Chapter 8: Weekend Education With Professor

The weekend finally comes. I spent the whole week chatting with Michael, masturbating anywhere I was, cumming and cumming and cumming. But now is finally the time when I get to play with Tommy’s cock again. Even though it’s only my second time I am very excited. He’s coming at around 6pm this Friday to pick me up at my place and my mom’s not here all weekend so I can be with Tommy non stop. His instructions were to wear the butt plug and a short dress when I meet him. I get in the shower and shave off every bit of hair below my eyebrows as usual. I get the plug and try to insert it in my ass. But it is so tight and so painful I’m unable to do so. I end up on all fours on the floor of my bathroom trying to push that plug in without success. I tried to make it wet with water but it seemed to be worst. I tried sucking on it and making it wet with saliva and that seemed to help a little, when I managed to push it through my ass while screaming from pain. As per Tommy’s instructions I’m not putting on any underwear and I grab a short tight black dress with a naked back dress. I get out and Tommy is there waiting for me. I get in the car and he just looks at me smiling. I didn’t know it yet but this was going to be a very long weekend filled with new experiences. He starts driving:

Tommy: “I’m so glad to see you lil slut. You are mine for the full weekend, right?”

Me: “Yes daddy that’s right”

Tommy: “Mmm love it. Now let me explain how this is going to go and a few set of rules: 1. I am always your daddy - when we’re out you are my daughter and when we’re alone you are my naughty lil slut 2. You do not have any limits for me - I will enjoy you to the fullest extent. The only things we will avoid is animals, scat, blood 3. Your top priority is always to please me and make me cum so you better learn how to get pleasure out of it for yourself 4. If I judge that you have broken any of the aforementioned rules you will be punished”

Me: “Yes daddy I understand”

Tommy: “Good, and do you have everything I asked you to purchase?”

Me: “Yes daddy, all in my bag”

He turns into some small parking and tells me that first we’re going to have some dinner and then we’re going back to his place. All I’m thinking is the plug in my ass, it’s is still painful and I am supposed to sit on it through dinner until we get to his place.

Tommy: “Now come on baby, I dreamt about your throat since last time, I need you to empty my balls before dinner”

He gets his cock out and I sort of lean into him over the middle console of the car. He get a good hold of my hair as I am getting closer and directs me towards his balls.

Tommy: “Mmm suck on them baby make me rock hard for you”

He pushes me towards his balls and I open my mouth and run my tongue around them, take them in and out of my mouth, while he jerks off. Then he pulls on my hair and pushes me down again but on his cock and I take him all the way in.

Tommy: “Mmmm fuck yes I’m not going to last long with that deep teen throat”

He pulls on my head slightly until half of his cock is in my mouth and starts moving his hips and fucking my throat until he pushes my head back on his cock and cums in my throat. It’s weird but I needed that so much since last time. I manage to swallow most of it and he makes me lick whatever leaked out of my mouth.

Tommy: “Let’s go it now”

We get to the restaurant and he has a table booked there. We sit down he orders drinks while the waiter looks at me suspiciously but complies. And we chat about everything and nothing - I told him about myself how I got here, the troubles that I had in school with Jane and Matt and how I got invited to that Halloween party where we met. By the end of it we were done and went out and back in his car. We get to his place and before we get out of the car he tells me to put the collar on, which I do. We walk to his apartment and as soon as we’re past the door he tells me to get on all fours and grabs the chain to my collar and walks me to his living room.

Tommy: “You know what I missed with you last time, babygirl? I didn’t use your tight little teen whore ass.” He gets me to the couch and bends me over the arm of the couch. “Now pull on that dress of yours and show me that ass babygirl” I am fully in execution mode at this moment, I don’t think I just do whatever he says. “Mmmmmm yes baby, such a nice little ass, let me play with that plug, I’m proud that you were able to put it in and keep it in the whole night” He takes the plug and starts to slowly move it in and out of my ass, which is painful but I think I got used to its size and it is quite pleasing actually. He ends up pushing the plug back in and comes around to my mouth with his cock out.

