A friend of the family got me a part time job at a large Law Firm working in the mailroom. Basically my job was to deliver mail to the legal staff and also move boxes full of legal document down in the archive rooms. It wasn't the most exciting job but it paid quite well as I was on casual rates and it was a good chance for me to meet new people in an environment that I had never worked in previously.
During my rounds I got to know several of the staff quite well. There were a lot of beautiful women working in the firm and I used to love going to their offices for a delivery but there was also several men that I found myself attracted to. One man named Ben definitely caught my attention, and I think I caught his attention as well. He was about 6 foot tall and quite athletic looking. I'm usually attracted to older men but there was something about him.
AS this was a reasonably prestige's Law Firm I had to dress quite well to come to work. Usually I had to wear shirt and tie and pants. It was also quite an intimidating place as well so there was no wearing women's panties under my clothes, I was very straight down the line. Fridays though were casual dress day. Jeans were allowed so I usually just wore jeans and polo shirt to work. On this certain Friday I had to drop a parcel off to Bens office.. Usually when I entered the office he would give me a little smile and I would flirtingly smile back but on this day he was much more reserved. Almost nervous to receive the package from me. I just presumed that he was having a tough day at work. So I dropped off the package and left. I had a few other deliveries to do on his floor and I went past his office a few more times afterwards. The first time I went past he was very secretively opening the parcel. I couldn't really see what was in there. the next time I
went past I saw him looking at what was in there and he had something in his hand. AS he was looking the phone rung and he clumsily dropped the item onto the floor. It was a DVD, and from the very quick glance I took was a picture of a dark skinned woman rather scantily clad. I also caught the word Male from the quick peek. Hmmm a picture of a woman (or so I had initially thought) and the word male. What would go with that I was thinking. maybe the word SHE? Made sense, or I hoped it did. So Ben was into his She Males was he? Nice, I thought to myself as I got suddenly very aroused.
The next Friday that I worked I decided to take a risk. I was quite confident that it would pay off. I wore a polo shirt that was a little shorter than my usual shirts. It literally only went down to my belt line on my pants. I wore a pair of low cut jeans that only just went above my butt. under the jeans I wore one of my little black thongs. I had to be careful all day when I was doing a delivery to not bend over too much or face away from the person I was delivering to. That was until I went into Bens office. bens team were working on a large court case. They were getting constant deliveries to them of documents and interview disks. I knocked on the door and Ben was on the phone. I had a box with disks in it and he motioned for me to drop them on the floor in the corner. I positioned myself was that I was facing away from him and did the slowest straight legged bend over that I could. I could feel my shirt climbing up my back and I also knew that my jeans would now be exposing the top of my ass crack. I also knew that my thong would now be sitting about an inch above my pants. I had practiced in the mirror that morning. I knew what he could see. I put the box down and wasted a few more seconds pushing it in under the desk. I knew that he was looking at me from behind because as I was pushing the box under I turned my head slightly and saw his feet pointing in my direction. I stood up smiled and left the office.
Every second Friday night was staff drinks in the large boardroom on the top floor. I had been once before but really did not know anyone that well to socialise. I still didn't but I had a few beers anyway. After those beers I really needed to piss. As I was standing at the cubicle having a pee, Ben sided up next to me on the next cubicle.
"Some of my team are going to Bar ####### for more drinks after this. I cannot invite you along as they would find it a bit weird to have one of the mailroom staff tagging along. But make sure that you are there at Midnight. Just be near the front entrance." Those were my instructions. I went back down into the office and called my parents to tell them that I would be late home. I still had 4 hours to kill so I went to the movies. I saw one of the Lara Croft Tomb Raider movies. Angelina Jolie always made me horny.
5 minutes to midnight, I was out the front of the club. I couldn't get in. Only little sluts in short skirts got in on there own after 10pm. Maybe another time ; )
Ben exited the club just after midnight. He was on his own. He didn't say anything to me he just motioned with his head for me to follow. So I did. We started walking back towards the office and when we got there Ben swiped us both in. In the lift we went up to a random floor and got out. the toilets are right near the lifts and he went into the men's toilet. I kept on following. once inside;
"Turnaround and face the mirror and pull down you jeans, but not those sexy little panties" I did as I was instructed. I undid my belt and dropped my jeans to the floor.
"Lean forward and rest your elbows on the counter" Just after I did this I heard him spit and then I felt a wet hand slide in under my thong. He rubbed it all around my asshole. I heard him unzip his jeans and within seconds I could feel his cock rubbing on my ass.
"You like wearing girls panties, that must mean you like being fucked like a girl as well. Well does it!?" He demanded as he spanked my ass really fucking hard.
"Yes, I like being fucked like a little girl" I replied trying to sound intimidated as he clearly was getting off on the whole power thing.
