My Best Friend's Boyfriend

All characters are over the age of 18.

*****

-Previously: Mason and Jessica had sex in his car, and he didn't pull out. Jessica is worried because she isn't on the pill, but figures that she probably won't get pregnant from one time. Mason dropped her off at home, where Jessica ran into a horny Oliver, who had been waiting for her. She refuses to have sex with him.-

Oliver didn't take my denying him sex very well. Not well at all, actually. He complained that he had been waiting for hours, and I owed him because he made me cum earlier, and I was being a prude. Then he stormed off. What a great boyfriend.

The rest of the weekend passed without incident...probably because I holed up in my bedroom in hopes of avoiding Anneka and Mason. I wondered if they were having sex. Surely they were. Mason kinda seemed like the kind of guy who had an unquenchable libido. It, oddly enough, made me kinda jealous. I knew I shouldn't be, and that the best course of action was to pretend that nothing ever happened between Mason and I, but how could I? Anneka was probably off sucking his dick right now. I shuddered at the thought.

"Come on, pull it together, Jess." I told my reflection in the bathroom mirror. "Get over it. It was a one time thing. You have no right to be jealous. You love Oliver." I tried to convince myself. It wasn't working very well.

And then I remembered the feeling of all that cum inside me, and how it had pooled around me when I took a bath later that night.

There was so much...

I should never have agreed to sex without a condom. Actually, I should never have agreed to sex at all. That was obvious now. I decided that I probably wasn't pregnant and I had nothing to worry about. Nothing except the fact that I had cheated on my boyfriend with Mason, of course.

When monday came, there was no more avoiding my friends. Anneka greeted me at the front door, cheery as ever with bouncing red curls.

"Hey, Jess! You went kind of AWOL after dinner this weekend. Are you okay?" She asked, looking concerned.

I smiled tightly. "Yeah. I just had a...stomach bug. I wasn't feeling well."

"Aww," She said in a sing-song voice, looking sympathetic. She brushed a blonde hair out of my face. "I'm glad that Mason gave you a ride home when he did. He's just great like that!" She exclaimed, completely unaware of what had transcribed between him and I just a couple days ago.

"Oh, there he is!" She shouted, waving her tall green-eyed boyfriend over to us. Shit.

"Speak of the devil..." I mumbled under my breath. He approached us, a certain swagger in his step.

"Hey there, ladies!" He greeted, smiling as though nothing was different. Maybe it wasn't. Maybe everything could just go back to normal. But...maybe I didn't want it to.

Anneka grinned and pulled him into a kiss. He had to bend down, and she had to stand on her tippy toes to reach his lips. Their height difference was dramatic. I wondered if it ever annoyed Mason that his girlfriend was never on his level. He needed a nice tall girl...like myself.

I looked away to shield my eyes from the PDA going on infront of me. It just brought back memories of how his lips felt on mine...and that wasn't what I needed.

"Get a room!" I joked, trying to act natural. I wasn't doing a very good job.

Anneka pulled away from her delicious boyfriend, a string of saliva between their lips until it broke. Gross. "Sorry, Jessie. I just couldn't help myself." She teased, staring at him adoringly.

"Neither could I," Mason agreed, though he didn't take his eyes off mine the whole time he said it.

"Okaaaay, then..." I commented awkwardly. "Well, um, I have math class and I don't want to be late, so, um...see you guys later, okay?" I speed-walked away from them, feeling extremely guilty and uncomfortable. I could barely look Anneka in the eye. I felt like a total asshole, and a shitty friend. Yay.

"See ya later, sexy!" Mason called after me. I stopped and turned around, all the blood draining from my face. What did he think he was doing?! Anneka would surely notice that-oh. Upon further inspection, I realized that he wasn't talking to me, but instead to Anneka, who was running off to class, her ass swaying in her skimpy cheer uniform. I tried to suppress the jealousy brewing in my stomach.

After that awkward encounter, I couldn't focus at all in math class. My mind kept drifting back to the image of my best friend bouncing up and down on Mason's dick, of him cumming inside her little pussy. I wondered if she was shaved down there, and what her nipples looked like. I felt a wetness in my panties, partially from the thought of Mason, and partially from...Anneka?

Wait a minute. No way. I liked boys. Anneka's just my friend. Nothing more...right? My mind continued to wander, shifting to thoughts of her masturbating alone in her bedroom at night, her delicate little hands furiously working at her clit. I wondered if she ever imagined me doing the same thing. Probably not...

