Humiliated - at Hooters

My wife died about 15 years ago, leaving me a 41-year-old man with a sizeable insurance settlement and a 12-year-old daughter. The money was enough for me to be comfortable, and for work to be an option, not a necessity.

Jenny was a childhood friend of my daughters. As they grew up, Jenny grew to be an absolute knockout, it was not a huge surprise when she went to work as a Hooters Girl, I'd hear her discussing the money and fun they'd have with my daughter, trying to get her to join as well. After my daughter graduated college and moved to another town, I lost touch with Jenny, as did my daughter.

About 5 years later, I was in an adult store, buying a chastity cage and a butt plug for some online play, when I bumped into Jenny again. I was surprised, to say the least, but Jenny squealed and gave me a huge hug. "Mr. Little! It's so good to see you again!"

Jenny then got a little embarrassed about where we both were, you could see the flush climbing up her neck when she noticed what I was carrying "Oh! Mr. Little!" she exclaimed with a knowing wink "Whatever are you buying, let me see!"

She took the cage first "Hmm.." she read "Super small pink realistic vagina locking chastity cage for Sissy play." she paused for a moment "Mr. Little! I guess that's not just a name, huh?"

She took the plug "Hmm, this one seems fairly large, definitely not for beginners...Is this for you too?"

Talk about embarrassing! "Yes Jenny, those are both for me" I mumbled as my face became as red as a tomato.

"I think you'd better call me Miss Jenny from now on, Mr. Little, or I guess I'll start calling you little now. Oh, wait, you're not gay are you?"

"No, Miss Jenny" I sputtered. "I'm definitely not gay. I'm totally into women"

Jenny looked at me with her arms crossed "These types of toys aren't usual for Real Men, little. Do you fantasize about doing things with men too? I'll know if you're lying--don't worry, this will be our little secret!"

I looked down at my feet and mumbled "I'm only into women, Miss Jenny, but I do, sometimes, have fantasies where women make me do things with men for their amusement, Ma'am."

Jenny Laughed, "Ma'am, I like that, Little. This is very interesting. Here's a secret for you--I enjoy being dominant sometimes. Do you still have the same home phone?"

"Yes, Miss Jenny, it's still the same"

"Good. I'm going to call you tonight, little. 11:30. Have your cage on and your plug in when I call."

She then put my plug and cage on the counter along with the lingerie and vibrator she was buying "Pay for this, little"

I paid, and quickly left the shop. My god, what the hell was this? I was going to have to talk things through with her this evening, and explain that this was just a one-time game for me--I needed out, and fast! There's no way I could discuss my perverted fetishes with my daughter's childhood friend! This girl was even younger than MY daughter, I was more than twice her age!

As the evening rolled around, my resolve hardened. As exciting as this was, it had to end now. I was mentally prepared to break this off as soon as the phone call came in.

At 11:30, the phone was silent. I felt a mixture of relief and sadness as it remained silent until, at 12:30, the phone rang, and I quickly snatched it up.

"Jenny, listen, what happened at the store was certainly exciting" I began when she interrupted

"Now you listen, little! First--it's Miss Jenny to you. There may be other names later, but Miss Jenny for now. Second, my friend runs that adult store, and has given me your purchase history, as well as the video from today--you try to back out of this, and it's not going to go well for you. I'm not in touch with your daughter, but I still have her email and phone. Besides, I think this could be fun for both of us--I saw that little bulge in your pants at the store"

I was shocked, resigned, and excited all at the same time "Yes, Miss Jenny"

"That's better" she cooed, "Now, are you wearing your cage and your plug, little?"

"No, Miss Jenny"

"OK, I'll make a note of that for our next meeting. Go do it NOW, and I'll call you back in 10 minutes, wait by the phone on your knees, little" Click

I quickly did as instructed, although I had to ice my dick down to get it in the small cage. It took me about 15 minutes to do it all and get back to the phone, which sat silent for another 15 minutes before ringing again.

I snatched up the receiver and immediately heard "Everything done now, Little? and you're on your knees?"

"Yes, Miss Jenny"

"Good, let's begin. Talk to me about your fantasies, fetishes, etc. EVERYTHING, little. Leave nothing out."

We talked for 2 hours that night, and about another 8 hours over the next 2 weeks. I admitted all my dirtiest thoughts and fantasies to her--Femdom, Public Humiliation, Forced Bi, crossdressing, etc. She even got me to admit to masturbating over thoughts of her as a teenager. I always called her Miss Jenny, and she always called me little, and she always kept me caged and plugged for these calls, but other than that it was really like having a super dirty discussion with a close friend who listened well.

