The Hangout

Tess was the first face to appear on last week's hangout. He eyes flickered around the screen, and then her face transformed from blank concentration to smiling recognition. This was, shall we say, a relief.

I have been working with Tess for two years. In her mid-twenties, she is around half my age but we get on well partly due to the fact we share a sense of humour and taste in music and partly due to the complete lack of physical attraction between us. I'm no great looker (early 50's, overweight, balding and grey -- hardly catch of the century) and, whilst she is hardly unattractive, she's no great looker either... a little short, a little overweight, a little plain. She was soft and plump and pale. Don't get me wrong, there have been times when I've looked at her lecherously: the time when we had been moving desks and her blouse had gaped every time she bent over, revealing a small soft breast and pink little nipple; the days when she sat next to me and her short skirts rode up her thighs and her tights stretched thin. But nothing had ever come from it, not even remotely.

"Hi," she said, smiling, and the relief continued to build. "How are you doing?"

I smiled back broadly "Fine thanks. You?"

"Yeah, all good.... busy...."

She was sat on her bed, legs crossed. She was wearing black leggings and a short black denim skirt, a tight black top which was showing a little bit of cleavage and a beige cardigan. Tess had a round face with a small mouth and a fringe of dark hair which slanted across her forehead. I hate that haircut. Apart from sitting in front of a computer working all day, I have been passing the lockdown time by making porn fakes of a number of my colleagues and she has proved the hardest to get right. I'm divorced and live alone, so it's not as if I have much else to do in the evenings, and I have no intention of sharing my pornographic masterpieces online -- they are for my own personal pleasure. I had been slightly disappointed with some of my early efforts but have realised that the key is just to paste the face (and not the hair) onto pictures and then mess around with colour and hue and temperature until the skin colour of the original and new face matched. For most of the women this has been easy and I have made some fantastically perverted pictures of the women I work with in any number of compromising positions, but that fringe has made it hard to put Tess's face onto any other picture. It has driven me mad.

I was about to apologise, when a ping announced that someone else had joined, the boxes re-arranged themselves and Laura appeared. Now Laura -- she was someone who I definitely fancied and who I'd had a great deal of success on faking. She was a tall elegant redhead, slim with pert breasts and long legs and a handsome husband and she was completely out of my league. The nearest I have ever going to get to having sex with her was superimposing our faces onto picture of people fucking and the playlist I've created on Pornhub called "thing's I'd like to do with Laura" : 247 videos of pretty redheads being used and most definitely abused. Fucking, sucking, gangbangs, anal, double anal, nipple clamps, tit torture, piss and self pissing, large insertions, strange insertions, fisting, anal fisting, self-fisting and bukkake -- I've found a video with them all and thought of Laura as I watched them, dick in hand until I came.

"Hiiii," she drawled, and the moment for my apology passed. She was sat on a sofa, leaning on the arm with her legs tucked up next to her and a large wine glass in her hand. I must admit, I was slightly disappointed by the fact she was wearing jeans and a t-shirt and not a pretty little dress, but beggars can't be choosers.

One by one, other people joined the meeting. We had decided, early on when lockdown was looming, to meet between 8.00 and 9.00 every Tuesday if we could, to keep our spirits up and for those of us who lived alone to see a familiar face. This was meeting number five or six, I'd lost count to be honest, and numbers had dwindled slightly over the weeks. Rosetta had dropped out for example, which was a pity because she was by far and away the prettiest of my colleagues even if she was a bit of a pain in the arse (she'd earned the nickname "princess" quite early after joining the company). Steph still joined us, her massive tits sometimes showing more than she'd like if she got the camera angle wrong, and Big Rose (big as in tall as well as big in other ways) was always there too. There were a few more that dipped in and out, a few of the younger men and older women, but we were the core, sat by ourselves with a glass of booze.

By 8.05, everyone who was going to be there was there and all the usual social niceties had been completed. I sat on the floor with a beer in my hand and my laptop on the table in front of me, relaxing against the sofa behind me. I'd almost forgotten my fear. Almost.

"So, what's the weirdest thing that's happened to anyone this week?" Steph asked in her Aussie twang.

Tess's face lit up; my heart sank. I knew what was coming, the only question was how bad this was going to be.

