The Midnight Favor

It was early June, and college had just let out for the summer. I picked up my girlfriend, Amy, who was in her first year at university, and we set out for a three-hour drive toward her parents’ place outside of Scranton, PA.

Amy was a fit, five feet eight softball player who over exerted herself in everything, especially her schooling.

As soon as I had pulled up to her university, I noticed the look of exhaustion on her face. It was enough proof that she would be sleeping the entire road trip.

Of course, I was right.

Amy and I had met in high school and fell in love. She had always been an over-achiever, but ever since she started college, it put pressure on our relationship.

Her balancing the stress from school, work, and sports caused a little tension between us.

We also have not been as intimate as we used to be in our high school years. The few times we actually did, she didn’t show as much enthusiasm.

Don’t get me wrong, I still loved her, but I was hoping this summer break would benefit us greatly and possibly rekindle that spark from when we first met.

After a long drive, we pulled up to her parents’ two-story brick ranch home. Amy woke up from her nap, and we carried our bags to the front door to greet her parents.

Her mom and dad were in their late fifties, and they celebrated their thirtieth anniversary last year. They were the stereotypical parents whose best days were behind them.

They might have been married for three decades, but everyone secretly knew they weren’t happy or in love and only stayed married because of their children’s sake.

Of course, their oldest was Amy, my girlfriend of three years, who I loved.

Then there was also the other daughter…Sydney.

Sydney recently graduated from high school. She was only one year younger than Amy, but she was the complete opposite of her.

Amy was very outgoing and athletic and had been rocking a toned body from participating in sports for the past six years. Her gorgeous dirty blonde hair, perky B-cup breasts, flat stomach, and tight ass were guaranteed to turn heads.

Sydney, on the other hand, was into digital art, fan fiction, and indie music, and she wasn’t as outgoing. Even though we went to the same school, she always hung out with a different crowd.

Sydney was much shorter than her older sister, standing at five feet one with some curves.

She got a cute face with a little bit of a tummy along with an ass that was a little bigger than that was average for girls her size. Her breasts, on the other hand, were…massive.

I tried my best to not get distracted, especially since she was my girlfriend’s sister, but it was very difficult to not glance at her size 30H breasts once in a while.

I only knew this because I overheard it in conversations about how she has a hard time finding bras and shirts that fit.

After exchanging hugs with the parents, Amy and I went inside.

“Hey guys!” Sydney shouted from the other end of the living room.

She had a huge smile on her face as she speed walked to us. She hugged her sister first, as they seemed like best friends, then she turned to me.

“Great to see you as well!” she said, hugging me.

I tried my best to side-hug her without making it obvious that her short, curvy frame was a turn-on for me. “You as well!” I replied. “How have things been going for you?”

“Nothing much outside of graduation and going to a community college in the fall,” Sydney said. “I bet you two are happy to be on break.”

After exchanging small talk, Amy and I went upstairs to unpack and rest for a while. We talked about all the fun things we could do during the summer break, but it was clear that Amy’s head was full of thoughts about the next school year.

We eventually came down for dinner and talked with her family. Amy and Sydney told each other everything, so most of what was brought up was nothing new to them.

After dinner, Amy’s parents headed to their master bedroom for the night to watch Netflix until they both fell asleep. This was no surprise an everyday occurrence, especially since the spark in their relationship seemed to have gone out years ago.

Sydney, too, left for her room for the night. After placing the remaining dishes in the sink, Amy and I went to our room as well.

Shortly after we got comfortable, I started to massage Amy’s shoulders and upper back.

“Mmmmm, that feels really good,” she said, with her shoulders slouched back and her chin in the air.

“I’m glad,” I replied, kissing her forehead and slowly making my way down her lower back.

After I massaged her back for a few minutes, she grabbed her phone and started flipping through Facebook. I kept massaging her, working my way down her legs and then her feet.

After rubbing her feet for a few minutes, I ran my fingers delicately along her long legs, up her thighs, and over her hips. Then, I eventually touched her chin.

I gently turned her face toward me and kissed her passionately. She smiled and then went back to scrolling on Facebook.

I caressed her arms and asked if she wanted to get a little dirty tonight.

“I have a headache,” she responded. “Plus, I’m still tired from the drive.”

Not going to lie, I was a little irritated, especially since she used this excuse a lot. I understood we couldn’t have sex every time I asked, but we were going on three months now without a single fuck.

