tagTranssexuals & CrossdressersThe Fulfilment of Caroline

The Fulfilment of Caroline


The Fulfilment of Caroline

This is my first ever story, it is based in truth but develops into fantasy. The main characters are real. I have ideas for further chapters and would love some feedback and ideas where you would like the story to develop. There is sex but also a love story, if you just want gratuitous sex then this is probably not for you. Have fun, Caroline.

Chapter 1. My education and awakening.

Let me set the scene, I am Caroline and have been a transvestite for so many years I've lost count. I know this is nothing new to most of you reading this. I am a child of the 60's so you work out my age. A girl should never reveal her true age. Anyway like many, my dressing was put on a very low light on a back burner while I got on with married life children and work. Unfortunately after 20 years of marriage my wife died and I was bereft for a long time. My birthday a couple of years ago was a key point in my life, I realised that I was missing a huge part of myself, Caroline needed to express herself a lot more and discover her true self. I felt that I couldn't come out in my home town as I didn't want to put my children through any hurt.

I am a successful businessman working in the very male world of construction. I have a consultancy based in the North of England and work on high profile contracts all over the country. I have decided that the UK is big enough for me and have resisted the temptation to work abroad.


I decided that I would join a TV website and their chat room to find out more about the scene and where I might go. The internet was a revelation to me, I grew up in a provincial town convinced I was the only transvestite in the world and although by the time I reached my late teens I realised there were more of us, the internet has shown me the light. I joined a couple of chat rooms and enjoyed what could be described as a voyage of self-discovery. What I discovered was that I was not attracted to men in my female persona but I was attracted to other girls like me, I engaged in all sorts of cyber-sex and nothing really fired me up. After about six months of chatting I started to get really bored with the same old thing, men who wanted a wank and girls who wasted my time. I had a few regular girlfriends and we started chatting on regular Yahoo, eventually I left the TV sites and chat rooms and concentrated on my girlfriends with whom I felt I had a proper friendship. I still enjoyed cyber-sex with some and one in particular.


Lisa and I had become very good chat friends; we chatted most days and became very good friends. We trusted each other and discussed our families, our hope, fears, and jobs, everything friends talk about, over time we each opened up about our sexuality and then Lisa admitted that she had very submissive feelings and fantasies. I had experienced some sub and dome cyber-sex in the chat rooms and I knew how to play along but it wasn't really me somehow. Lisa was different, we had a relationship based on trust and friendship, I decided that we could explore a little fantasy and told Lisa that provided we both agreed that nothing would spoil our girlfriend relationship we could have some fun and explore.

The rabbit hole!

We started by creating two separate characters for ourselves, this was to separate the very real friendship of Michelle and Lisa from our fantasy. Lisa wanted me to control her and for her to have no will. I decided to call her "Bitch" no name but to emphasise her position with me, I became "Maam" again she couldn't know my name but had always to address me by my title. We created new messenger accounts using our new persona names, if Lisa saw that Maam was logged on she knew she had to be Bitch and vice versa. We started out very cautiously, I was very unsure of how far Bitch wanted to go or indeed how far I could go. We soon realised that we enjoyed our fantasy role play and from pure verbal abuse from Maam, we progressed to Maam insisting that Bitch inflict self-punishments for misdemeanours such as failing to address Maam properly, failing to show proper respect or using poor grammar in the chat. Maam was getting strict and Bitch seemed to love it. It occurred to me that Bitch seemed very earnest and appeared to take everything Maam said literally and could take more. We exchanged pictures sourced from the internet and Bitch got more and more adventurous, strangely Maam was getting into her stride even though it was all very new, this was a revelation to Caroline and a side she never knew she had.

I told Bitch that she was a worthless slut and wasn't pleasing Maam and that I didn't believe she was carrying out everything instructed to the letter. Bitch was beside herself and said she could prove it if I viewed her webcam. Pow! Another huge leap. I accepted her cam invite and there she was, exactly as she described, wig, full make-up, underwear heels and the toys. I immediately instructed Bitch to use the crop on her bum 3 strokes to each cheek, whack, whack, whack.... whack, whack, whack. This was getting interesting and I was discovering a new me. I instructed Bitch to put pegs on her nipples and her clit, and hey presto, they were applied. I started to think of the possibilities and my own clit became very hard.

