Strap-on cherry!

I have just given a lovely chap a nice massage and taken his strap-on cherry! Being very nervous he and I decided that a massage would be a good place to start his journey in to the world of BSDM. He wanted to see a fully equipped dungeon but not play in one, just yet! After having a peek inside we embarked on our pre session/massage chat and once he was settled in I removed his clothes, slowly.

He lay face down on the massage bed where I restrained his wrists. I gently stroked his flesh and with every delicate touch of my hand his body twitched. I then dripped warm oil on to his flesh and began to massage it in. He breathed deeply and slowly as my hands caressed and manipulated his skin, slowly working my way up and down his torso and teasingly pausing near his buttocks. He, feeling this raised his buttocks slightly in the hope my hands would slip between his legs and  grip his cock. But he would have to be patient.

I could tell the way he was beginning to fidget that his cock must be hard by now and was finding it uncomfortable to lay on. With his wrists still restrained he was unable to make the necessary adjustment, so me being the thoughtful Mistress that I am glided my hands up his body and towards his buttocks, as he raised them my hands slipped between his legs and reached under. There was one big almighty erection hiding under that body. With one hand squeezing his dick and one hand clenched around his ball sack, buttocks lifted quite high, it was a perfect opportunity to introduce him to the delights of a prostate massage. I removed my hand from his sack and slipped on a glove. Lubed his hole and began to gently tease it, but for the moment on the outside only. It wasn’t long before he started to push his ass back as if to offer it up. Actions speak louder than words and I could tell he wanted more. My finger slowly and carefully eased itself in to his tight virgin hole. He gasped, not out of discomfort but sheer pleasure. My finger slipped in deeper until it hit that familiar spot. When it did I moved it in a circular motion whilst easing his cock at the same time. He whispered “Oh wow, Mistress”. He began to rock and spread his legs a little more as he ‘got in to it’. I could see he was getting worked up, and I could also feel it, deep inside of him as that little sensitive area know as the prostate began to swell. The moment it did, I ceased working on his cock to prevent him from shooting his load.

I could tell he wanted more, much more than my finger, so I saddled myself up with my small beginners cock and harness and climbed on the massage bed behind him. I pulled his hips back and eased myself in. I thrust slow and deep as he moaned in exquisite delight. He was now ‘coming back’ on my cock, rocking back and forth on to it. I slapped his buttocks as he rode without a care. My hands now gripped his ass cheeks pulling them apart. As I slapped in to him again and again he continued to rock but much more vigorously than before.

“I’m gonna fuck your ass and take your strap-on cherry” I said as I slapped his buttock.

I then reached round his waist and felt his hard cock bobbing with his movement, it slipped through my fingers as they slid over the bulbous waxy head. This time as he rocked back and forth I gripped his cock. There was plenty of natural lubrication there now and it just slid in and out of my hand with ease. He threw his head back and my other hand grabbed his curly brown hair. He groaned and thrust hard back on my appendage when he paused. He wanted to know he had taken the whole length, but the excitement had gotten to much and he began to unexpectedly shoot his load. My hand still gripping his throbbing cock, squeezed to get all the spunk from him. He froze for a moment then panting heavily he lay forward and flopped as if all his energy had been zapped away. He looked up at me and smiled…“Wow Mistress, I’ll be back for more of that treatment” then closed his eyes while he recovered.