<p>“Weekday mornings are crazy busy,” Anna said. “Obviously. People need their coffee, after all.”</p><p>It was Derek’s first day at DiMaggio’s Coffee, the place where he’d be spending 30 hours a week during the last summer before he left for college.</p><p>He was still sweating from the early morning bike ride on a particularly humid day on the Connecticut coast. The air conditioning was going full blast though and he’d already started to cool down.</p><p>“Charles will teach you to work the register today and then you’ll be on your own for your next shift. Any questions?” Anna said.</p><p>Derek had a dozen questions, but he didn’t want to seem like an idiot. He found Anna irresistibly beautiful and far more sophisticated and worldly than him despite being only a year older.</p><p>“Nothing yet, he said. I’m sure I’ll have questions as the day goes on, though,” he answered.</p><p>Anna flashed a quick smile and said, “Don’t be afraid to ask. It’s better to ask a question you think is dumb than to make a dumb mistake. That being said, it’s okay if you screw up. We’re making coffee here, not trying to broker peace in the Middle East.”</p><p>Derek couldn’t help but laugh.</p><p>Again Anna smiled. “See! You’re already laughing. Don’t worry, it’s going to be a painless summer, I promise.”</p><p>Derek’s first day ended up being relatively easy, just as Anna had intimated it would, but that didn’t stop him from feeling exhausted when his shift ended.</p><p>“So, how was your first day?” Anna asked as they both clocked out.</p><p>“Really good,” he said. “Thanks to you, honestly. You really made it easy.”</p><p>It was true. Anna had been supportive and kind all day long, despite Derek having screwed up half a dozen times over the course of the day.</p><p>“That’s nice of you to say,” Anna replied. “I was like you last summer. Trying to make a little money before going off to college and not knowing what the hell to do. I didn’t have the luxury of a good boss though. The guy that worked here last year was a dick, and way too fond of touching the female employees.”</p><p>“Gross,” Derek said.</p><p>Anna laughed as she finished clocking out and grabbed her bag. She reached up and undid her ponytail, setting her shoulder-length curly brown hair free.</p><p>“God, the humidity is murder on my hair,” she said.</p><p>“It looks great,” Derek said without thinking. It did look great, though, at least to him. He couldn’t understand why she’d be unhappy with it.</p><p>Anna smiled at him. It looked even more radiant with her hair down. “You’re sweet,” she said. “Here, let me show you how to clock out.”</p><p>Derek stepped next to Anna in front of the computer and she showed him the fairly simple procedure of logging his hours to make sure his paycheck was accurate. He caught a faint whiff of her perfume and smiled as the feminine scent filled his nostrils.</p><p>“You smell great,” he said and immediately wished he’d clamped down on his brain’s desire to give voice to a thought without considering it.</p><p>Thankfully Anna laughed, and in a way that struck Derek as a sign of her bemusement. “You’re a little bit different, huh?” she asked.</p><p>“That’s not the first time I’ve heard that,” Derek said as he looked away.</p><p>Anna reached out and rubbed his arm. “Hey, different is good,” she said. “Trust me. Being like every other guy is not something to strive for.”</p><p>“It hasn’t been all that useful so far, if I’m being honest,” Derek admitted. “You’ve been to college, right? Be honest, do I really stand a better chance of getting a date there than I did in high school?”</p><p>Anna smiled at him and said “C’mon, let’s go,” as she slung her bag over her shoulder and walked out the back door. “You locked your bike up out back, right?”</p><p>“Yeah,” Derek said.</p><p>Anna walked towards the bike rack as Derek followed behind her. “Tell you what. I’ll give you a ride home. It’s hot as hell out here today so I’ll save you some sweat.”</p><p>“Will the bike fit in your car?” Derek asked.</p><p>“It will fit in my truck,” she answered with a smile while pulling out her keys and unlocking her truck.</p><p>Derek turned to see a battered blue F-150 just a few spaces away. “That’s yours?” he asked.</p><p>“Yup. A hand me down, really. My dad was going to sell it. I had to beg him to give it to me. It’s older than I am. We used to work on it together. I still change the oil myself,” Anna said as she beamed with pride.