My Stepsister’s Date with an Older Man
September arrived, and the campus was once again bustling with students, including Amy. I had been looking forward to our first meeting, but a part of me was nervous about seeing her after three months of no contact. Amy’s social graces were impeccable, and I had a feeling that things would go smoothly.
Amy arrived at our meeting, and we hugged in greeting. I made sure to keep a safe distance, not wanting my growing arousal to become too apparent. Amy gave me her sly grin as she sat down, but we both maintained a professional demeanor, at least on the surface. We spent a significant amount of time discussing her proposed project, which compared women’s age at first marriage in different countries and the reasons for any differences.
“Speaking of which,” I said casually, “are you keeping up with your commitment to date older men?”
“Kind of,” she replied with a grin. “Last May, I had an amazing experience with an older guy, but the others couldn’t compare. It was one or two dates, and then nothing.”
“Well, that’s a shame,” I said insincerely. “You’re young, smart, and beautiful. Economic research says you’ll do well in your career.”
Amy got up to leave, gathering her books and backpack from the floor. As she bent over to pick something up, her short dress rose tantalizingly, giving me a glimpse of her toned thighs. She turned as she slung her backpack over her shoulder.
“Hey, by the way, nice file cabinet. It adds to the salvage store décor.”
“It used to be fine,” I replied. “I nailed something up against it last spring, and it got bent out of shape.”
Amy burst out laughing, “Good one! You’re so bad.”
“Not what you said last year,” I grinned at her.
“No, it’s not,” she said, returning my smile. It was clear that she was teasing me, and I was more than happy to play along.
With that, Amy walked over to me, put her hand around my waist, and kissed me hard on the lips.
“Try to be a good boy this year too,” she said as she smiled, opened the door, and left.
Amy enrolled in my labor law class for the fall semester, and things quickly returned to their usual routine. She sat in the front row, wearing no underwear, and her legs were spread at a 45-degree angle every moment of every class. She smiled slyly at me each time she caught my eye, and I found myself stumbling over my words when asking her questions.
But it was torture. I had to stop using the chalkboard because every time I turned back to face the class, my eyes fell to Amy’s exposed pussy. I’m sure the rest of the students noticed. I had to grit my teeth and focus on the lesson at hand.
As the semester progressed, Amy and I both began to act more like that amazing experience in my office had never happened. I was a little sad, but not at all surprised. It was a one-time thing, after all.
But Amy had a September surprise in store for me, and I was about to find out just how much she had in store.
Amy poked her head into my office, “Professor, can we talk for a minute?”
“Sure,” I said, still not suspecting anything. “Do you have any questions?”
“No, I just need to calm down. I’m really nervous about the exam. Can you help me?”
“I guess so,” I said, still not catching on. “Come on in.”
Amy walked across the room, closed the door behind her, and stood in front of me. She smiled, and without a word, she began opening my pants.
“Amy, what are you doing?” I stammered, caught off guard once again.
“Relaxing,” she said nonchalantly as my cock sprang from my underwear. “This is how I relax.”
With that, she swallowed my cock down her throat, her lips moving along the shaft, her hand playing with my balls. I was surprised by how good it felt, and I found myself getting lost in the moment.
“Amy, I’m going to cum,” I muttered, not believing how good my cock felt in her mouth.
“Yeth pweez,” she hummed, her mouth still full of my cock. As she felt my body tense, she slid me out of her mouth and continued to stroke my cock furiously.
With a gasp, my cock began to shoot ropes of sticky warm cum across her face. I held her head so she couldn’t dodge my load, but it wasn’t necessary. She took it all in the face, smiling all the while, licking my cum from her lips.
When I was spent, she pulled my underwear into place and pulled up my pants. All with my cum covering her face. While I was buttoning up, she went to my desk and grabbed a tissue, wiping the sticky load from her face and neck.
“That’s better,” she said, giving me a peck on the cheek and leaving my office, still wiping cum from her face.
The exam later that day was a blur to me. Amy sat in the front row, calmly writing her exam, looking up and smiling innocently at me from time to time. Her blouse had several faint stains near the top, and I was sure they were from my splooge.
Once Amy looked up at me and licked her lips lasciviously. I’m sure I blushed. Thankfully, Amy aced the exam, and I didn’t have to face the dilemma of giving her a poor grade.
Amy was a frequent visitor to my office, and I never knew when she stopped by whether it was for academic reasons or carnal ones. My cock stiffened regardless, and more than once, I had to take care of myself, shooting cum across my desk when Amy left me blue-balled.
