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"Clare" - Chapter 7:- Dating Karen - "Dressing for a Meal”

"A nervous Clare prepares for her second date with Karen."

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Author's Notes

"It is 1987 and Clare is nervous about going on her second official date with Karen, mainly because Brenda is now organising it. Can Clare change her way of life and follow Brenda's instructions? Note: in the UK, OXO is a very popular brand of gravy cube."

Brenda's camera was clicking away. My butch lesbian girlfriend had not stopped chuckling since I had told her about last night’s date with Karen. Her amusement had been first spurred by the fact that I had told my second girlfriend all about my first, the ongoing relationship with Brenda.

Karen had taken that news surprisingly well.

However, it was what happened at the end of the date that had Brenda really chuckling and me standing here. It was something that Karen had insisted on for tonight’s date with her. It had to be arranged by Brenda and I needed to dress more like a man. It had been a surprising request or maybe a punishment for dating two women. I didn’t know.

But, here I am. Naked, except for a black, six-inch strap-on dildo, this is erect and wafting out in front of me. Brenda, her mood light and almost frivolous, she is making sure to photograph me from every angle.

However, standing here, I am confused and embarrassed. I asked myself, was this me?


*****


Earlier

With my brothers back at school and me still waiting to start college, I suddenly found that I had plenty of free time. I needed it, now I had two girlfriends.

I went over to Brenda’s in the early afternoon. I wanted to see her and tell her my pussy was now healed, but I also needed to report back to her about how my date with Karen went last night.

It was what I had been told to do.

However, Brenda got in first as she reminded me that this Friday, she would be taking me to “The Rainbow Bar.” It was the place where we first met. However, this time she wanted to show me off as her official girlfriend and introduce me to her friends.

“Could you stay over Friday night?” Brenda asked.

“Yes,” was my instant reply, my pussy now doing the talking, but in my head, I knew I would have to tell my mum I was staying at Karen’s or, more likely, Jaz’s. It would be yet another lie.

But it did remind me to mention the possible lesbian sex which Jaz wanted me to put on once again for her boyfriend, Rob, but only if David agreed I could do it

Brenda was delighted to hear that I had done such a thing. “Maybe you and Jaz can do a show for Tina and me, though as you both know, Tina doesn’t share her girlfriends.”

She paused.

“And since when did David get a vote, my dear?”

However, Brenda’s eyes gave the game away. She was teasing me.

I grinned and reminded her, “David will always have a vote.” This time I was determined to be a good girlfriend.

With that agreed, Brenda explained that she and Paula would be flying out to Madrid on Monday morning for a photoshoot. They wouldn’t be returning until Friday. She also told me that she made a good start on processing Sarah’s, David’s and my modelling shoot photos, but nothing was quite ready to see yet. I would have to wait until the weekend to see any of the results, and I made a mental note to tell Sarah during tomorrow’s phone call.

It was only then I had the chance to tell Brenda about last night’s date with Karen.

Once I had finished, she chuckled and stated. “You should have told me sooner, my dear.”

Then, in a wave of activity and laughter, Brenda fetched a new strap-on dildo from the ones she stored in the drawers in her dressing room. Then a flurry of phone calls, which resulted in the arrival of Paula to do my makeup and help dress me.

Brenda was giving me no choice. She was going to dress me like a man for tonight’s date, just like Karen had suggested. I was sure it wasn’t me, but any cries trying to dismiss this were quickly rebuffed as “nonsense.”

Brenda told me with a chuckle, “You need to try this at least once, my dear.”

So there I stood, posing. I had been washed and shaved. My hair had been pushed up under a flat cap, having put my foot down with both Brenda and Paula when it was suggested that I should have it cut short!

Neither David nor I would like that!

Other than the flat cap, the only item of clothing I wore was the black strap-on dildo. I just stood there, all but naked, modelling, Brenda clicking away.

 

Back to the Present

With Paula watching on, we were in Brenda’s private studio wearing a black six-inch strap-on dildo, my newly acquired fake cock. It was currently wafting around in front of me. My older bull girlfriend, with a camera in hand, was photographing me from every angle, telling me how good my piece looked on me. 

But I was confused and embarrassed. Was this really me?

Brenda had mentioned to me that I could switch between being a top or bottom lesbian. Maybe that was true, but I also knew I was not a lesbian. I certainly liked men and only ever wanted to be in a long-term relationship with one.

Brenda and Karen were nothing more than short-term sexual fun. Weren’t they? I mean, Brenda always gets bored with her girlfriends, and Karen, well, that was too new to judge.

“That’s good, Clare. That piece does suit you,” Brenda stated once again.