I didn't get much work done for the rest of the school day. I was distracted by sexual thoughts. I didn't know what the deal was, I hadn't been that constantly horny in a long time. When I went to the bathroom in 3rd period, my panties were soaked through with my juices. I masturbated on the toilet like a virgin amateur. Eww.

My shame-ridden toilet seat orgasm didn't keep me satisfied for very long. Twenty minutes later, I was ready to go again. I considered texting Oliver to skip class with me and have some fun in a janitorial closet, but decided against it. I just couldn't face him yet.

Last period, I had PE. I changed into my outfit, a pair of short workout shorts that barely covered my ass, sneakers, and a tank top that displayed my perky DD breasts. They tried to enforce a dress code during my sophomore year, but eventually gave up. Horny teenagers throughout the school greatly appreciated it.

In the locker room when we were changing, Anneka pulled me aside. "Hey, Jess, do you mind if I talk to you for a minute?" I nodded, anxious that she had found out about me and Mason.

"What's up?" I asked nonchalantly.

"Okay, don't hate me for asking, but are you and Oliver okay?"

I was taken aback. That wasn't the question I was expecting. "Yeah, we're fine." I replied. "Why? Is everything okay with you and Mason?"

"What?" She asked. "Me and Mase are great. I mean, don't tell anybody, but we fuck, like, twice a day. It's AWESOME."

She subconsciously started feeling her breast, probably replaying their sexual adventures in her head. Getting back on track, she took her hand off her tit. "I only asked about you and Oliver because he said that you were being weird. Somethin about you not wanting to have sex. Is that true?"

"What?! That was one time. I was just tired, and I felt sick. I can't believe he went behind my back and talked to you. He should have just asked me." I said angrily.

"Hey, Jess, don't be like that! It wasn't a big deal, he was probably just worried about you. And I kinda am, too."

"What do you mean?" I asked, growing concerned about the secrecy of my slutty car sex again.

"You've been weird all weekend."

"I told you, I was sick."

"I know, but like, at dinner you literally shouted 'Oh, God!'. Like, what was that about?!"

I sighed in resignation. I figured it would be okay if I told her about Oliver and I at the restaurant. We were always pretty open with each other about our sex lives, anyway.

"Okay, you're probably gonna think I'm a total slut, but I let Oliver finger me at the table."

Anneka's mouth formed a perfect 'O'. "No way! Oh my God, that makes so much sense. That's why you were all red and breathy!" She giggled. "That's so hot. Have I told you about the time I gave Mason a handjob at the table? And my parents were right there!"

'No, you didn't tell me, but your boyfriend did.' A voice whispered in my head. I told it to shut up.

"And this might be a little TMI," She continued. "But he cums, like, a lot, and I mean a lot, so he made this big mess. So to cover it up, I 'accidentally' spilled my grape juice on his lap. Isn't that hilarious!?"

I was already turned on watching her grope her breast, and now her talking about how much Mason cums? Yeah, the state of my pussy was hopeless. I hoped the wetness didn't soak through my shorts. That would be embarrassing.

"And I know I've already told you, but he's fucking HUGE. Like, pornstar huge. No, bigger. I'm talking mammoth. Like, over a foot long. And thick! He's so thick. And he's got a mushroom head, which is sooooo hot, but sometimes it's hard to fit in. I can only take about six inches max, TBH."

I laughed uncomfortably. "Can we stop talking about your boyfriends dick, please?" I pleaded, trying to stealthily ease some of the tension in my crotch by rubbing my clit through my shorts. I relied on the fact that Anneka was too caught up in her own world to notice.

"You're so right. We should talk about your boyfriends dick instead! So, what's Oliver packing? I can't believe we've never talked about this."

I was growing desperate now, my dry masturbation growing more needy and less discreet. "He's, umm, decent sized. You know, just...pretty average, I think."

I watched helplessly as Anneka's eyes drifted from my face towards my crotch. As soon as I noticed, I took my hand away and put it behind my back like a child caught with my hand in the cookie jar.

"Jess...were you just...touching yourself?" She looked up at me, curiosity and surprise written all over her face. I blushed in complete and utter embarrassment. She must have noticed how flustered I looked, because she shifted demeanor. "It's okay, you don't have to be embarrassed! All girls do it. It's nothing to be ashamed of." She put a hand on my shoulder comfortingly.

