Dylan was nineteen years old and worked the second shift at the corner convenience store. He has worked there for a year to help give him spending money while attending college during the day. Glancing down at his watch for the fifth time in the past hour, Dylan started to wonder where Shelby was. Shelby was an older woman, who for the past six months, has stopped in around seven o’clock to grab herself a cup of coffee. She was always dressed smartly in a dark-colored skirt and a lighter-colored button-down blouse to match her skirt. Dylan figured that she worked in one of the offices close by. For the past month, she had taken to flirting with him and it made him feel good.
Being a farm boy, he was kind of shy around girls so most of the girls on campus ignored him. Shelby, on the other hand, was a boost to his ego. So much so that he was going to take the plunge and ask Dana, his biology study buddy, to go to the movies with him Friday. She may turn him down but at least he had the nerve to ask her, something he would not have done before Shelby. For the next few hours, Dylan was busy, and Shelby slipped farther out of his mind. He figured that she had a date or something else more exciting than stopping in for her evening coffee and innocent flirting with a country boy.
Thirty minutes before shift change, he heard the door open. “I will be with you in a moment,” he said as he hurriedly finished wiping the counters around the soda and coffee machines.
“I hope you have made fresh coffee,” a soft voice said coming up behind him, her sweet floral scent invading his nose.
Dylan knew immediately who it was before he turned around. “Running a bit late, aren’t you Shelby?”
“Ah…. were you worried about me?” she asked reaching around him to grab a coffee cup, her body lightly brushing against his.
Dylan quickly moved out of the way, feeling his face turning red, unsure what to say. He wished he could go back ten minutes and not say what was on his mind. It was not right to be saying what he did.
“Coffee is fresh,” he told her, hoping she would forget what he had said before.
Shelby filled her cup and turned around to see Dylan going behind the counter. She walked up and asked, “What are your plans after work? Got a girlfriend or wife waiting on you at home?”
“No,” he told her. “Just have to study for a test tomorrow in Biology,”
“How about joining me down at The Burger Barn for something to eat?” Shelby asked. “I haven’t had time for supper, and I hate to eat alone. My treat,”
Dylan thought about it for a few minutes as he rang in her coffee before he said, “Sure, that would be nice, but I cannot stay too late.”
“Great,” she told him. “See you there after you get off shift,” as she took her coffee and left.
Dylan watched her walk out to her car, get in, and drive off. A few minutes later Mike, his replacement, walked in.
“Anything exciting happen this shift?” he asked. “Hanging around awhile?”
“You know being the middle of the week that nothing exciting happens,” Dylan told him as he walked out from behind the counter. “Sorry, I have a test to study for tomorrow so cannot stay,”
“Sure, see you tomorrow,”
Dylan went out and got in his truck, sitting there for a few seconds trying to decide if he should go to the restaurant or go back to the dorm and study. He was not even sure she was serious about stopping. Oh well, it will not hurt to just drive by and see if her car is there. I can always get something to go if she is there and is with someone, he reasoned. When he drove by The Burger Barn ten minutes later, Dylan was surprised to see her car in the parking lot. As if his car had a mind of its own, he found himself turning into the lot and parking next to her car.
Taking a deep breath, he got out and headed inside, prepared to find her sitting with someone else. As he stepped inside, Dylan glanced around before heading to the counter. He spotted Shelby sitting in a booth by herself, so he turned to head that way. Glancing up, a smile crossed her face as she watched him walk across the room to her booth.
“I was wondering if you were going to show,” Shelby told him as he slid into the booth across the table from her.
“Sorry to make you wait,”
“Were you having second doubts? Did you think I was going to stand you up?” she asked as she reached across the table, putting her hand on top of his, the tip of her shoe rubbing against his leg.
“What can I get you?” the waitress asked walking up to the table, saving Dylan from having to answer Shelby’s questions.
Dylan grabbed the menu and quickly looked at it before ordering a cheeseburger, fries, and a chocolate shake. “What do you want Shelby?”
“I will have what he is having,” she said. “And put it all on one check and give it to me, please.”
As the waitress walked away to turn in their order, Shelby kept her hand on top of his, raising it slightly to run her fingernails over the top, sending shivers up and down Dylan’s spine. He could feel his cock hardening against the zipper of his jeans. He reached under the table, trying to discreetly adjust himself. Shelby looked him in the eyes, smiling wickedly. She knew exactly the effect she was having on him.
“Do you live in the dorm or do you have your apartment?”
