An Online Double Date

We all know how online dating works, and all humanity is there! So how would it work for a much older man looking for a casual relationship? No moral judgements please; we all have our own crosses to bear.

So the parameters were set. 45-55+, within 20km, and a fairly anonymous photo posted. Not many 'swipe rights' coming with that, I guess.

Checking twice a day, swiping anything female! We all clutch at straws sometimes.

And then after a week, a match!

At least someone had swiped right on me. The name was Sarah, aged 47, and living 6km away.

But there was a 'but.'

The photo was of Sarah, and her mum. To be fair both were very attractive, but obviously Sarah's mum was late 60s, the same as me.

The initial messages were polite and introductory, and it became apparent that Sarah was actually advertising for a 'date' with her mum.

I was intrigued by this, and what Sarah was planning was to find an older man who would be prepared to meet Sarah with her mum on an accidental 'setup' meeting.

Sarah would appear to be an old friend, and they would all have coffee and conversation.

After the meeting, and at home, Sarah would ask her mum if she liked me, and set up a further date with just the two of us.

I'm always up for something a bit different, and so we decided to set something up.

Sarah was living with her mum after her own separation just a few weeks before. I guess that had brought them closer together, and her mum had said how nice it would be to have a 'boyfriend'.

I was sitting in Costas on a sunny summer afternoon when Sarah, and her mum, Maggie walked in. The acting began.

"Hi Sarah, fancy bumping into you, is this your mum?" I tried to look surprised.

To be honest I noticed Sarah first. She was dressed in black leggings, and a tight fitting white t-shirt, with a low neckline. She had a good figure, with short black hair, and green eyes.

Maggie was a curvy lady with large breasts, and grey hair, and sparkling eyes. Smiling, she nodded as Sarah said, "Hi John. Mum this is John, we worked together at Newton's School."

We all sat together for the best part of an hour, chatting about this, and that.

Sarah talked a little about her 'break up," and Maggie about her home, and hobbies.

I listened, and chipped in with snippets about my home circumstances.

When we parted, Sarah and I exchanged mobile numbers, as though we were old friends, and I said to Maggie, out of politeness, that I hoped that we would meet again.

By the time I arrived home, I had thought about the plan.

Maggie was a nice enough woman, but I wasn't sure if there would be any chemistry. Sarah was a different proposition, however, but way out of my league, probably twenty odd years younger than me.

About an hour after arriving home, I received a text.

'Thank you for today. Mum liked you, and so did I. I think she wants to meet you again. I will talk to her about it.'

I replied, 'Thank you too. Will hear from you soon. You both looked stunning.'

There was no further contact the next day. I just let it ride; so many online intros come to nothing.

Then the next morning, a text came through, asking if I wanted to meet Maggie for an afternoon drink in her local pub.

It seemed odd that everything was being arranged through Sarah, but I was happy to accept that for now. No doubt after this 'date' I would have more direct contact with Maggie, if it was to progress further.

The arrangement was to meet the following afternoon at 2pm in 'The Black Horse.'

As I was sitting in a corner seat at five past two, I was surprised to see Sarah walk in. Seeing me, she came over, and immediately started to apologise.

"I'm so sorry John, mum had a funny turn just before lunch, and I didn't want you to be let down, so I thought I'd come and have a drink with you instead. You don't mind do you?"

"Of course not, is she ok? Being left alone I mean?"

"Yes, she has these moments occasionally, I'm just sorry to disappoint you."

How wrong could she be. Sarah looked absolutely stunning in her summer dress.

"I'll get you a drink," I said, and went to the bar to get her a small lager.

Returning, I could see a couple of guys at tables nearby, admiring her tanned legs, and obvious cleavage.

"How are you anyway?" I studied her face as she replied.

"Oh I'm ok, my ex is being a pain, but one piece of good news is that he has moved out of our house to his new woman's, and as of today I can move back in. I've been at my mum's for six weeks."

"That sounds like good progress, is it far away?"

"No," she replied, "only about two miles, in fact I'm probably going to go and check things out later, after I've had my drink with you.."

"I bet he's left it in a bit of a mess," I added, smiling. "You may need to spring clean."

"Are you volunteering?" Sarah joked, and smiled.

"Well I'm an excellent driver with a 'Dyson,' and I'm tall to dust high up." I chuckled.

"Offer accepted," Sarah touched my knee, and added, "No, I'll be ok, I'm just joking."