</p><p>Derek felt certain there wasn’t another 19 year old girl in their little town that did her own oil changes.  He smiled dumbly while staring at the truck and then looking back at Anna.</p><p>“What?” she asked.</p><p>“It’s kind of hot that you can do an oil change,” he answered, and again he regretted not reviewing his thoughts before giving voice to them.</p><p>“You really are different,” Anna said as she walked alongside Derek as he pushed his bike towards her truck. “Most guys are not into a girl that knows how to work on a car.”</p><p>“Maybe we’re both a little different,” Derek said as Anna unlatched the tailgate so he could lift his bike into the truck bed.</p><p>“Very nice,” Anna said.</p><p>“What, you didn’t think I could lift it by myself?” Derek shot back with a smile. “I may be skinny, but there’s some strength hidden in this body.”</p><p>Anna reached out and rubbed his arm. “It was a compliment, Derek. I promise,” she said. Derek couldn’t help but find it thrilling that her hand seemed to linger a little longer than was necessary.</p><p>It was sweltering inside the car as Derek climbed in. He stole a quick glance at Anna’s long, lean legs in the shorts she’d changed into after work.</p><p>“Do you like what you see?” she asked.</p><p>Derek was mortified but thankful he hadn’t been staring at her breasts. “Yes. No. Sorry,” he stammered.</p><p>Anna laughed and Derek smiled as the tension that had immediately built up dissipated.</p><p>“You know, the day is still pretty young,” she said while turning the air conditioning up to full blast and putting the truck in reverse. “You want to go swimming before I drive you home?”</p><p>“I’d love that. Do you know someone with a pool?”</p><p>Anna backed out of the space and smiled at Derek as she put it in drive. “I do not, no. I do, however, know a great spot where we can take a dip in the ocean without having to worry about anyone else. How does that sound?”</p><p>It sounded like absolute perfection to Derek, but he didn’t want to betray just how exciting the idea of going swimming with Anna sounded to him. “Sounds great,” he said.</p><p>Derek didn’t bother mentioning that neither of them had a swimsuit. He figured they’d go swimming in their underwear, which he found exceptionally exciting.</p><p>Anna pulled onto Route 1 and drove for a few miles before turning down a quiet street. She guided the truck through streets that grew increasingly narrow as they neared the coast before pulling into a small, sandy clearing that definitely didn’t look like a parking lot.</p><p>“We’re here,” she said before hopping out of the truck. “Are you coming?”</p><p>Derek slipped out of the truck and followed Anna as she pushed aside a thick layer of branches and disappeared behind a wall of vibrant green leaves. He pushed aside the same branches and found himself stumbling along behind her and picking up lots of little nicks and scratches.</p><p>Thankfully, it wasn’t much of a trek to get to the shore. They emerged onto a small, surprisingly private strip of sand buffeted by massive boulders on each side. The water of the Long Island Sound was always calm, but this was even more so than usual.</p><p>“Isn’t it perfect?” Anna said as she pulled off her t-shirt and unbuttoned her shorts.</p><p>“Yes,” Derek said, though he wasn’t thinking of much outside of the sight of Anna’s surprisingly athletic body as she stripped to her underwear.</p><p>“Are you going to join me or stand there and stare?” she yelled while sprinting towards the ocean and diving under the surface of the cool water.</p><p>Derek felt a surge of excitement as he stripped on the beach and tossed his clothes aside. He sprinted after Anna and dove in just as she had.</p><p>The water was cold enough to briefly shock Derek into speechlessness. They weren’t far enough into summer for it to have warmed up yet.</p><p>“Holy shit,” he finally said. “That’s cold.”</p><p>Anna smiled as she ran her fingers through her wet hair and swam towards Derek.</p><p>“I know, right? It’s a good way to cool down though, isn’t it?” she said.</p><p>“Definitely,” Derek answered as he watched Anna swim closer.</p><p>To Derek’s delight, Anna swam right up to him and wrapped her arms around his neck. She smiled and then pulled him close for a surprising kiss.