I was 15 and the lady in question was an old family friend, 30 years old at the time. It was a delightful experience and I have no regrets at all. In fact we got together whenever we could (she lived in another state) over the next 15 years, until her death.
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Your First Time - Sex
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goddess_nemesis
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Thank you all for your responses. It has been interesting to read them all. Everyone has had different experiences and attitudes about their first times.
As I said my first time was a couple of months ago, and it happened in the backseat of my big old Caddie. Not an ideal location, but I'm content with how it happened. Sex to me is meant for two people in love. It was the way I was raised.
When my boyfriend and I first talked about sex, I told him I was still a virgin. He was a little surprised and he then told me how wonderful and fun sex was. 😀 He was being lighthearted about it, but I told him how I wanted my first time to be with someone I loved and that it felt right.
One night the lightheartedness turned serious and my boyfriend expressed concern about being my first. The last time he was someone's first was when he was 16 and having sex first time himself. Taking my virginity was scary to him because what if things don't work out between us and what if I regretted it.
After that conversation, I knew that he would be the one for me and that when it happened it would be right. I love him and he loves me, and it was good. 😀
As I said my first time was a couple of months ago, and it happened in the backseat of my big old Caddie. Not an ideal location, but I'm content with how it happened. Sex to me is meant for two people in love. It was the way I was raised.
When my boyfriend and I first talked about sex, I told him I was still a virgin. He was a little surprised and he then told me how wonderful and fun sex was. 😀 He was being lighthearted about it, but I told him how I wanted my first time to be with someone I loved and that it felt right.
One night the lightheartedness turned serious and my boyfriend expressed concern about being my first. The last time he was someone's first was when he was 16 and having sex first time himself. Taking my virginity was scary to him because what if things don't work out between us and what if I regretted it.
After that conversation, I knew that he would be the one for me and that when it happened it would be right. I love him and he loves me, and it was good. 😀
Mephistopheles
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I have taken a girl's virginity on more than one occasion and ever since I must say I truly cannot comprehend why jihadists would want 72 virgins.
The first time I had sex I was 17 years old. I was going out with her for a couple months and she actually initiated it. We had sex in the front seat of my car that probably lasted no more than 10-15 minutes. She told me she enjoyed it and I know I did. We dated for about another year before we both moved on. I still think of her from time to time. 
Heh, my first experience was a weird one... i mean way out weird..
When was your first time having sex? Summer of 2000. I was staying with these faire owners and somehow after a few drinks wound up doing to horizontal monster mash with this guy while his wife cheered me on.
How old were you? 19
Do you regret it? Not really... It was alot of fun.
Do you ever wish you had waited? Sometimes, but not because i didn't feel like i was old enough, simply if i waited maybe i'd be in a different place now.
Wished it had been with someone else? At the time you bet your sweet ass i did. I guess you could say it was the result of rebounding from one hell of a breakup. It was just another event that occurred during that time i tried to drink myself stupid to forget. Now, in hindsight, I feel better about the whole thing. It was still weird and kinda dumb.
Are you content with how it happened? Yeah... It was perhaps the only time up until this past year that i could connotate sex with the word happy.
When was your first time having sex? Summer of 2000. I was staying with these faire owners and somehow after a few drinks wound up doing to horizontal monster mash with this guy while his wife cheered me on.
How old were you? 19
Do you regret it? Not really... It was alot of fun.
Do you ever wish you had waited? Sometimes, but not because i didn't feel like i was old enough, simply if i waited maybe i'd be in a different place now.
Wished it had been with someone else? At the time you bet your sweet ass i did. I guess you could say it was the result of rebounding from one hell of a breakup. It was just another event that occurred during that time i tried to drink myself stupid to forget. Now, in hindsight, I feel better about the whole thing. It was still weird and kinda dumb.
Are you content with how it happened? Yeah... It was perhaps the only time up until this past year that i could connotate sex with the word happy.
Tiger.Lily
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When was your first time having sex? A cold December night in his bed.
