It was a Monday morning, the clock on the kitchen wall showed 7 a.m and I was enjoying my first cup of tea of the day. I started up my computer and as I waited I stood by the window of my first floor apartment looking down into the main street, watching people going to work and I smiled to myself remembering how that used to be me, but not anymore, not since I had taken a friends advice and found a better and more enjoyable way of earning some money.
I turned away from the window and sat at my computer and opened my personal diary page to check my schedule for today.
Martin....10.00 a.m. usual service 50.00 David.....11.30 a.m. usual service 50.00 Lee........2.00 p.m. new customer 75.00
( oral / anal / dom - sub roleplay / bondage)
Today was going to be quite rewarding financially mainly because of the services I would be providing for these guys as they were more than willing to accept my fees as they probably wouldn't get these services anywhere else.
I was in my late thirties, single and bi sexual and had regularly been meeting other guys for mutual, sexual pleasure at my apartment. I had been doing this for a few years when one of them suggested I could make a lot of money if I became a gay escort. He showed me websites on the net where escorts could advertise their services and he said that as I was more on the submissive side and quite kinky I would probably be quite popular with gay men who wanted something of the kinkier variety.
Apart from being bi sexual I was also into dressing up and after years of practice I was told that I made a very, convincing transvestite and apparently there were a lot of other transvestites on the internet who sold their services online, which obviously meant that this particular fetish was quite popular with gay and bisexual men.
It was only when I checked out these websites that I realised the potential in my friends suggestion. The fees that some of them charged for basic oral or anal relief seemed very high to me and when I thought of how many guys I had willingly given the same treatment to for free, over the last few years it seemed too good an opportunity to dismiss, without serious consideration. In my region alone I found fifteen other transvestite escorts, most of whom only provided oral and anal and as I looked at pictures of these escorts I realised that my friend was probably right because without boasting I knew I was much more convincing when dressed than most of these others.
All I had to do was register for my own webpage, upload a few pictures of myself dressed and a description of services available with fees and see what responses I received.
My webpage had only been advertising for about a week before I realised how lucrative this could turn out to be and now three months later I was seeing regular and new customers on a daily basis and enjoying fantastic sex and getting paid well for it. My email box was regularly full with requests from guys who had visited me before and also lots of new guys who had seen my webpage. I always replied to every mail and always asked for a picture or at least a description of how they looked, age, height, weight etc. and of course I would ask what services they required and I would let them know my fee. A few I would turn down if I thought they didn't look or sound right but on average I accepted most of them as turning down good money seemed rather wasteful.
So today I had three customers and would earn 175.00 which was amazing for just over three or so hours work. The rest of the week varied where Tuesday and Thursday I had two customers on each day, Wednesday I had just one and I noticed Friday was going to be very busy with five customers booked in, which was the most I would take on one day. Today I had Martin and David who had visited me several times each and both were very different in their requests, both were married and obviously used me for their kinky desires which their wives couldn't fulfill. Lee was a new customer and surprisingly very young at nineteen but looking at his picture that he had sent looked very inviting, particularly his huge looking cock, hanging down between his legs and I was really looking forward to being his submissive slut.
My daily routine was usually the same where I would select the various outfits I would be wearing which was usually determined by what each particular customer wanted me to wear, then an all over body shave as I liked to be totally smooth, followed by an anal cleansing which involved an enema which I repeated until totally clean after which I used a scented douche so that I was fully prepared to be fucked and rimmed too if required, without any embarrasing results.I would then take a hot shower and start getting my makeup on ready for the first customer of the day.
Martin arrived promptly on time and I greeted him at the front door wearing his favourite outfit which was a short pleated grey skirt with white stockings and navy blue knickers underneath, a white blouse and school tie, heavily applied makeup and a blonde wig with pigtails and a pair of black, knee high boots on my feet which all turned me into the naughty schoolgirl which Martin liked.He was about fifty in age, slightly overweight but had a lovely, thick circumcised cock which I always enjoyed sampling. I smiled and said hello inviting him into my appartment.
