My relationship continued with Douglas. I finished my first year in college. I grabbed a part time job so our meet-ups were a bit less as I too took an evening job. When we did see each other, we would have sex like we did the first time. Like two lovers that didn't see each other.
I was going into my my second year of college and heading into frosh week. Douglas had kept reminding of our time that he let me fuck him each time we previously met. I reminded him that he told me that I was going to get it. It was decided on a evening I was free from froshing, that he was going to cash that in. I didn't know what to expect. He called me up on a Thursday night and said daddy was ready for to give that lesson. I giggled on the phone and teased, asking what daddy wanted. He told me to get my ass downstairs now and he was going to show me. I agreed and quickly freshened up and made my way down.
Of all nights, this still stands out in one of my memories. It was probably the most intense me and Douglas got sexually. I arrived at his condo and knocked on his door. He greeted me in his robe and led me inside by the hand. He led me to the spare room and opened the door. My eyes widened. It was like out of page of a gothic BDSM handbook. There was a single bed with chains and handcuffs. There was a leather swing against another wall. There was a table next to the bed with several bottles and sex toys. Before this room was just a storage room before to when I saw iton previous occasions, but now it was turned into a leather lovers paradise.
He told me to take off my clothes. I played along and said make me. He began to aggressively undress me. He took my shirt off quickly and grabbed my jeans unbuttoning them fast and yanking them down. He exposed my tight white underwear that I wore below. He instructed me to get onto the bed. I crawled onto the bed. He got me to lay on my back. He soon grabbed the cuffs and chains and chained them to each post. He grabbed my hands and cuffed them to each post. My heart began to race. The unknown began to excite me but made me nervy at the same time. Douglas left the room.
I waited patiently for him. I laid their cuffed to the bed staring at the ceiling. I soon heard the tap of boots walking from the bedroom towards the room. I turned my head to the door to see Douglas stroll in. He was decked out in leather boots. He wore chaps that covered the outer parts of his legs. His crotch was exposed where a leather g-string with studs covered his manhood. His ass was exposed. He wore a leather jacket that was open and exposed his hairy chest and his pierced nipples. On his jacket was a silver badge. He wore on his head a leather policeman hat. He held in his hand a small police baton.
Douglas smiled wryly and said I was his prisoner for the night. I laughed and smiled. He sternly asked me if I thought he was funny. I played along saying no sir. He acknowledged this saying that I learn quick and said that I would refer to him as sir. He tapped my package with the baton. I was semi-hard. He asked if I was turned on by him. I replied yes sir. He asked me to show him. I said I couldn't, forgetting to say sir. He told me I was forgetting something. I said sorry sir. He said he was going to help me learn. Douglas grabbed my underwear and tore them off me, exposing me. I gasped as he did this. He threw my tattered underwear on the floor. I became hard. My heart was beating faster.
Douglas said he was going to make him his property. He went to the table and grabbed a baby blue cock ring. He came back and slid it down my cock. I felt my cock get harder from the pressure it applied to it. My breathing was deeper. Douglas told me that my cock was his but that it was not the only thing that was his. He began to uncuff me and instructed me to get on all fours. I replied with a yes sir. I got onto all fours. He cuffed me again to the posts. My heart began to beat fast again. He tapped my butt cheek with the baton. He asked if this was his ass. I said yes sir. He asked again. I replied again with the same answer. He asked me to say it louder. I replied loudly this time. He moved the baton and started to poke it through my cheeks to my hole. He pressed it against it. I gasped. He remarked that I seemed to like that. He asked if I wanted him to sodomize me. I replied this time with a no sir. Douglas said he didn't believe me and continued to rub the rounded end of baton on my hole. He pried my cheek and continued to tease my hole. Douglas asked again if I liked it. I finally let out a yes sir. He asked if I wanted it. I replied again with a yes sir.
Douglas walked over to the table of toys and grabbed a bottle of anal lube. He walked over to myself and pried my cheeks apart, squeezing lube over my hole. He massaged the lube on my hole before he started to finger some inside me. I silently gasped as he did this. I watched as he began to lube the rounded end of baton. I closed my eyes and took a deep breath. I felt Douglas pry my cheek wide and press the baton against my lubed hole. Slowly it slid in. I gasped and moaned. I gripped the bedpost. Slowly Douglas began to slide in and out the baton in my ass. I moaned kn pleasure. The baton stretched my hole good. I wanted to stroke my cock so bad. It was hard as a rock. Douglas would eventually stop telling me that was enough.
Douglas would put the baton down and went to the table. He would grab a medium sized ass plug. He doused lube all over it. He walked back to myself. He poured the lube again over my hole. I asked what he was going to do with me. He told me to shut up and take it like the cockboy I was. He pressed the plug on my hole and it immediately slid in. He would just leave the plug in my hole. My cock was screaming for attention, but I couldn't have the ways to cum because of the ring's pressure. Douglas said I was going to be punished because I didn't say ask what I was going to do to him sir. He grabbed a ball gag and put it over my mouth, gagging me. I breathed deeply once it was on me. He grabbed a whip with multiple ends on it. I took deep breath again.
Douglas began to gently whip my cheeks with the whip. He continued to humiliate me with his words calling me cockboy and asked if he liked it. The whip didn't sting which was a good thing as the ends were of cloth. He began to whip hard and it began to get my ass red. I moaned behind the gag. He asked if I wanted more. I shook my head no. He asked if I was going to be a good boy. I shook my head yes. I never thought I was going to enjoy BDSM but it certainly got me turned on.
Douglas put the whip down and walked to me, uncuffing the cuffs and chains. He motioned me on my fours and this time cuffed me to the posts at end of the bed. I was facing outwards. The pressure continued to mount on my cock and ass that was stuffed. He told me that he was getting turned on my be being like this. He asked if I wanted daddy's cock. I shooked my yes and got out a muffled yes sir. He said he couldn't hear me. I tried again with another muffled yes sir. Douglas began to rub his leather underwear against my face. I could feel his hard on underneath. He rubbed it against the ball part of the gag. I moaned wanting his cock in my mouth. He again asked if I wanted it. I again made another muffled yes sir.
He unbuttoned the clasps that attached his underwear to the chaps. He slid the chaps off. He slid down the underwear part only enough so his hard cock could flop out. He was hard and he also sported a cock ring on. He took the ball gag off my mouth and a held my head as he guided his cock into my mouth. He let out a moan and asked if I liked it. I let out a muffled yes. He began to fuck my mouth. He held my head as he pumped his cock in and out of my mouth. He said that my mouth waa his.