Diane Gets A Nasty Surprise

I had always been attracted to older women – I think it was something to do with the taboo of it all. The objects of my desire were usually friends of my mothers, my mates' moms, my aunty was pretty sexy and so were several of the supermarket checkout women.

The thing was I was only 18 and these women were all well into their fifties. They were always married, had kids my age or older and were generally unavailable.

But the younger women just didn't do it for me. I'd see an older woman and immediately get turned on by numerous things. Their more mature faces, the age lines around eyes and the face generally, the confidence that comes with age. Then of course there was their bodies – I love the older body with its imperfections, the fuller breasts starting to sag a little, the not so flat stomach and small bulges here and there. Don't get me wrong – I like a good figure, but just not some stick insect like twenty-something. I liked nothing better that waiting for an unsuspecting older woman to bend down in front of me and give me a good view down her cleavage.

But unfortunately like most 18 year olds I was stuck with girls my own age. Nice as though they were, not my ideal woman. But then again I had urges and wasn't about to turn down a blow job!

My latest girlfriend was Amy. She was a nice girl and we had been seeing each other for about 3 weeks. She had given me a blow job on the second date so I was pretty keen to take advantage of her willingness to keep me happy. Clearly after 3 weeks she was keen for me to meet her parents so here I was about to knock on the door and get introduced for the first time.

I had already noticed that the house was very nice – big, well presented and in a nice neighbourhood. I knocked on the door and waited. Amy answered the door and kissed me quickly.

I knew we were not staying long but she dragged me inside and told me that she wanted to introduce me to her parents.

She pulled me through into the kitchen where her entire family was. Her father was a nice looking man called John who warmly shook my hand and welcomed me with a big smile. Her brother seemed about 3 years older and also shook my hand. Then I got to her mother, Diane. She was stunning – she had dark shoulder length hair which was cut in a very fashionable style and subtly dyed. Her eyes were big and oozed confidence, she was dressed impeccably and her smile was very sexy.

Diane greeted me like I was a long lost son and immediately ignored my outstretched hand coming straight in for a hug. 'Dan' she gushed, 'It's so nice to finally meet you. Amy has told us so much about you.'

I was immediately aware of Amy protesting and telling her mother to shut up. All the while I was looking at Diane's body. It looked great for someone who was probably in her 50's.

I got to know Amy's family quite well over the next few weeks. I was often around there and would admire Diane and she strutted around her immaculate home. Every now and again I'd get a quick glimpse of cleavage and fantasise some more. She was always well dressed and very polite. They seemed a typical suburban family.

After about 1 month Amy asked me if I would go to her cousins wedding which was due in a few weeks. I knew that would mean the potential of a grope so happily agreed.

The morning of the wedding came around and I turned up at Amy's house. The family was all rushing around getting ready and I eagerly looked around for Diane to see what she was wearing.

As she entered the room I quietly gasped. She was wearing a skin tight purple dress which clung to her figure. It showed off every curve she had and looked fantastic. The skirt finished just above her knee and showed off a good amount of cleavage. I also noticed that her tits were not particularly big and were probably being boosted by a wonder bra. Her make up was immaculate as normal and her hair had been styled and cut. She looked a million dollars and extremely sexy.

To my surprise Diane turned to Amy and said, 'Amy, honey. What do you think – bra or no bra?' pushing her boobs up a little in her dress.

Amy looked at me a little embarrassed. 'Mum, bloody hell! Look you can't not wear a bra can you?'

The wedding was good fun but I was surprised at how much Amy drank. By about 9pm she was very drunk. I was sitting next to her and became aware of Diane stood next to me.

'Hey Dan, how is she' Diane asked.

'She's ok – just had one too many' I replied.

Diane laughed and put her hand out. 'Come on – I want to have a dance'.

Diane pulled me onto the dance floor and started laughing as we attempted to move to the music. After the first song, the music changed and a slow song came on. I was about to walk off when Diane put her arms around me. 'Where do you think your going?' she asked pulling me close.

'I...uhh' I stammered.

Diane laughed. 'Just enjoy the dance. I don't often get to dance with nice young men like you.' At that point I felt my body being pulled against her. I could feel her tits pushing against my chest and her thighs rubbing against mine. Her body felt so good.