" Take me to the bedroom Selina, Uncle Martin is very horny this morning"
I took his hand and walked him down the hallway to my bedroom, his hand already sneaking up my skirt, squeezing my panty clad bottom. Once we were in the bedroom Martin wasted no time getting undressed as I sat on the bed waiting. His thick, hard cock sprang into view as he removed his underpants and now totally naked he walked over to me and stood in front of me.
" In your mouth slut I want you to get it nice and wet"
I loved being talked to like that, it turned me on immensely and also had the same effect on Martin and I obeyed his demand and slipped my bright red lips over his cock, tasting the warm precome that was already liberally, dribbling from his cock.
" Oh yes suck it slut" he moaned.
His thick cock, stretched my mouth wide and I used my tongue to flick around the underside which I knew was the most sensitive area. He held my head in his hands and began thrusting his cock into my wet slippery mouth.
" You are a filthy tart Selina and you love Uncle Martins cock don't you?"
Obviously I couldnt answer him but moaned and moved my head up and down in the affirmative to his question.
" Oh fuck I am so horny, stop now before I get too carried away"
I released his cock from my mouth and looked up at him, waiting like the obedient schoolgirl I was supposed to be.
" You know what I want now don't you ?"
" Yes Uncle Martin"
Joining in with the roleplay and calling him Uncle always turned Martin on which I was more than willing to do considering he was paying me well for this pleasure.
I turned over on got onto my hands and knees on the bed and waited for him to continue. I felt his hands pulling my skirt up around my waist and I heard his lustful moans as he started to fondle and squeeze my pantied bum.
" Navy blue knickers are so sexy" he said, running his hands all over my panties.
Next I felt his hot breath on my bum as he rubbed his face over my panties, licking and kissing them all over, before he yanked them down exposing my smooth bum.He used his hands to pull my bumcheeks apart and again I felt his hot breath as he began to lick my tight smooth hole.
" mmmmmm your pussy smells and tastes divine Selina"
I loved being rimmed and I reached down to stroke my hard cock as Martin probed inside my arse with his tongue.
" Oh yes Uncle Martin,my pussy is tingling.Are you going to fuck me soon" I asked, playing along with the roleplay as Martin liked it. I felt him move away and then heard the loud slap and felt the sharp, stinging pain as he began to spank me.
" You filthy bitch, yes I am going to fuck you but not until you beg me"
" Oh please Uncle I need your hard cock inside me"
" Do you want me to fuck you hard?"
" Yes Uncle my pussy is aching for your cock"
Slap! another firm smack making my bum sting, then another slap and again until my bum started to tingle but I never revealed to Martin how much I enjoyed him spanking me as this would only spoil the roleplay where he had to think he was abusing me which was what excited him.
" Lube and condom? where are they?" he asked
I reached under the pillow where I had already put the lube and rubbers and held them out for him.
I stayed in the doggystyle position as Martin did the necessary, putting on a condom , followed by an ample amount of lube rubbed around my bum hole and as he slipped his fingers inside me, lubing me inside, I moaned with pleasure. Martin fingered me roughly, opening up my tight lubed hole so it was ready to take his hard cock.
" Right you slut I am going to fuck you hard now"
I braced myself as I felt Martins cock pressing against my hole and as I felt him pushing I tensed my stomach muscles and pushed with my arse muscle to open myself up and with one hard thrust he slipped his cock all the way in. The initial, searing pain always made me cry out which only seemed to add to Martins pleasure.
" Take it bitch" he moaned, slapping me hard on the bum. The pain and discomfort from his thrusting cock tended to last for a few seconds or more until I finally got used to the sensation of being full and gradually the pain turned into a nice numbing feeling as Martin plunged his cock into my arse, hard and fast. I had been fucked many times and although the pleasure for me usually came from knowing the guy fucking me was enjoying it, there were also rare occasions where it really felt good and I had on a few occasions actually come myself whilst being fucked without even touching my cock. But with Martin it tended to be rough and slightly uncomfortable which was after all how he liked it so I was willing to take the discomfort and one good thing was he wasn't able to fuck me for too long before getting close to coming.This particular morning as he was especially horny he only managed two or three minutes of hard fucking before he pulled his cock out of my arse and I knew what was coming next.
