My One and Only
The funny and inept story of my initiation to sex
Intro: This is a true story—the sometimes comedic, sometimes pathetic, almost always inept story of my entry into the wonderful world of sex. You’ll notice, I’m sure, that there’s no anal. In the early 60’s asses were for shitting, not for fucking. It wasn’t until the late 60’s—the onset of the sexual revolution—that we learned about things like the female orgasm, and the ass’s multi-functionality.
It’s just past 10 a.m. Saturday morning, Memorial Day weekend, 1962. It’s a beautiful spring day, the kind I find most often in the Northeast. Temperature in the mid-70’s, low humidity, and just a mere hint of a breeze, so I’m comfortable just wearing a college T-shirt, Bermudas (what they called shorts in ancient times like the ‘60’s) and low-cut sneakers with no socks. The sky, a deep azure shade that makes me feel I can see forever, is punctuated only occasionally by fluffy white cumulus clouds, themselves portents for more such glorious days to come. I have my parents’ bungalow on the north shore of rural Long Island for the weekend. I told them I wanted to go fishing. The blackfish should move inshore now and I do plan to fish a lot, but right now I have another matter in mind.
I’m in my dad’s Impala wagon heading west on Route 25A, the main east-west artery serving the north shore, heading toward the neighboring town. I turn just past the local dairy (yes, real cows!) and approach her house. Making the turn, I think back to how we met last summer. It was a party for her mom’s fortieth. My best buddy Ray works at the local supermarket weekends and summers where Mom is a full-timer. After intro’s to her mom and dad and birthday wishes we headed for the real reason we came—free beer. They had a kiddy pool just stuffed with ice and Pabst Blue Ribbon. Beers in hand we walked over to a small circle of kids sitting on the lawn nearby. Ray sat on one side and I found myself facing him next to a skinny dishwater blonde who I soon learned was the daughter, 16 years old, and looking forward to her senior year. We all chatted and joked for the duration of the party, becoming more chummy as the beer kept flowing. Eventually, I asked her out and she said ok. We set a date for the following evening.
I picked her up and we headed for the local drive-in. If you’re under 30 it’ll be hard to understand why anyone would go to a movie to sit in your car, listen to bad audio loaded with static, and occasionally try to watch through a teeming rain. But, at the time, it was a lot of fun and it was a great place to make out and more. I picked a slot about two-thirds toward the rear and close to the center. I rolled the window about halfway up and put the speaker on it. Then I surprised her by getting out and walking around to the passenger side, where I got back in and sat next to her again saying, “There’s a lot more room over here and the steering wheel won’t get in our way.”
I put my arm around her and we snuggled close waiting for darkness to fall. Shortly, the cartoon started. That’s another thing—every movie show always started one or more cartoons. I forget what it was—I never saw it. I leaned into her and we started to kiss as it began. She was a pretty good kisser with relaxed lips, sliding her tongue into my mouth as I eased mine into hers. Pretty soon we were in full make-out mode and we were climbing all over each other, grinding our crotches into any body part available. After a few minutes I told her, “I want you to touch me,” and moved her hand to my shorts, just over my now rock-hard cock. She was tentative at first, but didn’t seem to mind rubbing me so I unzipped and took it out. I was already very stimulated so, of course, I was very erect. Again, she was eager to touch and stroke it. By the time the feature started my cock was in her hand and she was caressing it with zeal. Once she showed willingness to fondle me I figured the time was right to try to touch her. I placed my hand on her right thigh and slowly moved it up and down . I slid my hand into those tight shorts and was rewarded with a warm moist sensation. She moaned softly into my mouth as I rubbed her pussy lips. It was only a moment before my fingers began exploring deep into her cunt. It was the first time I had ever touched a pussy. I was surprised at how hot and wet it was, and it smelled just great. Her moans became audible through our ongoing kisses. When I finger fucked her fast and hard she started to buck like a wild bronco.
We dated about forty times that summer but that was as far as we went. Why? Today we would have fucked at least forty times, but this was the 60’s and there were statutory rape laws in force. She was too young and I didn’t include five years as a guest of the state’s penal system among my long-term plans. Now, however, she was a year older and 100% legal.
