The Midnight Favor
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B. Anonymous
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Chapter 1
June had just begun, and the college semester had wrapped up for the summer. I swung by to pick up my girlfriend, Amy, who was wrapping up her freshman year at university. We were headed on a three-hour drive to her parents’ house, nestled in the outskirts of Scranton, PA.
Amy was a fit, five-foot-eight softball player who always gave her all, whether it was on the field or in her studies.
As I pulled up to her dorm, I could see the exhaustion etched on her face. It was a clear sign that she’d be snoozing for most of the journey.
And I was right.
Amy and I had been high school sweethearts. She’d always been a go-getter, but since starting college, the pressure had started to strain our relationship.
Juggling school, work, and sports had put a bit of a strain on us.
Our intimacy had also taken a hit. We weren’t as close as we used to be back in high school. The few times we did get intimate, she didn’t seem as into it.
Don’t get me wrong, I still loved her. But I was hoping this summer break would help us reconnect and reignite the spark we had when we first fell in love.
After a long drive, we pulled up to her parents’ two-story brick ranch house. Amy stirred from her nap, and we grabbed our bags and headed to the front door to greet her parents.
Her folks were in their late fifties and had celebrated their thirtieth anniversary the previous year. They were the quintessential parents, living in the past.
They’d been married for three decades, but it was an open secret that they weren’t happy. They were staying together for the sake of their kids.
Their eldest was Amy, my girlfriend of three years, who I loved dearly.
Then there was their other daughter…Sydney.
Sydney had just graduated from high school. She was a year younger than Amy, but they were as different as night and day.
Amy was outgoing and athletic, with a toned body from six years of sports. Her dirty blonde hair, perky B-cup breasts, flat stomach, and tight ass were head-turners.
Sydney, on the other hand, was into digital art, fan fiction, and indie music. She was more introverted. Even though we went to the same school, she hung out with a different crowd.
Sydney was much shorter than Amy, standing at five feet one, with a curvier figure.
She had a cute face, a bit of a tummy, and an ass that was slightly bigger than average for her size. Her breasts, however, were…huge.
I did my best not to get distracted, especially since she was my girlfriend’s sister. But it was hard not to sneak a glance at her size 30H breasts every now and then.
I only knew her size because I’d overheard her talking about the difficulty of finding bras and shirts that fit.
After exchanging hugs with Amy’s parents, we headed inside.
“Hey guys!” Sydney called from across the living room.
She had a big grin on her face as she hurried over to us. She hugged Amy first—they were as close as sisters could be—then she turned to me.
“Great to see you too!” she said, hugging me.
I tried to give her a side-hug, trying not to make it obvious that her short, curvy figure was a turn-on for me. “You too!” I replied. “How have you been?”
“Not much, just graduated and getting ready for community college in the fall,” Sydney said. “I bet you two are glad to be on break.”
After some more small talk, Amy and I headed upstairs to unpack and relax. We chatted about all the fun things we could do over the summer, but I could tell Amy was already thinking about the next school year.
We eventually came down for dinner and chatted with her family. Amy and Sydney were best friends, so most of the conversation was familiar territory for them.
After dinner, Amy’s parents retreated to their master bedroom for their nightly Netflix binge until they fell asleep. It was a routine occurrence, especially since their relationship had lost its spark years ago.
Sydney also headed to her room for the night. After we’d cleared the dishes, Amy and I headed to our room too.
Once we were settled in, I started massaging Amy’s shoulders and upper back.
“Mmmmm, that feels really good,” she said, leaning back and tilting her head back.
“I’m glad,” I replied, kissing her forehead and slowly working my way down her back.
After a few minutes of massaging her back, she picked up her phone and started scrolling through Facebook. I kept massaging her, working my way down her legs and then her feet.
After a few minutes of foot rubs, I traced my fingers up her legs, over her thighs, and up to her hips. Then, I gently touched her chin.
I turned her face towards me and kissed her passionately. She smiled and went back to her Facebook feed.
I stroked her arms and asked if she was in the mood for some fun.
“I have a headache,” she said. “And I’m still tired from the drive.”
I won’t lie, I was a bit annoyed. She used this excuse a lot. I understood we couldn’t have sex every time I wanted, but it had been three months since we’d last made love.
And she’d slept the entire drive. If anyone should be tired, it was me.
“Okay,” I replied, trying to hide my disappointment. I didn’t want to start a fight or add to the tension.
I picked up my phone to kill some time.
A few hours later, Amy was fast asleep.