"Some very kind person sent me..." She leaned forward to pick something, exposing her cleavage a little more. "....THIS!" With a flourish, she held up a fox tail butt plug.

The fox tail butt plug I had sent her.

There is no excuse for my behaviour; I know that I overstepped the mark and that my private fantasies should not have spilled over into reality. I know that middle aged men should not send unsolicited sex toys to young women. All I can offer is an explanation. The previous week, she had been talking about how her sister had asked her to read a bedtime story for her niece, a way for the young girl to keep in touch with Aunty Tess. The main character in the book was a fox, and she had quipped about getting in touch with her foxy nature for the reading. Everyone else had laughed. I had gone online and drunkenly ordered a 4-inch fox tail butt plug. At least I ordered it in black to match her hair. The following morning, I had woken up filled with guilt and remorse and tried to cancel the order. Unsuccessfully.

The faces on screen said it all: everyone (apart from me) was wide-eyed with a mixture of shock, horror and hilarity. I don't think anyone noticed that my own face was more horrified than amused, they were all focusing on Tess.

Amid the screams of laughter (and one bemused look from a more innocent member of the group), I could hear the questions beginning.

"What the fuck....?" Was the main one, expressed in different ways.

"Who..." was the next most common, and neither made me feel better about myself.

"Have you tried it out?" was Laura's question, which made me feel a bit better about myself and led to more laughter.

"Err... it's a bit... big?" Tess replied and, thankfully, the conversation began to move on without my having been exposed as a perverted old letch.

I did notice, however, that Tess kept on fiddling with the toy, stroking the tail, cupping the bulbous metal head in her hands. And smiling.

The hangout carried on. I don't know whether it was the alcohol consumption or the tone set by Tess's revelation so early on, but the talk took on a distinctly sexual nature. It started as double entendres and the sort of "Oooooh, matron!" comments so beloved of the Carry On films and early 90's Viz magazines. As usual, it was Laura who took it to the next level by talking about how she'd had to stop having sex earlier because her cat was watching".

"You had sex this afternoon?" asked Tess incredulously. Laura rolled her eyes.

"How did you know?" asked Rose before realising what she had asked, giggling and rephrasing. "How did you know the cat was watching?"

"You don't have to be on you back, Rose." Laura replied. "We could both see the cat!" Rose, bless her, blushed so bright you could even see it on the video. "And it really put poor Andy off!"

"I was texting you this afternoon!" Tess re-joined. "You weren't..."

"It's called multi-tasking..."

And so it went on, getting more and more risqué. Some people began to drop out of the chatroom, which only seemed to encourage Laura as she was left with people she was comfortable with. Steph made her excuses as soon as the conversation turned to breasts (she really is very sensitive about the size of her tits; I mean, they are massive!), leaving only myself, Laura, Tess and Rose. As it approached the "official" cut off time, Laura began to try and persuade the other two to flash their boobs and I realised just how drunk she was.

"Go on," she slurred, "No-one will know apart from Kurt and he won't tell, will you?"

I shook my head and grinned like a Cheshire cat, wondering if I could reach my key board and begin to record what was on screen without anyone noticing. Faking porn pictures was one thing, having a video of your friends flashing their tits was another!

"I will if you will..." Rose announced hesitantly!

"After three?" Tess asked. I couldn't believe my luck.

"One," Tess announced, reaching up to take hold of the neck of her top. Laura bent forwards and gathered her top in her hands at the waist, while Rose, to everyone's surprise, turned her back to the camera and took her top off completely.

My left hand crept towards the keyboard.

"Two..." Even more surprisingly, Rose reached behind her and unclipped her bra before shrugging out of it letting it fall to the floor. Concentrating hard so nobody could see, I managed to press Window G and start recording.

"Three!" I sat and grinned as the three women still on my screen exposed themselves -- to varying degrees. Laura, had simply lifted her top to reveal a very nice pair of tits encased in a light blue bra, made out of sheer material which meant that her large pink aureole were clearly visible. Tess had pulled her top down and the bra cup that covered her left breast so that one pale boob was exposed. Rose, of course, was the only one fully topless and turned around to show off a pair of fantastic DD's that carried on moving even when she stopped turning and then continued to bounce in the second or two it took her to realise that the other two were still fully clothed.

