Jacqui Steps Out

This is a true story – every bit of it. I would like to dedicate it to the two men who shared that fantastic night with me but who never knew quite what it meant to me.

*

He'd been planning it for weeks. Now it was going to happen.

The business to the North had provided the opportunity and he had everything with him. In the boot of his car was the small briefcase that contained everything he needed to be his other self.

He was trembling as he pulled the car in to the motorway services and took the case with him into the Gents. He found an empty cubicle that still had a coat hook intact on the back of the door and started to strip.

His male attire discarded, he popped the catches on the case and took out a pair of black lace, tummy control panties and eased them over his shave and wax'd legs. His pubic hair was gone too and he pushed his smooth cock and balls so that they were encased by the panties and tucked snugly away at the top of his thighs.

One day he intended to master the technique of a female impersonator he'd seen on television, actually pushing the balls back up inside his body. For now though, he looked tidy enough in that department and was beginning to feel really excited.

He pulled on the sheer black hold-up stockings and then clipped on the black bra. The yellow sweater dress followed before he pulled his jeans back on. The sweater dress was gathered round his waist for now and would look like nothing more than a sweater for the time being. He stepped back into his loafers, put his male clothing into the case and, remembering to flush the chain, he left the cubicle, looking no more or less like the man who had entered it minutes before.

Back in the car, his heart now beating strongly, he drove to a quiet corner of the car park, before squirming slightly in his seat so that he could pull his jeans down and off. He then replaced the loafers with a pair of pointed toe, black patent high-heels and started to apply his make-up.

Face on, he teased his hair like his friend Ray had shown him, to pull it from his regular slicked-back style into a tight, girly bob. Then the finishing touch. From inside the case, two silicone breast forms, which he pushed up inside the sweater dress and into the bra. He felt so good, and so hot.

The next stage would be the first big test. He drove back onto the motorway as far as the next services, parked and got out again, this time going into the ladies, handbag on his arm.

Again he used a cubicle, as all ladies do, and this time he really did want to pee. Taking a panty liner from his handbag, he slid it into place in his panties to prevent any seepage spoiling the knickers and, pulling a condom over it, pushed his cock back into place.

Outside the cubicle, he washed his hands and, using a compact from his handbag, checked his make-up. Women came and went round hi, without a murmur. He was now a she. Jacqui was ready.

What Jacqui really wanted now was to find a man. She realised, however, that it would have to be a man that knew, and she did look very convincing. So a gay haunt was required and she knew just the place.

Ten miles from home, lay-by offered the perfect scenario from about 9 o'clock every evening. By the time Jacqui got there it was 9.45 and the lay-by was very busy. She found a space towards the end of the queue of parked cars and reversed back into it, noticing a silver 4-by-4 parked immediately behind.

After stopping the car, she looked round to assess who was there and what to do, when saw the interior light of the 4-by-4 being switched on and off. She did the same with hers.

To be sure there was no confusion, she got out of her car and want round to the boot, bending into it enough to reveal the tops of her hold-up's under the hem of the sweater skirt.

She turned, as if to check for oncoming traffic before returning to her car, and looked straight at the drivers place in the 4-by-4 at the same time.

Returning to her car, her heart now pounding with nerves, she saw in her mirror, the guy get out of his vehicle, lock it and walk to the passenger side of her car.

She opened the door to let him in.

He was gorgeous. Dressed all in black leather, including gloves, he was about 5'10", clean-shaven, with beautiful crystal blue eyes, and a rugged clean-shaven jaw. He smelt of expensive cologne and she knew that he knew and all would be OK.

"Wow" said the man, looking at her as she sat there.

"Wow, yourself", giggled Jacqui.

He leaned towards her and they kissed, their tongues quickly and urgently finding each other, his gloved hand on her knee.

She parted her legs slightly as his hand travelled slowly up her thigh. As it reached her panties, she felt her cock twitch and knew she would come straight away if he touched it.

Squeezing her legs shut, she removed his hand, looking in his eyes and laughing as she did so.

She leant forward and unzipped his leather trousers reached inside and slowly pulled out a circumcised cock that was at least 7" long, quite thick and already glistening with pre-cum.

Looking at him and licking her lips, she moved her head down so that her lips brushed the helmet of his cock. She pushed the tip of her tongue into his cock hole and then eased her lips and then all her mouth round his shaft.

She wanked him with her right hand as her mouth sucked him off. She paused momentarily to let her tongue flick the tiny loose flap of skin under the helmet.

Returning to her task she now sucked him more vigorously than before and she felt his arm reaching round to cup her as cheeks. How her ass felt hot and desperately wanted him to fill it, but that would have to wait for maybe another time.

