Toy For the Night

"Take your time," Mariah said. "Go easy."

Ali nodded and descended. I watched and anticipated the entry of her pussy. Instead, I felt my head press against something tight and slightly warm.

No way. There's no way...

"I don't know girls," Ali muttered. "I'm not sure I can do this."

"Oh yes you can!" Emma replied encouragingly. "Just take your time and go slow. Rub your clit too. That'll help you relax."

"Besides!" Mariah added. "Look at our toy! He's practically begging you to give him your asshole!"

Mariah was right. I was nodding frenziedly and praying silently for Ali to proceed. Anal was one of the only frontiers we'd never trekked in the bedroom and after being worked up by all these girls, the desire to be let in was at a bursting point.

"Ross," Ali said, "give me two reasons why I should let you in my ass."

"I'll...I'll...I'll buy you that-that necklace you've been wanting!" I stammered.

She thought for a moment and grinned.

"I have been wanting that necklace for a while now," she chuckled. "And what else?"

I racked my brain as fast as I could, thinking of ways I could convince her to let me in. It didn't matter how much thought I was giving it at this point. I didn't care. All that mattered was getting into her tight little asshole.

"I know!" she interrupted. "You can be our toy again sometime! How does that sound girls?"

The others' faces lit up.

"I'd love that!" Annabelle gushed. "God, there's so much more I want to do with you babe."

"Me too!" Emma added. "That cock of his is spectacular! Hell, I want some more!"

"Hell yeah!" Mariah cried.

"Well Ross," Ali said. "What about you? Be our toy again for some anal?"

I should've given it more thought, but the temptation of Ali's asshole was way too powerful.

"YES!" I screamed. "YES I'LL DO ANYTHING! I'LL BE YOUR TOY AGAIN! JUST...PLEASE LET ME FUCK YOUR ASSHOLE..."

They broke out in laughter. On my left, Emma sat against me, patting my head. Mariah sat on my right and rubbed my belly, nodding approvingly.

"Good choice," Emma whispered. "Now just sit back and relax okay?"

I nodded several times and smiled.

Down at my cock, Ali began her descent. The head of my cock slowly pushed her tightness and entered a warm orifice, the likes of which I'd never felt before. After, I think, a minute, she'd worked the entire head in her, cradling it in her extreme tightness.

"Jesus!" she grunted. "Oh my god this feels so tight!"

Annabelle squirted some more lube on her hands and applied a fresh coating to my cock. Then, she put lubed two fingers on Ali's clit and started massaging it gently.

"Just breathe sweetie," Annabelle murmured. "You're doing great."

Ali nodded and let out a small moan. She took a deep breath and continued her descent, gritting her teeth.

Meanwhile, I was in La-La Land. The more of her asshole I felt on my cock, the harder it was to retain my composure. I was already giddy from having my head in her and every inch after was more intense than the last. Her asshole cradled my cock perfectly, warming and massaging it with every contraction and slight movement.

Finally, after what must've been 5 minutes of rubbing and heavy breathing, the last inch of my cock disappeared in her asshole. Her pert bottom pressed on the tops of my thighs and she smiled triumphantly.

"Hooray!" Annabelle cheered. "Your first time having anal! Ross is this your first anal too?"

"Yesss..." I slurred, rolling my head.

I must've been making the funniest faces because everyone was giggling with how I was acting. I mean, shit. My cock was completely buried in my girlfriend's asshole and her 3 gorgeous friends were rubbing me all over like I was a fucking king. Maybe this night wasn't so bad after all.

Ali started riding me slowly, adding even more heat to my cock. As she rode, Mariah and Emma put their tits in my mouth and let me suck and motorboat them. The cherry on top was Annabelle, who crouched down and had taken my balls in her mouth, sloshing them around and making them nice and wet. Lost in euphoria, I hadn't noticed each of them playing with themselves as they pampered me in all the right places.

"Rosssss oh my godddd!" Ali moaned. "Your cock feels sooooo good in my ass!!!"

I grinned and went back to sucking Mariah's tit.

Her riding speed increased. The bed starting shaking as her thrusts down got more enthusiastic. To keep steady, she leaned forward and put her hands on my stomach. As her speed increased, the pleasure and excitement did too. She started moaning louder and panting heavier as what must've been an orgasm drew near.

"Baby I'm gonna cummmmm!" she wailed, thrusting harder and harder. "I'M GONNA CUM I'M GONNA CUMMMM!!!!"

She shrieked and held me tight as she plummeted into an abyss of pleasure. I felt her nails dig into me as her asshole tightened even more, cranking up the pleasure once again. I let out a loud cry of pleasure as well because, well, it was probably the greatest feeling on Earth.

She didn't come down from the high very quick. It seemed to hit her in small bursts, keeping her clutching me for a while. When she finally did recover, she slid off me and crawled forward to give me a deep kiss. She sobbed quietly and I consoled her with my words.

"You're alright babe," I whispered. "I'm here for you. You're okay."

As I comforted her, I felt the cuffs leave my body. I hesitated for a moment, but I wrapped my arms around Ali and stroked her back while she continued to sob quietly.

"That w-was perfect..." she whimpered. "You're just the best, you know?"

I nodded and smiled. I planted a kiss on her lips and helped her roll off to my side. I stroked her hair gently and chuckled as I watched Annabelle grab my cock and prepare to mount it. She looked to me and I gave her a wink and nodded.

---

By the end of the session, I'd had some of the best sex of my life. Each girl rode and sucked me at least once each. I brought them to, probably, 15 orgasms total, both with my cock and my tongue. When I finally got to cum, probably 30 minutes after the anal with Ali, it was wild. I came in Emma's mouth. Instead of swallowing, she gave Annabelle a deep kiss, passing my load and her spit to her mouth. Next, Annabelle passed the load and their spit to Mariah. Finally, Mariah passed it to Ali, who stuck her tongue out for me to show off the cum and saliva. Without flinching, she swallowed the entire thing and stuck her now-empty tongue out, proudly letting me know how much she enjoyed it.

After we'd all rehydrated and used the bathroom (UTI's are no joke!), we went down to the pool and washed off with a skinny dip. We were hesitant at first, but Emma assured us that the pool's filters would remove any of the nasty stuff we left behind.

When we were all done swimming, we dried off and headed up for bed. As we reached the top of the stairs, Emma had an idea.

"Say," she suggested. "What if we all slept together tonight?"

"Your call Alina," Mariah added. "He's your boyfriend after all."

Ali and I exchanged glances. I shrugged and she smiled.

"I'd like that," she replied. "I think Ross would too."

They giggled and the five of us walked into Emma's room. Emma's bed was even bigger than mine and Ali's. I climbed in the middle, followed by Emma and Annabelle on the left. Ali and Mariah climbed in on my right.

I looked left and right and then sighed happily.

"You know girls," I said. "This was a great weekend. I think I'm gonna remember this for a long time."

They giggled and snuggled closer.

"What's so funny?" I asked.

"Look down babe," Ali laughed.

I glanced down and saw it. My cock was hard again and forming a tent in the blankets.

"Maybe we should take care of that for you," Emma said. "Would you like that?"

I looked to her and smiled.

---