Mother Starts Dating

I was concerned for my mother. My Dad had left her for another woman almost a decade ago and in that time she had only dated one guy. She had become insular and didn't socialise with anyone. In fact the only time she really talked to anyone outside of her job was when I would come over for Sunday dinner.

One night, as we relaxed after dinner with a bottle of red wine, I asked her why she didn't sign up for a dating site.

"I did, but it wasn't really my thing"

"Your thing?"

"I didn't meet anyone I really liked"

"But you did meet people?"

"Well yes, but.."

My mother trailed off and played with the rim of her wine glass. I cocked my head quizzically and waited, she finally relented.

"They were all younger guys, much younger, and they only wanted," she paused and lowered her voice, "sex."

I threw my head back and laughed.

"HAHA! That's what all young guys want! Plus, Mum, I'm 35 now, you don't have to be embarrassed talking to me about sex."

"But it is embarrassing!"

"Mum," I put on a serious tone while smiling, "don't you remember when I was a teenager and we had to have a long talk about the girls I was bringing home?"

My mother was blushing now and finished her glass before pouring another. I chuckled again, not wanting her to feel too embarrassed, but I was also keen to push her further. My mother is notorious for giving up an idea and I was really concerned that she was lonely. I was also a little bit drunk and feeling cheeky.

"So you didn't ever chat to any of them?"

"No! Like I said they were only after a one night stand and I've never..."

I let that one go as she took another swig of her wine.

"I don't know, sometimes you have to talk to these guys online first, they might be really nice, even if they are only after one thing." I gave her a comical wink. "And besides, there's nothing wrong with a little bit of sex."

My mother flicked me a look of humour mixed with annoyance. I decided right then that I would try and get my mother laid. It was probably the wine talking, but it seemed like a great idea to cheer her up and the more I thought about it the better the idea seemed. I just had to figure out a plan of action.

"Tell you what Mum, what don't you grab your laptop and we'll fire up the site and see if there's any guys online who want to chat?"

"I don't know..."

"C'mon Mum, you gotta meet someone somehow," by 'meet' I meant 'fuck', but I didn't say as much. "Besides, I'll be here and I can help you with what to say."

She looked at me skeptically.

"What've you got to lose Mum?"

"...ok," she agreed and got up to get her laptop and I refilled both of our glasses, figuring booze would help her be a bit more relaxed with the guys online.

She returned with the computer and took a couple of big sips while the site loaded on her screen. It was a site I had never used, but had heard of. It was a local site for our city and like all singles sites it had a well known hook-up culture. Mum quickly typed in her log in details.

First she showed me her profile. She'd chosen a pretty dull picture for her avatar, just her sitting on a park bench while on holiday. That was the first thing I decided to change. I slid in beside her and asked to take the controls. She relented and immediately stood up and took a swig of wine.

I looked through her images and found a nice one of her from last summer sitting the sunshine showing off a good amount of cleavage. My Mum has a nice looking pair of tits. She lost a whole lot of weight during the divorce and in doing so, created a waistline that emphasised how big her tits actually were. I paused briefly as I was a little surprised that I was thinking about my Mum's tits, but shrugged and uploaded the image.

"Oh that's a nice photo, I forgot about that" said Mum looking over my shoulder.

"Now let's think about what we want your profile to say"

"Well it doesn't say much right now..." Mum started to talk when she was interrupted by a beep from the computer.

At the bottom of the screen a small dialog box was flashing with the username BigDave87. I clicked it and the message was revealed: Hey bb, hru?

"Mum sit down, this guy wants to chat" I said, rising from the chair. She sat down and asked what to do. "Clicking that button will show you his profile and you just type to him in the box down there."

She clicked the link and as his profile loaded she asked, "What did he say?"

"He said, 'Hi Baby, how are you?' Don't worry about the weird abbreviations, just write how you'd write"

"Ok...Oh my god! He's 28!" For reference my mother is 60.

"You don't have to marry him Mum, just chat."

"What should I say?"

"Hahaha! Well, he asked how you are so why not tell him?"

She began typing:

"Hi there, I'm doing well. How are you?"

The response was almost immediate.

"Great! Love the pic u just uploaded!"

Mum turned and looked at me with a curious look on her face.

"There must be some sort of alert function that shows people if you updated your profile. In any case it was a compliment."