How old were you? 15 -- about two months before I turned 16.
Do you regret it? I'm not sure. I was rebounding from my first love whom I had wanted to lose my virginity to more than anything. So when this guy came along, we dated for a little while, and then I just didn't care anymore. He'd had several partners before me so I figured at least he'd know how to take care of me and make sure it was as painless as possible. I didn't love him, and our sex life was horrible because I wasn't comfortable with him -- but I knew what I was doing when I met dREW so I was able to make his first time incredible. And that's the only reason I don't regret it. Then again, would it have been more "ideal" to lose it to the guy after him who I loved (and still care for)?
Do you ever wish you had waited? I would have done it before then, given the chance.
Wished it had been with someone else? Possibly. I would have lost my virginity to the guy before him if I had been given the opportunity. We tried to create that opportunity countless times, in fact. It just didn't happen. But if I hadn't lost it to who I did then I wouldn't have been able to make dREW's first time magical.
Are you content with how it happened? Fuck. No.
How old were you? 15 -- about two months before I turned 16.
Do you regret it? I'm not sure. I was rebounding from my first love whom I had wanted to lose my virginity to more than anything. So when this guy came along, we dated for a little while, and then I just didn't care anymore. He'd had several partners before me so I figured at least he'd know how to take care of me and make sure it was as painless as possible. I didn't love him, and our sex life was horrible because I wasn't comfortable with him -- but I knew what I was doing when I met dREW so I was able to make his first time incredible. And that's the only reason I don't regret it. Then again, would it have been more "ideal" to lose it to the guy after him who I loved (and still care for)?
Do you ever wish you had waited? I would have done it before then, given the chance.
Wished it had been with someone else? Possibly. I would have lost my virginity to the guy before him if I had been given the opportunity. We tried to create that opportunity countless times, in fact. It just didn't happen. But if I hadn't lost it to who I did then I wouldn't have been able to make dREW's first time magical.
Are you content with how it happened? Fuck. No.
Chloe_Vlad
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I have taken the virginity of several men and I hate it. Nevermind that the first time you sleep with someone it is less than perfect, but with an unexperienced virgin is even worse.
I lost my virginity to another virgin when I was 17, we had been together for months and were committed to each other. It was wonderful and I do not regret it at all. While I do not regret taking the my subsequent partners virginities, I wish that their first times could haven been with someone who really loved them, and that was not me.
When was your first time having sex? August of 1998
How old were you? 17
Do you regret it? Not at all, it was with my first true love. It was an awesome experience. I initiated it, was in control, and he respected me. I knew how to please myself and the tension between us was building. We had done all kinds of other experimenting, this was just the next big step.
Do you ever wish you had waited? No, it was a hot night. I was never one of those girls who had to wait for the moment to be absolutely perfect, life isn't perfect. It was in my bed, with the lights off and the glow in the dark stars above us. It was so hot that the sweat was dripping off us. And I got to drive him home afterwards with the top down on my convertible.
Wished it had been with someone else? No. He was, and still is, the most compatible person I have ever been with. He was, and still is, my best friend.
Are you content with how it happened? Yeah.
__________________
How old were you? 17
Do you regret it? Not at all, it was with my first true love. It was an awesome experience. I initiated it, was in control, and he respected me. I knew how to please myself and the tension between us was building. We had done all kinds of other experimenting, this was just the next big step.
Do you ever wish you had waited? No, it was a hot night. I was never one of those girls who had to wait for the moment to be absolutely perfect, life isn't perfect. It was in my bed, with the lights off and the glow in the dark stars above us. It was so hot that the sweat was dripping off us. And I got to drive him home afterwards with the top down on my convertible.
Wished it had been with someone else? No. He was, and still is, the most compatible person I have ever been with. He was, and still is, my best friend.
Are you content with how it happened? Yeah.
__________________
hisdarkangel
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When was my first time?
