Brian was a long distance trucker. A huge giant of a man who loved: football, beer, cars, transport cafes and women; in particular waitresses, just like any other trucker in the world. He was a married man, but sadly his sexual relationship with his wife was over. This wasn’t his choice. She told him that she was no longer interested, that they were both getting too old because of their approaching retirement. She said she would much rather watch the TV or play bridge with her friend Margaret. This didn’t frustrate Brian too much because he was constantly trawling across Europe, necessitating many nights away from home. He often reasoned to himself that if he wasn’t there, he couldn’t miss it.
However, he didn’t go without satiating his carnal desires. Brian had a particularly naughty relationship with a young waitress in her twenties called Jenny. Jenny worked in a small, dark and greasy transport cafe on the edge of a major motorway. To many people this would have been the worst cafe they could work in, and if the environmental health department came to visit, they would shut the place down merely on the appearance of the customers. Some of these men were among the filthiest creatures in the United Kingdom, but Jenny loved working among them; she loved big, dirty men. The dirtier the better, in every sense of the word. Brian was well aware that he wasn’t her only lover, and he was happy in this knowledge; it didn’t over complicate things at home. Jenny would get as much action as she wanted, when she wanted. There was something about her climbing up into those huge trucks, she would tell him, to spend the night cuddled up next to a big strong, dirty trucker, that put her at peace,.
Brian was no longer a young man and he was going to retire. In fact he was on his last European haul when he dropped in on transport Jenny, as he liked to call her, for the last time. She also knew it would be his last visit. They had spoken about it at length the last time he saw her, two weeks earlier. Over the years they had built quite a relationship together. They had become so close that they often joked about being a real married couple. Jenny told him that she loved fucking him the best of all because he was an attentive lover. Too many of the others finished too quickly, she said. She also told him that he was the only one who could make her climax so quickly and so intensely. This made Brian feel good, although he had no reason to believe her; but he also reasoned that Jenny had no real reason to lie to him either, they owed each other nothing. It was true, he was an attentive lover, but only with Jenny. He loved the feel of her soft, youthful skin. He just felt like taking care of her all the time; he couldn’t help it. He liked wrapping her up in a couple of blankets and getting her nice and warm before he fucked her senseless. It gave him an enormous sense of well being when they had sex and they lay together afterwards in each other’s arms.
Brian pulled into the truck park at around six in the evening, after telephoning ahead to see if Jenny was working. He was so excited and he could barely wait. He bought Jenny a gift from his travels and he couldn’t wait to give it to her. It was a beautiful dress with shoes, underwear and stockings to match. Brain had always brought gifts for Jenny, and she had accumulated quite a wardrobe full of sexy little outfits and lingerie that she had decided she only wanted to wear for him alone. She loved to dress up for him.
He walked in and ordered his usual double egg and chips and a pot of tea, before he went to wash himself up a little in the shower cubicles. Brian was about the only trucker who used the showers. He remembered when they had them installed and he and Jenny had spent the evening fucking in and out of them. He didn’t speak much to Jenny, only enough to ask if she was coming to call on him later, then he left the cafe and retired to his unit outside. Brian always tried to play it cool when he returned to the cafe after a couple of weeks. He insisted that she didn’t serve him because he couldn’t resist touching her. He liked to think that none of the other staff knew the two of them were screwing.
When it was time for the cafe to close up, Brian started to get a stiffy just thinking about his little transport Jenny climbing the steps to his cab. He got his cock out and wanked it a little to satisfy his craving. He contemplated bringing himself off in preparation for a night of sex but decided against it; Jenny always made him want it several times anyway. Suddenly the cab door opened and he quickly wrestled his cock back into his trousers. Luckily the cab door was so high up that when it was opened from the ground you still had to climb the steps before you could see in. He flushed and then smiled when he saw Jenny jump into the passenger seat. He turned off the TV and kissed her hard and deep. “I’ve got you something sweetheart,” he said, in his usual winning way.
“I knew you would,” said Jenny, “I wonder, do I perhaps have to wear it?” she asked, laughing out loud.
