"Is there anything else you've always wanted to try?"
In my experience of discovering BDSM with others I have learned that it makes us realise that fantasies can be fulfilled and curiosities can be satisfied. Once the trust necessitated by bondage play has been established, new possibilities open up. Hence why, on a few occasions, the answer to my question above has been "Anal sex".
Pleasuring myself with someone's asshole is, for me, the ultimate act of domination. This taboo orifice is the last bastion of a submissive's bodily privacy. Once it has been surrendered we both know that they have physically given themselves to me entirely. It's a big responsibility, but one with such wonderful rewards for both.
Of course, the recipient of anal sex isn't necessarily submissive. This is purely my view of it with Dom-tinted glasses. There is also some preparation involved; here's a handy list:
1. Hygiene. Allowing the sub to have some private bathroom time. Douches make the job more thorough, but it's important for participants to be realistic about perfect cleanliness.
2. Stretching. Depending on the size of what's about to be inserted, working up to it with a smaller toy may make anal sex more comfy for both. Tip: put metal butt plugs in the fridge before play for a fun sensation.
3. Lube, some types of which are made specifically for anal play. Keep it within easy reach.
Cleansed, stretched and lubed, my sub is ready for me. On their back, ankles handcuffed to wrists (or secured to a spreader bar), they present themselves. Taking a good portion of lube, I slick my fingers and gently probe, ensuring a good coating inside and out. Finally my condom-clad cock is slimed too. Ready.
Slowly, slowly, I push against that tight ring, watching my sub's face for signs of discomfort. The swell of my glans is the key point, one which can prove to be a bit too much 'nope'. But when it pops in there is then very little resistance there.
Consistent, pleasant tightness, like being gripped in a fist, awaits. A perfect O is formed by her mouth, matching the perfect O that has welcomed me in. It is a look of surprise; surprise at this new sensation and how pleasurable it feels.
Only once has someone orgasmed whilst I made love to their butt. They'd never had anal sex before and the joy of being there as they made this amazing discovery about themselves was truly memorable and a real honour. Lots of hugging ensued.
This leads me neatly on to summarising that care is key when it comes to anal sex. Taking care when preparing, carefully penetrating and being ready with armfuls of aftercare. Such an intimate, delicate act requires this approach. The rewards are a feeling of deep submission for one and benevolent power for the other.