Written by cottonthong
11 Apr 2017
My First Time (Losing my Virginity)
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I had barely been kissed before my first real boyfriend & sexual experience occurred. I was 28, worldly wise, confident, had spent 2 years overseas, outgrown a shy interior/exterior. I was ready!.. He was my best friend’s brother, 10 years older and my kind of hot! That rugged outdoorsy MAN! We had known of each other, he had been living overseas with another girl, returned to SA and I newly returned, both single. I had become quite aware of my “virgin” status, he was unaware and I did not tell him. Our first evening out together was great fun, I had transport he didn’t at that stage, I recall having to take him home, we sat in the car for a bit which quickly turned into a heavy kissing session… neither of us were living under roofs that were conducive to privacy (later only to be discarded as an issue). On another night out, that ended with a twist, and “too late” to take him home ... the thought of sex occurring never crossing my mind (but on my mind). I was still staying with my folks after returning from overseas. We arrived at my home quite late, my folks were fast asleep, we quietly snuck through to my bedroom, bumping into my mom in the corridor on her way to the bathroom, in her half asleep state she didn’t think much of it.
My bedroom was big, with my bed on one side and a sofa couch against the window. I prepared that for him while I went off to clean-up. Returning to my room I did feel a sense of anticipation, but shrugged it off and kissed him goodnight and got into my bed, can u imagine my folks finding us sleeping in the same bed? - my father was old school, he would need to have shaken his hand first….(lol).
Lying there I can recall trying to keep it out of mind, but as usual, he always surprised me with most things with very little subtlety, and in the midst of the darkness a voice calls out “is your bed noisy”.. I think I said something along the lines of “I don’t think so / it’s never been tested” AND WITH THAT he vacates the sofa and climbs into bed with me….. I’m thinking “my parents!!!” and he straight away says.. "don’t worry we’ll be quiet"….. so I run with it… letting go, thinking will he realise it’s my first time. We kiss heavily, he’s on top of me, he kneels up motioning towards removing my pyjama top, he slowly slips it off over my head ….. we kiss again as he motions down my neck, to my stomach, his hands curl into my pyjama pants as he slowly tugs them down, stripping them off in one quick action… I am shaking, almost shivering, I’m nervous, so nervous, MY SOCKS ARE STILL ON!. He continues down past my navel to my pussy, burying his face in it… unsure of this feeling… I'm still nervous and literally shaking, perhaps the cool air played a part. Even though I was a virgin I had fantasised about sex and positions and I knew what an orgasm felt like, I had practiced on myself. Used all manner of tools to simulate penetration, nothing of which ever had any effect on me… He rises up again and covers my body with his, my legs open instinctively wider, it’s now that moment, I'm anticipating it…. I let go and let it happen, he struggles a bit at first then I feel a sudden “pop,” it's indescribable, ever so slightly uncomfortable, he is in, he starts moving in and out more urgently (he is a little intoxicated), I'm not, it feels ok, nothing spectacular, nothing uncomfortable anymore, and in that moment it as gone. He slips out and heads back down to my pussy, more play on my clit, it feels awesome… one of my positions I’ve fantasised about comes to mind, I want to try it.. I stop him and ask if we can try it.. a kind of scissor missionary….. and as he enters me, the feeling is so great!! I'm loving it as he thrusts back and forth and in that moment he says… we need to stop, I can’t, and slips out and passes out next to me. I’m like - damnit, I was actually enjoying that!!!
We fall asleep … and I sneak him out the next morning early and take him home…