Daddy's CD Waitress

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Good," he murmurred in reply. "Give me a couple of weeks to set it up."

We returned to Earl's chalet later that evening, and I slumbered contentedly while wrapped in his arms and wearing the nightgown he had first given me just a couple of weeks before.

We slept late, and the next morning awoke slowly in the big bed as the sun sent its bright rays into our room. We snuggled for a long time spoon fashion, and then Earl slipped his dick inside me and gave me a slow ride from behind as he languidly stroked me to a gentle cumming.

"Oh, Daddy, I love all this!" I cried out as I rolled over to face him after our lovemaking. "This week-end has taught me so much, already," I said as we kissed and snuggled some more in the bed while under the heavy comforter over us.

We both snoozed for a few more minutes, and then slowly arose and took a leisurely shower together. Afterwards, Earl enjoyed watching me dress up as a young coed while he slipped into his male clothes.

I put on a white garter belt with four suspenders, and a pair of medium taupe seamless nylons that would be correct for daytime wear. Then I added a pair of sheer white nylon brief style panties and a matching white nylon seamless cup bra. It was as sheer as my panties, and I was pleased that my so natural feeling false breast had stayed firmly attached during all the activities of the night before and our shower of the morning.

I couldn't help but appreciate the look of slight arousal my false tits gave with the way the stiff nipples poked against the cups of the bra. The thin material would let the nipples be noticeable through the other layers of clothing I would wear, and I was sure draw attention from onlookers.

"Like the way I look, Daddy?" I asked as I padded around the bedroom in my stocking feet, knowing he was staring at me. I let a full length white slip slide sensuously down over me before I sat at the stool before the vanity and tried my hand at putting on make up.

"You sure do look pretty," Earl commented and gently kissed my shoulder as I

applied my make-up. "And, it appears," he went on, "You've already gotten the knack for putting on make-up, I see."

I smiled happily back at him in the mirror as I put on a base over my skin and almost non-existent beard which I had shaved super close that morning. Then came a light powder over the foundation and soon I had my eyes made up with a look of innocent surprise and my lips were full and shiny under a coating of glistening red lipstick. Only a hint of rouge touched my cheeks and I suddenly was fully convincing in my appearance as a young college age girl.

I slipped into a white polyester blouse with full sleeves and a peter pan collar that seemed to accentuate my long neck and let my false nipples be noticeable through the material layers.

The plaid mini-skirt was next, and I was pleased that my slip stayed just above the hemline that was only a couple of inches below the dark brown reinforcement welts of my stockings. Any sitting would have to be done with care, as my skirt and slip would naturally ride up and expose my hosiery tops...... but then again, did I want that??

A pair of black flats fitted my feet perfectly, and I was astonished at Earl's ability to find just the right sizes for me. A light blue cardigan angora sweater went over my shoulders that complimented one of the plaid colors in my skirt.

Clipping a pair of small gold dot earrings to my ears, I turned to Earl and asked, "Where to, Daddy?"

"How about some breakfast, Darling. Then I thought you might like to do some shopping. I saw you admiring that floor length pink nylon peignoir set last night, and maybe you would like to see about my buying it for you."

"Oh, could I?" I squealed almost in teenage girl delight and hugged him.

"See," he chuckled as he enjoyed my hugs and enthusiasm. "You're already adapting to the feminine role. You reacted just like any other girl would."

"Thank you, Daddy," I smiled and kissed him lightly as we headed to the door. "I wonder if any other 'girl' would be getting all the cock I've been able to enjoy."

"You're quite the minx, you little slut," he laughed as he locked the door and we decided to walk down to the center of the small resort village and have our first meal of the day before doing the shops.

"Well, you can take all the credit for making me the slut I am, Daddy," I laughed as we walked along in the late morning sunshine and I again enjoyed the breezes wisping past my nylons.

"You've given me a permanent case of 'hot panties', Darling. Small wonder you can have your way with me at any time. I wonder what my mother would think of all this."