About a month later, Jenny called me on a Wednesday and said "Little, go to Victoria's Secret at the mall tomorrow at 11:00 AM sharp--right when they open. Plugged and caged. Ask for Alice, she's a friend of mine. You will call her Miss Alice. Do and buy whatever she tells you. We'll talk on Sunday" Click

Wow, OK. This should be fun. I was excited for the next day and had a hard time sleeping.

The next morning, I got up, showered, shaved, and put on/in my toys, got dressed in jeans and a polo. I got to the mall at about 10:30 and wandered around, making certain to be at Victoria's Secret at 10:59--I wanted to make Jenny proud.

As the metal screen lifted, I was engulfed in a cloud of pinkness and perfume. I walked in, and a salesgirl, who couldn't have been more than 18, approached me and asked if I needed help "Yes, please. I'm looking for Alice"

"I'm Alice, how may I help you?"

"Oh, umm, hi Miss Alice, Miss Jenny told me to come see you this morning"

"Really? Interesting. I don't know any Jenny. And why are you calling me "Miss Alice?"

I was beet red! What was going on? How was I going to gracefully exit out of this?

"Just fucking with you, little. That is your name, isn't it?" she laughed

"Yes, Miss Alice. Thank you, Miss Alice!" To say I was relieved would be an understatement!

Alice took me around, grabbed a few matching bra- and panty sets, and then took me to the changing room and entered with me. "OK, take off your shirt, little--we need to measure you for a bra"

Oh wow. I took off my shirt and hung it on the peg provided, and Alice quickly and deftly wrapped my chest with her measuring tape a few times "OK our biggest size is a 46, and it looks like you need a 48, little. We have extenders that can take care of that little problem, but I think a 44 will be better. With a 44 we can get a C cup, but with a 46 you'd have to go with a Double D--I don't think you're ready for that yet.

The then held up a few bras, pink and either lacy or frilly, and settled in on one super lacy one, and one push-up bra with a lot of frills. She turned to me and ordered "Drop trou, little"

I did as instructed, and she just stared at me and tapped her foot...."Underwear too"

I slid my boxers down, and stepped out of them Alice laughed "Cute cage! Turn around and bend over, Jenny told me there's a surprise there too?"

I did as I was told, and got an actual snort-laugh out of her. "Wow, I can't believe she got you to do this! Pathetic" She then measured my waist, making sure to brush my cage a few times while doing so, and said "OK, an XL. Here's the choices for matching panties--boyshorts or thongs? Nah, let's go with both. Here, put these on." She handed me one of the bras and the matching boyshorts.

The boyshorts were easy to put on, the bra took a little more effort. Alice laughed "You'll learn"

Once I had them on she took the 3 other panties and other bra and said "OK, you can get dressed now, meet me at the register. Touch NOTHING but your clothes" She walked out, leaving the curtain half open.

I quickly dressed, afraid of what might happen if anybody saw me, and almost ran to the cash register.

"OK, 2 bras and 4 pairs of panties for you, and the bustier suspender belt and other lingerie you are buying for me, that'll be 287.50, little"

I quickly paid, and thanked Alice for her assistance, and left to go home.

This had been so thrilling, and was such a turn on. But I knew what Jenny wanted, and I waited patiently for Sunday.

Sunday night, I eagerly waited by the phone, and (For a change) it rang right on time

"Hey little! Alice told me all about your shopping trip! That sounded hilarious, I wish I could have been there. Ah well, next time!"

I was going to be doing this again?

"Little, I have a plan for you. You are going to remain caged ALL week. 24/7. You will come to my Hooters next Sunday at 10:30. We're practically dead at that time. You'll wear your plug as well as your new push-up bra and thong panties under normal clothes, but you may remove your cage in the parking lot before entering. Bring $500. See you then, little!"

To say my cock was straining at it's cage would be an understatement! The week dragged on forever, and the weekend was even worse! I showed up at Hooters at 10:15, sat in the parking lot, removed my cage at 10:25, and headed in the door.

The place was EMPTY. 1 waitress, a bartender, and Jenny, who was the trainer/manager for the restaurant. As I walked in, Jenny whispered to the waitresses who giggled, one hopped up and said "Welcome to Hooters, I'm Heather, and I'll be your server tonight. follow me, please" I sat down, and she said "Your order will be out in a minute"

What order? I looked over at Jenny, and she was just sitting there with the bartender with a HUGE grin on her face.

After a few minutes, Heather brought me a kids' menu chicken tenders and a glass of milk "Enjoy little!" she said with a laugh and walked over to gossip with Jenny and the bartender.

