A long time ago I wrote this little piece about The Shy Guy.
Assuming you have now read that snippet I'm going to tell you that for the last year and a half I have continued to talk to him, at some point he even ended up as one of Facebook friends. We kept talking, him usually starting the conversation as like I said, I did lose interest at times. I can only keep a conversation going for so long without the other person chipping in after all.
But talk we did and slowly The Shy Guy became less shy. We talked about the usual inane stuff, tv books etc and sex of course. We became quite flirtatious even. He often requested I send him pictures, which I refused. It's very rare that I send pictures to someone I haven't met in person.
The Shy Guy eventually even suggested we meet for sex since it had been a very long time for him (about two years). I did think about this for awhile but in the end I decided against it. We'd been friends for a long time and I didn't want to ruin that.
I kept thinking about it however...
A week ago I decided to take The Shy Guy up on his offer. He was a nice guy, local and umm... apparently rather well endowed. But this had taken me several months to decide and by now The Shy Guy was hesitant. He'd been my friend through all my sexual adventures and felt I was now reaching for the 'bottom of the barrel'. Not the case. I don't do that kind of thing. If I choose to sleep with someone it's because I like you in some way or another.
The Shy Guy and I talked a lot more often that week. I sort of felt like I was doing some sort of audition, I'm not sure why though as our conversations were the same as they'd always just more frequent. Whilst texting me Friday night The Shy Guy said that he was in town and that maybe we could meet up for half an hour or so before he had to go to a meeting. I said no but said he was welcome to come over afterwards. For a first time meeting with a person half an hour just wasn't going to be enough for me.
He eventually decided that he would come over. When he opened the door I was slightly taken aback by the fact he looked exactly like his photos and by the fact he was a good four or five inches taller then me. Hard to do considering I'm 6 foot tall.
I invited him and put on a Doctor Who dvd. We sat there for the entirety of the episode, making stunted conversation. When the episode ended there was that kind of awkward silence before we somehow ended up talking about his dogs. This brought The Shy Guy out of his shell. I believe we talked for half an hour or so until I finally found the nerve to invite him to my room and show him my toys.
As much as we were both there for sex, The Shy Guy was a bit shocked by my bluntness, but hey.
We went into my bedroom and I showed him each of my toys, talking about them and telling him about their little quirks. When I was finished, unsure of what to do next, I kissed him.
Well! By golly was there a reaction then! The Shy Guy enthusiastically kissed me back, running his hands along my breasts and up under my shirt. We made out, groping each other as he tried to undo my bra. I pulled my shirt off and helped him. Still kissing him I straddled him, grinding my crotch against his groin. He was definitely hard.
I climbed off him and guided his hand to the waistband of my tights. Slipping his hand between my legs I encouraged him to rub my clit and then to slide his fingers inside of me. He was a bit rough but damn it felt good. As The Shy Guy did this I undid his fly, rubbing his cock through his pants and then sliding my hand between skin and pants. He winced as I did this and I admit I was probably a little bit rough.
I slid my tights off and his jeans soon followed. I continued to stroke his cock before I did what I really wanted to do. I leant forward and placed his cock in my mouth, sucking gently. I was so scared that I was going to ruin the fun early by doing this. Remember that The Shy Guy hadn't had any action in quite some time. But risk it I did. The Shy Guy certainly seemed to enjoy it.
I soon went back to kissing him and whilst I did this he continued to stroke my clit. It felt really good. I ended up burying my head in his shoulder as he did this and were it not for the lack of rhythm I would have came.
It was at this point when I decided to ride him. I slid him in between my thighs and up into my pussy, rubbing my clit as I did so. Due to the clit rubbing earlier, I very quickly found myself cumming. I continued to ride him, really feeling him thrust inside me. This guy hadn't been kidding about his size at all.
The Shy Guy eventually told me he was close and his thrusting became harder. Damn it felt good.
The Shy Guy turned out to be one of those silent orgasmers, I could barely tell when he came. This was a tad disappointing only because I find it so hot to hear a guy moan.
We continued to kiss for a little while, just lying there before it was time for The Shy Guy to head home.
I'm still unsure what the aftermath of us sleeping together is going to be. I definitely want to do it again but as yet the only answer from The Shy Guy is 'We'll see'. We're still talking though I sense The Shy Guy has regressed slightly back into shyness but then it could also just be my over eagerness to talk to the people I sleep with making things seem this way. But still talking is a good thing. In the end, I guess we will see and hopefully it will be each other we'll be seeing.