Principal Skinner

The other day Bad Boy and Kitty were talking on the phone. I was telling him the story about E2 as well as my threesome experience since we haven’t had a chance to chat since that. Bad Boy was telling Kitty that his group at work was talking about online dating and safety compared to meeting someone in a bar and going home with them. Bad Boy has voiced his concern for Kitty’s safety on many many occasions and although I assured Bad Boy that my days of meeting strange men in hotel rooms for the first time was over, he made me promise to text him the name and phone number for anybody new that I did decide to meet.

No sooner did I make the promise, Kitty came across a new potential playmate on Ashley Madison. He claimed to be a principal of a local high school. This intrigued Kitty. How many of us fantasized about fucking our high school principals??? Well Kitty sure as hell did!! So Principal Skinner (Thanks Blogging Bestie for helping to give him a blog name) caught Kitty’s attention right off the bat and it took him no time at all to send Kitty the most beautiful picture of his huge rock hard cock. The sight of it made Kitty’s mouth water not to mention my pussy.

He wanted to meet desperately for a drink and Kitty knew that meant a blow job in his car. Fool Kitty once… So…yes…it was Kitty’s recommendation to meet at a hotel. E2 left Kitty wanting more. He left me empty. Principal Skinner assured Kitty he could not meet me over the long weekend as he had a house full of company for the holiday. 

Kitty, preparing for my own company and festivities let the subject lie.

Saturday morning I got a text from him asking where I would be in the afternoon. He was out of the house for a meeting and could get a room for us. Kitty faced with the decision to blow off housework for the sexual satisfaction I had been craving since the week before accepted Principal Skinner’s invitation and met him at the hotel not before texting Bad Boy as promised his first name and phone number. “Tags too”, Bad Boy texted back but before I was able to text them Principal Skinner was standing at my car door ready to escort me to the room.

He stood at least 6 foot 4 inches and a good 225 pounds. He towered over Kitty and although his face bared a striking resemblance to XXX he frightened me just a little bit. It was at that moment that I swore to myself I wouldn’t be doing this again.

He led me to the room by my hand, closed the door and immediately began kissing Kitty. I began to remove my clothes and he watched me as I pulled my blouse over my head and pants down to my feet revealing my supple breasts and already moist pussy. Kitty reached down and could feel already that his cock was hard and it was huge. Kitty unbuttoned his shorts to expose his cock. “Well…get down on your knees and suck it,” He commanded.

Kitty followed Principal Skinner’s orders looking up at him as I sucked on whatever I could fit in my mouth. He was extremely patient with this as Kitty moved slowly preventing myself from choking. He grabbed my hair but did not force me which gave me the impression many women had been unable to fit his entire cock into their mouths.

“Get up on the bed and lay face down.”

 Kitty followed orders although I was turned on; I was also quite frightened at the same time. He began kissing the tops of my shoulders, licking then biting…biting HARD. All I could think of was that he was going to leave marks and maybe just maybe it wouldn’t matter once my body decomposed in the shallow grave that Bad Boy and I joked about on several occasions.

Kitty leaned into the pain at first but then quickly turned over when the pain turned to tickling. Principal Skinner threw my body around like a rag doll, fucking me in every position until he finally let me ride that huge cock of his. He sunk in deep and Kitty felt like cumming almost immediately as he said, “You like that big cock don’t you?”

“I like that big cock,” was all I could say as he moved his hips to the rhythm that I started. Kitty touched my nipples as I rode him then he cupped his hands over mine. Once again he said, “you like that big cock, don’t you?” And before I could agree, I let out a moan and scream, “I’m cumming!”

We continued to move together after Kitty’s first orgasm and I was sure I could and WOULD cum again. The beauty of Principal Skinner being so much taller than Kitty is that he was able to fuck Kitty is just about every position where as shorter men are sometimes unable to fuck Kitty doggie style for whatever reason. Considering this 

Kitty requested, “Fuck me doggie style.”

Principal Skinner picked his head up from between Kitty’s legs as he was giving Kitty some pretty decent oral at that point. He flipped me over again and easily slid his cock in from behind fucking Kitty harder and faster than I can ever remember. He paused for a moment, laid Kitty on my side then lay on his side with our legs intertwined then slowly fucked kitty until his face became flush and Kitty could tell he was cumming.

