Kelly's First Date

Kelly

I graduated from high school in June of nineteen sixty-six. It was not a public school but an all-girl, very strict catholic school. Most of the teachers were nuns and they all stressed that sex was reserved for procreation and that guys were evil. My parents were very protective of me. So were all of my classmate's parents, and most of my class, myself included, had never gone out on a date. Much less having French kissed a guy and forget about letting anyone touch me.

People always tell me how "pretty" I am, but I can never see it.

Looking in our full-length mirror, I felt self-conscious. My legs are shapely, my butt is round and tight, and my boobs started filling out last year. I can only guess my size; my mother always buys shapeless cotton bras and "granny panties." The last bra she bought me was a thirty-two c cup that my boobs filled out completely. Round and firm with super sensitive nipples, more than once, I spent extra time soaping them in the shower.

I was looking forward to a fun summer. A friend had found me a job at the local "Dairy Hut" that my father's close friend from our church owned. I needed the money and wanted to get out in the real world and meet some boys. I thought everything was settled; then Vicky appeared on the scene.

My parents have been chosen to represent our church at a week-long series of seminars out of town. There was no way they would leave me alone, my mother's friend from college, Vicky, offered to take me to her apartment in New York City for a week. I acted like I didn't want to go, and I knew that would make my mother force me, and it worked.

Vicky was a little wild in the early sixties, and what she did for money needed to be clarified. When the subject was brought up, my mother always said that Vicky was a personal assistant, I didn't know what that meant. But she always drove a new car and wore beautiful clothes. I couldn't wait.

Vicky picked me up on Wednesday, and we set off for New York.

I had on a plain white summer dress and flat shoes. By contrast, Vicky wore a tight floral dress with white heels. She was so youthful at thirty-nine years old we could almost pass for sisters. It was less than a two-hour drive. I loved speaking with her; she treated me like an adult. We mainly talked about my graduation and what I was going to do. Finally, she brought up boys.

"Are you serious about anybody special?"

I turned beet red, "I've never been on a date," I whispered.

She turned and looked at me, "With those legs and boobs, you should be beating boys off with a stick."

"Tell my mother I can't even pick out my own clothes." I was on a roll as I told her how strict my parents were. Vicky replied.

"Well, we've got a week to make some changes."

I was nervous and wasn't sure what she meant.

"You must learn to control men by preying on their weakness; they are very visual and easily controlled."

I was so naive, "What do you mean, Vicky."

I'm like an aunt to you, so it will be my job to give you the facts of life. There's a gas station coming up, and I need gas and want something cold to drink.

"Sure I said. While you're getting gas, I'll go inside."

"You're not going anywhere; the gas guy will get it for us for free."

I was so excited I had no idea what to expect. We stopped short of the gas pumps. Vicky sat up in her seat and pulled her dress up, exposing her stocking tops and garter clasps. I was shocked,

" Vicky, what are you doing?

"Men are suckers for stockings and a good set of legs; now watch and learn."

We pulled up to the pumps, and a kid in his twenties walked up to the car; his eyes went straight to her exposed legs.

"Fill me up," she purred. He nearly fell over his feet, trying to hurry. After he started the pump, he came up to clean the windshield.

"You don't have to do that," Vicky said. She turned, looking at me and winking.

"I don't mind. It's part of my job." He kept cleaning the glass on Vicky's side while hardly touching mine.

"Look at the bulge in his pants, Kelly; he likes my legs."

I glanced at him, and my eyes nearly popped; he had a huge bulge in his pants that looked like it would break his zipper. I had never seen anything like that before; I felt tingling in my crotch. I so wanted to touch myself.

Vicky paid for the gas and asked the attendant if cold drinks were inside as he made change; she leaned back and said, "My feet are killing me in these heels. Would you be a dear and get two for me?"

To emphasize the point, she pulled up her leg, showing him her heels and more leg almost to her panties. "Yes, right away." He returned in a minute, handing them to her.

"You're such an angel; what do I owe you, dear?" At the same time, laying her hand on his arm.

"It's my pleasure," he said as Vicky winked at him.

When we were on the road again, Vicky laughed.

"See, I told you men are easy. Never underestimate the power of nylons and heels."

I was stunned but later found out she was right; I adored her confidence; I would have died of embarrassment, doing what she did. What fascinated me was how casual she was with her exposed stockings.

