New Mother, New Life Pt. 01

When I was born I was immediately given up for adoption. I was what was known as a 'Magdalene baby', a product of 20th century catholic Ireland where women who conceived out of wedlock were sent to a convent to give birth and work like a slave in the laundry as penance for their 'sin'. The church made life cruel for these women and to make things worse most were separated from their child at birth.

I was told that I was immediately taken from my natural mother at birth and given to my adoptive family. I have had a wonderful family life and could not have asked for more but I did yearn to know more about my genetic mother so, aged 23, I set about finding her.

The process of finding her was much simpler than I had imagined. The name Helen Rosin McKee and a date of birth were given to me by the state adoption agency. She was born in 1965 meaning she would have been only 14 when she gave birth to me. I felt heartbroken when I realised this.

Within a couple of hours of searching online I was sure I had found the person I was looking for; she was a prominent dressmaker for the rich and famous based in Hammersmith, London. Once I saw her photo online I was almost certain it had to be her. I built up the courage to write her an email:

"Dear Helen, This may seem like a complete shot in the dark but I was given up for adoption by a woman of your name on June 9th 1979. I wonder if it was you. If not, then please write back so that I can continue my search. If it is you, then please write back because I would love to meet you. If you do not wish to meet me then I understand and I will leave you be. I would like to get to know you and share my life with you.

Sincerely, Charlie"

Two days later I received an email:

"My Dearest Charlie, I never expected this day would come. I was forced to give you up on the day you were born and have thought about you every day since. I have regretted everything about this and I am very sorry about what happened. I would love to meet you and get to know the person you have become. Helen"

Here we were, separated by all these years, and living less than 10 miles away from each other in London. It was indeed a small world. After exchanging a few emails we agreed that there was a lot to talk about and arranged to meet.

I had promised myself to be completely honest with Helen because, emotionally, I had nothing to lose, only to gain. My seemingly 'perfect' family life had been marred by lying and dishonesty with my parents over a number of things, especially the fact that I was a transvestite.

Twice during my teenage years women's clothes were found in my room and thrown out by my mother, no questions asked. The last couple of years had seen my cross-dressing intensify since leaving home and I knew it was something deep inside of me which I could not ignore.

I kept my body trim and my skin smooth because I loved feeling feminine. The gender confusion sometimes felt so strong that it felt like cross-dressing was not enough. Regardless of what I felt, there was no reason why I should tell any lie to this person.

At 2pm on a pleasant spring day I went to meet Helen at her favourite riverside restaurant. I was very nervous waiting there for her and even more nervous when she walked in and I saw how amazingly beautiful she was in person.

Her long blonde hair fell to one side of her shoulders and she wore a stylish, sexy figure-hugging leopard print dress which showed off her amazing legs and hourglass figure. Her platform heels made her seem taller than me. She was truly a femme fatale.

When she removed her sunglasses I saw her face for the first time in person. She looked so young, certainly younger than her 37 years, I would never have believed her to be my mother only for our shared characteristics; big blue eyes, high cheekbones and exactly the same cute little nose. It was uncanny and as our eyes met we both knew that this was for real.

"Charlie?"

"Helen?"

I stood up and we both nervously smiled as we didn't know whether to hug or shake hands. We hugged tightly and wept with both happiness and sadness.

"Oh my, you...you look just like, oh God...it's great to see you," she said in a well spoken slightly posh English accent, visibly shaking a little, just like I was.

Her eyes did all the talking and I could not take my gaze from deep beyond them. It was like I was looking into my own soul. She stared back intently as we cherished this moment.

"You are more beautiful than I had imagined...wow! Now I knew where my good looks came from!" I nervously joked, which made us both laugh.

We sat down at the table, both of us feeling awkward and weird. Once the wine flowed, so did the conversation. She had gotten pregnant by a young teacher with whom she had been infatuated but he disappeared to the U.S. once their secret was out. There was no option but to give up the baby and she was eternally remorseful about that. She had moved to London aged 16 and cut her career in dressmaking never to return to Ireland.

