When I Saw My Crush There, I Had To Join In

It was a Saturday night, and around 20 of us gathered for a friend's 30th birthday celebration. He reserved a penthouse suite for the occasion, and a mixture of boys and girls were invited. The venue looked really expensive, and it had a big private rooftop pool, which was heated, along with a jacuzzi to relax in.

The atmosphere was lively from the start, and as the night unfolded, I started to feel pretty damn drunk. So me, and my friend, James, went up to the pool, and as we got up there, I noticed my longtime crush, Hanna, was stripping down to her bikini. Hanna, with her long blonde hair, piercing blue eyes, around 5ft7, and perfect curves, looked incredible. I thought this was my opportunity, so I stripped down into my boxers and jumped in the pool.

‘’Hanna! Had no idea you were joining us here tonight?’’ I said, with a big smile on my face.

‘’Joseph! Would I miss out on this place? Hell no! This is my friend Erica!’’

‘’Nice to meet you, Erica, and this is my friend James!’’

‘’Ohh, you are both cute, my type of guy…’’ Erica said.

James was sitting on the edge of the pool in his boxers. Hanna began to move closer to me, and within seconds, she grabbed me, and gave me a kiss.

‘’Someone a little drunk?’’ I asked.

‘’A little bit… Here to have a good time though, so give my friend a kiss too.’’

Erica made the first move, and gave me a quick kiss.

‘’Now let's have a 3-way!'’ They both pulled me in and kissed me while James sat there awkwardly.

Another girl walked over, someone Erica knew, her name was Isabella. She was bisexual and on the shorter side. She had nice tanned skin, looked a little latino, really pretty, and muscular legs with a big bubble butt.

‘’Hi guys, mind if I join in the fun?’’ She asked with a cute smile on her face.

‘’Of course not, more the merrier.’’ James laughed.

‘’More? GEM! Get over here!’’ She screamed to her friend.

Gem came walking over, a little more on the larger side but still very pretty and definitely fuckable. She was in a short cute dress that showed off the bottom of her big arse nicely.

‘’We are outnumbered now, James!’’ I laughed.

‘’I am sure you two could handle us all. Couldn’t you?’’ Hanna joked.

‘’Let’s find out,’’ Gem said.

Straight after she said that, she placed herself down on James lap and began kissing him. While I was watching, I felt Erica's hand brush across my boxers, and it gave me a big erection immediately. She grabbed Hanna’s hand and placed it on my hard cock, and they both yanked my pants down.

‘’Wait…’’ I said, nervously.

‘’No! Sit on the lounger there!’’

I sat on the lounger with my hard erection out, and Gem looked over while smiling at me, pulling James’ boxers down. I had Hanna and Erica running their tongues up the length of my cock, and James had Gemma and Isabella fighting over his cock, licking and sucking every inch of it in a double blowjob.

‘’Who is fucking me first?’’ Hanna asked.

‘’Me and my tongue,’’ Isabella said while moving up behind her.

Hanna was bent over and still sucking my big dick, Isabella pulled her bikini bottoms down, and when she started to lick, I felt Hanna’s breathing get heavier.

‘’Oh… God, Isabella, you are so fucking good! Someone fuck my arse now!’’ She screamed.

James had always been one for anal, so he jumped right up, grabbed her hips, and slowly pushed it in.

‘’Fuck! Joseph, let me ride your cock at the same time! I want to enjoy a double penetration!’’

I froze for a minute, I didn't expect this party to be like an amateur orgy, and well I wasn’t happy that my good friend had his cock inside my crush's arse. It was an opportunity to fuck her though, and I didn’t want to disappoint her, so I agreed to let her ride me.

‘’Fuck it! Climb on it then!’’

Slowly lowering herself down onto my cock, while James pushed deeper inside her arse. She started to pant and moan, getting louder with each push. Her pussy was soaking wet and extremely tight. I just wanted to cum inside her.

Isabella then walked over to Hanna, pushing her face in towards her pussy.

‘’Lick it, and suck my clit, massage it properly.’’

While Hanna was eating her pussy, Erica came to help, licking Isabella’s arse and fingering her.

‘’Don’t be greedy, let me have a cock too,’’ Gemma said while fingering herself.

I wasn’t too comfortable watching James in her arse, so I jumped at the chance. I lifted Hanna off me and walked over to Gemma. I grabbed her by the ankles and pushed them up onto my shoulders, sliding my cock inside her. Her wet pussy was tighter than Hanna’s, and it surprisingly felt better, so I started to fuck her faster. After a few big pumps, I pulled out but accidentally fired my load all over her.

‘’Oops… Sorry!’’ I laughed.

‘’That was quick…’’ She said while finishing herself off.

James loudly moaned as he pulled out of Hannas arse and then fired his load all over her cheeks. The girls jumped in the pool to clean themselves up, and they shared a giggle between themselves. Me, and James chilled with a beer.

We all spent the rest of the evening having a swim, more drinks flowed, and we danced the night away. I pulled Hanna for a chat at the end of the night, just to see if she wanted to go out one day, but she turned me down. She said she was disappointed that I stopped fucking her and that I chose to finish off with Gemma.

Considering she had my friend's cock up her arse, and basically a big orgy, I thought it was acceptable, but according to her, it wasn’t. I went home in a bit of a negative mood, but once I slept on it, I woke up feeling incredibly good. Just knowing I’d fucked her, and how jealous she got showed that she liked me at least a little bit. 

The next few weeks, I put some extra effort into winning her over. Hey, nothing ventured, nothing gained.