The Fulfilment of Caroline Ch. 02

"Martin, please let me say this as I only have the courage to say it once, please don't interrupt. I told you I wasn't like other girls and that's true, Martin I am a transvestite, I have only been out and about as a girl for just over a week. I don't want to go back to being full time male again I want to live most of my time as female. I am bisexual and have a transvestite girlfriend. I really like you and enjoy your company, I understand if you don't want to talk to me again but I thought you needed an explanation at least. I'm sorry if I lead you on."

There was silence on the other end of the phone, "Are you still there Martin?"

"Sorry" He said "That was a shock, I thought there might be something, you were married or had a boyfriend or something but I'm completely shocked." He laughed then, "I thought I was a man of the world but you certainly fooled me."

"I wasn't trying to fool you Martin. I was just being who I wanted to be. I didn't intend to meet you and like you and certainly not to make a fool of you. I'm sorry I hurt you, I won't call again."

I put the phone down and sat on the bed and wept a little. Two minutes later my phone rang. I answered and it was Martin.

"What happened there?" he said, "I didn't say you hurt me and I didn't want to hurt you either. I enjoyed our meeting and you are the best kisser I've met in years." He laughed again and so did I. "Look I'm in this area for a few more days, can I take you to lunch? I want to see you again."

I was shocked, I said I was OK to meet tomorrow but after that I would be busy until Friday. I had business to attend to. Martin asked where we could meet. I said I would go to the Hotel at around one o'clock if that was ok. He agreed and after a little small talk he said goodnight and see you tomorrow.

I lay back on the bed thinking "Oh my god, what have I done?" there was a light knock on the door and the door opened slightly and Helen put her head round the door.

"How did it go? What did you say? Are you OK?

There was concern in her voice and I started to cry again, Helen burst into the bedroom and sat on the bed and held me close, she didn't say anything she just held me close. I pulled myself together and told Helen that everything was fine, I needed to freshen up but I'd come back to the lounge and tell them what happened.

I cleaned my face and touched up my lipstick and went into the lounge. I explained what had happened in the conversation and Martin's invite to lunch. The girls were so excited, they wanted to know how He sounded and whether I thought he was trying to get into my knickers. We all laughed when I said He knew what was in my knickers and I didn't think he needed another one as he already had one.

Kim asked, "What are you going to wear?"

Helen and Kim dragged me to my room and were throwing clothes out of my wardrobe and onto the bed, in no time my bed was covered and the girls were pulling outfits together and holding them against me. I just stood there and let them have their fun.

"You need an LBD." Said Kim

"LBD? What's that?" I asked.

Helen and Kim both looked at me and laughed, "Little Black Dress!" they shouted in unison.

"No time for shopping, I, meeting him at lunchtime."

Kim said I'll get you ready and take you shopping in the morning; Helen was upset as she had to work and wanted to come with us. I excused myself saying I needed beauty sleep more than they did so I cleaned up and went to bed.

LBD

Kim woke me up and said don't get dressed until we have de-fuzzed you. We had breakfast and then Kim set about my legs, underarms and other areas with an epilator, it hurt a little but Kim explained that I would get used to it and it was better than shaving.

Kim helped me to choose underwear, she picked out matching black lace bra and knickers and black hold up stockings. I asked if this was a bit over the top for lunch. Kim told me that if I felt sexy then I would be sexy and Martin would not be able to resist.

"Come off it Kim, I'm going for lunch and nothing more."

"We'll see." She said.

I dressed in underwear and wore a black skirt, blouse and black court shoes. I chose a black handbag and a black coat. Kim helped me with my make-up and I must admit I was pleased with the result, very classy I thought.

We left the house and drove in my car to town, Kim had a good idea of where she wanted to go. We walked in to a small boutique type shop and Kim immediately steered us towards a saleswoman. Kim obviously knew her and introduced me to Marion. They started discussing me as if I wasn't there. Kim and Marion picked out several dresses while I wandered around looking at various dress racks. Kim called me over and we all went to a changing room where I tried on the different dresses. Some fit really well and looked ok but I wasn't blown away by any of them. Kim and Marion looked at me and I said.

