Sexual Relationships
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Storytime about my first time. Self reflection and opinion gathering.

Storytime about my first time. Self reflection and opinion gathering.

I've lost my virginity over one year ago. This story has been bugging me ever since, so I decided to write about it to make my thoughts on it clearer and what better way then sharing it here on GAG where someone may even be patient enough to read it and give his/her opinion?

As I'm not used to write such long texts, I hope in your comprehension if you find any mistake or inconsistency. I'll also be describing the sexual acts in a bit of detail, skimp through if you dislike that. But enough with this, let's get into the meat and potatoes of this story...

Storytime about my first time. Self reflection and opinion gathering.

My background

My sexuality activated pretty early and ever since then I've had quite a strong sex drive. I masturbated often and got incredibly interested in sex and related subjects. I watched porn, read adult magazines and quite an amount of informative materials about sexual education, intercourse and so on...

I was quite the shy kid. In the span of 6 years I had 4 girlfriends (none of which lasted more then 2 months), but the amount of sexual acts I performed could be counted on one hand in total: I fingered two, once; I gave oral to another, once; I received some sort of tentative blowjob from another, once. All in all, my sex drive get growing with nothing to calm it other then masturbation. It was like a raging flame in my mind (and lower abdomen), fanned by the strong winds that are hormones.

Coincidentally, the strength of this flame was part of the reason I struggled to find someone to help me quell it as I feared that if I was given too much stimulus, I would end up letting loose all of my pent up lust on my partner, ending up in who knows what situation... Certainly not a good one, I thought.

So as the year passed, I came to form some sort of "ideal first time" that took root in my mind. This ideal time had a few characteristics:

-Experience: If possible I wanted to have my first time with someone with more experience then me, so that she could guide me or at least put me on the right road (sexually speaking).

-Length: I wanted to be able to have sex multiple times during the first day, in order to unload as many of the techniques I gathered as possible. That meant I wouldn't want to have just one hour or less at disposal.

-Passion: As I said, my sex drive was pretty high. I wanted to find a partner that could take it without shying away in the middle.

Then, when I was 20, I met her.

Storytime about my first time. Self reflection and opinion gathering.

The girl

We met online, through a dating app. We started a conversation and our chat escalated incredibly quickly. We shared similar interests, sexual ones included (to my surprise and joy). In a few days we exchanged more texts then I did in weeks with most of my EXs. We talked about everything and nothing and enjoyed it. She seemed like a serious girls who likes to live life to its fullest. She told me she lost her first time being raped. Though sad, the fact that she felt close enough to tell me this impressed me and I promised myself I would help her get over it, if she needed, or at least hear her out. She didn't want to get into details so soon, so we put it off for later on in the relationship. But we definitely clicked so, after a week, we decided to meet up.

We seemed to go well together in real life too. In a few hours we were already creating our own pink space, and eyes left space to lips that left space to hands... We were both surprised by how well we matched, so we were quite sad when we had to leave.

But Lady Luck seemed to be on my side, as had the whole apartment for myself right on that very same weekend. I weighted my options and saw that all the cards were in place. I just had to make my play. With throbbing heart I invited her over and she accepted.

Storytime about my first time. Self reflection and opinion gathering.

The act

The day she came over, we first had a romantic walk through the city to... buy condoms. Incredibly romantic...

As we got home, we didn't waste much time. The attraction between us was incredible and the texts we kept sending all day long (and especially the night) just fanned the flames. We got to the bed and I started off by giving her oral (she already said she didn't like to give oral, so that was the only choice I had for foreplay). I quite enjoy pleasing my partner, so I glued my upper mouth to her lower one for a good 10/15 minutes. But I didn't have the courage to take a good look, so I couldn't pinpoint her clitoris exactly, making my technique a bit sloppy and less effective. In the end she didn't cum. It didn't seem like she disliked it, though, so I was still quite content.

