Sissy Joanne has been in chastity for quite a while. 92 days to be exact. I have devised a plan for her to be allowed out of the device, but it comes with a price. No no, not financial this time. This time the cost will be pride and privacy.
I secured a motel room. Not a nice hotel, a cheap sketchy motel. The kind with outdoor entrances to all the rooms, exterior stairs, and colorful patrons hanging out on the balconies. This room is at the end of the isle on the top floor. It's as far from the staircase as possible and in plain view of the roadway. Inside the room there is a box of random loose keys (approx 30 of them), 1 sissy outfit laid out on the bed, and 9 Sissy outfits in locked banker bags. There is also an empty banker bag with an open lock. SJ had to take off her boy clothes and place them the open bag and put on the outfit laying on the bed.
I also secured a 2nd motel room. It's on the other side of the motel, on the top floor, at the end, also as far as possible from the stair case. It faces another road, not as well traveled but still a public road. I am in the 2nd room.
SJ had to walk to me, in full Sissy flare, and first bring me the box of keys. When she arrived in my room, I showed her the chastity key, dropped in the box, shook it up and allowed her to select 1 key. She had to walk all the way back to her room before she was allowed to check the key.
It's possible it opens her chastity cage, her boy clothes, or another outfit, OR nothing at all. In any case, she had to walk back to me with the results and to get another key. She might be in a new outfit, or unlocked in the same outfit, or in her boy clothes (oh wait, I forgot, I didn't actually include THAT key in the box yet).
This goes on for no less than a couple hours, walking up and down the stairs, around the corner of the motel. Full view of the other guests, the street.. she's a bit wobbly in the high heels, and her dresses are a bit short, and her wig is a bit sideways after all the walking. She was getting a bit sweaty and full blown panic was sitting in. She knew chastity release was possible and couldn't believe it was really taking this long. Several outfit changes, none of which were into boy clothes of course. I really think she was ready to take the 'buy out' at that moment. So, I decided it was time for her to take a break from the walking around and broke out the other reason for her to keep going. I opened the bathroom door and let my other little slut out.
Her name is Prissy, and she had endured the same ritual for the previous several hours until she did find her chastity key. She has been patiently waiting for SJ to find hers so they could play (surprise for SJ) but since it was taking sooo long, I decided to give SJ some incentive to walk faster and get through the box.
Prissy stood in front of SJ, her little sissy clit was raging and desperate. She had also been in chastity for nearly 3 months. I instructed SJ to drop to her knees, I barely got the words out of my mouth and she was on the floor. SJ sucked Prissy for all she was worth. Prissy had 88 days of built up cum and frustration ready for SJ's mouth. I kept rattling the box of keys while SJ was performing for me. It was perfect motivation! Prissy wasn't going to be able to last long anyway, but SJ did a perfect job of making her cum really fast. I didnt let her clean the cum off of her chin, I thought it would make a nice addition to her current ruffled and satin dress. I sent Prissy back to the bathroom and locked her back in. I sent SJ back to her room with another key. She found her energy again and was almost at a run in those heels now.
Lucky for her, this was the last key for an outfit. It was a crazy whore ensemble. Think, "Pretty Woman" mini dress with the sides cut away. Platinum blonde wig. Bright red lipstick, and 6" platform heels. SJ nearly cried when she saw it. The balconies had been filling up with guest watching her. There was a big crowd paying attention. She had been able to mentally block it out until now, but this outfit was screaming 'take me' .. She put it on, and opened the door to come back to me. Her chastity cage felt tighter than ever as she made this pass back to me. Men were making comments to her, she started walking faster. Another man started walking behind her, and somehow she found a way to run in those heels.
I opened the door and let her in, just as my friend outside (the man 'chasing' her) gave me a wink and turned the other way… I told her to try another key from the box while she was in my room. It didn't open the device. Try another, no good, and another, still locked. SJ stopped and looked up at me, and smiled and laughed, she figured me out. The key I dropped in at the beginning, was not her key. It was another dummy key to keep her running.
I pulled the REAL key from my pocket and handed it to her. SJ unlocked herself, and Prissy was released from the bathroom again. The tables turned from before and Prissy helped SJ unload her shame and embarrassment.
They'd each had 1 orgasm but I had several more in mind for the day. I made them perform for me. Various sex acts on each other and of course, I had my time with them one on one as well. (that's for another story)
After a couple hours of play time with my girls, I gave SJ her key for the boy clothes still locked away in her room. I locked her device again, and sent her on her way. Yes, 1 last pass across the parking lot dressed like a whore. Only this time, she'd been used like one too.
Source: reddit.com/r/eroticliterature/comments/30t0ud/how_badly_do_you_want_out_of_chastity
Very nice and lovely story. Two lucky sissies!