Family and Friends Miss Playoffs

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19 yr. old and friend entertain family and then dad's friends.
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Imstillfun
Imstillfun
10,226 Followers

It was Sunday morning. I just woke up and I had as a message from Kara. I'd been buried at work and hadn't talked to her for 3 days. Kara is my BFF. My name is Lisa and I'm 19 years old.

She asked me what I'd been doing and I told her a work project and that I was sorry to be out of it for so long. She started telling me about what was going on. We chatted for a while and then she invited me over. I never said no when she invited me. I liked hanging out with her. I said yes and we made plans. I felt relieved for the return of my normal life.

I got out of bed to get dressed. Normally I would just throw on Jeans and a T shirt. After all, I was just going to Kara's house. I go all the time. Today I stopped and thought. I looked in my closet. As I did I started thinking.

Kara lived at home. She had a younger brother who was 18. I'm 5'2", 110 lb, 36c, with dark brown hair down the middle of my back. I always catch him checking me out. He follows me around like a puppy dog. He's an A student, very smart, but I didn't think he had much experience with girls. I'd never heard of him dating.

I remembered that Kara once said she'd even caught her father checking me out. We always joke that I should flash them my tits and see what happens.

I admit I liked the attention and after working so hard I was feeling flirty and a bit of I want to go wild.

Just as we joked about her family checking me out. I would point out that her younger brother was always trying to peep on her. Kara was 19, gorgeous, 5' 7", 125lbs. She had dark skin and dark hair. There was some Hispanic in her. She had a high firm ass and great tits. She'd just laugh and say she'd caught him looking. She even once told me she caught her father looking down her shirt. He had turned bright red and turned away.

I figured I was just going over there. If they were going to check me out I should look good. I grabbed a short denim skirt. It barely covered my ass. I found a fitted white button down top and one of my sexiest bras. It was pink, push-up and barely covered my nipples. Last I added a cute pink thong, I wore sneakers. I wanted to look casual.

I put the outfit on. I looked hot. You could see the bra through the shirt, but that was OK in today's casual styles. If I bent over a little my ass started to come into view. I left enough buttons unbuttoned so I was showing cleavage.

I jumped in my car. I noticed as I did my skirt slid up and my panties were showing. I thought it would be fun to get stopped by a cop. Then I wondered if Kara's brother or father were home. I found myself hoping they were.

Kara's brother answered the door. At 18 he was cute. He was also awestruck. He just stood there blinking. I knew he had a crush on me, but this was adorable. Finally I said, "Can I come in."

He moved out of the way and tried to stammer something. It was funny. Kara came down the stairs. She looked at me and then at her brother.

She laughed and said to me, "What are you trying to do, kill him?"

I laughed. Her brother told her to drop dead and ran out of the room.

Kara looked at me again and said, "What's with the outfit?"

I replied that I thought I'd give her brother a treat.

She laughed and said, "Well, everyone's home, so I'm sure you're going to get attention in that."

Everyone. Oops, I forgot about Kara's mom. I mean she was cool, but I had no idea how'd she react. Then again, I'd seen her dress to go out. 5'6" maybe 140, but she was built and knew how to show it off when she wanted too.

I walked into the house. Mom and Dad were in the living room.

Dad was the first to see me. At first he just stared. Then he said, "Hi Lisa, haven't seen you all weekend, how have you been."

Lisa's mom turned to look at me. I answered her Dad. "I'm doing great Mr. H. I've been buried in a work project."

"Hi Mrs. H," I said.

"Hi Lisa. Don't you look hot today. Whose heart are you trying to break, or catch. I pity him."

"No one special," I replied. "I've just bed cooped up so long I wanted to dress up a bit."

"Well," she said, "judging from Ricky's reaction, you've succeeded."

I looked where she looked. Kara's brother was just standing there staring.

His face flushed, and he said, "Mommmm!!"

I walked over to him. I'm only 5'2", he was taller. I knew when he looked at me he could look right down my cleavage.

I smiled at him and said, "It's ok Ricky. I'm flattered you think I'm pretty. Any girl would be happy with attention from someone as sweet as you."

I kissed him on the cheek. He just blushed.

Mrs H said to me, "classy." Referring to how I handled Ricky.

Kara said, "Let's go up to my room."

I don't think anyone realized Ricky was right at the bottom of the stairs. As I followed Kara up he was watching me. I was pretty sure he could see up my skirt. Just for fun I dropped my phone. As I bent over to get it, turned, looked at Ricky, and blew him a kiss. I'm pretty sure my entire ass was on display. I thought to myself that left him with masturbation fantasies for years to come.

