Experimenting with Friends
Two of my best buddies, Dave and Jeff, and I were always bored. We spent endless summer days trying to come up with games to pass the time.
We would sit in my treehouse, in the woods behind my house, and think of anything to entertain ourselves.
One day Dave suggested Truth or Dare. The Truth option quickly became boring because there wasn’t very much that we didn’t already know about each other.
Suddenly the game just became about the dares. My buddy “Jeff” was the first one to accept a dare. We dared him to strip naked and run from my backyard, up the driveway, out to the mailbox by the street. He climbed down, removed his shorts, underwear and tee shirt and began running. He’s through the backyard and approaching the back of the house, when suddenly my mother walks onto the back deck to yell to us and see if we wanted anything to drink. She immediately is shocked when she spots Jeff. He freezes like a deer in the headlights and my mother asks him what the hell is he doing. He explained that he slipped and fell into some mud and was just coming to use the hose to wash off. My mother laughed, told him to point his erection in the other direction because she didn’t want to see it, and hurry up. When she turned to go back into the house, Jeff scrambled up the driveway to complete the dare. Just as he reached the mailbox, my sister pulled into the driveway. Amused, she asked him what he was doing. They knew each other pretty well, so Jeff confessed about the dare. She laughed and told him to get into the car. She drove him back down the driveway and walked with him back to the treehouse to see what we were up to.
Dave and I saw the whole thing but couldn’t hear them and we were panicking as my sister and Jeff were now headed out towards us.
My sister, Sally, yelled up to Dave and me and asked what we were doing. Jeff confessed and told us he already confessed to the dare. Jeff grabbed his clothes and was about to put them on when my sister told him to stop. She told him to leave his clothes on the ground and climb back up to the treehouse. She followed him up.
She informed us that we were in big trouble, unless we all agreed to let her come up with the dares. We were all nervous, but agreed.
She told us that we’d all be naked soon enough so we might as well just strip now. We reluctantly accepted and stripped.
She was pretty impressed with the power she had over these 3 boys who she had known their whole lives.
With a huge grin on her face she ordered me to sit directly in front of her. Then she ordered Dave to stand behind me and rest his erection on my shoulder. She then ordered me to suck on it for 10 seconds. She started counting when I closed my lips around Dave’s swollen cock. When she got to 10, I gave it one deep suck and then let him go. Dave is bursting at the seams. He’d never had anyone suck him before and suddenly he’s doing it in front of a girl he’s had a crush on forever.
Next she wants to mess with Jeff, so she tells Dave to lay face down and tells Jeff to rub his swollen cock between Dave’s ass cheeks for 30 seconds. Both Jeff and Dave objected until she offered to remove her shirt if they complied. Dave immediately lays down and Jeff starts slowly humping his friend. Sally slowly counted to 30. By the time she got to 20, Jeff got a pained look on his face. By 25, he was cumming all over his friend’s back.
Sally was thrilled, and she immediately took off her shirt and bra to hold up her end of the bargain.
Now shirtless and very horny she can’t wait to see what we’ll agree to next. She very keenly noticed that I didn’t really object when I had Dave’s cock in my mouth so she decided to try it again, but deeper and longer.
She ordered me to sit off to her left, and then ordered Dave to put his cock back in my mouth, but this time for a minute. Dave said he wouldn’t do it. Sally then stood up, removed her shorts and then sat back down in her underwear. Dave was thrilled to see my sister topless and in her underwear so he stepped forward and put his cock in my mouth. Sally started counting as I closed my lips around it and gently massaged it with my tongue. Jeff was laughing, Sally was counting, Dave was squirming and I was in heaven.
Before she got to 30, Dave panicked, pulled out of my mouth and exploded all over my face. Sally loved it, and as she shifted her position we could see wetness leaking through her cotton panties.
She then announced that it was my turn to be her “victim”. She demanded that I stand up and that Jeff and Dave position themselves so they can place their lips on either side of my cock and they are to move up and down my cock together for a full minute.
Jeff and Dave both objected, so Sally stood up again and removed her soaked undies.
They quickly complied.
I’m now standing directly in front of my naked sister while my 2 best friends are running their lips up and down my erection. I’m staring straight at her and watching her play with her pussy while counting slowly. Jeff and Dave settled into a nice rhythm as my orgasm quickly built.
Holy shit I’m going to cum in front of my naked sister. I don’t ever know where she was with her counting when I shot straight onto her naked tits.
We were all spent. Dave had cum on his back, Sally had it on her tits and I had it on my face.
We all quickly got dressed, and without acknowledging each other we climbed down from the treehouse and went our separate ways without saying a word. Except Sally. She’s walking alongside of me, puts her arm around my shoulder and said “that was fun, we’ll have to do that again”.