"Shit!" she shouted, before trying desperately to cover herself with her hands. She bent over, laughing, her blonde hair falling across her face. After a few seconds during which Laura and Tess bot quickly covered themselves up, she sat back up, still laughing and still covering her chest with her arms, clearly embarrassed but seeing the funny side of what had happened.

"Did you enjoy that, Kurt?" she asked.
"Yup!" I managed to reply. "Any chance of another look?"

With a smile, she dropped her hands to reveal her breasts again, wiggling her shoulders so that they jiggled from side to side. Laura and Tess a small round of applause; I gave my hardening cock a squeeze. And with that, Rose bade us a cheery good night and left the hangout.

"Bye Rose!" said Tess, somewhat belatedly. She held the bulbous head of the butt plug up against her cheek and looked straight at the camera. "So, Mr Brown, what do you expect me to with this?"

In retrospect, I should probably have apologised at that point; in retrospect, I should have said sorry and said goodnight. In retrospect, I should have stopped drinking a little earlier and chosen my next words a little more carefully.

"Shove it up your arse?" I suggested.

Laura laughed and Tess looked at the butt plug with wide eyes." You think that's going to fit up my bum?" she asked in mock incredulity.

"To be fair, I did buy you some lube as well..."

By now Laura was almost wetting herself laughing. "Go on Tess," she said between giggles, "Give it a go!"

"No!" She seemed genuinely shocked now. "I mean... it's fucking huge!" I did feel a bit guilty about that -- I had bought the largest option I could find. "I mean... how does anyone fit one of these up there?"

Again, maybe I should have bitten my tongue.

"You just need to stretch it a bit using your fingers first."

Again, Laura dissolved into laughter, "Go on Tess! Get your knickers off and get your fingers up there!" she hooted. I must admit, in the past I've felt bad about the way that Laura treats Tess; she sort of eggs her on, encourages her to do things that maybe she wouldn't do herself. I'd seen it again a few minutes earlier -- Tess had exposed herself while Laura had only shown us her (admittedly sexy) underwear. I could see Tess was a bit pissed and I knew Laura was three sheets to the wind, and maybe I should have stepped in.

But, lets face it, I wanted to see Tess shove that plug up her arse.

Really wanted to see it.

I could see that Tess was wavering, that she needed just a little shove and the alcohol and the peer pressure would push her over the edge.

"I bet you could easily fit it in with a bit of lube." I ventured. "I bet Laura could."

"Where do you think Andy's dick was when the cat was watching us?" she responded (another little snippet of information to be stored away for later -- Laura does anal!). "I mean, if you don't think you can..."

Watching all of this back later (yes -- I was still recording and yes, - I knew I shouldn't have been), you can see the point where the switch flicks in Tess's head. She takes a large swig of wine and giggles, then goes from sitting to kneeling very quickly. Her hands disappear beneath her denim skirt where her thumbs obviously hook into the waistband of her leggings and pull them down her thighs. She sits back down and pulls them down her legs and off over her feet and at this point you realise that her black knickers are in there as well, as they separate from the leggings when she throws them onto the floor. There's a quick glimpse of a hairy pussy as she does this, and then she kneels up again and sits back down with her ankles either side and behind her. The black skirt now covered her vagina and contrasted against the paleness of her thighs.

"Go Tess!" Laura shouted, and started whooping and waving a hand around like she was at a baseball match.

"So, what should I do, Kurt?" Tess asked. "You're the expert."

"Start by just squeezing a little lube onto your fingertip and then rub it into you bum hole." I told her. I watched as she put a pea sized dollop onto her index finger and reached behind her. She winced slightly as the cold gel made contact with her skin, but then sank back onto her haunches.

"And then just sort of... slip it in!" I suggested. Again, you can see from the look on her face the exact moment when her finger slips up her arse. I began to have doubts at this point. Was this fair? I mean, had she ever explored herself anally? Had she ever put a finger up there, never mind the biggest butt plug I could find? She began to move her body slightly, a sort of up and down, forward and backward sort of motion as she began to ride her finger.

