I have always been sexually submissive, hence my username on this website. I have found, however, that as I get older, I have begun to lean toward the Dominant side. I am 62, financially secure, and still in decent shape for my age. I retired from my 9-5 job last year because I was burnt out and financially could afford to make the transition. My wife, unfortunately, passed away from cancer two years ago. So here I was, lots of time on my hands, financially secure, but looking for something to do. I decided to pursue my dominant inclinations.
I put a post on an adult website looking for a submissive to play with. I had never had much luck on these kinds of websites, but figured, what the heck.
Are you tired of dealing with life by yourself? Overwhelmed? Need someone to provide direction in your life and relieve you of all those responsibilities? Over your head financially? If you meet the following requirements, contact me, I can help.
Female, age 21-40, attractive, height/weight proportional
Flexible schedule
Submissive
Desire to be humiliated
Must be local and willing to meet for a face to face interview
A strong desire to be trained and owned
I included my contact email and posted my ad on a Friday after a couple of vodka tonics. Over the weekend I received the usual flood of initial responses from people who didn’t even come close to the requirements I had listed. Most of them were blatantly looking for a free handout and nothing else. The next couple of days did not yield any other responses at all, I considered pulling my ad. On Friday morning, a week after posting my ad, I logged on as I sipped my morning coffee. I found this email in my inbox, it had been sent late the night before:
Hi. I saw your ad. I have never responded to an ad like this so don’t really know what to say. I’ve had a horrible week, but they are all horrible it seems. I just can’t get ahead and I sure can’t catch a break it seems. I’m a single mom of two young boys. They are great kids, but really wear me out after a long day at work. My husband divorced me over a year ago and have I yet to receive a dime in alimony or child support. I’m tired of dealing with lawyers! I checked out this website because I AM submissive, or at least I think I am. I never really explored this side of me, but think I want to. I meet all of your requirements…I am 29, people tell me I am cute, and I live here in town. I guess my schedule is as flexible as anyone’s schedule can be these days. But it was your last bullet that really intrigued me, I think I need that. Please contact me.
She signed her email SJM and provided her contact info. I felt my cock begin to stir as I read her note and continued sipping my coffee. This response seemed legit and certainly heartfelt. I immediately wrote her back:
Hi SJM,
Thanks for your reply and I am glad you are interested. You certainly seem to have your hands full! If you would like to meet for your face to face interview, meet me at the Sly Fox Saloon tonight at 6:30. Wear a hot pink top so I know who you are. Grab a table and I will join you when I arrive.
I went about my day, wondering periodically if she would get cold feet or actually show up tonight. I decided to get to the Sly Fox a little early, grab a seat at the bar and observe her when she came in. Sure enough, right at 6:30 a cute little blond entered the bar. She was wearing tight yoga pants and a hot pink sports top, she looked like she had just been working out. Her hair was pulled back in a ponytail (which I love) and she looked nervous as hell! She reminded me of Mariel Hemingway, only younger and prettier! My first thought was “who the hell would be dumb enough to divorce this pretty girl!?” She was beautiful. Not “Playboy model” beautiful, but more like “girl next door” beautiful. She seemed to have an air of innocence about her.
I watched her as she scanned the room. She found an open table and took a seat. After ordering and receiving a glass of wine, she headed for the ladies’ room. She was surprised to see me sitting at her table when she returned.
“Oh, ummm, hi,” she stammered as she sat across from me.
“Been working out?” I asked.
“I wish. No time for that unfortunately. I just put these comfy clothes on after work,” She smiled a megawatt smile as she talked.
“What’s your name?” I asked.
“Sara Jane,” she replied. “What’s yours?”
I ignored her question and we went on to exchange small talk for the next several minutes. She explained that her ex-husband had the boys every other weekend and this weekend was his turn. I noticed the wine relaxing her and as soon as she finished, I ordered her another glass. We talked over drinks and appetizers for the next hour or so, and finally I decided to move forward.
“You know, besides this interview, there are a few small tests you need to pass. Assuming you pass the tests, you then get a preliminary acceptance into my training program,” I explained. “Your preliminary acceptance lasts for 30 days. Assuming I am pleased with your performance during that time period, you then will be accepted into my full-time training regimen,” I continued.
