By the time I was a senior in high school my best friend and I had both become very sexually active. We were both cheerleaders and practically

7 years

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By the time I was a senior in high school my best friend and I had both become very s******* active. We were both cheerleaders and practically imseparable. She had a steady boyfriend but I prefered just dating. We double dated most of the time and would end up parked somewhere making out. She had been putting pressure on me to do it without a condom sometime telling me how much different it was. Since they were going steady they did it a lot I finally agree that I would do it when I felt comfortable with the timing. One Saturday night we were parked and she knew I had just come off my period. When we parked she just told the guy I was with that I wanted to try it without a condom. I was upset that she had not let me decide when to do it but I dated him pretty regularly so I didn’t say anything. When he wanted to know if I was sure I told him I was ok with it. The feel without a condom was a little different and more arousing. I wasn’t sure what to expect other than he was going to c** in me instead of the a condom. I was just relaxed enjoying the s** as alway when he sent a powerful shot deep in me. My whole body shook and I yelled “Oh my God…oh my God” as he just kept c******. My friend sat up and looked over the front seat telling me I wasn’t supposed to enjoy it THAT much. My date just ask if I was ok. When we finished had to put kleenex in my p****** to catch what he had done and I could feel it running out of me all the way home. After we were home my friend called to see how i liked it. I told her I was going to kill her if I got pregnant since he had done so much. I was a nervious wreck for the next 3 weeks waiting for my next period. I was a couple of days late which added to the scare but it finally came. I never did it again until I got married without protection.

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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.