It was something of an understatement, after several months of lockdown, to say I needed a haircut. I had been growing it before, but it was definitely long now, and messy. And altogether too masculine.
I started to fantasize, and look at pictures, and ask for opinions on crossdressing web forums. I dream of having a style that could be made to look reasonably acceptable in my vanilla daytime life, but also look hot and feminine when I wanted to explore. It is ironic that I would describe my vanilla life as ‘daytime’, seeing as that is precisely when I do my exploring and play with my femme side.
OK, time for a short back story, and a description of ‘exploring and playing’. I’m a completely ordinary person, if a little sensitive, and cursed with too much imagination, and time on my hands to indulge it. I have a platonic relationship with a wonderful, though stressed and menopausal wife. I am also a closet sissy bitch.
Now, this doesn’t actually require a femme hairstyle. I have a selection of wigs that look reasonably convincing, with eyeshadow and mascara, lip gloss and blusher, silicone breast forms, short skirts, stockings and heels. I love glamour and femininity; indeed, following the demise of any kind of sexual relationship with my wife, I’ve committed to feminise myself to keep this connection alive. Becoming the woman for me includes doing the things women do, especially the kind of women that appeal to me. I love to be fucked in basques, suspenders, heels, jewelry and Chanel No5, or slutty clubwear on my knees in a slutty club. Feeling a woman’s lingerie brushing against you feels wonderful; from the inside, clinging to one’s shaved and moisturised skin, it feels amazing. But I get a special thrill going out in public.
Dressing to go out in public is a different matter to dressing to appeal to a niche market in a CD club. Curly blonde wigs, huge boobs, false eyelashes and french maid outfits get you the right kind of attention in that context (‘I like my trannies to look like trannies’, said one dominant guy as he enthusiastically fucked my mouth), but not necessarily on a market town high street. I dream of being androgynous. I love boyish girls with short hair and feminine boys. I’m just about slim enough to explore that look without attracting too many critical eyes.
I have a definite scenario and look in mind, and keep coming back to it. I’d ideally look like a woman from a distance but as I’m not pretty enough to be a girl up close, I would still have to look stylish and confident. I have most of the items already – slightly flared faded jeans, short ankle boots with a 3″ heel, skinny vest top, a shoulder bag (ostensibly a ‘man bag’) and mirror aviator shades. I need to buy a short, baby pink hoodie. Of course, I’ll be wearing black bra, panties and holdups underneath, and I have some D cup breastforms which fill the bra nicely. I have worn this look on several occasions, almost exclusively at home, with a short, blonde wig. But the right kind of haircut could really make the difference.
I’d finish off the style with clear nail varnish, lipgloss and mascara, hoop earrings and a pretty velvet choker. It may seem far fetched that, despite my absolute depraved, trashy behaviour with loads of men, the thing I most fantasise about is to dress as described, and sit on a park bench in a public area, light a cigarette and smoke in full view of everyone.
Part of this is that I have a massive, obsessive attraction to women who smoke, but I have never smoked in my life – I associate smoking with cool, aloof girls, so it’s the ultimate expression of femininity for me. I recently bought cigarettes and a lighter, and have had a few attempts at smoking, but I have to be dressed as a woman to even contemplate it, which hopefully means I won’t develop a habit!
I had a hairdresser’s in mind, in a nearby town where I didn’t have to worry about a friend of a friend being in the next chair as I asked for the style I wanted, and I intended to case the joint; however, finding it empty on a Tuesday morning, with the only occupants being one bored-looking hairdresser and her phone, I walked straight in. She was maybe late 20s – early 30s, tatooed and pierced with heavy eye makeup and platinum blonde hair. She looked quite stern, initially, but had an attractive voice and a friendly manner.
She brushed my overgrown mop vigorously, this way and that. “OK, what are we doing?”
