Nicky stared into Nero's deep black eyes. He had so many feelings he couldn't speak. An indescribable mixture of pleasure, pain excitement and fear. Physically he knew his insides had to rearrange themselves totally. After all the monster cock inside his small frame was taking up more than half of his pelvis and abdomen. Even when he tried to breath he felt he could only breath so much and he had to stop. Nero's monster cock was against his diaphragm! Although he had just cum, Nicky had been so conditioned to cum from anal sex that he could feel another orgasm building again. He immediately felt flush....
ONE YEAR EARLIER
Exactly a year ago to the day Nicky had made a firm decision. He was going to learn how to cum from pure anal sex. His penis was so tiny that there was no way he was going to have penetrative sex even if he wanted to, which he didn't. So he knew that he would do what a good sissy should do and train his body to be conditioned to be used for receptive anal sex. He had been looking at sissy porn and hypnos for a while and him and his best friend Sammi had gotten into it in a big way. They had read that the way to train yourself to cum from pure anal is as follows. First, get yourself a toy. Preferably one at least 7 inches long. It should be easy to grip from the bottom. Second it should be positioned close to the anus ready for insertion. Then, start jerking your penis and aim to get to the point of orgasm. Just before you make yourself cum from penile stimulation, stop jerking and grab the dildo. It should be inserted as deep as it can possibly go into the rectum. A squatting position is ideal for this training. Start sliding it in and out of your bottom as rapidly as humanly possible. It should be in and out in and out with barely any pause. If you time it right then you should cum hands free.
Sammi and Nicky took these instructions to heart and when they went home from boarding school they each vowed to master the delicate art of the anal orgasm. Buying a dildo was tricky for both of them as they were living at home and couldn't travel but they did have amazon accounts and so they both bought toys online. When Nickys arrived he was pleased to see it was discretely packed. he knew his dad suspected he was gay and also knew his dad tracked his internet use. But what the heck did he care. His dad never confronted him so he just carried on looking at porn and getting horny like any teenage boy. On the night he got the dildo, he got ready.
He had hidden the dildo under his bed and waited till he knew he wouldn't be bothered by his dad. He and Sammi were sissy sisters and wanted to try training their pussies together. So he set up his phone so the camera was facing him. He got naked and prepared. He lay a towel down, ha lay the dildo on the towel and used a small tub of vaseline to lube up the dildo. Next he called Sammi on Kik for a video chat. Sammi (who had a thing for fairies and pixies and liked to go by the name Sprite) answered. Sammi was set up the same way with the same dildo. They remained hushed and as they squatted down their tiny cocks hardened. Sammis cock was longer than Nickys at a whopping three inches hard. The sissies were nervous but excited and they talked to each other as the jerked, each fascinated by each others bodies. As they pumped their cocks they both started to feel the orgasms coming on. Reaching for the dildos they primed their anuses simultaneously. Nicky struggled to push the head in, but Sammi was a bit stronger and had been using his fingers for a while, managed to slip the toy in easily. Once both bois had the dildo in, they needed to jerk their micrococks again to get the orgasms to return. They moaned as precum oozed out of their boiclits. Using their free hand they slowly slid the dildo in and out of their slimy rectums. The dildoes glistened as they slid in and out. There were hints of pain as the sliding increased in pace but as their rectums relaxed, the pain was replaced with pleasure.
Nicky came first. Tiny spurts of boi goo erupted from the now flaccid clit. His knees buckled and he could no longer hold the squat. It had taken a whole 3 minutes of anal frigging before he had climaxed. Sammi was close behind at 5 minutes. Sammi, who was taller than nicky but equaly thin, collapsed on his towel too. As they both pulled their dildoes out, small globs of mucous mixed with vaseline plopped out of their boi pussies. They sighed and briefly chatted before agreeing to do this every night of the summer.
When summer was over four months later, the bois were pros. Frigging their anal holes for between 3-5 minutes was about as much vigorous exercise as their skinny bodies could take. Thankfully their training had taken their time to cum down to mere seconds. Sammi could last maybe 10 frigs of the dildo and his tiny cock was spurting thin strands of almost clear cum. Nicky could cum as soon as the head of the dildo penetrated his anus and the shaft was in. Although now he managed not to collapse into a heap. He would use all his willpower to stay squatting and after a few minutes he would do another quick slide...in.... and out.... and his second orgasm would wash over his pathetic body. Sammi again needed a few more frigs but he also had mastered the multiple anal orgasm. Now to put the practice to the test.....
PRESENT DAY
Nicky's anus was dilated more than it had ever been with his toys. Despite the recentness of his previous orgasm, he came again from the mere fact that Nero's cock was so deep in him. He was not able to hold his body upright and he went limp with Nero's monster cock deep inside him like a huge meat spear. Nero wrapped his massive arms around Nicky and stood up carrying the boy fully impaled balls deep. He could feel Nickys skinny butt cheeks against his groin folds and his cock got even harder if that were possible. Nicky was now completely owned by Nero. His asshole was spasming around the base of the massive cock and Nero's cock was still increasing in hardness and girth. Nero knew that Nicky would not last even one of his fucks let alone multiple. If Nicky had his way Nero was convinced he would pass out from a real pounding especially in the warm environment of the steam room. He decided to carry the limp boy to his bedroom and finish his fuck there.
