In the big city far away from home, where I visited and sexworked every month, I had a boyfriend named T who I would hook up with when I was in town. Sometimes when I was a lucky boy, he would surprise me by making the three hour or so trip to where I lived, waiting and standing at the door to my corner apartment as I made the final climb up the stairs coming home from work on a Friday afternoon.  

He was the first, and still some twenty-five years later, the only boy who ever truly owned my bi-heart and with whom I was intimate with on a private, personal relationship level. While I was not in the position or mental frame of mind in my life to commit to a monogamous or committed gay relationship (both he and I loved fucking women too much), I still loved my time spent with him, as we were free to see other people - in my case, other women, one of them we both shared. He knew about my sexwork, after all he had introduced me to my mistress and some of her clients, who later became my own. I knew this aspect of my life would be fleeting and passing, and in time I would have to let it all pass. But until that day came, which I placed on my 30th birthday, I would live every second until then to the fullest. 

In those days I was a closeted goth boy, and a closeted bisexual. In the town I lived, during the week I maintained my appearance as normal and straight on the rails as possible. However as soon as I got home on Fridays and through the threshold of my front door, off came the suit and on went the black make-up and goth clothes as I turned off my hetero-switch. Whenever I was around him, at my apartment, at his place, or at the clubs in his home city, I loved how he brought out a feminine side in me, he was so gentle and kind to me and made me feel comfortable with the bi-boy emotions that I had. I loved it whenever he bought me roses. If I was visiting him, I would be open with my bisexuality and we’d be walking around the gay neighborhood where he lived, holding one of his hands while my other held the red flowers he had just bought me. He made my heart flutter all the time, I loved holding and touching him, my arm around his waist in genuine affection.

While publicly (well, publicly in the confines of the social scene we lived in) I came across as the submissive one in the relationship and I felt comfortable playing that role, me being an androgynous crossdressing goth and him maintaining a buff male appearance, in the bedroom I often had to assert myself and take charge as he was shy and uncomfortable about the physical sexual side of our relationship. This was where I made him feel comfortable with himself, whether it was encouraging him when touching me between my legs, that there was nothing wrong to have my cock in his hands, or when I was gleefully sucking him off in bed and telling him it was okay what we were doing. When we fucked, I was always the bottom, from behind bent over, and I told him, ‘just imagine I’m your dreamgirl and she is letting you fuck her ass – don’t think I’m your boyfriend, but your girlfriend’. If he felt uneased, I’d sometimes ask him the name of a woman he’d like to sleep with, and then I’d answer to that name for the rest of the night. I did not mind being his fantasy fuck or him thinking of someone else, if it meant getting his hard cock inside me. He never put my penis in his mouth and I was fine with that, as I could get that action from casual women I knew on the side.

* * * * * * *

One night when I was staying with him, we went out to the club and hours of drinking and dancing got both of us horny. That night I had been wearing black shorts with fishnet tights underneath and doc martens boots along with a band t-shirt and a dogcollar – when we got back to his place, as soon as we got through the door we quickly ran to the bedroom, I pulled my shorts down to my ankles, and bending over on the bed, instructed him ‘fuck me, now. I don’t care just rip a hole in my tights and just go for it, boy’, as I was too impatient to bother untying my boots.

Hours later, after we had fucked and fell asleep still mostly clothed, my shorts still around my ankles, he woke me up, wanting to talk.  

‘You know, that was really good tonight. I liked fucking when you still had your tights and boots on.’

I replied, ‘Really? Nice, I’m glad, makes me happy to hear that.’ I leaned over to him, and put my hand on his face to caress him, ‘you know, boy, if you want we can do that more if that’s what you like doing and makes you feel good.’

I then joked, ‘just make sure I have a good supply of fishnets on hand, because this pair have been destroyed’, poking my fingers through them and ripping out some more holes over my leg.  

We didn’t discuss this any further that weekend and it wasn’t brought up when we talked on the phone between visits, and his enquiry that night slipped from my mind.

* * * * * * *

A month or so later, I’m heading up the stairs in my apartment and I see boyfriend standing at my door. I smiled welcomingly at him, as if the week of work stress had suddenly lifted off my mind. He’s standing there with a bouquet of red roses and a pink box with a big ribbon bow on it.

We get inside my door, close it behind us, and I lean him up against the wall, pecking him on the check. ‘Hey boy, so what’s all this for?’ I kissed him again, longer this time with some tongue, waiting for an answer, but he seemed all nervous or unsure. Finally, quietly he replied ‘I want to ask you if we could try something’ –‘sure – what is it boy?’

‘Do you remember when we fucked after going to the club?’ – ‘oh for sure yes I do!’, thinking back to that night causing a stir inside me.

‘Do you also remember back when we first started sleeping with each other and you told me to think of you as a girl when we fucked?’ – ‘yes’ I replied, now trying to figure out where this was going.

