“Alright everyone sit down in your seats. Let’s get started. We’re already running way behind and the first meeting of the year is the most important, it sets the tone for everything else we will do.” Kendall yelled as she barged into the room. “EVERYONE QUIET”.
I looked down at my phone it was 6:58 and the PTO meeting was scheduled to start at 7:00. Only in Kendall’s world is two minutes early considered late. Whelp, its going to be another long year in Kendall’s PTO, but by now I guess that I’m somewhat used to it and actually find all the crap she dishes out to everyone hilarious.
As Kendall took the podium she launched into “I’m Kendall Yancey and…” This is usually about where I tune out, so how about a little about myself. My name is Colin. I’m 29 and lived in Baltimore my whole life. During my senior year of college, I had a one night stand with another girl from my class and she got pregnant. She was from a very conservative family and was going to go through with it and we were going to try and make it work. We had a plan all set, but she died during birth and here I was a 22 year old guy three months out of college with a newborn son named Duncan. Allie was from the West Coast so I was totally reliant on my family to help. Lucky for me my mom and five older sisters jumped in to help. To this day they are always watching him and taking him places. Its never hard for me to get a night off, and often times they’re pitching in without me even asking. Between his cousins hand me downs and six different back to school shopping trips, I don’t think I’ve even taking him for clothes since he was in kindergarten.
“Colin. Colin. Hello.” Kendall’s wrath jostled me out of my daydreaming. “Are you going to be able to set up the dunk tank booth again at the fall carnival?”
“Yup.” I replied giving her a thumbs up. She was hot as hell, but a total bitch. She was 5’9″ with platinum blonde hair and a permanent tan. Her high powered career, made her keep up her appearance dressing fashionably at all times and even upgrading from a B cup to D’s last year. My understanding was she was from South Florida and met her ex-husband in law school at the University of Miami. He then got her to move up here saying he wanted their daughter to be closer to his parents, when in actuality it was because he wanted to go back to banging his high school girlfriend. Four months after they got here, Kendall found out about the affair, but had a house and great job, so she decided to stick it out. Rumor has it she hasn’t really readjusted to single life after all these years and quickly shoots down anyone who talks to her in any romantic way. I wonder the last time she got laid. Maybe that’s what makes her such a frigid person. I wonder if she just kind of lays there thinking of the next person she can yell at. What if she’s a freak in the sheets. Wait a second, I got it, I got it. She’s probably just like my buddies ex. Super dominant outside in life, but put her in the bedroom and she’s a total submissive. It always sounded hot, maybe I should give it a shot.
At almost 10 pm, Kendall finally adjourned the meeting. Usually I was like most of the other parents and couldn’t wait to high tail it out of there so that I didn’t get berated by Kendall or assigned to some dumbass PTO sub-committee, but tonight I stuck around. “Kendall, I have an idea about an activity I’d like to try this year. Can we meet sometime for coffee to discuss?”
“When? I don’t have time to do that, Colin. Can’t you just tell me now?” she responded.
“We’ll I just came up with the idea, and I’d like to put some more thought into it before telling you. Can you meet on Saturday at 10?”
“Let me see.” she replied, pulling out her phone to check her calendar. “My ex has my daughter for the weekend. So I was going to spend the weekend doing work. I guess if I had to I could push a few things until later I could squeeze a quick meeting in at the coffee shop in the lobby of my office building.”
“It’s a date” I said as I winked at her and turned away.
I dropped Duncan off at my sisters apartment downtown, and walked the few block over to the address Kendall had given me. At 10:03 Kendall burst through the door loudly talking on her cell phone. She sat down across from me and scribbled on a napkin what she wanted and motioned for me to go get it for her. As I was waiting in line she finished up the conversation she’d been having. I came back to the table and started to talk, but as soon as I opened my mouth her phone rang and she spent another five minutes being the most obnoxious person in the room. It was now almost fifteen minutes into our meeting and nothing had happened.
“Ok Colin. I’m here. What do you want? I don’t have all day.”
“Why Kendall. Thank you for joining me. My day is going swell, how about yours?” I replied in a very mocking tone. I was about to take a big risk here and figured it was going to be my way or no way.
“Really? Did you not hear me? I told you I’ve got a lot going on and I’m not here to chit chat.”
“Ok then. Honest question. Do you get laid a lot? Probably not, right? When was the last time?”
Kendall’s jaw just about hit the floor. “I beg your pardon, but Colin you are way out of line.”
“Was it your ex? Before you were divorced? How many years has that been? Yikes.”
“Excuse me, but we are not having this discussion.” She began to stand and gather her things.
“Kendall, shut up and sit back in your fucking seat.” My increased tone changed the look in her eyes, and she lowered herself back down.
