Daddy's CD Waitress

My college graduation was just a few weeks off, and I looked forward to it as I had my recent twenty second birthday. My widowed mother ran a boarding house along with being a secretary in an office downtown. To help out, I did the odd jobs around the house and usually prepared the dinner for ourselves and the boarders.

Finances caused me to stay at home and attend the local community college.

I was a bit shy, and my small build and fine features made me look younger than my real age. I was called "Baby Face", behind my back, and was somewhat a loner. One of our men boarders I did consider a friend. He was understanding, and always made me feel comfortable in his company, the other two ignored me.

With a lot of free time, and since I was out of school early and helped around the house, my time was left unsupervised. One day I discovered a pair of my mother's nylons she was throwing away. Always curious about girls, I wondered how these felt when a girl wore them. As you can guess, I tried them on and the result was electrifying!! It wasn't long before I was sliding them on almost daily, soon added a pair of my mother's panties I'd slipped out of her dresser drawer. I quickly learned to hold my hosiery in place with rubber bands as garters.

I loved strutting around my third floor room clad in these garments, parading back and forth in front of the closet mirror. I'd often dart into the bathroom, when home alone, to masturbate until I achieved an orgasm. The friendly male boarder had the only other room on the third floor, and he usually came home just before dinner.

One day in the bathroom, playing with myself while wearing in my feminine items, the friendly boarder walked in on me. I realized I hadn't shut the door all the way.

"Oops," he said when he saw me sitting there with dick in hand and wearing panties and a pair of nylons. "I thought the room was unoccupied. Sorry," he muttered as he quickly backed out of the room fully aware of what I was up to.

I was humiliated, and quickly stripped out of my things and wrapped a towel around myself as I headed for my bedroom.

"Wait a minute," I heard his voice call from his room, and glancing back found him beckoning to me. "I don't want you to feel embarrassed about this. I understand," he added, "I was your age once."

His words were meant to make me feel better, but, still blushing, I turned and resumed my hasty retreat to the safety of my room.

Wait , wait a minute," he repeated. "I want to apologize, all right?"

At his insistence I let him lead me into his room. Offering a chair, he explained he did "understand", but that if I was going to try dressing in girl's clothes I should do it right. He confided in me that I should try new nylons instead of old 'runned' discards, and something proper to hold them up - like a garter belt. He knew how to appeal to what I wanted, and soon had me confiding in him.

He learned my measurements and promised some new articles for me the next day. I was so happy to have such a good friend who didn't think me a freak.

The next afternoon, as soon as I'd arrived home, Earl called me into his room and handed me a package. Inside I found two pair of sheer black seamless nylons with reinforced heels and toes, a frilly pink garter belt with satin ribbons on the garters, and a pair of pink nylon brief style panties that were sinfully sheer and revealing.

At his insistence I tried on the garments right there, "so that he could be sure he had purchased the right sizes." I loved the wonderful feel of the clothing, and didn't object when he helped me put on the garter belt and attach my stockings.

It was thrilling to walk around so clad in front of another person, especially one who approved of my desire to dress up in girl's things, and my initial nervousness at dressing up in his presence disappeared despite my now having a hard-on. Earl talked me into wearing my new outfit under my boy's slacks and shirt to help Mom prepare dinner that evening, knowing full well how stimulated my feminine garments would keep me.

"You can come back up and 'get off' later on," he advised.

His reference to my masturbating seem natural, and I didn't give it a thought. I did help fix dinner, and found my every movement delightful as the wonderful garments rubbed against me in such a sensual manner. I was turned on like crazy, and had a raging hard-on that was difficult to hide from view. I wore a loose white apron to keep it from everyone's sight. I could hardly wait to clean off the table and wash

dishes so I could head back upstairs and take care of the "problem" in my panties.

When I went up to do my homework I found Earl waiting in the upper hall.

"Well?" he intoned. "Don't they feel great? Does it make you feel truly girlish?"