" Fuck that was quick, on your back bitch"
I lay out on my back and waited for the usual ending to our session. I watched Martin peeling the condom off his hard cock, discarding it onto the floor and then he straddled my chest, kneeling up so I didn't have to take his full weight. He shuffled forward on his knees so that now he was kneeling right over my face. As I looked up at his hairy balls and cock I knew what was required of me. His large round bumcheeks were hovering directly above my face and I used my hands to pull his cheeks open, revealing his tight, smoothly shaved bumhole.
" Lick it slut" he ordered.
At least his hole smelled clean and I actually enjoyed doing this, rimming his smooth hole as he slowly stroked his hard cock above my face. Hearing him moaning encouraged me and as I pushed my tongue into his arse he let out a loud gasp of pleasure.
" Oh fuck yes that feels good"
The rimming could sometimes last for up to half an hour until Martin eventually stroked himself to the point of no return, but this morning I probably tongued his arse for ten or fifteen minutes before he quickly slid back and lowered his hard cock into my open mouth. He kept wanking himself into my mouth until he spurted his heavy comeload down my throat. From the position I was in I always felt I was going to gag as he spurted down into my mouth, but I always managed to greedily swallow every drop which I loved doing. After wiping his spent cock across my lips Martin got up off the bed and that was the session over.
" Thanks Selina, that was as good as ever" he said, handing me the fifty pounds payment from the pocket of his trousers. He then got dressed and as usual left straight away
" I'll be in touch for next weeks session" he said as he left the bedroom leaving me to recover on the bed.
I waited until I heard him leaving through the front door, glancing at the bedside clock I realised that the usual hour session had been slightly shorter today and so I had about forty five minutes to get ready for my next customer who was David.
David was totally the opposite to Martin as in he was quite shy and more submissive in his demands which made a nice change for me. I got dressed in his favourite PVC basque, with black panties; black seamed stockings which were attached to the basque by eight suspenders which took a while to fasten in position. This outfit was finished off with a short, black wig and very sexy black thigh boots. I touched up my makeup and also made sure I was clean and fresh anally with a quick clean and some more scented douche. Most of the session with David took place in the bathroom and when he rang the doorbell that is where we ended up, where David stripped off revealing his quite hairy body, totally naked except for a pair of black tights and a white thong that he was wearing. He liked to crossdress but not fully just some tights and panties which apparently belonged to his wife. David was probably a bit younger than Martin, mid forties, balding and he had an average sized uncut cock which he sometimes struggled to get hard. David also preferred it if there was no conversation just the odd words here and there to tell me what he wanted.
The reason we were in the bathroom was because David had a huge fetish for watersports and we spent most of the session indulging in this. He liked to wet himself through the tights and panties as I either rubbed his cock through the hose or let him rub against my face so he could pee over me. He would drink pints of water before visiting me so at least his pee wasn't too strong and yellow, but almost clear instead which I didn't mind too much in fact it was quite horny surprisingly.
I sat on the toilet seat and started to stroke the bulge at the front of his tights and panties. His cock felt semi hard inside the nylon and as I gently teased his balls he sighed and started to pee himself. The crotch of his tights and panties started to get wetter and wetter as he let go his stream of pee. I felt it warm and wet, running over my hand and down his legs and over the tiled floor. He kept peeing himself until he was literally soaked and when he had finally finished I peeled the saturated tights and panties down his legs and dropped them into the sink. He always liked to start the session like this but I knew he would soon be needing to pee some more and as I took his small semi erect cock cock into my mouth I could smell the intoxicating aroma of spent pee and also taste the tangy flavour. I started to slurp noisily on his cock which almost immediately started to leak precome onto my tongue and then he sighed again and I knew what to expect as he again started to pee. I wouldn't drink his pee but just let it flow freely into my mouth, letting it dribble out down my chin and all over my PVC basque and panties and stockings. As soon as he had finished his second long pee, the floor of the bathroom was virtually flooded but at least with it being tiled it was easy to wash down and dry.
