tagTransgender & CrossdressersGet Ahead, Give Ahead

Get Ahead, Give Ahead


'How do I get ahead in this business,' Jim, the young, eager new intern asked me one day, 'I've been here for months and I don't seem to be getting anywhere.'

'You want the bosses to notice you,' I replied, watching as Jen, another intern who had started at the same time as Jim and was now the company director's personal assistant, sashayed by, 'Start wearing short skirts and stockings!'

We laughed about it and that's where I thought we left it. A couple of weeks later, though, and we were rooming together at a conference.

I was a mid-ranking manager at the company and I guess Jim saw me as someone to try and impress and ask for advice if he was to get on in the business. Even so, I was slightly surprised to see how he'd taken on my latest bit of advice when I got back to the room after the conference dinner.

I hadn't seen Jim all evening and now I could see why, he had been up in the room dressing up. As I came back in, I was confronted with the sight of the office intern dressed in a pair of nylon thigh high stockings whose lacy tops were barely covered by a little pinstripe miniskirt just like the ones Jen liked to wear. He had a pair of patent leather pumps with six inch pointed heels on his feet. The top buttons of his feminine blouse were unbuttoned to reveal a padded black lace bra.

His face was painted in girly make up with scarlet lipstick and a wig of wavy blonde hair completed the look and made him almost unrecognisable as the guy I knew. So much so that for a moment, I thought Jim had scored a girl or had a stripper sent up.

'Is this the kind of thing you meant?' he smiled, both sheepish and seductive, 'Is this the way to get ahead?'

I didn't really know what to say to this. He really did look pretty like a sexy slut office girl the way he was dressed and it seemed to have screwed with any way I had of thinking straight. It had been a while since I'd seen my wife in such sexy things as my male intern's bra and stockings.

'Let me show you what a good service I could provide,' he walked over, those heels giving him a feminine sway to his walk, I couldn't take my eyes off those long legs in their sexy nylons, 'I'll show you how good a head I've got for this business.'

Before I really knew what was happening, he had started to kiss me. His hand ran down my chest and was unzipping my pants. I realised my dick was getting a little hard.

I tried to put a stop to this.

'Jim stop it, don't be ridiculous. I've got a wife back home. And besides, I'm not into other guys.'

'I'm not either, I'm just trying to give myself something extra the other guys won't give,' he said, 'And give you what your wife won't! She won't ever know. Nobody will.'

He was right. My wife hadn't gone down on my dick in what felt like forever. She hadn't made this kind of effort with heels, short skirts and stockings in a long while either. I might not have been into guys, but right now the one in my room looked more like a hot woman than she did.

He was right too about how she wouldn't ever have to find out what went on in this hotel room. I could get my rocks off with this sexy boy babe tonight and then go back to normal after I got back.

I ran my eyes hungrily down Jim's girly dressed up body. It certainly looked feminine enough to fuck.

All of a sudden, however, I noticed one thing that wasn't so girly. Sticking out from beneath that slutty little miniskirt was the circumcised head of a horny young man's dick, already glistening with his precum.

Jim was obviously not wearing any girly panties under his little skirt and that skirt was so short that it barely managed to cover his manhood. Now, as the situation obviously began to excite him, that manhood was swelling up and that growth had pushed it out beneath the bottom of his skirt.

Even as I eyed him up, his dick was getting harder and that was pushing the skirt up, making it rise to expose him.

Oddly, it was the sight of this aroused manly member that started to fascinate me. I was keen on how easily I could tell that Jim was into what was happening from the growing cock beneath his skirt. The combination of very feminine clothes and underwear and that hard dick was strange and alluring.

I pushed him down onto his knees and dropped my pants around my ankles. My own dick was getting to a state where it was nearly as hard as his.

He looked a proper little slut on his knees in his little skirt, lacy bra exposed, looking up into my eyes, licking his lipstick wearing lips, anticipating getting a taste of me.

'OK,' I said, 'You want to really impress the bosses, you need more than just dressing to impress. Show me what you can really do. Give me head and get ahead.'

He grabbed my semi-erect cock in his hand and started jerking it as he licked around the head. Before too long, he had opened his mouth and let my shaft slide between his scarlet lips.

He sucked and slurped all around my dick, letting it grow longer and thicker in his mouth. I'd never been given head like this by a real girl. It wasn't that he was particularly skilled at it, just the eagerness with which he stroked my shaft and sucked the head was enough to bring me to loud groans and sighs.