I started to explore how far Bitch would go...

"Have you got a dildo Bitch?"...

"Yes Maam"..

"Well show me you stupid slut"..

."Sorry Maam, yes Maam, here it is".

Bitch produced a dildo about 7" long and reasonably fat.

"Suck it Bitch, deep throat that cock for me, show me you're worth my while."

"Yes Maam",

Bitch started sucking and licking the cock but only managed about two thirds of the dildo before she gagged.

"Deeper Bitch, I want to see all of it in your throat."

"Sorry Maam I can't".

"You useless slut, why do I bother with you?"

"Maam, please Maam, I will practice I promise, please keep me Maam."

I decided to see how much punishment Bitch could take so I told her to bend over and use the crop on her pussy........and she did,

"Harder you pathetic Bitch."

Bitch complied with my demands and eventually had red welts all over her arse and around her beautiful puckered hole. I was really getting into Maam, I was truly surprising myself

Where to Go from Here?

Bitch was getting more and more submissive, I decide that she needed a completely new look, different from Lisa and I also needed a new look for Maam, I decided Bitch should be blonde, curly haired and always in pink, and corseted. I loved the Goth look and went for long dark hair, dark clothes and heavy eye make-up. I dictated my requirements to Bitch and she lapped it up. I was cruel, I told her she could not address Maam until she was properly attired. I logged out and back on again as Caroline. Lisa followed and attempted to discuss Bitch and Maam, I immediately explained that we could not discuss our other persona and if she wanted to discuss she needed to please Maam and do as she was told. We continued our normal chat including our sexy chat as Lisa and Caroline.

The next day we chatted again as Lisa and Caroline and again for the third day after Maam's demands. On the fourth day I logged on and saw that Lisa wasn't there but Bitch was. I re-logged in as Maam and immediately demanded to see her. On came the cam and I was utterly delighted to see the vision before me. Blond curls piled high on her head with tendrils around her face and cascades around her shoulders, a beautiful pink lace up Basque with matching knickers, pink stockings and white heels. To say I was knocked out was an understatement. I didn't tell Bitch of course, I punished her for not getting in touch sooner, what a total cow; but what can I tell you, I was truly getting into the role. Now time to turn up the heat!

I had been buying more clothes since my wife died and I had a decent wardrobe, I also had quite a few dome outfits, I didn't like rubber, PVC was ok but leather...oh now there's a material to stir your soul. I had red and black leather basques, some skin tight trousers, a dress and my favourite of all a cat-suit. I decided I wanted to meet Lisa so I took a week off work, booked a hotel and drove down to a town close to Lisa. I asked Lisa to meet and she agreed but I ordered Bitch who had no choice.

I drove down to the hotel on a Friday afternoon in my company estate car. I arrived at the hotel which was in a pleasant area surrounded by countryside; I booked in and decided I would commence my fem change with a luxurious bath, full body shave, eyebrow trim and moisturise. I had planned to stay in the hotel in male mode but as soon as I arrived I wished I had been brave enough to go fully enfemme for the duration... next time. I ate a meal in the hotel with male outer clothes but all my underwear was Caroline's that was it.. definitely fully fem next time. I spoke with Lisa on the phone from my room and she agreed to come round to the hotel for 11 the next morning. I was very excited, Lisa had been going out dressed for a few years and I was hoping she would help me with that huge step.

The First Meeting.

Lisa knocked on my room door and when I opened the door we both fell into each other's arms for the longest hug and tentative kiss. I felt whole and complete for the first time in years and knew that this was me....forever.

We finally managed to separate ourselves and we chatted like old girlfriends, you would never have known this was our first meet. Eventually we started to get a little hungry and Lisa offered to take me out to a bistro in town, I was nervous but having decided I wanted my fem side to be more full time I asked for a little help with my make-up and choosing some more appropriate day wear and went out. I completely fell in love with being out, no-one batted an eyelid (except a few guys checking out two hot MILF's) the meal was lovely the conversation perfect and Lisa was wonderful helping me, correcting little mistakes and coaching voice tone. We left the Bistro and decided a little shopping trip would be in order. Another first for me and I admit I got carried away, with this much additional wardrobe I'd need another suitcase to get everything home.

