Just as Jeremy slipped inside, he felt two cushy pads gently squeeze against his head, as Claire fished him out of her. “Sorry about that,” she apologized, blushing as she set him back down on the ground and scooted away from the edge of the couch. “I got a little… too into the moment, ya know? Really sorry, that’s super unprofessional of me.” She grimaced, avoiding eye contact. She was the one hundreds of times his size, but she felt too awkward to look him face to face.
“Um… it’s… you’re fine, at least you weren’t trying to hurt me I guess.” Even still… almost swallowed alive by a giant pussy, he thought. Not how I expected tonight to go in the slightest.
“Well, I’m guessing you’re not gonna be into this,” she continued, breathing in slowly as she worked up the courage for her proposal. “But theres still one last thing we can try,” she said, turning over onto her hands and knees. “And it’s my favorite.” The shrunken man watched as Claire’s ass suddenly loomed large in front of him, stretching so far to either side that he felt like he had to turn his head just to take it all in. And there, in between her bubbly cheeks that wobbled with every slight movement, was the crown jewel. “Obviously I make sure to always clean it really well before—“
“I don’t know about that Claire,” he interrupted her, feeling both entranced and fearful of her at once. “Your… vagina. That was already so much, and claustrophobic, and—“
“You don’t need to go in all the way!” she promised, turning back around. “Nothing you’re uncomfortable with. But it’s my faaaavorite thing to do with guys your size.” He scratched his head, not wanting to let her down, but still hesitant about the experience. “How about this: we can race for it,” she said with a smile. “I’ll put you down on the other end of the hall, and give you a big head start, like 60 seconds or something. And the first person to make it back into my room gets to choose. I’ve done it a few times with guys before, so I know the perfect distance so that if you’re fast enough, you can definitely win, but if you’re slow enough I will too. That way it’s fair.”
She had such a sparkle in her eyes, such an excited aura about her, that he felt like he couldn’t say no. Giving him a fair shot, and even if he lost and had to go through with it, he knew that ultimately he wouldn’t have anything to be scared of. “Alright,” he sighed. She practically squeaked with happiness and bent over to pick him up carefully in her hand, before carrying him over to the door and peering outside. It was empty out, so she pushed the door wide open and quickly scurried halfway down the hall, stopping right next to an electrical outlet.
“OK, here should be good,” she said, and put him down between her feet. She was still naked of course, but clearly didn’t have any reservations about her public nudity in case anyone walked in on them. “Ready?”
He took a deep breath and stanced up, focusing on the doorway at the end of the hall. “Yeah.”
“Go!” He took off running as Claire began to count upwards from 0, watching him sprint away from her. “16, 17, 18…” He felt like he was making good time so far. At least she’d been honest; the distance seemed just far enough that he really did have a shot at making it. “34, 35, 36…” It had been over a decade since he was in high school track, and while he was somewhat in shape, he was clearly starting to feel the burning in his chest. He’d always been a sprinter. 100 meters, sometimes 200 meters. But a minute of running was closer to the 400 meter mark, if not a little more. And his stamina was simply not good enough that he could carry on at the same speed for a full minute. “56, 57, 58…” He was close though, and with seconds left until Claire started running, he tried his best to fire his legs back up, knowing he just had to last a few more seconds. “Sixty!” Shit, it’s too far still! Claire didn’t go easy on him, and started sprinting right away. And the distance was so short because of his size that she passed him in just a few seconds, sailing over his head back into her room.
He collapsed on the floor, instantly exhausted. Just another 5 seconds or so, and he probably could’ve made it. A younger, healthier man in his position could’ve made it. But he just wasn’t quite good enough. He heard Claire crawling back over to him, gently picking up his body before closing their door again. “Well, at least you gave it a good try,” she said softly, trying to make him feel better. “At least the upside is you don’t technically need to do anything,” she explained, rolling over onto her stomach and kicking her feet up behind her. Jeremy didn’t fight back as she carried him behind her and set him down on her lower back. “And it’s obviously a lot tighter back there, so you can’t ‘fall in’ like you did before. Only as far as you wanna go.” He didn’t say anything in response, but made his way towards her bum, trudging in the narrow space of her crack as she pried her ass cheeks apart. “But I also realized that I haven’t actually made you orgasm yet. And this night’s supposed to be about you. So I’ve got a way I think I can make us both happy.”
She used one of her hands to keep her cheeks from closing in around her friend, while her other one reached back just as he arrived at her rectum. As he stared at the daunting hole, he felt himself suddenly picked up, and she slowly lowered him right above her anus. As his feet made contact, she gently pushed him further inside. His dick hadn’t actually withered away in a while, but it started surging again. As much as he was scared, he couldn’t help but feel secretly excited by the idea. “OK, I won’t suffocate you like I said, but I still need you to keep your arms at your sides,” she instructed, and he did as he was told. She lowered him all the way down to his waist, and then began pushing even further. His arms were now stuck, pinned to his side, as she slowly pushed him up to his upper chest. But just as he was starting to feel uneasy, she began pulling him back out. But then reversed herself, and pushed back down again. Then pulled him up. Down, and up, and down, and up. The back and forth motion was already massaging his dick, but the realization that Claire was using him as a dildo for her asshole nearly sent him over the edge. She sped him speed, and he felt like he was on a rollercoaster as she pumped him in and out of her, rubbing his dick in the process while he was helpless to do anything but enjoy the ride. He could tell he was seconds away from climaxing, and he closed his eyes, ready to finish. Just as he was about to climax, she let go of him with his body stuck halfway inside her hole, and then pulled away her other hand so that her cheeks slammed back together around his body. He cried out in surprise, but the finishing touch was enough for him, and he felt himself explode. Still tightly gripped by her rectal muscles, he felt warm and cozy as he released himself into her, letting gravity allow his cum to trickle back down into her asshole.
“Thank you,” he panted, relaxing his body, and Claire closed her eyes too, a content smile on her face as she figured she’d let him sit in her ass for a little while longer. Since Jeremy obviously wasn’t complaining. After going so many months without any sexual experiences, he’d finally just had the best one of his life.