Thoughts On Finally Losing My Virginity...

A_dub

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So I'm knocking on 40 (about 2 years shy but thats close) but had never actually done the deed (until last Sunday) or been out on a date. I know that may seem hard to believe but it is what it is. Anyways she's a recently divorced woman that I met on a dating app.

Most of you all are probably wondering how on earth its possible to go so long without any sort of success in dating/sex. Well I realized recently that my standards were unreasonably high. I had suspected it before, but close friends eventually managed to convince me that since I'm no George Clooney I shouldn't expect to be dating a supermodel. Sounds pretty basic, but its harder to practice in real life (at least for me).

Oh any for anyone wondering I only lasted a minute the first time but she impressed in that I managed to go 5 times in less than 2 hours :D
 

insert_8

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So I'm knocking on 40 (about 2 years shy but thats close) but had never actually done the deed (until last Sunday) or been out on a date. . . .

Most of you all are probably wondering how on earth its possible to go so long without any sort of success in dating/sex. . . .
Based on what you've said here, I believe you. My wife and I were 23, which - even in 1974 - put us in a small minority of "late bloomers". Two of our three kids were over 30; I don't know about the third.

You surely must know that abbreviated information like you posted is almost begging us preverts to ask for more details.

Did she know it was your first time? Before, or after, it happened? Who initiated the sex? Did she do anything that seemed to make it special for you?

What were your intentions and attitude going into the encounter? For instance:
  • One-time thing, just to get the first-time out of the way?
  • A casual relationship where you can learn the ropes and get some practice for a few weeks or months, before moving on?
  • Trying her out, to see if there's potential for a relationship?
  • Intending to do whatever it takes to make her a long-term relationship?
Do you feel the same way afterwards?

I know something about cumming WAY too quickly the first time! I was NOT prepared for the incredible sensation of her vagina enveloping my erection! And, I bet you were in missionary position.

Five times in two hours is definitely impressive. We did twice in two hours; five times in 24. I remember being just a touch sore "down there" after that first day.

As for physical attraction . . . I was in my 30's, and VERY married, when I figured out that I lusted after super-model types because I had been conditioned to do so. An interesting occurrence at work made me realize that I was attracted to intelligence in women!
 
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insert_8

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A_dub

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Based on what you've said here, I believe you. My wife and I were 23, which - even in 1974 - put us in a small minority of "late bloomers". Two of our three kids were over 30; I don't know about the third.

You surely must know that abbreviated information like you posted is almost begging us preverts to ask for more details.

Did she know it was your first time? Before, or after, it happened? Who initiated the sex? Did she do anything that seemed to make it special for you?

What were your intentions and attitude going into the encounter? For instance:
  • One-time thing, just to get the first-time out of the way?
  • A casual relationship where you can learn the ropes and get some practice for a few weeks or months, before moving on?
  • Trying her out, to see if there's potential for a relationship?
  • Intending to do whatever it takes to make her a long-term relationship?
Do you feel the same way afterwards?

I know something about cumming WAY too quickly the first time! I was NOT prepared for the incredible sensation of her vagina enveloping my erection! And, I bet you were in missionary position.

Five times in two hours is definitely impressive. We did twice in two hours; five times in 24. I remember being just a touch sore "down there" after that first day.

As for physical attraction . . . I was in my 30's, and VERY married, when I figured out that I lusted after super-model types because I had been conditioned to do so. An interesting occurrence at work made me realize that I was attracted to intelligence in women!

Brief answers:

1) Did she know it was my first time? I don't know. I definitely did not divulge the information and she didn't ask, because she probably thought what late 30s guy has never done it before? What would I have said if she had asked at some point? I honestly don't know.

2) My intentions? Really probably all of what you said and none of what you said haha. I'm just gonna go with the flow.

3) The very first time I actually chose to have her on top thinking I'd last longer that way. 60 seconds later that turned out to be a big fat lie :p . We ended up doing a little of everything (missionary, doggy, cowgirl, reverse cowgirl). I think the longest I lasted was probaly 7-8 minutes towards the very end. Needless to say she did not orgasm from my cock, but I got her there with my [presumably] good oral skills.
 
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DiamondJoe

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So I'm knocking on 40 (about 2 years shy but thats close) but had never actually done the deed (until last Sunday) or been out on a date. I know that may seem hard to believe but it is what it is. Anyways she's a recently divorced woman that I met on a dating app.

Most of you all are probably wondering how on earth its possible to go so long without any sort of success in dating/sex. Well I realized recently that my standards were unreasonably high. I had suspected it before, but close friends eventually managed to convince me that since I'm no George Clooney I shouldn't expect to be dating a supermodel. Sounds pretty basic, but its harder to practice in real life (at least for me).

Oh any for anyone wondering I only lasted a minute the first time but she impressed in that I managed to go 5 times in less than 2 hours :D
Well, congratulations there, OP.

Just remember, however you feel, whatever anyone says, we all had to start somewhere.

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un_cut69

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I think you should tell her that she was your first.
While you might be embarrassed, I bet it will make her go wild.
I remember when I was a virgin, I was on the fence about spilling the beans to the girl.
However once I did it seamed that her sexual desire to make something happen with me grew exponentially.
 
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