Message from Maddy
Seeing those words the next morning instantly gave me morning wood. But unfortunately, the message was a blue box.
{“Holy crap!!! Did I do that lolll?”}
She was referring to my erection, and obviously already knew that she was responsible for it.
{“of course! Wish I could’ve watched when the gown came off…
”}
I wanted to see how far Maddy was willing to go.
Now that graduation was done, I was seeing more of her. Our interactions were becoming increasingly awkward given the pictures we’d exchanged, which we obviously couldn’t discuss around Mom and Katie. There was a lot of catching each other’s eyes and quickly looking away.
“So Mads, who ya bringing to the wedding?” Katie asked one night at dinner.
“Huh?” Maddy responded, confused.
“Oh, Maddy I never got around to telling you cause of all the grad stuff. Your uncle has given all you guys a plus-one for his wedding,” Mom explained.
“Ohhh,” Maddy thought out loud. “Well, I’m not seeing anyone,” her eyes darted at me and then instantly back to Mom, “so, guess I’ll just go stag….are you guys bringing people?” She directed toward Katie and I.
“Jordan and Kelly, surprise! Surprise!” Katie said.
“That’s fun!” Maddy said.
“Yeah, you should bring someone, don’t wanna be stuck dancing with Brian and letting him cop feels all night at the reception,” Katie said.
“Katie be nice!” Mom said.
“C’mon you know I’m right,” Katie tilted her head at our mom. Mom rolled her eyes but she did slip a little smirk on her face. “Mom said we can just bring a friend, too.”
“Really?” Maddy asked.
“Yes, I don’t want you to feel left out. It’s not as if your brother and sister are bringing
real dates, anyway,” Mom said, seemingly more annoyed with Katie than myself.
“Yeah, you guys are cheating!” Maddy started. “We all know Katie’s gonna spend the whole night with Kelly and Drew with Jordan, haha.”
“Hey, no one’s judging you Mads. It
is pride month, after all,” Katie said.
“The wedding’s in August,” I said.
“Shut up, Drew. Bigot,” Katie joked. Mom laughed, and rolled her eyes at us.
“I’ll ask Kenzie and Ara,” Maddy said.
“Oh, sweetie, you just have a plus-ONE. I could call Jim and see, but you should probably plan on just one of them for now.”
“Okay,” Maddy said, dejected. “Doubt they could both come, anyway.”
“Are you girls packed by the way?” Mom asked, changing the subject. Mom, Katie, and Maddy would be flying out to Stanford for one more college visit as Maddy was still undecided.
“Mom, we don’t leave for 3 days,” Katie said.
“I know, but I hate it when you two do everything last minute.”
“We’ll be fine.”
Mom brushed Katie aside and turned to our younger sister. “Maddy, I want you to pack today, okay?”
“How come I have to but not her?!” Maddy protested.
“Well, because…” Mom looked at Katie and laughed to herself. “Because there’s no controlling her!”
“Ha!” Katie said triumphantly, grabbing her dishes and strutting out of the room.
“You realize how backward that is, right?” Maddy said.
“I know, I’m sorry, Maddy. But if I push her too hard, she’s gonna…” Mom paused, and wiped her eyes. Oh, no. Here we go again…
“That’s okay mom!” Maddy cut her off. “I’ll go pack now, okay?”
“Okay,” Mom smiled at her youngest daughter.
Maddy gave me a quick look and walked up to her room.
Message from Maddy
Maddy snapped me while she was upstairs packing and I was downstairs watching TV. I was alone, and felt safe opening it.
{“Greedy!!
but I don’t send videos
”}
Well, I was glad she knew what I was asking for at least. Or at least didn’t act like she was clueless. I responded quickly.
{“haha did you send pics b4??
”}
Maddy is typing…
Message from Maddy
{“touché lol”}
{“maybe u can try on some of those Stanford outfits for me…”} I texted back.
A couple minutes passed.
Message from Maddy
Red box! Oh shit! I clicked on it, but was disappointed to find Maddy fully dressed in the pic, wearing a sexy skirt suit. Her blouse was only buttoned up 3/4 of the way, definitely not how she’d be wearing it on her visit.
