Feeling Shameful at Hooters
Around 15 years back, my wife passed away, leaving me a 41-year-old man with a significant insurance payout and a 12-year-old daughter. The money was sufficient for my comfort, and I no longer had to work due to financial security.
Jenny, a friend from my daughter's childhood, grew more attractive as they grew up. Her job at Hooters sparked conversations between her and my daughter about everything related to fun and wealth, with her convincing my daughter to consider joining the same. Eventually, my daughter graduated from college and left town, and we lost touch with Jenny.
Five years later, I was browsing through an adult store, purchasing a chastity cage and a butt plug for some online play when I encountered Jenny unexpectedly. My surprise was palpable as she ran towards me with a warm embrace and the words, "Mr. Little! It's incredible to see you again!"
Jenny noticed the items I was holding. "Oh my, Mr. Little! What's this? Let me see!" She touched the cage with a knowing wink.
"Super small pink realistic vagina locking chastity cage for Sissy play." She read out. The silence in the store felt like an eternity before she asked, "Mr. Little! Your name is just not just a name, huh?"
Next, she picked up the plug. "This is quite large and definitely not for beginners...Is this for you too?"
"Yes," I stammered, embarrassed.
She remarked with a slight smirk, "I think you'd better call me Miss Jenny from now on, Mr. Little, or I guess I'll be calling you 'little' now. Oh, wait, you're not gay, are you?"
"No, Miss Jenny," I said quickly. "I'm definitely not gay. I'm purely into women!"
Jenny crossed her arms and raised an eyebrow as she spoke, "These types of toys are more associated with what people call Real Men, little. Do you have fantasies about doing things with men too?"
I lowered my gaze, "I am only into women, Miss Jenny, although sometimes, I have fantasies about women making me do things with men for their amusement," I said hesitantly.
Jenny smirked again and said, "I like that, little. Here's a little secret for you--I like being in charge sometimes. How about your home phone number? The same one?"
"Yes, Miss Jenny," I replied.
"Good. I'm calling you tonight at 11:30. Make sure you're wearing the cage and the plug. It'll add to our fun!" She placed my plug and cage on the counter beside her lingerie and vibrator.
I paid for my items and quickly left the shop, confused and a little frightened. I knew this had to end. I needed a way to break it off and fast. As exciting as this was, I couldn't share my perverted fetishes with my daughter's childhood friend, who was even younger than my own daughter. She was more than twice her age!
The night approached, and my resolve grew firmer. I was ready to terminate this fun, exciting game and communicate openly.
At 11:30, the phone remained silent. I experienced a mix of relief and disappointment as it stayed mute until, at 12:30, the phone rang.
"Jenny, listen, what happened at the store was thrilling!" I started cautiously, but Jenny cut in:
"You listen closely, sweetie. First, it's Miss Jenny to you. There may be different names along the way, but Miss Jenny for now. Second, my friend manages the adult store; she's aware of your purchase history and the video from today. If you try to walk away from this, it won't end well. I don't have your daughter's details, but I do have her email and phone number. Furthermore, I believe we can both benefit from this dynamic--I spotted your erection at the store."
Shocked, I told her, "No, Miss Jenny."
"OK, I'll make a note of that for our next session. Return and put on your cage and the plug. And please wait by the phone on your knees."
It took me 15 minutes to slip into the cage and plug, but when I got back to the phone, I had to cool my erection to fit the tiny cage. I waited by the phone for another 10 minutes before it rang.
I picked up the receiver and immediately heard, "Your preparations complete, Little? And you're on your knees?"
Low down, let's dive in. Spill the beans about your desires, kinks, you name it. Scrutinize every tidbit. No secrets spared.
We chatted for two hours that night, and an additional eight hours over the following two weeks. I confessed all my filthiest thoughts and fantasies to her—Femdom, Humiliation, Bi, cross-dressing, you name it. Even admitted to wanking over fantasies of her in her heydays. She'd address me as Miss Jenny, and I in return called her little, keeping me contained for these chats, but otherwise it felt like having a raunchy conversation with a dear friend who listener extraordinaire.
A month later, Jenny phoned me one Wednesday afternoon and said, "Hey little, drift to the nearby Victoria's Secret at the mall tomorrow at high noon—right when they open. In skirts and chained up. Speak to her as Alice, she's a friend of mine. Follow her instructions precisely, and we'll discuss this Sunday." Click.
Whammy! Sure thing. Excited for the rest of the day and had trouble snoozing.
The following day, I got up, washed up, fluffed and set my plugs. Dressed in blue jeans and a polo. Arrived at the mall at half-ten, planning to be at VS on time, wanting to make Jenny proud.
Coated in a haze of pinkness and aroma, I walked in, and a girl no more than 18—young as they come—approached me. "Can I help you find something, sir?"
"Yes, please. I'm seeking Alice."
"Alice? Don't think I've met an Alice here. And why the polite speech, sir?"
Red-faced, "Just joshing you, ma'am."
"Indeed? It's Ed. You look familiar."
Awkwardness setting in, realizing how to slither out hassle free!
"Yes, it's really me. Sorry for the confusion, ma'am!" Thank goodness for that relief.
Ed took me around, selected a couple matching sets of bras and underwear, and directed me to the changing room. "Strip your shirt off, buddy. Measuring time."
Wow, holy moly! I obeyed, hanging my tee on a hook, while Ed swiftly measured me for a bra. "As a 46, you'd need a Double D, but a 44 can offer a C cup. Given your current situation, we'll stick with the latter."
She then presented two choices: a lacy bra with plenty of frou-frou or a bouncy push-up bra. "Choose one, buddy. Now bend over and undo your pants."
