Transgender First

[subserviant]

I finally did it .It had taken a long time ,now its was down to a few hours .I had been considering going for a massage with a transgender woman ,that is one who was gendering from male to female .I pursued the adds in Backepage ,Leos List and others .Her photos had done it .I had fantasized about seeing a so called ladyboy ,Sherry filled my wants to a T .
Judging from her pictures it was difficult to believe she wasn’t all woman ,asian ,stunningly beautiful ,I dashed off a message .

 

[jrambat69]

Been wanting to do something like this but so scary now a days on who to trust weather their real or not. Glad to here your first was great

 

[subserviant]

I found it a little strange that after I made contact ,she sent back another message asking me to send her my expectations .Well this was not what I expected . Should I keep it simple ,oh just a massage ,but then she did say in her ad that she did prostrate massage so what the hell I decided to go whole hog .
I began the reply by telling her my desire to be dominated ,it was another option that was mentioned in her ad .I also mentioned a video I had watched where a man was secured to a massage table naked while the transgender domme walked slowly around him pinching his nipples ,his penis ,squeezing his testicles ,finally removing her penis from her clothes ,holding the guys head while placing the head of her penis against his lips .
I left it at that ,wondering if I had gone to far ,but then she had asked Her response was immediate
Yes ,she had no problem with what I had asked for ,in fact she was looking forward to meeting me .It turned out she is a natural dominante ,enjoying dominating a man .
I have a time open this evening ,7pm ,send back a reply ,oh and don’t be late if you accept .
A shiver went through me ,holy shit here was the opportunity I had dreamed about ,I had only to think about it for about 2 seconds ,yes 7 is good .I’ll be there .
She sent her address .I needed to get to the bank ,not knowing if she would take a money transfer ,so better be prepared .Shit it was already 4 I had to bag my ass in gear
I had to enter my pin 3 times ,my hand shook ,my mind raced ,she charged 200 but what about a tip ,not wanting to take to much ,after all I had no idea what I was facing ,she could be out to rob me .Stop it ,My mind raced in a hundred different directions ,just do it .
Hurry home quick shower ,still a half hours drive .

 

[subserviant]

I would have made it with time to spare except for that damn detour ,getting behind a slow moving vehicle ,well still not to bad I figured ,only a few minutes late .I was a bit surprised ,her place was on the outskirts ,a nice place ,older but the that well maintained manor house look .
She was every thing I had ever dreamed about ,gorgeous ,I first thought she must have been an associate ,no one could look as good as her and not be all woman .Unmistakably Asian ,she was the perfect Ladyboy or at least as far as I knew how Ladyboy's where supposed to look .Her demeanor however was anything but gracious ,I introduced myself ,Your late ,I should cancel our appointment ,however since this is your first time we will continue with the appointment .
Not what I was expecting .I stammered out the reason for my tardiness only to be silenced by ,I dont want to hear excuses your late now we will carry on .
I followed her down a hall to a room set up with furniture and a massage table ,she picked up what was a print out of my email explaining what I was seeking ,I noticed a silver tray on a side table ,had enough wherewithal to drop the envelope containing the cash into it .
I found it interesting she began, that the video you mentioned also happens to be one that I also like ,only it stops short of what you really want ,that is to be dominated .For the first time she smiled a little ,I can certainly take care of that ,only it won't happen this visit to any great extent ,if you are really serious it will happen subsequent meetings .
I nodded in agreement already certain I would be back,often .
She turned ,standing with hands on hips feet apart ,strip ,every thing off lets see what you look like .
My heart skipped a beat ,this is what I had hoped would happen but at the same time a wave of embarrassment flooded over me .Every thing ? Socks to ?
What did I just say ,you will find to your dismay if I need to repeat an order the punishment will be extreme now do as I told you .
Standing in front of her was acutely humiliating ,my hand automatically dropped to cover my gentles ,it brought a snort from her If that's all I had I would try to hide it as well ,hands at your side.
She slowly walked around me ,you have let yourself go ,a prod to one of my ass cheeks ,you need to work out .
I protested ,I do work out ,every day .A slap to the back of my head ,shut up ,I dont want to hear from you unless I tell you to speak ,is that understood .
Yes ,I answered meekly ,waiting ,wondering what was next .
On teh table face down she ordered .

 

[subserviant]

Wow from nice to bitch in 2 seconds ,but then it was what I had asked for ,a Domme .I didn't know what to make of her explaining that we would only touch on the things I had mentioned in her online questionnaire ,but then I knew from the moment she opened the door that i would be back .Now lying face down naked ,I ran what I had told her through my mind,remembering how I had told her it was a fantasy to be made to give her oral ,but also that juts the thought of finishing to completion ans swallowing was so revolting to me that unless I was some how secured in no way could i do it ,by the same token I had explained that the thought of being secured filled me with concern ,as I in no way wanted to be completely helpless with some one I didn't know .
She had not addressed the issue in the return email ,and had not brought it up since my arrival ,so I assumed it had been forgotten and really I had no need to worry as this first visit was going to be pretty much a straight massage .She was very good ,I felt an immediate relaxation ,after a few minutes I almost fell asleep .The stroking of my ass brought me back ,the tip of her fingers tickled my oh so sensitive rose bud .
Are you ready to the prostrate massage ,a little lube ,then one finger slide inside ,the after a bit another finger .I was in heaven ,my loud moan brought a chuckle .You like this ,her fingers now slide in and out of me ,in effect fucking me ,My ass raised ,seeking more ,right at that moment I would have done anything just to have her continue .
Unfortunately it came to an end .Our time I'm afraid is up ,as she stripped off the glove . Could I please get another hour or more I pleaded ,
I'm afraid I have another client booked but if you wish I will check when I have more time available .
She opened a laptop ,Friday ,I have a free afternoon and evening except for an hour at 6,if you wish I can work around around that appointment ,I can give you some thing to do to keep you entertained ,it up to you of course ,I do have special pricing for over nights ,we will be able to address all your fantasy .
I agreed ,absolutely ,I didn't care what the price would be ,my only problem was that it was Wednesday ,how the hell was I going to make it until Friday .
You had better get dressed she smiled ,it probably wouldn't look good to walk out naked .

