The VIP’s Entrance

{ June 25, 2007 @ 10:41 pm } · { Anal, Osiris, Sex }

I’d rather call it my “VIP’s Entrance” than my “Tradesman’s Entrance” since that would imply I’d let any Tom, Dick or Harry (or actually just Dicks) into mine. I’m referring to my anus of course, for want of a blunter word.

I’ve only ever known one man to say he wasn’t into anal sex. Funnily enough, that was Osiris, but he hadn’t tried it at the time. I can only presume he changed his mind between then and now because he did annouce the other night that he was “Obsessed with anal sex”. I really couldn’t disagree.

So most/all? men love anal sex, and why wouldn’t they? It’s warm, it’s tight, they are in you, they are having you. I doubt that it’s as common for those on the receiving end to be so vocal in their praise of their arses getting pounded sore. There’s even plenty of gay men who won’t take it up the arse, and that’s saying something.

I suppose I should point out that I don’t think it has to be an unpleasant experience to be butt-fucked, but personally I never know how it’s going to go, so there’s always some apprehension. Relaxation is really crucial, foreplay is crucial, and a tonne of lube is paramount. Sometimes though, even if you have all those things it’s still uncomfortable anyway and you might not be able to carry on with it. Osiris and I have had a couple of sucessful attempts but also a couple of unsucessful attempts. He hasn’t managed to cum up there since he doesn’t dare go that hard yet, but we will get the hang of it. We’ve only ever done it with me bent over but next time we’ll try it with me on my back so he can watch my face while he fucks me in my not-so-holiest of holies.

When I was a young teen the thought of anal sex didn’t enter my fantasies much. I couldn’t possibly imagine how a penis could fit up there without force and how it could lead to anything pleasureable. In fact I remember being in school when I was about 14 or so, sat in the dinner hall eating with friends. There were some older girls sat with a boy and since they had their gaggle around him, they were teasing him and asking personal questions. I heard one of them say “So is it true that a man’s g-spot is up his bum?”. I don’t think the boy really knew but he played along and said that’s what he had heard too. Her next question was probably not the most fitting I’ve heard asked round a dining table, but a valid one nonetheless; “Does it feel really good when you take a shit?”.  He laughed and pretended he came when he was on the toilet but then seriously answered no, it just felt like you were taking a shit. The answer didn’t surprise me really, I was convinced no pleasure could be derived that way anyway, my opinion was that an arsehole had one purpose only and that’s to deficate out of.

Of course it’s a woman’s perogative to change her mind. In fact I think I must have changed it pretty soon after my earwigging episode at the school dining table, because I was actually wearing my school uniform the first time anyone ever stuck a finger up there. I remember feeling vaguley surprised when it happened but I had consumed a lot of alcohol in a short space of time prior to that, so at the time I chose not to object. I would tell you more about it but I don’t really remember much of it. Afterwards I seem to remember thinking it was a bit weird but not necessarily bad.

As I grew a little older I fell in love for the first time, me and him were both young and inexperienced but my god we were willing to learn. We’d both had a sexual partner before but hadn’t got to stage where we actually felt comfortable with a partner in our own skin, until we met each other that is. Then sex suddenly wasn’t something that I’d do either drunk or with fumbling embarassment in the dark. All that was gone almost over night; sex became a passion, a hobby, a sport! As all young couples who are first in love and exploring their bodies together; we shagged like bunnies. Lights on, lights off, flaky ceiling or blue skies, it didn’t really matter. We tried everything we’d never done before and had a lot of fun finding out “What goes where”.

This guy was the first one who ever had anal sex with me. We’d had some failed attempts that left me thinking that maybe I should just stick to a finger and not be so greedy, but my partner urged me on. Finally one night we got home drunk, that probably helped. We’d been to a friends fancy dress party and were sleeping over at his parents house for the night. He was dressed as a cowboy, spurs and all, and I was dressed as a saloon girl with a dress that was basically a pair of knickers at the front but had a long train at the back. It was red and black and I had long gloves and a feather boa. I was looking and feeling kinda sexy!

Wasn’t long before we were at each other, the boyfriend suggested I keep the dress on and bend over, and that’s just what I did. My fishnets were already long gone, so he pulled down my knickers and started fucking me like that. After a while he said a phrase that I didn’t then realise I would hear so often over the years; “Can I fuck you up the arse?”. I was well up for it so and I gave an affirmative response and after some fingering and clit rubbing and a few winces here and there, he was in. There’s nothing quite like a cowboy taking you anally from behind to sober you up in 3 seconds flat.

