I have been a closet cross dresser for many years. A few people knew but it wasn’t well known and that is how I liked it. I enjoyed dressing up and prancing around my flat in ladies clothing but I always had fantasies about going further. I kept stopping myself from doing anything further but there was that burning desire to be truly slutty inside of me.
One of my best friends, Hannah, knew about my cross-dressing and whilst she wasn’t interested, she loved the fact that I was so different from all her other male friends. I had even cleaned her house whilst dressed as a maid on one occasion and she laughed all afternoon as I totted around in my uniform and heels. One day we were just hanging out and I asked her what it was like giving a blowjob and she replied, ‘well why don’t you just find out yourself sissy?’
I looked at her and said that I was straight and she laughed, ‘you may fancy women but you also want to know what it is like to be one’. I conceded that I thought about it but it wasn’t something I actually wanted to do, ‘shame’ she said and we carried on drinking and just chilling out.
Towards the end of the night she asked me again if I wanted to suck cock and I said that I’d like to but that I was scared and I know that I’d wimp out. She smirked and said nothing and I went home.
I woke up with a terrible hangover but in my own bed and my phone buzzed, ‘what if I put you in a situation where you would really struggle to get out of sucking cock, would you be interested?’ I did a double take, it was from my friend and she seemed deadly serious. I didn’t reply straight away and instead spent the day watching shemale porn and fantasising before texting back asking what she had in mind.
‘Well I’ve sucked many cocks and it is great fun, I would really like you to experience what it is like being me for a day and night…’ I thought about it and responded that I would go for it believing that I would be able to get out of it easily enough if I really didn’t want to.
I thought she would just get a guy to come over and try to get me to suck his cock. I thought I’d just be able to say no and walk away. I hadn’t read her text fully.
A few days later my phone buzzed with a simple command, ‘be at mine by 6AM on Saturday’ and that was that. I spent the next couple of days pondering what I was going to do, what was she planning for such an early hour in the day?
Come Friday night I shaved off all my body hair as usual and prepared myself for if I was actually going to go through with it. I set my alarm for 4:30AM and tried to get some sleep. It was a relatively futile experience but I must have drifted off at some point because I was awoken by my alarm and I got out of bed. I had no idea what I was to be dressed as but I knew she wasn’t really into the scene so I walked over to hers in male clothes and rang her doorbell at 6AM.
She opened the door with a cheeky smile and beckoned me inside, ‘so today is the day you suck on a cock’ she opined.
‘I guess so,’ I replied, ‘but why am I here so early in the morning?’
‘Well I offered you the chance to be like me for a day and a night and I have to work on Saturday’s so should you.’
I hadn’t thought this one through but I was interested, very interested to see what she had in mind.
She told me to strip and then brought out the surprise of the day so far, a metal chastity device. She told me that it wouldn’t be freed until I had given a blowjob and done a good days work at the type of job she had to do when she was younger. if I wimped out then she would release me without question, but that I would have to be released at her place and nowhere else, the key would not leave her flat.
I didn’t think much of much and just nodded and she applied ice to my privates to get them nice and small before forcing my penis into the metal device and locking it shut. She then put the key away into a drawer by her bed and said it was time to get dressed.
First she put on a pair of silicone breasts that were placed upon my chest and attached with a glue type substance. I was sure they would just fall off and I’d look stupid but she held them for a minute and then took her hands away and they felt like they were clinging to me. ‘How long will this glue last?’ I asked and she didn’t answer and carried on with what she was doing. I should’ve asked more question but I was in a haze daydreaming about what was going to happen.
Next she put a pink pvc bra on me and it cupped my pert boobs nicely. Then she instructed me to step into a pair of pink pvc ruffled knickers, I was starting to sense a theme. Then came the pink stockings and garter belt that were attached and then came the corset. I had never even thought about wearing a corset before but she assured me that it was needed to make me look all the more feminine. She seems to take pleasure into lacing me as tight as possible and like before, it was all pink PVC.
Then I saw the dress, it was a heavy duty thick pink PVC maids dress. I had worked out what my ‘job’ would be fore the day and expected I’d be cleaning her house at a maid whilst she worked. I stepped into the dress and she pulled it up and did the zip up before I heard a similar click at my neck. I quickly reached back and there was a padlock around my neck at the top of the zip.
I looked at her and she said, ‘well you wanted it to be difficult to get out of and trust me, this isn’t the half of it.’ I suddenly got scared and said that I wasn’t sure if I wanted this and she just looked at me and said, ‘when I was 16 I would work all day Saturday and then go out to the park and suck the cocks of my friends for alcohol. You won’t have to do that but you will be sucking a cock for money so you’ll know what it feels like to be a cheap slut like I was.’