It was now time for the main course. With a beating heart I pushed my shy self to go all in and said:

"X, would you like to have my first time?"

When she froze for a moment, I immediately thought: "I FUCKED UP!". But it was to be expected. After all I knew she thought I had prior experience after we met in the park. I also avoided answering when she asked me about my sexual experience, allowing her to believe that I did indeed have much experience behind me (I have a bit of a mischievous character, that was my way to surprise and prank her at the same time). But in the end, she answered with a meek "yes".

Although the answer sounded a bit plain, I didn't think much of it and got a condom on. She helped me getting in and I popped my cherry with a thrust. I was nervous and constantly checking her reactions to see if she was in pain or if she felt good. But I remember the condom being surprisingly uncomfortable and thinking that it might help me to last longer.

As I started to move I was beginning to be aware of something I notice while I was eating her up: I couldn't quite understand the signals her body gave. Not knowing if what I was doing was right or wrong threw me in a bit of a panic. I wrecked my brain for clues as to what I could be doing wrong. Maybe it was because of my natural shyness or because of how nervous I was, but I didn't ask her if she felt good when I did something rather then something else. All our dialogue consisted in a reciprocated "How is it?", "Amazing!". And sure, it was amazing, but probably not in the way she meant, for me. After all I couldn't quite say I was enjoying myself... I was finally realizing a dream, but at the same time I was focused on remembering too many things at once, correlating them to the current situation to find a clue of what the hell was I doing wrong or good, all the while trying to keep my lust in check so that it didn't explode...

Her expression didn't help me either. I thought she started to feel that something was off about me, and that made me even more nervous. I tried to maintain a cool facade, as if I knew what I was doing, while wrecking my brain about how to act more natural while keeping my lust reined. After all I knew that true passion was key to having enjoyable sex. We changed positions a few times.

And so, after what I thought were 10/15 minutes, I came before bringing her even close to orgasm. I realized I made a better job with my tongue then my dick. But she didn't have a dissatisfied look, so I was still a bit content for being able to last that long. I thought it wasn't bad for the first time and that I could do better next time.

We took a shower together (another dream fulfilled for me) and things heated up again. She started rubbing my dick on her vagina. Then, just like that, she asked if she could put it in. I was stunned since I didn't understand why would she take such a risk, but replayed that I could go grab a condom. She refused, dismissing it as a joke.

Despite what she said, though, a few minutes later she was grinding hard against my dick, bringing it terribly close to her entrance. It was incredibly exiting, and she seemed to be getting close to climaxing, but my danger sense tingled. I didn't like how she kept getting my tip closer and closer to her entrance, pushing every time a little more... my danger sense was tingling. Moreover she didn't seem to be perfectly shaved as I felt that my dick would start bleeding before she could get to climax. So I stopped her, got a condom on and got back to fucking.

This time she got closer to her orgasm, but I came before she could. I couldn't even muster energy to try finishing her off by mouth, as I felt completely dry (something I never experienced, even when cumming several more times in a shorter amount of time). Ashamed, I apologized for not being able to make her cum this time again. She seemed to understand and soothed me, saying that it was alright as she didn't cum easily anyway. But I thought it wasn't quite alright, as she showed quite the frantic expression when she tried to came before, mixed with a bit of... dissatisfaction? Impatience?

Nevertheless I suggested we go for a third round, but she refused this time. I dropped it there since I didn't feel right pushing her and we went to sleep.

The next day we quarreled. It wasn't anything big, but the air between us kept getting more tense. In the end, when she left, we seemed ready to start quarreling again...

The aftermath

At this point I should specify that we used to communicate better through text rather then voice (it may has something to do with me being more proficient in written English). So once we were both home, we started chatting about what we didn't like about one another. There is no need to report the conversation here, but I'd like to highlight a few points.

The first is that she admitted she wasn't feeling sexually attracted to me. That surprised me at first, but came to hurt me only later, after reflecting on it.