“Yes you do sweetheart,” said Brian, joining in, “you go put it on girl, I’ll wait here and keep the bunk warm.” He passed her the box. She looked delighted with it when she saw the pink ribbon wrapped around it. Brian pinched her cute little ass as she jumped out the cab and headed off to the shower rooms to change. Because the manager had caught onto Jenny’s habit of spending the night with the truckers, he had taken advantage of the situation by giving her the key to lock up at night and open up in the morning; this way she could also get in and out whenever she liked.
Brian waited for around five minutes before grabbing a large hold all and getting out of his cab. He locked up and headed over to the cafe. He was determined to make this evening as special as he could for Jenny. He had planned a little surprise. He silently crept through the doors and put an ear to the shower room where he heard Jenny giggling to herself and shuffling about. She always took a long time getting ready, even if he only bought her a thong; she always insisted on looking just right, and perhaps tonight, he thought, she may want to look extra special. Brian also wanted to look good so he reached into his bag and took out a crumpled tuxedo, a pair of candlesticks, matches and a bottle of champagne. He stripped himself off, down to his shorts and silently hoped she wouldn’t come in now; although it wouldn’t be too much of a hardship, he thought. Brian’s body was pretty good for a sixty four year old man. He took care of himself and he had never allowed booze and cigarettes to get a hold of him. His skin was that of a middle aged man, and his physique was muscular in many ways. He had a little loose skin here and there as anyone of that age does, but his stomach muscles were still quite prominent and he had strong, broad shoulders and thick, powerful arms. He stood for a moment and considered himself in the reflection of the cafe window. He was sad to be leaving all this behind, but he wasn’t going to let it dampen his spirits. He pulled on his jacket and trousers and leaned a little closer to the window to do his bow tie; his eyes were very much those of a man in his sixties. He smiled to himself and switched on the CD player behind the counter. He had brought along some of Frank Sinatra’s more romantic tunes to play over dinner. Dinner wasn’t much however, it was a plate of pasta salad that had been hastily shopped for and prepared at his last stop. Brian lit the candles and sat down in the dim light to wait for his Jenny.
“Jesus Christ John! What are you doing man?” shouted Jenny as she opened the doors. She laughed out loud when Brian stood up and approached her. She was looking at his steel toe capped boots; not quite the thing for a dinner suit. She looked fantastic. He held her hands and tipped her back a little to get a good look at her. The clingy, silk dress he bought was perfect, and it certainly clung to all the right places. Jenny looked like a movie star. She had clearly taken her makeup bag into the shower room with her because she had bright red lipstick on and a pair of lovely, glittery earrings.
“You look absolutely wonderful baby!” he said grabbing Jenny around the waist and spinning her around to the sound of the jazz band on the CD player. He put his huge hand on her ass and felt it through the silk dress. Then he hoisted up the dress in several movements to grab a hold of her tight ass in the new, white thong, and toyed with the lacy tops of the hold-up stockings he had bought her to go with the dress. They were at just the right height for him, just below the line of where her ass cheeks met her thighs. His big cock twitched through his trousers and the silk dress.
“My, you are happy to see me like this aren’t you,” she giggled. “You’re an old romantic Brian. What have you got over there? Food and wine, and…”
“Erm,” he said loudly interrupting her, “champagne actually. Nothing is too good for this evening, including the steel capped boots!” He whisked her off to the table and sat her down to eat.
It took Brian all his strength to keep his hands off her at dinner, but he managed it if only because he wanted to savour his last evening with her. He eyed her tits hungrily, wrapped up neatly in that dress, exposing the large cleavage, tantalising him. Jenny knew what she was doing to him, and when they finished their food she stood up and moved the candles to the next table. “Hey, you don’t have to do any waitressing tonight my love,” said Brian, “We’ll do it together in the morning before you have to open up.”
“I’m not cleaning up big Sir, I’m making space,” she said with a naughty looking smile on her face. She continued to move everything else quite carefully off the table in absolute silence. Brain just looked on; he loved to watch her move.
“Can I get you anything else sir?” she asked in a mock innocent voice, leaning over to collect the last plate, giving him another glimpse down the front of the dress.
“Well you could let me shag you senseless waitress,” said Brian, laughing.
