Friends Helping Friends Pt. 03

I was lying on my bed looking at the ceiling and thinking about Anna. If I was a betting man, I'd bet that she was starting to like having sex with me, and it wasn't just a friend helping a friend. Then the other part of my brain knows that I was basically a hurt puppy, and she could just be pitying me. But swallowing my cum seemed a bit more than pity. Those thoughts filled my brain every day and every night. Sean never seemed to be any the wiser, nothing ever seemed different at work.

I hadn't hung out with them in a while, they were busy with whatever, and I just didn't get a chance to go over. One day, it was a Thursday, and Sean and I were smoking behind the shop building. "We gotta hang out tonight," Sean blurted.

"What's tonight?"

"Nothing, we just haven't hung out in a while and Anna was saying she wanted to make dinner. You can come eat; we can go out after."

"What's she making?"

"I don't fucking know, you coming over or not?"

I laughed, "Yeah, I was just curious. I'll grab some shit for shots, we can toast."

"Nice," Sean stated, "I gotta go unload the truck, just come over whenever."

I nodded and he ran off.

***

I brought over some Crown, and some cranberry juice. We made "Washington Apples" and ate some spaghetti. It was good, both of them. After we ate, we wanted to go to a bar and keep the party going, so we walked down the block to a shithole called "The Joint." It smelled like stale beer and vomit, and the locals there smoke so many cigarettes, your eyes water if you stand near them.

"What are we drinking?" I asked.

"I'm getting a Cosmo; I don't know about yous." Anna offered.

"Shot and a beer baby," Sean added.

"I'll go with that too, Cosmo is too girlie."

"Pssh, whatever dude, I'm the one that will be drinking a glass of vodka, you guys are pussies."

The night progressed, and the shots and drinks went down.

I was getting pretty drunk. Beers, I can drink all day, but adding booze into the mix and my head gets a bit swirly. Anna pulled Sean up when she heard a fun song she liked, she danced around him while he swayed and looked like he wasn't really into it. I sat and watched. Anna was wearing nothing special, a T-shirt and jeans. Sean was in his T-shirt, cargo's and sandals and I was in a t-shirt and jeans. I didn't have much to look at in the bar. Other than Anna's ass, that is. The song ended and Sean ran to his chair to avoid dancing to the next song. He slammed the rest of his beer and got back up to get more drinks from the bar.

Anna walked over to me; I was sitting so my lap wasn't under the table. She looked over to Sean who wasn't paying a bit of attention, and she sat on my lap. "You want to dance?"

"No, I do not," I said with a funny tone.

"You's are no fun."

She stood up before Sean turned around and while standing up she reached down and grabbed my junk. My eyes widened as she walked over to Sean to help him carry the drinks. I knew it. She likes it. I thought. Or she is just being a tease.

I shook off the rush of adrenaline and the two of them sat back down. Sean bought us another round, cementing the fact the rest of the night was going to be a shit show. At least for his lightweight ass.

Another song came on and Anna got up to dance, Sean refused this time and there was no way I was dancing so she danced around us while we sat at the table. I thought it was hot, but Sean looked annoyed.

We finished that round, and it was time to meander back to the apartment.

We walked down the road and into the complex. We were passing the pool when Sean blurted, "Let's jump in the pool!"

Before we could say anything, Sean was through the gate and pulling his shirt off. She jumped right in. We followed him in and stood by the side of the pool as he flailed around. I took off my shirt and jeans and was down to my boxers. I jumped in the deep end and went down to the bottom. I came up and cleared the chlorinated water from my eyes only to see Anna pulling off her shirt. She was in a sports bra which looked enough like a bathing suit and then she dropped her jeans. She was in boy shorts, which again, weren't very revealing and could pass for bathing attire. She jumped in and swam over to Sean and started to make out with him. I floated around for a bit until Sean said, "I gotta get out. I'm not feeling great."

Sean climbed out of the pool and plopped onto a lawn chair. He was breathing heavy and doing a lot of sighing.

"You alright buddy?" I asked from the deep end.

"I'm fine, I just gotta rest my eyes a minute." He mumbled.

"Sean?" Anna called.

"Dude, Sean, you alright?" I yelled.

Just then we both heard a loud grunt followed by a loud snoring sound. Sean passed out. Again.

"You boy can't hold his liquor." I said laughing.

I swam over to where I was able to touch the bottom and was headed to get out of the pool when she grabbed me by the waist band of my boxers.

"Lucky for you I guess," she whispered. She swam over to the side of the pool right in front of Sean. She took a handful of water and tossed it at him, but he kept snoring. She spun around and leaned with her arms on the edge of the pool.

"Well?"

"Well, what?" I asked.

"If I have to spell it out, we might as well just call it a night." She said.

I made my way over to her and she turned around. My dick was getting harder with each lumbering step closer. She placed her elbows on the side of the pool and inched up behind her. We both looked over to Sean who was still snoring away. I pulled down her panties just enough, so her pussy was exposed. I pulled my dick out of the hole in my boxers and slowly nudged it into her. She pushed back on me, and I popped inside.

I began slowly, pumping in and out keeping the waves to a minimum. With all the booze I was able to last much longer. I could pump harder and deeper with more confidence. I fucked her, right in front of her boyfriend. I was pulling her toward me and slamming into her with all the force I could muster, while in a pool.

She put her head down onto her arms and was biting her forearm to hold in her moans and gasps. I kept fucking her. This time I was going to show her I wasn't some sad sack who came to quickly. I kept fucking her.

Sean stirred and I pulled out and dove backward. I came back out of thew water like nothing was happening and noticed he was still out. She laughed. I breathed a sigh of relief.

She turned back around but I guess my fear caused my erection to go down. I needed a bit of help. I pushed my soft penis on her butt and she reached back and grabbed it. It started to get hard immediately but she had other plans. She turned around, took a deep breath and went under. She put my dick her mouth and sucked on it until it was just as hard as before. She came back up, wrapped her legs around my waist and sat on my dick. I pumped with all I had. Watched as Sean slept and then back to her face. Her eyes were rolling back in her head. I was making her cum. I pumped harder. I was going to cum, I was trying to pull out, but she wouldn't let me. She didn't want to ruin her orgasm. I whispered, "I cumming."

She whispered back, "Do it."

I let go, I came in her pussy hard. She came on my dick just as hard. After it was over she let up on her grip and pulled back. My cum was floating out of her pussy and into the pool water. She swam away to the steps and got out. She walked over to Sean, "Hey." She said shaking him. "Hey!" she yelled. Sean startled awake.

"Come on, I'm freezing we gotta go home."

Sean stood up, and they grabbed their things. My erection was gone, and I was able to climb out of the pool, I grabbed my things.

"How long was I out?" Sean asked. "What were you guys doing?"

"Not long," Anna stated. "We just fucked around for a bit."

Sean yawned. "That's good." He lumbered toward the gate.

Anna looked back at me and shot me a wink.

I smiled.

We left the pool.

Best night at the pool ever.