She heard his breathing quicken as she sucked and wanked, sucked and wanked. Still sucking, she stopped wanking him to cup and stroke his balls, and then returned to wanking, her fingers moving in sync with her mouth to give him the ultimate feeling.

He grunted, bucked his hips slightly and pumped fresh, hot, salty spunk deep into her mouth. Jacqui kept sucking and kept her lips clamped to his shaft so that nothing escaped. Reaching for her dash she pulled two mansize tissues from the box she kept there and moved them into place round and on top of his cock as she slowly pulled her mouth. Only now did she swallow the cum that had collected in her mouth and throat, letting him see her do so, a tiny drop dribbling from the corner of her mouth.

They kissed again, just lightly brushing their lips and she now lay back in her seat, opening her legs again and looking invitingly at him. The gloved hand was there like a shot, and just as she knew she would, she began to cum instantly, filling the condom he had wisely pulled on at his last motorway stop.

At the height of the sensation, she grabbed his hand to stop him going any further. That had been great, but now she wanted to kiss this handsome stranger goodbye and go and clean up.

When he started to speak, she kissed him and with a look made it clear they were done.

The stranger back in his own car, she drove about 3 miles to a roadside café, used the ladies to freshen up and dispose of the condom and sat down to a salad and a cup of tea.

As she ate she was aware of being watched. Worried that she'd been found out, she looked up slowly to see a rather rough looking man, slightly overweight and in need of a shave, looking back at her from across the café. He smiled, she smiled back.

He came over and sat opposite her. He told her he was a trucker, with his lorry parked outside and he'd noticed she was by herself. He offered to pay for her food and when she said "no" he insisted and paid for it anyway, together with his own bill.

His next line was so obvious, Jacqui almost laughed in his face, but controlled herself as he asked her if she would be kind enough to go with him to his truck to show him on his map where the next town was that he was heading for.

Wondering what the hell she had got herself into, let alone how she would get out of it, she agreed, and had to lean on him as they walked across the pebbled car park, as he tottered slightly on her heels. As she did so, she could see the bulge growing in his jeans.

He helped her up into his truck, and got a full eyeful of panties and stocking tops as she climbed in. Once in the driver's seat, he muttered something about his maps being in the sleeping space at the rear of his cab and he climbed through to find it.

Within a minute he said he wasn't sure which map and could she help him work out, so she carefully eased her way in to find him naked with a fat, uncut 9" prick being worked furiously in his hand.

She smiled at him and kissed him and took over the wanking, her mind working overtime as to how she would come out unscathed, as it appeared obvious that the trucker thought she really was a girl.

Her pushed her down and said he wanted to fuck her.

"Y-you can't!", she stammered.

"Come on babe. You know you want it. Don't tell me you didn't know what you coming in here for!"

"Yes, I do, but I can't. It's my time of the month. My period."

"I don't mind a bit of blood!"

"Oh, but it's more than a bit."

Still wanking him she looked into his eyes, and inspiration struck.

"Would you like my ass instead?"

His eyes lit up. Now all she had to do was make sure she dropped her panties just far enough and kept his hands from her "cunt".

She turned over, and eased her panties down exposing the smoothest, sweetest-smelling ass that trucker had seen in months.

"Be gentle" she said, and then let out a little scream as she felt the think 9" of hard cock being pushed into her.

His huge hands landed either side of her head as he pushed deep into her anus, her eyes almost screwed tight with the pain.

As he fucked her, the feeling eased and she not only began to enjoy it, she could feel herself becoming aroused.

His breathing was quicker now, and accompanied by grunts of pleasure as well as effort.

She clenched her ass muscles round him.

"Do you like my tight little ass?" she teased.

"Oh fuck, yes!" he panted. "Oh yes!"

"Fuck me!" she yelled, "fuck me. Fill me with your hot, sticky spunk. Come on, cum inside me. Fuck me."

It took only seconds more, before she felt his cock throb and pulse four, five, six seven, eight times pumping creamy, hot semen into her. When she thought he was spent, his weight pressed hard on her back, a ninth throb seemed to deposit as much as the first eight altogether.

She eased him off her and he rolled over, sweating profusely on to his back. Grabbing a towel that lay across his bed she wiped as much of the residue away before pulling her now soiled and sticky panties back up and into place.

Leaning over him, she looked into his eyes.

"That was great", she said, and then lying, added, "you made me cum too. Next time you can fuck me properly."

She kissed him and left him lying there panting as she carefully negotiated the cab, climbed down and walked back to her car.

She felt used, filthy and wonderfully satisfied.

She would find a place to clean up and change back, knowing now that she was ready for the world to meet Jacqui on a regular basis. And it seemed the world was up for it, too.