When She became He

A Good Friends Advice

"You need a good massage"

You know how it is, when everything is going so well, the only way to go................, is down. Let me explain. It started when I just knew I had to dump my boyfriend, even that was a loose term. The first part was true, in two ways, he had a cock, therefore a boy and he was a boy, not a man and, He, was no longer my friend. He had to go. Then, I had been thinking about how to dump him when I walked into my boss. And knocked him over.........., I was in a hurry. Staying late to get told off made me miss my bus and train connection. Then it rained.

The rain wasn't really the problem, my top was. It had been a beautiful morning and I had decided not to bother with a bra, the top was fine dry, actually it was even better wet. Completely transparent, not what I needed waiting for the next bus, that and my nipples. Usually I'm proud of them, quite full and pointy, when I'm turned on they are very sensitive as well, they're just the same when they are cold and wet. You could see everything......., and most people were turning for a second look.

The bus ride wasn't so bad, I could sit and sort of hide, the train was full. I had to stand and I do mean full. My poor nipples were being rubbed raw by the crowd around me, I was sure they had pressed in close after I boarded and nobody moved away when seats emptied. I thought my run of bad luck had finished, the extra body heat around me was drying my top and the sun was starting to break through, just the car ride home left.

Remember what I said, about going down, the car wouldn't start. A phone call and another wasted half hour, waiting for the tow. I was home but it didn't stop, both the power and phone company's' had joined f***es to empty my bank account, it didn't even stop there. I love/need my coffee........., I hate black coffee, I was going to pick up a bottle of milk on the way home, I had finished the last this morning.I just had to have my morning coffee......., that meant a walk to the shop.

"Cover Your Ass" I thought as I planned this little outing, I was not going to have this turn out as bad as the rest of the day. Walking shoes instead of heels, a jacket, just in case the sun and rain were going to play nasty, money, always important, keys, I wanted to get back in, anything else? Cell phone, in case of, well, just in case and I headed out on my great expedition............., to get milk.

See, forward planning helped I thought as I headed home, successful in my quest. The bottle of milk clutched firmly in my hand I turned into the home stretch, my home in sight and, as I came around the corner, my phone rang. One thing at a time, I stopped, dug out my phone and answered it..............., just as a truck came around the corner and............., found the puddle, the puddle I was stopped beside. Right beside. The shock of being drowned made me drop the phone.

In sight of home and safety, just a bit more and I would be nice and warm with my coffee and it was worse than the rain earlier. That had fallen down, okay, I got wet, my nipples stood out. This was like jumping feet first into a cold swimming pool. The cold water transformed from a nice puddle, just lying there, into a fire hose being aimed up my skirt.........SHIT.

I was thoroughly soaked so what the hell, I bent over to pick up my phone to discover, that was not all folks. The back of my dress had been f***ed up my back, and stuck there. When I bent over, a couple of the local learned just what a wet thong looks like from the rear. By the sound of the whistles they liked the view. Milk in one hand, I wasn't going to put my prize down for anything now and phone in the other, I thought, what the hell and shook my butt to try getting my dress unstuck.
The increase in whistles told me they really liked the view, and the show.

I could feel my cold wet dress hitting the backs of my legs, something had worked, just as a got the key in the lock the phone went off again. At least it had survived the dunking..........., no it hadn't, there had been no puddle left by then. I was wearing it.

Once inside I decided to do some more careful planning, 1 put the milk away, 2 put the kettle on, 3 run a bath, 4 undress, 5 put the wet dirty clothes in the washing machine, 6 check the bath, 7 check the kettle and make a coffee, 7,no 8 check the bath, it should be ready, 9 answer the damn phone. It was ringing again but I didn't want to answer, just yet, I blamed them, whoever for my misfortune. I needed my coffee first. I was feeling better all ready and turned................, and stubbed my big toe. Walking shoes verses stairs, stairs win. OUCH.