Just after I had said that he put the tip of his cock in line with my man pussy and without hesitation rammed it right in. I gulped for air as I had not seen how large it was but it sure filled me up.
"So you're a little slut!, look at yourself in the mirror slut! look at me fucking your slutty ass in your slutty little panties!" He said aggressively. Boy was he loving this little control of power he had going on. I really think that he must have had a bad day and he was venting his frustration on my ass because he was really fucking me hard and from the look on his face in the mirror it was quite a release of anger.
It didn't take very long when he pulled out and said "Turn around and on your knees" Just as I did he shoved his throbbing cock into my face and it started spurting out some beautiful warm cum all over my face. Not being one to waste I quickly put it in my mouth as to avoid spilling too much. I must say, his cum was some of the nicest tasting cum I have ever swallowed.
" Oh my fucking god that felt so good!" he exclaimed. "I really needed that"
"Sure sounds like you did" I said back.
"We should do that again some time. I'm going back down to the bar. See you next time you're working." He said as he zipped up and walked out the door.. that was it. Time to go home. I washed my face off and sat on the toilet and wiped all the juices from my now loose and very wet hole.
It was 3 more Fridays until I worked on a Friday again. It was the odd Friday so there was no staff drinks. I had to make a delivery up to Bens office.. this was the first time that I had seen him since our previous encounter. I only had a letter to drop off for him. So I knocked on the door and went in. He said thanks and then wrote something on a piece of paper and handed it to me. He then answered the phone.
Same time, same bar tonight. Bring something to wear.
"bring something to wear?" I thought to myself. Could only mean that he wants me to do a dress up for him. As there was no staff drinks I had to go home and then make an excurse to go out again that night. I told my folks that me and one of my mates were going to the movies and that I was staying at his place. I used a friend that lived a fair distance away and that I know my folks don't have a contact for.
Midnight arrived and out came Ben. Once again we walked back to work and I followed him into the toilets.
"You bring something to wear?" he asked.
"Yep" I replied as I unzipped my bag and revealed A nice black skirt and singlet combo and red bra and thong set. well I already had the thong on but I revealed the bra. I also had my wig and some makeup in the bag as well as a pair of sandals for my feet.
"Get dressed then. I'll be back in a few minutes" I did as he asked, albeit very cautiously as I was in the toilets used by all staff on this floor. I had really hoped that everyone had left by now.
I put on my bra and inserted my fake tits. I pulled the tight singlet over my head and slid the short skirt over my chubby ass. I then put on my wig and did a hasty job on my lipstick and eye makeup. I had just finished when I heard the door open.
"Fuck!!!!!!" I screamed and ran into the closest sit down cubicle and slammed the door behind me. that wasn't fucking Ben. It was Stuart. He is one of the top Partners in the firm.
The door opened again. "It's ok. He's with me" Bens voice said.
My heart was pounding like a machine gun as I opened the door.
"Well, well. What do we have here?" Stuart said in his deep voice full of authority. Stuart was the sort of man the demanded attention. He was also the sort of man that I found very sexy. It's wasn't so much his mid 50 years of age or his slightly overweight frame or even his half bald head of hair. It was the powerful aura that he displays. It was his look of dominance that I really loved about older men. It was a look that made me want to do anything for them.
"Hi I'm Jacki" I said almost in fear.
" Hello Jacki, aren't you a pretty little girl" He replied as he turned to Ben. "I'll see you at the car in 10 minutes" he said to Ben and left the toilets. "Where are we going?" I asked Ben
"Wherever Stuart wants" came the reply and continued " Here's the thing. I'm Stuarts boy. I do anything and I mean anything for him. That included getting him a little girl. Can you be that little girl for him?"
" I sure can!" I said with joy.
The car was in the basement car park. to get to it we needed to take the lift to the ground floor and hop in another lift down into the basement. I was a bit nervous about this. it wasn't exactly dark in the building and if we came across anyone I would be very exposed. We walked to the first lift. Nobody was in there I breathed a sigh of relief. Exiting at the ground floor. there were two people in the foyer. They looked like a couple. Luckily it was a large foyer and they would have been about 30 meters away as although they looked over at us they would have just thought that I was a chubby girl in clothes too tight for my body. We continued to the final lift. Upon exiting we had to walk past the security guards office to get him to open up the roller door for us.
" Hi I'm her to drive mister ##########'s car for him. Can you please open the door when you see us leave." Ben asked him.
"Yes sir, I'll do that for you" came the response. He looked straight at me.. He was only about 2 meters away so there was no hiding but I didn't really care now anyway. He was an older Asian man and if wanted to have a good look I was happy for him to.
We walked over to the car, and what a car it was. It was a large silver Mercedes Benz and it must have been worth a fortune.
"Hop in" Ben said as he opened the back door. So I got in. "Stuart will be down in a minute" he told me while closing the door.