Mum turned back to the screen and typed: thank you.

"Add a smiley face," I said. She looked at me again. "Trust me." She typed in :-) and hit enter.

"Oh! It converts it into a little drawing!" she exclaimed, "that's neat!"

The chat box blinked again.

"Ur welcome! You've got a great smile and nice looking body! Very hot!"

Mum blushed and quickly replied again.

"Thank you ;-)"

"Oh! The smiley face is winking this time?" she said pointing at the screen.

"I think you made a typo," I told her, "the winky face is little more flirty, so it doesn't matter."

The chatbox updated again.

"Anytime lol! I think I would love to see more of you."

"Tell him you'll upload some more photos later," I said.

"Are we?" asked Mum.

"Maybe, but we'll cross that bridge later"

Mum typed in the reply, the response once again came swiftly.

"Lol! That'll be great, but I was meaning over a drink sometime?"

"Maybe, we'll have to see ;-)" typed Mum without my prompting.

"Cool! My name's Dave by the way, what's yours?"

"Di"

"Nice to meet you Di :)"

"Nice to meet you too Dave"

By this time Mum seemed more relaxed so I just let her chat

"So do you think you'd like to have a drink with me, Di?"

"We might be able to do that. Though I have only just met you."

"Well I can tell you that I'm a nice guy lol!"

"And I am a nice lady ;-)" (I wondered if Mum realised that by winking she was being more flirtatious).

"How nice? ;-)" he replied with a wink of his own

"Very nice!"

"Not even a little bit naughty?"

Mum glanced at me and I said "Sounds like he wants you to get naughty" before realising what I had just said to my mother. She turned back to the screen without questioning me.

"I can be naughty from time to time ;-)"

"Ha, good to hear! We might have be naughty together."

"Maybe ;-)"

"Have you ever met anyone off this site before?"

"No, in fact I haven't even chatted to anyone before tonight"

"So I'm your first? ;-)"

"So to speak ;-)"

"Oh, so you're experienced in other areas? ;-)"

"You could say that"

"Nice, I like a woman who knows what she's doing"

"What about you? Have you met anyone from here?"

"A few. But always keen to meet more."

"So are you more interested in one night stands?"

Alarm bells suddenly went off in my head. My goal was to get my mother laid, but she was still looking for a boyfriend. The chatbox blinked before I could suggest anything to her.

"Sometimes one night stands are fun. But I like multi-night stands lol!"

I froze as Mum started typing back.

"Well obviously I'd also prefer more than one night"

I was confused by this response but she hadn't shut him down. The box blinked.

"I'll have to do my best on the first time then. So shall we meet up?"

For the first time in a while Mum paused and looked at me.

"Well he seems nice and doesn't look too shabby," I said.

While she had been chatting Mum had been looking through his profile. He had a bunch of photos up of him put partying and drinking. He seemed like an average 28 year old, a little bulky with a goatee, not stunningly handsome, but it was a singles site after all.

"But he's so young! And I'm pretty sure he's just after sex" Mum said.

"That may be true, but you haven't been on a date in a very long time and what's wrong with at least meeting him for a drink?"

"I suppose you're right"

"And look," I said, not really thinking, "if anything does happen just bring him here where it'll be safer. You know I only live one street over."

Mum looked at me for a while, then smiled a little and said "ok." She turned back to type.

"I think we could do that. Are you ok with how old I am?"

"Why would I be? Like I said, I'm after a woman who is experienced."

"Are you inexperienced? lol!" As weird as this whole situation was, seeing my mother write "lol" was even weirder.

"Lol, nope! When we meet I can hopefully show you how experienced I am."

"You might be able to teach me something."

"That would be fun! So when shall we meet?"

Mum paused for what seemed like an eternity then finally typed again.

"How about Friday after work? There's a bar in town called Pico's, do you know it?"

"I sure do! I'll see you then Di, have a lovely night"

"You too, see you Friday, bye"

"Bye"

Mum closed the window and then the laptop. She picked up her glass and went to drink, before realising that it was empty. She looked at me.

"Well, that was... interesting"

"You did manage to get a date though"

"I'm pretty sure he has more than a date in mind." she frowned.

"That might be true, but you're a grown up Mum, you can handle these situations. Also there's nothing wrong with a little casual sex."

She raised her eyebrow at me.

