Cory's Senior Year

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

She had Cory stand up. She unbuckled his belt and opened his pants. She slid his pants down and saw a big bulge in his underwear. "Oh," she said, "Looks like you don't need much preparation." She kissed the bulge in his underwear, then slowly slipped them down his legs. He was fully erect. She licked his cock up and down a few times. She didn't give him the blowjob he was expecting, thinking he might not last long enough for the next part of the lesson. She had him kneel down behind her as she got down on all fours and continued the instructions. He slowly slid his rock hard cock into her pussy. He couldn't believe how good it felt. Mrs. Strom sighed. Then he began to pump -- slowly and methodically. She matched his rhythm. She was warm and wet, lubricating his cock. Cory felt warm.

Before long, it was more than he could handle. He felt a tingle up and down his spine. He pumped harder. "Oh man," he cried as he sent pulses of hot cum inside of her. He was panting and his skin was shining from a thin layer of sweat. He pulled out his cock, which was already becoming limp. Mrs. Strom turned around and sucked him off while his heart rate came down.

"Good," she told him. " Very good. You're a quick learner. That's all for today's lesson." She handed him his pants and then got up and started getting her clothes back on.

Cory couldn't believe it. He felt like he was floating on air. He wanted more. As he got dressed he thought, "My first sex lesson. I can't wait to tell Tyler." TYLER! Cory had already asked if there were any openings at the store, and his boss was looking into it. But they always looked out for each other. Maybe he could find a way to get Tyler a lesson, too. "Y'know," he said to Mrs. Strom, "you really should give lessons."

"Oh really?" she asked with a laugh. "And who would I give them to?"

"I have a friend who would like to get one."

"I see. What's he like?" She pursued the conversation with a little interest.

"We're practically twins!" Cory responded enthusiastically. "He's my best friend, Tyler."

She laughed again, reached into her purse, pulled out a card and handed it to Cory. "OK, my lawn needs mowing. Tell him to stop by after school tomorrow. I'll help him out."

"Thanks, Mrs. Strom." He said.

"You're welcome. Well I'd better be going. Thanks for your help today. See you again." She gave him a little kiss on the cheek.

"Thank YOU for the,,, uhh... lesson," he said with a smile. And they each went their own way.

After work, Cory had to see Tyler to give him all the news. In Tyler's room, he again closed the door and, with a huge smile, said, "You'll never believe what happened at work."

"No way. Again?" Tyler asked.

Cory proceeded to tell the whole story. Tyler was getting so hot that he took his shirt off and loosened his belt. He figured he'd need to masturbate soon. Cory decided to help his friend out. So as he continued with the story, he started removing Tyler's pants. He stroked Tyler's cock as he talked. When he finished telling about the lesson, he gave Tyler a blowjob. He pumped Tyler with his mouth and Tyler moaned with appreciation. Cory was still high from the experience a couple hours before, and he was really enjoying watching his friend react to his actions. Tyler loved the feel of Cory's warm, wet mouth sliding up and down his smooth, hard cock. Soon he began to shudder as his cum filled Cory's mouth. Cory cleaned him up and swallowed. Tyler laid on the bed for a moment. He finally said, quietly, "Thanks, buddy."

"There's more," Cory said with a smirk. He handed Tyler Mrs. Strom's card. "She needs her lawn mowed tomorrow right after school."

Tyler looked confused at first. As it slowly dawned on him what Cory was telling him, his facial expression changed to excitement. "Sweet. I'll be there."

After that Cory had to get home for dinner. The next afternoon Cory had his usual bike ride and shower (with masturbation session) and started his homework. Just then the phone rang. It was Tyler.

"Thanks, Dude," he told Cory. "You're the best friend ever."

"Yes I am," Cory said with a big laugh.

Chapter 4

After school on Thursday, Cory went to work. He always liked his job -- for a part-time job. But now he looked forward to it even more. He wondered if this was how it would always be. Did these women do this with Colin?

He checked in with Blake, then with Laura. She told him there were 2 ladies coming in today. The first would only be for a few minutes and the second a half-hour later. So Cory began his usual unloading boxes and bringing them to their rightful departments. At 4:00 he went to the women's department eager to see today's customer. He wondered if she'd be like the first two. He stepped out onto the sales floor and stopped, dead in his tracks. Standing there, talking to Laura was Mrs. Dixon -- Jessica's mother!

She looked at him and said, "Hi Cory," with a smile.