Plus, she had slept the entire car ride over. I was the one who was supposed to be tired.

“Okay,” I resentfully replied. I made sure not to sound upset by her response so I could avoid unnecessary conflict and additional tension.

I, too, then reached for my phone to pass time.

Within a few hours, Amy passed out.

I had a hard time sleeping, so I headed toward the door to go outside for some fresh air. But just before I grabbed the door handle to step out of the bedroom, I heard a light knock from the other side.

I waited a few seconds and then opened the door.

It was Sydney…wearing nothing but her underwear and a tight t-shirt that did not do a good job of hiding her large breasts.

“Hey, sorry… I was trying to get a hold of my sister,” Sydney quietly said.

“She passed out about an hour or two ago,” I replied, making every effort to not stare at her chest.

“Oh, okay…um…is there any way you could help me then?” she asked.

“What’s up?” I replied.

Sydney gestured with her right hand for me to follow her, and so I did.

She went into her bedroom, and I waited at her door, thinking she was gonna show me something.

“It’s okay, you can come in, silly,” she said.

As I walked into her dimly lit room, she asked quietly if I could shut the door so as not to wake anyone in the house up. I obliged and very quietly closed the door.

She pulled a shoebox from underneath her bed.

“You got some new shoes?” I asked.

As Sydney opened up the box, my eyes widened a little at what I saw.

“Nope, something even better,” Sydney responded.

Amy’s sister sat on her bed and went through the shoebox.

Inside the box were a few bags of weed, some edibles, and what looked like four to 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 replied.

“You are just as fun as my sister,” Sydney jokingly said, taking another bite of the edible.

I chuckled a bit, and as I sat down on her bed, I asked her how she got all of this.

“I have good connections,” she said. “You seem kinda stressed. Here, try this.” She broke off a chunk of another edible and leaned toward me to put it to my lips.

I was a little hesitant, but when she leaned toward me to put the edible in my mouth, more of her cleavage started to show. I got distracted enough and gave in. I opened my mouth and let her feed me the edible.

“Hey, that’s not bad!” I said softly as I swallowed.

“I’m glad!” Sydney responded cheerfully. “I made these myself.”

She put the bag of edibles back into the box and grabbed a pill bottle with the label peeled off.

“What’s that?” I asked.

“Hard time sleeping?” she responded, handing me two pills.

I smirked and took them. She then gave me a glass of grapefruit juice to help down it.

I thanked her as she put the pill bottle back into the shoebox and slid it under her bed.

“Does your parents know you have all that?” I asked.

“Nope, it’s our little secret,” she said. “Speaking of secrets, you have some yourself, don’t you?” Sydney mysteriously asked.

“None that I am aware of. Why do you ask?” I said.

“Oh, don’t be coy with me, handsome,” she sharply responded. As she spoke, she leaned over and gently placed her small hand on my upper thigh.

“I…uhh… What are you doing?” I nervously asked as I moved slightly back.

Oh, I indeed was nervous, but I also felt sorta guilty for not moving completely away from her either. I kinda wanted to, but at the same time, I didn’t.

“What does it look like I am doing?” she said seductively as she ran her fingers from my left thigh to her breasts. “I noticed that you have glanced at my chest before. They are remarkable, aren’t they?”

I was silent. I tried to look somewhere else, but there was no hiding it.

“Is my selfish sister depriving you of your needs?” she seductively asked.

“Huh…hu…how did…” I quivered.

“Oh, I know,” she interjected. “We tell each other everything. It’s a shame that she has been so caught up with everything that she makes little to no effort for you.”

I started to get a little dizzy. My heart raced and to add to my nervousness, I started to get hard…really hard. “What, what did you give me?” I asked.

Sydney smiled and calmly said, “As I said before, I gave you an edible I made myself.”

“No, the pills,” I said. “The pills. You said they were sleeping pills.”

Sydney’s smile got even bigger. “Oh, I never said they were sleeping pills. I just asked if you had a hard time sleeping. The pills had nothing to do with that.”

She slid her fingers back onto my upper thigh, then said, “And for the record, when I asked for your help before you entered my room, you not once asked what it was for.”

“You…you knew, didn’t you?” I muttered.

“Oh, 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, casually going slightly further and further up.

