Don’t Worry Buddy, It’ll Happen

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Anal Toy

*This story is told from the perspective of three characters. These include Justin the boyfriend, Stacy the girlfriend, and Sam the best friend. There will be a heading with that character’s name whenever the story changes to their perspective.*

Justin

I felt bad for my best friend, Sam. He’s a really good dude, but unlike me, he didn’t have a girlfriend. We had both just turned 21 over the last couple of weeks. After a failed attempt to help him meet some girls at the bars, we stopped back at the apartment I shared with my girlfriend, Stacy.

“You boys are back already? No luck I take it?” Stacy asked.

“Nah, couldn’t keep any of the girls talking to us.” Sam said.

“Awe, that sucks! Don’t worry though, you are such a cute and nice guy. You will totally meet a girl soon.” Stacy said, resting a reassuring hand on Sam’s shoulder. Stacy was a sweet girl and an amazing girlfriend. She was 20 years old, funny, kind, and undeniably beautiful. Long brown hair, her eyes were a mix of blue and green, fair skin with a few faint freckles that you would never find if you weren’t looking for them, and an amazing body. Slender, cute and perky breasts, toned tummy and legs, and a perfect smooth pussy. She waxed regularly, so she was always smooth. I had gotten to know her body well. Over the last few months, we had been going further and further. We hadn’t had sex yet, but we had seen each other naked, a lot. A lot of handjobs and fingering and we even discussed trying oral soon. Stacy wanted to take things slow. She said she felt her last couple boyfriends used her for sex, so she wanted to take her time. I didn’t mind, I’ve gone 21 years in life without having sex. I could handle waiting until Stacy was ready.

I was at a dead end helping my pal, though. I’m the guy with the experience and I should be able to help, but maybe he just lacks something I have.

Stacy

I felt bad for Sam. I could tell he was getting frustrated. This wasn’t his first trip out with Justin to meet a girl. To be fair, even though Justin is a wonderful boyfriend, he might not be the best wingman. He’s not exactly smooth. He likes to think he’s a suave ladies’ man, but if I were being entirely honest, if I had met Sam first, there is a very good chance I would be his girlfriend, not Justin’s. Instead, here is this handsome and great guy, who mysteriously keeps striking out.

“Maybe we aren’t going to the right places?” Justin suggested.

“Or,” I interjected. “Maybe it’s not the place, but the company?”

Justin and Sam glanced at me and then at each other.

“I’m serious!” I said. “Did you stop to think two dudes approaching women might intimidate them? If I go with it might seem more disarming. And I can give you a woman’s perspective.”

Sam shrugged. “I guess it’s worth a try. Justin, you wouldn’t mind?”

“Nah,” Justin replied, shaking his head. “I know I have nothing to worry about.” At least he’s confident.

“Perfect! So Sam, coffee tomorrow? We can figure out all the deets?” I asked.

“Sounds great! I’ll even buy!” Sam said.

Sam

I walked up to Nikki’s Coffee, a small coffee shop literally on the same block as Justin and Stacy’s apartment. Stacy already had a table when I entered. She immediately noticed me, a warm smile appeared on her face. “Hey Sam, over here!”

“Hope you haven’t been waiting for long,” I told Stacy.

“I just got here myself, no worries. I already got us each a cup, single sugar and a splash of almond milk right?”

“Uh, wow. Yeah, that’s exactly how I take it. How in the world did you know that?” I asked.

“From last time Justin and I met you here. I overheard you ordering. It’s just like I take mine, so it stuck with me. I suppose great minds think alike.” Stacy replied with a wink.

I joined Stacy at the table, taken aback by her kindness. “Thank you, you’re amazing. But I thought I was going to buy?”

“I guess you’ll just need to beat me to it next time.” Stacy said. “So, Sam, you’re a good-looking guy. You’re chill, sweet, funny. Why are you single?”

I laughed, “thanks for saying that. Guess it’s confidence. Was always the quiet skinny kid until a year ago when I started working out. Now that I’m actually fit and more confident, I just don’t know where to start. Justin insisted he was going to take me out and get me laid. Said he’s become somewhat of an expert on women.”

Stacy mid-sip from her coffee brought her hand to her mouth and stifled a laugh. Barely avoiding spitting out her coffee. She swallowed and laughed. “Oh my god, he’s gotten such a big ego. I’m Justin’s first girlfriend. I wouldn’t say he’s any kind of expert.”

I shrugged, “to be fair, he attracted you. That’s a big accomplishment, if you ask me.”

Stacy blushed.

I continued, “if you don’t mind me asking. How did Justin first attract you?”