She would leave with a little wave and a smile on her face, a smile that said “I know you’re going to be jacking off in five minutes.” Sometimes she raised the back of her short skirt as she left, flashing her tight little ass at me, and revealing her lack of underwear as she slid through the door.
Once, I broke my cardinal rule of not making the first move when her relaxation visits became too far between. Amy was sitting across the desk from me, leaning over and showing me the latest results from her senior project. Not accidentally, I think, she wore a loose top and no bra, so I could see her small breasts and erect nipples.
I was paying no attention to what she was saying. I went across the room, closed the door, and without a word, I went to where Amy was sitting, grabbed her by the hair, pulling her out of the chair and onto her knees in front of me.
Rather than being shocked, Amy was smiling up at me.
“Would you like me to suck your cock, sir?” she asked.
I opened my pants, grabbed her hair roughly in one hand, my hard cock in the other, and forced my cock into her mouth and down her throat. I moaned and threw my head back as I reveled in Amy’s incomparable head technique.
I was more aggressive this time, trying to take back control as I held her head in both hands and roughly fucked her face.
Amy seemed to enjoy it all, as she slid my cock out of her mouth to lick and suck my balls. She stroked my wet cock as she looked at me with those blue eyes and said, “I’m going to put your cock down my throat, and you’re going to shoot your load straight down my throat.”
It was an amazing feeling as my cock slithered down her throat, Amy not gagging a bit as she swallowed me whole. I was close, and it didn’t take many strokes in her tight throat before my cock did as she ordered, and emptied my load down her throat.
“That was amazing,” I panted, as I buttoned up and pulled up a chair beside her.
“Thank you, Professor,” she said, “I’ve had a lot of practice.”
“Yeah, I have a question about that Amy,” I said, coming to my senses faster than I would have liked. “Why an old guy like me? Why now? Why not last year? You must have your choice of any number of young studs with large cocks they would love to give you.”
“Oh, you know,” Amy said, “Guys hit on me all the time. And truthfully, sometimes at a club where nobody knows me, I’ve taken a guy into the men’s room and gone down on them. Only two or three times, I guess. But the truth is, if you haven’t figured it out by now, I guess I’m what they call a cumslut.”
“A cumslut?” I repeated, intrigued.
“Yes, a cumslut,” Amy said, “I love making men cum, I love watching them cum, I love wearing their cum, I love eating their cum as often as I can.”
“Amy, I don’t know what a cumslut should look like, but they don’t look like you,” I said, chuckling.
“Thank you, Professor,” she said, “Part of being a really good cumslut is to not look the part. Guys cum harder when they’re surprised. You did.”
“But again,” I pressed, “Why me? Why now?”
Amy just smiled and said, “You’ll have to ask me again sometime, Professor.”
Amy’s eyes sparkled with mischief as she leaned back in her chair, her slender fingers drumming a rhythmic beat on the armrest. “I’m glad you understand the situation, Professor,” she said, her voice husky with desire. “I have to be careful about my reputation, and I need someone I can trust to… take care of me.”
“I see,” I replied, still trying to process the enormity of her admission. “So, you visit me because I’m… safe.”
“Exactly,” Amy nodded, her ponytail bobbing up and down. “You give me what I want, and you’re discreet. I know I can count on you.”
I nodded, feeling a mix of emotions swirling inside me. Part of me was flattered by her trust, but another part was concerned about the power dynamic between us.
“That makes sense,” I said finally. “But what about… cumsluts? Is that something you choose to be, or are you born that way?”
“I don’t know about other girls,” Amy said, her expression thoughtful. “But I think I was born this way. I know it sounds crazy, but I just… crave it.”
“An awful experience?” I asked, my brow furrowing in concern. “What makes you think that?”
“It was my first time,” Amy said, her voice barely above a whisper. “I was 14, and it was… traumatic. But at the same time, it was… exciting.”
“Exciting?” I repeated, my voice incredulous. “Amy, that’s not something to be excited about.”
“I know,” she said, her eyes flashing with defiance. “But I was. And it’s been like that ever since. I just… can’t help myself.”
I sighed, feeling a sense of wonder at her complexity. “Amy, I’m so sorry,” I said finally. “I had no idea.”
“It’s okay, Professor,” she said, her smile softening. “I’m not looking for sympathy. I just want to be honest with you, and I want to be honest with myself.”
“I appreciate that,” I said, feeling a sense of gratitude towards her.
“I’m glad we can talk about this, Professor,” Amy said, her voice filled with a sense of longing. “It means a lot to me.”
“Me too, Amy,” I said, my voice filled with emotion. “Me too.”
Amy leaned forward, her eyes locked on mine. “I want to show you something, Professor,” she said, her voice husky with desire.
“What is it?” I asked, my heart pounding in my chest.