"Like crazy," I admitted. "Girls are so lucky to be able to wear such wonderful clothes. I've had a hard-on ever since we got me into these! You should see the great 'throbber' they've given me!!" I went on, recalling how we had both laughed at the hard-on I'd developed almost immediately when I put my new lingerie on.

Wanting to see if it was true, he got me to slip off my clothes and model my out- fit for him again. There I was in his room parading around in my panties, garter belt, and sexy nylons, enjoying how it felt and knowing it was thrilling him, too. I found it exciting when he complimented me on how pretty I looked.

"I owe you something for interrupting you like I did yesterday," he said and then before I realized what he was doing he stroked my dong through the filmy panties.

"As kids we used to have 'circle jerks' where we'd jack off the guy next to one side so that when we each did it we completed a full circle being jacked off. I owe you a good jacking off for what happened and for your bravery."

I knew I should resist, my mind said I should stop him, but he knew what he was doing and the wonderful feelings were too intense for me to act. I stood there leaning against him as he fondled me through my silky panties and was unresistant

when he lowered the front and began to languidly jack me off.

"There are a lot of girls who would love to look as good as you do in these clothes you have on," he whispered to me as he slipped his other arm around me and held me close to him as he worked on me. "I think you are very lucky to wear these sexy garments and enjoy them while you look so pretty."

"Oohhh, yesss. Oohh, th-thank you. I-I even, oohhhh...., feel pretty," I found myself muttering as the sensations overran me.

"I think you like what I'm doing to you, don't you Eric," he asked as his other hand slid down to cup and feel up my ass through the sexy panty material as he kept running his hand up and down my cock. "I think you really want me to make you cum, and feel soooo good while you wear your pretty panties and nylons."

"Oohh..... Ye-yess... Make me cummm! It has never felt.... ummm, oohh... this good when..... oohh yesss... when I do it to my.... ummmnn, oohhh... myself."

"Would you like me to get you a pretty nightgown to sleep in?" he inquired as he slipped his hand inside my panties and played with my ass as he increased the tempo of his jacking me off. "Would you like that, and perhaps model it for me?" he went on as a finger toyed with my butt hole and I began to stiffen to shoot.

"Oohh... ohh... Ohh yesss, please do!! Oh-ohhhhh.... I-I'm cummeenng!!" I burst out and began to fire spurt after spurt onto the carpet as he kept up his assault on me while I soared into the throes of my orgasming!

I left his room a little later, feeling guilty but eager to try all this again. The next night I was sleeping in a long feminine silky sheer nightgown he'd given me. Soon he had me shaving my legs, and this greatly increased my sensitivity to my nylons.

Each time I would model the new items for him as he jacked me off. Our sessions were becoming more and more passionate, and he kissed me one day as I came.

Within a week I was captivated by him, and could hardly wait to dress up in some sexy number and be with him. We had progressed to jacking each other off, and I was always thrilled to feel his stiffness in my hands and make this older man shoot his cum in such strong streams while I enjoyed working on him.

Between kisses, one afternoon, he asked if I would like to go up to his cottage for a week-end. He would explain to my mother that he needed my help putting in his dock for the summer and would pay me for my labor. I would be able to dress in feminine clothing for the entire week-end and pretend I was a girl!

I immediately jumped at the chance, and that evening at dinner he casually made a comment to my mother about needing help on putting in his dock at his cottage.

"Maybe Eric could lend you a hand," my mother responded innocently. "Could you pay him instead of someone else you might hire?"

"Why not," Earl replied. "I usually pay twenty to twenty-five dollars, and I'm sure Eric could use the cash. If we can get the dock in the lake then perhaps he can help me put the boat in as well. If we don't get it all done next week-end maybe he can return in a week or so and we'll drop the boat in the lake then."

Mom was delighted, and asked me if I'd agree to helping Earl. It took restraint to not act too excited about the prospect of going with him for the week-end.

The dinner table conversation drifted to other subjects, and soon everyone was talking about the local theatre which was in the final stages of being refurbished and had begun showing movie classics. Wednesday evening it was holding a special showing of "Psycho", even though renovations were incomplete.