"In fact...I can help you out if you want." She smiled sweetly. She was pretty. Really pretty. I hadn't noticed before today, but she was hot, too. She was short, with a plump ass, B cup breasts, and a tight muscular waist. I didn't want to admit it, but...I wanted her. I wanted her to do things to me...dirty things.

She stepped even closer, backing me into a corner. "It really wouldn't be that big of a deal. I could just help you with your little problem. As a friend."

Looking around, I noticed that the other girls had cleared out of the locker room. They were probably out running their laps right now, which meant that they wouldn't be back for about another hour.

"It wouldn't be that big of a deal..." I repeated, my voice soft and breathy. Anneka pressed her body against mine, her face directly in my breasts. She planted kisses over my firm tits, reaching her left hand up to grab a feel.

"I've always loved your boobs, Jessica..." She whispered. "So nice and perky. Will you show them to me?"

I couldn't exactly say no, so I nodded in agreement and removed my tank top. Anneka looked pleased. "I like that bra..." She told me, admiring the black lace detail caressing my breasts. "but I would like it better on the floor." She said, smiling, the innocence gone from her sweet face.

She reached behind me and effortlessly undid the clasp so that the bra fell off me onto our feet. "Much better." She told me happily. "God, Jessica, you have great tits." She placed her mouth over my nipple, and sucked lightly. Nobody had ever done that to me. It felt exquisite.

I removed my shorts and panties without being instructed to. "Ah," The redhead breathed. "Your little problem. I'm gonna take great care of you, okay Jess?"

I nodded, excited. I'd never done anything with another girl before. Anneka trailed kisses down from my breasts towards my crotch, looking up at me the whole time with her light blue eyes. She planted a final kiss on my pussy, where my pubic hair would have been if I didn't keep my cunt bald.

With great expertise, she placed the tip of her tongue at my entrance, then licked from there to my clit. My knees felt weak with pleasure, and I sat down on one of the metal changing benches.

"Lay down." Anneka instructed, and I did as I was told. I leaned back with my knees up on the bench, in a position similar to the one I'd be in if I was giving birth.

She began to eat me out like a damn pro. She changed pace, slower then faster, changing tactics every now and then. She inserted her tongue into my entrance, then focused on my clit for a little while. It was heaven on earth. I'd only been eaten out one other time in my life, by Oliver on my 18th birthday a few months ago.

She stopped to insert three fingers into my pussy with one hand, and play with my clit with the other. I guess being ambidextrous came in handy during sex. She sped up, pumping her fingers in and out of my pussy faster and faster. She was in just the right position so that she was hitting my g spot. She was worlds better at fingering than Oliver was.

"Anneka, I think I'm gonna cum...!" I moaned. She just smiled naughtily, increasing even more in speed. I felt my orgasm build then break the surface, so intense I physically shook. Then, strangely, my vagina released a clear liquid, onto Anneka's freckled face. She opened her mouth to take in the liquid, clearly pleased with herself. I moaned loudly, all the while, enjoying what was probably one of the best orgasm's of my life, only second to my one with Mason in his car.

Several shots of the liquid released my vagina, wetting the bench, Anneka's face, and her red hair. I'd heard myths of squirting orgasms, but had never experienced them. I figured that female ejaculation was a fake trick for pornos. I was wrong. My orgasm faded, and I came down exhausted and thoroughly pleasured.

"Oh. My. God." I panted, sitting up. "How did you do that?"

"Ah, just a trick I learned a little while back. Pretty neat, huh?"

All I could do was nod in agreement, enjoying my post orgasm high. "I'm sorry I squirted in your hair." I apologized. She didn't seem to mind.

"It's okay, Jess. You couldn't help it. Besides, there are showers in here. I can just rinse it off."

I dried off with a towel and got dressed while Anneka bathed in one of the locker room showers. My first time with a girl, my best friend of all people, and I had to admit that it was pretty good. She wasn't as good as Mason or anything, but still way better than Oliver. Actually, the more I thought about it, the worse my boyfriend's sex game seemed. He was my first boyfriend, the boy I lost my virginity to, and seeing that (until this weekend) he was the only person I'd ever had sex with, I didn't know any better.

PE ended, and I drove myself home. I pulled up my Period Tracker on my phone, an app I downloaded on my phone a few months ago to keep track of my monthly cycle. My good mood was ruined by the display infront of me on my screen. I was three days late.

-TO BE CONTINUED-