I walked through the gate and knocked on the breezeway door. She came out wearing the tiniest pair of pink short shorts I had ever seen. They were like a second skin. I could see the top of her pussy, what’s now called a camel toe. Her sleeveless T-shirt was just as tight and it was clear she wasn’t wearing a bra. Her A-cup titties stretched the taut fabric and I could see her nipples clearly outlined. She never wore such sexy clothes last year. I guess she had grown up a lot over the winter.
“Hi, I wasn’t expecting you. What a nice surprise,” she said.
“I just got home from college last week and this was the first chance I had to come out here. My dad had me working ever since I got home, but I told them I wanted to go fishing, so here I am. Your mom and dad around?”
“No, Mom’s at work and Dad had to go to the store, but he should be home soon.”
“Listen, I have my parents’ place all to myself, why don’t we go over there where we can have some privacy?”
She wrote a note explaining where she would be and a minute later we were headed back to my place. I pulled the wagon up the lawn all the way to the back door. As we walked into the kitchen I spun her around for a long passionate kiss. She wrapped her arms around me and I put my hands on her firm ass pulling her vulva into contact with my thigh. We rubbed each other nonstop until I broke the kiss and pointed her toward the living room.
“Let’s go in here,” I said, pointing to my parents’ bedroom. I started to take my shoes off and she followed suit. I removed my shirt and shorts saying, “I think this will make things a lot easier.” She said nothing but stripped down along with me. I took her hand and led her to our destiny. We lay on the bed and soon we had picked up exactly where we left off last summer. My penis was hard when we walked into the room and she started jerking me immediately—slow steady strokes with just a little pressure from her hand. She wasn’t going to jerk me off this way but the feeling was still exquisite. Our kisses were long and deep; she shuddered when I put my finger into her and worked it around, abusing her pussy. It wasn’t long before we were totally absorbed in each other. I pulled back from the kiss, looked into her eyes and said, “You know, we dated a lot last summer. I think we’re ready. I want to go all the way with you.”
“Oh, c’mon, we’re as ready as any couple will ever be. I really want you. It’s all I’ve been thinking about for months”
Well, shit damn fuck! I thought. I never expected this. She was always so compliant in the past. I pulled away from her and lay across the bottom of the bed, leaning my head on my right hand. What the hell was I going to do now? If we didn’t fuck it was going to be a long, long weekend. I hadn’t planned on spending ALL my time fishing. Now, I’m usually pretty observant and that’s when I noticed something that seemed peculiar. At least, I thought it was peculiar. If I were refusing sex I’d be lying there with my legs together and, maybe my ankles crossed. But she had her legs apart at least 90 degrees and her knees up. I was looking right up into her wet hot pussy, still dripping from my fingering. Was this a signal that she really wanted me to go further; that she wanted me to take charge? Did “no” really mean “yes?” --only one way to find out.
I got up and cautiously moved between her legs; so far, so good. She actually spread them a bit further which I interpreted as a good sign. I moved forward and we embraced, holding each other tightly. We resumed our kissing. After a minute or so I raised my hips and moved them forward. With a perfection of aim I had never known before and would never know again, I eased effortlessly into her. As I did so, she pulled me to her in a powerful embrace and kissed me with a passion I had never imagined existed. Her pussy was soaking wet but she gripped me tightly. I lunged into her several times before celebrating to myself, “AT…LAST…I…AM…FUCKING!!”
Technically, I had lost my virginity about three weeks earlier when I took a known nympho to a college dance and then convinced her(it hadn’t taken much) to fuck me in her car afterwards. Unfortunately, I was too damned excited and came when I entered her. My entire fucking experience had lasted maybe a half second. How embarrassing!--all my hoping and planning betrayed by an overeager cock.
