Jessica's First Time at the Bar...

Editor's note: this story contains scenes of incest or incest content.

*****

Jessica followed Tom into the bar, walking carefully, feeling very self-conscious. Already she had received a number of strange looks, smirks, as she had slowly tottered across the car park in her high heels. Not just the high heels. The bright red lipstick. The eyeshadow. Nail varnish. The blue patterned summer dress. Long dark hair, tied in a pony tail with a bright ribbon. But she had kept going, following Tom from his car. Even Tom had felt a bit nervous bringing Jessica with him to the bar, to meet his four friends.

Of course they were old friends – the five had known each other for years, and had drunk in the same pub every Thursday evening for at least 20 years. Sometimes one, or another might be missing on work or holiday. But they were always there, in the same corner – through the door, round to the right, in the hidden alcove, with it's four chairs, low table and padded bench along one side. About the only thing they didn't do was sit in the same chairs every week. They were so regular that even the landlord was now considered part of the group, and would often sit chatting with them when there was little else to do in the bar.

They were all in their mid forties. Some married, some divorced. The truth was they hid nothing from each other, and once, after too many drinks, and the landlord letting them stay after closing time, they had gang-banged one of the barmaids, who seemed more than happy to join in their fun.

But this day it was different. This was the first time Jessica would join them. They had agreed it would be fun to have her there, so here she was, arriving about 9.30pm with Tom, her stepfather. Nervous, but determined to be there.

As they entered the bar, turning to their seats the other guys were already there, and cheered – reservedly – as Tom arrived, one of them wolf-whistling, looking at Jessica. They sat her on the most prominent seat, Tom taking a spare place on the bench.

The four men chatted, greeting Tom, openly staring at Jessica, one frowning, the other three "gawking" at the girl sat before them. Denny brought Jessica a drink – a coke - and placed it in front of her. She was shaking with nerves, but the drink calmed her – a little.

The men chatted a little longer, until there was quiet. Denny looked at Jessica. "I suppose it's me first!" He looked at Jessica from his seat on the bench. "Why don't you come and sit on my lap, babe..."

It had started two weeks before. The guys had been in the bar, with Denny complaining he was lacking female company. He had been divorced only eight months before, but everyone reckoned it was good for him. He wife had been difficult. She had a history of affairs, and Denny had taken her back each time. Finally it had ended – she had simply moved out, taking all she could to set up home with her toy boy. Physically he was a great muscled rugby playing specimen, and Denny, as much he enjoyed jogging, couldn't compete. Even Denny, within weeks, found himself much more relaxed, easy going, enjoying time with his friends and without his demanding wife! But now – he was missing female company. And couldn't find anyone.

It was from there the conversation had descended to... well the first comment was that he should maybe widen his horizons, that he should look at other options, that he should go one tinder, and grinder, and... The conversation had veered round to a different question. Could they? If they couldn't find a woman, would they do it with a transvestite, or a trap, or a sissy... Denny reckoned he probably would. Or could. Tom wasn't sure. Pete and Greg weren't sure. Jack reckoned he definitely couldn't. Brian the landlord said to would try any hole that was available to him...

The conversation moved on, almost forgotten...

It had continued on the Sunday afternoon after. Tom had come home early in the afternoon. On a Sunday he would visit his mother, but this Sunday his aunt was there so he left early – they would talk about "the good old days" for hours! Tom had been married to Kathy for two years, although they had lived together for a year before that. Tom had been in a couple of long term relationships before that, but Kathy was the one, and they had married. Kathy's son, Tom's stepson, Josh also lived with, having recently started an apprenticeship at a local printer. He was approaching his nineteenth birthday, and was doing really well in the work.

Tom liked Josh, although he could never quite make him out, and Josh tended to be quiet, keeping himself to himself. Tom was what some might call "a traditional" man. He enjoyed sport – mainly watching it. He enjoyed spending Thursday evenings with his mates down the pub. He worked as an engineer. Josh was quite different. He had long hair. He was artistic. He was slim, five foot nine. He was gentle. He was sensitive. Tom also admired Josh's determination when he needed it – and it had took real determination to get his ideal apprenticeship at the printer.

Tom had returned home, walked into the house to almost silence. It seemed no-one was there. He remembered – Kathy had gone around to her sisters – and it would be late before she got back. Together they could chat for the world championship. Perhaps time for a run – Tom went upstairs to get his tracksuit...

