I was a sixteen-year-old high school Junior in the Spring of 1966. Like many boys my age, I had a major case of insecurity, especially around girls. I had heard all the guys’ locker-room talk about what they had done with their girlfriends. All I had ever accomplished with a girl was get a quick kiss in the bushes when I was about 13 years-old. I guess I was a late bloomer.
About a month before school let out for the summer, I bought an old car and enjoyed my first taste of freedom. No longer was I dependent on Dad for transportation. The car was a 1951, two-toned green, Chevy Deluxe, and it cost me all of $50.00. It was old, but it looked decent and ran well. It only used a quart of oil a week, and the six cylinder engine got pretty good gas mileage, not that gas mileage was a major consideration in 1964. Gas was 25-30 cents a gallon.
I was the only guy in my group to have his own car. That made me rather popular among my peers. Four or five of the guys would each chip in 50 cents for gas, and we could cruise all night.
Throughout the nearly completed school year, I had been enamored with the sister of a classmate. She was a Freshman and had recently turned fourteen. Ann and I had chatted many times in the hallways of our school or at ball games. She had a giggle in her voice that I just loved hearing. She seemed sweet, but since I had no car, there was no way I could take her anywhere on a date.
Shortly after getting my car, I worked up the courage to asked Ann out. I asked her if she’d like to go for a burger at the local A&W. At the time, I couldn’t afford much more. I began breathing again only when she said she’d go with me.
Ann was cute and petite. She stood 5’5 and weighed maybe 100 pounds. Her eyes were deep brown. She wore her hair in the typical styles of the 60s. It was either piled high on her head in a beehive or flipped up at her shoulders. Her hair was held in place by a heavy coating of hair spray. Ann, and her friends, must have kept the hair spray industry in business. Many of the guys joked about not smoking around their girlfriends hair. We feared a wild spark could trigger an explosion of all that hairspray.
Friday evning I went to Ann’s home to pick her up. Instead of waiting in her driveway and blowing the horn, I got out and knocked on her door. She invited me in to meet her parents. I was scared to death, but stood straight and walked in.
Her mother gave me a look that could have frozen a tropical paradise. Her father, however, offered me a beer. Hoping to make a good impression, I told him that I couldn’t drink at that time. Since I would be driving Ann to the A&W, and didn’t want to get into any trouble. I said I’d have to pass on the beer. I then told him I’d be happy to have a beer with him when we returned later, if he still wanted me to.
Ann father smiled at me, but said nothing.
Ann’s mother asked me a million questions. Her father just continued to smile at Ann and I. He winked as we headed for the door, and told us to have a good time.
Ann was wearing her typical attire, a colorful blouse and blue jeans. Her blouse seemed a bit to small and the button between Ann’s breasts seemed about to let go. Ann’s breasts were small. They seemed to be about the size of oranges. However, her tight blouse tended to show them off nicely.
During the 10 mile ride to town and the A&W, Ann sat near the passenger door. We talked about many things, but mostly school stuff. As we pulled into the A&W, I told her she was my first real date, and I was a bit nervous (scared to death was more like it).
Ann smiled and slid over to sit close to me. When I got the car parked in a drive-in stall at the A&W, she took my right arm and draped it over her shoulders. She then leaned over and kissed my cheek.
The car-hop came and took our orders for Trojan Burgers, onion rings, and root beers. The Trojan Burger was a feature of that particular A&W. It was named for the local school’s sports teams. Over the succeeding 35 years, I have never been able to find a burger that tasted quite as good, or made as much of a mess.
After finishing our burgers, and a second root beer, it was well after dark. Ann and I began heading back to her home. She suggested we take a different route. A route that took us over the county’s back roads. About half way to her place, Ann pointed to a secluded turn-off and told me, “Pull in there.”
The turn-off wound about 100 yards off the road and into some woods. If she hadn’t known it was there, we would never have seen it.
I was so naive! I had no idea why she wanted to stop there. Ann was about to show me why.
I pulled to the side of the road, turned off the car’s engine, and left radio on. It was, of course, playing 60s rock-n-roll. Ann turned and gave me a firm tongue-in-cheek (her tongue in my cheek) kiss. She then twisted around until she was lying cradled in my left arm. She took my right hand and pressed it tightly to her left breast.
I moved the seat all the way back to give her as much room as possible. I may have been inexperienced and naive, but I was not stupid. I began kneading her breast through her clothing. I felt her nipple begin to harden.
Ann softly said, “Unbutton my blouse.”
