On the second floor, it was much less crowded and less wild, but there were still several dozen bodies on the floors, in chairs, on tables, etc. connected to one another. There were several people standing around watching and when their big group came in, two of those people quickly came close and introduced themselves.
"Welcome in guys! Do any of you have experience with anal already?" One of the women asked.
Serena, Stacy, Willow and Naomi, along with their partners all said they had some experience.
"Okay then! You guys can follow me and we'll get you situated." The woman brought them away to a free area on the second floor while the other woman led the rest of them closer to the rest of the club members who were standing and watching.
"I know you girls might be nervous, but don't worry. The first time is always the scariest but you'll come to learn just how good taking it up the butt can feel." She smiled to the girls.
Selia's nerves didn't really go down much, but with a light tap to that ass, she glared at Leon before smiling. The 6 of them were then directed by the woman and another woman and man who came to help, and the 6 of them got prepared.
"So, the first thing you always want to do is warm up your anus." The woman who was helping Selia and Leon here introduced herself as Harper.
She asked Selia to lie down and relax, to which the blonde did anything but relax. Harper smiled and worked to calm her down as she brought out a tube of lube and put it in Leon's hands.
"Lather your finger up and make sure to spread some on her butthole too. Then move very slowly and wait for her to start loosening up."
Leon nodded and did just that, rubbing the lube all over his finger and then onto Selia's chocolate starfish. She flinched at his touch and the cold liquid, making her anus pucker. Leon watched his fingers touch her untouched backside and quickly grew hard, anticipating what would come soon.
Harper smirked, but kept her words to herself as she watched as these students discover something new to pleasure themselves. She always enjoyed watching new blood grow and continued to direct Leon to take great care of her anus.
"Slowly put your finger in a little, and make sure to tell him if it hurts too much." She said and turned to Selia.
The blonde nodded nervously as she watched Leon's finger press against her anus. She unconsciously tightened it as he slipped his finger in, and she quickly felt a burning sensation.
"It hurts!" She grit her teeth and Leon quickly stopped.
"Try to relax, otherwise it will hurt more. If you let him in slowly your asshole will loosen up quicker and soon become pleasurable." Harper explained.
Easier said than done though, as it still took a while for Selia to loosen up enough for him to push in further. Her nerves were still high, as she was scared of putting something back there, but more specifically, the something between her partner's legs.
Leon had gotten naked as well by now and his large, thick dick reminded her of just how small her hole was. Her pussy had gotten used to him by now, molding to his dick, but her butthole was completely untouched.
She had only stuck something in it once out of curiosity and got a similar painful burning sensation from it and had avoided it since. But now, she was trying to face her fears, and Leon's eager face encouraged her to try and relax.
"There you go, its not as bad now right?" Harper smiled, seeing Selia's face relax more.
Leon's finger had finally made it all the way in, and after slowly removing his finger and adding more lube to it and her hole, he went back in and slowly moved around, widening her back entrance.
"Don't leave her pussy lonely~" Harper teased and encouraged Leon.
He didn't hesitate, and brought his other hand to her lips that glistened slightly.
"Ah~" Selia moaned strangely, as her clit was pleasured while her ass was invaded by his finger.
She couldn't look at him as she made those strange noises, earning a giggle from Harper who told her to let loose. The better she felt overall, the better it would be in the long run. If she remembered her first experience with anal as a pleasurable one, and not one full of pain, then she would be much more open to it in the future.
"Add another finger." Harper eventually said, making Selia's eyes go wide.
She had just started getting used to one, but now another finger was invading her hole, stretching her out just as it had before. Leon moved nice and slow, letting her get used to a second invader and it took much less time for her to start feeling better.
"Hmmm... try adding a third finger." Harper pursed her lips and said after a while.
"A-Are you sure?" Selia asked worriedly.
Even though her pussy felt good, and her ass wasn't as bad as the start, it still burned and she didn't think she could fit anything else in there.
"Well, 2 is fine to start out with, but if you're looking to fit that thing in you, you'll need at least 3 but probably more." Harper pointed to Leon's cock.
Selia gazed at it too, remembering their ultimate goal of penetration but still seemed apprehensive.
"J-Just go slow." She mumbled to him and turned her head away blushing.
Leon smiled at her and slowly pulled out to lube himself up again. Slowly, a third invader was added and Selia tried to grip the floor beneath her as she sucked in her breath.
"Stop! Stop!" She panted, feeling her asshole burn immensely.
Leon instantly stopped his hand, but continued to rub her clit and lips with his other hand. She continued to moan with a mix of pain and pleasure, slowly getting back to a relaxed state. Wanting to make sure she felt good more than bad, he brought his lips down to her flower and lapped up her nectar.
"Ah~" her normal sweet moan came out as he attacked her flower bud.
Her focus soon drew more towards her pussy, allowing her to relax a bit more and Leon to slowly continue his trek through her colon. Selia felt weird from all the pain and pleasure, unsure which was stronger and where they both started and ended.
At some point, the pain she was feeling started fading away, and by the time she knew it, three fingers from Leon were as far as they could go within her butthole.
"Good job!" Harper clapped her hands quickly, clearly excited, "Why don't you start moving your hands a bit more so she gets used to the feeling."
Leon nodded and started to slowly move his fingers in and out of her stretched anus. Selia sucked in her breath, giving more spread out moans as she focused on the feeling of her backside, trying to decide if it was still painful or pleasurable.
Leon didn't stop his attack on her pussy, soon making her quiver as she came. She panted through her orgasm, making her anus squeeze around his fingers. The foreign sensation for both of them got them all hot and bothered, and Leon wished that time could move faster so he could start ramming inside her.
Harper seeing his sorry state, scooted over closer and wrapped her delicate fingers over his member. Leon moaned in surprise, pausing his movements to look down at her hand around him.
"Don't stop." She reminded him, "You just looked pitiful so I'm just helping out a little~"
She smiled while Leon went back to slowly fingering Selia's butthole. The blonde he was in couldn't help but glare at Harper, as she pleasured her partner while she suffered under his touch. She pouted, and tried her best to relax more so that he could get inside her already.
Her pussy was dripping and she was desperately in need of some dick and now she no longer cared where it went in. A few more minutes went by and Leon came in Harper's hand, while Selia was finally prepped for penetration.
Removing his fingers, he admired how her asshole gaped and puckered with her breathing. She blushed as he gawked at her but spread her legs out inviting him.
"Make sure to take it slow you two. Have fun~" She smiled as she licked his cum off her fingers before walking off.
Harper had done her part to get them started, guiding them to the moment of truth as Leon's tip pressed against Selia's anus. She clenched at his touch, but did her best to relax as he slowly pushed in.
"Oh my god, why are you so big!" She complained, digging her nails into his shoulders as her butthole was stretched to the max.