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Times in my Life - Truth or Dare
28/02/2026
Back in 1978 I was an 18 year old just finishing up high school in a small town in Canada. I was into sports and also had very high marks so fit in also with the studious kids who I guess we call geeks.

I was a part of multiple groups and not really a member of any. I had an on/off relationship with a girl all through high school and as this is vent took place we were on break

I had a good friend named Doug who was a typical geek. Afraid of girls and a bit of a loner. Him and I were partnered with two girls Amy and Brenda on a history project and we spent a lot of time together in the library working on it.

Both girls were very plain. Nothing special about each one other than they were super smart. Amy was a medium build, short dirty blond haired girl with great big glasses that covered most of her face. She might have been a bit chunky but no means overweight. She always wore very baggy shirts and pants or long skirts so really hard to tell. Brenda was much the same. Maybe a little thinner. Glasses. Medium length hair. Through high school she had struggled with acne. But was well past that now. She also wore glasses. But they were super thick.


We got a great grade probably thanks to the two girls and someone suggested we should celebrate. So by passing notes back and forth we agreed to skip an afternoon and meet on a sailboat at the local yacht club that Amy had access to

Doug was all for it and he talked me into going as he had a real crush on Brenda. I was ok either way. So one sunny early June afternoon we all left school and headed to the boat. Doug and I stopped at my house and I grabbed a bottle of cherry whiskey ( a good Canadian drink at the time ) some coke and ice and away we went. We found the boat and went down below. The two girls were already there. So we sat down and we made our drinks and started to talk about various things. We drank and talked and I remember that boat was very warm. It we did not want to open the hatches as we did not want anyone knwk we were there

As we got bored we decided to play truth or dare and away we went. Started with innocent stuff about an ill and friends. And we were going round and round. Basically all picking truth. At own point when it was turn I was asked if I ever had sex. My answer was yes. Next to go was Brenda and I asked her the same question. She also said yes. Off course the same question was asked of the other two and both Amy and Doug said no. Next question to was who in the room (cabin ?) I would like to kiss. Knowing that Doug had a thing for Brenda I choose Amy. There laughs and we poured another round.

And it was really getting warm in this cabin. Finally we decided it would only be dares from now on. Doug’s turn and Amy dared him to kiss Brenda. So he leaned over and they shared a quick 10 second kiss. Brenda’s turn and she wa scared to kiss Doug. Again a small kiss but they were into a bit more this time. Amy’s turn and I dared her to kiss Doug. I think she was expecting me. But she reached over and kissed Doug with a lot more gusto than Brenda had. My turn next and Amy dared me to take my shirt off.

As it was really warm I happily did ! Well as you guessed and it did but take long for all the shirts to come off. Doug and I shirtless and the girls in their white bras. As I looked the two girls over I could see that they were hiding nice bodies under their always present baggy cloths. I would guess them both to be nice c cups and perky. Amy’s skin was a very light colour while Brenda was a little darker but not by much
Another round of drinks and the three of them were starting to feel the buzz. I was always allowed to drink at home so I was doing ok.


The game now changed. First to go was Doug and he was dared to take Brenda the V berth and make out for one minute. Away they went and we closed the door and they went in. Amy and I looked at each other and I reached over and felt her rust over her bra very firm !! After the minute went by the two came out and you could see they were very red and Brenda’s hair was mess. So mission accomplished. Brenda was up next and Amy dared her to take off her bra. Did not take much coaxing but she did and we were rewarded with a nice firm pair of tits topped by nice brown nipples.

Amy up. Off came her bar. Another fine pair of young tits. Her bright pink nipples pointing up . My turn and I was dared to take off my pants and off they came and you could see my hard cock through my underwear. Doug was next to lose his pants and he had a nice visible tent in his boxers. Brenda was up and Amy dared her to go in the V berth with her. This was an interesting twist. Away they went and you could hear them talking quietly. Doug and I just looked at each other and he had the biggest smile. I don’t think he had ever seen a naked pair of tits before.

When the girls came out they had lost their pants and were now juts in the white cotton panties. I think Doug almost came in his pants The girls said that they had decided that we just take turns in the berth and see what happens. One person would go in and the other three would play fingers ( an old 70’s game ) and they would send the loser in with a 5 min limit. I said I would ho first. So I went into the berth and as hot as the cabin was this place was hotter. Only consolation was that it was basically a bed with lots of pillows.

Brenda came in and shut the door behind her and laid on the bed with me. We started to kiss. French kiss as they called it. Lots of tongue and I wanted no time feeling those nice tits. They were very firm. Her nipples getting harder as I played with them. I had to take her glasss off as they kept getting on the way. And we resumed our kissing. I think we both reached for the other underwear at the same time. Me slipping my hand in feeling her nice soft bush. And worked my hand down until I could feel her wet pussy. I ran my fingers up and down her slit as she had her hand in my underwear her hand wrapped around my cock.

I my mouth off of hers and started to lick her nipples Licking and sucking them. Her pussy kept getting hotter and wetter. I tried to work a finger in her. But felt resistance. I asked her if she was a virgin. Even though she had said she had had sex I could tell she had not. She admitted that she lied. It was ok. The make out session was good. Her pussy felt amazing. And her tits a nice firm handful. Soon there was knocking on rye door and we broke it off straightened out underwear. She put her glasses back on and we went back out. We were both wet with sweat. You could tell that the other two had been making out as well as they were a bit disheveled
Amy said she would go in the berth next and I assumed Doug would follow. But he kept nodding towards Brenda as I knew he had a crush on her so I “lost “ and went back into the hotbed berth.

There I found Amy on her back. Her underwear gone. Her sparsely covered pussy on display. I wasted no time climbing on her and immediately started to suck on her tits. This girls body was amazing. And she had been hiding it under her frumpy clothes. Tits were firm. Her nipples on top. Bright pink areolas. And pencil erase nipples about 1/2 long. I sucked those babies and tweaked the other. I moved up to kiss her and she was on fire.

As we kissed I moved to the side so I could move my hand down to her pussy and found it soaking wet. Her pubic hair was fine and soft and absolutely soaked. I rubbed her clit and played with her hole. Sticking a finger in I found no resistance. And soon was finger fucking her. She was so wet and her pussy was practically gushing. She was trying to free my cock and fumbling with my underwear. I sat back and pulled them off revealing my nice hard 7” cock. She had her hands on it in a flash and was stroking it up and down.

ASI went back down and started to kiss her again and playing with her pussy. She asked me if I wanted to go all the way. I said I did but did not have a condom. She wiggled free and reached into her purse and pulled out one. She must have got it from a vending machine as it was a bright red. She opened the package a handed me the rubber. I rolled it onto my cock and soon had my cock against her opening. It slid smoothly in and she was soon bucking up to

Meet my thrust. We were both soaked with sweat our hair drenched. We did not fuck that long. My ball were ready to burst and soon I pushed into her and filled that condom up. She was happy. I guess I was her first. We kissed for a bit and then finally went out into the cabin. The other two looking at us like we were strangers. We were soaked with sweat our hair matted. The day ended too quickly. It wa s the only time her and I hooked up. But will never forget that sailboat.
Poster: JD


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