My Summer Endeavours

CHAPTER 1

I woke up on a sunny Friday morning at about 8am. I just had that feeling that this was going to be a very enjoyable day. Little did I know how the day was actually going to unfold. I hopped out of bed and briefly checked myself out in the mirror. "Hmm... My abs need a bit more work", I said to myself right before I headed out of my room to take a nice cold shower. The area I lived in had recently gotten really hot so I often wake up all sweaty and smelly.

I got into the shower and proceeded to clean myself as I thought of what I should do today. "Maybe after breakfast I can play a video game for a while, and then probably head out to the public pool", I thought to myself as I pushed the tiny lever to shut off the water and start soaping myself up.

As my hands moved downwards my mind drifted off a bit and I started to recall my last dream. It started playing out in my head as I walked into what looked to be a hotel room and saw my mom seated on a chair at the far end of the room, and a red-headed woman lying on the bed, naked, talking to her.

The conversation died out as they took notice of me and my mom introduced me to the lady whose name I do not remember. "She's pretty horny and ready for a nice hard fucking. You think you can help her out?", my mom asked me. I nervously nodded and then slowly walked towards the naked lady.

I started to strip while she stared lovingly at me. When I took off my boxers and my hard cock sprung free the naked lady commented, saying "That's a pretty cock you got there". She motioned me to move forward and as I got to just about 3 inches from her she gently grabbed my dick and started sucking on it.

I started to jerk my hand a bit faster on my cock as I remembered how good it felt, or at least how it would've felt, to have her beautiful red lips around my cock as she slowly bobs her head up and down my hard shaft, bringing me closer and closer to orgasm.

That was just about as much as I remembered but I extended the scene as I wasn't quite done in the shower. I thought of her taking my cock out of her hot mouth and turning around while scooting a bit forward so I could crawl onto the bed with her and give her the fucking she desperately needed.

I held my cock at the base as I guided it into her warm wet opening, and she gave out a long low moan as I slipped it into her as deep as it could go. Then an instant later I started drawing back and pushing forward ever so slowly and before I knew it I was picturing us in the midst of some very hard and very fast sex, with my mom still on the chair fingering herself as she watched. A while later the redhead started shuddering and making short, high-pitched sounds as she rode out a very intense orgasm.

As I pictured mom cumming on the chair as wel lI felt my oncoming climax and let myself ride the waves, as I was also shooting my load in the shower. Apparently I didn't completely close the door on my way in (in our house, an open bathroom door means that it's empty) and I was so lost in my fantasy that I didn't hear my sister walk in.

The shower water wasn't running so I guess she thought nobody was inside. After my very satisfying cum I decided to step out of the tub and get some toilet paper to wipe off the cum stains since it doesn't mix with water very well. I pulled the curtains open and was quite shocked to see my older sister standing there with her eyes wide open and a smirk her face, and in her underwear no less.

My dick had gone a bit softer 'cause I was standing in there for a while after my orgasm but as I noticed the very odd predicament I felt my downstairs member start to fill with blood once more.

She started to speak and said "Sorry, I didn't hear the shower so I thought no one was um...". Her words trailed off as she noticed my cock hardening and her eyes darted towards it. She stared for a few moments at my dick as I also studied her body for the first time; her cute nose and beautiful lips, her firm round breasts held by a green and black zebra striped bra with a revealing amount of cleavage, the wonderous curves of her hips, her slim and slightly toned-

"I thought nobody was inside", she continued to speak.

"Can I uh... can I finish up in here Julie?", I asked her, and she replied "Oh yeah, yeah, sorry", as she turned around and walked out of the bathroom. I followed her out with my eyes and stared at her ass as she walked away and reached behind her to grab the doorknob and close the bathroom door.

I stood thinking to myself about what just happened and asked myself "Why? Why on this day?". After a while I came back to my senses and grabbed the toilet paper and procceded to dispose of the cum and finish up with my shower in a mortifying rush. Boy, was this going to be an awkward summer.

