First Night


Looking back now, Mike could see how Mandy had skilfully manoeuvred him into stockings and suspenders: right from the time they had discussed Gary’s up coming party.

Mandy had suggested a feminine character and Mike’s immediate reaction had been a pantomime dame.

No, Mandy had said, not when all the others would think of the same idea. He could hear her say it even now, “Be original, novel, be unique!” yes, but what? They’d run through all the female characters, any number of princesses, Cinderella and �yes Snow White. Mandy had said that was just right as Snow White was sweet pure and innocent.

“And gullible.” Said Mike to himself with perfect hindsight.

A trawl through the cheap clothes shops uncovered a whole new world for Mike; a dangerous one where the adrenaline high became almost addictive as he searched through the rails of dresses, skirts and tops. A little patience was rewarded with the discovery of a long white button through skirt and a t-shirt style top with sculptured patterns and motifs.

The girl at the checkout eyed Mike suspiciously. Mike felt he must be blushing, but tried to carry it off as an ordinary, everyday affair. He stepped out of the shop clutching the plain white carrier bag, and found he’d been holding his breath. Two deep breaths and he was well enough to walk home.

The following day, a more confident Mike ventured into the town’s department store. He’d walked through the lingerie department many times carefully studying the garments while appearing not to look at them.

“Looking for something nice for your girlfriend?”

Mike had almost died as the sales assistant spoke. He stepped back and tangled himself up in one of the display stands. He recovered enough to nod.

“Looking for a three-piece set in white?”, and she went on without waiting for a reply, “Now this is nice, with the lacy panels, and suspender belt, here.”

Mike was horrified. Surely everyone in the shop must be looking at him. And she was still talking at the top of her voice.

“Do you know what size she is, your girlfriend, her bust and cup size?”

From his minimal research in a thick shopping catalogue, Mike had decided 36b was nicely middle of the road. “Yes, we’ve got plenty in that size. Would you like some shiny white stockings to go with it? They’re a very popular line with the young ladies.”

She waved a packet at Mike, and he managed to smile and say, “Yes”. He paid, and set off for the shoe department.

This was far less traumatic. He selected a pair of size 8 white sandals from the “sale” racks before anyone accosted him. Then he hurried home to try everything on. Mike waited until the house was empty, and the he locked his bedroom door – he couldn’t risk his Mum or brothers finding him dressed up. He put the bra and briefs on, stuffing a rolled up sock in each of the empty cups. The suspender and stockings were a little trickier. Mike had to reattach the suspenders to the stocking tops when he discovered the secret of being able to take his knickers down without undoing everything.



Next came the white sculptured top, and Mike looked down admiringly at the mounds on his chest. He stepped into the skirt; the waist was elasticated and very easy to adjust.

He tried it with just the last few buttons undone near the hem. He undid more buttons, two at a time, and tested the effect by walking up and down. He finally settled on about three quarters undone. Mike put the sandals on, and walked up and down some more. He was aware for the first time of the sensual effect of the skirt moving against his legs as he walked. But it wasn’t complete yet.

There was a male hairstyle and hairy legs to be sorted, and make-up to be applied. The ever helpful Mandy said she would help with all that.

The night of the party came and Mike got his bundle out of the house without his mum seeing it. He drove the short distance to Mandy’s flat, his heart thumping with anticipation. Mandy’s husband Tom was out when Mike arrived. She ushered him into the box room and gave him her shaver.

“You’ll have to do something with those legs.” She smiled and left the room.

Mike stripped to his underwear and began shaving his legs. He decided to shave under his arms too, and then removed most of the body hair he could reach. Mike tingled inside as he slipped the stockings on. Everything that touched his silky smooth legs felt strange, exotic and exciting. Mike finished dressing and called Mandy.

She came in wearing just her French knickers. Mike was used to seeing Mandy less than fully undressed, but he had never seen her topless. As she painted his finger nails and set about restyling his hair, he pondered on the unusual relationship Tom and Mandy had. He wasn’t sure they actually went wife swapping, but they both played the field independently. He was sure Tom wouldn’t think anything of seeing Mandy half naked with a man dressed as a woman.

Tom arrived home at that moment, put his head round the door, smiled, and went to the kitchen to make a sandwich. Mandy finished Mike’s hair and applied hi make-up. He peered at himself in the mirror and. Who was that looking back? It wasn’t Mike. But it was Mikki!

Mike watched the television for half an hour while Tom and Mandy got themselves ready. Mike couldn’t settle. He practised trying to walk elegantly, with some success. Then Mandy and Tom came into the lounge, and demonstrated their Pantomime Horse costume.

They gathered up their bottles and cans, and left the flat, walking a short distance down the road to Tom’s Car. The wind blew Mike’s skirt open to reveal the stocking tops and suspenders. Some passers-by stared at his exposed thighs, and a rush of adrenalin surged through his veins.

He half turned towards them and the wind lifted high enough for them to see his lacy briefs: they whistled appreciatively. From that moment, Mike was hooked – he would have to do this again!

The party was a pleasant enough affair, teeming with pantomime dames but only one Snow White. Several people thought he was a girl: a testimonial to Mandy’s skill with hair and make-up. Mandy danced with Mike several times, always when there was a slow, smoochy record on. She held him close, pressing her body against his.

Towards the end of the evening, Mandy took Mike upstairs away from the noise to talk. “Well Mike, how are you enjoying being dressed up?”

“It’s great!” He paused. “The only problem I’ve got is when I get excited.”

Mandy’s brow furrowed into a question.



“These briefs aren’t really large enough.” And Mike lifted up his skirt to show Mandy his swollen, semi erect penis trying to climb out of his knickers. Mandy’s eyebrows went up, and she smiled.

“Actually, I came to ask if you mind going home now. Tom’s had far too much to drink, and I’ll need some help getting him into bed.”

“Yes, of course. We can go right away.” Mike was looking forward to walking outside in the breeze again.

Getting to the car and then walking back to the flat was as exciting as before, even though there was no one to see Mike’s display. With some difficulty, they got Tom upstairs and into his bed. Mike and Mandy retired to the lounge.

“Why don’t you stay the night?” Mandy suggested, breaking the silence as they sipped hot coffee.

Mandy moved closer to Mike on the sofa. She put her arm around him and kissed him. Mike was too stunned to object, and then he found he didn’t want to object. Her hands gliding up and down his leg smoothed his psyche.

Unselfconsciously, Mike’s hands explored the natural curves of her body. Her hand moved to his penis and she gently caressed it to it’s full stature: it burst out of the briefs. Mike’s hand in response, delved inside Mandy’s knickers, finding comfort in her warmth. He stroked her clitoris with a gentle rhythm.

While their coffee went cold, they warmed up, delving and exploring each other. Mandy stood up and held her hand out to Mike. They walked to the spare room and closed the door.

“Let me undress you,” Mandy whispered. She slowly took off his clothes, making every movement a sensual stroking sensation that held Mike in a state of euphoria. She left his suspenders and stockings on. “I want you to make love to me still made up like a woman.”

Mike now knew where it had all been leading to. She wanted him as her TV lover. Mike took her clothes off as she lay on the bed in front of him, and he surveyed her body.

Why should he complain?

He would never turn down the chance of sex with Mandy, whatever the preconditions.

Mike climbed onto the bed and set about his first night of TV passion with Mandy.

The End

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