About PlayfulAshley


Hi, Just a laid back CD here. I love reading the stories on here and have enjoyed writing a couple myself.

I'd love to hear from some others into cross-dressing as well. If you want to friend me, please at least put some effort into your own profile first.

Also, I do have pics posted, but they are set to only allow my friends to see them.

Let the games begin....

Relationship Status:
It's all good as long as we're having fun
Favorite Books:
Not really a big book reader, I typically stick more to magazines and articles.
Favorite Authors:
Check out who I'm following below...
Favorite Movies:
Comedy, action and adventure, drama, and of course PORN, lol!!


Date Joined:
20 Mar 2011
Last Visit:
02 May 2018
Page Viewed:
39,458 times
Days in Chat:
Days on Site:
Forum Posts:

Latest Forum Posts More forum posts »

Topic: sex during period
Posted: 21 Apr 2014 13:18

Love it. I feel it to be very intimate. I dont find it any more gross than cum. I mean it happens, whatever, a womans fertility plays a huge role in her sensuality and her period is just another part of that. That being said.... my wife is grossed out by it, lol! Eventually I get her hot enough where she gives in. I even give her oral when she allows, doesnt bother me in the slightest.

Topic: mutual masturbation
Posted: 21 Apr 2014 12:55

Really hot for 2 reasons... 1- it like live porn, lol, and 2- you learn a lot if you pay attention, your partner will demonstrate how they like to be touched.

Topic: Why swallow?
Posted: 21 Apr 2014 12:40

Its hot based on you showing you'll do anything to please and it is a very intimate thing. Also it feels better to finish with a nice warm mouth wrapped around you.

Topic: Best tips when giving a guy head?
Posted: 21 Apr 2014 12:37

Number one is confidence, own it and desire it. Next I'd say start with his balls, they are really sensative and a hot sloppy tongue bath feels incredible. Just a little bit of teasing licking on the head and shaft. Then when you suck, don't cheat and use your hand, turn your mouth into a hot wet hungry pussy. That cock should be sliding in and out of your mouth like a wet pussy. After a while ask him were he wants to cum and accept his decision as if it were yours. If he turns the tables on you DO NOT THINK ABOUT IT OR BE INDECISIVE, tell him wantonly where you want it like you have never wanted anything so bad in your life.

Topic: high heels
Posted: 21 Apr 2014 12:29

As a bisexual crossdresser I am going to answer yes from both perspectives, lol! Heels are sexy, I mean as long as you have sexy heels.... there are some short or unflattering heels out there.

Topic: Porn
Posted: 21 Apr 2014 12:25

I find myself using youjizz.com mostly

Topic: snowballing or cum kissing
Posted: 21 Apr 2014 12:21

I've managed to kiss my wife a couple times with cum on her lips. I love it, she's weirded out by it:( I'd LOVE to snowball with her, but she refuses...

Topic: golden showers
Posted: 21 Apr 2014 12:04

Never have but would try if asked. Met a chick once who had an idea I thought was pretty hot. She wanted a guy to stick his cock in the side of her pantys just enough to reach almost the bigining of her pussy lips, then start pissing on her. And I spoke to another that wanted to give head and have the guy start pissing while she was sucking and not only drink that down, but finish the blow job as well. Not sure that second one is possible. .. I'd have to be on the verge of pissing myself to be able to do that.

Topic: Tasting your juices?
Posted: 21 Apr 2014 11:31

I do, and my prefered method, though prteety difficult is to basically put my legs over my head as far as I can usually using a peice of furniture to keep me there, and shooting it directly into my mouth. Due to the awkwardness of the position there is always a little bit to lick off my lips and face;) also love making out right after 69, tasting that sweet "his and hers" mixture;)

Topic: What's on your sexual bucket list?
Posted: 21 Apr 2014 11:21

Oh the things on my list....;) well here's a few:

-I want to be in a pitch black room with a bunch of people and have an anything goes free for all.
-3 way with 2 women
-sex with a tgirl
-3way with a guy and girl
-be taken by a woman with a strapon while crossdressed
-be at the center of a bukake while crossdressed
-suck a dick through a gloryhole
-oddly specific, but have a girl jerk off a bunch of dudes into a cup to for me to drink
-have a chick snowball with me

I got more, but I only have so much time lol!

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Stories Published By PlayfulAshley All Stories »

The Booths

Not sure where to begin. I guess I will start with my name which is Brian. I am a twenty-one year old with a thin frame making me look much younger than I am, and I have always had a fascination with adult video booths. Perhaps it began as a child with the mystery of that building in our small town all lit up with neon and colorful markings, but it definitely set in as a teenager when...

Added 24 Oct 2016 | Category Gay Male | Votes 8 | Avg Score 4.63 | Views 6,027 | 3 Comments

Free Clothes

I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you...

Added 07 Mar 2014 | Category Crossdressing | Votes 14 | Avg Score 5 | Views 33,593 | 9 Comments

TV Repair Man

DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing from the first person perspective simply because it is a fantasy and it’s just more fun that way;) About a month ago my TV broke and it is kinda big and expensive, so I decided to have it fixed rather than buy a new one....

Added 04 May 2011 | Category Crossdressing | Votes 38 | Avg Score 4.94 | Views 26,496 | 14 Comments

Ashley’s First Time With a Guy

Ashley’s First Time With a Guy DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing simply because it is a fantasy and it’s just more fun that way;) So it all started on Valentine’s Day of that year. My wife and I had gone to dinner and got a hotel room for a romantic...

Added 03 May 2011 | Category Crossdressing | Votes 73 | Avg Score 4.94 | Views 55,008 | 31 Comments

Friends Comments

Happy Birthday from the Lush team.
31 Dec 2017 00:20
05 Jun 2017 04:08
Happy Birthday from the Lush team.
31 Dec 2016 00:20
21 Nov 2016 02:38
12 Sep 2016 03:32
Happy Birthday from the Lush team.
31 Dec 2014 00:20
05 Sep 2014 03:27
Happy Monday.

14 Jul 2014 13:12
07 Jul 2014 03:52
26 Apr 2014 02:06
14 Apr 2014 15:31
Thanks for the add
04 Apr 2014 21:51
hi thanks for the add
04 Apr 2014 15:01
25 Mar 2014 06:10
Thank you for the ad.
25 Feb 2014 20:40
Nice having u as a friend
25 Feb 2014 18:24
Thank you for voting on my story! Just love your pics, so horney xx
25 Feb 2014 12:31
09 Feb 2014 02:52
Happy Birthday from the Lush team.
31 Dec 2013 00:20
Thank you Ashley, I love your photos YOU ARE HOT!!!
06 Jan 2013 08:22
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