“Maybe I should use it on you,” I mumbled to myself, my butch girlfriend lost in taking photos to hear my words as I delivered the requested pose.    

“You know Clare; your name can be used for both boys and girls,” Brenda teased, as she adjusted my position and made sure my fake cock was erect.

“Yes,” I said. It was something I had been teased about in my distant past, a time I never wanted to go back to.

I said to Brenda. “When I was much younger, I was sometimes teased about it though I have never met any males with the name Clare.”

“They are mainly Americans, my dear. I only bring it up as a bit of fun. But if you ever make the permanent move to become a man, you will not have to change your name.”

Flash… Flash… Flash

Brenda took three quick photos, all capturing my reaction to her goading. They turned out to be superbly funny, but ones that I did not want anyone to see, especially David.

But it did give me a brief, almost unintentional thought; maybe it was possible to have two personas’ in the future, one female and one male. However, that original idea was quickly replaced with one that said that was ludicrous.

With the photo session over, Brenda told me she would keep everything safely stored, just in case I wanted to make some money in the future. She was once again hinting to me that they could be privately sold by Brenda to the Lesbian 100 Club. 

We said goodbye to Paula, who was off on her own date and walked back to Brenda’s dressing room. 

“Now, my dear,” she said. “I have some clothes here which will suit you, but first we need to fasten your piece in position. She unclipped the plastic cock, and I bit my lip as Brenda’s hand slid between my legs; the piece hanging there, the double hinge working well. Then she gave me a pair of baggy jeans, which I put on. There were no panties as I still wore the harness, the fake cock held in position in my right trouser leg.

“Remember that to piss, you need to take it off,” Brenda instructed, though that was fairly obvious.

I looked at my reflection in the mirror, something I often did. My top half was still naked, my nipples hard, pointing. They were telling the world, despite what I said, that I was turned on.

Brenda beamed, and I gasped, as from my waist down, I looked just like her. I needed some of me, so I put on the red stilettos I had purchased from Karen’s shop. My desperate action made Brenda laugh, but I felt better. The shoes had that familiar feeling.

Next, Brenda handed me a black lace bustier. Its breast cups nothing more than a thin black mesh. They were as near as damn transparent, my areolas and hard nipples showing clearly through. The lower part of the bustier stopped just above my belly button, but it had four straps hanging down. Brenda clipped them onto my strap-on harness.

It was then I realised my girlfriend had planned well ahead. Before even I was aware of going on a date dressed, more like a man.

The lace ribbon that ran down the garment back, Brenda tightened, which raised my breasts and made them look at least one size bigger. The two shoulder straps were then adjusted.

“I can’t wear this,” I complained to Brenda. “It’s see-through. I will be arrested.”

Brenda chuckled and handed me a large, white, shiny blouse. It felt like silk, and it partially obscured what I was wearing, though my nipples were still just visible. I still felt like I was on show.

“Don’t worry, my dear, you not going anywhere too public.”

As I suspected she might do, Brenda had arranged my date.   

“I have a driver and a car all booked, so you can have a drink,” Brenda grinned. “And you are both booked into Club o-X-o. It is a private member’s club.”

I had never heard of it. Brenda handed me a membership card, an envelope, a fake I.D. and one hundred and twenty pounds in cash, all in ten-pound notes.

“Club OXO,” I remarked while looking at the card. “Isn’t that a gravy stock cube?”

Brenda laughed.

“It is, my dear. But this club is very private, slightly off the radar, if you know what I mean. It is an underground club strictly aimed at girls like us. The logo is meant to be very subtle, and it stands for Opulent and Obsessive.”

“But you must understand, Clare; the real name is only known to its selective members. You will appreciate why after your visit tonight. Make sure Karen is aware you will not be home before midnight. The club only opens at ten, Wednesday to Saturday.”

“So, what am I meant to do before then, dressed like this?”

Brenda laughed again.

“Don’t worry, Clare, you are not going to be arrested. Donna, your driver, will look after you tonight. She will be here a little early. But the plan is to pick your submissive girlfriend up at seven. Then take you both somewhere very private, where you will not be disturbed, and you can have a romantic meal.”

“Remember, you're in charge tonight. Drive the conversation, especially as you wearing this.” Brenda grabbed my piece and squeezed it. “I promise you, my dear, it is going to be very private, and Karen will thank you for it.”

I eyed Brenda suspiciously. “So, I need to be twenty-one to be a member of club OXO?”

“Yes, and it is o-X-o. You now have an I.D. to say you are that age and also a membership card. Remember, you are a fully paid-up member for the next twelve months. You can go there any time you want to, Wednesdays to Fridays; you don’t need me.”