The washing machine was humming away, the bath was as hot as I could stand, the coffee was perfect, a taste of heaven, I picked up the phone. A few more scratches but what the hell, it still worked and searched missed calls. Three, all from the same number, Karen, my long time girl friend, I pushed recall and reached for my coffee. She answered so fast I nearly dropped my phone and my coffee, she must have been ready to call me.

Of course she asked why I hadn't answered earlier, I didn't want to relive the whole miserable day so I just said I was busy and then she dropped the bomb. Karen loved gossip, lived for it and didn't think before she spoke, she had seen my 'boyfriend' with another girl.

My now ex-boyfriend, so what. I actually think she was disappointed when I didn't explode and told her he was already an ex. Not worth going to the next stage, I hadn't had sex with him yet, thank god. He was a pussy hunter, I could hold my head up, he didn't score with me. Karen was disappointed, although not for long as she headed off on a new line. A friend had had a massage and had raved about it, the best thing since canned peas and sliced bread. I had to try it, to get over my break up. Yeah, right.

I didn't bother asking Karen if she had, it wasn't her style, she just passed on the info she gathered so it sort of went in one ear, and out the other until she said "her", how she just knew what ladies wanted. I switched to listening mode. A good female masseur was hard to get, maybe I said when Karen had a break. She was one of those, she talked, you listened, she didn't have time for two way conversations. As soon as she heard the 'maybe' she told me she would txt the number, she was so good it was by appointment only.

When I heard that it was back to 'in one ear' mode and enjoyed my coffee, I never let a cup go cold, and nearly dropped the cup, again. She was two streets over, I sat up, regretted that, cold air on my poor nipples, slid back and asked Karen to repeat the address. I knew that street, I even thought I knew the house and filed the info. It was Thursday and if Friday was going to repeat today, well, this weekend. It depended on the cost of the car repair.

I heard the washing machine stop, made my goodbyes fast using that as an excuse. She was a good friend but, and hung up. Just in time for it to ring again. I nearly dropped it, again, it was the garage, only a lose wire and it was on it's way here courtesy of a mechanic who lived close by. No charge if I could drop him home.

Things were looking up but, don't temp fate, another list before I moved, 1 get out of the bath and get dressed, well that was two, but, 2 warm clothes, 3 socks with my walking shoes, my toe still hurt. Not much of a list, I can do this........., and looked at the phone in my hand, 4 and 5 move the phone and coffee cup out of harms way.

I opened the front door and looked for puddles, all clear, patted my keys in my pocket, yep they were right where they should be and thought about making this, my lists, something to do on a regular basis, put a bit of order in my life and not just muddle through. My car glided to a halt. The mechanic was the older of the three I knew worked there and was thankful. One younger ones was known as a boy racer. It would be no trouble dropping him off where ever he lived, the price was right.

Back home, the car in the garage, no problems, the washing in the dryer, no problems, sorting out the mail, the phone account wasn't mine, I had assumed because it was in my box, it was mine, wrong but no problem. Things were looking up and the weekend was looking good, all I had to do was get through Friday, it wasn't even the 13th.

Early morning coffee, perfect, a car park close to the terminal, perfect, train and bus on time, I was waiting for Murphy............, things just couldn't go this well, could they. Yes they could, the boss had had another accident and it wasn't my fault. The gossip, his wife had swiped his head with a frying pan. Domestic troubles. I smiled to myself as I dialed the number of my weekend, 'I love me' plan. I was going to have my massage. My lists came back, scratch 'I love me' insert 'I feel me'. Don't tempt fate by being greedy, and I didn't need a boyfriend..........., yet.

I had to wait until eleven on Saturday, but even that was good, somebody had cancelled and, I had a seat on the bus, I had a seat on the train and, the car started. To top a perfect day, it was warm, the sun was shining and expected tomorrow.

I was sitting, enjoying my second cup of coffee, just waiting for ten forty, it was so good I was going to walk, house-hold chores done when it came to me, people got a massage to feel good, I already felt good. It could only get better......., if I made another list............., I couldn't think of anything to put on my list. Appointment, made, dressed right, easy to undress, done, coffee, done, ready on time, I was early. I had a sudden belly full of butterflies, what had I forgotten? I was nervous.

