Loading...The name’s Michael. I’m an Irish boy from nowhere in particular, and the bright-red ponytail I wear is more than enough proof of that. I dress well enough when I need to; my work wardrobe usually consists of black wingtips, tight-fitting black slacks that are a little loose around the knees to allow for bending, and a dark solid button-down. I’m a relatively fit guy; I bike to work every morning and jog in the evenings.
I’m not what you’d call “buff” but I get the occasional look from the ladies in my totally unprofessional ragged jeans, faded t-shirt, and worn-comfortable sneakers on my days off. My green eyes probably don’t hurt my chances at getting a date, either. I work for a proofreading firm that takes in about fifty thousand documents a day; there are eighty-two of us altogether, including three editors-in-chief and a managing editor.
This story’s about the managing editor. My job has always been as a personal assistant to the managing editor, a lovely dame named Collette. She’s got sharp, strong features but curves like you wouldn’t believe. Her soft, chocolate-brown hair always hangs straight to the sides and curves just under her chin; she’s got these gorgeous blue eyes you could just get lost in; and she’s a little pale but attractively so. She doesn’t wear much make-up, thankfully; she just throws on some violet eye shadow and red lipstick – the kind that doesn’t smear, fade, or come off when you kiss your lover – and dons a pair of dolphin or panda earrings. It’s always the same with her: dolphins or pandas. Her black button-down is always neatly tucked into her knee-length, wine-colored pencil skirt; she always has black stockings; and she always wears dark-red heels to match her skirt, although they’re not the stiletto kind. No woman in her right mind would wear stilettos.
Of course, there’s just one little thing that a few people around the office have noticed that’s out of the ordinary about Collette. She’s a he. See, that’s the thing about our company: it’s very open to the LGBT community. Collette had her name legally changed a few years ago but she’s never had the surgery; I guess she likes it that way. She has had all of the hair on her body (other than her head) professionally removed, though, so the only indication that she’s a he is her strong features; she had her Adam’s apple removed a while back. She has this cute voice, too; it’s a little deep but very feminine. It’s natural, oddly enough, whereas a lot of people will have their vocal cords altered if they want a feminine voice.
Oh, and that’s the other thing about me: y’know all those ladies I mentioned getting sultry looks from on occasion? Well, I’ve never dated a woman. That is, I’ve never dated a biologically accurate woman. See, that wouldn’t work for me because I’m gay. The office certainly doesn’t mind, and most of the people around here don’t ask or tell. It’s not that we have a rule about it; it’s just that most people don’t care. One of the first things you’re asked when you’re hired is if you have a problem with the LGBT community – not if you’re for or against gay marriage or anything like that but just if you’re okay working with people that probably don’t date people of the opposite sex. It’s just to make sure that there aren’t a lot of problems in or out of the workplace.
So back to Collette, you’re probably wondering how I know so much about her. Well, the answer to that is a long story. I hope you’re relaxing because it’s a very sensual story, and I’d hate for you to get all tensed up when you’re tense enough already – unless that’s how you relax. In that case, proceed. Are you relaxing? Good. Then sit back, read on, and enjoy.
When I first became involved with Collette, I had just turned thirty a week before. It had hit me long before my birthday that I was old now. Oh, it wasn’t that I was eighty-something and had a multitude of medical problems that I knew were all going to kill me in a short while. It was that I couldn’t be considered a kid anymore. I’d always been “the kid” to everybody around the office, in my family, and among my friends. My friends still call me that from time to time but it’s all in good fun. Death doesn’t scare me; even getting older doesn’t scare me. What scares me is getting [i]old[/i], and the prospect of actually dying – as well as what lies on the other side – scares me even more. So I wasn’t exactly feeling peachy now that I had leapt the first true hurdle of adulthood.
When I went to work that fateful Monday morning at nine o’ clock, things all seemed relatively normal. We’d had an extremely mild winter, which was weird, and it was a little drizzly. It was cold. But other than that, it wasn’t a bad-looking day. The sun might even come out later, according to the weather man. I clocked in, headed to my office, and said hello to a couple of people on the way over there. I yawned at least twice, although nine isn’t frightfully early. You know how it is, though: you go out with your buddies, you have some drinks, you stay up a little late, and then you go to work a little tired the next morning. Anyway, I also did my usual eyeballing of Collette’s beautiful, shapely ass when I walked by her office; it’s right next to mine and she NEVER has the door closed. I hung up my coat and hat in my own office, checked my e-mail, and headed next door to begin the day.