“What about Karen? She is only seventeen.”

“Don’t worry, she is with you. Guests only have to be eighteen, which makes her close enough. There is something else. I know the owner well. Just give the note I gave you to the lady at the door. I promise you there will be no issues getting in.”

I looked at the envelope. It was sealed and had Millie written on it.

“Don’t worry, my dear, the note just says to let you in. It has my signature, so there will not be a problem.”

I looked at Brenda, then at the money. “I can’t take all this. I should pay my way.”

“Nonsense, my dear. The club is expensive. It will be free for you to get in, but you have to pay twenty pounds for non-members like Karen.”

“I want you to have this experience. Just stay an hour or two, and enjoy it. Donna, your driver, will take you and Karen home. Tonight is all about new experiences, enjoying your girlfriend's company, and I guess it is part of growing up.” 

I looked at everything once again. The money, the membership card, the I.D. and the note, and I thanked Brenda with a kiss. I am normally fiercely independent, but tonight I sort of liked the idea of being spoiled.

Once again, Brenda took me through to her studio, though this time with no resistance from me. There, she spent another thirty minutes photographing me. By the end, I had sort of forgotten that I had on under my white blouse and in my jeans. My clothing had been on and off so many times it had become very natural.

At the end of the session, I thanked Brenda. I then made a phone call to Karen to tell her the new arrangements and then a phone call to my mum saying I did not need her car tonight. We were trying a new club in town, and I might be a little late home.

It was nice for once to tell her the truth and not a little lie. Though there was no doubt she would have been shocked by what I was wearing and the sort of private club I would be attending tonight. However, there was one thing we both had in common. Just like me, my mum would have called the club OXO after the stock cube.


*****


With everything in place and an hour to kill, Brenda and I sat there chatting and drinking a glass of champagne. It was a drink I could get used to.

My flat cap had gone. My hair was now in a ponytail, and as we talked, I realised every item of clothing I wore had been bought by Brenda. It was a strange feeling, as with my mum's help, I had been buying my own clothes since I was fourteen and I told Brenda just that.

She smiled at me, then mentioned that I might need to get used to it. Then she produced, with a grin, a beautiful silver anklet. It was made up of three chains; the top one had Brenda’s name on it, the middle one mine and the lowest Karen’s. It wasn’t as subtle as the o-X-o membership card, but I liked it and understood it. Brenda fastened it around my right ankle, though it was somewhat hidden by my jeans.   

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It wasn’t long before the door buzzer went, and Brenda let in a lady dressed in a light grey old-fashioned chauffeur uniform. Complete with a gold braided jacket, driver's cap and britches. I tried my best not to laugh, but she had dressed so typically Brenda, over the top.

But in a way, the chauffeur and I had both dressed for Brenda; it was my girlfriend’s way, having people dress the part like we were playing roles within her unique world.

Brenda introduced me to Donna, our driver, and another of her list of ever-expanding lesbian friends. It was explained to me that she occasionally drove Brenda to events in one of her special cars, especially ones in town. She was talking about London.

Donna was a lesbian. Brenda made that very clear in her unique way, her exact words, “Donna likes to fuck other girls.”

Our driver was attractive, mid-thirties and had dark short hair, a medium build and brown eyes. Though, at five foot two, maybe a little shorter than girls, which I was naturally attracted to.

With seven o’clock fast approaching, we all went down to see this special car. Brenda had told me it was a short limousine and one of four cars she had garaged; the others were a gold Bentley, a red Ferrari, and a yellow Volkswagen minibus. The last one was kept purely for nostalgia.

What she did not tell me was the short limousine was bright violet and had blue lights under it, which Donna turned on and then off. I giggled. The car was clearly like Brenda: overstated, unique.

Inside, it was more of the same: two bench seats, a table, and a bar with a bottle of champagne on it. Towards the front, a bed just behind the driver's privacy screen and those blue lights seemed to be everywhere as they ran around the ceiling, the bar and the table. With its dark, smoked windows and the blue lighting, it felt like a mini palace.

I squealed in delight, as I didn’t know what to say, as I felt like Cinderella going to the ball. Yet, in reality, I was the girl dressed like a man, going on a second date to two places that I knew almost nothing about.

I really didn’t know what to say to Brenda, so I thanked her with a kiss.

Then she showed me something about the car which I had never seen before. You could only get into the back of it from the kerbside. To do that, it had two doors on the same side, and they opened just like French doors, and they could be locked in the open position.

Brenda chuckled at my inquisitive expression. “Have fun, my dear, and I will want to hear all about it,” she said as she passed me a glass full of champagne.

