Chapter 8

My bike ride was vigorous on Friday morning. I returned home at seven after an hour’s ride. Since I began riding, I measured my workout in time, not miles. Mom and Dad were in the kitchen, having breakfast before leaving for work.

“Mom, do you know where Kyle is taking me for dinner tonight?” I poured a glass of orange juice and leaned against the counter to drink it.

“Yes.”

“Will you tell me?”

“No, Kyle wants it to be a surprise.”

“MOM! I don’t know what to wear.”

“Meet me at my office at lunchtime. I’ll help you pick something appropriate.”

“You aren’t going to tell me, are you?”

“No, I’m not, so stop asking me.”

I finished my juice, went upstairs, and took a hot shower. I shaved my legs, then my vulva, and trimmed my mons. As I ran the razor over my hairless crotch, I thought about the feeling of having my sister do it for me.

Out of the shower and dried, I applied lotion to my entire body. Looking at myself in the mirror, I decided my hair needed a trim. I went into my bedroom, called the salon my mom always took me to, and made an appointment.

Friday was one of my gym days, and I considered skipping it for the day, but my sister’s words returned to me, and I decided to go. I put on underwear, shorts, and a top. After grabbing my gym bag, I left the house.

I went through my routine, showered, and left to go home and get ready for my haircut. When I arrived at the salon, it was ten, and they put me in a chair. After a brief conversation with the stylist, she went to work. When she finished, my hair was about two inches shorter and off my shoulders. The stylist curled it and used hairspray to hold it in place.

Driving to Mom’s office, I decided this would be like getting ready for my prom.

Mom was able to leave when I arrived, and we went to a shop downtown. She searched through the racks and found a cute black cocktail dress. Mom took me into the dressing room and had me try it on.

The dress fit like a glove, accenting my hips and chest. The deep vee of the neckline stopped between my breasts, and the back was almost as low. Looking down, I smiled at how short the cute garment was. Not so short I wouldn’t be able to sit down, but short enough to catch Kyle’s eye.

“You look very nice in this dress, Trish. Do you have shoes and lingerie to go with it?”

“No, Mom.”

Mom told me to remove the dress and put my street clothes back on. She paid for the dress, and we went to a shoe store where she found a pair of strappy black shoes with three-inch heels.

On the way back to her office, Mom told me to go to the lingerie shop, take in the dress and shoes, and ask for help picking out the perfect bra, panties, and stockings to go with it.

“No one is going to see my underwear, Mom.”

“You will.”

I remember being told sexy lingerie was to make me feel good, so I agreed to do what she told me. After dropping her off, I drove to the shop and took my new things inside.

I found a woman who looked my sister’s age and asked her for help. I explained I was going to dinner with my boyfriend and wanted lingerie to wear with my new dress. After removing the clothing from the garment bag and showing it to the woman, she took me into the dressing room and told me to undress.

While I removed my tee shirt and shorts, the woman left returned with several bras and held them to my chest one at a time. One of the bras had small sheer cups that fastened in front. She suggested I try it on with the dress. After putting the bra on, the woman measured me and left, returning with the same bra in a different size.

Once I had the bra on, she adjusted the thin straps and had me put on the dress.

By the time I was finished, I had the new bra and a pair of matching panties. The panties were cut high on my hips and trimmed with scalloped lace. I asked about stockings and a garter, but she suggested thigh-high stockings because they didn’t need a garter to hold them up.

With my things in hand, I headed home to wait until it was time to get ready, sitting in my bedroom and checking my email, trying to kill time. After deleting the spam and answering Lindy’s email, I surfed the web.

I’d learned everything I knew about a guy’s cock on the Internet, save the bull they teach you in school. I hadn’t been very interested in the male body until lately, but now I wondered what a real cock looked like. I saw the photos on the monitor and wondered if all men’s cocks were the size and shape as the ones I saw.

