jennachaste

jennachaste:

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I finally had a weekend for myself and of course I took the chance to finally get some more cocks! As it’s a Saturday night, I thought I’d get plenty at the glory holes. But I was totally wrong about that … The place was a fucking graveyard.

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But after quite some time a guy…

jennachaste

jennachaste:

Ladies and gentlemen, this is it. I finally did it! I lost my gay virginity!

I couldn’t take it anymore, so I got my ass off the bed, pushed my medium sized buttplug up my ass and went to a place with glory holes.
What happened:
- I blew an older man to orgasm and swallowed his load (so fucking…

Anonymous asked:

Hi Jenna! I've finally taken the plunge and allowed my Mistress to become my keyholder indefinitely while she trains me. I've only dabbled in self-control before now and never for more than 48 hours or so; how long would you recommend staying locked up for as a starting period, a week or something? I'm just concerned about safety, getting used to it, etc. Thanks!

My very first lockup was just 3 days. Then a week. Then 10 days. And so on. I can’t say how long you should be locked up since I don’t know what kind of device you’re using and what your habits are. Just take your time and get used to it. No need for a rush.

Anonymous asked:

I have super kinky fantasies but no way to fulfill them, including chastity. Having no partner for this self chastity would be fun, but I don't know where to start... Any ideas? Cost efficiency is important as I'm only a freshman in college, but effectivity is just as important! Sorry for the triple ask!!! Is there anything I can do to make it up?

It’s okay, don’t worry. The cheapest way to purchase a chastity device is on ebay (look for CB6000/s or Bon4 or Birdlock). Then slowly get into it by leaving the key in your room when you go to class or you go out. Just be safe. Don’t lose the keys and don’t get caught by the wrong people. Losing control might sound hot when you’re horny, but in real life things often look different. I wish you the best of luck! And don’t forget to send me some pics ;) Kisses, Jenna

pinksissychloe

pinksissychloe:

Sometimes you just need to be filled up, and this friend of mine is the perfect toy to do so. This one is currently my largest toy, and is 2” wide by 8” long. I still need to warm up a little for it, but there’s really nothing like being filled to the brim.

I took some follow up pics, but wasn’t that happy with them. So for the sake of professionalism, I suppose I’ll need to be filled up again and take some more. Life for a sissy can be so hard sometimes.

pinksissychloe

pinksissychloe:

This is the first in a (hopefully) series of posts showing off my toy collection, and what better way to start than with my very first toy. He might be the smallest in my collection, but there’s a reason I call him ‘Old Reliable’. With almost no warmup, I can have him slipped in and rubbing oh so deliciously against my prostate in no time at all. No other toy in my collection hits my sweets spots quite like this toy and even 20 minutes later I’m still leaking from my session with him. The nice thing about the size as well, is that it makes it really easy to pick the pace up and hammer all my sensitive spots. Remember folks, you don’t have to be big to make your sissy squeal, just make sure you know all her spots :)