First on web cam then in real life
This all started with one of my brothers friends (I'll call her Hannah) Hannah is a very bubbly beautiful woman, the vibe she puts out is always positive, she has those kind of eyes which always give her away, there's no way you can't notice those "come to bed eyes" when she gives them.
After dinner one day I went up to my room, I turned on my computer and went on msn (yea this was a while ago we we're around 16-17) Out of the blue I got a nice hello with a wink face from Hannah. She instantly started being flirty, and through cyber actions pinched me and began to get ruder. Right away I was getting excited I didn't think twice about getting some tissue from the bathroom and closing my bedroom door.
I began to tease myself through my jeans by rubbing my shaft, getting more into the conversation, she then came up with the idea of turning on our webcams, me being quite naive at this point, I wasn't sure what to expect, but just went with the flow. We turned them on and waved and laughed, she admitted to how horny she was feeling and when she saw me come alone it made her gush, she has always thought I was cute and attractive.
She began to ask me if I masterbated, I told her yes, being 16 that was part of my daily routine, I asked her if she wanted to see my cock, I had never done this before, so at first I just showed her the head of my now fully erect cock until finally revealing the whole thing. She responded by giving me a thumbs up with both hands, I moved the camera away and put it back to showing, I told her that she was the reason it was hard and I need to wank now she had made me horny, i asked her if she wanted to see me cum, and she said yes.
Before I did I asked to see her breasts, which she didn't want to at first, but eventually agreed and flashed me and teased me by rubbing and squeezing them. I then pointed the webcam down and moved the seat back for it to get a better view, there I was jacking off for my brothers friend horny as hell. Next thing I saw is her camera move to which she was also masturbating on webcam for me, and it wasn't long before I told her I was about to cum and I shot my load all over myself.
Feeling deflated catching my breath after having the best orgasm to date, I don't know if she reached her climax, all I know at that point that I had just had someone watch me for the first time, and it was awesome! Moving the cam back up to my face, she asked me if I had ever tasted my own sperm, and at that point I hadn't, she asked me all cutely if I would for her, and I didn't enjoy it which she saw from the expression on her face, but all together it was worth it.
One evening she had come round to visit, my brother was out at another one of his friends, so she chose to chill with me, I think we spent a good while playing tekken, but my mind was on other things which led me to begin to get an erection. We soon got bored of tekken and began talking, we didn't bring up the webcam night at first but soon things went that way, she said something which led to us play fighting on my bed, still being a bit naive about these things I didn't notice any obvious signs, all I could focus on was the obvious erection which she must have noticed pressed against her legs several times during us wrestling and what not, we both lay down on the bed catching our breath, I was slightly worried about her feeling my erection, and lay there quietly.
She then made the first step and asked if I had masturbated again since I put on the show for her, I told her I hadn't stopped thinking about it and I have done it every day since (it must have been a week or two) she said "I know you're horny now I could feel it when you had me pinned down." I was a lot shy in person with her than I was on camera to her.
I asked her if she was horny too and she said yes, soon the mood changed, I told her I felt like I needed to do it, She got off my bed, and went and made sure the door was closed properly, before turning round and telling me to stand up. I stood up and she took my place on the bed, she had a skirt on (she would wear skirts a lot) she looked up at me with the most sexiest sparkle in her eyes, she told me to take off my jeans, I slowly removed them whilst watching her lift up her skirt, she spread her legs so I could see her camel toe through her panties. My boxers weren't doing a great job of restricting my throbbing cock, she looked down and smiled.
I then pulled down my boxers letting my hard member free. I wasn't the biggest, but with how hard it and the situation I was in, it wasn't small either. Hannah reached into her panties and began to masturbate in front of me, looking down at my cock again and then back up at me trying to get my attention back to her face as i was just staring, wishing to see what was going on under her panties.
She lifted her legs up and slid her panties off, she then spread her legs revealing her juicy pussy, she then began to rub herself, I was still in disbelief of what was going on before my eyes! I slowly began to reach down and began to jerk off "there you go take your time" I was doing it slowly as possible picking up the pace as I watched her do the same.
She lifted her hands to her mouth and sucked on her fingers before entering them inside her. As she began to thrust them in and out, doing it harder and faster, next thing I know her body started to move as she let out some soft moans, she was cumming, and cumming hard, in front of me, which drove me to my limit, and I shot my load all over my bed and her leg before getting weak at the kness and nearly falling onto her.
Lying down next to her, with my dick slowly getting softer, she leaned over and kissed me before putting her panties back on. I pulled up my boxers and jeans making myself decent, she left soon after that but not without giving me another kiss and a cheeky smile. That was the start of a few different events to a great and extremely naughty friendship. More to come soon!