</p><p>Derek closed his eyes and marveled at how eagerly Anna kissed him. She pushed her tongue into his mouth and he opened and accepted it. She had a firm grip on the back of his head too. He loved every second of it.</p><p>The bright, joyful smile on Anna’s face when she pulled back from the kiss thrilled Derek. She was only the third girl he’d kissed and the other two hadn’t seemed to enjoy it nearly as much as Anna did.</p><p>“Use your tongue a little more,” Anna instructed him before pressing her lips against his one more.</p><p>Derek happily followed her direction. He moved his tongue in concert with hers and the kiss felt even better. He loved how soft her lips were and how insanely arousing it was to do something as simple as rub his tongue against hers.</p><p>“Just a little slower with your tongue,” Anna said quickly as she came up for air.</p><p>Her tongue pushed gently into his mouth again and Derek followed her directions once more. He moved his tongue slowly, trying his best to match the speed she moved at.</p><p>“That’s really good, Derek,” Anna said as her hands moved to either side of his face. “You’re a quick learner. I like that.”</p><p>Her voice had taken on a lusty quality that filled Derek with desire. He’d only ever heard a girl talk like that in porn videos.</p><p>“Are you a virgin, Derek?” Anna asked as her hand disappeared under the water and moved down his chest and over his stomach.</p><p>“Yes,” he answered as Anna grasped his stiff cock through his boxer shorts.</p><p>“I think we can change that,” she said before kissing him again. Anna slowly stroked his cock under the water as their tongues danced.</p><p>Derek moaned into her mouth. He felt overwhelmed in the best way possible. He’d begun his day thinking this cute girl was going to be his new boss for the summer and it seemed like it was going to end with him losing his virginity.</p><p>“Follow me,” Anna said as she released Derek’s cock and swam towards the shore.</p><p>He followed eagerly, enjoying the view of her ass in wet panties on the few occasions it bobbed above the surface of the water.</p><p>Derek felt a little embarrassed when he realized he was going to have to walk onto the beach with a boner. He knew his cock was a little below average and he didn’t want her to suddenly lose interest in having sex with him. There was no way around it though.</p><p>He followed Anna out of the water and onto the sand. She quickly glanced at wet boxer shorts and obvious erection before offering Derek her hand as he approached.</p><p>The kissed again as Anna unhooked her bra and freed her perky breasts. She took Derek’s hand and guided it to her B cups.</p><p>“Be gentle,” she said.</p><p>It was the first time he’d touched a bare breast and Derek could barely contain his excitement. He’d enjoyed over-the-clothes touching with his two previous girlfriends but had never made his way to the bare flesh.</p><p>“They’re perfect,” he said while gently playing with Anna’s breasts.</p><p>She laughed before kissing him again. Her tongue eagerly invaded Derek’s mouth and she moaned as he gently rolled her nipple between his fingers.</p><p>“You’re making me wet,” Anna whispered between kisses.</p><p>Derek considered moving his hand between her legs, but thought better of it. He’d never touched a girl’s pussy before and he didn’t want to ruin his chance to have sex by doing something stupid.</p><p>“Take your underwear off,” Anna said as she stepped back.</p><p>Derek did as he was told and quickly pulled down his underwear. He kicked them aside and looked down at his hard cock. There was no question it wasn’t impressive, but Anna already knew that and she was still there with him.</p><p>“Lie down,” she said while pointing to the sand.</p><p>Derek got on his back without hesitation. All he could think about was finally losing his virginity. He’d fantasized about this moment for years and it was about to happen.</p><p>Given his anticipatory lust, Derek was surprised when Anna stood over his head and looked down at him.</p><p>“Have you ever gone down on a girl, Derek?” she asked.</p><p>“No,” he said while shaking his head.</p><p>Anna squatted over his head effortlessly and just like that her pussy was inches away from him. A thin layer of cotton was all that stood between him and the thing he craved most in the world at that moment.