That is so hot! I wish I could of had a sister like you. I'm so fucking horny 😋 now.
Me and my friend were in high school and we let his younger sister watch us. One day he fucked her on a dare. He had a nice size dick. She said it hurt. He didn’t stop, then I fucked her for sloppy seconds.
Had the neighbor boy, was my " vaginal substitute" for my Sister and his Hot Mom
Wow, hot times. I grew up in the city and my parents sent me to summer camp every year. Didn't like the idea at first, but after getting to the camp, it was cool.
It was a boys summer camp and some counselors were female hs and college students working for the summer.
There was small boats to row around a lake, sports, skinny dipping, hiking and classes.
At night we jacked off in the shower and cabin. And dick sucking, some guys ass banging.
I will say this every time I read these stories; where the fuck was I growing up?! Seems like everyone had jerk off and suck buddies but me and I’m jealous
I just had one, and it went on for years. He was mine 😂
Well I was thirteen the first time I did stuff was with this older guy that lived in the same building. OMFG is adult sized erection going into my early teen but hurt like all living hell. I avoided him from them on. I did not try anything with another boy until I was almost fifteen and I made sure he was younger than me. His did not hurt at all.
This was the summer before freshman year in High School. The experimenting lasted the rest of the summer and then my friends both went to private schools and we lost touch (literally).
Years later, my girlfriend and I were set to have a threesome with another guy. She asked if I was going to be OK with some inadvertent touching. I confessed that I had given handjobs and blowjobs as a teenager. She was thrilled.
My couple of friends didn't have a didn't have a treehouse, we had a very small wooden fort made of odds and ends that our dads had put together for us when we were all preteens. We'd play there often and we did have a couple of cool sleepovers in it as young kids.
As we got older, around twelve, thirteen, the fort had deteriorated some but we kept it together. One of my friends would hide Oui & Hustler magazines his older brother gave him at the fort in a plastic shopping bag. We'd take turns going there to jerk off as the others kept watch for adults.
Eventually we got into doing anal sex to each other with the use of a dab or two of Suave Hair Conditioner that one of us brought to the fort, originally to use it to jerk off. We skipped the usual mutual jerking and sucking and just went directly to laying on our tummies for each other.
It all sort of faded out by the time we approached being sixteen and all five of us sort of just moved on. I have lost track of our little group of five over the years but I still recall all of the shared experiences we had at that little fort in the woods. BTW... those woods and fields are now part of a Walmart parking lot LOL
I only experimented with my best friend that I trusted would keep our secrets when we were almost thirteen. First each of us had admitted to each other that each of us masturbated very often.
We'd often admitted when was the last time each of us masturbated and some general details of when, where and how if one of us asked the other.
During a sleepover at my friend's house we ventured online and discovered porn sites clicking between guys jerking off and regular sex vids. Slowly we honed in on guys doing anal to girls. We experimented with fingering ourselves as we jerked off while looking at the porn vids that night.
In the following weeks each of us would finger ourselves as we masturbating. Each of us admitted that it made us orgasm faster. Eventually, during a sleepover at my house I suggested taking turns doing anal sex to each other. He was a little hesitant until I took the initiative and got on my tummy and lowered my PJ bottoms exposing my butt.
His pulling down his PJs and getting on top of me was a bit clumsy and I had to guide his erection. I was surprised at how uncomfortable that initial penetration felt but he squirted out into me with just a few humps and pulled out. I could not help passing gas when he pulled out. It made us both sort of giggle.
He then laid next to me and I had him part his butt cheeks with both hand making it easy for me to find my target in the first try. He drew a deep breath as I slipped into him, but he, like me, did tolerate that very first penetration pretty well. I also was ejaculated quickly into him as deeply as I could. I rolled off of him and we laid there in silence a few seconds.
We figured out that right after school we could go to his house to do it again because his mom did not get home until almost 6pm giving us at least 2 hours of privacy. We did it almost everyday after school. When summer break from school rolled in we did it almost daily in the morning hours. We did this all throughout middle school.
My buddy and I started to jerking off together when we were 12. By the time we turned 13 we were sucking each other, 6 months later we were fucking each other and practicing for when we got girlfriends.
I’m an old man but I fantasize about sucking a cock while a woman watches
You should do it. Everyone is shocked at how many traditionally straight men love giving handjobs and blowjobs. They also completely underestimate how much women love watching.
Mmm I’m an old man but I fantasize about sucking a cock in front of a woman while she masturbates
Story too long. Please post the condensed version
Dude. Get an attention span. Wtf
American do not have long attention spans
I do
Me2
Huh???