I could feel myself stirring as we slow danced. No matter how hard I tried, I couldn't stop it. I knew I was getting a full blown hard on.

Diane giggle at one point and deliberately pulled me closer.

In my head I was wondering if she could feel my erection pressing against her. As the dance finished, she released her grip slightly. 'I think you enjoyed that Dan' she whispered and walked off.

I wandered back to Amy but could not find her. One of her cousins told me she had been taken off home by her dad to sleep things off.

I wandered about for 10 minutes or so then decided I would go home. After all the wedding was not my family. Just as I was about to leave Diane called out to me.

'Dan, are you leaving? Well John's taken Amy home so I said I'd walk back with you. Is that ok?'

'Yes, no problem' I replied, and waited for her to say her goodbyes.


It was about a 20 minute walk and as we set off down the road Diane took hold of my arm claiming that her feet were hurting. She had clearly had a few drinks and was a little unsteady.

She turned to me after about 2 minutes and said 'Dan – I never asked you what you thought earlier?'

I was confused. 'What do you mean Diane?'

Diane stopped walking and turned to look at me. She grabbed her boobs and pushed then up laughing. 'Bra or no bra?'

I was a little taken aback, but the drink had kicked in a long time ago. 'With a figure like your's Diane, no bra defiantly.' I teased.

Diane playfully hit me. 'Cheeky bastard' she said laughing. The looked at me smiling. 'So what do you think of the dress?' She posed with hands on hips.

'I love it' I said. 'It really suits you. Not many women your age could get away with that.'

'Thanks Dan' Diane purred smiling. 'Do you know what? My husband thought it looked a bit too tarty. He said it showed off too much of my figure and if I didn't wear a bra then everyone would see my nipples.'

To tease me she then said 'So you would you prefer I hadn't worn a bra?'


I was rather stunned when she then quickly told me to wait there and disappeared behind a hedge. Then Diane proudly returned without her bra on.

'Is this better?' Diane smiled.

I laughed and flirted 'It's fantastic – I've never seen a better pair of tits on any woman'

Diane replied 'Do you not think it's too much for a woman my age to be showing her breasts and nipples off?'

'Certainly not' I replied. 'If you've got it you should flaunt it.'

Diane laughed and kissed me on the cheek. She looked at me and said 'Dan, I'm flattered by your attention but if you're hoping for a quick shag then you'll be disappointed. I've never cheated on my husband and besides you're my daughters' boyfriend. It just won't be right.'

I must have looked disappointed because she held my eye for a good few seconds.

I looked down at her and said 'I sorry Diane. You're a very attractive lady. I apologise of you thought I was taking advantage.'

Diane giggled again. 'Dan, it's ok. It's been a long time since I've felt an erection like that against me.' She then laughed as she could see my embarrassment.


As we walked in silence Diane suddenly pulled me into a small ally. She pulled me close to her and started to snog me as she leant against the ally wall. As she kissed me I made a grab for one of her breasts. At first she pushed my hand away but as I tried a second time she clearly decided she didn't mind.

As I pushed my hand down her dress I heard Diane gasp that we were entering dangerous territory. I pulled her tit out of the top of her dress and tweaked her nipple. Diane gasped and pulled me closer.

I felt her hands on my crotch as she rubbed my erection and started to undo my zip. In return I started to pull up her dress and my hand reached down to her wet knicker covered mound. Diane slightly resisted then gasped as I rubbed her pussy through her knickers and kissed me harder.

As Diane's hand pulled my cock out of my trousers I pushed two fingers into her wet pussy. Diane groaned loudly and gasped 'Dan, stop please.'

She used all of her strength and self control to break away from me gasping 'Dan, I'm sorry, I shouldn't have done that. I told you I wasn't up for sleeping with you and that also meant being fucked up an alley.'

I smiled at Diane and pretended to look really disappointed. She laughed – partly embarrassed and partly because of our predicament. She was about 35 years older than me, up a dark ally with one of her tits hanging out and had just grabbed her daughters boyfriends cock and whilst he fingered her pussy!!

I could see Diane looking down at my cock so I pretended to meekly say 'But what am I gonna do about this' pointing at my erection. 'It's your fault – I've had it every since you decided to rub your body against me during that slow dance.'

Diane looked at me for a few seconds then said 'Right, just this once and never tell anyone. I'll give you a hand job – after all I am partly to blame.'

