I still keep in touch with my babysitter Lori. I'm in college and it seems that she thinks I need her to keep me in check because of my behavior. She always promises me discipline punishment and spanking to keep me from screwing off. 

To refresh the memory, Lori is about seven years older than I am and she has been my babysitter for a long time. I am now nineteen and in my freshman year of college. Lori about twenty-six years old.

Lori gives me the usual discipline punishment and spanking routine over her knee. She informed me before I left that if she had to come up here to the college to administer a spanking, she definitely would. She doesn't give a shit if we get caught or not, or who knows about it.

I call my babysitter on Thursday afternoon. Being honest with her, I tell her that I am screwing off sometimes and slacking this month. Lori, in turn, says that she's coming up to give me an over-the-knee spanking.

Lori over the phone says, "So, what are you telling me? You've been screwing around?"

"Yes, Lori, I can't lie to you. I never can and never will."

"So what are you telling me, that I have to come up there and spank you for screwing off?"

"Yes, Lori, and I'll prepare for you by the time you get here."

"Yes, that's right and be ready. I'll be leaving in the morning so when you get out of class, I'll be there waiting. "

"Yes, of course, Lori."

"We will go eat first and when we get back, it's punishment time."

"Lori, It will do me some good."

"Yea, I know you're looking forward to it, you naughty boy."

"Yes, I am and I need it too."

"Have a good night tonight. No jacking it off  and I love you."

"I love you, Lori."

I decide to go to bed around twelve tonight after watching some Tv. My roommate John has already turned in for the night.  I fall asleep no problem since I know I have to report to school tomorrow too, besides seeing Lori afterwards.

I awake about seven-thirty. My classes start at eight-thirty which leaves me plenty of time to get ready. As I'm having coffee I receive a text from my babysitter, Lori already. It says, "Okay, I'm leaving my house at ten-thirty so I'll be there at twelve-thirty or so. Don't make me wait for you, buster, or else."

I reply, "Okay, Lori, I'm up and ready."

In the fifth and last class of the day before the weekend I think of her and her arrival. It s nearly twelve-thirty now the class is almost over. My new friends, Kelly and my roommate John want to get together with me but I have to tell them a friend is coming over and we'll be quite busy. I start to mention we may go get something to eat and talk about. They leave it at that.

I start walking and I get near the parking lot, Lori is there waiting for me. She's dressed very nicely and professionally. She's dressed like a secretary, wearing a black leather skirt and a solid white button-down shirt. Her soft black leather pocketbook is new. Her shoes are medium heel black stiletto shoes. The smell of leather is all over her. There's something sexy about a woman in leather.  

Lori says, "Hey there, buster." We hug and greet and kiss on the lips and let go.

I reply, "Hey, how was the drive here."

"I did okay coming up here," Lori replies.

"That's good though."

"Okay, so you want to go get something to eat before our business? "

"Yes, Lori, of course."

"Okay, get in the car."

She drives a new black dodge charger. It is extra clean and is smelling extra good. It smells of leather inside the car too and I love it. The seats are made of black leather. She seems to like it too. There's a blue hard case suitcase in the back seat too.

Lori begins to ask, "Should we do Starbucks?"

"Yes, Starbucks is fine."

"Okay, away we go."

She drives us off to Starbucks and decides were going to hang out for a while. We get to Starbucks and she pulls in the fifth spot and turns the car off.

Lori begins to ask, "Hey, so what's the story with you? Why are you screwing off?"

"I just miss you, so I began slacking off, I think, to get attention."

"Okay, what am I going to do with you?"

"Give me a spanking? I want to be with you."

"We are together, Steve."

"I miss our together time."

"Yes, I do too but I have been firm with you about this."

"I did meet other friends but I've known you for so long."

"I am not going anywhere, Steve."

"Okay, promise?"

"I promise and before I go, I'll give you the spanking you desperately need."

"Shall we go inside, Lori?"

"Yes, we shall."

"Okay, stay there."

I get out and open the door for her and hold out my hand. She takes my hand and holds my hand softly. I hold the door open for her as we walk hand in hand into Starbucks.

We start to order two grande coffees. I pay the barista and receive the coffees. We begin to dress our coffee at the condiment counter adding sugar in the raw and a splash of milk. We sit at a table across from one another connecting our hands. Her hands are so soft as we talk about our relationship over coffee and where it is going. Lori and I decide to take the relationship to the next level. We start to talk about the future together.

We arrive in the parking lot and get back to the dorm. I'm told to grab her suitcase and carry it for her.  I open the door for Lori again and shut her door. She locks her door and pockets her keys. I carry a suitcase which doesn't seem heavy. We get to the dorm room without anyone noticing. My roommate, John, and Kelly seem to still be out.