Kara and I went to her room. Nothing special. Just girl talk. After about an hour I wanted a coke. I asked Kara if she wanted one. She said sure. So I got up to go downstairs and get them.

Mr and Mrs H were still in the living room. The couch had a view of the kitchen. A dirty thought crossed my mind. I thought about Kata and my joke about flashing her dad too.

As I walked past them I said, "Just getting some cokes."

I went to the cabinet to get some glasses. At 5'2" I had to reach. I could feel the air on my ass as my skirt pulled up.

Then I went to get some ice. The ice maker was in the bottom freezer. I bent over to fill the glasses. I was sure they both got a good look at my ass.

I filled the glasses with coke and headed back upstairs. As I walked past them, Mr H tried not to look at me, but Kara's mom just smiled.

"Got everything you need?" she said.

"Yes thank you," I responded.

I headed back up to Kara's room. I told her what happened.

"Well aren't you the little slut," she said.

I told her it was kind of exciting to be checked out like that. We talked for a while longer. Mrs H asked if I wanted to stay for dinner.

We all sat at the table. Mr. H on one side of me, Ricky on the other. I knew that by looking down they could both see my panties. Mr H was about 6' and certainly got a great view of my cleavage. They both spent dinner trying to not get caught looking. Kara noticed. I'm pretty sure Mrs. H did too.

Dinner was nice. I really like Kara's family and the added sensation of showing off just added to the fun.

After dinner Kara and I went back up to her room.

"Wow, my dad was really checking you out," said Kara.

"I noticed," I said. "It kind of turned me on."

"I gotta admit, it looked fun," she replied," I was kind of jealous.

We hung out a bit more and it was getting to be time to go. We said our goodbyes and I headed downstairs to let myself out. Mrs. H was still in the living room. I said goodnight.

Mrs. H. came over to me. She took my hands and kissed me on the forehead. She'd never done that before. Then she whispered softly in my ear. "Great ass. If you got it, flaunt it." She then lightly kissed my earlobe.

I was stunned. I stammered, "Thank you."

She laughed and said, "Don't be a stranger. We'd like to see more of you. Lots more."

With that I left. I got in my car and took a deep breath. I could not believe she said that.

I had just got home from work the next day when Kara texted me. I replied.

"Hi"

"OMG, OMG, OMG"

"What happened?"

Kara told me that after we talked. She decided to get a coke. She told me she heard the TV downstairs. She usually sleeps in just a big oversized T. She said she'd been thinking about what I did to Ricky and her dad and that nobody'd seen her ass in a while. So she threw on a T that just barely covered her ass. When she got downstairs Ricky was watching TV. When he saw her he couldn't stop looking. She said it made her feel kind of sexy.

She said went to the fridge. She could tell Ricky was watching her. The urge just came over her. She bent way over. To get something out of the Fridge. Her T shirt slid way up and her ass was completely showing. Then she remembered she wasn't wearing panties.

"LOL. you slut"

"I know! But it just felt so wrong and so hot. I liked it"

"LOL. yep, sounds slutty to me. I love it!"

Kara told me she stayed like that for a second and then turned and saw Ricky staring. She thought he'd look away.

"I think he was so shocked he was mesmerized."

"LOL. wouldn't doubt it. You have a great ass. Probably the first pussy he ever saw"

"Yeah, no doubt

She went on that since he was staring she looked back at him and, still bending over a bit, put her fingers to get lips and said Shhhhhh.

She then stood up to go back upstairs.

As she walked by Ricky watched her. When she got close he said, "Kara. You are so beautiful."

It was so sweet. He was looking at me with these big puppy dog eyes."

She kissed him on the forehead, thanked him, and told him that was sweet.

"That was kinda sweet," replied.

"Yeah, I thought so."

She went on. It was so sweet that when she got to the bottom of the stairs she stopped to look at him. She said "promise you won't tell?"

He promised

She pulled her T shirt up to her waist and turned around for him.

"LOL. OK, that is slutty. But sounds fun."

She told me it was. Ricky just said he loved her and she went upstairs.

"I can't believe how hot, and sweet, it was."

"Sounds it. Bet he'd die if we did it together."

She LOLed. We chatted a bit more. Then said good night

After that I watched some TV, and then I went to my room to climb into bed. I lay down, closed my eyes, I started thinking about my conversation with Kara. I fingered myself to orgasm thinking of Kara and Ricky, and fell asleep.

