Mark & Connie Persuasion

This story contains characters from other stories but is intended as stand alone.

All comments and feedback are gratefully received as I'm hoping the feedback will encourage improvements in my work. This is a work of fiction from the deep dank recesses of my mind and any resemblance to real people is purely accidental.

This story depicts anal sex between consenting adults, if this not to your liking, please visit some of my other submissions, otherwise I hope you enjoy.

----------

They had similar roles in their company which meant Mark didn't get to see Connie or her partner Rich much unless they met up at various customer sites or it was a quarterly team meeting back at head office. It was a running joke between the three that they were ships that passed in the night and Mark wondered if their schedules ever put much strain on Connie and Rich's relationship given, they were sometimes on different customer sites. A constant running joke was the way Connie sometimes dressed whenever she needed development resource from the coders she would dress accordingly. It was always professional in dark blue trouser suit, but underneath was a crisp white T-shirt. That in itself sounds unremarkable, but her secret weapon was the push up bra that positioned her tits prominently.

Mark considered them an impressive sight and often chided her about it but used in the hushed confines of the room her developers sat -- with little or no female contact from one day to the next -- guaranteed that they hung on her every word, and they were putty in her hands especially when she stood at the side of their desk leant forward with her arms leaning on the desk as it accentuated her cleavage. Don't get me wrong they weren't the sort of tits that gave her backache but on her tall slender form even their modest size looked impressive.

As was the custom when the implementation folks were engaged at the same customer, they would often meet up of an evening in a restaurant to chew the fat on a variety of topics from their individual projects to their personal lives. Invariably they would consume a fair bit of alcohol which loosened tongues and on one such occasion a couple of months ago Connie had confided to Mark that she particularly missed Rich sometimes as she missed his ability to 'scratch a particular itch' as she put it and was intending on shopping online for some vibrators to help with the itch.

Mark had cheekily offered his services to scratch the itch, he liked Rich and had been half joking. He had had a few assignations with a few of his female colleagues and figured his words unimportant. Little did he know that Connie had not been as affected by the alcohol as Mark had thought and she had squirreled away that little nugget and passed it on to Rich at the next available opportunity. Unbeknown to Mark the two lovers had only recently been talking about spicing things up by involving a third party but couldn't agree on who it would be.

The stars aligned to position Connie, Rich and Mark at the same customer and at the same hotel for the same three nights. Naturally the three dined together on the first night and it was during their usual jovial banter that Mark asked "I appreciate you've only seen each other at weekends for the last few weeks but as you two are in the next room to me tonight could I request that you dial down your nocturnal romping's the next few days as some of us need our beauty sleep more than the rest of you.

Connie and Rich fell into fits of giggles and when Rich countered with "You'll have to come and join us then" Mark joined them. He hadn't realised that Rich was only half joking. Connie excused herself from the table and Rich leant forward and asked in hushed tones "What do you think of Connie?"

Mark didn't catch on at first and simply replied "I think she's fantastic, I wish I knew my side of the product like she does hers but then she was a user way before joining us on the dark side."

Rich shook his head, "No, No. Not like that. Wouldn't you agree she is gorgeous and sexy in equal measures?"

Mark looked back at him quizzically wondering 'where is this going?' before replying "I will freely admit she is gorgeous and would probably turn the queerest of blokes straight. You my friend are punching well above your weight with her? I have often wondered what she sees in you but then women are wired differently to us."

Rich nodded thoughtfully "Fair comment" he added "But if I weren't on the scene would you be hitting on her. You being a free agent and all"

Mark kept quiet for a while and gave Rich a suspicious expression just as Connie returned to the table. She saw the two expressions and used one of her stock lines "Why the long face Dobbin?"

Mark was unsure how to paraphrase the conversation, but Rich beat him to it saying, "I merely asked our esteemed colleague here if he thought you were hot?"

Connie looked shocked and replied, "You didn't?" but then immediately turned the tone around by asking "And? What was your answer?" smiling back at him.