She asked about my life and I trotted out some boring things about myself. I was entranced by her beauty and felt so excited that I just blurted out that I loved her dress and I asked her where she bought it.

"It's an original." she said, "I made it myself, like a lot of the dresses I wear. Why? Do you like fashion?"

"I love women's fashion. It's so...I dunno..." I said, tailing off.

"Are you gay Charlie?" she asked frankly without any hesitation.

"No, I'm not gay...but I am a transvestite." I admitted, firmly and honestly.

Her eyes lit up and her whole face smiled:

"That's perfectly normal Charlie. I'm sorry for asking you that. You are young and free and there's no need to conform to silly stereotypes. I meet all sorts of people in my line of work."

Her reaction comforted me in a way that I had never felt before. She was warm and affectionate, upbeat and open-minded...the very same personality as me...and I felt like I had found what had been missing from my life all this time.

"You know, before you were born I was certain that I was carrying a girl." she said.

"Weird" I replied, "but it kind of makes sense, I was sure I was a girl all through my childhood. All my cousins were girls and they practically raised me so I feel more comfortable around women than men."

"Too right," said Helen, "if I have to be honest I really don't have much time for men. If you ask me it's all about girl power!" We both laughed.

"So you don't have a boyfriend then?" I asked, genuinely perplexed, looking at this stunning woman who could have her choice of any man.

"Why would I tie myself down with one man? I do prefer the company of my girlfriends but guys can be fun sometimes too. I guess you'd call me bisexual or maybe more of a 'lipstick lesbian' if you had to put a label on it!"

My jaw nearly hit the table. This wonderful beautiful free spirit was being so honest and genuine with me that I felt humble and lucky to have found her. As we talked I could not take my eyes off her and I hung on every soft word she spoke.

We left the restaurant and took a walk by the river in search of a nice place to continue the reunion of a lifetime. We stepped into a quaint pub and ordered some white wine. We spoke more about life. She did most of the talking. Her stories of flings and affairs with random eighties pop stars astonished me.

I was enthralled with her life and everything about her; her beautiful blue eyes which looked youthful, adventurous and wild, her long blonde hair falling around her slender neck, her beautiful breasts bursting out of her revealing dress which caught the glances of almost every passing man. I didn't just idolise this woman, I wanted to be her!

We left the pub at about 8pm, by now quite drunken but very happy. After 10 minutes walk we found ourselves at Helen's house. It was a large apartment where she both lived and worked with a comfortable living space and a huge variety of various dresses and costumes at the workshop end of the apartment.

"Be a sweetie and undo my zip please." she said turning her back to me holding her hair bunched up on top of her head revealing her elegant neck.

I unzipped her dress and it peeled away from her body suddenly leaving her there in her underwear; a white bra and panties with nude shiny hold-up stockings. Her slightly perspired skin glistened in the light and the scent of her perfume was wildly enticing.

Her body looked incredible. She turned around and bent down to pick up her dress, her full, orb-like breasts seeming to spill over the top of her white bra. Her small silky panties seemed perfectly moulded to her hips and the shiny tights drew my eyes to her sexy legs.

I remember how lucky I felt at that moment as I looked at this beautiful woman, both vulnerable and sexy in her state of undress, and more than accepting of me, a virtual stranger in her presence. I felt a real connection.

"Come, put these on." she said, handing me a pair of black knickers.

I was shocked:

"Wha...?"

"Well, you've already told me that you prefer women's clothes so why spend a moment longer dressed in those things when you would be happier in something of mine?", Helen said in a matter-of-fact tone.

I didn't hesitate and couldn't take my clothes off fast enough. I pulled the black silk panties up my legs and snugly around my crotch. At that moment I felt happier than at any time in my life so far. Here I was actually being encouraged to dress up!

Helen then gave me a matching black bra and black stockings which I slipped into like an expert. A pair of her panties padded each D-cup of my bra. She held up a silk negligee for me to slip my arms into:

"Come on so Charlie, let's do your makeup and see what a pretty girl we can make of you!"

