Nice Guys Finish Last

Note: Everyone in this story is 18. Also, I know no one in this story is married, but Loving Wives still seemed like the most appropriate category. Enjoy.

*****

Tyler was nice. A consummate gentleman. He always treated me so well. Never pressured me into anything. Always said the sweetest things and thought up tons of great little romantic gestures. He was the kind of guy you could bring home to mom. All my friends liked him. He got good grades, and was decent at sports. Enough to start on our varsity soccer team by the time we were seniors.

Unfortunately, halfway through that senior season, we got a transfer student, Mike. Mike played Tyler's position, and he was much, much better at it. The coach pretended that Tyler would get to keep his spot out of loyalty, but when Mike subbed in and scored two goals immediately, everyone knew what was coming. Tyler road the bench the rest of the season. He watched from the sidelines as Mike scored the winning goal in the state championship game.

The whole time, Tyler never complained. He practiced diligently, mentored the younger guys on JV, and even helped the coach with the gameplan once or twice. At the end-of-season banquet, he won a special award for sportsmanship and leadership. Mike won MVP.

After that banquet, I finally let Tyler fuck me. He'd earned it, I guess. After two years of sweet talk and loyalty and romantic gestures, I figured I owed him that much. Plus, I could tell he was really bummed about Mike winning MVP, even if he wouldn't show it. It was his first time, and as far as he knew, it was mine as well.

It was ok. My parents were out of town, so we went back to my place. He spent a lot of time eating me out. I'd let him do that a few times, so it wasn't anything new. After like 15 minutes I got bored as usual, so I faked an orgasm. Really flexed my acting chops this time.

I brought his face up to mine and whispered, "Hey, you should go grab a condom." His eyes lit up like a child on Christmas.

"Really?!" He said breathlessly, "Are you sure?"

I laughed, "Of course I'm sure, silly. It was all I could think about watching you on stage in that nice suit of yours. You looked so damn sexy."

I guess I had actually been pretty horny during the ceremony. But, whether it was because of Tyler was up for debate. A lot of the other boys looked damn good too. I'm a sucker for a guy in a suit... I'm a bigger sucker for a whole team of guys in suits.

Tyler was beyond excited. He tried to kiss me, but I pushed him away gently. "No, Tyler. You just went down on me. You know I don't like that."

"Right, sorry," he said, disappointed in himself for forgetting. Remembering what was about to happen, he got up and bounded over to his clothes. He pulled a condom out of his pants pocket.

"Oh, were you expecting this tonight?" I love taunting him.

"I mean, I've just been carrying it for a while now," he said sheepishly.

I laughed, "Come over here and just fuck me, would ya?" He smiled and made his way across the room.

He was slow and gentle. Like always. After a lot of kisses all over my body, he tore open the wrapper, put the condom on, and started rubbing the tip of his dick up and down at the entrance of my pussy.

"Well, what are you waiting for?" I said, half playful, half exasperated. He laughed nervously and thrust into me.

The look on his face was priceless. It was like he was seeing God. His dick felt ok, not the smallest, definitely not the biggest. He went slowly for a long time, asking if I was ok more than once.

"Oh, right. I'm supposed to be a virgin," I thought to myself.

"Uh, yeah. It hurts a little, but not as bad as I thought it would."

I guess my real first time had hurt a bit, but I got past it pretty fucking quick.

He picked up the pace. I could tell he wanted to cum really bad, but he held it back. Classic Tyler, always thinking of others. As he pounded away, he buried his face in my neck and began kissing, and biting it haphazardly. It was fine. I was getting a bit bored. My gaze wandered around the room and passed by my phone on the bedside table. I saw the notification light blinking. While Tyler was preoccupied, I reached over and picked it up.

It was a text from Sarah, my bff.

It read, "Hey girl, you'll never guess who's dick I took tonight."

I grabbed Tyler's head and pressed it further into my neck and hair. I moaned to make him think I was really digging it. I looked back at the phone and started typing.

"Was it your cousin, Sarah. Because I really don't need to hear about that again."

"Second cousin! That's a very important distinction. Plus, I only ever sucked his dick..."

"Whatever, I just don't need any more of your incest stories."

"I hate you. Anyway, no. Ya girl here bagged the MVP."

"Oh, shit!! You fucked Mike!!"