My first time was the day before my 19th birthday in my room with my current fiance, Zak, also known as "Powah" on here. The day itself was amazing...lots of romance and foreplay, along with a full on tickle session that really got us in the mood, and eventually, it just lead there. We had talked about it beforehand, but not when it would happen. We sort of got caught up in the moment, so to speak.
How old were you?
Hours before turning 19. He was 18.
Do you regret it?
Not one bit. I loved him dearly then, and I still do.
Do you ever wish you had waited?
Meh...not really. We've had too much fun with it, frankly, and in the end if something happens to one of us or we separate (hopefully not), I will never regret giving my V card to him, and vice versa.
Wished it had been with someone else?
Again, no. I love him and I will never regret giving it to him.
Are you content with how it happened?
It was pretty good...the whole day in general. The only downside is that we both had colds on my actual birthday, so we couldn't do it for my birthday, which sucked ass cuz 1. we were sick on my birthday and 2. I was horny as hell cuz I had just lost my virginity the day before. But overall, it was good (and good to finally get it out of the way). =P
My first time was the day before my 19th birthday in my room with my current fiance, Zak, also known as "Powah" on here. The day itself was amazing...lots of romance and foreplay, along with a full on tickle session that really got us in the mood, and eventually, it just lead there. We had talked about it beforehand, but not when it would happen. We sort of got caught up in the moment, so to speak.
How old were you?
Hours before turning 19. He was 18.
Do you regret it?
Not one bit. I loved him dearly then, and I still do.
Do you ever wish you had waited?
Meh...not really. We've had too much fun with it, frankly, and in the end if something happens to one of us or we separate (hopefully not), I will never regret giving my V card to him, and vice versa.
Wished it had been with someone else?
Again, no. I love him and I will never regret giving it to him.
Are you content with how it happened?
It was pretty good...the whole day in general. The only downside is that we both had colds on my actual birthday, so we couldn't do it for my birthday, which sucked ass cuz 1. we were sick on my birthday and 2. I was horny as hell cuz I had just lost my virginity the day before. But overall, it was good (and good to finally get it out of the way). =P
MrMacphisto
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So I'm wondering, when was your first time having sex?
1999
How old were you?
20
Do you regret it?
The sex itself, no. The girl it was with, yes.
Do you ever wish you had waited? Wished it had been with someone else? Or are you content with how it happened?
I wish it was earlier, and with my senior prom date. She was nice, but we had no chemistry.
I'm content that I got some experience, but I was probably too drunk at the time to appreciate it much.
1999
How old were you?
20
Do you regret it?
The sex itself, no. The girl it was with, yes.
Do you ever wish you had waited? Wished it had been with someone else? Or are you content with how it happened?
I wish it was earlier, and with my senior prom date. She was nice, but we had no chemistry.
I'm content that I got some experience, but I was probably too drunk at the time to appreciate it much.
When was your first time having sex?
In my then boyfriend's apartment on the living room floor
How old were you?
19-and in IMO, far too young
Do you regret it?
Looking back, hell yeah!
Do you ever wish you had waited?
Yes I did, but I was a bit buzzed and under a lot of pressure. We were together 10 months; guess it was time to do something. I took pride in my virginity and really wasn't in a hurry to "get it over with." I wish I would've been stronger and held out for a better timeframe.
Wished it had been with someone else?
Because of what he did afterwards, yes I do.
Or are you content with how it happened?
Not really-it felt like someone took a vacum hose and stuck it up the yadda yadda! Not much fun at all. We had sex a few more times and I just never found it enjoyable-it was just duty and expectation. Besides, he traded me in for what he thought was a better model. By the time he showed up back in my life again, I was pregnant with my son. He took me to dinner and told me he wished the child was his. Oh well....unfortunately he left this world way too soon and I do think of him from time to time.
Down the road many years later, it became something totally different. I had a great time with someone who was sensual and sexual. He was attentive and had a tickling streak long before I landed on this forum. It was not meant to last unfortunately, but I now know what I want and like and can express it freely without shame.
In my then boyfriend's apartment on the living room floor
How old were you?
19-and in IMO, far too young
Do you regret it?
