Sickness, or a Blessing?

So about three years ago I went to the doctors about a strange rash that covered my legs, arms back and chest. I had the usual tests and all came back negative. Other symptoms included weight loss (I had dropped 25 kilos in just under 3 months), vertigo, itching and then came the pain. Eventually I was admitted to hospital. Bedbound and almost incapacitated I was on the receiving end of a rather unpleasant bed bath when the nurse queried "is your penis shrinking?" I once wielded a thick 7 inch long cock. With the aid of a mirror I was horrified to lay my eyes on my shrinking manhood, it was now less than an inch, and my balls were almost invisible.

With this perplexing revelation to hand the doctors performed one more test, then I was diagnosed with Complete Androgen Insensitivity Syndrome CAIS for short, and seemingly I was among the first genetic males ever to contract it.

I entered into a modified HRT program and within 3 days the pain and the rash were gone. Despite my still dissipating manhood my libido was returning.

After a few weeks my body was healthy again, but my mental state was less then repaired. The medication I was prescribed was designed to help mature women through the menopause, and I was a bundle of hormones. I started attending a group therapy session at my regional hospital, and I found out that while I was the only "man" I was not the only one suffering as I was.

After most sessions we ended up in a nearby wine bar. My super charged libido was matched by most of the ladies in the group. More often than not I accompanied one of the group members home.

Alas, it was not long before my shrinking penis made penetration virtually impossible. It certainly was not pleasurable to my female companion. My cock once my pride and joy, now resembled a large clitoris. My testicles had ascended back into my body so my empty scrotum looked like hideously saggy Libya lips.

The hormones turned my manly stubble to thin and wispy barely noticeable hairs. My hips and waist began to enlarge as did my pectoral muscles giving me a b cup chest. My manliness was a thing of the past, all I was missing was a vagina and a gspot, well and the desire to be a woman.

Sam was a 53 year old divorcee, who had a rather traumatic time when her change came about. A beautiful woman, with smooth olive skin, short cropped coal black hair and emerald green eyes. Around the same time of her menopause starting her husband decided that he was due an upgrade in the wife department. So he purchased a newer younger model, in fairness he made sure that Sam was well looked after.

She had a wicked sense of humour and made me smile even on the worst of days. Orgasms had become a long forgotten thing of the past, my dick was too small for penetration, and my balls no longer produced seminal fluid, I would masturbate to the point of boredom but never did I cum. Sam changed that. She noticed that when we spent time in bed that I never offered her my neither regions to allow her to pleasure me. One night she got me drunk, got me naked, lowered her luscious pussy onto me and writhed as I expertly ate her out.

I was so focused on in her delicious pussy that I failed to notice that she had taken my little clit into her mouth and was sixty nining me. I did feel her index finger probe my ass hole, and I really felt it when she began to tickle my tender prostate.

The first orgasm I had, had in two and a half years blew my socks off. I honestly couldn't speak for twenty minutes. I had a ringing in my ears two days later. I felt like a man again.

Sam and I became close. So close that I totally misread the signals, and proposed to her. She was not ready for another husband especially one as pitiful as I was. But she let me down gently, we started to spend less and less time with each other. But we were still friends, and we still slept together from time to time.

It was on one long lonely weekend that something new happened. I still blame the hormones I was taking but new desires crept upon me.

I was lying naked in bed trying desperately not to be horny and failing rather miserably. Unable to bring myself to orgasm, my mind turned to Sam. But before I fell into another bout of self-pity and tear soaked tissues, I remembered what I liked to do most, other than lapping away on her sumptuous pussy. I loved to watch her dress. It was so deliberate, so elegant, and so precise. Never a hair out of place, her makeup was perfection. I was always captivated by the transformation from a naked middle aged lady to a glamorous woman who would not be out of place on a Hollywood red carpet.

Even if she was just putting a pair of old jeans and a shirt, to go for a walk in the park she followed the same ritual. It would take forever, apparently it drove her ex-husband mad. But I loved the show.

One night was extra special. We were going to her ex-husbands wedding. She spent the day at the spa. When she got back her skin was radiant, she had perfect French manicure and pedicure. Even after this she went into her routine. As I thought about it, my juices started to flow. I was getting worked up in to an oragismless frenzy when I remembered that we came back to my place after that night and her clothes were still in my wardrobe.

