Her Trick, My Treat

*This is my entry into the Halloween contest and my second story. Any feedback and votes would be greatly appreciated. Thank you and enjoy.

**Edited on 12/12/23

I was up late the night before Halloween, working on an essay for class. All I wanted was to binge-watch all things horror, but like usual, I had procrastinated till the last night. My teacher was old-fashioned and insisted on a printed copy being turned in at the start of class tomorrow. I tried to focus on my paper but left Facebook open, and the message notification distracted me. I wondered who would message me so late, and after a solid two minutes of work, I welcomed the distraction.

It was Lilah, my first ex-girlfriend's little sister. All thoughts of working on my paper vanished when I saw it was her messaging me. A couple of weeks earlier, she had friend-requested me. I wasn't even friends with her sister anymore. I accepted and, within a day, noticed some of the sexy pictures that she was posting. The last time I had seen her, she had been a short, loud girl who was as quick to scream a cuss word at me as she was to try and kick me in the balls, which always seemed to be one of her favorite games.

In my senior year of high school, shortly after I turned eighteen, I lost both of my parents in a car crash. I had tried to stay with my brothers, but things didn't work out with them, and I ended up moving in with my girlfriend Vivian's family. Her mother took me in, and I became a part of the family. It was just Vivian, who was a few months older than me, her mom, and her fifteen-year-old sister Lilah. Lilah became like the little sister I never had or wanted. I tried to get along with her, but she had this amazing skill of always being able to get under my skin. This skill combined with her knack for preventing Vivian and I from having sex too often by annoying us, made getting used to her almost impossible.

They had different fathers, but neither was involved in their lives, so Vivian and Lilah lacked a male authority figure. I admit sometimes I overstepped my place and scolded Lilah for her crazy actions. I tried my best to try and help her out because I could see from her rebellious nature that trouble was going to find her easily. I was critical of Lilah and tried to help her out when she was in trouble, thinking that maybe we could reach an understanding, but that never happened.

I felt comfortable in that family and was starting to feel at home, but I eventually found out that Vivian was cheating on me nearly the whole time I was living with them. Her best friend ended up telling me. When I confronted her about it, she acted weird when she denied it. It didn't take long for all of the lies to come out. I packed my stuff and managed to move in with my best friend. Over the next three years I would occasionally talk to Vivian, but I would still feel that pain of betrayal and how the future I had thought we were starting to build towards had all been a mirage. I never heard from her sister.

Once I accepted Lilah's friend request, I went through her pictures. She was still petite, but her body had developed curves in the last three years since I last saw her when she was fifteen. She now had firm b cup tits and a tight but well-rounded ass. In one of the pictures, she was sitting on her bathroom counter and wearing a pair of short shorts. They only reached the bottom of her ass, and most of her thighs were on display. I stared at this picture and had a difficult time accepting that the cute little girl had evolved into this sexy young woman. To add to the strange sense of familiarity to her appearance, she still had the same haircut she had when she was little, straightened past the shoulder black hair.

In the next picture, she was bent over towards the camera in a low-cut shirt that showed off most of her cleavage, flipping it off and sticking out her tongue. There was a metal stud in the middle of her tongue. Being with a girl who had piercings was always one of my fantasies. I wondered if she had any other piercings in other places.

I continued to look through her pictures. She didn't have a lot since this seemed to be a new Facebook account, so I didn't feel like too much of a creep when I made it through all of her photos.

She messaged me a simple "Hi." I couldn't believe that the girl I had just been picture creeping through over the last couple of weeks messaged me. I tried my best to wait a few minutes before responding so I didn't seem too eager. I lasted all of thirty seconds before I responded with "Hello."

"How are you doing," she asked.

"I'm good you? We haven't talked in forever."

"Lol, I know. I'm eighteen now by the way."

I knew she had been eighteen for a few months from her Facebook profile. This made me feel a little less like a pervert while I had been looking at her pictures. "What, that's crazy. Last time I saw you, you couldn't even drive yet."

