Sorry for the delay, folks.  June is a notoriously busy month for me and I’ve been busy… *ahem* in other ways as well.

Picking up where I left off…

As I said, Rebecca and I continued talking throughout the week, and the following weekend she came to my place.  I took her for another nature walk, we made out in the bamboo forest, went to dinner (Italian) and then it was back to my place to watch a movie and play a board game… but you all know how that usually turns out.

Sitting on my couch talking led to sitting on my couch making out, then to sitting on my bed making out.  Some clothes were shed.  I sat her up so I could pull her shirt off, and she laughed and went, “what are you doing?”

“What do you think?” I said slyly.

“You can’t take off my shirt when you still have all these clothes on!” she said.

“Well, then, you’d better do something about that,” I said cheekily.  So she grabbed my shirt and pulled it off, and didn’t offer any more resistance as I pulled hers over her head and flung it aside.  Now she was in her bra and pants, and I removed those shortly afterwards.  And then we were both in our underwear in no time at all.  I knew this was it.  It was going to happen.  Our hands roamed all over each other’s bodies for the longest time, just taking it all in.

Her breasts looked like they were straining to be free of her bra, so I decided to help out. I knew she wouldn’t stop me.  One of the hooks came undone easily, but the other was stuck and I was having  a hard time with it.  We both laughed about it, but I finally got it off and there they were… big, magnificent breasts hanging right in front of me.  Mmm.  Oh yeah.  I kissed and caressed them and sucked on her nipples and basically went to town.

Then she pulled my shorts off and started to blow me.  It wasn’t at all what I expected it to feel like.  It felt warm and wet and really good but weirdly different at the same time.  I wasn’t used to that kind of stimulation and it wasn’t doing a whole lot for me, but I still enjoyed the sensation.   After a minute or two of that I couldn’t wait any longer.  I told her I wanted to be inside her.  She grinned at me and said, “finally… I’ve wanted you inside me all night!”

She dropped her panties, I deftly rolled on a condom, and then she mounted me.  I couldn’t feel much with the condom on, which kinda sucked, but I was inside her!  I did it!  We went at it like rabbits, trying out a few different positions.  We ended with missionary and I nearly pounded her into the wall.  I was making a bit of a racket, making the headboard thump and rattle.  Then we just lay there until 3AM, naked in each other arms and keeping our breathing in sync.  Eventually we drifted off to sleep.  The next morning she told me her vagina was a little sore but very happy.  Good deal.  I had gotten her off at least a couple of times during the night.

The next night she wanted to see me again.  We went out to eat, sat on the beach in the darkness, and then headed back to her place.  We tried watching another movie but we were only five minutes into it before she said, “Let’s go to my bedroom.”  This time the clothes came off even faster and I made it all about her.  I kissed her, caressed her, fingered her, licked her, pinned her down and flipped her around, and massaged and grinded her until she had orgasm after orgasm. The best part was when I spanked her.  I went from grabbing her ass cheeks to lightly swatting each one in turn.  Then I started smacking her harder and harder until her flesh rippled, gently massaging with my hand in between each slap. She bit and scratched me and made a great deal of noise and completely soaked me when all was said and done.  Afterwards she basically passed out and we slept until 6 AM.

A week later I told her I was a virgin.

I had to.  The thing was, I was having performance problems during all the aforementioned.  Trouble cumming or just staying hard.  I couldn’t get off that first night with her, so things actually didn’t last very long.  After a lifetime of porn and masturbation, I was struggling to adapt to new stimuli.  I was so used to my own hand. Not to mention my dick was suffering from a bit of stage fright.  I didn’t want her to think there was something wrong with her, so I finally fessed up.  I had to.  On a scale of 1-10, 10 being the most shocked, she registered a 7 at the news.

Things became much easier after that.  Even though I had lost my virginity by that point, I was still stressed out that I hadn’t told her and that in itself was just making things worse.  I also ditched the porn and masturbation and saved myself for her.  It was almost a couple of weeks before we saw each other again, due to work schedules and then both of us going out of town at the same time.  Finally we were back in each other arms again.  She came back to my place.  We started watching yet another movie but we both fell asleep.

