Flirting with coming out to my daughter and wanting to be exposed as a sissy to the world

Some of my girlie clothing and sexy lingerie is just too damn pretty not to be seen!

Transvestite steals daughter's dress

Sissy Exposure

I’m sure I’m not the only cross-dressing sissy who gets all dolled up in the privacy of his own home and thinks: ‘What a waste that there’s no one here to see how cute I look right now!’ I’m spending more and more time on my transformations now – doing full hair, nails and make-up almost every time – and I always wish a big strong man was there to appreciate the effort I’d made, as well as fantasising about my ex-wife seeing me fully feminised and playing with anal toys. But apart from online sissy exposure, the only time my feminine outfits ever get seen is when I drive out to toilet blocks to suck off strangers! But that takes a hell of a lot of nerve, so I only pluck up the courage every once in a while.


Sissy T-girl borrows daughter's cute prom dress

Coming out as T-girl

So, I’m mostly still pretty much stuck in the closet, although I have thought about coming out as a transvestite to my 19-year-old daughter (who stays at my place quite regularly). I’m not sure she needs to know that I often borrow her knickers (including her dirty ones) or that I’ve nicked a few of her dresses (including the purple prom dress in these pics), but I have a feeling she’d be okay with the general idea of me dressing up. And I wouldn’t be surprised if she’d be willing to help me with my nails and make-up, or even to go out clothes shopping with me. She’s a really great girl, and I almost told her the other night, but finding the words came really hard! I just couldn’t quite manage to blurt it out.

I think one thing that probably held me back was the chance that she’d be unable to keep the secret and would tell her mum. And while a part of me would love my ex-wife and her hunky new man to know I’m a cross-dressing sissy slut, another part of me is terrified about the prospect of opening up the closet door and never being able to shut it again.  But I guess that’s always the risk with coming out – once you’ve done it, there’s really no way of going back. But I know I cannot keep these sexy outfits hidden from the real world forever. And more and more, with each passing day, I have the desperate urge to be shown off as a girl.


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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.

Married man becomes sissy slut

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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The sweet humiliation of meeting my ex wife’s incredibly hunky new boyfriend‌

He’s taller than me, more muscular than me – and he’s undoubtedly far better hung than me!

Cross-dresser in lingerie

Transvestite Sissy Cuckold

According to my 19-year-old, my wife has had a couple of boyfriend since leaving me. Neither of those have been serious, though, but that’s all changed in the past few weeks when it seems like she’s fallen head over heels in lust with a guy who I got to meet last week. And I can see why she fell for him!  Cos, Jesus wept! He’s 6 foot 4, with a bodybuilder’s physique and he almost broke my arm when he shook my hand. He was towering over me like some masculine god and I actually felt quite weak at the knees. We’re talking about a genuine macho stud – and he rather appealed to the simpering sissy side of me.

In fact, a part of me wanted to let him know that I was wearing knickers and stockings under my suit when we met. Or to maybe suggest he comes inside and fucks my ex wife in front of me – or even for me to dress up in my girl clothes and for my ex wife and I to share him together. I haven’t always had cuckold fantasies, but when I was going through my three years of total impotence, the thought of my wife with another man was always strangely appealing to me. And now, having discovered she was setting up home with a proper hunk of beef, I found myself getting really horny at the thought of watching her in action with her real man lover!

British tranny in white lingerie

Limp-dicked Sissy Loser

But I was in a state of shock, in some ways. Even though my daughter had already warned me about how tall, muscled and manly my ex wife’s new partner was, I wasn’t expecting such a crushing blow to what remains of my masculinity. I mean, he completely dwarfed me in every way – and I had a damn good look at the front of his jeans and could tell he would have dwarfed me in the bedroom, too. Not that that’s particularly difficult, of course! Even with the help of a hard-on pill, I’m lucky to push beyond four-inches in length. But this guy – I’m guessing eight or nine at full-length. And I bet he doesn’t need impotence cures to be able to get a hard-on each night like I do.

