I am a fairly new submissive. I started a fascination with feminization when I was 13. By the time I was 15 my stepsisters were having a ball turning me into a girl. They showed me how to do my nails, helped me with makeup and helped me dress feminine, like wearing girls jeans, blouses skirts and the most exciting, lingerie. When I was 19 one of the older sister's girlfriends was at the house and I walked into the TV room. I didn't have shoes on and was wearing shorts. I was also wearing tan pantyhose. The girlfriend whispered to my sister, which I heard, "is he wearing pantyhose?' "Yes" she said, "and panties." He's been gradually feminized since he was 14 and loves it. Then I heard her ask my sister "do you think he would benefit from some special discipline.?" My sister quickly replied, "benefit. He'd love it." I won't go into the rest of that scene or my first couple days in submission. But, on the third day my now-mistress announced that this was the day I'd get my first chastity device. She told me we were going to a "special" shop and that I would be in restraints since I was newly in training. That meant I was collared and on a leash. I also was handcuffed and the cuffs attached to a waist chain, just like in prisons. I liked it. We got to the shop and she went around the car and opened my door and helped me out. She took the leash and led me into the shop. There were other people there but it was obviously a very high end sex shop so I did not stand out. There were a couple other girls there with boys on leashes. So my mistress says "we have a shopping list. Let's start with nylons. I want off-black. His sister tells me he wears garter belts so that's good. I won't have to break him in. " She picked out several pair of stockings. "Next he will need a cock cage." The girl showed us several. My mistress asked me if I had a preference. I'd never been put in one so I said I didn't know. "Fine, we'll take two steel cags. But I want one with the eye at the top so I can hitch a leash to it. The salesgirl put each one in a silky bag and a nice box. The my mistress said, "and finally we need to get him his own personal spanking strap. I have others and I also use a belt and switch but he has not received his first whipping yet so I want it to be with his own strap." we went into an adjoining room and was all bondage and punishment equipment. My mistress led me over to one wall that had all sorts of whips and straps. "We'll get two. A longer one and a short one for over the knee beatings." She took two off the wall and showed them to me. "Well, what do you think? Do you think these will work." "Yes ma'am. I'm sure they will." The sales girl then said "Usually when a mistress gets a submissive his first strap she likes to try it here to be sure. Do you want to try?" "Absolutely." "Good. Give me his leash. " she led me through this room into another smaller room and had a couple chairs, some wall hooks and two different kinds of benches which I soon found out were punishment benches. "Come over here and let me take your jeans off. It's kind of hard if you're cuffed up." She unhitched my jeans and pulled them down. "Do you want to leave the cuffs on or take them off." She was asking me so I said to leave them on. "OK. We'll leave your panties on too. " She led me over to a kind of leather covered table. "Now lean over the table and put your head on that pillow." I did as I was told. Then she asked my mistress if she was ready. She said yes. "OK. Are you ready?" she asked me. "Yes ma'am,." Then there was a pause and the first stroke hit my behind. It make a loud crack and stung. "I'll give you five more so you can see how it feels." She proceeded to give my five fairly hard strokes. "OK. Stand up. How was that." "It stung mistress," "I can see you're getting hard so you must have enjoyed it." "Yes mistress." "Good. I'll let you cum when we get home." The sales girls pulled up my jeans and hitched them. Before she zipped them up she reached inside an stroked my hard cock a couple times." "I'm sure we'll see you again. Cut to the cage. I was put in the cage that night and told I would be left in it for the next day or so. That night I was diapered over the cage which included tight plastic panties. My point is that I slept with the cage on and it was not bad at all. After my mistress locked me in it I got very hard and found out first hand how the cage works. For other submissives just starting, being caged and sleeping caged is not bad. I wear nylon panties during the day which works out well too. Good luck.
Hey Robbie, are you familiar with the following section of CM? https://www.chastitymansion.com/forums/index.php?forums/member-fiction.19/