tagTranssexuals & CrossdressersThe Fulfilment of Caroline Ch. 02

The Fulfilment of Caroline Ch. 02


Thank you to everyone who gave such lovely feed-back on Chapter 1. I must say I was surprised that my first effort received such positive comments. I hope you all enjoy Chapter 2.

Caroline has visited Lisa an on-line friend and made some life changing decisions. She has found a flat and a new female friend. She has also played out some BDSM fantasies and wants to explore more.

You really need to read Chapter 1 to get the full effect but I'm sure you will catch up if you don't. As in Chapter 1, there is sex but this is a love story first and foremost.

The aftermath

I awoke on Friday morning with Lisa at my side fast asleep. I felt that this was the most natural thing in the world. Lisa looked radiant in her nightie and almost had a smile on her face. I felt tightness in my chest as I looked at my lover and realized that I had fallen deeply in love. I gently got out of bed so as not to disturb Lisa, I filled the kettle and made coffee, Lisa stirred slightly at the noise but didn't wake. When the coffee was made I gently kissed my lover awake.

"Rise and shine sexy!" I said, "We have a busy day ahead"

"MMMMMM" moaned Lisa, "I was awake but I was re-living last night and didn't want it to end"

"Don't worry my pet; we will have lots more nights and days like that and better I'm sure"

We sat in bed, very close sipping our coffee.

"What's the plan today then?" asked Lisa.

"Well I want to have a drive in the car and we also need to go and see the café and I want to call in on Helen"

As I said this I saw a cloud wash over Lisa's face and then lighten, I realized that Lisa was still a little jealous. I would have to do something about this.

We showered and dressed smart casual for breakfast then out in the car for a tour of the area, me driving and Lisa navigating, there were some lovely areas and close links to motorways and commuter A roads to London and the south coast. I could see that this was an idea area to set up a business catering for Transvestites, with this size of catchment area there were bound to be plenty of potential customers.

At 11.00 o'clock, Lisa and I parked outside the café; we sat in the car for several minutes watching the front and the high street. There were several smart shops but not a lot of pedestrians or window shoppers. I thought about it and realized that passing trade was not going to be my main customer base.

We went into the shop and the owners showed us to the smaller private room which had been cleaned since my first visit and the tables set with fresh linen, clean cutlery and crockery. We were offered tea and coffee and asked if we wanted lunch. I declined lunch but we were served tea and coffee and scones. The owners presented all of their books and even at first glance the figures didn't look good. I still believed I had a decent plan and if everything went wrong I'd get my company to turn the place into flats. I asked the owners if they had a figure in mind.

"Well....we have about 20 years on the lease but it has been offered to us to buy for £5,000, we had the building valued for insurance last year at £275,000 and we think the goodwill and stock is worth about £15,000. What do you think?"

I said, "I will have a think, and come back to you later today, I need to look at other properties and possible options. I would need to re-vamp the place for my ideas which will add cost and there may be somewhere which would cost less overall."

"We are open to offers" they said with a clear pleading look in their eyes.

"I'll take the numbers and come back to you later today but in essence you want £295,000, how quick could we move if I agree?"

They both looked at me and I could see that they were tired out, weary with either the work or worry.

"We can be out I a month, we have a flat on the coast and we need to rest there"

I felt sorry for them but £300K was a lot of money.

"I'll get back by 4 o'clock; talk to you soon." And with that Lisa and I left.

We drove round to Helen's and asked her if she had time to come up to the flat over lunchtime for a chat. We got the papers and were looking them over when Helen came up. She looked at them and said.

"No wonder they want out!"

We looked at the local agent on the internet and decided that £300k was too expensive, especially as the goodwill didn't seem to exist. I decided that the building was worth £260 in its' current state and goodwill was worth £10k, add to that the lease cost of £5k I needed to find £275,000. I knew I could raise that.

Lisa and I went out shopping and called back at the Café and made our offer...blimey, there I was again "our offer" Lisa really was in my psyche. I told the owners they could let me know Monday. We went back to the hotel and Lisa looked sad, she had to go home that night but would be OK for our night out together on Friday. I remembered I had asked Helen so I asked Lisa if she minded if Helen went. Lisa's face clouded over again.

"Yes OK, I suppose she can come if you want." Lisa was almost petulant.