"Yeah, I am all grown up now," she said.

"How have you been?"

"I'm doing bad. Like always, it seems," Lilah said.

"What's wrong?"

There wasn't a response for a while, so I started working on my paper again. A couple of minutes later, she responded. "My boyfriend cheated on me."

The thought of someone cheating on such a beautiful girl didn't make sense to me. "That is really dumb of him. I'm sorry."

"Thanks, it just really hurts. I loved him, and I have no one to talk to."

"I'm here for you."

She sent several smiley faces and responded, "Thank you."

"If I were your boyfriend, I would never cheat on you," I said as I started to feel braver. She sent me several hearts, and I sent back a hugging emote. I thought about how intricate courting must have been in the past and how now, a well-timed use of an emoji went a long way toward getting a guy a foot in the door.

We messaged throughout the night, asking each other about our lives since I broke up with her older sister. I found out she had been living with her ex-boyfriend but was now staying back home about forty minutes away from me. Despite the calmness in her messages, I learned that she had had a rough time in the last couple of years. She was guarded about what she said, but I knew it was due to her recent breakup and probably some others.

I checked my phone and realized it was past three in the morning, and we had been messaging each other back and forth the whole time. I hadn't made much progress on my paper, so right when I was going to say that I was going to go to sleep so I could work on it, she said she was tired and wanted to go to bed. I said good night, and a minute later, she said, "I love you."

I reread those three words to make sure I was reading them correctly. The three dots popped up, showing she was still typing. I expected her to say something more, but then they disappeared. My heart started to beat faster, but then I realized it was most likely the sibling type of love. We used to say it a lot when I lived with them. "I love you too," I responded.

I don't know how I was able to focus on my paper because I had an erection nearly the whole time from the conversation. Even though nothing sexual had happened, just connecting with her again had made me happy; apparently, it made my dick happy too. After two hours, I finally finished my paper just as the sun was rising. I quickly scanned the paper for spelling errors, and after a couple of fixes, it was as good as I would get it.

I hit the print button and turned my monitor off. I lay down while my printer screeched and screamed during the birth of my paper. I hoped to get a few hours of sleep before class at noon. As I thought about my conversation with Lilah and her pictures, I started to get hard again. I knew I wouldn't be able to get to sleep without masturbating.

I pulled out my phone to find something to masturbate to. I was thinking about going to a porn site, but when I opened my phone from the lock screen, it was still in the middle of Lilah's pictures on Facebook. I started at the first pictures and undid my pants. As I swiped through her pictures, I saw her developing breasts begin to get bigger and her feminine figure starting to become more pronounced. She must have hit puberty late.

As her body developed, so did her photography skills and confidence. She started using different angles in her pictures, letting me see how perfect her whole body was. She wore more revealing clothing and posed in sexier positions. I squeezed my phone as I approached my climax and quickly swiped through the last of her photos. The last one was of her in shorts and a crop top, bending over towards the camera and sticking out her tongue. The sight of most of her thighs, flat stomach, cleavage, and tongue piercing put me over the edge, and I started to cum. I caught most of it in my hand and cleaned up with tissues I kept beside my bed. I set my alarm for before class, and then I fell asleep.

I think I dreamed about Lilah, but they were those half-formed dream fragments from when your brain just barely reaches into REM sleep before peaking, and I started to wake back up. My alarm blared, and when I saw the time, I realized I must have hit the snooze button several times. I bolted awake and rushed to get ready for class.

As I rushed to shower, fragments of my dreams returned. Images of Lilah topless, but her tits were covered by the fog of the unknown. Of her lowering down onto her knees and unbuttoning my pants. Of her licking along my shaft with that tongue stud of hers. I still had an erection from when I woke up, and it was throbbing from my imagination running wild. I didn't have time to masturbate and tried my best to ignore my desires.

