Hooking up with your sexting buddies in real life

[RacyWilde]

*

Very slow updates

I’ve had an amazing sexual adventure a couple of months back, the first (and definitely not the last) one of it’s kind. I wanted to open some conversations on certain topics, and rather than creating separate threads for each topic, I thought it would be handy to have it all in one place. I guess this thread is about everything to do with hooking up with your sexting buddies (or strangers) in real life for some naughty fun. I’ll use my story as a guide to elicit conversation, and so I can ask questions in context. Please feel free to contribute, give advice or ask questions.

As a story has a structure - a beginning, middle and end - I’m planning for this thread to move quickly to get through my sexual adventure in good time.

And starting…… now!

 

[RacyWilde]

Finding a wedding date

*

As some might know, earlier this year I was desperately looking for Melbourne litsters to meet (aka hook up with) while I was in town. I had to go to a family wedding - ugh - and so by hell or high water, I was going to make the most of it. I was determined on having a fucking good time!

I was going to be in Melbourne for ten days and I was planning to fill up my schedule with as many people as possible to take the wedding blues away. And, I needed a wedding date! No way in hell was I going to sit there at the wedding while family came up to me one-by-one to complain about me leaving Oz and not returning for 12 years. I needed a buffer!

As most of my sane Aussie friends had already moved on, I needed to find someone new that could pass as an old friend. I tried Lit first, being mighty desperate, but I didn’t account for the lack of Melbournians on here. So, I actually started looking at escorts, thinking that would be the easiest - I pay him, he does what I say and I get a happy ending. Plus, my ex was going to be at the wedding with his new wife and I wanted to walk in confident, with a sexy adonis by my side. Yes, I’m childish like that. While searching the escort personals for Melbourne, that’s when I found out how much a pussy licking cost!

Thread link: http://forum.literotica.com/showthread.php?t=1378640

But all these escorts just seemed like regular guys anyway (with ripped abs), so I decided to try and find a guy myself. Surely some guy would see the fun in going on a blind date with me to a wedding - I hoped. I had 20 days to find someone.

I put an ad and pic up on Reddit, not expecting much. (You can still find it if you’re tricky….lol.) Holy Moly!!! I got hundreds of replies from around the world. People were willing to fly in from the UK, Germany, Denmark, and the US. *Blush* I certainly didn’t feel worth it, so I picked a local guy, "Waterboy" who promised me he could look a plausible 30 as he had a full beard. (Very much afterwards I found out he was only 23! Nearly twice my junior )

Waterboy and I chatted for maybe 5 minutes on Skype and I knew he was perfect for the job. That dude could talk!! OMG, I had daydreams of just sitting back at the wedding while he entertained the table! I was excited. But, we never quite had a conversation after that initial Skype chat, we just wrote comments here and there, back and forth, every few days. I thought it odd that he didn’t want to develop anything more with me or take it to sexting, or sharing pics of each other for that matter. In fact, we never actually saw each other’s face until the night we met.

There was one thing I was tossing up… my straight, vanilla wedding date had absolutely no idea how kinky or naughty I was planning to get with a handful of others while in Melbourne. Since he hadn’t shown any interest in getting sexual with me, I thought I would forget to mention it…lol.

Q.
I’ve found that I’m the type of girl who changes according to who I’m with. If I’m with a monogamous, vanilla guy, I work within his boundaries. When I’m with a sexed-up, kinky sissy I go all out. I’m a girl for everybody My question is - would you tell the monogamous, vanilla guy just how kinky you can be to push his boundaries? Or do you keep sexual experiences separate so they don’t influence your hook-up partner and let the experience naturally develop? (I have got myself in a tricky situation before when I’ve told and the person said, “So, why can you do that with him and not me?” Yikes!!)