"I know it's not an LBD but I saw a black and white dress which I liked over there."

I walked over to the rack and pulled out my size. I tried it on and I loved it. So did Kim and Marion. It was a simple shift dress with black panels down both sides and white centre panels. I looked super slim in it and I knew this was the one.

Marion and Kim found some jewelry to match and I left the shop feeling like Julia Roberts.

I dropped Kim off and then went to meet Martin. I was very nervous and was regretting the decision to drive myself. I waited in reception and Martin came in after a few minutes, I stood up and without hesitation Martin walked up to me held my hand and kissed me. I was blown away, He knew all about me and he kissed me in public!

Martin whisked me off in his BMW to a country restaurant out of town. I had a wonderful time and martin was charming and witty. I learned that he was divorced, had children and lived alone in London. He was a Financial Advisor and was usually in the area several times every month. I was honest with Martin and explained that I was hoping to open the café and would be catering for the LGBT community. I told him about Lisa and how we met. I also told him I was flattered by him and was loving his company.

By mid-afternoon, Martin had appointments to go to but he held my hand as we walked to the car and as he opened my door he pulled me to him and kissed me deeply. I now knew what women meant when they say "melted in his arms" the kiss was magical and I felt more feminine and sexy than I ever dreamed I could. Martin asked if he could see me again and I didn't hesitate to say "YES!"

Martin took me back to my car and we kissed more until he really did have to leave. I drove back to Helen's in a daze; I don't remember anything about the drive at all. I sat in the lounge re-living every moment of the lunch and especially the kiss. I was dreaming and I realised I really liked the butterfly feelings I had when I was with Martin. Oh no... more complication!

Closing doors

Helen and Kim came home after six; I had changed into casual and had made a chicken salad for tea. I was ambushed by both of them for details, which I duly gave over our meal. Eventually they calmed down and I asked what I should do about meeting Sam tomorrow. I wanted to be Caroline but I also needed to explain things to Sam in a gentle and controlled way. I decided to wear plain fem jeans and a blouse with a plain sweater over the top; I would wear underwear but no bra and wear my male trainers I asked if Helen would do my hair in the morning including some highlights, I wanted to encourage my real hair growth and style into a feminine style. Helen agreed and we spent the rest of the evening discussing hair styles and colour options. I wanted to keep my nails but I decided that they needed to come off, Helen and Kim helped and after a while I had clean nails buffed and coated with clear nail polish.

The following morning I went to the salon with Helen, she trimmed my hair but wouldn't give me all the details on the style. Helen coloured my hair but again wouldn't give all the details, I really trusted her.

After an hour or so of pampering Helen showed me the results, I was amazed, I had my own mousey brown hair coloured all over to a dark blonde with golden highlights. The style was a kind of pixie cut, spiked on the top and sides as much as my short hair would allow. My ear piercings were clearly visible. I loved my look and I kissed Helen, thanking her profusely.

I was too nervous to do anything so I stayed in the salon clearing up and helping where I could. Eventually it was time for me to go and meet Sam at the hotel. I called her and told her I would be there in ten minutes. I arrived at reception and Sam was waiting. I didn't give her time to react; I just walked up to her said hello and whisked her out to my car. I let her in and shut the door, jumped in the drivers' side. I asked her not to say anything until we got to a picnic area and then I would answer all of her questions.

I parked up and turned to Samantha and said, "Do you feel repulsed by my new style?"

"Not at all" She replied, "You are one of my dearest friends, I'm intrigued though. Do you want to tell me?"

I started at the beginning, telling her how I'd been a lifelong cross-dresser, how my wife had known but how we had kept everything in the bedroom. I explained how I had been chatting on-line and how I had developed friendships. I didn't explain too much about the sex but I did hint that there had been some intimate contact between Lisa and I. Sam was very quiet, calm and understanding. I told her I had made several new friends as Caroline and had been almost one hundred percent in female mode since I had arrived. I left out my meeting with Martin and the visit to the club.

I asked if Sam wanted to go for a coffee, we drove back into town and went to a nice bistro and sat in a quiet corner to continue our chat. Sam hadn't said a great deal but when we sat down she complimented me on my hair and said I looked better than I had in years. I beamed and blushed too. I explained about Helen and Kim and also how Tina had done my nails. Sam noticed quite a few other things too, women's clothes, plucked eyebrows and my ear piercings. Sam said she was happy for me and wished me every happiness.