We arrived at her apartment around four. It was on the twentieth floor, and I almost fainted when she opened the door. The apartment was breathtaking; it overlooked the Hudson River; I made up my mind on the spot. I wanted to stay here forever.

Vicky ordered some appetizers from the restaurant on the first floor.

She poured me a glass of wine; I was shocked,

"I've never had anything to drink in my life," Vicky smiled.

"You're old enough. Just take it slow."

I carefully sipped it, loving the warm feeling spreading over me. The food came, and I had never had shrimp cocktail before. I wanted more of this lifestyle, I ate most of the appetizers, Vicky laughed.

"Come on, let's go to dinner so we can come back and relax."

I felt so important being with Vicky. She was so pretty, and everybody knew her. She looked elegant in a black V-neck dress with dark stockings and heels. When we were seated, the restaurant manager came over, kissed Vicky's hand, and asked if she would be staying for an extended visit. I was shocked; I thought she lived here all the time.

Vicky introduced me and said we would stay for a few weeks. He bowed and kissed my hand; I never felt so special. After we finished dinner, I noticed we never received a check for the meal. Vicky got up and walked over to the manager; she said something to him and kissed him on the cheek.

Back in her apartment, I sat on the couch, enjoying the view; Vicky poured another glass of wine for us and sat close to me, our legs touching. I turned to her,

"I don't think I'll ever be able to wear high heels without falling."

"Nonsense, let's try right now." Vicky went to the bedroom and returned with black three-inch heels. I slipped off my flats and into the heels. I stood up, wobbling a little; I could only go a few steps, then fell onto the couch laughing. Vicky caught me, saying let's go to bed. We have a big shopping day ahead of us.

I finished brushing my teeth when Vicky called to help remove her necklace. I was surprised she was still in her underwear; she noticed I looked shocked.

"What's the matter, Kelly?"

"I have only seen stuff like this in magazines."

"Oh, you mean my garter belt and bra. Don't tell me you still wear a panty girdle; they're for old women. Your mother should be ashamed. You're a young woman. You should feel pretty."

I removed her necklace, still blushing, embarrassed, and turned on simultaneously. I said goodnight and went into my bedroom.

I lay in bed wondering what this feeling I was experiencing was all about. My hands went to my crotch, applying light pressure. I had experienced the same feeling in the shower; the nuns in school had warned us about self-abuse. I felt guilty, but it just felt so good. I fell asleep squeezing my hands between my thighs, feeling frustrated.

Vicky was up early, and after breakfast, we headed out shopping. I tried to tell her I didn't have much money, but she kissed me on the cheek, saying not to worry, it was her treat.

The morning flew by; it was unlike anything I had ever experienced shopping.

Vicky knew everybody in the shops; I lost count of the dresses and skirts she bought for me; the best part was we didn't have to carry anything. The salesgirls sent all the clothes to her apartment.

Over lunch at a small cafe, Vicky said how much fun she was having.

"When we're finished lunch, we will get the important stuff,"

she said, winking at me.

"Vicky, you're spending too much on me. How can I ever repay you?"

She smiled and took my hand.

"We'll make it your graduation present from me."

The afternoon was much like the morning, a whirlwind of shopping. Vicky bought me three pairs of high heels. Then we headed to the lingerie shop, the only store I felt nervous about. My mother bought all of my underwear at a variety store.

Of course, Jan, who ran the shop, knew Vicky. I felt like a child. All the women in the store were so beautiful and worldly.

We went into a private dressing room. Jan said the first thing was to get undressed. While stripping, Jan brought in two glasses of wine, and I eagerly drank mine.

I pulled my simple dress over my head, standing in my white cotton bra, panties, and panty girdle.

"I mean everything, honey," Jan said.

I was blushing furiously, but Jan was professional. She returned with an assortment of bras, panties, and garter belts. After settling on the correct sizes,

I nestled my thirty-two D boobs into a black lace bra and pulled on matching panties and a garter belt. As I clipped my garters to dark suntan stockings, I realized the bra cups were cut so the tops of my tits showed; I looked and felt like a "Bad girl." I wondered if this was a sin.

Vicky and Jan looked me over. I felt very self-conscious standing there in my underwear as they inspected me, adjusting my garters and remarking how guys would give me anything I wanted, just for a smile.

