I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell me that Miss Class was waiting and asked if she should show her in. I agreed and sat back to watch the view of Paula's nice arse as she walked away from me. A twenty two year old gorgeous blonde, Paula was the kind of person who brightened up any office with her presence, especially when she walked the other way and gave a view of her perfect round arse. I probably wasn't the only guy in the office who'd wondered what it would be like to fuck that sweet arse.
It's not that I deliberately hired a sexy babe to work as the receptionist, she was perfectly qualified for the job, although perhaps subconsciously I favoured her above other candidates. It's just that, having hired her, I found it hard not to stare with that cute arse always in my face whenever she came by my office. In the same sense, I couldn't help staring at the gorgeous creature who walked in after her and think that maybe she was in fact the perfect candidate for the secretary job.
Tracy Class was absolutely stunning in every way. Tall, taller than I was, and with an hourglass figure, narrow waist and huge tits that were practically bursting out of her pinstriped blouse. This was a woman who couldn't look restrained, repressed and unformal, however she dressed. Even given that fact, her outfit was a hugely sexy turn-on look. She was dressed completely in the style of a stereotype sexy secretary; tight, figure hugging blouse unbuttoned down to her impressive cleavage, a pencil skirt covering her thighs and the rest of her long legs in shear stockings with a seam up the back, black six inch heels on her feet. She had dark hair, tied back from her face with the full, pouting lips that any man longed to see around his dick and dark green eyes behind rimless glasses.
She sat in a prim and proper manner and answered all of my interview questions in a direct, clipped accent and in a manner that was completely everything that I wanted to hear from an efficient, respectable candidate. I could barely concentrate, however, so much was my attention directed towards Tracy's large round breasts and perfect figure. Even while she told me all about her great organisational skills, all I could think about was violating that pretty, proper mouth with my cock, I was even getting a little hard and aroused just thinking about it. Thank God I was sitting down and there was a desk between us to cover my embarrassing arousal.
All this was going well enough but it was as we came to the end of the interview that things started to get particularly interesting. We just asked every candidate no matter what job a standard question to sum up at the end and that question was, "What do you think separates you from the other candidates and what do you think you in particular have to bring to the company that nobody else does?" Everyone tended to come out with some pretty similar answers to this one but Tracy Class had something a little different.
"So, you want to know what makes me special?" she said, with a lascivious accent that belied the restrained sensibilities of her earlier answers.
"That's right, Tracy," I replied, "Just tell us why I'd rather have you as my secretary than anyone else."
"Well, I've one very special feature," she grinned naughtily.
At this point I expected her to go on about how well qualified she was but instead she sat back on the chair and uncrossed her stockinged legs. Inevitably, I tried to sneak a look up her pencil skirt at her panties beneath as she opened up her legs but just now I didn't get the chance. However, Tracy wasn't going to stop there and, to my wide eyed astonishment, she reached down and pulled up her skirt around her waist, showing me her stocking tops, the bare skin of her thighs and the black satin panties she wore beneath. What was even more remarkable was when she pulled these panties aside and pulled out that little something that made her special. It was her cock, eight inches long, thick, veiny, uncut and semi-hard. Yes, Tracy Class, the hottest, sexiest job applicant I had ever had, the one that I had been fantasising about just a few seconds earlier was a shemale, a chick with a dick, and that dick was growing ever harder as she began to stroke it in front of me, in my office, in our interview.
"You wanna know what makes me special?" she asked, stroking her hard cock, "How many of the girls who applied can show you this?"
I sat there transfixed, not knowing what to do as my interviewee masturbated her cock in front of me. I couldn't help but stare at it. It held an incredible fascination, this hard, masculine cock protruding from Tracy's gorgeous curvy womanly figure. Although it was weird, I knew I was incredibly turned on, the revelation of Tracy's shemale status seemed to make my own cock even harder under the desk. It seemed that Tracy somehow knew this too as she gave me a dirty grin.
"Don't just stare at it, honey, why not come and get a taste?" she said.
As if in some kind of hypnotic state, I felt myself obeying, getting up from my seat and coming round to her side of the desk, I dropped to my knees in front of her. I had always thought of myself as a very straight, woman loving kind of guy and had never even thought about sucking a cock before but this one looked so good. I knelt between her stocking clad legs and stared at it, it looked even more alluring close up, poking out from where her satin panties were pulled aside.