"C'mon Mum, you aren't in an old folks home yet..."

"Ha! Thanks!" She interjected sarcastically.

"You know what I mean. Go have a drink with this guy, you never know, he might be a great guy."

"And if he wants more than a drink?"

"And if he wants more than a drink, you're a grown up, you can decide whether you want to do that. But please, have an open mind about this Mum. Meeting people is fun, remember?" I smiled widely at her and she smiled back.

The rest of the evening wound down and I walked home. On the walk I wondered if I had pushed too hard. I'd check with her again on Friday.

It was such a strange idea for me. I had never thought of my mother in a sexual way before, and I still don't. When I was a teenager, my mother had sunbathed naked on our balcony where no one could see her... except me as I walked through the house.

The image of her standing up one day and asking me to bring her a glass of ice water is stuck in my head. Hands on her chubby hips and wearing nothing but sunglasses. As a shy teenager, and her son, I didn't linger on her body long but I still looked her up and down. Back then she was much bigger than she is now. Short and quite round, with large, plump hanging tits and a pussy covered in light brown hair.

Now, as an adult, I still had no desire to fuck her. But for some reason the thought of hooking her up with guys for one night stands was incredibly exciting.

The week flew by and I hadn't heard from my mother, then on Friday I got a text message.

"Is it ok if I text you tonight to keep you up to date? I'm a bit nervous"

"Of course," I replied, "text me updates and let me know if you need me to come get you or anything."

"Ok. Thanks!"

I got my first text at 5:30pm.

"Heading to the bar now"

Then at 6:30pm.

"He's very nice, but very young!!"

Then at 8:15pm.

"Still at the bar, he might be growing on me."

At 9pm.

"Having a great time! Thanks for making me do this! :-)"

Finally at 11pm.

"Sorry this is going to sound crazy but I just realised that forgot to put away all my laundry! Just in case we end up back at mine for a drink, would you do me a BIG favour and pop over and tidy them up? We'll be about an hour or so"

"Haha! Sure Mum, this is a role reversal, me cleaning your laundry! Also glad you're having a great time!"

I put some jeans and a hoodie on and walked over to Mum's place. Using my keys I went in and saw the offending laundry drying in the middle of the living room. Mum's house is pretty small, but perfect for an older woman living alone. The living room comes off the front door and is a big open space including the kitchen area to your left. The main bedroom is at the far end of the living room on the right. Next to that is the spare bedroom which shares a small ensuite with the main bedroom. And then there's the main bathroom on the other side of the spare room and then you're back to the front door. So she was right to worry about the laundry as it was taking up a lot of room in the small house.

After folding up the clothes and putting the basket at the bottom of Mum's closet, I was folding up the drying rack when I heard a car pull up outside and people talking. That was my Mum's voice! I looked at my watch, 11:30! They were early! I grabbed the rack and shuffled into the spare room, shutting the door softly behind me just before I heard the door open.

"And this is my place, sorry it's so small." Mum sounded happy and a little drunk. "Oh, my son must've left the lights on."

"Your son?" The other voice was clearly a man's but sounded just as drunk.

"Oh he popped by earlier to do some chores, don't worry! Now let's have that drink! Take a seat, I'll grab it."

I sat down softly on the bed in the dark room, realising I was trapped. From the other room I heard my mother clinking glasses and rummaging through cupboards.

"I know I've got a nice bottle of wine here somewhere... must be in the bottom cupboard."

More rummaging noises then the young man, who I assumed was Dave said:

"That's a great view!"

"What? Oh you!" I heard my Mum reply.

I was confused until he replied.

"No seriously, on your knees with your ass up like that... and in that dress, damn! It's a thing of beauty!"

I don't know if I was more shocked to hear his comments about my Mum's ass or her reply.

"Hahaha! Good to hear, though I thought your plan was to get me out of this dress?"

"Yeah it is! All in good time though."

"Good because I found the wine!"

I heard my Mum pick the glasses and walk from the kitchen to the lounge, then nothing just murmuring. I was intensely curious and thats when I remembered the vent. To keep airflow moving between the rooms Mum had a bunch of vents installed, connecting each adjacent room. I looked up at the wall, the vent between the living room and the spare bedroom was above the bedhead. I climbed up as softly as I could and peered through the grate in the vent.

In the room was an amazing sight. My mother was kissing Dave, or more correctly, he was kissing her.

