TipsySkin @tipsyskin.bsky.social · 05/10/2026Still couldn't achieve hand free and had to finished with a ruined orgasm. But even with stopping jerking it way before I could "feel" the pleasure of a proper orgasm, I exploded so much cum out... I swear this might have rewired my brain in a dangerous way. 010
TipsySkin @tipsyskin.bsky.social · 05/10/2026I got it suctioned on the wall and fuck myself standing like that into a dazed. Had a legitimate POOL of precum at my feet. Should've took pictures, but was too much into the zone to care. 110
TipsySkin @tipsyskin.bsky.social · 05/10/2026It changed everything. I was able to get it all in with relative ease. And it felt AMAZING. I think having the whole thing put pressure on the front instead of only having it half in with the head directly (and harshly) jabbing the prostate is the way the way to go for me. 110
TipsySkin @tipsyskin.bsky.social · 05/10/2026Pegtember 13 --- Outfit: Pic related. Since we're near the end of that month long challenge, I wanted to try using the realistic dildo I've had for a long time but never liked using (never felt good). AND OH BOY, after a full month of stretching my ass and training my prostate... 140
TipsySkin @tipsyskin.bsky.social · 04/10/2026Need tall women who will force me to wear platform shoes so my ass is at level with her strap. 010
TipsySkin @tipsyskin.bsky.social · 04/10/2026I was planning on filming the entire thing, however, my camera overheated ~20 minutes in... I apologize profusely *naked dogeza*. In the end, I went for a ruined orgasm. Even tho by now, jacking my dick doesn't even feel good anymore. It's clinically just to drain my balls~ 020
TipsySkin @tipsyskin.bsky.social · 04/10/2026Pegtember diary 12: ----- Outfit: Vid related. Buzz day~ An hour+ of getting my prostate battered by strong vibrations. I feel like I'm repeating myself, but I was going insane near the end. Constantly kept on the peak of horniness, without being able to cum from it... Despair. 152
Reposted by TipsySkinArarity @ararity.bsky.social · 03/10/2026 Let me be your spooky secret this halloween 🔥 59220
Reposted by TipsySkinArarity @ararity.bsky.social · 02/10/2026Taking care of your morning wood is my calling 💋 58915
TipsySkin @tipsyskin.bsky.social · 03/10/2026Little PSA to say that even though we're now fully in Locktober, I started Pegtember on the 4th. So I still a have a couple of days of pumping my ass into a (hopefull) handfree orgasm. And since I post my dairies a day or two after the fact, you can still expect a few of them~ 061
TipsySkin @tipsyskin.bsky.social · 01/10/2026That being said, I was still SO HORNY after shooting all that. As I was about to clean up, I got hard again looking at myself in the mirror... I used my Edge 2 for a bit, then got back to milking my prostate with my dildo for a final ruined orgasm. I'm going crazy for real. 010
TipsySkin @tipsyskin.bsky.social · 01/10/2026Pegtember diary 10: ----- Outfit: Pic related. Had time to shave again and dress up like a good little slut! Which means pictures time for you! <3 I also took a video of my riding and giving myself TWO ruined orgasm~ Bad news is, I fucked up the SLog settings, so it looks BAD D: 1102
TipsySkin @tipsyskin.bsky.social · 01/10/2026Hearing the chain of my collar cling along while I make my morning coffee dressed like a slut is driving me wild 😵💫 010
TipsySkin @tipsyskin.bsky.social · 30/09/2026Took this from earlier this month. I LOVE how I start leaking as soon as the dildo goes in... Peak boy slut behavior. 0122
TipsySkin @tipsyskin.bsky.social · 29/09/2026I was legitimately going kinda crazy by the end of it from the lack of orgasm. I couldn't handle it anymore and gave me something like 4 ruined orgasm until I stopped feeling horny... I kinda lost the count. Closest I was to just give up and finish properly. BUT I HELD ON! 011
TipsySkin @tipsyskin.bsky.social · 29/09/2026Pegtember diary 09: --- Outfit: Naked with collar on (Pic unrelated!) Started by bouncing on it, I'm getting seriously addicted to feeling my ass filled... Ended by rotting my brain by watching porn while the Edge 2 was buzzing my prostate. 141
TipsySkin @tipsyskin.bsky.social · 29/09/2026Holy fuck, I woke up HORNY as HELL today. Getting kinda desperate to give my hog a good squeeze tbh... 😵💫 010
TipsySkin @tipsyskin.bsky.social · 26/09/2026At some point, my dick got really hard and twitchy. I felt like I was about to cum hands free. Alas, it didn't happen, but it felt SO FUCKING GOOD, HOLY. 021
TipsySkin @tipsyskin.bsky.social · 26/09/2026Pegtember diary 08: --- Outfit: Naked with collar on. (Pic unrelated!) Spent a whole hour turning myself dumb by watching porn while my Edge 2 was rocking my prostate. I leaked so much pre-cum I didn't even need to give myself a ruined orgasm to avoid blue balls. New achievement! 162
TipsySkin @tipsyskin.bsky.social · 26/09/2026This also made me realized I was wearing a collar every time cum was drained out of my balls this month. And that's insanely hot to me. 030