Fifteen minutes later, I was out the door. I made it to class just in time and turned in my paper on the professor's desk. I took my seat towards the back of class and settled in. I was exhausted and had an hour and fifteen minutes to survive before I could go home and nap before my next class in two hours. I tried my best to pay attention for all of five minutes, but I had already read the books the professor was droning on about and had no interest in taking notes. I stacked up several books and laid my phone sideways against it.

I spent ten minutes browsing the internet and different social media sites. I found myself looking back through Lilah's pictures when I got a message from her on Facebook Messenger. "So, I take it you liked my pictures?"

I didn't know what she was talking about. I wondered how she knew I was looking at them and if she knew what I had used them for. I looked at her pictures and realized my mistake the night before. I accidentally liked one of her oldest pictures. As I traced back through the photos I masturbated to the night before, I realized I accidentally liked increasing amounts of them as I had squeezed my phone tighter. While before I had skipped liking a few photos every now and then, once I got towards her newest pictures and where I had reached my climax the night before, I had liked every single photo.

I decided to try and play it cool even though I felt anything but. "Yeah, you are really beautiful. I had to like them."

"Especially the ones where you can see my tits and ass?" Lilah asked.

Shit, she got me. I decided to double down and hoped for the best. "Yeah, how could I not like those?" Feeling emboldened from not being able to take care of myself when I woke up, I added, "I wish I could see more." Unlike the previous messages, she didn't read this one immediately, and I felt like I had finally overplayed my hand. I could probably expect a call from her older sister later yelling at me for perving on Lilah.

I tried to focus on taking notes as a distraction from my embarrassment. I still had my phone open and would glance at it occasionally. Fifteen minutes later, I saw that she was typing. I was ready to apologize when she said, "Here is some more." In the picture, I could just see her upper body and face. She had her shirt off and was just in her red bra, which complimented her slightly bronzed skin. She was pressing her tits together so that the amount of cleavage between her tits looked even better. She had to be a b cup at least, the perfect amount to be able to rub my cock between and tit fuck. My erection twitched at that, and I looked around to see if somehow someone noticed my erection and could read my thoughts. Most other students were also on their phones, so we might as well have been in different worlds.

She sent another picture with her bra strap sliding down her shoulder slightly. In the next picture, the strap hung loosely on the inside of her elbow. In the next, the straps were entirely off, and she was holding up the bra by cupping it against her tits.

"I'm not going to be the only one sending pictures, am I?" She asked. I couldn't believe that this was happening.

"I'm in class right now," I said, wishing I was home.

"So?"

Lilah's argument was more persuasive than any academic paper could ever be. I got up and left the classroom. There were about thirty minutes left of class, so I felt I had enough time to see how this played out. I walked downstairs to the basement level of the building, which was always less crowded than the floors above. I went into the furthest stall from the door.

I had never masturbated in a public setting, and I was nervous about getting caught, but the thought of getting the pictures to continue from Lilah helped me get over my nerves. I pulled out my dick and started to stroke myself. I opened my phone and flipped through her pictures. Once I was fully erect, I held my dick up with my palm supporting it from below to provide some scale. My dick was six and a half inches long, which was about average, but it was thicker than average, a fact that I had always been proud of.

I had never sent nude pictures before, so it was a day of many firsts for me. I switched to my camera and took a picture. I looked at the picture to make sure it looked good, but I wasn't a scholar in taking or viewing photos of dicks so I figured it was good enough. I sent the picture before I decided to back out.

Lilah immediately responded, "That looks like a mouthful ;)." She then sent me another picture. Her bra was gone now, and she was covering up her perky tits with one arm. She had placed her arm so that I could see the bottom curves of her breasts; her nipples were barely covered. She looked down and slightly to the side, strands of her dark hair draping across her face.

In the next picture, she was cupping her tits and pressing them up and against each other. Her fingers were sprawled out, and her middle fingers just barely covered up her nipples. I could see some of the edges of her areolas that were pink. I masturbated faster. I couldn't believe that I was seeing so much of this beautiful girl.

"I'm about to cum."

"Send me a picture when you do."

