This is a little story I wrote, before I started on a two-story set of serials. It introduces the reader to a place that appears in the following posts.
Marianne

The Flip Side

I didn’t get caught up in cross dressing until I was in my late teens. It was a slow, but inexorable process. I suppose it came about from my choice of work. I wasn’t good enough for university, so left school when I was sixteen.

I was born in Winchester at the turn of the new century and named Philip Anthony Jackson. My schooling was a very simple affair, seeing that the primary and secondary schools were less than a few minutes from where we lived, on Milverton Road. I was given a nickname early on, through school I was known to all as Flap, short for Flap Jack.

My first job was at the Fulflood Arms, a pub that was not much further from home than the schools were. There, I started as a general hand, helping out in the kitchens, unloading the beer trucks, cleaning the bar and the rooms when we closed. It was mindless, but it did pay enough for me to indulge in the one thing that I loved, buying records. I had a small record player with a CD player in it and I did have a small collection of CDs, but nothing beat the sound of vinyl.

The Arms had a Sunday special, the Vinyl Afternoons from one to seven, with a local guy bringing his turntables and boxes of discs. The pub also had some discs, and I would try to be near when they were being played. One Sunday, the turntables were there, but the guy wasn’t. About midday, the boss asked me if I would fill in, so I dashed home and came back with my own box of discs. That Sunday changed my life.

I took charge of the turntables and played my discs, the pubs discs, and the ones the customers had brought in. As the hours slipped by, I became adept and choosing the following tracks, even doing the backwards trick – with my own discs – of course. The owner of the turntables came in around six and sat with a drink as I worked. When the end of the session came around, the customers took their own discs to go home for Sunday dinner. He came over to me.

“Philip, my boy. You’re a natural with this. I’m at the end of my DJ career. I have to go into hospital next week. How would you like to buy the set up? It includes the turntables, a spare set, the amps and speakers, along with all the boxes of discs.”

“I would like that. How much would it cost?”

He named a figure which I thought was ridiculously low, so we shook on it. I negotiated with the publican to store the gear in-house and arranged to pick up more boxes of discs that he had, some turning out to be olden goldies. I continued working in the pub for another year, becoming DJ Flap on Sunday afternoons.

One day, there was a new face in the bar as I was working the turntables. At the end of the session, he came over as I was clearing up.

“Hey, you’re good. How would you like to work six evenings a week in my nightclub?”

It turned out that he was the owner of Popworld, in Southampton. The idea of being a full-time DJ was like a red rag to a bull. Two weeks later, I had left home and found a bed-sit on Graham Road, in Southampton. He helped me move my boxes to his nightclub, as he had all the rest of the gear in place. All I had at home was the turntables, amp and speakers.

I stayed at Popworld for over a year, working six nights a week. It was a good gig, and I saved my money, eating in-house as I had done while at the Arms. It was hot in the club for me as I pranced around behind the turntables. I spent most evenings in a sweaty tee and loose slacks. He already had a big selection of discs, so I had a lot to choose from. Towards the end of twenty-eighteen, I was offered another venue to play at.

This was one that I had heard about. It was called The Box and Edge, or just the Edge. It was a gay nightclub and was very popular. Popworld had been getting some poor reviews, so trade had dropped off a bit. The boss had been hinting that he was thinking of dropping my hours or dropping my rate, so somewhere else was like a lifeline. The only drawback was that there were posters and advertising for DJ Flap, so the owner slipped me a few quid if I didn’t use the name.

The Edge was a short walk from where I lived, and it took less than an hour for me to load my own boxes into the van that was sent for me. At the Edge, I was able to add all of the boxes of golden oldies, seeing the clientele were more likely to groove to older stuff. I had extended versions of Village People, along with others that Popworld thought old hat.

My time at The Edge was magical. I was reborn as DJ Phlip. The clientele were very forgiving and were happy with the older stuff. Around four in the morning, everyone was so wasted that having something to sing at the top of your voice had a lot of attraction. Most nights, around that time, I would kick off a disco hour with ‘Born to be Alive’. As time went on, I started emulating the fashions and got some lighter tees in softer fabrics, and even started wearing leggings. I looked a bit odd, but it was cooler, and I didn’t look as odd as some of the dancers. The place was open from ten to five in the morning, so I was home and in bed most of the day.

Of course, there were special nights for drag queens, so I was expected to look the part. I started as just a guy in a dress, but seeing how good some of the customers looked, I started to try to, at least, look like I was trying. Like I say, it was a slow process, but I began to feel cool and comfortable in a skirt while I was at work. So much so that on the drag evenings I would spend a couple of hours getting ready before I would walk to the club in a skirt or dress.

