The Switch
Part Three
“Harold, get in here now!” Jake shouted. Three weeks ago, Jake had come into his brother’s life but every day, his brother was acting like less than a brother and more of a sister. And now, today there is lipstick on Jonathan’s coffee cup! “Harold, when you told me you were going to make my brother more submissive, I did not think that included turning him into a woman. Look at him now. He is wearing make-up, lipstick, he loves female undies and stockings, and he has started to grow breasts. I thought the estrogen you were giving him was to make him less of an asshole and more submissive to me. What the fuck man? What are you doing to him? What happened to the exercise routine to get him rock hard abs? Answer me dammit!”
Harold replied that he was just following his instructions. “I said turn him into a submissive, embarrass him a little, but you have gone too far here.” “We can fix this Sir. Leave everything to me.” Harold replied. For the rest of the morning, Harold worked on a new tape for Jonathan to listen to. Meanwhile, there was a delivery. The new clothes Jake had ordered for his brother had arrived.
Jonathan was taken to his room and watched the spirals. He now loved watching them and felt so safe and so serene every time he did. This has become his happy place. A file flashed pictures and words over and over and he stared at the monitor . “Good boys are submissive boys” “Obey” “Give in to your Master” “focus” “Controlled” “Mindless toy” “Good boys are obedient boys” “Suck cock” flashed across the screen while pictures of men in jocks, football uniforms, military uniforms, suits, and leather were inserted. “You want to be like them” “Be a submissive boy” “Give in” “This is who you are” Some of the men were sucking cocks while in leather or wearing a suit and loving every moment of it; some showed their rock hard abs, flexing and posing. There was a voice that asked “This is what you want, right Jonathan?” and he started to drool. “Repeat after me, over and over—Yes, this is what I want.” And he repeated it over and over for Master. Harold turned off the monitor as Jake entered the room.
“Time for you to get dressed brother. Look at your new outfits I bought for you.” Jonathan stopped and was told to strip. Harold cleaned the make-up and lipstick off of Jonathan as Jake told him to put it on the clothes he was handed. He slid the black silk boxers on over his caged penis, the black ultra sheer OTC’s then the black silk shirt with his diamond cufflinks, black sequin pants, black velvet shoes, black sequin bowtie, and black sequin jacket with white trim along the lapel and pockets. Jake put a black and white polka dot pocket silk in Jonathan’s pocket and added a black lapel flower. He handed Jonathan a ring with the letter J formed in diamonds on an onyx stone and three bracelets for his right wrist, two with a watch for the right one. “Now you look like my brother!” he said and took his arm to escort him to dinner. As they walked, Jonathan’s rock hard nipples pushed against the tight silk shirt he was wearing. The fabric was making his shaved cock rock hard in its cage; so hard that he screamed in agony. As they approached the table, Jake escorted his brother to one end and held his chair while he sat down in his new suit. Before Jake sat down, he told his brother to raise his eyes and look at him. “I want you to really take a good look at me!” he said and Jonathan saw the man he once was staring back at him. “You look fantastic—even more like me than you did when you first arrived. It’s like looking at myself in the mirror.” Jake replied, “Does it make you happy that I have been turned into you? It means you can do whatever with yourself while I am now trapped as this pretentious asshole. One of us has to be you and from what I was told, you needed to be taken down a peg or two.” “Taken down a peg or two? Look at how I was dressing although I do like this outfit you picked out for me. But please, if it is okay with you, no more women’s clothing?” Jake nodded and sat down for dinner. “I have ordered steaks for us this evening. From now on, you and I will eat the same meal. You will have to take your diet pills and I will be hiring a trainer for you. I want you to rebuild that body of yours, no waist, rock hard abs and a big chest. Sound good?” Jonathan smiled at his brother. “If that pleases you brother, then yes.”