"I did!! And, it was fucking good. Now I get why Leah snatched him up in a relationship so quick. Not that it's stopped him from banging half the girls in the school lol. He told me I was the third this week, not including Leah. Fucking prick. How about you? You finally let Tyler toss one in ya?"

"Yeah actually. He's going at it right now. Trying so hard not to cum lol. It's adorable. "

"What?! No way! I thought you were gonna string him along until he fucking proposed lol."

I opened snapchat and took a quick selfie video. Making sarcastic faces at the camera like this sex was blowing my mind. I added the caption "Proof" and sent it to Sarah.

"Haha, atta boy Tyler. Always working hard. I'm happy for him. It's about time he got to try out his girlfriend's pussy. Everyone else already has ;)"

"Hey, I've been good. It's been like a whole month."

"Riiiiight. A whole month my ass. I ate your pussy fucking yesterday."

"Oh yeah lol. Well you don't count. That was just a nice favor between friends ;)"

"Uh huh, well I hope Tyler appreciates the favor your doing for him. Your pussy is dope. He should feel lucky to get a crack at it. I'm gonna get to bed. Fucking the MVP all night really takes it out of you. Have fun with Mr. Sportsmanship or whatever."

"Lol, fuck off."

Tyler was barely hanging in there. He'd been holding back cum for like 10 minutes now.

"Ooh, that's it," I said. Someone give me a fucking Oscar. "Are you gonna cum for me baby?"

"Can I cum on your tits?" he managed to grunt.

"No baby, you know I don't like that. Just use your hand like when I blow you."

He looked disappointed, but didn't argue. He pulled out, ripped off the condom and finally came by jerking off onto his hand.

"Dont get any on the blanket," I said. Handing him some tissues from the night stand. He cleaned himself up, then came back to bed to snuggle.

"That was amazing," he said breathlessly. "Did you cum too?"

"No, but it's ok. I came earlier when you were eating me out. It still felt really good. Especially since it was my first time. Thank you for being so gentle."

He smiled and kissed me. "I love you," he said, quietly and earnestly. Another first.

"I love you too." He smiled wider than I'd ever seen, and held me even tighter. We stayed like that until he fell asleep. I carefully extricated myself from his grasp and walked over to the bathroom with my phone.

As I peed I opened it and saw a new snap from Sarah. It was a selfie of her with a big shit-eating grin. Fresh cum all over over her face. The caption said, "Came back for seconds."

Jealousy and arousal washed over me. Mike had looked really good tonight. Hell, he looked good every night. I started touching myself, but the snap went away.

Shit, forgot to screenshot it. I kept touching myself and flipped over to a file on my phone reserved for sexy pics and saved snaps. I scrolled through, spending a few seconds on each picture. Most were nudes from Sarah, but some were of her with other people, guys and girls. Some were with me. Some were my own pics with my own guys and girls. Each one hotter than the last. I could feel myself building to orgasm.

Eventually I found my absolute favorite pic. I was in the middle on my hands and knees. Not looking at the camera, too focused on what I was doing. Jason, another guy from the soccer team who'd played Tyler's position before graduating last year, was in front of me. His dick almost completely stuffed down my throat. His buddy (Phil, I think) was railing me from behind, bareback. They were looking at the camera laughing and high-fiving.

In front and to the side was Sarah in all her glory. Miller Lite in one hand, flicking off the camera with the other, cigarette hanging out of her mouth. Completely naked from the waste down and wearing only what I recognized as Tyler's old warm-up jacket. Her face was again covered in cum from the photographer of this lovely scene. Don't remember his name at all. Definatly fucked him later that night though... I think.

As I took in this beautiful portrait of perhaps the single sluttiest moment of my life, my crowning achievement, my hand kept working on my now soaked pussy. An orgasm came pulsing through my body. I tensed up and convulsed as I was transported back in time to that night in Jason's basement.

The smell of sweat and cum and sex and beer. The feeling of choking on a nice big hard cock while another filled me up from behind. The sound of Sarah, laughing and calling me a whore and a dirty slut. The knowledge that she was absolutely right. The sound of flesh smacking against flesh, echoing off the bare cement walls. The amazing, completely unique feeling of hot cum spurting out from the cock inside me. Filling me up with that hot sticky mess that I can never get enough of. I came, hard. Trying my best to stifle my moans so as not to wake Tyler in the next room. Eventually the orgasm subsided. I was able to uncurl my toes, and focus my eyes again.