“That’s better, now let’s cut the crap. Your hot. Like super hot. And don’t think no one noticed how your boobs grew literally overnight last year, but here’s the thing. You’re too fucking bitchy to everyone around you. Last spring I heard some of the other dads referring to you as ‘Kuntdall’. You obviously get off on overpowering everyone you meet, but I figured you out the other night. You act as a total dominant in your normal life, but to counteract that you crave the ability to be a complete submissive in bed. You have an intense desire to please a master and do everything according to his wishes. I can tell by the look on your face that you are in disagreement, but trust me, I’ve known women like you before. You’re a complete slut for obedience, and clearly you just haven’t realized it yet. I’d say that I could be totally wrong, but I know that part of what you get off on is knowing that I always know what’s right for you. So here’s the deal. I am going to allow you to become my slave and give you the opportunity to fulfill all of my desires. I’d like you to think about it today, tomorrow, however long you need. When you’re ready to start actually living your life call me and we’ll go from there.” With that I stood up and began to walk out. Before reaching the door I turned back to the table where Kendall was sitting completely stunned. I bent down and cupped one of her breasts whispering “Dirty Fucking Whore” into her ear. With that I was out the door and one the rest of my day.
I got such a rush from my diatribe, but actually had pretty good rest of the day too. I went back to Veronica’s place and we took Duncan to the last Orioles home game of the season. After the game Duncan and I took our dog for a walk at the park and grabbed a pizza from our favorite place for dinner. As we sat on the couch that night watching a movie, the phone rang. Duncan raced off the couch to grab the phone from the receiver on the kitchen counter.
“Hello Duncan. This is Ms. Yancey, Jackie from school’s mom. Is your Daddy there?”
“Ummm. Dad. Ms. Yancey is on the phone and want’s to talk.” Just hearing her name made me start to stiffen in my pants. I took the phone from Duncan and walked upstairs to my bedroom.
“Kendall. How are we doing this evening?”
“I’m good, Colin. How are you?”
“Wow. I think that’s the nicest you’ve ever been to anyone ever. I’m surprised you’re calling already. I’m guessing that you’ve thought about our talk today.”
“From the tone of your voice I’m going to guess you might even touched yourself today. How many times did you masturbate today Kendall?”
“No. You meant to say ‘i masturbated twice today, Sir'” I commanded.
“i’m sorry. i masturbated twice today, Sir” Kendall awkwardly muttered.
“That’s better. But now tell me this. Do you think that thats a good thing?”
“Ummm. i don’t know. i guess so. It certainly felt good.”
“Thats wrong again. I don’t recall you asking for permission to masturbate today. You do realize that I now own you, right? And more importantly thats now my pussy. You wouldn’t touch another person’s genitals without asking first, so why on earth would you masturbate my cunt without asking if it was ok?” I know she was shocked by hearing this because even I couldn’t believe that I’d gone there.
“Sir. i’m sorry Sir. It’s just that i was thinking about things today and my pussy got wet and at first i was just seeing how wet it was and it felt good and i just kept going. And then i did it again.”
“You must be a dumb fucking whore who can’t learn anything. It’s MY pussy, not yours. Are you going to be difficult for me to train? I swear to god I’m not going to waste my time if you’re not willing to do everything I asked.”
“Sir. No Sir. Again my apologies. It is your pussy, your cunt. i will do anything if you allow me to play with your wet hole again in the future.” The game was starting to click for Kendall and she realized it was fun and incredibly hot.
“The sorry’s are nice, but I do believe that we are going to need to punish you for what you’ve already done. What are you wearing?”
“i just got home from the office. i still have on my suit and skirt and heels. Plus my bra, panties, and stockings.”
“Take off everything except the stockings and heels. Let me know when you’re done.”
Kendall took the next plunge down the rabbit hole and got naked in the middle of her living room, save her stockings and heels like her master asked. i’m done, Sir.”
“Good. Head into the kitchen and grab a metal whisk from your utensils. Then walk up to your bedroom and lie on your bed.”
After a minute of silence Kendall said “i’m ready Sir.”
“You have been a very bad slut tonight Kendall. You’re now going to punish yourself. Spread your legs and I want you to smack your pussy as hard as you can with the business end of the whisk.” I heard a slap followed by a slight shriek of pleasurable pain. “Do it again.” Another hit. “Do it ten more times.”
I counted them out with her. Once we got to ten, Kendall was breathing heavy and I asked “How does my cunt feel?”
“It burns, Sir. But may i tell you a secret?”
“i liked it, Sir.”
“That’s too bad slut. I was going to let you masturbate again, but if you’ve already had some pleasure then I guess that is enough. Good night Kendall. We will talk again soon.”
“No! Sir please. It wasn’t that pleasurable please let me masturbate.”
