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This is a short work of fiction, but as with all good tales, there is an element of truth in there, as well.
In my mid to late twenties, I started a new job as a delivery driver for a well known company, delivering mail order items and such to customers homes. My route would take in several counties, including deliveries around my local area. I remember one evening, coming back to the depot after my deliveries, and all the drivers were laughing and guffawing away to each other.
‘What’s so funny?’ I inquisitively asked.
‘Graeme here, was greeted by a tranny this afternoon when he was making his drops. He hasn’t shut up about it since he got back!’ replied old Edward, a guy who thought he’d seen it all.
‘Really?’ I asked, but my cock was already becoming slightly aroused at even the mention of such a sight. ‘Did he dress nice for you?’ I playfully teased Graeme, the youngest of the drivers in the fleet.
‘Nah’, he responded, ‘He was dressed like an old granny, in a tweed skirt and fluffy slippers!’
My cock rapidly deflated. I left the other guys to laugh about it as I handed in my paperwork to the office, before punching out for the day. And that was that for a while. It would occasionally come up as something to tease Graeme about over the next couple of months, but was eventually forgotten about.
One rainy Autumn afternoon, I was approaching the last of my drops for the day in a sleepy little village. The delivery was to a new build bungalow on the outskirts of the village, part of a new estate awkwardly shoe-horned onto the corresponding land, looking completely out of character with every other property in the area. I ventured into the back of my van and found the parcel, and quickly ran up the garden path to avoid getting soaked. I rang the bell and waited for the occupant to answer the door. Within moments, the door opened and what was I greeted with? You guessed it! The same sight that Graeme was greeted with a few months earlier. I managed to conceal my surprise rather well, I thought as I got him/her to sign for their parcel. I was rather taken by the attention to details, such as the beautifully manicured and painted fingernails as he signed for his delivery, and the elegant ladies timepiece on the opposite wrist.
‘Terrible weather, isn’t it?’ he said in an effeminate voice.
My eyes were drawn to his immaculately applied make-up, the quality of the very good wig, the button earrings, the ensemble of his woolly cardigan, checked skirt and tan tights and his feet adorned in fluffy pink open-toed slippers, showing off his painted toes.
‘Oh.. yes. Luckily, I’m nearly finished for the day. I won’t have to drive in this for much longer.’ I answered somewhat belatedly, after getting a good look at my colourful customer.
‘Would you like a cup of tea before you go?’ he asked, catching me somewhat off-guard, smiling coyly.
‘That would be lovely’, I canlı bahis şirketleri answered. ‘Just let me turn off the engine and lock the van.’
Already, I was wondering what lay beneath his sensible skirt, hoping I’d get more than a drink of tea!
I entered into the finely decorated bungalow, and admired the beautiful antiques as I passed the living room towards the kitchen after removing my rain soaked boots. My host was preparing a pot of tea, laying out two cups and saucers from a flowery porcelain tea set. As he poured the water into the pot and let the tea infuse, he told me to sit at the table in his soft voice. He smelled good, as well. There was an overwhelming odour of lavender, sweet and heady.
‘You can’t stop staring at me, can you?’ he proclaimed from seemingly out of nowhere.
He was right. I couldn’t.
‘I’m sorry,’ I apologized, ‘but you are the first transvestite I’ve ever met.’
He chuckled and gave the pot a stir.
‘I must say, though, your make-up and wig is very good.’ I complimented my host.
‘Well, thank you, young man. I just prefer being a woman. There’s nothing sexual about it. When I come home from work, I take off my clothes and slip into what you see, and I feel relaxed. At ease. In fact, when I put my suit on to go to work, that’s when it feels like I’m dressing up, playing another character.’
‘Nothing sexual at all?’ I asked as I leaned in. ‘Did it start out as something a little bit racy, though?’
‘Aren’t you a nosey one?’ he smiled as he poured the tea into the cups, fetching them to the table, before bringing the sugar and a little jug of milk.
‘It did at the beginning. But that quickly wore off. Now it’s just about enjoying the liberty of the clothes themselves.’
I took a sip from my tea. I noticed how my host’s legs were crossed over, pointing towards me in a very inviting way, and I admired the smooth nylon clad calves as the slipper on the end delicately hung in mid-air. I felt a mixture of excitement and dread, because I really wanted to tell my tea drinking friend that I too liked dressing up in women’s underwear, but only to get my rocks off, not to form an alter ego for myself.
‘I have dabbled with stockings and suspenders in the past.’ I awkwardly blurted out. In the past? if you mean by ‘the past’, last weekend when you wanked yourself silly wearing a basque and a pair of black laced top hold-ups, then yes, ‘the past’ indeed!
He looked a little bit shocked and surprised, and looked me up and down over the edge of his teacup.
‘I knew there was something about you.’ he said. ‘We could have a look through my underwear drawer, see if there’s anything you like in there…?’
My cock immediately hardened, and it did not escape the attention of my host, either. Rubbing his immaculately manicured hand over my bulge, he softly whispered, ‘I’ll take that as a ‘yes’, then..?!’