{“was just about to send this haha”} her caption read.
I texted back. {“dang…will definitely be turning heads out there!”}
She responded {“
”}
I left it at that, not wanting to come off as too pushy or desperate.
The next day I was off and went for a bike ride through the park. Everybody raves about Central Park, and rightfully so. It’s a cool oasis in the middle of the concrete jungle. A nice way to get away. But when you’ve grown up on west coast parks and mountains, it’s hard to be impressed.
I sped through the paved pathways, constantly avoiding the tourists (of which 10 months ago I basically was one) who wandered out in front of me.
Bzzzz……Bzzzzzz……Bzzzzz
I felt my phone vibrating in my pocket. I slowed my pedaling down and squeezed on my breaks, before pulling off to the side of the trail to come to a stop. The serious bikers zoomed past me and I could feel a breeze each time as they didn’t even bother to slow down.
Message from Maddy
Message from Maddy
Message from Maddy
Wow, three of them. That was probably good news….
I found a shaded spot where my view wouldn’t be disrupted by the glare of the sun. I opened up her messages.
Boom! First pic was a bikini shot. She appeared to be in a dressing room and was wearing a red high-rise suit. She looked stunning, as always. I read her caption:
{“Drew! Which one you like the best?!?!”}
The timer ran out and Maddy’s next pic popped up. This one was a one-piece. Leopard printed.
{“2!!!”} her caption said. Swimsuits were nice, but I sighed as I realized I would not be receiving nudes.
Maddy’s last pic was her in a more traditional, lower cut suit. This one was light blue, skimpier, with strings. Definitely my favorite.
{“last 1!!”}
I thought about it for a sec. And I thought about Maddy wearing that last skimpy bikini around Stanford, all the California bros checking her out. A rage of jealousy came over me. I realize this was stupid, but I replied back:
{“think I like the 2nd!”}
It covered up the most. I stashed my phone away and continued on my route. I felt my phone buzz a bit later but wasn’t in a rush to open the message. I figured it wasn’t anything good. I rode for almost two hours before stopping at one of my favorite local deli places. I grabbed a sandwich and enjoyed it in the park before continuing on my ride back home.
When I entered the condo Mom was the only one home.
“Hi Drew!” She greeted me, cheerfully.
“Hey, mom,” I replied.
“You wanna help me with dinner? Both your sisters will be joining us as well,” Mom asked.
“Sure thing, but mind if I shower real quick?”
“Of course! Go right ahead, I’m gonna start getting stuff ready.”
I raced upstairs into the bathroom. I opened up Maddy’s response.
{“Ok! I ended up getting all 3 of them tho lol”}
I sighed. I could already see her drifting away on the back of some tool’s surfboard. Wearing her little powder blue bikini. The douche teasingly tugging at her strings….
I wasn’t gonna give up without a fight.
I pulled out my phone and filmed my mirror reflection as I stripped my shirt off. I made sure to flex every muscle I could, without making it obvious that I was doing so. My skin was nice and bronze by this point in the summer, and the sweat gave it a nice glimmer. I lowered my shorts down to reveal a bulge formed under my boxer briefs. I said nothing, and didn’t look at the camera as I stripped. I strategically stepped in front of a flower vase, and lowered my briefs. The flowers covered my cock – barely – but you could definitely see my rippling quads and the rest of my nude body in the video. I stopped filming and watched it back. Don’t get me wrong, the video was pretty douchey. But it’s hard to be a guy and not come off douchey when doing these things. And I thought I looked good. I typed out a message:
{Nice! Was hard to pick anyway!}
I fired off my video to Maddy, showered quickly, and came back downstairs to help Mom.
I began chopping up some garlic and onions. Mom had already gotten water boiling and had patted dry and seasoned some chicken breasts. She had also sliced up a zucchini into rounds.
“Drew, do you know if Maddy’s been seeing someone?”
My hand slipped and I nearly sliced a finger. My mom’s comment came out of nowhere.