Obeying yet again, I received another snort-laugh from Ed. "I can't fathom Jenny persuading you to do this. Cute." As she measured my waist, grazing my collar with a giggle, "Large it is. Check out these options for boy shorts. Settle on girl shorts or thongs—I suggest thongs."
When I attired, Ed offered, "Choose your order, pack these, and hit up the tills. Helo a glorious moment."
I paid, thanked Ed for her service, and left, delighted by the experience.
This had been so pulsating, such a thrill. But I know Jenny's motives and awaited Sunday.
By Sunday evening, I sat salivating, awaiting the phone. (For a change) it rang on time. DJ and her playful tone, "Hey little! Alice told me about your shopping trip! What a hoot! Wish I could've been there. Hang tight, buddy! Next time!"
So, it's going to happen again?
"Small buddy, I've got a strategy for you. For the entire week, you'll be kept chained up 24/7. Meet me at Hooters on Sunday at 10:30. It's practically deserted at that time. Wear your plug along with your push-up bra and thong underwear beneath ordinary attire, but without the chastity device in the parking lot prior to entering. Carry $500. See you then, small one!"
Weeks passed by, each day feeling longer than the last. Finally, Sunday came, and I arrived at Hooters at 10:15. After parking, I removed the chastity device at 10:25 and made my way in. The place was vacant. There was just one waitress, a bartender, and Jenny, the trainer/manager of the restaurant. As I walked in, Jenny whispered to the waitresses who snickered, one of them smiled at me and said, "Welcome to Hooters, my dear. I'm Heather, and I'll be your server tonight." She led me to a table while I sat down. "Your order will be ready in a short while," she said with a grin.
Jenny strolled over to the bartender, and they both solemnized with smirks.
At 11:00, Jenny approached me again and said, "Tonight's going to be amusing. I've been planning this for quite some time, but getting the team on board is what took the longest. Just go with it, little one. Your safeword, should you require it, is pineapple. Do not use it." She invited the bartender to stand up and locked the door.
We returned to the staff changing room, where we were joined by the two kitchen workers.
Jenny announced, "Everyone, this is little. This is Heather, Suzie, with Tom and Jeff from the kitchen. Gentlemen, disrobe to your underwear! We're about to partake in a masturbation contest! Whoever lasts the longest. Little's mine, Heather, you've got the second pick."
As Heather picked Tom, the guys turned their clothes inside out, drawing laughter from the females when they saw my bra and thong. Jeff commented: "Wow, Jenny, you weren't lying, were you?"
Jenny chuckled and clarified, "Alright, here's the rules: Only use your hands to pleasure your partner. Now, little guy, I want to see how quickly you make him cum!" She pulled down my underwear and began to rub my penis. "Look at how tiny it is! What a tiny little pee-pee my tiny little boy possesses."
After a brief period of time, it took little effort to reach my climax. I shot my load into a plastic container that Jenny quickly grabbed, and the others followed suit with longer bursts.
The women laughed at the jokes surrounding my small size and Jenny's deception. But I was hard again by the time the others finished.
Suzie exclaimed, "Hey, Heather, get the salad. While you're retrieving that, I want to check how short little truly is!"
As Heather disappeared, Suzie rapidly whipped out a ruler and measured my penis. "Cripes, it's only three inches! I didn't realize they came this tiny!" They all cackled as Jenny helped me dress, and as she did, Heather returned with a house salad. "Here you are, little, my apologies for the child-sized portions before, but I needed to ensure there was space for your salad. Would you like dressing?"
I nodded, "Yes, certainly! What style?"
Jenny, along with Heather and Suzie, had gathered their plastic cups of earlier ejaculate. Jenny said, "Enjoy your meal, little one."
I knew this was a challenge and refused to let Jenny down. I knelt between my legs and ate the salad as if it were a dish reserved for dogs. The room resounded with remarks like, "My word!" "No way!" "I don't believe he'd actually..." "What a loser."
When I finished the salad, Jenny said, "Now, clean the dish, little." And I did.
Tom excitedly exclaimed, "Jenny, my turn! You said the winner gets a blowjob, so let's get started! I've fantasized about those lips on my dick!"
Jenny chuckled, "Tom, you misunderstood. I said the winner gets a blowjob, not that I'd be the one to perform it."
Tom was a bit puzzled, "Alright then, who's taking over? Heather? Suzie?"
Heather and Suzie giggled together, looking at Jenny expectantly.
Jenny smirked, "You two can watch as little becomes the cock-sucking sissy you've envisioned."
I quietly chimed in, "Mr. Tom, may I please give you the blowjob you've earned, sir?"
Tom was a bit taken aback but Suzie quickly interjected, "Come on, Tom, let the faggot give you the blowjob we promised. We'll also remove our tops and let you and Jeff play with our tits while he performs."
Intrigued, Tom consented, "Alright, little. Just be careful not to bite."
I eagerly began licking and sucking Tom's balls, gradually moving up his shaft. Since he'd just cum, it took me around 15 minutes to bring him to climax. He shot his seed into my mouth, which I gladly swallowed.
When Tom's erection had softened, he needed to go to the bathroom. Jenny chuckled, "Well, little, it's time for you to drink his urine as well. The obedient slut you are will do whatever I command."
Tom released his stream, and I struggled to keep up with its pace, swallowing most but a few drops escaped.
We left the restaurant, Jenny took my hand, and announced, "Little, we're heading back to your place tonight. We have a lot to discuss, and I want to make plans for our future endeavors."
That night was my initiation into the world of oral pleasure with Miss Jenny, a story for a different time.