“Well, we had a class together fall semester. I noticed Justin stealing glances at me first day of class. When we were leaving, he asked if he could walk with me. He was cute, güvenilir bahis so I figured why not? We chatted, he asked for my number and we texted. Funny thing is, Justin isn’t the typical guy I go for. I had just broken up with my high school boyfriend a few weeks before. We had this long distance thing going on throughout freshman year, but it was just too much. So by the time Justin was talking to me, I was ready to move on. He was a good-looking guy who came by at exactly the right time.”

“Wow.”

“Oh, but he’s a great boyfriend! For real, aside from being a bit to full of himself and clumsy with certain.. activities, I’m happy I am with him.” Stacy took another sip of her coffee. “But, we are here to talk about you. What exactly is happening when you go out with Justin?”

“I don’t know where it’s going wrong. The times we meet girls, things seem to start out well. I’ve even had some approach me, but they seem to lose interest within a couple minutes of conversation.” Sam said with a shrug.

“I feel like there is something you aren’t telling me.” Stacy narrowed her eyes. “It’s Justin, isn’t it? He’s making things weird and scaring them off, right?”

“Um…”

“It’s ok, you can be honest!” Stacy said, reaching across the table putting her hand on mine to reassure me.

“Yeah, I feel bad saying it, because I know he’s trying to help.”

Stacy gave my hand a squeeze and smiled. “Let’s get a fresh start. We’re going to go out and do it right! It’s a crime a guy like you is single.”

God, Stacy was great. Justin was my best friend, but all I could think about was how much I wish Stacy was mine.

Stacy pulled her hand back to take a sip of coffee. Then with a chuckle she looked at me and said, “oh and it’s no surprise about Justin. He’s used all of his cheesy moves on me. Speaking of Justin, he’s probably back at the apartment now. Why don’t we head back and hang out?”

Justin

The door of our apartment opened and in walked Sam and my girlfriend. I had to restrain myself not to laugh. Stacy didn’t know what she was getting herself into.

“Well? What did you guys figure out?”

“We’re going to go clubbing tomorrow!” Stacy answered.

“Clubbing?” I asked. This would be good. I tried clubbing before meeting Stacy. You never get a girl going clubbing.

“Yes! Now, if you boys don’t mind, I need to look through my closet and figure out what I’ll be wearing.”

“How about we get a beer? Stacy is going to take forever to look through her clothes.” I suggested to Sam. I figured their clubbing attempt would be hopeless and I should throw Sam a bone. Maybe I could give him some last-minute advice.

“Sounds good to me.” Sam said.

Stacy gave me a kiss, then started towards our room. “Enjoy yourselves boys. Just don’t be too long, ok? It’s already getting late.”

Sam and I headed down to our local bar and ordered a couple of beers.

“Hey man, I appreciate you being cool with Stacy helping me out.” Sam said.

“No problem, but just in case things don’t go how you are expecting, I thought I should give you some advice. After all, I’m getting action on the regular here. I know a thing or two.” I said, throwing back my drink. “When you are talking to these girls, you gotta act like you aren’t interested. Give one-word answers. Ask them to repeat themselves as if you had something more important to do than listen. Girls crave that kind of stuff. And this is the most important thing. Once they take the bait, you need to be assertive. Tell them what they want, you know, boss them around a little. Chicks absolutely love that.”

“Yeah, I’ll keep that in mind. Thanks Justin, I appreciate the advice.” Sam said. And boy would he be finding out how valuable my advice was after striking out a time or two with Stacy helping him out.

Sam finished up his drink, and we both headed home.

Stacy

I had just finished picking out my clothes for the next day. I had stripped down to my panties and was going to get ready for bed when Justin came home.

“Hey babe, hope that’s not your outfit for clubbing!” Justin teased.

“Well, so what if it is?” I teased right back at him.

“I suppose I’d need to teach you a lesson.” Justin said, pulling me in and kissing me.

As usual, Justin’s hands went straight to my breasts. I needed to get around to teaching him some finesse. He tended to grope my chest wildly. He pulled my panties down and got himself undressed. We made our way to our bed, still making out. It was hard to get into things when he played with my pussy. Each time I felt like there was some rhythm going, he’d break it by switching between fingering me and rubbing my clit. Finally, after subtly moving his hand back into position and telling him not to move it, I got Justin to focus on my clit. At last, I had small orgasm. I wondered what I should try next. So far we’d only done things with hands. I was feeling like we should move further. I considered maybe giving Justin a blowjob. Then, as I started rubbing his dick, güvenilir bahis siteleri I was reminded about one of the things holding me back. His penis size was, well, less than impressive. Easily the smallest of the guys I’ve been with. Eventually I’d find a way to work with it, but for now I decided to stick with the handjobs. It didn’t take long anyway. After about a minute of playing with his dick, Justin was grunting and cumming.

