been trying to decide how to talk to you about this and while I usually struggle with confrontation like this, I don’t want to spend the weekend going over it in my mind again.” He looked down for a moment.

  “This is about Bethany?” As if on queue, I saw her in the corner of my eye. I quickly shook my head at her and she left the office once she realized Mr. Matthews was there with me.

  “Yes.” He nodded. “I tried to rationalize it in my head. I’ve had a weak mind. I’ve thought about—damn have I’ve thought about it—but you did it. You didn’t just think about it, you didn’t go home and masturbate to the thought—you actually did it.”

  “I did.” My anger started rising as he referenced her in a way I didn’t like, but I bit my tongue since he did control a good portion of my fate.

  “It is just further proof that Grantham University is the work of the devil. These freaking kids, man. They’re devils in tartan skirts—bullies in knee socks. I can’t do it anymore.” He finally lifted his head.

  “You’re quitting?” I raised an eyebrow in surprise.

  “No.” He shook his head quickly. “I need my pension, but I can’t stay here until I retire. I need you to get me out of this nightmare.”

  “What are you suggesting?” I narrowed my eyes at him.

  “I don’t like this school, but it’s a necessity. Hell, it keeps these bastards out of regular schools. I’m glad they’re all in one place—I just don’t want to be trapped in here with them. If you would write me a letter of recommendation, I could find a different school. I would even teach in the ghetto!” There was a hopelessness forming on his face, even as he laid out what he wanted in front of me.

  “I see...” I nodded and sighed.

  “I don’t want to say anything about what you did. I used to respect you; I really did. I felt like you were in hell with us, so you could relate. Since you’ve started turning things around, it feels like there a divide. S
ome of the students respect us and that is a nice change, but you can’t change them all. It just isn’t possible. I need out, Mr. Thorne.” His expression continued to reflect concern as he struggled with his words.

  “So you don’t respect me anymore?” I tilted my head and stared him down.

  “It—it is hard to respect you when you’re having sex with one of the students. Not just any student—the queen of this nightmare.” He took a hurried breath and exhaled sharply.

  “I’m going to level with you, Mr. Matthews.” I didn’t feel like I had much to lose with him. He already knew something much worse than what I was about to tell him. “I’m not Sloane Thorne.”

  “What?” His eyebrows almost touched his hairline. “Of course you are.”

  “No.” I shook my head back and forth. “Grantham University broke Sloane—even worse than you. I’m his twin brother, Anton.”

  “Anton?” He tilted his head in contemplation. “Wait, Anton is in prison.”

  “I was.” I nodded and smiled. “But I’m out now and I saw a chance to do something good with my life. So, while you’re judging me, just remember what kind of man I am. Things have changed because I’m not afraid of these students. I put them in their place and if their parents decide to fuck with me, I put them in their place as well.”