The bar was quite noisy with groups of people meeting after work to relay the day’s events. There was a football game on the TV screens which was attracting loud groups of men, all with their opinion on how their team was performing.
Jan sat in a booth towards the back of the bar on her own. She was contemplating life – it had not been a good day. She had been late for work, had lost a big contract and had been given a hard time by her boss. To add to her bad luck her husband had called to tell her he was stuck in a meeting and not going to be back until the following day.
She was tired and pissed off. ‘What am I doing with my life’ she asked herself, whilst on her third drink. ‘Why am I putting up with all this shit at my age?’ she mulled over in her head. Jan was 58 years old, had four children and 2 grandchildren. Her children had left home a few years ago, and she was feeling unloved. Her husband spent far too much time at work.
Jan still tried to look after herself although age was defiantly catching up on her. She had shoulder length brown hair that was dyed to hide the grey. Her face was developing small wrinkles on a daily basis. Her body was starting to go south – her breasts used to be a nice firm shape, but were now starting to sag. Her stomach used to be flat, but now showed the signs of four children. When she bent over there was a series of bulges and ripples that appeared. She used to be a size 10 but had now developed into a size 14. However Jan gave herself a hard time – she was actually a lot better off than most 58 year olds. On the positive front she was still a good looking woman – her facial features did have wrinkles but a lot of people thought they suited her. Her eyes were still sparkling and she knew how to apply make up to make the most of her features. Her boobs were sagging and her stomach bulging, but it was no where near as bad as most women her age.
She grabbed the waitress’s attention and ordered another drink. The bar was getting busier with groups of people milling about all over the place. There was loud laughter from a group of 5 young men who were stood a few feet from Jan’s table. They were getting very animated about something.
The waitress came back with Jan’s drink and she drifted back into thought.
Jan suddenly became aware of a voice. ‘Excuse me’ the voice said. ‘Excuse me’ the voice said again.
Jan looked up. One of the men from the group of five was standing by the table. He was holding Jan’s coat. ‘I think this is yours’ the man said with a smile. ‘It was on the floor.’
Jan took the coat, ‘thank you’ she said, smiling at the man.
‘You looked deep in thought’ the man said, ‘sorry to disturb you.’
Jan smiled, ‘I’m sorry, it’s been a long day.’
The young man flashed a big grin ‘don’t take life too seriously’ he replied and turned to join his friends.
Jan thought to herself ‘he’s right, enjoy life. Christ, I’m taking advice from someone younger than my kids!!’ She chuckled to herself.
A few minutes later, the waitress came back to her table and handed her another drink. ‘I didn’t order that’ she said.
‘It’s from that gentleman’ the waitress pointed to the man Jan had spoken to a minute ago.
As Jan looked over, the man smiled and raised his glass. He walked over to her table. ‘I hope you don’t mind’ he said, ‘but you looked like you needed another one.’
Jan was already feeling the effects of the alcohol. ‘Thank you’ she smiled, ‘you really shouldn’t have bothered.’
The man flashed his big grin again. ‘Actually there was an ulterior motive’ he said. He pointed over to his friends. ‘My friends and I were just goofing around making stupid bets.’
The man paused, and then continued, ‘we’ve been celebrating my promotion for a few hours now and with every drink someone makes a stupid bet. If they lose they buy the next round – simple really.’
Jan was listening, ‘Really’ she replied, ‘so, why are you telling me?’ she asked.
‘Ah’ the man smiled, ‘Good question. The guys saw me hand your coat back and gave me the usual ribbing about trying to chat you up. I told them I was just being polite, but they didn’t believe me. Anyway, they bet me that I could not find out if you were married, and your age.’ The man flashed the grin again.
Jan laughed. ‘God, young guys are so immature’ she said. ‘If you had been a group of girls then you would be having deep conversations about who is having an affair with who, who hates who and that sort of stuff.’ She laughed again.
The man held out his hand, ‘I’m Dan’ he said, ‘nice to meet you.’
Jan shook Dan’s hand, ‘Nice to meet you Dan, I’m Jan’, she replied. ‘So how old do you think I am?’ Jan asked.
Dan smiled again, ‘Ah, now that’s tricky – I don’t want to upset you.’
‘Be nice and I won’t be upset’ Jan teased. She was quite enjoying chatting to a good looking young guy.
Dan looked at her, ‘Ok, here goes’ he said. ‘I think you are probably one of these women who are actually older than she looks. You look about 46 or 47, but I’m guessing you’re a bit older than that.’
Jan pretended to look shocked, then laughed, ‘That’s pretty good. I’m actually 58. So I’ll settle for looking younger.’