My dick was throbbing, and I enjoyed what I had seen, but I wanted more. "Send me a picture showing me your full tits."

This time, it took her longer to reply, and I started to slow my jerking down in case I got something better to look at. She responded, "Why see them in a picture when you could see them in person? Tonight work?" I had no plans for Halloween other than watching scary movies. The thought of being with her in person, of fondling those perky tits and her petite body pressed up against me put me over the edge. I moved my hand over my erupting head and caught most of my cum. Three thick ropes of cum shot into my hand and stretched across my fingers. I switched to my camera and took a picture of my cum filled hand, and sent it.

"That's a lot! Make sure to save some for later."

"I will try, but who knows? I might get bored during my next class."

"Careful, you might get caught and be known as the chronic masturbator at school," she sent with a tongue-sticking out emoji.

"Good point."

After being tensed up for so long, I leaned against the wall and wiped my hand off with toilet paper. I washed my hands and walked back to class. I was only gone for about 15 minutes. When I returned to my seat, I wondered if anyone suspected what I just did. I tried to suppress my smile. I was so happy that I felt like I would float away.

Lilah told me there was a costume party later on and asked if I wanted to be her date. I said yes, even though I hadn't bought a new costume this year. She asked if I had a costume with a mask, and I told her I had a Michael Myers one from last year. She said that was perfect. The rest of the day passed uneventfully. My other classes were the ones I liked more, but after what happened, I think the one I left to sext Lilah in would always have a special place in my memories.

I finished my school day at five and went home to get ready. When I stepped out of the shower, I saw Lilah messaged me, asking when I would head over. I said I would be there in forty minutes and rushed to finish getting ready.

Once ready, I put her address in my phone's GPS and started driving. Lilah lived in the next city over that adjourned the one I lived in. While I lived near the heart of the cities bunched up in the desert, Lilah lived in one of the outskirt cities that was more open desert than developed city. The sun was on its slope downward as I pulled onto the freeway and started the longest leg of the drive.

I was listening to music from my phone connected to my car's Bluetooth when the messaging chime interrupted my music. I unlocked my phone and looked down at what she sent me.

"Here's a sneak peek." The following picture was taken at a downward angle, showing off her entire body. She was wearing a tight white button-up top that had a large opening on top that showed off her cleavage. One hand was under her shirt, caressing her tit. She wore a plaid skirt that didn't even go to the middle of her thighs. She had her legs slightly opened so that the skirt rose up, allowing me to see most of her inner thighs. While I had seen her in less earlier, the outfit added to her sexiness, and I couldn't wait to see it in person.

I pulled off the freeway about ten minutes from her address and followed a narrow two-lane road. For the next five minutes, nothing but cactuses and other desert plants were growing along the lanes. When I started to get closer to the address, the road expanded to four lanes, and buildings cut away increasing amounts of the desert. I lost track of how many housing developments in construction I passed.

The address led to a nice but uniform-looking neighborhood. Palm trees lined the streets, fitting because Lilah lived on Palm Avenue. I pulled into the driveway and messaged her, telling her I was there. I got out of the car and saw Lilah standing behind the screen door. She looked like one of those beautiful dancers who danced behind screens, using their figures and lithe movements to attract. I had only ever seen them used in movie backgrounds and mostly laughed at them, thinking of them as sexy shadows. Looking up at her silhouette, I now understood how the unseen could be so desirable.

When I was walking up the steps, Lilah opened the screen door. I started to say hi when she rushed out the door and slammed into me with a hug. I wasn't expecting the hug, so I nearly stumbled back down the steps. I hugged her back and absorbed her momentum by spinning her around like I used to when we would goof around together. She couldn't have been more than 110 pounds. Lilah laughed as I spun her, and I laughed with her.

I set her back down in front of the door. I was a full head taller than her, and she looked up at me. She was wearing make-up that was just the right amount to accentuate her natural beauty and wasn't caked on. Her eyelashes were curled, and she was wearing black eyeliner. The makeup complemented her hazel eyes, which were sparkling with happiness.