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.
Last time my brother’s girlfriend was over she asked me if I wanted to hang out sometime. I didn’t know Cathy well. She was 1 year younger than me. I’d spoken to her a few times but really only knew her as my brother’s girlfriend. I was home for the summer most of my new friends were from school and I’d lost touch with most of my high school friends. She seemed nice so I said yes.
Last weekend she asked if I wanted to go swimming. They had a pool, it had been hot, and so I said yes. I threw on a miniskirt and top and I threw 2 bikinis in my purse. I wondered which I’d try. I’d wait till I got there. One was much skimpier for tanning. I didn’t bother with panties. I admit I don’t always wear them and I was just changing when I got there.
When I pulled up to the house there were a ton of cars outside. I was a little peeved. I figured she was having a party and didn’t tell me. I didn’t want to hang out with a bunch of 18 year old high school kids. I figured I’d make some excuse and just leave. A woman in her 30s opened the door. 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,” she said.
She introduced herself as Judy, Cathy’s mother, and invited me in. There were a bunch of people outside. From what I could see they were all in their 30s and 40s. Judy explained that they were her husband’s pickup basketball friends from the league. There were more men than women.
Cathy came in from the back.
“Oh great, you’re here,” she said. She dragged me to her room.
I asked what was going on. She told me about the party and that she invited me because they were her dad’s friends and she wanted someone to hang out with. I had to ask why me. She must have other friends; we didn’t really know each other except through my brother.
I remembered that I’d actually walked in on them having sex in the basement more than once. I assumed they were pretty active as they must have done it more than I caught them. She said she hadn’t seen or heard much from my brother lately
I said I was sorry, but she stopped me. She went on to say that she was only 18 and never expected my brother to “be the one” but that she had always admired me and wanted to know me better. She didn’t want my brother to be our only relationship. She figured that was over, so she’d invite me over.
It was mature and sweet. I just said, “Cool.”
We chatted a little. For someone who dated my pain in the ass brother she was actually sweet, smart, and mature. We talked for a while about her and I got to know her better.
We got on the subject of sex. She told me that she’d only done stuff with my brother but at night she watched Internet porn. Almost everything turned her on. I laughed. I admitted I’d slept with 3 guys and none of them were very good.
We talked a bit more. I liked her. We were becoming friends.
She then asked if I wanted to go swimming. I said sure and pulled 2 bikinis out of my purse. She started undressing. I watched her as she undressed. She was pretty much a younger version of her mom. 5’7, 120 lbs, dirty blonde shoulder length hair, maybe 34c tits. Her mom was probably about 10 lbs heavier.
She turned and saw me looking at her as she undressed. She 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. She was now naked.
“You’re turn,” she said. She pulled me to my feet and unzipped my skirt. It 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,” she said.
She then pulled my top off over my head. I wasn’t wearing a bra either. She looked at me and said, “I love your tits.”
She reached over, cupped one and lowered her head to suck on it. I moaned and put my hand on her head. This was 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.
She went to her drawers and pulled out a tiny bikini. It was yellow. I reached for mine. I picked up the more coverage one. 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 my bikini on as she put on hers. For 18 it was very revealing. It barely contained her tits. Half her ass was showing. I was one to talk. Mine fit the same way. We headed out to the pool. As we walked out back, every one stopped to look at us.
Judy said nothing about the bikinis. She made no notice. She announced that I was Leslie, Cathy’s friend. She started to introduce me around. There were 4 couples, 4 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 would watch 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.
The party started to dwindle. All the couples left. It was just Jack, Judy and 4 guys. 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.
She announced she was going to go change. She was still in her bikini. The guys protested. That made her laugh.
One guy eventually said, “At least let us choose what you change to.” She laughed and told him he was silly.
The guys started trying to convince her. She laughed and called to Jack for help. He held up his hands and said, “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 2 summer dresses. The guys said they couldn’t pick that way. She’d have to try them on. Judy said OK and went to her room.
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 had not noticed what was going on. I called it to her attention. We were both lying on lounges. She turned her head to watch.
Judy came out in shorts and a top. The slow turn was now standard. The guys rejected it. They told her dresses only. She looked to Jack for help. He just raised his beer and insisted that he was not a part of this. She went in and came out in a knee length dress. The guys rejected it again. She groaned, grabbed a beer and went back to try something else. This went on for a while. The dresses became more revealing. The guys started joking she was getting closer. She giggled and said they were not going to be happy till she was naked. The guys all laughed and agreed.
She looked to Jack for help again. He just held up a palm and said she was on her own.
A few more dresses. Each a bit more revealing. All rejected. She finally came out in a red sundress. It came an inch below her ass and was very low cut. It showed a lot of cleavage. It had to be worn braless. When she did her turn a bit of her ass showed from my angle. She was either wearing a thong or going commando. The guys rejected it, but she said this was it. She didn’t have anything else. They grudgingly agreed.
The guys continued to talk/flirt with her. 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. I got up to use the bathroom. As I passed the kitchen she was working at the counter. The guy was like 2 inches behind her 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. He followed as she got to the door, she wiggled her ass at him and 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.
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