Now I was humping merrily away. I didn’t care that she just lay there passively, I was still fucking and I was really enjoying the slurping sound that was coming from her cunt. Suddenly, another thought struck—if I’m not careful I could wind up married to her! Yeah, I know-- why? But, that’s the way it was then. That’s how a lot of really shitty marriages began. It’s bad enough to be a kid with a kid, but imagine being a kid with TWO kids—a baby and a husband. Well, that’s another thing that wasn’t in my long range plans so I moved up onto my elbows , looked her in the eyes with what I thought appeared to be genuine sincerity and said, “I have too much respect for you to take a chance on getting you pregnant. I’m going to get some protection.” Good God, how do I come up with this crap? It was total bullshit but she bought it.
I pulled out, walked to my room, my cock dripping her secretions on the floor, and retrieved a condom from my top drawer. When I returned I made a big show of putting it on before climbing back onto the bed where I said, “Now, where were we? Oh, yeah, I remember.” And I again entered her sweet velvety pussy. It took a few minutes to get back into it again. Condoms then were really crude and extremely thick by today’s standards. Eventually, I did cum and cum good, after all it was my first real fucking cum. Did she cum? I have no idea! I didn’t even know then that girls could cum, so how would I know what to look for? So far as I know girls didn’t cum until the sexual revolution in the late 60’s. I’m sure it was a real surprise to a lot of guys—it was a hell of a revelation to me.
We lay there for a few minutes until I climbed off her. We snuggled for a while until she said, “I should probably get back. Let me up so I can clean up in the bathroom.” She grabbed her clothes and walked off. I took off the rubber and wrapped it in a paper towel before throwing it in the trash. She came out just as I was finishing dressing. She showed me her shorts; the zipper was broken.
“I’m worried my Dad will notice,” she said. “Can you fix it?”
I took the shorts which were little bigger than one of my handkerchiefs, and checked it out. The handle was broken off so there was nothing I could do.
“When you go into the house go right to the bathroom. When you come out you can tell him it just happened. Don’t worry, it’ll be fine,” I commented, adding, “Let’s go out tonight, ok?”
She told me she had a date and didn’t know how to get in touch with the guy, but she would break it when he picked her up that evening. We kissed again and I took her home.
That evening I was parked around the corner when he showed up. The asshole didn’t even go to the door. He just beeped his horn and waited. I was glad she was dumping him. No sooner had he angrily peeled out down the block than I cruised up to the door. She was waiting for me in another really tight pair of shorts and, again, no bra; we soon headed for the drive-in. Later I cursed myself for my stupidity. I could have just as easily have taken her back to my place for a good fucking instead of spending my money doing the same things we did last summer. I parked about 3 blocks from her house on the way home. I didn’t have to ask her; she shrugged out of her shorts and T and was ready to receive me. I’m tall so I had to bend my knees in order to fit into the Impala’s front bench seat (no bucket seats then). My sneakers were sticking out the window, a sure tip-off as to what we were doing, but, fortunately, nobody drove past while we fucked away. This time, and every time afterward, I slipped on a rubber. I wasn’t taking any chances. I had a harder time in the car sticking my cock into her tight hole but she was so wet that her natural lubes worked as nature intended. In an instant I was sliding in and out energetically. Again, she didn’t move, and to be honest, I didn’t know she was supposed to so I didn’t complain.
We made arrangements to go fishing the following morning. I picked her up around 10, stopping at a deli for some lunch and at the bait store for some sand worms, hooks, and sinkers on the way back. I had gone fishing yesterday with Ray and he was going to join us later on. Actually, I told him we were getting to the beach around 12 and asked if he would stay away until one. Of course, I expected him to come early so he could catch us fucking. That’s why we got to the beach by 11. To get there we had to walk down a path through the woods. These are private beaches so there’s never a crowd. On this day we were the only people visible for miles. We set up our towels near the water, and I got my rod (no, not that one—my fishing rod) ready. Once baited, I cast the sinker and hook out into an area I knew to be rocky. I set my rod into a sand spike, a long piece of tubing with a point on one end which is driven into the sand and holds the rod when you’ve something better to do. I definitely had something better to do.
“Ok,” I said, “I’m ready. Let’s do it again.”
“Here?” she replied, “What if someone sees us?”
“Like who? There’s no one here except us.”