No, the whole thing was really rather humiliating when you think about it. They’d only come to pick up my daughter, but I invited them in for a coffee and had to watch them hold hands, put their arms round each other – and just generally behaving like two teenage lovers. And there was pathetic, little me, wearing women’s lingerie under my male clothes and not really knowing quite what to say. And worst of all, was knowing that as soon as they left, I’d be swallowing a Max Strength Golden Root sex pill and jerking off while imaging the two of them having sex together. So, it’s no wonder my ex wife left me, really. Because a woman needs a real man – not a limp-dicked sissy like me.

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A shopping spree for poppers, pills and other things that turn me on‌

You just can’t beat browsing the magazines and DVDs in a good, old-fashioned sex shop.

Impotent cross-dressing sissy

Shopping for Sex Supplements

I still do nearly all my shopping offline and have a particular fondness for the look and feel of a proper British sex shop. We used to have a couple here in Ipswich, but now we just have a really good branch of Pulse & Cocktails, but it’s not much of a drive to get to Secrets in Bury St Edmunds or the Private Shops in Southend, Peterborough or Cambridge. I could spend hours in these places checking out the top shelf magazines and fetish mags or choosing some hardcore DVDs to watch. I also stock up on sex pills when I’m there and room aromas like Liquid Gold. And I occasionally buy myself a sex toy, too, because I like to be able to see how big the length and girth of a dildo is before I take it home, lube it up and shove it up my arse.

I have mates – grown men – who tell me they’re terrified about going into sex shops, but I’ve never once felt nervous in any of these places. The staff are always really friendly and they couldn’t give a shit what stock you buy. I’ve gone into the Cambridge Private Shop a lot in the past few months and bought MILF DVDs, lesbian DVDs, plus a couple of gay mags and some tranny magazines, as well as a big black dildo and a realistic white rubber cock. And the staff don’t think it’s weird at all that I’m trying all these different fetishes. They’re just totally matter-of-fact about it.

Divorced man explores cross-dressing

Wigs for Cross-dressing

The other thing I love about shopping in sex shops is that you get to buy real products like DVDs and print mags. Because I still prefer to look at porn the old ways – and I love the feel of a mag in my hands or the excitement of popping a DVD into the player and pressing ‘Play’. I also currently have this recurring fantasy about reading a dirty magazine with another man. I’d have popped a sex pill well-in-advance, and as we turned the pages together, our dicks would get all big and stiff. And so we’d pleasure each other manually while enjoying the pictures of the naked girlies on the pages. Then we’d spill our loads all over the mag and make the pages stick together with our spunk.

So most of my sex life is offline based, although I’m not a total luddite. The one thing I’ve found to be lacking in most sex shops is good stuff for cross-dressers, so I bought my fake tits and new wig online from Nice’n’Naughty and I buy lots of my lingerie from Sex Toys UK. Oh, and did you spot the new wig in the pictures? I’m experimenting a bit more with cross-dressing at the moment and have now worn a wig and some lipstick for the first time. And who knows where that might lead?

Discuss knicker sniffing and pantie preferences with sexy British housewives…

Knickers and panties phone sex

From an impotent sissy cuckold to a cross-dressing slut with sex on the brain‌

Further thoughts on my complete change in attitude to anything to do with sex.

Sissy flashers knickers

Cures for Impotence

In the darkest days of my three year spell of total impotence, I never really thought about sex at all. I knew my dick didn’t want to get hard and I had absolutely no interest in fucking my wife, so I just sort of accepted life as a eunuch. You see, I was suddenly a man without any sexual desire at all. I couldn’t get aroused by adult magazines or dirty DVDs or even by passing a sexy woman in the street. Nothing seemed to excite me. And my dick was forever flaccid and limp.

Of course, the change came after my wife left me and I started taking hard-on pills – more often than not Max Strength Golden Root. And the results were instant! The sheer excitement of seeing my dick standing upright for the first time in months made me start to see the world in a whole new light. And suddenly I was able to read top shelf mags again and watch endless porn films late into the night. I was also able to visit massage parlours and get jerked to a climax by some lovely escorts. And once again I could look at a sexy woman in the street; and even though I knew she was well out of my league, I could still feel that tingle in my crotch that told me there was some life down there.