Amy smiled, her lips curling up in a mischievous grin. “Just wait and see,” she said, her voice filled with excitement.
I nodded, feeling a sense of anticipation building inside me. What was she planning? And would I be able to handle it?
Amy stood up, her dress fluttering around her ankles. “I have to go, Professor,” she said, her voice filled with a sense of urgency.
“Okay,” I said, feeling a sense of disappointment wash over me.
“Don’t worry, Professor,” Amy said, her smile softening. “I’ll be back soon. And when I am, we’ll have our graduation celebration.”
“What do you mean?” I asked, my brow furrowing in confusion.
“Just wait and see, Professor,” Amy said, her voice filled with excitement. “It’s going to be… unforgettable.”
I nodded, feeling a sense of trepidation building inside me. What did she have planned? And would I be able to handle it?
Amy turned to leave, but not before giving me a sly smile and a wink. “Don’t worry, Professor,” she said, her voice barely above a whisper. “I’ll take care of you.”
I watched her go, feeling a sense of wonder at her complexity. Was I in over my head? And did I care?
As the days passed, I found myself counting down the hours until graduation. What would Amy have planned? And would I be able to handle it?
The day of the ceremony finally arrived, and I found myself standing in line with the other faculty members. Amy was nowhere to be seen, but I knew she was out there, waiting for me.
As the ceremony began, I scanned the crowd, searching for a glimpse of Amy’s bright smile. And then, suddenly, I saw her.
She was standing in the front row, her graduation gown gleaming in the sunlight. But it was what she was holding in her hand that caught my attention.
It was a large, red rubber butt plug.
Amy grinned at me, her eyes sparkling with mischief. “Time for our graduation celebration, Professor,” she said, her voice husky with desire.
I felt my heart pounding in my chest as I watched her make her way towards me. What did she have planned? And would I be able to handle it?
Amy reached me, her eyes locked on mine. “Let’s get started, Professor,” she said, her voice filled with excitement.
I nodded, feeling a sense of trepidation building inside me. What did she have planned? And would I be able to handle it?
Amy took my hand, her grip firm and confident. “Come on, Professor,” she said, her voice husky with desire. “Let’s make some memories.”
I followed her, my heart pounding in my chest. What did she have planned? And would I be able to handle it?
We made our way to a nearby table, where a large, red velvet cloth was spread out. Amy grinned at me, her eyes sparkling with mischief.
“Time to get started, Professor,” she said, her voice husky with desire.
I nodded, feeling a sense of trepidation building inside me. What did she have planned? And would I be able to handle it?
Amy reached for the butt plug, her hands grasping it firmly. “Time to take care of business, Professor,” she said, her voice filled with excitement.
I felt my heart pounding in my chest as I watched her prepare to insert the plug into me. What did she have planned? And would I be able to handle it?
Amy’s hands moved swiftly and surely, the plug slipping smoothly into me. I felt a sense of surprise mixed with pleasure, as my body adjusted to the new sensation.
Amy grinned at me, her eyes sparkling with mischief. “How’s that, Professor?” she asked, her voice husky with desire.
I nodded, feeling a sense of wonder at her complexity. What had I gotten myself into?
Amy reached for me, her hands grasping my shoulders firmly. “Time to get started, Professor,” she said, her voice filled with excitement.
I felt my heart pounding in my chest as I watched her prepare to take me. What did she have planned? And would I be able to handle it?
Amy’s lips moved down my chest, her tongue tracing a hot path down to my groin. I felt a sense of pleasure mixed with surprise, as my body responded to her touch.
Amy’s hands moved swiftly and surely, her fingers wrapping around my cock. I felt a sense of wonder at her complexity, as she began to stroke me with a confident, practiced touch.
Amy’s eyes locked on mine, her gaze burning with desire. “Time to cum, Professor,” she said, her voice husky with excitement.
I nodded, feeling a sense of pleasure mixed with surprise, as my body responded to her touch. What had I gotten myself into?
Amy’s fingers moved swiftly and surely, her touch sending me soaring into a world of pleasure and desire. I felt a sense of wonder at her complexity, as my body responded to her touch.
Amy’s lips moved up my chest, her tongue tracing a hot path back up to my lips. I felt a sense of pleasure mixed with surprise, as our mouths met in a fierce, passionate kiss.
Amy’s hands moved swiftly and surely, her fingers wrapping around my cock once more. I felt a sense of wonder at her complexity, as she began to stroke me with a confident, practiced touch.
Amy’s eyes locked on mine, her gaze burning with desire. “Time to cum, Professor,” she said, her voice husky with excitement.