Everyone in the house wanted to go, but we understood the theatre was sold out.

"Let me call the manager," Earl offered. "He is a friend of mine, and I'll ask if any seats are still available if anyone is interested." He disappeared into the other room to make the phone call, and in a few minutes returned with a broad smile on his face.

"Yes, he has a few seats he can set up in a couple of areas still being renovated, we can't all sit together, but he thinks he can get all of us in so I made a commitment that we'd all be there." We were all abuzz, and I was especially delighted with Earl and what he had done for everyone in the house as well as for me for the upcoming week-end.

We had dinner early the next evening, and afterward everyone went to their rooms

to get whatever they needed to take to the show. Earl stopped me in the hallway on our floor and asked me if I would be "wearing", our code word for me having on any lingerie under my outer clothes.

I admitted I hadn't planned on it, so he invited me into his room and presented me with a pair of sheer white flare leg panties with scads of soft lace at the hem.

"Try these, they're different than the brief style panties you usually wear, and will be a lot of fun for you to have on. No one will know but us, do it," he insisted.

I quickly got out of my male clothes and slipped on a garter belt, nylons, and the silky panties. They felt wonderful, but I didn't have time to admire them as the rest of the house was waiting for me downstairs so I hurriedly pulled on my slacks and a pair of socks over my stockings before slipping into my loafers. As I rushed down the steps to the living room I found my penis flopping around inside the silky confines and I knew Earl had meant for me to be turned on all evening at the show. I couldn't resist a slight smile and wink at him when no one was looking.

We were among the first to arrive at the theatre, and the manager apologized for not being able to put us together. My mother, and the secretary who had a room on the first floor, were given the best seats, located in a private box off to the left and just below the balcony. They would have an excellent view of the film, and could only be seen from the balcony, which was closed we were informed. Earl tossed a coin to see where the remaining four of us would be seated.

The other two guys got seats off to the side toward the rear, and Earl and I had to settle for the other two seats which we all thought were singles. Earl whispered that we'd be sitting in the balcony, where the manager had held seats for whoever lost the toss.

I found Earl engineered the coin toss to favor the two of us.

"Sorry about the balcony seats," the manager offered. "That's the unfinished area, but I was able to get a couple of seats open for the overflow of your group. I hope you don't mind. You should be able to see the film just fine, though."

Everyone had been happy with the seating, and Earl and I took the stairs to the balcony, where they didn't know we'd be, as the manager closed off the steps behinds us with a decorative rope and hung a sign "closed" on it.

Four seats were actually available, with the rest of the area being covered with canvas to protect the upholstery from paint being applied to the remainder of the ceiling. Scaffolding was everywhere, but did not restrict our view of the screen. I found we could see the private box where my mother and her friend had seats.

"We've the whole balcony to ourselves," Earl whispered in my ear as he ushered me into the row at the back of the balcony and I moved down to the seat furthest from the aisle. Even with the house lights on, no one could see us from even the rows closest to the screen and stage, had they turned around to look for us.

As the lights dimmed and the previews began, Earl's hand held mine, and asked how I liked my new panties had had given me.

"They're kind of exciting," I giggled. "I find I flop around in them, and it is difficult

to avoid having my hard-on show in the front of my slacks. But I love wearing them, and will want to wear them often. My nylons make my slacks feel so very silky and sensual against my legs.

"Thank you for the gift of these panties," I said as Earl's hand free hand moved over and gently massaged my penis.

"I kind of feel like I'm sitting in the theatre with my girlfriend," he murmured as the first preview ended and a second began. "I hope you don't mind," he said as continued to feel me up while releasing my hand to put his arm around me.

"N, no," I stammered, somehow surprised at his sensual assault on me and yet not wanting him to stop. "I, I just don't want to get caught and get into trouble."

"Nothing to worry about," he grinned. "I told the manager to leave us alone so we could have fun with each other, no one will come up with the stairs roped off with the sign. The manager is gay, and understands," he added as his free hand undid the zipper of my pants.