Lisa's education.

I needed to sort this out and quickly, Lisa was my lover, Helen was a true friend and I knew would be a friend to Lisa too if she could get past this jealousy.

"Remember I own you Bitch" I said.

Lisa immediately changed into her submissive self, eyes downcast.

"Look Lisa, I love you, I really love you, and I have found someone who I want to spend my life with. We have to get over your jealousy. What would happen if during our playtime as Mistress and Bitch I introduced others? It would be sex and pleasure and not love. Helen has been a real friend to me so far; I wouldn't have a flat or a potential business or be thinking of moving here without her. She wants to be our friend together and she wants to explore our lifestyle. She might even be our sex partner one day but please understand it's you and me always, you are the only reason I'm here."

Lisa looked up with tears in her eyes.

"Forgive me Mistress"

"Not Mistress now, I only said that so you would listen properly. It's me Caroline"

"Sorry Caroline, I love you too but I can't help feeling jealous of your other friends, I do like Helen, I do. I promise to accept her and try not to be jealous."

We kissed deeply and I slowly stripped her of her clothes, laid her on the bed and quickly stripped to join her. We made love gently but with huge passion, I sucked her clit and she sucked mine, we played with each other's pussies and I dove my tongue deep into her pussy, tasting the sweet musk and slightly acrid taste of her, I loved it, I lay on my back and asked Lisa to make love to me, not fuck me, make love to me. Lisa got the lube and lubed my pussy and opened me up gently with her fingers, she placed the head of her clit against my opening and pushed. There was no pain just a beautiful feeling; Lisa ploughed deeper until we were locked together hip to hip. I pulled Lisa down and we kissed deeply tongues fighting each other our passion building, Lisa gently started to withdraw and push back, gentle slow strokes, my legs locked around her waist and I pushed my bum back to meet each thrust. My own clit felt fit to burst but I resisted the temptation to stroke it, I wanted to concentrate on the sensations in my pussy. Lisa started to move deeper and quicker our pace building, she stopped and untwined my legs to put them on her shoulder and started to thrust much harder, I could feel her beautiful clit massaging my prostate and the heat of our bodies and her considerable effort making love to me. I tried my best to hold off Cumming, I wanted to cum in my beautiful lover. Lisa was breathing quickly and I knew she was close.

"Fill me up darling, I love you"

That was all it took, Lisa exploded in my and collapsed on my chest, I held her tight until she came down from her climactic high. She eased out of me and scooted down to suck her essence from my gaping pussy. She lapped and sucked me clean then came to my face and kissed me, sharing the last of my cum with me. I turned her around and she knelt on the bed, I lubed her pussy and played with her clit gently whilst opening her up. I positioned myself behind her and thrust deep and hard into her pussy. Lisa gave a sharp intake of breath and a low moan.

"Fuck me." Lisa said, "I'm yours, I love you, cum in me. Pleeeease!"

I started thrusting in and out I couldn't last long I knew that, Lisa had kept my prostate massaged and I wouldn't last long, I just made love to her hard and fast. Surprisingly I did last more than a few minutes but I soon felt that familiar build-up of pressure from deep within me, I gave a final thrust and exploded deep within my lover. I felt as though I was filling her with my life blood. We collapsed on the bed and I stayed planted inside my beautiful partner until eventually I slipped out. I did exactly the same as Lisa, bending down to lick and suck her pussy until she was clean. Lisa rolled over and I kissed her hard, forcing my seed into her eager mouth.

We lay back on the bed and slowly came down together, gentle caresses and lighter kisses replaced our earlier urgent lovemaking.

"Do you understand now Lisa? I love you and only you. I wouldn't let anything spoil what we have and what we will have. Other friends may play with us but in the end it is always you and me. I want us both to have Helen as a friend. Oh and by the way, she does great make-overs and if we do this business Helen will be a key part of it."

Lisa closed her eyes and I saw a tear squeeze out and slowly make its way down her cheek, I gently kissed it away just as I had done to my own children when they were little. Lisa opened her eyes and nodded her head.

"I understand" she said "I'm sorry I got jealous, I just never expected to find someone like you and then I thought you wanted someone else. I love you so much."

I stopped her saying any more; I kissed her and held her tight.

Eventually, we had to get up and shower, Lisa got ready to go home.