That Tuesday after work, as I usually did, I picked up my iPad and texted Kara.

"Hey Slut. Lol. Whatcha doing."

"You would not believe what happened."

"What?

She told me that after everyone had gone to bed last night Ricky knocked on her door. She opened it. He had this shy little kid look on his face. She asked him if everything was alright and he said yeah. Then she asked him if he needed anything.

"What did the cute little perv want?"

She told me he was looking at the ground and said, "Can I see your butt again?"

"LOL. he is a little perv."

"I know. But it was kinda cute"

"Yeah, It is. what'd ya do?"

Kara said she kissed him on the forehead and told him to go sit on the bed. She was still dressed from the day. She told him if he promised not to tell he could watch her change.

"LOL. you are a slut. Sounds fun!"

"I know. I couldn't believe I was doing this."

"So, tell me everything. What were you wearing."

Kara told me she was wearing a skirt and top.

"That all?"

"No, I was wearing underwear."

"I said tell me everything. Details girl. Details."

"LOL. OK OK."

She said she was wearing a lacy white thong and matching bra. She got back to her story.

He promised not to tell and sat on the bed. He had his hands folded on his lap. He looked like he was sitting in church. She realized he was trying to hide his erection.

She turned on some music and decided to tease him a bit. She stood facing him and slowly unzipped her skirt. It fell to the floor. She stepped out of it and slowly turned around showing off her ass. She could see his hard on through his pajamas it was too big to cover with his hands.

She then pulled her top off and threw it at him. He grabbed it and used it to cover his crotch.

She reached to undo her bra. It was a front clasp one. She stopped went over to him and said , "You do it."

"OMG, he must have died."

"He just stared at me."

Finally she convinced him it was ok. He reached out, fumbled with the clasp, and finally got it undone. She had her hands over the cups so it didn't show her tits.

She stood up and said, "ready?"

He nodded and she let the bra fall off her shoulders to the floor.

She cupped her tits with her hands and said, "Have you ever seen tits before?"

He just stammered something

"LOL. you tease"

"I know, but it was so much fun I couldn't help myself."

"I could have watched."

"Who you kidding. You wou would have undressed me."

"True. Don't stop! Then what."

Then she turned her back to him and slid her thong slowly over her ass and let them fall to the floor.

As she did he groaned and then said "oh no!"

"Oh no?"

"Yup, the poor kid came on my top. LOL"

"LOL"

He started to apologize. She told him it was OK and that sometimes girls found it flattering when boys couldn't control themselves. Here she was naked and comforting him.

She told him it was time to go. He better clean up and go to bed. He nodded and got up to leave. She picked her thong up off the floor and asked him if he wanted to take them with him. He just nodded. She handed them to him, kissed his cheek, pushed him out the door and shut it.

"OMG. that is so hot," I replied

"That is so wrong."

"LOL. I know that's what makes it hot."

The next day was crazy at work. I didn't get home till late. I got online. Kara messaged me.

"You are a bad influence."

"LOL, I know. What happened."

"Well little perv came to my room last night. He looks so pathetic. I told him he could watch me change again. This time while watching me change he pulled out his cock and started jacking off. I was shocked he was so brave. Plus he had like a 7 or 8" cock.

"Wow, that's pretty cool! I wonder how big your dads is."

"Let me finish. So I undress while he jacks off. Then I give him my panties and send him to his room. I got to admit. I was a little tempted to help him. LOL."

"Naughty Naughty!"

"Oh yeah, like little miss show him all, wouldn't be tempted."

"Tempted? Hell yeah, hey, I'd even watch you. :)"

" :). OK. anyways. You know I always sleep in a big T shirt."

"Yeah."

"Well lately I've been sleeping in shorter ones. It's fun. Ricky and dad would look at me as I went to the kitchen or something. Mom saw it yesterday and said. 'A little short isn't it?' I just told her I was comfy. She said, 'well, you do look cute'."

"That's pretty cool."

"But that's not all. So the other day I go downstairs to get something to drink. Dads in the living room. I remembered flashing Ricky and how fun it was. I said, 'hi daddy.' as I walked by. Then I went to the fridge, bent way over to put ice in my glass. I knew he could see my ass and pussy."

"You are turning into a slut. I like it."

