As I turned my key in Brenda’s front door lock, I felt nervous—really nervous—and that was so unlike me. Today was October 6th, 1987, the day of my femme girlfriend’s eighteenth birthday. It was also the day Karen wanted me to take her virginity, but only if I dressed like a man, and I mean really dressed like one, not just pinning my hair back and easing into a pair of jeans.
During our last conversation on the subject, Karen made it very clear. She wanted her deflowering to take place on her eighteenth birthday at Brenda’s apartment. That made sense, as we didn’t have anywhere else comfortable and close to go, and I certainly could not afford a hotel.
But there were also two conditions.
The first one is that I must dress like a man. This I had done before. However, this time, Karen insisted that I had to do it properly, which meant short hair and less makeup. I gasped when I realised that my natural, long red, brown, and blonde locks would have to come off.
For the first time, we argued. I reminded her that she was meant to be my femme and submissive to me!
However, it was the last request that I found the most odd. Karen wanted me to wear a man’s military uniform. She didn’t care what type it was as long as it looked smart and had a few medal ribbons on it. She later reminded me that she had a thing about women in uniforms.
Karen made it quite clear that if I didn’t commit to doing this for her, then she would find someone else to be her first. I frowned as we continued to disagree. I told her that my hair was part of me; it helped define who I was and that David would be upset if I cut it!
My so-called submissive girlfriend’s touch had me eventually giving in, and then, with an evil smile, she told me that I would find a way to make it happen. Though unsaid, I suspected that dressing up and having short hair was all part of a punishment for my failing to commit to a monogamous relationship with Karen.
So here I was, arriving at Brenda’s hours early. Just so I have time to get ready and hopefully meet my younger girlfriend’s aspirations.
Karen and I had now been ‘dating’ for nine weeks, and I had been trying to give it a real go and make it work. I had even reduced seeing David and Brenda to just one day a week so I could spend most of my free time with Karen. I liked her, but I was not ready to be exclusive like she wanted.
The subject of what type of relationship we had was becoming a bit of an impasse. Karen wanted exclusivity, at least with women. She seemed to like David and didn’t mind me seeing him, which I found a little strange.
But I have insisted that our relationship should remain an open one. It was too early to think differently, and I had no plans to stop seeing and sleeping with other women.
The other thing that was making me nervous was tonight’s eighteenth birthday party. None of Karen’s family knew that she and I were in a relationship. Actually, none of them knew that she was gay.
Other than her best friend, Shana, she had not told anyone about her sexuality. Karen had kept it secret and had been waiting until she turned eighteen and legally became an adult to tell her mum. This was something she planned to do later in the week.
“Hi Paula,” I said as I announced myself and walked into Brenda’s apartment. As well as being Brenda’s Personal Assistant and part-time lover, Paula was a professional make-up artist, and she was there to help get me ready.
“Where is Brenda?”
“She’s in the lab working on a project and will soon be with us,” Paula replied with a hint of a French accent. “Until then, I have been instructed to get you ready.”
I followed Paula to the other end of Brenda’s huge penthouse apartment, which had been designed and built to suit her flamboyant and exuberant tastes. We walked down the corridor, past the kitchen and the multitude of colour-themed bedrooms. Including Brenda’s, there were nine of them, each decorated in their own unique way.
Brenda was my top, my older butch lesbian girlfriend, though, despite me telling her that it was old-fashioned, she insisted on calling herself a bull dyke. However, when I compared her to other butch lesbians, like her best friend Tina, I didn’t see it. With Brenda, there was softness and femininity, which I liked, even though she insisted on wearing a plastic fake cock inside her trousers.
At the end of the bedroom corridor, we turned left and entered the large chill-out area. It was a place filled with chairs and settees; it was a spot where people could relax and talk. Finally, we turned right and went through the security door into Brenda’s private photography studio. It was a place where guests were not allowed, an area where my girlfriend could photograph her subjects in complete privacy.
