Cindy Vanderhoff Part 1

“I don’t think he’s going to last much longer,” the doctor told the family gathered around the bedside. “His breathing is forced. He doesn’t seem to be aware of his surroundings. I’m sorry.”

“Cindy Vanderhoff…” 

They turned to look at the old man who had just mumbled this name. His eyes fluttered and then opened. He looked around the room like he was searching for someone.

“Cindy Vanderhoff…” he repeated in a raspy whisper.

“Who is he talking about?” The doctor asked.

No one knew. The old man closed his eyes. Time went backwards. The memories came flooding back. 

**********

The year was 1957. I was seventeen years old and entering the 12th grade. We lived in a suburban community just outside of Cincinnati where all the houses look the same. When I wasn’t in school I was working at the local hardware store. I had been on a few awkward dates, but most of my knowledge about was from listening to other boys talk in the locker room, and most of the time they didn’t know what they were talking about.

My lack of experience with the opposite couldn’t be pinned to any one thing. I wasn’t a bad looking kid. At five foot nine and 165 pounds with brown hair and blue eyes, I was more or less average. I wasn’t a jock, although I had joined the track team and was a mediocre long distance runner. I did make good grades in school, but that wasn’t going to impress many of the girls.

Our school had three kinds of girls. The “popular girls” hung in cliques. They were worried about protecting their reputations. What they did when they were alone with their boyfriends was never discussed. Then there were the bookworms, jocks and nerds who didn’t thrive on trying to impress boys with their looks or femininity. Finally there were the fast girls who liked to fool around. Some girls could straddle two categories but it was difficult.

Cindy Vanderhoff was in a category all by herself. She was beautiful by any standard. She had high cheekbones, big brown eyes and a perfect smile with pearly white teeth. Her soft brown hair bounced against her shoulders when she walked. Her sway was graceful and feminine, and her shapely breasts rode high on her chest. Every boy in the high school secretly lusted after Cindy. I was no exception.

Cindy had transferred to our school in the middle of last year. She was outwardly friendly to everyone, but had remained a mystery. She avoided hanging with the popular girls despite their best efforts to draw her into their cliques. Her best friend was a homely looking bookworm named Betsy Cox. Normally Betsy would have been classified as a nerd, but there were rumors that she had “put out” for some of the boys at the local college.

High school boys were like putty in Cindy’s hands. A smile and a friendly greeting in that soft and y voice had them tripping over themselves. She played hard to get and wouldn’t go out on a date until she had been asked several times. She seldom dated the same boy more than once. Some of those that went out with her said she was a cocktease. Others claimed to have gone “all the way,” but no one believed them.

Cindy and I had one class together, World Hi. She was always nice to me and said hello when we passed in the hallway, but I had no illusions that her interest was at all romantic. That didn’t stop me from fantasizing. I had spewed a lot of semen, imagining what it would be like to kiss her and feel her breasts or see her naked.

One afternoon, shortly after the school year began, Cindy and her dad walked into the hardware store where I was working. She came over to say hello, putting her hand on my forearm, and looked up at me with her big brown eyes. She was saying something, but I was so excited from her touch that it didn’t register. I mumbled something unintelligible in response.

“Good,” she said as she was leaving. “Then I’ll see you at sixthirty on Friday, Paul. It’s okay that you don’t have a car. We can walk to the movies. Do you know where I live?”

Cindy scribbled her address on a piece of paper and handed it to me. Her smile was a killer, sending my heart fluttering. She squeezed my arm and walked away. I watched the back of her pedal pushers sway back and forth with each graceful step. Cindy Vanderhoff, the hottest girl in school, had asked me to take her to the movies. I couldn’t believe it. 

I was terrified when I showed up at her house on Friday night. She opened the front door and greeted me with that heartmelting smile. She wore a green skirt and a white blouse. I had on a nice pair of pants and a button up shirt. She invited me inside to meet her parents. If they only knew how often I jerked off to images of their daughter they would never have let me go out with her. After a few minutes they let us escape.

“You look very handsome tonight,” Cindy said as we walked out the front door. “I’ve wanted you to ask me out for a while and thought maybe you didn’t like me. Betsy said you were just shy and that I should take the initiative. I hope that’s okay.”

I don’t remember much of what we discussed during the walk to the movie theater. Cindy did most of the talking. About halfway there, she slipped her hand into mine. Our fingers intertwined. I paid for the tickets and bought some popcorn. We sat near the back, holding hands. Part way into the movie, Cindy looped my arm around her shoulder and snuggled closer. She rested a hand on my knee. My cock jumped.