“I’ll be right back with a towel!” I said. By the time I came back, a naked Justin was passed out on his back, snoring. I wiped up the cum and lied down on the bed next to him.

I wasn’t ready to sleep yet, honestly my orgasm wasn’t even that great. I felt a little unfulfilled. At any rate, I was bored and texted Sam.

Me – Hey Sam, I’m excited about clubbing tomorrow! =)

Sam – Me too Stacy! Thank you so much for going with me tomorrow. 🙂

Me – Don’t mention it! Just think, this time tomorrow you might be sharing your bed with a lucky lady! 😉

I glanced over at Justin. He was still sound asleep. His now soft penis had receded into just a small nub sticking out. Not exactly a sexy image. Suddenly I found myself jealous of the Sam’s hypothetical woman I just dreamt up!

Sam – Haha, well I hope so. Would be nice just to meet someone nice who I have fun with, a girl like you.

Sam – Sorry… I shouldn’t have said that!

Me – No, it’s fine. Actually, it’s really sweet. Thank you! I should really be getting to sleep though. Goodnight Sam!

Sam – Goodnight Stacy!

Sam

“Tonight is the big night Sammy!” I said to myself in the mirror. Maybe I was aiming high. I’ve never had luck before, but maybe it would be different hitting the town with Stacy. At any rate, giving myself a pep talk wouldn’t hurt.

I did a double take of myself in the mirror. I had grown very proud of my body. It represented a lot of hard work. After years of being ‘the skinny kid’ I was now a changed man. It was still fun checking out my muscles. After a bit of flexing, I looked down. Just having finished ‘man-scaping’ I was wondering if I should have left some hair. But the clean look did seem to emphasize everything, although I probably didn’t need to. I have no actual life experience to judge by, but my dick was like what I’d seen in porn and I heard those guys are bigger than normal. Hopefully, I’d have a chance to show it off.

I was genuinely excited for tonight, but as much as I tried to ignore my own feelings, my thoughts weren’t exactly where they should be. Spending the night with Stacy honestly had me more excited than hunting for women. Starting to touch myself, I thought about her. I looked at my hard cock and imagined Stacy wrapping her hand around it. Imagining what she must look like naked and stroked myself, faster and faster until I came.

After cleaning up I checked my phone, realized the time. Shit! Supposed to pick Stacy up in 15 minutes. Quickly, I got dressed and headed over to her apartment.

Luckily, I wasn’t too late. Justin answered the door when I arrived. “Hey Sam, Stacy is just finishing up.”

“Ok great! You really don’t mind that your girlfriend is taking me to the club to try to get me laid?” I asked, just to make sure there would be no hard feelings.

Justin laughed and shakes his head, “Man, don’t worry about it. Stacy would never want to cheat on me, I have no worries whatsoever. If anything I hope Stacy doesn’t get jealous.”

“I don’t understand. Why would she be jealous?” I asked.

“Because I’m going out to the bars. I’m undoubtedly getting hit on tonight.” Justin replied.

Just then Stacy walked out and oh man. She was a knockout. I only hoped Stacy and Justin didn’t notice me checking out her ass in her tight and very short skirt.

Stacy

“Hey Sam! You are ready to hunt with the expert?” I asked.

“Um, yeah.” Sam answered. He seemed a little distracted. In fact I think I caught him checking me out. Which honestly, flattered the hell out of me.

“Awesome! Justin honey, you going to be ok?” I asked my boyfriend.

“Heck yeah, I’m going drinking with Dennis and Wade.” Justin replied.

“Ok, don’t drink too much!” I kissed Justin and headed out with Sam.

The club was pretty wild and so much fun! I hadn’t been clubbing in a long time. “Hey Sam, you want to make some of these girls jealous?”

“How would we do that? And what would that do?” Sam asked me.

“Trust me, women can be as competitive as men. Let’s dance. Just take my lead!” I told Sam, taking him by the hand and leading him to the dance floor.

Sam was an amazing dancer! Time was a blur. We just kept drinking and dancing all night. At one point I was dancing in front of Sam, grinding my ass on him. I could feel his hard erection against me. Maybe this was too much with my boyfriend’s best friend, but I reminded myself it was just dancing. It wasn’t a big deal.

At one point, Justin texted me. He had drank a little too much and was spending the night at his friend Wade’s iddaa siteleri place. I didn’t mind, I was having so much fun! Maybe too much.. I was supposed to be helping Sam meet some girls, instead I was keeping him to myself. I couldn’t help it though.

