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

"Do you want me to suck you," I asked as I kissed his neck and felt him up. "I feel I should repay you for what you did for me, Darling."

"Later, Erica," he whispered and kissed me softly. "Tonight before we go to bed

you can get on your knees and suck me off, okay?"

I merely nodded and smiled up at him as I snuggled closer and we each played with each other. Off in the distance in the box, I could see Sally with her head under the skirt of my mom's dress and watched as my mom's head rolled back as she began to shudder through her cumming. Maybe getting away to spend week-ends with Earl would be easier than I had thought.

"Friday, I want you to come home from your classes as early as you can. It will give us more time together at the lake."

"Sure, Earl, Darling. I can get out at noon if that will help. We have a workshop that I've already done so I can skip that."

"Good. I've gotten some other new clothes for you, and they will be on top of the other garments of yours you keep in my bureau. I'll want you to use dipilatory on some new areas that I'll define for you tonight. That way you will feel as feminine as possible. Also, I'll want you to wear exactly what I have laid out for you. I will be there as soon as I can so we can leave. Understood?"

"Y-yes, I'll do it," I said, admitting to Earl I liked having him dominate me. By the time he'd zipped up my pants, I was agreeing to using the dipilatory all over and to reduce my pubic area to just a narrow feminine vertical patch. My balls and cock would be totally hair free, and I would powder my body before putting on whatever surprise he had in store for me to wear for the trip.

The last few minutes of the movie we watched without feeling each other, so that our hard-ons would go away before we headed back to the rest of the crowd.

No one let on what they had done with each other during the film, and that was just as well, it occurred to me. "No questions, no answers necessary," I thought.

That night, after everyone had gone to bed, I crept into Earl's room as agreed. I wore my pretty white sheer nylon babydoll nightie and a pair of sheer white string bikini panties over a white satin six suspender garterbelt and black seamless nylons. I knew Earl liked to see me in that outfit, and I was eager to please him in every way I could.

Creeping through the dark hallway, I found his room and let myself in without knocking. Earl was laying on his bed in the nude, slowly stroking his stiff rod that was standing upright from his reclining form. The lamp on the nightstand outlined his strong form in the dim light, and I once again admired his masculine good looks.

"I'm beginning to think more and more like a girl," I thought to myself as I eased onto the mattress next to him.

He wrapped me in his arms and we kissed deeply. I let him pull me closely to him, and did not resist when he lay atop me as we necked. I found it thrilled me to feel his stiff dick rubbing mine through my panties and sheer nightie.

Slowly, he began to rock against me as we lay there in each other's arms. The thrust of his pelvis and stiff pecker against my own through my panties was a new

form of excitement for me and I realized I would cum just from our mutual rubbing.

"It feels sooo good when you lay atop me and dry fuck me," I said softly as I smiled up at him when we paused for air.

"Do you want me to suck you off like you did me, or would you rather do this?"

"Do you like it?" he asked, thrusting once more and continuing the rythm.

"I love it," I breathed. "You're going to make me cum if you don't stop. Or is that your plan, Darling?"

"No, I want you to suck me off and be my pretty little cock-sucker. This week-end I'm going to get you into this position again, only I'll have my big dick up your sweet little asshole and will fuck you like the girl you would like to be."

We kissed again, and then he guided me to the side of the bed, where I knelt and felt his stiff dong before tentatively taking it in my mouth and imitating what he had done for me in the balcony of the theatre.

This was a totally new sensation for me, and as I had found a few days earlier I was discovering a new thrill for me. I loved the stiff and yet pliant feel of his dick in my hand and even more so in my mouth. I enjoyed feeling the corona of the head of his dick with my lips and tongue and then the feeling it gave me to have as much of him inside my mouth as I could while I suckled on him.

Teasing the sensitive underside of his cockhead turned me on all the more, but I didn't realize how instantly addictive cocksucking could be.

As I knelt on the carpet my slippery nylons made me slide about, but I didn't mind the sexy distraction as I enjoyed what I was doing for Earl. I cupped and felt his soft furry balls in my hands, and stopped to kiss and lick them from time to time.

