This is my second post. It’s a long one. Check out the other one if you want one from my adult life!
So this happened in high school. I grew up in the Midwest. Not a small town, but not a huge city either. I grew up middle class, played sports, did well in school. My best friend was the same, but his family was loaded. This happened at their house.
The players:
—Me (16 or 17)
—Mark (best friend)
—Ryan (another friend)
—Jill (his older sister, college, ~19)
—Dani (her best friend)
—Liz (Dani’s younger sister, my ex)
At the time, I was really into playing sports. Not great, but I played. I was about 5’10”, 170lbs. Pretty slim. (In college is hit around 6’3”, 215) The thing was, I was already well hung. Looked even bigger because I was so skinny. That comes up later.
My friend’s family was loaded. They came from money and turned it into more money. Hard workers. They had everything. One weekend, the parents left town for a work trip. Ryan and I were going to stay the weekend at Mark’s. My parents didn’t care, because we’d drink but weren’t big parties.
We got food and watched movies. Played video games. Did stupid shit outside. They had a huge house out on an acreage. We got pretty drunk. Mark the most.
We were in their basement theater room watching movies around 10 when someone came in. It was Jill and Dani. They were in college and got dropped off there after they went out for a while. Both pretty tipsy.
They came in, made a ton of noise and then we all started hanging out. Drinking more.
Dani was an absolute knockout, but a huge bitch. Totally full of herself. Jill was down to earth. A huge smartass. And she’d tease me all the time. Not sexually. Just making fun of me, but in good fun.
I was infatuated with Jill. Some was the attention I got from her and her personality. Also her looks. Naturally beautiful face. Sandy blonde hair. A bit thicker and muscular from years playing soccer. About 5’5”. And…big tits. Like a teenager, I was obsessed with big tits. I had jerked off so many times thinking about her.
So we’re hanging out, drinking and laughing. Jill starts mocking me, making fun of my shirt. I was an athlete, but also kind of nerdy.
We all went up to the kitchen that had a huge tv room next to it. We got some food and drank a bit more. Mark and Ryan went and sat in the tv room. I was with Jill and Dani at the counter in the kitchen.
I should also mention Jill would tease me other ways. She always knew when I was sneaking glances at her tits. She’d arch her back or lean in if she had a low-cut shirt. This time was an arch, because she had on a tight sweater. My eyes locked on and I could feel myself getting hard.
Dani, the asshole, got a text. Her boyfriend, also an asshole, was coming over…but luckily just to pick her up.
She left and Mark passed out. Ryan, Jill and I watched a bit of a movie. Then she said it was time for bed. She was the least drunk, but said she had enough. She smiled at me then left. I watched her ass as she went away.
Ryan eventually passed out. I couldn’t sleep. I grabbed a mixed drink, some water and then headed to the theater room to watch something. Remember I said they were loaded? This house was massive. The theater room clear on the others side of the house from the bedrooms. I thought I’d have privacy.
I started watching something. I’m sitting there in a tshirt, baggy sweats…and briefs. Not boxer briefs. I liked briefs. Well, I started playing with myself. I was a bit drunk and horny.Then I decided to play Mario Kart on the giant screen for some reason.
A few minutes later, I got startled hearing footsteps. I hadn’t heard anything other than the game. I figured it was Ryan, because mark was shitfaced. Nope. It was Jill. She came back out of her room and was worried I drove home when she didn’t see me, but came looking for me when she saw my car outside.
“What are you doing, weirdo?” My heart jumped.
“Oh, hey Jill. I thought you were Ryan.”
She plopped down next to me. The theater room had long couches for seats. In the sim lights, she looked amazing. Hair down, black tights, baggy tshirt and definitely no bra.
She challenged me to play and kicked my ass. They had a bar in there, so she went and grabbed a drink. She came back and we talked and decided to watch something.
During the discussion, she said, “I heard about you and Liz. Sorry you guys didn’t last.” We has just broken up. It was rough. First serious girlfriend and we took each other’s virginity.
“Thanks. I don’t know what happened. It just…” Jill put her hand on my arms to comfort me, because she could tell it hurt.
Then she said laughing, “I also heard about you and Liz.” Dani had recently walked in on us. Both naked on the bed. Not having sex, but close. It was mortifying. I knew exactly what she meant.
Blushing hard, I said, “you heard about that?”
Jill: “yeah, Dani told me. Everything.”
I was so embarrassed. I didn’t know what to say. “Everything?”
Jill: “yep, but Liz told Dani everything before that, so I heard about you two even before that.”
I’m speechless. I just stared up at the screen.
Jill: “sounds like Liz enjoyed it. And sounds like you’ll have no problem finding someone else.”
“What do you mean?”
“Dani said Liz enjoyed the physical stuff…and Dani said you’re packing.”
“Packing?” I didn’t know the expression.
Jill laughed and gestured at my crotch. “She said you’re huge.”
My face was flush. My heart was pounding.
Jill got serious. “I’m drunk. I want to see it.”
I looked at her. “What?!?!” She was smiling. I could see those big tits in her shirt. I felt myself getting rock hard.
She put her hand on my thigh. “Come on…”
I lifted my shirt then untied my sweats. I started pushing them down, lifting my butt to slide them down further.
Jill: “ha! Holy shit. You wear briefs! I didn’t know that part.” I started to pull my sweats back up. “No no no, I’m sorry.”
I sat there, sweats down to mid thigh. Huge hard bulge it my briefs. Her eyes were locked on. I looked over and she smiled, then leaned in to kiss me.
“I’ve seen you staring” she said. “It always turns me on. And I loved hearing Dani talk about you.”
Her hand moved up my thigh as she kissed me deep. Her hand grabbed me, 8” fully hard. She purred. Stroking it, squeezing it. Then she stopped.
“Pull it out.” I did it slowly, fully hard. Her eyes got wide. She took her hands back then pulled her shirt off. I finally got a look at those amazing tits. I instinctively started stroking then leaned to kiss her.
Her hand replaced mine, stroking my thick cock. “I haven’t had one this big, this thick.” My mouth moved down her neck to her breast. Licking and kissing. Sucking the hard nipples.
She pushed me back then lowered her face. I could have cum as soon as her mouth touched my cock. I played with her tits as she sucked me off.
She quickly stood up. She pulled off her leggings. “Take off your shirt” she said as she pulled my sweats off as I sat there.
She straddled me. My briefs still on but pulled down enough to get my cock and balls out. She kissed me as she slid down my cock slowly. Her shaved pussy so wet. So tight. “You’re huge” she whispered.
She started riding me slowly. I said, “but…”
She knew what I was going to say. “I’m on the pill.”
We started kissing as she rode me. I knew I wouldn’t last long. She started moaning loud and hard. She has an orgasm and started playing with her tits. “Fuck yes…”
“Jill, I’m going to cum…” I panted.
She pulled me out, still straddling my legs. She took my cock in both hands and started stroking. It felt incredible. I was playing with her tits and nipples.
My heart pounded. I was breathing hard and my cock exploded as I groaned. Cumming all over her hands, my stomach, her tits and stomach. She smiled and laughed. “I needed that” she sighed.
We made out then went to the guest bedroom/bathroom on this side of the house. We showered together, snuck upstairs to get changes of clothes, then went back to sleep together in that guest room.
The next morning, the other guys had no idea. It was our secret…and it wouldn’t be the last time.
Source: reddit.com/r/gonewildstories/comments/sirtsf/mf_my_best_friends_sister
This was hot as hell. Jill sounds incredible