Next David liked to rub his face against my panties, sniffing his own pee and licking my hard cock through the sheer, wet fabric. I would then remove my cock from inside my panties and David would suck me off for a while but I never let him make me come as this would only take away my sex drive completely and I still had Lee to service later on and I wanted to be as horny as possible for his lovely big cock. After sucking me for a few minutes David then had me lay out on the wet floor so he could finger my arse. As he did this he would wank himself off and usually this would get him fully erect. I enjoyed watching him wank as he fingered my arse.
After about ten minutes or so of this David got up and stood over me and again he started to pee. Aiming his cock downwards he would pee over my legs, then my body and finally my face. I was by now totally drenched in his pee and would strip out of my soaked garments. We both got under the shower together and soaped each others bodies down and after we had dried ourselves off David would sit on the toilet seat and I would kneel in front of him and he would wank himself off hard and fast which could last anything from ten to twenty minutes until finally he just said the word
" Yes" he groaned.
This was my signal to take his cock in my mouth and I sucked hard on it until he filled my mouth with his hot come and David was quite a heavy comer and seemed to spurt jet after jet of come which I kept swallowing down until he finally finished.
After David had paid and left I had over an hour to get myself prepared for Lee, my very young new customer and I was getting quite excited at the prospect of being well and truly used by him. He sounded quite kinky and I was more than ready to provide any pleasure to his lovely big cock. I gave myself a clean enema and douche followed by a quick shower. Next I topped up my makeup and finally I got dressed in my red minidress, chocolate brown holdup stockings, a white silky thong and black mule 4" heels and topped it all off with a long blonde wig and just hoped that Lee would be pleased with how I looked. He arrived a little late and when I opened the door and saw him holding a large holdall bag I thought he looked like a little boy lost looking for somewhere to stay. He was quite tall, very slim and dressed in shirt and jeans and I watched his reaction as he looked me up and down, smiling as he did so. He didn't appear to be nervous and when I invited him in he marched straight down the hall, looking around the place.
" Which room is it?" he asked
" Second on the left if you mean the bedroom" I answered, following him down the hallway.
He entered the bedroom, throwing his large holdall onto the bed and proceeded to get undressed. I was a little surprised by his confident, forward manner which seemed unusual for someone so young in a situation like this, but then again I wasn't used to customers so young as Lee was.
" I prefer it if there isn't any talking except when I tell you to do something" he said
I nodded my head and went over and sat on the bed and watched him undress. He was down to his boxer shorts and when he slipped them off I stifled a gasp as I saw his gorgeous, huge cock. It looked aroused but not fully erect and sort of pointed out from his crotch and arched slightly downwards in a long curve. It was certainly the biggest I had seen in real life and at a guess I would say it was over ten inches in length and very thick, circumcised with the head about the size of a large plum. After stripping naked he reached for the holdall and took out what looked like several lengths of rope and I realised what he wanted to do.
" Lie on your back with your arms and legs spread out" he asked.
I did as he said and watched as he tied firstly my right wrist then my left wrist to the legs of the bed, then he moved to the bottom of the bed and did the same with my ankles, so now I was spreadeagled with my short red dress pulled up high, exposing the bulging crotch of my white panties. Lee joined me on the bed and seemed to enjoy the view as he stared down between my legs and rubbed his hand all over my panty covered cock, which felt very good for me and just as I was really getting to enjoy his gentle stroking touch, he stopped.
" Right I need my cock sucked now " he said, moving up the bed so he was kneeling by the side of my head. He started wanking his huge cock, rubbing it all over my face and I could feel the slippery precome on my skin and the wonderful musky aroma from his cock smelled lovely.