I was eager to make him cum and find out what cum would taste like. "Will I like it?" I wondered, "Or, will it make me sick?" were thoughts racing through my mind as I slavishly suckled on his dick, letting out slurping sounds every now and then and playing with myself through my silky panties with my free hand.

"Ohh, Baby....." Earl moaned at last as he began to fuck back at my lips. "I'm going to cum, Erica...... Get ready to suck down my cum juice, Baby!"

As he spoke I could feel his balls begin to tighten, and then his dick began to throb in my mouth and fire forth spurts of his hot cum juice for me. His cum juice was somewhat thick and silky, while mild to the taste.

I found his shooting was very quickly filling my mouth, and I had to gulp down his nectar as fast as I could to avoid spilling any of it. The taste was decidedly pleasant, I determined, and I would also learn it was an addictive taste.

"Ohh, you're a fine cocksucker, Erica," Earl moaned at last as I finally let his now deflating tool slip from my still sucking lips. "You really made me cum. I'll have to give you plenty of chances to suck me off on our week-end at the lake."

"Oh, I hope so," I laughed quietly, in the semi-darkness as I played with myself through my panties. Soon Earl had me jacking myself off for his enjoyment.

Friday after school we were on our way. I had arrived early and used the dipilatory on my legs, arms, underarms, and chest as Earl had directed. My lingerie, under my masculine outer clothes, was a thin white nylon bra, white satin garter belt with six suspenders, black seamed nylons, sheer white nylon brief style panties, and a thin white nylon camisole over a pair of while nylon slack liners. It all felt wonderful under my shirt and trousers, as well as making me very horny.

Earl wanted me wear lingerie under my boy's clothes, "to take advantage each minute available to dress up like a girl." His ploy really was to have me constantly turned on during the drive so that his moves on me would be accepted.

My nylons pulled tautly against the suspenders of my garter belt and felt so sensual inside my slack liners and trousers as the car motored along the highway. My hard-on was straining against my sexy panties as I reveled in the pleasures derived from my undies that so sensually rubbed against my skin.

Outside town he reached over and held my hand as we drove, occasionally rubbing my legs with his hand while telling me that he'd added some wonderful items to my wardrobe. As he talked I learned he found a new dress for me and a skirt and blouse, even a girl's bathing suit as well. Some new pieces of lingerie along with make-up were awaiting me, as were my first pair of high heels.These were exciting words for me to hear, and I found myself unable to wait.

"To spend a few days living as a girl is too thrilling!" I though to myself as we drove along.

I liked having Earl hold my hand, and thrilled to the feelings on my legs as he made my slacks slide against the nylon liners and silken stockings encasing my limbs.

Boldly, I reached over with my free hand to rub his dick through his pants as he drove, finding I was becoming hooked on his love muscle. I began to fantasize about rubbing our two cocks together, and hoped he'd let me if I asked.

"Be careful, young lady," he admonished while smiling at me, "You could make me have an accident." I was happy to notice he did nothing to stop me from feeling him as we drove, and was pleased that he referred to me as "young lady".

I found I enjoyed this David Niven look-alike guy, and anxious to model for him whatever he had selected for me to wear that week-end. "A whole wardrobe of girl's stuff!" I thought to myself, and felt like a real Cinderella.

"What if someone sees us?" I asked suddenly with a bit of concern in my voice.

"My cottage is a two-storey 'A-frame' chalet out at the end of a peninsula. The only person who could see anything is a neighbor who wears nothing but women's clothes and everyone thinks he's a woman. You'll be okay, but if anyone asks anything just refer to me as 'Daddy'."

"Okay, 'Daddy'," I grinned and slid my hand inside the waist band of his trousers to toy with his stiff meat without any layers of clothing to interfere, and found my- self eager to see this neighbor who liked to wear the same kind of clothing as me.

"I think I'll have to give you a new way to cum this week-end," he laughed, inter- rupting my musing as he turned off of the freeway onto the road leading toward the lake area. "I think you're getting horny wearing your finer things on this trip," he went on as his right hand toyed with a garter tab holding my stocking and I suddenly realized even that was exciting me.