Nicky felt Nero hold him close to his body. Nicky felt that here was a man who was the ultimate protector. Next to Nero, Nicky felt weak and pathetic, which of course he was. However he also felt that Nero would keep him safe and as long as Nicky was his sissy, Nero would do anything to keep him his. Nero was such as contrast to Nicky. Nicky's tiny frame was made to look and feel even more so when juxtaposed so clearly in such a compromising position. There was nothing left to the imagination whatsoever.
Nicky saw Nero grab the back pack in the one hand and with his other arm held the boy firmly with only the arm and Neros Cock keeping Nicky from sliding down the slippery black body. Nicky wrapped his skinny legs round Nero to get some purchase as he was carried up the stairs. Nicky felt cool as the AC in the house was on. He watched the house pass him by. he noted that in the hall, Wade the valet, was standing to attention looking like a statue. But with careful observation one could see Wade's eyes were following the couple with Nicky firmly ensconsed around Nero's mega cock. Wade did not bat an eyelid and betrayed no emotion or judgement.
Each step up the grand staircase towards the bedroom caused the shaft of Nero's cock to slip an inch or two into his body, then slid out by the same amount. Nicky did all he could to stop himself peeing as Nero made the climb up to the bedroom. Nicky felt the huge cock sway deep inside his guts from side to side with each step. The sensation was like having a metronome inside his guts swinging rhythmically from side to side. it made him somewhat nauseous but also it felt like pure pleasure. He was also about to cum again from the rectal stimulation but by a miracle, he held off. Finally the big black man arrived at a door and used Nicky's back to push the door open. Nero dropped the backpack and used his now free hand to shut the door. As he did so Nicky briefly glimpsed a huge double king bed made with a soft fleece sheet on top. Nicky could no longer contain himself. his microcock which was now rubbing against the massive mans lower abdomen squirted out several drops of clear fluid as he came. He moaned loudly and finally his legs could hold on no longer around Neros monstrous waist. With the cum, Nickys anus spasmed feebly around Neros now fully hard cock. This made Nero even more horny and he couldn't wait to begin the fucking. If only Nicker knew that his anus was only starting to be stretched and worked!
Nicky had a tiny bit of pee left in his bladder and this leaked out as soon as his orgasm faded. Again Nero felt this and felt awesome power over this tiny sissy wench. He hadn't even thrusted a single time and yet Nicky had cum three times. Once from the most miniscule of oral stimulations and twice from anal sex. This was going to be so much fun!
Nero towered over the bed and gently lowered Nicky down onto the bed. 2 inches of his cock slide out of Nickys ass as he lowered the boi. Nicky moaned with pleasure and pain. Neros cock was truly massive and Nicky had gotten used to the slightly narrower base in his hole. Now the thicker shaft was stretching him a little he really felt it. Nero then grabbed the boi by the backs of the thighs, still wearing the sexy thigh high legwarmers. The shorts had been ripped off. Nicky also still had the skinny tshirt on with the sexy choker. Nero let go of one of Nickys legs and grabbed the t shirt roughly. Nero pulled and Nickys body lifted off the bed slightly causing Nicky to moan again. Nero pulled harder but this time he jerked the shirt. It ripped in the middle. Nero jerked again and again ripping the shirt in half. With one hand, Nero tugged under the boi and the remains of the shirt slipped underneath Nickys slick white body. Nero could now fully appreciate the sissy that he was about to pound into oblivion.
Nicky was so slim. His ribs were visible and his pecs were practically non existent. On a girl there would be small mounds of breasts but on Nicky's chest there was just beautiful pale skin and tiny hard pink nipples. Ribs were seen the whole way accross his chest making him look frail and delicate. Nero's cock throbbed at the sight of him. Nero grabbed the bois thighs again and pushed them back towards his chest easily. Nicky's flexible hips allowed Nero to push them all the way back so the knees were touching his ears. Nero saw the lad's feet poking through the legwarmers. They were pale white and his nails were painted in the french style. Nicky's face was a mixture of beautiful and afraid. His lips were dry and he tried to lick them to moisten them. To Nero it looked like Nicky was a kitten. Nero looked deep into Nickys blue wide eyes. He said "Ok Nicky. I am going to fuck you now." Nicky's eyes were already wide but they got even wider. His fear made Nero hornier. "I take a while to cum and i will probably stay hard after I do. So don't expect me to pull out ok?"
Nicky had no choice. He nodded. Nero then said "and once I've cum I'm going to thrust balls deep. And wait. And wait, until I am rock hard. Then I'm going to fuck you again and again until my balls are dry. OK?" nicky noted there was a firmness in Nero's voice. He knew this wasn't a question. It was a statement. He nodded. Nicky could see on the clock on the other side of the room that it was 3pm. Nero slid his cock out almost 10 inches in one slick movement. This caused Nicky to cum again making the boi's anus spasm uncontrollably. Nero slammed his cock in balls deep! No mercy. Nicky gasped! No words came out. Nero pulled out 10 inches and slammed again. Then he started to rhythmically fuck the boi. nickys anus spasmed again and again.... The fucking had begun. Nicky passed out from pain, orgasms and exhaustion many times. But every time he came round, the monster cock was pounding his sissy rectum. It wasn't until around 9pm that Nero started to slow down. By this time Nicky was sobbing quietly to himself. He was in ectasy but was tired hungry and thirsty. But he realised at this point, he was also in love.