"You deserve to be happy, you are a lovely person."

My eyes were moist so I leaned over and hugged her. When the coffee was served, I started to discuss the business and also my business plans here. I offered Sam a position as my Senior Manager in the company, she would have executive control and I would meet up once a month to sort out management issues. Sam was more than happy and we then discussed the café. I needed the finance through the company and Sam would have to arrange it. I needed the café in the company name as I didn't want my real name on any documents, it had to be Caroline. Sam was certain she could make all of the arrangements.

I asked Sam to dinner but she said no. "No?" I asked "Did you male other plans?"

"I was hoping Caroline would come out with me."

I was floored; I hadn't expected that at all.

"Are you sure?" I asked, "I don't want to make you uncomfortable."

"I'm sure." She said, "I have a feeling I will be seeing a lot of our business partner Caroline."

We finished our coffee and I drove Sam back to the hotel. I arranged to collect her at seven thirty and I dashed home to plan what to wear. I showered and called Helen at the salon. She agreed to come home to help with my make-up. I wanted to look classy for Sam.

I decided to wear the LBD again but this time I wore tights which were not as sexy as the stockings I wore for Martin. I chose a lace bra and panty set with a satin full slip. I also chose lower heels and I picked out a light wool cardigan for later if it got chilly.

I showered and was dressed in my underwear and slip when Helen came home. I let Helen loose on my face; she was fantastic and made me feel relaxed and totally feminine. I really needed to do something to thank Helen for all she was doing for me.

I thought I looked great, my wig was primped and preened and I wore my favourite perfume. I was very nervous but Helen told me I looked a million dollars and kissed me lightly on my cheek. I collected my clutch bag and purse and set off in the car to pick up Samantha.

She was waiting in reception and didn't recognise me as I walked in; it was the best compliment she could have paid me. I walked up to her and said quietly,

"Are you ready to go Sam?"

Sam was wide eyed and in a state of shock.

"Y.y.yes, I'm sorry I didn't recognize you, I wasn't sure what or who to expect but you are so much better than I dreamed."

I linked my arm with hers and we walked out to my car. I drove to the restaurant in silence, Sam was checking me out I could tell. We arrived and we were shown to a quiet table. I asked for water and Sam ordered wine as an aperitif. I broke the silence by asking Sam what she really thought. Sam looked a little embarrassed but I gently stroked her arm and said.

"Sam you are my best and oldest friend and colleague. I am trusting you with all of this, you have the power to cause me great damage but I trust you completely. Please tell me what you really think."

Sam looked at me and started to speak, "You are lovely, I never dreamed you would look so good. You are very natural and I can tell that this is something from within you and not some phase or kink or something you just want to try for a while. I think you look fantastic. I want Helen to do my hair and give me some tips on make-up too. I want to surprise the family when I get home. Do you think she could fit me in?"

"Let's call her now and ask, I leaned over and kissed Sam on the cheek. Thank you I said, that means so much to me I can't tell you."

I called Helen and she agreed to do Sam's hair the following morning at nine o'clock before her first booked customer. She said she was looking forward to meeting her."

We ordered food and we chatted like old girlfriends, Sam was totally relaxed and I knew I had made the best choice in confiding in her. We discussed the café and Sam questioned the business plan and what I would be offering apart from Coffee. I didn't go into too much detail but I explained that there was a demand for alternative lifestyle services and facilities. I couldn't explain too much as I was pretty sketchy about the details myself.

Sam agreed with the plans and would sort out the finance through the business. I needed to sort out giving her proper authority at the bank and with the accountants but would do that over the phone tomorrow. I then told Sam that I was giving her a pay rise and give her other perks. Sam was delighted to be given the opportunity but would need to keep close contact to make sure she was guiding the company as I wanted. We agreed that she would come down at least once a month and I would go back as soon as I felt comfortable.