"Yes, Daddy," I laughed, and suddenly blushed like a girl as I grinned at him. I star- ed down at my hard-on making a tent shape in the front of my slacks, and knew I just had to get off soon.

"I guess I need to suck you off again," I admitted, blushing at my blurted words.

Our journey took us through a small village along the edge of the large lake, and I saw the long peninsula running out into the water. We arrived at the chalet which I discovered was a year round home.

He carried our things into the building, and then led me into the kitchen where he said, "A toast to your femininity." Earl winked at me raising a wine glass and offering me a fresh soft drink.

"Here's to a week-end for you, and a chance to live every moment as the beautiful young lady you want to be, and we know is hidden inside," he concluded and kissed me lightly on the forehead as we clinked glasses.

I smiled in response and joined him in his toast to me. His arm around my shoulder let him easily lead me through the chalet showing me all the rooms and their furnishings.

We ended the tour in the upstairs bedroom, where my new outfits were on display. A dress, skirt and blouse, plus the high heels, more nylons, make-up, a wig, scads of sexy new lingerie, and all for me!!

"Oh, Daddy!! How can I ever thank you enough?!" I squealed as I hugged him and

admired the wonderful outfits I would enjoy wearing.

"I think we can find a way, Erica," he muttered as he tilted my chin up and kissed me deeply. Our glasses found their way to a table top and we continued to kiss deeply as he undid the front of my slacks. It was time for a "circle jerk", and I was needing it!!

As we necked he undid my shirt, removing it, along with the slacks and slack liners with only my boyish slacks and my loafers on, leaving me clad in just my lingerie.

It was different this time as Earl stripped nude. I loved how I must have looked to him clad in just my white camisole, panties and black nylons with garter belt. I felt so sexual, and needed release.

His hard meat jutted straight out and looked so powerful, I couldn't resist wrapping a hand around it and stroking him as we fell onto the bed sheet kissing. Earl fondled me through my panties, and soon I was panting and wanting more.

We were really getting into the kissing end of it this time, and he was really getting me worked up. It was thrilling to neck with him.

He lubed his finger and slid it in my ass. He'd done this before to get me excited and I moaned with delight and anticipation as he slowly worked it in.

"Let me lay on top of you," he whispered, "I want you to feel more like a girl."

Cooperatively I let him slide up over me and spread my nylon sheathed legs as he wiggled between my silken knees. His finger in my ass teased me to new heights of wanting to get off, and then he removed it as our tongues dueled.

"I'm going to make a real woman of you this week-end, Erica," he whispered into

my ear as he kissed and licked at it. It was then I thought I felt his finger push against my anal opening, and relaxed to allow him to slide it inside.

"I'm going to fuck you, Erica," he hissed while kissing me. "I'm going to fuck your boi pussy and take your pretty little cherry! When I slide my hard dick up your cute little back cunt I'm going to fuck you silly!!"

At first I thought he was kidding, but then I realized it was his cock pressing into my rectum and suddenly understood what he meant. My eyes welled up with fear, and I clenched up my ass muscles, but I was too late as he had already pushed the large purple corona of his dick inside the ring of my opening. I was torn with desire and fright at the same time.

"Plea-please sto-op, it's go-going to... oohhh, Earl!! It's go-ing to hu-urt.... Oohhh, Da-ddy!!!, you're sho-ving i-it all-ll th-the wa-ay in-side me!! Oohh, mmngfh, ....ooohh ye-yesss!! I ha-ad no-o idea!!! Ohh, Da-ddy, fu-fuck me-ee!!" I managed to blabber as the sensations took over and the pain I had feared never material- ized. All I wanted was to be his little girl and get a good and thorough fucking!

"You like this, don't you Erica?" he whispered as he kept his pistoning of his prick in and out of my virginal ass. "You needed for me to fuck you, didn't you?"

"Oo-ohh, ye-ssss, Da-ddy!!" I blubbered on as his pounding of me forced my words to come out in broken gasps while I bounced against the mattress. "I-I thi-ink I'm go-ing to-o cu-ummmm!!" As I cried out I began to spurt forth hot cum from my cockette and felt Earl stiffen and then begin to throb inside my back passage.