As I surfed, I saw a newsgroup displaying pictures of amateur men and women. I clicked on one photo after another, realizing cocks were diverse in size. One series showed a young couple in various sexual acts.

I studied each photo as it appeared on my screen, seeing how the girl wrapped her hand around her lover’s member and stroked it. I saw her kissing, petting, and putting it into her mouth. I also saw pictures of the man with his mouth on her breasts and crotch.

The pictures made me feel funny inside. I rubbed myself as I came to the end of the couple’s photos. Leaning back in my desk chair, I thought about the pictures and how things that repulsed me a few months ago were now intriguing and exciting. My sister’s vivid descriptions of her sexual adventures were at the forefront in my mind.

At three-thirty, I went to my bathroom and filled the tub. Baths weren’t my favorite, but I didn’t want to get my hair wet. I added bath oil to the running water, let the tub fill halfway, got into the warm water, leaned back, and relaxed as the fragrant bath oil soothed my body.

While I lay there, I scooped water with my hand and poured it over the exposed parts of my body. My hands went to my breasts, and I began to toy with my nipples as I rolled them between my finger and thumb, pulled on them, and rubbed them with the palm of my hand.

My pussy received the signals from my nipples as it did when Kyle touched my breasts. While pinching and pulling at my nipples, I discovered the line between pleasure and pain. I moved one of my hands between my legs and continued my self-discovery.

Usually, I concentrated on getting myself off, but today, I was more interested in what got me there. I moved the fingers of the hand between my legs lightly over my labia and my clitoris. I pushed a finger into my opening, cringing as I stretched my hymen. Searching, I found the opening in the membrane and let my finger enter me. I could feel the silky walls of my pussy and moaned as my finger moved as deeply as possible.

I didn’t intend to bring myself to a climax, but I did. My fingers on and in my pussy and playing with my nipples caused a satisfying orgasm. After resting for a few minutes, I finished my bath and stood in the tub. While the water drained, I used the removable shower head to rinse myself from the neck down.

I dried my body, wrapped the towel around my waist, touched up my hair, and applied a little makeup to my eyes and cheeks. In my bedroom, I slipped on the new lingerie. As I checked myself in the mirror, I smiled and felt the lace tops of the stockings.

I slipped the dress on and pulled the side zipper up. The shoulder straps were barely wide enough to hide my bra’s straps, but the dress fit so well that they didn’t show. I sat on my bed and put on the shoes, buckling the straps around my ankles, then put on my new necklace and centered it on my chest. Luckily, I owned a small black purse to go with the dress.

I went downstairs and sat in the family room, waiting for Kyle to arrive. My parents came home early from work to see me before my date. Dad let out a wolf whistle when he saw me. Mom told me to stand up and turn around so she could see how I looked. When she lifted my dress to see my stockings, I looked to see if my dad had watched.

“You look lovely, Trish.”

“Thanks, Mom. I hope Kyle likes it.”

“If he doesn’t, he’s dead,” Dad said with a chuckle. I knew my dad saw my stockings.

At five minutes after five, the doorbell rang, and Dad went to answer it. Kyle came into the family room behind my dad and stopped dead in his tracks when he saw me. We stared at one another as Kyle smiled from ear to ear.

“Wow, you look great, Trish.”

I went over to Kyle and kissed his cheek. “You look very handsome tonight.”

Kyle wore a light gray pinstriped suit with a black shirt and a gray tie. His shoes were polished to a very high sheen. I put my hand on his shoulder, felt his jacket’s fabric, and then took his hand.

Mom told me to wait a moment, left the room, and returned with a camera and a black lace shawl. After draping the shawl over my shoulders, she posed Kyle and me for pictures. Once she finished, Kyle and I left.

Parked in the driveway was a black limousine. It wasn’t as long as the ones we rode in for my sister’s wedding, but it was very nice. A woman dressed in a skirt, white blouse, and tuxedo jacket stood at the rear door. Kyle and I approached the car and got in when she opened the door for us. I got in first, trying to keep my dress from going too high. Kyle got in after me, sitting close as the woman closed the door.