TipsySkin @tipsyskin.bsky.social · 23/09/2026Pegtember diary 07: ------ Outfit: Naked with collar on. (Pic unrelated!) Bought myself an Edge 2! This thing absolutely rocks. Buzzed myself for a full hour. Still had to finish myself with a ruined orgasm, but it was a positively mind melting experience. 030
TipsySkin @tipsyskin.bsky.social · 22/09/2026Week 3 of only cumming while my ass is full and my prostate is getting milked. 020
TipsySkin @tipsyskin.bsky.social · 18/09/2026What's a guy gotta do to get used and abused in here!? 022
TipsySkin @tipsyskin.bsky.social · 18/09/2026Need a dominant girl to lock me in chastity and force me to watch porn while she milks my prostate. Constantly reminding me that I don't get to fuck cute girls, but they do get to fuck me... :s 030
Reposted by TipsySkinTipsySkin @tipsyskin.bsky.social · 17/09/2026Dressing up and setting up a camera is hard work when you're a slut in heat who can't stop leaking... 083
TipsySkin @tipsyskin.bsky.social · 17/09/2026Dressing up and setting up a camera is hard work when you're a slut in heat who can't stop leaking... 083
TipsySkin @tipsyskin.bsky.social · 14/09/2026Couldn't get in the headspace to achieve dry orgasms either. I really need to find myself a sugar mommy to lock me down in her basement so I can be a slut all day with peace of mind 🥴 021
TipsySkin @tipsyskin.bsky.social · 14/09/2026The house was busy so I had to keep it quiet. Couldn't crossdress and take picture because of it. ): Unfortunately had to finish myself of with TWO ruined orgasm again. But the ride felt amazing and I did cum buckets. Above pic from previous day, showing off the toy I'm riding :3 110
TipsySkin @tipsyskin.bsky.social · 14/09/2026Pegtember diary 06: ------ Outfit: Naked with only my collar. After 4 whole days of chastity, I had some time to ride it again :D The knot at the base went in right away. Humped it so it pushed against my prostate. It was the closest I've felt to actually cumming from my butt. 1101
TipsySkin @tipsyskin.bsky.social · 14/09/2026The masculine urge to put on a skirt and be called a good boy. 041
TipsySkin @tipsyskin.bsky.social · 12/09/2026Going to bed with my balls full and tights. I need to peg myself soon or I'll lose it. 030
TipsySkin @tipsyskin.bsky.social · 11/09/2026PSA: I'm too lazy to revive my Fansly, but I DO dump everything I take on the 5$ tier MEGA archive of my 3D stuff. The one from either P*treon or SubStar. Just saying~ :3 042
Reposted by TipsySkinJaxPlatinum ✨ @jaxplatinum.bsky.social · 08/09/2026Do you like femboys that only wear silver 🩶 and black🖤? #femboy #chastity #twink #trans #nsfw #femsky #skyhub 414219
Reposted by TipsySkinTipsySkin @tipsyskin.bsky.social · 09/09/2026Pegtember diary 05: ------ Today's nipples status: Hyper Sensitive. At some point I ended up dry humping the floor while feeling my dildo/plug move up and down against my prostate. Became a moaning mess. 2 dry orgasm. Finished with TWO ruined orgasm. To really drain my balls. 131
TipsySkin @tipsyskin.bsky.social · 09/09/2026Unfortunately, I have some work coming up. So no time to train my ass like a good little slut for a few days :( Will be posting pictures and some clips that have been piling up in the mean time tho :) 011
TipsySkin @tipsyskin.bsky.social · 09/09/2026Pegtember diary 05: ------ Today's nipples status: Hyper Sensitive. At some point I ended up dry humping the floor while feeling my dildo/plug move up and down against my prostate. Became a moaning mess. 2 dry orgasm. Finished with TWO ruined orgasm. To really drain my balls. 131
TipsySkin @tipsyskin.bsky.social · 08/09/2026Need a womb tattoo, but designed around prostate stimulation. 010
Reposted by TipsySkinGummyGhostGirl @gummyghostgirl.bsky.social · 07/09/2026Ooo someone looks a little pent up in that cage 💕🔐💕 7868147
TipsySkin @tipsyskin.bsky.social · 07/09/2026Pegtember diary 04: ------ Was crazy horny all morning and I wanted to take better pictures today. UNFORTUNATELY, I was too focus on camera stuff that I got huge performance anxiety. I.e. I couldn't even stay hard for it D: Still a nice ride, but not great. Got a few pics tho. 152
TipsySkin @tipsyskin.bsky.social · 07/09/2026I'm not kidding when I say I'm a faucet. This was me while I was setting up my lights and camera. It's not easy to be a leaking little hoe. 1103
TipsySkin @tipsyskin.bsky.social · 07/09/2026Day 4 of pegging myself to an hand free orgasm. Woke up so horny I put some girly clothes on right away. Issue was, I was leaking so much I couldn't take two steps without leaving a literal trail of precum on the floor... Had to put a condom on just to be able to walk around 🫠 040
TipsySkin @tipsyskin.bsky.social · 06/09/2026Finished myself with another ruined orgasm while I was riding my toy, but the way it was grinding against my prostate while my cum was pumping out felt like I was surfing on a small, warm, and soft orgasm. Took a warm bath with my collar afterward, felt so nice. 11/10 session 🫠 130