"Okay Lori, no one's here, good."

Lori says, "I know I'm happy about being able to be with you."

I reply, "Yes me too."

"You want to get started."

"Yes, please."

"Okay, first pull your pants down."

My penis begins to grow as I pull my pants to my knees. She stands tall and firm as she shows firm control over me. Lori stands over an inch taller than me without her heels. She changes her white shirt blouse and puts on a short-sleeve leather shirt type blouse. She takes out a pair of handcuffs from her suitcase.

Lori starts to say,  "Mmmm, you're growing hard already."

I reply, "Yes, Lori."

"That's what I like to see. Are you comfortable?"

"Yes, I'm very comfortable."

"Walk towards me."

"Yes, Lori."

  "It's Mistress Lori to you."

I walk towards her and put my hands in front so she can cuff me.  She takes the handcuffs and cuffs my hands in front of me. She pulls my boxers down to reveal my hard penis. Lori sits down on the chair, licks her hand and starts to jack me off as I stand still. My penis throbs in her hand as she works it. She works it faster, yanking on it.

Lori says, "Step out of your boxers  I have these for you."

"They look like girls' bikini briefs."

"Yes, they are but they're unisex, put them on as you will be taking your spanking punishment in them."

"As you wish, Lori and I kind of like them."

"You're silly."

I agree as I step into them she helps me in them and pulls them up. I feel sexy in them as they held my penis in one. spot. Although they feel embarrassing, they do feel good and she wants it this way as well.

"Now, over my lap, you go."

"Yes, Lori."

I feel her hand grab me as I'm put over her lap. I'm now over my babysitter's lap again taking a spanking. It's where I want to be. I feel my hard-on in my new girlie panties pressing her leather skirt-clad lap. I feel comfortable submitting to my babysitter over her lap.

Lori begins to say, "Okay, I will now start the spanking. Are you ready for your punishment?"

I reply, "Yes!"

"Yes, what."

"Yes, mistress."

"Yes, mistress what?"

"Yes mistress Lori, I'm ready for my spanking."

"Very well."

I feel her start to rub my ass and then spank me on both ass cheeks with her soft bare hand. I feel stinging already even though we just started. Lori's hand is six in women and not too small. She makes sure it starts to redden up as she examines her work on my behind.

"Did you learn your lesson young man?"

"Yes, Lori but I need my discipline."

"Very good, you know your place."

"Yes, I do."

"Are we disciplined?"

"Yes, Lori, I'm disciplined."

"Do I have to come and discipline you again next month?"

"Hopefully, I won't need it, but I want it." 

"Ok, and how badly do you want it?

"Yes, I feel I need the discipline very badly."

"You know this spanking is good for you because when you take discipline like this, it makes you a better person."

"Yes, mistress Lori."

"You know your place as I am your mistress."

"Yes, I learn to respect this way, and you're always right, Lori."

"How about if I just fuck you in the ass with a strap-on dildo again. Would you like that?"

"Yes, Mistress Lori I would like it."

"Yes, and rough and hard, right."

"Yes, I'd love it."

"Don't forget to call me mistress and thank me."

I feel more smacks coming down from her hand on the backs of my legs too. The redness starts to show too. She continues her spanking as she gives me a wedgie, pulling my panties up. With my hands cuffed I have very limited movement as her hand goes to my hard penis through the panties.

"Thank you, mistress."

Lori rubs it over and over massaging my balls and crotch. She starts to administer more punishment as the door opens and John and Kelly walk in on us. They shut the door behind them.  Lori continues the spanking as she doesn't care.

"Thank you, mistress."

Kelly says, "Oh my God, dude, wow. What's going on? I didn't know you like this sort of spanking and BDSM thing, I'm impressed and in shock."

John says, "Yea, you're somewhat quiet and sometimes grumpy."

I reply as I'm over her lap, "Yes, I admit I like it, and this my babysitter Lori."

They both say, "The babysitter?"

"I'm Lori, yes guys, I'm the babysitter. Steve needs some discipline so I'm here to properly punish, discipline and spank him as you two can watch and get off on it, so don't interfere. He has to obey me and no one else, got it?"

John and Kelly both answer, "Yes we got it."

Kelly says, "wow, this is so hot."

John adds, "yes, I know."

Lori says, "I will be spanking him in front of you two, as I embarrass him."

Kelly starts to say, "Check out the girl panties you have on bro."

I begin to say, "Okay I know, don't rub it in."

