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Let's share stories about our awkward first experiences with sex

>be me
>trapmode looks, thin body, babyface, long hair
>hanging out at mall
>see a guy and a girl i know from my local college
>acquaintances but not exactly friends
>chick looks like the most stereotypical deviantart user or hot topic shopper
>dude's a bit on the chubby side, has a bit of a beard, not too bad though, maybe 7/10
>they decide to chat it up with me
>talk about video games and movies and shit
>they seem pretty cool, presumably a couple or something
>we all decide to go see Captain America 2 at the mall's movie theater
>only ones there
>we're still chatting, waiting for the movie to start
>suddenly the conversation turns very sexual
>they jokingly invite me to their orgy
>slowly it becomes clear that they aren't joking
>movie starts but can hardly focus on it because the guy keeps whispering dirty shit in my ear
>after the movie we head over to his apartment
>he takes us up to a nearly empty room upstairs with nothing but a mattress and a couple old chairs and magic the gathering cards on the floor
>him and the chick almost uneventfully strip naked
>i try to follow suit
>the chick is all over me, really wants to make out
>sosoft.png
>we make out while he watches and starts to jerk off
>she keeps telling me how much she likes how femme i look
>after about 10 minutes of this shit, i'm pretty damn hard
>I try sticking my dick in her
>it's like trying to force a hot dog up a faucet
>it's just not going in, im just hitting a wall
>manager to shove the tip in, and it feels great
>really warm
>i keep trying to thrust further in, but it's not happening, and the frustration just makes me more flaccid, making it more difficult to continue
>we both kind of laugh and are embarrassed and go back to making out as the guy keeps jerking off over us
>eventually make her cum with my fingers and he cums on her back
>i never cum myself

could have gone worse i suppose