Mark sat there gapping for a while before answering with a drawn out "Yes"

Connie reached up and bunched her boobs together "What the girls? my exquisite butt? or my lusciously long legs?"

Mark replied "Yes" before qualifying his answer "All three of those and would you mind not jiggling the girls around. It's making my trousers uncomfortable."

"See. I told you" Rich interjected, adding "Who can you rely on in a tough situation? If we can trust anyone it's Mark."

The quizzical look returned to Mark's face and so Connie, digging her elbow in her partners ribs, went on "Rich and I want to ask you a big, big, big, big favour and there is no shame in saying no, we just ask that you keep this between the three of us." Mark stayed quiet so she continued "A little dicky bird in the office tells me you know a thing or two about anal sex." In truth it could have been one of three of their colleagues, but Mark wasn't sure which one Connie knew, he had a suspicion but remained tight lipped in case he guessed wrong, and it started the conversation down a path he didn't want to go. "Well, it's something Lumpy here and I have wanted to try for some time now, but we need a mentor to help us if you get my drift?"

"Well," Mark started "You have to take your time. You especially" he waved an admonishing finger at Rich. Looking back at Connie he continued "You need to prepare yourself thoroughly. This is no room for your usual wham bam thank you mam approach. But with time and no small amount of patience it can be an extremely pleasurable experience for both parties. But you can get all of this off t'internet. It's not rocket science and there must be a shed load of detail out there."

Connie was leading the conversation and replied "Yes we know, we've done all that but... I don't know... it still felt alien when we try somehow. What we need is someone detached to take us through it. Someone who doesn't want to form emotional ties associated with intimate contact. First and foremost, someone we can trust and someone who finds me attractive and won't mind sampling the goods while showing us. That's four different people we want in one person." And then levelled Mark with one of those stares that made him feel like he was in an interrogation spotlight.

"The fact we're having this conversation here and now, I'm guessing you are looking at me to be the mentor?" asked Mark, both nodding in unison. Turning to Rich he asked, "You are willing to share this vision of loveliness with another bloke if I teach the two of you about fucking her up the butt?" Rich nodded so Mark turned to Connie and asked, "And you will undress in front of me and then willingly give yourself to me if I show you?"

Connie also nodded immediately adding "Yep that's the deal" playfully bringing her arms in so that her tits were bunched up.

"Wow" replied Mark as he sat back in his bench seat with a bewildered expression while the other two stared at him expectantly. Connie never doubted for a minute it was a good thing to ask Mark, what she was apprehensive about was would he go for it. Mark looked from Rich to Connie and back again, his face giving nothing away while he mulled it over in his head 'I get to fuck her butt', 'but then Rich will be there watching', 'but I get to fuck that lovely shapely butt' back and forth his mind went and it was almost painful for the other two until he answered. "Ok, I will do it" the two let their breath out that they had inadvertently been holding "On two conditions." They both sat there expectantly again as Mark went on "It's going to be weird doing it with Lumpy present and so it'll just be the two of us the first time and I will teach you how to teach him." Connie and Rich both looked at each other and nodded before turning their attention back to Mark. "Secondly if you are going to engage in anal sex, then you also need to experience double-penetration as well which is when this dodgy fucker gets to take part."

Connie and Rich exchanged another look, smiling broadly before Connie replied, "It's a deal" with a wide eyed expression.

Mark then looked at Rich who had an equally broad grin and the younger man added "I'm fine with it. If her ladyship gets what she wants, I'll get my jollies later."

Mark was genuinely surprised but stated "To make this a success it deserves there are some things we are going to need to make your first time as painless as possible."

Connie responded with "I'd like to think we have most of that already but what do you need?"

Mark held out his fingers to count off "Lube for a start, it comes in many forms."

Connie immediately responded with "Yep, got that. We got a couple of different types, but we purposely bought the numbing sort. It's something I read somewhere. What's next?"

Mark nodded approvingly and counted off another finger "Some kind of toy would be good, either a vibrator but a butt plug would be better."