"Ok, but I can give you a lift over there now if you want?"

"Are you sure John? That would be a really big help. Just to have a look at it, to see what state it's in. I'll call mum to see if she's ok."

And so we drove the short distance to her house. I continually glanced at her legs, which showed below her short dress. I was hoping she didn't notice. Nothing worse than a pervy old man!

We pulled up outside the three bedroomed semi-detached house, and Sarah led the way up the garden path, and I asked if it was ok if I came in with her. I wasn't sure if she was going to be shocked by the state that her ex might have left it in.

In fact it wasn't too bad, which surprised Sarah, and she certainly looked relieved. There was even some reasonably fresh milk in the fridge, and she made us both a cup of coffee.

Sitting on the sofa both of us started to 'open up' about our relationships.

It seemed quite odd, because Sarah was quite frank about some aspects of her failed relationship. I thought that our age difference was probably the reason, more like a father/daughter chat.

The paradox of that was my inability to ignore the amount of bare leg that she was allowing me to see, as she curled her legs up beneath her.

I'm afraid more than once she saw me looking out of the corner of my eye.

When it was my turn to tell about my last relationship, and how I missed the intimacy of someone else, I was sure that she deliberately crossed, and uncrossed, and moved her legs to give me more of a view. But I wasn't totally sure!

Then Sarah dropped the bombshell.

"I'm going to say something that may shock you."

My face must have looked a picture.

"Yes, go on."

"My mum didn't really have a funny turn, she's perfectly ok. I wanted to see you alone. Does that shock you? That I find you attractive? I've always found older men attractive."

I stuttered with my reply.

"Sarah, I cannot deny I'm very surprised, but absolutely delighted, you silly girl."

I moved the few feet from one end of the sofa to beside her, in less than a second.

We both wanted to kiss.

I looked her in the eyes, and she smiled before parting her lips slightly. Her tongue slowly moved its way along her top lip, and back along her lower lip, moistening the pink textured skin. The kiss was soft, sensuous, and tasted divine. Her tongue flicking into my mouth, and flirting with mine.

As the kiss ended she held my gaze. She put one finger to her lip as if to imply, "Don't speak."

I remained just inches from her face, breathing in her perfume, excited by the kiss.

I felt her fingers tugging my belt free, and then unzipping my trousers.

"Lay back, John," she whispered, "this is going to be all me, relax."

I did as she requested, and I allowed my trousers, and boxers to be removed.

It was then that I felt the softness of Sarah's lips once more, but this time slowly sucking the head of my cock. I could feel it hardening as her tongue circled, and recircled it.

The whole of it was inside her mouth, but as she played with it, it lengthened, and she began to move her head up and down. I heard a loud moan, the moan was coming from me.

Sarah had told me to relax, but that was difficult for a man who'd not had sex for months. My cock was ready to erupt, and as if she had a sense of that, Sarah sat up. I watched as her eyes focussed on mine again.

I saw her lift her dress over her head, revealing her matching cerise lingerie. She unclasped her bra, her breasts dropping free, nipples hard, and pert. She half stood, as she slid out of her panties, her eyes piercing mine with her desire.

And then spreading her thighs, I watched as her pussy, wet with her juices, lowered itself onto my cock. That feeling, unfamiliar through the passage of time, revived memories of how it used to be.

Sarah placed her hands flat on my chest, and raised herself up, before plunging back down, rubbing her clit against the top of my shaft. She was adept at the technique of holding back my orgasm while building her own.

I watched her as she closed her eyes, gasping shorts gasps on each rise and fall. I reached to cup her breasts, feeling the hardness of each nipple, squeezing each in turn, bringing a quiet squeal from the back of her throat.

Her breathing became quicker, and her gasps turned to short groans, and there was no way I was going to last much longer.

"I'm cumming John, god I'm cumming," Sarah went still, pushing down hard on my cock, and gritting her teeth. I felt her pussy pulsate, becoming wet, and I simply started to empty myself into her, with a loud, grunting sigh.

Our orgasms seemed to last for a long time, and eventually Sarah sunk down onto my chest, still gripping my shrinking cock in her soaking pussy.

"John, that was magical, thank you," she said, still out of breath.

"It's me who should be saying that," I said half laughing.

We stayed like that in each other's arms for several minutes, until reality kicked in.