It was at the top of the stairs that he realised he wasn't home alone. There was a light coming out of Josh's bedroom, and some gentle sounds, people talking. Tom walked quietly along the corridor and looked in. What he saw was a shock.

Josh was lying on the bed, dressed in bra, panties and stockings talking to someone on the internet who was watching him. And it was clear he was rubbing himself through the panties, and whoever was on the other end was enjoying what he saw.

It was obvious Josh hadn't realised Tom was there. Tom continued to watch. The person on the internet was clearly encouraging Josh, and Josh was rubbing his cock through his panties, rubbing faster and faster, moaning as he did so. Tom watched as Josh lowered the pink panties off his cock, to the top of his thighs. He grasped his cock, pumped, moaned, the voice on the internet telling him he wanted to see him cum.

Tom thought Josh's cock looked good – a good size – and found himself enjoying what he watched.

Josh's was pumping harder, faster, and suddenly moaned loud and long, as his cum spurted out of his cock, over his chest, over his hand.

Tom also heard a voice on the internet moan, the voice of a man cumming, then saw the internet cut out.

As Josh came down, he rolled onto his back. Tom walked in. "Josh. Don't move. Did you enjoy that?"

Josh jumped. He hadn't realise Tom had come home early. Or had been watching. He didn't move. He was paralysed with fear, and embarrassment. Tom spoke again, his tone friendly. "Did you enjoy that?"

Josh spoke, his voice trembling. "Yes."

Tom smiled. He was enjoying this moment of a sudden. "What did you enjoy most about it?"

Josh realised he perhaps wasn't in trouble, that there was something else going on. Josh stumbled. "Um, being watched. In mum's clothes. Um, someone seeing me cum."

Tom still stood, then sat on the edge of the bed. "You ever done it for real? Dressed for someone?"

Josh replied, still nervous. "No, um, but I want to."

Tom smiled again. "You have now. I was watching you. You made me hard. What are you going to do about it?

Josh was startled. "Um, do you want me to suck you?" Why did he say that? He had never done anything with anyone. He has seen it on the internet...

Tom smiled – it was just what he wanted. Tom quickly undid his trousers, lowered them, lowered his boxers, and pulled Josh's head towards his cock. Josh quickly took Tom's large cock into his mouth, began to suck. Tom was amazed – he was so good at it – instinct! Tom held Josh's mouth on his cock and fucked his mouth faster and faster. Within seconds Tom was spurting into Josh's mouth, Josh swallowing as fast as he could. Tom held his head until he had emptied his balls into Josh, then let him go.

Both relaxed. Tom smiled at Josh. "You are hot. So let me understand. You like dressing? You like other men seeing you, doing things? You want to try some more...?"

Josh nodded – yes – that was just what he wanted...

"Okay Josh, we'd better get cleaned up before your mother gets home. Perhaps we can do some things sometimes. Perhaps I can help you?"

Neither said any more, but Tom went to his en suite, Josh to the family bathroom...

It had continued over the next few days. Tom and Josh didn't get any more chances to "do something." They were never alone at the house, or when they were there was no certainty that Kathy wouldn't come back and find them. But between the Sunday and the Thursday Tom's mind had whirred. There was Josh who wanted more. The conversation about doing it with a transvestite. When he saw his friends on the Thursday he had a suggestion that maybe they could think about for the following Thursday. He didn't say who, or give away any other details that might identify Josh. He was clear he couldn't guarantee anything, but they were interested...

It continued on Monday evening after the weekend.

Tom and Josh had been chatting. Tom had suggested to Josh that Thursday evening could be a good time. He explained the conversation he had with his friends and what they thought about cross-dressers. Kathy went to her evening class on Thursday. He could get Joshua ready, they could go before she returned to see Tom's friends, and see what happened... Josh was overcome with nerves, but it was a fantasy that could come true. He had courage, he would try.

"The only thing," Tom said, "Is that we need to get you a good name. Josh, Joss, Jess, it's obvious – on Thursday you will be Jessica."

Josh felt odd. He was going to become a real, well he wasn't sure a real what. And he had a name which he liked. Jessica...