 

[RickTango]

Q.
I’ve found that I’m the type of girl who changes according to who I’m with. If I’m with a monogamous, vanilla guy, I work within his boundaries. When I’m with a sexed-up, kinky sissy I go all out. I’m a girl for everybody My question is - would you tell the monogamous, vanilla guy just how kinky you can be to push his boundaries? Or do you keep sexual experiences separate so they don’t influence your hook-up partner and let the experience naturally develop? (I have got myself in a tricky situation before when I’ve told and the person said, “So, why can you do that with him and not me?” Yikes!!)

[/QUOTE]

I think honesty is the best policy. Maybe that vanilla monogamous guy/girl is just waiting for someone to explore his/her kinky fantasies with

 

[30bandits]

wish you were near me racy...

 

[RedSilk69]

Looking forward to Part 2!

And I agree: don't assume. They may appear and only have been vanilla, but that doesn't mean there aren't chocolate chips or swirls in there

 

[RickTango]

Looking forward to Part 2!

And I agree: don't assume. They may appear and only have been vanilla, but that doesn't mean there aren't chocolate chips or swirls in there

Or rocky road or pistachios ...

 

[midwestdude]

......

 

[RacyWilde]

Q.

I think honesty is the best policy. Maybe that vanilla monogamous guy/girl is just waiting for someone to explore his/her kinky fantasies with

wish you were near me racy...

Looking forward to Part 2!

And I agree: don't assume. They may appear and only have been vanilla, but that doesn't mean there aren't chocolate chips or swirls in there

Or rocky road or pistachios ...

Maybe you could bring it up casually? Ask him what he is looking for in his love life. If he has a clear plan or direction of marriage and kids, then he may not be interested. But if he doesn't really have a plan per say, he may just be a gentleman and not going into sexting right away. I mean believe it or not, there are some of us out there who don't want to sext immediately and try to respect thales ladies boundaries.
That being said, I always thought it would be SOO HOT to hook up with someone from lit, if even for a night to live out some fantasies.

Thanks for the replies!

You'll hear more about what happens between us in the story, but until then.... lol...

We are still in contact, like we were before we met - sporadically, and never seem to be on at the same time - but I can't seem to get him to sext with me...lol. Like even share pics, or write a realistic roleplay... even a couple of lines to leave for me so I can write back. (Believe me, I've initiated lots and have sent him lots of naughty pics, which he appreciates, but doesn't reciprocate.) He describes himself as a 'man whore' in RL...lol, so it's not like he is intimidated...lol. And it's not like he doesn't like me - we plan to meet up again next year when he travels to Europe. It's so frustrating...lol ;P

Usually, I would have given up on him a long time ago... but (as you'll see in the story) I can't...lol. This one is special! Haha!

 

[midwestdude]

......

 

[Kimleigh]

Can't wait to read more!

 

[naughtynjmale]

you should just

tell him what turns you on, what you like sexually.

Otherwise, if you dont you will never know if he is into also, but afraid to bring it up to you, or you will get frustrated .

 

[RacyWilde]

Can't wait to read more!

Ooo... there is sooo much more...lol.

tell him what turns you on, what you like sexually.

Otherwise, if you dont you will never know if he is into also, but afraid to bring it up to you, or you will get frustrated .

Yeah, usually I'm the type of girl that is way more kinky than most men. When I start chatting with someone I go straight to the top - I want pegging....lol. Then I have to negotiate and usually I only am allowed a finger.

 

[RacyWilde]

Equipment and Clothes

*

For the Melbourne trip I had so many things I wanted to do, but a lot of things were still up in the air because I needed to meet people in person first before agreeing to get kinky with them... and I was still gathering. I know that life happens and I supposed many would not be able to make it, I'll get stood up or we just wouldn't click. Still, I wanted to be prepared to have a really kinky time.

I was quite lucky because I have a friend in Melbourne who is just as kinky as me, and very handy with tools. He made me an adjustable spreader to use for my stay. I also gave him a shopping list of essential supplies to gather before my arrival. I didn't want to waste time searching for rubber gloves and bamboo sticks, etc, when I could be fucking. My list also included drop sheets and another doona, a body pen, wet wipes and stacks of condoms.... you get the gist...lol. There were some personal items I would need to get for myself, of course, such as a new strap-on, but just as long as the niggly stuff was out of the way... I was definitely planning to make the most out of Melbourne!