"Sarah, I know all of that was very sudden, but I have to ask, is that it? Or can I see you again?

My face told its own story.

"John, I said that was magical. I want it again, but we need to be careful. I don't want to hurt my mum." Sarah's face was sad.

"Yes, I understand. I will be discreet. I will run you back to hers if you want, to get your car, but I want to see you again soon, if possible."

Sarah smiled, "Yes me too, let me get this place sorted, and you can come for a meal."

So I drove Sarah back, and dropped her around the corner from her mums, and went home to mine in a fog of thoughts, and questions.

We texted each other over the next couple of days, and as soon as Sarah had the house sorted, she sent me the invite I'd been waiting for. I was invited round on Friday evening.

I arrived punctually at 6.30pm carrying a bottle of wine and some flowers. I was still an old romantic, or should I say traditionalist.

Sarah greeted me with a beaming smile, a hug, and a kiss.

"Oh that's so nice of you, you shouldn't have," she said, taking the flowers to put them in a vase.

I followed her into the kitchen, admiring her body, which was sheathed in a tight fitting black dress, with thin straps over her shoulders, and, obviously, not wearing a bra. With her short black hair, her long neck, and bare shoulders, she looked sensational.

"I hope you like fish? I thought something light in this hot weather."

I nodded enthusiastically.

"I love fish, and if I'm going to seduce you, young lady, then it is ideal."

I smiled, and our eyes locked onto each other.

"Oh, and what if I resist?" Sarah's expression was somewhat flirty, and teasing.

"Then naughty girls will have to go on the naughty step, or even worse." My expression was of mock sternness.

"Oooh sir, I'll be good, I promise," and Sarah blew me a kiss and laughed.

She turned, and poured the wine, and we sat at the breakfast bar, and talked 'sensibly,' until the meal was ready.

It was a delicious meal, and the wine flowed, but the sexual tension was always there.

Sarah was even more open about her relationship with her partner. How he had been unfaithful more than once, and she had 'strayed' with an old boyfriend. But Sarah also revealed how she had dabbled with mildly kinky stuff in her twenties.

Her ex wasn't into that, and since the shine went off their sex life, she had just relied on vibrators, and masturbation.

All of this conversation seemed to heighten the anticipation of the evening, and added to the several glasses of wine we had consumed, there was only one way it could go.

"Well young lady, that was a delicious meal. Now I think we should relax, and enjoy what the evening brings."

Immediately I had used the words 'young lady,' it was like a signal switching Sarah on.

Smiling broadly, she replied, "Yes sir."

"You go and relax on the sofa, and I'll join you in a minute."

Sarah did as she was asked, while I stayed a moment in the kitchen just to collect a tea towel.

"Close your eyes young lady," I said as I came to join her in the living room.

She didn't say a word, but I could tell that she was excited, just by the way her breasts were rising, and falling.

I walked behind the sofa, and folding the tea towel into a long band, I placed it over her eyes, tying it behind her head.

"As you know it's all a matter of trust when blindfolds are involved. I won't be tying your hands, or feet, but maybe that's something for the future. This is just some gentle play, but if you misbehave, you may go over my knee."

"Yes sir," replied Sarah, in a hushed voice.

I leaned forward, and kissed the side of her neck, softly, fleetingly, but just enough to hear a quiet sigh.

Placing my hands on her bare shoulders, I slid the straps of her dress downwards, and as the dress fell away from her breasts, I stroked my fingertips across both nipples. The quiet sigh became louder.

I walked around the front of the sofa, and taking her hands, pulled her up, so that she was standing in front of me. It didn't take much to help the dress slip to the floor.

"Let me look at you," I said, stepping back to admire her body, with only a black thong hiding her pussy.

Self consciously, she stood with one knee bent in front of the other.

"I want you to stand with your feet astride, young lady, so that I can see how wet you are."

Sarah shuffled slightly, before spreading herself, revealing her soaking wet thong.

"Well young lady, you seem to be in a state of arousal, what have you got to say for yourself?"

Again she fidgeted slightly, before replying guiltily, "Yes sir, I'm finding my situation slightly awkward."

"Indeed," I replied, "It may become more awkward. Take off your thong."

"Do I have to sir?"

I didn't like the questioning of my instructions.

Taking her hand tightly, I pulled her to the chair that was on the other side of the room, and sitting myself down, I forced her over my knee.