I was more than happy to settle for that and couldn't quite believe my luck.

Diane pushed up against me again and before she could resist I kissed her hard as she took my long, thick and very firm cock in her hand.

She started to wank me hard and I gasped in between snogging her. 'Hold my balls too'.

As Diane worked her hand expertly up and down my cock I could feel myself getting very excited. I rucked her skirt right up over her thighs so I could grope her ass with one hand while with the other he pulled the front of her dress down to expose her breasts and nipples. I was now thrusting hard against her hand as she kissed me and fondled my balls. Her wanking technique was perfect with long hard strokes along the entire length topped off with a twist as she got to the end of my cock.

Diane was clearly enjoying it given the effort she was putting in. At one point she gasped 'Come on Dan, Shoot your load. I've had lots of practice wanking cocks, but never one so young. Do you like the older woman playing with your cock?' Diane could clearly feel my thrust against her hand. 'How good would it be to fuck me Dan.' Diane purred. 'Would you like to be between my older woman's thighs instead of in a dark ally?'

As Diane talked dirty to me I knew I was about to cum. Diane worked me hard with her hand. As she felt my balls tense she knew I was about to unload. I felt her kiss me even harder as her tongue pushed deeper into my mouth. I could feel her quickly trying to pull her dress further up to stop me spunking all over her clothes. But as I climaxed I pulled her close an felt my cock being pushed hard against her stomach which sent me over the edge – the feel of bare flesh sent me into overdrive and I spunked a huge stream of cum against her stomach as I gasped loudly into Diane's mouth. As she kept working her hand up and down my shaft I could feel spurt after spurt of cum shoot over her body – I knew it was all over the front of her dress and knickers.

As I was cumming Diane was teasing me. 'That's it baby – come for mommy' she whispered along with groans of appreciation as she felt my hot cum against her bare flesh. 'Come on Dan, give me your spunk.'

When I eventually did release her Diane laughed and said 'Fuck what will people think? A 53 year old woman with her breasts, thighs and ass uncovered cum all over my belly and a spunk covered skirt, spunk stained knickers, and a young stud with a long dangling semi erect cock.'

As she re – arranged her clothing she cursed me. 'Shit Dan, you've spunked all over my dress. Just the sort of thing a young buck would do without a second thought for how I'll explain that to my husband'.

I laughed and said 'It's your own fault. You started it and got what you deserved. I just wish I'd shot my load somewhere else!'

Diane looked at me. 'Well let's see how it goes. If you catch me on a particularly horny day perhaps I'll jump on your cock and let you fuck me senseless!!'

Diane then turned and started to walk home.

The walk home was quick and a little awkward – I think we both knew we had done something we shouldn't have. As we reached her house I could see that the lights were on. Diane unlocked the door and I followed her in. John her husband was watching TV. He told me that Amy was fine but asleep and thanked me for walking Diane home. As I made my excuses to leave Diane walked me to the door.

She opened it for me then looked around to check her husband was still watching TV. He was so she turned back to me and put her arms around my neck. She kissed me hard and pushed her body against me again. My cock instantly went hard. She broke off the kiss and laughed whispering, 'I can still feel you're cum on my stomach. I am so turned on right now – just standing there talking to husband knowing I'm covered in someone else's spunk!!'

I smiled and put my hand down t rub Diane's pussy. She pulled away and said 'Wait for it Dan. You'll get your chance when I'm ready!'

Four days later I got a call on my mobile from Amy.

'Hello' I answered

'Hey handsome' I knew it wasn't Amy. 'It's Diane, I borrowed Amy's phone to get your number.'

We had a quick chat before Diane said. 'Look Dan, I need some help with a few things in the house. Could you come around and give us a hand?'

I jumped at the chance thinking this was clearly code for 'Come over and fuck me senseless.'

I was surprised when I rang the doorbell and John, Diane's husband answered the door. He explained to me that he needed some help moving some stuff in the garden. I was gutted. As I walked into the house I saw Diane, who greeted me like normal and thanked me for agreeing to help. I knew she could sense my disappointment and gave me a wink when her husband was not looking.

I worked with John in the garden for two hours non stop. Then Diane shouted out from one of the windows upstairs that she needed some help moving furniture. John turned to me and asked if I would mind.