Sexy time came in the morning.  Touching led to caressing which led to articles of clothing dropping off one by one.  She climbed on top of me and started rocking back and forth, rubbing her pussy against me.  We had prior discussions about safety and this time we went condom free since the proper precautions were in place.  It was unbelievably hot and wet inside her.  So THAT was what it felt like… I lasted only five minutes before I exploded. No wank can ever prepare you for that feeling.  It was amazing.  And messy.  I didn’t realize how messy sex was.  When you cum inside someone it all just kinda runs back out.  She had to wrap herself in a towel before she got back into bed with me.  I was in a blissful daze.  And I’d finally broken the wall so there were no more performance problems or anxiety after that point.

We went for round two later in the day, and that was all I could manage.  She had to get going, and I didn’t have any strength left.  It took me until midway through the next day before I fully recovered.  But ever since we’ve been having sex any chance we can, and by that I mean during whatever time we have free on weekends.  Although, we did manage one mid-week rendezvous during our lunch breaks.  I came three times in an hour and I was barely able to stand after that.  Of course, I always make sure she’s satisfied as well.  And then the following weekend we went at it until I was physically drained.  The last orgasm I had with her was the most intense yet and I was shaky afterwards.

Anyway.  So that’s how I lost my virginity.  I got off to a slow start with mixed results, but now I’m on a roll.  It wasn’t as big a deal as I thought it would be.  It wasn’t life-changing and I didn’t feel like a brand-new person afterwards.  The first time wasn’t nerve-wracking or awkward.  Maybe a tiny bit awkward, but that went away with practice.  If anything it was a bit surreal.  A sense of, “Wow, am I really/finally doing this…?”

One change I’ve noticed is that my libido has calmed down quite a bit.  Ironic.  I thought finally having sex would send me into overdrive, but finally understanding the mystery has taken the edge off for me.  Perhaps it’ll go crazy again over time, but for now I’m experiencing a new-found and much welcomed peace and calmness.

In the meantime we appear to be an item.  We talk every day and see each other whenever our schedules permit.  I don’t know how this will all end, but so far so good.  I’m very happy being with her and it’s such a pleasure waking up next to her in the morning.

In the end, it was worth all the struggle, frustration and heartbreak.  I feel like it happened at the right time and with the right person, and I’m glad I didn’t do it “just to get it over with.”  Sometimes the old cliche is true – it really does happen when you least expect it or when you’re not looking.  I just had to date three dozen girls before I found her.  I know some of you are struggling with your own virginity and/or just trying to find that someone special.  I urge you not to give up, no matter your age or circumstances.  Maybe take a little break and spend some time finding yourself first will help, like it did with me.  You can find success too.

Now the question is what to do with this blog.  I’m going to leave it up for all past, present and future readers.  I’ll continue to check in and post the occasional update, but for the most part my journey is over.


First dates:  37
Second dates:  5
Third dates:  3
Cancellations:  9
Stood up:  2
First kisses: 3

74 thoughts on “Success

  1. Congrats and hope it all stays well for you! Glad you waited for the right person. That’s what I always tried to do and my first sexual experience was with someone I was very into because it wasn’t something I regretted down the road.

  2. I’m so excited for you. Best of wishes on the rest of this journey. And can’t wait to read more about your dad.

  3. Whoa!! I almost can’t believe it, but what a great conclusion to this long journey. Next step is navigating a relationship, which is a whole different world 🙂 I’ve been waiting for this too, keep us updated!

    • We’re not officially in a relationship but essentially we are. And so far I don’t even have to make an effort at it, everything just comes naturally with her. She’s a very caring, understand and accepting person and I’m very lucky to have her. It also helps that we’re very much alike, have similar interests, and are on the same page on the important things.

      • Those are all great things to start with, I’m so happy to hear it! There are inevitably challenges that will come but it sounds like you’re both in a great place!

          • Meh, my professional life is crazy and I’m making some big transitions but my personal life isn’t. Gave a relationship with Brent a good honest try but in the end it didn’t feel right to me, despite how close we are. We still hang out a couple times a week as friends. I’ve been slow at getting back in the dating game, honestly just enjoying single life at the moment. We’ll see! Have been doing a lot of writing for school and my interest in blogging has faded but I still love reading!