"Oh, you know Cory?" asked Laura.

"He's practically one of the family. He and my daughter Jessica have been friends forever."

"Hi Mrs. Dixon," Cory finally said.

"Cory," Laura said to him, "Mrs. Dixon is here to look at those shoes on my desk. Would you go get them, please?"

"Sure. Be right back." He felt relieved that she wouldn't be coming into the dressing room. Not that he wouldn't love to see a lot more of Mrs. Dixon. After all, she and Jessica look a lot alike. He'd probably like banging her almost as much as he wanted Jessica. "Stop it!" he thought to himself. "It's one thing to do it with those ladies you've never seen before. But this is Jessica's mother. You've known her practically your whole life."

Cory came back out with 2 boxes. He and Mrs. Dixon walked to a sitting area in the women's shoe department where she could try on the shoes. "Laura tells me you have the new job of being the valet, here. How do you like it?" she asked.

"Oh, it's pretty good, I guess." Of course, he couldn't say to her what he really thought.

"Some pretty influential people come here. Getting to know some of them can be a pretty good thing for you."

"No kidding," he thought.

"Having contacts like that can help you in the future when you're looking for jobs and such."

"I wonder if that's what happened with Colin," he thought again.

"Ooo, these shoes are a bit tight."

"They're nice. You should get them for Jess," he said with a wink.

"Ha. I haven't picked out shoes for her since she was 6," she chuckled. "She wouldn't be very happy with me. Let's try that other pair." She put them on and walked a bit.

"Oh, I forgot. I'm supposed to ask if there's anything else I can get for you."

"No. I need to get going. Why don't you take this other pair back and I'll take these to Laura. Good luck with the new job."

"Thanks," he said. "See ya later." And he disappeared into the warehouse. When the next VIP customer came in, Cory again went up to greet her. "Cory," Laura said, "I'd like you to meet Ms. Welles."

"Hi," Cory said a little too enthusiastically. He couldn't help himself. This woman wasn't like the others. She had long, blonde hair. And her body had much more pronounced curves. Her breasts seemed to him to be giant -- although, in reality they were just a little more than average. Ms. Welles also seemed a little younger. Or was it just her personality? She didn't have the wealthy, sophisticated, elegant appearance. It was more like the models he and Tyler saw in sex magazines. She had full lips with bright red lipstick, and blue eyes that you would do anything for. There was no ring on her finger so he guessed she was single.

"Hi Cory," she said back with a big smile. "Gosh Laura, you sure hire some good-looking guys here."

Cory got a big smile on his face.

Laura asked Cory to bring Ms. Welles to the back and then get the dresses hanging outside of her office. When he walked in with the dresses, Ms. Welles closed the door behind him and said, "Laura told me you're taking Colin's place. I think you're a great choice."

"Well, I'm doing my best. Do you need anything else? Coffee?," he asked. He really wanted to see all of her.

"Can you undo the zipper in back for me?"

"Sure." He nearly tripped over himself to help.

"Thanks." And she slipped out of her own dress and reached for one of the new ones. She was wearing a bra. Cory thought it was probably to keep those breasts from swinging around too much and coming out. He thought that might be embarrassing -- but he'd love to see it. Cory had seen this dress with one of the other ladies. He didn't like it much. When she got it on, she asked what he thought.

"Actually, I'm no expert, but I don't like that dress."

"I want to be in style. Do you think girls your age would wear it?"

"I doubt it. It looks like..." he was trying to come up with the right word. "...like a paper bag."

"OK. Forget that one. Next." The next dress was light blue, sleeveless, large V-neck and looked like it would be difficult to cover her breasts. "Looks like we won't be needing a bra for this," and she took hers off. Cory almost fell over. They were awesome. She put the dress on and, he didn't know how, was able to cover her breasts. But it somehow enhanced their appearance. "What do you think?"

"Wow," was all he could get out. "That is hot."

"That's all I need to hear," she said. She faced him and looked over her shoulder in the mirror. She could see his mouth was open while she made some minor adjustments. "I can see what you like," she said. "Do you want some of this?"

"Oh man. Do I ever," He said letting out the breath he was holding.

"Good. I like to share with cute, young guys." And with that invitation, Cory stepped closer and instinctively put his hands on her body. He didn't start with her breasts, but on her sides. Slowly, lightly rubbing her all over. He wasn't even thinking about what Mrs. Strom said about seeing the girl as the most important. At this moment, Ms. Welles was the most important. Eventually his hands came to those big, soft breasts. He gently squeezed, then leaned over and began to kiss her neck. "Mmmm, you know how to do this well," she sighed.

