More Ramblings

<NikkijMadison> i crashed

<WannaBeSissy> No worries, glad you came back

<NikkijMadison> shock wave crashed

<WannaBeSissy> Ahhhh, yeah, it locked up my browser a little bit ago.

<NikkijMadison> why does that happen

<WannaBeSissy> Because CM is lazy & still using all the same stuff as they did shortly after the site opened as I understand it.

<WannaBeSissy> They treat it as the Craiglist of BDSM personals. It works, it's just not pretty, and has it's issues.

<NikkijMadison> okay

<NikkijMadison> is that why some people cant use chat

<WannaBeSissy> Stupid people largely, and iPhone, iPad, Android users.

<NikkijMadison> ic

<WannaBeSissy> Only reason it won't work on a PC is because people were stupid, and have a virus that has screwed up their web-browser.

<NikkijMadison> ic

<NikkijMadison> so will Thursday night girl suck you tonight

<WannaBeSissy> She does usually. She just needs to work on not using her teeth some. Why?

<NikkijMadison> sex is always on my mind

<WannaBeSissy> lol

<NikkijMadison> she needs more practice

<NikkijMadison> wow

<NikkijMadison> you have sucked clitty right

<WannaBeSissy> Never

<NikkijMadison> would you

<WannaBeSissy> Never had clitty penetrate me; been blown by a tgirl however.

<NikkijMadison> you do her booty

<WannaBeSissy> I'd let a tgirl have her way with me at this point.

<NikkijMadison> so never sucked cock either

<WannaBeSissy> Never

<NikkijMadison> but you would suck me

<WannaBeSissy> Didn't do her booty. She was my introduction to anal toys when she blew me.

<WannaBeSissy> I would

<NikkijMadison> yum

<NikkijMadison> and your SF GF now?

<WannaBeSissy> Now I would suck or let her fuck me.

<NikkijMadison> cool

<WannaBeSissy> Back then I was like 21, and extremely skiddish.

<NikkijMadison> is she good looking bitch

<NikkijMadison> i had my first bj at 17

<WannaBeSissy> Let me find a picture...I think she looks pretty good. Has some work to do, but she had her jaw reconstructed to look correct.

<NikkijMadison> stroked my first cock on someone else at 12

<NikkijMadison> been dressing since teens

<WannaBeSissy> lol, I was a good mormon kid. Left me seriously fucked up sexually. Didn't even have a blowjob till 21. Finally had sex at 24.

<NikkijMadison> sorry about that

<NikkijMadison> i would come home from school at 12 and go to friend’s house on the way.... the three of us would stroke our dickies

<NikkijMadison> ok

<NikkijMadison> we then went to stroking each other

<NikkijMadison> i would fuck her often

<NikkijMadison> jennifer across the street would come over too

<NikkijMadison> she would watch us

<WannaBeSissy> Yeah, kinda mad I was so skiddish back then. She comes to town periodically & we've teased each other mercilessly. She knows next time I'm finally game.

<NikkijMadison> show us her panties.... never saw her naked pussy then

<NikkijMadison> cool

<NikkijMadison> until a high school reunion

<WannaBeSissy> Hah, damn cock tease women. I just tie them up & take their panties.

<NikkijMadison> i was 12

<WannaBeSissy> lol, well yeah

<WannaBeSissy> Wasn't till 16 my body finally demanded attention more attention than my nerd activities.

<NikkijMadison> i ran into her at a dance club in dc about 10 years ago

<WannaBeSissy> Hopefully you did her.

<NikkijMadison> i recognized her

<NikkijMadison> she didn't me until i told her my name

<WannaBeSissy> And?

<WannaBeSissy> lol

<NikkijMadison> i was enfemme of course

<NikkijMadison> she sucked her off

<WannaBeSissy> Nice

<NikkijMadison> in the backseat of her car

<NikkijMadison> saw her off and on for about year

<WannaBeSissy> Hot

<WannaBeSissy> Love fucking or sucking in a car. Always feel like I'm in High School doing that.

<NikkijMadison> she was fascinated by me especially since i went by jennifer at the time

<NikkijMadison> i loved the name and she was jennifer not a jennie

<NikkijMadison> so and i will always remember that

<WannaBeSissy> Yeah, that's what I'm finding out s most women are fascinated by it, and want to fuck even more.