‘Well, I am wondering if you would dress up like a girl for me, one night, when we fuck?’ – I was instantly excited by what he was proposing – ‘Sure of course I can! And you know, I have a corset, skirts too, that I wear at the bars and clubs and elsewhere dancing, I can wear that in bed if you like. Heck, I’ve worn skirts around you here at home, so sure let’s do it!’

He then handed the pink box to me: ‘I bought something for you to wear as well, but I understand if you say no. I should have asked first but I saw them last week and got them. They’re something I never seen you wear and as far as I know, you don’t own in your closet.’

I gave him a silly grin, and tugged on one end of the bow, ‘well, let’s see what this is all about then, hey? By the way, this is such nice wrapping, not sure I want to ruin it’ I playfully giggled.

I undid the bow and slipped off the lid. Inside was some pink tissue paper which I dug through, pulling out a pair of black stiletto high heels. ‘Oh, now well this is interesting! And not what I was expecting’. I held them both up in my hands and twirled them around to get a better look. They appeared to be five or six inches high. ‘How high?’ I asked, holding up one of the shoes, and he replied ‘five – the saleswoman said start with five’. His answer didn’t register with me at the time, but later I would wonder what exactly had he told the shoe saleswoman that day when buying them.

I then looked at him, and he looked unsure and perhaps dejected that he maybe had crossed a boundary with me. I touched his chin, ‘hey boy, you want me to wear these for you? I will, if it makes you happy. I never tried to wear women’s shoes before, so no harm trying.’ I then noticed in the bottom of the shoebox a pair of thigh-high lace tights. He returned my earlier joke about ripped tights, ‘I got you these as well, so I won’t have to rip open any more of your fishnets!’ I laughed and smiled approvingly at him.

That evening before we went to bed, I showered and shaved my legs and body – something I already did but wanted to make sure I would be smooth all over for him. I then took the tights out of their package, sat down and slowly started to roll them up my leg. I loved the feel of them stretching over my legs as I pulled them up. They were opaque black, with a two inch band of lace along the top.

I then stood up and slipped my foot into the left shoe. I was surprised that boyfriend managed to figure out my foot-size, as those women’s size 11 fit perfectly. I slipped on the right heel, and immediately steadied myself against the wall in the bathroom, now standing up in these five-inch heels. After a couple minutes getting used to standing and walking in them, teetering less and less, and figuring out toe to heel, or heel to toe (I cannot recall now what it is) to walk about in them, I felt pretty confident I was not going to trip myself up. I grabbed my corset, wrapped it around my waist and latched myself tightly inside it.

I cautiously opened the door, called out to boyfriend, apprehensive but also coyly, ‘are you ready, hun?” and slowly, carefully, made my way clicking along the hardwood floors to my bedroom where he was waiting. In the hallway there was a full-length mirror, which I used for last minute checks before I headed out the door, be it work or the clubs or wherever, and now I stared at myself standing there, my cock hanging down hard, naked except for the corset, stockings, and heels. I twirled my legs around to get a look at how my legs and ass looked from being lifted by the heels. I really liked how they elevated my ass, making it feel even firmer.

‘Hmm not bad, at all’ I mused to myself as I turned around and made for the bedroom and my waiting boyfriend.

After I had walked in and stopped in the doorway, he stared back at me astonished. When he had bought those shoes, he was probably unsure what I would look like, standing there, in front of him, in them. I could tell from his wide eyes that he liked what he saw. Before I climbed on to the bed where he was sitting, I asked him, ‘So, what is my name for tonight?’ I liked what he chose and I moved towards him – from then on, we would always use that name to signal whenever he wanted me to dress up this way for him.

As we fucked that night, I was enthralled and arouse by how much I enjoyed my feet being arched and restricted in such an angled position, as well as the pressure on my feet whenever I bent over for him. Previously whenever we had sex, it was always from behind me – but tonight was a first for us, as he then threw me over on my back, climbed on top of me, grabbing each heel as he then spread my legs wide and back behind my head.

He felt so good as his manhood sunk inside of me, and seeing my boytoy happy brought a huge smile to my face. I put my hands on his shoulders and pulled him closer to me, kissing him, and then nibbling on his ear. I whispered, ‘thank you for this, thank you for making me feel so good tonight. I love being your girl-boy always’

Months later, once I got used to this role in bed, as well as coming to terms how this corresponded with my own sexual identity and feelings, I would surprise him in return by also wearing a black wig and black lipstick. At the fetish clothing store in the city he lived in, I bought a latex bra with inflated tits that I wore for him.

In time T and I would go our separate ways due to uncontrollable relocation situations that life throws at you, as well as the relationship strain that was inevitably fated to develop between us, but I continued to wear this persona that T had instilled in me, as I transformed it into my subsequent sexwork for the mistress. And sometimes when I was at home alone, and thought about him, I would slip into a skirt and heels for the rest of the night as I made dinner, or watched television on the couch, sometimes touching the heel point with my finger, thanking him silently for the gift he gave me that Friday afternoon.