I was 18 when I first discovered online websites like swingingheaven and where you can connect with strangers and potentially meet for fun. A little bit about me, I'm 5'7, 110 lbs, slim, ethnically Indian, with an average sized cock. Personality wise, I'm shy/introvert, so communication whether it be verbal or written is not one of my strengths, moving on. I was a virgin at the time with the only experience of kissing and at 18 years old, hormones were raging and was horny all the time. I was jerking off 2-3 times a day to satisfy my urges and I wanted to have sex and finally experience the real thing and not just jerk myself off anymore. After surfing through several sites, I connected with an older women, a cougar and started talking with her. Little bit about her she's a black 5'8, somewhere in her late 30's women , with curves in all the right places. We started exchanging emails and this continued for a few weeks, just getting to know each other our likes and dislikes in the bedroom, what my expectations were for my first time and what I wanted to try etc.. We eventually set a date and time to meet up at her place so I could lose my virginity. I got to her place around 1 in the afternoon, was extremely nervous, not knowing what was going to happen. I rang the doorbell and she was waiting for me and opened the door and she welcomed me in and gave a hug and then went to her room. The room was dim light with only a night lamp on, with some music playing. I sat down on the bed and she turned the TV on to watch just to ease the nerves. She came and sat down next to me and I was glancing back and forth between the TV and her, while trying to have a conversation not knowing how to proceed further. After a few mins, while staring at her, she moved in to kiss and I reciprocated and we kissed for some time, while exploring each other's bodies with our hands with mine squeezing her tits and nipples and her rubbing my cock through my pants. We eventually broke the kiss and undressed, she laid on her back and I moved on top of her and we kissed some more. I started kissing other parts of her body like her neck slowing moving to her boobs and I played with them for some time sucking them, biting the nipples, squeezing the other one with my free hand and alternating back and forth. Eventually I moved on to the pussy and started giving her head and fingering her and felt the pussy getting wetter and wetter, because my fingers were able to slide in and out much easier. We then proceeded to a 69 and that was the first time I got a blowjob and the sensation was nothing I had experienced before in my life. I thought I would cum but since I was also focused on licking her clit and pussy, I didn't and I pulled out and got up and then we took a small break and cuddled for the next few mins and basically calm down, because I know for a fact if I didn't I would have cum. We then resumed again with her stroking my cock and my fingering her and now it was time for the SEX. She opened her drawer and pulled out a condom and as I was putting it on I came prematurely in the condom, could have been the nerves or the excitement. It didn't end there tho, since it was my first time, I got hard immediately and put another condom on. She then got on top and started riding me, that didn't last very long either, it was max 1 min and I cummed again. We cuddled for about 30 mins after and I came home afterwards. The whole session lasted about 3 hours and that was how I lost my virginity. I still see her every month and it has only gotten better since that first time, but I doubt there will be something like that first time again. I have made a lot of progress since then I don't cum as easily so we are able to try different position, also able to make her squirt every time now, which is pretty nice. That is my story, would love to hear people's comments and critique it if you want. ENJOY READING!