"I know. Somehow I think it's your fault, but I'm loving it. Anyway. As I'm bending over Dad says, 'Have told you lately how pretty you are?' I just stayed bent over and looked at him and said, 'no, that's so sweet of you.' I then stood and faced him. Yawned and stretched my arms over my head. My pussy was totally showing."

"OMG. What did he do?"

"He asked why a pretty girl like me didn't have a boyfriend. I went over and sat on his lap. He's in a pair of soft shorts. My bare ass was right on his lap. I hugged him and said, 'Because no one compares to you.' I could feel his cock getting hard. I wiggled my ass on it kissed him goodnight and ran to my room."

"OK that is hot. Hell. I'd sit on his lap too. We should do a sleep over."

"Totally," Kara said.

When I got home Thursday Kara wanted to know if I wanted to come over. I said OK and just drove over in my work clothes.

Today I had worn one of my sexier outfits. All this talk with Kara was making me feel a little wild. It was a wrap dress of a clingy material. When tied it crossed my tits and you could see my cleavage and bra. If you looked you could make out my nipples. The bottom of the wrap opened about 2" below my pussy. Sitting at my desk it had completely fell to the sides and showed my panties and a bit of belly.

I am admin help in a small office. I sit behind a desk all day. No one could see. It felt kind of hot knowing I was exposed and no one could see. I wondered what Kara would say.

I let myself in. Kara's mom was in the living room.

"Hi Mrs. H," I said.

She turned looked at me and said, "Hi Lisa, isn't that a sexy dress."

I knew it was, but I played it off. "Just something I wear to work," I said.

"Well, it's adorable," she said. "Kara's in her room." Then she laughed and said "Don't let Ricky see you in that dress, he'll probably have a heart attack and die."

I laughed and went up to Kara's room.

"Some dress," she said.

"Like it," I responded.

"Yeah, I do. You'll have to let me borrow it someday."

"Your 4" taller than me. Your pussy and ass would be hanging out,"

"So?" She said.

We laughed and started talking. I was sitting on the bed. Just like in the car my dress parted and my panties were showing. Kara noticed, called me a slut and we laughed. We spent some time hanging out. All of a sudden her brother knocks on the door.

Kara told him to come in. He came in and was surprised to see me there. He then noticed my panties were showing. He turned red and looked away.

Kara said, "what's up."

He stammered, "Never mind. I'll talk to you later."

Kara said, "It's Ok, what's going on."

At this point she knew what he wanted and was just teasing him. He looked so cute. Between looking at me, being 18, and wanting to see his sister naked. It was just adorable.

"Come on in," Kara said. "I've got a surprise for you."

He came in the room.

I was sitting on the bed. Kara told me to come over to her. I got up and stood near her and her brother. Next thing I knew Kara was reaching for the tie on my dress. If she untied it, the dress would fall apart. I'd basically be in my bra and panties. I could have stopped her but the idea turned me on. I let her pull the string. My dress fell open. I was standing there in a matching bra and a really small see through pair of a cross between boy shorts and bikini panties.

Ricky's mouth dropped open.

I pulled the dress back, so could see better, and put my hands on my hips. "Happy" I asked?

He nodded.

I said to Kara, "I better be going."

I looked at Ricky standing there just afraid to move.

I said, "I've got something for you." I slowly wiggled out of my panties and handed them to him. I then tied my dress back up.

Kara just smiled at me and mouthed, "You're such a slut."

She then scooted Ricky out of her room.

"I bet he jacks off with those for a month," she said.

"That's gross," I said. "We will have to keep bringing him new ones."

I let myself out and headed home. It was about 10 and I went to my room. I climbed into bed. My fingers reached for my pussy. I realized that I fingered myself to sleep every night for the last few nights. I think that was more than the last 2 months. I smiled, and did it again.

Saturday Kara texted me and asked me if I wanted to hang out. She said her mom wasn't home. I told her I had to shower and would be over after.

I jumped in the shower thinking about the stuff that had been happening. I grabbed the shower massage and brought myself to a nice orgasm. I then dried off and went to my room to change and grab clothes.

I decided to wear a short white sundress to Kara's. It was a shirt dress and buttoned all the way up the front. I buttoned only the essential buttons. The dress was a gauzy material. With the light behind it, it was barely there. I put a yellow thong on under it. You could see the contrast. I grabbed a pair of tiny boy shorts panties and short tank top to sleep in.

I jumped in my car and headed to Kara's. I let myself in. Her dad was in the living room watching a game.. "Hi Mr H. "Where's Kara?"

Imstillfun
Imstillfun
10,226 Followers