Observations on Dating

Boy meets girl

Colin here, you could say I began growing up in the mid-90s or at least that was when my interest in the fairer sex surfaced. And so began a five year stint of frequent masturbation as I tried to figure out how to get girls to open their legs.

Looking back perhaps one of my advantages was I was totally comfortable talking to girls but when it came to asking for a date or even just to hang out, I kinda lost my voice (not literally) but I totally lacked the confidence. School would be in class with girls, sometimes exchanging almost flirtatiously smiles and comments but not having the wherewithal soon follow up then of course I'd go home and exercise mostly my right hand.

About a month into this awakening as I call it, I happened to find myself chatting to Genevieve. We were just gossiping and talking a bit about schoolwork and she said something kinda cheeky, I do remember what now that we end up rolling around on the bed, wrestling and tickling. Then I got the upper hand and sat on her hold her down and as I looked into her eyes there was a kind of magic happening so I kissed her and blow me, I lowered myself down and kissed her and she responded. We made out for about 15 minutes before she said she had to go. I don't think she really had to that was probably just as much out of her depth is what I was even though we were enjoying ourselves.

Genevieve and I remained friends that we never got as physically close for several years. I was a lot more confident after that and I asked a few girls out on dates. We did a lot of kissing and cuddling and one of them gave me a blow job but no matter how hard I tried, I couldn't get inside their knickers although getting undressed that they represented some small success.

Outside of school we gossiped about who was going out with and doing what to who but I never believed half of that stuff. I was still only 15 at the time and some of the slightly older guys and began teasing me about still being a virgin, for some reason I wasn't in any position to deny that but then I started spending a bit of time with a girl called Glenda.

We went on a few dates and I finally got her naked and we got as far as having oral sex but she was also a bit off and on, like once I just got her undressed and she decided she had to go and do something else leaving me laying on my bed and having to relieve myself. I persevered and she invited me to her place and her mum was really nice. She offered soft drink and cookies when I called by which was becoming more frequent toward my 16th birthday.

By then Glenda was becoming a bit more controlling which I didn't like them but she seemed like the best chance I had of getting laid. Then one Saturday we had arranged to go together and help set up for a party. When I arrived to pick her up, she had gone out but am invited me in, quizzed me about my schoolwork, she made coffee and we fell into a general conversation.

I was thinking it was time to leave when she asked me how I was getting on with Glenda. I wasn't sure what to say so began mentioning a few things that we enjoyed you know like music and the idea of being successful that kind of drove us to do well at school. I do know what it was, perhaps I looked a bit frustrated that she told me to wait.

She left the room and came back a minute later then said with the same sparkle in her eye as Glenda when she was leading me on "I'm not sure of your intentions with Glenda, but I think she's just gonna keep on stringing you along and to you get bored. I disapprove and told her that she should be fucking you but I guess you know that she won't be told that on the other hand...."

She looked at me more intently and then her dress fell to the floor and she didn't have a stitch underneath. I didn't have time to react before she had her arms around me saying "you do look rather delicious and I'd rather like to eat you up."

My testosterone boiled over at that point that she giggled and suggested that I get undressed. We went through to her bedroom and an hour later I felt as if I'd become a man. Over the next month she'd let me know when she had the house to herself and argue over for a fucking good time. Susie was nice looking and I couldn't tell that she had three kids.

I was still going out occasionally with Glenda and becoming increasingly bored with her because she was still playing the same game whereas with Susie her mother I was free to experiment and she gave me a lot of guidance. But I was becoming attached so I went over one day to find that Susie was out with Glenda but her sister opened the door when I knocked and like she was wearing this totally transparent kind of slip.

She said nothing about Susie being out and invited me in then she cornered me and said that she'd like a bit of what I've been giving Susie. Just her seminaked presence was enough, we spent an hour fucking there then she took me back to her apartment and we spent the day together most of it in bed having sex, talking about sex and afterwards I didn't know whether I was confused or what?

So Susie kind of palmed me off to her sister Becka although we had a threesome one evening and they teased me about how they were training me. Not long after my 16th birthday which was kind of non-event, I got chatting to a girl from my school, she is a year older than me and works part-time in the pharmacy.

There were talking about the party we had both been to this she surprised me by inviting me to a party she was going to and I spontaneously said yes. It was a Saturday night and after spending a couple of hours with Becka that morning, playing sport in the afternoon I was kinda rushed to get to this party but I made it just on time to meet her outside.

We had a few drinks in a conversation got a bit more flirty, and then we were making out and our mutual desire took us to a bedroom. I was so amazed she didn't play hard to get and we had a wonderful time together. We continued to go out together on occasions and I occasionally spend time with Susie and Becka although not together.

I was still going out with Glenda on occasions as well and she'd sometimes accuse me of losing interest in her. By then I was a lot more confident and we got to that stage where I had her naked, I was trying to talk her into going all the way that she was still playing hard to get so I rolled off the bed got dressed and said there was something I had to do. She called me a dirty rotten barstard and I never went out with her again although I saw her auntie Becka a few times.

By the time I was 17 if I was feeling the need I had a number of girls I could call up, visit and half of the time we'd end up having sex. If there's a moral to the story, if the girl is a bit tricky, check out the mother and rest assured success comes to those who do not give up.


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