“What about Raymond?”
“Don’t worry about him. I told him to come down around one so he’ll probably be here around 12:30, hoping to catch us, so we have an hour or more. It won’t take us that long.”
She started to remove her shirt (another T) and shorts. This was the first time I actually looked at her pussy in daylight. Yesterday I was so excited trying to fuck her I didn’t really look too closely. I could see she was a natural blond. Soon she was naked except for her sneakers. North shore beaches are loaded with billions of pebbles and walking on them can be agony until your feet toughen up. I pulled down my bathing suit and filled the rubber with my pulsating cock. I was just about to shove it in when my fishing rod bent over 90 degrees. Shit, what fucking timing—I had a bite and a good one! I jumped up tripping on the suit and grabbed the rod and reel. I was hopping all over with my suit around my ankles.
“Get up and pull my suit up, will you?” I yelled. It must have been quite a sight! I was playing the fish, trying to keep him out of the rocks, suit stuck on my shoes, rubbered cock sticking out at attention, moving like a hobbled horse while she was chasing me butt naked, trying to pull up that damned suit. Eventually we got it done, just in time, as I landed a five pounder. I hooked the fish up to a stringer, anchored it in the shallow water, and returned to her. This time my rod was again in the sand spike, but the hook and sinker dangled in the light breeze. I wasn’t taking any more chances.
I told her I wanted to try another position. “Huh?” she asked. “Yeah,” I replied, “why don’t I lie down and you can just sit on my cock? I hear from my friends that it can be really fun that way. And, besides, I can rub and play with your breasts. I don’t think I’ve ever really played with them. I was always occupied somewhere else.”
“Okay, I guess,” and she moved to the towels. I lay down first and she positioned herself over me. We obviously weren’t very experienced, either of us, so it took a while before we were able to connect. Finally, I fingered her to make her wet; my cock was still granite. I arched my back and pushed in about two inches. I pulled her down to meet me and eased further in. Now I started humping, slowly at first then harder and faster. I grabbed her small firm ass and pulled until I was in all the way. Once there I moved my hands to her tiny tits. They were small but her nipples and areoles seemed too big. Maybe that meant she was going to grow as she gained weight. I hoped so. I rubbed her hard nipples between my fingers, pinching and rolling them. She moaned loudly. I was really glad there was nobody around; I was sure she would be heard. Now we were bucking into each other as she rode me hard, rubbing what I later realized was her clit into the friction of my pubic hair. I could feel my cock moving in, out, and all around her hot box. Suddenly, I exploded into the condom—once, twice, three times. And then, one final spurt. I lay there exhausted from my exertions, but happy-- extremely happy. I pulled her down to me and kissed her for what seemed to be an hour.
“Do you think we should get up and dress? I don’t want to be caught like this.” She made a lot of sense so she backed off me. I was pretty soft now. I took off the rubber, dug a small hole in the sand, and dumped in the condom and wrapper. We dressed quickly; we weren’t wearing all that much when we started. I washed my hands in the cold salt water and resumed fishing. Sure enough, Ray joined us about 15 minutes later—only 45 minutes early. If he was upset at missing us he did a good job of hiding it. We fished throughout the afternoon collecting a few four to six pounders. We decided to give the first fish to her Mom so I cleaned it on the beach at water’s edge. We walked up the ravine and I took her home. I’d pick her up again around seven and I had already decided I wanted more.
I try to learn from my mistakes so no drive-in tonight. We drove straight to my place. I had some beer in the fridge, but she refused. It didn’t matter, I knew she would fuck me before the night was over. We sat on the couch and watched some TV, but neither of us paid much attention. We kissed and groped each other and soon enough we were both naked. I’m not sure exactly how it happened but we were where I wanted to be. I was massaging her breasts and pinching her firm nipples.
“Let’s try something else tonight. What d’ya say?”
“I don’t know,” she replied. “What do you want to do?”
“Well, I was thinking of oral sex.”