Helen took her time doing my makeup. She blitzed around me using ten times more products than I would have normally used. As she worked away, at least twice I noticed her body sensually touching and brushing against mine.

Without letting me look at myself, she took a long blonde wig from one of the many cupboards of her work area and I put it on. Finally, she allowed me to look in the mirror and I had to fight back the tears from the emotion I felt. We could have been long lost sisters. We hugged lovingly making up for all the lost years.

She led me to the far side of the apartment where garments and costumes of all sorts hung. I tried on lots of clothes most of which were Helen's own creations. Her eye for fashion was incredible and she took photos of me wearing some of the dresses.

She chose a blue lycra mini-dress for me to wear for the evening. It felt divine on my skin. We retired to the living room for a cup of tea. Helen kept the conversation going:

"You look so pretty, you look more like a Charlotte than a Charlie... yes, Charlotte, Lottie perhaps?! Your youth and good looks are an asset to you and don't you ever forget that. When I was younger I became an escort to make ends meet. It was my own decision and I was always in control. My clients were wealthy and I made a lot of money catering to their needs. I know men better than they know themselves. That's why I prefer women. I think men are the weaker sex and women are stronger. I count myself lucky to have such insight into humanity but the downside is that I don't think very highly of men anymore. You are obviously not the average male and I would love to share what I know with you. Do you understand what I mean?"

"Is it that all men are pigs?" I asked.

"Well, not necessarily, but they are sexually weak in comparison to women and once you understand that, it can be exploited to one's advantage. Sex is there to be enjoyed and if you really enjoy doing something then why not be paid to do it?! I believe that most people have to wrong attitude to sex. If you want to do something then you should do it. I have had very few regrets living my life like this. Charlie... my dear Charlotte," she took my hand in both of hers and looked me in the eyes," I would love for you to understand and share in the wonderful life that I've had. You should use your beauty to your advantage and get the most out of life".

"You look gorgeous Charlotte. I've had many transsexual clients over the years and most of them would kill for your looks. How do you feel about dressing up like this? Is it just a sexual thrill or something you would like to do more full-time?" she enquired, trying to understand me.

"I don't know really, a bit of both maybe?" I suggested.

"I did notice how very turned on you were trying on those dresses earlier, your little cock was weeping" she said, her sexy mouth dancing and her white teeth beaming as she smiled.

I blushed.

"If it is a fetish then you then you will probably want to change back once you've had sexual release" she said suggestively, "would you like me to help to release some of that pent up tension?"

As she said this her hand moved up my inner thigh across the soft material of my dress which sent an instant message to my cock to swell up and bulge out of my knickers beneath my tight dress.

"Once you learn how to take control, things become very enjoyable." she said, talking lowly, almost whispering, in my ear.

Her hand moved gracefully up to my swollen cock. I almost felt an electric shock when she grabbed hold of it through the silky soft material and squeezed it gently while looking me in the eye.

"Would you like to become part of my world?...To understand the power that a woman holds over a man?" she asked teasingly.

"Yes mum" I said, confused and entranced, realising that it was the first time I'd referred to her as 'mum'.

"Call me Helen, Charlotte. Think of me as your big sister, here to teach you the ways of the world."

She kissed me lingeringly on the lips, the taste of her lipstick and soft sensual mouth was the most amazing thing I had ever tasted. A million thoughts shot through my mind at once. Was this wrong? Was this right? If it was wrong, it felt very nice.

There was no denying the attraction I felt for this woman from the moment I first saw her and everything she spoke about all day had made complete sense to me. We were soul-mates to say the least...with the ultimate physical bond.

She was so worldly that I felt like my sheltered life had kept me living in ignorance, unaware of what was really going on around me. The moment of that kiss had felt like an awakening...as if I had been reborn.

Helen stood up in front of me and undone the tie of her negligee to reveal her underwear. Her white bra held her double D breasts into the sexiest cleavage I had ever seen up close in real life.

Her slim waist curved down to her feminine hips. Her white silk high-cut panties which she had been wearing all day appeared bright and flawless against her tanned skin and the large lips of her pussy formed a visible silk silhouette.

