I once met another cute guy at a bar. We were both horny and went back to my place. Unfortunately as we had another drink we discovered that we were both tops. He was so cute – just like a boy. He was shorter, thinner and he had this cute little butt I was just dying to get my hands on and _d_i_c_k_ into.
Thinking I could get my way with him I devilishly suggested we make a wager. We would compare _d_i_c_k_ size and the guy with the smallest _c_o_c_k_ had to submit to a good old-fashioned spanking and then hard ass _f_u_c_k_ing. We agreed in advance that the spanking would consist of thirty good swats with a variety of implements and that the _f_u_c_k_ing would last as long as the winner wanted.
I was so sure I would win because he was shorter then me. He was so small and compact, so boyish. I was definitely looking forward to _f_u_c_k_ing his cute little ass!
Unfortunately, for my butt, this little guy had one of the biggest and thickest _c_o_c_k_s I've ever seen. What a surprise! As I looked at his massive _c_o_c_k_ I realized getting _f_u_c_k_ed by him was going to be one very hardest _f_u_c_k_ings I've ever had. _s_h_i_t_!
With a laugh he teased me about my smaller _c_o_c_k_ and modest sized balls. Then, with a grin he asked if I wanted my _f_u_c_k_ing "hard" or "soft". Feeling relieved I said, "Oh, I'd like a soft _f_u_c_k_ing please!" He then said, "OK, if you really want it. I'll spank you really hard, to get this little _c_o_c_k_ of yours soft! Then, when your little _c_o_c_k_'s completely soft you'll really feel my big _c_o_c_k_ _f_u_c_k_ing you!"
I couldn't tell if he was joking, anyhow I assumed he was joking and somewhat reluctantly I went over his lap for the spankings. I was not crazy about sticking to the deal, but after all, a bets a bet, right? He reached around and held onto my _d_i_c_k_ with one hand and spanked with the other. Quickly I discovered that this little guy could really spank hard! The first thirty swats with his hand had me wondering what I had gotten myself into but I still had my erection - not as big as his, but at least I still had it.
As he gave me 30 with the paddle and then 30 with that dammed razor strap I had to admit I'd really underestimated his strength. Although he didn't have huge muscles these swats were really hurting! Also as he spanked my butt hard my _c_o_c_k_ slowly began to shrivel up. As my _c_o_c_k_ got smaller he seemed to have this sense of glee about it. As my butt got redder and redder and my _c_o_c_k_ smaller and smaller he was just laughing and smiling with pleasure. Every so often he would squeeze my little _c_o_c_k_ and make a comment like "Well, I'm happy to see you're learning your lesson LITTLE boy." or he'd say "There's nothing nicer then feeling a boy's _c_o_c_k_ shrivel up during a good hard spanking!" Frankly there was nothing I could think of to say to these comments, besides I was really too busy concentrating on the pain in my butt to worry about my penis.
By the time the strapping was over my erection was nothing but a distant memory. He had my entire penis and balls in his hand and was loving every minute of it.
He then let me up from his lap for a break before the final spanking. The final spanking was to be with the hairbrush. Something he said "He loved to give, but I would hate to receive!" As I stood in front of him rubbing my buttocks frantically he continue to joke and tease me about my shrunken penis. Meanwhile his penis looked even more massive then before! Even I had to admit that his _c_o_c_k_ looked about ten times larger then mine. Mine was like a little boy's and his was, a symbol of true manhood. As he played with my tiny _c_o_c_k_ he continued to ask rhetorical questions like "Well, it's very small now but I think a good dose of the hairbrush can make it even smaller, what do you think?" What could I say? Looking at his big thick _c_o_c_k_ along side my little thing I don't think I've ever been as embarrassed or humiliated in my life.
With this great big smile of satisfaction on his face he said, "It looks like you're gotta get your wish and experience a 'soft _f_u_c_k_ing'. What do ya think of that?" I was not looking forward to it. I had never liked getting _f_u_c_k_ed much in the first place but taking his big _c_o_c_k_ without even a hint of a hard-on was definitely going to be a painful experience.
"OK kiddo", he said, smiling and patting his lap enthusiastically. "Let's get your little _c_o_c_k_ down in my lap and your cute butt pointing up so we can give you 30 good hard ones with the hairbrush! OK?" Once again, I reluctantly got over his lap. Again he reached under and gathered up in his hand what he referred to as my "little-boy" _d_i_c_k_ and balls.
This hairbrushing wasn't going to be any fun but I had lost the bet so I had to take it. Besides I thought, how much can a little hairbrush hurt? Oh my God, that hairbrush was by far the worst yet! Try as I might to stay still, each swat from that hairbrush was like getting stung by a hundred bees. He raised the hairbrush high above my butt and brought it down with as much force as possible. I was swearing like crazy and he seemed to love this reaction. After each hard swat he gave it plenty of time to sink in. This also gave him ample opportunity to tease me about my _c_o_c_k_ further, adding comments like "It's nice to see that when a boy is well spanked his attention is fully focused on his back-side and he's not thinking about his little penis." I had to admit, as that dam hairbrush toasted my butt my shriveled up little _c_o_c_k_ was the last thing on my mind. The only thing in the world I was concerned with was the fire in my butt. After each swat I yelped and I kicked. I might have tried to get up but his grip on my little _c_o_c_k_ and balls kept me firmly in place.