We both focused on 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 on my bulge. She caressed it and gently massaged my hard-on. Licking her lips, she grabbed the waistline of my pajama pants with her both hands.

“Wait, I don’t think—”

Before I could finish the sentence, she jerked my pants down to my knees. There was a moment of silence. Her eyes widened and her jaw dropped.

My fully erect penis was now on full display in front of my girlfriend’s sister. In the silence, I was sure I heard a slight gasp from Sydney.

“…wow,” Sydney said. “How…how big…?”

“T…t…ten inches hard,” I stuttered. My heart was still beating fast. As turned on as I was, I still carefully reached for my pants.

“Oh, no, you won’t,” Sydney demanded.

She grabbed my wrists and slammed them next to my shoulders. She then swung her left 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 closer to me and smothered my face with her large breasts.

“Oh, I am so sorry. Were you trying to say something?” Sydney teased as she slowly rocked back and forth on top of me, grinding on my hard cock.

She then pulled back, only far enough to remove her breasts from my face. She leans in and with the most seductive voice, she whispers in my ear… “You deserve better.”

As she moved closer, we locked eyes. She then kissed me, sliding her tongue into my mouth.

I easily gave in and did the same to her.

She grabbed part of my neck and turned my head to the side. She slid her tongue up and down my neck and left a few passionate kisses.

She then pulled up my shirt, slowly kissed my chest, and soon worked her way down. Right when she reached my lower stomach, she started to caress my balls with her right hand.

My head was full of rushing thoughts. As much as I wanted this, I had to remind myself that I was with Amy. With that in mind, I made another attempt to stop her.

I got up a little and said, “Listen, I don’t…”

But it was too late.

We locked eyes again as she grabbed my large member. She licked her lips and then took me in her mouth.

The room was silent, and all I heard was the sound of her swallowing me. It felt euphoric. I immediately was overwhelmed by the pleasure. I lay back as she continued.

We no longer locked eyes as hers rolled back, just like mine did. I helplessly lay there as she continued to worship my cock. Her breasts bounced with each shake of her head as she slowly worked her way more and more down my shaft.

At first, she took in three to four inches, but that became six to seven inches in no time. I never had a girl go down on me this far, including Amy.

What started out as a passionate blowjob soon became an experience I had fantasized about for many years.

Sydney slowed her pace down my shaft, adjusted her body, and grabbed each of my thighs firmly. She pulled her head up just enough to hover directly over the tip of my penis.

I could feel her breath, as it was only less than an inch away from my swollen member. I tilted my head up to look at her.

She licked her lips and went down on me again, but this time, much slower. Her mouth felt so good. Her tight throat swelled to accommodate my large member, only this time she had gotten even farther.

My jaw dropped. She now probably had around eight to nine inches of my throbbing cock inside her mouth and had not gagged at all.

She pulled back, only to swallow me again and again…and again.

I immediately arched back a bit as she devoured me. I grabbed the blanket that was within my reach, and I let her have her way with me.

She quickly got used to my large cock, and then she slurped me out. With a smile on her face, she licked up and down my long shaft…and my balls.

Her enthusiasm, along with her mouth skills, was pushing me to the edge real quick.

She grabbed my shaft and stroked it with her tiny hands. Yes, hands… She used both. There was precum leaking out of me.

Her eyes were fixated on the tip of my cock as she licked her lips. She then put one hand on my thigh and continued to jerk me off with her other hand while licking the precum off.

“Mmmm, you taste really good,” she said as she continued licking.

After flicking her tongue right underneath the head, she slid her tongue all the way down to my balls. She hovered her mouth over the right side and licked a few more times before she sucked on it.

A jolt of pleasure went up my spine, and I felt even closer to cumming. And to my amazement, she sucked even harder and swallowed my entire right ball.

My eyes immediately shot right through the back of my skull. I was shaking. It was only a matter of time before I burst.

After taking care of the right side, she did the same to the left. More precum oozed out of me and starting dripping down my shaft onto her tiny hand. She felt it and quickly stopped to lick it off.

“You are about to cum, aren’t you?” she quietly asked as she continued to passionately lick my throbbing, hard cock.

“Ye…yes. I don’t think I can hold it in anymore,” I responded.

“Good,” she said, then squeezed my cock and leaned toward my face. “I am 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 the palm of my hand on her right cheek. “So be a good boy for me and help me go all the way down,” she demanded with a wink.