CHAPTER 2

After I left the bathroom and got dressed to start my morning I lied on my bed for a while and kinda soaked in the weirdness of the morning so far, and how it would affect the future; all the fmaily gatherings that would be filled with tension, all the silent dinners, all the dull home-alone nights we'd have in case mom was out somewhere or fell asleep early.

(Our dad had divorced our mom and left her for a younger lady.)

A while later I decided to head downstairs and grab something to eat so I could officially begin the morning, in my sense.

I saw my mom at the dining table having her breakfast and we exchanged good mornings, then she told me a bit about her plans for the day (our usual chitchat).

I still stood a bit away from the table while I was listening to her talking and as she started eating she picked up one of her sausages (we always have the thick ones) and fed it into her mouth my mind wandered off and fell into another extended play of my previous dream in the hotel room where, this time, my mom was the one sucking my hard dick with her eyes closed just as they were right now.

My mom snapped me out of it when she said "Honey, you're staring". I came back to and told her I had gotten lost in my thoughts for a moment. I then moved towards the kitchen to get myself some food and I felt a part of me bump into the counter just a little bit, then I realized I had gotten hard whilst thinking of my mom's hot mouth. I hoped she hadn't seen that, or at least didn't relate that to her eating the sausage.

------

A few minutes after finishing her meal, she returned downstairs as I was still eating my food and gave me a kiss on the cheek as she said goodbye and left for work. My mom was a somewhat successful businesswoman so she rarely needed to go to work early.

After I finished my food, I decided to start on my gaming time so I headed for the TV, switched it and the console on, grabbed my treasured red and black controller and got my game on.

A few minutes later I heard a door open and close, then some footsteps down the stairs and I tried as much as I could to look like I was lost in the game as she passed by and headed for the kitchen. I paused the game and followed her.

"Hey, can we talk?" I said as she was pouring her cereal into a bowl. She turned around and I couldn't help but glance at her boobs as they appeared, now holstered by a low-cut white halter top. I could still see the valley between her breasts and I noticed that she wasn't wearing a bra. Just as you'd expect, I started to get hard. I asked her how long she had been in there and she replied...

"I got in just before you finished."

"Well, that doesn't really make it any better."

"It's okay Danny, I mean we all masturbate sometimes."

"Well, I didn't really pick the best time to do so."

"Oh I don't know, you could've just left the water running. That way I wouldn't have come in. That's what I do."

"I guess I didn't really think of that", I said, "I got lost in my thoughts during the shower, I hadn't really planned on doing it then and there. Thanks for understanding, Julie." Then I moved in to hug her as I finished.

"No problem, it happens."

As she stepped out of the hug to grab her cereal and walk out of the kitchen I realized that I had forgotten about my erection and it had been pressing it against her for the duration of the hug. Also, on the off chance that she hadn't noticed, she might have seen it before that. Anyways, I chose to brush it off since she didn't say anything about it either and go on with my day.

I had gone back to playing my game for a bit and Julie eventually joined me there to watch and take a short turn playing as well. A few minutes after she handed the controller back to me she asked me like she'd ask any normal question...

"So how big is it?"

"Huh?"

"How big is your penis?"

"Why do you ask?" I tried my best to sound as casual as possible when I asked that question. I even carried on playing as I said it.

"None of my ex-boyfriends and not many of the pornstars I've seen have one as big as yours, so I was just wondering how big it is."

I had thought of lying to her and giving her a false measurement, but then I told her its actual length. "It's um... it's just under 10 inches long."

After a moment of silence she then added, "And how thick?"

"I didn't know measuring thickness was a thing, I've never checked that."

"Hmm...that's pretty big." She said, as she continued to watch in silence. Then she rose from the couch and said she was going to pee. She also asked if I wanted to go with her to the library but I kindly declined and told her I was thinking of going to the town pool with some of my friends. She said "alrighty" and carried on to the bathroom. I went to my room a bit later to change into my swimming trunks.

Afterwards I went back downstairs to turn off the console and TV and just when I thought of going to Julie's room to inform her that I'd be taking off she appeared at the stairs ready to go. She was wearing the same white halter top but had changed into a pair of tight black skinny jeans. She also had tied her long blonde hair into a ponytail and had painted her lips a faint red colour. I couldn't help but stare at her very attractive figure as she walked down the stairs. Thankfully she was looking at her feet the whole way down or she would've seen the perverted look on my face.