After the movie ended, we walked back to her house. We reached her front porch. I was nervously trying to decide whether I dare kiss her goodnight when she invited me inside. We went into the front room and sat on a loveseat. Cindy explained that her parents wouldn’t be home until later. She snuggled close and pulled my arm around her. 

“You can kiss me if you want.”

She tilted her face towards mine. I was in way over my head and nervous that I wouldn’t live up to her expectations of what a kiss ought to be. She leaned closer. Our lips met. Hers felt so soft and sensual. It wasn’t just a peck on the mouth. It was a real kiss. I had kissed a few girls, but nothing like this, and certainly not with the hottest girl in school.

Cindy threw her arm around me, gently massaging the back of my neck. Her tongue brushed across my lips. I opened my mouth. My hand slid to her waist and pulled her closer. Our tongues swirled together in a dance of passion. Her fingers ran through my hair. She moaned into my mouth. Her lips moved to my neck. She kissed and nibbled on the thin skin, then slid up to my ear. 

“You’re a good kisser,” she whispered in a soft, y voice.

We resumed kissing. I eagerly welcomed her tongue back into my mouth. Her hand slid to my chest, rubbing it tenderly. My cock felt like it was going to rip through the front of my pants. What happened next left me breathless. Cindy took my hand, the one on her waist, and moved it over the shapely swell pushing out from her blouse. I thought I must be dreaming. The hottest girl in school wanted me to feel her up. 

This was completely new territory for me. I had no idea what I was supposed to do. I pressed my palm over her breast and rubbed it in circles. My fingers gently squeezed the soft tissue. She moaned into my mouth, encouraging my exploration. Cindy lifted her arm to give me better access. I fondled her more aggressively, squeezing firmly with my fingers through her blouse. I had never been so turnedon in my life.  She finally pulled away from the kiss.

“Don’t tell anyone I let you feel me up,” Cindy said. 

I nodded. Who would believe me anyway? We continued kissing, and I continued squeezing her soft breast. Her hand rubbed my chest and then my stomach. I was seeing stars. My hard cock was about to explode in my pants. Before that happened, she pulled away and stared at me with those big brown eyes, like she was sizing me up. 

“Can I trust you?” Cindy asked.

I nodded, my breathing unsteady. What happened next made me wonder if I had entered the twilight zone. Cindy unbuttoned her blouse. When she was finished, she reached behind to unfasten her bra. She took my hand and moved it to the warm flesh of her naked breast. Her lips moved back to mine, and we resumed kissing. 

My head was spinning. My heart raced. Nothing had ever come close to the excitement I was feeling. I gently squeezed the soft tissue with my fingers. My poor cock was throbbing and leaking like crazy. It didn’t help when Cindy dropped a hand to my thigh. She moved her lips to my ear.

“Touch my nipples,” she whispered.

Did she really say that? There was one way to find out.  I brushed my fingertip across the hard tip pointing out from the top of her breast. Cindy moaned. I gently rolled it between my thumb and forefinger. Her hand moved higher on my thigh, dangerously close to my throbbing cock. I moved mine to her other breast and repeated the ritual. Her breathing became heavier. She pulled my head down and slumped back on the couch, guiding my lips to her nipple.

“Kiss them.”

I had to be dreaming. I took her right nipple into my mouth, rolling my tongue over the hard nub poking out from the top. Cindy’s moans became louder and more erratic. I moved my mouth to her other breast, raking my teeth across her nipple. Cindy stiffened. She gasped and shuddered. She pulled my head up and kissed me hard, her tongue swirling in my mouth. 

Cindy slid her hand over the bulge pushing out from my trousers. I was seeing stars. Her fingers squeezed my cock. She moved her lips to my ear and pushed her tongue into the cavity. It was too much. My cock pulsed. Spurt after spurt of hot cum exploded into my briefs. She must have sensed something had happened. She pulled away and looked at me.

“Are you okay?”

“Um, yeah. I just, um, need to use your bathroom.”

“Sure. It’s down the hall.”

I went to the bathroom and was able to minimize the damage before it had seeped through to my pants. When I returned, Cindy was sitting up on the couch, her bra in place and blouse buttoned. She stood and smiled at me.

“My parents will be home soon, so you better go. I had a really good time tonight, but you’re dangerous to be with, Paul. I’ve never gone that far with a boy. I hope you don’t think I’m fast.”

I wanted to believe her, but it didn’t make any sense. I figured I was just another one of her cockteasing victims. Was she going to tell Betsy Cox that she made me cum in my pants and get a big laugh out of it? I didn’t care. It was a night I would never forget. I had felt and kissed the naked breasts of the hottest girl in school. 

At the front door, she kissed me goodbye, but it wasn’t much more than a peck. I returned home. That weekend, I pounded my cock raw, reliving the experience.