I'll say from the start, this is a long post. But if you like stories of "firsts" and don't mind that it's not an IRL meet up, then read on! I hope you like it :)

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All of this was because I decided to post in r/sissypersonals

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- THE START -

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Very recently I stopped lurking and started sharing on some sissy subreddits. I've rapidly been dipping my toes in deeper sissy ponds. A few nights ago I posted to announce that I would have some alone time to explore being a sissy further and invited people to reach out to me. Honestly, I was fully prepared to have no one contact me, as I know I'm not as gurly as some of the other sissies here (seriously, some of you gurls are drop dead gorgeous!). I was planning to lock myself into my cage that night. In my head, I imagined staying locked for two weeks (a personal best) and see how slutty I could work myself up to be by the end. I have been listening to Bambi Sleep and dressing as often as possible. Happily, my post did not go without reply.

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The first guy I chatted with was super nice! He was a switch, so he teased me and made me dress in my lingerie for him. I was telling him how I planned to make myself smooth, but was going to do it later so that timing would work out with other things going on in my life. He encouraged me to do it that night and to my surprise I found myself continuing to do exactly as he said. All my rational reasoning and planning went out the window with almost zero effort and soon I was eagerly spreading depilatory cream all over my thighs, tummy, clitty, and bottom. And before I knew it, I was sending him photos of my smooth, bald privates, my clitty glistening from the shower.

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I went to my room to get ready for bed and was about to go to sleep when I decided to check my phone one more time. To my surprise there were multiple new messages from different senders. I opened one and began chatting to a dom, who I addressed as "Sir". I told him I wanted someone to boss me around on camera and he replied by telling me that is precisely what he wanted to do too. In my head, this was a plan for at the end of the fortnight in chastity and I was going to go to bed now that we'd noted our mutual interest. But once again, I found myself offering little resistance as Sir started teasing me. 

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It's such a different experience being a sissy, being the object of male desire. I'm not sure if the thrill of it made me more willing to submit or if that's just where my mind is at currently, but submit I did. Initially, I kept thinking that I would put an end to it at my leisure, before any sort of climax, when I wanted to sleep. But Sir kept asking for more and I kept doing as I was told.

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Quickly we moved on from dirty texts fantasizing about what we would do if we were to meet, to Sir giving me instructions. I got out of bed and put on my sissy maid outfit and began sending Sir slutty photos of with my clitty dangling freely from below my sheer, lace skirt, and my nipples visible through the mesh.

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"Good sis. Rub that asshole for Sir. I want to see your finger inside that sissy pussy," he commanded.

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And so I rolled onto my back with my legs in fishnet thigh-highs held in the air. I sucked on my middle finger before inserting it inside myself to the last knuckle. My free hand held down the record button on my phone as I massaged my sissy hole for the camera, whimpering as I hit the right spots. In return, Sir sent photos of his cock. It looked big enough for two hands and then some. And thick.

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"Good sissy. You sound so hot. So desperate to please," he commended, "Does my sis have any toys that she plays with?"

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I paused for a moment. Wondering if I was really about to pull out my toy box for a stranger when I had planned to sleep. Plus I usually clean myself thoroughly before doing any penetrating. Earlier that day I had read an article that said that 9/10 times, as long as you have a fibrous diet, you should be able to have backdoor fun without douching and get to the end still clean, so I thought I'd take my chances.

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With an eagerness that surprised me, I opened up my toy box and laid them out before sending Sir a photo. In the photo, neatly laid out, were the following:

- nJoy PureWand (resting in it's pink satin lined box)

- Fox tail buttplug (pink)

- a 12" dildo

- a 8" dildo

- Lelo SmartWand (large)

- Aneros Helix Syn

- 2 shots of Jaeger (Just kidding! Any Chappelle fans? No? 😅)

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"Start with the second. We will save the big one for when you're ready to sissygasm," Sir instructed.

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Sir told me to fuck myself with the 8" dildo. I couldn't be bothered getting lube and I had recently discovered, thanks to Bambi Sleep, that I could deep throat that cock, and so I took it upon myself to send Sir a video of this, gagging noisily before I reached the hilt. Perhaps a little too cocky!

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I recorded a video of me slowly sliding my sissy hole down and around that delicious cock, making sure that my maid uniform was visible as I did so. My cage was so tiny that only my balls were visible for most of the time as I thrust the dildo in and out of my eager hole. While on my back, I brought my knees to my shoulders and held them down with my arms as I continued to fuck myself.

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I mounted the dildo on the floor and crouched over it, bouncing up on down, feeling the head of it slide along my girly insides while my clitty bounced uselessly under my skirt.

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"Thank you, Sir! Thank you so much for letting me ride this cock. I wish it was Sir's tasty cock inside me," I moaned as Sir had demanded.

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Next, Sir had me ride the 8" dildo while I sucked on the 12". The 12" is big and thick. It barely fits in my mouth. But I still tried to deep throat it, gagging uncontrollably every time I went for it, but always going back for more to please Sir.

Sir and I went back and forth on whether or not I should be allowed to cum. Sir made me beg, but when he finally said yes, I realised I actually wanted to stay committed to my self-imposed two week chastity sentence and told Sir I didn't want to cum. I tried to tell Sir that I wanted to do it for him, but he had his mind made up. He wanted me to cum.

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"Take that fucking cage off and empty your balls while you ride that toy and thank Daddy!" he ordered.

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I did as I was told, despite not wanting to cum for the sake of my chastity. The cage came off and my clitty was freely flopping in the air as I continued to ride the dildo. After focusing on my sissy hole for so long, my clitty was taking some time to come back into focus and so it remained soft and I decided to let it warm up at its own pace while I focused on my sissy hole.

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Up and down I bobbed, leaning back on my hands so that the head of the dildo rubbed at the base of my clitty from inside of me. I felt warmth spread through my body as I rode the dildo. Then, suddenly, I felt this wave wash over me that I had never felt before and to my utter surprise, my clitty was twitching limply, shooting streams of sissy juice out. I had my first ever sissygasm!

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"OMG!!!!! Sir, I've never ever done that before! Ever!" I exclaimed with excitement and pride.

"Good girl," he replied.

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Sir began telling me how close he was to cumming and had me parade in front of the mirror in my sissy maid uniform for him to help, whispering and moaning sweet nothings into the mic for him, telling him how grateful I was and how badly I needed his cock. He began telling me how he would cum in my open mouth and yet again I found myself in disbelief as my clitty started to get hard again from thinking about it. I confessed my state of arousal and Sir commanded me to stuff my straining clitty back into its cage.

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It was an absolute struggle. It took almost ten minutes for my clitty to calm down enough to contain it and even after that, it throbbed painfully and eagerly in its cage, begging for release. Despite my begging, Sir did not budge.

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"This is what you wanted. One orgasm is enough. Don't think I'm weak. Two days, no touching. Sissy stays locked up until I message again," he said.

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And then the chat went silent. Now I'm patiently waiting for Sir to contact me again, being a good sissy until then, staying locked, but trying to make myself as frustrated as possible.

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- THE END - 

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I hope you enjoyed this as much as I did! 

If you have any feedback on my writing, I'd love to hear it! 

If you have any suggestions for what could happen next, please share!

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And for those of you that prefer the movies, here's some of the videos I sent to Sir. Apologies for the quality - like I said, it was not planned.