He wandered into his beautifully feminine bedroom, canlı kaçak iddaa a pink duvet with patterned flowers covering the king-sized bed, a dressing table covered in make-up and skin cream, and various glitzy outfits hung over chairs and on the backs of doors. My eyes were on his lovely bubble butt, as he sashayed ahead of me, making that otherwise boring skirt swing from side to side. He closed the curtains to block out the grey, leaden sky, and lit up the room by the two bedside lamps on either side of the oversized bed.
‘Let’s have a look,’ he said as he rummaged through a drawer in his wardrobe, reappearing with a pair of gorgeous black seamed stockings, and a black suspender belt beautifully surrounded with lacy frills. My cock twitched once more in my pants, my erection now starting to become uncomfortable.
‘I’d love to see how these look on you!’ he playfully teased. ‘Go on, put them on.’
I quickly took off my top, unbuttoned my trousers and then awkwardly removed my boxer shorts, allowing my cock some freedom before removing my slightly damp socks.
‘Aren’t you a big boy?!’ I was teased again. I blushed.
I rolled up the stockings on each leg, my companion watching my every move, a naughty twinkle reflected in their eye from the bedside’s lighting, before fastening the suspender belt around my waist and fastening the stocking tops.
‘Oh, you look lovely, dear. Come, take a look in the mirror.’ he encouraged me.
I watched myself in the mirror, my cock framed in delicate nylon and lace, the tip of my penis glistened already by pre-cum. My friend wandered round behind me, his hand gently caressing my buttocks, before fetching it to the front and grasping my throbbing cock. He brought his body close up against my back, and I could fell him grind his own hardened cock against my buttocks, whilst slowly wanking my penis.
I removed his painted fingers from my member and turned to face him. He brought his beautifully glossy red lips to mine and we slowly started exploring each others mouths with our tongues. I moved my hands around his body, before surreptitiously unzipping his skirt, breaking off from our kiss to see it slowly slip to the floor. My curiosity was sated. Beneath his skirt he was clad in a pair of tan nylon tights, which covered a quite big pair of pink knickers, beautifully edged with delicate white lace, and the outline of a very excited prick inside, with a wet patch starting to make his glans seem more pronounced.
‘You’re not too small, yourself!’ I commented and he gave out a manly laugh, breaking from his female alter self momentarily.
My fingers hooked in both his tights and panties, before edging them slowly down and watching as his member was freed, his peeling foreskin revealing a glistening purple headed tip, attached to a thickly blue veined shaft approximately seven inches in length. I placed the tights and panties canlı kaçak bahis directly under his scrotum and this pushed his cock and balls forward. I couldn’t resist. I started off by slowly wanking his cock, pulling back his foreskin all the way to reveal his gleaming helmet, covered in his pre-cum. And then I went to my knees, and stuck my tongue out to lap at the sweet love juices covering his ample member. He moaned in delight as I teased him with my mouth. And then I started to take him in to my mouth, feeling the pronounced veins along his shaft as I ran my mouth and tongue along his length. His breathing quickened. I reached around to stroke his bottom as I bobbed my head back and forth, his backside still covered in nylon.
‘Oh, God! I’m going to cum! I’m going to cum!’ he shouted out, an air of panic in his voice.
His cock twitched and a huge load of sperm shot directly down my throat. Another twitch, and more love juice was sent directly into my stomach. Another twitch, but this time it coated my tongue and palette, and was followed by a few more little ejaculations of cum, which I gratefully swallowed.
‘I don’t think that’s the first time you’ve done that, is it?’ my half dressed companion gasped, his face all flushed.
‘You may be right there!’ I cheekily retorted.
My own cock was still rock hard, my penis tip glistening with the artificial light of the room. My friend shuffled along the bed to open one of the bedside drawers and produced a small tub of vaseline.
‘Do you want to fuck me?’ he said, smiling coyly over his shoulder.
Smiling back, I placed a couple of fingers into the jar and liberally coated my cock with it, as my companion eased down his tights and smothered his anus with the lubricant.
I grabbed my cock and eased it towards his balloon knotted hole, pushing against his opening until there was a little pop and my helmet was sucked inside. I slowly pushed myself in a little further as my friend gasped and I felt his arse pull on my cock, inviting him in just a little further with each slow and deliberate stroke, until finally, the nylon and lace of my suspender belt pressed up against his pale buttocks. He looked over his shoulder, a look of lust in his eyes.
‘Fuck me! Fuck me hard!’ he barked.
Who am I to disappoint a ‘lady’? I obeyed and dutifully pounded away, the slap of my scrotum bouncing off his pale backside. After only a couple of minutes, however, the onset of my own orgasm was apparent.
‘I’m cumming…!’ I roared out with guttural pleasure as I filled him with my seed, jet after jet shooting into him.
I collapsed onto his back, panting, before giving him a gentle peck on the cheek and withdrawing my semi aroused cock from him, my sperm slowly running down his thigh.
Post orgasm, I felt silly now dressed in stockings and suspenders and started to unfasten the stocking tops. My friend rolled over on the bed and said, ‘Why don’t you keep those? It’ll be a reminder of our time together.’
‘Well, thank you very much. I’ll think of you every time I’m beating my meat in them!’ I replied
‘No, thank you! I was expecting a special delivery today, but I definitely got more than I bargained for..!’
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