“I live in the dorm,” he told her. “Cannot afford an apartment yet,”
“Then I guess we will have to go back to my apartment because if I remember from my college days you were not allowed to have a member of the opposite sex in your room…and you also have to worry about your dorm mate barging in,”
Before Dylan could reply, the waitress brought over their shakes. He quickly took a sip, trying to figure out just what she was up to.
“Your apartment?” he asked quietly when the waitress walked away.
“Yeah, I am a bit too old to have sex in the back seat of the car,” Shelby told him matter-of-factly like she did this all the time. Seeing the deer-in-the-headlights look on his face, she leaned forward, whispering, “I want to fuck you,”
Dylan, who had just taken a drink of his milkshake, began to cough, his face turning red at her bluntness. He was once again saved from commenting by the waitress bringing over their food. Once she left, Dylan busied himself by putting ketchup on his plate and then on his cheeseburger.
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When he did not reply to her comment, Shelby gave him a quizzical look, waiting to see if he would say anything. Then it hit her…I bet he is a virgin, she thought. Damn, been a while since I had a virgin to break in.
For the next several minutes, the only sound was them eating. Finally, Dylan broke the silence by saying, “Shelby….”
“Just say yes,” she said interrupting him. “You won’t be sorry, I promise.”
He stared at her, trying to figure out if she was serious or teasing him. He had some experience with girls but never scored a homerun…only third base and Shelby was an experienced woman he figured. Dylan wanted to say yes but he did not want to embarrass himself with his inexperience.
They finished and headed to the cashier, Shelby never getting a yes or no from Dylan. She figured that she would have to take the lead and show him just how much fun it would be. Once the check was paid, they walked outside. Being a gentleman, Dylan walked her over to her car, which was parked next to his truck at the end of the row in front of the restaurant.
“Thank you,” he told her as he stood there waiting for her to open her door and slide inside before he went to his truck.
Suddenly he found himself pushed against the door; Shelby’s body pressed close to his as her lips found his. Taken by surprise, his lips were slightly opened so she took advantage as she slipped her tongue inside, tangling with his. Once again Dylan could feel himself growing hard as she ground her pelvis against his crotch. Dylan’s arms reached up and entangled his fingers in her hair, kissing her back. When they broke apart, both were breathing heavily.
“Come home with me,” Shelby told him as she reached down to cup him through his jeans.
“I need to study for my Biology test tomorrow,” he protested weakly.
“What I plan will be more fun than studying,” she said as she kissed him gently.
Looking down into her face, Dylan could feel himself wavering. He knew that he should go home and study but another part of him wanted to go home with Shelby. Shelby could see that he was not completely convinced to go home with her, so she gripped his cock before she ran her hand up and down the front of his jeans.
Finally, Dylan whispered, “Yes, I will go home with you.” He had never missed a test or class yet in Biology so he knew missing one class would not hurt him.
Shelby smiled, saying, “Follow me,” as she got in her car.
Dylan quickly got into his truck and back out after she did. He followed her out of town until she turned off onto a gravel driveway, which led back to a small log cabin. It never entered his mind that maybe she was leading him into a trap; that she planned to rob and kill him. Stopping in front of the cabin, she turned off the motor and got out, waiting for him to do the same. Once in the cabin, Shelby kicked off her shoes and turned to face him.
“Want something to drink?”
“No thanks,” Dylan told her, wanting to keep his wits about him.
“Okay,” she said as she reached down and unbuttoned her blouse, slipping it off her shoulders, dropping it to the floor. Her skirt soon followed, leaving her standing there in a white lacy barely-there bra, matching thong, and garter belt, which held up her black stockings.
Dylan just stood there, staring at her. For being an older woman, she was stacked with firm boobs that were straining against her bra, begging to be free. Stepping up to her, he reached up and rubbed the palms of his hands over the front of her bra, causing her nipples to pucker into hard little buds. Shelby placed her hands on his cheeks, pulling his head down to hers to kiss him, nipping at his bottom lip.
As they kissed, her hands moved to the bottom of his tee-shirt, trying to tug it upwards. They broke apart long enough for Dylan to pull his tee-shirt over his head, dropping it to the floor. Seeing his muscular chest Shelby could not help running her hands down his chest, taking time to pinch his nipples before they moved to his belt.
Dylan just stood there, letting Shelby do what she wanted as she worked his belt open before she worked his zipper down. Hooking her arm around his waist, Shelby tilted her head back, offering her lips to him. As his lips claimed hers once again, Shelby’s hand reached inside his open zipper to caress and squeeze his cock.
Stepping back, Shelby dropped to her knees on the carpet, working his erection out of his underwear. Holding him gently in her left hand, Shelby leaned forward, her tongue swishing over the head. Stroking him slowly, she wrapped her lips around the head, her tongue licking and then sucking him as one hand reached back inside his underwear to massage his balls.