Sara Jane listed intently as I explained, just nodding, watching me closely, and sipping her wine.
Finally, I said “Do you want to proceed Sara?”
She lowered her eyes and said softly “Yes.”
“I didn’t quite hear you,” I said curtly.
“Yes, I want to proceed,” she said, this time looking me squarely in the eye.
My heartrate increased; this was going to be exciting! “Excellent,” I said. “You asked me earlier what my name is. You will call me Daddy.”
She quietly said, “Yes Daddy.”
“Time for your first test,” I told her. “What color panties are you wearing?”
She hesitated slightly, then said, “White.”
“What material are they made of?” I asked.
Sara looked up at the ceiling as if trying to remember, then said, “I think they are cotton.”
“Go to the ladies’ room, take them off and bring them to me,” I directed.
She smiled, grabbed her purse and stood to head to the ladies’ room. I didn’t want her to have the luxury of sticking her panties in her purse, I wanted her to have to carry them across the bar in the open. “Leave the purse,” I ordered.
She nodded and went to the restroom. I watched her ass in those tight yoga pants as she walked away and thought how nice it will feel to pound that tight little thing someday. While she was gone, I went into her purse and took a picture of her drivers’ license; always good to have that info. She was back a few minutes later and took her seat across from me. She reached under the table and tapped my knee, handing me her panties. I reached for her panties and purposely held her hand firmly as she handed them to me, staring into her eyes. That moment seemed like it lasted forever, but in reality, was less than a minute.
I took her panties from under the table and examined them. “Rule #1,” I said; “NEVER wear cotton lingerie with me again.” She nodded. “Rule #2, only wear white lingerie if I specifically request it.”
“Okay,” she said shyly.
“Excuse me?” I asked with exaggerated indignation.
“Yes Daddy,” she said softly.
We chatted a bit more as we finished our drinks. “How are you doing financially?” I asked.
Again, that shy, demure look that was beginning to give me a hard on. “Well, the boys need some back to school supplies. I haven’t been able to get them what they need,” she said.
I opened my wallet and slid two, crisp hundred-dollar bills across the table toward her. Her face lit up like a kid on Christmas morning. She leaned across the table and gave me a kiss on the cheek. “Thank you, Daddy.”
Since she was free that whole weekend, we made plans for a nice dinner the next night. Before she left I had her put my cell number in her phone under ‘Daddy’. Likewise, I entered her info in my cell. “I’ll text you tomorrow about dinner,” I told her as we left the saloon. She gave me another peck on the cheek and drove away. I drove home and felt my cock straining against my blue jeans. I immediately began planning her next test for Saturday night.
On Saturday morning I texted Sara Jane and told her what I wanted her to wear to our dinner that night. I was fairly blunt in my first text:
I’m not a big fan of flats. Rule #3: wear high heels every time you are with me unless I say otherwise. I don’t care if you’re wearing a skirt, leggings, blue jeans, or running shorts; you will wear high heels. I AM a big fan of nylons, both thigh high stockings and sheer to the waist pantyhose. I know girls your age prefer the bare leg look, but you will wear nylons when in my presence (Rule #4). If you need money to buy nylons and/or high heels, let me know.
Her reply text was simply: Yes Daddy.
My second text to Sara:
We’ll meet at Morton’s Steak House at 7:00. I want you to wear a short black skirt, black high heels, nylons, a white blouse and a black bra. Wear your hair down and do your make heavy.
She replied: Okay Daddy, see you then.
I got to Morton’s around 6:45, ordered a drink for me and a glass of wine for Sara Jane. I brought a little bag with me that held some goodies for her second test. Sara arrived right on time. She looked amazing; I wasn’t the only guy staring as she strolled in. I’m sure the other customers thought I was taking my daughter to dinner! She had followed my orders to the letter. Sara had on a short, faux leather mini skirt, off black nylons, 4″ closed toe, pointy, black patent leather heels, a white silky blouse that allowed just a glimpse of her sheer black bra underneath. Her blond hair was back in a high and tight ponytail. Her makeup was a little heavier, but not slutty. I instantly got hard; thank god I was sitting down!
“You look great!” I said as she gave me a kiss on the cheek before sitting across from me.