At this point I was panicking big time but she carried on and whilst I was trying to say I didn’t want this she took photographs of me to use as blackmail in case I was to back out. At this point I had no make-up on so it was clear it was me and I slumped in my chair. She seemed serious. Quickly a pair of high heels were fitted on to my feet and yet again padlocks applied. I have no idea how tall they were but I was used to four inches and these didn’t seem too much more so I was pleased. Unsurprisingly they were pink.
Then she started on my make up and boy did she do a job on me. I was rubbish at doing my own but she took her time and made me look like just any other young slutty girl going for a night out, only I wasn’t, I was going to work.
I sat there whilst she got herself ready for work and then took me it was time to leave. I didn’t want to leave as I knew someone would recognise me and she put me in front of a mirror and told me to stare at it. I couldn’t recognise myself so how could anyone else? I walked outside of her front door into the cool morning air feeling a mixture of liberation and being petrified. She drove me out of town and pulled into a small car park outside of a motel and handed me an envelope and told me to go in and ask for the manager and give her the envelope. This was my last chance to back out but even if I didn’t want to suck cock, I was very interested in being a maid for a day so I got out and closed the door. She smiled and blew me a kiss and drove off.
Walking into reception it was still early and before anyone was booking out, approaching the young woman on the desk I suddenly felt very self conscious once more. I was dolled up like a cheap slut and I was about to actually talk to someone I didn’t know. Plucking up the courage I went and asked for the manager and told the young lady that she was expecting me, she asked for my name and I said, ‘Allyson’ and she picked up the phone and said to the manager that I was waiting. She nodded and put the phone down and said that I should wait in reception for her.
I sat down and watched the odd person walk in and out and give me a look but no-one said anything. The young lady at reception kept giving me funny looks and I started to think I should just run but where would I run to dressed like this? Suddenly I saw that this was a great plan to stop me quitting as I had nowhere to go and it was doubtful I’d get anywhere without money and my keys were left at my friends place.
After what seemed like an age the manager came out and approached me, Allyson I presume?’ before I could reply she said, ‘please follow me.’ I followed her to her office and she shut the door. I passed her the envelope and she filed it away in her drawer.
‘So Allyson, I’ve been told you want to see what it is like being a young girl in a dead end job? Well I’m going to give you that experience today. I know you are a man, well a pathetic excuse for one anyway, but today you will be our maid.’ She then passed me a pink overall and told me to put it on and then passed me a name badge engraved:
Parkland Motels Sissy Maid Allyson Trainee Cleaner
She told me that I was to never take off either the overall or name badge whilst on duty, should I do so then Hannah would be informed that I hadn’t done the required work and therefore face the punishment. At this point she passed me another envelope and told me to open it:
Today you will work as a maid and if you don’t reach the required standards then I will not pick you up this evening. If you reach the standards that Parkland Motels expect from their trainee cleaners then you’ll have earned the second envelope. Failure to do so will mean that this evening you will be having to find your own way home this evening.
I hope you enjoy your day sweetie.
I looked at the manager and put my name badge on to my overall and she smiled and told me to report to the laundry for further instructions.
Walking out of her office, the first thing I was thinking was that I was only qualified to be a trainee cleaner, how low was I? Then I saw a map of the motel on the wall and went to the laundry. Inside was a rather large older lady who saw me and told me to enter. ‘So you are the sissy who is going to do my job for me all day today? Excellent. First of all empty all the bins from all the public areas, then vacuum through the building and when that is done please report back here.
The reality of actually working wasn’t as exciting as I thought it would be, certainly not in this heavy pink dress and the high heels. My thighs were already on fire and I was sweating profusely but I got on with it knowing I would look back on this and be terribly excited. I got many looks from customers and a couple of guys were eyeing me up. A hen party saw me and my name badge and all wanted to have their photo taken with me so I posed for them. After vacuuming the whole of the motel’s public areas, I returned to the laundry and was told I would spend the rest of the day ironing and on call for any emergencies.
This was dull as anything and I hated ironing but it was a dead end job and I was starting to feel a bit like that is where I belonged. All I was thinking about was ensuring there were no creases in the sheets and I became obsessed by this. A couple of times the phone went and I was sent out on errands to clean up spills or empty overflowing bins. Mostly though I realised just how boring this type of work was.
