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An extended fantasy tale of a young man who gets dumped by his girlfriend, and finds adventure from a dating app. In the summer before he goes to university, he improves his knowledge of women, of sex, and of himself. He’s surprised by many older women who are seeking adventure for themselves.


It had been five months since Chloe had dumped me. It had hurt so much, she was my first teenage ‘love,’ but I gradually began to feel better about it as time passed, although the landscape for girls out there looked pretty barren. It was then that my mate Darren excitedly told me about the ‘app.’

A whole rash of dating apps had appeared in the public domain, and he found out about it from listening to an aunt who’d been inundated with offers when she’d gone online with it.

He’d overheard his mum talking to her on the phone, and the amount of laughing and giggling were a sure fire way of getting him interested.

“Gary, it’s crazy, I’ve got two dates this week, and that’s within a day of joining,” he said, “all you need are some decent selfies, you pay £9.99 for a months membership, and you’re away!”

The temptation was too great, that evening I went to my room and downloaded the app. I had a pretty good selfie of myself, and added a couple more of me that I’d taken, one on a bike, and another beside a swimming pool.

The profile details were as descriptive as I thought reasonable, just a teenage guy wanting someone to ‘buddy up’ with for the summer, until going to uni in September. I paid the membership fee, and waited briefly for ratification.

Straightaway I began a ‘search’ and there were literally loads of girls, and women, who looked incredible. Of course it was pretty obvious some of the pics were heavily manipulated, but then the phone went mad, and started pinging from ‘likes’ for me!

I realised quickly that I should have added filters, because there were ‘likes’ from all over the country, indeed all over the world.

I fixed the settings so that I restricted it down to a ten mile radius, that reduced the selections down dramatically.

I chuckled to myself when one of the first girls I saw was Millie Jones. She was a year above me in school, and her photo was a travesty of what she actually looked like. I looked at all of those in my area, and swiped right on a couple that looked really attractive, but also seemed to have a profile description that wasn’t too contrived.

However, I hadn’t set an age limitation in the filters, and there were women up to the age of fifty odd that were appearing. Then just before I was about to remedy that, there she was!

Mrs Anderson lived two doors up from me. There was no doubt it was her, the profile pic was not manipulated. Neither were the two accompanying ones. One of her in a party dress, and the other, with her face hidden, dressed in some very sexy lingerie. The shock to me was that she was married, and she was asking for ‘someone much younger to bring the fun back into her life, nsa, discretion assured.’

I knew her name was Megan, but here she was using the name Marilyn, and she was saying that she was forty six. I definitely knew that she was in her mid fifties.

The devil in me somehow took over, and I swiped right. As soon as I’d done it, I regretted it, but felt a chill of excitement in discovering her secret.

For the next hour I amused myself with searching and swiping, even obvious mismatches I swiped right. In return I got some responses, but chickened out of going further, except for one girl, Tammy, who was mid twenties, and in hospitality, which is where I wanted my career to go eventually.

She was working and living in a hotel and restaurant on the other side of town. I hadn’t been expecting a response when I swiped her. I was sure a twenty five year old wouldn’t want to meet up with an eighteen year old boy.

I actually brought this to her attention in our messaging, and she dismissed the age difference as ‘just a number.’

It got to about ten thirty that night when mum shouted up to say she was going to bed, and asked if I wanted a hot drink. I declined, and went back to messaging Tammy.

In between there were occasional ‘hits’ from others on the app, but when I looked they were nowhere as attractive as Tammy. Then, to my surprise, a ‘like’ came from Marilyn!

I wondered quite what to do, so at first I did nothing. The messaging with Tammy came to an end as she had to go to bed, she told me she had an early start the next day, however, she did promise to message again.

I looked at the clock, it was 11.20pm, and the devil in me returned. I messaged ‘Marilyn’ with a simple ‘hello.’

Immediately, there was a reply.

‘Gary, I obviously recognised you, please be discreet, there are certain reasons why I’m on here. I’m sorry if you think I’m bad.’

I looked again at her profile, and to my surprise she’d changed the description to ‘mature woman looking for friendship,’ and the lingerie photo had been deleted.

I Escort Küçükköy sent a diplomatic reply just saying, ‘no problem, your secret is safe.’

When I got a ‘thank you, my name is really Megan,’ back, I wondered if she would acknowledge anything about it, should I see her in the street.