“Thanks! Seems like I don’t hear that much these days,” she sighed.
We enjoyed a wonderful meal and just chatted like old friends. I was growing to like this little girl. Toward the end of the meal I reminded her that tonight would be her second test. If she passed, she would be entered into my training program on a 30-day probationary period. If she made it through the 30 days, I would take her on as a full time submissive. Sara Jane listened intently and nodded as I reminded her of my requirements.
“Okay, I understand,” she said as I finished my explanation.
I handed her my little bag across the table. “There are instructions inside,” I said as she took the bag from me.
She opened the bag and read my instructions:
Take the bag and go into the restroom. Take your blouse and bra off and put on the sheer white, nylon, sleeveless top. It’s actually a body suit, so it will snap between your legs. I have included a small hairbrush and some hot pink hair ribbons. Put your hair in pig tails and tie a bow on each one with the hot pink ribbons. Put your blouse and bra in the bag. When you come back to the table, I expect you to be carrying the small pink teddy bear I included in the bag.
Sara looked up at me with her mouth agape. I could see the hesitation in her eyes. I knew all sorts of things were running through that pretty little head of hers. She nodded and headed off to the ladies’ room.
She was gone for at least 15 minutes, maybe more. When she finally returned to the table, she was carrying the bag and had not changed her blouse. She sat down across from me with tears in her eyes. “I can’t do this. Not here,” she whispered.
I didn’t say a word. I reached into my wallet and put money on the table for the bill. I grabbed a fresh drink napkin and scribbled down my address. Handing her the napkin I said, “If you change your mind, here’s my address.” I stood up and walked out of the restaurant.
It was a long ride home. I rode in silence, consumed with my thoughts. I was angry for sure, but mostly disappointed. I was disappointed in myself. Maybe I pushed her too far, too soon? Maybe I misjudged her, who knew? I felt like I had blown a golden opportunity. I got home, poured myself a nightcap and then went to bed.
In the middle of the night I heard my doorbell ring. I rolled over and looked at the clock, 2:15 AM. ‘Fucking neighborhood kids’ I grumbled. I sleep nude just for comfort, I threw back the covers and grabbed some boxer shorts next to the bed. I whipped the front door open. Sara Jane was standing there. Her makeup was trashed, she had obviously been crying. She seemed a little tipsy, but not shit faced drunk. She was wearing the sheer white nylon top, her tits clearly visible through the thin material and looking very hot. Her hair was in pigtails with the hot pink ribbons tied in a bow on each one. She clutched the teddy bear under her arm.
“I’m sorry Daddy,” she said softly, staring at the ground.
“Sorry for what?” I asked nonchalantly.
“For disobeying and being a bad little girl,” she said.
“Look at me Sara,” I said with sternness in my voice. She looked up. “What happens when bad little girls disobey?” I asked.
“They get punished?” she questioned.
“That’s right. Do you want to be punished Sara?”
“Yes Daddy, I’ve been bad and need to be punished,” she said softly as she met my gaze.
“Hand me your teddy bear,” I said.
“I named her Isabella,” she said smiling.
I took Isabella and set her on the table next to the door. “Take your skirt off and hand it to me,” I told her. She didn’t hesitate for a moment. She reached behind her back, unzipped her skirt, and let it fall to her feet. After she handed it to me, I said, “Kneel down Sara.” Again, she followed my direction immediately. “Clasp your hands behind your head,” I continued. In this position, her beautiful tits were thrust forward, straining against the sheer nylon.
She looked so beautiful and vulnerable in this position. Kneeling on my front porch, hands behind her head, sheer white top, sheer to the waist pantyhose, no panties, black patent leather high heels, and no skirt. With her hair in cute little pigtails and hot pink ribbons, she looked up at me expectantly.
I reached into my boxer shorts and pulled my cock out. “Open your mouth little girl,” I said with lust in my voice. She probably thought she was going to get to suck my cock. Instead, I started pissing on her. “Keep that mouth open!” I ordered. I soaked her face, hair, and tits in my hot piss. Her wet top showed off her tits perfectly! I then aimed for her open mouth. “Swallow my piss Sara,” I ordered. She obeyed.
