ok so the first one: It was my first serious girlfriend and I, being one of the only 3 skaterbois in our town, ended up getting one of the hotter girls at school. so about 3 or so weeks into it we are at her place watching some shit disney cartoon and i decide to make some moves. Now for the past 3 weeks all my friends were doing the little teen shit where they ask you about everything possible and talk about pussy and tits non-stop so i had some pretty fucked up expectations. I had already gotten some breast work in and i was ready for some sweet sweeti clam. i start sliding my hand down her pants and i feel the 80's afro and i know im near the gold mine, so i keep going. at this point ive realized this is more hair than i could ever wish to have on my head and im getting kind of grossed out but i need to touch it, i need to feel the sweet soft spot i had seen in hustler and club so many times.
so i finally get to it, and its soaking wet. i feel like im going to start crying im so excited. and naturally at that age i have no idea what im doing so i diddle around a bunch like Michael J Fox with finger paints. i did this for probably half an hour when suddenly her parents call us upstairs for dinner. as we start going up the stairs, her infront of me, i decide to give my fingers a quick and subtle sniff. its the finest scent i had ever had. everything i imagined it would be, and more. there was nothing like it and i couldnt believe how good and powerful it was. i was dreaming of this for so many years..... then i snap out of it and realize not only have i stopped mid way up the stairs, but she is staring right at me, along with her mom and dad at the top of the stairs. i thought fast and pretended to be scratching my upper lip but not a word was said during dinner and we didnt talk again until about a year ago when she moved to my city for school.
the second one: so it was a couple years after the first one and me and my new girlfriend had been playing the "lets do it everywhere we can get caught" game. we had never got caught and we were pretty stoked on how hard we were killing it. now this girl was a freak, a pervert. i was still at the beginning of my little sexual life and i had experienced things that would make Hughe Hefners balls drop. we used to always watch movies in her room but with the sound off and go at it over and over again for hours. we werent even kissing, just teens4cash style super fucking like we had been bucking lines of powdered redbull cut with meth.
so one night we are going at it and decided to play the anal boink game. we are plowing away on the floor, with nothing covering us because we are idiots, when i hear feet land at the top of the stairs beside the door. quickily thinking i pull the blanket off the bed beside us and huck it over us with one arm, her mom comes in and sees us laying on the floor watching conair with the sound off, i have no shirt on and shes in just a bra. she is panting away and says between breathes "its so fucking hot in here mom, check the heater downstairs". so her and her mom get into this arguement about the heat while im STILL currently balls deep in her asshole, trying my hardest not to start crying and shit myself on the floor beside her naked daughter. eventually she left and i pulled out and went home and re-thought my life. i just moved a block away from her so life is about to get interesting.
and the last one (Pretty much all my awkward moments have been sexual because i have terrible luck and never think out what im doing):
My friend is trying to hump this girl at school but she isnt giving it up, so finally they plan a movie night and she is bringing her cockblock friend. so he tells me to come along and keep her busy while he plays doctor in the other room. i agree because i know something awesome will come of it. I may be a shit person but sometimes im a good friend. sometimes....
so the night comes and we are all in the tv room upstairs, watching some movie in the dark when the cockblock friend starts jabbering. i have no idea what she is saying because she is a woman, and i dont care. so somehow we walk out of the room so she can show me something in her room. she closes the door and jumps on me. she wasnt ugly but she wasnt super hot so i just let it happen because im 17 and my penis is my only prized possession. so we are making out for a while, with the brightest lights i have ever seen on and she decideds to rip my pants off and start blowing me. the fucking day is mine!
a few minutes go by, just enough for me to close my eyes and start enjoying it when she suddenly stops. i layed there for a few more seconds expecting her to continue but she didnt. i open my eyes and she is sitting on the side of the bed with her back to me and i look over her shoulder. Her massive father is standing in the doorway looking at his topless daughter with her panties around her ankles, with some skrawny pussy laying beside her, with a shiny wet boner. Immediatly i go deer in the headlights and freeze up with the most incredible fear i have ever felt. this man is fucking huge, like a fucking giant, and he is enraged. its dead silent for what seems like an eternity when she mumbles out "daddy..." and her dad says nothing for a couple more seconds. for some fucking reason (to this day i cant figure it out, maybe the stress and pressure just got to me) i burst into the craziest laughter i have ever had. tears in my fucking eyes giggling and saying sorry every breathe i get. he stomps out of the room and she chases after him, so i pull up my pants and run as fast as i can to the tv room to grab my friend and get the fuck out. not only is he ready to go, hes pushing me out the door. we ran for a good block then laughed all the way back to my house. i never spoke to that chick again even though she was in nearly all my classes.
i still feel bad that he never got anything that night because when me and cockblock left the room all the girl he was with did was talk about what me and the other girl were probably doing.