There was nothing so I put another dab of deodorant, just for something to do. It was time. Nothing happened, I got there, it was the house I had remembered, yes, I was on time, it was clean and tidy and she..........., Oh My she was built. Her breasts a little bigger than mine, her low cut top showing they were nice and firm, also showing no bra, a sexy little short denim dress and long black hair. Very polite as she showed me where to undress and handed me a warm towel. I knew why she had a following.

The massage area even looked good, a well set up area with the table padded, bottles of oils and scents, warm and inviting. I lay as directed, on my front with the towel d****d across my butt. Surely Murphy would leave me alone today. I waited.

Soft music started as she entered, she had a pointer and asked if I could see any area of the chart that was a problem. I hadn't even seen the chart before I was so happy nothing had gone wrong and explained that this was just a relaxing massage.

She asked me what I did as she lightly ran her fingers up and down my back, her voice soft, soothing and then an equally easy to take scent as she told me to relax. I did, so much so I nearly drifted off, the scents, the music, they were just little add-ons to the feel of her hands. It was a deep massage but not one that would hurt. I closed my eyes and let my mind drift.

It must have drifted a fair distance. I felt her softly shake my shoulder and ask me to turn over, I smiled a silly smile and told her I couldn't. I was so comfortable. A gentle hand rested on my bum and pushed, I rolled, my hand caught under her skirt and lifted it as I rolled away from her. My arm was useless until I got my shoulder a little higher, her dress came with my arm until.............., A COCK.

"She" had a cock. It was funny, I think, I had reached balance point and flopped onto my side. "Her" cock was stiff enough to hold the dress and the head poked out a little, inches from my bald pussy, "she" had moved closer to the table to help me turn. I watched as "she" blushed and tried to cover it with her dress, that wasn't going to work, "she" was getting harder. I must admit I was paying close attention as "she" lifted "her" dress and tried to tuck it back into her panties. That wasn't going to work either. I was looking at a nice hard cock.

"Don't you think you would be more comfortable if you took your panties off?" I asked, trying to sound casual.

"I usually do, but only after the second or third time with a client, I'm sorry but while I was doing your back you......, you were leaking, I got a little carried away, I'm really sorry"

"Stop saying sorry and strip off, you do do naked massage's, after all I'm naked", I realized I was naked, no towel anywhere, then I realized I was more than naked. One leg bent and raised, the other flat, had opened my slit, I was leaking I was so wet. Her cock was still very close.

"You wouldn't mind?"

I lay fully on my back and spread my legs as far as the table would let me. I wasn't just wet. I was horny. "Strip, you can see my pussy, I want to see your cock. All of it. Fairs fair" and lifted my head. I did want to 'see' her.
I did want to see her cock but strangely it was her eyes that drew my attention, her make-up, still perfect, highlighted the fact she was looking down. I expected that, a bald pussy, her cock, there was 'sex' in the air. I didn't expect to see her looking down and..........., away. Murphy had struck.

I realized I was playing foot and mouth games, my foot, my mouth and had another thought. Had it become 'feet' when Murphy's Law had kicked in, had I gone to far when I had, and I had, 'ordered' her to strip. No time for a list now, Damage Control.

"Look, that has to be uncomfortable and I want you to be............, relaxed, so I can relax and enjoy the front half..., of the massage. You have done a great job so far and I would really like you to continue. Ha, just think that we are at a nudest camp and you are the masseur. And another thing, I had a real shitty day on Thursday and you are my 'I feel good' therapy, and, it's working. Please, just get comfy..........., so we can continue", this time I lay back and closed my eyes as I felt her hand rest on my thigh, very close to 'home base'. And a gentle squeeze................

