The Toolman sent me a message asking me if I had any holidays planned. I thought that was an odd question but answered that I was away for a week next month, and asked him why he wanted to know.
“I have to have knee surgery so I thought I would do it when you aren’t around.”
Before I could react to that he asked me when my birthday was. I told him it was three months away and asked him why he wanted to know.
“You will see.” He replied with a devil emoticon.
What is with all the forward planning? Obviously he doesn’t think we are going to end our arrangement any time soon.
We went on to plan our next rendezvous. He told me he wanted to be dominated and his limits pushed next time I saw him. Telling him I planned to make him see stars, I asked him to buy a cock cage so I could be in complete control of his pleasure and he was excited by the idea.
While The Toolman went shopping, sending me photos of the options to approve, I got to planning.
When the day arrived and he told me he was on his way I issued my first instruction. I told him to let himself in, greet me with a kiss but not say a word, strip for me and put on his cage.
I dressed in a sheer, skin tight dress, pulled back my hair into a ponytail, applied red lips and high heels. I lay back on my sofa, filing my fingernails short and waited for the door to open.
The Toolman was disobedient right away. He came over and kissed me as instructed and told me I looked beautiful. He apologised for not being completely ready and excused himself to the bathroom to douche and prepare.
When he returned naked and holding his cock cage I made him stand in front of me while I examined him and helped him squeeze into the apparatus. His large cock was already semi-hard and it was impossible to fit into the cage but I made the best of the ill-fitting situation. The cage had chains attached to the belt circling his waist and his arms could not move more than a few inches from his sides.
When he was as enclosed as possible I ordered him to sit on the couch. Sliding my dress up my hips I straddled his lap and told him to worship my breasts.
“Yes Mistress.” He closed his eyes and pressed his lips against the lacy fabric of my dress. Through the sheer lace he tongued and kissed each breast lovingly. When he had paid them sufficient homage I stood up and turned to face the other way.
“Now worship my ass, Slave.”
Again, he kissed and licked and nuzzled into my body through the dress, covering every part of my round ass with his mouth. I told him that he wasn’t doing a good enough job and led him to the bedroom.
Dropping a pillow on the ground for him to kneel on, I got on all fours on the bed and lifted my dress up to my hips again so he could get closer and worship me properly. He tongued my ass gently through my panties, kissing the cheeks and burying his face into me.
When I had been sufficiently turned on my this I told him to lay on his back on the bed. While he lay there I stroked his body softly, making it even harder to wear the cage he was already spilling out of. I knelt next to him and positioned myself over his chained right arm.
“You may use one finger to see if you have turned me on.” I told him.
The Toolman obeyed, sliding a single finger into my wet, tingling pussy.
“You are very wet Mistress.” He informed me happily.
I let him continue this for a moment before I moved away and positioned myself between his thighs. Crouched there I gently inserted a butt plug then removed his cage.
“This is in my way now.” I told him as I unchained him. I stroked his engorged cock softly and asked him if he was ready.
“Yes Mistress.”
“Do not touch your cock.” I ordered.
“Yes Mistress”. Good Slave.
I twisted the butt plug around a little before removing it and inserting a small vibrator. I knew The Toolman was hoping for me to go bigger than the item I selected but I had a plan. I played with the vibrator settings for a while before finding the hard pulsating vibration setting I wanted.
I lubricated my fingers and slipped two inside him, pushing the vibrator up close to his prostate. Immediately he moaned and twitched with the intensity. I massaged and moved my fingers inside him, occasionally massaging his perineum but staying clear of his balls and penis. I wanted his cock to be aching for me to touch it. From time to time I would give it a swift lick to make him jump before returning my attention to his ass.
Changing the vibration settings every now and then, I could feel his ass getting wetter and knew the orgasm was coming. His head was thrown back with the pleasure, his face pained with ecstasy, and he was moaning with every move I made in him.
“Oh God I’m gonna cum.” He cried out.
“You may touch your cock now.” I generously told him.
The Toolman grabbed his aching cock and began to stroke it as I furiously massaged and fingered him. He exploded with a loud cry and breathlessly thanked me.
“Did you see stars?” I asked.
“Yes Mistress.” He panted.
“Well you have been a good slave so you can worship my pussy now as a reward.”
“Yes Mistress”.
He caught his breath and moved down between my legs where he licked and kissed me for a long, luxurious time. Whenever he would lose concentration or my excitement waned I would chastise him.
“Don’t just lick me! Worship my delicious pussy.”
“Yes Mistress”
Soon enough I orgasmed and pulled him up to fuck me. We fucked over and over for hours, the intensity of the emotion sometimes almost too much for me. Looking into his eyes and feeling his passion as he kissed me and held me was overwhelming.
When we finished we lay back talking and I couldn’t help myself.
“How was your date?”
The Toolman told me he had met the woman for a drink but it hadn’t worked out. He said she had been very flirty and sexual over text but in person she recoiled from his sexual advances and flirty banter. The date was over quickly and I was thrilled.
“You can tell me when you have a bad date. But don’t mention the good ones.” I told him.
I got the feeling he is on the dating apps a lot, trying to compete with me. Is he playing catchup? I don’t understand why he would feel the need to do that. He has had so many more sexual partners than I have in his life.
Does he value quantity over quality?
We talked about the various pressures in his time-poor life and he told me he would love to have a beach day like I had the previous week, where he could just chill and relax. When I said he was welcome to join me on the beach any day he wanted, he responded with a cautious “maybe”.
He was also yawning and falling asleep. Once again, aware of his hour-long drive home, I told him he could stay over if he wanted to. He responded with a cautious “maybe”.
The Toolman washed and packed up his tools and went on his way.
Later that night I sent him a message telling him I want to spend more time with him. I told him that I knew he didn’t have much time to spare but I hoped that he would choose to hang out with me more sometime for a sleep over or beach day.
The Toolman has read this entire blog. He already knows the thoughts I have been having about him and I didn’t see what harm it could do to open myself up a little more.
It was true. I did want to spend more time with him; to see if I could get the “boyfriend experience” from him. I already knew the sex was unbeatable and that he cared. What was stopping us from seeing what this might be?
My fear of being hurt is far less than my fear of regret. I don’t believe in forever and know relationships end in heartbreak but to me a few weeks of tears and sadness is a small price to pay for what might be months of happiness and fun.
I could see he had read my message but he didn’t respond. Wondering what that meant, I made the decision to take matters into my own hands. I vowed to be open to what might be with The Toolman and not try to counter his resistance.
I would wait for his reply and if it never came I would move on swiftly.
I may have over corrected 