“Kendall, you will learn that I know what’s best and you will learn to trust me. Good night”
“Good night, sir. Thank you.”
“Oh and Kendall. One more thing. Don’t touch yourself tonight. You don’t have permission.”
“i know sir. i’ve learned my lesson.”
I yelled downstairs to Duncan that I was going to go to bed for the night. During my conversation with Kendall, I’d obviously given myself quite an erection and figured I may as well take care of it. It didn’t take more than a few strokes until I had a few thick globs of cum around my navel. I figured Kendall had been good enough tonight so I snapped a quick picture of the jizz, taking care to not get much else in the frame and texted it to her saying “Look what you made me do, whore”. And with that I passed out for the night.
I didn’t hear anything from Kendall and was unsure if she was having second thoughts about things, until she asked me to stay after that week’s PTO meeting. When the cafeteria was clear I approached her. “Good evening, Kendall. How have you been? I was surprised I hadn’t heard from you the last few days. You know, since our Saturday night phone conversation.”
“i’m sorry, Sir. The truth is i was a little embarrassed and confused and not sure what to think about things. That was until i saw you tonight, and a wave swept over me and my crotch got insanely wet. i was so worried that someone would notice while i was up here speaking tonight. You couldn’t tell, could you Sir?”
“I couldn’t tell” I said. With that I bent down and reached up her legs towards her mound feeling the warmth and moistness. When my fingers got to her panties I realized that they were soaked. I looked her dead in the eye and said “I can tell now though. Unfortunately, I can also tell that you have quite a bit of hair down here. Owned sluts should always be shaved completely bare for their master. Also, they should never wear underwear so that master can ensure their cunt is properly manicured. Lets take care of this tonight.” I hooked pinched the wet fabric between her legs and pulled them down just past her knees until the fell freely to the floor. “Pick them up.” Kendall bent down and picked them up. I was surprised I’d expected something a little more conservative, but it was actually a skimpy thong. She handed them to me and I refused. “Ball them up and place them in your mouth. When we get to our cars you may remove them.” From her eyes and her wrinkled forehead, her mind was obviously saying no, but when she placed onto her stuck out tongue her body was obviously saying yes.
When we got to the parking lot, I told Kendall to drop to her hand and knees in front of me. Confused again, I shot her a stern “Do not question me look” and she got down. “Ok Kendall, you may spit your wet panties out now.” She did as she was asked and looked up at me. I bent down and patted her on the head. “Good Girl. Now get into your car. Your ex has your daughter tonight, right? I am going to follow you to your house and we will give you a smooth shaving and make it a proper slut cunt.” As she got into her car, I told her to hike her skirt up so that she could let the fall evening air cool her hotness. Again a confused look, but she did as she asked.
I followed her home. Fortunately she didn’t live to far. I was so hard and spent most of time rubbing myself through the fabric of my shorts. I pulled into her driveway and quickly exited my vehicle I got to Kendall just as she was getting out of the car. I noticed she instinctively tried to pull her skirt back down, but I reached out and stopped her. “Keep it hiked up.” Seeing her waddle to the front door and try and fiddle with her keys in the lock while holding her skirt above her hips was hot. We entered the foyer and I as soon as she hung her purse on the hook I slapped her on the ass and said “Upstairs. Bathroom.”
Kendall undressed as we walked the stairs. By the time we got to the bedroom all she had to do was hold onto the dresser for a moment to undo her heels. We entered the bathroom and Kendall turned the shower on and stepped in. I sat on the toilet seat and stared at her as she trimmed her pubis seperated from it only by a quarter inch piece of glass.When she was done I reached in and shut the shower off. “Step out now, Kendall.” I grabbed a towel off the hook on the wall and started patting her down and drying her off. “Widen your stance and spread your legs. I need to make sure you’re fully dry.” After her skin was dry, I led her to the bed and pushed her on her back. I took a moment to look over her fully sexy naked body. If only all the other PTO dads knew what was happening right now. I crawled towards her and pushed her legs apart, causing her lips to be very exposed. “Kendall, show my new look cunt to me.”
“Sir you’re only inches from it. What more would you like me to do?”
“From now on when I ask to see my cunt, you will reach down with your hand and use your fingers to spread your lips and show my glistening wetness. Let’s try again. Kendall, show my new look cunt to me.”
She reached down and parted her lips. She’d apparently just gotten a manicure and the fresh nail polish looked great against the wet pink backdrop. As she sat there with my pussy wide open her scent started filling my nostrils. I loved her musky smell. “Show me your clit, slut.” She did. “Rub it.” She did. “Keep going.” She did. Her moans got deeper and faster as she worked herself into a frenzy.
“Master, i’m getting close to cumming. Can your slut please cum, Sir?”
“Take your fingers off your clit.” Again she obliged. “Do you squirt?”
