inner game · self-improvement

The night I lost my virginity

For those of you who have kept up with my life story, you know that I am quite a late bloomer. It would not be until after college that I ended up losing my virginity.

Whoa wait what happened?!?!?

So this is something that need explaining and I’ll try to do it as short as possible. Basically in adolescence, I was not interested in the girls in my area (think ratchet and ugly) and I had overbearing parents. In my college years, pursuing women was more of an on and off type of thing. I started out with a lot of optimism but I was at a commuter school so logistics were not in my favor, had a few almosts but it never panned out since it felt like high school with my parents nearby,

When I transferred to a typical state school, I had troubles fitting in socially being a transfer student and all. Being that we were in the south, it is not that easy to find a morally “relaxed” crowd outside of Greek Life and frat guys are not going to let an outsider in easily. Due to so much that went on with college, my depression, a year spent contemplating suicide, and family problems; I finished school a kissless virgin. 

Looking back at it, it was kind of out of choice and I blame myself. I had decent looking girls into me but I was almost always trying to chase the hottest girls on campus, who were usually in sororities and went for particular kinds of men. Even in college, I had some chances but I kind of blew it. Due to being a bit too aggressive and creepy at my previous commuter school, I held back a lot more than I should have and had a good bit of limiting beliefs too.

Life after college.

After college, in Atlanta, I’d go out and meet women at bars but it never really amounted to much more than a makeout. I was in my first toxic job I talked about and even though I started with optimism, the environment burned me out emotionally and socially. My refuge was found in a small Church near my house and it is hard to pursue pre-martial sex, and not feel guilty about it, when you are in that situation. Once again, I held back a lot at bars and could never really close the deal with women, some who were showing me strong signs.

A life changing decision I made.

At my new workplace, I needed a better social media presence and part of that involved having a good headshot. I had never taken photography seriously in my life at that point or even social media presence to be honest. Given that I had made great money and had a lot left in the bank to spend, I decided to look online  and spend money on a good photographer that was well-reviewed. Apparently, the drive was going to be about thirty minutes on a Saturday afternoon and I went for it.

I get greeted by the guy’s dogs, two beautiful Huskies although he lived in Georgia, then again I am not PETA so who am I to tell the man how to live his life. For the shoot, I came extra ready and even gave him pics of people I want to look like. After some work and angle adjustment, we were able to make two hours fly by and get about eight shoots off of it. At the time, I was about twenty pounds lighter than I am right now. I was informed that after we had done shooting, he will do some work on photoshop and other tools to brush up the pic and I headed home. The next day I get the pics, they were beautiful and I put them up on social media as well as dating apps. 

The flood gates open.

After having well done photos up on dating apps like Hinge, Tinder, and Bumble; I got close to over 20 matches on each of the apps. Bumble in particular was kind to me in Atlanta and I had over 50 matches in a period of a week. After a month, I had a 100 matches on both Tinder and Bumble. I had my first ever date while visiting a relative in a nearby college town the following week, it was with this hipster brunette and went nowhere. Next, I had a date after returning to Atlanta with this Lebanese girl and that ended in a kiss but I got too drunk. The girl kind of looked like Kendall Jenner in some weird way, she had a similar type of appearance and that was actually my first long makeout session with a girl, and I fail to pull the trigger……

Such a validating feeling when it happens!

I would have a string of dates and continue having them for the next couple months, then bad news hit again. Things were not going too hot at my new workplace and I get drawn into a Friday afternoon meeting during lunch with my boss and HR on the line, they fire me on that day. I still had a good bit saved up and got a great deal of severance, fortunately. 

After taking a weekend to relax and get sad about it, I found that the dating apps keep churning out matches to where I had to turn the notifications off. I was like, leave me alone, I need to cry about my job loss! Yes, it got to that point for me. 

“Say something nice: You look great in panties!”. No but really, very validating feeling!!

I’d have a date with this tall Colombian brunette from Seattle which seemed to go well, we were chatty with each other. Something about her vibe just really got me, I was feeling it, and I was going to try and take her home. Despite that, I could not close the deal with her because I was a bit hesitant.

Match here, match there, and whoa hold, what’s your name!

I would match with this one girl on Hinge and for the moment, it was a bit too good to be true. Ever had those moments where you kind of think that it might be a bot or some girl trying to get more Snapchat followers instances? She was a beautiful tanned brunette from Vermont of all places, definitely wanted to hear her story about how she landed in Atlanta. I didn’t chat on Hinge too long with her, opting to go for the number instead.

First rule of online dating, go for the number!

It doesn’t hurt to try my luck plus she liked a picture of my Halloween costume, so I started the chat. After a bit of back and forth, I get her number and we are texting each other. We are supposed to meet the coming weekend, it is on a Sunday night, and I am excited to see if she is actually the girl from her pics. Come to find, a few hours earlier, she has to reschedule the date itself. 

So after a week of interviews, we finally end up meeting up the following weekend and it is on a Sunday night. I schedule the date at a bar about half a mile of a walk from where I live. Arrive at the bar and I wait for her, there is a seat that I have saved. Me and the bartender make small talk, at this point I am a regular but they have a different dude. At one point, I even tell the guy, if some landwhale walks through we can have a fun chat about how fake online dating is and how I got catfished.

In she comes.

As it neared closer to eight, she walks through and I did not get catfished at all. While she had glasses on and her hair were more curly, the tanned skin still shined and that cardigan looked amazing on her. I get up and hug her, she is maybe a couple inches shorter (I am 6’1). Looks wise, I’d say if you have a thing for tanned brunettes, she would definitely be your type. 