I didn’t have long to wait. Mum left for work quite early, and I was in the habit of going for a run as soon as I’d got up. The next morning I went out around nine ‘o clock, so after I’d done my five miles it was nine thirty by the time I returned.

Even before I’d got anywhere close to my front gate, Mrs Anderson, Megan, was standing by her car parked on her drive. It was pretty clear she wanted to intercept me.

As I got close, I slowed to a walk, and saw her look towards me rather guiltily.

“Gary, could you spare a minute?” She looked incredibly attractive in the sunlight, and I was trying hard not to look too closely at her cleavage, which showed off her most natural assets.

“I’m feeling really awkward. Last night… the messaging… that app. You must think I’m really terrible.”

“Not at all, Mrs Anderson,” I replied politely, wondering how terrible she might be when she was naked! “I’m sure there are lots of reasons…” I wasn’t really sure how to continue.

“For goodness sake, please call me Megan, look, come round the back, the neighbours here are so bloody nosey.”

That was the moment I knew my luck might be in. I was sweating after my run, and I felt slightly self conscious about that. As I followed her indoors, Megan handed me a small towel from a pile of washing in the kitchen, asking me to sit on a stool at the breakfast bar.

“Oh god, I don’t know where to start Gary, you must think very badly of me.”

I shrugged my shoulders, “It’s your life Mrs Anderson, sorry, I mean Megan. I guess you don’t want your husband to know.”

She looked guilty again, “Dave, I’m not sure how he’d feel. Part of the problem is that I found out about him having an affair. We nearly broke up, but kept together because of the finances. I’m not really sure if he’s still seeing her.”

I watched Megan nervously tidying the breakfast things away, I wondered whether her husband still enjoyed her body, it was certainly one that must have given him enjoyment earlier in their lives.

“So are you getting revenge?”

My question may have been a bit naive, typical of a teenager.

“No, not totally, I just feel I’m missing out on so much, sometimes I need something more than just… this!” She nodded towards the washing, the dirty mugs and plates.

I looked at her, and saw the tears trickling down her cheeks.

“Don’t cry, I think I probably understand.”

It felt odd standing up, to put my arms around her, trying to comfort a much older woman.

And then the sobbing really began. Her whole body shook as she buried her face in my shoulder, adding her tears to my perspiration.

“Now, now,” I whispered into her blonde hair. My hands and fingers rubbing her back, to try and soothe her distress.

She pulled her head up, and looked at me, our faces inches apart. I could see her sad green eyes, the dampness of her cheeks, I could smell the lightness of her perfume, and my eyes studied her plump, full lips.

I knew I wanted to kiss her, she seemed to want me to, and I did. It surprised us both, a kiss of only a few seconds, but the depth of feeling, our eye contact, brought another, much longer kiss, and I felt her whole body relax in my arms.

When the kiss ended, she pulled her head away again, and whispered, “We mustn’t.”

“Why,” I asked, “isn’t this what you wanted?”

She said nothing, but she must have felt my cock hardening between us.

She kissed me again, this time her lips parted wider, allowing my tongue to explore, at the same time she pushed her hips into me, moving just enough to bring me to a full erection.

“Quickly, in here,” Megan grabbed my arm, it seemed she had made her decision, and pulled me into the lounge towards a large settee, “please fuck me Gary, I want you to.”

When she saw me standing there, unsure, she took the hem of her t-shirt, and dragged it over the top of her head.

“Get undressed… please.”

In a matter of seconds we were both naked. I watched as she lay back on the cushions, parting her legs slightly, her full breasts spreading either side of her body, her pink nipples, standing up proudly.

Briefly she looked at me, my body still hot from my run, but now my cock was pointing upwards, as hard as it had ever been.

She reached up, putting her arms around my shoulders, and her thighs parted, as I lowered my body on top of her. I was nervous, yes, I’d made love to a few girls, but never to a mature woman like Megan.

My cock found her pussy immediately, and so wet was she, that I sank deep inside her. I could see her eyes close as she let out a gasp, “Oh Gary, wow, you feel so good. Please just don’t move, stay there, Mecidiyeköy escort I want to feel you, enjoy you… god, how wonderful that feels.”

I leaned forward, and kissed her, as she seemed to luxuriate in her pleasure, while I was composing my self control.

Eventually she opened her eyes, and looked at me, “Fuck me now, as hard as you like, I just want to feel you cumming inside me.”