Lori continues the spanking as she gives me an atomic wedgie with the panties on. She rubs my penis from the bottom as she pulling my wedgie up in the back. Now she starts spanking me again as more skin is being exposed. She then grabs her paddle from the bag to make it more interesting.

"Thank you, mistress."

Kelly says, "Oh my God."

The black leather paddle is studded on the sides and Lori purchased this for her to use on me when I need it. Lori brings the paddle down on both cheeks hard as she pulls the panties up and down again wedging them. She removes my panties altogether. 

"Thank you, mistress."

Kelly starts to say, "Oh my God, this is so hot."

Lori starts to say, "Spread your legs open."

I spread my legs, Lori uncuffs me and she access to my penis. She begins to jack me off from underneath. I feel my penis feel up against her leather skirt. It's now in her hand as she beats it. 

John seems to get off and begins pulling down his pants as Kelly joins in by kneeling in front of John and helps him remove his pants. Kelly pulls down boxers as his erect penis pops up and out in front of Kelly.  She begins to beat him off on the chair. He enjoys it and tilts his head back. 

Lori keeps beating me and whacking me off in-between her legs as she starts hand spanking me again. She starts lecturing me about misbehaving and that she will punish and spank me again if she has to. 

Crack, crack, crack.

Kelly opens up her mouth swallowing his hard penis. She swallows it down to the base and they look as if they're having fun too. She begins beating him off as he maintains the hardness. She jacks off him off steadily

Lori continues her punishment on my ass and not letting up. Her hand grips around my penis firmly, wanking it over and over again. She tells me she will embarrass me and put me over her knee again.

"If I have spank you again in front of others I will. Do you understand?"

"Yes, Lori."

"I will embarrass you in front of everyone, even if it's your teacher that you like."

Kelly says, "You like a teacher, Steve?"

John says, "Wow this is fun."

I answer, "Yes Lori I understand."

Lori says, "Even if I have to use the strap-on on your ass again."

Kelly replies, "Wow, Oh my God, I want to watch."

John says, "Hell, yea."

My face turns beet red as they now know I like taking it from a girl with a strap-on. Kelly goes down on John as his dick throbs. She works it as she's going down to his base and deep throats him. She sucks on the tip and pays attention to the sensitive head.

Lori continues her lecturing and spanking session as she beats me off. Lori then removes the handcuffs as I hang my hands down. 

Lori says, "Okay, now get up. Mmm, you're very hard still. How is this feeling, huh?"

I reply, "I feel so good, Lori."

"Very obedient, thank you."

"Yes, Mistress Lori."

Lori begins beating me off from the chair. I stand still as I take the wanking. Her soft hand feels my penis is slick already. She beats it faster. She yanks it more as I'm heading for orgasm.

Kelly swallows John continuously faster. She grabs his balls and massages them. She swallows him down to the base. Kelly knows John is approaching orgasm as well and seems like she's trying to get him to last past me without cumming in her mouth.

Lori knows this as she in competition with the younger Kelly and whispers in my ear about not cumming yet. I nod my head in agreement with her as she wanks me off. 

John may be too late as Kelly is giving him head he may be the last point of no return. Kelly sucks him off, like a lollipop but tries not to go too hard.

Lori, sucking me off too, knows from experience how far to go with me to last longer. Kelly and John seem like they will lose to the experienced Lori. She grabs my balls with her soft hand and releases as she has her mouth around my hard dick.

Kelly sucks it like a lollipop slow but John starts to lose it as he precums in her mouth. Kelly grabs his balls too. John cums in her mouth though as releases. Kelly tastes it as she licks it. 

Kelly says, "Nice going. I wanted you to outlast him, you bastard."

John, "Oh I know, but I couldn't."

Lori says, "That's what happens when the experience is involved."

I start to say, "You know it, mistress."

Kelly says, "That's so hot that he calls her mistress. "

Lori sucks me off as she knows how close I am. Lori massages my balls again. She whacks me off again, beating it slow. Lori swallows me again down then to the tip to play with the head. I begin to cum in her mouth as she takes it. Some go down her throat and some out of her mouth onto her cheek. Lori pulls it out.

I start to say, "I had so much fun, Lori, even though we got caught."

Lori says, "I don't give a shit about getting caught."

"I know you don't."

"I'm so glad to hear that and I'm coming in a month so behave."

"You're staying tonight right?"

"Yes, with you."

"Good, we all will  be comfortable."

 "I'm sure we will and we can cuddle."

That night, Lori spends the night as we hold each other comfortably in bed and sleep well all night long. John has Kelly with him in his bed too.