Gordon

As the only member of the trio who has been in Shailene's class before, and the one who seemed least 'experienced' and therefore least likely to have any infectious diseases Gordon is given the pride of place at her pussy. While the ass is traditionally the greatest risk of infection she KNOWS that there will be blood in her hooch this time, whereas her backdoor is only a 'maybe'. She places Chuck back there, figuring that as the most experienced he is least likely to actually cause any damage, and also knowing that he keeps a condom in his wallet for these situations. Ronny is left with her mouth, because she knows from the talk around the school that he has an exceptionally large cock and she doesn't want to risk that in either of the holes that she has less control over.

"Now." Shailene states when all of them are in position and the three dicks, none of them tiny, enter her.

The pain in both front and rear is intense, and she has to fight back the tears that want to come to her eyes which she knows will wilt her young partners erections ending this orgy almost before it begins, but with an effort of will manages it. Focusing instead on the intense arousal she has felt since making landfall she starts rocking back and forth on the two cocks inside her fore and aft and licking long and lovingly on the one off to starboard.

Chuck and Gordon can feel each other through the thin wall of flesh separating the two tunnels in which they have embedded their shafts. They have compared their dicks before in the locker room and are aware that while Chuck's is longer Gordon's is thicker, which suits their postilions in this instance perfectly. They also are both aware that Ronny's dwarfs them both, and have commented to him before that he should go into the porn industry. At almost the same instant the thought crosses both their minds that if they had a camera set up right now this scene they were all in would make millions on any pay site on the internet.

The fuck session gets more and more intense as it goes on, with Shailene orgasming after only a minute and a half, and then again two minutes after that. Ronny tries to get her to do deep throat early on but she gags hard and slaps his hand when he tries to hold her head in place, at which point the other two give him a look which tells him: 'Don't you DARE screw this up!' and he contents himself with a slightly more 'R' than 'X' rated blowjob.

By miracle, happenstance, or the whims of fate: the four of them all cum simultaneously, Shailene for the fourth time, and even more drenched in sweat than before they collapse together in a pile of satisfied and well fucked flesh, trying desperately to not fall asleep in this compromising position.