About 5 minutes later Stuart arrived and Ben let him in the other rear door..
"hello sexy" he said as he sat on the seat next to me. "Lets go Ben. Take us for a ride to the coast."
With that Ben hopped in and we drove out of the car park, past the waving security man and headed on our little joy ride.
Stuart was a man who knew what he wanted. "So do you think you can make daddy happy young girl" He asked me.
"I think I know a way" I responded putting my hand on his inner thigh.
"Yes I think you do" he said smiling back.
I unzipped him straight away. Pulling down his underwear a bit I reached into his pants and grabbed on his almost erect cock pulling it out of the pants. It felt nice and I stroked it up and down ensuring that it got as hard as it could. Meanwhile he was exploring my body with his hands. Rubbing me all over my back and reaching in under my skirt and feeling my white ass cheeks. I loved being fondled.
He was very hard and it was a nice cock to look at. It was probably about 8 - 9 inches and had a slight curve towards to top. I wanted it and I lowered my head into his lap and started licking around the tip. He moaned as I liked all around the head of his cock and made it nice and wet. after teasing him like this for a few minutes I opened my mouth and took about half of it in. I pulled my lips nice and tight and gave him a firm suck up and down on the top half of his pleasant joystick. He was really enjoying it as I could sense his breathing intensifying. His hands also became a bit more daring and I felt him pull my thong to the side and start exploring around my love hole. I was still pretty dry down there and he firmly pushed a finger in. I enjoyed having something put in me while not lubricated. It gave a different feeling.
I kept sucking on him lowering myself down more and more until I was fully deep throating him. While I gave him a nice hard blow job he started finger fucking me faster and faster. My dry pussy was not getting wetter and wetter as my ass juices started to flow. I could feel him tense a bit when he pulled my head up and demanded I stop. He clearly wasn't ready to cum yet and I didn't want him to either.
"Hop on" He said. I went to slide onto his lap facing forward but he said "no turn around and face me"
I knew that I couldn't get him real deep in me facing that direction but that's what he wanted so I obliged. I stretched my groin so I was straddling above him. Grabbing his cock with my hand I positioned it and lowered down onto him. Even though I could only get about half in wile in this position it sill felt great.
"Mmmmmm, good girl. Give daddy a kiss as he gives you a ride on his rocket." I leant in and gave him a passionate kiss on the lips. It quickly became an intense kiss and his tongue was exploring every centimetre inside my mouth. I did the porno kiss and we had a big tongue wrestle that got rather wet and sloppy. His mouth was starting to get covered with my lipstick.
I kept riding him like this as we had a serious make out session.
"Where do you want to go now?" Ben asked from the front. He must have been getting a good show in the rear view mirror.
Stuart pulled his mouth from mine "Take us to that car park on the head land that I like" Stuart instructed and went back to our tongue wrestle.
The car stopped. It was very dark outside. "Let's get out and give ourselves some more room" Stuart said. Sounded good to me.
Stuart gave me a hand out of the car and led me around to the bonnet. He turned me around and pushed me down on my chest. I knew what was coming. I had a quick look around. there was another car that I could make out about 70 meters away. It seemed like there was nobody in it. Or maybe there was. It was too dark to tell and too dark for me to care.
"Ohhhhhh!" I moaned as Stuart pushed himself into me again. This was better.. I could really feel him going deep inside me now. I looked up and even in the dark could see Ben in the drivers seat in the car. He had his cock out and was giving it a good pull.
" That's a good girl. Take daddy deep inside you. Can you feel daddy's big cock inside you?"
"Yes daddy. You're cock feels so nice deep in my bum" I said playing along. He seemed to like this answer as he started thrusting even harder. Once again I think he was about to cum when he pulled out suddenly.
"Ben, wont you join us?" He asked
"Gladly" Ben said leaping out of the car. Ben walked around the car and knelt down in front of Stuart. I was a bit surprised. I thought that I would have to service Ben but he seemed to be intent on servicing Stuart as well. I guess he had told me that he was Stuarts boy so this must be the anything that he does for him.
"Yes good boy Ben. Jacki, get down and help Ben making daddy happy."
I got off the bonnet and knelt down on the concrete with Ben. We took turns in sucking on Stuarts shaft. Yet again Stuart stopped us suddenly. He really must have been near blowing by now.
"On the bonnet Ben" Stuart told him. Ben jumped up and laid himself chest down on the bonnet. Stuart stood behind him and slowly pushed himself into Ben. Ben was a lot more aggressive than I was. I was playing the part of the good little girl but Ben was the bad boy.
"Yeah fuck me hard, fuck my ass hard daddy. Fill my cunt with your big cock.." Just as he was when he fucked me previously, Ben was just as angry when on the receiving end. "Fuck me harder, harder, fill my stomach with your cum." Damn! I thought.