She then grabbed both of my thighs, unhinged her jaw, and slid her tight throat down my long, hard cock. Her lips that were wrapped around my large 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 then slid my fingers into her hair.

As I gently gave it a tug, she immediately responded by squeezing my thighs even harder.

Her head wasn’t bobbing up and down as much this time. 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 fourth 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. All it took was one shove and before I knew it, I bottomed out in her mouth.

She let out a pleasurable moan and stayed there for a few seconds before coming back up.

“That’s my boy,” she happily gasped, 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 am about to cum!”

Sydney once more took all ten inches of me into her mouth and fixed her eyes on me.

I stared into her lustful eyes and released it all in her mouth. I arched my back again from the immense pleasure and my legs started to slightly spasm.

As I unleashed my load into her mouth, she simply just 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 pleasurable moan.

As she continued to lock eyes with me, everything got really quiet. She then audibly gulped the last of my load, smiled at me, and slowly slid me out of her mouth.

“Mmmm, sooooo good,” she whispered as she kissed the tip of my cock.

As I tried to catch my breath and thoughts, I suddenly realized I forgot about Amy. I pushed up, but Sydney continued caressing my large, swollen member.

“Where do you think you are going?” she asked.

I was speechless. Sydney stood up and leaned toward me with each of her hands on my thighs. She had a huge grin on her face, as if she was up to something no good.

“I am not done with you, sir,” she commanded.

“Wha…what do you mean?” I quivered.

I knew that was a dumb question. I just experienced the biggest orgasm of my life, and she probably wanted me to return the favor to her…but her next words caught me off guard.

“Those pills are still at work,” she said as she grabbed my aching cock. “And I will make damn well sure I get every drop of use out of them.”

I noticed my cock was still fully erect; I was amazed that it was immediately ready for more.

Sydney stood up, crossed her arms, grabbed the bottom of her shirt, and pulled her shirt up over her head, first exposing her stomach, and then her chest.

As soon as the shirt came off, her wonderfully large breasts bounced right in front of my face. I was mesmerized.

She tossed her shirt to the corner of her room and slowly reached for her underwear. With a thumb on each side, she slowly slid them off while swaying her body from side to side.

I sat on her bed in awe. She walked up to me, straddled me, caressed my face with her hands, and then slid her tongue into my mouth. I held her tight as we passionately kissed.

She gently squeezed my neck, forced me to lie down on her bed, and drew closer to kiss me some more. Then she hovered her face over mine with her eyes mostly closed and lightly kissed my face.

“Now…I am going to turn around and bury my wet pussy in your face. I want you to eat me out like it’s your last night on earth. Meanwhile, I will be treating myself to my new favorite toy…,” she said, grabbing my cock.

I didn’t say anything. I nodded and watched her turn around.

What hovered above me was a beautiful sight. Her ass was plump, and her tiny pussy was completely shaved. She lowered down on my face and I indulged her.

She tasted so sweet…so good. I was on cloud nine. As soon as my tongue quickly hit her clit, Sydney’s body jerked in surprise.

Even though my head was buried under her, I heard her mumble, “Holy shit, he’s good down there too?”

As she started to relax, I just continued to eat her out. I could tell she took real good care of herself based on how she tasted. I felt her lean forward and soon my throbbing cock entered her mouth again.

It took all the strength I had to not stop what I was doing, but I managed to keep going.

After a few minutes, she stopped and slowly sat up. T put more pressure on my head, but at this point, I loved every bit of it. She sat there for a minute, gently running the tips of her fingers on my hard cock as I continued to eat her out.

She then eased off me and moved her fingers up my body, past my chest, onto my neck, and then my face. She leaned in and kissed me again, only this time she got to taste her juices on my lips as well.

She then grabbed my wrists and set them on each side of me.

She looked at me and whispered, “I want to fuck you so hard right now.”

She didn’t sound as demanding this time. She was probably a little nervous. She probably never had something this big inside her before.

I do not know what happened to me, but my primal instincts took over, and I replied, “What’s stopping you?”

Her eyes widened with surprise, her jaw dropped a bit, and her breathing got a little heavier. She probably didn’t expect that answer from me…neither did I.

She lifted her left leg over me, grabbing my cock. I lay there as she positioned herself above me. Her wet pussy was now hovering directly on top of the tip of my penis.