I was having trouble sleeping, so I decided to step outside for some fresh air. But just as I was about to open the door, I heard a soft knock from the other side.
I waited a few seconds, then opened the door.
It was Sydney…wearing nothing but her underwear and a tight t-shirt that barely contained her large breasts.
“Hey, sorry… I was trying to get a hold of Amy,” Sydney whispered.
“She fell asleep a couple of hours ago,” I replied, doing my best not to stare at her chest.
“Oh, okay…um…could you help me with something?” she asked.
“What do you need?” I replied.
Sydney motioned for me to follow her, and I did.
She led me to her bedroom, and I paused at the door, thinking she was about to show me something.
“You can come in, silly,” she said, her voice light and teasing.
I stepped into her softly lit room, and she asked me to close the door quietly so we wouldn’t wake anyone. I did as she asked, shutting the door with care.
She reached under her bed and pulled out a shoebox.
“Did you get new shoes?” I asked, trying to lighten the mood.
As she opened the box, my eyes widened at the sight.
“No, something even better,” Sydney replied, a mischievous glint in her eyes.
She sat on her bed and began to rummage through the shoebox. Inside were several bags of weed, some edibles, and about four or five pill bottles with the labels worn off. She took a small bite of an edible and offered me a piece.
“Not tonight, but thank you,” I declined politely.
“You’re just as fun as my sister,” Sydney joked, taking another bite of the edible.
I chuckled, and as I sat down on her bed, I asked her where she got all of this.
“I have good connections,” she said simply. “You seem stressed. Here, try this.” She broke off a piece of another edible and leaned toward me to offer it.
I hesitated, but as she leaned in, her shirt slipped down a bit, revealing more of her cleavage. Distracted, I gave in and let her feed me the edible.
“Hey, that’s not bad!” I said, surprised.
“I’m glad!” Sydney responded cheerfully. “I made these myself.”
She put the bag of edibles back into the box and picked up a pill bottle with the label peeled off.
“What’s that?” I asked, curious.
“Having trouble sleeping?” she responded, handing me two pills.
I smirked and accepted them. She handed me a glass of grapefruit juice to wash them down.
I thanked her as she put the pill bottle back into the shoebox and slid it under her bed.
“Do your parents know about this?” I asked.
“No, it’s our little secret,” she said. “Speaking of secrets, you have some yourself, don’t you?” Sydney asked, her tone teasing.
“None that I know of. Why do you ask?” I responded, playing along.
“Oh, don’t play coy with me, handsome,” she said, her voice dropping a notch. As she spoke, she leaned over and placed her hand on my thigh.
“I…uhh… What are you doing?” I asked, my voice shaky as I shifted slightly away from her.
I was nervous, but I also felt a strange sense of guilt for not moving completely away from her. Part of me wanted to, but another part didn’t.
“What does it look like I’m doing?” she asked, her voice low and seductive as she ran her fingers up my thigh. “I’ve noticed you looking at my chest before. They’re pretty impressive, aren’t they?”
I was silent, my eyes darting around the room, but there was no denying it.
“Is my selfish sister neglecting your needs?” she asked, her voice dripping with seduction.
“Huh…hu…how did…” I stammered.
“Oh, I know,” she interrupted. “We tell each other everything. It’s a shame she’s been so preoccupied that she hasn’t been taking care of you.”
I started to feel dizzy. My heart was racing and, to add to my discomfort, I was getting hard…really hard. “What, what did you give me?” I asked, my voice shaky.
Sydney smiled and said calmly, “As I said before, I made you an edible.”
“No, the pills,” I said. “The pills. You said they were sleeping pills.”
Sydney’s smile widened. “Oh, I never said they were sleeping pills. I just asked if you were having trouble sleeping. The pills had nothing to do with that.”
She slid her fingers back onto my thigh, then said, “And for the record, when I asked for your help before you entered my room, you never asked what it was for.”
“You…you knew, didn’t you?” I muttered.
“Of course I knew my sister was asleep. I made sure her Facebook status was offline long enough to know when to come over. I only wanted you,” Sydney said.
Sydney’s fingers slowly slid up and down my thigh, inching further and further up.
We both watched the movement of her fingers until I realized the pills I had taken earlier were kicking in much faster than I had thought. I was rock hard and there was no way of hiding it.
Sydney carefully slid one of her hands onto my bulge. She caressed it and gently massaged my hard-on. Licking her lips, she grabbed the waistband of my pajama pants with both hands.