As we were eating our meal, Lisa called. I told her I was out to dinner but wanted to see her as soon as possible. I said Sam would be going back tomorrow afternoon so I would be free from about three o'clock. I told her Maam wanted to see her too. Lisa sounded excited when she said;

"Yes Maam, I will come round. Do you want me at Helen's dressed?"

"Yes I do. Please make sure you are ready."

We ended the call and when I looked up, Sam had a quizzical look on her face. I explained that it was Lisa and that we had a bond and a relationship that was also physical. I asked Sam not to judge but she interrupted.

"I'm not judging Caroline, I'm fine with it really I am. When I was at Uni. I had a fling with another girl; we were pretty wild at one time. We used to go to a punk club and there were all sorts there. Gay people, straight people, I never knew any transvestites but I met some pretty androgynous guys who wore a lot of make-up and Goth and Punk clothes. I believe in live and let live, I'm pleased that you are having fun, you have friends and it's about time you had some time for yourself."

I reached over and hugged her close, "Thank you." I said "You really are a friend."

We finished our meal and I drove Sam back to the Hotel. I left her at reception and said I would pick her up at a quarter to nine the following morning for her hair appointment. I went back to Helen's and she was waiting for me and wanted to know everything. I opened a bottle of wine as I hadn't had a drink all evening; I kicked off my shoes, sat on the settee with Helen and told her all about the evening and Sam's acceptance. Helen was very happy for me and said she would make sure Sam got the best make-over in the morning. Helen hugged me close and asked me to bed with her. I accepted the invitation and prepared for bed wearing a satin negligée and no wig, I primped my own hair and I loved it. I was looking forward to having longer hair.

I joined Helen in her bedroom and it was clear Helen wanted to make love. I had a little guilt feeling about Lisa and also Kim but Helen explained that she had agreed with Kim that they had a relationship but that it was not exclusive and both were OK to meet other people, Helen also said that Kim wanted us all to be together as much as possible. Helen also pointed out that Lisa had a wife and would obviously be having relations. I accepted the logic and slipped into bed. Helen and I made love slowly, plenty of kissing and exploring of bodies. I stripped off my negligee and we made love in several positions, Helen was very passionate and also loved to ride me on top, she sucked and bit my nipples and I loved all of it. Helen climaxed several times and when I was getting close Helen climbed off me, removed the condom and sucked me until I came in her mouth. Helen showed me all of my cum in her mouth and then swallowed. It was very erotic and afterwards we kissed, I loved tasting my cum in her mouth. I scooted down and ate her out for a final orgasm and then we collapsed into the bed, cuddled up under the duvet.

When the alarm went off in the morning Helen and I kissed and Helen immediately wanted to take advantage of my morning glory. I accepted the invite and we made love again, fast and furious, Helen came twice and I flooded my condom buried deep inside her.

We showered and had coffee and toast before leaving, Helen to the salon and me to collect Samantha. Sam was waiting outside; she had checked out and had packed her car. We drove around to the salon where I introduced Sam to Helen, they kissed each other and Sam said she was grateful that Helen was looking out for me and that I was her dearest friend. Helen said I was her best friend also and would make sure I was OK.

Helen asked what Sam wanted with her hair. Sam was very brave and said Helen could give her a make-over.

"I need a re-vamp" she said "I want to spice things up a bit but I need to make sure I don't look like a bimbo, Caroline has put me in charge of her business."

Helen sat her down in a chair and spent ten minutes combing and feeling her hair.

"Are you happy with the colour?" she asked.

"Anything you want but probably best not Platinum blonde." Laughed Sam.

Helen washed her hair and proceeded to trim and cut her hair. Then she coloured her hair and put highlight strips in.

Sam asked what colour she was going to be. "My surprise." Replied Helen.

Helen covered the mirror with a towel; we had coffee while waiting for the colour to react.

Eventually Helen washed Sam's hair and proceeded to blow dry it, she trimmed some more and applied some mouse and more styling. Helen was finally happy and removed the towel. Sam's hair had gone from being straight brunette below the shoulder to a slightly lighter shade at shoulder length, with lots of layers, her fringe and the sides were feathered and framed her face. Through her hair there were dark blonde highlights. Sam turned her head and her mouth was wide, after a few moments she squealed in delight.