“You mean you want me to put your penis in my mouth? I don’t know if I can do that”
“Sure you can. And don’t forget, I plan to put my mouth and tongue on yours.” I really didn’t want to say “cunt” and I wasn’t sure how she’d react to “pussy.” So I figured she would know what I was talking about. “Tell you what, I’ll go first, then you, and maybe we can do 69, too. Ok?”
She gave me a look that said she was unsure so, since she didn’t openly object, I went ahead and did it. I knelt on the floor in front of her and pulled her hips to the edge of the couch. I put each hand on a leg and pushed them up and apart, baring her pussy to my tongue. I started with a big slurp that ran the length of her slit. I didn’t know much about her anatomy so I thought that if I just licked everything in sight I’d eventually hit some of the right spots. I licked all around her and sure enough she started to heat up. Her cunt started to drip and I found I loved the flavor of her. The more she leaked pussy juice the more I licked it up. I was having a great time and it seemed to please her, too. She moaned so loudly I thought she was a mooing cow. She started panting. Between that and the moaning I knew I was doing something right so I kept doing the same things. An idea struck me—what if I stuck my tongue into her? I figured she liked my fucking her so she’d probably like that, too. I learned very quickly just how much she did like it. My first clue came when she shouted, “Ooooohhh, do that some more. Don’t stop don’t stop don’t stop. Oooooohhh, ooooooohh!”
This was obviously the time for her to suck me. She was so hot I thought she would do anything. I moved back lying on the floor, pulling her with me. I moved her into the 69 position. I may have been naive, but I could figure that much out! She didn’t hesitate. She was rabid with desire. As soon as I resumed licking and sucking her she started in on my cock. First, she put her mouth against the side of my shaft like she was eating an ear of corn. “No, put your mouth on top and move it up and down.” She took one look at me, I guess for reassurance, and took me into her mouth. Fucking was great I decided, but this was something special. I could feel her tongue rubbing against my shaft every time she moved it in and out. In spite of all the fucking we had done earlier I had still come home and jerked off afterward. I used to be able to do that three or four times a day, so I was ready to cum again in no time. “I’m going to cum,” I said. She backed off; I wrapped my hand around hers and finished the job. I splurged all over her face, chest, and hand, a lot of it dripping on to my abdomen.
“That was great,” I said.
“Yeah, I liked it, too,” she replied. “It was easier to do and more fun than I thought it would be. I liked when you did it, too. Oh, it made me feel really, really good.”
“Then, I guess you wouldn’t object to doing it again sometime?”
“Yes, oh yes, as long as you’re going to do it to me. God, I’m a mess. I don’t know if I can make it to the bathroom without dripping all over.”
“Let me get up, then. Roll over and I’ll be back in a sec with some paper towels.”
We cleaned up and settled in to watch the TV. We both needed to rest before getting down to the serious business of the night – the fucking. By now it was totally dark, the only light coming from the screen. We usually leave the doors open but I got up and locked them. I didn’t want to be disturbed when the right moment arrived.
It took a while but we were young so we were able to recover after an hour or so. I knew she was ready to move forward when she sidled over really close to me on the couch. I was slouching so she put her head on my shoulder. This was the sign to start kissing her again, so I did. After all we had been through over the past two days I wanted to be really tender and sweet. My first kisses were soft and slow with just a teasing tongue, only intended to warm her up a bit. It didn’t take long; soon we were like animals in heat, clawing and grabbing at each other. It felt like the couch was bouncing all over the room. It wasn’t, of course. That was just us. I tugged at her clothes—for some idiotic reason we had dressed again. Once she was naked I literally ripped mine from my body. We came together in our lust. Thank God I had the rubber handy or I would have gone in bareback and who knows what consequences might have occurred. We rutted on the floor, first me on top plunging into her hard. When she responded I plowed her even harder. Then we switched and she rode me harder and faster than earlier on the beach. We switched back for the finish which came when I drove into her HARD. We pulled into each other as I emptied my balls into the condom. A rest, this time a very long rest, was needed before either of us could move.
Tomorrow was Monday, Memorial Day, the day I had to drive home. We decided to meet in the morning and fuck before going to the beach to fish. I took her home, returned to the bungalow and fell into a deep sleep.