“Err, not that I know of? She said she wasn’t last night. But how would I know?”
“Oh, I don’t know. You two get along better than Katie and Maddy, so I thought she may have said something to you. She seemed to make it a point last night to say she wasn’t seeing anyone and it just got me wondering you know?” Mom asked.
“Uh huh.”
“And then today, we were shopping, and she just seemed a little extra bubbly and checking her phone a lot. And she took FOREVER to try her swimsuits on.”
I gulped.
“I just thought, maybe she was asking for an opinion from someone different than her mother.” Mom said.
“Yeah, I don’t know. I don’t think she would tell me though. Was probably just texting and asking her friends,” I replied. Mom didn’t look convinced. “Look, ma. When she’s seeing someone seriously, she’ll let us know. If she really liked someone, I’m sure she would bring him – or her – to the wedding.”
“Oh, it will
definitely be a him,” Mom chuckled. “Katie – I never know. She surprises me all the time and doesn’t seem impressed by anyone. But Maddy, she’s ALWAYS been boy crazy. I mean, even last fall when you showed up was too much for her. She was – oops!” Mom flushed and covered her mouth.
“She was what?” I asked.
“Nothing, Drew. I’ve already said too much.”
“Aww, c’mon!” I let out. But I quickly contained myself. I didn’t want to come off as too curious.
“Drew, don’t tell your sisters what we talked about, okay? They should be home shortly,” Mom asked.
I sighed. “Alright.” I opened my phone and saw that Maddy had watched my video. But she hadn’t responded.
The two of us finished the prep work and I grilled the chicken breast. We tossed everything together in a sauce to complete a chicken pasta dish. Mom poured us all some red wine right as my sisters showed up.
“Mmmm that smells good!” Maddy said. But she didn’t make eye contact with me, nor greet me.
“Yeah, wow Mom, thanks,” Katie said.
“Don’t thank me, thank your brother! I did the easy stuff,” Mom said.
“Thanks Drew,” Maddy said, shyly. She gave me a quick smile. She made her way to the dinner table.
“Since when can Drew cook like this?” Katie asked. “I wasn’t even aware he could boil water.”
“Speak for yourself,” I said, “Last time I saw you in a kitchen you served me pink chicken and tried to claim that it was ‘sushi-grade’.”
“Bahahaha!” Katie burst out laughing. “I was like 12!”
“Oh my God, how did I never hear about this,” Mom said. “You didn’t eat it did you?”
“He DID!” Katie continued to laugh.
“I took A bite!” I protested. “And then instantly spat it out.”
“How you guys made it as far as you did, I’ll never know,” Mom shook her head. “C’mon, let’s eat!”
We all sat down and began chowing down.
“Gotta say lil bro, you outdid yourself. This is delicious,” Katie gave me an uncharacteristically genuine compliment.
Maddy shook her head yes, but didn’t look up.
“Did you ever think about working in a kitchen?” Katie asked.
“No. But I’ll be honest, this is just following a recipe – and it’s not even my recipe, it’s mom’s,” I said.
“Whoever’s it is, it’s good,” Katie started. “It’s actually pretty impressive you’re able to cook like this, and STILL can’t get laid.” Ahhh, there’s the Katie I know and love.
“Katie!” Mom scolded her.
I caught Maddy’s eyes for a split second. Even she was giggling.
“Mom, I’m JOKING!” Katie said.
“We don’t need to talk like that at the table. And YOU’RE one to talk, anyway!” Mom said.
“Hahahhaah!” I couldn’t contain myself at the rare Mom-Burn. Katie shot me a
really? look. But Mom had actually gotten her to blush.
“Wow, Mom. That hurts,” Katie said sarcastically.
“Oh, hush, I know you got thicker skin than that. But I’m sorry. I just want you guys to stop teasing each other,” Mom said.
“I’m sorry Drew!” Katie said. Obviously not meaning it. I just smirked at her.
We finished our meals and Maddy ran up to her room afterward. Katie and I put on a movie. Mom originally joined us, but got too tired about a third of the way through it and went to bed.