It felt weird, very strange. There’s just no other way to say it, and I do apologise but it felt like a poo in reverse. It was nothing like a finger being up there, I quite liked that, still love it in fact, but it doesn’t compare with something the size of a penis going up. He had a couple of minutes up there but then it grew a little too intense and I had to ask him to stop. I never had good anal sex with that guy, in fact I don’t think we really managed it after that, time makes me forget, but I was at least glad I’d tried it, even if it had produced some questionable sensations.

My first love faded after about 2 years and I just had casual partners or none at all for a year or two. Then Storyteller came along, we were together for quite some years and even though I spent that time hiding most of my fantasies from him, we still managed to connect on a sexual level and have some good vanilla sex. We even managed to pull off anal quite well, albeit after much pratice. We still had the times that were non-starters but with him I found I could actually orgasm myself when we did it. Even so, it was an activity that we didn’t partake in all that frequently. I used to joke to Apollo that I only did birthdays and Christmas.

Now I’m with Osiris and although he started off carefully, also asking if it was ok, as we are getting into it a little more each time, he has become more confident in asking for and getting what he wants. During his last visit he demonstrated to me that he doesn’t even need to ask at all, since his authority is greater than mine, he can just decide.

We were lying on my giant bean bag together, as we like to when we are in the flat. I wasn’t wearing any underwear, since I don’t when I’m in the house, and as usual he was taking the opportunity to have a feel and a slap whenever he got the urge.

“Go and get your plug”, he eventually said.

It wasn’t a question, it was definately an instruction, so I did as he asked without any fuss. I had a pretty good idea what was coming. He only ever tells me to get it out when he wants to fuck me anally. I handed him the lube and the plug and feeling a teeny pang of shame for what was about to happen, I lay back down on the beanbag, on my side with my rear facing him. He lifted up my skirt and parted my cheeks and worked some lube into and around my hole. He played with his finger briefly before sliding the plug in. I lay there quietly adjusting to the sensation, and adjusting to the fact that whatever was about to happen was out of my hands now and I should just do as I was told.

I didn’t have very long to relax to the feeling of being plugged before he turned me onto my back and got inbetween my legs. Already erect, he started fucking me and every stroke caused the plug to push into me more. He stopped before he came, got up and told me to follow him into the bedroom. I waddled after him as gracefully as you can waddle, saying nothing, but feeling like my cheeks were probably burning. He gestured to me to get on the bed so I climbed up and looked at him to see where and how he wanted me. He had me face the head of the bed on all fours, then placed a pillow beneath me and told me to wait. He walked to the dresser and opened the drawer. I heard the jangle of metal and knew it was the two sets of handcuffs that he had told me to get prior to his visit. He came back to me on the bed and took each of my wrists in turn, placing them in the cuffs, fastening the cuffs to the latticework on the bed, and then locking everything in place. Once I’d been secured he took his place behind me, slapped me a couple of times and then eventually removed the plug. I heard him unscrew the cap on the lube and he lifted my skirt and began working it into me. I tried my best to relax because I was keen to be able to take him, and it just took a couple of attempts for him to enter me. He fucked me slow at first, stroking my clit with one hand. Using the other to hold me and push himself further in. When he was up to the hilt he increased the pace, the feeling was very intense but he was able to stay in a while, I was getting uncomfortable but I didn’t say anything, but he could tell from the look on my face when it was time to stop.

He offered to get me some water but I was fine so we carried on. He lost the condom, turned me over and locked me in again. I had the chance to have a quick suck of his cock before it went back inside me, but this time in my pussy. He fucked me really hard and came easily. When he was done I asked if I could cum too and he obliged by fingering me and stroking my clit, and for extra horniness he slapped and pinched my tits, which had me exploding into orgasm in no time. I came long and hard and when the waves of pleasure and spasms had passed, I lay there catching my breath, mind still reeling and body tingling. No-one had ever taken me like that before in my life and I felt on top of the world now that Master had. I knew something special had just happened, the shift in power between us was very apparent and I felt so close to him, to my master. He’d taken me and made me his and the feeling was sublime.

So much for Christmases and birthdays anyway, looks like I’m working to a different schedule now.