Cross-dressing sissy expanding his anal horizons with ever-larger dildos and vibrators‌

My dick might be tiny, but my dildos certainly aren’t!

Transvestite in black lingerie

Sissy Anal Training

I took my anal play to a whole new level last night during a three-hour session of cross-dressing, porn watching and dildo training. I put on a black lingerie set that had I originally bought for my ex wife as a birthday present. It was one of the many underwear sets that she never showed any interest in wearing for me, but at least it got some usage last night. I teamed it with some black stockings and a pair of strappy silver high heel shoes, then I took a Max Strength Golden Root hard-on pill and waited for my knickers to start to bulge. Then as soon as I was hard and horny, I put a gay porn DVD in the DVD player, then took out one of my biggest dildos and shoved it deep inside my arse.

I’ve been practicing with ever-larger dildos in the past few months; and my anus is really enjoying the ride.  If I use enough anal lube, then I can now easily handle a 9-inch length and I’m steadily getting used to bigger girths, as well, all of which adds to the sweet sensations I feel in my arsehole. I can remember how my wife always used to look at my tiny penis and try to pretend that size didn’t matter, but now that I’m the one on the receiving end, I know only too well that extra inches means extra fun. There’s just something really special about being jammed to the brim with a rock-hard phallus; and my penis always throbs when I’m working a big dildo back and forth inside my back passage.

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Transvestite Dildo Play

Of course, dildos are fantastic and help deliver some incredibly intense and creamy climaxes, but nothing can beat the real thing – and I’m getting hornier and hornier for cock all the time. I’ve made two visits to toilet blocks with lingerie on under my male clothes this week, but not had any luck in getting laid. I’ve also been out to a dogging spot; but there was nothing happening there either. But that’s the trouble with hunting for dick in public places. Sometimes you get lucky and sometimes you don’t. It won’t stop me from keeping on trying, though!

And if I go to a place and nothing happens, then I can always come back home and play by myself. And I’m getting used to lubing up my anal tract now and steering a dildo inside my ring. I’ll normally stand one upright on a chair, so I can bounce up and down to my heart’s content. I also have one with a suction cup that can be fixed to a wall, which means I can back onto it and pretend I’m being shafted from behind. It’s a Loving Joy Mr Big realistic dildo that you can purchase online from SexToysUK. I bought the 7.5-incher originally, but I’ve just placed an order for the 10-incher today. And I simply cannot wait to sit down on that!

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My top tips for taking ever-increasing sizes of dildo up your arse‌

If you think your dick delivers sexual kicks, then you just wait till you discover what your anus can do!

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Anal Training for Men

Very few of my masturbation sessions don’t involve the use of a dildo these days. I was 46-years-old when I first stuffed a dildo up my anus and was immediately blown away by how exciting it was – and I regret not having discovered much earlier just how much fun can be had from practicing anal penetration. There are pleasure sensors throughout the sphincter that respond amazingly well to any kind of stimulation. What’s more, poking around up there always seems to deliver an exceptionally creamy climax. I guess it’ something to do with milking the prostate gland – and how it stimulates a really thick flow of cum.

Like most men, I was nervous the first time I took a dildo up my bum. But it’s really nothing to worry about – just as long as you follow a few simple steps before you start. Firstly, if you’re worried about the shit element, then a good dump beforehand is a wise idea. And if you’re OCD about cleanliness, then you can use douches and enemas kits to have a really thorough cleanse before you sit down on something throbbing and hard. But me, I’m not too bothered about a little bit of dirtiness, so my first step is to use some ID Lube to lubricate both my arsehole and the toy I’m using. I will also take a sex stimulant – normally Hard Man pills for anal play – and maybe also open a room aroma like Liquid Gold. All these things help get me excited but also help relax the anal tract, after which I’ll be ready to choose my weapon and thrust it where the sun don’t shine.

Transvestite using sex toy

Anal Lubricants

Obviously all anal virgins are best off starting with a smaller dildo, rather than leaping straight in with a 15-inch black bad boy! And be gentle with yourself – just push it in with the merest hint of force and then give your anus plenty of time to get used to the feel of being jammed full of cock. I wouldn’t recommend you immediately just start ramming it in and out of your ring, but instead just slowly ease it back and forth and let your sphincter pulse around the shaft and head. And if it feels too tight, then don’t be afraid to pull the dildo out and add some extra lube. Or if it feels too small, then get out a bigger dildo – and slowly work your way up in length and girth.