"You can touch it, baby," Tracy said.
Taking my hand in hers, she moved it onto her cock so my fingers wrapped around her shaft. It felt excitingly warm and alive in my hand.
"Come on honey, wank me," she smiled.
Once again, my reaction was almost instinctive as my hand began to rub up and down her dick, masturbating her as she got ever harder. I leaned my face in closer to where her sheer stockings ended and the bare skin of her thigh began, kissing along her soft, feminine thighs, I soon found my lips alongside her cock. Still jerking her off, I pulled her dick up and moved my lips to her shaved balls, beginning to suck on them. As I masturbated her, I moved my lips all over her balls and began to lick up the base of her hard cock shaft.
"Ah, uh, yes, that's it, lick my balls, honey," Tracy moaned, "Now how about you wrap those pretty lips round my cock?"
I did as she said once more, my tongue having reached the swollen purple end of her masculine part, I flicked my tongue around the tip and opened my lips to let it in. If the feel of her cock in my hand had been something else then having it in my mouth was even better, warm and sensual, I could feel her arousal all through my mouth and it felt great to be the one giving it to her. OK, so only a few minutes earlier I had been thinking about her going down on me, but if anything the sensations from taking her cock in my mouth were even better so unexpected were they.
"Suck me baby, suck me like a dirty sissy whore," Tracy moaned, bringing her hand to the back of my head and pushing me down on her cock.
I had never sucked cock before but I'd had it done a fair few times to me and I'd seen my share of porno so I'd like to think I knew what I was doing as I opened my throat to let more of this hot woman's eight inch monster down my throat before pulling back and bobbing up and down on the full length of it, all the while using my hands to play with her balls and arse. I was no longer in control of my actions, I was taken over by lust to swallow this strong, beautiful woman's large cock. My mouth watered and I slobbered all over it, no longer concerned by how easily I had been swayed to suck cock.
"Oh Fuck, oh God, you dirty bitch," Tracy moaned, "I can't believe you've never sucked cock before, you're a natural sissy and you're turning me on sooo much."
"Mmmmmm, ugh," I could only gargle, my mouth filled with her tasty meat but she knew from my eagerness how much I was loving this.
"Oh yes, come on," Tracy cooed, "Tell me how much you love it, beg for it, slut."
"I love the taste of your cock, Tracy," I said, taking it from my mouth as I continued to stroke her shaft, "I'm a sissy cockloving bitch and I can't help but want to taste your big, fat cock," I didn't know where all this was coming from, this was a side of me I had never seen before but I couldn't control it, "I'm your sissy bitch and I wanna make you cum, I want to swallow your cock and drink your juices."
Tracy laughed, "You were right, honey," she said, and I suddenly noticed her attention wasn't directed at me.
I had been so intent on giving my shemale secretary interviewee my very best cocksucking efforts that I had been blind to anything else going on around me and now I noticed that Paula the receptionist had joined us in the room. I stopped dead, I couldn't believe the humiliation.
"See what I mean, Tracy," Paula grinned, as it began to dawn on me that these two knew each other and had set this up, "I knew he was just a sissy at heart."
"You're right," Tracy purred, "You wouldn't believe how quickly and easily I had him sucking cock."
"Ha, I knew it!" Paula exclaimed with me still feeling totally humiliated and not knowing at all what to do, still on my knees and with my lips still around Tracy's hard cock, I could hardly get up either as this would show my receptionist and her shemale pal just how hard my cock was and just how turned on I seemed to be being discovered by a hot woman sucking off a shemale, "I always thought he'd be just the sort to enjoy a good cocksucking, look how hard he is!"
As she had been talking, Paula had walked over and knelt over by me, bringing her face down close to where my own flushed red looking one had just let Tracy's cock out of my mouth, but it was still dangling angonisingly and tantalisingly close and I could barely take my eyes off it to look at the face of the beautiful blonde kneeling beside me. Paula had reached beneath me and was feeling her hand over my crotch, simply brushing her fingers across it, she could not only tell just how hard cocksucking and humiliation made me but could make me just little bit harder. Now Paula was unzipping my trousers and pulling them down around my knees, completely exposing my hardness.
