Be My Bitch?!?
OK. Here’s the story. “Don Draper” and I have been emailing quite regularly since the night we first hooked up. He’s back at the National Park where he’s a Park Ranger, and I’m still here in SF — taking the occasional client, writing my blog. Because there are no trannies roaming around with the buffaloes, Don hasn’t had many opportunities to play. As a result of his sexual deprivation (or so I guess), this wholesome, All-American, you-would-never-guess-in-a-million-years-to-be-a-tranny-chaser has turned into nothing less than a freak with these lurid fantasies that he writes me.
I love it. Such interesting material for my blog. Just you wait til we get to the end. Nothing short of OMG. Promise.
Although I have always known Don was a submissive, I just thought that submissive meant getting on your knees, blowing Cassandra, and then bending over. Apparently, that’s like, the very beginner level of submissiveness. I would guess Don to be at the expert level. Maybe not quite a submissive “Guru” yet, but getting there.
He keeps telling me, Cassandra, I want to please you. Tell me what you want me to do. I’ll do anything.
Anything, he added emphatically. Almost as if in code.
It freaked me out ever so slightly, because I’m not a domme! There are only so many sexual positions I can order him to do via G-Chat! Yet, Don always wanted more. What is it that he wants me to order him to do and why can’t he just come out and say it?
As the date of our second rendez-vous approached, I actually sat down to brainstorm what other activities I can order him to do. Beyond doggystyle, missionary, and riding the tranny, maybe we could move the setting out of the bedroom… and into the bathroom! Maybe I could bend him over the sink and fuck him. Or I could sit on the toilet, with the lid down of course, and then he could ride me. And then make him scrub the toilet afterwards. Perhaps make him scrape off the dried toothpaste trails in my sink. Is this what he meant by being ordered to do stuff that pleased me?
The thought of household chores opened me up to endless possibilities. I could make him vaccum the living room. Wipe the windows down with windex. Load the dishwasher. Clean out the fridge.
All while he’s wearing a baby doll lingerie dress with stiletto heels, of course. I felt so satisfied with myself. I am so smart. It’s a win-win situation all around: I get great sex, he gets to obey my commands, and my house gets cleaned. Cassandra, you have truly outdone yourself.
You want to know what really happened?
He came over the next time he was in town. His eyes had a little more wrinkles than I remembered, but still very sexy. I put a wig on him. It was the perfect color on him — blended in with his skin so perfectly — I really am quite good with these things. But somehow he ended up looking very… Spinal Tap. Like a rocker from the seventies. Doesn’t matter. I fucked him. FOUR TIMES. He really got his money’s worth. And, then, finally, after four orgasms apiece, we had our post-coital conversation.
Cassandra, he says, wow, you are such an amazing lover. I want to please you. I want to submit to you so bad.
I’m a little bit confused, because I thought he had just submitted to me. Four times! What else does he want?
I want to be your slut. I will do whatever you tell me to do. I will suck off whoever you tell me to suck. Just tell me who you want to fuck me and I’ll let them.
Okay, here I get what he’s trying to say. It’s really nothing out of the ordinary. Lots of guys who come see me have the fantasy of being “forced” to be a slut.
I’ll service your customers for you. Put me to work.
Ummmm…. I’m not sure how many of my customers would pay for aging Led Zeppelin rockers, but I’ll play along.
Make me walk the streets of the Tenderloin in fishnet stockings and high heels. I want to be your whore.
Okay, we’re seeing the exhibitionism here. He needs attention. Got it. I’ll explain to him later how the streets of San Francisco are friggin cold! all year round. I would have never became a ho if it wasn’t for CraigsList.
Make me wax my body. Make me get piercings. You can even hormone me up if you want… what ever makes you happy.
I swear, you cannot make this shit up! Who writes this stuff? Who would ever believe me?!? Did Don just go from a tranny chaser to a closeted transsexual?
Of course, if Don is a transsexual, I would support “her” all the way. But I’ve known many transsexuals over the years, and they’re nothing like Don Draper. Come to think of it, all the transsexuals I know have been Asians and Latinas. A few black Tgirls. Maybe Don is what a Caucasian transsexual looks like? Regardless, I will support her. I will, I will, I will.
Even though I think what Don Draper really wants is to have his own boobs to play with! And conveniently place the blame on me. “I” made him do it.
But I don’t even like boobs!
This is America. The land of the free. Why do you have to make anyone “force” you do to anything? If you want to be a crossdressing (or, in his case, a transsexual) prostitute, follow the advice of Nike:
Just DO it!
Tags: sleazy, Submissive straight men
DD wants to please you. Right now, he has little interest in going out and dressing for himself. He gets a rush when someone uses him. If you really like the idea of helping him in his transformation vanilla to whore it can be really positive.