When I was told my day was finished I realised I hadn’t eaten all day but had been so busy I had just forgotten. Then suddenly I remembered the cock sucking aspect of the day and I tried quickly to work out how I could get out of it.
Knocking on the managers door she welcomed me in and told me that I had done an excellent job and if I ever wanted to work as a cleaner or chambermaid then she would hire me in a heartbeat. I had this enormous sense of pride at this and I couldn’t hide it and beamed a smile across my face. She then passed me the second envelope:
If you are reading this then well done on being a good little trainee cleaner. I am so proud of you. Your client is in Room #39 and he will pay you $2 a blowjob. Should he not receive a blowjob or be unsatisfied then I will be informed and I will not come to pick you up later on this evening. Should he believe you are worthy of his $2 then I’ll be informed and I shall pick you up.
The manger told me to keep my overall and name badge on when going on my job. I’m guessing she knew exactly what was in the note. I turned around and gulped before exiting and walking to the lift and going up to the second floor and found room #39 and took a deep breathe and knocked.
‘Who is it?’ came from a deep voice in the room.
‘Allyson from the Parkside Motel’ I replied and he opened the door.
‘Are you the sissy whose going to give me a blowjob?’
‘Yes sir’ I said and he waved me in.
‘So I’m told this is your first time, well you know what, lets not play around, you are just a two-dollar whore to me, on your knees and do your thing.’
I was stunned at his forthrightness. He was an older gentleman, the type who probably has to pay for blowjobs all the time. I was repulsed by him but I also knew the predicament I was in. I could run away and try and get back to town whilst dressed like this and hope I didn’t get accosted by someone worse or I could just go ahead and sucked this fat unattractive man’s cock.
Looking him in the eye I knelt down on my knees and unzipped his fly and fished out his penis. I had never touched another guy’s penis before but whilst I was repulsed, I suddenly felt this urge to do a good job. I started to wank him off slowly and licked and sucked his balls. Suddenly his penis was starting to grow to a decent length and I closed my mouth around it and began to gently bob up and down on it just like how I liked my cock sucked. He told me what a dirty little whore I was and that turned me on more than anything and I started to bob my head up and down on his cock with real vigour.
It was like a challenge. I had to earn his reward and I found myself hearing all these nasty words about me and sucking this man’s cock. I was having an outer body experience briefly whilst this was going on and I could see this cute little girl sucking this fat guys cock but she seemed so happy. I was brought back to reality as I felt his cock spasm and as it did he placed his hand behind my head and forced me forward so that I couldn’t get away. Moments later gross salty sperm flooded my mouth and the only way to get it out was to swallow and I gulped it down like a real pro. 15-20 seconds later he was spent and he retracted from my mouth. I had done my job and suddenly I found myself leaning forward and sucking his cock clean and looking up at him and the words, ‘thank you sir’ came from my lips. I couldn’t believe it.
He threw two dollars on the bed and picked up his phone, ‘Hey Hannah, the dirty bitch earned her two dollars,’ and hung up the phone. ‘You may leave’ and I picked up my money and left the room. I stood there bewildered wondering what was next and what had just happened. I walked back to the managers office and she told me to wait for Hannah to pick me up.
I sat there trying to work out exactly what had happened. I had just sucked a cock, not only that I did it for money. I clasped those two bucks firmly, I had earned them. After a long wait Hannah walked in and before I could say anything she asked me to step outside so she could talk to the manager.
Standing outside the office I wondered what they were doing but then I was to find out. After being asked to step back in, the manager offered me a role as a Saturday and Sunday cleaner and that I’d also be working as a hooker for punters at $10 a bob, the money would be split between the manager and Hannah. I would have to live on site from Friday night to Monday morning when I would be free to go to my regular job. If I chose not to take the job then a video of my first blowjob would be e-mailed to my boss and then I would be a laughing stock.
‘Once you’ve paid me back for all you are wearing you’ll be free to go,’ Hannah said but she also explained that by then she expected I’d be too addicted to the cock to want to give it all up.
I could easily pay for all the clothes she had bought me but I was so stunned that I didn’t know what to do.
‘Every Friday you’ll arrive at 7PM in full uniform and I’ll put a padlock around your neck and heels, you will be released at 7AM on Monday, yes you’ll sleep in your uniform so you are always ready for a punter,’ said the manager and prompted me to sign the contract that was in front of me. I signed it using my real name, Hannah kissed me on the cheek and the manager told me that I had another client in room #57 and then room #32 and #74 before going to the kitchen to do all the washing up from dinner before bed.
My weekends would never be the same again…