I hesitantly approached it, unsure of why I felt such nervousness in my own bedroom. There hanging on the inside of the door was her elegant emerald green strapless ball gown. Her matching shoes sat where she left them at my front door, her lingerie was still in my washing room (unwashed) and her matching clutch bag was sitting on a shelf in my wardrobe. I held the dress up to my body, the smooth material sent shivers down my spine as it lapped across my naked body, as I inhaled her odour waves of eroticism washed over me.

A wonderful idea came to mind. I gathered her things and set about the strangest thing I have ever done.

Sam always started with a glass of wine. I ventured into the kitchen and poured myself a liberal serving of chateauneuf du pape, but like Keith floyd I was pretty sure that I would need the bottle, so I brought it into the bed room with me.

I stepped into the shower cubicle with my Philips electric hair trimmer and set about trimming my body hair. Once I had done this I took my Mach 3 and liberally applied shaving foam on my legs, arms, chest and pubic area. Carefully and painstakingly I removed every single hair from below my neck. Sam would wax or use an epilator, I didn't have either at hand my manly shaver did the trick.

Hairless Sam would step into the shower, if she had time she would run a bath and soak in it along with a peach flavoured bath bomb. I was in too much of a rush so I showered. She had left some of her products in my bathroom and I followed her tried and tested grooming regime to the letter.

I washed my shoulder length blonde hair with her very expensive shampoo, once I rinsed I massaged in the equally expensive conditioner and left it, while I washed my face with a face wash. I poured her French shower creame onto my loafer and washed my chest, as much of my back as I could, then my belly, privates and finally my legs. Once my skin was cleaned I rinsed out the conditioner with ice cold water.

Stepping out of the shower I wrapped a long white towel around my body just under my arms, and twisted another towel around my hair. It was time for another hit of the wine. I didn't have her expensive moisturiser so I liberally began massaging nivia after shave balm into my skin. Taking my time to ensure I did not miss a single millimetre of my skin.

I finished off the bottle of exquisite wine and returned to the kitchen to retrieve another. Wrapped in my bath towel, I felt deliciously feminine as I did.

Returning to the dresser I began to apply what was left of her makeup. I watched her do this several times but I could not remember the order of things. So I googled it YouTube is a wonderful tool.

I blended in the foundation and tried my best to even it up. Then using a concealer I hid by blemishes. I brushed in some eyeshadow, and struggled with mascara but not as much as I struggled with the eye liner. Then on to the lipstick a nice red colour, I did enjoy applying the lipstick for some reason.

I will be honest, my first attempt at doing my makeup was a complete dog's dinner. I am sure the bottle and half of wine was no help either. I washed my face and started again. The second time wasn't much better, so off with her head again. The third time while not a charm, was good enough for me.

Next was the lingerie. WOW

The feeling of rolling those hold ups up my freshly shaven legs was sensational. It was so good I took them off and rolled them back on again. Sensational or maybe it was the wine talking. Sam always started with her tights or suspenders, oddly if she wasn't wearing trousers she would then put her shoes on. I was planning on wearing a dress, so I slipped my feet into her sexy black satin stilettos with a chrome heel, the sole of the heels matched her dress. It was a tight squeeze, the shoe were a size 7 but my size 8 feet slipped in with a little wiggle.

Although I was now three inches taller, it wasn't the new found height that stood out. It was the way the shoes made me stand, my calf's seemed fuller yet slimmer, my naked ass seemed appeared pert and somehow my whole body shaped changed.

Once I had got over admiring myself, I pulled Sam's black lace panties on, but not before I gave them a quick sniff. I could just make out the odour of her sultry pussy musk. The bra was one of those strapless things that stuck to your chest and pulled together to form cleavage. As I have said before I had a little a or b cup. With this bra I was approaching a c cup, with a magnificent plunging cleavage that any bimbo in her twenties would be proud of.

After another slug of wine I unwrapped the towel on my head, and set about blow drying my hair. Sam has short hair so I have no real point of reference on this. Like I said I have long blonde hair so I dried it and brushed it. It looked too much like me no matter what I did so I decided to pull it into pig tails. Not that glamorous but different enough from my everyday appearance.