"Check" came Connie's reply sticking both thumbs up, adding "I packed both and have multiple sizes of both. Anything else?"

"Wow" replied Mark, "You have done your homework, haven't you? The only other question then is when and where?"

Connie shrugged her shoulders, cast Rich a quick glance and replied "Why not here and now? Well not right here in the restaurant, I meant here at the hotel. You get what I mean. Look, I know this is monumental, it's as monumental for us as it is you and we really, really appreciate it. We had struggled with the dilemma of who to ask for help, we'd debated it for weeks and then this project landed, and it felt like everything had dropped into place at just the right time. I never intended to give up my cherry to just anybody, it had to be you as we didn't have a Plan B."

Mark was momentarily stunned and didn't reply straight away but eventually he said "Well if it's any consolation I wouldn't do it with just anyone. It is worth it however as long as you don't get put off by the early fumbling's -- in other words persevere as it will be worth it in the long run. I have to say the one thing that swung it for me was the thought of that lovely butt of yours. It's going to be a pleasure to help you on this one and as for double penetration, now that really will rock your world."

All three made their way back to their rooms and a plan was formed so that Rich would crash in Mark's room so that Connie was a bit more comfortable in her own surroundings -- the fact that their rooms were identical and of a generic hotel room design found in thousands of others was neither here nor there. As Mark entered Connie's room, he pushed the door shut and Connie stepped forward to push him against the door. She then reached up her hands and took his head in her hands as she leant forward kissing him squarely on the lips. As she pulled away, she said "I really can't thank you enough. In truth I couldn't imagine doing this with anyone other than you and Rich" and then kissed him again.

When she pulled away a second time, Mark slapped her butt playfully and instructed her "Okay young lady, let's have those clothes off" as he sat on the edge of the bed. She giggled and went and stood in front of him as she reached down for the bottom of her top and then pulled the top up and over her head. Mark nodded approvingly and said "Nice". She then hooked her thumbs into the top of her trousers and pushed them down past her knees and once they were pooled around her ankles Connie stepped each foot out so that she was stood in just her bra and panties with her hands on her hips. Mark smiled broadly and nodded saying "Very nice indeed. I can see I'm going to enjoy this. Now the rest if you please, we're going to take a quick shower making sure you're nice and clean and relaxed". Once she removed the last few items Mark stood and stepped towards so that he could take her in his arms and kiss her once more. He then slapped her butt once more saying "Go get the shower going while I take my stuff off." Connie did a little trot to the bathroom while giggling, from the impression he got Mark surmised that she was looking forward to the experience.

When he got into the bathroom Connie was already under the jet and had liberally soaped her body up. Mark climbed inside the bathtub and stepped behind her, inadvertently pressing his hard cock into her lower back and got a "Mmm, nice" in return as Connie reached behind her and soaped his cock up while Mark wrapped his hands around her and cupped her tits in his hands, working her nipples with his thumbs.

Mark then switched and took over the soaping of her butt, paying particular on her sphincter which seemed to ready accept his thumb as he worked it around. "That's a good sign and is the first step. Are you okay with that? Not uncomfortable?"

Connie looked over her shoulder at him and replied "No, all good so far. It feels a little weird but a nice weird. I have tried to practice pushing a vibrator up there but it's Rich's cock I've struggled with."

"Good girl. I hope he appreciates what you're doing for him." Mark stated while continue to lavish attention on her shapely butt.

"Oh, he does, I hope we both end up enjoying it and it helps knowing that you have some experience. We haven't had much joy so far, but I think that was partly down to me being so nervous. This feels differently somehow. More relaxed" came her reply.

They rinsed off and while still dripping wet made their way to the bed. Mark took her in his arms to kiss her once more to kiss her before saying "Now I want you to fully understand this. At any point you become uncomfortable with any of this you just shout up. The only expectation from me is that you have an enjoyable experience. Got it?" Connie smiled and nodded and kissed him again, before he said, "Go find me all the stuff you've brought so I can see what I have to play with."