Finally my spanking was over. Holy _f_u_c_k_ did it hurt! I danced from leg to leg and rubbed my butt furiously. As I jumped around, swearing, and gasping he looked with delight at my little _c_o_c_k_ flapping around harmlessly. He was proud that the spanking had been a very effective punishment, something I would remember for a long time. This whole experience had brought back memories of when I was a kid, I had totally forgotten how much spankings really hurt!
While I continued to rub my bottom and cool myself down he casually unwrapped a condom and proceeded to unfurl it onto his huge _c_o_c_k_. I hardly noticed as he moved a pillow into the middle of the bed in preparation for my final humiliation. After a short time he motioned me towards the pillow and said, "Get your butt on top of the pillow and I want to see that soft little _c_o_c_k_ of yours pointing backwards and towards your feet." Hesitantly I obeyed and lowered myself on top of the pillow. As requested I pointed my little _c_o_c_k_ backwards, in total defeat.
What a contrast we would have appeared to an observer. Him on top of me, from behind, with his big thick _c_o_c_k_ aimed towards my asshole, excited, empowered, a man in his prime, ready to _f_u_c_k_ – good and hard. Then me, submissive, defeated and totally humiliated. My _c_o_c_k_ lying limply on the pillow, my sore butt sticking up, exposed.
He, ready to experience the ultimate pleasure. Me, submitting my asshole to the pain of his massive penis.
With a chuckle, he said "OK kid, because you took your spanking so well I've decided to give you a little lube. Not that much mind you, just a little. After all, we want you to really feel this." With that I felt him part my buttocks and I felt a small dab of lube on my asshole. If it was at all possible my _d_i_c_k_ must have shrunk even further. I was scared.
I then felt his huge _c_o_c_k_ up against my asshole. How on earth was I ever going to take this? He began pushing inside me. "Ahhhh _s_h_i_t_!!" I gasped as he pushed further. "Ouch!!!! Fuuucckkk!!!" I cried. I tried to pull myself away just a little but he simply moved forward as well.
"Ouch!! Please - it's too big." I begged. He was still just a little way in but he decided to give me a moment to rest and lecture me. "That's a good boy. You're doing well. I know it hurts, especially when you've got a limp little _d_i_c_k_ like yours. He gave my shriveled _c_o_c_k_ a little nudge with his hand. I could tell he got pleasure knowing that his _c_o_c_k_ was probably fifteen times larger then mine at that moment.
I panicked, I didn't know if I could take any more, his massive _c_o_c_k_ was literally splitting me apart. I needed more time and more lube so I decided to try and make a deal. "Look," I said desperately, "I'll take twenty more with the hairbrush if you give me some more lube."
"Well," he said, after thinking quietly for a moment. "I don't think twenty is enough for more lube ....If you take forty, and you be sure to keep your _c_o_c_k_ completely soft I'll let you have some more."
Sensing a bargaining possibility I said, "Please sir, I'll take 30 and keep my _d_i_c_k_ completely soft for more lube."
But he just laughed and said "Look kid. You've got your choice. Either you take forty extra hard swats with the hairbrush then I give you a little more lube, or we continue your ass-_f_u_c_k_ing right now. What do you want?"
Once again he had me, either I was going to be split open by his massive _c_o_c_k_ right away, or I could take some more swats and get a little more lube. I knew my decision, "OK sir, I'll take 40 more swats, please pull out."
After a few moments he pulled out. It felt so much better, but not for long. I felt him reach for that damm hairbrush and for the next ten minutes I received the 40 extra hard ones I had negotiated for. I also kept my penis completely soft, not that there was much chance of it getting hard. This was pure punishment, not _s_e_x_!
Finally after the forty swats had been delivered we were back where we started earlier. His hard _c_o_c_k_ up against my ass-hole, ready for a ride. Gratefully I felt more lube being squirted on my boy-pussy. He pushed in. I yelped, and I kicked, and I begged but there was no stopping him this time. As he moaned things like "Ahhh ....this is so good." I pounded my fists on the mattress and yelled "Ouch! _f_u_c_k_ it hurts!" The more I begged the more he seemed to enjoy it. For thirty minutes he _f_u_c_k_ed and _f_u_c_k_ed my asshole. When he was finally done he pulled out with a pop.
I thanked God, it was over! As we lay there resting for about twenty minutes I felt completely relaxed. I actually got my hard-on back again but when he discovered it he made me stop touching myself and put on my underwear. Actually he gave me the option of jerking off and then taking 100 with the hairbrush but I wasn't interested in having an orgasm that bad!