I gently kissed her as Donna looked on before I slipped carefully into the rear bench seat and giggled, my appearance all but forgotten. I had never been in a limousine before, or in a car that could light up.

Brenda poked her head in and reminded me, “Donna will look after you both.” Then whispered, “Don’t forget to tip her and give her a little treat.”

She then winked at me; I wasn’t sure what she meant by a little treat.

“We chat tomorrow,” and with that, I was off.


*****


Donna and I chatted as we made the fifteen-minute drive into the city’s dock area. It was where Karen lived. As she drove, I explained to her that Karen was my second girlfriend and that I also had a boyfriend, so technically, I was bisexual. But our chauffeur seemed well briefed by Brenda, and nothing I said seemed to surprise her, which made me wonder if she had seen this all before. 

Karen and I had arranged to meet in a social club car park, which was just down the road from her home. What I hadn’t told her was I was going to turn up in a bright violet limo, but at least the undercar lights were off; it still being light outside.

As we pulled up, I noticed Karen gawping at the car, unaware I was inside. I opened the window and shouted to her. My girlfriend’s expression told me that she couldn’t believe I had turned up in such an extravagant vehicle, and in truth, neither could I.

With Karen more interested in the car, it was only as she got into the back with me that she realised what I was wearing. She started to giggle and then kissed me.

“Hi, you look lovely,” she whispered, then kissed me once again before my girlfriend scanned my body. She seemed to like what she saw.  

“You look lovely, too,” I giggled. She really did.

Karen was wearing a very short black dress, this one cut tighter and shorter than the one last night, and it extenuated her figure. A black jacket covered her shoulders, and knowing that we were going to a club later, her makeup was also a little heavier. She had on a pair of black high heels, but what surprised me was that they were even higher than mine!

It turned out that, just like me, my girlfriend loved her high-heeled shoes.

But there was something I needed to do, and my hand travelled down to Karen’s thigh. As it did so, I grinned at her, having wanted to do this last night before she pushed me away. Then, Karen had told me that I had to wait until tomorrow night; till now. My fingers moved under her dress and found the top of her knickers.

My smile got wider, and Karen gasped as my fingers slid lower and into her panties. There, they confirmed what she had mentioned last night. She did have a ginger minge. 

With Karen panting, I withdrew my fingers and passed her a glass of champagne. She sipped it and then asked me if I had dressed like that for her.

I replied that I had, but once Brenda heard what you had requested, I had been left with little choice.

Karan put a hand on my crutch and felt my piece.

“Just checking,” she explained, and then whispered, “Not that I have ever felt one of these before.”

That caused me to giggle; I didn’t say anything, knowing I had touched quite a few.

I was feeling relaxed, and I enjoyed Karen checking me out. It hadn’t felt strange at all, though maybe it was the wine beginning to have an effect.

We snuggled close. I was feeling less apprehensive about what the night had in store for us, which was just as well. As I realised, the car hadn’t moved, and Donna was watching us both make out in the back seat. I tried not to blush; I knew she had been watching my actions. But there was part of me that enjoyed that thrill, as long as it was not in a photo.

Donna smiled and told us that she had to make one phone call to check everything was ready. As she spoke, her eyes flicked from me to my girlfriend’s legs, and it was clear she liked what she saw.

The car had a phone, which our chauffeur used to call our destination. It was the first time I had ever seen one outside films and the telly. Karen and I just snuggled up, drank our champagne, and listened to the conversation. It soon became clear everything was in order, and that we would be at our secret destination in around fifteen minutes.

With that, Donna closed the privacy screen, and we glided away, turning east, away from my and Brenda’s homes. We were going to an area of the city that I didn’t know so well.

The journey gave me time to tell Karen all about Brenda and what had happened since our date last night. Once I finished, I proudly showed her the silver anklet. Karen noticed that it had her name on it. She liked it, and said she wanted one too!

Then, I clarified its meaning.

“Brenda sometimes calls me a lipstick lesbian or a femme…” I went on to explain Brenda’s interpretation of our relationship. That according to her rules, I was meant to be submissive to her, and she was dominant to me. Though, as I said it, I wasn’t sure that would ever happen. 

“So, Karen,” I said as I finished talking about Brenda. “That is why she put her name above mine on the anklet. She was saying that she is my top, and I am her bottom; that I am meant to follow her rules.”

Karen giggled and then again scrutinised the anklet, her fingers touching her name on it.

“So am I meant to be submissive to you, Clare?” Karen questioned, her name being on the bottom chain. She then giggled and swallowed the rest of her champagne. I sensed Karen wasn’t entirely against being submissive, but was that what I wanted?