The second was how I got bitchy about her "ruining" my first time. In the first place it was my own fault for being so nervous, so it was pointless to point her finger against her. But what really scared me was that I nearly blurted our something like "you of all people should know how important it is being able to choose your own first time." Knowing her circumstances, these were incredibly cruel words, yet I felt justified saying them just because she accepted having my first time without feeling particularly attracted to me...?

The third was that she accused me of lying to her about this being my first time. I made a rule for myself to NEVER lie to my partner, and I made it clear to her. So, while her saying "You going 30 minutes your first time and your good technique make it impossible for you to be a virgin" did elevate my confidence in my sexual prowess, it also shattered my lingering dreams of an "ideal first time" and hurt me in a way that I find hard to describe.

In the end, the relationship we built in less then 2 and a half weeks didn't hold the pressure and we decided to distance ourselves as friends. Later on that year I manifested an annoying case of HPV.

Storytime about my first time. Self reflection and opinion gathering.

Conclusions

I think I have a few things to learn from this. First would be to wait longer for a relationship to stabilize before bringing it to the next level, at least if it is the first time (especially with all those conditions I wished to fulfill). Two weeks was way too short a time to get to know each other properly.

Second, to ALWAYS have the condom on. I think the last part of the story is clear on that.

Those are a few of the lessons I decided to take from this, but I'm still left with many questions...

Why did she have sex with me if she wasn't sexually attracted to me?

Did me being too tense cause her sexual attraction drop?

Did the how and/or when I asked her if she wanted to have my first time force her hand in saying yes? Maybe I should have just stopped when she didn't seem completely sure about it.

Should I have tried to make her cum with my mouth again or more?

Should I have tried my luck with a third time? Maybe I would have been able to be less tense, the third time.

Is it bad for me to feel resentment for her? I absolutely don't act on it, in fact she hasn't even noticed, but the feeling still lingers and bites back at me every now and then. I wonder if it's a justified feeling or just the fruit of my immaturity and unacceptance...

Anyhow, if you read so far I'd love for you to leave a comment or an opinion. If you even have an answer to any of the questions I've been left with I couldn't ask for more.

Hoping this wasn't too boring to read, I wish you a good day/night.

0 2

Most Helpful Guy

  • Overall, your story suggests a preoccupation that, while not unknown or necessarily bad, is disproportionate. You, like many humans, especially males, have a strong sex drive. There are all sorts of personal and evolutionary reasons for that and it does not really merit much examination. Other than to add that you should do your best to control it and not let it control you.

    Beyond that it is difficult to say very much. I do not know you. I do not know the other person (s) involved and I am only getting your perspective. So that makes it exceedingly difficult to proffer objective advice.

    For example, from the sound of it, your break-up the next day was all based on the sex. That may or may not be true, but there is no way to know for sure. Certainly your motives, at base, were to use her. Flat out - and that can add tension where that is not understood between both parties.

    The bottom line is, however, that you appear to be overthinking things and are a bit too preoccupied with the what and not the who. In total fairness, I've been there and done that. However, unlike yourself, I did not conflate the two in my mind and therefore, however things worked out, I did not dwell on it.

    As to your questions:

    Why did she have sex with me if she wasn't sexually attracted to me? Didn't you do the same? You did not know her and jumped on what amounted to first impressions. She wanted sex for sex and you did not matter all that much. Again, that can work as long as you set your expectations accordingly.

    Did me being too tense cause her sexual attraction drop? Probably. Though there is no way to know for sure. It depends on how it impacted your performance. She wanted your body for sex - and from the sound of it, you turned a simple sexual experience into a form of psychotherapy. That would be tiresome if nothing else.

    Did the how and/or when I asked her if she wanted to have my first time force her hand in saying yes? Maybe I should have just stopped when she didn't seem completely sure about it. Yes, from the sound of it, you did everything but give her your driver's license and medical records for the last ten years. Without meaning to offend, it comes off sounding a little desperate and a little sad. Again, no way to know for sure, but it sounds like she gave you pity sex, did not enjoy it all that much and felt regret about it.