“Yes Sir. But only when i masturbate my pussy hole. i don’t know why, but i never have just playing with my clit.”
“Squirt me in the face, you wet whore.”
Kendall spread her pussy with her left hand giving me a great view. She then entered her hole with her right index finger. A few pumps and she added her right middle finger. She kept plunging in and out her, hips bucking off the mattress in pleasure. A few more strokes and her back arched putting her wetness within inches of my face she removed her fingers and unleashed a fury of juices directly into my eager face. I let the cum run down my face and drip back onto the sheets.
I stood up and looked back at Kendall in her post orgasmic daze and gave her a smile. “Good night whore” and with that I was back to my car.
Kendall and I texted a every few days. Sometimes it was in the mornings before work, sometimes it was in the evenings before bed. One day she even texted me in the middle of the day.
“Sir, i’ve been so horny all day. Its really hard to keep from touching myself. Everytime I put my hand on my knee, can feel the warmth and wetness radiating from under my skirt and it gets me wetter. Can i please masturbate your cunt?”
I’d been on the phone with someone for work when I saw the text from Kendall come through. I hurried off the phone relishing the opportunity to help Kendall take this step.
“You’re such a dirty slut. If I’m going to grant you permission, you have to do exactly what I say.”
“Duh. i’m your slave, i always do whatever you say.”
“Indeed. You’ve proven yourself to be a very competent cunt. Get up and shut your office do, but do not lock it.”
“But what if someone comes in.”
“Then they will see a you going to town on yourself. If you get horny and want to masturbate at work then you will do exactly as Master says.”
“Yes Sir. i am laying on my couch now. My skirt is pulled up to my hips and your cunt is fully exposed.”
“Show me my cunt.” A few moments later the picture came in. There was Kendall’s lips spread wide open and dripping with her sex juice. “Very nice. You may play with my vagina now.”
Two minutes later my phone beeps again. “i’m ready to cum now Sir. Please grant me permission to make your cunt cum. She is so wet and needs to release.”
“Cum for your Master.”
“Thank you Sir. i won’t disappoint you.”
Another five minutes goes by and I get another update. “Thank you again Sir. i came four times, my thighs are completely soaked, but i am finally satisfied.”
“You’re welcome Kendall. Have a good rest of the day.”
There was no PTO meeting that week because of Parent-Teacher conferences, so we didn’t see each other, but Thursday afternoon I got a text from Kendall saying she’d like to see me, was I free for dinner Friday night. At first I wasn’t 100% sure what she was after, but she responded to my “Sure. I’ll make reservations and text you. 8 work?” with a kissy face emoji and I knew that it was game on.
I called up a steak house downtown and made a reservation. I then called my secretary on the intercom and told her that I was going to be taking the rest of the afternoon off. I got on the highway and headed towards the mall. I figured that if she wanted to get taken out in public by her Master she may as well look the part, and since this was a fun game for me too, I was going to dress her how I wanted her to look. I was really glad that the first night I’d been over to her house I had peeked at her dress and shoe size, since I’d never had any real reason to purchase women’s clothing. Sure I could have asked my sisters for help, but that would have lead to a series of questions I really didn’t feel like answering. Who are they for? Why are they so revealing? Where are you going? Yeah definitely better I’m going by myself.
I parked outside one of the high end department stores. I found the women’s section and wandered around. It took me a few minutes, but I found a ton of little black dresses. A very attractive sales woman approached. “Did you find what you’re looking for?”
“I am pretty sure I am in the right section, but never realized how many black dresses there could be.”
“Are you shopping for something special? What kind of style does she usually wear? Any specific designers?”
“I’ve got no clue. We don’t really know each other like that too well. Its really hard to visualize them hanging on all these racks. You actually look very similar to her and are similar in size can you hold them up in front of your self so I can get an idea?”
“Sure. Usually I don’t do this, but for some reason I feel like helping you out.”
We went through rack after rack of dresses. Dana, as I learned her name was, kept trying to tell me about this one and that one. Cuts, fabrics, designers, trying to get me excited by showing she was more than a dumb college student working in retail to pay tuition, but nothing was clicking for me. Eventually we found one, that seemed like it was almost perfect, but no where near revealing enough. I told her the problem and she assured me that it would a tight fitting dress. I told her that was good and all, but I wasn’t looking for just a tight fit. I said that the front would need to be much lower cut, and the bottom came to just above her knees and was at least 6 inches too long.
“Whoa, Colin. I guess you’re planning on this being a hot date. Are you sure about that. Its probably too much skin for most women and we don’t even sell anything quite like that.”
“She’ll wear whatever I give her to wear. She aims to please. Do you know where I could get something like that?”