As I came back to reality, I looked down at the photo. My eyes were drawn to the timestamp. 08/11/2018. The day before Tyler's 18th birthday. That birthday was the first time I'd let him go down on me. It was my gift to him. I'd even started to blow him, but I stopped, telling him I just wasn't ready. He was very, very disappointed, but he understood. He really is just such a nice guy.

...

I was a good girl for a while after that. Maybe Tyler was rubbing off on me. I didn't cheat on him once through the winter. I mean, except for Sarah, but that doesn't count.

Good God, no one in this world can eat pussy like her. I think she was single-handedly responsible for every orgasm our school cheer squad ever had. Lord knows their football player boyfriends weren't getting it done.

Anyway, Tyler and I had a nice time. We spent most of our last year cuddling up and watching movies in my basement. Usually we'd get 20 minutes in before hands started wandering and foreplay got started. He was actually getting pretty good. He started being able to make me cum for real, and I finally coaxed him into being less gentle and fucking more me like the whore I am. I actually thought I might be able to make this work, and not return to my old slutty ways.

Of course that didn't last long. As spring rolled around, senioritis ramped up hard for all of us. People started skipping or leaving early. Even the teachers seemed checked out. Then, the house parties started up.

Everyone wanted to make the most of the last few months of our high school experience. That meant sneaking booze, parties whenever someone's parents left town, and the desperate search for sex. No one wanted to graduate as a virgin.

I swear, Sarah was making it her mission to make sure that didn't happen. It seemed like every weekend I got another snap of her with another random guy's cum covering her face. Or leaking out of her pussy. That girl should really be on birth control. Occasionally, there was one with some new girl's face buried in her snatch, but she was on a streak with the guys. She was calling it the season of the dick. I told her it was stupid, but I was also insanely jealous.

Her reputation at school had gotten out of control. Every single dude had either fucked her or was trying to. They didn't have to try very hard. It was a matter of scheduling more than anything. She'd even taken to skipping class to fuck in the janitor's closet... and the girls' locker room... and the boys' locker room... and her car... and my car... and Mr. Taylor's office... and Mrs. Taylor's office. That marriage was definitely on the rocks.

It became known that if you wanted to get some before graduation, you had to talk to Sarah. She loved it. I'd never seen her happier than taking dick after dick. Of course I heard all about it. She would whisper stories about her adventures whenever she fingered me. It always made me so fucking wet. My favorite part was that she'd taken to making guys take condoms off. Nothing sounded hotter to me than stopping everything, ripping off the condom, and shoving a guy back in. The looks on their faces must be priceless. I always managed to cum when she'd describe them cumming inside her. She told them she was on BC, but I knew the truth.

The risk factor were so fucking hot. Here was my best friend, living her best life, getting filled up by random dudes on the daily, and I'm stuck at home with my boring sweet boyfriend. It was becoming more than I could take. The next time a house party came up, I made sure I was gonna be there.

It was at Leah's house. She told me to invite Tyler, but I guess it slipped my mind. As far as he knew, I was home studying for AP exams. He'd been really disappointed. He was looking forward to getting some, but he understood. School comes first. Now he was at home, probably jerking off to the memory of me finally letting him cum in my mouth. I'd had to give him something before I went to this party. I'm not cruel. He'd thought we were being so naughty, a bj in the school parking lot. Oh Tyler, he's so innocent.

...

I walked in with Sarah. She was immediately swarmed by guys. Some new ones, but by this time, most were looking for another go. Tonight was about me, though. Sarah was determined to get me what I needed. The way she shooed those boys away was masterful. They all thought she was easy, and they were just passing her around. But, she had them wrapped around her finger, at her beck and call.

She's an inspiration.

We made the rounds. Talking and flirting. There were some cute guys, but no one who really impressed me. This was my return. My big reopening. I had to have something top shelf. Plus a lot of the guys had a laser focus on Sarah. They'd heard what was up, or they knew first hand, and it was like I was invisible. Multiple guys missed their chance with me because they were too busy drooling over her. Boys are dumb.

Sarah and I were hanging out drinking in the kitchen, commiserating about the lack of a good option, when Leah and Mike walked in. They were arguing in hushed, angry tones. The whole time, they kept shooting furtive glances in Sarah's direction. I could guess what this fight was about.