I nodded, feeling a sense of pleasure mixed with surprise, as my body responded to her touch. What had I gotten myself into?
Amy’s fingers moved swiftly and surely, her touch sending me soaring into a world of pleasure and desire. I felt a sense of wonder at her complexity, as my body responded to her touch.
Amy’s lips moved up my chest, her tongue tracing a hot path back up to my lips. I felt a sense of pleasure mixed with surprise, as our mouths met in a fierce, passionate kiss.
Amy’s hands moved swiftly and surely, her fingers wrapping around my cock once more. I felt a sense of wonder at her complexity, as she began to stroke me with a confident, practiced touch.
Amy’s eyes locked on mine, her gaze burning with desire. “Time to cum, Professor,” she said, her voice husky with excitement.
I nodded, feeling a sense of pleasure mixed with surprise, as my body responded to her touch. What had I gotten myself into?
Amy’s fingers moved swiftly and surely, her touch sending me soaring into a world of pleasure and desire. I felt a sense of wonder at her complexity, as my body responded to her touch.
Amy’s lips moved up my chest, her tongue tracing a hot path back up to my lips. I felt a sense of pleasure mixed with surprise, as our mouths met in a fierce, passionate kiss.
Amy stepped back, a triumphant smile on her face. “Congratulations, Professor,” she said, her voice husky with desire. “You’ve been cummed.”
I looked at her, feeling a sense of wonder at her complexity. What had I gotten myself into?
Amy grinned at me, her eyes sparkling with mischief. “Time to celebrate, Professor,” she said, her voice filled with excitement.
I nodded, feeling a sense of pleasure mixed with surprise, as my body responded to her touch. What had I gotten myself into?
Amy reached for me, her hands grasping my shoulders firmly. “Let’s go, Professor,” she said, her voice husky with desire.
I followed her, my heart pounding in my chest. What did she have planned? And would I be able to handle it?
We made our way to a nearby table, where a large, red velvet cloth was spread out. Amy grinned at me, her eyes sparkling with mischief.
“Time to get started, Professor,” she said, her voice husky with desire.
I nodded, feeling a sense of wonder at her complexity. What had I gotten myself into?
Amy reached for the butt plug, her hands grasping it firmly. “Time to take care of business, Professor,” she said, her voice filled with excitement.
I felt my heart pounding in my chest as I watched her prepare to insert the plug into me. What did she have planned? And would I be able to handle it?
Amy’s hands moved swiftly and surely, the plug slipping smoothly into me. I felt a sense of surprise mixed with pleasure, as my body adjusted to the new sensation.
Amy grinned at me, her eyes sparkling with mischief. “How’s that, Professor?” she asked, her voice husky with desire.
I nodded, feeling a sense of wonder at her complexity. What had I gotten myself into?
Amy reached for me, her hands grasping my shoulders firmly. “Time to get started, Professor,” she said, her voice filled with excitement.
I felt my heart pounding in my chest as I watched her prepare to take me. What did she have planned? And would I be able to handle it?
Amy’s lips moved down my chest, her tongue tracing a hot path down to my groin. I felt a sense of pleasure mixed with surprise, as my body responded to her touch.
Amy’s hands moved swiftly and surely, her fingers wrapping around my cock. I felt a sense of wonder at her complexity, as she began to stroke me with a confident, practiced touch.
Amy’s eyes locked on mine, her gaze burning with desire. “Time to cum, Professor,” she said, her voice husky with excitement.
I nodded, feeling a sense of pleasure mixed with surprise, as my body responded to her touch. What had I gotten myself into?
Amy’s fingers moved swiftly and surely, her touch sending me soaring into a world of pleasure and desire. I felt a sense of wonder at her complexity, as my body responded to her touch.
Amy’s lips moved up my chest, her tongue tracing a hot path back up to my lips. I felt a sense of pleasure mixed with surprise, as our mouths met in a fierce, passionate kiss.
Amy stepped back, a triumphant smile on her face. “Congratulations, Professor,” she said, her voice husky with desire. “You’ve been cummed.”
I looked at her, feeling a sense of wonder at her complexity. What had I gotten myself into?
Amy grinned at me, her eyes sparkling with mischief. “Time to celebrate, Professor,” she said, her voice filled with excitement.
I nodded, feeling a sense of pleasure mixed with surprise, as my body responded to her touch. What had I gotten myself into?
Amy reached for me, her hands grasping my shoulders firmly. “Let’s go, Professor,” she said, her voice husky with desire.
I followed her, my heart pounding in my chest. What did she have planned? And would I be able to handle it?
We made our way to a nearby table, where a large, red velvet cloth was spread out. Amy grinned at me, her eyes sparkling with mischief.