Dan feigned shock, ‘Wow’ he said, ‘You look fantastic Jan. You look great. There is no way you look 58, wow.’
Jan soaked up the compliments. ‘So how old are you Dan? I’m guessing not much more than 23 or 24?’ she quizzed.
‘I’m actually 22’ Dan said smiling again.
Jan laughed, ‘God’ she said, ‘I’ve got three children older than you. Your making me feel old. Perhaps I shouldn’t even be in this bar?’
‘Don’t be stupid’ Dan said, ‘You better looking than most women in here’ He flashed that big grin again.
Jan laughed, ‘Dan your flirting with a woman old enough to be your mother. You should be ashamed of yourself. What would my husband say?’
‘Yes’ Dan exclaimed, ‘So your married – looks like I win my bet.’ He laughed aloud.
Jan smiled, ‘Go and claim your drink’ she said, beckoning to his friends.
Dan wandered off to claim his glory to a big cheer from his friends. Jan was left pondering the thought of flirting with Dan.
She found herself thinking he was very good looking, nice body, nice face; he appeared to be good fun. But he was younger than her youngest child. She was far too old for him. Why would he be interested in her?
Jan again got lost in her thoughts until she was aware of someone standing next to her. She looked up to see Dan standing there with a drink in his hand. He offered it to her.
‘Here you go’ he said, ‘You won me the bet so you deserve a drink.’
‘I can’t’ Jan smiled, ‘You’ll get me really drunk, I’ve already had five.’
‘Don’t be stupid,’ Dan insisted, ‘enjoy yourself, and relax.’
Jan laughed and accepted the drink. ‘Cheers’ she said.
‘Do you mind if my friends come over?’ Dan asked.
Jan looked over at them. There were four of them and they all looked relatively sensible and safe. ‘No’ she said, ‘Go ahead’.
Dan beckoned his friends over who all introduced themselves.
Over the next hour there was lots of banter, laughter and more drinks. Jan found herself getting drunker than she had been for a long time. But she was enjoying herself. She was 58, and having a good time with 5 young boys. The more she drank the more good looking she thought Dan was. She imagined herself being kissed by him, being seduced by him, being fucked by him. Then told herself that he would not be interested in a woman her age – stop being so stupid.
By the end of the evening everyone was pretty drunk. The boys were all flirting with Jan. There was a lot of lewd suggestions and innuendo. Jan had enjoyed it. It was good to be the centre of attention for once.
The bar was starting to clear when Dan announced that everyone should come back to his apartment for more drinks. This was met with roars of approval from all his friends.
Jan started to put her coat on. She was drunk, tired and needed to go home. ‘What about you Jan?’ Dan said, ‘are you coming?’
Jan smiled, ‘You don’t want me there Dan’ she said. ‘You guys enjoy yourself. I’ll get a cab home.’
‘I tell you what, come back for one drink, then I’ll call you a cab’ Dan replied smiling. ‘You know you want to. You’ve had a good time tonight and we’ve cheered you up. You owe us. Come on.’
Jan was looking at Dan thinking ‘why is this good looking 22 year old inviting me back to his apartment? He should be chasing someone his own age.’ Then she made a decision – fuelled by the drink. ‘Ok’ she said, ‘but just one.’
Dan smiled and motioned for her to leave the bar.
Dan’s apartment was a five minute walk away. It was clear and tidy, but quite small. Dan poured drinks and the music was switched on. Jan asked where the toilet was and was pushed in the direction of a door in the hall.
When she came out, Dan was waiting. ‘Thought you had got lost’ he said. ‘I was worried you needed rescuing.’
Jan laughed. ‘Do you always flirt with women old enough to be your mother?’ she asked.
Smiling Dan said ‘only the good looking ones – and you definitely fall into that category – you look great.’
Jan could not believe that this good looking young boy was being so forward. But she also knew that she could give as good as she got on the flirting front. She knew it was wrong but could not risk a reply. ‘You wouldn’t know what to do with a woman my age’ she teased. ‘I’ve got kids older than you. In fact I think I’d eat you alive.’
Dan laughed, he clearly enjoyed the flirting. ‘You may be old enough to be my mum, but that’s half the appeal’ he said. ‘Besides, a woman your age should be grateful of the attention from someone younger like me!’ Dan joked and winked at Jan.
Jan pushed him playfully, ‘you cheeky sod’ she said.
Dan looked at Jan and leaned into her kissing her long and hard. Jan felt his tongue push into her mouth as he pushed his body against her.
