I met him on the subway. He was acting like an asshole, drunk, spitting, harassing and old lady on the train. He got off and I followed him.
He went down a lane behind a row of abandoned buildings. I guessed him to be about 20-21, not too tall, 5'8" maybe. He was wearing a baggy pair of jeans and a bright yellow T-shirt. His dark hair was jelled into some kind of "just woke up look".
I knew I was crazy for following, I mean he could have a gun or knife, which knows, but I just couldn't help myself. He didn't notice me following him.
He came up to the back door of an old shop, he put his shoulder up to the door and gave it a bump, it opened right up. Just as he was about to go in I yelled at him to stop. I expected him to run, but he didn't.
I told him that I saw him on the subway and that I was disgusted with his behavior. Especially to harass the old woman, I mean she was practically in tears. I was very surprised when he agreed that his behavior was horrible.
He started going into the building, he asked me to follow.
He said his name was Rory, he had been homeless for a month now and that he had enough friends to lend him their showers to stay clean but that he was living in this room. He said his mother had up and left with some guy, he hadn't heard from her in 3 months. After she left, he could not pay for their apartment so he got kicked out.
Rory, stood up and said again he agreed his behavior was out of line, but that he just lacked structure and guidance in his life. That he hadn't been given any good direction since his father died when he was 12.
He said to me very non-shalantly "will you help me".
I was not sure what kind of help he was hoping for, I assumed it was a pitch for some money or something. Before I could say anything he walked back to closet opened the door and pulled out this leather razor strop. It was 2.5 inches wide, 18 or so long and had thick leather handle sewed on it.
He held it up and said that the night before his father died he gave him a good spanking with his hand, but that the told him next time he was in trouble the pain in his ass would come from this. He said he felt so scared but that he knew his father meant it and that it was because he loved him.
He walked over to me and me if I would beat him. He handed me the strop, and said he needed a dozen hard strokes.
I did not answer if I would do it or not. but he started undressing. his shirt came off, his smooth chest was defined and his as were hard and he had a slight line of hair running from his belly button down. He could see that I was not very responsive, he assumed I was not into giving him a spanking, he offered to do whatever I wanted after I beat him. he rubbed his balls in a suggestive manner.
He went to undo his jeans, I told him to stop for a minute. I confirmed back to him, "you want me to beat your bare ass 12 times with this. And then you will do whatever I want".
he nodded his head yes.
I told him that I would have to do some of it my way. I was still sitting on the floor, he walked closer to me and I reached up and grabbed the waist of his jeans. I undid the button and zipper and they fellt o the floor.
Rory was wearing a pair of plain white boxers. I quickly dropped them to the floor. I was face to face with his flopping cut 5 inter. It was under a nice little bush and his balls were big and hanging. I motioned for him to lay across my lap.
Rory did not complain, I positioned him so his balls and _c_o_c_k_ were laying against my left thigh. I told him to spread his legs wide. I began to massage his nuts through hi slegs, he then started to wiggle when I tickled his ass hole. i gave him a few warm up swats with my hand. jsut enough for his bubble but to go pink.
He did not react to the spanking, he was in another planet.
I instructed him to stand up an dbend over an old crate. His pants were still around his ankles. He stepped out of his pants on one side and spread his legs far apart. his balls were in perfect view and so was his pink hole, it was like it was winking at me.
I picked up the strop, and stood behind him. He was mildly shaking.
I took a few practice swings and told him that he would have to count. I raised it up and WHOOSH, SMACK. It was like the wind was knocked out of him.
After what seemed like forever he yelled ONE!
I raised the srop again, and SWOOSH, Crack.
THis time his yell was more muffled but quicker.
WElts from the two strokes started to appear.
I raised the srtop again and brought it down almost instantaneous he yelled THREE. Strokes 4, 5 6 followed quickly.
After seven he seamed to wilt. his response seemed more automatic.
The eleventh cracked on his ass and he again jumped like after the first few. He count came slower.
his ass was now a mess of welts and bruises starting to appear.
I raised the strop and brought it down as hard as I could. Rory cried out in pain for the first time. Until then it had just been muffled grunts.
I dropped the strop and d went closer to examine his ass. The crimson and purple stripes were very defined. The welts rising quickly. I reached through his legs, and took a hold of his _c_o_c_k_. It was now 8 inches and swollen.
As I rubbed his head and pre-cum leaked out I told him that he wasn't really a bad boy and that I felt he earned his lesson. he began to cry again.
I instructed him to stand and I took a seat onthe crate. I pulled him closer and took his 8 inch swollen dick in my mouth. THe taste o fhis pre-cum made me almost shoot my load.
After lavishly licking his _c_o_c_k_ and massaging his balls he blew his bad boy load in my mouth.
Rory thought he was done.
I then instructed him to resume his position over the crate.
He began to pancick, he thought i was goingto strop him again.
I had other things in store for his hot striped bubble but. I noticed a box of condoms when I came in and took one out, I asked him if he had lube.
He replied he did in a duffel bag onthe floor. I rummaged through till I found the KY.
He was bent over the crate again and whimpering that he wasn't gay and that he really didn't want to be _f_u_c_k_ed. He offered to give me head but I told him to shut up.
He started to cry again, said he was a virgin. I calmly told him there was a first for everything as I undid my pants. As I put the condom on my swollen _c_o_c_k_ he was whimpering. I lubed my _c_o_c_k_ and took a finger full and began poking his hole.
He cried again but said he knew he told me he would do anything. After inserting two fingers and playing his hole out I started pressing my anxious _c_o_c_k_ against the rim.
Slowly I pressed as he began to scream. I finally pushed my way into his tight hole. His burnt bubble but swallowed my whole _c_o_c_k_. As I thrust I could feel the heat from his beaten ass against my pelvis.
I finally blew and as I pulled out and removed the condom Rory just lay still across the crate.
I pulled up my pants and helped Rory stand. I walked him over to the old mattress on the floor he used as a bed and he flopped face first on to it.
I asked him if it wool be OK if I checked up on him in a day or so. he agreed.
It was now raining. I took a T-shirt he had laying on the floor and wet in the rain and returned to lay it across his ass.
I left, but looking forward to checking on Rory. I was wondering if he learned his lesson or if future stropping would be required.
I like to write from the perspective of the spanker, but was hoping to write story in conjunction with someone who likes to right as the spankee. I think it would be cool to post the same story from two perspectives simultaneously.
Interested? Let me know: stu999@hotmail. com