Catching Riley


I pulled into the driveway of my parent's house around 5:15 with my Dodge Caliber loaded down with everything from my college dorm.

"Finally," I sighed aloud as I shifted the car to park.

It was finally summer break and after a completely grueling junior year of college I intended to spend each and every day of it relaxing.

My parents had phoned me earlier in the month to tell me that they would be spending the majority of the summer in Europe on a second honeymoon. I tried to sound disappointed during the call but all I could think about was having the entire house to myself for a while.

Still sitting in my car, I looked up to see my neighbor, Riley, huddling with a group of girls, each of them decked out in graduation regalia posing for a picture.

Riley and her parents had lived next to my family and me as long as I could remember. Our parents had always been close and we had been forced to make polite conversation at various barbeques and dinner parties through the years. Riley and I didn't have much in common other than the fact that our parents enjoyed throwing lavish parties and expected us to be the best of friends.

Riley was three years younger than me and, guessing from the graduation party going on at her house, she had just graduated high school.

I chuckled, shrugged off my seat belt, opened the driver door and climbed out of the car to unload all of my dorm things.


The next morning I woke up feeling like I had been hit with a ton of bricks. I looked at the clock and read "8:45."

"Great." I said aloud.

Why didn't I wait until the morning to get all of that crap out of my car? A 6 hour drive would have been enough activity for any normal person but I had to get it all over with last night.

I knew that in this much pain I would never get back to sleep so I climbed out of bed and headed for the medicine cabinet. I took some ibuprofen and decided to go laze in the hot tub on the second floor balcony.

As I was setting the hot tub up I looked down at the fence that separated Riley's parent's property from my parents' property and I spotted Riley in her yard close to the fence, spread out on a yellow beach towel applying sunscreen.

My jaw dropped. I know that it's cliché to say "she grew up," in moments like this, but it was truly the only words that made sense in my brain at the time.

Growing up, Riley was, for lack of a better word, awkward. Her legs were always too long for her body and she had little to no shape. She wasn't ugly; she just wasn't someone I gave much of a thought about dating.

Taking a second glance down at her I noticed that all of that had changed. Her hips and abs looked shapely now and her body had grown into her legs. She wasn't rail thin but from the looks of her body she must work out at least once a week. Her breasts filled the cups of her bikini top nicely and I guessed she was either a large B cup or a modest C.

She pushed a strand of her light brown hair behind her ear and sat the sunscreen bottle down. I suddenly became very self-conscious standing over her ogling like I was so I slinked down into the hot tub and tried to relax.

Thirty minutes later I stood to go to the kitchen and fix myself some breakfast and I stopped before I even got out of the hot tub. I shifted and did a double take to make sure that what I was seeing was actually happening.

The bottom to Riley's bikini lay discarded next to her right hip and she was absent mindedly flicking her middle finger across her slit. I couldn't tell if her eyes were opened or closed because she was wearing sunglasses.

I watched her for several more minutes as her finger became more deliberate and her thighs began tensing up. I felt hot all over and blood was quickly rushing to my cock.

I can't explain the logic or the reasons behind the next thing that happened, even if I wanted to.

I sloshed out of the hot tub, dried my hands on my towel and quickly grabbed my cell phone. I snapped three pictures in succession of Riley with her hand manipulating her crotch and headed inside to slide on shoes. I crept around the fence and silently walked up to her until I was standing two feet above her head. I was able to snap three more pictures before she realized what I had done and stood up, obviously angry.

"What the fuck are you doing, you perv?!" She said as she wrapped her towel around her body.

"You're the one laying outside without your bikini bottoms flicking your clit at 9AM, not me."

"That is NOT what I was doing and you don't have any proof anyway..." She trailed off.

I snorted and held up my phone that displayed my evidence.

"Chase! Delete those pictures or I'll tell my father!"

It took everything in me not to laugh at that last bit.

"You go right ahead and tell your father but you better be prepared for me to share these pictures with him."

"Go ahead. Show him. I was just... sunbathing." She said, halfheartedly.

This time I actually did laugh.