Getting hard thanks to impotence pills

Enhancing Sexual Confidence

Of course, in my case, the thrill of being hard again also led me to start exploring new kinks, but even if I’d never got into cross-dressing and sticking dildos up my bottom, then I still would have been really grateful for this sexual reawakening. Because the most important thing for me is not that I can now get hard and climax again. It’s more that I now feel completely and utterly alive again. Because my cock isn’t dead now, like it was for all those years, which in turn made me feel sort of dead inside. Because when a man can’t get a hard-on that’s pretty much how he feels. It takes away all his confidence and makes him feel embarrassed and ashamed.

But I have all my confidence back now – and have no shame at all about my years of limp-dicked cuckoldry. And I no longer even feel upset or ashamed that my wife cheated on me with two much more masculine men than me. Nor that I now like to put on corsets and stockings! And to sniff dirty knickers! And to experiment with guys! No, none of this feels embarrassing to me, because I love that I now think of sex all the time. It’s a fantastic thing to have on the brain, especially when compared to all those boring months of living like a monk.

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Dropping my girlie knickers in a public toilet to satisfy a real man‌

Being straight and fancying women doesn’t mean I can’t like having sex with men, as well…

Knicker flashing cross-dresser

Bi-curious Cross-dresser

About a month ago I decided to start wearing female lingerie underneath my male clothes all the time. I started out by just swapping my boxers shorts for knickers, but then got a bit more confident – and soon I was going to work or the shops with a corset and stockings, or maybe a bra, thong and suspender belt, underneath my suit. The only time I don’t do it these days is if I’m playing sport that day and will be getting changed in front of my mates. God, I can picture the looks on their faces – and imagine the wisecracks – if I was to drop my trousers and flash a pair of pink panties at them. I’d never hear the end of it!

Anyway, one of the advantages of wearing lingerie under my male clothes is that I can use it to seduce men in public toilets. As I’ve mentioned before, I’m mostly straight – but when I’m wearing pretty undies and stockings, I’m always open to being groped (and more) by a man! So, yesterday I found myself in a toilet block in a multi-storey car park. And it was a quiet one with very few people about. And this guy walked in – a tall, manly guy – and I just let my trousers fall to the floor, revealing a pair of black silk stockings and some slutty red knickers.

Married man in lingerie

Shameless Sissy Slut

Of course, the guy didn’t know how to react at first – and I did fear getting beaten up for a bit! But I’d already taken a hard-on pill and was starting to feel incredibly horny, so I asked if he wanted to see some more and then unbuttoned my shirt to expose a red basque. And the guy seemed quite excited by now, so I walked into a cubicle – and sure enough, he followed me in. Then he made me strip right down to my undies and started to kiss me and to grope my arse. In fact, his hands were running all over my body, really savouring the thrill of my lingerie-clad flesh.

Now unlike me, this guy was in no need of a Golden Max to get hard that day. He had quickly stiffened to an impressive length, so I dropped to my knees and swallowed his cock. I was keen to feel it inside my anus, so I was careful not to give him too much oral pleasure – then I stood back up, yanked my knickers down and let him ram his dick through my hole. And he fucked me like a man in a hurry – like a man who was terrified of being caught! So, it was all really hard and athletic and powerful – and it sparked all kinds of intense shivers in my arse. And never more so than in the magical moment when his purple cockhead started to throb and spew hot spunk inside my anal tract.

And I actually climaxed myself at that point – at the very same moment when his spunk spurted out. I’d been jerking myself off throughout the anal fucking; and it was feeling his climax that tipped me over the edge. And as a thick spray of jism shot out of my much, much smaller cock than his, I realised just how lucky I was to have discovered cross-dressing in lingerie. Because it’s amazing getting fucked like a woman gets fucked – and to see and feel things from a feminine point-of-view. And that’s why I know this won’t be the last time I’ll be standing in the gents with my knickers round my ankles. Because I’m really keen to explore much more of my bi side more – and I’m sure there’s plenty of masculine guys out there who’ll be more than willing to help.

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‌Exploring the reasons I turned from a typical horny man into an impotent, limp-dicked cuckold‌

What exactly were the reasons why I didn’t get a hard-on for over three years?