“Wait, I don’t think—”
Before I could finish my sentence, she yanked my pants down to my knees. There was a moment of silence. Her eyes widened and her jaw dropped.
My fully erect cock was now on full display in front of my girlfriend’s sister. In the silence, I thought I heard a slight gasp from Sydney.
“…wow,” Sydney said. “How…how big…?”
“T…t…ten inches hard,” I stuttered. My heart was still racing. As turned on as I was, I reached for my pants.
“Oh, no, you won’t,” Sydney demanded.
She grabbed my wrists and pinned them next to my shoulders. She then swung her leg over me and positioned herself on top of me.
“Listen, I…I can’t. I’m with—”
Before I could finish my sentence, Sydney leaned in and smothered my face with her breasts.
“Oh, I’m sorry. Were you trying to say something?” Sydney teased as she slowly rocked back and forth on top of me, grinding against my hard cock.
She pulled back, just enough to free her breasts from my face. Leaning in, she whispered in my ear with a voice that dripped seduction. “You deserve better.”
Our eyes met as she moved closer, and then her lips were on mine, her tongue slipping into my mouth.
I didn’t resist. I returned her kiss, matching her intensity.
She gripped my neck, turning my head to the side, and traced a path with her tongue up and down my neck, leaving a trail of heated kisses.
Slowly, she lifted my shirt, pressing kisses to my chest, and then lower. When she reached my lower stomach, her right hand began to gently stroke my balls.
My mind was a whirlwind of thoughts. As much as I wanted this, I couldn’t forget about Amy. With that in mind, I tried to stop her.
I sat up slightly, starting to say, “Listen, I don’t…”
But it was too late.
Our eyes locked again as she took hold of my cock. She licked her lips and then took me into her mouth.
The room fell silent, the only sound was her swallowing me. It was euphoric. The pleasure was overwhelming. I lay back as she continued.
Our eyes no longer met as hers rolled back, mirroring my own. I lay there, helpless, as she worshipped my cock. Her breasts bounced with each movement of her head as she took more and more of me into her mouth.
At first, she took three to four inches, but soon it was six to seven. No girl had ever taken me this deep, not even Amy.
What had started as a passionate blowjob quickly became a fantasy come to life.
Sydney slowed her pace, adjusting her body, and gripped my thighs. She lifted her head just enough to hover over the tip of my cock.
I could feel her breath, tantalizingly close to my swollen member. I lifted my head to look at her.
She licked her lips and descended on me again, but this time, slower. Her mouth was heaven. Her tight throat expanded to accommodate me, and this time she went even deeper.
My jaw dropped. She had taken eight to nine inches of my throbbing cock into her mouth without gagging.
She pulled back, only to swallow me again and again…and again.
I arched back as she devoured me. I grabbed the blanket within my reach, surrendering to her.
She quickly adjusted to my size, and then she pulled me out of her mouth. With a smile, she licked up and down my shaft…and my balls.
Her enthusiasm, combined with her skill, was pushing me to the edge.
She took hold of my shaft and stroked it with her small hands. Both of them. Precum was leaking from me.
Her eyes were focused on the tip of my cock as she licked her lips. She placed one hand on my thigh and continued to jerk me off with her other hand, licking the precum off.
“Mmmm, you taste really good,” she murmured, continuing to lick.
After flicking her tongue under the head, she slid her tongue down to my balls. She hovered her mouth over the right side, licking a few more times before sucking on it.
A jolt of pleasure shot up my spine, and I felt even closer to cumming. To my surprise, she sucked even harder, swallowing my entire right ball.
My eyes rolled back in my head. I was shaking. It was only a matter of time before I exploded.
After giving the right side attention, she did the same to the left. More precum oozed out of me, dripping down my shaft onto her small hand. She felt it and quickly stopped to lick it off.
“You’re about to cum, aren’t you?” she asked softly, continuing to lick my throbbing, hard cock.
“Ye…yes. I don’t think I can hold it in anymore,” I managed to respond.
“Good,” she said, squeezing my cock and leaning toward my face. “I’m going down on you again. Only this time, I want all of you…and I mean ALL of you.”
She took my right wrist and gently placed my hand on her right cheek. “So be a good boy for me and help me go all the way down,” she said with a wink.
She then gripped both of my thighs, unhinged her jaw, and slid her tight throat down my hard cock. Her lips, wrapped around my member, were now only an inch away from the base of my cock.
And as she commanded, I gave in.
