I’m not sure how I let all this happen, but last weekend was the craziest weekend of my life. My name is Leslie. I am, 19, 5’ tall, and about 100 lbs. I am home from school for summer vacation.
I have a younger brother, a Senior in High School. We have had a typical relationship. We either love hating each other or we hate loving each other. At this time in our lives we were becoming the kin of good sibling friends that we would be for the rest of our lives.
He has a girlfriend. Her name is Cathy and they have been together of a year and a half. They are intimate. I know because I walked in on them the second night I was home. I didn’t know her and hadn’t met her up until that night. After I quickly closed the door, I made myself scarce for a while. They took their time finishing up and when they came out of the room they looked a bit unsure.
“Hi. I’m Cathy.”
“Hi I’m Leslie. I’m sorry to have busted in on you like that.”
“It’s ok. Better you that his folks.”
“How long have you two been together?”
“You mean dating or fucking?”
“I guess fucking.”
“A little over a year. We come over here when your folks are out because things at my house are a bit out of control sometimes.”
We talked some more as my brother puttered around the house. They acted like my mom and dad did. They seemed to have a seamless relationship. She was 1 year younger than me and since I was home for the summer and all of my friends were from college, it was looking to be a lonely summer.
“Leslie, we have a pool at our house. Why don’t you come over and visit?”
She seemed nice so I said yes and on Saturday I planned on going over to Cathy’s house with my brother, but at the last minute he got called in to work at the Home Depot. I was going to stay home, but he and Cathy encouraged me go. So I went to my room to pack. I was on the college swim team and had brought my training equipment home so I could workout with my old swim club and had it in a mesh bag that would let it dry out each day and not get moldy or grow fuzzy stuff. I dumped the training fins, and the hand paddles, kickboard, and snorkel out of my equipment bag and tossed in two bikinis, a water bottle, sun screen and one of our huge beach towels.
I pulled on a pair of shorts and a tank top. At school I seldom wore panties or a bra and I didn’t bother with them now. I wasn’t sure which bikini I was going to wear based on the situation at Cathy’s pool. One covered my cheeks and all of my breasts. The other was much skimpier for tanning and had a thong bottom and allowed my breasts a lot more sun.
I got into my car and punched Cathy’s address into my phones Google maps. It told me the drive was about 20 minutes and I started the car and took off. When I pulled up to the house there were a lot of cars outside the house.
I was a little peeved figuring she was having a party and didn’t tell me. I didn’t want to hang out with a bunch of 16-18-year-old high school kids. I was just getting ready to turn around and drive away when Cathy came out of the house to get something from one of the cars. She saw me and waved, and I was stuck.
I parked and grabbed my bag out of the trunk. I figured if it was a bad situation that I’d make some excuse and just leave. When Cathy let me in I was greeted by a woman in her 30s, as it turned out I found out later she was 39. She was wearing a cute bikini and had a black wrap around her.
“Oh, you must be Leslie, Cathy told me that you were coming over. I am Cathy’s mom, Judy. Please come in.”
As I walked, Judy headed off to the back of the house and Cathy led me through the living room. I passed a big set of picture windows and looked out the window to the back yard. There were a bunch of people outside around a bi pool. From what I could see they were all in their 30s and 40s. Judy explained that they were her husband’s friends from his basketball league. There were more men than women.
Cathy came back for me, since I had stopped to take in the situation.
She took my arm and dragged me to her room. When we got to her room I had to start asking questions.
“What is going on?”
“My parents have a big party about every month. Everyone is my parents age and having you here gives me someone to hang out with.”
“Why me? You must have other friends.”
“Actually, I don’t have any friends other than your brother. My family is kind of unusual and I don’t want others to know about them. Your brother found out by accident and I thought that he would leave me, but he didn’t. He doesn’t care for my family a whole lot and doesn’t come over here when they are having a party, unless he has to.”
“Don’t be. I’m 18 and I never expected your brother to be ‘the one’, but he is understanding and accepting of the situation with my family. I love him and he loves me. I used to watch you at the swim meets last year. I watched you and your brother interact and that was what made me want to meet him.”
“I have to ask. I have never asked your brother, but from seeing you two together I have always wondered. Have you and your brother ever hooked up?”
“Really? You two seem so close. I watched how you touched each other and it seemed more than brother sister touching.”
“I guess we were curious, we saw each other naked and we used each other to learn about the opposite sex. But we never hooked up. We felt each other up and I learned how a dick works and he learned how to touch a pussy. We never had sex.”
“Did you ever give him a blow job?”
“No. I jacked him off a couple of times to see what came out. Then I did it again to see how far he could shoot.”
“He shoots pretty good.”
“I know he shoots a lot. I don’t know how good he is.”
“Maybe someday you should find out.”
“Nah, he isn’t my type. Beside now, I know and I can get my own guy.”
“Have you had many guys?”
“Only three. I was a virgin until I got to college. My first was with a guy on the team at a party. We both got drunk. He is still my best friend, but we don’t date. I think he might be deciding if he is gay.”
