Friends Helping Friends

My name is Derrick, and I am 22 years old. I guess I'm a 6.5 out of 10, skinny, but muscular, not boney. I moved to a new state a few years back and had a hard time making friends. Eventually I got a job at a bookstore, working behind the counter and restocking shelves. It was boring as hell, and the people purchasing college books took out their frustrations on me as if I set the prices. There was one thing that made it okay, another employee named Sean. He was a funny guy, a couple years older than me and he liked to smoke weed. We quickly became friends and he was literally the first friend I'd had since moving.

Sean had a girlfriend named Anna. She was his age but didn't look much older than 21. She had blonde hair, freckles, huge boobs and a tight little butt. Every time she would come to pick up Sean in her truck, I'd get a little wave, and it was a nice rush of energy for the rest of the day. To say I had a crush was an understatement. I hadn't touched a girl since my high-school girlfriend that I left 3 years ago so falling in lust was easy. My loneliness, and lack of female companionship, was beginning to drive me insane at that point as well. This was a bit before the internet, so I was stuck going to sleazy porn stores to buy magazines and videos. Jerking off was getting old, but it was my only release.

Back to my story...

Sean and I eventually began hanging out outside of work. We'd go to shows, bars, or we'd just hang at one of our apartments. Anna was always with him. And I was always stealing looks at her. Over time all three of us grew pretty tight. Anna would try and bring me around her girlfriends, but they were a bit older and I had zero game, so I was striking out left and right. Anna felt bad for me, but it didn't stop her from busting my balls about it. One day I stopped by their apartment to hang out and do some bong rips. Sean was on a beer run, so it was just me and Anna.

"Heather said you were cute." Anna said after blowing out a hug amount of smoke.

"Oh yeah, so what's her deal?"

"She's dating someone, he's real douche-bag, he's a firefighter who thinks he all cool. But he's just a fat loser."

"So, you're telling me this because...?

"Haha, I just wanted you to know that she thinks you're cute. And maybe if she breaks up with him you can swoop in."

"Oh, yeah, I'm a huge swooper. I'll knock her off her feet with all my car washing money."

"There's always a chance," she said passing me a fully packed boing.

"I guess."

"How long it's been?" she asked.

"Been what?"

"Since you had sex with something other than your hand?"

"I'm not telling you that."

"That long huh," she laughed. She could see I was annoyed. "I'm only kidding, it'll happen dude, you just gotta keep trying."

"Yeah, thanks for the sage advice."

I took a hit of the bong and choked. She laughed.

The front door to the apartment opened and Sean walked through carrying a 12 pack of Corona. "What's up bitches, smoking without me?"

I had a ton left in the bowl, so I passed it to him. He grabbed it, sucked out the rest and blew out a huge plume of smoke, no choking or coughing. He laughed, turned to his 12 pack, and handed me a beer.

We drank the beers and smoked some more. I passed out on their couch, as usual, and they went to bed, probably to have sex.

***

That was our routine, drink, smoke, hang out, fall asleep; they go and bang. You'd think I would stop going over, partly because of jealousy, but partly because I was just a third wheel. I didn't stop though. On the off chance I'd catch some cleavage, or a whale tail out of the back of her jeans was enough to keep me going back weekly.

One day we were at their complex pool. I was excited, Anna, in a bikini, I couldn't think of anything else I would want to see more. We put all of our things on the deck chairs, and I took off my shirt and shoes. I was in my jean shorts, and of course Anna had something to say.

"Nice jorts," she and Sean laughed.

"You laugh, but these are comfortable."

"That is until they get wet and weigh 200 pounds," Sean added, they laughed again.

Sean took off his shirt, kicked off his flip-flops and immediately dove in. I walked to the edge of the pool and dipped my toe in to feel the temp. Anna wasted no time and pushed me in. Luckily, the water was warm, so I wasn't too upset. We all had a laugh at my expense.

My laughter trailed off when Anna began to pull off her white dress. She was wearing a light pink bikini that rode halfway up her butt cheeks. The top could barely contain her double D boobs. She adjusted the top, but no luck, no nip-slip. I had to look away before either of them realized I was staring. She grabbed her drink and sat on the side of the pool, her legs dangling in the water.