"I doubt if she has had time, what with her friend Sally probably playing sixty-nine with her or fucking her while wearing her dildoe panties."

"I want to sixty-nine with you, Darling," I whispered as we neared the village and

we headed toward the nearby restaurant.

"This is the restaurant Hedy owns and operates," Earl told me as we stepped in off the street. "You find it has excellent food on its fine menu."

Hedy was already there, and hard at work acting as hostess. It surprised me that no one in the small village realized she was really a male, and yet her appearance would convince anyone of her natural femininity. It just seemed she had probably been in bed with most of the town.

"Good morning Erica, good moring Earl," Hedy said as she met us inside the door. "I've saved just the perfect table for you two."

We let Hedy lead us to a table next to the window overlooking the sidewalk. Earl pulled out a chair for me and I found myself seated next to the glass enjoying the fine view down the picturesque street of shops. Across the way I could spot the shop with the pretty pink peignoir set in the window, and smiled inwardly to myself that soon I would have it in my size.

"Here are our menus," Hedy commented as she leaned over the table handing them to us and giving me a good view down the decollatage of her blouse as it gaped open long enough for me to see. "I've seated you here for a purpose," she spoke quietly so only we could hear.

"A couple of my customers were in earlier, and I told them about Erica. I said if she came in I would seat her next to the window so they could check her out. I know they will pay well for the priviledge of getting into your sweet little panties, Erica," she finished and nodded to me and smiling.

I looked at Earl in surprise as Hedy left us to seat other customers and asked, "Don't you think she is hurrying things a bit, Daddy?"

"Naw, that's Hedy," he replied. "You can always decline if you don't feel comfort- able with the person she wants you to be with, you know."

"I guess, so," I replied and went back to scanning the menu.

A waitress came along shortly and provided coffee as she took our order. "Oh, by the way, the owner said for me to tell you she has called some friends of hers to stop by while you are here."

"What does she mean by that?" I whispered after the young girl had departed.

"It means, she has you on display in the window for potential customers. She's going to tell them you are here now and they can walk by and see if they like what they see. You're on display, Darling," he added, smiling at me over the brim of his coffee cup as he noted my slight discomforture.

I looked around, and felt somewhat more at ease that no one was paying any attention to us except for an elderly man I had spotted watching me hungrily when we first entered the restaurant. A quick check of myself in the relfection of the glass told me everything was alright, and then I noticed my hemline had already ridden up to expose part of the lower reinforcing band of my stockings.

I smoothed my skirt and tugged the hemline down as best I could, dismayed that a hint

of the dark lower band of my stocking could still be seen. It would be obvious to the discerning eye that I was wearing nylon stockings and not pantyhose. I moved my napkin to hide the little bumps made by my garter tabs and then spotted that the slight ridge made by the tops of my nylons couldn't be hidden from the view of the knowing observer.

I looked over at the older man, as Earl scanned a newspaper left on the chair next to him by a previous patron, and found him still looking at me with the same hung- er in his eyes.

"Poor thing," I thought to myself, "He probably hasn't gotten his gun off in a long long time."

I smiled pleasantly when he noticed me observing his watching me, and was greeted with a pleasant smile in return. He looked a bit like Clark Gable, I noted and seemed to have kept himself in good shape.

It was then I threw caution to the wind to have a bit of fun with him, and turned slightly in my chair so that he had a better view of my legs. Without looking directly at him, I checked out the rest of the restaurant and found the other diners busy with their meals as Earl and I sat in the far corner next to the window. No one could really look at us except for the singular diner seated about fifteen feet away.

Gazing out the window, I admired and daydreamed about the pink peignoir set across the street in the shop window as I gradually moved my knees apart and let my silent observer see more and more of my legs. I carefully shifted my focus to glass of the window itself so I could see my admirer in the reflection.

I began to understand how girls must feel when they have such attention from a man.