Very slowly she took more and more of him into her mouth until her lips were pressed against his pelvis, the head pushing against the back of her throat. Shelby relaxed her throat, taking him farther down. Slowly she brought her lips back up his erection until she just had just the head between her lips and then she took him back deep in her throat. Shelby continued to move up and down his cock, her hand still working on his balls. Shelby could feel him getting harder and harder, his pre-cum dripping onto her tongue. She increased the pressure and pace until she felt his fingers in her hair, his moans getting louder and louder. Suddenly Dylan became quiet just before he coated her throat and mouth with his seed. Shelby sucked harder, taking all he was giving her. When she had sucked him dry, she moved back, letting him slip from her mouth before getting to her feet. Taking him by the hand, Shelby led him to her bedroom.
Once in the bedroom, Shelby unbuttoned his jeans and pushed them down his hips to the floor, his flaccid cock still dripping down his inner thigh. Turning and sitting on the edge of the bed, Dylan toed off his tennis shoes and pushed his jeans off along with his socks. Standing in front of him, Shelby unfastened her bra, slipping it off, letting it fall to the floor. She leaned down and unhooked her stockings, rolling them down each leg before she removed her garter belt and thong.
Strolling over to him, her fingers tweaking her nipples, she reached out and pushed him back on the bed, his feet hanging over the edge before sitting on his chest. Leaning down, Shelby offered him her breasts. Dylan reached up and gently tugged on them, hoping that he was doing it right.
“Are you a virgin?” Shelby asked. When she saw his face redden, she knew that he was. “Don’t worry, you won’t be in a few minutes,” as she got up. “Scoot up on the bed.”
Dylan did as she told him, waiting to see what Shelby was going to do next. Crawling up the bed, Shelby straddled his face, rubbing her pussy against him.
“Lick me,” she ordered, “and touch me there,” as she guided his fingers to her clit.
Very softly he rubbed her and ran his tongue up and down her wet slit. Leaning forward, Shelby began to work on him again to get him hard. As he licked her, he increased the pressure on her clit, causing her to wiggle and moan around his cock as she licked and sucked him. Soon Shelby could feel an orgasm building up inside her belly, slowly setting her insides on fire. She began to wiggle and push against his face.
“Yes,” she moaned. “I am about to cum. Rub me harder, shove your finger in my pussy,”
Dylan did as she told him and soon she let out a scream as her juices flooded over his face, her body twitching as she was consumed by a mind-blowing orgasm. When it was over, Shelby moved down to lay beside Dylan, still stroking him.
“Damn Dylan, for your first time, that was mind-blowing,” as she leaned over to kiss him, tasting herself on his lips. “Now it is time to ride,” as she sat up and moved down toward his hips.
Throwing her leg over his body, she began to rub herself against his semi-erection as she leaned forward, sucking on first one and then the other nipple. Reaching down, Shelby guided him inside of her and sat up, gripping him with her inner muscles. Gradually she began to move up and down, rotating her hips, making him groan.
Dylan just laid there, unsure what to do. Reaching out, Shelby took his right hand and brought it to her pussy, guiding it to her clit. Instinctively, he began to rub his thumb over it in circles. Shelby could feel him getting harder before she reached behind her to squeeze his balls gently. As they both got closer and closer to the edge, Shelby increased her motions until she was riding him hard and deep. Her juices started to flow, covering his cock.
“Yes, yes, yes,” he hollered, rubbing her clit harder as he felt his balls tightening.
Unable to hold back any longer, he filled her with his cum, setting off her orgasm. When they were spent, Shelby rolled to his side, his arm going around her to give her a one-armed hug as they kissed.
“This was better than studying for a Biology test,” Dylan whispered.
Shelby chuckled and then kissed him. “Rest and then we will take a shower and do it again…if you want to that is,”
When Shelby woke a few hours later, she realized that she was alone in the bed. “Dylan,” she called out but got no answer. Crawling out of bed, Shelby realized that his clothes were no longer on the floor. Going out into the living room, she peeked out the front window. His truck was gone. “Shit,” she muttered. “I was so looking forward to round two. Oh well, I know where he works. Nothing says we cannot do it another time,” as she headed to the shower.
When Dylan pulled up in front of his dorm, he turned off the motor and sat there in his truck for a few minutes, thinking back on the evening. He knew that he was a coward for sneaking out of her cabin, but he thought that was for the best. He did not want to see the disappointment of his performance in her eyes when they woke up. Little did he know that she wanted a repeat performance, which he soon found out when she showed up at closing time that night, inviting him over to her house.