—————–
Morgan, Honey, I respectfully DISAGREE. Him taking hormones has *nothing* to do with “pleasing” me. It’s his own fantasy, his own fetish, his own desires, that he’s projecting onto ME! I’m fine with everything he wants to do but I think he should own up to it instead of saying it’s for me. Because it’s not for me. Starting hormones is serious business. I think he needs to ask himself if he’s really TG or if it’s just a sexual fetish. If it’s the latter, then own up to it rather than making it seem like I forced him into it. That’s all. I still like the guy. The wonders never cease with my customers, that’s all. C
I have to agree with you Cassandra, for the most part, concerning your response to Morgan. He trusts you completely (obviously, else he would not be so eager to let you steer his life (or “transformation”) so completely. I agree with Morgan in that it can be a positive thing (and for both of you if played properly). Is there any chance he has someone in mind to do this roleplay with *already*? I mean….when I have a fantasy and bring it up to S/someone, I already have the next step thought out and nearly (if not) planned. Perhaps he just wants you to orchestrate it. (Again, he should own up to it, making you a party to it, rather than simply an unknowing accomplice) Regardless, you should educate him on the pros and cons of all involved. My advice: No makeup or wigs or hot clothes. Sit him down and ask what his superiors in the forestry service might do if they saw his tits. Love your patience…AND your frustration, girlie.*wink* Thanks for sharing.
—————-
Ian: I know — he has his job to consider! I can’t imagine him hiking the trails very well in platform stilettos. I tell you, Ian, I used to think there has to be a book offer on my life, but now I think maybe the real stars are guys like DON. I know it doesn’t shock any of you (who I venture to guess may harbor a bit of the same impulses) but trust me, it shocked the hell out of me when he told me his female hormone fantasy — and it’ll shock the hell out of America. Random House — CALL ME! This is a best-seller! Cass
Oh yeah….and he’s doing what’s called “Topping from the bottom” Steering where HE wants it to go by leading You to the next evolutionary step in his fantasy.
—————-
Ian — what ever happened to vanilla tranny sex. Won’t anyone settle for just giving me blowjobs and bending over anymore? I tell you, it’s all because of the internet. Too much! TOO MUCH! C
I kinda discounted the hormones thing. I thought that was just crazy talk – one too many porn fantasies. But I don’t know DD so that could have been serious. The only thing I really saw was DD has a fantasy of being used as a whore. He wants you to whore him out, but if it isn’t something you enjoy I just don’t see it happening.
—————
Morgan — thank you so much. I think you really nailed it with this comment. It seems to be the general sentiment with all the comments that DD’s hormones fantasy was just crazy talk. I think you’re right that his real fantasy is to be used as a whore. I have no problem whoring him out, but it’s the whole hormone talk that really threw me for a loop. Shocked the hell out of me, but apparently all my readers saw right through it. Now… an even more important question: do you think men will want to pay for the 70′s Spinal Tap aging rocker TV look? C
Hmmmmm…well, Cass this is a close call for me between two interpretations and I’ve tried to put myself in both his and your position in order to pic one.
In one interpretation Don wants to be a tranny and wants you to take responsibility for his transition. In another interpretation Don is just trying to satisfy his fetish for being dominated and emasculated until he reaches some limit.
Judging by items from a previous post about Don (eg. He wanted to spend the night with you while not dressed as Cassandra.) I tend to favor the later interpretation.
He probably needs to be forced to perform humiliating and embarrassing acts of emasculation because it offers the most intense emotional experience for him. In other words, he gets off from emasculation and not feminization per se. For him, sexual bliss is defined by being the crossdressed bitch of a gay CD.
His requests may seem very theatrical to many people but to him it is primal to his sexual satisfaction. If you can’t find a way to combine his fetish with your preferences then eventually your compen$ation might not be worth the burden of having to provide fresh new erotic thrills for him.
One suggestion is to have him buy some false breast to wear around. Maybe if you “force” him to wear panties until your next meeting he’ll be more content. Can you imagine him telling his girlfriend why he’s wearing pink panties and false breasts when they are together – “My transvestite mistress forces me to.” – it would be like a castity belt (unless he does this already
). If that’s not enough for him, game over.
Brian
—————
Brian… I agree. After reading all the comments I’ve arrived to share your conclusion: DD likes to take it to the limit of emasculation to thrill him. Hormones is just crazy talk. Regarding his girlfriend… it seems like his days with biological women are over. He says he can’t get hard with a girl unless he’s in love with her. He really likes CD, TV’s, TG’s (his favorite combo is boobs with cocks). He’ll be back for a stretch after next April. If I’m still doing this by then I’ll definitely keep you guys updated… Who is the real Don Draper? LOL, C