I wandered upstairs to the room in question and as I walked in Diane was stood in the door opening dressed normally in a top and skirt.

'I was wiping spunk off my stomach for days young man' she greeted me with a wagging finger. 'And you came all over my dress leaving a bloody great big stain. I think you owe me an explanation young man. I'm a married woman' she teased.

I smiled at her forwardness. 'It's your own fault – you shouldn't be so damn sexy.'

Diane winked at me again and said 'It's nice to get attention from someone young enough to be my son. Even thought it's totally wrong, I never thought someone your age would be interested in a woman my age.'

I laughed. 'Well you did offer me a handjob – what bloke would turn that down?'

Diane hit me playfully. 'Fuck off' she said. 'You make me sound like a right slut. You wanted to fuck me but at least I had some self control.'

I pulled her close to me and kissed her hard.

'Dan we need to be really careful – we could get caught' Diane gasped. 'John's downstairs and Amy could be back anytime.'

I looked disappointed and Diane stared into my eyes then kissed me with her tongue. 'I didn't say we couldn't – just we need to be careful. I'm married. I could get in a lot of trouble.'

Diane smiled that sweet smile again and said, 'Look if you promise not to tell anyone then, I'll do whatever you want within reason. You seemed to like my tits the other night' Diane said as she rubbed her hands across her chest and pushed her tits up towards me. 'Do you want to see them?'

'Yes' was all I could manage. She lifted up her top and her tits flopped out – she wasn't wearing a bra. In the day I could see that they had that little bit of sag that all older woman's tits have. The areola's were about 2 inches across and stood out with puffiness that I love. The nipples were huge. As big around as my index finger and an inch long. I felt like I was drooling.

Diane pushed my head down and told me to suck her nipples. My mouth latched on to one of her nipples with my mouth. She groaned with pleasure and I began to suck. She was holding my head against her breast and squealed as I gently bit her nipple then pulled it and twisted at the same time. I could feel her starting to grind her hips against my thigh.

I took that as a sign and reached down under her skirt and cupped her pussy with my left hand. Diane was starting to get very wet and I knew she wasn't wearing panties. I also noticed she was shaved clean – something I had not noticed the other night – she also had a big clit. As I continued to suckle her tit I shoved two big fingers in her and she really started to buck against my hand. I pulled her nipple hard again with my teeth and she grabbed my head with both her hands and smashed it to her breast. It was hard to breath, but I kept on sucking her nipple. I was ramming my two fingers in and out of her pussy, which was surprisingly tight. I began stroking her G-spot and she stiffened and let out a quite wail as she shot fluid from her cunt all over my hand and clamped her thighs tightly around my hand.

Diane was shaking and had an animalistic look to her face and said, 'I want to suck you now. Treat me like a total whore and fuck my mouth hard – as if you're trying to fuck my daughter. Use my mouth as your own personal fucking tool – make me choke and drink your cum.

That was as far as Diane got. I pushed her down to her knees and rammed her mouth down on my cock.

'Now suck it you bitch!' I ordered.

Diane desperately worked her mouth up and down. I could tell it was a long time since she'd done this to her husband. She had no finesse, but the eroticism of having an older woman knelt before me sucking me off was incredible.

'Yeah, that's it.....deep down. Take it. Oh yeah... How old are you, Diane?'

She gasped for air, 'Fifty three.....I'm fifty three'

I pushed my cock back into her mouth, roughly.

'How does it feel sucking a younger mans cock? I'm young enough to be your son. How does it feel having your son's cock in your mouth, Diane?' She stiffened and moaned helplessly as I held her bobbing head.

I felt my cock swell in her mouth, then I was ejaculating, spurt after spurt deep into her throat as she swallowed convulsively.

She tore her mouth away and rocked back on her heels, coughing as my hot sperm slid down her throat.

'Oh my God.....' Diane retched. 'Fuck, you bastard' she coughed. 'Jesus is that how you treat Amy? If it is then I want more. I've never been fucked in my mouth like that.' Diane looked at me like I had just unlocked some kind of inner sexual demon in her.

'I want to fuck you Diane. Right her, right now.' I said to her.

Diane looked at me thought for a moment. 'Dan I can't. Not here. Johns downstairs. We just can't.'

Just at that moment the sound of Johns voice came up from the garden. He was shouting for Diane.