"Ha ha ha, Tracy," Paula laughed, running her hand along my cock, "It's barely half the size of yours. I never realised my boss was such a little man underneath it all!"
"How does that make you feel, little boss man?" Tracy laughed, "On your knees in front of your secretary looking at her cock and finding it much bigger than yours?" Frankly, it was an incredible turn on, "No wonder you're such a sissy cocksucker when even a girl like me has a bigger cock."
Embarrassingly, this teasing did nothing to stop my little cock from being harder than ever, something that wasn't helped by Paula running her hands all over my arse, massaging the cheeks and occassionally slipping a finger inside and fingering my anus.
"Hey Tracy, you should really have a go at his tight sissy arse," she was saying.
"Mmm, yes," Tracy moaned, "This sissy looks totally fuckable but let's make him beg for it, eh Paula?"
"Oh yeah," Paula grinned, slapping me across my naked arse, "It'd give me a kick to hear my boss beg for your hard cock."
I blushed redder than ever at the words that were coming out of my pretty receptionist's mouth as I knelt humiliated on my office floor. It was going to humiliate me a whole lot more to start begging for it but frankly I really was starting to want Tracy to fuck me, to get my arse used by her big monster cock. With such thoughts running through my head, I knew that I would sooner or later have to give in to them.
"Come on slut boy, beg for it," said Tracy, playfully slapping me across the face with her erect member.
What choice did I have, really?
"Please fuck me Tracy," I sighed, "I want you to take my cherry and fuck my sissy arse. I want to feel your big hard cock sliding deep inside me. It's sooo much bigger than mine, a little cocked sissy like me deserves to be fucked up the arse like a girlish whore."
"Wow, well, when you put it like that, how can I refuse?" Tracy giggled at my willingness to humiliate myself in front of these two beauties.
She moved around behind me still stroking her big manly cock as her receptionist friend explored my arse with first one, and then two fingers, loosening me up so as to better prepare me for the huge thick meat that was about to enter me.
"Ohh," I gasped as Paula shoved a finger inside me, "That feels great Paula, your finger feels so nice inside my arse, I can't wait for Tracy's big hard cock."
"Steady there," Paula laughed, "It's going to take a lot to get that inside you, you'd better be ready for it."
"Ah, oh, come on, give to me, make me your bitch," I gasped as Paula withdrew her fingers and guided Tracy's cock to the entrance to my arse, the head of it now just nestled between my arse cheeks.
"Oh God," I yelled in pain as Tracy pushed her cock up inside me, desperately hoping nobody in the office would hear and come and see what was going on.
Despite my girlish squeals of pain, Tracy continued to push inside me, I felt in agony and completely impaled, stuck on Tracy's massive cock, I was totally in her power and that was a feeling that I was starting to like.
"Now your going to take it like a real sissy slut," Tracy told me as she withdrew her cock before slamming it into me once more.
I could feel the material of her skirt falling around my waist and her shear stockings brushing against my thighs as she stood over me, her legs astride mine, plunging her cock deep inside me. Looking behind me, I could see her proper secretarial look was beginning to go as her long dark hair had been untied and fell all around her face. Paula had pulled her blouse open and was now suckling at one of her massive breasts, having pulled it free of her black bra. I was still in quite a lot of pain, feeling totally filled by Tracy's big cock of which almost six inches were now buried inside me, but it was starting to feel pretty good too. With my arse filled like that, I was feeling her cock stimulating in me in places I'd never even thought about before and my own cock was still rock solid with arousal. By the time Tracy had stuck her whole cock inside me and I was stuck on it, barely able to move, I was really enjoying it in spite of the pain.
"Oh fuck, your little arse is tight," Tracy moaned, "It's been a while since I've taken a sissy's cherry and it feels so good on my big cock. Don't worry baby, I'll be gentle with you."
"Uh, ah, no, fuck me harder," I sighed, moaning like a dirty whore, "Fuck me. Fuck me like a little bitch, I wanna be used by you."
"OK then," Tracy giggled, "My, you are one eager sissy slut."