“Time to get started, Professor,” she said, her voice husky with desire.
I nodded, feeling a sense of wonder at her complexity. What had I gotten myself into?
Amy reached for the butt plug, her hands grasping it firmly. “Time to take care of business, Professor,” she said, her voice filled with excitement.
I felt my heart pounding in my chest as I watched her prepare to insert the plug into me. What did she have planned? And would I be able to handle it?
Amy’s hands moved swiftly and surely, the plug slipping smoothly into me. I felt a sense of surprise mixed with pleasure, as my body adjusted to the new sensation.
Amy grinned at me, her eyes sparkling with mischief. “How’s that, Professor?” she asked, her voice husky with desire.
I nodded, feeling a sense of wonder at her complexity. What had I gotten myself into?
Amy reached for me, her hands grasping my shoulders firmly. “Time to get started, Professor,” she said, her voice filled with excitement.
I felt my heart pounding in my chest as I watched her prepare to take me. What did she have planned? And would I be able to handle it?
Amy’s lips moved down my chest, her tongue tracing a hot path down to my groin. I felt a sense of pleasure mixed with surprise, as my body responded to her touch.
Amy’s hands moved swiftly and surely, her fingers wrapping around my cock. I felt a sense of wonder at her complexity, as she began to stroke me with a confident, practiced touch.
Amy’s eyes locked on mine, her gaze burning with desire. “Time to cum, Professor,” she said, her voice husky with excitement.
I nodded, feeling a sense of pleasure mixed with surprise, as my body responded to her touch. What had I gotten myself into?
Amy’s fingers moved swiftly and surely, her touch sending me soaring into a world of pleasure and desire. I felt a sense of wonder at her complexity, as my body responded to her touch.
Amy’s lips moved up my chest, her tongue tracing a hot path back up to my lips. I felt a sense of pleasure mixed with surprise, as our mouths met in a fierce, passionate kiss.
Amy stepped back, a triumphant smile on her face. “Congratulations, Professor,” she said, her voice husky with desire. “You’ve been cummed.”
I looked at her, feeling a sense of wonder at her complexity. What had I gotten myself into?
Amy grinned at me, her eyes sparkling with mischief. “Time to celebrate, Professor,” she said, her voice filled with excitement.
I nodded, feeling a sense of pleasure mixed with surprise, as my body responded to her touch. What had I gotten myself into?
As Amy walked into my office, I couldn’t help but notice the confident stride she had. Her eyes sparkled with mischief, and I knew I was in for a treat.
“I’m glad I caught you before the ceremony,” Amy said, her voice husky with excitement. “I want you to meet my family.” She drew me close in a friendly hug, her body pressed against mine. “I’m naked under this robe,” she whispered in my ear, her breath sending shivers down my spine.
I tried to play it cool, but my mind was racing. I had experienced this before, but it never got old. I smiled and hugged her back, pretending to be oblivious to the fact that she was completely naked beneath her robe.
Amy’s parents, John and Jeanette, arrived soon after, and we exchanged pleasantries. Amy’s sister, Emily, was also with them, and I couldn’t help but notice the way they all seemed to be sizing me up.
As we chatted, I couldn’t help but think about Amy’s words. “I’m naked under this robe,” she had said. I wondered what other surprises she had in store for me.
After what felt like an eternity, the ceremony finally came to an end. I dragged myself back to my office, exhausted and sweaty. Amy texted me, saying she would be another hour, attending the awards luncheon with her family.
I decided to take matters into my own hands. I pulled out my aching cock and began to stroke it, thinking about Amy and all the things we would do together. I knew I couldn’t wait much longer.
Amy showed up soon after, still wearing her academic cap and gown. She looked stunning, and I couldn’t help but feel a surge of excitement. “I’m going to be clean before we get dirty,” she said, leading me to the shower.
As we showered together, the water cascading down our bodies, I couldn’t help but think about all the things I wanted to do to her. And to her sister, Emily.
Amy grabbed my arm, pulling me towards the stairs. “Sit down on the top step,” she said, her eyes sparkling with mischief. I did as she instructed, and she climbed up beside me, her legs spread wide.
I knelt down, my eyes fixed on her wet pussy. I inserted a finger, feeling her warmth and wetness. My tongue probed between her lips, searching for her clit.
Amy gasped, her body trembling with pleasure. I thrashed her clit with my tongue, feeling her body respond to my touch. She came hard, her body shaking and twitching like she was on fire.
As she sat up, her face was a mask of determination. She grabbed my waistband, pulling my pants down to my ankles. My stiff, bobbing cock sprang free, and Amy attacked it with a series of slaps, hard and fast.