When we returned to the hotel, we had coffee in the restaurant I didn't even think about it until I gave my room number to charge it! What the hell I was having too much fun. Lisa said there was a TV friendly club nearby and that we should go. I looked it up on the web and there were all kinds of TV styles, including fetish, hmmmmmmmmm now should we go as Maam and Bitch? Not this time I decided, Lisa and I were having so much fun getting to know each other I was nervous about pushing the boundaries too far too fast.

Lisa needed to go home and change, I went up to my room and reflected on the day. I realised how much I had denied Caroline in my life and resolved to change my whole life from then on. I needed to be Caroline, just how much I wasn't sure but I was sure it would be so much more than I had ever previously imagined, a day with Lisa was like a re-birth. I took a long bath, and then relaxed before getting ready for a nightclub date with Lisa. I had so many new clothes to wear I took an age deciding what to wear, what style should I go for, how racy should I be? Eventually I decided on a mini dress in black with a lace bodice and long lace sleeves, I decided on tights rather than stockings as I was a little unsure that showing stocking tops would be the done thing. I then did my make-up, I even used my IPad to look up an on-line tutorial for smoky eye make-up, and after a couple of attempts I was happy. I brushed my hair, put on my jewellery and put on my new jacket, black with large gold buttons; my new shoes were black patent courts with 4" heels. I filled my new clutch bag with essentials make-up, purse, some cash, emergency cards, tissues and room key. I took the stairs down to the hotel lounge to wait for Lisa. I was being careful walking in my new shoes and was looking at my feet as I descended the stairs to the lounge, when I looked up there were a number of business men looking at me, I blushed and moved to sit down near the entrance door, I clutched my handbag like a safety blanket, sure that these men were all laughing at me. To my surprise the barman came over with a glass of white wine and said it was a token from the gentlemen at the bar for brightening their evening, to say I was stunned was an understatement, I blushed beet red but I took the wine and toasted the guys at the bar who all toasted back. I sipped the wine, fighting the urge to gulp it down and bolt for the door. Thankfully, Lisa came in and sat down, she had a taxi waiting so I waved at the guys and left.

"So tell me who your admirers were Caroline?"

I blushed red again and related the story to Lisa in the cab; we giggled like school girls and laughed all the way to the club. We went next door to a restaurant for a bite to eat then made our way to the club around 9.30.

Dancing in Heels

The club had a lounge bar which led into the disco, we went to the bar and ordered drinks, there were loads of very beautiful girls around, I felt self-conscious as I didn't believe I looked anywhere near as good. Lisa told me to relax and we went to find a seat, some of Lisa's friends came over and I was introduced as a new girl, I have to say all of Lisa's friends were very friendly and welcomed me into their circle without any question or fuss. After a little while we went into the disco and I danced with Lisa. For the first time in my life I was dancing in heels, I had never been a good dancer but Lisa helped me to relax and we didn't try anything too complicated. By the end of the night I was on a complete high and my calf muscles were on fire from such a long period on my feel in heels. I couldn't have felt any better.

As Lisa and I left the club I asked the question I'd been desperate to ask for hours:

"Do you want to come back to my room?"

"Yes" was the reply followed by the most sensual kiss I'd ever experienced.

The ride back to the hotel went by in a blur, kissing and cuddling with Lisa in the back seat; I didn't even consider the taxi driver! We stumbled up to my room barely able to keep our hands to ourselves, once in the room we calmed down a little, enough time to strip to underwear, hang our dresses up and get a glass of wine each from the minibar. We sat on the bed and gently caressed each other, I leaned back and Lisa dropped to her knees between my legs and gently removed my straining knickers to reveal a very full erect clit. Without waiting she lowered her lips to the head licked the pre-cum and then took me deep in her mouth. I could not believe the sensation, my toes curled and I was gripping the bed sheets, without realising it I let out a long moan and lay down unable to support myself. I was in total heaven. Lisa came up to join me and I kissed her with a passion I hadn't felt for years I pushed her onto her back and removed her knickers and without a nanosecond delay engulfed her beautiful clit. I had never sucked a she-male clit before but I thought she was wonderful tasted fantastic and it appeared to be the most wonderful thing in the world to me. I savoured her taste, her feel and played with her sac and pussy, I bathed her all over with my tongue, planting kisses over her thighs and pussy, I even explored her pussy with my tongue, when she moaned I explored deeper and harder, I loved it and wanted desperately to please my lover.