Looking back, hell yeah!
Do you ever wish you had waited?
Yes I did, but I was a bit buzzed and under a lot of pressure. We were together 10 months; guess it was time to do something. I took pride in my virginity and really wasn't in a hurry to "get it over with." I wish I would've been stronger and held out for a better timeframe.
Wished it had been with someone else?
Because of what he did afterwards, yes I do.
Or are you content with how it happened?
Not really-it felt like someone took a vacum hose and stuck it up the yadda yadda! Not much fun at all. We had sex a few more times and I just never found it enjoyable-it was just duty and expectation. Besides, he traded me in for what he thought was a better model. By the time he showed up back in my life again, I was pregnant with my son. He took me to dinner and told me he wished the child was his. Oh well....unfortunately he left this world way too soon and I do think of him from time to time.
Down the road many years later, it became something totally different. I had a great time with someone who was sensual and sexual. He was attentive and had a tickling streak long before I landed on this forum. It was not meant to last unfortunately, but I now know what I want and like and can express it freely without shame.
Mephistopheles
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Indeed. I spent half the time I was with those girls comforting them and explaining how and what happens, telling them to say stop if they wanted it, yada yada, and trying to be careful instead of just enjoying the sex we had.
desdemona
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When was your first time having sex? Summer of 1990
How old were you? 19
Do you regret it? Not really. I was in love with the guy in my own way. And I knew I wasn't waiting for the perfect moment or a storybook romance.
I did enjoy the sex, but in the end, the relationship was a mistake.
Do you ever wish you had waited? Sometimes, but only in the sense that I regretted the relationship (not the sex or losing my virginity) when it ended.
Wished it had been with someone else? Looking back, yes. But it all worked out in the end.
Are you content with how it happened? LOL. Well, it wasn't in the back seat of a car...so yeah. I was far too eager to spread my wings and this was my summer of rebellion. I later got caught with him in my bed by my parents (I was home from college). I think that was a wakeup call in more ways than one.
How old were you? 19
Do you regret it? Not really. I was in love with the guy in my own way. And I knew I wasn't waiting for the perfect moment or a storybook romance.
I did enjoy the sex, but in the end, the relationship was a mistake.
Do you ever wish you had waited? Sometimes, but only in the sense that I regretted the relationship (not the sex or losing my virginity) when it ended.
Wished it had been with someone else? Looking back, yes. But it all worked out in the end.
Are you content with how it happened? LOL. Well, it wasn't in the back seat of a car...so yeah. I was far too eager to spread my wings and this was my summer of rebellion. I later got caught with him in my bed by my parents (I was home from college). I think that was a wakeup call in more ways than one.
penny lane
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So I'm wondering, when was your first time having sex?
I was a sophomore in college. Like others who posted before me, I inherently knew that sex was for adults, so I did make an effort to wait until I was over 18.
How old were you?
I was 20 years old...close to being 21.
Do you regret it?
Yeah, I wish I would have waited for when I was in love.
Do you ever wish you had waited?
See previous response.
Wished it had been with someone else?
Yes, I wasn't in love at all with the guy I did it with for the first time. I wish I had waited.
are you content with how it happened?
I agree, there's too much emphasis put on the first time. You're nervous, and (at least for me there was) so much pressure to do it. I didn't enjoy it at all. After it happened, the guy dumped me a few weeks later. It put me off of having sex for a long time.
I was a sophomore in college. Like others who posted before me, I inherently knew that sex was for adults, so I did make an effort to wait until I was over 18.
How old were you?
I was 20 years old...close to being 21.
Do you regret it?
Yeah, I wish I would have waited for when I was in love.
Do you ever wish you had waited?
See previous response.
Wished it had been with someone else?
Yes, I wasn't in love at all with the guy I did it with for the first time. I wish I had waited.
are you content with how it happened?
I agree, there's too much emphasis put on the first time. You're nervous, and (at least for me there was) so much pressure to do it. I didn't enjoy it at all. After it happened, the guy dumped me a few weeks later. It put me off of having sex for a long time.
