I Got Caught Again

So a few of you may have seen yesterday that I had posted about my roommate seeing me through the crack of the door riding away on a dildo. I could not stop thinking about it so last night I followed some suggestions left by commenters about what to do next.

Last night I purposefully left the door open just a little bit, like last time and made sure I was facing away so that I wouldn't know if he saw me. So like the other night I stripped completely naked and started to ride away on my biggest dildo, working my ass up and down that thing. It felt so good to fuck my ass like this, and after a short while I was moaning like the little slut I am. There's no way he couldn't have heard me the door was open and I was pounding my little butt for ages.

Eventually I need to stop for a second and just sit all the way down and let out a massive moan, and then I hear my door close. He was absolutely watching me from the hall. As much as I was to just get up and go and check, and maybe convince him to join me, I'm way to horny at this moment, so just continue riding and moaning away for a while longer.

After probably half an hour I get up and put some clothes on to go to the bathroom. After I leave I notice my roommates door is pretty open and he's sat watching porn and jerking off like he had nothing to lose. Clearly he liked watching me ride cos he seemed insanely horny. As much as I wanted to I didn't wait around to see him cum and left him to it, but I think if he catches me again I'm just going to walk over to him and get that cock out for me to play with.

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u/Trapped_Boi — 1 day ago

I Dressed Up and Went Out

The other night I was super horny and as usual this mean that I was riding my dildos, but something just wasn't hitting right. I was feeling good, but I couldn't shake how much I wanted to put on a cute skirt, bra and tiny little crop top and go for a walk. So that's what I did. I got all dressed up and put my vibrator in and went out. I only went for a short walk around my neighbourhood, but it made me so fucking horny. When I finally got back to my flat I realized that my little clit had leaked through my underwear and was dripping down my leg. It was fucking crazy, I'd never been that horny before and never leaked like that, but I guess I can. I spent the rest of the night pounding my butt with dildos and eventually used my vibrator to make my little clit cum while I lay there shaking.

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u/Trapped_Boi — 2 days ago

I'm used to leaking, but that was different

So usually when I play I'll get some pre cum leaking out which I love and would do anything to make it happen even more. But the other night I was playing as normal and leaking a little bit before I took a break to get some food and water. Then I went back to playing with my dildo on the wall and backing myself against it, and out of nowhere cum came out of my dick, but it wasn't cum or precum it was weird. It had the consistency of cum, but the colour and taste of precum. I never had this happen before, I didn't cum, I didn't orgasm in any way and my dick was completely limp. I could feel it coming up through my dick as my dildo pressed against my prostate, and it felt amazing. How do I make this happen again, I haven't had any luck whatsoever in recreating this, but am definitely going to keep trying. If I can make myself cum precum while limp I don't think I'd ever need to touch my dick again.

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u/Trapped_Boi — 2 days ago

I Got Caught

So I've been a little addicted to my dildos recently. Every night I'll be riding away on them having the time of my life, for hours. There's nothing I've been enjoying more than being completely naked and exposed. I've been doing it almost every night for a few months now without being caught by my roommate once, however the other night I didn't realize the door was open just enough that anyone walking past might see in. So I was riding away for a while before I realized that my roommate was standing looking through the gap in my door. They didn't notice that I'd seen them, and I didn't want to stop so I just kept riding harder and harder, breathing heavier, and moaning loudly, giving them a proper show with my dick flopping around in the air. I have no idea how long I was doing this for, or how long they were watching, but the next time I looked they were gone.

I'm not worried about them judging me or anything we all have our kinks and interests, but they are one of the cutest guys I know, with the nicest toned body. It was a few days ago that I saw him and I haven't caught him staring since, but maybe tonight I'll leave the door a little open, being a little louder, kinda hoping he will catch me and maybe give me a hand.

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u/Trapped_Boi — 2 days ago

When I finally did it

For years I've been exploring my sexuality and dipping my toe into cross dressing a bit but for the longest time I couldn't force myself to dress up and go out. That was until I eventually decided to bite the bullet, dress up and find a hook up. I had hooked up with guys in the past but never dressed up so this was a huge step for me.

This was all a few months ago, but I had mentioned to a FWB I had, let's call him Danny, that I liked cross dressing and had a few bits that I could wear if he was into it, and to my surprise he offered to buy me some more clothes, but only if I wore them on the way to his place next time we met. So I ended up buying the cutest skirt and t shirt combo as well as my first pair of heels, made sure I was clean and shaved for Danny and headed out to his place. I have to say I was so scared when I first left mine all dressed up, I felt so exposed, I was wearing a mask so no one could recognize me but still, the thrill was insane.

By the time I got to Danny's my heart was racing and my legs were visibly shaking. I knocked on the door and I swear it felt like an age before he answered the door, but when he did all he had to say was "Good Girl," and I was immediately putty in his hands. He led me up to his bedroom and proceeded to use my holes however he wanted, I was his little slut for him and him alone. He probably fucked me for well over an hour before finally letting me go back home, still dressed up of course.

By the time I got home I was so tired from everything I just crawled into bed and fell asleep fully clothed. When I woke up I saw that he'd sent me a photo of the cutest dress he'd bought me, saying it was waiting for me. I was so excited to have someone feminizing and buying clothes for me I could've cum on the spot, but I'm a good girl so waited till I saw him next.

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u/Trapped_Boi — 2 days ago

I Think I've Broken Myself

I've been exploring my sexuality, especially my sissy side, for a while now and I think I've broken my dick. I've been training my ass a lot recently and now I can easily take my biggest dildo and ride it for an hour without stopping. It feels amazing so good that I often forget about my dick entirely, just letting it flop around a leak while I ride. Then last night I just wanted to jerk off and cum, but it took ages before I even got hard and even when I was hard I just couldn't cum. There was pre cum, so much pre cum, but it felt like I could only edge myself eventually I gave up and just went to sleep. Then when I woke up I had a while before work so I decided to just fuck my ass and within minutes my limp little dick was leaking out cum. It felt amazing I don't think I can ever go back to jerking off, fucking myself just feels way too good, and the orgasm are just so much more intense. I've definitely ended up losing my once big hard man dick and now I have a limp, leaky, useless clit and a gaping pussy as my only sexual organ. I can never go back to being a real man, I'm slowly becoming a horny little slut and I fucking love it.

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u/Trapped_Boi — 2 days ago

I Just Can't Stop!

So recently I've had a lot of time to myself and I've been using it to explore a lot. Different toys and positions all with the goal of maybe one day having a dry orgasm. I've managed to cum a few times laying on my side and fucking myself with a dildo that's got just the right curve to brush my prostate until I shake, and cum all over myself. The feeling of cumming from just fucking myself is so intense it makes me want to give up stroking entirely and just fuck myself all day everyday, but that can wait. In the meantime I'm going to have a whole day to myself next week and I fully intend to do nothing but play, ride and fuck myself until I cum over and over again.

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u/Trapped_Boi — 3 days ago