"Come and kneel next to us Jacki." Stuart said. I'm going to take my cock out of Ben and put it in your mouth and I want you to suck it like a good little girl"
"ok daddy" I said positioning myself next to him. Stuart pulled out of Ben and put it in my mouth.
"Does that taste nice Jacki? Can you taste Ben on my cock?"
"Mmmmmm, yes daddy, your cock tastes real nice. I can taste Bens ass on it. Fuck him more daddy. Let me taste more of him" I almost demanded of him.
Stuart turned around and re-entered Bens awaiting ass. Once again Ben was letting it all out his aggression demanding that Stuart fuck him harder and then came this little doozy.
"Fuck the shit out of me daddy! make the little slut lick the shit of your cock" Ben screamed
I was a bit nervous about that one. Not really sure that I was ready to be a shit eater. Stuart sure tried though. He really started hammering Bens ass as hard as he could. I awaited patiently hoping that Ben was nice and clean inside.
Ben was going wild "Yeah harder daddy, harder. I can feel you pushing up into my bowels. Take it out and make the slut clean you off"
Well here goes I thought. I closed my eyes not wanting to see what Stuarts cock looked like. I thought that if I cannot see it, it cannot hurt me. I had never tasted shit before so if it was on there and I could not see it I might not notice. Cock always smelt a bit like fart when you taste it from someone's ass so maybe it'll just smell the same.
"How does that taste Jacki?" Stuart asked. "Is it nice?" I opened my eyes again as it was already in my mouth now. I gave it a good suck and swallow and then said.
"Tastes great daddy. Give me more" and went back to sucking. It didn't taste that much different and I did not know if anything was on his cock at all until...
"yeah, suck that shit off his cock you little slut!" Ben said insultingly. I really did not need to hear that. I gagged for a second. "Block it out Jacki" I thought to myself. It didn't taste any different, there was nothing there. But he was relentless.
"Suck it. Eat my shit off him!" Ben was enjoying degrading me. He was an angry little man. It was the first time I have ever wanted to stop sucking. I gagged occasionally and tried to ignore it. Stuart was pulling my head into him so there was no escape. I just took it. I also got over it pretty quickly.
"Lay on your back Ben. Lets see Jacki suck you why I fuck her pussy again"
Ben did as he was told. I stood up and leant forward and started sucking on his cock. this was actually the first time I properly saw it. His cock was about 7 inches and quite fat. It was also very hard. He seemed to like it rough so I gave him a real rough and sloppy blow job. there was plenty of saliva spilt as I gave him a nice and nasty deep throat. Stuart in the meantime was behind me ramming his rod deep into me again.
"That's the way Jacki. Suck on Ben like a good girl." he panted while drilling me from behind.
"Yeah suck me hard. Suck me like you sucked my shit of daddy's cock!" screamed the viscous little man.
It wasn't long before Stuart was ready to explode again. I think he was ready this time.
"Quick Jacki. kneel in front of me" he said while pulling my shoulder down. Almost as soon as I had knelt in front if him he squirted loads of warm cum straight onto my waiting face. It didn't taste as good as Ben's but cum is cum and I love it. It dribbled down my front and onto my clothes. I tried to catch as much as I could in my mouth but it was a massive load.
That was it. There was no opportunity for Ben to cum. This wasn't about pleasing him. this was about Stuarts fantasy of fucking his own little boy and girl. "Take us back to the office Ben. Jacki can get cleaned up in one of the showers there"
Ben placed a towel on the back seat and he and Stuart sat in the front. We drove back into the car park and the men got out of the car. I was filthy. Dried up cum covered my clothes. My makeup was smudged all over my face. It was now 3am. I got out of the car. I didn't really care. I was totally unrecognizable now if not before. we walked past the security guards office. He popped his head out. he looked at me. and it was a thorough look, looking right up and down my body, fully noticing all of Stuarts cum covering me.
"Did you have a nice night Mr Stuart?" he asked
" A very nice night thank you" Stuart replied and we kept walking. when we were about 10 meters passed I looked back. He was still looking. well lets give the old fella something to jerk off about I thought and lifted my skirt to reveal my red ass to him. I gave him a smile and he was staring at me with a big grin. I rubbed my ass a bit for him and lowered my skirt back down. We then hopped in the lift. The lift and foyer were empty, fuck knows if there were any security camera's and I didn't care. Stuart and Ben were recognizable not me.
I hopped in the shower, cleaned off. I did not see either man again that night after getting in the shower. I could not go home as I told my parents that I was staying at a friends place. I slept in the office and left early in the morning.
I really hope you enjoyed this adventure. I love hearing peoples opinions whether they liked my stories or not. Please let me know, I love receiving feedback. You can email me at looseboy_girl@yahoo.com.au. Let me know if you enjoyed the story and if you would like to hear more.