"Oh God yeah," I moaned as she ploughed so deep I could feel her balls slapping against my arse, "I just love the feel of a hard cock inside me and just love getting fucked hard."
As I was enjoying the intense pleasure of my busty secretary ploughing her big cock deep into my virgin arse, my pretty receptionist Paula had left her place where she was sucking and licking Tracy's breasts and moved around in front of me. With her back to me so I could stare at that gorgeous round arse of hers, she unzipped her skirt and pulled it down, bending over to shove her panty clad arse close to my face. As she stripped from her panties too and turned back to face me, I could see she was sliding her fingers deep inside her shaved cunt. It was quite a sight and one that I had only thought to see in my wildest fantasies. Of course, in those fantasies I was never on my knees being fucked doggystyle by the big long cock of a gorgeous, busty secretary but, hell, this was much more fun.
"I know that it's cock that you really love now boss," Paula taunted fingering her pussy right in front of me, "But I've seen you eyeing up my sweet arse, how would you like a piece of it, just like Tracy has got you."
"Oh God, Oh fuck, yes," I yelled, both in answer to her question and because of the hard and heavy arse fucking the sexy shemale secretary was giving me, "God yes, I want your beautiful arse Paula."
"Go on then, eat me, you dirty sissyboy," she said, turning around and shoving that perfect round arse right in my face.
OK, so, if anything this was even more humiliating. Me, the big important boss of the whole company on my knees, sticking my tongue in the warm arsehole of my pretty receptionist and having my own arse fucked by tranny Tracy. Of course my own rock hard arousal was showing to anybody who happened to stick their head round the office door how much this kinky situation was turning me on. After a while in which I had got to taste the inside of Paula's arse, sliding my tongue inside her even as Tracy withdrew her cock from tearing into my arse, I had got her pretty wet.
"OK, sissy," Paula sighed, "I need you to fuck my arse, now."
Tracy pulled out of me and sat herself back in my office chair. She looked absolutely gorgeous, the complete image of a well fucked slutty secretary except for the big erect cock sticking up between her legs, her hair was a mess and her eyes behind her glasses had a sexy glint, her blouse was open with her massive breasts pulled out over her bra, her skirt hung around her waist and her legs in sheer stockings and heels were open to show off the full length of her hard cock.
"Come over here and sit on my lap, sissy bitch boy," Tracy beckoned.
Well broken in to do just what she wanted, I meekly walked over and lowered my arse onto her cock until I was totally impaled on her big pole with my littler cock sticking up from me now, I faced away from her so I could feel her huge round breasts pressing into my back. Now, Paula came over to me and looked down at us.
"You make quite a picture, the manly boss impaled on the sexy secretary's big cock," she laughed, looking down at my little meat, "I just hope you're up to satisfying me with a little sissy cock like that, I'm so used to Tracy in my arse."
She sat down on my cock and even though that big shemale dick that was inside me had been there before me, her arse still felt pretty tight and it was just amazing to finally be inside it, not to mention the brilliance of being sandwiched between two such hot women, one with that little something extra. I was now in control of how I would ride Tracy's firm cock and found myself bouncing up and down on it, even as I pulled up from her cock, I slammed into Paula's gorgeous arse.
"Oh fuck, you're one eager sissy," Tracy moaned.
"I'd never have guessed quite how keen you would be for a hard cock up your arse," Paula sighed as I thrust back up into her, "I thought you'd take a bit more persuasion than this but it turns out you really are just a cock loving sissy."
"Oh god yes, oh fuck," I moaned, loving every second of this kinky office threesome.
"Oh yeah, your tight sissy arse is gonna make me cum," moaned Tracy.
"Ah, oh, ooo, fuck, Tracy," I moaned, picking up the pace at which I rode her firm cock, determined to make this hot, gorgeous woman cum, "Oh God, I wanna feel your cum deep inside my tight virgin arse, cum for me, Tracy."
But it was Paula who went over the edge first, throwing back her blonde hair and her body convulsing as she bounced up and down on my cock and furiously rubbed her pussy until it leaked all over her juices. She put her clothes back on and stood back to watch the end of the show as her sissy boss rode that hard shemale cock. Without Paula's arse to stimulate my cock, I had to stroke it myself as I bounced up and down on Tracy's cock.