Ashley’s Crossdressing Adventures free porn video

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It's Sunday and Mommy wants to hear what sissy things I have been up to, and don't leave anything out Sissy Ash, Don't be shy, out with it sissy, I already know you love being a complete sissy!

Did you buy anything sissy? Yes Mommy, I did, I want to hear, everything you bought you little sissy, let mommy remove your bra, to access your sissy nipples,

Mommy I bought 4 pairs of sheer nylon panties to add to my collection, pink, blue, white and yellow.

What else sissy? I ordered 3 packages of diapers, Pink design, all white and Pride colors, sissy you like to wear diapers now? Well, mommy will have to treat you like the baby you are! That should be fun!

Anything else? 4 different colors of plastic pants to wear over the diapers, wow, you sissy!

Mommy I can't wait to be a sissy girl full time 24/7, I will support you being a girl as much as you are willing to do, especially when you retire, if you come out as a lady, more and more people will find out about your feminine sissy ways,

I know mommy, that's okay with me, you're such a naughty little sissy Ash! If you want to be a sissy, you need to act, talk, walk and continue to work on your makeup, I want you to be cute and girly, especially very feminine,

Think about the future, getting your ears pierced, work on your figure, I would like to see real breasts too! Only going to be female clothing for you, mostly skirts and dresses, must wear bras during the day, nylon type panties, feminine blouses.

How does that sound sissy? That sounds like a dream mommy, glad to hear that sissy! At some point we are going to go out together, once you look passable,

I never thought my husband would turn out to be a sissy trans- lesbian who enjoys wearing girly, sissy items and diapers too! But I rather enjoy your sissy ways,

What else Sissy, mommy I forgot I also got a dildo/penis, I know sissy, are you gay sissy? I'm not gay for man, Well, what you want to do with that penis sissy? Don't be shy!

I have fantasies playing with and sucking on penises, of course she males, I want to see you sometime pleasuring that penis, does it cum sissy? Yes mommy! You little sissy girl!
Well if you want to be a girl, penis is more suitable for me, no vagina for you, sissy you are complicated, you're a lesbian, but you like penis instead of vagina, mommy I just identify more with females, men are yucky, I enjoy ladies with penises.

Sissy have you ever touched or played with a real penis? Tell the truth sissy, I won't judge, I bet you have sissy, maybe once mommy, what do you mean maybe? Out with it sissy, when I was younger I responded to a TS ad, and nervously made a appointment,

It was supposedly a massage from a TS Lady, once I arrived, she was wearing only a bathrobe, she just showered, after saying hello, she asked what I wanted to do, she told me to lay down, took off my pants and of I was wearing panties, she complimented me, said they were pretty!

She was asian, she then removed her bathrobe and revealed a good size penis, she asked what I wanted to do, I told her I would like to play with her penis, it was a fantasy of mine, she said sure, so I started to stroke it, it was so hard, she then got in a 69 position and we both sucked each other's cock,

She wanted to try to stick her penis in me, but it didn't feel that great, not my thing, So we continued to play with each other's penis, and feeling excited I told her to cum on my face! So I masturbated her till she came all over my face!

What a sissy you are! This is the type of sissy stories I want to hear from you, real stories! I need to hear more from you next week, I'm sure you have many,many sissy stories you need to confess to mommy,

Now sissy, while I play with your sissy nipples, and you completed your true sissy adventures, your secrets are safe from me, as long as you continue to share, you can cum in your sissy panties now!

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18.04.2022
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Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

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***A crossdressing story***(All characters are fictitious...maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her...

Steve the Crossdressing Cat Lover

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please.Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land Steve has that he'd keep a couple of horses to ride but no. The barn is filled with cats that curl up and sleep...

Crossdressing

Mother and Crossdressing Son Fantasy

Mother and Crossdressing Son FantasyThe story is about how my passion for wearing women's lingerie helped me to establish a more intimate relationship with my mother.I'm a 42-year-old man and I still live at home with my mother. My Father passed away 20 years ago. We live in a suburban bungalow and I have a nice little apartment in the basement. It's not as private as I would like. That's important because four years ago after discovering a number of chat sites where men present themselves in...

Crossdressing at the cinema

I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...

Wifes crossdressing fantasy Part 3

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her, but what? I thought and thought, but I couldn't think of anything to equal what she did for me on our anniversary....

Crossdressing

Wifes Crossdressing Fantasy Part 2

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. Since my wife shared her fantasy with me and made me her bitch, our love life has changed. Now I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before. When our anniversary came around, a month or so after my initiation to dressing up, my wife announced to me...

Crossdressing

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