Most of my friends had lost their virginity by the time we started our junior year of high school. I hadn't dated anyone steady prefering to play the

7 years

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Most of my friends had lost their virginity by the time we started our junior year of high school. I hadn’t dated anyone steady prefering to play the field so I had kept mine intact. My sixteenth birthday was in October so my friends began putting pressure on me to loose it on my birthday. After lots of back and forth discussions I made the decision to do it. I picked a certain guy I wanted for my first time planning it for the day of my birthday at my party. That evening everything went as planned so after we celebrated my birthday the guy and I left the others in the family room heading to the bedroom. It was kinda embarrassing u********* in front of him but once we were in bed I calmed down. Nobody had ever gotten to second base with me with only a couple even getting to play with my t***. We kissed for a while as he played with my t**’s then he started f******** me which again was a little embarrassing but good. I didn’t know what to expect but soon he had me pretty excited telling me he thought I was ready. He put a condom on then got on top of me. While he was f******** me he had mentioned how tight I was then when he tried going in me he was having trouble. He said I needed some more lubrication so he got some hand lotion and used it on me. When he tried again it hurt a little but he took his time finally being able to get all the way in. He took his time to make sure I enjoyed it then he told me to get ready he he was going to come. When he did my whole body shook then just went limp. When I finally caught my breath I told him I hadn’t expected that but it was awesome. Then he told me it was because I had been so tight that the condom broken so he came in me. He didn’t stop because he didn’t have another one and wanted to make sure I got my birhtday wish. We didn’t tell anyone what had happen but they found out a couple of weeks later when I got my second unexpected birthday present when I didn’t start because I got knocked up. After some thought I decided to have the baby then gave it up for adoption.

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In truth bored_april you been nothing but a disappointment in my life. What a waste of a human being

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When I was younger, about 16, I was insatiable and as a result of having my first anonymous hookup with another kid that was 16 (off omegle of all things) I sought to have more.
In this effort I downloaded Grindr and lied about being 18, eventually finding someone who hosted an anon darkroom not even 5 minutes away and who was more than happy leaving their door unlocked and a** ready. After I was invited over and tentatively entered their place I immediately set about u*********, going to nothing in a minute and slowly started up the steps to his room. Once in his room I was approached in the dark by him – a 30-something yr old man who was equally as naked but twice my size – and he reached down and started to blow me once he settled on his knees. Within minutes once I was sufficiently erect I prodded him onto the bed and had him bend over, eventually sliding in without any additional lubrication and begun to – at the age of 16 – f*** this older mans a**. I went for about 20 minutes by my estimation and slowly over the course of the f****** went from doggy, to sideways to having him lie fully down whilst I went to town on him.
Eventually I finished in him and got up and left. Once home I gushed to him about how much fun it was and how I appreciated him taking a chance with me, with some more conversation eventually leading to my age being revealed and – to my own surprise – him revealing that he’d prefer it if we kept going in spite of it. I’d meet him continuously, probably once to 3 times a month or even multiple times in the same week until I moved away at 18. I never saw his face but I remember being inside him so vividly.