Uncharted Territory
When I think about my life as Cassandra, I can honestly say this is something I’ve stumbled upon by chance. I’m not a woman trapped inside a man’s body. I have no need to be a woman just to have sex. But OMG!!! Dressing up and having sex with men whom I would have never imagined to secretly love cock. Straight men who love giving head! And then begs me to fuck them up the ass. It is still surreal. Not just sometimes but all the time.
And so, forgive me, if I don’t understand this life. I don’t know how much to invest in it. I wonder at times if I’m just an observer or if I’m really a part of it.
A while back I had sex with a pretty hot stud. If you watch Mad Men he is the Don Draper character. Totally Jon Hamm. Chiseled jaw, 6’2”, beautiful muscular body that’s not gym-perfected. Muscle tone that comes from doing manual labor and not Gold’s Gym. He works as a park ranger.
The money’s good as Cassandra but the real gold is the cast of characters who I have sex with. This guy… who’s so masculine, who appears so sure of himself, who’s a man amongst men… he just wants to be submissive. He is the exact opposite of his public persona behind closed bedroom doors. Do you think people who are not a part of this subculture will ever believe my stories?
When we had sex he sat on my face while sucking me off. His pink rosebud was like a flower that blooms only for me. His face has lines and stuff from working out in the sun all day but when his undies came off his ass is so amazingly white and taut. Still so young and fluffy. Pillowy. It makes me wonder what it’s like to sleep with my face buried in that blossom.
After that first stage of sex he sat at the foot of my bed with a stunned and puzzled expression. He didn’t look at me. He stared into the air in front of him and said
Wow… have you ever thought about having a boyfriend?
Of course I was secretly flattered. But I didn’t even consider it.
Naaah, I told him, it’s too hard having a BF when you’re a prostitute.
I’m not getting invested as Cass. I’m just not. At least that’s what I tell myself.
But you know what he said that was music to my ears? When I got all horned up and I wanted to fuck him really bad he said, we’ll get to it I promise but I want to suck your cock a little bit longer.
Can there be a better combination of words in the English language? Someone who just wants my cock in their mouth a little bit longer?
We’ve been chatting on line. I’m bored at my day job and nothing makes the day go by faster than having dirty talk. And we fucking take it there. We’re both freaks.
In a few weeks he’s coming to see me again. I’m going to dress him up. It’s a pretty important fantasy for him. I don’t know how turned on I will be when he is completely made up. But even before Cassandra I used to fantasize about taking a really masculine straight stud and put him in silk panties with a lace trim and then running my tongue along that spiderweb edge.
I told him I’m going to put him in a baby doll lingerie dress by Betsy Johnson.
It’s funny. It’s never the Chace Crawfords and the Zac Effrons who want to crossdress. Rather, it’s usually these super masculine men who are the pillars of traditional masculinity. Football coaches, steelworkers (the kind you see at the Black Hole at Oakland Raiders Games), former Green Berets, Firemen (America’s finest frequently ask for barebacking), construction workers. The ones with the impossibly strong square jaws. The five o’clock shadow that appears by noon.
It’s going to be a lot of work to turn this guy into a decent looking girl. I’m secretly hoping he’ll be satisfied with just wearing lingerie.
He’s spending the night. He says he wants to wake up next to me. Why do you want that, I ask him. He says he wants to feel close to me. I told him he won’t be waking up to Cassandra. I don’t go to sleep with make-up on. It clogs my pores.
He says it will be a next step for him too.
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Tags: intro
I think this is leading to a climax of irony for Cassandra.
A “straight man” who desires to be in a traditionally-womans roll (bottom) with a man who dresses as a woman. This is a very dominant experience for Cassandra and very submissive (intimate) one for “Don.”
This may progress to “Don” dressing as a woman (Donna?) while in a woman’s traditional sex-role, in bed with (Kass?) an uncrossdressed Cassandra. This is a real twist on the kink – wow.
It will be incredibly hot and intimate for him and some exceptionally great sex for you. You’ll be thoroughly TOPPING this guy physically, emotionally and psychologically. I think it would be hottest if you have him just wear the lingerie.
Sometimes you resolve an irony when you take it to its limits…hmmm. In other words, sometimes a straight guy just needs to be a gay. It could be over-the-top for you.
xoxo,
Brian
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Brian Brian Brian… somehow I think all of you guys know more than you’re letting on. This is a little secret men’s club. Nothing I write about seems to shock you guys (as it does me!). Don Draper wanting to crossdress and be pounded like a little girl… who’d ever believe it. And, yet, you guys think it’s the most natural thing in the world. I sure hope my next encounter with “Don” (or he may be Bette Draper by then) will be as hot as our first time. I will certainly fill you in on the details. Thanks for reading, Brian. Cass
I think you are who you are, and you are someone else too. Just as Don is who he is….but he is someone else.
Some may call the pursuit of being another person a “distraction”, but I think it is more an “evolution”. We try new things as we are interested in them…..new chapters in the book of us. Where your story goes (and with whom) now is going to be based on the introspective thought (truth of what you want) and outside stimuli (possibility) you allow to influence that thought process.
Perhaps you won’t get invested as Cass, as you’ve said Is it a possibility you will allow yourself to get invested as your..Self? (As I don’t know your real name) I think, even in considering him to spend the night…..you already have. You mentioned in a previous post “Self Actualization”~wink and smile~
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Ian… This rabbit hole is deeper than I thought. I’m trying to understand you guys. But the more I know, the less I’m sure of. What’s the motivation for straight men to crossdress and assume the role of women? Is there an element of transgenderism here? If I took a poll of all of my customers/readers, do you think most of them are closeted crossdressers too? Are you? All the literature seems to be focused on the MTF transgenders, but nothing seems to be written about the men who admire and chase MTF’s. What’s going on with these men? Cassandra explores…
Life is an adventure, dear. I’m crossing my fingers for you and Don…
-Ruby
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I guess his nickname is Don now… I was going to nickname him Lone Ranger because he works as a Park Ranger and it must get awfully lonely in the National Parks (I don’t picture many trannies running among the bisons in Yellowstone,, hehe). But Don Draper he shall be… and maybe I get to be Bette Draper. January Jones is sooo lovely, don’t you think?
I believe we (your customers and readers) are simply the bell-shaped curve. There are extremes on either end and a whole lot of combinations in between. I don’t think the numbers matter so much as the connection or relation the individuals find with you (or your profession by proxy). It’s about the individual psychology that endears. For some it’s a sympathetic connection, some a sexual one, others just curiosity. If there were a majority, I think it would be the “curious ones” looking for a safe way to explore another lifestyle. I’m not a crossdresser, though I have had tights/pantyhose on before. (take a guess, go ahead….I’ll be honest about why) I am bi, but not closeted to my g/f about it. Oooh yeah….Cassandra is not the only one who explores.*wicked grin*
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Ian! *HUG* thank you. You are pretty awesome. Your girlfriend is lucky. *I* am lucky to have you as a reader. Do me a favor and always be honest with me: let me know when I start venturing down the wrong path, k? Cass