When I finished pissing on her, I slammed the door in her face. I came back a moment later and tossed her a clean towel. “Dry off and then go shower,” I said. I showed her where the guest bathroom was. “After you shower, you can sleep in the guest room,” I said. I went back to bed and immediately jerked off thinking about what had just transpired. God she was hot! I quickly fell asleep thinking about what a wild night this had been!I woke up to use the restroom, it was 5:30 AM and still dark outside. As I swung my legs out of bed I almost stepped on Sara Jane! She was asleep on the floor next to my bed, curled up like a little puppy. She had her hair up in a towel on top of her head from the shower, not a stitch of clothing on her wonderful young body.
“Jesus Sara, what are you doing? I thought I told you to sleep in the guest bedroom?” I said gently.
“I wanted to be near you Daddy,” she whispered.
“That’s nice, but you’re going to catch pneumonia. I should have put the heat on last night,” I said with paternal concern. I helped her off the floor and walked her to the opposite side of my bed. Sitting her on the edge of the bed, I removed the bath towel from her head. Even with rumpled hair and no makeup in this dim light she was gorgeous. I grabbed one of my long sleeve t-shirts and helped her put it on. I laid her back on the bed, resting her head on the pillow. I grabbed a pair of my sweat socks from my drawer and put them on her pretty little feet. I pulled the covers up to her chin to keep her warm and started to walk away.
“Thank you for tucking me in Daddy,” she said sweetly.
My heart melted. I went back and kissed her on the forehead. “Get some sleep Baby Girl. I’ll check on you in a while,” I said quietly.
I went out to the kitchen to start the coffee, my hardon poking out of my boxer shorts.
The house was quiet as I sipped my coffee and played on my phone. Around 10:30 AM I heard the pitter patter of pretty feet on the wooden floor. I guess she had gotten warm and taken the socks off. I heard her pee in the toilet and then flush. More pitter patters. Then I heard the distinct sound of high heels heading toward the kitchen, she had found her heels by the front door. I looked up and saw Sara Jane standing in the doorway. She was naked from the waist down, except for her high heel pumps. My long sleeve T-shirt barely covered her ass and cunt. She cradled Isabella in her arm. Damn she was hot!
“Morning Daddy,” she said sweetly.
“Good morning Baby Girl, did you sleep well?” I asked.
“Oh my God! This is the most uninterrupted sleep I have gotten in months! I feel great!” she said cheerily.
She walked over to where I was sitting on a kitchen chair and gently pushed my legs apart. She put Isabella on the kitchen table and stepped between my legs. Wrapping her arms around my neck she gave me a long sexy kiss.
“Thank you for taking me back Daddy,” she said, “I need a relationship like this more than I ever thought. I actually enjoyed it when you pissed all over me last night, so erotic and so humiliating!” she continued. “But most of all, I want to be trained and owned, just like your ad said.”
I smiled and nodded. “Just remember, there are no more second chances,” I warned. She nodded her acknowledgement.
Lifting her T-shirt, a bit, I looked at her cunt. “Rule #5: the only hair on your body will be on your head. I suggest you go fix this,” I said sternly as I gestured to her pubic hair.
“Ok Daddy, I’ll be back shortly,” she said obediently. Before she walked away, she patted my cock through my boxer shorts and said coyly, “When do I get to play with this?”
“That privilege must be earned Sara. I’m confident you’ll get there, however. Now go shave that hairy thing!” I chided her. She smiled and strutted off toward the bathroom.
When I decided to pursue my dominant side, I also decided to convert my former game room into a bondage ‘playroom’. The room is a finished space over the garage and only accessible by an inside set of stairs. I’m pretty handy with a hammer and saw, so I am building most of the equipment myself. For the more elaborate pieces, I plan to order those online. While Sara Jane was shaving her pussy, I went upstairs to get a little work done on the room. After a while, I heard the click-click of her high heels on the wooden floor again.
I went downstairs and walked into the living room. Sara was standing in the middle of the room, stark naked except for her high heels. She had combed her hair back into a high and tight ponytail and she had applied bright red lipstick. She had a pair of sunglasses on, her hands were on her hips and her legs spread about three feet apart. Her now shaved cunt was on full display.
“Do I pass inspection Daddy?” she purred.