"Fuck Me" I heard,


Lisa grabbed my head and in a throaty voice said

"Please make love to me, I've never been fucked before but I need you to take me ...Now!"

How could I ignore such a plea? I knelt between her thighs and placed my clit against her wet pussy,

"I have no condoms" I said,

"Just do it darling" said Lisa.

Slowly I pushed my hips forward until my clit pushed past the first resistance, I stopped and asked if she was OK, Lisa nodded and said

"Fuck me properly Caroline"

I started pushing deeper then pulling back, slowly I was going deeper each thrust and Lisa was pushing back, when I was all the way in I rested and looked into the eyes of my lover, I saw two things, deep love and animal lust. I started to thrust in and out and at the same time I gently played with her clit. I felt so right and so complete I knew that this would be my life in future. I was building momentum and also pressure inside, I could hold myself no longer and with a huge thrust I embedded myself completely and came deep inside Lisa. I have never had such a powerful orgasm, it seemed to go on forever and I collapsed onto Lisa completely drained. Slowly I regained my composure and Lisa was holding me tight and kissing my forehead gently. I looked up at her and gently withdrew from her tight pussy. Lisa immediately pushed me onto my back and dived head first onto my clit, cleaning every last drop of cum from me, I pushed her back and returned the favour cleaning her pussy and holding my juice in my mouth. I climbed back up and kissed Lisa, pushing all of my juice into her mouth, Lisa was a little shocked but recovered quickly, opening her mouth to show me her mouth full and then slowly swallowed, this seemed to me to be an act of love but also total obedience. I was thrilled. Lisa then asked what else I wanted. There was no question; I needed to be fucked and to be made whole. I asked my lover to make love to me, I lay on my back and Lisa descended to my pussy with her exquisite tongue and proceeded to drive me wild. I begged

"For God's sake fuck me, fill me I need you so bad"

Lisa knelt up and placed her clit against my pussy and pushed. I didn't feel any pain, my pussy was so relaxed and I felt so good that I was totally ready and accepting of the invasion.

"Fill me up"

I said and Lisa started a slow rhythm gradually going deeper and making me whimper. I was moaning and thrashing around the bed and Lisa was nailing me harder and harder, I felt complete and totally wanton at the same time, I had never before been so vocal or totally lost during love-making. This was new to me and I knew I could never go back to my previous pedestrian love-life. Lisa was pounding me now and I was thrusting back as hard as I could, how she was lasting this long I didn't know but I could feel my own love-juice rising.

I screamed "Fuck me, fill me, I'm gonna cum again"

Lisa slammed into me and I felt an eruption in my pussy and then my own clit spurt. I nearly passed out with the feelings I couldn't make sense of it, what had triggered me, how had I cum without touching my clit? I lay there and Lisa withdrew and gently lay down beside me, we cuddled for a long while, basking in an afterglow of total union in lovemaking.

I looked up at her and said, quite sincerely

"I love you Lisa, with all my heart I love you."

Then Lisa met my gaze and said

"I love you too" with that I cried and she held me tight.

How did this fit in with me being a dome? Here I was crying and deeply in love with another girl. I drifted off to sleep in Lisa's arms deeply contented and at the same time very confused. Could I ever be a dome for my lover Lisa? I awoke in the early hours and quickly realised where I was, I gently rose and went to the bathroom, I sat down to toilet that was natural, as I washed my hands I saw my reflection. What a total mess. Make-up a mess, smudged eye make-up, running mascara from crying and wig skewed and hair a mess. I used make-up remover to clean up, moisturised and straightened my wig, brushed out my hair and removed my underwear and put on my nightie. I went back to bed and lightly kissed my lover. Lisa stirred and asked;

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byCarolineShaw© 4 comments/ 21258 views/ 11 favorites

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