Ms. Welles reached down to pull Cory's shirt off over his head. Then he helped her slip out of that hot dress. He caressed her bare chest and stomach. Then he kissed her all over. He ran his tongue around her nipples, and all over. Down, down, down until he was kneeling beneath her. She helped him pull down her panties to expose a completely shaved pussy. Cory didn't hesitated. His tongue went right to work. He was pretty sure he was doing everything right by the moaning sounds she let out. She ran her fingers through his hair. Cory liked that. He inserted his finger and felt that she was dripping. He licked and massaged for a long time until she began to pant, and shudder. Soon she began to convulse with pleasure. She was coming and he made it happen. He always heard from his guy friends that it was practically impossible to make a woman cum -- especially for inexperienced guys.

When she recovered, Ms. Welles knelt down face to face with Cory. She was naked and now it was time he was. She kissed him right on the mouth and slowly opened up his pants. She motioned for him to stand so she could remove his pants (after he kicked off his shoes). Then she had him lie down on his back and she lied down next to him. She rubbed his chest and licked his nipples to make them hard. She made her way down, rubbing and kissing him. Next she moved to the inside of his thighs. She cupped his scrotum and with her first 2 fingers gently caressed the perineum behind his scrotum. Back and forth. Cory thought he would explode. He never explored that area before. It was a wonderful sensation. She moved her mouth in and began to suck his balls. Cory let out a moan. She moved her tongue all around, then along the shaft of his cock, which was pointing straight up as stiff as it had ever been. "You have a nice cock, Cory," she said. That boosted his confidence. She explored all over, careful not to bring him over the top too fast. She took his whole cock into his mouth without any trouble. When she thought he was getting too close to climax, she backed off and started on his balls again.

After she brought him up and down a few times, she stopped. She turned and straddled him. She guided his penis into her pussy and slowly slid down on it. Cory's eyes rolled up into his head. She worked up and down a little, again making sure he didn't cum too soon. After a moment she dismounted and laid down next to him so they faced each other. "Bring it back inside me," she whispered. It took him a second, but he found her pussy with his cock and inserted it. It felt warm and wet. It felt so good. She kissed him hard while he slid in and out. "Yes Cory. Just like that. Keep going. Cum inside me."

He pumped. He breathed harder, his heart beat harder, he moaned. "I'm gonna cum," he said.

"Yes, Cory. Do it. Do it hard."

Then Cory's cock burst with everything he had. His eyes were closed. He felt like he was sending gallons of cum inside her. He was panting. He let out one final moan as the last drops left his cock. He slid his limp cock out. Ms. Welles gave it a few licks. "That was great," he said, panting a little less.

"You were very good. I'll have to come back soon," she said. "For now, I still have another dress to try on."

"Wow," Cory thought. Could she really be planning to come back again and again? Would the other ladies be thinking the same thing? Mrs. Lambert did say he'd fill in for Colin nicely. Is that what she meant? He was starting to like his job even more.

Ms. Welles tried on the last dress while Cory put his clothes back on. She decided to take the hot blue one. They chatted a bit more. Cory told her if she really liked cute guys, he could recommend someone. "Sure," she said. And he told her about Tyler. "Sounds like a nice guy. I'm going out of town for a week. But after that, bring him over to my place some time. The three of us can watch a movie and find something to do after."

"Wow. A threesome? That'd be awesome!" he said excited. She wrote down her address and phone number and handed it to him. After saying goodbye she went off to check out, and Cory went back to the warehouse just as he'd done before. He couldn't wait to tell Tyler.

When Cory got to Tyler's after work that day, he was beaming. Tyler could tell something good was coming and closed the door when they got into his room. Cory said, "You're gonna need those clothes off." He helped Tyler undress and had him lie down on the bed. He wanted to try out that technique behind the balls that Ms. Welles did for him. So as Cory started telling Tyler how she rubbed his chest, he demonstrated. As he moved to Tyler's legs, he didn't tell him what she did. He just cupped Tyler's balls as she did and massaged behind them with his fingers.