Then came the suitcase packing. Now, I know I went a little overboard, but I wanted to be prepared for anything. I didn't want to get into the middle of a session and kick myself for not brining the nipple clamps. I did have a sissy that I was keen to dress up too. He has a cheerleader fetish (him being one) so I added into my case micro skirts and bras, a set of pompoms... (He already had some of this stuff, but I'm pedantic in what I like - and maybe just a little bit of a control freak...lol) but I also included some of my vaudeville costumes - feather boas, nipple tassels, body jewellery and such. I love the classic expressionist and vintage Moulin Rogue style. I had a mind to make my sissy a burlesque harlequin for my own selfish pleasure.

https://static1.squarespace.com/static/5422133fe4b0149fd0c4be81/t/5750d1fcc6fc086bf677cdf1/1464634842153/?format=500w

I did ask on the threads here about how to humiliate a sissy. I'm not the humiliation or degrading kind (not for males, anyway) and I needed some extra scenarios planned that would give my sissy what he needed. Mind you, you may think some of the costumes would have been humiliating enough, but not so, as we both loved him dressing up.

Thread: http://forum.literotica.com/showthread.php?t=1402417

I got some great input from the thread, though at lot involved being outed in public. This didn't suit either of us as I would not have wanted to bump into a family member or he, his boss or colleagues. However, I did have another humiliation sissy who I was conversing with at the time. (I never depend on one showing up to the ball - I always invite three, four, five...lol. I am never sorry. ) He was eager for me to lead him around the city streets club crawling in a collar.

It was only a couple of days before I left for Melbourne when I got the idea for an intimate humiliation. I had named my sissy Tingeling. Even though he was only going to be mine for a week, we thought it appropriate he had a name, chosen be me. He had had several other cutsie names before by other Dommes but never one in another language. Tingeling is the Norwegian name for Tinkerbell, after the sound she makes when she talks or flies. I called him Ting for short (which he had no clue it meant 'thing' in Norwegian, as in 'object'. hehehe.) The name was quite fitting, and actually made me all giddy whenever I thought on it.


https://s-media-cache-ak0.pinimg.com/originals/95/6a/45/956a4580962ee25e2841645ca1946e79.jpg


I'm a Femdom who does not like talkers. If a sub/sissy cannot control themselves, the first thing they put on when they get to my hotel room is a gag or a blindfold - they will only ever have the privilege of looking at me or talking to me if it damn pleases me - they have to earn it. I don't get off on being treated like a school teacher - "Yes, Miss", "No, Miss", "Three bags full, Miss". So... to my point...lol... Since there was going to be no talking in our session by him, I decided to make his cock "ring" every time he made a move. I have this quaint little silver bell... perfect to tie on the end of a cock cage or just under the rim of a free cock. His yes' would be two rings. His no's only one.

A kik vid I sent to one of my confidants.... I was so excited when I found my bell!

http://racywilde.com/wp-content/uploads/2017/05/8b78f687-bb0f-4e2b-b000-05f2e9bc51e3.mp4


The night before my trip, I laid out all my things. Among the black velvet and leather, animal prints and various shades of red lace were some of my more peculiar items such as top hat, venetian mask and faux fur leopard leg warmers. I took a picture and sent it to some of my Kik buddies... Somehow they all noticed the vintage gas mask sitting in among the fine fabrics. (Ah, more to tell on that later!) With some of my BDSM equipment and sex toys, my suitcase was so packed it was hard to fit my street clothes in...lol.

http://i.imgur.com/oF3Cm7M.jpg

Even though I wasn't planning on wearing everything... I wanted to be able to dress according to my mood. Sometimes I want to be a sadistic cheerleader, other times a Red Woman, or even a Jessica Rabbit - it all depends of the wind. Though, I leave nothing to chance. To arrange such a successful sex fest with all the right looks, partners and tools, you have to be highly organised. There are elements that are beyond your control where you have to improvise, of course, but by controlling all else, making sure all details are crafted for maximum effect, a dominant woman will be at her best.

https://s-media-cache-ak0.pinimg.com/736x/5d/d2/97/5dd2977c728b0a71a4669d66b3077e73.jpg


Q.
When you go away for a little kinky fun, do you have certain toys you always take with you? Certain lingerie or clothes? Do you organise or improvise your kinky fun?

