16 comments/ 245368 views/ 21 favorites Step by Step Sissification Ch. 01 By: satinmarabana Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff. -- It all started when I was shopping for new bras and I saw him. He was standing around the lingerie area but not like another bored husband. He was far too interested in the dangling panties on hangers, letting his fingers carefully touch their fabric while trying not to be seen. I thought it was curious but hardly dared to hope that I'd at last found another of that most rare of species: the sissy man. I found the bras I needed but I hung out longer to observe him. I needed to know one way or another. He made his way slowly through the racks, through the bras, the panties, the slips, and the sexier nightwear. He gravitated back to the panties and then stuck near a particular rack. I think he saw me look at him and it almost scared him off but I bought my bras and pretended to leave the area. He waited and then I could see him fingering the panties and his face turning flush. In a jerking movement he grabbed a pair of hanging red satin thong panties and knocked three other pairs to the ground. I had to laugh softly as he hurried to put them up on the rack again, his face very red. His courage hadn't left him and he went up to the counter to pay for the panties. The sales girl kind of glanced at him buying one pair of panties like that but she didn't really care. A sale is a sale. He really did it, gripping his plastic store bag, and moving to leave the area. I saw his pants were bulging significantly and I made my decision. I rode the escalator down and loitered around the bottom. I made sure my shirt was adjusted to show off 'the girls' just right. He came riding down about half a minute later. "Excuse me, could you help me please?" I asked him, flashing him a smile and letting his eyes flick to my breasts. "Uh, sure," he stammered. "This will seem so silly but I hate to eat alone. I'll buy you lunch if you come eat with me. Won't take long." I groaned inside. It was a pretty poor proposition so I let my hand brush his forearm 'accidentally'. "Yeah, for a beautiful woman like you, it would be my pleasure," he replied and my estimate of his smoothness rose immensely. We went to the mall food court and bought some wraps. He insisted on paying for both meals which put the encounter into the realm of a date in my book. We sat and exchanged pleasantries. I waited until his guard was down and then I snatched his lingerie bag. "Oh, I loooove Macy's! What did you get?" He tried to grab for it but it was too late. I'd pulled out the red satin thong and held it between my fingers. "That is so sexy!" I enthused as his face went red again and he almost seemed like he was going to have an attack of some kind. "I bet they are going to look amazing on you." That got him. His jaw literally dropped open as he stared at me. I put the thong back in the bag and handed it back to him. "But they're not..." he began in sort of strangled whisper. "Not for you? Oh please sweetie, it's obvious they are for you." I slipped a shoe out of one of my heels and snuck it up to rub his crotch. "You're so hard I bet you can't wait to put them on!" That blew his mind. Here was this pretty stranger telling him that she knows he wants to wear panties and that it gets him very aroused. He looked like he would faint. I slipped my foot back in my heels and took his hand in mind. "Honey, don't get so worked up. It's all right. Nobody else saw you and I'll never tell. It's perfectly all right. In fact, it's pretty sexy if you ask me." "You think guys in panties are sexy?" he asked in amazement. "Yeah, well, cute guys like you, in the right lingerie and acting like they should... yeah, very sexy." I bit my bottom lip for effect. Didn't take much effort, I really was getting turned on by this, by his sexual energies. "What do you mena acting like I should?" Ah, now we were in the negotiation stage. Priceless. "Well, acting like they want to, embracing it and being, well, you know." "Being a what?" "A sissy!" That got an angry look at me. "I'm no sissy," he hissed. I thought, 'Good, this filly has some spirit left in her.' "Oh, well, I'm sure your right then. You wouldn't be interested in wearing panties and showing them to me, in wearing what I told you and doing what I told you..." He swallowed hard and looked around. "Or would you?" Step by Step Sissification Ch. 02 Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff. -- "Oh, well, I'm sure you're right then. You wouldn't be interested in wearing panties and showing them to me, in wearing what I told you and doing what I told you..." He swallowed hard and looked around. "Or would you?" We lapsed into silence at that plastic food court table. I'd basically asked this stranger, the man who'd bought himself a red satin thong, if he wanted to be a sissy or not. I