With a trembling hand, I clumsily unbuttoned her top. As I opened her blouse, it fell away leaving just a bra covering her breasts. “That too!” she said, as she rolled onto her right side and hugged my neck.
Reaching behind her, I fumbled with the clasp of her bra. I eventually got the clasp open, and, with Ann’s help, removed and tossed her bra into the back seat.
Her firm young tits were a little more than a good hand full, and her nipples were very hard. I gently rubbed, squeezed, and pinched her tits and nipples.
Ann was soon moaning and rocking in my lap. After a short time, she took my hand from her chest and guided it slowly to her crotch. As I rubbed her crotch, she began lifting her hips to meet my hand.
Becoming bolder, I unbuttoned her jeans and lowered the zipper. Reaching inside her pants, I found and began rubbing her bush through her panties. Ann pushed my hand down further until I was rubbing her pussy’s slit. Her panties were soaking wet. Pushing them aside, I continued stroking up and down her slit with my middle finger.
Near the top of one of my strokes, I must have hit something tender because Ann abruptly tensed. I felt what seemed like a small, hard, pebble above her wet hole. When I caressed it, Ann grabbed my hand, pushed it harder into that little hard spot. She gasped, “Oh yes! Right there!”
After a short time of gently rubbing that little pebble, Ann began violently thrusting her hips up to my hand. Not knowing what else to do, I just continued rubbing that little pebble, albeit a little faster and firmer.
Ann soon began to relax, and, with a deep sigh, lowered her hips back to the car seat. She then rolled onto her right side and slid back from my belly a bit. She started rubbing my dick through my pants. It didn’t take her long to loosen my belt, unbutton and unzip my pants, pull my shorts down, and take my dick in her hand. That alone nearly got me off. She was the first person to ever touch my dick other than myself, at least, since I was a baby. Ann was stroking up and down my dick with her left hand while she kissed and licked its head. I was soon about ready to cum.
I told Ann of my impending eruption. She tightened her grip on my dick and sped up her stroking.
When I erupted, she kept pumping until I was dry. She then sat up, wiped her hand on tissues from her purse, and gave me a very passionate kiss.
We reassembled our clothes, and, while holding each other tightly, I slowly drove her home.
When we got to her place, I had that beer with her father. He seemed to enjoy my company, and I enjoyed his. Most of Ann’s family resented her father’s heavy drinking. Ann had explained to me why he drank so much. I soon came to understand his need for alcohol. He was very ill, and he used beer for pain relief. He suffered from cancer and passed away a few months later.
I didn’t drink very often, so I nursed one beer for nearly an hour. By that time, it was getting late. So, I said goodbye to Ann’s father. Ann accompanied me as I headed to my car. On the way out the door, Ann’s father told her to be sure to give me a nice good-bye kiss. I almost felt bad knowing what we had already done. Almost!
Ann and I made a date to see a movie at the local drive-in Saturday night. As I opened my car door to leave, she not only kissed me goodnight, but firmly rubbed my crotch before she went inside.
Whew! What a first date.
About 6:30 Saturday evening, I picked Ann up at her home. Her mother had already gone to work. Her father asked where we were going. I told him we’d be getting a burger and going to a movie. I didn’t tell him the movie was at a drive-in. He told us to have a good time and waved as we pulled out of the drive.
As soon as we hit the road, Ann slid close to me and kissed my cheek. I draped my arm over her shoulder. When she swivelled slightly to her right, my hand, more or less naturally, settled on her right breast. I lightly rubbed her breast through her blouse and bra. Reaching into into the top of her blouse, I squeezed her left tit through her bra.
Ann then exhibited some contortionist abilities and removed her bra without disturbing the buttons of her blouse. That gave me much easier access to her tits. Opening her top two blouse buttons, and sliding my hand into the gap, I began gently rubbing and squeezing her tits. Her nipples were soon hard little knots pushing against her blouse.
Ann didn’t replace her bra when we got to the A&W. She merely fastened one of the two open blouse buttons. Her firm tits and hard nipples seemed to be trying to escape her blouse all the time we were at the A&W.
After eating, we went to the drive-in. I found a place in the back line to park, bought us some drinks, and settled in to watch the double feature.
Ann laid her head on my shoulder. My right arm returned to her shoulders, and my hand to her right tit. Her left hand was rubbing the inside of my right leg. It was obvious we wouldn’t be seeing much of the movie.
I was about to learn why drive-in theaters were called passion pits. As the lot lights dimmed, and the screen came to life, I unbuttoned the top four of Ann’s six blouse buttons. Her firm young tits were fully exposed to my hands and eyes. Her hardened nipples were about the size of an elementary school pencil eraser. They almost looked out of place on her petite tits. Gentle pinching of those nipples brought groans from Ann and her breathing grew rapid.