“Well if you like this dress, we do have an in store tailor that could alter it to fit at no cost. I really want to help you out so I’ll even wear it so they can get the measurements to your liking. You won’t be able to see the final version on me, but I think its our best bet.”
“Perfect. Can you help me with shoes too?”
“Absolutely. I am a shoeaholic. Come with me.” I watched her ass sway in her tight pants as we maneuvered through the store. “Based off of what you’ve told me about your friend, I am guessing you want a high heel? Something strappy and 4″ high? I’d recommend something silver in color to complement that dress.”
She pulled a box off the shelf. “I really shouldn’t do this.” She looked up at me and put her finger to her lips shhhing me. She put them one and did a quick walk for me.
“Dana, they look great on you, but I think my friend should have something taller. I want her to really stand out on our date.”
“Then we will get the 6″ version. Size 8 you said right. Would you like to look at some lingerie as well?”
“Sorry, but I don’t think a bra would work well with the dress we picked especially after they are done changing it around and I don’t let her wear panties.”
Dana’s jaw opened wide with that one and I gave her a wink. “So I guess that’s it? Lets get you rung up and so we can get the dress upstairs since they don’t take anything new after 3.
She rang me up and we headed up to the tailor. Dana went behind the dressing screen wearing the dress and wobbling a bit in the higher than she was used to heels. She grabbed for my hand as she stepped onto the platform. The seamstress quickly marked up the upper section saying that there will plenty to look at there. She then started pinning up the bottom hem. After a few pins I said no ladies, higher. So she removed the pins and went higher. No still not high enough. Dana looked me in the eyes and said that they really couldn’t go much higher, since if they did my dates genitals would practically on view all night. I couldn’t believe what I said next and judging from their faces neither could they. “Not my problem.” So again the dress went higher and finally to my satisfaction. As the seamstress was working I kept catching glimpses of Dana’s purple panties. She clearly saw me checking them out since when I looked at her her face was bright red. I gave her a wink and said that I had a few other stops to make in the mall and that I would pick up the dress from Dana in an hour.
The second stop I had to make at the mall was an adult store. I figured if we were going to have a night of Master and slave play, we’d need some toys. I started with the DVD section and picked up a few in case we needed some inspiration. In the toy section I got a set of four leather straps that I might want to use to tie her to the bed. Also into the basket went a blindfold and a ball gag. I hadn’t done anything like this before so I was kind of working off what I’d thought I’d seen porn stars do. I wasn’t sure how used to anal sex she was either so I got Kendall three sizes of butt plugs figuring, if we didn’t use them tonight we would at some point. Knowing that she hadn’t been too sexually active lately, I figured I’d be a gentleman and threw a bottle of lube in as well. After checking out, I still had a half hour until Kendall’s dress was done.
I hated malls and was just wandering around aimlessly when I walked past a designer jewelry store. In the window was a photograph of a beautiful woman wearing a necklace with a silver heart on it. Inscribed on the heart was “Please return to Tiffany”. A lightbulb went off in my head and I turned back to the store.
Another beautiful saleswoman approached me. “How can I help you?”
“I’d like to purchase one of those necklaces the woman in the picture was wearing.”
“Which necklace is that?”
“The one that says ‘Please return to Tiffany’. How long does it take to do the engraving? I have to pick up my dates new outfit in 30 minutes”
“That’s our signature pendant, Tiffany isn’t the woman in the picture, it’s our company name. This Tiffany and Co. a high end designer jewelry store.”
“Ok, well you offer engraving right? Can’t you make something for me. I’ll pay whatever it costs.”
“Lol. What do you want it to say?”
“Like the picture says ‘Please return to’ but instead of Tiffany, I want it to say ‘Master.'”
With that her demeanor changed. She would no longer look me in the eye, just down at the sales counter. “Sir, i am unsure what i can do, but i must do as you please. Even though you are not my Master, it is always my duty to do what you ask.”
A few minutes later she comes back. “Sir, i found one that we got in the back that was missing the Tiffany and Co. part of the original engraving. Technically it’s supposed to be destroyed, but i convinced my manager to sell it to you for half price and do an engraving for free.”
“Perfect. Thank you.”
10 minutes later she’s wrapping my necklace up. “It has been my pleasure to serve you, Sir. i hope that i’ve served you well.”
“You have. I am very happy about this and I know that my sub will enjoy it.”
A few minutes later and I am back to Dana’s register to get the dress and on to my car. As I sat in the seat of my car I realized that I had a raging hard on. I quickly snapped a pic and sent it to Kendall. “Excited for tomorrow.” As I got back onto the interstate my phone dinged. I picked it up and it said “me too” accompanied by a picture of Kendall’s pussy spread wide and dripping wet.