 

[Lookin2880]

I've never had the chance to meet up with any of my sexting buddies. Part of me really wants to, but part of me worries that it won't be as good as what we pretend to have.

Maybe it's just me......but I can dream for a good time. Who knows, maybe someone can prove me wrong.

 

[spanky5147]

sadly, never had the chance. well, there is one that is on here and lives about 45 minutes away but refuses to meet anyone in person. my loss,

 

[RacyWilde]

I've never had the chance to meet up with any of my sexting buddies. Part of me really wants to, but part of me worries that it won't be as good as what we pretend to have.

Maybe it's just me......but I can dream for a good time. Who knows, maybe someone can prove me wrong.

Yes, that is the problem with fantasy - it gives you unrealistic expectations. If you really want to meet a particular person in real life you have to drop expectations and go with the flow. A good way to prep is by having as much skype - vocal and visual - time as possible. That way the person becomes real and you won't have your fantasy of them to measure them against when you meet.

sadly, never had the chance. well, there is one that is on here and lives about 45 minutes away but refuses to meet anyone in person. my loss,

Oooo! That's hard being so close. I make it a rule never to fuck in my own pool. I prefer to travel out of country to meet up with people. It means there is no pressure of them falling into your life. But, it does make it really hard when you meet someone you want in your life. I have experience at both ends. I love being able to leave a country and say to my fuck buddies 'goodbye, it was fantastic' but it's hard on me with my lovers - you feel loss and grateful at the same time. Loss that you don't exactly know when you'll see them again, but grateful that you are both willing to overcome that challenge together.

 

[13Fantasies]

Thanks for the replies!

You'll hear more about what happens between us in the story, but until then.... lol...

We are still in contact, like we were before we met - sporadically, and never seem to be on at the same time - but I can't seem to get him to sext with me...lol. Like even share pics, or write a realistic roleplay... even a couple of lines to leave for me so I can write back. (Believe me, I've initiated lots and have sent him lots of naughty pics, which he appreciates, but doesn't reciprocate.) He describes himself as a 'man whore' in RL...lol, so it's not like he is intimidated...lol. And it's not like he doesn't like me - we plan to meet up again next year when he travels to Europe. It's so frustrating...lol ;P

Usually, I would have given up on him a long time ago... but (as you'll see in the story) I can't...lol. This one is special! Haha!

I'm more interested in how I become part of this sexting with Racy club.

 

[spanky5147]

Oooo! That's hard being so close. I make it a rule never to fuck in my own pool. I prefer to travel out of country to meet up with people. It means there is no pressure of them falling into your life. But, it does make it really hard when you meet someone you want in your life. I have experience at both ends. I love being able to leave a country and say to my fuck buddies 'goodbye, it was fantastic' but it's hard on me with my lovers - you feel loss and grateful at the same time. Loss that you don't exactly know when you'll see them again, but grateful that you are both willing to overcome that challenge together.[/QUOTE]

Yeah, I understand her not wanting to meet in rl. My loss. Another of my life long regrets is not taking full advantage of opportunities when they presented themselves. My wife did, many times. I chose not to. Anyway, hopefully there is still time for me to take advantage of future opportunities.

Maybe I should travel more, hmmmm

 

[LordofChocolateSauce]

*

As some might know, earlier this year I was desperately looking for Melbourne litsters to meet (aka hook up with) while I was in town. I had to go to a family wedding - ugh - and so by hell or high water, I was going to make the most of it. I was determined on having a fucking good time!

gosh i arrived at the party too late