I walked up to her and said in a low voice, “Whatever you do, keep your hands on your hips and your legs spread apart.” I went into the kitchen a grabbed a very large cucumber from the counter.
I walked up to her and said, “Don’t move an inch Sara.” I rubbed her naked cunt with my fingers, probing her growing wetness. She let out a soft moan as I slowly inserted my middle finger into her cunt.
“Oh Daddy, it’s been so long!” she moaned.
I added a second finger, and then a third. Her hips were beginning to buck back and forth.
“Don’t move Sara, stay still,” I hissed in her ear. When I felt she was wet enough, I began to insert the large cucumber into her now dripping cunt. The cucumber slipped in easily, inch by inch. I kept working the cucumber in deeper and deeper. I then began an in and out motion, slowly at first, but soon picked up speed. Her hips began involuntarily bucking back and forth again. Her hands were still on her hips, but now her head was thrown back in her growing ecstasy. With my free hand I reached up and began twisting and pinching her nipples. That did it, the nipple play pushed her over the edge. Her knees began to buckle.
“Don’t you fucking move Bitch,” I hissed. I couldn’t see her eyes because of the dark sunglasses but felt certain they were rolled back in her head.
“Your pussy seems stretched out; have you been fucking someone recently Sara?”
“No Daddy! I promise! I haven’t been fucked in over a year!” she said in desperation.
“Do you use a dildo at home?” I asked as I continued to assail her cunt.
She hesitated, then said very tentatively and quietly, “Yes Daddy I do.”
“How big is your dildo Sara?” I whispered in her ear.
“It’s big Daddy, the biggest I could find. It’s a replica of a horse’s cock,” she said.
“A horse’s cock!? You’re a little slut, aren’t you?” I asked. What color is your dildo Sara?” I continued in a teasing voice, still attacking her cunt.
More hesitation. “It’s black Daddy, big and black” she moaned.
“So, you like big black cocks, is that right Sara?” I asked. She didn’t answer. “Answer me Sara, tell me you love big black cocks!”
She was screaming now, “Yesss! I love big black cocks!” She let out a guttural moan as she orgasmed. Her knees buckled and I let her slowly sink to the floor. I thought seriously about slipping her heels off and sucking her pretty toes but decided that could wait for another time. I stood over her, my raging hard on poking out of my boxer shorts. I stroked my cock and shot a huge load of come on her as she lay on the floor, still enjoying her orgasm. She barely noticed that I had shot cum all over her tits and face.
I went to the kitchen and got a teaspoon. I knelt down next to her and scooped up my cum with the spoon.
“Open your mouth Sara,” I told her. She did as she was told. I fed her my cum from the spoon. “Good girl Sara. It makes Daddy happy when you eat his cum,” I said.
She put the sunglasses on top of her head and looked at me. “I like making Daddy happy,” she said with one her megawatt smiles.
“By the way, you have passed my test and are now in my 30-day probationary training program,” I told her.
She seemed very happy to hear that.
“What’s your schedule today Sara?” I asked as she got up off the floor.
“I thought we could go shoe shopping!” she said excitedly. “If I’m going to be wearing heels all the time, I need at least 3-4 more pairs.”
It took me, like, a nano-second to agree. High heel shopping with this gorgeous young thing? Who could turn that down!?
“Sounds wonderful!” I said. “What are you going to wear when we go shopping?”
“Hmmm. Well, if Daddy approves, I have a fresh set of work out clothes in my car, I could wear that?” she said with hope in her voice.
“Sure. Go get your stuff, no need to get dressed,” I said mischievously.
Sara Jane looked at me, she knew I was serious. She moved toward the front door, dressed only in her high heels and sunglasses. Gathering her courage, she opened the front door and stepped onto the front porch. She still had my dried cum remnants on her tits, hair, and face.
Sara’s car was parked in the driveway, close to the sidewalk that leads to the front door. It was broad daylight out and Sara walked quickly down the front sidewalk, completely nude. Being in heels, she couldn’t run. Her blonde ponytail swished back and forth. She quickly scooted to the car, grabbed her gym bag from the back seat and hurried back to the front porch. She stepped inside and pulled her things from her bag. She was beaming, obviously proud of herself for completing her task.