Eventually Sam and I figured we had drank too much as well and he helped me back to my apartment. We laughed and joked as we stumbled along. Finally we arrived at my apartment. “Can you help me to my room Sam?” I asked, trying hard to keep my balance as I spoke.

“Sure thing.” Sam said, although he was barely in shape to even walk straight himself.

We got to my room. I gave Sam a small peck on the lips and said, “thank you.” Then leaned in and kissed more. I meant it only to be a friend’s kiss. Maybe there is no such thing, but in my drunken state I thought there was. Now we were beyond a tiny peck, our tongues were wrestling for dominance. I broke the kiss and told Sam, “I think I need to go to bed. You can sleep here too.” Stumbling toward the bed and slipped my panties down. I was so drunk it didn’t register as a bad idea. I still had my skirt on, anyway. Next thing I knew, I was sound asleep.

Sam

I couldn’t believe I just made out with Stacy. What’s more, she had just pulled down her panties, then passed out on her bed. When she did, her skirt hiked up. There she was, over the edge of the bed, legs spread, skirt up, and pussy on full display.

I couldn’t believe I was looking at the pussy of my best friend’s girl. It was a pretty slit, clean. If someone could be a pussy model, it would be Stacy. Her pussy glistened in the small amount of light coming from the door. Stacy must have been wet. In addition, her lips spread just enough to see her clit. I felt myself getting hard and tempted to reach out and touch her, but I knew that would be a mistake. I picked her up and moved her fully onto her bed. Then I stripped down to my boxers, which is how I always sleep, and laid down next to Stacy. Maybe not the best idea to strip to my boxers and go to my best friend’s bed with his girlfriend, but sometimes things seem like a better idea when you are drunk. Besides, we were only going to be sleeping.

Stacy

I woke up a bit groggy. Confused about where I was and what was going on. I looked around the room then at Sam sleeping next to me. Then I remembered I was so hammered I stumbled into my room and fell asleep. Sam must’ve had a similar experience. He was just in boxers, sleeping on his back. He was a handsome guy for sure. My gaze moved downwards from his face over his fit body. I wouldn’t mind if Justin had some muscles like his friend. Then my eyes moved further, stopping at his boxers. Sam must’ve had morning wood. There was a large tent in his boxers.

My curiosity was overcoming me, and I leaned in for a closer look. Instinctively I reached out and lightly touched the soft boxer material that covered end of Sam’s erect penis. Confirming he was still asleep, I glanced up at his face. Satisfied he was sound asleep, I gently reached for his waistband and pulled them down, freeing Sam’s penis and allowing it to flop onto his tummy. Quickly, I look at his face again to ensure it didn’t wake him. Looking now at Sam’s exposed genitals. Wow, he was much bigger than my boyfriend. His balls, probably a little bigger, I guess? Honestly, I don’t usually pay as much attention to that part. In fact, I had never taken the time like this to just take my time and closely look at a guy’s genitals in detail like this. Gently, I touched them cradling Sam’s scrotum. It was soft. He had also shaved clean, which I thought was nice. I just slowly massaged his testicles and continued taking in the sight. Sam’s penis seemed to get even larger yet. Damn, he was so much bigger than my boyfriend. Delicately, I felt his hardness with my fingers and moved one hand between my legs. Was I not wearing any panties!? I had forgotten I was so wasted I didn’t even care that Sam was in the room with me when I pulled them down. Had he had seen anything? I mean, I still had my skirt on, so I was probably still covered. Then I smiled at myself. It was rather silly to be concerned about Sam seeing my pussy as I was stealing a look, and a feel, of his penis.

I started to moan as one had rubbed my clit and the other gingerly explored Sam’s privates. The sound of my moan seemed to wake him a little. Quickly, I pulled his boxers back up and lied back down.

Seconds later, Sam woke up, rolled to his side and looked at me. I slowly opened my eyes, pretending like I had just woken too.

“Good morning,” Sam says.

“Good morning. Sorry I passed out so fast when we got back.” I said.

“No, it’s fine. I passed out right after you. I guess we overdid it on the booze.”

We both giggled.

“Yeah, maybe next time we drink a little less.”

“So you’ll still be my wing-girl then? I didn’t make an ass of myself when I was drunk?” Sam asked.

“Are you kidding? I had a great time! It was so much fun hanging out and dancing. Sorry we didn’t find you a girl though.”

“That’s ok, I still had a lot of fun too. Hey, you want to grab some breakfast? I’m still feeling affects from that alcohol and I’m sure some eggs and coffee would help. I’ll buy, what do you think?” Sam asked.

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