It was a wonderful sensation to realize we were cumming at the same time, and I hugged and kissed him as we soared through our throes of our passionate orgasms!

At last he softened and slipped out of me and then gently helped me off of the bed and into the bathroom where he stripped me and we showered together.

"For the whole week-end I want you to think of yourself as a girl. Wear only girl's clothes and expect to be treated just as if you were 100% female. You will be fucked and sucked just as if you were the girl you really want to be, because we both know you enjoy it and want it."

"Oh, yes, Daddy," I agreed as he toweled me dry and then dusted me with powder before leading me into the closet and helped me select a fresh outfit for the rest of the evening. I was so eager to try everything he had proposed, and it sounded just idyllic to be a girl for a whole two days and be regarded as such.

Soon I found myself wearing a pretty pink garter belt with six suspenders and lots of lace trim. Under the satin ribbons at the garter tabs were the tops of a pair black seamless nylons running straight up my long legs. A very sheer pair of pink nylon panties cradled my cock and balls, and the stimulation of the outfit was al- ready making me return to hardness.

A bra of pink satin with seamless cups was fitted around my hairless chest and a pair of very realistic silicone breasts, with stiff nipples, were inserted into the cups and I felt the adhesive gluing them to me. They weighed and bounced just like the real thing, and I marveled at how much they added to my feeling like a girl as I was unable to resist staring down at them and feeling them as if trying to feel myself up.

Earl let a pink nylon full slip drift down over me that had about three inches of lace along the hem, and then came a white long sleeved blouse of polyester and a tight mini-skirt in black. The hem of the skirt reached about five inches above my knees, and matched the length of the slip. My stocking tops were barely hidden from view. My loafers were sufficient for this evening, I was informed as I could wear my high heels the next day and learn how to walk with them.

Earl helped me with my make-up, and I loved the feel and attention my face was getting. The false eyelashes dramatized my eyes and made them look seductive, while the blonde wig in a curly shoulder length style gave me a convincing feminine look. Delicate pearl dangly earrings and a matching necklace completed the outfit and I turned to see the result in the mirror and nearly swooned!

Looking back at me was a beautiful young girl, although I knew instantly it was me and I was still eighteen.

"I look lovely!!" I cried and jumped up and down as I squealed with joy just as such a girl would do. My false tits bounced up and down in my bra, and I realized even further just how a girl would feel!

"Oohh, Daddy!! I'm loving this!!" I exclaimed and gave him a big kiss that left some of my lipstick on his lips, to our mutual delight.

"Well, how would you like to go for a walk and see how your public approves of your appearance? I'm sure you will get many approving stares, and lots of the young boys would like to figure out how to get into your pretty little silky panties."

"Oh, let's do it!" I burst out, confident no one would realize I was really a guy in girls clothing.

"I don't know how I can repay you, Daddy," I said as he handed me a purse to carry and threw a cardigan sweater over my shoulders as we headed for the door and into the growing dusk of the warm spring evening.

"Well, tonight you and I can play some other games in bed before we go to sleep. By the way, you will sleep with me each night while we are here."

As I moved in the skirt I found it restricted my steps, and yet made my slip rub against my nylon clad legs and panty clad ass to excite me more than I could have imagined. My bra, and the slip over my chest thrilled me, too, and I knew I was ready for whatever he wanted of me I was so turned-on.

At the door I let him take me in his arms, just like a girl, and give me a deep French kiss that lingered and I felt his hard-on through his pants with my free hand.

"Ohh, yess, Daddy. Whatever you want to do to me is fine. I want you to fuck me again, and again." I whispered as we paused in our kissing for a breath of air. "Of course, I'll still get to suck your cock. Won't I, Daddy?"

"Oh, yes, you sweet minx," he laughed and lightly spanked my ass through the layers of thrilling material. "Just don't let your outfit turn you on so much that you show off a big hard-on in the front of your pretty little skirt."

We both chuckled as we went out the door, but I was sure I could hide even the most rampant of hard-on with my purse held in front of me if necessary. Earl knew what he was doing, and I was loving it. He had me ready for passion whenever he wanted and would soon have me trained as a cock loving transvestite slut.