It was at around ten-thirty that I started to notice certain things about Collette. First, she didn’t seem to be very happy herself. In fact, she seemed a little weary – not tired, mind, but mentally or emotionally weary. We talked for a few minutes; I got her to open up and found out that her sister was getting a tumor removed from her right leg. Apparently, she’d had it for a while but hated doctors; now, she had no choice but to remove it. It was apparently difficult to remove but Collette had referred her to a tumor specialist; he was really good. Collette was still worried, though, because even the best doctors stood a chance of leaving part of it behind. You just couldn’t plan for everything. The second thing I noticed was that Collette’s ring finger no longer held the sterling silver wedding band she always wore. It turned out that she had just finalized a divorce initiated by her husband of five years; supposedly, he was actually bisexual – not gay, as he had told Collette when they got married – and had been cheating on Collette with some blonde bimbo from the south side of town (a very poor area whose most outstanding feature was its red light district) for about six months. Needless to say, Collette wasn’t not a happy boss.
I told her I’d take her out for drinks after work if she wanted, and she said she’d enjoy that. Then we got back to work. My lunch break came at twelve-thirty, and I always head out to the Arby’s nearby. I absolutely love roast beef sandwiches. I offered to bring Collette something but she opted to take an early lunch instead (hers is at one). We ended up taking an hour for lunch instead of our usual half-hour, which meant we’d both be working an extra half-hour tonight; we didn’t mind, though.
We sat and talked and ate for the majority of that hour, and we really enjoyed one another’s company. At one point, I started flirting with Collette without even realizing it; she didn’t seem to mind, though, and went right along with it. She seemed to be into me, and I’d been into her since I’d started the job six years prior. I’d gotten an Associate’s in General Writing, which included proofreading and elective languages (Spanish, Japanese, and Russian in my case), and gone on to get a Master’s in English Literature before coming to work for Collette. She’s three years older than me and started as an editor; she was promoted to editor-in-chief (one of three) after three years on the job, which was when I came to work for her as an assistant. After three more years, she had been promoted to managerial editor and I was retained as her personal assistant since she hated having to train someone new.
When we got back to the office, Collette told me that she’d enjoyed our lunch (she had insisted on paying for it all) and that she’d love to do it again tomorrow. She rescheduled her lunch hour specifically for that reason. At around three-thirty that afternoon, she called me into her office and asked for some documents. I gave them to her and we looked over them together. Then we talked for a few minutes on a more personal level; she asked me if I was dating anyone. I wasn’t. She passed it off as not wanting to take up anyone else’s time by having drinks with me after work but it was kind of an obvious ploy. I think at this point she was particularly vulnerable, considering everything that was going on in her life. At the end of the day is when things got interesting.
Everyone else was gone, except for a few people doing server and physical maintenance. Collette and I were the only ones doing any real work, and we were trying to use the time to get ahead of a few things so that we wouldn’t have as much work the following day. When all was said and done, Collette closed the door so that we could talk without being disturbed by Clayton, a guy who likes to overhear everything and spread as much gossip as possible. When she’s preparing to leave work, Collette always closes the blinds so that no one can see in her office. When she closes the door, it’s usually to discuss a managerial subject; it’s rather common so Clayton probably wasn’t too worried about it. At least, that’s what I thought. I had no idea what was about to happen, nor did I know what Clayton would be doing just outside the door while Collette and I were…well, I’ll just tell you what happened.
Now remember: Collette was rather vulnerable but she’s the boss. She was sitting on the edge of her desk and I was standing before her. We were talking quietly so that Clayton wouldn’t overhear any juicy gossip that he might be able to spread. At one point, we somehow ended up talking about Collette’s love life. I had never had much of a love life, though I wasn’t exactly inexperienced when it came to romance. I’d had two boyfriends in my life; the first, when I was fifteen, had been all about the sex. He’d been my first. Todd had been all right but looking back on it, he hadn’t been great. Then again, we were both teenagers. The second, when I was getting my Masters, was James. James was all about the romance but we’d gotten into bed a few times. He was pretty good.