The next morning I lugged most of yesterday’s purchases up to my office. I kept all the sex toys other than the butt plugs and lube in the car. I gave the stack to my secretary along with a card I’d written the night before and told her to call a courier to bring it to Kendall’s office.
At 12:30 the courier came by and picked up the packages and I knew I’d hit a point of no return. Forty minutes later I got a text “Thank you Sir. i will see you tonight.” The rest of the day just kind of dragged on and it was all that I could do to keep myself busy. Finally five o’clock came and I was out of the there as quick as I could. I picked up Duncan at school and took him home to make him dinner. I was glad he was so excited about sleeping over at my sisters house because he knew that he’d get to stay up late with his cousins and that his Aunt Jenny always made chocolate chip pancakes on Saturday mornings, that he really didn’t ask anything about my plans for the evening. After he finished eating we packed his backpack up and drove the six blocks to Jenny’s house. I always used her for the babysitter when I had dates, knowing that she was the least likely to be judgemental or ask questions, and most importantly not start talking to the rest of girls in the family about who Colin’s out with. That being said there’s still no damn way I was telling her that I was going out with Kendall Yancey. No way could she possibly keep that under wraps. I said hello to everyone and quickly hugged Duncan tonight and got out of there so I could get home and get ready.
A shower and a shave, and I was getting dressed. I thought about rubbing one out quickly to help calm my nerves, but knew it’d be much better to save my load for later in the evening. I still had quite awhile until I was supposed to meet Kendall at the restaurant, but with nothing else to do headed downtown to have a drink in the restaurants bar.
I checked in with the hostess and sat at the bar watching a hockey game, snacking on some peanuts and checking my phone. At 7:45 I got a message from Kendall. “Running a little late. Sorry. Be there soon, Sir.”
“Hurry up I don’t like to be kept waiting.” I replied.
“I’m sorry, Sir. I am just trying to make myself look as good as possible for you. At first I was not so sure about this outfit, but once I saw myself in the mirror wearing it, I know why you picked it for me.”
I chose not to respond, making her think I was frustrated with her. Instead my cock was throbbing in my pants in anticipation for the head turning beauty that was headed to meet me. At eight the hostess came over to my seat and told me that my table was ready and I should follow her to my table. I stood up and adjusted my pants so my bulge wouldn’t be on display for everyone.
It was still just barely eight so I just sat the menu on the table and waited for Kendall to arrive. A minute later a waiter came by. I ordered another beer and a glass of white wine for her. I had no idea what she liked, but I figured it was a fairly safe choice. I look down to check my phone and no updates. When I glanced out to the window I see Kendall walking towards the door. The hostess walks her to our table and I stand to greet her. I remove her jacket and hand it to the hostess. I give her a hug pressing her body flat against mine and whisper into her ear “Good evening, slut.”
“Good evening to you as well, Sir.” Kendall says as she breaks our embrace and I point her to her seat. I was really glad that we’d gotten the best table in the restaurant. It was a bit of a corner booth allowing us to sit basically side by side. In addition it was on a raised platform facing the main entrance and dining room. Plus the restaurant didn’t use tablecloths. All this added up to is my cunt being on full display to anyone else who happened to look over during our dinner. It only took as the waiter coming over with our drinks before I knew my plan had worked. As I complimented Kendall on filling out my outfit better than expected I saw the waiter stare and trip briefly. He caught himself without spilling anything, but all three of us knew that we knew he’d seen the display.
“Ugh. Um. I see your friend has joined you. Here are your drinks.” He set them in front of us clearly looking down Kendall’s shirt and more than likely seeing a bit of her nipple. “So do you uh uh know what you uh want to eat yet?”
“Hey man no worries. It’s ok to look. If I didn’t want guys to oogle her goodies, I wouldn’t let her leave the house dressed like that.”
“i love being on display like this for My Master.” Kendall chimed in. “i live to please Him and this is what He got for me to wear tonight. Look it even says so on my collar. See.” she says holding her necklace up to him “Please return to Master”. I couldn’t believe how submissive she’d already become in only a few weeks. None of this was stuff we’d really talked about at this point so she must have been doing some learning on her own. I filed that under things to talk about at dinner tonight.
We ordered. The filet special for me, a stuffed chicken breast for Kendall. Apparently we had the same train of thought for discussion points. “Sir, is it ok for me to call this necklace my collar? When I opened the box I go so wet just reading your name ‘Master’. i’d like to always wear it, facing in when i’m in my vanilla life, but facing out when i am being a slut. i just want to always have a reminder of you owning me.”
I was so taken aback by the comment. She must have read the surprise in my eyes, so she grabbed my hard on in my pants and stared in to my eyes giving me the puppy dog look. “Please Sir? i’ll do anything you want.” She grabbed my wrist and inserted it between her legs to feel her wetness. Her thighs and the seat were an absolute mess. I stuck out my index finger and she buried her face in my neck as I inserted a finger in her slit. Kendall let out a light moan in my ear and I slipped in and out a few times. I could tell she was getting close to cumming, but the waiter brought over our dinners just before she could.