"Riley, you are going to have one hell of a time convincing your father that you were 'sunbathing' while your bikini top was still on and your fingers were furiously flicking between your legs."

"Ugh. What do you want from me?" She said, practically defeated.

I thought about her question for a minute. What DID I want? I honestly had no intention of doing anything with the pictures other than embarrassing her in the middle of masturbating... But for some reason, what came out of my mouth was, "I'll let you know tomorrow."

I left her standing there, angry and embarrassed and walked back to my property to think about just what it was I wanted from her.


I had just finished dinner and was opening my first beer of the evening while I thought about the incident with Riley from earlier that morning. She looked so helpless that I actually felt pretty bad about what I had done. I had no real reason to do it other than the fact that I could. The more I thought about it, the more I realized that she had stirred something inside of me and I didn't know anything other than the fact that I wanted to watch more.

My parents had sent a text at 3:00PM asking me if I would go to the lake house they owned and stay for a week to be sure that everything was in working order before the people who were scheduled to rent it for the summer got there.

I suddenly knew exactly what I wanted from Riley. I sipped on my beer and wondered how I went from feeling guilty for ogling Riley to taking pictures of her masturbating and confronting her with them... to blackmailing her into coming to the lake house with me for a week so that I could watch her do it again...


I awoke early the next morning and took my laptop and my breakfast out onto the patio. I ate and read about various sports news, waiting for Riley. I hadn't told her when I would let her know what I wanted from her but I knew that she would be over here as soon as her parents left for work. I finished my bowl of cereal and logged into my email while I waited.

Like clockwork, at exactly 7:30 Riley was walking up the path to my back porch. I didn't try to hide my smile. "Hey Riley, what can I do for you?"

"Don't play coy with me, Chase. Stop being an asshole already."

I closed the lid to my laptop and positioned my chair more towards her and said

"I don't think that you are in a very good position to be making demands."

I patted the chair next to mine and said "Come sit. We'll make a deal."

She looked exasperated but scared enough to do as I said. This time I hid my smile.

"I... enjoyed what I saw yesterday... and if you were willing to spend a week with me at the lake house, I will delete the pictures and we can forget this whole thing happened."

Her face got red as she realized what I had just asked her.

"You want me to spend a week alone with you, practically in the middle of nowhere, being your fuck-buddy?? Yeah, ok. That's not creepy at all!"

"I don't want to have sex with you. Well, let me rephrase that, the trip will not consist of me having sex with you. Not once."

"Then what exactly is it that you want? I know you don't want to take me to an empty house four hours away just to watch Disney movies and skip for a week."

I chuckled. "I want you to repeat yesterday in different scenarios, while I watch. You know, minus the whole part where you got butthurt when you found out I was watching."

"What are you going to do if I don't go with you?"

If she seemed scared when she asked this, she hid it well.

"I'll make sure those pictures get to your parents. Maybe not tomorrow, or anytime soon, but you'll know that I'm going to and every time they call your name you're going to worry if this is the time you have to explain to your parents why they just received pictures of their daughter playing with her pussy on their front lawn, in broad daylight."

She sighed. "My parents are never going to agree to let me go. We barely get along when both our parents are throwing parties. They're going to know something is up if I ask to go away with you alone for a week..."

"You're 18, you're a big girl. I'm sure you'll think of something." I winked at her.

As I stood up I added "I'm leaving at 8AM Monday morning for the lake. I'll be gone tomorrow until late afternoon. I expect your suitcase packed and ready to go when I get in tomorrow. I'll leave you a key to the back door and you can bring it in. If I come home and the kitchen is empty, I'll assume you would rather share those pictures with your parents and act accordingly."


I spent all of Sunday preparing for the trip. I was pretty confident that Riley would lie her way into going away with me so I prepared for such.

First I hit up the grocery store for non-perishable food and non-alcoholic beverages then I made a stop at the mall. I purchased various skimpy lingerie items and bikini sets that were barely her size. My last stop was at the novelty shop where I purchased several different sex toys and a bottle of personal lubricant.