    Should I have tried to make her cum with my mouth again or more? Well, again, there is no way to answer the question. I was not there and doing it. You were. That said, given that she sounded reluctant and you spent a lot of the time closely examining your every feeling and reaction, it is not impossible that you failed to put enough effort into making her feel good for her sake. Rather, to the extent her pleasure mattered at all, it was to make her good so you could feel good about yourself. Not hard to see how that can go wrong.

    Should I have tried my luck with a third time? Not from the sound of it. This is the most self-serving question. You were starting to argue and bicker and it all fell apart and your question is - Should I have had more sex? Huh? Not sure you would have gotten it had you tried.

    Bottom line. Congrats on losing your virginity. However, it sounds - and I do not mean to offend - like you were not emotionally mature enough to have it. You built it up in your head, tried to make it what you wanted it, were preoccupied with every feeling you felt and only tangentially with pleasing her except to the degree it made you feel good about yourself, and was bewildered when it ended badly.

    Believe me, I have had every kind of sexual experience. One night stand. Casual relationships. Purely animal and primal. Deeply loving. They are all superficially the same and yet were all different. You accept them for what they are. You do not, as you seem to be doing, put them under a microscope, treat the other person as a lab experiment, and then wonder why it did not end well.

    • That is a great analysis, thank you like always for your extremely detailed answers! From it, I think I failed to report a few elements of the story that could clarify some parts and change the meaning of others, but your main points are valid and I shall reflect on them. Sincerely, this got posted after I wrote it for the third time, as it got scrapped 2 times while I tried typing it on the mobile app (worst mistake ever). So after nearly 3 hours of rewriting the same thing I was kinda spent and forgot to include some things. I will probably edit this later on...

    • ... I CAN edit it, right? o. O

    • Not to worry and glad I could help. I would say that certainly you can edit, but throwing in details more or less at random is apt to confuse matters as not. My advice would be to take whatever merit in the advice people have offered you and modify it to take into account the details that you did not include. That said, I - and I am certain others - would be happy to answer other questions you have. However, remember, we are all going on about our business doing other things and it is not likely that your story will be as vivid in our memories as when we first read it. That is apt to make any further advice we give you somewhat more conditional and general. So you can revise, but your best shot - at least in this format (talking with someone you trust face to face is another matter - was your initial article.

    • Show All

Most Helpful Girl

  • I'm so sorry that your first time was unsatisfactory. It sounds like something you placed a lot of importance on. In truth I don't think anyones first time is perfect. You might've been expecting a lot of things after consuming a lot of sexual media in your lifetime, and that's pretty much never lived up to the first time. I don't think you should be too hard on yourself about it, nor her for that matter; after all, who knows how it could've gone had you waited for someone else? I only hope that in hindsight you'll realise more and more how little it actually matters in the grand scheme. You never forget your first, but I'm sure you'll have much better sexual experiences that will shrink your first time into absolute insignificance. I've always resented the way people make a huge deal out of your first. I get that it's important, but It's never the best sex of your life. It's usually your worst in fact. Don't overthink this

    • You make a good point. I agree that having more sexual experience will help me put it into a better perspective and I reckon that Tha lack of it may be what made me put it into so much thought up to now. But writing this I sincerely wished to find some points on which I could better myself on this aspect, and so far the answers are helping with that. For that, I thank you

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What Girls & Guys Said

1 1

  • Good mytake.

  • I am sorry for that... Whenever you have a date just let it go without a book to read what to do.. just be yourself and act on moment.. anyway you got expieriance and you will be better next time..

    I do not know why she accept your first time.. but no one will take it if she did not like you.. nevermind it happened.. good luck in your next

    • Thanks for your advice

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