  4. This is awesome man. Well done. Question though, you’re cumming inside her without a condom? I hope she’s at least in the pill. I’d hate for your next blog to be called “Unfortunate Baby Daddy”. Condoms can desensitize esp when you’re used to doing it yourself to the point of no orgasm. Had happened to me a handful of times. Good job of getting off masturbating and porn. That’s the right way to go. Save it for her.

    And seriously, baby daddy drama us no joke if she’s not on the pill.

  5. Oouuu ! This was amazing to read ! Im very happy for you and I hope everything goes well with her, she sounds like a gem 🙂

    • I will say be careful about who you have unprotected sex with – it needs utter trust from people who know each other. You two have only just met after all.

  6. Congrats! But as it happens, there is life after losing your virginity. The descent into the rabbit hole of romance doesn’t stop there. So maybe don’t totally abandon the blog and keep us posted 🙂

  7. I am still a virgin at 27 and haven’t found the right person yet. I have been very busy with work at an internship. Grad school also has been keeping me busy, so I haven’t had much time for dating or relationships. Congrats!

  8. Congrats dude, all the best to you two! I guess it’s the same with everything in life, you first have to shovel a shitload of shit to earn something good/beautiful.

    • lol I’ve certainly shoveled a lot of shit, but it was all worth it. I learned a lot about myself in the process that will help me going forward, and now I can be in a position to help others who are struggling like I was.

  9. I hate to be the one to rain on the parade, but I was honestly a little disappointed by the lack of details. My first time was with someone that I didn’t like and I didn’t even want to do it, but I can still remember what he wore, smelled like and said. I would have thought you’d be overflowing with details.

    I am glad that you got past this hump though and it’s smooth sailing from now on.

  10. Oh, Lad…Lad…Lad…

    For the third consecutive day, I remain a giddily welled up, semi-incoherent gibberer. Until able to relate my thoughts cogently, please accept the following as expressive proxy:

  11. ….*sigh*…what a journey this has been! So glad I’ve gotten to know you through this blog but so glad for you that it’s finally over! Can’t wait for updates as we go along dear friend. XoXo.

  12. I am so incredibly happy for you!! Although will miss reading about your wild dating adventures… I feel like we were one of each others first followers! Will certainly continue to follow along your new blog. Keep us updated with how this relationship goes. Enjoy every minute of it!

  13. I have followed your blog for a long time and while I`ll admit that I kinda wished you would stay a virgin because of my own frustrations with women, now that it finally happened it is a big inspiration for many. After so many setbacks where many would have given up, you always bounced back and accomplished it. Now I want to give more effort to be active towards approaching/dating and I think this will help many other people too towards finding someone or just get more knowledge and actively pursuing this area of life. I think you should keep this blog which will help many 🙂

    • I’m planning on keeping this blog up. I hope it will be a source of inspiration for others, or at the very least educational. Definitely put the effort into dating, and put effort into yourself as well to be the best you can be. That seems to be the ticket.

    • Thanks for the congrats and the best wishes. So far everything is working out really and I feel it will continue to do so. And I’ll have to check out your blog too. I’m always looking for new ones to follow.

  14. I really enjoyed hearing this from a man’s perspective. Also interested to read the effects of porn first hand in a way that is honest and realistic. Obviously since this was a year ago I am keen to know what happened next! I shall have to explore more of your blog!

    • Yeah that was definitely an unexpected consequence for me. I think a lot of it was mental too, because as soon as I fessed up that I was a virgin my performance problems and anxiety went away. I’m curious though to see what happens the first time I get with another girl.

  15. I also like the way you cared about her response and were sure to give her pleasure rather than just take your own. This is pretty rare so you should realise that your attitude and general nature already hold you in a good position to satisfy and keep a partner. I’m sure I will have more to say as I read through your blog. Would you be interested in being interviewed for my blog? I’m just doing the third one now but you can read the other 2 on my site at – in the sidebar ‘Interview with my first follower’ and ‘Interview with my second follower’. From hereafter I will just drop the first, second etc 🙂

    • Is it really that rare? Interesting. Ha, well in any case it didn’t help me keep her, although she had her own issues. And yeah, I wouldn’t mind being interviewed. I haven’t gotten around to looking at your blog until now but it looks intriguing. I’ll have to catch up on yours as well!

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