After dinner, instead of going to the study, Jake took his brother into the dressing room. “Open your closet. Go ahead, open it.” Jonathan did so and saw his power suits were now all gone. Replacing them were silk suits and shirts, new shoes, leather pants, chaps, jackets, shirts—an entirely new wardrobe. “I want to see you in leather and take you out for a drink. Is that ok with you?” Jonathan nodded as he was speechless. His brother has really outdone himself with the new clothes. “Shall I put some leather on now?” he asked and Jake said “Fuck yeah!” Jonathan took off his suit and put on the leather chaps, a leather jock strap, high leather boots, a leather shirt, leather bowtie, cross chest strap and belt, and a cap. “This feels great on me! I love it. Thank you Jake!!! You are the best brother ever!” He couldn’t contain his excitement and screamed as his caged penis grew again and there was no room. It didn’t matter though as the weeks of unreleased cum now dripped out of the cage and all over his leather jock. “That’s ok brother” Jake reassured him. “We all have accidents and it may be time to remove that thing.” Jake then removed the chastity device but Jonathan said he felt naked without it. “You’ll get use to not wearing it but I do have something else for you to wear.” Jake pulled out a leather hood and told his brother to put it on. “I can’t see” he told Jake but Jake said that is the point. While the mask covered his face, there was a hole for his mouth. Jake told him to open wide, shoved a penis shaped gag in and attached it to the mask. “You will get use to it as you are to sleep with this on every night but for now, take it off.”
They went into the study where Jake had yet another surprise for his brother. He had him kneel before him so he could put a steel collar on him. Attached to the collar was a chain. Jake then led his brother over to a machine that he bought and instructed him to sit down. Jonathan complied and Jake bent down to turn it on. “Get ready, this may hurt. But you’re a big boy now so no crying. Ok?” Jonathan said ok and he flipped a switch. Immediately, a large penis rammed into Jonathan’s ass and went in and out, over and over. Jonathan wanted to scream but he didn’t. He was just fucked over and over. Jake watched drinking his scotch and water with his cigar, blowing the smoke toward his brother. “How does that feel? You like it? You know, wearing chaps makes it easier to fuck you with your clothes on.” Jake said. Jonathan said it hurt at first but he is getting use to it. Jake stopped the machine and told his brother he would use that machine daily, and that if he wanted to wear his leathers while doing so was ok. Jonathan loved the idea and let Jake know that would be outstanding. Jake then led Jonathan over to his chair, had him kneel in front of him and suck his cock.
Jonathan sucked for what seemed to be an eternity but did so with passion. He was in love with his brother’s cock. His lips caressed it carefully, kissing and sucking his balls and coming back to the shaft. He sucked it right in and took it all the way. Jake pushed Jonathan’s head deeply into his crotch shoving his cock the deepest ever but Jonathan loved it! He was now an expert cock sucker; so good that he could suck the semen right out of Jake’s cock before he was ready to release it and not let a drop out of his mouth. He loved sucking his brother dry and the salty taste of his semen had replaced the euphoric feelings it once had after drinking a cognac or two. After his brother had fully released into his mouth, he would start to kiss his shaft. Jake decided it was time and they finally retired for the evening with Jake reminding Jonathan about his hood. Jonathan loved the smell of his new leathers and wanted to wear them to bed. Jake told him that would be fine and helped him put the hood on, strapping it around his head. “Harold will be assisting you in the future.” Jake told his brother. He then shoved the penis gag in and secured it to the hood. “Now go to bed boy! You have another big day tomorrow.”
Jonathan laid in bed recounting what had transpired today. His brother had shown him how much he truly loves him by correcting what that evil man Harold had been having his do. He did not know why he started wearing make-up and lipstick; he just knew it was Harold who took him to the salon and had him learn how to apply it. He did like his new hairdo—the blonde curls looked great and he had never had his hair this long before but he could not help but wonder if the hood would mess up his hair. And leather and silk clothes—mmm! They felt wonderful against his body. He did have a supportive brother who wanted him to just relax, unwind and be himself. Tomorrow, he thought, I will wear the white leather suit he bought me with the white leather shirt and bow tie. And add the white velvet shoes! I’ll look so stunning in them with my platinum hair. Can’t wait to see what he has planned for me tomorrow. But we do need to get rid of that nasty Harold. How can I get Jake to understand he needs to go?
Jonathan did not sleep a wink. He laid in bed with the thoughts of getting rid of Harold monopolizing his thoughts. Gone were any thoughts of business, finance, or even riding. Gone were the thoughts of taking one of his Porsche’s out for a spin. He no longer wanted to dress in power suits. Leather and silk were all he needed.
Jake also laid in bed thinking of how great his brother looked in leather and thought of taking him to a gay bar dressed that way. He would look like a dom in them but once others in the bar learned how submissive he really has become, he could offer up his brother for $100 a fuck and $50 a blow job. Maybe we should take pictures of this happening and then blow them up to use as wall art, he thought. But then he thought of how vulnerable he was tonight, how submissive he has become and how he needed his older brother to protect him. Yes, he was the older brother by 5 minutes which is why he should be the dominant one of the two. He finally fell asleep dreaming of what fun he could have with his brother.