Learning Even More

It had been nearly a week since their first date and things seemed to be going well between Sasha and Chad. On this Thursday afternoon, Chad approached Sasha as she was at her locker getting her books from her next class. He wrapped his arms around her and kissed the back of her neck and moved up to her ear so that he could whisper something to her.

“Meet me in Coach Turner’s office after school. I have a surprise for you.” Chad said.

“I love surprises. I will be there.” Sasha said as she turned around in his arms and kissed him on the lips before pulling away and they both made their way to their next classes.

. . .

That afternoon after she was done with her classes, Sasha made her way to Coach Turner, or as she called her, Aunt Jenn, since her family and Patrick’s family were very close. As she walked into the office, she saw Aunt Jenn and Chad sitting there talking. When they heard the door open, they both turned to her and Aunt Jenn smiled.

“You are really going to love this, sweetie. I am not going to join in on this, but I will be here to give you some tips if you need them.” Aunt Jenn said.

Sasha smiled back with a little bit of a tint of pink forming on her cheeks as she thought about Aunt Jenn watching her get fucked. At the same time though, she was definitely turned on by the idea.

“Okay. I could use the help being that I am not that experienced sexually. What are we doing today anyway?” Sasha asked as she looked at Chad.

“We are going to try anal today. I think you would really enjoy that.” Chad said.

Sasha was a bit afraid of anal, especially since Chad wasn’t small by any means when it came to his cock, but she was willing to do whatever it took to make Chad happy. Who was to say that she wouldn’t like it just like Chad said.

“I am willing to try it.” Sasha said.

“Good. We won’t continue if it hurts you too much.” Chad said.

“Okay. I am kind of apprehensive about this. I am excited, yet scared at the same time.” Sasha said.

“Don’t worry, Sasha. I will be here to give you tips the whole time.” Aunt Jenn said.

“Thanks.” Sasha said as she walked over to Chad and the two of them started to kiss.

Things grew heated between the two of them and it didn’t take long for both of them to start losing their clothes. Aunt Jenn was so turned on by what she was seeing, she stuck her hand down her pants and started to rub herself as the two teens were finally completely naked in front of her.

Sasha didn’t waste anytime in dropping to her knees in front of Chad and started to suck his cock with her blowjob skills that she had worked up over the years, since she wasn’t ready to fuck any of her past boyfriends.

“Oh shit! So good!” Chad moaned as Sasha took his whole dick into her mouth and down her throat and let it sit there for a five count before pulling back and catching her breath.

Sasha had blown Chad enough now to know what he liked, so she didn’t waste any time playing around and just went straight to work on him. After she had deep throated him for a while, Sasha pulled back while continuing to stroke his cock.

Chad knew what was coming next, so he prepared himself for it. Sasha first started to lick both of his balls, but soon enough, she took one of them into her mouth and sucked on it while still licking it with her tongue.

“Fuck yeah! Suck my balls, baby!” Chad moaned and Sasha switched to the other ball to give it the same attention as the one she had already been sucking on.

Aunt Jenn was sitting at her desk with her one hand down her pants and the other one up her shirt playing with her tits, really getting into things now. She was moaning as she continued to masturbate while watching the scene in front of her. She watched as Sasha went back to sucking Chad’s cock and couldn’t help but give the younger girl some encouragement.

“That’s right, sweetie! Suck his dick hard!” Aunt Jenn said and it seemed like Sasha took her advice as she started to move at a more frantic pace than what she had been before.

Chad knew that if Sasha continued like this, he wouldn’t last for much longer, but he wasn’t ready to stop her yet, so he let her continue. Sasha was really talented at blowjobs as she was taking him deep into her mouth without at a speed that shouldn’t be possible and she was barely gagging at all. She must have sucked a lot of dick over the past couple of years if she was that experienced.

“Fuck! I’m getting close.” Chad moaned.

Sasha didn’t want him to cum yet, so she slowed her pace and Chad was actually pleased with her doing that as well, being that he didn’t have to get her to stop right away. Sasha sucked on him for a few more minutes at this slow pace and then she pulled back and smiled up at him.

“You are so amazing at that.” Chad said as he helped her up to her feet and led her over to Aunt Jenn’s desk and leaned Sasha over it.

Sasha looked back at Chad with apprehension in her eyes, but was happy when she felt him line up with her pussy instead of her ass. He pushed half of his length inside of Sasha and she moaned in delight as she felt him stretching her tight pussy.

“Oh yes!” Sasha moaned as Chad continued to push inside of her until he was balls deep.

Chad then pulled back and thrusted into her again. He soon had a nice rhythm going and was going at medium pace now so that he felt good, but it wouldn’t push him over the edge too quickly.

“You’re so tight, baby!” Chad moaned as he continued to fuck her.

Aunt Jenn was sitting on the other side of her desk, still playing with herself. She was looking right at Sasha’s face which was in a look of pleasure and she was also watching Sasha’s tits bounce with each of Chad’s thrusts into her. If it wasn’t for Sasha being new to everything, she would have definitely joined in on the action, but she didn’t want to overwhelm the younger girl by having to learn about anal and having to learn how to be with a guy and a girl at the same time. That might just be too much for her.

“You’re doing good, sweetie. Let him loosen you up and then you will be ready to take it in the ass.” Aunt Jenn said as she smiled at Sasha, who nodded and smiled back at her.

