A fifty-five-year-old man wrote:
It was a true disaster. The girl was six or seven years older than I was, and she found out that I was a nineteen-year-old virgin. Alter pulling me into her bedroom, we started kissing and groping each other. It took about forty-five seconds of her hand for me to cover her with my come. How embarrassing!
A thirty-three-year-old woman wrote:
It sucked. It was with my ex-husband who was my boyfriend at the time. Wham, bam, and then he said he couldn’t wait to tell his friends. As I look back on it, I wonder now why I married him at all.
A forty-three-year-old woman wrote:
The only reason I did it was because my sister, who was younger than I was, had been doing the deed for a while. At the time I was almost nineteen and I guess I let my boyfriend talk me into it.
After I had my clothes off, I chickened out and told him I did not want to do it. He would not let me stop and forced me to do it anyway. No amount of crying or begging made him listen. To make matters worse, my sister was in the next room and heard me crying and pleading with him to stop. She couldn’t do anything about it. To me sex sucked and I saw no future in it.
A fifty-year-old woman wrote:
It was painful, I was afraid, and I hated it. I did it that once and didn’t do it again for two years.
A thirty-year-old woman wrote:
My first time was with this guy I really liked. He pressured me into it, telling me he’d love me more if we did it. I guess I fell for that, so we went to his house and had sex on his bedroom floor. Not only did it hurt but I bled a lot. He never talked to me again.
A fifty-six-year-old man wrote:
My first time, and hers, was on our honeymoon. We got all hot and I pushed my cock into her. As hard as I tried, I couldn’t get all the way in. Frustrated, we tried again later and the same thing happened, and continued happening all that week.
When we returned she went to the doctor and it turned out that her hymen was very thick and it had to be surgically broken. Once it was, and she waited as long as the doctor said, we finally did it. Maybe because we had had to wait too long, it was explosive for both of us.
A nineteen-year-old woman wrote:
My first time was really bad for several reasons. First of all, I was too young, only fifteen at the time. Second, we were both virgins and very stupid about sex. We lasted maybe a minute before we both got scared and stopped. Then, until I got my period three weeks later, we were scared to death I was pregnant, even though we used a condom and he never got off. See how stupid we were?
Of course, some lucky folks really enjoyed their first time.
A twenty-seven-year-old woman wrote:
It was a very good experience, with a guy I really cared about. He spent a lot of time making sure it was great for me, exciting me orally and making me come that way before he even tried to enter me.
A twenty-five-year-old man wrote:
I was quite young, maybe fifteen or sixteen, and my friend’s mother seduced me.
My friend had left me at his house and had gone fishing. His mother asked if she could make breakfast for me and I said sure. After breakfast she asked me if I thought she was attractive. I said, “Yes,” and she asked if I would like to kiss her. Boy, did I. About five minutes later our clothes were off and she was on top of me on her bed.
It was wonderful but a little weird. I had masturbated by that point in my life but actual intercourse was truly a new and amazing experience. After I came my dick went so limp I was terrified that I would never have an erection again. Boy was I wrong. She and I had a relationship for about a year.
A thirty-nine-year-old man wrote:
My first time was really good, partly because the girl knew what she was doing.
We had been petting very heavily for several dates and I knew it would happen soon. One evening she was wearing a jumpsuit that unzipped all the way down the front. We went out on the back porch of her house and she unzipped her jumpsuit and stood there, waiting. I peeled the soft cotton flannel off her shoulders and just looked at her lovely body for several minutes.
Then we stretched out on the floor and after several minutes of foreplay she reached for my cock and guided it into her. She had been with several partners before and knew the way to make love. She showed me how to play slowly and we fucked each other for several minutes before I came.
A fifty-eight-year-old woman wrote:
The first time was when I was sixteen and my boyfriend was twenty. I was on vacation with my family and my best girlfriend, and he and my friend’s boyfriend drove down to see us. He half forced, half pleaded with me to go all the way to prove I loved him, and that I hadn’t been with anyone else while I was away.
It was in the backseat of his car, with my family’s cottage just a few hundred yards away. Although he was very tender and kept telling me how much he loved me, it certainly wasn’t as wonderful as I thought it would be. The car was cramped, and because I was a virgin, there was the usual first-time mess to clean up.
It did feel pretty great once the initial pain was over and I could feel his cock explode inside me. Although it would be a while before I experienced my own orgasm, it was really something to have this big strong man exploring my body, inside and out, and enjoying it so much.
A forty-two-year-old man wrote:
It was while I was in college when I was in my early twenties. I started to date a divorced woman who worked in a snack bar near campus. The first time we went out we went back to her apartment and started fooling around. I was surprised that she wanted it as much as I did. After that first time, we “did it” every time we dated.
One of the really fun things we did a lot was to shower together. Sometimes my dick would get hard from the excitement of just thinking about the next time we’d be under all that hot water.