Sean and I swam around, grabbing sips from our beers and just shooting the shit. The sun was hot. The beers were going down easy, some would say way too easy for Sean. He was getting hammered and I was really starting to feel it. Sean could hold his weed, but I had him beat when it came to booze.

Anna never got in the water, so there was no way I could get a shot of her nipples through the light material. Bummer for sure. That didn't stop me from checking her out any chance I could. The sunglasses helped. But again, I had to be subtle.

It was starting to get late, and we ran out of beer, so we gathered our belongings and headed back to their apartment. After we ate some frozen pizza, Anna and I looked around and Sean was nowhere to be found.

Anna got up and looked around and found Sean had passed out cold on the bed, still in his wet clothes. She came back to the living room and said, "That pussy passed out. I even tried to smack his ass, he just grunted."

We had a laugh, and Anna retrieved her cushioned bag that held her glass pipe. We smoked some weed and that really kicked in the booze for both of us.

Anna stood up and pulled off her white bikini wrap and threw it on a nearby chair.

"This dress is getting on my nerves."

Thank God for AC, it was cold in their place. Her nipples were on full display and my dick was pressing against my still damp jorts.

Anna turned on her stereo and the sounds of Bob Marley filled the room.

I was sitting on the couch, and rather than going back to her chair, she came to the couch and sat very close to me. So close that she was sort of leaning on me. My dick was now at full attention, and it was quite uncomfortable. I had to rearrange my junk, but it wasn't possible with her right next to me. She took a toke from her pipe and handed it to me. I took a rip and placed it on the coffee table. I used that motion to shift my penis, so it was facing up into my waistband.

I sat back and Anna put her arm around. "How are we going to get you a girlfriend?" she asked.

I shrugged my shoulders and tried to keep my racing heart and sweaty palms a secret.

Anna stood up suddenly and left the room. She came back and said, "that pussy is still out. I just pulled off his shorts and threw a blanket on him. He better not puke in the bed."

"Should I go?"

"Why?"

"I mean, he's asleep, it's getting late."

"Fuck that, we're hanging out, fuck him." She laughed and I smiled. "I think I have some vodka; you want a shot?"

"I guess."

"That right there." She scolded.

"What?"

"Yeah, I guess. Make a fucking decision. Girls like that. You want a shot? Hell yeah I want a shot." She paused. "Well?"

"Hell yeah I want a shot."

"There ya go!" She leaned over me and put her hands on both of my shoulders. She shook me with a huge smile on her face. Her tits were inches from my face, but I wouldn't dare look down. "Confidence! That is the key!" She pushed off my shoulders and went to get the vodka.

She came back with two glasses full of vodka, not shots. She sat on the couch, but this time facing me with her one leg pulled up on the couch and the other touching the floor.

"What the fuck do you call these?"

"Shots!" She laughed. "Ready?"

"All this?"

She looked sternly at me, "Dude."

"Bottoms up!" I exclaimed.

Anna back handed my shoulder, and we clanked glasses. I took a deep breath and chugged the glass full of vodka. We both gagged a bit and grunted. "Holy shit," she blurted. "That was rough." After she said that she leaned back onto the armrest behind her. When she did so, her bikini bottom shifted, and her left pussy lip popped out. I nearly came in my pants right then. I looked away before she noticed I could see her bald lip.

She sat back up and looked down, "whoops," she said. She adjusted her bottoms. "You didn't see anything did you?"

"No," I stammered.

"You didn't?"

"Nope," I said shaking my head.

Anna stood up and walked in front of me. I thought I was about to get kicked out of the house. She placed her glass on the coffee table and turned back to me. She took her hand and pulled her bikini bottom to the side revealing her entire naked pussy. "How 'bout now?"

My eyes were wide and fixed on her beautiful pussy. It was shaved to the skin with not a single bump. She was fair skinned, so it was slightly pink. It was glorious.

Once I snapped back to reality I managed to blurt, "What are you doing?"

She laughed, put her vagina away and said, "Nothing. What are you doing?"

"You're drunk, I think I better leave."