Monday morning I was up early. I packed the car so I’d be ready to go when the time came. Once I had cleaned myself I threw on my bathing suit, my sneakers, and a fairly clean T-shirt, one of the few I had left. I went to pick her up. We made the now usual stops—the deli, the bait shop, and, this time, the pharmacy. I was out of rubbers. At the bungalow she raced inside almost before I had a chance to stop the car. By the time I entered she had removed her clothes. “I want to suck you again. Will you eat my pussy?” “Oh, you know it,” I replied. Soon I, too, was naked. She grabbed my erect cock and tried to pull me to the floor. “No, not the floor, I have rug burns all over my ass from last night. Let’s jump into my parents’ bed.” Instead, she led me into my room and the small twin bed I had occupied only two hours ago.
“I want to use the smaller bed. We’ll be closer together.”
“I don’t know how we could be any closer than we’ve been all weekend. You’ve practically been inside my skin.”
“Maybe, but you have definitely been inside me,” she said as a final statement before kissing me hard and hot and pulling me onto the bed. We writhed sinuously on top of the covers as our heat built steadily. She pulled back from our kiss, lowered her head and took me into her mouth. “I never thought I would like this, but, you know what, I love it. It gives me such a feeling of power over you.”
“All I can tell you is that when you do that to me I can’t resist you. Swing that pussy up here and let me lick it for you.”
She must have used some perfume down there because she smelled of lilac-- on the outside, anyway. Once I had pried her pussy lips open she tasted as sweet as yesterday, but better. She must have just showered because she tasted so fresh and clean. While I sucked and kissed her hole her mouth was impaled on my cock. The sensation of her tongue squeezing my cock in her mouth and throat was addictive. I couldn’t get enough. “I want you now; I need you NOW!” I practically shouted. I was so hungry—starving for her sex. I got up, positioned her with her butt facing me and drove my cock into her hole. If she hadn’t been so wet I’m sure I would have really hurt her. Instead, her natural lube made it an easy entry. I humped her doggie fashion until she reminded me that I had forgotten the rubber. Damn, I was so caught up in the passion of the moment it hadn’t crossed my mind. I withdrew quickly, opened the box in my shorts, rolled it on my throbbing cock and put it back into her waiting heaven. It couldn’t have taken even ten seconds. I never moved so fast. Too soon I could feel my balls contracting as a thick stream of semen pulsed into and through my cock. My whole body spasmed as my orgasm passed through me. When it ended we were both drenched in sweat. I fell on top of her and we rested, eventually falling into a light sleep.
We woke and dressed only five minutes before Ray knocked at the door. We gave each other knowing looks and laughed. He probably thought we were crazy. We fished until about two in the afternoon. It was ok but not great. We each caught a couple of fish and threw all but two back. Ray kept them; I already had enough to take home. Once Ray had gone I used the outdoor shower again. I tried to get her to join me, but she wasn’t interested.
I asked her, “One more time?”
She shook her head, “No, thanks, I’m kind of sore down there. I’m not used to all this screwing. Can’t we wait until next weekend? But…I…could…give you a going away present, though.” She dropped to her knees and took my dripping cock into her mouth.
“Ok, that’ll give me something to look forward to and this will sure as hell help me remember you.”
“Me, too,” she said smiling around my dick. She licked my head then moved me deeper into her throat. She gagged a bit; she’d never taken me so deeply. She regained her breath and got into a steady rhythm, increasing the pressure on me as she went. I had cum pretty hard earlier so I was slow to repeat. However, after about twenty minutes I felt that familiar pressure build in my balls. This time I exploded into her mouth but she didn’t pull away. She drank it all and even licked my cock clean when I was finished.
I dressed, put the fish into a cooler with some ice, locked up, and took her home. Then I proceeded on my long drive hoping I’d miss the bulk of the traffic and looking forward to the rest of the summer.
I had quite a few lovers over the next few years until I married. Most of them were better at sex than she was, but I wasn’t going to complain. I knew then that we would fuck many times over the coming years. She was my first and, at that point, my one and only.