Austin's Diary - The Night

The Night:

I made it through the day somehow, nothing interesting for the diary unless reading about boring dead people floats your boat. School work and more endless school work. Milton’s obsessed. He and Tilden used to ride my case, but now it’s the professor with obsessive compulsive disorder.

“Boy, where are your books? Boy, have you finished that assignment? Do it better, boy.”

Is it ever good enough? I’m not a good student; I’ve never liked school. I get restless; I like to daydream. Last year I daydreamed about Milton. The dreams carried me through many a math class. Milton doesn’t do the dreaming or the restlessness. More work or he drags me to the gym. He kicks my butt when we workout together. 

Enough nattering, the day finally ended without any more disasters from yours truly. I even behaved at dinner and wasn’t banished to the kitchen and cold rations.

“Upstairs.” 

I’d been sitting downstairs with a book. Yeah, I’ve taken up reading for pleasure. It beats doing the laundry or the dishes, and idle hands and idle minds get drafted for those jobs.

Milton reached down and pulled me out of the chair. We didn’t usually retire this early. Retire--too many books. I’m even starting to talk that way.

The bedroom felt empty without Sheldon. He was usually sprawled out on the bed with his laptop. He was addicted to very bad homemade movies posted on the internet. 

“Sheldon’s fine. He’s going out to dinner at one of those two hundred dollar a person restaurants,” Milton said.

He’d known. He’d known I was thinking of Sheldon.

“It’s just us tonight, cub.” Milton ran his thumb down my cheek and kissed my lips.

Sheldon had always been the buffer. Milton knew what no near eighteen-year-old told anyone except under duress. I’d given and received plenty of hand jobs, but I was an anal virgin. I’d sucked cock a few times badly from the neat demonstration given by Sheldon, but the only thing up my ass had been my finger. Try telling this to the big dom you’re madly crushing on. A brutal hour on my knees on the study floor had made me spill it all along with tears and snot.

“I needed to know. I could hurt you otherwise. Learn to be honest with your dom.” Milton had pulled me to my feet, kissed me, and then thumped my ass for making him force the words out of me. Sheldon had been a sweetheart, folding me into his arms and regaling me with tales of Milton and marathon interrogations.

Here I was alone. My virgin ass not long for that title.

“We’ll only go as far as you’re ready. I know where your limits are even if you don’t, boy.”

Milton’s hands dropped down my front; my pants fell to those deft hands and then my boxers.

My God! Milton had dropped to his knees and swallowed me in one shocking gulp.

“Come when you want, boy,” he said, pulling back, his warm hands kneading my balls.

His lips on my cock, his hands on my jewels, my shirt tails flapping on my ass, I lasted about two-seconds. I tried to warn him, but he seemed oblivious and swallowed easily. He caught me as I wobbled on weakened knees.

“Thank Landon some time for teaching me that,” Milton said, his brown eyes laughing behind his glasses. “More relaxed now?”

All I could do was nod. A stranger would have thought I was drunk.

“Sit on the bed for me.” 

I flopped on the bed, my head still spinning with pleasure. Milton with slow, deliberate motions stripped off his shirt. Dark hair covered his chest and ran in a thick trail to parts unknown. I’d seen him naked; don’t get me wrong, but I’d never seen him put a show on before. My wilted cock thought the view was nice and tried to show some interest.

“Teenagers. Enjoy it while you can,” Milton said with a grin and reached for his belt buckle. 

The bottom view was more lovely than the top even with all the good parts still hidden behind boring light blue boxers. I could see the swell. I have an imagination. He dropped his boxers with a deft flip of his hands and stood magnificent, exposed and huge. No, I didn’t get out a tape measure, but he was big. He was a big man; he should be big, and that was going up my ass.

“Easy,” Milton said gently. He strode over to the bed, every centimeter of him awe inspiring. His hands found my shirt, and I was as bare as him. His hands found everywhere. Fear and apprehension turned to pure lust. I wanted more. I wanted everything.

“No, I’m driving. Keep your hands above your head.”

I’m keeping the rest of the details for my memory only. I’ll only say he was a great driver, none of the bumbling of two teenagers trying to figure it out. I guess there’s some benefit to being older and experienced.

****

“Austin, are you awake?”

He’d felt me move. I’d been draped over his chest where he’d very determinedly put me last night. “Need to pee.”

“Go.” Milton shooed me from the bed, but my freedom was short lived, not entirely a bad thing. I liked his arms around me, but I’d been restless the last hour, and he would know if I even breathed faster. He would feel every shift and every breath. “Sleep or talk?”

“It’s two in the morning.”

“And you’ve been up for an hour,” Milton countered. He’d known. So much for subterfuge. “I’m paying close attention to you. So what’s up?”

I’d just had mind blowing sex, and he wanted to have a philosophical conversation. Crazy. “Nothing,” I grunted.

“Austin, we can do this comfortably in bed with the dim light of the moon, or I can flip you over my knee and turn on all the lights. Which will it be?”

Milton always offers such inviting choices. “I was just awake. We went to bed early.”

“We weren’t exactly sleeping.”

“Milton!”

“Austin!” Milton shot back in the same tone. His hand rubbed my bare back, heavy and reassuring. “And I thought it was my generation who had difficulty talking about sex. I thought your generation was all over that hang-up.”

I grunted again. A grunt is a useful noncommittal noise. Unfortunately Milton’s not satisfied by grunts.

“I’ll lead here,” Milton said, sitting up and pulling me into his arms. “I scared you this morning.”

“No,” I protested.

“Austin,” Milton scolded. “Teen bravado is dangerous as a submissive. Healthy fear can save your bacon.”

“Yeah, OK.”

“Good boy.” Milton kissed my forehead. “I needed to find your limits. I didn’t know for sure, and more dangerously you didn’t either. I was pushing this morning.” Milton brushed my hair back and kissed me again. “Eventually you’re going to like it with some pain and at least a hint of fear, but right now you need to learn about pleasure without pain. It would be easy to train you that sex is only available with humiliation and pain from your dom. We’ll do vanilla for a while then we can play. There are places I won’t go.”

“Limits?”

“Some hard and some soft. You understand this better now?”

“Yes.” I snuggled against Milton’s broad chest. He was right. We’d talked about limits, but it had been nothing but words, a string of vowels and consonants.

“I was on your limit this morning.”

“Yeah.” It was easier to admit buried in his chest. “But it was hot.”

“I saw. Pressure gets you hot, but too much right now will break you. Disobey me here, and you’ll be a very unhappy cub.

“Yes, sir.”

“Good boy.” Milton’s hand stroked down my back. Tomorrow we’ll review limits, but it’s time for rest now. Go to sleep, cub. You were very, very good.”

“Always the teacher.”

“Sleep, cub.” Milton’s hand moved dangerously toward my ass.

***
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