I’m a pretty tall girl, about 5’10", so I stand out a bit. I’ve got a curvy body (I think) and modest-sized breasts. I don’t have a model’s figure, but I play a little amateur volleyball in our neighborhood, so I’ve got a bit of an athletic build, maybe? Anyway, the point is that I think I’m good-looking, at least. I just can’t figure out why no one was interested in me back then. I’m not lacking in confidence, but I also didn’t want to come off as desperate to others.

Toward the end of that year, I came up with a plan: find a guy who, like me, wasn’t getting much action and manipulate him into sleeping with me. Sounds a bit like a villain move, right?

So, I started looking around and decided I should aim for someone older since all the guys my age already had relationships. Plus, I didn’t want it getting around at school that I was being promiscuous. I also had a bit of a thing for older men at the time—something about the idea of an older man fantasizing about me was such a turn-on, hehe.

And, there was already one guy in mind. The campus security.

The plan was simple, but the execution felt like it was slipping through my fingers.

I had been eyeing him for weeks, ever since that first night when he had caught me sneaking back into the dorm after curfew. His stern look had melted into a smile as he recognized me, and we exchanged small talk about classes and campus life. He was older, maybe in his mid-thirties, with a rugged charm that made my stomach flip. Tall, broad-shouldered, and always dressed in that crisp uniform, he was the epitome of authority and control. And tonight, I was going to make all that control unravel.

I pulled my phone out again, scrolling through the messages I had sent him over the past few days. Teasing, suggestive, each one more daring than the last. I wanted to push him, to see how far I could go before he finally snapped. And now, here I was, standing in the dimly lit corridor, waiting for him to respond to my latest text.

“Meet me at the old library entrance. There’s something I need to show you.”

My thumb hovered over the send button. I took a deep breath, my nerves tingling with anticipation, and pressed it. The message sent with a satisfying ding, and I slipped my phone back into my pocket, my eyes darting towards the security camera again. Would he come? Would he even read it in time?

The minutes ticked by like hours. I shifted from foot to foot, the cold floor seeping through my sneakers. Just when I thought he might not show, I heard the soft click of footsteps echoing down the hall. My breath caught in my throat as he rounded the corner, his tall frame silhouetted by the fluorescent lights.

“What are you doing out here so late?” His voice was low, authoritative, but there was a hint of curiosity in his tone.

“Couldn’t sleep,” I replied, my voice barely above a whisper. “Thought I’d take a walk.”

He narrowed his eyes at me, his gaze sweeping over my form. I could feel the heat of his scrutiny, and it only spurred me on. I stepped closer, my lips curling into a coy smile.

“Is everything alright, Mr. Thompson?” I asked, my voice dripping with innocence.

He crossed his arms over his broad chest, muscles straining against the fabric of his shirt. “You know the rules, Annabelle. No wandering around after hours without a good reason.”

“Oh, I have a very good reason,” I said, my eyes locking onto his. “But it’s a secret.”

His brow furrowed, but there was a flicker of interest in his gaze. I could see the wheels turning in his mind, the struggle between duty and desire. I knew he wouldn’t be able to resist me for long.

“A secret, huh?” he repeated, taking a step closer. “Care to share?”

I shook my head, my hair brushing against my cheeks. “Only if you promise not to tell anyone.”

He didn’t move, but his posture softened slightly. “Alright, Annabelle. What is it?”

I bit my lip, hesitating for just a moment before reaching out and placing a hand on his arm. His muscles tensed under my touch, and I could feel the heat radiating from him. “Follow me,” I whispered, pulling him towards the old library entrance.

He allowed himself to be led, his hand resting lightly on the small of my back. The air between us was thick with unspoken tension, and I could feel the weight of his gaze on me as we walked. When we reached the entrance, I turned to face him, my back pressed against the heavy wooden door.

“What’s inside?” he asked, his voice low and rough.

“Just a little spot I found,” I replied, my eyes never leaving his. “No cameras, no interruptions. Just us.”

His breath hitched, and I saw the struggle in his eyes. Duty fought with desire, and I could see the war raging within him. I reached up, my fingers brushing against his cheek, feeling the stubble beneath my touch.

“Please,” I breathed, my voice trembling with need. “I need you.”