"What do you want Charlie?" she asked provocatively.

I couldn't answer.

"Would you like to touch it?"

I leaned forward submissively and she urged my head towards her crotch with her hand. My mouth and nose met her soft panties and began to lick the thin material which covered her pussy.

My nose pushed between her pussy lips as deep as her panties would allow me. I circled my head to stimulate her by flicking my nose against them as deeply as possible, trying to trigger it. I could feel her pussy getting wetter.

She moaned with restrained pleasure as I did so which made me want to go further and deeper. The scent of her pussy was the best I had ever tasted and I yearned to touch its flesh. My hands rested on her soft smooth legs and the strongest desire I had ever felt for a woman overcame me.

I licked and sucked her lips through her panties enlarging and swelling them. Her panties were now wet from her juices which I drank down with pure uninhibited thirst.

With seductive grace she slid her panties off and gently pushed me back in my seat. She lifted my dress back to expose my crotch. My cock was rock solid, almost in pain, and weeping with pre-cum from this magical experience. She leaned forward and kissed me on the lips once more. My mouth must have oozed the scent of her pussy juices.

Her hand dropped to my cock. Her thumb and forefinger encircled the base of my cock and back of my balls with a firm grip and pulled them away from my crotch stretching my genitals out away from my body like they were some useless appendage.

Her other hand then touched me in a place I'd never been touched before. Her finger rubbed furiously on the area between my balls and my ass, flicking across the skin and swollen cartilage at the very base of my erection.

I moaned with unbridled ecstasy as she did and would have come except for the tight grip she had of my genitals. She moved forward on to my lap with the swollen, damp lips of her vagina touching the bulging head of my 7" cock.

I could not believe that I had been brought to the edge of cumming so many times already that evening and I could not bear much more. Her moist pussy lips enveloped the head of my cock teasingly and rested in that position as she squatted above me. Her cleavage of her soft breasts brushed against my face and her hard nipples prodded through the soft satin material of her bra.

Looking into my eyes, with one gentle movement she pushed forward and I was inside her. Momentarily, I worried about cumming inside of her and making her pregnant but her confidence in the lead role made me feel at ease.

She thrust her hips back and forth along my cock, sliding herself along it at an awkward angle giving the feeling of maximum friction for both of us. My cock swelled even bigger within her as it sloshed around the heavy juices and walls of her cavity.

I could not bear to take anymore and groaned in a higher and higher pitch as I began to climax. As she heard this she seemed to switch on automatically, mimicking and matching each of my groans like an echo of pure desire.

We looked deep into each other's eyes and felt an amazing bond. She thrust her hips with rhythm lowering herself on me with my cock going deeper and deeper until I hit her g-spot.

A huge gush of warm wet orgasm sprayed onto the head of my cock, surrounding it and causing a smooth slimy vacuum within her cavity which triggered a loud wail from me as my cock exploded.

As I wailed and came, she pushed herself up firmly from my lap, suddenly releasing my cock and leaving me there spurting semen all over myself and the beautiful blue dress which she had so graciously given me earlier. I felt embarrassed and ashamed of what I'd done but she looked at me smiling:

"You see what I mean about the power of a woman? You would never have had the courage to initiate sex with me but when I took the lead you just followed. Don't feel ashamed, it's just because you are male. Stick with me girl and I will show you how to get what you want when you want and enjoy every minute of it!"

She slipped back into her negligee and as she walked to the bedroom I could see the all the seductive confidence and elegance of a Hollywood sex siren. She was amazing. She was everything I aspired to be. I wanted her. I would do anything to be her. What did she mean by "stick with me"?

I cleaned myself up a little but sitting there in the wet semen-stained dress I tried to make sense of the wonderful and crazy day I'd just had. She was the sexiest, most inspirational, most uninhibited person I had ever met.

I kept wondering what she meant by "stick with me". Was she inviting me into her life? If she was then there was no question that I wanted to stick around and learn the ways of the world from her.

To be continued...