<NikkijMadison> she got married and i havent seen her since

<NikkijMadison> she love the enfemme me

<WannaBeSissy> Nice

<WannaBeSissy> I rather like the tgirl you.

<NikkijMadison> i alsoo met robbie about five years ago... one of the guys i stroked at 12

<NikkijMadison> he was across the bar at a local restaurant in annapolis

<NikkijMadison> with a girl

<WannaBeSissy> nice

<NikkijMadison> i sent them drinks

<NikkijMadison> then walked over to introduce my self

<NikkijMadison> i said you know me as Jimmy

<NikkijMadison> He almost fell off the bar stool

<WannaBeSissy> hah

<WannaBeSissy> I can't wait to do that to a few people I know. Keeping it extremely under the table so if I do come out about it, I can choose when & how to fuck with certain friends.

<NikkijMadison> its cool

<WannaBeSissy> So what else happened?

<NikkijMadison> i have dressed enfemme since about 23 almost every weekend and since about 28 daily

<NikkijMadison> with robbie

<WannaBeSissy> Yeah

<NikkijMadison> he and mindi fuck me now

<WannaBeSissy> That's good, I thought so.

<NikkijMadison> he invited me to a mini reunion with about 8 folks from high school

<NikkijMadison> we met at another bar close by

<NikkijMadison> i was the hit of the reunion

<WannaBeSissy> Cool

<NikkijMadison> stevie the other guy who I stroked with at 12was there

<NikkijMadison> he couldn't take his hands off me

<WannaBeSissy> That's fantastic

<NikkijMadison> when i was still in annapolis he would come by and suck me off on a daily basis

<NikkijMadison> he's never fucked me

<NikkijMadison> i think he is jealous of me

<WannaBeSissy> lol

<NikkijMadison> hes in a vanilla relationship and secretly wants to be me

<NikkijMadison> robbie was funny too

<WannaBeSissy> Yeah I will never understand that. I tried to do vanilla for a long time, and I still don't get why people do that.

<NikkijMadison> he told mindi about our stroking deals but that we had never sucked

<NikkijMadison> but i said we did

<WannaBeSissy> Yeah, I'm of the mindset I'll do anything with women & tgirls. Straight up men I'm thinking escort or pro dome only.

<NikkijMadison> i met him at a fraternity party after football game asked him about the girl who sucked him off in the parking lot near the stadium

<NikkijMadison> he did and i raised my hand

<NikkijMadison> that was me

<WannaBeSissy> Nice

<NikkijMadison> i just love sucking cock

<WannaBeSissy> I'm sure I'll freak out the first few times with a tgirl, but will go through with it. Would prefer to honestly be tied & raped the first few times with a tgirl

<NikkijMadison> will sf gf do that

<WannaBeSissy> Thinking I'll enjoy sucking tgirl cock.

<WannaBeSissy> I've taught her how to tie & got her to stop being submissive only. She's a switch now so it's highly likely.

<NikkijMadison> its awesome

<WannaBeSissy> errr tgirl clitty

<WannaBeSissy> Keep having to correct myself.

<NikkijMadison> have you said she or her with anyone yet

<NikkijMadison> used

<WannaBeSissy> Never done a 3 some.

<NikkijMadison> its hot

<WannaBeSissy> I bet

<NikkijMadison> done many

<NikkijMadison> like doing couples where hubby is the cuck

<WannaBeSissy> Have a standing offer from a tgirl friend that was nominated for tgirl of the year for the AVNs in 2011. She & a GG friend want to eiffel tower me.

<NikkijMadison> awesome

<NikkijMadison> her name

<WannaBeSissy> Skiddish when the offer was made, but gonna take her up on it when she comes back to town.

<WannaBeSissy> I forget her real name, but the porn name is Brittany.

<WannaBeSissy> Shes absolutely stunning.

<WannaBeSissy> Never even had a strapon used on me. Just haven't had the timing right, but wanna do it.

<NikkijMadison> its awesome

<NikkijMadison> i get hit on by lots of married too

<WannaBeSissy> Shooting for hitting yours & her level. Would be disgusted with myself if I ended up looking like these horrible drag queens. Don't get me wrong though, I LOVE seeing a good drag show.

