A few years ago we used to regularly play with another couple and often used to attend their play parties. It was at one of these parties I have my first strap-on experience. I was on my hands and knees and another woman was fucking me from behind and I have to say the whole experience was incredibly fun, I seem to recall she was also wearing a cowboy hat at the time! Looking back although the experience was enjoyable the strap-on part of that experience wasn’t really for me. I find dildos to be…well…hard and I’m aware that sounds ludicrous but hear me out. Even the hardest cock isn’t as hard as a normal dildo, when I’m in control of a dildo I can feel how hard to go but when someone else is in control, especially with hip thrusts I can end up feeling bruised. With a real cock there is a slight softness and the cock owner can feel, at least partially, how hard those thrusts are too.
My second experience was on the other end of the strap on, with the same couple but luckily for me it wasn’t a party situation this time around. Once i worked out how to climb in the straps and we had it placed correctly, I climbed on top of her and the realisation of how difficult it is to be a cock owner suddenly hit me. Kneeling and aiming the cock in the right direction was almost impossible, attempting to balance myself on one hand whilst I guide with the other proved to be impossible and her cry of ‘not that hole’ just tipped us over the edge of uncontrollable giggles! Once they had subsided and we were capable, we undid the straps and dropped it on the floor and continued to have fun with the odd moment of giggles reoccurring.
Then whilst Sir and I were exploring fantasies with each other I asked if he ever though of taking anal play a step further and try pegging. He admitted it had crossed his mind out of curiosity, although it was something I hadn’t really thought about previously I was so excited I had found someone so open and willing to experiment so before he changed his mind we went out and visited our local toy shop, online delivery would take too long!
We spent a long time in the shop deciding which one would be the best. Nothing too big but also we didn’t want anything too small either. Also because I hate the hardness of some toys, especially anally we thought something with a bit of give would be the best. Finally we settled on a jelly dildo, knowing what I know now I obviously would have chose differently but at the time the size and softer material made it the ideal choice.
When we were home and ready to try it out I got myself into the harness, well I say myself but he had to help me because I actually got myself in a right tangle with straps everywhere! Standing in front of him kissing and hugging him I could see in his eyes how weird it felt having another cock rub up against his, I have to admit I played with that just a bit, there was a fleeting moment where I wanted to tell him to kneel and suck it but even back then, before our D/s dynamic was clearer I knew exactly where that would have gotten me!
When he was ready he bent over the sofa, having learnt from earlier experience of not being able to see or feel where I’m going in a missionary type position and also knowing I prefer anal in that position. I lubed up and started playing with him with my fingers, getting him ready and relaxing him into it. Then I tried to push into him and that’s where we realised jelly is too soft. I needed something harder to actually go in the direction required. Even with a firm grasp around the shaft it would not go in the direction it was supposed to, slipping and wobbling off all over the place. He started sniggering which really didn’t help, his butt cheeks were covered in lube trails, I had lube over both my hands by now and then the dildo actually popped out of the O-ring and landed with a splat on the carpet. Both of us had collapsed into a giggling mess, our sides ached and tears rolled down our faces.
All in all I think we’ve come to the conclusion strap-on play isn’t really a thing for us, we haven’t tried it again. I have no idea why I’ve kept it but every now and again I come across it whilst looking for something else and it makes me giggle all over again at the memory!