I slid my right hand around the base of her neck and threaded my fingers into her hair.
As I gently tugged, she responded by gripping my thighs even harder.
Her head wasn’t bobbing up and down as much this time. She was making more effort to force her way all the way down.
She let out a slight moan as she continued to work her way down. She had about three fourths of an inch more to go… So I gave it to her.
With my right arm, I forced her head all the way down my shaft. One shove and I was fully inside her mouth.
She let out a moan of pleasure and stayed there for a few seconds before coming back up.
“That’s my boy,” she gasped happily, then immediately went down on me again and again. She was now able to take all of me in without my help. And she kept going.
My shaft tensed up, and I felt a strong buildup of pressure inside me. Soon, I hit the point of no return, and I knew there was no going back. I quickly whispered, “I’m about to cum!”
Sydney once more took all ten inches of me into her mouth and looked up at me.
I stared into her lust-filled eyes and released everything into her mouth. I arched my back from the intense pleasure and my legs started to spasm.
As I unloaded into her mouth, she simply lay there, smiling at me with my entire cock inside her mouth, taking it all.
She did it. She was the first and only girl to take all of me in her mouth…and she drained me.
I relaxed, and she let out another moan of pleasure.
As she continued to lock eyes with me, everything went quiet. She then audibly swallowed the last of my load, smiled at me, and slowly slid me out of her mouth.
“Mmmm, so good,” she murmured, her lips brushing against the tip of my cock.
I was gasping for breath, my mind spinning, when I remembered Amy. I tried to sit up, but Sydney kept her hand on my still-hard cock.
“Where do you think you’re going?” she asked, her voice playful.
I was at a loss for words. Sydney stood, her hands resting on my thighs, a mischievous grin on her face.
“I’m not done with you yet,” she declared.
“What…what do you mean?” I stammered.
I knew it was a stupid question. I’d just had the most intense orgasm of my life, and she probably wanted me to return the favor. But her next words took me by surprise.
“Those pills are still doing their job,” she said, her hand gripping my aching cock. “And I’m going to make sure I get every last bit of pleasure out of them.”
I looked down and saw that I was still fully erect. I was amazed that I was ready for more so soon.
Sydney stood up, crossed her arms, and pulled her shirt over her head, revealing her stomach and then her chest.
Her large breasts bounced as she tossed her shirt to the corner of the room. She reached for her underwear and slowly slid them off, her body swaying from side to side.
I sat on her bed, completely captivated. She walked over to me, straddled me, and kissed me deeply. I held her close as we kissed.
She squeezed my neck gently, pushing me back onto the bed, and leaned in to kiss me again. Then she hovered over me, her eyes half-closed, and kissed my face lightly.
“Now…I’m going to turn around and put my wet pussy in your face. I want you to eat me out like it’s your last night on earth. Meanwhile, I’ll be enjoying my new favorite toy…,” she said, her hand on my cock.
I didn’t say anything. I just nodded and watched as she turned around.
The sight above me was breathtaking. Her ass was round and full, her pussy completely bare. She lowered herself onto my face and I eagerly tasted her.
She was so sweet…so delicious. I was in heaven. As soon as my tongue touched her clit, Sydney’s body jerked in surprise.
Even though my head was buried between her thighs, I heard her mumble, “Holy shit, he’s good at this too?”
As she relaxed, I continued to eat her out. I could tell she took good care of herself by the way she tasted. I felt her lean forward and then my throbbing cock was in her mouth again.
It took all my willpower not to stop what I was doing, but I managed to keep going.
After a few minutes, she stopped and sat up. She put more pressure on my head, but I was loving every second of it. She sat there for a moment, her fingers lightly tracing my hard cock as I continued to eat her out.
She then moved her fingers up my body, over my chest, up to my neck, and then my face. She leaned in and kissed me again, this time tasting herself on my lips.
She took my wrists and placed them on either side of me.
She looked at me and whispered, “I want to fuck you so hard right now.”
Her voice wasn’t as commanding this time. She was probably a little nervous. She’d probably never had something this big inside her before.
I don’t know what came over me, but I found myself saying, “What’s stopping you?”
Her eyes widened in surprise, her mouth fell open slightly, and her breathing quickened. She probably hadn’t expected that response from me. I hadn’t expected it either.
She lifted her left leg over me, her hand on my cock. I lay there as she positioned herself above me. Her wet pussy was now directly above the tip of my penis.
“Do you have any cond…uhhh—”
Before I could finish, she lowered herself onto me, taking me inside her.