I had never really thought about 'T Girls', cross dressers or even Shemales, they had never crossed my path, until now, and decided not to ask, not to probe. It was obvious she was shy or......., a submissive. I had no experience with that side of thing's either. Whatever she was she was all woman in getting undressed. I didn't hear a thing and at least one hand was touching me the whole time as she worked her way down to my toes. I opened my eyes to tell her I was ticklish. She was naked.

I f***ed my eyes to become a camera, open, a quick photo, then shut. The picture was taken and embedded in my brain and like a good photo, you had to look at it carefully............ It started with her smile, her whole face smiled, a lovely slim neck down to firm shoulders down to perfect breasts. OMG, perfect ski jump breasts with dark pink, nearly rose coloured nipples. They say a picture is worth a thousand words..........., I think they are right, I couldn't see her cock from this angle but all I had to do was rewind the film, just a little.

It wasn't long, it wasn't fat, it was cut and the head.........., I hit zoom. It was one of those with a very flared head, you know the type, once they're in the ridge stops it from slipping out, and, if the owner knows' how to use it, You can feel it, your cunt just grabs it. Opp's, I felt a tissue touch my lips. I don't think 'leaking' was the correct term just now.

She had got to the top of my thighs, on the outside and I followed her fingers in my mind as they caressed their way up to my shoulders. I knew she was going to start working down. I knew I was going to climax when she got to my breasts. Somehow I also knew she was getting her pleasure by giving me pleasure. I didn't just relax, I let my body go. I was floating in a sea of sensations, I was 'feeling me', feeling good.

It was as if I had left my body and was looking down, seeing and feeling.
I was in a new state, one I had honestly never been in before. I loved it, a state of pleasure with a touch of sexual feeling. The normal for me was a state of sexual feeling with a touch of pleasure, my whole world had been turned upside down and inside out by her/him, whatever. Fuck it felt good............, then, it just got better.

This was another place I had never been, woman on woman, but, the feeling of her breast on my b**st, her hard nipples on my hard nipples, first softly then harder.......OH YES, OH FUCK............., a tissue was not going to help now. I climaxed.

It was the hardest thing I had ever done..............., nothing.

I didn't just lie there, my body was moving............, but it was her, she was giving, just as I knew she wanted to and I was receiving, not taking. Heaven.

OH Shit............, she was heading south of the border..........

A very talented lady, her breast was still in contact with mine, her arms were stretching, taking those magic fingers closer. Over my belly, down, closer. I was going to die........, over my mound.......closer........., shit. She missed. Close, but to either side of my aching clit. Stop, wait, they came back. SHIT, she missed again. My body had taken over, bucking and twisting, trying to get those fingers on the right spot. It didn't help, she was playing with me, torturing me.

I felt her breast leave mine, I felt her fingers slip deeper between my wide open thighs, I felt............., OH GOD............., I felt her hot breath blowing on my exposed clit. This was what she had been waiting for, watching for. My hood had drawn back. My clit was hard and exposed, another breath............, it couldn't get better, could it?

My knees lifted and parted, my hips lifted, searching.........., I didn't do it, at least I hadn't told my body to do it......, another breath. I was about to beg for release when.

She sucked my clit into her mouth.................

Goodbye climax. Hello Orgasm..............

My whole body shook, trembled as she sucked harder, and then............

I felt a finger snake in between my open lips until it was buried. Another suck, another wave of pleasure to ride............., another sensation..................

Again my body was doing it's own thing.................., my fingers closed around the cock that was now resting in my hand..........., I squeezed. She sucked. She curled her finger and hit the spot...................

I died............

I didn't want to wake up, I was in heaven and By God I wanted to stay. But gentle kisses and light licks brought me back to earth, the other, just as important. Her hard cock was throbbing in my hand.

"Please, I croaked, I tried again, "Please, let me suck you. Please......", I begged.

She looked up, smiling, "Would you, I don't usually................"


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Posted by chchboy
3 years ago    Views: 983
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3 years ago
3 years ago
A wonderful story, for heavens sake don't stop there,,,
3 years ago
Best story ever keep going
3 years ago
Please continue.
3 years ago
Fantastic boy i need a massage now thanks