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 while, 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.
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.
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.
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.
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.
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.
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 her. It was the fastest fuck I have ever had, but at that point
in my life, absolutely nothing could possibly have been more satisfying.
M
any 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.
There’s no specific “best,” just many times with my husband. It is so
great
because there is total trust between us. We each know that if we are trying something new, and one of us isn’t completely
enjoying it, we can stop without guilt. The greatest thing about sex with my hubby, he is a
giver!
He wants me to climax every time and he feels like he isn’t doing his “job” if I haven’t! He is
not
at all selfish!
What a difficult question to answer! I don’t know that I could ever narrow it down to one particular episode—I know for sure
I have lots and lots of fond memories. One of the things my wife and I have going for us is our honesty.
It all began one day long ago when I got us a day-use hotel room. I sent my wife there with the key, told her to read the
instructions I had left her in the room and follow them to the letter. She did, including writing answers to a series of questions
about what she thought I was going to do with her and to her and how she felt about it. I had made a list of possible activities
including blindfolding, light bondage, fairly aggressive spanking, oral and vaginal intercourse.
Later I read the answers, learned a lot, and we’ve been communicating honestly and clearly since then. How fond a memory that
day is—especially since she felt so close to me, too. She calls it one of our “special” times.
I feel that the best sex is when I feel totally excited and the person with whom I am making love is so into me and I am so
into him that it just flows. It feels so good with no inhibitions or holding back. Just pleasure.
The best sex probably was the time that I was stroking my wife’s clitoris and I kept doing it. She asked me to stop but I
kept it up. I also kissed her breast and sucked her nipple, but she told me to stop so she could focus. She began to wriggle
and move wildly after several minutes while I slowly continued to rub her. All of a sudden she started shaking violently.
I continued to stroke as she came once and then a second time. I mounted her and as my penis slid into her vagina, she came
again. When I started to climax, she shook and went crazy and cried. It was fantastic. We do it that way occasionally now,
but it isn’t the same as that first time.