My hand hovered over the 6-pack of condoms at the register and I remembered that I had promised her that I would not try and fuck her during this trip. At the last minute I decided to toss them in anyhow, just in case. I made a mental note to tell her about that purchase and assure her that I did not intend to use them.


It was 9:00PM before my car reached my driveway. I hopped out and gathered up the bags of clothes and toys that I had purchased and took them inside. I walked straight through the house and when I reached the kitchen I smiled. A large black suitcase was sitting by the counter.

I dragged the suitcase to my room and dumped out the things I had bought Riley onto my bed. I unzipped the suitcase and found practical things like 5 pairs of jeans, an assortment of t-shirts and tank tops, pajama pants, and cotton capris. I pulled all of the clothing she had packed out and stacked it in my closet and replaced it with the items I had purchased for her. I tossed the toys in, along with a value size pack of rechargeable batteries, a battery charger, the personal lubricant, and the condoms.

Satisfied that I had packed everything she would need I zipped her suitcase up, quickly packed my own, and stowed them both away in my car.


I woke up at 6 and after a long shower and some breakfast I took a caffeinated soda out onto the back patio. I made a mental list of all the things I had intended to bring and slowly checked them off, one by one. I was just getting to "lake house keys" when Riley came walking through my yard, wearing white denim shorts, a turquoise tank top, and converse sneakers. She was carrying a purse and a car charger for her cell phone. I smiled.

"All ready to go, I see," I said as I stood up and stretched.

"I had to lie to my parents and call my best friend and ask her to lie for me as well."

I detected a hint of grumpiness in her voice.

"Did you tell your best friend the truth?" I said with a smirk.

"That I got caught diddling myself in my yard by my pervy neighbor and he threatened to show the pictures he took of me doing it to my parents if I didn't go away with him, alone, for a week to do it in front of him over and over? Yeah... I told her all about that."

She crossed her arms and let out an exasperated sigh.

"When you put it that way, it makes me sound like a sexual predator. You are eighteen, you know. And I'm not going to do anything to you but watch you "diddle" yourself, as you so eloquently put it..." I pushed my chair up to the table and motioned for her to walk ahead of me.

"You want me to believe that you honestly have no expectations at all going into this weekend?" She laughed dryly as she waited for me to unlock the car.

I unlocked the doors and we both got in and settled in for the long drive ahead.

We were on the highway 10 minutes away from our neighborhood before I responded.

"Riley, I don't expect sex from you. This week is not about you being my sex slave. I admit that I did purchase condoms just in case because it's better to be safe than sorry, but they're in your suitcase and you decide if they get used or not. That decision is not mine."

I paused and let her have time to respond.

"What... exactly do I have to do, then?" She shifted uncomfortably in her seat as she said this.

"Masturbate. A lot. While I watch." I smiled and looked at her from the corner of my eye.

She smiled and said "Well, when you put it that it doesn't sound creepy at all."

It hit me that I agreed with her, but instead of discussing it further I turned up the radio and headed towards the lake.


50 minutes into the trip the GPS lost signal and started trying to reroute us home. After spending 20 minutes on the side of the road trying to get the stupid thing to reset, we were finally able to get back on course.

It had been nearly an hour and a half since Riley last spoke. When she finally did she said,

"This trip is longer than I remember. Maybe it was because I always brought something with me to break up the time."

She shifted in her seat and picked at a loose string on her shorts.

The highway was relatively empty and the GPS seemed to be behaving, so I felt comfortable relaxing in my seat and turning cruise control back on.

"I guess since you need something to break up the time the week is going to start early. Unzip your pants."

She hesitated for a second; I guess she was hoping that I was joking, and obliged.

"Slide your shorts down just far enough to comfortably reach your hand in."

She had on fuscia panties with black lace covering the fabric. I gripped the steering wheel a little bit tighter.

"Ok. We're going to play a game that will last until the GPS says that we have 15 minutes left. If you disobey any of my commands there will be severe consequences.

She gulped and said "Ok..."

"Slide your hands down your pants and slowly play with your pussy. Don't rush to cum because we still have two hours and you don't get to stop until we're there."