I cannot even remember the conversation word for word since it was a while back but we chatted about her experiences and what brought her to the city. We chatted about what she liked and how her experience on dating apps has been, she told me about the crazy guys she has met. I tell her that I have had a decent enough experience but said I want to kind of go north. She asks me why, I tell her that people are just way more laid back there while here in Atlanta, they’re kind of uptight. Now she agrees with me, we chat a bit about the tight morals of the city.

What apparently brought her to Atlanta was interest in the film industry but the project she wanted to get on got cancelled. Before she knew it, she had found more opportunities in film and kind of wanted to stay in the city a bit before going back up north. From what she said, she wanted to eventually end up in NYC.

As we chat, I tell her that it feels like being in Atlanta is like being in a Private Religious school or something where if a guy holds hands with a girl, there is that sense that “he should not be doing that”. Then she agrees and says “fuck yes”, I said I am going to put her in timeout for cursing and call her “young lady”. Maybe I sounded cheesy and my lines were not working but damn, she was hooked and its not what you say but how you say it. Most of all, I looked at the emotions in the air and they seemed so upbeat.

At some point, it comes down to just capitalizing when emotions are hot, striking while the iron is hot as the saying goes. So I decided to ask her what she has going on for the week, the entire next day is free for her. I let the date go on for a bit more and after I close out my tab, we have both had close to a couple drinks. Now I talk to her about the reconstruction in the area and how nice the apartment is, we chat about it. 

Date ends.

As the date ended, I stuck on the topic of how good the apartment looks and how we are so lucky with the buildings they have had in the past couple years. We step outside from the bar and I am chatting with her, she is not keen on leaving, and there is an awkward silence. I go in for the kiss and she kisses me, we lock lips for a while until a couple women pass us and an elderly woman gives us an awkward look. As she passes, we both laugh a bit and I tell her we should go back to my place to check it out, her breath is fast and she is aroused, we go back.

We arrive at my apartment and the vibe is intense, we can feel it in each other’s breath as we walk to it from the parking lobby. As we walk there, I arrive in my room and immediately as the door closes, we are eating each other’s face. Now it is a tie between who is more aggressive but she was really into pushing the action. I am so grateful at that point that I had done a week of no fap.

More action.

We make out and she is pulling off her clothes, I am almost nude and she is down to just her panties which were white and went well with her tanned skin. I pulled them off after I had sucked on her hard pointy nipples, something she really liked. Before I knew it, I was actually on my knees pulling down her panties, she had kind of a landing strip of dark brown hair and because of all the emotions in the air I ate her out. At one point, her knees started to shake as she let out a loud moan. Somehow her body smelled that smell of hazelnut and I could tell it was somewhat more natural than a cologne.

I put her over my shoulder and luckily, I had a handful of condoms in the drawer near my bed. The slim yet tall body was easy to carry and I gently threw her down, eating her out a bit more before I got hard. As soon as I got hard, she blew me but we got into a sixty-nine position; I ate her so that her knees shook a bit and her pussy landed on my face. We had a slight laugh over it and she blew me a bit more as I sat up straight. 

As soon as we were ready to get down to business, I tried to put on a condom and failed. I tried to put another one and failed again, she was laughing at this point. Third time around, I said fuck it and forced it on as I was hard. We spooned a bit and then she rode me, I was surprised I lasted over a minute given how my heart was racing and blood just boiled. After a minute, I came, first time ever. We made out a bit and then after an hour, I led her back to her car.

I’d never see her again after that because I never made an effort to reconnect with her, I had too many options I wanted to try out. We texted back and forth but she had a busy schedule given what was going on with her life. Still, I learned how some of the best nights of your night can happen unexpectedly.


6 thoughts on “The night I lost my virginity

  1. Thanks for the article man. It’s kind of weird how similar my life has been to how your early life was. Obviously not exactly but I also went to a commuter school and have no sexual experiences at age 23. (kissless virgin) Despite all that, almost everywhere I go I get smiles from women and often female employees at any place I go to often smile and their face lights up when I make eye contact. (I dress nice and workout)

    Anyway I’m been trying more online dating and getting a few matches although I feel like Tinder is mostly bots for me. I’m going to take a break from online dating as I find it really distracting and plan on returning in about a month when I sort some things out.

    Basically I feel like my experience will be similar to yours when I finally lose mine. Right now, I’m just focusing on developing my skills for my career, working out to get in great shape, and pretty soon taking updated photos with a pro photographer in LA.

    Thanks man and take care.

    1. You are definitely on the right path with what you are trying to do, that much I can say with confidence. What I will be doing and am working on is releasing a guide for online dating, it is going to be in a series but I think you might find it useful. One thing we are going to focus on is what kind of photos you want to take in order to get the results you want with online dating.

  2. It’s now very typical for a Millennial male to be a kissless virgin by age 25. After 2015, it became the rule, not the exception.
    In modern day USA, I estimate that 80% of today’s 25 year old males (i.e. born circa 1995) are still virgin. Of these, I estimate that 80% have never had their first kiss.

    1. I am one of them at 23 yrs old and that’s hoe ai found this blog. Terrible adolescent life,shitty dumbass parents,crap friends,depression at hs. College was better,but it was commutter school difficult to pull girls if you’re starting from a defecit in socializing and don’t have any guidance,long term confidence and support from the people around you. I think it’s very common amongst asians to be virgins late in their twenties because of their culture.

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