About thirty minutes after Mom shut her door, Katie slid over on the couch next to me. She began casually rubbing my thighs.
“Ohhh,” I blurted out, surprised.
“Shhhh,” Katie whispered. She reached her arms under her shirt and finessed her bra off without exposing anything. She rubbed her toned legs against me, and slid her other hand onto my abs. “Gotta admit, it’s pretty hot when a guy can cook,” she said.
“Oh yeah?” I said.
“Mmm Hmmm,” she muttered.
I reciprocated her thigh massage. My dick was already stiff. I let it rise up under my athletic shorts with pride.
“Oh, hey there,” Katie whispered. She hungrily pulled the waistband of my shorts and underwear down and my erection sprung out freely into the living room. She grinned and began tying her dark brown hair into a ponytail. She looked at me, and her big brown eyes bore into my own. “Quiet, okay?” She commanded. And then she bent down to my groin, and inserted my penis into her mouth.
“Ohhhh fuck!” I let out. Not too loudly, but loud enough for Katie to look back up at me. Seeing my hot big sister with my cock in her mouth as she gazed into my soul was more than enough to make me cum, but I fought it off.
Katie refocused on my dick. Using one hand to jerk my shaft, and the other to caress my balls, she gave me the best blow job of my life. I tried to reach my hands down to her own privates, but the way she was sitting, her puss was too far away. So, I slid my hands up and rub and squeezed her big tits.
BZZZZZZZZ BZZZZZZZZ
I felt my phone vibrating in my pocket. Which could only mean one thing.
Maddy. Was she working on her own version of my shower strip video I sent earlier?
“Mmmmm,” Katie mumbled and her eyes shot to my pocket as she continued to gargle on my cock.
I heard the shower start upstairs. OH SHIT! But I forced my mind to go elsewhere. I didn’t want to ejaculate 60 seconds into Katie sucking me off.
I lifted Katie’s shirt up, and her fabulous rack bounced into my view. FUCKKKK.
“Mmmmmm,” Katie moaned again as I exposed her boobs. She began going deeper and deeper, nearly getting my entire dick down her throat. Without gagging.
I continued to squeeze and jiggle my sister’s hooters, as they hung and swung freely beneath her chest. I wasn’t going to be able to last much longer. I felt Katie’s tongue licking against the cut end of my cock when she retracted to the tip. And then her cheeks squeeze against my shaft as she gave a full effort suck when she slid back down to the base.
“Katie!” I whispered.
“Hmmmm?” Her voice was muffled.
“I’m gonna….”
“Mmmm hmmm,” She continued to rhythmically pleasure me with her mouth. I took that as an okay.
I focused on the whole picture in front me. Katie’s big naked tittes, her shiny dark hair pulled back, and her pretty eyes and face as she buried them into my cock and balls. My toes clenched, and I felt an incredible jolt as I busted into my sister’s mouth.
“MMMMMM! MMMMMM!!!” Katie’s muffles had more startle in them. She kept her lips wrapped around my dick, taking in all the semen. Her eyes flickered back up at me with amusement. She slowly and cautiously pulled away, keeping her hands over her mouth, as her cheeks were puffed out like a squirrel full of nuts.
Katie got up off the couch and quietly ran into the bathroom, presumably to spit out my ejaculate. I sighed, slightly disappointed, as a part of me was hoping she would swallow it. If she had, I don’t think I ever would’ve gotten that image out of my brain. I quickly cleaned myself up with some nearby tissues and pulled my shorts back up. Never know when someone could walk out.
Katie re-emerged but didn’t say much. She picked up her bra, smirked at me, and said, “night” before hurrying up to her room.
“You don’t wanna finish the movie?!” I cried out after her.
“It was boring!” Was all she said before swinging her door shut.
By the time I lumbered upstairs myself, both my sisters’ lights were turned off. I went into my room and checked my phone.
{“
”}
{“u kindaaa have a nice body
”}
Well, it wasn’t a video, but I was happy enough with Maddy’s response.