With Brenda still not in sight, I walked across the studio, taking in the detritus of past photo shoots and thinking I must ask my girlfriend about the story behind that large pink teddy bear that sat on a shelf and overlooked proceedings.
We turned right once again and walked into the studio's large makeup and changing room. It had a bathroom in it.
“Strip and shower,” Paula barked, her French accent suddenly gone. “Nous avons besoin de temps, beaucoup de temps,” she suddenly said, as if I knew what that meant!
I turned, stripped, shaved, and showered quickly, knowing the longer I thought about it, the more nervous I would get.
Brenda was there when I came out of the shower.
"Hello, my dear,” she said before she kissed me. “Are you ready for this?” she then asked, her eyes hungry and scanning down my naked body.
“I guess” was all I could muster as I slipped on a dressing gown and sat at the makeup table, the mirror reflecting my current girly features. I then looked at my hair; I had told Karen that I would have it cut short. It was something I was now deeply regretting.
“Brenda, it’s just my hair,” I desperately said. “I don’t want it cut and shaved short, how about if we only cut half of its length?”
“I believe Karen wants the sides shaved,” Brenda remarked. “We can keep the top longer,” she grinned.
That wasn’t very helpful, though I noticed she seemed to be enjoying herself at my expense.
Paula held up some clippers. “I will need to cut your hair first before I use these.”
“Why does Karen want you to have short hair?” Brenda asked with a smirk, which gave me the feeling she might already know.
“Punishment,” I replied, now wondering why I had agreed to have it cut, though I knew. It was my own fault; my pussy was so aroused I had gotten caught up in the moment being keen to please my femme girlfriend.
“Punishment?” Brenda and Paula questioned simultaneously. Both were clearly enjoying themselves at my expense.
“Yes, punishment, because I continue to see other women... As you both know, she wants me to be exclusive.” Then, clutching at straws, I said. “But it's your fault, Brenda. You wanted me to have a second girlfriend, and now look where it has gotten me.”
“My dear, I think your cunt had more to do with it than me. I know you, Clare. It is one of your most endearing attributes—the inability to say no when your juices are flowing.”
Paula and Brenda laughed, though to me, this time it sounded more like a cackle.
I took my long, reddish hair in my fingers and remembered back to Wednesday night when Karen and I were making out in my mother’s car. She was fingering me, my body responding as we kissed. I had been close, moaning, my head stuck in a cloud fuelled by sexual urges and a whirlwind of impure thoughts. For fuck’s sake, I had not been thinking straight when I said I would cut my hair!
“Is there another way?” I asked as I looked hopefully at Brenda and then Paula, who now had a pair of scissors in her hand.
“I do not want my hair cut short!” I exclaimed. I was thinking about how long it would take to grow again and, more importantly, that David would hate it!
Then I felt fingers in my hair, and I waited for the worst, but all I heard was cackling.
“Clare, my dear, we are not going to cut your hair. There is no punishment. Karen called me and told me she had been teasing you, but I also wondered if she meant enough to you to go through with it. I think we now know the answer.”
I started laughing, relieved, though I also wanted to scream and nudge both Brenda and Paula.
“I agreed to play along with the rouse, as it was fucking good entertainment.”
Paula agreed; the scissors were now gone.
For the next hour, I just sat there as Paula folded and pinned my hair up until all of it was sitting neatly on top of my head. She then put a strange type of net over it, which felt funny. She explained that it was a skull cap often used in the movie industry. On the upper side of it was short brunette hair.
Paula blended the skull cap in to match my skin and then redid my makeup. However, unlike in the past, when she made me look like a man, she kept my feminine features, telling me that this time I needed to look and be myself and not a character from some stage show.
I was now in the hands of the smiling Brenda. In many ways, today was just as important to her as it was to me. I was her project. Not one of her seventeen official girlfriends that had come before me had a second girlfriend, and only a couple had a boyfriend. I had both. She often told me that I was special or unique, though I didn’t see it that way.
