This is a print version of story Losing my Virginity by Alex923 from

Losing my Virginity

I confess that I lost my virginity when I was 13 to my s****r’s best friend. Her name was Claire, taller than me but she was 16/17 at the time, quite thin and with hot ginger hair. I’d always kind of had a crush on her partly because she always wore skirts. One night, was at home alone. My parents were out at some party and my s****r was on a school trip. About 9PM there was a knock on the door, go downstairs and answer the door, its Claire, looking kind of d***k standing there in the rain; she says “Hey Alex, is Jenny (My s****r) there?” I then tell her that Jenny is on the school trip. She thinks for a second then remembers saying “Oh right!” She then asks if she could come in out of the rain. I say yes, she comes in and sits at the kitchen table I offer her a drink, and she replies by asking me if I like vodka. I say that I don’t know because I’ve never tried it she pulls a small bottle of vodka out of her bag and asks if I’d want to try. I agree and we proceed to finish the bottle, which was only about half full. When I say “we” it was manly her, I had one vodka coke and didn’t really like it, but drank it anyway.

I ended up quite tipsy as it was my first real drink. We sat there and talked as she finished the vodka and I just had coke with a little vodka. The conversation eventually turns to her asking me if I have a GF, which I didn’t, and then what I’d done with girls, I say that I’d only kissed, which I hadn’t. This is where things really start to hot up, she then asks me if I’m a good kisser, I tell her I’m not sure, that’s when she spontaneously kisses me and before I realise she has her tongue down my throat, we kissed for a little while and then she stops as suddenly as she had started and says I was OK. We sit there in an awkward silence for about ten seconds, when she says that she’s got an idea, then grabs my hand and basically drags me upstairs and into my s****rs room, and pulls the curtains, by this time I’d sat down on the bed, but she told me to stand up. Then she almost ripped my shirt off me and then took hers off then her bra, I just stood there in awe when she took her bra off and then hung it over my face then she pushed me over onto the bed landing on top of me her bare chest pressed against mine, then kissed me once quickly and said “I take it you don’t have a problem with me taking your virginity?” I just about stuttered “N-N-No” she kissed my chest and says “Great!” and proceeds to take off my jeans, once they’re off, I still have my boxers on and she stands up and says that she’ll let me take her skirt and panties off. I do so very carefully and when her panties reach her ankles she grabs my boxers and yanks them down. That’s when I get my first chance to look at her pussy, not shaved, some short ginger pubes, she says my dick looks cute, and lies down on the double bed and gestures for me to lie down beside her, when I do she take my hand and shows me how to finger her as she jerks me off, a bit pointless as I was already as hard as I’d ever been.

After a little fingering and jerking off she stopped and sat up on her knees and kissed me a few times and told me to just lie there, she’d do the work she then sat over me cowgirl style with her pussy just out of reach of my cock and takes it and rubs it against it a few times before slowly inserting it, she moans softly and so do I, as it was the best thing I’d felt in my life so far, she slowly fucked me and bends down and starts kissing as she continues, the kissing only happens for a bit as she’s soon gasping and moaning my name, she tells me to grab her ass and give a little help, when I do the feeling in my cock becomes a million times better. She continues moaning my name and I start moaning hers, her moans soon turn into almost screams just as I cum inside her, we both stop then and before she even moves after getting her breath back she says “My god Alex that was the best sex ever!” She eventually gets off and heads into the bathroom, and I just lie there on my s****r’s bed having just fucked her best friend, when she came out of the bathroom she tells me to get up and take my clothes into my bedroom and not to get dressed while she’ll tidy up Jenny’s room.

I go into my room and pull my curtains as it’s now dark, set my clothes on the floor and sat down on the seat and waited for Claire she appeared a few minutes later with her clothes which she set on the ground next to mine and then lifts out two pieces from the pile, a pair of tights, obviously my s****r’s and a roll of toilet paper, sets them on my desk and then closed the door and sits down on the beanbag I had in my room. She then proceeded to tell me what we were going to be doing as my parents were not going to be back for another six hours, and my s****r for three days, she was going to dress me up as a girl, her exact words were “You’re going to look cute with tits and in a skirt” She then grabbed my boxers and put them on then my jeans and t shirt, she looked weird but still hot, she then told me to stand up and she handed me her panties to put on, then Jenny’s tights, I had no idea how to put them on, I tried a few times but just humiliated myself, when she showed me how it made so much sense then Her skirt and bra. As she was folding toilet paper to put down my bra she said that next time she was home alone she’d invite me over for “a lot more fun than tonight.” When I was finally dressed as a girl, she took me into the bathroom and showed me what I looked like in the mirror. Not too bad but I felt better than I looked, she just told me to relax and get used to being a girl. After a while she says that she has to go, so we swap clothes and she takes my number and says that she’ll text me when we’ll meet up again and for me to only text her if I have an empty house. I agree, we kiss and she goes on her way. About twenty minutes after she left I went into my room and noticed her panties on the floor, I was wondering if they were hers or my s****r’s for a few minutes until she text me asking if she’d left them there, she told me to keep them as a present until we next met.

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