Before I started dressing there were already a few of the regulars who had become very chatty and bought me drinks. After I started turning up in a skirt, one of those became very friendly. Dan was a few years older than me, and a good-looking guy. He would often spend time dancing with the girls in the club but would often be near me as I worked. Sometimes, in the early hours, I would put on a very long disco disc, some went for more than ten minutes, and I would step out on the floor, and we’d dance.

It didn’t matter to the boss or the customers how I dressed. I would notice other pretty boys become pretty girls and I didn’t feel out of place. In the end, I was dressing as a girl most of the time and my hair had grown long enough to look right. Buying clothes had taken a bit of money, but I considered it well spent when I was able to go to op-shops as a woman and browse in the racks without being noticed.

Unfortunately, things took a turn for the worse when Covid hit us in twenty-twenty. The club had to close during the lockdowns, and I was able to get my boxes of discs taken back to my home. It was a trying time for a while, but it did pick up, as far as I was concerned.

I was searching the radio for something to listen to when I came across a station which was known as Voice FM. It was a community station, operating twenty-four seven, and I was amazed to find out that it operated out of the Youth Club on the corner of Graham Road. I walked there one Friday evening and spoke to the DJ, volunteering my services. I was wearing a dress that evening and gave my name as Phillipa. They knew of my time as DJ Phlip, so I was taken on board to do a nightly show of dance music, using my own discs. For the first time in my life, I was using my feminine voice whenever I spoke on air.

I started my shows with slower music, livening it up as the hours went by. Inside two weeks I started getting people calling in, and I had to learn how to talk to callers and play music at the same time. The hours weren’t bad, and I was usually in bed by midnight. Before the first lock-down was lifted, I was doing voice-overs for advertising and getting paid for it, recording the audio and couriering it to the customer.

I didn’t go back to The Edge when it reopened, staying with Voice and doing the extra paying work. Eventually, someone knocked on my door to ask me if I was interested in public speaking gigs, seeing that my voice had a sexy huskiness. That led to me taking on speaking engagements, like describing fashion shows, recording voice-overs for TV adverts, and the like. The outside work had to stop with further lockdowns, but the voice-over gigs remained. I had earned enough money to be able to record at home. I used my existing mixer and microphone and had picked up a unit that would record directly to CD or USB stick.

As far as I was concerned, life was cruising. I stayed in my female persona, happy to be able to pass in the street, as well as on-air. Unfortunately, my world was turned on its head by new technology. The station went to fully digital, and I took my boxes of records home. It was a new age, where you could run a radio station with a lap-top and an account with Spotify. Vinyl was yesterday’s old hat.

With time on my hands, I started going back to the Edge for a couple of hours an evening. About the fourth time, Dan was there and came up to me and hugged me like there was no tomorrow.

“Phillipa, I’ve really missed seeing you. They told me that you were doing shows on the radio, and I’ve heard a few adverts with your glorious voice. How are you?”

“I’ve been better, Dan. The radio gig has ended as my vinyl is no longer up to scratch.”

“Don’t worry, they will realise that it has an atmosphere that you don’t get with digital. It’s good for classics, as you can hear every note from every instrument, but dance music needs atmosphere. How are you for a job?”

“If I say that I’m between engagements, you’ll get the idea.”

“Would you like to come and work with me? I have a string of music and record shops along the coast, and I need someone to help me get the right stock. With your skills, you should fit in well.”

“I don’t have a car.”

“That’s all right. You can move in with me. I have a couple and I have plenty of room. What do you say?”

I looked him in the eye and my tongue wetted my bright red lips. He took the hint and pulled me to him, giving me my first kiss as a woman. In fact, I think that it may have been my first kiss as a person. Seeing that The Edge was a gay club, I had no doubt that Dan was gay, and, seeing how I was now dressed, so was I. We didn’t stay long, and he drove me to his house in one of the better suburbs. There, he took me to bed and taught me how to make another man happy.

The next day, we went to his warehouse, and we drove a van to my lodgings, loading up all my things. The records and equipment went back to the warehouse for storage. Me and my clothes went back to his house. After all that lifting and carrying, we both had a shower. Mind you, it could have been the extra session in bed that made us smelly. We had lunch and then we went back to the warehouse to put the van back.

There, he sat me in the office and showed me the extent of his empire, and I was given all the names of the suppliers and shop managers. From then on, we worked together, played together, and slept together. With my input, we brought the business into the current century and improved the sales. He had been right, as vinyl did make a comeback and we were able to stay ahead of the market.

As time passed, I suggested that he may be happy if I had the correct plumbing. We discussed it for a while. He had no desires to play with my penis, so agreed. I had the operation, recovered, changed my name and got all the right paperwork. That’s when we got married. I wore white and it was a glorious wedding, with us going to Paris for a week afterwards. He was now happier with two places to put his member, and I was happy whichever one he chose. We were in love and life was good, now that I was playing the flip side.

Marianne Gregory © 2025