“Err… OK… can you do it nice and short at the back, but layer the sides… leave the fringe long…”
She looked a little surprised, but I had prepared for the moment, with a couple of pictures on my phone. I would show her the first and gauge reaction before showing the next couple. “Here…”
The first pic was a split screen, showing a handsome young guy from the front and a very cute girl from the side, with the same cut. She had a good look, smiling. “So it’s like a unisex cut… I can get the volume at the crown, lift it…” she shaped my hair with her hands and I started to feel more confident. I showed her the next couple of pictures – both girls.
She smiled again, seemingly understanding the vibe. “It’s a pretty style.” I felt myself stir and was reminded of the sheer lace boy shorts under my jeans. “It’s going to really suit you.”
We decided on a wet cut and she shampooed my hair, which I hadn’t experienced for several years. Women really treat themselves at the hairdresser’s and rightly so; why not feel special once every few weeks?
She patted my hair semi-dry and led me to the chair, selecting her scissors, combs, thinners. She started to cut, chatting. “So where are you going, first, with your new look?”
I knew what she was asking, I knew she knew. “Have you heard of a club called Angels?”
She didn’t look surprised. “The mill… on the London Road? That’s the…”
I dutifully finished the sentence she had deliberately left hanging. “…private club. Yes.” I paused then added “I like to go to crossdressing nights.”
She clipped away, unfazed. “I bet you’ll look really cute with this style.”
I blushed and she responded with a smile, teasing me. “You’re quite feminine. I can picture you in a little sequined dress.”
A grin escaped me, as did a surge of pre-ejaculate. What aspiring sissy didn’t dream of a situation like this?
She carried on. “You’ll have to tell me sometime, about all the things you get up to at Angels…” She frowned, concentrating on getting the sides even and the parting in the right place. “About here?”
This was the perfect time, I decided, for the bombshell; the opportunity I’d hoped for. I produced my phone once again, finding the picture. “I dunno… Like this…”
The picture showed an extremely pretty, lithe young woman with her strawberry-blonde hair in a perfect pixie style, and a huge, distended foot-long black cock in her mouth. She studied the pic. Did I detect just the merest hint of amusement on her lips? She never acknowledged the elephant’s trunk in the room. “Yes, the parting is a bit higher… and it looks slightly longer on the fringe side… like this…” She primped, adding volume at the crown. This was now a full-on womens’ hairstyle, and I wondered if I could make it look even semi-masculine. “Do you mind it being longer on this side?”
“No, I really like the way the girl in the picture looks.”
“Yes,” she replied, “so do I.” She turned and bent down, rummaging in a drawer, and her short ribbed top rode up her lower back slightly, giving me plenty of opportunity to see a small tattoo at the base of her spine, A ‘Q’ with a black playing card spade symbol inside. Otherwise known as a queen of spades tattoo – the internationally recognised symbol of a woman dedicated to sex exclusively with black men.
My face must have been a picture as she turned back to me with hair dryer and she beamed, quickly regaining control as she blow-dried my hair. We made eye contact and shared a wordless joke as she deliberately styled me to look as feminine as possible. She grinned a silent ‘what?’ and I grinned back, shrugging gently. All finished, she produced a mirror and showed me the back, so girlish and prissy, long at the crown and really short and shaped into the neck. I imagined a velvet choker and gold earrings, and almost had to physically restrain myself from masturbating.
She finished up and the salon fell silent. I looked so cute. I wanted to ask her to come to the park with me, sit with me while I ‘smoke a cigarette like a sexy girl’ – I wanted to use those exact words. It would be wonderful to sit there with her, chatting and both smoking, but she took the gown off me and I stood up. I felt a pang of disappointment as I saw her reach into a tiny leather rucksack and produce her cigarettes and lighter, probably about to go on a break. Damn my reserve!
I paid and headed for the door, and she gave me a gentle slap on the buttock. “So, you going to take me to Angels, sometime, babe?”
We both grinned. “I would really like that, honey.”
“Hit me up on Insta.” She blew me a kiss as I left the salon, and as I felt the cool breeze gently ruffle my crown I flicked my long fringe from my eyes.