 

[subserviant]

I was on cloud nine ,the 15 minute drive home seemed to take forever ,I stroked myself through my pants resisting the temptation to pull into a side road and jerking off wanting to relive what had happened earlier ,that feeling of ecstasy,I shivered running it through my mind ,it was all I could have dreamed of ,the feeling of her fingers inside me ,I wondered if this was the way a female felt when getting a dick inside her .
My mobile dinged just as I shut my pickup off .The message from Sherry simply read You are not to abuse yourself ,I will find out from you if you do not obey ,The punishment for disobedience will severe .
That was it ,forbidding me to jack off .Fuck it ,how would she ever know ,I hurried to the bedroom ,stripped off ,began pumping ,seeing her in my minds eye ,it took only a few minutes ,the orgasm was mind blowing ,never in the many times that I had masturbated came even close .Then the guilt ,shit what if some how she got it out of me and cancelled Fridays appointment.I am not a good liar ,but then she may not even ask .I thought about what she had said about finding some thing to entertain me ,another thing to worry about The wait was going to be a long one

 

[subserviant]

I made sure I was on time for our next meeting ,I toyed with the thought of being intentionally late to find out what the punishment would be but was concerned that she might tell me to get lost ,there was no way I wanted to screw up .The smile as she opened the door ,seeing her , I felt my dick getting hard ,hopefully it would get soft before we started the massage ,it was embarrassing enough to strip in front of her let alone having a boner A bit of a surprise as we went not directly into the room where she had taken me the first time but into a living room den of sorts .
She sat ,crossing her legs showing some thigh ,my throat was dry ,with anticipation and nerves Waiting ,strip every thing off ,it wasn’t what I expected ,not out here but I hastily obeyed .She grinned at seeing my woody ,I assume your happy to see me ,her grin getting wider .I sputtered out a yes ,my embarrassment now acute .
She gazed at me ,I have a proposition for you she began .But first ,how many times have you jerked off since Wednesday .Remembering her order ,I stammered I suppose a dead give away ,Eerr none I replied .Your lying ,tell me or you can leave ,I want the truth .
My face felt like it was on fire ,4 times I mumbled ,I’m sorry but .Enough ,you disobeyed .we’ll deal with that a little later ,And believe me for your disobedience and your lying you will be sorry .Now for my proposal.The boy I had doing my cleaning and chores has resigned ,I am offering you the chance to serve me in that capacity .Suffice to say you will be my maid ,if you accept we can get into the details
A rather awkward moment ,standing bare ass naked being offered some thing I had only dreamed of .
Yes ,yes I would love to I replied immediately.She smiled ,you might be less eager when you Find out what a demanding task master I can be .
At that moment I wouldn’t have cared what she said ,I was elated.

 

[subserviant]

I immediately began having second thoughts after she explained what would be expected of me .It was going to be quit a commitment ,but then I reasoned in my mind I had nothing else going on I had recently sold my software development business for an obscene amount of money ,so no work commitment ,still ,
You will be responsible for the complete cleaning ,the laundry ,doing any errands ,on occasion being involved with myself and a client .You will be required to be present when ever I tell you .If I think of anything else I will tell you .I require complete obedience ,if you do anything that displeases I will punish you as I see fit .if the infraction is bad enough ,you will leave .Well ?
I only had to mull it over for a few seconds ,Yes I still agree ,my reply probably over eager .
Excellent ,I believe we are going to get along famously .Now to the matter of your disobedience in regard to abusing yourself .
She beckoned me into the massage room ,picked an instrument from a shelf .An evil smile crossed her face .I warned you the punishment would be severe .This is a fun little toy I picked up in Europe ,its a suction device ,not unusual in its self except that the upper limit is such that it can actually pull a penis completely from the body ,or so I was told .She motioned me to her ,my dick now rather flaccidTaking my penis in one hand inserting it into the clear plastic tube ,,she pressed a button ,it activated a small pump attached to the tube by a medical type hose .The result was immediate,my cock was sucked in stretching it ,the pain shot through me ,I actually screamed trying to pull away Her laugh sent shivers up my spine as she pushed the button again .
I guess I had forgotten that she was all woman but still had the strength of a man ,kneeing me .I dropped howling in agony ,begging her to stop ,I was fully expecting my dick to be ripped off .She knelt Pulling my head back .So have you learned your lesson ? I could only nod my head violently
She released the pressure .Your cock will hurt so much for a few days so unless your a complete masochist you won’t have any desire to jack off .Just be warned this was just a little warm up session,if I have to repeat it ,well you now know what will happen .I lay on my side holding my balls afraid to even touch my cock .
After a few moments she lightly kicked me in the buttocks,Time for you to go to the kitchen ,I have a client coming ,you have dishes and a bathroom to clean .
She led me into the house proper ,showed me where the cleaning supply’s where ,as she turned she took my still burning cock ,gave it a couple of hard wanks ,again the pains shot through me Smiling ,we’ll have some fun after I get done ,a light slap to my balls ,she went to greet the visiter