Time now for the dress. I once more took it out of my closet, as the material washed against my smooth skin it felt different it was electrically charged sensuality. Im sure if my penis could still get hard, it would be putting eyes out. But as I said I no longer had a penis of any kind. My little boy clit was throbbing though.

I stepped into it and pulled it up. Thankfully since my rapid weight loss I was a slightly slimmer than Sam so the dress fitted quite nicely. I let out a little gasp, when I first saw my reflection. I was taken aback by the woman standing looking back at me in the mirror. My heart was palpitating, I'm sure this is what it was like for a bride when she first put her wedding dress on, on her big day.

I picked up my phone to snap a photo of this wondrous occasion. That's when I noticed a message from Sam.

"Honey, this would be Greg and I's twenty fifth wedding anniversary, I really don't want to be alone tonight. Would you mind if I call over?"

This was followed by another message two hours later. "I will just call over. You must be out. Maybe I can surprise you when you get home. I got us something to play with, I think it will take both our minds off things ;) I will be there some time after nine"

The clock on my phone said that it was nine fourty five...

Bugger

Sam and I where lovers, well friends with benefits. But this was premised on the fact that deep down despite my medical flaws I was a heterosexual man. The person in the mirror looked anything but a heterosexual man.

And that dear readers is when Sam entered the room. As always she looked resplendent, in a white flowery summer dress, a straw summer hat, white stiletto heels and immaculate make up.

Sam didn't see her boyfriend in a dress. In the short seconds before she turned to leave both embarrassed and emotionally distraught, she saw a girl that her boyfriend had chosen to be with instead of her. The anniversary had trawled up her pain at being rejected by her ex-husband, now she felt that I was rejecting her as well.

Through her tears she almost whispered "I'm so sorry please tell Stephen, that I'm sorry."

As embarrassed as I was to be caught in her clothes. I loved her too much to see her wounded in such a painfully familiar manor.

Through closed eyes and gritted teeth I mumbled "Sam, it's me." I couldn't dare open my eyes, I feared so much hurting her, and her approval was about all I had these days.

"Stephen?" I could only manage a nod.

"Why?"

I still had my eyes closed, and tears were starting to choke me. "I don't know."

"Why won't you look at me?" she gently almost mournfully asked

"I cannot face disappointing you." She stepped closer to me "My darling." With that she kissed me, and I experienced my first lesbian kiss. The coatings on both our lips felt slick the combined taste of the lipstick blew my mind. Her hands reached up and took me by both cheeks and she pulled me closer.

As our embrace slowly but passionately subsided I opened my eyes to see her smile. In the time that we had spent together I had of course made her smile. I like to think that I even made her happy. I am not sure how, but the emotion on her beautiful face was somehow different.

As I gazed at her, I bit my bottom lip, and I swear I could see a fire erupt in her. She pounced on me. We fell onto my bed and she straddled my waist. Her hands and lips ran riot over my face and body. She ground her crotch against my pelvis.

Just as suddenly as she started she stopped. She leapt to her feet and unzipped her dress. It fell to the floor revealing her nakedness. She may be in her fifties but she spent as much time in the gym as she did she did in her twenties. She had her boobs done for her fiftieth birthday so they seemed as perky as a teenagers. Not even a hint of saggy skin anywhere.

I lay there on my back with my knees up, still fully dressed in her lingerie, her green ball gown and her black heels, she parted my knees and looked the skirt of the dress, and said "god we have good taste" she began to delicately began rub her soft hands up my nylon encased legs. I let out a soft moan as she reached my panty line. Softly she pulled the panties to the side and slipped her fingers onto my boy clit then down to my back passage, my body shuddered.

She pushed my knees further apart, and lowered her head toward my crotch. Pulling my panties to one side she began to perform cunnilingus on me. It felt wonderful, she took my two centimetre engorged clitoris into her mouth. As I looked down at her from between the mounds of my own breasts, something felt right.