Last edited:
How old were you?
18
Do you regret it?
Not at all, it was with my first girlfriend.
Do you ever wish you had waited? Wished it had been with someone else? Or are you content with how it happened?
I'm content. I'm glad it happened with someone I loved and trusted at a time when I was emotionally mature enough to handle it.
18
Do you regret it?
Not at all, it was with my first girlfriend.
Do you ever wish you had waited? Wished it had been with someone else? Or are you content with how it happened?
I'm content. I'm glad it happened with someone I loved and trusted at a time when I was emotionally mature enough to handle it.
Tortuga
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with a guy...
When was your first time having sex?
I don't remember, it was a couple months after I moved to Tampa,FL 4 years ago.
How old were you?
20
Do you regret it?
At the time no, but now I do. Because he turned out to be a total douchbag, and I have a restraining order on him.
Do you ever wish you had waited?
Not really, I was 20, it was bound to happen eventually.
Wished it had been with someone else?
I wish it was someone else. Because the guy I lost my man-sex virginity with, he turned to be really harsh. And later in our relationship, I was on my monthly, and he tried to rape me. Then he ended up stalking me afterwards, hence the restraining order.
Or are you content with how it happened?
it happened...move on
When was your first time having sex?
I don't remember, it was a couple months after I moved to Tampa,FL 4 years ago.
How old were you?
20
Do you regret it?
At the time no, but now I do. Because he turned out to be a total douchbag, and I have a restraining order on him.
Do you ever wish you had waited?
Not really, I was 20, it was bound to happen eventually.
Wished it had been with someone else?
I wish it was someone else. Because the guy I lost my man-sex virginity with, he turned to be really harsh. And later in our relationship, I was on my monthly, and he tried to rape me. Then he ended up stalking me afterwards, hence the restraining order.
Or are you content with how it happened?
it happened...move on
Tortuga
Verified
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with a girl
When was your first time having sex?
It was my 16th birthday, some friends of mine took me out. My secret girlfriend at the time, she drove me home, we pulled over in some woods.
How old were you?
16
Do you regret it?
Oh god no, it was the first passionate moment I've had.
Do you ever wish you had waited?
no
Wished it had been with someone else?
hecks no. She was gorgeous and I was very happy with our relationship.
Or are you content with how it happened?
Absolutely.
When was your first time having sex?
It was my 16th birthday, some friends of mine took me out. My secret girlfriend at the time, she drove me home, we pulled over in some woods.
How old were you?
16
Do you regret it?
Oh god no, it was the first passionate moment I've had.
Do you ever wish you had waited?
no
Wished it had been with someone else?
hecks no. She was gorgeous and I was very happy with our relationship.
Or are you content with how it happened?
Absolutely.
Soda Bobinski
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I was 17 & it happened in my bedroom ( which was also the attic ) & Extreme's More Than Words was playing.
The song lasted longer than I did.
The song lasted longer than I did.
When was your first time having sex?
She was my year 11 formal partner. It was like 4.30am, we had come home from the formal after party and were terribly, terribly drunk. I don't really remember much, and it's probably for the best that I don't remember much.
How old were you?
16
Do you regret it?
A bit. Only cuz we were both so wasted, could've been a little more romantic, but oh well.
Do you ever wish you had waited?
For her consent? Probably...
Wished it had been with someone else?
Mmmm, yeah, would've liked to have lost my v plates with the girlfriend I was with afterwards. She was also a virgin.
Or are you content with how it happened?
I'm content. These things happen, what can ya do?
-Xionking
__________________
She was my year 11 formal partner. It was like 4.30am, we had come home from the formal after party and were terribly, terribly drunk. I don't really remember much, and it's probably for the best that I don't remember much.
How old were you?
16
Do you regret it?
A bit. Only cuz we were both so wasted, could've been a little more romantic, but oh well.
Do you ever wish you had waited?
For her consent? Probably...
Wished it had been with someone else?