It continued on Thursday evening – Tom's wife Kathy had gone out to her evening class. Tom took the carrier bag out of the cupboard in his "mancave" and gave it to Josh. "Think you should put these on. I'll be up in a few minutes to get your make up right."

Josh took the carrier bag upstairs and took out the items in it – various clothes, still wrapped in their original wrapping. Josh took all his clothes off, and began to unpack and put on the clothes. There was a pair of pink lacey panties. They fitted – just. He knew if his cock showed signs of life it would be a struggle. Josh wasn't sure whether he needed the bra, but it was there – matching the panties, so he put it on. He struggled a little with the bra, as he did with the suspender belt. He put on the stockings, and again had a bit of trouble with the suspender catches, but eventually got the idea. The cotton blue flowery summer dress was the easy part – it was short, but not too short.

Josh looked at himself in the mirror. He thought he could be passable as a girl, but a bit of make up would help. He thought too – he was no longer, for the moment, he: he was she. He was no longer Josh, he was now Jessica. His nerves tingled as he thought about it...

At that moment Tom came into his bedroom. For the next few minutes they did stuff to Josh's hair, leaving him with a pony tail tied in a large pink ribbon. Tom put on bright red lipstick, and eye shadow, and a little blusher, then declared Jessica was ready.

Josh – Jessica – looked in the mirror. Yes, he was Jessica, and his thought was: "...and Jessica is a bit of a slut!"

A few minutes later – after Tom had taken some photographs of Jessica – they left for the pub, parked in the car park and made their way across to the man entrance, Tom leading the way...

Denny had looked at Jessica. "I suppose it's me first!" He looked at Jessica from his seat on the bench. "Why don't you come and sit on my lap, babe..."

It took Jessica a moment to process the invitation. He had never been called "babe" before. He liked it. And the invitation – slowly he stood from the chair, eased around the side of the table to stand near Denny. Denny reached out, took his hand and pulled him to his lap.

Jessica had registered Denny – the same sort of age as Tom. Filling out a bit with age. Balding. Handsome. Confident. Warm.

As Jessica sat on Denny's lap, her feet to one side, Denny whispered in her ear. "My you are a pretty thing. I bet all the men would love to have you on their lap. I'm going to kiss you, long and hard, because you are so sexy and hot."

For Jessica it was bit embarrassing, but she loved the girly compliments she was getting. She could only ponder for a few moments as Denny pulled her mouth towards his, and she felt his lips against hers. It was electric. Amazing. Terrifying. As their lips met the other guys around the table cheered.

There was a pause, then Denny had his tongue in Jessica's mouth, was probing, and exploring, as he held her tightly in his arms.

It was the most amazing thing Jessica had ever experienced.

The kiss lingered, Denny was good, and Jessica felt his hand resting on her leg, then riding up the outside of her thigh. Jessica tensed, and Denny released the kiss for a moment. He whispered "Relax honey, we'll only go further when you're ready." Again their lips came together, the kiss continued.

Suddenly there was a commotion somewhere else around the table. The kiss was broken. It was Jack, looking really embarrassed. "I'm sorry guys, this isn't for me. Need to get home to the wife." He put on his coat and left. While he was leaving Jessica looked around the group again trying to remember names of those who remained. Tom she new, obviously. She was pretty sure there was Brian, the landlord. The other two Pete and Greg. Pete smiled and spoke. "Come on Denny, time the rest of us got some of this action. Pass her over here."

Denny smiled. He lifted Jessica and placed her on Pete's lap. Pete was much taller. Slim, athletic. He too pulled Jessica into a kiss, his hand immediately under Jessica's dress. Immediately caressing Jessica's thighs between the tops of her stocking and panties. It was only then that Jessica realised she was rock hard...

Then she was passed to Brian, the landlord who commented generally "I like a nice tit." Again, Brian was quite tall, and towered over Jessica. He had a thick mop of hair, a quick smile. As they kissed, Jessica felt Brian running his hand over her chest, then putting his hand inside the top of the dress reached under the bra and Jessica felt his fingers holding and pinching his nipple. Until this moment they had meant nothing to Jessica, but suddenly there was a leap of electricity from the nipple to her cock.

