Story: How I Finally Lost My Virginity

By Dean

A few weeks ago I lost my virginity to a hot girl.

This would not seem like a big deal for a lot of guys but it was for me because I am 26 years old. That’s right I was a 26 year old virgin.

“some kind of virgin freak”

I am not an ugly guy, I am actually pretty decent looking and I work out. Sometimes girls check me out, when guys look at me they don’t think ‘that guy must be a virgin’. I am pretty sure I don’t look like a virgin.

Over the last few years whenever I had told guys and girls that I am a virgin they have looked at me weird, like they were trying to figure out what was wrong with me, like I am some kind of virgin freak.

Most people assume that I am heavily religious but I’m not, that isn’t actually the reason. Sure I went to Church occasionally and I was baptised but my family was never really strict on it and we got away with a lot growing up.

I grew up in a family where my step-father and I were the only boys. I had three sisters and two of those three sisters had teenage pregnancies, so me being the youngest this was a pretty strange upbringing.

By the time I became  a teenager I was already an uncle two times over and seeing how hard my sisters struggled with their dead-beat baby daddies and having to endure years of being woken up at all hours of the night by screaming babies; I became a bit terrified of sex.

My parents didn’t discourage this either, when I said ‘I don’t want to have sex until I find the right person and get married’, they couldn’t be happier! And they went out of their way to encourage this.

I believed that the virgin way, was the right way all throughout my teenage years and on a few occasions, I even told girls that wanted to have sex with me, that I can’t, because I’m not ready.

The problem with this is, if you are a young good-looking guy and you are dating girls, most pretty girls seem hellbent on having pre-maritual sex, it’s not the 50’s anymore and when you tell a girl that you are dating that you plan on keeping your virginity until marriage… Well that tends to be a real deal-breaker.

“virgin men aren’t as sought after as I once thought”

It wasn’t until I was in my early 20’s and I had just come out of a sexless long-distance relationship that I realized that virgin men aren’t as sought over as I once thought they were. In fact, if you are a 20 something virgin then this is actually really unattractive.

The thing is, I always thought because virgin girls seemed to be so attractive to guys because of their innocence and purity that it would be the same kind of thing for virgin guys… I was wrong.

I realized that I had been missing out on something really great for all these years and all because of a really old fashioned ideal which wasn’t working for me at all.

“the time had come to lose my virginity

So after a lot of thought and reflection on the subject, I decided that the time had come to lose my virginity, I didn’t want to be the virgin freak anymore I wanted to be a normal guy just like everyone else.

It turned out that this was harder than I thought.

I joined dating sites, I started going out more to nightclubs, I tried doing just about everything under the sun to lose my virginity but every time I tried something always went from and a couple of times I would get really close then I told the girl I was a virgin and she lost interest.

This went on for years.

I know that I could have just hired a top class prostitute or gotten with a fat chick but I still had my pride and I would rather die a virgin than lose my virginity like that, not to say I wasn’t tempted at times.

It wasn’t until I was 26 years old that I decided to try something different, so I started looking at dating and seduction advice sites and taking pointers.

For me one of the biggest things that I did was I improved my style.

“I didn’t look like a desperate virgin anymore”

I went shopping with my older sister who co-owns a womens boutique fashion store. She had always been telling me that I needed to get some better clothes so for once I decided to take her up on her offer.

We went to a few men’s stores, places I would never normally step foot in and I put on clothes that I would never normally wear but once I put them on, I looked and felt great, it really opened my eyes to how much I had been under-dressing.

After spending several THOUSAND dollars on new clothes, we went back to my place and she threw out about half of my old clothes, some of them I really didn’t want to let go but she reminded me that I had agreed to this so there was nothing I could do.

The next weekend I got dressed and ready to go out and I didn’t look like a desperate virgin anymore, I looked like a player who gets a lot of action.

I went out with one of my friends who already picks up a lot of girls and I told him that tonight is the night that I lose my virginity.

I was in the zone, I was prepared, I felt like a million dollars in my suit and when I hit the bar I noticed a  lot of girls eyes were on me.

We got to the nightclub and I approached a few girls and the conversations seemed a bit awkward, one girl that I was chatting up seemed really interested in me but then her friend dragged her away to the bathroom before I could do anything.

We went and sat down and I looked around the nightclub, checking out the girls that were there. I made sure that I didn’t make it to obvious so I didn’t look sleazy.

Then I got up to get us both a round and a really pretty brunette girl I had seen earlier making eyes but I hadn’t approached, she came up to me and asked ME if she could buy me a drink.

From there it was on, she had some friends there and my buddy was keeping them entertained while we were dancing and next thing I know we’re kissing and I’m squeezing her ass.

“let’s go back to your place”

And then after a while she grabbed my arm and whispered into my ear, ‘Let’s go back to your place’ and I’m thinking wow, this is all moving along pretty nicely, as long as I don’t make any virgin mistakes I should be okay.

So I tell my buddy that we’re leaving and he is grinning from ear to ear, he knows that it’s actually happening for me that this is the night that I lose my virginity and he approves of the hot girl I am with as well.

We get in a cab and we get to my place and as soon as I step in the door I feel suddenly nervous like I am just meeting her again for the first time. It’s different without the music and all the other people, it’s intimate.

I turn on some music I already had ready and I ask her if she wants a drink, she says yes, so I open a bottle of champagne and we laugh as the cork pops and then I pour us both a glass of champagne.

I’ve only just taken a sip of champagne and I’m waiting for her to have a sip of hers when she puts the glass down on the kitchen counter instead and starts going down on me in the kitchen.

“I’ve had oral sex before I’m not THAT much of a virgin”

This girl is so keen and it’s great, I’ve had oral sex before I’m not THAT much of a virgin so this is nothing new but this time I know that I can take it further and I guess thinking of that got me really excited.

I didn’t blow my load then and there, don’t worry.

I tell her ‘lets go to the bedroom’ and she goes along with it and then I am undressing her and she is undressing me and I am laying on the bed. At the time I couldnt’ help thinking of that scene in ’40 year old virgin’ where he has all those troubles with the condom, well that didn’t happen THANK GOD.

“I am no longer a virgin”

I put it on and I lay down on the bed and she is naked and she has a beautiful body and then she is on top of me and I am up inside her, I am no longer a virgin.

I lasted quite awhile at least five minutes, I was really happy with myself because I totally feared that I would just blow my load straight away. I’m glad I gave it a jerk before I headed out because it probably helped the situation.

I have to say as great as sex was, it wasn’t anything like I had built it up to be in my head. I had all these ridiculous expectations like the gates of heaven would open up and I would be filled with an incredible life altering ecstasy but really… It wasn’t anything like that, it was great and I can’t wait to do it again but the only thing that changed after was that I felt my confidence improve a lot in the following days and I am glad to have it over and done with, that’s one less mystery of life.

To anyone who is an ‘older virgin’, if you think you are doing everything right and it’s just not happening for you, then think again. Take it back to square one and don’t be afraid to ask for some criticism. No-one should rush into sex but they shouldn’t leave it for as long as I did because now I have a good decade of virginity to make up for.

Wish me luck.

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Story: How I Finally Lost My Virginity