When I started to move, I withdrew slowly, almost all the way out, before plunging back into her. I was being too slow because she repeated, “Harder, fuck me harder, please.”

And so I did. I felt her legs wrap around me, clasping my buttocks, her finger nails digging into my shoulders. I began to pound into her, the sound of flesh hitting flesh as my hips bounced against her open thighs.

It really surprised me how quickly she came. I heard her breathing quicken, I felt her gripping me more tightly, she started to pant short breaths, and finally was swearing loudly as she came.

“Fuck… fuck… FUCK!” her whole body shook, and trembled, her hips lifted me upwards, and then her cries subsided, but her body continued to push against me. She wasn’t finished, she wanted more.

“Oh go on Gary, don’t stop, please don’t stop.”

I didn’t stop, I wanted to cum too, but it wasn’t immediate. By now I was sweating again, drops of perspiration were falling onto her face. I noticed her tongue licking the salty taste, before closing her eyes again.

“Oh god, I’m cumming again Gary, oh my god, go on, yes… yes… YES… YESSSSS!”

With a grunt, I couldn’t hold back. I jerked once, twice, three times, and then held myself deep inside her, as the rest of my spunk pumped it’s way into her cunt.

“Stay there, inside me, don’t move.” Megan’s fingers wiped the sweat from my forehead. “Gary, I don’t want you to think I’m terrible. That was magical, you’ve made me very happy.”

I wasn’t sure what to reply, it was certainly a fantastic fuck, and I knew I wanted more.

“Can we do it again?” I asked.

“Bloody hell, what now?” she said, and we both laughed gently.

“I’d love that, but we must be careful, your mum would be horrified, Dave can go to hell, but I don’t want to rub his nose in it, and well, the neighbours, Mr Simpson over the road can go stuff himself.”

My cock was shrinking, and suddenly it slipped from Megan’s pussy.

“Ohhhhh! Mmmmmmm! Oh god, I can feel we’ve made a mess on the cushions.”

We both got up, my spunk seeping from her pussy, and while I put my running kit back on, Megan had to go and have a shower.

“You go back home, I’ll message you later Gary.”

Sure enough, back at home I showered, and by the time I’d dressed a message had arrived from Megan.

‘Thank you Gary, it was wonderful. I want more of you.’

Even that short text made my cock twitch, and I’d almost forgotten about Tammy, but sadly there were no messages from her. There were however, a few other likes from a variety of girls and women.

The app was so addictive, and the morning had gone so well. I spent until after mid day on it, until I felt the pangs of hunger, and I went to the fridge, suddenly remembering mum had left me a job to do. The grass needed cutting front and back. I grabbed a sausage roll and a tomato, and poured a glass of fresh orange juice. Eating rapidly I grasped the nettle, and got the mower out of the garden shed.

I knew it didn’t take that long, it wasn’t a vast lawn at the back, and the one at the front was tiny. By the time I had almost completed the front one I had built up a sweat in the warm sun. Glancing up the road, the thoughts of the morning returned. Megan’s house was less than a hundred yards away, and as if to reinforce the memory, she appeared in her front garden.

She didn’t wave, but just looked, I’m sure she was conscious of any neighbours watching, especially Mr Simpson from across the road. I looked over, and I knew he was out, his prize possession, his classic Ford, was absent from the drive.

As if by telepathy our eyes connected over the intervening distance, and with an imperceptible nod, Megan disappeared back indoors. It was 2pm, how long before her husband got in from work?

Quickly I shoved the mower behind the side gate, and walked to Megan’s house. She was hiding behind the partially open front door.

“Quick, this way,” she ushered me inside.

Not a word was spoken, I was shoved back down on the same settee as in the morning, and Megan fell to her knees, undoing my belt, and the zip on my jeans.

“God Megan, you’re insatiable!”

“Shut up, just enjoy, I told you I wanted you.”

In seconds her mouth was around my cock, and her head was moving up and down. In no time I was stiff and groaning out loud.

“Fuck Megan, you’ll make me cum… shit… slow down!”

But she had no intention of slowing down, she had a challenge, and she wasn’t going to stop until she’d met it. Occasionally she stopped, and her tongue would Merter escort bayan loop its way around the head. I just couldn’t hold back.

“Megan… fuck I’m cumming.”

I groaned, and the feeling of orgasm was throughout my whole body. I went on spunking into her mouth, and I could feel her swallowing it several times over. As I sighed, and relaxed back into the settee, I watched her lift her head. She held my cock, squeezing it, and licking the last drops of semen, exuding from the head.