" Open your mouth" he said
As I parted my lips he swung one leg across my chest, straddling me and with his hand he moved his huge wet cockhead into my mouth, spreading my lips and jaw to the limit. I could only take his cockhead and a couple of inches of his thick shaft, but I think he realised this and thankfully didn't try and force me to deepthroat which was something I wasn't able to do. He started to fuck my mouth slowly and it was an amazing sight just watching this huge cock in close up, sliding in and out of my mouth. I had no idea how long Lee fucked my mouth like this but when he removed his cock from my mouth and got off me and moved down the bed to get between my legs I became a bit nervous as I knew he intended to fuck me now and I had never taken anything near as big as his cock before.
He reached into the bag and brought out some lube and then I really did get nervous, because he then squirted some of the lube onto his cock and started rubbing it in which meant he didn't intend using a condom. He pulled my panties to one side and lubed up my bumhole and my mind was in turmoil as I had never been fucked bareback before because of the obvious dangers with sexually transmitted diseases, but on the other hand I had always wondered how different it would feel to be fucked naturally and to actually feel someone coming inside me was something I always wanted to try.
I know I should have stopped him but my horny, curiosity got the better of me and I thought if he wanted to fuck me bareback then I would let him. I felt his large cockhead pressing against my tight hole and I pushed with my arse muscle and as he pushed I felt myself being stretched wider than ever before as slowly entered me. I didn't feel an awful lot of pain, just this sensation of being stretched so wide and I was glad that I had been fucked earlier by Martin as this had opened me up and prepared me for Lee's much larger cock. I looked up at Lee and his face was a sight to behold, eyes closed and mouth slightly open he appeared to be enjoying it and as he continued to slide more and more of his cock into me I felt myself being stretched and filled to a limit I had never been to before and although it did feel slightly uncomfortable, it also felt very pleasurable too and I had this funny sensation of wanting to pee myself. Lee pushed some more and I dont know what it was but it felt as if something was restricting his cock and then I felt something give and he slipped deeper inside me and I felt the urge to pee even more now, but it also felt like I was going to come too and as Lee opened his eyes and looked down, the expression on his face was a picture
" Jesus, you've taken it all" he said.
I couldn't quite believe that I had taken his whole cock and even better I couldn't believe how much pleasure it was giving me and I was convinced that the more Lee fucked me the closer I was getting to coming myself which would definitely be a first for me, to actually orgasm myself whilst being fucked was certainly a pleasure I craved. Lee started to increase the tempo and began thrusting into me harder and he was breathing heavier, giving all the signals that he was very close to coming. I closed my eyes and tried to concentrate on my own orgasm which I was certain wasn't very far away and unable to use my hand to wank myself was getting to be very frustrating.
" I'm nearly there" Lee said and he started taking long, deep strokes which felt absolutely amazing and I felt the familiar tingling sensation in my balls and hoped that Lee would just hold out a little longer.
Thankfully he did and I felt myself start to come. I looked down at my cock and it looked really weird watching it jerk a few times before it spurted jet after jet of come over my stomach. Lee was looking down at my spurting cock too and he started to come too deep inside my arse. I couldn't remember having such an intense orgasm before and just as mine subsided Lee started to have his and I felt his cock swell inside me, then it spasmed and jerked and I felt his hot come spurting deep inside my arse which was a strange but wonderful sensation. Lee's orgasm seemed to last for ages but finally he slowly withdrew his cock from my arse, totally spent.
" That was something else" he gasped, as he recovered from the wonderful fuck he had just given me.
He moved up the bed and untied my wrists, then he untied my ankles and I watched as he got up off the bed, his big cock now hanging down between his legs and I started to feel a little guilty that he was supposed to pay me for what had been a very pleasurable experience for me and hopefully him too.
Lee reached into the holdall and handed me the 75.00 and then gathered up the pieces of rope . He got dressed and I just lay on the bed totally exhausted.
" Thankyou for that, hope to see you very soon" he said and then he was gone.
I lay on the bed for awhile, thinking over what had been a very good day where I had earned 175.00 for doing something that I loved and realised how fortunate I was to be so happy and well paid in my work.