“Good girl,” I told her. “Put on the tank top, no bra. Get the pantyhose from last night in the guest bathroom and put them on also. Then your work out shorts. I’ll give you a break and let you skip the heels, so your tennies are fine.”
“Ummm…the pantyhose are probably still soaked with piss,” she said meekly.
“Is that a problem?” I asked.
“No Daddy, I’ll put them on,” she said.
She came out of the guest bathroom with her hair still in a ponytail and had freshened up her makeup. The white tank top did little, if anything, to conceal her beautiful tits. The cool autumn air made her nipples stand at attention and press against her shirt. Her hot pink work-out shorts looked really hot with the dark, sheer to the waist, pantyhose. For some odd reason, I was also turned on by her wearing tennis shoes with the nylons, it looked different and oh so sexy!
We headed to the mall in my car. “Rule #6,” I said, “When you and I are in public together, you will not speak unless I ask you a direct question. Even if a waiter or salesperson talks to you directly, you will not answer them, I will answer for you. Understood?”
Sara Jane nodded her consent.
“Daddy, I need to pee really bad,” she said as we drove.
I reached in the backseat and grabbed a small towel I always keep in the car. I handed her the towel and told her to sit on it. She placed the towel under her butt on the car seat.
“Pull your shorts down to your knees,” I directed her. She obeyed. “Now piss yourself.”
Sara hesitated slightly, then I saw her right hand move to her cunt. She rubbed gently, coaxing her piss out. She sighed contentedly as her piss soaked her pantyhose and the towel she sat on. The car was soon filled with the acrid smell of Sara Jane’s piss.
“Does my Baby Girl feel better now?” I asked.
“Yes Daddy, thank you.”
She sat in her puddle of piss, her shorts still down around her knees the rest of the way to the mall.
We got to the mall and headed for the large, upscale department store. I knew this store had an extensive ladies shoe department with lots of sexy heels. Also, right across the aisle from the shoes is the hosiery department. I had a feeling we’d be visiting both today!
As we walked through the shoe department, I told Sara Jane that I would decide what shoes we buy for her. I selected a 4″ yellow, patent leather, pointy toe pump for starters. A sales lady approached us.
Looking at Sara, she said “Hi! I’m Jillian. Can I help you find something today?”
“She would like to try these on,” I responded, handing her the yellow pump.
“Sure thing, what size?” she asked Sara.
Sara looked at me. “She’s a size 6,” I told Jillian. I had looked inside Sara’s high heels earlier at home to get her size.
We took a seat while Jillian went to the stock room to get the shoes. Jillian looked to be in her mid-40s. She was very trim and very Goth. She had that pale white skin, accentuated by her jet black, long straight hair. Her makeup was dark and heavy.
When Jillian came back, she had picked up on the fact that I was doing all the talking.
As Jillian helped Sara step into the yellow pumps, she said, “Ummm…her stockings are wet.”
“She had a little accident on the way here,” I said, “Didn’t you Sara?”
Sara Jane blushed bright red and looked at me, seeking permission to speak. I nodded ever so slightly.
“Yes Daddy, I did,” she said quietly.
She looked adorable standing there in those 4″ yellow pumps, wet dark pantyhose, and hot pink gym shorts, staring meekly at the ground.
She walked around a bit, getting a feel for the high heels. When she sat back down, I told Jillian we’d take these and also the same high heel in lime green and red, both patent leather.
“We saw some snakeskin heels as well, are those the same style?” I asked.
“Same brand, but the snakeskin ones have a 5″ heel,” Jillian responded.
“Perfect, we’ll take a pair of those as well,” I told her.
I handed Sara Jane my credit card and said, “Go across the aisle to the hosiery department and get some nylons. Get sheer to the waist pantyhose and thigh high stockings, every color they have except white. I like Wolford and Plantino brands.”
“Yes Daddy, be back in a bit,” Sara Jane said.
When Sara left, Jillian looked up at me and said sarcastically, “Cute little pet you have there.”
I smiled at her. “Yes, she is, just not house broken yet,” I replied chuckling.
Jillian was sitting on the footstool from when she had helped Sara into her pumps. I looked down at her and noticed for the first time her very healthy bust line and cleavage. I had always been attracted to Goth girls, and Jillian was one of the prettiest I had ever seen.