I put my dress back on and slipped into white heels. I walked back into the shop, getting used to my heels.

"You look great, Kelly, and thanks for your help Jan." Vicky embraced her. We returned around five o'clock, and I was amazed that all of our bags were with the doorman, who brought them up to Vicky's apartment.

Since we had a late lunch, we decided to have something sent up later. Vicky was often on the phone; I could never make out what she was saying,

She spoke softly with a husky voice that she didn't use with me. It could only be a man; I heard her say something about Saturday night.

We had steak for dinner; we rarely had food like this at home. I wanted to live with Vicky forever.

We sat on the bed, checking out what we had bought. I had another glass of wine, and I was feeling a little tipsy. Giggling I said,

"Vicky, I think I'm drunk."

"You're just a little high. Now let's see your new undies."

I could never undress in front of anyone, even in school, but the wine made it seem all right.

I stood up and unzipped my dress as Vicky sat back, sipping her wine.

I stepped out of my dress and stood before her,

"I feel so sexy; thank you so much; I love everything."

"Try on your black heels and see what they do for your legs."

I slipped into my new shoes, "See how they highlight your calves and thighs."

Vicky said while handing me a full glass of wine. I felt emboldened by the wine and struck what I thought was a sexy pose; I loved how I looked in a garter belt and nylons. The stockings reached high on my legs, making my legs seem longer.

I walked across the room, a little unsteady. My boobs jiggled in my lace bra.

I felt so grown up, standing there in my heels. I wasn't shocked when Vicky reached up and took my hand. I foolishly thought she was trying to steady me.

But she continued pulling me onto my bed until I was lying beside her. I was shocked and scared, but she smiled and kissed my neck.

She nuzzled my neck and whispered, "You've never let a boy touch you?"

I shook my head no. She removed her dress and lay next to me.

"Just relax and let yourself go," Vicky said in a soothing voice.

"Vicky, what are you doing? You should stop. It's not right, were both girls." She smiled; her kisses lit a fire. I didn't object when her hand brushed my thigh and then my sensitive mound, lingering there with light pressure. Her mouth moved from my neck to my lips and kissed me gently, her tongue probing mine. I was in heaven. I don't care what I had said, I never wanted her to stop. My pussy was begging to be touched. I had never kissed anyone like this before, much less a woman. My head was spinning, and she was in complete control; I would do anything she wanted.

Her hand moved to my tender breast and squeezed hard; it hurt and felt good at the same time. Vicky broke our kiss, pulled down the cups of my bra, and attacked my nipples with her hot mouth; I thought I would explode. She alternated, sucking and biting my swollen nipples as she lightly trailed soft kisses down to my navel. Hooking her thumbs in my panties, she pulled them down.

I was trembling like a leaf as her mouth neared my pussy. Even as I began to protest, I spread my legs as she clamped her mouth on my soft folds, her tongue torturing my clit. I had never experienced anything like this before.

I never wanted this feeling to stop; without thinking about it, I wrapped my nylon-covered legs around her head, urging Vicky's tongue deeper. She moved her hand and pulled at my nipple, which put me over the top; my pussy spasmed, and contractions wracked my body as my first orgasm washed over me.

Covered in sweat and still shaking, Vicky embraced me, kissing me full on the lips. I could taste my juice on her lips and kissed her deeply. She sat up, looking me in the eye.

"I'm glad I was your first." She whispered.

She held me close, and we fell asleep in each other's arms. It felt so good; our bodies intertwined, one of her stockinged legs between mine.

I woke at seven with a hangover and a massive dose of guilt; I still couldn't believe what had happened. I could hear Vicky humming to herself in the kitchen; she didn't sound guilty, that's for sure. She walked into my bedroom in a short robe that barely covered her rear. I felt embarrassed, still in my garter belt and nylons.

"Come on, sleepy head, we've got much to do."

I was so embarrassed that I couldn't look her in the eye. Finally, she broke the ice saying we were both drunk and had some fun, no harm done. My cheeks were bright red; I cast my eyes down and said,

"I want you to know I'm not a lesbian."

She threw her head back, laughing. "Neither am I.

I like to have fun; you're a beautiful girl. Learn to enjoy your body."

I felt better but still uneasy.

Vicky was a whirlwind; she was showered and dressed in no time. I bathed quickly and put on a white lace bra and matching panties, with my garter belt with suntan stockings; I settled on a sleeveless blue dress that barely came to my knees and white heels.