<NikkijMadison> lol

<WannaBeSissy> Just don't wanna end up a drag queen.

<NikkijMadison> me neither

<NikkijMadison> but i will be a old bitch one day

<WannaBeSissy> oh?

<WannaBeSissy> Would assume you would be more for keeping things going, and doing surgery to keep things up.

<NikkijMadison> i will

<NikkijMadison> i hope i look as good as diane sawyer at 70

<WannaBeSissy> lol right?

<NikkijMadison> lol

<NikkijMadison> i never asked but are you dressed today

<WannaBeSissy> In panties currently. Still haven't changed from last night since I got home. Been working, and need to shower before I do anything clothing wise.

<NikkijMadison> yes you do

<NikkijMadison> just in panties

<WannaBeSissy> Tied a friend up, she tied me up, we played with nipple suckers, sucked, fucked, and slept at her place.

<WannaBeSissy> Also found out a 41 or 42 sized corset will work for me. About stole her corset due to how it looked on me.

<NikkijMadison> cool

<NikkijMadison> what did she think of you enfemme

<WannaBeSissy> She's bi; She was all for it. Wants me to come model what I have bought for her next time I'm over.

<NikkijMadison> cool

<NikkijMadison> you should

<WannaBeSissy> That's the plan. She's super submissive but wanting to flex her dom side. Told her if she wants me to model she's gonna have to flex the dom side since I'm unable to dom yet femme.

<NikkijMadison> i found that i prefer to be sub

<WannaBeSissy> As a guy I prefer to dom. Thinking maybe when the panties go on I go submissive. Wanna try to flex the dom over on the femme side a bit however.

<WannaBeSissy> But I'm so clueless still I dunno how to dom as femme.

<NikkijMadison> i can Domme cucks and some other tgirls

<NikkijMadison> but i enjoy being the submissive

<WannaBeSissy> lol, that's good. I'd love to sub under Nikkij. Could certainly dom her as a guy if she wanted too.

<WannaBeSissy> Errr sub in person. Already am subbing this way IMO

<NikkijMadison> i dont consider me domming you

<NikkijMadison> just giving a girl assistance

<NikkijMadison> although i could leash and cage you

<WannaBeSissy> Well I'm being submissive at the minimum. Appreciate any guidance Nikkij gives me

<WannaBeSissy> Would love that.

<NikkijMadison> have you worn a collar and leash

<WannaBeSissy> I've worn collars a few times, and been lead around on a leash before.

<WannaBeSissy> But haven't done either extensively. Done very little on the submissive side since I've almost always domed.

<WannaBeSissy> Have a crap ton of toys due to doming. Always nice IMO when a submissive has their own toys.

<NikkijMadison> yes i do

<NikkijMadison> did you enjoy the leash and collar on you

<WannaBeSissy> Immensely

<WannaBeSissy> I think I'm honestly a fan of pet play so collars & cages are a hell yes.

<NikkijMadison> have you played doggie

<WannaBeSissy> never done pet play as a pet

<NikkijMadison> its cool

<NikkijMadison> also had horse tail as butt plug

<WannaBeSissy> Think in the next few weeks I'm going to construct a kind bed with a cage & toy storage below. Been wanting to do it for ages, but a friend finally made one.

<NikkijMadison> cool

<WannaBeSissy> Very interested in pony play also. Just a large amount of money to get it going right.

<WannaBeSissy> Very little I'm not wanting to do or have done & will do again.

<WannaBeSissy> Blood, scat & animals, and public spaces kink doesn't belong are my main limits.

<NikkijMadison> what bondage limits do you have

<NikkijMadison> not into public then

<WannaBeSissy> Into public in a kink play space. Not into involving people who didn't consent to being around kink however.

<NikkijMadison> this past summer i served a pool party in the tail, fishnet catsuit, black lacy bra and g string

<WannaBeSissy> Now if the kink was in public, but no one who isn't part of it knew, that's fine.

<NikkijMadison> serve party with gg dressed the same

<WannaBeSissy> Um, none? I love all forms of bondage.

<WannaBeSissy> That kina thing would be ok with me so long as no one would freak out.

<NikkijMadison> not into ropes, or cbt

<NikkijMadison> will do cuffs, gags, cuffs, collars, cages, animal cages

<NikkijMadison> have done golden but not a fav