Greg was different when she ended on his lap. A smaller man, slim, but with a beard. Kissed by a man with a beard. It felt funny. Even weird. But in a nice way. And he did something different. He held Jessica's hand and guided it to his own cock. He undid his own flies and guided Jessica's hand inside. Jessica guessed what she would like someone to do to her, so did it to Greg, holding, and squeezing and putting his fingers through the fly of Greg's boxers to hold and squeeze his now hard cock.

Jessica knew she was doing the right thing as she heard Greg moan into the kiss they held. But then more – he had lifted her gently, pulled Jessica's dress up at the back and had his hand under her. Jessica felt it – the fingers slipping around the side of the panties, and pushing gently into his bum. The fingers were probing her hole. Jessica tensed, then slowly relaxed as she enjoyed the violation of her most intimate spot.

There was a commotion. This time it was Brian the Landlord. "Stay here guys – have to lock up, and then I'll be back."

Jessica remained on Greg's lap, and felt his finger push through the ring, while they still kissed. It was such an invasion, but Jessica knew it was okay.

Jessica felt the finger removed, and felt herself placed back on Denny's lap just as Brian returned, having locked the door of the pub.

"Do you know what we're going to do now, babe?" Denny whispered the question in Jessica's ear, but loud enough for them all to hear. Jessica shook her head.

"We're going to get you to kneel on the table, lift up your skirt, pull down your panties. And then we are going to fuck you. Both in your mouth, and in your mancunt. Do you want us to."

Jessica was terrified but never knew why she said yes.

It was only moments before she was on the table, on hands and knees, ready...

Ready, but nothing happened for a few moments. They were looking at her. They were looking at her hole. She was a sex object. Her mancunt. Asshole. Anus. She didn't know what to call it. Her thoughts were abruptly brought to and end as she felt something push at her hole. Hard, warm, greasy. Then pushed harder and harder. Jessica closed her eyes as she was invaded. Hands gripped her hips, until she felt it slip through the ring. Jessica had tensed, but slowly relaxed. It was so so tight. But whoever it was had used lube. And then it was being pushed further in, and then out, and then a bit further in, and a bit further and a bit further. The invasion was complete as her mancunt was being filled.

At last it could go no further – she felt the balls of the man against her. Then a voice whispered. "Open your mouth babe." Instinctively Jessica did. As she did she felt a cock enter her mouth.

For a moment it seemed still, but then she felt the movement. The man pulling out and back in her ass, the other almost in rhythm in her mouth. She was totally violated, and loved it, even though her ass felt stretched far wider than was possible. Yes, she had sucked Tom, but now to be doubly invaded...

The two men began to fuck her ass and mouth strongly, sliding their cocks in and out of her. She was being used. Taken. The cocks slid faster and faster and faster, until the man in her ass, slammed in hard, cried out, and was pumping deep in her guts. He was filling her with his spunk. It only brought the other man to his orgasm, and Jessica felt sperm being pumped into her mouth. She had to swallow – the man was holding her mouth on his cock as he spurted the salty slightly bitter liquid into her throat. Jessica swallowed as hard as she could, until the two men were slowing down, their cocks shrinking inside her. She heard the men speak. "What an amazing tight fuck." "What a fantastic cocksucker." And she felt it was a compliment. She also heard the voice say to her "don't move, stay where you are."

Then felt another man pushing at her mancunt. And another pushing at her mouth. Within seconds she was being fucked at both ends. And the same thing – she felt the two men cum together, and found herself swallowing more cum.

Jessica wasn't aware of the struggles going on in her step-father's mind. This was his stepdaughter. This was Kathy's son. But so hot. Quickly his lust overcame his scruples as he fucked Jessica in her mancunt.

And then more – two men – second time around, taking much longer, fucking mouth and ass. And then two more... Jessica was just pleased that they had lube, and they weren't cruel, but after the men finished her ass felt sore, as she was allowed to get off the table and sit on a chair.

Denny smiled at Jessica, then spoke to her. "Babe, you were fantastic. But we've all come twice, and we haven't let you come. Why don't you wank off so we can all watch?"

Jessica felt she had given everything, this would be nothing more. She hitched up her dress, grasp her cock and began to stroke. She knew it was a good size. Within seconds she was shooting her cum in the air, up her front, all over her hand.

The five men and Jessica dressed, sat around and chatted for a few moments. They agreed it was time to go home. It was Denny who had the last word. "Are you happy for me to take Jessica home for the night – get her cleaned up, let her sleep.