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A most unexpected encounter (neglectedmom x Elembivos)

'That was so hot when you squirted, at that moment I really thought to drop my pants and to take you right there and then. And the waitress, I think that she had a thing for you with how she looked at you. But no, I don't know her. It had been some time since I was at the restaurant, most of the time Dan and I meet at his club.'

Grabbing his phone, he smirked as he saw the text. 'He asks if I went home alone?' Turning his head to Emma, he looked at her for a moment as an idea popped up in his mind while his hand stroked further along her thigh, getting closer to her mound. 'What do you say, should we answer him?'
 
‘She was a cutie’ Emma said regarding the waitress and quickly pivoted to the text Mr. Cross received from Dan

‘It depends, I assume you know and trust him very well? If so I don’t mind you sharing with him that you didn’t go home alone’
 
Leaning over to Emma, he kissed her softly before he leaned against the bed again. 'I do trust him, very much. He knows me probably better than most people do.'

Tapping on his phone, he clicked on the reply button but before he texted, he looked at Emma again. 'Dan is the guy that I had the threesomes with in the past. I trust him.'

Moving his hand in between her legs, he began to type and read it to Emma before he send it. 'She is right next to me right now and I'm telling her about what we've been up to in the past. That should answer your question.'
 
‘Wait, really? You guys have done this together before? How many times? Is he big too? How did you know the women? I have so many questions now’ Emma asked excitedly

This was a bit of a surprise to her and was curious how much he would share and be completely honest about
 
Matt liked her reaction and how curious she was. It felt not only right but really good to finally be able to talk with someone openly about his desires and experiences.

'We did that with two different woman so far.' His hand wandered on along her mound to her labia, Matt wanted ... needed to know if this conversation affected her as he thought it would.

'The first time was with his ex girlfriend. Dan is big too, not quite as big as me but still very big. She always teased me that it was impossible to have a bigger one than him. One day then, Dan and I decided to proof her wrong. The second time was with someone he had hooked up with. She had always fantasized about a threesome just like you did. We made that fantasy come true.'

Parting her labia with his fingers, he continued. 'I would bet that when he saw you yesterday, that he thought about to sit down opposite of you. I saw the way he looked at you when he introduced himself to you.'
 
‘Oh wow’ Emma said, things were getting more involved and interesting as time moves on

‘Well in fairness I would be shocked if anyone was bigger than you so I didn’t expect him to THAT big’ she thought about her next words for a moment

‘I wonder if his waitress has ever been involved with him? They both were very, very nice looking’
 
The more that they talked, the more began Matt to feel aroused. Emma's open interest in the waitress as well as in Dan and his past only fueled this arousal further.

'I don't know for sure. He is currently single and I could imagine him and her being involved. She would be his type. So that's certainly possible. Did you like the waitress?' Thinking for a moment, another thought crossed his mind. 'Have you even been with another woman before?'

His phone vibrated again and when Matt checked the text, he smiled again. 'Dan asks me to tell you that it was a pleasure to meet you yesterday and that he hopes to see you again.'
 
‘Yes, I have been with girls before’ Emma said and was not going to tell him his daughter was one of them

‘Tell him I said thank you again for dinner and that it was very nice meeting him and his staff as well’

Placing her hand on top of his and showing him how to stroke her clit…
 
Relaxing his hand, he let her show him how she liked it to tease and stroke her clit before he took back the control and moved his finger, teasing her before he stroked right along her nub.

'So if I should see her again and she asks me for your number, you wouldn't be opposed to me giving it to her?'

Grabbing his phone, he began to type his reply to Dan while the finger of his other hand never stopped stroking along her clit.

'She says that she enjoyed the dinner and to meet you as well as your staff.'

Turning his face to her, he looked at her. 'Two guys that are huge at once, does that thought scare you or excite you?'
 
Moaning ‘mm hmmm’ and nodding her head saying it would be ok to give her her number

Watching him type the reply to Dan and responding his question

‘A bit of both to be completely honest, I won’t even know what to do in a situation like that, I would need lots of direction
 
Teasing her clit some more, It was almost as if he was a young guy again who had touched a woman for the first time and then couldn't get enough of it. But unlike a young guy has he developed patience and enjoyed the teasing game just as much as sex itself.

'You don't need to know what to do when you are with two guys, especially not when the guys have been involved in a threesome before. Just do what feels right or let the guys take the lead.'

His finger moved on from her clit along her labia. 'What you need to know is what your limits are. What are you okay with and what not? That needs to be talked about beforehand. Let's take me and Dan for example, we both are sexually not interested in each other. So our full attention would be on you all the time. Would you like to experience two dicks at once, for example one in your mouth and the other buried in your pussy or do you want them one after another? Or would you be comfortable if one guy goes down on you after the other guy came inside of you? You don't need to answer that right now but it's something you should think about. I would love to explore that with you but want you to think about your limits beforehand and talk to me about them.'

Lifting his flat hand a bit, he tapped on her labia twice, then parted her labia with one finger, teasing her entrance before he moved with his finger along her inner thigh.

'One rule that I have is that anyone involved can always say stop and the others will accept that. No one asks why or tries to push on, a stop means stop. If the one who says stop wants to talk about that, okay but otherwise it will only be accepted and everything stops.'
 
Moaning as he rubbed her clit and asked her these questions she was so turned on by the conversation

‘I want to experience it all Mr. Cross. Two dicks at a time would be amazing and I’d be open to even trying double penetration though you both might be too big for me there. And I’m glad you two don’t play with each other, that would be a huge turn off for me’
 
Stroking with his finger further along her thigh, he grabbed it and pushed it aside a bit before pulling it up so that her legs were spread and bend, opening her up further to him.