Tommy: “Now come one baby you’ve got a few seconds to make my cock nice hard and wet before I use your slutty ass. I recommend being a sloppy little whore with your spit because I won’t be using any lube” I get right to it, spitting on it, trying to get as much saliva as I could on his cock while sucking it deep. He suddenly pulls out and gets behind me “Now you’re a good slut” he removes the plug “you should learn to appreciate the pain” and pushes his cock as hard as possible into my ass.

Me: “AAaaaaaaaaaaaaaaaaa” it is so painful, it’s really not the same size as my plug. And despite pushing hard into me I can feel his entire cock is still not in me. He gets his cock out of me and pushes one more time, this time he goes even deeper and I can feel his balls bounce off my pussy. He must be all in.

Tommy: “Oh my god baby, I remember your pussy being tight as fuck, but your 15 year old ass on my 51 year old cock is something else. I’m going to destroy that ass baby” it is so painful for me at this stage I’m both screaming and tears are running down my face. “Oh baby, you’ll learn to appreciate the pain look at all these women” he turns on the tv and it’s showing some girl getting her ass wrecked and cumming at the same time. But I don’t feel like I’m really there yet. He starts moving in and out slowly at first and then he fucks my ass hard with long strokes as I am screaming. He grabs the chain of my collar and pulls on it and whispers “such a horny little slut, do you realise you’re getting ass fucked by 51 year old guy you met only once before?”

Me: “Aaaa aaaa yes daddy”

Tommy: “Look at the tv” he says while buried deep in my ass “That’s called a full nelson position baby, a 15 year old lil slut is perfect to be used like that”

I see a guy there sitting on the couch and a girl folded in half on him with his hands behind her back. Not sure how to describe this so look it up if I’m not clear. He gets out of my ass and I just feel it so sore already. He sits on the couch and I get on him with my ack turned to him. He gets his cock in my ass again. He grabs my legs and pulls them behind my head, who thought doing gymnastics would have help at that, and rests his hands behind my head. And now he just starts fucking me like crazy. I am in so much pain but I don’t know why the feeling is different in this position.

Me: “Mmmmm daddy I think I’m cumming”

Tommy: “Oh my god baby, come on, cum on my old perv cock”

Me: “Oh fuck daddyyyyyy” as I can feel both my pussy and ass contract multiple times

Tommy: “Mmmmmm take that you fucking whore” As I feel his cock get even harder and feel him cumming inside my ass. He moves in and out a few times and removes his cock from my ass and puts me next to him on the couch. I’m just laying there on my side, a bit besides myself. He comes towards my face and grabs me squishing my cheeks “Now that’s a good lil teen whore” and as I try to say yes daddy, he pushes his cock into my mouth, not really fucking it just moving in and out a little bit “Clean that cock for me you dirty high school bitch” it’s a weird taste mixture of his cum and my ass but not unpleasant. We end up showering and get to bed.

As I wake up slightly he’s still sleeping and I can’t believe it. I’m living the life here. I feel like an adult, hooking up with him like that. As I am lost in my thoughts, Tommy also wakes up. As he sees that I’m awake as well he gets up and out of the room. He comes back with the crop.

Tommy: “On your belly now” I turn around and he hits my on my ass with that crop

Me: “Aaaaa”

Tommy “Sorry daddy”

Me: “Sorry daddy” he does it 9 more times with each time me saying sorry daddy

Tommy: “Do you even know what you’re sorry about?”

Me: “No daddy I don’t”

Tommy: “When you wake up before me you should be sucking my cock, I should be waking up with your 15 year old throat squeezing on my cock”

Me: “Yes daddy I’ll do it now”

Tommy: “Forget it, now the house needs some cleaning” a bit weird I guess but I can do that “and put the maid outfit on” As I am getting dressed he also says “your punishment is not over yet by the way”

I get to cleaning the house, I do the dust, floors and surfaces, while Tommy watches porn in the living room. It is soon lunch and I hear Tommy order some Uber eats. As I am done cleaning the doorbell rings.