"Tell Helen she can come tomorrow and wear something revealing, it's not a conservative sort of club. If she has fetish wear, wear that."

"Here's her number, it would be nice if you invited her" I said.

Helen's surprise

After Lisa had gone home I was at a bit of a loose end, I had a bath and made sure I was still smooth, I pampered myself a bit with moisturizer and face cream. I lounged in my room until my phone rang. It was Helen, Lisa had invited her out with us and Helen was ringing me to say she would love to but didn't want to push in on our relationship.

"Nonsense" I said "We both want you to come, you are our friend and we want to share some fun."

"I really don't know what to wear though Caroline."

"I feel a shopping trip coming on; do you want to see what I'm going to wear?"

"Love to" said Helen "See you in half an hour?"

"Great" I replied.

So thirty minutes or so later Helen knocked at my room door. I asked her if she had any hang-ups about Lisa and I or any aspect of Lesbian, Gay or Transgender lifestyle or sexuality.

"I don't know if I'm honest" Helen replied, "I don't know enough about it. I liked to role play when I was married but He didn't get it at all. He was strictly wham, bam, thank-you and fall asleep. I would have liked to explore a lot more but haven't had the opportunity since I've been on my own."

I stood up and opened my wardrobe; I showed her the outfit I had bought for the club.

"Oh my god, that's gorgeous, totally outrageous but stunning. I wish I was brave enough to wear it." Helen sat down with a dreamy look in her eye.

I asked "Are you free tonight?"

"Yes" said Helen, "Why?"

"Come on were off shopping." I grabbed Helens hand and we left the hotel in my car. I drove to the adult store Lisa had shown me. "I'm buying you an outfit for tomorrow and no argument."

I took Helen inside quickly so that she had no time to argue or to think that we were actually going in to an adult store in her home town. I walked up to the counter and the same assistant who had served me last time was there, she recognized me, (or more likely my credit card) and asked if she could help.

"I need an outfit for my friend, were going to a club tomorrow and I'm wearing the outfit I bought the other day"

The assistant who introduced herself as Kelly immediately showed us to the clothing section and asked for Helen's preference.

"Rubber, Leather, PVC or other fabric?"

Helen was speechless, I asked Kelly to give us a minute, I linked my arm with Helen and escorted her around the racks.

"Look, this is a special place we will be going, I've never been and no-one will know us. We can be whoever and whatever we want to be. According to Lisa there will be all sorts there from normal club wearing girls, guys and TV's to real fetish wearing types. I decided to go all out as I wanted to indulge my fantasies and those of Lisa. Let yourself go Helen, go for it girl!"

Helen relaxed a little; we walked around the racks feeling the different fabrics.

"Ok Helen, tell me what you don't like." I said.

Helen said, "I like the soft leather but not the thick hard stuff, I quite like rubber too but some of the smell puts me off, I'm not keen on PVC but I really like the Velvets, lace and silks. I would quite like a Gothic look, not Goth but more classic Gothic."

"Brilliant!" I signaled Kelly over and explained what we were looking for.

Kelly was fantastic picking out outfits and accessories to compliment them. Helen had a pile of outfits and we filtered them down to about five then headed for the changing room. I stayed outside but Helen pulled me in to help.

"You're a girlfriend Caroline, no secrets between girlfriends."

I started to get aroused but concentrated on helping Helen in and out of the various outfits. We got down to two outfits and Helen looked stunning in both. My own favourite was a corset top dress in purple velvet and satin with black lace high neck collar. The skirt was mid-thigh length with underskirts in lace. Kelly had accessorized with lace gloves, fine fishnet stockings and stiletto ankle boots. Helen loved it but also liked a more risqué outfit with a black rubber dress which was strapless and very figure hugging, the skirt was again mid-thigh but the back was open to just below her cute bum and had straps and buckles across the opening. Kelly had accessorized with latex stockings, knee boots and elbow length latex gloves.

Kelly invited us to have a drink in a lounge area and to wear the outfits to make our mind-up. Helen was really torn between the two.

"Why not have the most outrageous outfit." I said, "You may never go again if you don't like it, but you might regret it if you don't"

Helen took a deep breath, "The Rubber one, I've never considered anything like this before, I feel totally outrageous but I would like to wear it at least once."