Mmmm, yeah, would've liked to have lost my v plates with the girlfriend I was with afterwards. She was also a virgin.
Or are you content with how it happened?
I'm content. These things happen, what can ya do?
-Xionking
__________________
AdamSterling
TMF Expert
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My first time...
When was your first time having sex? How old were you?
16 July 1998 -- my 25th birthday.
Do you regret it?
Absolutely not. It was with the women I loved. I eventually married her. (We have since broken up, but them's the breaks.)
Do you ever wish you had waited?
I think I waited more than long enough!
Wished it had been with someone else?
At the time, no. After all this time... still no.
Are you content with how it happened?
Yes. She was a ticklee, and I'm a tickler and foot fetishist. Tickling (and foot play) was incorporated into sex (and foreplay) every time we were together.
Since then, I have incorporated foot play and/or tickling into every intimate encounter I've had, with the exception of one woman from three summers ago.
She was misinformed on the definition of the word "fetish" -- she thought all fetishists were only capable of drooling over their particular kinks. She was amazed that I actually had a brain -- and self-control!
I had to tell her that she knew WAY more fetishists than she thought... but I was the first fetishist she knew that was out about it. (I'm not out in public with my kinks, but I am definitely out to women I date!) Eventually, she understood, but we were not the best match. I wish her well -- and that applies to all the women I've been with. (Yes, even the ex-wife. I'm not bitter.)
Thanks for the opportunity to express myself.
When was your first time having sex? How old were you?
16 July 1998 -- my 25th birthday.
Do you regret it?
Absolutely not. It was with the women I loved. I eventually married her. (We have since broken up, but them's the breaks.)
Do you ever wish you had waited?
I think I waited more than long enough!
Wished it had been with someone else?
At the time, no. After all this time... still no.
Are you content with how it happened?
Yes. She was a ticklee, and I'm a tickler and foot fetishist. Tickling (and foot play) was incorporated into sex (and foreplay) every time we were together.
Since then, I have incorporated foot play and/or tickling into every intimate encounter I've had, with the exception of one woman from three summers ago.
She was misinformed on the definition of the word "fetish" -- she thought all fetishists were only capable of drooling over their particular kinks. She was amazed that I actually had a brain -- and self-control!
I had to tell her that she knew WAY more fetishists than she thought... but I was the first fetishist she knew that was out about it. (I'm not out in public with my kinks, but I am definitely out to women I date!) Eventually, she understood, but we were not the best match. I wish her well -- and that applies to all the women I've been with. (Yes, even the ex-wife. I'm not bitter.)
Thanks for the opportunity to express myself.
LindyHopper
2nd Level Red Feather
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So I'm wondering, when was your first time having sex?
High school boyfriend of then-3 years, in the privacy of my own home.
How old were you?
17.
Do you regret it?
No. It was with the right person, at the right time.
Do you ever wish you had waited?
No. After the third time (not the first time, which was awkward and a touch painful), I actually wondered why I'd waited so long. 😛
I wish our culture didn't make such a huge deal about The First Time. Some people end up missing opportunities because they feel compelled to wait. Some people jump into any old encounter to get the first time "out of the way." Either way, people aren't doing it on their own natural timetable, and are set up to fail due to unrealistic expectations about what The First Time is supposed to be like, and what it's supposed to mean. You can have much better and more meaningful sex once you know what the f*ck you're doing.
High school boyfriend of then-3 years, in the privacy of my own home.
How old were you?
17.
Do you regret it?
No. It was with the right person, at the right time.
Do you ever wish you had waited?
No. After the third time (not the first time, which was awkward and a touch painful), I actually wondered why I'd waited so long. 😛
I wish our culture didn't make such a huge deal about The First Time. Some people end up missing opportunities because they feel compelled to wait. Some people jump into any old encounter to get the first time "out of the way." Either way, people aren't doing it on their own natural timetable, and are set up to fail due to unrealistic expectations about what The First Time is supposed to be like, and what it's supposed to mean. You can have much better and more meaningful sex once you know what the f*ck you're doing.