Jan knew it felt good. She knew it was wrong. But she was also feeling a desire in her stomach that she had not had for a long time. She wanted him badly. She knew it was the drink, but she wanted to fuck him. She wanted to show him how sexy an older woman could be.
Dan pulled back, looking at her waiting for a reaction.
Jan smiled and whispered ‘for a young boy you’re not a bad kisser.’ She then pushed him back against the wall and returned his kiss with equal passion. Her tongue pushing hard into his mouth, her body pushing against his. She could feel his hard cock pushing against her stomach. ‘Where’s your bedroom?’ she whispered. ‘I’m gonna show you how good an older woman can really be. I want to fuck your brains out Dan.’
Dan needed no encouragement at all. He took Jan by the hand and led her into his bedroom. He shut the door and immediately started pulling Jan’s top off. He then stood back looking at her admiringly, before pulling her skirt down around her ankles.
Jan pushed Dan back onto his bed. She stood above him in just her bra and pants. She realised how ironic this was. She was 36 years older than this younger man she had only just met. Here she was standing in front of him practically naked, drunk and about to have sex with him. She was suddenly conscious of her older body – the bulges and imperfections that come naturally with age. For 58 she looked pretty good. But her tits were starting to sag a bit, her stomach was not as flat as it used to be and she knew that when clothes were not there to hold things in place there were the signs of aging.
Dan was looking at her. She could see his eyes wandering all over her body. He sat up and kissed her again. She could feel his hot breath against her face. She felt his hands reach for her bra clasp and undo it. Her bra dropped to the floor and Jan felt her tits hang freely. Before she knew it Dan’s hands were pulling her knickers down.
Jan knew she was now totally naked, standing in front of a fully clothed man who was young enough to be her son. Dan kissed her again and she felt his hand grasp one of her tits. His hand felt rough against her tit. He was rubbing it hard, pulling her nipple roughly. Jan gasped with pleasure. She knew this is what she needed. This was no time for slow seduction. She wanted hard, rough and dirty sex.
Jan pushed Dan back onto the bed. He looked up at her naked body. She was trying to discreetly pull in her stomach and push her shoulders back to give her boobs a bit more lift. ‘Do you like what you see?’ she asked.
‘Oh yes’ Dan replied. ‘Just as I thought – a fantastic body for a woman your age.’
Jan smiled, ‘why thank you young man’ she said. ‘I do try to keep in shape. Unfortunately there is not much you can do about natural ageing.’ Jan pretended to push her tits up a bit.
‘You look great Jan’ Dan said. ‘I like women who look real and have natural bodies. There is nothing wrong with a bit of natural ageing. I think it looks sexy.’
Jan laughed, ‘Dan you flirt! You’re only saying that because you want to get inside my knickers and fuck me!’
‘Perhaps’ Dan replied. ‘But it’s true. I like the fact your body looks real. Your tits look great. So what if they are starting to sag a bit. So what if your stomach is not as flat as it used to be – what do you expect at 58 years old? I think given your age you look fantastic. I’ll bet you’re a better shag than most women half your age. And you’re far sexier.’
Jan smiled at the flattery. ‘Thanks’ she said ‘I think that’s a compliment. When you get to my age your body starts to do its own thing a bit – but I’m glad you like it. You’re going to get the full mature woman experience here you know. Sagging tits, stomach bulges and ripples and a well used pussy.’ Jan rubbed her wet fanny. ‘Just remember I’ve had three kids, so I’m not as tight as I used to be. You’re going to need a big cock to fill me up!’ she teased.
Jan leant over Dan and started to pull his clothes off quickly. As Jan pulled his boxer shorts down she gasped in delight as his cock sprang free.
‘Fuck, it’s bigger than I thought it would be’ she said. ‘You should have no problems filling me up with that.’
Jan reached out and roughly grabbed Dan’s cock. It twitched as he gasped. Jan gripped it hard and started to wank his entire shaft. ‘Do you like that?’ she whispered as she kissed him hard. ‘I want this badly Dan. I’m not going to hold back, which means your cock is going to get some rough, hard treatment. I’m not going to spend time slowly warming you up. You’re going to fuck me hard and rough ok?’
Dan groaned again, ‘Yes. It feels great but do it harder. I want you acting like a total slut.’
‘If a slut is what you want then that is what you’ll get’ Jan smiled. Her hand started wanking Dan’s cock fast, with long hard strokes right up and down the entire shaft. Jan had never gripped a cock as hard as she was doing now – it felt as if she was about to do Dan some damage, but he seemed to be enjoying it. As she reached the tip Jan twisted her hand before a hard downward stroke. Jan had never wanked a cock this hard before, but was determined to give this young boy the sexual experience of his life – one he would never forget.