"I don't like having my wishes questioned, young lady. You had been warned, and now you must pay the consequences."

Sarah started to struggle slightly, her breasts rubbing against my trousers.

"Please sir, I'm sorry, I'm really sorry," Sarah pleaded.

"Too late I'm afraid, your bottom will be getting very sore."

Taking the thin silk of the thong, I tugged it down her legs to her ankles.

With one hand pressing her body downwards I landed a hard smack on her right buttock.

"Ow!" She cried out.

The second smack on her left buttock was followed by a louder shout, "Oooww."

There followed a dozen smacks across her backside, as she struggled, and yelled for mercy.

As I stopped, Sarah realised it was over, for now. Her breathing slowed, as she whimpered slightly.

"Maybe that taught you a lesson young lady," I said, as I smoothed my hand over her reddened buttocks.

"Yes sir, thank you sir," she said in a croaky voice.

Meanwhile my fingers were stroking the back of her thighs, and then moving over the warmth of each cheek. As they smoothed the flesh, they strayed slightly between the cheeks of her ass, and Sarah's whimpering became silent. She moved slightly to part her legs, almost inviting me to venture further.

"I think you should relax now my little one, there is no more pain, just pleasure."

Sarah visibly did relax, and as my fingertips reached her pussy, she sighed with satisfaction.

Her pussy was almost dripping with her juices. My finger slid between her pussy lips, and found her clit. It was so engorged that the little bud stood out proudly, and as my finger ran over it Sarah shook with pleasure, and let out a loud groan.

"Ohhhhhh, please," she cried, as I dragged my finger back over it.

I only had to repeat this twice more, and as I circled it again, she started to cum.

I held onto her, as she shook with the orgasm.

" Oh John, I don't know what you did but do it again."

"I'm sir to you, young lady," I said sternly. " Do you want another spanking?"

"Oh no, no, I'm sorry, sir, I was just so wound up."

I reassured her that I'd forgiven her that moment of indiscretion, and I allowed her to stand up.

I was smiling as I removed the blindfold, and as Sarah became accustomed to the light I kissed her softly on the lips.

"I don't know if you enjoyed that little bit of role play?" I enquired nervously.

"John I thought it was so exciting, really. Although my bum is sore!"

"Well Sarah, I haven't finished yet, with your permission?"

"Oh John you are silly, a real gentleman. But can you show me how a gentleman makes love?"

I needed no second invitation.

Sarah lay back on the sofa with her pussy pink, and exposed, glistening in the light from the table lamp.

I began to undress, taking off my trousers, my shirt, my boxers, exposing my cock, which was seeping precum from the tension of the last half hour.

I lowered myself to kneel on the floor beside the sofa. I looked at Sarah, and she knew exactly where I was going. I lowered my head, and my tongue took a first delicious taste of her pussy. There was a deep sigh, as she arched her back, and I started to lap those juices up.

There is nothing better than burying your face in a succulent pussy. The juices smeared over your face as you lick deeper and longer. There is an art to that technique of licking, and sucking the folds of a pussy, and the bud of a woman. If you can read the signals, you can hold her on the edge. Just far enough away to know how far to push, hearing the audible sounds of pleasure, assessing the needs of when you should plunge over the edge.

Sarah was the perfect foil. We seemed to have a unity of purpose, and she too, held herself ready to let go.

When she came the sofa seemed to shake with her hips pitching up and down. She gripped my head between her thighs, as her pussy seemed to pour more juices down my chin.

As the room quietened fom her exultations, I looked up at her laying back in the cushions with eyes half closed, catching her breath.

When they opened, she smiled at me between her thighs, willing me to raise myself up, and kiss her.

I moved my face towards her. She watched as my lips, still damp with her juices, touched hers. We kissed, and then an almost startled look, and a moan, as I entered her. She had suddenly remembered that I hadn't cum, and my cock was waiting for its pleasure.

As I pushed deep into her she couldn't help but say, "You devil John, ooooooh fuck me."

The sofa absorbed the impatience of my thrusting. Sarah's pussy juices made a delicious sound as my thighs met hers.

I was not expecting her to react as she did, given that she'd cum twice already, but as we found a rhythm that suited us both, I realised that I could make her cum again. And cum she did. After some minutes she was meeting every thrust I made with a cry out loud. I needed no encouragement, and with both of us bathed in sweat we both found ourselves staring into each other's eyes, almost urging each other on.