Vicky announced we were headed to the hairdresser. I wore my blonde hair straight. She said I needed curls, not asking my opinion.

We spent two hours there, and I liked my new look.

Vicky took me to a small restaurant. It was after two, so it was nearly deserted; we sat in a secluded booth, and she ordered two glasses of wine. The waitress never questioned my age.

After we ordered, Vicky leaned across the table and clasped my hands,

"We've got to talk about what I do for a living."

I started to tremble, "It's ok, Vicky." I understand.

"No, you don't; I'm a personal assistant."

"I go out on dates with wealthy businessmen who are lonely and will pay for my company."

My mouth was hanging open.

"Do you sleep with them?" I was afraid of what the answer would be.

"Only if I want to. I'm not a hooker."

"What about last night?"

Vicky smiled, "I wanted your first experience to be good. You worry too much. Now let's eat; we will talk later."

I couldn't believe we had lobster for lunch; Vicky's life seemed good.

Later at the apartment, we sat on the couch; I felt so at ease with her. She tucked her legs under her, exposing her stocking tops. I reached out and stroked her thigh,

"These are beautiful nylons," I commented.

"I buy only the best," she smiled. Then came the bombshell.

"I'm going on a date Saturday night; he has a friend; would you like me to set it up?"

I felt like I would faint, "Oh, Vicky, I don't know what to do."

"You'll be with me, and it would be a good experience, and you'll have fun."

I said, "What if he doesn't think I'm pretty?"

Vicky stood up, don't ever worry about that, dear; you don't realize the power you have."

Later in bed, feeling the wine, I let my hand stray to my soft slit and didn't hesitate to slip my finger into my aching cunt; it felt so good that I started moaning and moving my hips. I went deeper and soon brought myself off. I lay there shaking, wishing I had been with Vicky a year ago.

We went shopping Friday morning; Vicky said I needed a dressy cocktail outfit for our date. We went to a small shop, and she picked a black dress I would never have considered; it was short, tight, and low-cut. The saleslady suggested a waist cincher rather than a corset, and Vicky took both with the dress and a pair of off-black stockings.

We were sitting on the couch after dinner. I put down my glass of wine and turned to Vicky,

"What will I have to do on the date?"

she touched my cheek tenderly,

"Don't worry, these two men are in their sixties, in town for a meeting, and want to go out with two beautiful girls. I'll be with you. Nothing is going to happen."

I barely whispered, "What if he wants sex? I've never even seen a man's thing." I emptied my third glass of wine.

"Just remember you're in control, men think they are, but believe me, we can always get our way."

"Next to legs, men love tits; they love to suck on them and even fuck them."

This statement shocked me. "How could somebody do that to my breasts, Vicky?"

"You really are innocent; wait here; have another glass of wine, and I'll try and answer your questions. I have a phone call to make."

Fifteen minutes later, Vicky asked, "What's on your mind, dear?"

"I don't know where to start," I said.

I loved Vicky; she made me feel so at ease; I could never have asked my mother these questions, even if she knew the answers. With what Vicky explained, I hoped I was ready for my first date with a man older than my father. Saturday came, and I was up at six o'clock in the morning feeling more nervous than I can ever remember.

Vicky went to the dentist while I went to the pool to get a little color; that was a big mistake. I borrowed one of Vicky's suits; all she had were bikinis. I didn't realize how much bigger my chest was than hers. My boobs bulged out of the top, which barely covered my nipples.

As soon as I lay down, a guy about thirty sat down next to me; I felt vulnerable lying there while he was sitting so close to me, looking at my exposed chest. He tried to make small talk, and I blurted out that I was engaged. He smiled coldly.

"I don't see a ring or your boyfriend, so relax."

At the same time, he brushed one of my boobs with his fingers. I started to panic; no one was around.

"My name is Rick. Why don't we go to my room and get to know each other."

It was more an order than a question. He took my hand and started to pull me up. I glanced around wildly. Thank God the lifeguard came on duty.

"Let me go, or I'll scream." I shook his hand off, and he stepped back, my boobs almost overflowing with the too-small top.

"I'll catch you later, you fucking tease, and teach you a lesson; I'm going to have a lot of fun with you." He smirked, reaching out and pinching my nipples.