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Sissy Maid Allyson

The tumblr of a middle-aged sissy living in north Kent England, who is struggling with finding her true self, concentrating on maids, nurses and school girls and oh so wonderful bondage..

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hellopinkpill:

satinsissy247:

femininesentiment:

ilovesuckintrannycock:

karriecd:

jennachaste:

Since I still get asked a lot on how to do it, I’ll try to sum it up quickly for you guys :)

DISCLAIMER: I am not a doctor and I realize that not everybody is built the same. What works for me does not necessarily have to work for you. I also realize that there’s a difference between milking your prostate and having an anal orgasm. Short explanation: Milking feels nice and ends with ejaculation while an anal orgasm explodes inside your body and doesn’t always mean you eject semen.

STEP 1

Chastity. You don’t need a device to lock your penis away (even though I think it’s fucking awesome). But you shouldn’t jerk off for at least 10 days if it’s your first time. That’ll help, also when you’re having moral doubts for whatever reason. 

STEP 2

Hygiene. Give yourself an enema and make sure that you’re really clean. And make sure that ass is completely hairless. Objects entering your anus will pull on your hair down there and it will not feel nice.

STEP 3

Choose the right weapon. For me, a realistic dildo works the best. And it’s shape is very important. See this picture?

The parts that I circled is the most important ones and are going to rub against your prostate. That’s right. Don’t poke your prostate like you’re trying to stab it. Firmly scrape against it with that part of the glans instead. Forget about your own penis. Don’t even touch it. I mean it. Only one cock matters right now a nd it’s not the one attached to your body.

STEP 4

Relax. There is absolutely no need to hurry. You don’t have any other place to go right now. It’s very important that you explore your ass gently with lots of lube until penetration does not feel uncomfortable at all. Fuck yourself for a while and don’t think about how much time already passed. Watch some anal porn while you’re at it and try to visualize how you might cum from getting fucked in the ass. Remember that awesome sex is mostly happening in your brain.

STEP 5

The right position. I have no explanation for this. But when I started with regular anal masturbation, doggy style worked the best for me to cum from getting fucked. But every person is different.

STEP 6

Don’t be a lazy fuck. Some people play with their asses for hours and expect a miracle to happen. That’s the wrong idea, in my opinion. You gotta work that cock. Like this:

Well I realize that this little animation might look a bit silly. But that’s actually what I usually do. While my sphincter stays mostly relaxed during my fuck sessions, I flex the inner part of my ass against the cock that’s pounding it. 

STEP 8

Practice. It took me over a year to learn this. And when I first fucked the cum out of my balls anally I was playing with myself for more than an hour. But today it only takes me a few minutes, when I’m in the right mood. Don’t get discouraged if it doesn’t seem to work. Give your ass a few days rest and try again. And remember that no part of this should ever hurt. If it hurts you’re doing it wrong and you should stop before you injure yourself. Seriously.

Good luck and happy assturbating!

this is amazing! thanks for the advice!

Excellent advice for all gurls trying to have anal sissy gasm’s! Took me a fair while to get it sorted as well! But never fail now! Practice makes prefect ladies! ❤️❤️

Indeed!

💖 Love!

Great advice.

Thanks!!

🤔

(via mistressaliceinbondageland)

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My good friend Delilah Knotty posing for my other friend @sandragibbonstv.

Maid Monday

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That’s it princess, take it deep and swallow it all.

Like me, you’ve been dressing in stockings and women’s clothes, and painting your face with makeup for years as you’ve lost battle after battle trying to be a man you knew deep down you were not, and could never be.

This is the final defeat. The abject surrender. The final act of emasculation that confirms you as a faggot for life.

Whe he’s finished you can have a good cry in my arms. I know how it feels.

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Video clip: The new housemate (1:56)
See the full video at Rubbersisters.

Rubbersisters are great!!!

(via sissynessa)

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Video clip: Sissy training (1:02)
See the full video at The English Mansion.com

What would be better- a couple of hours of this with no orgasm, or an orgasm 2 minutes into a couple of hours of this…?

Super amazing video

Id love for my Beautiful Mistress Kittyn to do this to me

Her sissy cumdumpster slut Peaches

Wow. That’s fucking hot!!!!💦💦💦💦💦💦💦💦💦

(via sissysnow)

humiliationfantasy:
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(via maidsophia)

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Country side shoot with Billy Bleat. Feel free to share and repost :)

You are so cute.

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These heels all but insisted I take them out of the cupboard today =D

Patreon covered my laser hair removal treatments again this month, which means I get to drop another set of little videos for y’all (next weekend? we shall see!) - the voting on there has yet to decide whether it’ll be butt or penis play, it’s neck and neck right now!

I can’t say enough how grateful and in spired I am by the support. It genuinely is the difference between stopping because of the time sink of constant shaving and being able to take pictures whenever I have free time, so it’s those fine folks who make this smut possible =D

(via timb040)

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Now who out there wishes to be Mommy Milly’s submissive sissy maid?? And what does the word servitude mean to YOU??

Always remember who is in charge!


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SIssies, Bimbos, Gooners, Littles, Submissives, Mini-Giantess, Big Boobs

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Rachel Solo a slightly exotic look and a super gorgeous face

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We love to look like a woman… We love to feel like a woman… We love to act like a woman… And we love the taste of hot cum from your pussy or anywhere else…

How did you think a night out for your girly man was going to end? 😉