“I’ll get you a few fresh napkins to clean up your mess” he said.
Kendall was blushing a bit, so I replied for her. “I’ll take one for my hand, but she’ll be just fine sitting there like that.”
We unrolled our silverware and even though both of our dishes were quite good, we were both excited about the night that lay ahead and only ate part of our meals. We worked ourselves back up chatting about more of her D/s research, to the point where when the waiter came back to see how our meals were, I just handed him my AMex card and told him we were all done. He said from what he’d seen of our date so far he understood why we were eager to get home.
As we walked towards the exit, an elderly gentleman grabbed me by the wrist as I passed his table. He pulled me towards him and discretely said “Go get ’em, tiger. Fuck her brains out.” It was all I could do to not over laughing and as I write this it makes me chuckle still. I wonder if his wife that was sitting across from him ever questioned him as to what he said. I caught back up with Kendall. The hostess went to hand Kendall jacket back to her, but I stepped in and took it. I think they were expecting me to be a gentleman, but instead I said “she won’t be needing it. This way to the car Kendall.”
I’d been very glad that I had the foresight to tell Kendall to take a cab to the restaurant. I laid her coat across the back seat and opened the passengers door for her. As she sat she put her whole crotch on display for me, which I always liked seeing. When she was settled I reached up and undid the strap around the neck of her dress letting it fall so that her tits were on display and shut the door. I walked around to my side of the car, got in, and backed out of the space. Apparently Kendall had a real knack for serving, because before we were even out of the parking lot she had unzipped my pants and pulled my cock out. I’d gotten a blowjob in a car once in high school, but it was the first time I’d gotten true road head while driving, and it was just as thrilling as I’d expected. As we rounded the corner into Kendall’s subdivision, I came several deep long shots into the back of the throat. She stayed down on my penis until we pulled into her driveway, as she swallowed every bit of cum that I’d made.
“Kendall, you’re not going to try and retie your dress before you get out of the car, are you?”
“No Sir. i learned last time that you like seeing me on display, even if one of my neighbors could see.”
We got out and I got her jacket and my bag of toys from the back seat as she fumbled in her purse for her keys. We entered the house and she locked the door behind us while I hung her coat up. I took her hand in mind and said “We will now go upstairs to play.”
We got up to the bedroom and I threw Kendall on the bed. By now her dress was off down to her hips and the top straps were actually down by her knees. I grabbed her ass and easily yanked the dress over her waist and completely off. It actually got stuck on one of her stilettos, so I figured they needed to be removed too. Kendall was now laying fully naked on the bed except for her collar. I lifted her knees towards her head and gave a quick tug on her butt plug. “Well keep that in until I’m ready for that hole.” I warned. I quickly removed my clothing and in the nude, I flipped the dresser lamp on so I could find the pack of leather straps I’d purchased. I turned around, I saw Kendall with her index finger and middle finger inserted deep into my cunt.
“Who the fuck do you think you are and what the fuck do you think you’re doing?” I snarled.
“i’m fingering my pussy.”
“Wrong.” A one word reply.
I stared at the foot of the bed trying her ankles to the corners of the footboard so she was fully spread out. Next I climbed into bed to do lash her wrists. I got the one on the close side of the bed easily, but to reach across to the other side I had to cross over Kendall’s body. I made no effort to be gentle and dragged my sex organ over her face pressing it into her cheek as I secured her final limb. I crawled back out of bed. “Kendall you were going to be tied up and blindfolded regardless so that I could have some time to play with you as I saw fit. But now because you have such a wanton disrespect for me you are going to be punished.” I returned to the bag for the blindfold and slipped it over her head.
I exited the room and walked back downstairs to the kitchen. It took me a few minutes to find a good wooden spoon and a glass. I filled the glass with ice cubes and headed back upstairs.
“i’m glad you’re back Sir.”
“Shut up. You’re not allowed to talk right now. You’re a naughty cunt and I am now going to teach you a lesson.”
I set the cup on the nightstand and kneeled over her body, resting my ass on her tits, facing the bottom of the bed. I took the the spoon and with a quick motion slammed it down towards my cunt. Kendall screamed not expecting it “Motherfuckerrrrrrrrrrrrrrrrrrr.” I’m sure she would have popped up, but with her hands being bound she was powerless. I wanted the first to be extra hard for the sheer shock value, and then rest with a more moderate tone. With this being the first time I was punishing her in person and it being a lesser offense I didn’t want to over do it. Nine thwacks later and her lips had a serious pink color. “Do you think that’s enough, slut?”