"Look. Sean is passed the fuck out. I may be drunk, but I also know you haven't had any pussy in, what, years?"

I tried to talk but she interrupted. "Listen, I am willing to let you use my holes but with a few ground rules."

I couldn't speak.

"One, no kissing."

I was still at a loss for words.

"Two, you can lick it but if I think it's weird, we're going to stop. Three, no cumming inside me. I am on the pill, but you have to earn that. Four, this is just a friend helping a friend, we aren't going to fall in love. I'm with Sean. You need help, and I can help you. Deal?"

I tried to speak.

"DEAL?" she said again.

"Deal." I managed.

"Fine, let me go check numb-nuts and I will be right back."

I sat on the couch wondering what the hell just happened. What am I going to do when she gets back? Sean is my friend. What happens if he wakes up? I don't have a condom. I'm going to cum instantly.

I heard her coming back into the living room. "He's still out. I got this." She threw a condom at me, which I clumsily caught. She picked up her pipe, took a long drag then blew it out in my direction. She flopped down on the couch, looked over to me and said, "Well?"

I slowly stood up and began to unbuckle my damp shorts. I was already rock hard; anyone could see at this point. In true Anna fashion, "Looks like you're ready to go?"

I dropped my pants, and my fully erect dick was facing right at her.

"Not bad, I was hoping it wouldn't be tiny. Thick is good."

I looked down and then over to her. She pulled her bikini bottoms over her butt and then tossed them onto the floor with her feet. "Me first," she added.

I pushed the coffee table to the side as I knelt before her. With her feet on the couch, she spread her knees. I had a direct shot of her clit.

I slowly moved my head closer to her pussy, still in shock and still very hard. The pre-cum was already dripping down the tip. I slowly moved my hands to her thighs, and she jumped slightly. "Your hands are cold...keep going though, it's okay."

I moved closer until I was face to face with glory. I reached out to her pussy and spread her lips. She shuttered when my tongue grazed her clit. I continued. I slowly licked her pussy and clit as she moaned. I licked faster and focused on her clit. I was a bit rusty, but I got into a rhythm that seemed to be working. She grabbed the back of my head and pushed me hard against her pussy. I licked and sucked feverishly. She moaned more. Finally, she began to convulse. She whispered, "I'm cumming," and let out a sigh. She squirmed around a few seconds more as she finished her orgasm. When she stopped, she looked down at me; I was smiling. She patted me on the cheeks and said, "alright, let's see what ya got."

I was nervous putting on the condom, but I got in on without incident. Anna remained in the same position; knees spread. Her wet pussy right in front of me. "I know you haven't done this in a while so feel free to just jizz."

I nodded and positioned my dick right at the entrance to her pussy. Here it was. The moment of truth, the moment I had been dreaming about. She reached up and pulled my butt cheeks toward her and I entered her all the way to the base. She moaned.

I began to pump slowly. She wasn't wrong. I was going to cum quick, but I didn't want this to end, not yet. I grabbed for her tits, moving her bikini top to the side. Another dream come true; her pale nipples were inches from my face. I was slowly moving in and out of her. I grabbed her breast and squeezed, she moaned. It wasn't in the rules, so I leaned over and put her nipple in my mouth. She reacted strongly and began pulling my butt into her faster. This was not looking good for me. I felt my body tense, I was going to cum. I reached the point where there was no turning back, I came, I came hard. It felt as if I was filling her insides. I kept pumping until all of me was inside that condom. I slowed down. "Did you cum?" she asked.

"Mmmhmm," is all I could muster as I backed up.

"Awesome," she pulled her bikini top back over her boob, and I pulled out. "Not bad for a slump buster, eh?"

"I'll say."

Anna reached down and put her bikini back on.

I was standing with a semi hard dick and a half cup of jizz dangling from it.

"Boy, looks like ya had a lot in there."

I laughed. "Thank you." I said sheepishly.

"No sweat. Let me know next time you're in need of my services. I think I'm going to hit the sac, no pun intended." With that she stood up and scooted past me. She smacked my ass and ran into her bedroom.

I stood there stunned. That truly was the best day of my life.

So far