He was much taller than her, which is easy because she is kind of short. But he was also much bigger. BigDave's screen name was not a lie. He looked a bit chubbier than in his photos though it was hard to tell as he had both arms wrapped around my mother holding her tightly to him as he bent over her. Her arms were loose at her sides holding the bottle and two glasses. As I watched Dave slid one of his hands down her back and onto her ass, and squeezed.

As he did I heard my mother make a noise I had never heard from her before. It was a long low moan. At that moment my mother sounded like every horny teenager and old whore. The dress Dave had complimented was a long, sleeveless red dress that had ridden up a little as he groped at her ass. She kept softly moaning.

Dave pulled her upright and took the bottle and glasses from her, setting them on to the coffee table, before reclining on the couch. Mum stood there, swaying a little, I could see a slight smile on her face.

"Come here," Dave said, beckoning to her.

My mother walked over to him and bent down to kiss him, giving me an unexpected view of her ass similar to what Dave saw before. I could see her panty-line through the dress, but I was surprisingly impressed by my Mum's ass. It was nice, round, and perfectly wide when she bent over. It wasn't "pert" or "taught" but it was a hot ass alright and Dave was correct when he said it was a "great view".

Dave pulled my mother closer so she was standing between his legs as he sat on the couch, still kissing him. She was close enough for him to reach out with those big hands and grab her ass again, causing more moaning from my mother. This time though he spun her around, so now she was facing me directly (or rather the wall I was spying through). She teetered as she spun, but he grabbed her hips and held her steady. I noticed her tits moving in the low-cut dress; Dave would've had a fantastic view when she was leaning in towards him before.

Then, still with a firm hold of her hips, he pulled her towards him. Her ass finally ended up in his lap and I saw her let out a surprised "oh!" as he pressed against her. I realised the Dave had his growing hard-on nestled between my mother's butt-cheeks.

He leaned forward and kissed the exposed skin of my mother's back moving his hands up her body as he did. Mum began to moan louder as Dave's big hands reached her tits. He grabbed one in each hand, still kissing her back and neck. Fondling her breasts, weighing them, rolling his fingers up over her nipples, which I could start to see sticking through the fabric of the dress.

Then I noticed Mum was grinding, just slightly, against his crotch. This is exactly what I was wanting, for Mum to get laid and enjoy herself. The sight of the two of them working their way up to fucking was making me feel incredibly good, and I'll admit there was a slight stirring in my pants too.

Dave's rolled Mum's left nipple between his thumb and forefinger through the dress fabric before giving it a squeeze. Mum hissed in pain and pleasure.

"Ahhhh, not so hard!"

"sorry baby, you've just got me all fired up," Dave replied.

"Mmmm I can feel how 'up' you are right now," Mum purred back at him.

"Really?" He said slyly, "How fired up are you?"

Dave let his right hand slide down over Mum's body (still seated between his wide legs) to her knee, where he grabbed her dress and began to gather it up. He kept slowly pulling it, with his other hand still on her breast and his mouth on her back and neck, until her dress was mainly gathered at her hip.

Dave then began stroking Mum's exposed thigh. After the third stroke he held her knee and gently opened her legs. The look on Mum's face said "I'm nervous, but I really want to feel this", and she obliged, spreading her legs for him. Her gathered dress still covered what was left of her modesty; Dave's hand moved slowly down her thigh and under the dress.

His hand moved slowly and Mum moaned again, closing her eyes a little. Then I saw Dave's hand flick, and Mum's eyes opened wide as she gasped.

"Wow, baby, you are soaking wet! And I love a nice hairy pussy." I guess she still didn't shave it.

Mum closed her eyes again as I could see Dave's hand moving rhythmically under the red fabric. She leaned back into him, which pushed her (apparently) wet pussy onto his hand and spread her legs wider.

"You like what I'm doing to you?

"Mmmm hmmm" Mum nodded with her eyes closed.

"Does the little old lady want some more?" Dave said in Mum's ear. It was the first time I had heard either of them reference the age difference.

"Yes please" my Mum replied in a whisper.

Dave moved his hand in a slow circle then sharply flicked it again. Mum gasped and then moaned. She was breathing heavily and I could see her chest starting to blush.

"That's two fingers in your hot pussy" Dave whispered to her, before kissing her neck again.