I’m still not sure exactly how it all played out; I was kind of in a daze by the time we were finished. I think, if I remember right, we were talking about who was and who wasn’t a good kisser and ended up deciding to try our own hand at it. Collette’s lips were soft and lush, and her skin was smooth and a little warm to the touch. She seemed to enjoy my own lips and the shaved body that she had drawn close to her. The more I kissed this beautiful crossdresser, the less I could resist the tantalizing taste of her teasing tongue. I sucked on that tongue for a full ten minutes, and she returned the favor with gusto. Soon, my hands were roaming down Collette’s body in a very slow and exploratory fashion. She was quite physically fit herself, it seemed. She stood to let me run my fingers across her ass, and I dug them in for a nice squeeze. It only made her kiss me more passionately. Our bodies were almost entwined now, so close were we to one another. She put her arms around my neck as I started massaging her firm cheeks, our lips locked in an endless struggle for erotic supremacy.
Finally, I couldn’t take it anymore. My hands returned to her blouse, and I started undoing the buttons one by one. When I got near the bottom, I had to pull her blouse up out of her skirt to undo the last two buttons. I ran my fingers down Collette’s soft chest and firm stomach; I could tell she did crunches regularly but hadn’t worked her pecs much. I didn’t care. We caught our breath when I broke the kiss, and I put my lips to her shoulder as I slid the dark-blue silk away from it. She tasted wonderful, like a delicacy whose flavor I couldn’t quite place. I kissed my way down to Collette’s right pec as she leaned back against the desk once more and ran my tongue slowly around her nipple. Finally, I teased it a little before sucking on the tiny thing. I paid my boss’ other nipple no less homage, and then I kissed my way down her masculine stomach. Her belly button was an outie and I flicked it a few times with my tongue just to get a giggle out of her.
Then I was sliding her maroon skirt up her legs. I ran my hand up under there and felt the Holy Grail hiding beneath lace panties, which I soon discovered were as blue as the Arctic Ocean. When I pulled them down a little, I saw the most beautiful cock I had ever laid eyes on. It was half-hard and already six inches long. How she managed to hide it, even beneath her skirt, was beyond me. I ran my tongue across her smooth sac and took one ball into my mouth. I sucked on it for a while, listening to Collette’s breathing change. Then I switched to the other ball, and I ran my hands up her body as I took it into my mouth. My nails dragged across her skin, leaving marks behind as I dropped her sac. My tongue ran up the shaft of the now fully-hard cock before me. I did not immediately wrap my lips around it, though. I kissed the shaft and sucked on it a little; I used my teeth on it but only lightly. I heard Collette moan a little, half-grunting in pleasure.
Then I ran my tongue up that long, hard shaft once more – until it covered that delicious cock’s bulging head. I slid my mouth down over my boss’ cock slowly, enticingly, but did not go all the way down on her. I came back up, teasing her as I slid back down once more. Three or four times I did this, and then I finally sank all the way down. I missed about two inches of it but I don’t think Collette gave a damn at that point. As my right hand continued to run its fingers and nails along her body, my other hand squeezed and caressed Collette’s balls. I pulled up from her cock slowly and just sucked on the head for a few moments. Oh, she was definitely moaning now. Collette put her hand on the back of my head as I went down on her once more. I twisted my head a bit and squeezed her sac before coming back up. She grabbed my ponytail and started holding onto it for dear life. I kissed my way up and down the shaft once more, and then I again started sucking on the head.
Collette was caught somewhere between ecstasy and agony. I was teasing her brutally; she was experiencing so much pleasure, yet I kept drawing back just as she was starting to tense up. I went down on her again, one hand squeezing her balls and the other pinching her left nipple. After a while, she couldn’t take it anymore; when next I went down on her, she pushed me all the way. I almost gagged but somehow managed to take in the whole thing. I squeezed her balls a little harder than I meant to and practically ripped her nipple off with my fingers. But when I came up, she was just barely holding it in.
One long, slow lick of her shaft and head was all it took to make Collette explode.
I drank every last drop.