For a moment, he hesitated, his eyes searching mine. Then, with a growl, he closed the distance between us, his lips crashing down on mine. The kiss was fierce, urgent, and I moaned into his mouth, my hands clutching at his shoulders. He pulled me closer, his body pressing against mine, and I could feel the hardness of his erection through his uniform pants.

His hands roamed over my back, sliding under my shirt to caress the bare skin underneath. I arched into his touch, my body responding eagerly to his ministrations. He broke the kiss, his breath coming in ragged gasps as he looked down at me, his eyes dark with lust.

“Are you sure about this, Annabelle?” he asked, his voice gruff.

I nodded, my heart pounding in my chest. “Yes. Please, don’t stop.”

Without another word, he lifted me, pinning me against the door as he kissed me again, his tongue delving into my mouth. I wrapped my legs around his waist, grinding myself against him, my core throbbing with need. He groaned against my lips, his hands gripping my ass tightly as he ground his hips against mine.

“God, you’re so fucking tight,” he muttered, pulling away to nip at my neck. “I want to feel you around me.”

I whimpered at the sensation, my hands fisting in his hair as he continued to trail kisses down my throat. He paused at the hollow of my collarbone, his teeth nipping gently before he spoke again.

“Tell me what you want, Annabelle.”

I gasped, my body shivering at the intensity of his words. “I want… I want you inside me,” I confessed, my voice breaking. “Please, I need you.”

He growled, a sound of pure possession, and set me down gently on my feet. His hands moved quickly, unbuttoning his pants and freeing his hard cock. I watched in awe as he stroked himself, his eyes never leaving mine.

“Spread your legs,” he ordered, his voice commanding.

I obeyed, my thighs trembling as I widened them. He knelt before me, his hands gripping my hips as he placed a gentle kiss on the inside of my thigh. My breath caught in my throat as he began to work his way up, his lips and tongue teasing every inch of exposed skin.

When he reached my core, he paused, looking up at me with smoldering eyes. “Tell me how wet you are for me,” he demanded, his voice hoarse.

“So wet,” I admitted, my cheeks flushing with embarrassment. “For you.”

With a wicked grin, he leaned in, his tongue flicking out to taste me. I cried out at the sensation, my hands clenching in his hair as he began to lick and suck at my sensitive flesh. His technique was masterful, driving me wild with pleasure until I was bucking against his mouth, begging him for more.

“Please,” I gasped, my body trembling with need. “I can’t take it anymore.”

He pulled away, rising to his full height as he guided his cock to my entrance. I could feel the tip nudging against my tight folds, and I whimpered, my body quivering with anticipation.

“Relax,” he murmured, his voice soothing. “Let me in.”

I nodded, my eyes fluttering shut as I tried to calm my racing heart. Slowly, he pressed forward, his cock stretching me wide as he entered me. Pain mingled with pleasure, and I bit my lip to stifle a scream as he filled me completely.

“Fuck, you’re so tight,” he groaned, his forehead resting against mine. “So goddamn tight.”

I clung to him, my nails digging into his back as I adjusted to his size. When the initial sting passed, I began to move, lifting my hips to meet his thrusts. He groaned, his hands gripping my ass as he started to fuck me with slow, deliberate strokes.

“That’s it,” he encouraged, his voice rough with need. “Move with me, baby.”

I did as he commanded, my body moving in sync with his as he began to pick up the pace. Each thrust drove me closer to the edge, and I could feel the pressure building inside me. He gripped my hips tighter, his thrusts becoming more forceful as he pounded into me.

“Harder,” I begged, my voice breathless. “Please, harder.”

He complied, his movements growing more frantic as he fucked me with abandon. I cried out, my body arching off the door as I felt the first waves of orgasm crash over me. My inner walls clenched around him, milking him for every drop of pleasure.

“Fuck, I’m coming,” he snarled, his thrusts jerking as he spilled inside me. His cock pulsed with each spurt, filling me with his warmth. I cried out, my body spasming as I rode out the aftershocks of my own orgasm.

The heat of his body pressed against mine, and I could feel the sticky warmth of his semen filling me up. Mr. Thompson held me close, his breath hot against my ear as he whispered words of encouragement and praise. I was still riding the high of my first orgasm, but a new hunger was already stirring inside me.