"Do you mind dropping me off at the library since you're taking the car?", she asked.

"Yeah sure, let me grab my keys."

We remained silent all through the drive up until she pulled out her phone and connected it to the car then played our favourite album. We gave each other a smile as the first song started playing and before we knew it we were singing along to the songs. At about the start of the fourth song we had arrived at the library and as I stopped so she could get out she said " see you later" as she disconnected her phone then turned to get out of the car. I watched her ass slowly move away as she got out and closed the door as she spun around to give me a little wave. I drove away and headed for the pool as I thought to myself "I never realized how hot my sister was".

------

I had decided to head back home a while later and pass the time. I had arrived at about 4pm, and as I got in I saw Julie on the couch watching some series. I joined her and sat down to her right, right next to her.

"Hey. How was your day?"

"Oh, you know, the usual pool stuff. You?"

"I read some books, then went to a friend's house to eat and hang for a bit, then came here."

"Cool."

As we sat watching the show (it was one of our favourite shows) there came a scene on screen in which a girl at a bar had grabbed one of her friends and started making out with her. We carried on watching and I started to feel my genitals filling with blood. I didn't wanna squirm or anything to signal my predicament so I just sat still watching them share their spit. I guess Julie's eyes had wandered to my crotch and then, with a grin on her face, she said...

"Someone's enjoying the show."

I was a bit taken aback by her comment, but then I just went with it and replied, "Well it's hard not to get aroused watching two hot women kiss on TV."

"For you, maybe."

"So you're not even the slightest bit turned on by this?"

"Well, I'm not really into lesbian stuff so nah, not really."

After the scene had ended she stood up and asked me if I wanted to join her in her room to listen to some music. I said "sure" and followed her there, staring at her ass all the way.

After a while of listening to music, my eyes began to wander around her room and I happened to spot something purple and shiny under her pillow. I asked her as I got up from my seating position on the floor "What's this thing?" and as I pulled it from under her pillow I realized what it was. It was her dildo. It's smaller than my dick, I thought to myself as I held it in my hand.

"That...is my bedroom companion. For when I'm in the mood."

"I see. How long have you had this?"

"About three years."

"But you just turned 20 a month ago. How'd they let you get it?"

"They didn't. They let mom get it."

"You mean that's mom's dildo?"

"No you idiot. She got this for me as a while back. I was still new to the whole sex thing then so I told her about the first time I played with myself in the shower and my first orgasm, and she went and got me that so I could um...get the whole experience."

"Wow" was all I could spit out of my mouth then.

"Yeah."

After a moment she then said "Looks like someone liked hearing that story" as she blatantly stared at my very hard dick pointing away from me in my shorts.

"Uhhh...errmmm..."

"It's okay Danny, I don't mind. It was a pretty hot story after all." She winked right after she said that.

We continued listening to some music, occasionally shifting to her laptop to check out any new songs that our favourite bands would've released and any other songs we'd find on the web. Eventually we heard our mom's car pull up downstairs and we went to say hi and help carry anything that she'd be carrying.

------

It had become nighttime, the three of us had eaten dinner (our dad had divorced our mom and left us for another woman) and mom had retired to her room to do some work and, eventually, sleep. I was downstairs on the couch watching a late night movie, but later on I decided on bringing down one of my porn movies to watch on the big screen.

I had gotten into it and ended up pulling my cock out of my pants and started wanking it, when I heard a little shuffle behind me. I quickly turned my head and saw Julie standing right behind me leaning on the couch. She had a wicked smile on her face as she said "Don't stop on my account." I sat still, dick in hand, looking her in the eye without a word from the both of us for a few seconds until she said...

"Oh come on. We both do it, does it really matter if I watch just this once?"

"I don't know sis. This feels kinda weird for me."