Not wanting it to end, she rose up and kissed me passionately once more. Then she got around behind me and started kissing my neck as she undid the buttons of my shirt. She unbuttoned my slacks (I’ve never worn a belt; I’ve never needed to) and started massaging my own cock. It wasn’t long before all six inches of it were hard as a rock; Collette’s was longer than mine but mine had a little more girth to it than hers did. Still, when my slacks dropped and she was pulling down briefs, I wasn’t going to complain. She made me bend over the desk and started running her tongue over my balls from behind. My cock she pulled back, making me grunt, but again: I wasn’t about to complain. She sucked on my cock a little, which was surprisingly erotic in this position, and then ran her tongue and teeth over my ass for a few minutes. Finally, she slid the tip of her cock between my cheeks.
It hurt a little, as such things always do, but there was more pleasure than pain as she slowly buried her shaft in my ass. Then she pulled it out just as slowly, only she left the tip in; she slid it deep into me a second time just as slowly as the first. I could feel her warm, hard shaft inside me as she scraped her own nails down my back. What was it Lady Gaga said in that one song? Oh, yeah: “When it comes to love, if it’s not rough, it isn’t fun.” Well, that perfectly described what we were doing. I’d tried to be gentle but where my marks were temporary, I think Collette’s nails actually left some lasting marks behind. But the pleasure and the pain mingled in a confusing jumble that was highly erotic as she slowly filled me with her long, hard love missile. By the time either of us was anywhere near ready to let loose, Collette had me moaning and breathing as though I’d been underwater for way too long. Even better, as her nails dug into my bag, her other hand was stroking my own hard cock.
Collette came first, her hot semen filling my insides. I laughed and moaned at how good it felt, and then I started to tighten up as well. Drawing me back to her so that I wouldn’t mess up her desk, she made me lean back. Then her hand sent me over the edge, her cock still inside me and the awkward position lining the unbelievable ecstasy with just the slightest twinge of pain. I cried out, unable to contain my joy as she kissed my neck. I shot all over my own chest and stomach; I couldn’t help it. I might have wondered what her plan was had my mind not been blown like a fuse by the intensity of my orgasm. When she pulled out, she turned me over and leaned me against the desk. Then Collette’s mouth attached itself to my stomach as she cleaned me up.
But Collette didn’t stop there. She orally massaged my balls for several minutes after she had cleaned me off. Then she was licking and kissing her way up my shaft. Soon, she was going down on me. She wasn’t nearly as slow as I was; I think Collette was eager to taste me again. If one were to ask how it was that Collette kept me hard for so long and made me orgasm not once but twice in a very short span of time, I would not have had an answer that I could explain in words. Suffice to say that this half-German, half-Italian beauty made me fully realize just how much I’d been missing since my college lover.
Collette’s mouth was like a cattle prod as she sucked and licked and kissed my cock. Her lips and tongue had me gripping the edge of her desk with all the strength I could muster. Unlike me, though, she seemed to enjoy deep-throating. She pushed her mouth all the way to my balls and slowly came back, making me jerk about a little. She licked the edge of the tip, making my legs heat up like a fire was raging inside them and my cock tingle. Then she sucked on the head just as I had sucked on hers, and then she went down on me once more. All the while, her hands were drawing nail marks on my chest and stomach as well as squeezing my balls into submission. When I started tensing up again, it was no wonder why. When I let loose a second time, she drank me like she was desperately draining a beer.
When I was done, she rose up again and started kissing me. I could taste myself in her mouth, and I’m sure Collette could taste herself in mine. We kissed for a while, just sharing body heat as we caught our breath. We stroked and caressed one another as we kissed, our passion still going even as our bodies started to tell us that they were tired. That had been exhilarating, exhausting, and incredible. Once again, our tongues wrestled. Once again, we stirred each other’s passions. After a while, though, we knew we had to get going or people would wonder what the hell was going on in that office. They probably already were.
We dressed and got everything ready for the next day. As we were about to leave, Collette and I both heard something just outside the door; it sounded like a zipper. As Collette was straightening her hair and clothes, I peeked out side. There was no one there. Nobody was looking this way so there was no telling what people might or might not have heard. But I closed the door again and kissed Collette again, ignoring the rest of the world. She mentioned drinks, something I’d just about forgotten, and I mumbled a response. Then we shut everything down and left the office. Collette locked up, I made sure my office was locked up, and then we headed out for some much-needed beers.