A forty-seven-year-old man wrote:
My first sexual experience was a bit belated since I was probably nineteen or so. I was attending a local community college and had gotten a job as the lab assistant in the photo department. I’d asked a student to model nude for me and, amazingly enough, she agreed. After I took several photos of her I developed them and just stared, imagining—well, you know what I was imagining. A few days later she came to my house to pick up the pictures and to make me dinner. After dinner she took me to my bedroom and we did it. I still have copies of the photos.
And then there were these answers.
A sixty-eight-year-old man wrote:
The first time I had sex was in the back of my old car. I had taken a girl who worked in the same office out and she and I drove into the country and parked. I suggested we would be more comfortable in the backseat, and she didn’t argue. I kissed her and soon we were “frenching” passionately. She made only nominal protests as I progressed into her panties.
After I had fingered her for a couple of minutes, she allowed me free rein. Since she knew I was a virgin, she opened my trousers and fished for my erection. She caressed it and soon I straddled her, in preparation to enter what was for me unknown territory.
As she aimed my cock at her wet, juicy opening I ashamedly poured all of my promised goodies all over her. I couldn’t think what to say, so I said nothing. She gave a look of disbelief and asked if I had come and I just nodded.
She scolded me and said that she had really wanted me. I apologized for what had occurred and said that it was because it was my first time. I said to just wait and I would be ready again in a short while.
“How long will it take?” she asked and I said I would be rearmed and ready for action again in fifteen or twenty minutes. I have to give her credit, she didn’t make a big thing out of the incident. After a few minutes, she recommenced stroking me, and in a short time, much less than the fifteen minutes I had expected, I was stiff. This time I made my first entry into the wet, willing, and waiting body.
Maybe it was good that I had had a premature explosion, since I was able to last quite a whi
le, and we both built up into a climax simultaneously. After a suitable period of rest I managed to get it up for a third time and we did it once more. She congratulated me for being able to have three orgasms in a relatively short space of time.
A seventy-seven-year-old man wrote:
My first time I was in high school and going steady. We were both seventeen and virgins. We had done a lot of petting but had never gone farther than touchy-feely.
After our senior prom we headed for the local lovers’ lane and our petting escalated to full intercourse. We were in my mother’s 1936 Buick and somehow we left a stain on the passenger’s side of the front seat. When my mother found it the next day I caught holy hell! On top of that, I hadn’t been smart enough to use a condom and for several weeks I was scared she might have gotten pregnant. We were lucky that time, but I made sure to have condoms with me from then on.
A forty-seven-year-old man wrote:
My first time was at a drive-in movie. I was seventeen and had been dating this girl for about four months. We had been to the drive-in several times and had made out but never touched each other’s private parts. One evening we went there on a double date and the couple in the front seat were going at it hot and heavy. Eventually the girl began going down on her boyfriend. My date and I were making out, too, but we were both looking up front from time to time, watching what was happening.
When the couple went to the snack stand, I unzipped my pants and asked her to suck me like the girl in the front had been doing to my friend, but she said no. I begged, and she began to stroke my cock. I came in a few minutes.
About a month after the first time at the drive-in the girl and I were back there with the same couple. My date was giving me a hand job then dipped her head into my lap, just as the couple in the front were doing the same. In a way it was sort of funny, looking back, because my buddy had been kidding me about not getting any oral sex while he was. On this night we were both getting blown, and I think we each started moaning louder than normal because we wanted to show off a bit. It was a short showing off for me, because I couldn’t have lasted two minutes in her mouth before coming.
The next week we double-dated again with the same couple. While the girl in the front seat again began going down on her boyfriend I began exploring my date’s pussy with my tongue and then finger. After a while I showed her a condom and she nodded. I slid it on, then thrust into her. Her blouse was open, but her bra was still on as I started fucking her. I remember looking toward the front seat and seeing two sets of eyes admiring our actions. They were kind enough to turn away when they realized that I had seen them. That time I was first! He had gotten blown first but I was the first to get laid. I treasured that condom and carried it around with me for months.
A fifty-nine-year-old man wrote:
We were double-dating and in the backseat of my friend’s car. We were parked at an overlook doing some heavy petting when I got my fingers into my date. I just about burst my jeans but by the time I got them down, I had come in my shorts and no amount of anything would get my cock back up.
The couple in the front were sympathetic, as was my girl, but even though we dated for another year, I never got into her when I was hard. Looking back on it, that was probably a good thing, since we were not using any protection. The guy in the front seat on that famous double date wound up getting his girl pregnant.
A twenty-year-old bisexual woman wrote:
Which first time? The first first time, which was with a woman, or the first time with a man?
My first serious sexual experience was with my first girlfriend. We had been schoolmates, and after leaving school we gradually came out to each other through e-mail. After a while of meeting as friends and doing a bit of the London gay scene, we got together. Our “first time” happened, embarrassingly, in a pub toilet.