In six months I’ve gone from using tiny toys to being able to handle a nine-inch length. But size isn’t everything and what I like the most is the look and feel of the toy I’m sticking inside my body. For me, it has to be realistic-looking, so I can get a fantasy in my head about how I’m bending over and dropping my knickers for a real man who will fuck me hard. And it’s pervy, I know, but in the more intense moments, I also start to fantasise that my ex wife is in the room watching me getting fucked by a stud. Because I would love her to see the change in me since she’s left. Because she still thinks I’m a bedroom bore! Yes, she has no idea that I am now a cross-dressing, anal-loving, sex-mad freak who is forever hard thanks to sex pills and forever shoving big, thick cocks up his arse!

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‌Taking my orgasms to a whole new level with the help of an anal dildo‌

No man has ever experienced a true climax till he’s cum with a dildo deep up his arse!

Cross-dressing sissy uses anal dildo

Experimenting with Anal

Very quickly after my wife left home, I went from being a normal man with zero perversions to a kinky slut who was up for pretty much anything. Not only had I shamelessly sniffed and worn my own daughter’s dirty knickers, but the next thing I did was purchase a realistic-looking dildo and began to experiment with sucking and sitting on cock! I had used sex toys on my wife in the past – she used to make me do it when my dick didn’t work – and I had always been shocked by just how much pleasure she received from having one pumping in and out of her pussy. And she had always chosen enormous ones – perhaps to shame me for having such a tiny prick. But as an anal virgin, I went smaller to start with and purchased a six-inch dildo with sensible girth.

I dressed up in a bra, thong and stockings for my first session of anal experimentation. I also took a Max Strength Golden Root to get me hard, then I sprayed my arsehole with Pjur Backdoor Relaxing Spray and smeared my middle finger with some ID Lube. I had started purchasing most of my products from an online store catering to gay and bisexual men, as they seemed to be the best equipped for anything to do with anal play. And I remember being incredibly anxious about the prospect of losing my anal cherry, so I was determined to have all the proper products at hand. You see, I’d never had anything up my anus before and I was really scared it would hurt – or maybe even make me shit myself.

Shameless pervert cross-dressing

Stimulating the Prostate

It was something I was determined to do, though, because it felt dirty and sleazy and lots of fun. Also, I think a part of me wanted to do things that I knew would have really shocked my ex wife – and what could have been more shocking than the thought of me toying my own anus while dressed in girlie lingerie! And so, once the Golden Root had got my dick nice and happy, I pressed my middle finger against my ring, took a great big breath and then poked that finger deep inside. And I heard myself let out a tiny little gasp as it inched its way between my anal walls, but more importantly, I felt this nice internal spasm that made my cock bulge even more. So, yes, my arsehole seemed to like it! And yes, my penis seemed to like it, too!

And so happy that I could handle my finger, I then took out the dildo and smeared it with a lot more ID Lube. I wanted pleasure, not pain, so I probably overdid the lubrication, but it certainly made it much more easier than I’d expected for my virgin arsehole to accommodate the dildo’s entire six-inch length. I then started to ease the cock back and forward, repeatedly stimulating my prostate gland, which I quickly realised had just as many pleasure sensors as my helmet did – and maybe more! And as I picked up speed and fucked myself harder, I felt these intense spasms in the pit of my stomach. It was a completely overwhelming sexual sensation that seemed to take over my entire body – and even though I wasn’t even touching my prick, I felt the beginnings of a climax starting to happen.

Can you believe that? In a matter of weeks, I’d gone from being a man who couldn’t get it up for love nor money to a guy who could orgasm completely hands-free. Okay, I’d had to do some preparation – a bit of cross-dressing, a hard-on pill, some anal relaxant and a rubbery cock – but those things had combined to deliver a climax of the most incredible sensual force. My anus was pulsing and clenching and throbbing around that dildo’s juicy shaft; and I found myself properly bending over double from the intensity of the feelings in my guts. In fact, the sensations in my anus were completely overwhelming the climactic throbbing of my rock-hard dick – and I knew right away that this was just the beginning of my anal explorations. Yes, I knew I’d be needing a larger dildo. And also, perhaps, a real man’s dick…


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