Kyle and I sat beside each other and held hands as the driver pulled away from my house.

“This is very nice, Kyle. You shouldn’t have spent money on a limo.”

“No problem, my dear. The car belongs to the company my dad works for.”

I rubbed my thumb over the back of Kyle’s hand. “Are you going to tell me where we’re going?”

“Sure, we’re going to my house. My mom wants to see us before we go to dinner.”

“I meant, where are we going to dinner?”

“You’ll see.”

I shook my head and grinned, knowing I wouldn’t find out what was happening until we got to the restaurant.

The driver parked in front of Kyle’s house and let us out. Kyle got out first and waited as I climbed out. My dress rose as I tried to hold it down.

We went into Kyle’s house and posed for pictures. His Mom was teary-eyed as Kyle and I stood beside one another while his dad took pictures. She told me how beautiful I looked and gave me a hug.

Kyle and I left after fifteen minutes, got back into the car, and waited for the driver to take us to the mystery location. As we rode along Lake Shore Drive, I looked out the window at the lake. I put my hand on Kyle’s cheek, kissed him, and told him I loved him.

Putting his arm around my shoulders, Kyle pulled me closer as I put my hand on his leg and made a small circle with my finger just above his knee. When the driver turned onto Woodard, I asked where we were going again.

“You don’t give up, do you?”

“Nope, never!”

“Maybe I shouldn’t give up trying to mess around with you.” Kyle slipped his hand over my breast, squeezed it quickly, then removed it.

I tilted my head, looked into his eyes, and grinned. “Maybe you shouldn’t.”

Kyle furrowed his brow. I smiled, gave him a kiss, and sat back.

The driver made another turn onto another street, one I didn’t recognize. She turned again about two blocks down and stopped in front of a restaurant. The driver came to the rear door and opened it for Kyle and me.

“I’ve never been here before, Kyle. Is it good?”

“I’m sure you’ll like it if you like Italian food.”

I nodded, took his arm, and we went into the restaurant. Kyle told the woman at the desk he had a reservation and gave him his name. She picked up two leather-bound menus and led us to a table.

“Have you been here before, Kyle?”

“Yes, once when my parents brought me.”

I opened the menu and began to peruse the selections. A waiter came over, poured water into our glasses, and asked us what we wanted to drink. I ordered iced tea, and Kyle asked for a soda.

The dinner was served in several courses. The servers brought an antipasto, salad, soup, and pasta before the entrée. I had a veal dish, while Kyle had something made with shrimp.

The dinner took an hour to finish. I was so full I could barely move.

The waiter cleared the table, and Kyle reached to hold my hand.

“Thank you for the wonderful dinner.”

“You’re welcome. Want dessert?”

“Oh no, I couldn’t eat another bite.”

The lights dimmed, then came back up to their subdued level. The waiter came over with the bill, and Kyle gave him a credit card. After Kyle signed the slip, he stood up, walked to my side of the table, and pulled my chair out.

“Ready?”

“Sure, sweetie.”

Kyle took my arm and led me through the dining room. We went outside and into the waiting limo. I could see Kyle was hiding something, but I didn’t ask.

The driver took us to the Fisher Theater and went in to see Cats. I’d only been to a live play a couple of times. Both of them were amateur. I was mesmerized by the production and couldn’t remove my eyes from the stage.

During the intermission, we had sodas in the lobby.

“This is great, Kyle. I love the play. I love you.”

“I’m glad you’re enjoying yourself, baby.” Kyle kissed my nose.

We went back to our seats and watched the rest of the play. When it ended, we left and got into the car. Kyle leaned into the driver’s compartment, whispered something, then sat back.

Kyle put his arms around me, and we began to kiss. The driver closed the screen between her and the back of the limo. While we kissed, Kyle moved his hand to my breast. I pulled back after several minutes of heavy kissing and Kyle’s massaging.