Until Brenda, I had always thought I was a femme. It had been my butch girlfriend who had told me that I could switch to being a top. That is why she insisted on me dating Karen, and in doing so, I had come to realise that my older girlfriend might be right. However, privately, I thought it may be because I was more of a slut, it was a word I didn’t mind calling myself.
With Karen not arriving until two, we had plenty of time to finish my transformation into looking more like a man in uniform. We disappeared into Brenda’s dressing room. There on a hanger was a khaki army officer's uniform, complete with a set of medal ribbons. It was exactly what Karen had requested, and I thanked Brenda.
I also purchased two small gifts for Karen, which were gift-wrapped in their boxes. I was going to give these to her later, in private.
Brenda warmly looked at me and smiled, then said, “It’s the moment you've been waiting for.”
I wasn’t sure they were the right words, but I knew what she meant. My thoughts were reinforced when she got out of one of the drawers and got out two unopened white boxes. I knew they contained the two black fake cocks, which, six weeks ago, I had been measured up for.
Unlike the day, black strap-on, which I had vowed never to wear again outside the bedroom, these were serious dildos. They were custom-made by Brenda’s supplier to meet individual needs, each costing her well over a thousand pounds.
With a chuckle, Brenda opened the first box. Inside was a large, black fake cock. It was almost as large as the biggest one in my girlfriend’s collection. I looked at Brenda, thinking there was no way I could use it on Karen to take her virginity.
It seemed Brenda had read my mind. “Don’t worry, Clare, this one is not for today. It is for those future dates with those older lesbians who, as you know, are lined up waiting to go out with you.”
I knew Brenda had a long list of lesbian ladies who were looking for a date with me. At the top of the list was touchy-feely Helen. She was a lesbian friend of my bull girlfriend who had the habit of touching you as she spoke, and then there was Hazel, a hermaphrodite, yet she identified as a lesbian. She scared me and yet fascinated me.
However, I had decided that I would be cheating on David if I slept with her. He had given me the freedom to explore my sexuality, but on one condition, I could only sleep with other women.
I was not interested in most of the ladies on my girlfriend's date list. They were not my type, and I had emphasised to Brenda that it would be up to me to decide with whom I had sex, Brenda’s rules or not.
We had come to an agreement that, at the moment, it was all about Karen, and Brenda’s rules four and five were on hold. I had told my older girlfriend that she couldn’t ask me to date Karen seriously and then sleep around on her. She is not like you or me; she believes in monogamy. It was clear that Brenda hadn’t thought of that.
However, what Brenda didn’t know was that I had a private, short list of three ladies. It was headed by Millie, a dance teacher and fetish club manager who had the most perfect bottom. Then there was Linda, a married lady with whom I had a clandestine quickie in the Rainbow Bar ladies.
Finally, there was a young blonde, Debbie, who was hitting on me at college, though so far I had resisted. Unlike me, she had not come out as gay. It seemed she didn’t know how to. Instead, she had latched onto me, and we had become friends, though not once had her sexuality been mentioned.
We turned to the second white container, and I felt my pussy moisten.
Brenda passed the case to me: “Clare, it’s yours; treasure it.”
I opened the lid, and inside was the hand-crafted tool. Its smooth black skin had a gleam to it. To me, it looked just like what I suspected an erect black cock would look like, though I had never seen one in the flesh.
“My dear, why did you choose that colour?” Brenda asked. “You could have had one that matches your skin pigment.”
Brenda had many fake cocks, or pieces, as she called them—over fifty of them. I had counted. They came in different colours, shapes, and sizes. But that was not all. Some had bumps on them, and the textures ranged from hard to soft, smooth to rough. Others squirted, and then there were a whole series of anal versions. Each one slipped neatly into Brenda’s harness. She had informed me that she intended to fuck me with each and every one of them.