picked up my own Macy's bag. "I love their lingerie," I said casually while he agonized and his mind raced over my question. I pulled out two bras, each in rich satiny nylon, demi-cut. "I wish I had a 'girlfriend' that would tell me if these looked good on me or not..." I know it was cheating, but that's what you have to do with reluctant sissies. Tempt them with something sexual to get them to tell me the truth. No... to get them to admit the truth to themselves. I held the pink one up against my chest and looked at him. "A sissy is like a girlfriend. I could try on lingerie with a sissy and talk girl talk..." He almost groaned at that. "But, you aren't a sissy, are you?" I slipped my foot back up to his crotch and fondled his raging hardon with my stocking-covered toes. "Hmmm, seems like the jury is still out. Come with me." I stood and gathered my purse and bags. I started walking away and let him catch up. We returned to the Macy's lingerie department and I was glad when he stayed with me the whole way. I went to the sales girl. "The underwire on my bra just broke so I want to change into one of these new ones. Can we use the dressing room?" She nodded with a plastic smile, only her eyes giving away the mention of the man accompanying me. We headed back and picked the largest changing room. I pulled the curtain shut behind us and began to take off my shirt. I faced away from him as I did so, letting him watch me unhook my bra and take it off as well. I covered my breasts with my hands and turned to him. "If only you were a sissy, I'd let you see all this," I teased, letting my hands drop as I reached for my store bag. His eyes practically widened looking at my breasts which pleased me. They are pretty full and luckily they haven't really fallen on me yet. I slipped into the pink bra and hooked it in back. I looked in the mirror, adjusting it this way and that until it fit just right. "How does it look?" I asked him at last, turning to face him fully. He jerked his hand away from his bulging pants but not before I saw him. I didn't mention anything, but I let him gaze on how the bra lifted my breasts and gave me nice cleavage. I placed my hands on the bra and gave the girls a little squeeze. "I love how the demi-cut shows off more of my breasts. Do you like that?" Now he nodded his response, unable to get out an articulate word. I took off the pink one and tried on the green one, following the same routine. I eventually put the pink one back on and then pulled him to his feet. "Your turn. We'd better make sure your thong fits just right." He hesitated as I sat there in my bra and skirt. "Come on, unless you'd like me to leave." He didn't want that so he picked up his bag and just sort of played with it. "Oh, please, girlfriend, drop your skirts and try them on!" I chided. He pulled out the thong and held it in his hand, the price tag dangling. Time to play hard ball. "Okay, you proved your point. You're not a sissy and I should go now." I grabbed my shirt to put it on. "No, don't," he blurted. "Please, stay. I'll... do it." I sat down and got comfortable, my smile relaxed. I waited. Finally, he unbuckled his slacks, took off his shoes and slipped off the slacks. I grinned when I saw he was already wearing bright yellow panties with lacey edging. Perfect! "Those are adorable! And so sexy!" I enthused, reaching out and caressing his hip and bottom. They were satiny and shiny and the lace was thin and soft. "You look very cute in them!" This encouraged him and he took off his shirt too. "Now try on the thong." He hesitated and then pulled down the yellow panties. His cock was impressive and very hard. I giggled and winked at him. He fished out the thong and slipped it on. It didn't cover his cock much at all and he struggled to make it fit right. "Well, now that won't do..." I said softly. I grabbed his yellow panties and carefully wrapped it around his cock. I gripped it and started to stroke him. "Sometimes girlfriends have to help each other out," I explained softly. He stood there stiffly as I jerked his cock. It was less than a minute before I felt it throb and then the panties were filling with cum, lots of hot cum. I cooed, "Good girl, that's the way." He groaned softly. I slowly milked him and wiped it clean. "There you go," I said, taking away the panties from his soft cock and tucking the cock into the thong. "It's very pretty," I said, giving him a critical look over. "A basic of a sissy wardrobe..." I slipped the cum-filled yellow panties into his bag, put my shirt back on and put my other bras in my bag. I pulled a slip of paper from my purse and wrote my phone number on it. "If you call, you'll have to tell me that you're a sissy and then we can go from there. If you aren't a sissy, don't call." And I left him there, standing in a women's changing room wearing nothing but his socks and a red satin thong...