What a Bummer!

When I’m asked what I’m into and what turns me on I have a tendency to lapse into a list of what I don’t like, what turns me off, what I don’t want to explore.  It’s a much shorter list, but I tend to view it as a list of non-negotiables.  No matter which site I’m currently using to get my jollies, a guy whose profile says he wants to push boundaries will always be a no from me – my boundaries are there for a reason and I’ve no desire to have them pushed.

Outside of that list are the negotiables: things that don’t turn me on or that I’m not keen on or I’m nervous about, but am willing to do occasionally if a partner is very keen.  I’ve mentioned the spanking session with G, and impact play is one of those negotiables.  Another is anal.

I’ve had anal in the past, but I’ve found it to be unerotic at best, painful at worst.  It’s not something that will ever get me to orgasm by itself, and most of the men I’ve slept with have lacked the patience to warm me up sufficiently that it’s comfortable.  It feels like a lot of preparatory effort for not much personal payoff when there are a million other things that will get us both off.

After the candle session with G I was a lot more amenable to his experimentation, and when he said he’d like to dabble with anal on my next visit I agreed, on the condition that he would ensure I also got off (nothing’s free in my world!).  G has an average cock – very attractive, around 5-6” long when erect, not particularly girthy.  Ideal for anal as well as oral.  I’m not sure I’d have agreed so readily had he had an absolute monster of a penis!

I started preparing a couple of days before we were meeting.  It’s far from erotic but I find a low residue diet and a day of laxatives essential prep for anal, as well as a thorough enema on the day.  It’s essentially a messy business, but I will go to some lengths to ensure the mess is minimal.

All preparation done I headed to his flat.  We sat and chatted over a drink, but I was far more nervous than I had been on my earlier visits and just wanted to get things under way.  We headed to the bedroom, where he’d set up an over-door bondage kit on the door to the en suite with a library chair in its step form directly in front of the door.

We spent some time on the bed, kissing and stroking before G brought me to several orgasms with my favourite dildo, his fingers and his tongue.  When I reached for his cock he backed away, laughing that he didn’t want to orgasm so quickly when he had such big plans before moving back to focus on my pleasure.

It felt lovely as he used one hand to finger some lube in and around my anus while he continued to drive the dildo into me.  Eventually he decided that I was sufficiently lubed and he rolled a condom onto the dildo before gently easing it into my arse.  It was a stretch and there was a sting, but he was extremely patient and gentle as he worked it inside me.  When he could slide it back and forth with little resistance he brought me to a final orgasm fingering me against the fullness of the dildo, before taking it out, removing the condom and helping me to stand on shaky legs.

In our conversations and discussions he’d shared several favourite porn clips where couples were standing up to fuck.  I was a little dubious that it would be possible with me – my orgasms are so all-encompassing I wasn’t convinced that I would stay standing through them, and my arse is so huge I wasn't sure how satisfying it would be for either of us.  Nevertheless we had decided to give it a go.  G stood me facing the door of the en suite, my hands cuffed in front of me at shoulder height on the over-door kit, plenty of play in the tie so I had a fair range of movement.  He left my right foot on the floor but lifted my left to a step slightly higher than knee height but not quite hip height.  It was a lovely position, encouraging me to bend over to rest my elbows on the lifted knee, presenting myself wide open to G as he moved behind me.

I could feel the cool air against my overheated wet sex while G rolled a condom on and lubed himself up.  As he reached between my legs to rub my clit I gasped and jerked, and he laughed at how sensitive I was.  He slowly and gently eased his cock into my arse, gripping my hip with one hand while using the other to steady his entry.  After the dildo there was a slight pinch but it wasn’t uncomfortable, and he was soon moving more quickly and thrusting into me with more force.

It was completely unexpected when he reached around my thigh to ease the dildo into my vagina.  I’ve never experienced DP and although I have used a toy anally while having sex I’ve been used to it being a narrow steel wand or a small glass dildo.  The fullness of the dildo rubbing against his cock internally was an astonishingly erotic sensation.  As G started to lose control he dug his fingers into the flesh of my hip with one hand while roughly ramming the dildo into me.  Having movement in both vagina and anus sent me into a crashingly powerful orgasm.  The force of the orgasm came close to squeezing G out of my arse, and he stopped moving and just held himself deep inside me while he continued to fuck me with the toy until my orgasm eased.

As I came back to myself I could feel wetness running over my thighs.  I’ve never squirted, and this session was no exception, but I don’t believe I’ve ever been as wet as I was then, with G deep inside me, bringing me off with the toy while biting my shoulder and pouring filth into my ear about how he wished it was another man rather than a toy, how he’d like to see me taking multiple cocks, how he’d love there to be a room full of men with hard cocks just waiting their turn to pound into me and bring me off over and over again so that the waves of my orgasm would clench my arse around him and he wouldn’t even need to move to fuck me over and over.  I adore dirty talk although when excited I tend to be unable to string together the most basic of sentences, and that certainly had an impact on how wet I’d become.

Eventually my orgasm started to die down and G removed the dildo.  He kissed the back of my neck and moved down my spine, before putting both hands back on my hips and pulling me against him, burying his cock deep into my arse.  His movements became frantic once more, and he reached one hand around to grab my breasts and pull my upper body up as he slammed into me.  I felt his cock swell and felt the warmth as he came into the condom, and the sensation and raw lust of him losing control set off another orgasm for me.

G held his softening cock in my anus while I twitched around him, but when he reached around to stroke my clit the sensation became too much and my shaky legs gave way under me, only the bondage kit holding me up.

G moved the steps out of the way and unfastened the cuffs, sitting with me on the floor until I could stand up again.  We moved into his glorious shower and cleaned up, washing each other and enjoying the tenderness after the hard sex before heading to bed to doze and recover.

When I woke the next morning I was extremely achy – my thighs felt as though I’d done a million squats.  We had slow, relaxed morning sex, spooning and spending a great deal of time just stroking each other, trying not to do anything that would make aching muscles complain too much.

DP is still a fantasy of mine, though whether I make any move to turn it in reality is subject to considerable doubt.  I’m a coward at heart so the thought of two men makes me more nervous than aroused.  There is some potential with G but things between us are currently slightly awkward after a rather irritating social meet, so I’m not sure whether he’s someone I’ll meet up with again or whether we’ve parted ways.  For now I’m content for it to remain a masturbatory fantasy.