“Mmmmmm, I love that taste, Gary, you’re so sexy!”

I raised my eyebrows, “I might say the same about you, when I saw that photo you deleted on the app.”

“You mean in my bra and panties?”

I sat up, “Yes, you looked really sexy.”

“Ok, come round tomorrow morning, and I’ll show you for real!”

“Are you sure, if people see me coming round here all the time then…”

I must have looked unsure,

“Dave is leaving early, he’s got a job right up north so he’s stopping overnight tomorrow night, I’d love to tempt you, please come round.”

I smiled, standing up, pulling up my jeans, “Megan, you’re becoming very addictive.”

Megan stepped forward, and we kissed. It tasted of my semen, an odd taste to me, but the kiss was a promise of another day with her.

I left by the side gate making sure Mr Simpson wasn’t back home yet. By the time mum got home I’d tidied away the lawn mower and got organised.

“I bumped into Mrs Anderson on the way in Gary, she said she’d had a chat with you today?”

I went hot all over, keeping my back towards mum.

“Yes, it’s the first time I’ve really met her, she stopped me, not sure why.”

“Well she seemed very impressed, I even offered you to do any jobs for her, like mowing the grass, was that ok? She’ll probably pay you.”

I thought to myself that she’d paid me already, what the hell would mum think if she knew.

“Ok, well if she asks I might do that.” I was thinking any excuse to go to her house would be fantastic.

After we’d eaten I went back up to my room to have some space. I looked at my phone and there were yet more ‘likes’ from the app. Still nothing from Tammy, so I gave up on her, but there was another from a woman who lived a couple of streets away.

What was it with older women and young guys like me, I thought to myself? This was a Debbie, a fifty six year old. Her profile stated that she was divorced, and had grown up children, but lived alone. However, reading between the lines she wanted to ‘catch up’ on what she’d missed. On this app, that appeared to be a euphemism for sex. And her photos showed a very busty red head, with a smile that suggested all sorts.

For the hell of it I swiped right just to see if there was a ‘reaction.’

I heard myself say, “Fuck,’ when the ‘like’ came straight back.

I told myself not to react, I couldn’t go down this road, on top of my secret affair with Megan. But of course I did.

‘Hi there. Thanks for liking. You do realise I’m eighteen?’ The message was sent.

Ping! The reply came back from Debbie.

‘Yes I do Gary. You know I’m much older. Is that a problem?’

I took a deep breath, and started typing.

‘No problem Debbie. I am discreet if that’s what you want?’

The messages were now being exchanged thick and fast, and each one told more about her wishes. She was a solicitor, who was divorced, as her profile said, but she had wanted to ‘break out’ as she put it, and on a spontaneous whim, swiped right on my profile, mainly because I lived quite close, and also she just found me attractive.

I knew I was getting in deeper with each message, and when I received a quite explicit photo, I realised where we were both going.

‘Can I have one of you?’ the next message said.

I took a breath, I’d never ever done this sexting before.

‘You must be discreet please.’

The reply came back, ‘You need not show your face.’

I tried to rationalise it, and my daredevil streak took over again. I was already quite hard from the intimate texting going on, so I lowered my jeans and boxers, and found my cock in a very advanced stage of development! In the circumstance it didn’t take long for it to become fully erect.

I lay back, positioning my phone so that it only showed the middle of my body. My cock looked huge in the photo and I sent it immediately.

When there was quite some delay before I received a text back, I thought I’d blown it.

‘Omg. You’re so big. Gary you must make your girlfriends very happy!’

‘I don’t have any girlfriends.’ I replied, half lying, then regretting not telling the whole truth.

‘I want to meet you, can we meet in Costas?’

I replied, ‘Yes. I’m free tomorrow afternoon.’

‘Ok. 2.30pm. Tomorrow.’

As soon as I’d agreed I felt guilty. My emotions and libido seemed like a roller coaster. The app was encouraging me to lie just to satisfy my ego, and my desires. I’d now got two much older women at the same time.

When mum left for work the next day, she had no idea about my day ahead. I’d already received a message from Megan saying, ‘Your surprise awaits. Come at 9.00am. The kitchen door will be unlocked.’ So precisely on the dot of nine, I walked as confidently as I could, round to Megan’s house, and in through the side gate.

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