“Ohhh… You’re so big. I…I just, I…I needed this inside me,” she moaned. “I already feel so full.”
She was only about five or six inches down, but she was so tight.
She started to rock back and forth slowly, her hands on my chest. After a few minutes, she picked up the pace and forced herself down on me even further.
She was a good eight inches down. I hated to admit it, but I’d never felt this good during sex before. As guilty as it made me feel, I wanted more. I wanted more of her.
I grabbed her by the throat and sat up. Her eyes widened and her breathing quickened, but she kept moving. I pushed her onto the bed, my hand still on her throat.
Her large breasts bounced as she lay there, helpless under my grip. I put my other hand over her mouth. There was a moment of silence as I listened for any noise. The house was quiet.
I leaned in closer to her, replacing the hand over her mouth with a finger on her trembling lips, signaling her to stay quiet.
I whispered in her ear, “Do you want ALL of me now?”
Sydney nodded.
I leaned in closer and asked, “How bad?”
Without making a sound, she parted her lips and began to suck on my finger.
As I leaned back, she spread her legs before me.
I bent down, pressing the tip of my cock against her trembling pussy, and then slid all the way in.
Just like me earlier, she arched her back, letting out a barely audible gasp.
I stayed inside her for a moment, savoring the sensation, knowing that she’d taken all of me. Then I pulled back and thrust in again, watching her large breasts bounce in front of me.
She closed her eyes, one hand clutching the bedsheet, the other over her mouth to stifle any sounds.
I knew she didn’t want me to stop, and the trembling of her legs told me to keep going.
After a few minutes, her legs started to shake.
I gently rested my left hand on the upper part of her pussy, massaging her with my thumb, until I was stimulating her clit.
She released the blanket, wrapped her arms around me, and drew me closer. She lifted her head and whispered in my ear, “I’m cumming!”
In no time, her body stiffened and she buried her face in my chest, letting out a soft, satisfied moan as she surrendered.
I felt her juices pooling around my cock, and watched her body shudder as she climaxed. Feeling a sense of accomplishment, I slowly moved my cock back and forth, watching her body tremble even more.
“Please…,” she murmured. “I need just a little more.”
Without a second thought, I grabbed her ankles, spread her legs, and started to fuck her again, this time with more force.
She gasped as I filled her completely with the first thrust. I had to cover her mouth with my hand to keep her from waking anyone in the house.
After a moment, she opened her mouth, sucking on my finger again…and I let her. A few moments later, she gently pulled my face to hers and pleaded softly, “Please…cum inside me.”
“As you wish…,” I replied.
I slid my fingers up her body and gently squeezed her breasts as I started to fuck her even faster. Soon, I let go of control and fucked her as hard and as fast as I could, filling her small body with my large cock.
I felt the tension building again. I knew it was coming. In a matter of seconds, I whispered, “I’m cumming, baby. I’m cumming!”
Almost instinctively, Sydney wrapped her legs around me, stopping me from pulling out. With both of us shaking, it happened.
A powerful wave swept through my body as I came inside her. With all ten inches still buried inside, my cock pulsed, continuously pumping my cum into her.
After it stopped, we lay still for a minute or two, catching our breaths and calming down. I then pulled out of her, noticing a large amount of our juices flowing out of her. I lay down next to her on the bed.
We lay there in silence for a few minutes.
Once our breathing returned to normal, Sydney turned toward me and draped her arm over me, burying her face in my chest.
“You’re the biggest I’ve ever had,” she said. “Definitely, the best too.”
I didn’t say anything. I was still stunned by what had just happened.
Sydney lifted her head and once again lightly traced her fingers across my body, taking in the sight of what she had just “taken in.”
She then climbed on top of me and with a slight smirk she asked, “How do you feel now?”
I tried to answer but couldn’t find the words. I just nodded.
She smiled and got up. She drank water from a bottle and offered some to me.
After a few sips, I slowly got dressed and headed toward the door to leave, but she stopped me one last time.
“Before you go…,” she said casually.
I turned around, only to see her pulling up her underwear.
She walked over to me, placed her hand on my crotch, smiled, and said, “This is just the first night. I have a lot more planned for you, big boy.”
She winked at me, turned around, and walked back to her bed.
I quietly closed her door and tiptoed back into the room with Amy. I let out a silent sigh of relief that Amy was still asleep.
As I rested my head on the pillow, Sydney’s words echoed in my mind. I knew that this was going to be a summer like no other.