'Oh come on, baby, that's it, that's a good girl.'

His own dick had now pushed right up out from beneath that tiny skirt and I couldn't help staring down at it poking out like that, just above the lace stocking tops covering his thighs.

I ran my eyes along the curve of his calves clad in nylon stockings from the pointed heels of his pumps up to the bare skin of his thighs. I knew that I had to get myself between those sexy stockinged legs. I had to fuck this girly boy's ass.

'How's that for you, sir?' he grinned, licking at my quivering dick, 'Better than a stuck up real girl could do?'

'Oh yes, I've never had a girl give head so keenly. Let's see if a sexy dolled up boy babe can fuck better than a real girl too.'

I turned him round and bent him over the bed. Kneeling behind him, I flipped that tiny miniskirt up around his waist to reveal his bare naked hairless ass and thigh high nylons.

I pushed his nylon wearing legs open wide and positioned my dick, wet with the saliva of his cocksucking mouth, right behind his pert little ass with its tight hole.

'Fuck me sir,' he turned back and grinned, lipstick smeared and wig slightly adjusted, still looking like a sexy babe, but a dirtier one than before, 'Fuck me better than a real girl. My skirt wearing boy ass is so much tighter than a woman's cunt.'

It sure was. As I pushed right up inside him, his ass clenched tightly around my junk, making me get even harder. He gasped and still I pushed in until I was buried right inside and could feel his tightness all around me.

It was such a good feeling as I started pounding my intern's ass, seeing him bent over and stretched out on the bed, in his blouse and stockings looking just like a little secretary girl getting pounded by her boss.

My wife would never let me do her anally, but Jim was really getting into it, slamming his tight ass up to meet my deep thrusts. The tight feel of his warm hole wrapped around my dick was sending me into ecstasy.

'Oh baby, that's a girl, what a tight hole you've got, feels so good on my dick.'

'Mmm, tighter than a real girl?' he moaned, 'See how I can please you more, give you more. Your company needs someone like me.'

It was true, this was better than any fuck I'd ever had with a normal girl, he was so keen to do things other girls needed persuading into, to dress in stockings and miniskirts, to give head and take a dick up the ass.

It was so obvious that he was into it too and that got me off even more. I'd have thought that the give away feeling of my balls slapping his, reminding me that I wasn't doing a cute girl intern like Jen up the ass, but my male buddy, would have put me off, but it just drove me on more.

More than his moans and sighs of pleasure, I enjoyed how hard and excited I could feel my fucking was making Jim's dick.

Completely on instinct, I reached around between his legs and grasped his dick in my hand. I started jerking him off as I pounded his ass, enjoying the feel of his dick alive and excited in my hand.

I flipped him onto his back so I could admire that feminine dressed up body with his hard, erect masculinity jutting right out.

He lay back on the bed, spread his stocking wearing legs wide and I got in between them, kneeling with my dick in his ass and his long, sexy legs around my waist, pulling me deeper in.

As I grasped his dick and started wanking him, he tore the blouse open to reveal his black lace bra, looking for all the world like it was on the chest of a real woman. As he threw his dirty blonde head back and sighed like a girl, he began to fondle his chest like there really were tits in that bra.

It was quite a sexy sight, only enhanced by feeling his dick in my hand on the verge of reaching its climax from my anal pounding.

'Ahh, you don't get to see an orgasm like this from a real girl either,' he gasped as his cock blew off in my hand.

He was certainly right, it was a hot sight seeing what looked in almost every way like a slutty girl, shooting streams of sticky white cum right up over her blouse and bra, even hitting herself in the face with some.

That gave me an idea and I pulled my cock, so near its own climax, out of Jim's ass and stuck it right back in his face, wanking it off until it exploded a steaming, sticky hot load right down his cheeks, over his lips and into his mouth.

He licked and swallowed my salty spunk like I'd only seen from porn stars. Even when my wife had sucked my dick, she'd never swallow and now my male intern was doing it instead.

Watching his pretty, girly face as he licked his scarlet lips of my cum I knew that my earlier thoughts about going back to normal life after this had been wrong.

He'd been right all along to follow my advice about getting ahead in stockings and short skirts.

He's now got a permanent job at the company as my own personal assistant and he is very good at giving me just what I need!

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