Sissy discusses male impotence

Cures for Impotence

Now that I have my hard-on back, I am quite open to thinking about the reasons why I lost it in the first place. But that wasn’t the case when the problem first arose, because my initial reaction to my failure to achieve an erection was to bottle up my feelings and pretend it wasn’t happening. I felt embarrassed, ashamed, humiliated and like a complete and utter failure of a man; and I certainly wasn’t up for talking about it or even writing about in a blog like this. I just didn’t want to face up to the truth or confront the issue in any way, but looking back, I can now see what the issues were.

Of course, ageing must have been part of the problem. I never had an issue getting an erection in my twenties – in fact, I often had one when I didn’t want one! And my early thirties were pretty horny, too, but things started to go into a gradual sexual decline for me during my late thirties and early forties. The first thing I noticed was that my recovery time after orgasm wasn’t what it once was – and that I couldn’t get two or three erections in a row. It was now a case of just one hard-on per day, and not only that, but I’d nearly always need to sleep off a climax. But that’s just typical of getting older – just as, in much the same way, it now takes me longer and longer to recover from my weekly game of 5-aside. Everything becomes just that little bit more of an effort and takes a bit more out of you.

Transvestite with low sex drive

Sex Enhancement Pills

So, I think ageing was the reason why my sexual powers were dwindling, but I don’t think it’s the cause of me losing my hards-on altogether. I think the cause of my descent into total impotence was a heart-to-heart I had with my wife when, after 16 years of marriage, she suddenly told me she wasn’t enjoying our lovemaking and that I wasn’t giving her any sexual satisfaction. Now I already knew I wasn’t much of a lover – my dick is only tiny and I’m hardly Mister Macho Stud – but it was still a big blow to my confidence to be told it so bluntly by someone I loved. And then six months later my confidence took another blow when my wife confessed to having an affair with a man from work. And then 16 months later, she had another affair. But could I even blame her? No, not when, by that stage, I hadn’t once been hard for her in nearly two years.

Of course, my sexual confidence was now at an all-time low due to all these various factors – and my poor, little dick just seemed to want to shrivel away and hide from all the embarrassment and shame. I mean, it certainly wasn’t getting hard for my cheating wife – or even for porn mags or hardcore DVDs. No, not even a tiny hint of stiffness – just permanent flaccidity. And I did begin to wonder if it would be that way forever, but then my wife left home and I hit rock bottom, which meant that the only way now was up. And so I started to actually think about my problems… and that’s what led to me finding some answers. And the main answer was to, first of all, accept that I was impotent – and then to go out and actually try the things that can cure a limp dick. And that’s how I wound up taking impotence pills.

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A serious sex enhancement pill that can stiffen even the most impotent of pricks‌

Hard Man Max Strength sex pills give me three rock-solid erections in a row…

Shamed sissy husband sucks dildo

Sex Pills For Impotent Men

Despite my newfound love of wearing women’s clothing and the odd toilet meet with some bi-curious guys, I still consider myself to be predominantly straight. I love looking at women in lingerie, fondling bosoms and licking women’s pussies, and now that I’ve got my erection back, I also love having a woman climb on top of me and ride my dick. But when it comes to sex products, I nearly always find myself buying from websites aimed at gay men. That’s partly because I started out buying toys and lube for anal play – and since gay men are known for loving anal, I figured they’d know all about the best products for bum fun. But around the same time, I also watched a couple of documentaries about gay sex saunas and the European gay holiday scene. And I realised then that gay men take their sex lives incredibly seriously. They want maximum fun, so if they like a product, then you can be sure it’s a really good one.

And that probably explains why Hard Man Max Strength is the most potent sex enhancement pill in the business. The name and the packaging suggest it’s aimed at gay men – the logo of the builder on the cover always makes me think of the Village People – and it sure does pack a serious punch. The first time I used it was one hell of an experience – only 25 minutes to achieve full stiffness, then a stonkingly hard erection that I jerked off for nearly two hours. But unlike with the other sex pills I’ve used, Hard Man Max Strength delivered a second hard-on within the hour. And after wanking that off and going to bed, I then woke up with a morning glory!

