Roll playing!

Standing in the doorway was Ashley Roth, but not the Ashley I knew from yesterday at the party but from a decade and a half ago in high school.

She had dyed her hair blond like it was in high school, her make-up was the same, and she was wearing her cheerleader outfit from high school! Granted, it was a bit tighter, but all that did was raise the hemline of her skirt and push her already mammoth mammaries to try and escape the top of her bikini top. I also noticed she had a book bag with her. My mouth was hanging open, my lips were moving, but no sound was coming out.

"Hi Mattie!" She said it, sounding like the perky cheerleader she was dressed as. No one but her had ever called me Mattie except my mom, and I hadn't heard someone call me that since I was in high school. "I came to study for the test on Monday! Is your mom home? Or do we have the place to ourselves?"

She said as she stuck her chest out while grabbing her arm behind her back, selling it that much more by biting her lower lip too.

"Holly crap, Ash I can't believe you did all this!" I gushed.

She broke character for a second. "Master, I feel like I made a mistake all those years ago; I didn't realize then that you were really what I wanted.  Honestly, I think I thought I didn't deserve your love because I was such a mess back then! I want to try and start over.

I want to love you and you me, the way it should have happened in school. This is just a way I thought you could relive it, maybe to try and help you forget about that stupid girl who passed you up to date assholes." She was pleading. Then she was right back in character: "Well, Mattie, are you going to invite me in?" She asked. 

"Sure thing, Ash!" I said with a grin, This was going to be fun. "My mom is staying at my aunts this weekend so we can do whatever we want and not worry about getting caught." I continued grinning like an idiot. "Do you want something to eat? Or should we go study?" I asked. 

"I'm starving for something special; that's why we should go study immediately!" She said it intensely.

"Ok, let's go up to my room. Sorry if it's a little messy!" I lead her up to the bedroom again.

As we reached the bedroom, the anticipation was building. Once we got in the room, Ash sat down on my bed, and I sat on the chase lounge chair we had. She started to take a couple of books out of her backpack. I was thinking, 'Wow, she is really committed to this' She spreads a couple out and grabs a notebook and a pen. 

"Mattie, I have been having troubles in my human sexuality class." She said this while pouting. "Mr. Grover assigned 3 chapters for this test on the Kama Sutra, and I just can't seem to figure out these positions; they just seem strange to me!" She sighed "I am a hands-on learner; I have trouble conceptualizing these things when they are just old drawings in a book." She finished.

"I also have a book report on Nina Hartley's "The Guide to Total Sex." I am reading the chapter about role playing and being submissive to your partner.  

"Well, Ash, I have been doing some independent study on those topics, so I can definitely help you with those." I said, grinning. 

"Mattie, you're so smart; I just love your  BIG...brain!" She said it breathlessly and with a little chuckle at the end. 

"Which do you want to work at first?" I ask. 

"Hmm, I think I want to study you, Mattie!" She said she was patting the bed next to her. 
"Oh, really, Ash? I thought you were more interested in Jamie Tattleman..." I knew for a fact that he was the guy she dated after me, an upper-classman who convinced her to blow him after she would barely hold hands with me when we were together. He was a pot smoking skateboarding loser who barely made it through school, but he was 'like so gorgeous and deep' when they were alone. These thoughts started to sour me, but Ashley leaned into me.

"No way! He asked me out, but I told him I liked someone my own age, someone smart and kind, not some pothead who just wanted to touch my tits." She said it in earnest.

"Well, what about Morgan?" I said Morgan was Ashley's best friend in high school and one of the people who convinced her I was a loser and better relegated to being a friend she could lean on instead of a potential suitor. 

"Fuck Morgan! I found out not only did she sleep with her boyfriend after trying to get me to break up with you, but I found out she has been starting rumors about me because she is jealous." She practically growled.

"I asked my mom about what I should do, and she said that a person who loves you will stick with you no matter what; they won't try to change you. One day I will realize they have been there in front of me, and I didn't even know it. That's how I feel about you, Mattie; you love me for me, and I can't believe I didn't see it before. Please stay with me; let me show you tonight how much I want to be with you." She whispered the last part. 

"I have wanted to hear you say that most of my life, Ashley." You say, getting a bit choked up. You lean in, and you both kiss shyly at first, but it becomes more passionate and deeper the longer it lasts. Causing both of you to flush. 

"Ashley I am so happy we are going to be together, but you said you really needed help with your assignments. We should really work on those; I know it's not all that fun, but you need a good grade." I said, trying to convince myself that's what I would have said as a teenager instead of trying to go spelunking in-between those two mountains on her chest. "Which one do you want to work on first.?"

"Let's do the book report; I think I can get into the head space of being submissive more than these wierd pictures in the Kama Sutra." She said it with a wink.