The movie had barely started when Ann laid her head in my lap and smiled up at me. I continued rubbing and squeezing her tits with my right hand while stroking her hair with my left. She was soon cooing and moaning almost like a kitten purring.
I began moving my hand down her belly. A brief pause to open the button and zipper of her jeans, and I had easy access to her panty covered pussy. Her panties were already damp. After I had stroked her slit for a short time through her panties, they had become soaked with her pussy’s juices.
Ann lifted her hips and pushed her jeans and panties down to her ankles. With a few little kicks of her legs, Ann had her shoes, socks, jeans, and panties laying on the car’s floorboard. She dropped her left leg to the floor and laid her right knee against the seat back widely opening her crotch for my hand.
I stroked up and down Ann’s slit and gently spread her pussy’s lips open with my fingers. As I slowly rubbed her little pebble, Ann began lifting her hips off the car seat.
“Oh yes! Right there! More!” Ann gasp.
As she rapidly thrust her hips up to my hand, I shoved a finger into her hole. That finger was quickly joined by a second.
Ann, breathing very hard, reached down and held my hand tightly to her pussy, arched her back, and held her pussy high in the air. “Oh, oh, oooooh!” She gasped through rapid breaths.
I could feel muscles inside her pussy twitching around my fingers. Her freely flowing juices from her pussy, drenched my hand and left a wet spot on my car’s seat.
As Ann slowly settled down, she rolled onto her right side and began stroking my rock hard dick through my pants. Her face was only a few inches from my zipper. Almost before I knew it, she had opened my belt, unsnapped and unzipped my pants, and had my dick in her hand. She gently stroked the full length of my dick several times before starting to kiss and lick the underside of it.
Then, without warning, Ann sat up, turned her body to face me, and laid back. She placed her head on the passenger door armrest, lifted her left leg over me, and laid it against the car’s seat back. Her right leg was draped off the seat to driver’s side floorboard. Some time during the process, Ann had finished opening her blouse. It lay crumpled along her sides.
As I viewed the body before me, I was in awe. Ann was the first naked female I had ever seen. She was so beautiful. Her small tits were well proportioned to her petite body. Her belly was smooth, flat, and soft. There wasn’t an ounce of fat to be found on her young body. A small patch of dark curly hair covered her pubic mound.
I must have been staring at her, for after a while, she brought me back to reality. Holding her arms out to me, in a soft and sweet voice, she said, “Come here!” I twisted in the seat, pushed my pants down to my knees, laid between her legs, and kissed my way up her torso to her mouth. My legs, bent at the knees, rested on the driver’s door. My dick was only inches from Ann’s pussy. I moved up to where my dick just barely touching her pussy.
“Come on honey, make love to me, now.” She said, somewhat impatiently.
Naively thinking she was a virgin, as I was, I very slowly pushed into her hole. I didn’t want to hurt her. I had heard it hurt the girl the first time she had sex.
When I had about three inches of my cock in Ann’s pussy, she wrapped her legs around my hips. She used her legs to pull me all the way into her pussy. I met no resistance. She held me there for a short time. Then, relaxing her legs, she let me pull partially out before pulling me back in. Ann used her legs to set the pace of our stroking. She soon had me hammering in and out of her hot, tender, 14-year-old pussy. In what seemed like no time, we were both about to get off.
“I’m about to cum” I gasped.
She raised her knees to her chest, hugged me tightly, and said, “Me too.”
After several hard deep strokes, I slammed deeply into her, and she locked me there with her legs. Being held deep in her pussy, I pumped my load of cum into Ann. Her pussy muscles seemed to be milking the last drop of cum from my cock.
As our orgasms subsided, Ann lowered her legs. We lay together until my dick softened, and I pulled out. Holding each other as we came down, our breathing soon returned to normal.
I asked, “That wasn’t your first time was it?”
“No!” she said with a smile. She gave no further answer, and I didn’t asked any more questions.
We dressed and cuddled through the rest of the double feature.
Ann was my first lover and we were soon going steady. We dated through the end of high school and married the following September. Our marriage only lasted a few years, but they were fun years filled with sex. Ann loved to fuck.
Unfortunately, one man was apparently not enough for her. She was one horny little bitch that turned out to be a whore. It wasn’t long before she was giving her favors to someone new, as well as me.
She was a great fuck though, and serviced me well during our short marriage. Ann taught me much of what I needed to know about how to pleasure a woman. For that, I am still grateful.