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. She didn’t offer any more resistance as I pulled her shirt over her head and flung it aside. Now she was in her bra and pants, and I removed those shortly afterwards. Now we were both in our underwear. 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 my face. Mmm. Fuck 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 lot for me, but I still enjoyed the sensation. After a few minutes 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. 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 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. Trouble cumming or just staying hard. I couldn’t get off that first night with her, so things 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.
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, including on one of 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 shaking all over 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 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 all of 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 may post the occasional update, but for the most part my journey is over. Feel free to leave comments, and please check out my other blog. I’ve been slacking off with it but I’ll be posting more vigorously and very soon: https://descentintodadness.wordpress.com/
THE FINAL TALLY:
First dates: 37
Second dates: 5
Third dates: 3
Stood up: 2
First kisses: 3