'I don't have anything against bi or gay guys but it's just not mine and I can say for sure that Dan thinks the same. Double penetration though ... that is possible even with his and mine size, we tried that out. Though ... it would probably be very overwhelming for you to feel your pussy and ass both stretched out ... a thought that I like.'

His finger returned to her labia, teasing her before he moved his hand further until his finger stroked around her backside, massaging her puckered star softly. 'I know that you've never tried an anal plug before. Have you made any experiences with anal sex so far?'
 
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‘No I don’t have any anal experience but I want to try it and I can’t think of a better way than with you and Dan’ she replied excitedly

‘My pussy will never be the same after yesterday Mr. Cross, I am sure you’ve ruined several women that way’ she said as she reached over and lightly ran a finger over his length. He was soft as they spoke, his massive cock resting between his legs, over his fat balls that were bunched up on the bed beneath and his heavy cocks length folded over them and laying on the bed as well
 
Several thoughts crossed his mind at her response while he hummed softly, showing her that he liked it that she touched his length. Yes, he had threesomes with Dan before but never mentioned to Emma that he would have a threesome with her and Dan. Sure, that thought had crossed his mind but he never said it out loud. Taking how she spoke about it into consideration, it seemed that she not only was fine with the thought but even enjoyed it. She seemed to like Dan .. ... good.

'You will try it but only with me first. Your first time anal sex is something special and I want that all to myself.' He didn't mind to share his girl but there were some things where he was egoistical and taking her anal virginity was one of them. 'Good thing is that we have all the time that we want. We can have as many threesomes as we want and explore everything that you want.'

Stretching out his hand, he massaged her tight muscle on her backside with one finger while his thumb returned to her clit, stroking along it in the way that she had showed him earlier. At the same time he looked down on himself, smiling at the sight of her finger being so small when next to his length.
 
‘Ok Mr. Cross’ she said as she pressed her hips down so as to push herself on his finger with a bit more pressure

‘Have women been able to take this ‘there’ before?’ she asked as she looked down at his huge cock. She was hoping other women have either not been able to or wouldn’t try it at all
 
When she pushed her hips down, he pulled his finger along slowly, making sure that he wouldn't slip into her tight hole but keeping the pressure on her puckered star.

'Most woman are not interested in general in anal play, those that remain are scared of my size. There was only one woman that wanted to try it and could handle my size in her ass and that was a long time ago.' Placing his free hand on her cheek, he turned her face to him and kissed her deeply for a long moment before he broke the kiss and pulled both hands back.

Reaching out to the nightstand, he grabbed some lube that was in the drawer of the nightstand and got it next to him. 'I'm a bit surprised that you are willed to try but in the best way possible. Just know that if your pussy won't be the same after yesterday, it will be much more intense on your ass.' Pulling her in for another kiss, he looked at her for a moment. 'And much much more with one huge dick in your pussy and another in your tight backside.' Opening up the lube bottle, he kissed Emma once more.
 
‘I am willing to do anything for you Mr. Cross, all you have to do is ask or say the words. I have wanted you for so long that I am not going to let any chance go to waste’ she said as she returned his kiss before he took the lubricating gel out of his drawer

As he did she rolled over on to her stomach and looked back over her shoulder at him ‘I want this Mr. Cross’
 
Licking over his lips as she turned around and said those words to him, he couldn't deny that such offer did something to him.

'Anything is a big word and I want you to know that if you offer me anything, that I will take exactly that from you.'

Getting up and on his knees, he moved closer to where her face is, placing his still soft length so that his tip was right in front of her face while he looked along her body. 'Spread your legs wide for me and while you do that, take my dick in your hand, I want you to kiss it and lick it.'
 
On her stomach still she spread her legs for him

As she lifted his cock up off of the bed, looking up at him ‘Yes, Mr. Cross’ she said before she kissed his soft head and licked around the tip slowly
 
Nodding slowly at her, he groaned softly when she began to kiss the tip of his dick. 'Good girl, you've got no idea how much it turns me on when you hand all control over to me.'

Putting some of the lube on his thumb, he placed it on her puckered star and began to massage it in. 'The thing with anal sex is that most woman can't get off from anal sex alone. It can enhance the pleasure but only very few can cum from it.' Stretching out his hand, he moved his finger to her clit, stroking it. 'That's why this gorgeous nub of yours as well as your pussy needs some attention as well while I begin to prepare yourself for me.'

Teasing and stroking her clit, he moaned when he felt her licking his dick but didn't reward her with getting hard already yet. Instead he focused on her breathing and when he felt that he had teased her clit enough, he began to push his thumb with some more pressure against her puckered star. 'Breathe deeply and push against it.'
 
Moaning as he pressed her area between her butt and kissing his still soft yet huge head her legs spread even wider

‘I have a feeling I could cum just from being played with there’ she said with a cute smile
 
'You think so?' Smirking, he pulled his finger away from her clit and focused more on her puckered start, starting to move his thumb back and forth slowly after he gave her a moment to get used to the feeling of the thumb stretching you out.

'Damn you are so sexy, all I can think about in this moment is to get hard in your mouth and to finish inside of your ass. Do you think that you can take some more?'
 
‘Mmm hmmm’ she moaned as she let his cock fall out of her mouth to focus on this new pleasure she was experiencing

She was surprised how good it felt and how her body was reacting to it, feeling so connected to him probably helped but still it felt amazing to her
 
Her reaction to his touch made Matt wonder if she could actually be really one of those few that could cum from anal pleasure alone?

As his dick popped out of her mouth, he felt it twitch due to the possibility of her enjoying anal sex. Changing his position, he placed himself in between her legs and added some more lube to her butthole before he began to place two fingers on it and began to slowly work them in. 'Continue to breath deeply and tell me if it ever gets too much.' Starting slowly, he began to thrust with into her with two of his fingers.
 
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