“Sir, i will be grateful if you stop, but understand if you feel that i need to learn my lesson more. i submit to you because My Master knows all.”
I didn’t answer verbally, just another three whacks with the spoon. I followed this with five very quick slaps to my cunt with an open palm. Then another round of three spoon hits and five hand slaps. After this set I used my hand to separate the lips and probed her vagina hole with my finger. “You are very wet.” With that three more spanks. “One more.” This one I made very soft, just a tap, a brushing. Kendall let off an obvious sigh of relief, just what I was hoping for. I followed it with a very hard and violent wack similar to the very first one that I’d given. Another shriek from Kendall and I unmounted her.
I took the glass of ice cubes and crawled down between her legs. I took the first one out and rubbed it on her now very red labia. “Kendall, I call this punishment Fire and Ice. When the cube melted I pulled another one out. This one I inserted into her whore of a hole. I fished another ice cube out and started working it into Kendall’s clit. After it melted I took out the final cube and rubbed it on my fingers until they were nicely chilled. I then popped the cube into my mouth and lowered it towards my pussys lips. I used my frozen fingers to open her up and rapidly starting tonguing her pussy lips. The cold was very uncomfortable in my mouth, but I wasn’t about to show any signs of weakness, plus it was only a matter of time before the ice was done or she was ready to cum. I was right and just as I noticed the coldness beginning to fade from my mouth, Kendall piped up. “Sir, Sir, please. Sir. i’d like to cum. Please let me make cum in your mouth Sir.”
I pulled up from my cunt and gave permission. “You may cum into my mouth, slut.” I got back into position and kept lapping at Kendall’s crotch. In a matter of moments her lower back bucked up and forced itself into my mouth in the most intense orgasm that I’ve ever witnessed. Three minutes later, Kendall’s seventh wave of pleasure subsided and my face was absolutely saturated.
I wiped the cum out of my eyes and laid kisses over Kendall until I got to her face. I straightened my self so that my penis and testicles were right in front of her. I could hardly get the phrase “Pleasure me with your mouth” out before Kendall was going to town. She started by taking one nut in her mouth and sucking it. She opened even wider and was then able to get both of my balls in my mouth, alternating between sucking and licking them. I lift myself up and out of her mouth.
All this oral sex had gotten me rock hard again and I made my way back to Kendall’s legs. I positioned my cock head at her entrance. “Sir are you going to fuck me? Sir i’d really like to have you inside me. Please fuck your slut hard. It has been over three years since i’ve had a cock inside me and i need to have your perfect piece of manhood up in me.”
With that I slammed into the well lubed canal. Kendall had begged me to fuck her hard so I went in and out as rapidly as I could. Quicker and quicker, harder and harder. A few times I’d even managed to fully pull my cock out of my steaming pussy, but was fortunate to be able to slide right back in without missing a beat. I could feel the semen starting to rise and pulled out.
“No please Sir don’t stop.”
“Kendall I am going to untie you now.” I pulled her blindfold off and undid the leather bands. She laid on the bed staring intently at me as I put my toys back in my bag. “Get on your hands and knees with your ass in the air now.” Kendall shifted into the position. I got back into the bed and knelt behind her. I took a hold of the butt plug and tugged it to the point it started to slide out. I pushed it back in and Kendall gasped. In and out a few times and I was fairly certain she was as ready as she could be to get butt fucked. I pulled the plug fully out and set it on the nightstand. “It’s time.”
“Sir, please be gentle. i’ve never had anal sex before. i think my butt is very tight and I don’t want it to hurt.”
“You can’t be that tiny since you’ve been using the medium sized plug all night. Trust your Master. I will make sure it goes off well.”
“i trust you Sir.”
I reached my index and middle fingers into my cunt and got them saturated. I transferred the juices to her asshole trying to get her slick enough to easily take me. I repositioned myself behind her and stuck my cock back into my cunt doggy style to juice it up. I pulled out and slowly entered her asshole. Kendall gave a soft cry as I slid in all the way in until my pelvis settled against her cheeks. “Are you ok?”
“Yes Sir. i will be fine now that i’ve felt your full length inside me. Please have your way with my ass.”
Kendall didn’t need to tell me twice. I pulled out most of the way and then went back in speeding my pace as I gained rhythm.
“Uhhhh yeah Sir. Fuck my asshole. Fill me with your seed. Mark your territory Master.”
With that I came once again putting seven long bursts of cum into her anus.
“Sir that was so good. How come i’ve never done that before? I can’t wait until we do it again.”
I grabbed Kendall around the waist and rolled us together onto our sides taking care to keep my cock in Kendall’s ass. We fell asleep talking about what we’d do on the next go around as my cum dried on my dick which was still in between her cheeks.