</p><p>“I’m going to let you in on a little secret, Derek. Being great at eating pussy will make up for shortcomings in other areas,” Anna said as she reached down and pulled aside her panties. “Do you want to learn how to eat pussy, Derek?”</p><p>“Yes, please,” he said.</p><p>“You see this?” Anna said as she spread her lips and pointed to a little pink nub above her pussy.</p><p>Derek nodded.</p><p>“This is what you need to concentrate on. That’s my clit. Licking that is what’s going to make me and any other girl feel good.”</p><p>“Really?” Derek asked. It was genuinely surprising. He hadn’t thought much about giving oral sex to a girl, but he figured putting his tongue in her pussy was how it worked.</p><p>“I know my pussy is what turns you on, Derek. You’re not alone. Almost every guy is the same. Certainly most of the guys I met my freshman year were that way. They were all so disappointing, Derek. You won’t want to be disappointing, do you?”</p><p>“No, I don’t. I want to make you feel good,” Derek said.</p><p>“Good boy,” Anna said with a smile as she sat on Derek’s face. “Now show you mean that and lick my clit until I cum.”</p><p>For a moment Derek felt overwhelmed. He hadn’t counted on his first real sexual experience with a girl being him going down on her. He figured he’d be having sex. Instead, a girl was literally sitting on his face.</p><p>“Eat my pussy, Derek. Don’t disappoint me,” Anna said in a demanding tone that Derek found oddly arousing.</p><p>He moved his tongue back and forth over her clit. He had no real idea how to do it, so he copied the same speed he’d moved at when they kissed.</p><p>“That’s good, but a little faster,” Anna said as she reached down and rested a hand on the top of his head.</p><p>Derek licked a little faster, just as Anna had instructed him. When she moaned louder it made his cock throb. There was no question he enjoyed giving her pleasure.</p><p>“That’s good, Derek. Keep licking. Keep eating my pussy and you’ll make me cum. Be a good boy and make me cum.”</p><p>It was the second time she’d called him a good boy and Derek found it thrilling in a way he didn’t really understand. Almost everything that had happened since they arrived at the beach was new to him though, so he just went with it.</p><p>Anna closed her eyes and tightly gripped Derek’s hair as he continued to lick her clit. She moaned louder and began to subtly move her hips.</p><p>The sun felt warm on Derek’s exposed, hard cock as he licked Anna’s pussy eagerly. He felt the sand against his legs and ass and the sound of the small waves gently lapping at the shore mixed with the sensual moans of the girl sitting on his face.</p><p>Anna leaned forward and moaned. Her thighs quivered around Derek’s head. He felt certain she was having an orgasm and that he’d been the one to give it to her.</p><p>“That was very good, Derek,” Anna said as she stood up.</p><p>He looked up at her with hope in his eyes. Derek figured it was his turn.</p><p>“I have to get home,” she said. “Put your clothes back on and I’ll drop you off.”</p><p>Derek was disappointed. His cock was so hard it ached. He’d just made her cum. As far as he knew, that meant he got to cum.</p><p>“But, what about me?” he said. </p><p>“You’ll get what you deserve, Derek, but not today. You have to earn my pussy,” Anna said as she got dressed.</p><p>Despite his disappointment, Derek was excited to hear that there was still a chance. That’s all he cared about. He dressed and followed Anna back to her truck.</p><p>“You don’t mind having to earn it, do you?” Anna asked as she turned the key in the ignition.</p><p>“Not at all,” he said.</p><p>“Good boy.”</p><p>Derek wore a blissful smile on the drive home. He replayed the experience on the beach over and over, and each time it thrilled him.</p><p>“Thanks for the ride,” Derek said as they pulled into his driveway.</p><p>“My pleasure,” Anna said. “You did a good job today, Derek.”</p><p>He couldn’t tell if she was talking about work or the fun on the beach. He chose to believe it was the latter.</p><p>“I’ll see you tomorrow,” Derek said as he waved while walking his bike towards the garage.</p><p>Derek felt giddy. He was certain he’d have to wait until college to lose his virginity. Now it seemed like it might happen this summer. He resolved to do whatever it took to earn Anna’s pussy.</p>