We talked for a while about her and about sex and our thoughts. I got to know her better. I liked her. We were becoming friends.
“Come on, let’s go swimming.”
I pulled the two bikinis out of my bag as Cathy started undressing. I watched her as she began to strip. She was pretty much a younger version of her mom. 5’7, 120 lbs, dirty blonde shoulder length hair, maybe 34B tits. Her mom was probably about 10 lbs heavier.
She turned and saw me looking at her and smiled and started undressing for me. It was kind of fun. She had already pulled her top off. She lowered her hands to her waist and slowly wiggled out of her shorts. She was wearing a cute matching bra and panty set. Then she reached behind her and undid her bra. Her tits came into view. She cupped them with her hands and giggled. Last she pushed her panties down over her hips, exposing her smoothly shaven mons.
“You’re turn,” she said.
She pulled me to my feet and unzipped my shorts and pushed them down until they fell to the floor. I was a little shocked and not sure what to do. I let her. I also realized that I was liking it.
“Mmmmm, no panties. Hot. I thought you swimmers all shaved.”
“I don’t like to shave every day. I shave for big swim meets, but otherwise I let it grow and trim the edges, so it doesn’t bush out around my suit. Bushy hair sticking out of a swim suit is kind of gross, I think.”
“Do you have a thick bush?”
“Yeah, if I let it go I get really thick and curly and it grows all the way up to my belly button.”
“The black hair against your white skin is sexy.”
Cathy then took the seam of my tank-top and lifted it over my head. Since I wasn’t wearing a bra, Cathy took the time to admire my curves
“I love your tits. Are they a C cup?”
“Just. During the swim season when I am keeping my weight down, they are a B and are a little floppy. When I stop working out they fill out to just C and they fill out.”
Cathy reached over, cupped one and lowered her head to suck on the small red nipple. I moaned and put my hand on her head. This was kind of new to me. I’d kissed a girl a few times. Mostly when out with friends. Mostly to tease boys. I always liked it. Girls were much softer. I didn’t stop her. Again, I realized I liked it. She worked on the other one for a minute and then stopped.
“Please kiss mine, otherwise it won’t be fair.”
I leaned over and took one of Cathy’s very hard pink nipples into my mouth and took the time to feel the texture and the heat of her tit. Cathy looked down at me and caught my eye as she smiled. I changed over to the other nipple and noticed that she had begun to perspire a bit and her other nipple had a salty taste to it.
“Thanks, that was nice.”
Cathy went to her dresser and pulled out a tiny bikini. It was yellow and it was little. I reached for mine and picked up the one with more coverage. She looked at it, then the other and handed the smaller one to me.
“Let’s give the old men a thrill,” she said.
I pulled on the bottoms and set the thong between my cheeks, then put on the top and moved it around to cover as much of my breasts as could. Cathy’s bottom was also a thong but the top barely contained her tits. The string of her thong was so thin she looked bottomless from the back. I was one to talk. Mine fit the same way. We headed out to the pool and Cathy patted me on the ass a couple of times.
“These guys are going to go nuts!”
As we walked out onto the pool deck, everyone, men and women, stopped to look at us. Judy said nothing about the bikinis, but she smiled.
“Hey everyone. This is Cathy’s friend Leslie.”
She started to introduce me around. There were four couples, four single guys, and Cathy’s dad Jack.
I said the obligatory ‘Hi’s’ and then Cathy and I swam, hung out, and talked. Every once in a while, I would notice that the men and the women were staring at us. We ignored them and just hung out. They would try and engage us every once in a while, but it was mainly to get a better look. For the most part we kept to ourselves in the deep end. Cathy had gotten us big water bottles full of lemonade.
We were there for about two hours when the party started to die down. All of the couples left and it was just Jack, Judy, the four guys and us. Jack had a beer in his hands and was sitting in a chair with a mellow buzz. The four guys were chatting up Judy. She was liking the attention. She’d giggle or laugh every once in a while.
After a bit Judy announced she was going to go and change. She was still in her bikini. The guys protested. That made her laugh.
“At least let us choose what you change into.”
“Oh no. It would be silly of me to let you guys choose.”
The guys started trying to convince her to pull her top off and give them a good look. She laughed and called to Jack for help.
“You’re on your own. Leave me out of this.”
Everyone laughed, and Judy eventually said they could choose. She went to her room and came out with two summer dresses. The guys said they couldn’t pick that way. She’d have to try them on. “Ok. I’ll be right back.”
She came out in a calf length white sundress. It was very pretty. She did a slow turn for the guys. The guys all rejected it. She then came out in another calf length dress, did the same slow turn, and looked at them. They rejected that as well.
Cathy and I were laying on two rafts by then and she had not noticed what was going on with her mother. I called it to her attention. She turned her head to watch as Judy went back in the house and came out wearing shorts and a top. The slow turn was now standard.
“Nope! Go back to the sun dresses only.”
The guys all declared.
“Jack, what do you think?”
“Oh no. I told you, you are on your own.”
He just raised his beer and toasted her.