I cried out, my body responding to her touch. She squeezed my balls, holding them in her teeth as she sucked on my cock. I felt like I was going to cum, but it was like my body was frozen, unable to release the tension.
Amy’s finger snaked into my asshole, playing with my prostate. I felt like I was having a massive orgasm, but my cock wasn’t pulsing, and no sperm was shooting out. It was amazing, feeling like I was cumming hard, but I wasn’t.
“Don’t talk, don’t ask questions,” Amy said, her voice husky with excitement. “I’ll take your load when I’m ready. And it will be a big one.” She licked her finger clean, her eyes locked on mine.
I felt my cock pulse, but nothing came out. Amy smiled, her eyes sparkling with mischief. “It’s okay,” she said. “I’ll take care of it.”
As I gazed at Amy’s expectant face, I felt a surge of anticipation course through my veins. Her eyes sparkled with a mischievous glint, and I knew I was in for a wild ride.
“Fuck me, Professor,” she whispered, her voice husky and seductive.
I positioned the head of my cock inside her wet lips and pushed, feeling the warmth of her pussy envelop me. I loved watching my cock enter a tight pussy, and Amy’s was the best I’d ever had.
“See?” Amy said through her legs, still holding her ankles. “I told you you wouldn’t cum. But it sure feels like it, doesn’t it?”
I slammed my cock into her pussy a couple times to test the theory, and I have to admit, it felt incredible. But I was determined to hold back.
Amy took her pussy off of my cock and stood. “I’ve got to take that shower. We have a long night ahead of us. Could you get my bag downstairs? I forgot to bring it up.”
I pulled my scrubs up and tied them, still sporting a pole protruding from the front. I heard Amy start the shower and grabbed the bag, not looking inside. Big mistake.
Amy took the bag and closed the bathroom door. So much for showering with Amy, I moped. I went and got another drink.
I sat and quietly drank my whiskey while idly playing with the head of my cock through my pants. I stirred from my reverie when I realized that the shower had stopped, but I hadn’t heard Amy call or anything.
I heard a sound from upstairs, faintly at first, then stronger. I couldn’t place the sound at first—sort of a repeated sound, not rhythmic. Like something being slapped.
I tried to find the source of the sound on the first floor, but it was clearly coming from upstairs. I mounted the stairs, looked in the bathroom and the extra bedrooms. The only place left was my bedroom.
I pushed the door open cautiously, I didn’t know what to expect. The room was empty, but the mahogany French doors to the porch were closed. I had left them open.
The sound was coming from there. It had to be Amy, she hadn’t left and she wasn’t anywhere else. I went over and flung open the doors.
“There you are, I couldn’t figure…”
“Quiet! Speak only when spoken to!”
I was completely and totally stunned. Backlit by the setting sun was Amy, standing legs apart. Black thigh-high stockings, a leather bikers cap, slapping a riding crop against her hand and—wearing a big black strap-on.
“Amy, what the he…”
“I said quiet!” she snapped, smacking the crop against my arm. The crop left a large red welt on my arm. It hurt.
She moved the mound in my pants with the end of the crop. “Pants!” Not wanting another welt, and frankly getting into Amy’s German Barbie character, I quickly dropped my pants and kicked them aside.
My cock remained at attention. Amy walked towards me, grabbed my cock and pulled. “Hmmmph…” she said. Suddenly she raised the crop over her head and brought it down full force on the head of my cock. I was about to cry out, but Amy looked sternly at me and placed the crop threateningly against my cheek.
The head of my cock stung badly. But I was finding myself liking it. “Against the wall!” Amy pointed with the crop to the wall at the end of the patio.
“Hands against the wall! Legs apart!” Amy used the crop to spread my legs farther apart. She grabbed my sack and squeezed.
“So we do not misunderstand each other…these are mine. Do you understand?” I nodded. “I will do what I want with them and you will not object, yes?” I nodded again.
“Why did you come here tonight? You may speak.” I hesitated for a moment before answering.
“I live here.”
“Such frivolity will not be tolerated! If you live here, why are you naked against the wall of your own house?”
“I like being naked?” Thwack! Thwacck! “Ok, ok. The hottest woman I have ever known was supposed to come over and let me drill her pussy and ass.”
She reached between my legs and grabbed my dick. All of the swats with the crop were definitely putting a dent in my lust. “This little thing?” she asked, wagging my semi hard cock with her hand. “No woman will feel such a small member. Not even in their anus.”
“I haven’t had complaints.”
Thwwack! This was getting old. “Bend over the railing. Now!” I expected a thorough spanking with that damned crop.