We were out with a group of old friends, none of whom knew about us, and were hence unable to kiss, hold hands, or be anything other than “just friends.” So we nipped off to the ladies’ loos and though we started off just kissing, we ended up having what amounted to sex, while hoping none of our mates was wondering what had happened to us. It turned out later that since we had taken so long, someone had actually joked, “Maybe they’ve eloped together!” That friend didn’t know how right she was!
A year later I had several one-night fooling-about sessions with a guy friend that involved near penetration, but not real serious sex.
My actual, technical first time with a man happened a lot later, after a lot of varied sexual experiences, and so assumed much less importance in my mind. It was a bit of a nonevent really. It certainly didn’t hurt, because, since I was a very active child, I don’t think I had had any hymen for ages before that.
A fifty-year-old man wrote:
There are really two first times. Let me explain.
One first time was what you might call close-enough-to-intercourse. It was on New Year’s Eve in 1970–71 during a snowstorm in the backseat of my father’s big ol’ Chrysler. The woman I eventually married and I had been dating for six months and the time was right. I was nineteen, she was eighteen, and it was the first time for either of us.
Up to that point in our relationship we had been getting hotter and hotter—grinding, feeling, etc., but that night it just wasn’t enough. We just kept going, getting naked together and getting down to it. In actuality I didn’t enter that night but there was lots of fingering and such. Technically and officially it wasn’t the “first time” but I think we both agreed that after that night things between us were different. We had entered a new level.
The actual first time came sometime thereafter, again in the back of a car. It was quite anticlimactic—no pun intended. It was painful for her—bleeding, etc. and I came too fast—quite forgettable.
A sixty-four-year-old man wrote:
At the age of twenty-three, after approximately ten years of unsatisfied horniness, I was absolutely desperate and convinced that I would never get laid. Finally, one afternoon, I had a date with a girl whom I knew had had sex with a number of guys. My best friend Manny had been fucking her but they had broken up.
Linda and I had been obviously attracted to each other for a while and now that she and Manny had broken up, Manny had made it clear to me that he had no objection to my seeing her. He even let us use his place. We had a few drinks, started making out, and soon were both panting and sweating. Our clothing was gradually disappearing. I was down to my underpants and Linda was wearing only panties, but when I tried to remove them she stopped me and said, “I don’t do that anymore.”
Just my luck, I thought to myself, she has to pick now to reform and decide to stop fucking around. So, resigned to the fact that all I was going to be able to get was more heavy petting and a really bad case of blue balls, I continued sucking her nipples and stroking her cunt through and under her panties. We continued to get hotter and hotter, both sexually and physically (it was in the nineties that day), until I felt like I was about to explode.
Finally, frustrated beyond anything I had ever suffered before, I went to the other side of the room and knelt down on the floor facing the wall. I felt like a total failure. Here I was with a girl who had screwed around quite a bit, who was obviously as turned on as I was, and I still couldn’t get laid. I don’t think I had ever felt so bad about anything in my life. I was on the verge of tears and I certainly didn’t want her to see me cry.
Linda came up behind me and, obviously concerned, asked me what was the matter. “I can’t stand it,” I said, trying to keep her from hearing the tremor in my voice. “I’m so hungry for you.”
“But I was ready for you ten minutes ago,” she said.
Confused by her earlier comment, totally at odds with her statement, and afraid to believe what she was telling me, I turned and looked at her. As I watched, she removed her panties and stretched out on the floor next to me, never looking away from my face. I mounted her and started to come even as I entered h
er. It was the fastest fuck I have ever had, but at that point in my life, absolutely nothing could possibly have been more satisfying.
WHAT WAS THE BEST SEX YOU EVER HAD?
Many of those who answered this question described a position, an activity, a game, or a toy as the “best.” I can’t help but wonder why that one time would stand out. Wouldn’t they try the same thing again? To those of you reading and trying to decide how you would have answered this question, if you decide on one or more “best time,” consider how you can make it happen more than once!
Other letters describe activities that might not be your idea of the best sex ever, but understand that these are the opinions of real people. You may read a letter and think, No way! No real person ever did that! I don’t know, nor do I care whether each activity is accurately reported. Maybe some are fantasies of the best sex that might be. Even if they are merely fantasies, they are all tales of great sex for someone.
For me, describing the best sex I ever had is impossible. At different parts of my life, great sex had differing meanings. For example, in my still-virginal dating years, having a guy touch my breasts and get me all hot yet satisfied in some way was fabulous. Later, when I had fallen into a serious rut with my then-husband, doing something slightly out of the ordinary—which, sadly, happened rarely—was great. Now, since Ed and I share so much and can communicate so well, we make many of our experiences “the best.” Okay, that’s a cop-out, but it’s the best I can do. Many of my respondents had the same problem.
Naughty Secrets Page 2
