Tickling his prostate

As I have become more comfortable and confident with my dominant persona the relationship with Billy has broadened and the initial reason for our meetings become long overlooked. I had never successfully milked him and this irked me so I decided it was time to try again.  A text was sent and a time specified for us to reconnect. 

I carried with me a small bag with a vibrating prostate tickler that he had never previously seen, a short length of rope and my favorite leather strap.  The strap wasn't really needed but I like to feel it in my hand and it could always be used to bring him back into line if he misbehaved. Misbehavior was to be expected after so many weeks of work coming between us. 

The room was warm when I entered. As he presented himself naked at my feet both my coat and my dress came off to reveal a short slip and stocking tops. He nestled his head between my thighs and breathed deeply. His hands wandered attempting to lift the slip so more could be seen. I reached for the rope and pulled his hands behind him to quickly secure them. 

Today he was going across my lap for a warming hand spanking. How awkward it is for a tall man to fit across the tiny lap of a petite woman. His stiff cock pushed into my legs and I reached a hand under him to grip it hard. Holding fast I began to spank his cheeks making them pink but not warm. Heavens he does squeal and squirm, you would imagine the spanking was being given by a hefty man.

I grabbed the leather strap and let it fall. It is very satisfactory to hear the sound of it landing on flesh. Despite his yelping I managed to give him a good dozen purely for my pleasure.

Billy was released and told to bend over the chair with his legs spread. I reached for the gloves and lube and he understood what was to follow. I talked to him about how long it had been since I had tried to milk him and my desire to try again. I began slowly, circling the outside of his arse with two fingers, drawing out the time before penetration until his body was writhing for it. 

His arse hole was so tight but as my first finger entered he groaned with pleasure. A second finger spread his hole wider and I felt so much more competent to stimulate him. I touched the tip of his cock and let the precum heighten the sensation. My free hand stroked from the tip of his cock slowly back to the entrance of his arse. With each stroke his sense of bliss deepened. 

I took away my fingers and inserted the tickler. Setting it to vibrate I held it in place and continued to stoke his balls and cock. I can only assume that the pleasure was intense as billy became incoherent. 

Two or three times I halted this process to present a part of my body to him for worship. First to his great displeasure it was just one pussy lip. He got roundly castigated for complaining and replaced his sulky look with one that was more appropriately appreciative. Another time it was a pretty pink nipple, finally it was my clit.

Each break was just long enough that his arse hole tightened up and had to be reopened. Fingers followed by the tickler. Getting closer and closer to cumming. But I continue to be impatient..........milking did not occur this time either. I wrapped a fist around his cock and gave the instruction to fuck my hand.  Well bugger me! Billy fucked back and forth once or twice and then dropped his load.   

When it was finally possible to get sense from him he apologized, I had just taken him too close and ejaculation was impossible to stop.

Tenga Egg

I bought my first Tenga egg last Easter. The display in my favorite sex shop was simply too clever to resist. But as it is a male masturbation toy it sat on a table beside my bed for many months looking forlorn. It was Sheenv who suggested I should use it on my sub and I wondered why I hadn't thought of this myself. So rather than a treat for Easter it became a present for Christmas.

I sent billy a message telling him I had a special present to give him and that we needed to meet. The date was arranged and anticipation grew in both of us.

I didn't think that a session with the tenga should pass without stiff discipline, billy wasn't going to get pleasure without earning it. I took with me a strap and a paddle to increase the depth of endurance he would need.

Billy was eager to see me, naked and kneeling with a very erect cock. I caught it between my legs and leaned over him to scratch my fingers up his back. I spanked him a little with my bare hands and then ran my hands through his hair to pull his head into my belly.

"Are you going to be good for me today?" He assured me he would be but I doubted him. Grabbing his wrists I fixed them behind his back to remove his temptation to touch. I was in a teasing mood so now he was handicapped I let him nestle his nose against my pussy.

"Would you like some of this for a present?" Oh yes of course he would "you are not going to get any". He groaned a bit and later pleaded but on this day I was resolute. He got close to my scent a number of times to keep him hot and bothered but my taste was out of bounds.

I bent him over a chair to get his arse nicely presented. Beginning with my hands I warmed him up. Left hand on left buttock, right hand on right buttock. My left hand feels better, it gives a harder thump, my right is more slappy. He wriggles and squawks which amuses me. The paddle comes next. I am sure it is more enjoyable for billy than my hands with their variable stoke. It quickly and easily turns his buttocks red.

When I pick up the strap it is with much pleasure. It feels so good wrapped in my palm. I swish it to and fro just enjoying the way it moves. Then, with a gradual increase in strength with each stroke, it falls upon billy. It's tough. He jerks and repositions and needs the gentle caresses I give him between times. We carry on a little longer and despite the rigors of the strap billy remains aroused.

Which is good.

He is carefully placed on the floor and told to lay on his back. I touch his balls and roll them around in my fingers. Then ascertain that his cock is very needy for attention.

As I wanted the tenga egg to be a total surprise for him I fitted a blindfold.

I broke open the egg to find a flexible white sheath on a tiny stand. One side of the sheath was smooth, the other patterned. I took the lubricant and smoothed some onto billy's cock before placing the sheath onto him. Kept compact it just covered his glans and for a while I rocked it in this position. But I was keen to see it covering his cock so slowly extended it down. Stretched out it was much thinner but there was no diminution in effect.

I began an extended hand job.

The sheath made it easier moving smoothly under my hand. My hand grips, releases, grips, releases. It is like molding playdoh.

For billy the feeling is blissful. Relentlessly I take him closer and closer to orgasm until he cums with a huge explosion of ejaculate.

I have never seen him so wasted before. Billy is completely collapsed by the experience. I hold him tightly enclosed for more than five minutes before he can recover enough to be sensible.

"I don't know what that was" he tells me "but it was just like a real pussy"