I was thinking of ways to get that crop away from her and turn the tables. But she didn’t spank me. She got on her knees, spread my ass and began to rim my asshole. Damn. Amy’s tongue talents extended to eating ass.
I love this girl…Once her tongue was established on my anus, she reached between my legs and began stroking my engorged member.
“Amy, don’t. You’re going to make me cum. I don’t want to.”
“Silence, fool! Your ejaculation will come when I want it. Now spread your ass!”
I obeyed, and I felt the cold tip of the strap-on pushing up against my asshole. Amy pushed, nothing budged. She pushed harder. Still nothing.
Amy stopped and pushed two fingers in my ass to loosen my anal sphincter and give her access to my rectum. Now she pushed with the strap-on and my asshole began to give way.
The strap-on wasn’t that thick but felt huge in my bum. Amy kept pushing. I was grunting and trying to breath deeply to relieve the pressure. Didn’t help.
“You came here tonight to put your tiny cock in my ass, yes or no?”
“Yes”
“You thought I would let you in my asshole for free, didn’t you? You didn’t think I would be giving it to you in the ass, did you?”
“Yes. And no.” Finally the strap on was all the way in, as I could feel Amy’s warm thigh against my bum.
She started sliding in and out of my ass. I helped by moving my hips against her thrusts.
“You like it in the ass, don’t you? Tell the truth!” I had to admit, once she got all the way inside, I liked it.
The shaft was designed to curve and worked my prostate. It felt good. It felt better when she pushed it all the way in, leaned around and stroked my cock with her hand.
“That’s what you came here to do to me, no?”
“Yes. And I’m going to.”
“Perhaps,” Amy said, as she jammed her plastic dick inside me with violence. “But, tiny though it is, your cock is bigger than mine.”
She slid lowly out of my ass. “I have a bigger one. I am going to get it.” That’s it, I thought.
As she turned to go, I saw my chance. I grabbed one wrist and spun Amy around and roughly grabbed the other. Arms above her head, I pushed her against the wall and kissed her roughly.
Rather than protesting, Amy was smiling. An excited smile of someone who is getting exactly what she wants.
As I held her arms above her head, Amy raised her feet off the floor and wrapped them around my waist. I probed with my cock until I found her hole and I jammed my cock deep inside her, with vigor.
Truthfully, I kind of lost it. I was slamming my cock into Amy’s pussy as hard as I can. I am grunting, panting sweating as I am fucking Amy harder and faster than I have ever fucked anyone.
Amy is smiling and talking smack quietly during my frantic, hard fucking.
“Hey, Professor, did I hurt your big boy feelings when I spanked your little dick?”
I have Amy pinned, arms over her head, pretty much holding up her ass with my cock, and Amy is now glaring at me defiantly.
“I am fucking you as hard as I can still isn’t going to make your pencil dick get any bigger. Keep going bucko, I’ll tell you when I feel something.”
It’s crazy. I’ve never wanted to hurt someone with my dick. I know Amy is just talking shit, but it is making me wild.
The harder I fuck her, the calmer her voice gets. Driving me nuts.
“I let go of Amy’s arms and grab her ass. I carry her over to the stone railing and set her ass on the cold stone.
My cock never left her pussy. I put my arms around her hips and flexible Amy puts her black stockinged legs on my shoulders.
For the first time I notice her stockings are real silk. Really hot. But, it is a precarious position. If my hands slip, Amy tumbles the 15 feet or so into the garden below.
Even more precarious, Amy throws her head back, moans, and her leather cap falls into the garden. Soon she is back, looking right into my face, talking calmly.
“I know what it is Professor! You’ve never been fucked in the ass, have you? You took my dildo like a champ. You liked it, didn’t you?”
This girl is really getting to me, and I don’t know why. I am grunting and roaring and trying to fuck her harder still, to no avail.
We both shift our grips to clasp our hands behind each other’s necks, making it easier to hold on. That brings Amy’s calm, expressionless face within inches of my sweating, grunting, puffing face.
Amy’s hips absorb each thrust of my dick. To look at her face, you wouldn’t even know she was being fucked. Still driving me nuts.
“That’s why you’re trying so hard! You liked it in the ass! You’re fucking me dreaming of some guy doing you in the bum, aren’t you? You’re afraid you’re actually gay, huh?”
That’s it. I shrug Amy’s legs off my shoulders onto the ground and stand her up. I grab her hair roughly.
“Turn around! Bend over! Do it!” Amy obeys. But she’s smiling. She is making me do exactly what she wants.
Still holding a handful of her hair, I retrieve the riding crop from where it had been dropped. And I go nuts. Thwwaak! I spank her ass hard with the crop.