Soon she lifted her head, and turned her body so that I could taste her. She lowered her sumptuous pussy onto my face, and I went to town on her. It did not take long but I felt her tense up which usually was followed by her orgasm, just like clockwork she began to cum. Maybe it is the fact that I no longer can achieve orgasm but there is something so incredibly satisfying about lying under a woman as she cums in your face.

As her orgasm subsided, her breathing slowed back to normal and she recomposed herself. She said "thank you." I responded by giving her pussy which was still inches from my face another tongue lashing. She recoiled and rolled off me, she sat on her knees at the top of the bed beside my head. I could sense her looking me over.

"Sweetie please let me see just how beautiful you are?"

"What do you mean Sam?" I innocently asked.

"Stand up, and give me a twirl please." I did as she bade and smoothed out the fabric of my dress before slowly turning around a couple of times. It was when I had my back to her that she asked me to stop. I looked back over my shoulder and she asked me "Darling please bend over so that I can see that lovely arse of yours." Once more I did as she asked, I lifted the hem of the dress and exposed my satin covered ass. She was soon kissing my cheeks, before she lowered my panties parting my ass and sticking her tongue into my bottom. Her hand was creasing my nub of a penis. While this was never going to bring me to climax it was enjoyable.

So I was a little disappointed when she withdrew her tongue, only to replace it with one of her slender fingers, then another and another. I could feel her trying to reach my prostate, she wanted me to experience another orgasm. Alas I knew that it was unlikely to happen, like I said it was a thoroughly pleasant experience so I went with it.

I felt gaping when she withdrew her fingers from my opening. I looked back over my shoulder at her, she took her fingers from my anus and put them into her mouth and sucked on them before offering them to me. I unintentionally chuckled as I took a taste of my ass. As a viral twenty something male I often joked with my bloke type mates about getting a girl to go ass to mouth. Here I was dressed as a beautiful woman, standing legs spread, my girlfriend had just fingered my ass and now I was tasting it. Had I becum the ATM slut we craved only a few years ago?

"What's so funny?" Sam asked, as she walked to her bag that had been strewn on the floor.

"I just wonder what the me before the CAIS would think of this?" I noticed what she had pulled from her bag, it was a 'J' Shaped rubber contraption. One end was phallic shaped the other had a black tennis sized ball on it.

"What is that?" gingerly I enquired.

"Take off your dress and knickers, and lets have some fun." She disappeared into the bathroom as I disrobed. When she returned she was holding a tube of lube and the ball end of the rubber thing was buried in her pussy she was busy rubbing lube the protruding end.

"Why have I got the feeling that I'm about to lose my virginity?"

"Don't worry I will be gentle." She winked then said "To start with."

I lay on my back on the bed, and offered her my pussy. She liberally applied some more lube to her fingers and started to finger me again, spreading lube up my passage. I raised my legs up to give her better access, and she eased forward. I felt the tip of her cock touch my opening, and it instantly send shivers down my spine. She edged ever closer, and the sheer force of her pushed the tip into me. It was much bigger than Sam's delicate little fingers. Much bigger.

It felt like it would rip me apart, I put my upturned palms on her pelvis to slow her down while I got used to the length and girth invading my ass. She continuously whispered into my ear words of encouragement.

It wasn't long before her pelvis met my ass and she was completely inside me. We rested for a few seconds, and she undid my bra releasing my sensitive boobs then she took one of my little nipples into her mouth. I gasped as she gently bit down. Then she started to slowly move her hips and I felt something again. This was going to work, I might get to cum again.

"Sam, please don't stop, fuck me." I begged as I grew closer and closer. She happily obliged.

"Oh baby fuck me harder, I need this so bad." I urged her forward. She sat up and took my heels in her hands. She ploughed me hard, and I needed it. My knees where brushing my ears. I was soo close when she shouted

"I am cumming baby" to which I replied "Please not yet, keep fucking me. I am so close."

She kept her rhythm, she kept fucking my ass as hard as she could, I could feel the orgasm building and building from deep within me. Every stroke brought me closer and closer. Just when I thought that it was going elude me, it exploded out of me. I convulsed in ecstasy and I screamed the scream of a million satisfied women. Two strokes later she joined me, covering us both in her sweet urine filled cum. Before collapsing on top of me.