Laura was now covering her mouth with her hand, her eyes wide as she watched her friend finger herself. "Is that good, Tess?" she drawled mischievously.

"Err.... yes?" Tess asked, like she should know the answer but wasn't quite sure.

"How far up is it?" Laura asked. She was obviously enjoying this; her eyes were sparkling with pleasure.

"Right up to the .... knuckle!" she sighed.

"Can you wiggle it?"

The look on Tess's face said that yes, she could and yes, it felt good!

"Try two fingers," I suggested. "Put more lube on it first though!"

We watched as Tess rose slightly and removed her finger from her anus. As she bought it back in front, she shrugged the cardigan off behind her to reveal she was wearing a vest top beneath. She squeezed more lube onto both fore- and middle-fingers and reached behind her again. There was a small look of concentration, and then a sigh and a smile as they slipped inside her again. She bent forward more this time so that she could reach easier, giving us a fantastic view down her blouse of her hanging tits.

"Are you sure you're not just frigging yourself?" Laura asked. Her voice had lost the air of amusement from before and her face had a curious look to it now, a mixture of lust and curiosity. "Turn around, Tess, I want to see."

I thought that she'd say no, but I think she was beyond caring: she'd walked so far into this river that even if she stopped now, it would be as hard to go back to being good as it was to keep going, to misquote Macbeth. Or, to put it another way, In for a penny.... Whatever way you want to put it, Tess did as she was asked. She moved her laptop to the end of the bed and then lay down with her head on her pillow and her knees pulled up to her chest. The little denim skirt was hardly covering anything but it was pulled up to give us a perfect view (and we could see Tess looking at her screen to make sure it was perfect) of her pussy and pale skinned bum. One hand reached round and pulled her arse cheeks apart, the other found her puckered, well-lubed anus and slid two fingers inside.

I expected Laura to clap or to shout out in encouragement, but she just sat there, mesmerised, watching her friend finger fuck her arsehole. I couldn't just passively sit there anymore. I stood up and removed my jeans and boxers and the sat back down on the sofa, legs spread and cock in hand. I adjusted my own laptop screen so that I could still clearly see what was going on with the result that I was now clearly visible to my two female colleagues as I began to slowly wank my erection.

This seemed to snap Laura out of her trance. "Shit Kurt," she breathed, "Nice package! If I'd known you were so fucking big..." her sentence trailed off. Now, I know I'm not huge compared to your average porn star, but not many people are -- my ex-wife told me she'd had bigger but the cute young thing who was the catalyst for our divorce (well, she wasn't the reason for the divorce so much as me being caught fucking her was -- my choice and my mistake!) had always said that I was almost double the size of her previous lovers which I still find both sad and hard to believe. I mean, I'm a good seven inches so she must have had a run of fucking blokes with cocks no bigger than the butt plug currently in Tess's bedroom. What I can say is that on that night, for whatever reason (a heightened sense of arousal, foreshortening of the camera, the way I was sat) even I have to admit that my cock looked good. I held it between my thumb and forefinger and waved it around a bit so that Laura could see it in its full glory before wrapping my hand around it and carrying on pleasuring myself.

Another thought settled in the back of my mind -- what did she mean "If I'd known"?

Things began to happen fairly quickly now. Tess needed no more instruction and slid a third finger into herself, stretching her arsehole even further; her breathing was becoming more ragged and her laptop was definitely picking up a squelching noise has her fingers plunged in and out. I was surprised to see that Laura's hand had slid beneath the waistband of her jeans and was now surreptitiously stroking herself. I was even more surprised when her husband (the tall, handsome one I mentioned earlier) came into the room -- and she didn't flinch. Or remove her hand.

"I thought you'd have finished by now," he said, bending over and kissing his wife, before sitting down next to her. Either he hadn't noticed her playing with herself or he didn't care. "What's happening?"

"Tess's stretching her arsehole and Kurt's having a wank."

'Having' was very much the wrong tense at that point; her use of the past perfect assumed that I was continuing with my masturbatory activity. Andy's entrance, however, had frozen me like a pornographic statue. I mean, what is the etiquette when a man walks into a room to find his wife watching a work colleague spanking the proverbial monkey with her own hands delving in her knickers? Was he going to hit the roof? Hit her? Come and hit me?