“If you need help training the little bitch, let me know,” she said. Then she reached into her back pocket and handed me her business card, it read:
Mistress Jillian
Experienced trainer of naughty little girls
Her card had all her contact info as well. I smiled and pocketed her card. What a stroke of luck!
“I’ll be in touch,” I told her. We walked to the register and I paid for Sara’s high heels.
“You know, it’s my break time right now. Think the three of us can go back to the stock room for a few minutes?” Jillian asked with a sly grin.
“That sounds interesting. I’ll bring Sara in there when she gets back.”
Jillian winked at me and disappeared into the backroom. Sara walked up a minute later with a large bag of stockings and pantyhose.
“Hit the jackpot!” she said proudly, holding up the bag of Wolfords and Plantinos.
“Good girl!” I said, “I’ll take the bag, Jillian wants to see you in the backroom.”
Sara looked at me quizzically, “Okay Daddy.”
We both walked into the storeroom behind the register. Jillian was standing there and had just lit a cigarette. She is pretty tall; I’d guess about 5′ 10″. She was also wearing heels. Sara, on the other hand, is about 5′ 2″ at the most and had put her tennies back on after trying on the heels.
Jillian directed Sara to stand in the middle of the room. “Lift your arms bitch,” she said to Sara.
Sara looked at me, fright and concern in her eyes. I nodded for her to do as she was told. Jillian stood directly in front of Sara and stripped Sara’s tank top completely off in one smooth motion.
“Put your hands on top of your head bitch.” Sara complied immediately.
Sara looked so vulnerable and sexy in this position, her young, pert breasts jutting forward. Jillian took a long drag on her cigarette and blew the smoke directly in Sara’s face. She took a few steps back, picked up her phone, and took a few photos of Sara Jane standing there, naked from the waist up.
“What size tits you got sweetie?” Jillian asked Sara.
“36C,” Sara said quietly.
Jillian walked back over to Sara and slapped her across the face. “You’ll refer to me as Ma’am or Mistress Jillian. Got it bitch?” she said to Sara.
“Yes Ma’am,” Sara said as tears formed in her eyes. The slap had obviously stung and startled her.
Jillian walked behind Sara, grabbed her by the ponytail, and yanked her head back. She had set her cigarette down, so with her free hand she reached around Sara and started roughly squeezing and pinching her tits.
Jillian put her mouth to Sara’s ear and said seductively, “If your Daddy approves, I’m gonna have a lot of fun with you Sara. Tits are my specialty, and yours are sweet.”
Jillian released her grip on Sara’s ponytail and moved to face Sara. She stood with her arms folded, inspecting the innocent and vulnerable young, single Mom in front her.
“Your tits are pretty, but too pale. They need some color,” Jillian said.
She walked back to the desk and removed a wooden ruler. By this time, I was getting hard. I had set the bag of nylons down and was rubbing my growing hard on.
Jillian moved in front of Sara, and using the wooden ruler, slapped one tit, then the other. Sara winced, but kept her hands on top of head. I moved behind Sara and pulled her shorts down to her ankles. I pulled my cock out of my pants, grabbed Sara by the hips, and began rubbing my cock all over her nylon covered ass. Slowly and methodically, Jillian continued the assault on Sara’s pretty tits while I dry humped her butt. Tears were starting to roll down Sara’s cheeks. I stroked my cock and shot my load on her pantyhose covered ass. Sara was too focused on the tit whipping to realize I had just deposited my load on her ass. I pulled her shorts back up and used them to wipe the excess cum from my dick. I then pulled them up the rest of the way on Sara’s waist.
Jillian kept slapping Sara’s tits, gradually they both turned a bright pinkish-red. “There, that’s a much better color. Don’t you agree Sara?” Jillian asked her sarcastically.
Sara glanced down at her stinging tits and replied, “Yes Ma’am.”
Jillian threw Sara’s tank top to her and told her to get dressed. I grabbed our purchases and we prepared to leave. Turning to Jillian I said, “See you soon.”
As we walked through the department store, heading for the car, I walked behind Sara Jane. I could see a wet spot on the ass of her shorts from my cum deposit. ‘Life is good’ I smiled to myself!