He immediately moved down once more between Kitty’s legs licking, and sucking Kitty’s clit for orgasm number 2. Kitty was pleased. “So are you going to tell me your REAL name now?” He asked as we lay drained. 

In an effort to be playful Kitty said, “No” at first then got up out of bed and handed him my business card. He didn’t look at it. He just slipped it into his wallet.

We chatted for a few more moments. He was spooning Kitty from behind which is Kitty’s all time post orgasm position. We both said we needed to go and then he rubbed up against Kitty, instantaneously got hard as Kitty got wet, climbed on top of Kitty. He threw my legs over his broad shoulders and fucked me missionary style until I screamed with pleasure and he came for his second time.

There was no time to recover after that. Kitty and Principal Skinner both had to get going. He jumped in the shower quickly to wash off the afternoon’s sex as Kitty slipped back into my clothes.

As we left Kitty texted Bad Boy that I was safe and swore to myself that I would never do that again.

"Whole Lotta Love"

The weekend was jam packed with activity. Kitty had lots of vanilla errands to run and since I hadn’t heard from E2 I promised to take my kids to a movie and dinner. Sure enough mid afternoon on Saturday he texted, “What are you doing later?”

All the books and all Kitty’s vanilla friends say to tell him, “I’m going out with a friend.”  So I did. At the same time Kitty was texting a vanilla bestie who said, “It sounds like he’s trying to ask you out.”

WTF?!?!?!? Kitty just can’t win. So I told E2 I’d meet him afterwards. Although we hatched a plan, Kitty made the mistake I often make which is asking E2 how long it’s been…since he’s fucked. He said a few weeks. Why oh why does Kitty ask that question. The answer always seems to be the same and it always make’s Kitty feel bad. E2 asked Kitty, “What are you looking for?”

For the first time Kitty was able to describe what I am looking for. “I want to be someone’s #1. I’ve stood behind jobs, kids, wives and other girlfriends for years and now it’s my turn to be #1.” And while E2 said he understood, he assured Kitty that he was not looking for a girlfriend.

And Kitty being Kitty agreed to meet E2 at his place for a drink even though we want different things and even though I knew we would end up fucking.

E2 has a quaint little house on the water out in the country. It’s quite different from Kitty’s house at the beach. The view of the lake was incredible. E2 fixed Kitty a drink, turned on the classic rock channel on iTunes and we sat out on his deck talking for a few hours. He asked Kitty several times, “What do you think of this view?”

We talked about sex. We talked about work. We listed to Clapton, Pink Floyd and then…it was time for Kitty to leave.

“See, I kept my hands to myself,” E2 said “Maybe we can hang out again.” He stood up to give Kitty a hug…and then Kitty kissed E2…a gentle peck on the lips at first and then the kiss became deeper and more passionate. Kitty felt E2’s enormous bulge between us and I wanted him. E2 unbuttoned Kitty’s jeans and reached inside to rub my clit. Kitty reached in and felt his cock. It was quite possibly the biggest Kitty has ever seen.

“Let’s go inside,” Kitty said “Where do you want me?”

“On the Couch,” he answered. He turned off the lights and left the music blaring. 

Immediately I knew why he wanted to fuck on the couch…the view of the lake. E2 sat on the couch watching Kitty slowly take off my blouse. I slipped of my bra which E2 had unclipped out on the deck. He took off his shirt. Kitty slipped off my pants then knelt in front of E2 as he sat back. I pulled off his pants exposing his huge cock then slowly put it in my mouth trying to take in the entire thing. His hands gently rested on my head and I could hear him slightly say,”oh that feels good.” As the music pulsated. 

Kitty moved up and began to ride E2’s cock. His cock filled Kitty so much so that I could hardly move. He rubbed Kitty’s nipples sucking the right…then the left. The music was so loud. It was Robert Plant singing, “Whole Lotta Love.” Kitty was just about to tell E2 that I couldn’t come when he grabbed both of my nipples nibbling on each as I moved up and down on his cock to the rhythm of the music, “I’m gonna give you every inch of my love.” And then…as Kitty was nibbling E2’s ear, he was sucking my nipples, I was riding his cock and Robert Plant was screaming, “I’m gonna give you every inch of my love,” Kitty came and moaned in E2’s ear. He continued thrusting inside of Kitty and said, “How’s that pussy feel?” Kitty’s pussy felt pretty good but it was E2’s turn to cum. “Turn around,” he said. Kitty turned around and rode E2’s cock reverse cow girl. That’s when I saw it. That’s when I could see what got E2 off. As E2 fucked Kitty from behind, I could see the lake out of the window…the moon overhead. He was looking at it too.