“Let’s see where tonight goes,” I suggested, not feeling like trying to be dominant to Karen, or submissive to Brenda. All I wanted was to find the real me.

My comment, or maybe the champagne, had us both giggling. But I believed that switching, as Brenda put it, to become more of a butch lesbian was not really me. At best, it was something to be kept in the bedroom or for special occasions like tonight.

I looked out of the car window. We were still in the southeast quarter of the city, but now the sea was close to us on the right. The dockyards and its line of regimented cranes were now left far behind. We headed into the suburbs, and to a place where the wealthier people lived. The river estuary and its container ships would soon be replaced by pebbly beaches and leisure boats.

Across the estuary’s water, and only a mile away, was the pub, “The Anchorage.” It was where David had taken me only two days ago. It felt longer, but seeing the water made me think about him and our date.

I wondered what he was up to. Wednesday was the only night he didn’t see Sarah or me. Instead, he went to football training even though he was no longer part of the team. He had given up playing soccer so he could spend more time with me and Sarah. That thought made me feel guilty. Football had been his thing.

I asked myself why anyone would give up something to be with me, a girl who slept around and was not faithful. I had even told him that we needed to have an open relationship so I could sexually experiment with other women, and yet, he still wanted me.

As I watched the water drift past, I felt Karen’s hand on my leg. She was craving a little attention. I had been neglecting her, caught up in my reverie.

I turned, smiled and kissed her, then, with a giggle, slid in between her open legs. If I had my strap-on clipped in place, it would have been the perfect position to fuck her. She looked at me as if surprised I was there. I grinned and then kissed her again, this time more forcefully. I felt my pussy moisten as Karen started to pant from my more aggressive attention.

Maybe Brenda was right; I was Karan’s top, and she, my bottom.

“My mum and gran are organising my eighteenth birthday party, though I am not meant to know,” Karen stated as we broke apart. “I want you to come as my girlfriend.”  

“I like that, but I won’t dress like this.”

“Why?” Karen giggled. I sensed she knew the answer and was now teasing me. 

“Because it's not me!” I exclaimed.

Are you sure?

I wasn’t Brenda… But I did admit to myself there was a certain thrill with the thought of having a cock between my legs and fucking another girl with it. The rest felt nothing more than dressing for a part in a play.

I stared at Karen.

“Look, I want to go to your eighteenth birthday party dressed as me, a girl. This really isn’t me. I have dressed like this for mainly you, but also for Brenda… I think it is part of a game she is playing or, as she puts it, my lesbian education.”

Karen kissed me to shut me up!

“I know it isn’t you, silly. It was sweet you getting dressed up for me.”

She paused.  

“Look, Clare, I wanted you to dress like this to prove you wanted to be with me. It was sort of a test, and you can put that bit down to be part of your lesbian education.”

Karen giggled. “I did not expect nor do I want you to wear a fake cock all the time, though it has a certain charm.”

“Let’s be honest with each other. You are in love with another. You are also going to be sleeping around, where I am just starting to find the sort of relationship I want in the future. Though I know I am a lesbian, I want children and deep in here…” Karen tapped her head. “There are a couple of brain cells that want to try sex with a man, as I know that would have to happen if I want a family.”

I didn’t expect her to say that. It was unexpected, and I didn’t bother mentioning you could be inseminated in other ways.

I chose to look out of the car window once again, and I noticed we were climbing. We must nearly be there.

“Clare, I don’t care about Brenda. She might be fun, a passing phase, and for me, she can be a friend. Let’s carry on with our relationship. I like you, and most of all, I have chosen you to be the first person I want to be sexual with. That must mean something.”

“So, you don’t mind what I wear? I can just be myself,” I said, feeling that my mind was now a lot clearer. I had a vision of where a relationship could go with Karen, somewhere beyond just good sex.

“Exactly, but I do want you to take my virginity like I said last night, using a strap-on. I want you to do it on my eighteenth birthday, October 6th.”

I nodded and agreed.

“Before that, I need to meet Brenda and your parents and, perhaps hardest of all, tell my parents that I am gay. Maybe I should do that at the party, get it over and done in one go. You do understand, don’t you?”

I did, but not the part about coming out at her eighteenth birthday party. I thought that would be a disaster, and I told Karen just that. Then I backed it up with a kiss. It was only as we broke apart that I realised we had stopped, and Donna was opening the car's twin doors.

We looked out. Karen and I just gasped, then grinned.

Brenda had excelled herself.

Authors Note:- All characters engaged in sexual acts are 18+  ©2024 wxt55uk. This story may not be reproduced in any manner, without the express permission of the author.

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