"That's settled then, go change and I'll go and pay."

"No." said Helen, "I can't let you pay"

"Look, I want to make this my treat, I'm having a ball with you and Lisa and I want to celebrate my new found life with my two best friends. Please let me pay I hope we can all have fun and we all deserve it."

Helen smiled and kissed me on the lips, "OK Caroline, this time you can pay."

Helen changed and I paid for the complete outfit. I also slipped a riding crop and a collar and lead into the bag. Just in case Helen gets lucky I thought.

We left the store and decided to have a bite to eat; Helen invited me to her house so I accepted. Helen made a light supper. We chatted over a glass of wine and we looked the club up on the internet. There were some fantastic pictures and we were both excited about going. I text Lisa and told her Helen was coming tomorrow night. Lisa text back and suggested we met at a hotel nearby, another of her friends was staying there and we could meet up and finalise our make-up before we went to the club. I agreed and Helen phoned and booked a taxi to get us to the hotel for seven. We decided to wait and see what happened before we booked a return journey.

Helen asked me to come to the salon the following day as she had a surprise. We arranged to meet at one o'clock. I kissed Helen and drove back to the hotel. I showered and went to bed early, by the look of the pictures on the club website I was in for a long night tomorrow.


Friday morning I had a light breakfast and stayed in my room until it was time to go round to Helen's

"I've closed the shop for the afternoon she said, my friend is coming round to help us get ready" she said and locked the door behind me.

"Help us get ready?" I asked, "How?"

"Wait and see" she said, "Sit down and I'll start you off"

Helen removed my blouse and put on a shawl thing and sat me in a chair, she reclined the chair and cleansed my face completely of make-up followed by a moisturiser.

"Can you do me now?" she said.

I repeated the process for Helen and as I finished there was a knock on the door. Helen let her friend in and introduced her as Tina. Helen also introduced me as one of her dearest girlfriends and I blushed beet red.

"Right girls let's get started" said Tina

I was pushed into the chair, Helen left to make coffee. Tina started by cleaning my hands and filing and buffing my nails, then she glued false nails on and spent the next forty minutes filling and filing my nails. I didn't recognise my own hands; Tina then painted the nails in a deep burgundy colour followed by clear lacquer. Tina then glued some diamante crystals to some of the nails, I was staggered, my hands looked like they belonged to a film star (at least I thought so).

Tina said "Now don't touch anything until I say so."

I lay in the reclined chair gazing at my hands; Tina and Helen were standing behind me when I suddenly felt my wig being removed.

"What? No. Please don't."

"Shhhhhhhhhhhh Caroline." Said Helen in a soothing voice, "Tina knows and is excited to help. She is one of our potential beauticians if your business gets going."

I relaxed and Helen proceeded to wash my hair and to trim it. I didn't have long hair but it wasn't too short either. Helen explained that she was trimming it to encourage growth and that she hoped she could eventually get a feminine style which I could change if I needed to be male at any time. I was so happy I almost cried, I teared up and Tina said; "Get that over with before I do your make-up"

Tina started on my make-up, I felt fantastic as she massaged, plucked, smoothed blended and all sorts of other wonderful things. Tina applied false lashes to my eyes and my eyelids felt wonderful, the extra weight of the lashes and the coats of mascara were a constant reminder of my femininity. As Tina finished I tried to sit up but Helen pushed me back down.

"No peeking until we have finished"

I lay back in the chair and Helen re-fixed my wig, turned the chair around facing a wall and then allowed me to sit up. Helen primped and preened my wig making some more light adjustments and lightly trimming it.

Helen said "Close your eyes" and then spun the chair around to face the mirror "Open "she said.

I was astonished at the transformation; I was made up in a very dramatic style with accentuated cheeks, burgundy lipstick to match my nails and such a high gloss. My eyes were like nothing I'd ever seen before, fantastic colours and so sexy.

Even my hair was different; Helen had changed my wig to a very dark chocolate brown accentuated with deep burgundy highlights, very subtle but clearly there. It was longer than my normal wig straight but with a flick outwards at the ends. I was stunned into silence and just sat in the chair staring at my reflection.

"Don't you dare cry!" said Helen.

I jumped out of my reverie leapt out of the chair and hugged Tina and then Helen; I was babbling like an idiot I was so excited.

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