Tyler felt a tingle inside his body. "Oh that feels nice," he said. Cory worked that for a while. Tyler's cock grew longer and harder. Cory wanted it. So while he caressed, he took Tyler's cock into his mouth and began sucking. He tried to go deeper, but he could only make it so far. Cory decided to lie down on the bed next to Tyler in a 69 position so Tyler could have something to suck on. Tyler unzipped Cory's pants and worked out his cock, which wasn't too hard, yet. For several minutes they sucked each other. Each enjoying the warmth of the other's mouth. Tyler couldn't take any more. He gasped and unloaded into Cory's waiting mouth. Cory kept Tyler's cock in his mouth as long as he could. Then slowly slipped it out and swallowed.

"What are you doing in 2 weeks?" Cory asked him.

"I don't know. Why?" he replied.

"She told me we should go to her house for a threesome!" he said.

"Seriously?!?" Tyler exclaimed astonished.

"Seriously. We have got to go."

"Absolutely."

Chapter 5

That weekend was pretty much like any other with the gang hanging out together. Cory felt even more that he needed to spend time alone with Jessica, and it needed to be soon or he would burst. But he still didn't know how to go about it. He and Tyler went for a long bike ride on Sunday. They often went riding together. And like Cory, Tyler also enjoyed the breeze that riding commando provided. As they rode and talked, they were trying to find the right way for Cory to ask Jessica. Tyler had been encouraging him all along and said it needed to be first thing in the morning at school. Cory decided he would do it this week... some time.

That Tuesday at work Laura told him she had an early appointment. "Sorry about not telling you ahead of time. Mrs. Braun is already in the dressing room trying on a few things. Would you please take these 2 purses to her?" she said.

"Sure," Cory said eagerly.

Cory knocked on the door and said, "Mrs. Braun, Laura asked me bring you a couple purses to look at."

The door opened and Mrs. Braun said with a smile, "Thank you. Please bring them in." She was wearing a very formal, long dress that showed her slender figure. "You must be Cory," she said.

"Yes, ma'am. You look very regal in that dress. I bet this purse is supposed to go with it," he said handing her a purse.

"Oh yes, that will go very nicely. I would probably need new shoes, too."

"Would you like me to ask Laura if she has something?"

"Not just yet. I should look at this other dress." And just like before, she took the dress off right in front of him. Cory felt so lucky to have this job. And to think when he first heard about it, he didn't want to do it. Her body was very trim and had curves in all the right places. He could see, under her bra, that her breasts were not as large as Ms. Welles'. But still, they were nice to look at. He was getting hard with anticipation, hoping for another encounter.

He didn't have to wait long. As she was looking at herself with the 2nd dress on, she said, "Why don't you make yourself more comfortable? It's a bit warm in here and that shirt and pants must be hot."

Cory removed his shirt. "That must feel a little cooler," she said and he nodded. So he unbuckled is belt and dropped his pants to the floor. He felt a bit strange undressing in the room with the woman who was still wearing a dress, until she said, "Would you help me take this off?" He did and she continued, "Have you done this before?"

"Uuuhh... a couple times," he stammered. He was a bit confused since this was happening different this time.

Mrs. Braun stepped around behind Cory giving him a very quick once over. "You certainly are a good looking young man." As she said this she put a hand on his shoulder and began to caress it. Then she took both hands and slid them around to his chest from both sides. She slowly moved her hands all over his chest and stomach, paying extra attention to his nipples. Cory closed his eyes and took slow, deep breaths. Her right hand made its way down to his penis and scrotum. Her touch was so light and gentle that he could hardly feel it. He grew hard very quickly. Then she slipped her hands in the waistband of his underwear and slid them down so his cock sprang out. "Yes, very good looking," she said. She continued to caress Cory's cock and balls with the same light touch. Cory continued his slow, deep breathing, enjoying every moment.

Cory was completely hard now. Mrs. Braun asked, "Do you know many sex positions?"

Cory felt embarrassed because he really didn't know any. "Just the basics, I guess."

"OK, we'll have to teach you some more," she said. She had him kneel down. She laid on her back in front of him and put her legs on his shoulders. "Now slide your hard cock inside me." Cory's heart bean to pound as he did what she told him. "Good. Now start out slow and work your way up to as hard a thrust as you can. Soon they got a rhythm going. As Cory worked harder, he felt like he was a real man. He began to sweat as his cock slid in and out bringing him, and her, closer to climax. Soon Cory's body tensed and he shot several rounds of warm cum inside Mrs. Braun. She let out a soft moan. After Cory pulled out, he sat down and she leaned over and licked his cock. "Mmmm. Very good," she said. Next time I'm here, I'll teach you something else."