Knicker-wearing sissy's arse

Sexual Performance Enhancers

Now in my teens and twenties, I never once failed to wake up in the morning with a hard-on in my boxer shorts. But the early morning stiffness gradually disappeared over the course of my 20-year marriage, and so for Hard Man Max Strength to bring it back for me was a genuine shock and a really nice surprise. It also adds to my theory that these particular sex enhancement pills are quite a bit stronger than the others on the market. That’s why I only use them sparingly – say, if I’m planning to have a two-day session – and why I’d recommend getting medical advice if you’re on medication before using them.

Yes, these are fast-working pills that deliver a rock-solid erection and keep you feeling horny for days, so you can imagine how useful they’d be at a three-day gay orgy! So, no wonder so many gay men swear by them – and no wonder they’d been so useful in tackling my own impotence. Here’s how I rate them:

AVERAGE TIME TO WORK:  Under 30 minutes

STIFFNESS OF COCK: A stonkingly hard erection bulged out to maximum length (which in my case isn’t long, but still, it’s as long as I can get)!

LONGEST SESSION: Nearly 3 hours’ of prolonged masturbation

LIQUID OUTPUT: Put it this way… stock up on tissues!

RECOVERY TIME: Second hard-on within an hour of first climax, plus a third hard-on the next morning and a general feeling of horniness throughout the next day.

SIDE EFFECTS: A slight reddening of the face; and if anything, they get me a bit TOO sex-crazed.


WHERE TO BUY: Great value 4-pack available at esmale

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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!

Sissy gets hard-on thanks to sex pills

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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Enjoying a massage with a very happy ending on a business trip in Sheffield‌

It’s important to make the most of a night away on business – and that means knowing where the local massage parlours are!

Sissy male wanks in female clothes

Sex Enhancement Pills

I work in an office in the heart of Ipswich, but I get sent away on business at least once or twice a month. And even though it’s something that never once crossed my mind during my marriage, I now nearly always check out the massage parlour and escort scene wherever I’m going to be visiting. There are parlours here in Ipswich, of course, but they always feel too close to home, so it’s nice being sent somewhere where no one has a clue who I am. Then I don’t have to worry about being seen going in and out of the establishment, or of taking an escort back to my hotel room. Basically, I don’t have to worry about anything when I’m miles and miles away from home!

This month I was sent to Sheffield – a place that I’d heard was blessed with more than its fair share of massage parlours. I’d heard there were several based on Attercliffe Road, and so after taking a couple of Max Strength Golden Root, I wandered up and down the road and then chose the nicest-looking establishment. I was greeted by a really friendly lady who introduced me to two lovely girls – one a curvaceous blonde and the other a skinny brunette. I would have been happy to have been massaged by either of these ladies, but brunettes have always really done it for me. And so I picked my girl and then went into a nice, little room, took off my shirt and trousers and got a very relaxing and sensuous massage.

Anal play for sissy cross-dresser

Max Strength Golden Root

Now I had knickers on beneath my male clothes, but the girl didn’t seem to mind about that. We had a nice, little chat about my experiments with cross-dressing – and I even blabbered on a bit about my limp-dick problems with my wife. But there were no limp dick problems with this girl, because I’d taken a double dose of Golden Root hard-on pills to make sure I’d be rock-solid for my session. When you’re handing over hard-earned cash for a massage, then you really don’t want your dick to fail, so that’s the only time I ever double up! And thanks to the pills, it wasn’t very long before my knickers were totally bulging like mad! And they carried on bulging as the girl stroked my dick through my knickers, before pulling them down and giving me a tit wank followed by a few nice sucks and a manual finish.

All-in-all, I had a really lovely time with this girl, although I wouldn’t say I’m completely used to the idea of paying for sex. I know I’m not much of a catch, though, and the dating scene seems far too challenging at my age! Also, I’d hate to fall in love with a woman and for my dick to stop working, like it did with my wife, so right now escorts and massage parlours seem like the best way to fulfil my sexual needs. These girls are always easy on the eye, open to me cross-dressing and open to using sex toys on me. They also always wear sexy lingerie and stockings and suspenders. And not many women will do that for a man these days. But massage parlour girlies will!

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