"Want to pretend you are my girlfriend while we're here?" he asked, sliding his fingers inside my trousers and rubbing me through the silky panties.

"Ooh, Earl.....," I whispered in response as I let my head rest on his shoulder, "It would be exciting. You know I love what we do together. I've ju, just ne...ver," I began to stutter as I whispered when his hand slithered inside my panties, "done any..... Oohhh.... thing..... like thi....is oth...er......uummmnnn, tha..an wh..... , oohh Earl....." and stopped long enough to let him kiss me softly and put his tongue in my mouth. "wh...at we...'ve do...ne at, ooh, the house," I said.

"Just relax, Erica. Oh, yes, I'm going to call you Erica whenever you are 'wearing' for us," he said. "Look down at the box seats," he went on, and I found my eyes traveling to my mother and Sally the secretary who had a first floor room.

"Tell me what they are doing," he insisted as he felt my stiff member through the layer of silky material.

"Why, why they're..... they just kissed each other," I mumbled in astonishment. "Sally is feeling up my mom and kissing her," I went on in amazement.

"And you weren't aware they've been getting together for some time?" he asked as he kissed my ear and teased my stiff dick. I found it exciting, and began feeling him through his trousers as he kept on kissing me and feeling me.

Soon I was drooling with passion and not caring what my mother and her girlfriend were doing, although I could see her friend Sally had her hand up my mom's skirt.

"Slide your slacks and your panties down to your ankles," he whispered in the dark and I raised my hips to let him help me lower my garments.

As soon as my clothes were around my ankles, he slipped to the floor between my knees and turned me at an angle across the seat. In the dim light from the screen I could see my silky panties shining in the darkness in contrast against my shiny black nylons and dark trousers below them while in the distance I could see my mother being fingered by her girlfriend.

"You're going to love this, Erica," he whispered as he slowly jacked me off.

"Oohh, Earl, I just don't want to make a mess when, oooohhhh..., you ma..ke me, uummnnhh, cummm, Darling."

"I've got that taken care of," he whispered, and kissed the end of my pecker. This new sensation almost made me bolt upright from the seat, but he held me down and let his lips slip down over my stiff dick to engulf it with his mouth.

Slowly, he sucked on me and pulled his mouth up my shaft, only to slide it back down again and repeat the action.

I was lost in a whirlwind of desire, and ran my fingers through his hair as he work- ed on me. The heel of my other hand was in my mouth to prevent me from making moaning noises that I'm sure would have been heard by the theatre goers below.

His soft slurping on my cock was driving me wild, and I knew I had to cum soon! My hips began to thrust up to meet his lips as he sucked down on my dick, and I found I was tossing my head from side to side as he kept up his assault!

"Oohhh, Darling......," I breathed as he softly slobbered away around my dick, pausing only long enough to kiss and lick my balls before returning to my cock.

Suddenly I began to cum, almost without forewarning, and spewed forth copious amounts of hot gism as Earl continued to suck and move his lips up and down on my shaft. He kept sucking me until I could cum no more and began to soften in

his oral grasp.

Letting my slackening dick slip from his mouth, he eased back up next to me and held me in his arms as I tried to recover from the treatment he had just given me. I knew I wanted this to happen again and again, and hoped he would do me every time that I dressed in my pretty clothing.

"Still want to be my girlfriend next week-end?" he whispered in my ear as he kissed it and gently fondled my balls and soft pecker.

"Ohh, yess, more than ever," I murmured in response, and let him kiss me on the lips before sliding his tongue inside my mouth to give me a deep French kiss. I could taste a subtle sensation of my own cum juice on his lips as he kissed me.

"I've never cum that hard before," I admitted as I put my hand over his while he continued to feel me. "I hope you'll do it again, Darling."

Earl helped me pull my panties back up into place and restore my trousers to their normal position, but kept my zipper down so he could feel me anytime he wanted.

I reclined my head on his shoulder and gently kneaded his cock through his pants as we stared at the movie.