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does it hurt?

Posted by secretlynaughty on August 28, 2010

In my work I have a colleague who works out on the road only coming into the office for meetings etc. He is new to the work he is doing and I am his office contact and supply him with asĀ  much moral support as I do information. Scooby is a little older than me but only by a few years. He is also Gay and has been with his partner for many years. I have a very good rapport with Scooby. He has made it his mission to shock me ………..I keep telling him that he will have a hard job of shocking me…….he has no idea what I get upto.

I tease him relentlessly…….if he says he is parked in a layby I will reply ‘I’ve heard about men like you’. He loves our banter, I have shocked him once or twice like the time he told me that he would be staying in a certain area and I pointed out that there was a Greenhouse Club nearby.

A few days ago (I have no idea how this conversation got to this) he told me that he often gets asked ‘does it hurt?’ (remember this conversation took place during working hours whilst I was in an open plan office). His stock reply being ‘If I’m lucky’. Now I find that interesting. (oh I did manage to slip in a ‘yes it does’ comment).

Knowing that he is gay did help to know what he was saying. Obviously he enjoys the inevitable pain experienced during anal sex.

I don’t think I know any men who don’t like the idea of anal sex (even if they have never tried it) but as the giver rather than the receiver. I’m not sure what the percentage of men who have never had the opportunity to experience anal would be but I suspect it is greater than 75%.

Again this is one of those sex acts that my mind and probably most people’s pictures anal being performed on a woman on her hands and knees (a bit like my vision of a spitroast). In my younger days one or two guys (including my husband) tried to penetrate my bum but the pain was so excrutiating that I couldn’t do this. As soon as he tried to enter me I would be screaming NOOOO from the pain. I couldn’t imagine anything more painful.

But then one day laying on my bed with Nigel he told me to lay face down with my legs together and just relax. Once I was very relaxed he applied baby oil and slowly entered me. To my utter amazement the searing pain wasn’t there. The more he pushed into me and the pain was only minimal the more I relaxed and enjoyed the feel of him filling my arse. Nigel began slowly pumping into me, yes there was some pain but there was also a spreading feeling of pleasure, my arousal was building. I wanted to cum so hard, this mixture of pleasure and pain was incredible. I would highly recomend it to anyone (with the right partner). My clit is aching at the very memory of it now as I write this.

Since that day when Nigel introduced me to the pleasure of anal sex I have had wonderful experiences with 4 men in total (not all at once). The most recent being Dave, but even with these few men there were times when I just wasn’t able to indulge. Even with a man who I have had anal sex with there are still times when it is just too painful to get over that initial searing pain. Nigel like to give it to me up the arse several times in a session. There were times I could hardly sit after I had seen him, but it was so arousing.

I will have to ask Scooby whether he experiences the pain pleasure mix that I do or does he revel in the searing pain that I get when it isn’t right. I had just never given it any thought until now.

Does it hurt for you?

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