“Do you have any cond…uhhh—”

Before I could finish, she lowered herself on top of me, taking me inside her.

“Ohhh… You are sooo big. I…I jussst, I…I needed this inside of me,” she slurred. “I already feel so full.”

She was only about five to six inches down, but dear God, she was so tight.

She started to slowly rock back and forth with her hands on my chest, then 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 had never felt this good during sex before. As guilty as this sounded, I wanted more of it. I wanted more…of her.

I grabbed her by her throat and sat up. Her eyes widened and her breathing got even heavier, but she kept fucking me. I slammed her next to me on the bed with my hand still on her throat.

Her large breasts bounced as she now lay helplessly under my grip. I used my other hand to cover her mouth. There was a moment of silence to listen and hear if we had made any noise. The house was silent.

As I leaned in closer to her, I replaced the hand that had been covering her mouth with one finger over her trembling lips to let her know not to speak.

I then whispered into her ear, “Do you want ALL of me now?”

Sydney nodded her head in approval.

I leaned in further and asked, “How bad?”

Without making a sound, she parted her lips and passionately started sucking on my finger.

As I reclined back, she spread her legs before me.

I bent down, pressing the tip of my penis against her trembling pussy, and then slid my entire cock all the way in.

Just like me earlier, she arched back, letting out a barely audible gasp.

I pushed all ten inches in her for a few moments, enjoying the sensation, knowing that she took all of it. Then I carefully slid back and thrust back in again, watching her oversized tits bounce in front of me.

She closed her eyes, reached one arm up, grabbed a piece of her bedsheets with one hand, and covered her mouth with her other hand, trying to not make a loud sound.

I knew she did not want me to stop, and the tremble in her legs reassured me to just keep fucking her.

After a few minutes, her legs started to buckle.

I carefully placed my left palm on the top part of her pussy, then massaged her for a few moments with my thumb, until I was rubbing her clit.

She let go of the blanket, wrapped both arms around me, and pulled me closer to her. She then lifted her head up and whimpered in my ear, “I am cumming!”

In a matter of seconds, her whole body tensed up and she quickly buried her face in my chest. She let out a quiet, blissful moan as her body gave in.

I felt her juices build up inside all around my large member, and I watched her whole body quiver as she orgasmed. Feeling very proud of myself, I slowly thrust my cock back and forth, watching her body tremble even more.

“Please…,” she quietly begged. “I want just a little more.”

Without hesitation, I grabbed her ankles, spread her legs, and began to fuck her again. This time even harder.

She gasped as soon as I bottomed her out on the first thrust. I had to cover her mouth with my hand to prevent her from waking anyone in the house.

After a minute, she opened her mouth, only to suck on my finger again…and I let her. A few more moments later, she gently pulled my face toward hers and innocently begged, “Please…cum inside me.”

“As you wish…,” I responded.

I slid my fingers up her body and gently squeezed her large 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, impaling her tiny body with my large cock.

I felt the tension build up again. I knew it was coming. Within a matter of seconds, I quickly whispered, “I’m cumming, baby. I’m cumming!”

Almost instinctively, Sydney wrapped both of her legs around me, preventing me from pulling out. With both of us trembling, it happened.

A powerful rush swept through my body as I came inside her. With all ten inches still buried inside, my cock pulsated, continuously pumping my cum into her.

After it stopped, we were both still for about a minute or two, catching our breaths and winding down. I then pulled out of her, only to notice a large amount of our juices flowing out of her. I then lay down next to her on her bed.

We both lay there silently for a few minutes.

As soon as both of our breathing went back to normal, Sydney turned toward me and placed her arm over me while burying her face in my chest.

“You are the biggest I have ever had,” she said. “Definitely, the best too.”

I said nothing. I was still awestruck by what just happened.

Sydney lifted her head and once again lightly slid her fingers across my body, taking in the view of what she literally “took 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 simply 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 final time.

“Before you go…,” she casually said.

I turned around, only to see her pulling up her underwear.

She then walked over to me, placed her hand on my crotch, smiled, and said, “This is just the first night. I have a lot more in store for you, big boy.”

She then winked at me, turned around, and walked back to her bed.

I shut her door quietly and tiptoed back into the room with Amy. I let out a silent sigh of relief that Amy was still asleep.

As I reclined my head on the pillow, Sydney’s words lingered in my mind. I knew that this was going to be a summer like no other.