Connie rummaged through her case and came back to him with her hands full. He was pleased to see a couple of butt plugs as well as four different types of lube and a couple of vibrators. He placed them on the corner of the bed and then spun her around and had her kneel on the bed, nudging her legs apart so that her pretty rump was pointed at him. He licked his left thumb and then lodged it just inside her sphincter which he felt tighten at the intrusion. With his right hand he ran his index finger down her labia as it pouted at him. Connie flinched momentarily but then started to push her hips back at the enquiring fingers. Slowly she started to scrunch the bed coverings in her fists.

Mark then removed his thumb and replaced it with his pussy-soaked finger and worked that around just inside asking "You still okay?" He got a nod of the head as his only reply and so took hold of the nearest tube of lube and applied a liberal amount to his fingers and around her anus so that he could then work a second finger alongside the other. Connie gave another groan but this one was more a groan than a moan and was drawn out. Mark encouraged her on by saying "Good girl, you're doing really well." Mark then reached over for the slimmest butt plug, coated it with a decent amount of lube and then used the tip to replace the fingers he had just withdrawn.

Connie seemed to accommodate the change well and Mark encouraged gently saying "Ok, I'm going to apply a bit more pressure. I want you to try and relax you muscles back here as much as you possibly can." He then rummaged through the tubes to find the numbing lube he knew well and applied even more to the plug and her anus. Mark decided to take her mind of things by dipping is head forward and running his tongue along the length of her pussy just as he pushed the plug with a little more determination and found her butt accepting it readily. This was the time when he left the plug where it was and performed a contortion so he could give her pussy some concentrated licking. This had the required effect as she started to bounce her pussy up and down on his tongue as two fingers started to worm inside her pussy in search of her g-spot which was easily located once he worked out the right depth to intrude.

Just as she was getting close to her climax Mark extracted his fingers and his tongue leaving her hanging. He teased the end of the butt plug before removing it completely and had a grandstand seat as her sphincter slowly closed up again. This was the point when he grabbed the tube of lube once more and spread a generous bead along his cock as he massaged it in and pointed the spongy head at her anus. Connie took a deep breath and tried her best to relax back there. Mark reached forward and stroked both hands down her back bone and whispered "Ok, you might feel a little jolt but remember, it's only for the first few times and tell me to stop at any point."

"Ok" came the gasped reply and so Mark slowly pressed his hips forward and the head of his cock started to prise her sphincter open as she took a sharp intake of breath. He stopped temporarily but then pushed again and the tip progressed further still until he held still once more. Soon he found the head slipped inside and he held still once more.

Mark leant forward and kissed Connie's back asking, "How is that? The widest part is in you now."

Connie looked over her shoulder with a broad grin saying, "That was easier than I thought I can't believe it slipped in so easily."

Mark smiled back and replied that's down to two things "First and foremost you had already done most of the hard work preparing your butt. Secondly slow and steady wins the race. Tell Lumpy he has to go slow and keep checking with you. Finally, you did all the hard work by relaxing yourself" If truth be told Connie had completely forgotten about her partner sat in the room next door, she was so focused on relaxing her sphincter for Mark that she had blocked out everything else.

Mark then started to incrementally insert his cock inside her with each successive thrust until Connie felt his balls meet her pussy. She wriggled her hips to make sure and said in triumph "Is that it, are you all the way inside now?"

Mark nodded back asking "Yes, it is, are you still okay?"

Connie beamed back "I'm more than okay, that was a lot easier than I had anticipated. Like I said earlier, it feels a nice kind of weird." Mark leant forward again and kissed her back once more only this time he reached around and cupped her breasts as he slowly started to work his hips back and forth. Soon he found Connie responding by thrusting her own hips so that they were gaining their own momentum.

Mark slipped a hand down her stomach and came to rest on her pussy so that he could massage her clit between his fingers. This change prompted Connie to start bucking back more, seemingly groaning each time Mark was buried his dick in her butt. Eventually all the stimulation came to a head as Connie wailed loud enough for Rich to hear next door and her butt clamped down around his cock and her clitoris pulsed against his fingers.