Judy went in and came out in a knee length dress. The guys rejected it immediately. Judy groaned, grabbed a beer and went back to try something else. This went on for a while. The dresses became more revealing.
“Judy, you are getting closer.”
“You guys are not going to be happy until I am naked. Jack”
Judy giggle as she said that and looked at her husband when she pleaded out his name.
“You can handle it babe.”
After a few more dresses, each a bit more revealing, and all rejected by the four men, Judy finally came out in a red sundress that came just barely below her ass. It showed a lot of cleavage and showed that she was braless. When she did her turn a bit of her ass showed from my angle. She was either wearing a very small thong or she was going commando.
“Nope! You are hiding all the good stuff, Judy.”
“Well this is it. I have emptied my wardrobe.”
“Ok. I guess the guys and I will have to make due with that.”
With that, the guys continued to talk/flirt with her while Jack just sat nursing his beer. You could see the flirting getting a little more friendly. She would touch an arm or a shoulder. They would do the same, sometimes an arm around the waist.
She went to get some snacks. One guy offered to help and followed her into the house.
“Cathy, I need to use the bathroom. Where is it?”
“Inside and to the right.”
I got to the side of the pool and rolled off the raft and stood, adjusting my top. As I passed the kitchen Judy was working at the counter and the guy was glued to her back and talking softly in her ear. Every once in a while, she would giggle or laugh. Finally, she picked up the tray with snacks and turned around. The guy stepped back but was looking straight down the top of her dress.
Whatever he said made her giggle again. She turned to bring the snacks out. He swatted her ass. She looked at him pretending to disapprove and then walked away smiling. He followed and when she got to the door, she wiggled her ass at him and he swatted her bare cheek before she went out.
I hit the bathroom and went back outside. The group had formed around Judy again. At one point a strap fell off her shoulder. She fixed it. One of the guys pulled it down again. She protested and looked at Jack. He just shrugged. She left the strap down. The touching and laughing continued, but this time their hands were lower. Definitely touching her ass through the dress.
“Hey, Judy. Stand up and give us another turn. I didn’t get a good look at the dress earlier.”
“What material is that?”
He grabbed the hem of her dress and pulled it up. Everyone could now see that Judy was wearing a thong. She slapped his hand playfully, turned back to them and continued to flirt. Everyone was getting more flirty and soon hands touched her lower onto her thighs.
The men were now caressing and stroking her shoulders, arms, and her thighs. One of the guys began to fondle her ass under her dress. Judy slapped his hand but giggled and as I watched as more guys grabbed her. She continued to slap their hands away, but not as often and not as hard.
I looked to see if Cathy noticed. She did. She was watching intently. She saw me looking at her and she shrugged her shoulders. It was starting to get cold.
“Come on Leslie. Let’s go inside, I’m getting cold.”
We went back to her room and I pulled my tank-top and my shorts. Cathy pulled on a top and skirt, but no panties.
“Hey girlfriend, if you ain’t wearing underwear, neither am I.”
She then stepped up to me, grabbed my ass and kissed me. It was a nice kiss. I kissed back. We made out for a while. We kinda laid on the bed snuggling and kissing until we both heard our stomachs grumble.
Once downstairs, we saw that the party had moved inside. Jack was sitting in a chair, still nursing a beer. He didn’t seem drunk. Judy was sitting on a guys’ lap. It was the same guy who followed her into the kitchen earlier. The other three guys were standing around them.
Judy’s dress was bunched up at the top of her thighs. She was not sitting on the dress and the guy was wearing shorts. He definitely had Judy’s naked ass against his naked thighs. Judy turned her head and noticed us.
“Hi girls. How are you doing?”
“We’re good mom, just getting something to eat.”
When we got in the kitchen she looked at me and said in a low voice.
“That is going to be so fucking hot! Did you see the way they were touching her? And Dad just watching? I wonder if he’d let them fuck her. Wouldn’t that be awesome to watch?”
“Cathy that is a little bit sick, isn’t it. I mean watching you mom fuck other guys is a bit out there.”
“I guess I watch too much porn.”
We got our snacks and as we walked back in the living room we saw Judy kissing the guy. She stopped as soon as she saw us. I think she wanted to think we didn’t see. When we got to her room Cathy gushed.
“Did you see that? Mom was kissing that guy! Dad’s just watching. That is so hot. I wonder if we can watch from the hall.”
She opened her door quietly. We snuck to the end of the hall. We were as quiet as we could be. I’m not sure it would have mattered. All the attention was on Judy, who was now definitely kissing the guy. He had her dress pulled up far enough where we could see her thong.
“Hey this is not fair. Where is my kiss?”
Judy gave him an impish grin as she sat on the first guys lap and grabbed the second guys shirt, pulled him down, and kissed him.
“Hey! What about us?”
Judy laughed and proceeded to kiss them all.
The guy whose lap she was on used this opportunity to pull her dress up higher until it was almost bunched around her waist. One shoulder strap had fallen, almost exposing one breast completely. Another wiggle and her nipple would be showing.
“Another round of kisses please.”