I stood up for a moment, E2 stood up and I could hear him over the music say, “go down on me.” He stood facing the lake as I knelt in front of him trying once again to take in his entire cock. For the first time in a long time Kitty began to gag. E2 stroked his cock and held the head in Kitty’s mouth. Kitty sucked and licked until I felt the sweet taste of cum in my mouth. E2 let out one last moan. Kitty stood and tried to kiss E2. He pulled away. He didn’t want to kiss Kitty with the taste of cum still in my mouth.

“It’s yours,” I said

“Don’t use your tongue,” he answered.

This struck me as funny. Kitty gave E2 one last kiss and snuck my tongue in his mouth. Kitty is very naughty.

I haven’t heard from E2 today. I didn’t expect to hear from him. I don’t expect to hear from him tomorrow either. I knew what I was doing. I’m not sure exactly why I fucked E2 knowing it would be the end. Maybe Kitty is weak. Maybe Kitty is lonely for the touch of a man…any man or maybe Kitty just wanted to share a good feeling with a man that I have grown to like if only for one night.

Playing The Game

It's that time of year when Kitty gets pretty slow at work and that means Kitty goes looking for trouble. The past few weeks have been interesting to say the least. One thing that Kitty found interesting was Mother's Day. Even though Kitty does not consider myself high maintenance when it comes to such Hallmark Holidays it always fascinates me which of my lovers I hear from and which I do not. Kitty tries not to take things so personally but when I took a closer look at who I didn't hear from as opposed to who I did hear from well...it was telling to say the least. Some surprise texts/emails came from "The Salesman", "Bad Boy", "Down and Out", "Tom Hagen", and "Angry Guy".

Kitty will keep the list of who I did NOT hear from to myself but I am always curious as to what that means exactly. One person who I was surprised not to hear from is someone new. His name is "Esquire 2"/E2. E2 is an enigma to Kitty and actually any advice my readers have to offer would be appreciated.

E2 is single...well...separated. He's kind of cute and terribly funny which is a huge turn on for Kitty. E2 is also extremely perceptive which is also a big turn on. We had actually met several years ago when we were both married. More recently E2 began to socialize with one of Kitty's vanilla besties. Kitty uses the word "socialize" because my bestie insists they were not dating although by Kitty's standards they were dating with one exception...they did not fuck. The irony is that my bestie described E2 as a "pothead" and a "sex fiend". I think you all know where this is going...

So months ago Kitty made it my mission to meet E2 and hopefully hook-up. Fate stepped in and I needed his professional advice so I happily made an appointment with him dropping my bestie's name and damned if he didn't pick up the phone and call Kitty himself as opposed to having his secretary do it.

At our meeting I forget exactly what Kitty said but I made a joke about my phone having some unsavory things on it. After our meeting E2 took my number and we agreed to go out with my bestie for happy hour. No sooner did Kitty get home I received a text from E2, "wondering what's on that phone of yours".

E2 and Kitty have been talking and texting ever since. E2 is quite busy as you all can imagine and we talk about getting together for drinks...or fucking quite often but in the end...we don't.

This week E2 didn't text Kitty for two full day's. That's out of the norm for him but all of Kitty's sources say the same thing, "let him make the first move."

The fact that he went for as long as he did kind of hurt Kitty's feelings. Kitty was kind of getting a little wet for this guy and then...nothing.

This morning I woke up at 5 like most mornings. There was a text from him from last night saying, "behaving?"

Kitty: If I say no will you spank me?

E2: No problem

Kitty: What if you are naughty WITH me?

E2: U tell me

Kitty: I'd tease you

Kitty then went on to describe the lap dance I would do for E2 while his hands were tied. I'm not certain but I believe I got E2 fairly worked up. In the end Kitty had to head into the gym and told E2 to have a great day. So Kitty is trying to "play the game". I'm trying to let E2 hunt for me because all of Kitty's advisors say that men like the hunt. That's kind of difficult for Kitty. Kitty is impatient to say the least. But Kitty likes this guy and not just as a fuck buddy. Kitty can see myself with him. So Kitty needs to play this game with E2 in order to let him think he is hunting when in fact Kitty is really the hunter. So what do you all think? How can Kitty catch this one?

Back Seat

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