"Just give it a try, Danny." She said this with a loving look on her face. The kind of look a mother gives her little boy when he's afraid to get into a pool for the first time. I turned my head back to look at my busy, though not so busy now, hand and I slowly started to pull it up and down my shaft. Some moments passed by and then Julie suggested, "You should try lubing up down there. I bet it'd feel a lot better."

"I've never seen any of the guys do it in the porn I watch."

"That's because their dicks end up in wet pussies."

She then left the living room for a minute or two and as she came back she stood right in front of me holding a bottle of lotion. She told me to pause my jerking as she bent over and squeezed some out and right onto my cock. I took the hint and started spreading it all around my shaft as I continued to slowly jack my cock off right in front of my sister.

As I looked up at her I noticed she was wearing a really short nightdress that barely covered her pussy, and her boobs stretching the front of the dress away from her. My eyes fixed on her chest as I started to pick up my pace and, I guess she noticed me staring because she then undid the two top buttons of her nightdress, allowing me to see the bare tit flesh that was underneath. It wasn't much, but it was enough to send me into overdrice as I started furiously pumping at my dick, still gawking at her cleavage.

She bent over again, this time looking into my eyes as she said "Are you close yet?" with a sexy smile on her face. She wasn't standing very close to me so when she bent, I could see her face close to mine and her magnificent braless tits hanging out of the dress. This became too much for me and I moaned out loud as I started to cum real hard.

I felt the first powerful shot being ejected from my cock and, with my eyes looking right into hers, I saw the rope of cum fly from right out of view and hit her right between the eyes.

Surprisingly, she didn't back away but only close her eyes out of shock so the second shot, though not as powerful as the first, flew towards her as well and hit her right on her lips. The following shots didn't reach that far up and ended up falling on the floor making a puddle of cum right at her feet. I was still breathing somewhat deeply as she stood up straight and said...

"Wow. That's a lot."

"Well, I don't usually um... give out that much."

"I see...It went quite far. There's a lot of it on my face", she said with a little giggle.

"Yeah, sorry about that."

"Don't worry, not your fault." She went to the kitchen, grabbed a couple of napkins, came back to right in front of me, got down on her knees and started cleaning up the cum puddle.

"Thanks, sis."

"For what?", she asked as she looked up with a smile on her painted face.

"For cleaning that up for me...for suggesting the lube..."

"I should be thanking you, little brother, for the show AND the grand finale!"

I had tucked my deflating dong back into my pants wihle she was in the kitchen and after she was done cleaning up she put the used tissues in my hand as she said goodnight and walked back into her room. I couldn't help but notice she had a bit more swing in her hips than usual as she walked away.

I followed her, tissues in hamd, just a few seconds later and as I reached the top of the stairs Imanaged to catch up with her just as she had stopped at her door to open it. From the door of my room I said to her, "Goodnight Julie." She turned her face to me, gave me a little smile, and headed into her room as I then went into mine, disposed of the tissues, took off my shorts and hopped into bed. I fell asleep almost instantly.

CHAPTER 3

I woke up the next morning with my usual morning erection, and headed for the bathroom to pee. Even after the long pee my dick still hadn't gone down. Just as I finished up in there I realized that I had gone to sleep without my shorts and had walked out of my room with nothing on below my waist. Since all of my clothes, clean and unclean, were in my room I had to make a break for my room practically naked.

Just as I got out of the bathroom and reached right outside Julie's open bedroom she called out to me and I froze in my tracks.

"Where are your pants?"

"I slept without them last night and forgot about that this morning."

She laughed out loud and said "I see."

I still stood frozen at her door, and then after a few moments she asked me "Are you gonna go get dressed or what?"

"Oh, right right", I said as I kept on moving towards my room. As I entered, I saw my cum-stained shorts and I thought back to last night, and that some of my cum probably dribbled onto my shorts and I didn't notice. I folded it so that the dried up cum was hidden at the centre of the fold and held it in my left hand as I picked up the hamper from my room and took it downstairs to the laundry room.

As I entered the room I saw my mom already loading up the machine with some clothes. She was in her usual Saturday morning attire; oversized shirt and almost unseen panties due to the size of said shirt. She said good morning to me as I walked in, but she kept on adding her clothes to the machine.