Amy flinches, but keeps smiling at me. Thwwaak again! Amy now sports two bright red welts on her ass. Still smiling.
“Is that the best you can do? No wonder you like it in the bum! Can’t even spank a girl’s ass!” You’re such a little bitch.
I thought you were a man. I spank her three or four more times with the crop before throwing it over the rail in frustration. Amy is still smiling at me, even though her ass must be aching.
Next I start spanking her ass with my bare hand. Much more satisfying to see my red handprints adorning her pert little ass.
“That’s it bitch! Spank my ass, make me pay!” Amy is clearly loving every minute of this, the satisfied smile never left her face.
Soon her ass is completely red from the crop and my palm. I get behind her, grab her hair and push her head down.
I push her legs with my foot to spread her legs a bit wider. Amy rises on her tip toes, showing me her wet cunt and pink ass. My cock is about as hard as it has ever been.
Pulling her hair with one hand, and guiding my cock with the other, I push deep into her pussy; her tight, wet pussy.
“Ohhhh!” we say, almost in unison. That stroke was almost electric. I slam my cock inside her a few more times.
But that is not what I am here for. I slide my cock out of her cunt, nice and wet and glistening.
I place the tip of my dick against her asshole. Amy draws a breath sharply in anticipation. I push. Hard. No going slow to stretch her hole, no giving her time to relax or gape.
In less than a second, I am balls deep in her ass.
“Awwww! Damn it!” Amy shows her first sign of pain or discomfort.
“Shut up, you little bitch!” I surprise myself. I don’t talk like that during sex, even when talking smack. This time I meant it.
I slid my cock halfway out and slammed it back in. Hard.
“Hey! That hurts!” I thrust into her rectum again.
“I know. Get used to it!” Another thrust. Amy pulls her hair free of my grip and looks back at me. She is smiling again.
Her hand slips between her legs to play with her clit.
I grab her hair again and resume fucking Amy’s cute little ass. She is moving her ass with me as her sphincter begins to relax. Beads of sweat appear on her forehead.
Amy’s body convulses, wracked by a powerful orgasm. Her sphincter tightens around me, milking every last drop of pleasure from the moment. I feel a surge of desire, my cock yearning to deliver her another explosive climax.
I pull her hair hard, tilting her head back and arching her spine. I withdraw, then thrust back into her rectum with a primal growl.
“Do that!” she cries, her voice husky with need.
“Come on, Amy, give it to me!” I whisper, my words a sensual command as I drive deeper into her.
Amy’s body shudders, convulsing around me as she reaches another impossible orgasm. I feel my own climax building, my cock straining to release its pent-up passion.
“Ahhhhh, Jesus, fuck, yes!” I roar, my body exploding into a frenzy of pleasure as I spurt my semen deep into her ass.
Amy’s cries merge with mine, our voices a wild, animalistic chant as we surrender to the raw, unbridled passion driving us.
As my final thrust fades, I freeze, my cock buried deep within her, my heart pounding with exertion. I feel Amy’s body relax, her muscles releasing their grip on me as she gasps for air.
Slowly, our legs collapse beneath us, our spent bodies crumpling to the cold stone patio. We lie there, panting, our chests heaving with exertion, as the world around us dissolves into a haze of sweat and desire.
“What the hell just happened?” I ask, my voice barely above a whisper.
“Hahaha, that worked better than I planned!” Amy laughs, her eyes sparkling with mischief.
“What do you mean?” I ask, confusion etched on my face.
“I promised you an assfuck, but I wanted to push you to drop all your inhibitions and lose control. I was hoping to get you to let go and just fuck me like an animal.” Amy’s grin grows wider as she speaks.
“And did it work?” I ask, my voice laced with awe.
“God, yes! You were incredible. What made you think of the Annie Lennox thing?” I ask, my mind still reeling from the intensity of our encounter.
“I saw the music video in a bar and I knew it would work. I wanted to tap into that raw, primal energy and unleash it on you. And I think I succeeded, didn’t I?” Amy’s laughter grows louder, her eyes shining with triumph.
When we finally calm down, we peel ourselves off the patio and head inside to shower. We clean each other thoroughly, our hands gentle as we soothe each other’s raw skin. I watch, mesmerized, as the water washes away the remnants of our passion, leaving behind a trail of cum and sweat.
After our shower, we climb into bed, our bodies still humming with the aftershocks of our encounter. I grab an ice bag and gently place it on Amy’s welted bum, my touch soft as I try to soothe her tender skin.
As I lie beside her, I feel a pang of guilt, but it’s quickly overshadowed by my desire for her. I know I’ll do it all again, given the chance, and I wonder what other secrets Amy has in store for me.