He was staring intensely at me, and I decided to tease him further by moving my knees even further apart so that he would have a better view up under my skirt. I was sure he knew by this time I was wearing stockings and not pantyhose, and wondered what he thought of that.

As I reached for my coffee cup, I adjusted my position even more and glanced directly at the older man. He had a an obvious lump in the front of his pants, and when he caught me looking at him I smiled and spread my legs further as I ran my tongue over my lips in a most suggestive manner.

His voyeurism was interrupted by our waitress delivering his bill, and he had to fumble for his money to leave a tip and take the bill to the cashier.

As he passed our table he nodded and smiled at me in appreciation for the show I had given him, and I returned his nod with a soft smile of my own.

Earl was still engrossed in the sports section of the paper, and I noted the unisex restroom were near the cashier just before the door of the restaurant. The man paid his bill and stepped into the john to relieve himself before leaving. I knew he was probably going to jack off while in there, and an impulse struck me.

"Excuse me, Daddy," I commented to Earl. "I need to use the lady's room."

"Sure," he responded, not even taking his eyes from the newspaper as I left.

Luckily, Hedy was at the cash register and hadn't noticed the man enter the lava- tory nearby. It was perfect, and when I asked her where the restrooms were she directed me to the singular unisex door.

Inside was a short hallway, and at the end was another door that evidently led to the bathroom itself. Carefully, it walked down the short distance not letting the hard leather heels of my flats give away my presence.

The door was not locked, and pushing it open I was pleased the hinges were well oiled for it remained silent. The single stall door was pushed shut, but I could tell it wasn't latched and innocently I shoved against it to find the man seated on the stool with his dick in his hand just I had been caught by Earl only a few weeks before.

"Hi," I said looking into his surprised face and then down at his stiffness held in his hand. "It looks like the views up my skirt I was giving you have gotten you turned on. Like some help?"

Before he could reply, I leaned back and snapped the lock on the outer door and then entered the stall with him and dropped to my knees, grateful the tile floor felt so cool through my nylons.

"I just love to suck cock," I uttered as I took his stiff dick in my hands and kissed the deep purple head of his cock. "I knew I was turning you on, and feel that you complimented me by the interest you had in looking up under my skirt."

"Ohhh, yesss," he sighed as he leaned back against the wall behind the stool and I began to slobber noisely on his dick as I bobbed my head up and down while I sucked him off.

"EWWWW, Baby!!" he moaned, holding onto my shoulders and I rasped my tongue rapidly against the underside of the head of his cock while I sucked as voraciously as I could. "I'm... I'm going to cum....!!"

He began to buck against my mouth as he fucked my face and torrents of his hot white goo began to flood my mouth. My cheeks filled out with the amount of his cumming, and I struggled to continue to suck his pecker and swallow all he had to give me.

At last he stopped spewing, and relaxed while I felt his dick begin to soften. I felt a twinge of disappointment that it had been so short, but glad I could make him cum for me. "Gee, I do love sucking men off," I thought to myself as I kissed the head of his dick again and tongued his balls before tucking him back inside his undershorts and trousers.

"Thank you for making the day of this older man," he said finally as he stood up and gallantly assisted me in getting to my feet and then handing me my purse.

"You are a lovely young woman, and I appreciate your gift."

"And I enjoyed showing myself off to you. You turned me on, too, and I am happy I could suck you cock and drink your cum. Maybe sometime we can do it again."

I checked my make-up and found myself with nothing amiss except for a couple of dropelts of cum I'd missed which I gathered in with my finger and sucked into my lips.

He suggested I depart first, and then he would quietly leave the restroom a few moments behind me.

Returning to our table, I found our breakfast had just been served, and I smiled at Earl as he helped me with my chair.

"You're such a gentleman, Daddy," I said softly as I placed my napkin on my lap. I spotted Hedy smiling at me from the front of the restaurant and winking while she watched the older man walk out the door of the restaurant. "I'm so happy you brought me here for breakfast."