At 11:00 Jenny came over to me "Tonight is going to be fun. I've been planning this for weeks, but it took me a while to get the right team working together. Roll with it, little. Your safeword, if you need it, is pineapple. Don't use it. follow me" As she said this, the bartender locked the front door.

All four of us walked back to the staff changing room, and we were joined by the 2 kitchen workers as well.

Jenny said "Everybody, this is little. This is Heather, Suzie, with Tom and Jeff from the kitchen. Men--strip to your skivvies! We're about to have a jerk-off contest! See who can last the longest. Little is mine, Heather you've got next pick.

Well, as Heather picked Tom, the guys took off their clothes, there was a lot of laughing when everybody saw my bra and panties and Jeff commented "Jeez, Jenny, you weren't kidding were you?"

Jenny laughed and said "OK, here's the rules--do ANYTHING you want with your hands, BUT ONLY YOUR HANDS, to make your man" And then pointedly looking at me "Or little boy cum. Winning girl is the one who makes them cum fastest--they get $500, Winning man (Or boy) is the one who comes last, they get a blow job!"

"3-2-1-GO!" Jenny yanked down my panties, and began jerking my dick with her thumb and one finger "Aww, look at how little it is! What a cute widdle pee-pee my widdle boy has"

With more than a week of being caged, it didn't take me long to lose. I came in less than 2 minutes, to Jenny's joy. As I started to cum, she grabbed a plastic cup, and aimed all my cum into the cup. A practice that the other girls followed as an extremely well hung 8-9 inch Jeff came after another 5 minutes, with Tom, who was about 5 inches, following quickly after.

The girls all laughed, and they teased Jenny about being a cheater for bringing a two-pump-chump like me along.

Between the humiliating talk, and the sexy girls I was rock hard again by the time the others had finished.

Suzie said "Hey Heather--go grab the salad. While You're getting that, I want to measure little, I don't want people to say I'm exaggerating when I say how small he is!"

Heather ran out, and Suzie grabbed a tape measure "Wow--3.4 inches! I didn't know they came that small! No wonder you're called little! They all laughed while I stood there embarrassed, as Jenny pulled my panties back up.

Heather came back and set a house salad down on the floor. "Here Little, sorry for the kids' meal earlier, but we wanted to make sure you had room for your salad. Do you want dressing?"

I answered "Of course, please! What kind do you have?"

As I said that Jenny, Suzie and Heather grabbed their plastic cups of cum from earlier and poured them over the salad.

Jenny looked at me with a twinkle in her eye "Enjoy your salad, little"

I knew what she expected of me, and I really didn't want to disappoint her. I knelt down on the floor and began eating the salad like a dog. Everybody in the room laughed as I did so with comments flying around like "Wow" "No way" I didn't believe he'd actually do THAT" "What a loser" and so on.

When I finished the salad, Jenny said "Now lick the plate clean, little" and I did.

Tom piped up "Hey Jenny, this has been fun and all, but you DID promise a blow job to the winner--time to pay up! I've dreamt of those lips sucking my rod!"

Jenny laughed "Tom, you should have listened to the rules better! I promised the winner a blow job, not that I would give them the blow job!"

Tom shrugged "OK, Heather, Suzie, who's it going to be? I want to collect on my winnings!"

Heather and Suzie looked at each other and giggled, and then turned to Jenny expectantly

"OK, little. Time to become the cocksucking little sissy you've dreamed of being"

I looked at Tom, and knew enough from watching sissy porn and reading stories what to do "Mr. Tom, may I please give you the blowjob you have won, please Sir?"

Tom was surprised, but Suzie jumped in "Tom, you let the little fag give you the blowjob, we'll all take off our tops and let you and Jeff play with our tits while he does it"

What man could resist an offer like that? Certainly not Tom! "OK, little, I already know you'll swallow, but I'd better not feel any teeth!"

I knelt in front of Tom and began licking and sucking his balls, slowly working my way up his shaft. As he'd just cum before, it took me about 15 minutes to get him over the edge, and he filled my mouth with his cream, which I happily swallowed.

After he finished, I kept him in my mouth as he went soft "I need to pee" he said and Jenny laughed "Then pee, little will drink it down too! The little bitch will do anything I tell her to do"

Tom let go and a stream shot into my throat. I gagged as I tried to keep pace with his flow, swallowing almost all of it down, barring a few drops that escaped.

We all got dressed, and walked out of the restaurant, Jenny took my hand and said "Little, I'm going back to your place tonight. We have a lot to talk through and a lot of planning for the future."

That night was the first time I got to taste Miss Jenny, but that's a story for another time.