“Oh my God! So, good!” Sasha moaned as Chad continued to fuck her pussy closer and closer to orgasm.

Chad could tell that Sasha was getting close, so he started to thrust into her faster, so that he could her to cum and then he would reach his goal of fucking her in the ass. He knew what he wanted and he was going to get it. Sasha was playing right into his hands and she was become more and more of a slut the more that he taught her and the more that he fucked her. This was working better than he ever thought it would. Soon, Sasha would be doing anything that he said and he was so looking forward to that.

“I’m so close!” Sasha moaned and Chad picked up his pace even more once he heard that.

Sasha was taking it in her pussy so hard now that she could barely stand it. She knew that she was close and it was feeling so good right now that she didn’t care that this was happening a little quicker than she had hoped. At this point, her mind wasn’t on what was coming next, but what was happening now. As Sasha got closer to cumming, she started to thrust herself back into Chad and it was feeling even better. She soon fell over the edge though and she was squeezing tightly onto Chad’s cock.

“Oh! I’m cumming!” Sasha moaned as she collapsed onto the desk as she lost all of her energy for the time being.

Chad continued to fuck her until she came down from her high. He then pulled out of her pussy and was about to line his wet dick up with Sasha’s ass, when Aunt Jenn caught his attention. Chad smiled at her when he realized what she had in her hand.

“You have that just laying around in your office?” Chad asked.

“Always pays to be prepared.” Aunt Jenn said with a shrug as she threw him the bottle of lube.

Chad lubed himself up well and then he did the same to Sasha’s ass and he finally lined himself up. Sasha had a little bit more energy now, so she was up on her elbows on the desk looking back at him.

“Go easy, please.” Sasha said with a lot of nervousness in her voice.

“I will.” Chad said as he started to push his cock against Sasha’s virgin asshole.

It took some work, but he finally got the head of his cock into Sasha’s ass and he heard her groan at the foreign object entering her ass. He stopped moving and let Sasha get used to the feeling of him being in her ass.

“Rub your pussy, sweetie. It will help. Trust me.” Aunt Jenn said to Sasha as she continued to masturbate at what she was watching.

Sasha nodded and did as she was told. She was surprised when the pleasure from rubbing herself started to ease the pain she was feeling from having a cock in her ass. She looked over her shoulder and gave Chad a nod, letting him know that she was okay with him to move again.

Chad started to push more and more of himself inside of Sasha and soon enough, he was as deep in her ass as he could get. He stopped again to let Sasha get used to being full of his cock. Soon he started to thrust in and out of her while Sasha continued to rub her pussy.

Sasha was actually getting to wear getting fucked in her ass was feeling pretty good. She was moaning now in pleasure more so than pain and what pain she was feeling was a good kind of pain. She couldn’t believe that she was actually feeling good getting fucked in the ass, but she definitely was.

“Fuck! You’re so tight!” Chad moaned as he continued to thrust into his girlfriend.

“It feels great! Please don’t stop!” Sasha said and Chad couldn’t help but smile at his anal slut.

He sped up his thrusting and this pace was bringing both of them closer to cumming. It wasn’t going to take long for him anyways with how tight Sasha's ass was, but this was bringing him even closer to cumming.

Sasha knew that she was close and she was hoping that they came together. There was something about the thought of that, that was just so hot to her. She didn’t think she would cum from anal, but the pleasure she was feeling from her ass and also the way that she was rubbing her pussy was really getting her close.

Aunt Jenn was watching the action and she knew that she was getting close now as well. She couldn’t help it. Watching what was going on right in front of her was just too hot. She started to quiver a bit and then she fell over the edge.

“Oh fuck! I’m cumming!” Aunt Jenn said as she came hard on her hand.

This was enough to push Sasha over the edge as she opened her eyes and watched Aunt Jenn cum. “I’m cumming!” Sasha moaned as she released all of the tension that was in her body and collapsed on top of the desk again.

The way that Sasha’s ass tightened around him caused Chad to cum as well. “Shit! I’m cumming!” Chad moaned as he shot his load into Sasha’s tight ass.

As Chad came down from his high, he pulled out of Sasha’s ass and started to get dressed. He then looked at Sasha as the top half of her body was still on the desk while her feet were on the floor holding the rest of her up. She was still breathing hard and catching her breath and soon she stood up, but kept leaning on the desk.

Aunt Jenn looked at Sasha and smiled. “You did great, sweetie. If you ever have any questions about anything, do hesitate to ask. I don’t mind being your sexual mentor.’ Aunt Jenn said with a smirk.

“Thanks. I might take you up on that.” Sasha said as she turned to Chad, who had her clothes in his hands and was holding them out to her.

“So, how was it?” Chad asked as Sasha took her clothes and stood up completely to get dressed.

“It was great.” Sasha said as she felt the cum dripping from her asshole and running down her thighs and she couldn’t help but smile. She was lucky that she wore jeans today since it would cover all of the mess until she got home.

Once she was dressed, she walked over to Chad and gave him a kiss and then she turned back to Aunt Jenn. “Thanks for the encouragement and tips. It really helped.” Sasha said.

“It was nothing. You two get out of here. I need to get home. I am already here later than I normally am, but it was for a good reason.” Aunt Jenn said as Sasha and Chad nodded and left the office, with Aunt Jenn not too far behind.