“Mr. Thompson,” I panted, looking up at him with pleading eyes. “I want more… I want you to fuck my ass.”

He looked down at me, a mixture of surprise and desire flickering in his gaze. “Are you sure, Annabelle? That’s going to be intense.”

“I know,” I said, my voice steady despite the butterflies in my stomach. “But I trust you. I want to experience everything with you.”

He nodded slowly, a look of admiration softening his features. “Alright, sweetheart. We’ll take it slow, okay?”

He gently disengaged from me, and I let out a small whimper of disappointment, but he quickly moved to retrieve something from his pocket. When he returned, I saw that he had a small bottle of lube. He knelt down in front of me, opening the bottle and squeezing some of the clear liquid onto his fingers.

“Lean back,” he instructed softly, and I obeyed, propping myself up on my elbows. He spread my legs wider, and I felt his lubed fingers trace between them, circling my clit briefly before moving downward. I shivered as his fingers reached my entrance, and he carefully inserted one finger, then two, sliding them in and out to prepare me.

“You’re so tight,” he murmured, his voice thick with desire. “I don’t want to hurt you.”

“I know,” I replied, biting my lip. “Just go slow.”

He worked his fingers in and out of me for several minutes, each thrust bringing a new wave of pleasure and anticipation. Finally, he withdrew his fingers and positioned himself behind me. I felt another bead of lube drip onto my asshole, and he began to massage it in, his touch both gentle and firm.

“Relax,” he whispered, his breath hot against my skin. “Take deep breaths.”

I did as he said, trying to calm my racing heart and tense muscles. His finger pressed against my tight hole, and I clenched involuntarily. But he was patient, massaging the area and waiting until I relaxed enough for him to slowly insert one finger.

The sensation was strange, almost painful at first, but as he worked his finger deeper, I began to feel a dull, throbbing pressure that was quickly becoming pleasurable. He added a second finger, stretching me further, and I bit my lip to stifle a moan.

“Good girl,” he praised, his fingers slipping in and out of me rhythmically. “So good, Annabelle.”

His words fueled my arousal even more, and I pushed back against his hand, eager for more. He seemed to sense my growing need, and he withdrew his fingers, replacing them with the head of his cock. The tip pressed against my asshole, and I braced myself for the intensity.

“Ready?” he asked, his voice strained.

“Yes,” I breathed, gripping the edges of the library door for support.

With a slow, deliberate motion, he began to push into me. The sensation was overwhelming—pain mixed with pleasure—and I gasped at the intrusion. He paused when half of his length was inside, giving me time to adjust. The burn was sharp, but there was also an undeniable thrill in the violation of losing my anal virginity to this man.

“Let me know if you need me to stop,” he said, his voice tight with restraint.

“Don’t stop,” I whispered fiercely, pushing back to meet him. “Please, don’t stop.”

Encouraged by my response, he continued to push forward, inch by agonizing inch until he was fully seated inside me. I could feel every ridge and vein of his erection, and the fullness was almost too much to bear. But the ache was intoxicating, making me crave more.

“Move,” I urged, my voice trembling. “Fuck my ass, Mr. Thompson.”

He hesitated for only a moment before pulling back and thrusting back in, his pace slow but building. Each movement sent sparks of pleasure shooting through me, and I cried out, my nails digging into the wood of the library door.

“Oh God,” I moaned, feeling myself stretch around him. “It feels so good.”

He grunted in response, his thrusts gaining speed and strength. The friction between us grew more intense, and I could feel my climax building once again. My pussy clenched around the empty space where his cock had been moments before, and I knew I needed more stimulation to reach that peak.

“Finger me,” I begged, my voice breaking. “Please, I need to come again.”

Without missing a beat, he withdrew his cock from my ass and moved to kneel between my legs. He squeezed more lube onto his fingers and slipped one inside my dripping pussy, his other hand still teasing my clit.

The dual sensations were electrifying, and I felt my body start to tremble with the force of my impending orgasm. Mr. Thompson sensed it too, his thrusts growing more urgent as he sought to push me over the edge.

“Come for me, Annabelle,” he growled, his free hand cupping my breast and pinching my nipple. “Show me how much you love this.”