"So what I have figured out so far is that I am supposed to refer to you, Master, and you are supposed to call me ****, but I guess you can call me whatever you want as long as you are happy." She said this while looking at her notes. "Then I am supposed to trust you completely to make decisions for me that will give me mind-blowing pleasure while doing the same for you." She said this while putting her notebook down and standing up. Ashley stepped up to me and kneeled in front of me with her hands behind her head. "How can your **** serve you, Master?" She purred. 

I took Ashley's chin, and I lifted her face to look into my eyes. "I love you, Ashley; you are my ****, and I am your Master. I will do everything in my power to make sure you are physically and emotionally fulfilled. I will ask much of you sexually, but I guarantee you will be more than repaid for your efforts. Your purpose is to please me, and I will make sure you are fulfilled in every way possible in exchange for your love and devotion."

"I am ready to learn my first lessons, Master!" She said it excitedly. 

"Well, ****, you should know that even though it is pleasing to me, my slaves do not wear clothes. So strip yourself and then kneel before me."

"Yes, Master, this **** is sorry for not knowing your rules." She said, removing her clothes as fast as possible. "Will Master punish his **** for being bad?" She asked with a smile. 

"It doesn't matter if you want me to punish you; all that matters is pleasing me. So you will obey me to the best of your ability, and I will decide when you have disobeyed and deserve punishment.

"Yes, master, your **** obeys." She said this while looking down. 

"Now why don't you undress me, ****?" I commanded. 

"Oh yes, Master, my pleasure!" She carefully removed my shirt, pants, and finally my underwear. .

"Now ****, I want you to fuck me with the tits that you have teased me with for all this time!" I commanded with gusto.

"Yes, master, I hear and obey." Ashley's eyes were unfocused, and her response was monotone. Oops,  I must have been too forceful that time.

She grabbed her perfect rack and enveloped my dick, absolutely smothering it in her tit meat. I reached over to the nightstand and drizzled a little lube down the middle of the tit vortex for some lubrication. Pretty soon we were both moaning from the slippery sensation and, in my case, the gorgeous view. Finally, it came time to cum. 

"**** suck my cock. I am about to cum; swallow it all like a good ****." I said it as if it wasn't a choice—which, to be fair, wasn't. 
After slipping me in her mouth, Ashley started taking me all the way to the hilt.

While not as good as Jen's blowjob technique, I was in the mouth of someone I had fantasized about for years. So that more than made up for it. I blew my load, and what felt like my soul right down her throat, there was no doubt she was going to take it all without problems.

Popping off my dick with a loud slurp, she said, "Oh, thank you, master, that was delicious!" She gushed. 

"Now lay down on the bed. I want to fuck your throat to get me hard again." You say. 
Ashley complies; you let her suckle your semi-hard dick while getting a chance to use both of your hands to really knead those wonderful knockers as you slowly thrust into her throat. After a few minutes of that, you pull out and tell Ashley to lay down missionary style so you can look at her face while you fuck her and blow your load on her. Ashley spins around, knees up to her chest, and spreads to the sides. You waste no time and thrust into her volcanic snatch. 
"Oh, fuck, you are so hot! Your roasting my dick with your heat. It feels so fucking good!" I yelled. 

"Thank you, master; it is all for you! You're filling me up! I am so full!" She babbled. It didn't take long for me to feel the need to go off like a firecracker in my loins. I planted myself to the hilt before releasing my orgasm. 

She screamed, I screamed, and we all screamed for ice cream! I collapsed on her, breathing heavily, as did she. I felt like my wish had been granted, Shangri la had been reached, and my teenage self could die a happy man. 

I rolled over, and Ashley dropped back to her knees to clean my cock from our mixed juices before throwing herself on the bed next to me. We laid there on our sides, just staring at each other, both of us with goofy grins looking at each other. 

I was just about to say something when I realized what time it was. I rolled over in bed, grabbed my phone, and hit send before laying back to stare at Ashley. In a couple minutes, there was a knock at the door. Ashley moved to cover herself up, but I told her to stop and kneel on the floor. She looked a little confused but complied. 

"Come in," you say loudly. 
Jen and Nance are both wearing and carrying S&M gear. Nothing really radical, mostly the stuff that you got for Jen and what Nancy already had. Ashley looks surprised as well as excited. 

You turn to her and say, "Ashley, now starts your real **** training and your punishments." You say this to her. Wide-eyed, she just nods, waiting for the next order...

___
 
 - Thank you for reading my story. I wanted to mention that the winner of the last poll was Dt. Madison Peterman, to be honest I did not expect her to be as popular as she is and such I have had to revise a few plot ideas I have been working on.

-I also wanted to apologize this chapter is not up to my standards, I had to many feelings on how I wanted this huge event in Matt's life to culminate and I think it ended up a bit 2 dimensional. Lack of sleep, holiday, and wanting my cake and eating it too I think we're my downfall. I am going to do my best to salvage this 4-some. In the meantime enjoy the read!