Earl responded pleasantly, and we chatted about my shopping trip after breakfast as the older man sauntered down the street with a satisfied look on his face. He came by our window, walking slowly as if checking out the flower box outside and I smiled at him as I spread my legs wide open and let him look at me almost all the way up to my panties.

Seeing the man looking at me, Earl spoke up, "Hedy tipped me off about where you

went and what you probably did. That man is one of the guys Hedy told about you so I hope you made him happy."

"Oh, I know I did," I smiled back and then out the window to the man still gazing at me. "I think he liked the way I suck cock," I giggled and spread my legs open as wide as my skirt would allow and exposed the front of my panties down so he could see my dick nestled inside. It took considerable control not to be stiff.

The man blew me a kiss and slowly turned with a thumbs up sign and retraced his steps back to the restaurant. I watched at he came in and talked briefly with Hedy before leaving again for the final time.

I pulled my skirt back into place, and tried to hide my nylons as best I could.

During our meal Hedy caught my eye two more times and indicated a man who was approaching the window. Each time such a man would pass I checked him out first and found him to my liking. With each of them I spread my legs and showed off my nylon clad limbs for him as he gazed at me. Seeing my smile, they knew I liked what I saw, too and then I would open my legs showing the front of my white panties and let them gaze upon my own dick before closing my legs and pulling my hem back down to end their view.

I did notice a few men, both young and old, who checked me out as they passed our window, but they were not indicated as "johns" by Hedy and merely checked me out as a typical female. Some seemed to like what they saw, and I had to make sure my hemline stayed at a demur location even though at best it showed I was wearing stockings not pantyhose under my skirt.

Hedy brought us our bill, personally, whispering to Earl, "She has three guys who want to get into her panties. How about one this afternoon, another tonight, and perhaps she can let the older guy fuck her in the morning before the two of you have to head back to Erica's house?"

This became my introduction, and start, as a transvestite whore who loved being "Daddy's TV Waitress Whore" for him as Hedy pimped for me and Earl made love to me all weekend long each weekend that summer.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
23 Comments
Synthia44Synthia44about 2 years ago

WOW! This story had me shooting loads on each chapter. I have never cum as much as from reading your story.

I truly wish I was Erica.

Great story and well written.

jrrtolkien420jrrtolkien420over 2 years ago

Loved this story I so want to be a Daddy for a sexy CD.

pantycladladpantycladladover 4 years agoAuthor
Thank you for your comments

This note is directed primarily to the most recent anonymous writer: thank you for your kind and supportive words.

Oh how I wish I had a “Daddy” like that dear writer wrote about in her comments about this story.

I’m envious and my panties are tented out, in front, as I think about the fun you must have had with him. I’d love to hear more from you. You can reach me at:

pantywearingsissy@yahoo.com

Sincerely,

sissy erica

(My pen name, in Literotica, is; pantycladlad)

AnonymousAnonymousover 4 years ago
Fond memories

Great story, this brings me back to when I was 17 and was exploring my cross dressing and "daddy" phase in the late 1960's early 70's. I had a very hot sexual relationship with a 55 year old man at the time and when he discovered my panty secret he went all out for me. Thank you for bring back some of the finest memories in my life.

pantycladladpantycladladover 4 years agoAuthor
Thank you for your comments

Thank you for your kind comments about my stories. My writing is far from perfect and I know it. Letters with story ideas, suggestions, and just friendly comments are sincerely welcomed.

Letters meant to insult me will be ignored & discarded.

I write about what fascinates me as a Bisexual Crossdresser. Obviously I’m no oral or anal virgin.

Sincerely,

pantycladlad

pantywearingsissy@yahoo.com

Show More
Share this Story

Similar Stories

A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
My Seduction into CD'ing & Gay Sex Young college age boy learns the joys of CDing & Gay Sex.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
Drink or Dare A drinking game with new friends changes everything.in Transgender & Crossdressers
More Stories