She sort of whimpered and slid her hand down her panties. 10 minutes passed and I could tell she was already ready to go over the edge. I smirked.

"Move your shorts and panties down so I can get a better look."

"What if a car pulls up next to us??" She sounded genuinely concerned.

"Grab that blanket behind my seat and drape it over your knees. If a car approaches I'll warn you."

She slid her shorts further down and revealed her swollen, aroused, hairless pussy. She made gentle circle motions on her clit until she squirmed and then she stopped and began petting her pussy lips almost absent mindedly. My dick was threatening to break my zipper at this point.

"I'm going to ask you some questions while you continue to... break up the time... and I expect honest answers. It will really be better for you in the long run if you answer truthfully."

"Oh-o-ok." She gasped.

I could tell that she was desperate for an orgasm.

"How many times, on average, to you make yourself cum each day?"

She swallowed hard and slid her hand further down her pussy and slid two fingers inside.

"Three to five."

"Have you ever had sex with another person?"

"Yes. Twice over Christmas break."

She threw her head back onto the headrest and let out a small moan.

"Have you ever used toys before?"

She let out a loud moan and her hips rocked against her hand.

"Only a few times. I don't own any because they're too difficult to hide."

I could tell she wasn't going to last much longer.

"Stop playing with your pussy and play with your nipples." I growled.

She slid the blanket over her lap and pushed her tits up to the top of her bra.

"Lick your fingers and swirl them on your nipples like you do your clit."

As she followed my command her back arched and she moaned.

"Why were you playing with your pussy in my backyard?"

"I do it there all the time. It's the farthest place from my house where the maid won't walk in on me."

"Alternate between squeezing your nipples and swirling your fingers over them."

We were an hour and thirty minutes away and I wasn't sure my cock was going to last that long. My pants were already soaked through with precum.

"Do you like being watched?"

"No. It makes me feel weird." She gasped.

"Too bad." I laughed.

She continued on manipulating her breasts for thirty more minutes until a car pulled up directly beside us.

"Just stop for now and cover up with the blanket until they go away."

I could tell that she was extremely horny and in desperate need to cum. I smiled.

It took the car 45 minutes to exit but it finally did. There was 30 minutes left for me to help her break up the time.

"Put your tits away and start playing with your pussy. Don't you dare touch your clit until I tell you to do so."

She quickly obliged.

"Do you regret getting caught?"

"Y-yes." She stammered.


She gulped. "I feel embarrassed. This is something that is supposed to be p-private."

"You seem to be enjoying it." I grinned.

"I don't have a c-ch-choice."

"Nope." At this point my cock was so swollen and neglected that I would have given anything to switch places with her, just so I could feel some sort of relief.

"Stroke your clit in slow, soft circles. If you feel like you're about to cum, stop. You still have 15 minutes until we have to stop and get groceries. If you cum before then you will still be required to continue stroking your clit, regardless of how sensitive it is. Strip your bottoms off and spread your legs before you start."

She was drenched and hornier than I had ever seen any woman. Her fingers found her tiny clit and she started dragging her fingers across it in small circles. A moan escaped her lips.

"Have you ever done this before? Fucked yourself in front of someone on purpose, I mean?"

"A f-few times. Once at camp and a few times over at my friend's house."

"Is this the same friend that lied for you?"

"No. She would never even do something like this alone, much less with someone else."

"Oh... So you've done this with one of your friends??"

"Twice. Once because her boyfriend had just dumped her and she didn't know how, and once at a sleepover on a dare."

She threw her head back onto the headrest again and her thighs became rigid.

"How did you learn how to do this?"

She stopped moving her finger on her clit and gathered her breathing.

"I was lying in bed feeling to see if I'd missed any places when I had shaved and my finger slipped onto my clit and I kept rubbing on it. My body shook and it felt so good..."

"Do you want to cum right now?"


"How badly?"

"Very badly. I've never wanted to cum so badly in my whole life."

She struggled as she said this, and I noticed she had started slowly stroking her clit again.

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