After a few minutes Leah stormed off, shooting a nasty look at Sarah while she passed by. Mike just stood there, glaring off in the distance, looking annoyed. Without thinking, I grabbed another beer from a nearby cooler, walked over, and handed it to him.

"Trouble in paradise?" I asked. Mike accepted the beer, and his expression softened.

"Yeah, you could say that. Leah found out about my ride on the town bike over there," he gestured towards Sarah who was now flanked on either side by two guys from the basketball team. They were both like 6'5". She was in heaven.

"Yeah, I could see why she'd be upset. You guys are supposed to be the classy ones. Prom king and queen and all that."

Mike chuckled, "I guess that's what she wants, yeah."

"What do you want?" I asked. He seemed to think deeply for a second.

"Pussy," he said in a matter-of-fact tone. I burst out laughing.

"Wow, you're a man who knows what he wants, huh," I managed to get out through my giggles.

Mike was smiling mischievously, now. "I am. And, I'm serious. I'm a sports star. I'm the hot new kid in town. I get good grades. I'm in with the popular kids. Not to be a douche, but I could pretty much get any girl I want. Especially when everyone's looking for some before we all go off to college. I'd hoped Leah would be cool with it. Us keeping up appearances while still screwing around as much as we want. She gave it a try, but I don't think she was ready for the sheer volume, ya know?"

I chuckled, "Yeah, from what I've heard you aren't exactly easy to keep pace with."

Mike smiled. His eyes lingered on mine for a moment before moving over to the corner of the kitchen where Sarah was now down on her knees, a cock in each hand and a look of pure bliss on her face.

"That certainly didn't help anything. I knew for some reason that Sarah would bother her. That's why I didn't tell her for so long. It got back to her eventually. Your friend isn't exactly discrete, is she."

"Not quite." Sarah was now balls deep on one dick and stroking the other. Her shirt had magically disappeared. No bra of course. A small crowd was gathering.

"You know why Leah was so upset about Sarah, right?" I asked.

"No," he said, tearing his gaze away from the show going on in the corner. His tone was a bit surprised.

"They were together a while back. Like really together. Like young love, gross cutesy together."

"Really?" He said, shocked. "I never would have guessed that."

"Oh yeah, lost their virginities to each other and everything. They were actually really cute together. Made me want to throw up."

"Shit, if I had known...I mean, it's not like I had much choice in the matter. Sarah has a way of getting what she wants."

Mike pondered that for a moment. Sarah was now on her hands and knees getting spitroasted out in the open for all to see. People had started cheering.

"Hey, it sounds like she was ok with you doing other people. If she had a problem with someone specific, she should have told you."

"Probably," Mike shook off whatever was consuming his thoughts and turned his attention to me. "Hey what's your deal? I always see you with that guy. Tim something?"

"Tyler," I corrected him. "You took his spot on the soccer team, remember."

"Oh that's right, Mr. Sportsmanship. No offense, but that never made sense to me."

"How so?"

"Well, given the company you keep," he gestured over to Sarah. The guy fucking her had just cum.

He high-fived the guy in front, tagging him in. He took his place behind Sarah, put himself inside her pussy, already dripping with cum, and went to work. Another guy from the crowd walked up in front with his dick out. Sarah immediately latched onto it and started sucking. The crowd went nuts.

"I don't know, I just expected you to be a little more wild."

"Oh, I can get wild," I said, looking him directly in the eye. "I've just been taking a little break. Wanted something wholesome for a while. I think it's just about that time I got back out there though. Provided I can find what I want."

We were staring at each other now. Really seeing each other for the first time. Mike had stopped stealing glances at the girl getting spitroasted in the corner. His eyes were now only focused on my lips. He leaned in close. The crowd had gotten pretty loud, and he had to make sure I could hear. I turned my head and brought my ear close to his lips. Feeling the heat from his breath, taking in his scent. It was intoxicating.

"What is it that you want?"

I slowly leaned back. Looked him up and down. I cracked a grin and wordlessly took his hand. I began leading him out of the kitchen. I took one last look back at Sarah. I could have sworn I saw her wink at me, but it was tough to say. Her little tryst had turned into a full on gangbang by this point. She'd be busy for a while.