‘Your cock feels great’ Jan purred. ‘I’m going to wank it as hard as I can. I want you to cum in my hand; I’m going to make you cum all over me. I want you to cum on me.’ Jan could see Dan was already getting close to shooting his load. She could feel him thrusting in her hand. She could see the tension in his face.
‘Do you like being wanked by an older woman?’ Jan teased. ‘Do you want to cum all over an older woman? A woman you’ve only just met. You don’t even know me and I’m wanking your cock. What would my husband say if he could see us? What would my kids say? Do you think they would enjoy seeing me act like a total slag with a total stranger young enough to be my son. I want you to cum, now. Shoot your spunk all over me Dan.’
Dan was now thrusting his cock in time with Jan’s fast hard rhythm. ‘Uhh fuck Jan. That feels so good, don’t stop. Uhhhhh…fuck, please keep going, make me cum all over you. I want you to make me cum. Keep wanking me hard. Keep going I want to cum on you. Keep acting like a slag – it’s so fucking sexy.’
Jan leant over Dan so that her tits were hanging down over his cock. As she furiously wanked his cock she brushed his cock head against her sagging tits just to increase the sensations.
Jan looked down at Dan and knew he was about to cum. She gave him one last hard wank, then quickly bent her head down and buried his cock in her mouth. As she moved her head down Dan gasped in pleasure. Jan quickly kept up the rhythm with her mouth as she felt his cock tense. She knew he was about to cum and wanted to taste him.
Jan felt Dan’s hands on the back of her head, and then gasped as he pushed his cock up into her mouth and her head down onto his cock forcing his cock to the back of Jan’s throat. As he did this Dan’s cock erupted into Jan’s mouth, just as she choked and gagged at having a cock at the back of her throat. Dan’s spunk flooded her mouth as she swallowed. Then she pulled her head back and felt more cum shoot over her face. She felt a further three large blasts of cum hit her face, chin and tits before things subsided.
Jan looked down at Dan. He was staring up at her, looking very pleased with himself. Jan laughed, ‘Fucking hell Dan, you came all over my face you naughty boy! I’ve never seen someone cum so much before. You must have been storing that up for months!! Look I’ve got your spunk dripping off my chin onto my tits. That’s no way to treat a lady!’
Dan smiled and laughed, ‘you did ask for it Jan. You really shouldn’t be so sexy. And a woman of your age should no better than to act like a total slut!’
Jan gave Dan a sexy look. ‘I could tell you needed a real woman. Anyway, spunk is meant to do wonders for the skin.’ Jan purred as she wiped some spunk off her face and started to rub it into her tits. ‘Do you think it will help my sagging tits?’ she laughed.
‘Anyway now I’ve satisfied you, I think I need a bit of sexual satisfaction’ Jan smiled. ‘Let’s see how quickly you can recover.’
Jan climbed on top of Dan straddling him. She reached down between her legs and took hold of Dan’s cock, then started rubbing her pussy against his soft cock, pushing his soft cock head towards her wet pussy entrance.
Dan looked a little alarmed, ‘Jan wait, I don’t have any condoms.’
Jan looked down at him. ‘Fuck Dan, how unprepared are you? I thought boys your age always had condoms. Shit, what about your friends, will they have any?’
Dan looked a bit worried. ‘They don’t, if we need them we just tend to buy them there and then from a vending machine.’
Jan stared at Dan, thinking. She knew that it was stupid to not use protection. She knew it was unlikely that she would get pregnant, but she didn’t know where Dan had been, or who he had slept with. She also knew she was drunk, feeling very horny and not in the right frame of mind to make sensible decisions. Any decisions she made now, she would probably regret in the morning.
Jan’s urges and need for satisfaction was always going to win under the influence of alcohol. ‘I suppose we’ll just have to forget it then’ she teased.
Jan could instantly see the look of disappointment on Dan’s face. She laughed, ‘Dan you idiot, I’m joking. Forget the condoms and fuck me bareback, I’m not going to get pregnant at my age. You can spunk in me till your hearts content. Nothing will happen – its ok so don’t worry. It’s one of the advantages a woman of my age can offer against a younger model!! You can cum in my pussy all you like.’
Dan laughed, ‘If you’re sure’ he said. ‘What about STD’s?’
Jan laughed again. ‘Dan I’m telling you to fuck me bareback – if you don’t want to then don’t. I’ll take a chance that you’re ok. I want to feel you in me without ant protection. Just fuck me and fuck me now.’