“Alright sir! Anything you say,” she said, as she climbed onto the table on all fours, turned, and pointed her silk covered ass in his face. Brian watched in awe as Jenny continued to tease him by putting herself flat on her tummy so that only her ass was sticking up in the air through the dress. The split at the back revealed her stocking tops. Brian slid his hand slowly up the split and found her little thong, now wet with excitement and anticipation. He pulled it down steadily and made her tremble. The humour disappeared it what seemed like seconds, leaving only purely sensuous role-play. “Do me sir!” she said, “please do me, I need it hard. Give me a large tip; I am a good waitress you know.” She turned her head to look at Brian and stared into his eyes as he stood up and wrenched out his giant cock. He loved it when she looked into his eyes. “Please sir, now please,” she went on, “I need a tip, we don’t earn much these days you know.” Without a moments hesitation Brian grabbed hold of Jenny’s hips and pulled her back, making the dress ride up above her waist, exposing her wobbling ass and wet pussy. He pulled her hard but stopped her sliding off the table with his big cock as he shoved it inside her tight pussy hard. Jenny squealed a little and then relaxed. Brian felt good, his cock was nice and warm inside. He felt the wetness on the table with his hand and thought to himself that Jenny must love her clit gently rubbing on the wet plastic, gingham table covering as he pulled and pushed her onto his cock like a giant sex toy; she moaned pleasurably each time he moved her. He fucked her like this for a quite a while before she decided to change position. She reached behind and grabbed hold of his cock. After slapping it a couple of times on her naked ass, she got off the table and stood in front of him, looking at his twitching dick. He watched her let the dress drop to the floor and approach him slowly. When she got close she turned her back and indicated that she wanted him to unfasten her lacy bra. Brian did this expertly with one hand whilst he reached around the front to catch her falling boobs with the other; his years had provided much experience and served him well now. He tweaked her nipples hard and spun her around to put them in his mouth and suck on them. Jenny grabbed his wet cock and wanked it whilst he did this. He was so hard he thought he might explode in the palm of her hand. He moved from her tits to her wide and inviting mouth, and then from her mouth back to her tits again while she wanked him off harder and harder. Brian was getting very worked up over his beautiful prize and Jenny broke away from him eventually just so that he wouldn’t shoot his load. “You’re getting very excited Sir! Am I a good waitress,” she said, tapping her hand on the table, “hop up here and let me ride you.” She gave him a little squeeze of the balls and another on the end of his cock to desensitise it a little before letting him move. Brian didn’t complain, he moaned a little and jumped up on the table. Jenny fondled her tits for him for a little before getting on the table to sit on top of him. They moved slowly at first, savouring every movement, then Brian felt the urge to speed things up a little. He watched her playing with her clit whilst she rode him, and he stroked along her fingers gently. She was close to climax, he could tell by the way she was rocking on him with a downwards push. Then suddenly she leaped off his cock and slid up his body, ripping off his shirt to allow her access to his hairy chest. Much to Brian’s delight, she rubbed her clit up and down hard on his chest before pushing off the edge of the table where his head was hanging slightly off. Jenny was getting really hot and she thrust her pussy into Brian’s face, forcing him to lick and move in any way just in order to breathe, and it was here that Jenny finally came, all over Brian’s face. She shuddered and collapsed onto the floor as her legs gave way. Brian sat up, clicked his neck straight and shook his head.
“Jesus I thought you were going to smother me! What a way to go that would be,” he said as he walked around the table to get to her. He wanked his huge tool and watched Jenny get to her feet.
“Do you want to shoot it all over my face and tits Sir?” asked Jenny innocently.
“Oh yeah,” said Brian, wanking hard. He approached her and she grabbed hold of his balls and tickled them with her fingernails while he wanked. He twitched and jerked around while she flicked the end of his cock with her long tongue, and before too long there came a stream of hot cum across her face and down onto her tits, as he exploded, leaving little drips to land on her thighs and the cafe floor.
Brian sat down on the chair, out of breath, and Jenny remained on the floor. “So that’s it then,” she said, “the end of an era for us I suppose?”
“Not really,” said Brian, wiping his cock on a napkin, “I can dream about you,” he said sweetly.
“Not the same though, really” said Jenny sadly.
“No, not the same my love,” he smiled and took her hand.