tagTransgender & CrossdressersCraigslist Adventures 01

Craigslist Adventures 01


Disclaimer: this is a series of stories I started a few years ago, I now realize Craigslist personals are dead but I wanted to write about all my crazy adventures to re-live them and share with everyone. They are my true real life encounters from the past, as well as a few from the present that happened before the service shut down.

I hope you enjoy, it will be a rather long series, all your comments, feedback, and questions are always welcome. I try to respond to all.

Again these are all 100% true, every time I would have an encounter I would write notes of everything that happened, what I wore etc. because I knew I wanted to publish them one day. I sure have had a lot of crazy adventures.

Without further hesitation...


I've been searching through craigslist a lot lately looking at the m4t and m4m and mm4m and mf4t pages and have had quite a few conversations that I weren't sure if they would actually turn into a rendezvous or not but recently two of them did so I thought I would start to write about them, and they continued happening to me so I have a lot of stories to tell. Of course there were also a lot of times peopled flaked out and I was left fully dressed up super sexy with no one to entertain.

I used to have everything I needed to completely dress up including nice big breast forms. Then I lost everything so recently I have been getting all new panties, bras, new heels, stockings, some dresses and skirts and tops. I haven't bought new breast forms and really wanted the expensive ones that look so natural, but didn't want to pay for them so I thought it would be fun to post that I needed a man to buy me new breast forms and I would do naughty things to earn them. No idea where this might lead.

I got a lot of emails and chatted with a lot of guys but ended up talking to this one guy who owned a lake house near me the most.

We must have sent around 100 emails back and forth, he told me I could come over and sneak into his bathroom and get all dressed up and put my makeup on, then come out to find him waiting for me. That's a big fantasy of mine to be able to do that.

So we went back and forth for a little while, I sent him lots of pics of me dressed, but never had the chance to set anything up. Finally we were chatting one day and he asked if I could just come over later that night. I said yes that I would just get ready and do my makeup at my house and then come over.

Later that night after a full bottle of wine, I was wearing a pair of white satin and lace panties with a pair of white scallop lace top thigh high stockings and watching porn unsure if I would actually go over there. The wine was helping me though be a little more willing perhaps. I walked downstairs and opened another bottle and poured a glass, went back to the computer and saw he had emailed me asking when I wanted to come over.

It was currently just before midnight and he mentioned meeting between 12 and 1 am would work best.

To be honest, I was rather tipsy, thinking that I might actually do this, I might go over to his place, I'll get ready, I'll put on all my makeup and then decide. So I started with a heavy foundation and concealer, heavy black eyeliner, finished up with mascara and smokey eye makeup, literally just making me as slutty looking as possible. Wow, I feel I succeeded and looked hot and slutty. I added some hot pink lip stick and sparkly lip gloss.

That's the hard part out of the way, I put on my wig, matching white 36A satin push-up bra, and choose a hot pink long sleeve dress, super tight, that went just past mid thigh, the sleeves and most of the back were all lace. Such a sexy and feminine dress.

I finish off my outfit with glittery silver 4" high heel stilettos, and some jewelry, a wide choker, and a bunch of bangles on each wrist.

I do impress myself with how sexy I look. I take some pictures in the mirror. I sent them to him and he replied with a wow, and how hot I looked, and to please come over!!

Oh my God I'm actually doing this, I'm super tipsy and I grab my keys and walk downstairs, and out the front door, into the night air, my stomach is so nervous, but at least it's a short walk to my truck, I get in.

The drive seems to take forever. I'm so nervous, I think about turning back, but instead I continue on and suddenly I'm turning into the driveway. The front porch light is on, up two flights of stairs to get to the front door. Again I think about just leaving, but I see the light go off then back on again, so I know he sees me.

My 4 inch heels hit the driveway, I straighten up, and pull my skirt down to cover my stocking tops and nervously ascend the stairwell to the top porch and doorway.

He opens the door, gazes at me in awe, telling me I'm way more gorgeous in person, he hugs me, rubbing his hands up and down my back, then inching down my ass cheeks, caressing my firm ass, lightly grazing his lips against my neck, whispering how good I feel.

He is completely naked, pulling me into the house and closing the door behind me. He continues caressing me slowly, strongly squeezing my ass and rubbing his hands up and down my back and ass cheeks.

He grabs my hand and leads me into the next room where there is a couch in front of a huge plate glass window showing a clear view to the neighbors house and what looks like a living room. All the lights are out so I dismiss it.

His cock was semi-hard, I felt it when he was embracing and caressing me. I sit down on the couch in front of him with his cock directly in front of my face. I look at him, he says to suck his cock please.

I take it into my mouth, slowly, lips press firmly against his member, letting my tongue caress the delicate underside of his cock. He's almost instantaneously hard, pushing at the back of my throat, but not yet. I slowly pull back out then do it again, only going back down half of his shaft, he wants me to take the whole thing, but I will tease him first and make him beg for it.

So I slowly suck him back and forth, in and out of my mouth. His cock is very average in size, not very long or fat, so after just sucking on part of his dick, I look up at him making eye contact and I take him all the way inside my mouth, slightly into my throat with my nose up against his pubes I breath through my nose and try not to choke

He blurts out "oh my God!"

I pull all the way out and do it again. He's probably getting close to coming, I can feel it. I've been sucking on him like this for almost 10 minutes so I wrap my lips tightly around his cock and slurp up and down his entire shaft more quickly.

Again he blurts out, "oh fuck, oh fuck!"

He grabs the back of my head and with that spews his cum into my mouth, I pull away and swallow it all.

Mmmmm. Yummmm.

He walks me out, hugs me again and we say goodbye. I gingerly walk back down the stairs and to my truck to drive home.

I'm so excited for what just happened. I get home and go online to email him. Just a simple message, "I loved your cock in my mouth."

My late night booty call sees I'm online and messages me to see if he could come over. I tell him not tonight, tomorrow night though. More on him later.

I take off my dress and heels and go to sleep.

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by Anonymous

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by Brian7005/22/18


Sexy fun quick bj, thanks. Xoxo, Brie

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by Failedscout05/17/18

Thank You

I for one am really going to miss CL. It was a great place where you could find like minded people for any fantasy, fetish or kink. I am thankful that it was out there for the time that it was and thatmore...

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