Reader Stories: Crossdressing, BDSM, Possible Domming and Other Things Your Cubemates Desire

Ah, my dears. You are so good to me. Always sending me funny little stories, smart thinky articles, and heartfelt missives on your sex lives (or lack thereof).

And I cruelly repay you by saving them for later, then forgetting to run them. But today, I shall make up for this, putting some of the backlog into a big ol' virtual sack and depositing it unceremoniously on your Internet doorstep.

In some of the stories below it was hard for me to find a point of reference for the particulars involved (and even got a little cringy at times), but what I find fascinating is the fearlessness all the writers had in uncovering and exploring their desires. Maybe they didn't want to want what they wanted, but they kept wanting it anyway.

"Underneath it all, we are wild and we know it"--Reginald A. Ray

--Let's start with this one from..let's call her Pia: "I have always been very adventurous in bed," she wrote, by way of introduction. "Even my virginity was taken in a kinky way. I have been in a relationship for seven years with a wonderful man but I was getting very bored and needed to let my kinky side come out again. He was not kinky at all. I was the closeted freak. I finally came clean early this year and he was ok with me exploring within a clear set of boundaries. Doing some research, I found FetLife, where I talked with local people. I found a submissive's discussion group, met some wonderful people, got invited to a tasting of kink party, and the rest is history. This is my journaling before my first scene. I thought it would give you a good intro.  I have been journaling every scene I have had so far, some are more graphic than others."

The Nerves of My First BDSM Scene
     As Saturday approaches, the nerves and butterflies increase. I have been pondering a lot about having the guts to do what I am about to do on Saturday.
     Since I decided to go into the community, I have met a number of wonderful people and I have gathered the guts to surrender to my desire. This particular lady has given me the warm and fuzzies since I met her. She is wonderful, open, warm, welcoming, and a bunch of other things that make you want to trust her. Her girlfriend is also super nice, caring, protective, funny, etc. What I want to say is that I really like both of them. I am not bisexual but BDSM is about much more than just sex and I feel very comfortable with her.
     That is the reason why I decided to go for it. I trust her, and I have become a Violet Wand fan, or like she put it, a juice bug. I never in my life thought I would enjoy and crave electricity!
     I have been so nervous about it, not it it ... but about the party attached to it. Since the first time I went to a play party, I have been in a constant state of admiration; admiration for the freedom and acceptance of women of all shapes and sizes. It was a huge lesson for me from the beginning. Every time I went to parties I thought that I want to be like that when I grow up; I want to be that free. I want to disrobe not worrying about what someone else might think, but just for the pure pleasure of it all. Just because I cannot wait to feel that intense sensation on every inch of my skin... and oh my god, I do! I wanted a seasoned Violet Wand user to show me new heights. I just cannot wait.
     A friend of mine just told me how hot it is what I am about to do and he also told me that the one block I have is my own thoughts. He is so right; I get too deep in my own head and overthink everything. His advice: just do it. He sounds like a Nike commercial but he is right, and I want to do it. I want to close my eyes or look deep into His eyes and get lost in the raw sensation of it all. All I want to do is feel and not think.
     Ironically, today I read the following:  Love YOU. – Let someone love you just the way you are – as flawed as you might be, as unattractive as you sometimes feel, and as unaccomplished as you think you are. Yes, let someone love you despite all of this; and let that someone be YOU.
     And I think I usually do ... but this ... this is a huge deal for me. I will do it and I will enjoy it, because it is totally out of my comfort zone; and someone once told me that life begins at the end of your comfort zone. So life ... here I go.
     Can't hardly wait for tomorrow!

    
--The next story is How I Became My Wife's Wife.  I'm not sure if the author wants me to put his name so I'll just say his name is D. D, if you want to write in and claim ownership, I'll be happy to put your name on here.

     Hi.
    My story is a bit unique, but I thought I'd share. You see, my body isn't always right. I enjoy being a man. I enjoy it immensely. I love using my penis to take my wife to the brink of ecstasy, hold her there, and with a lunge, send her into a blacked out world of fireworks that has a population of one: The entity we become together.

     I love being a man who's unabashedly and irresistibly attracted to women who outweigh me, and at 6'1", you know what that means. I love all the sensuality available from such a body. Easily my favorite thing about being a man is feeling every inch of my penis moving inside my wife's finely textured pussy. See, what passes as a g spot for other women, my wife doesn't have. That peculiarly textured area occurs right behind the bone, and is easily tongue-accessible, making her one of those few women that come hard from being fucked hard.
     She gushes cum and covers me with it.
     And squirts.
     Oh yes, I love being a man.
     As both a former cheerleader and a former stripper, you can imagine the body issues my size 22 wife had when we started dating. She's down to an 18, now. Nevertheless, she bought this outfit early on to wear for me. The top is sleeveless with a plunge neck, and the skirt is my favorite length: long enough to cover her ass, but not long enough that she'd wear in public.
     A few months before we got married, she wore it for me again, we screwed like porn stars (again), And she went to eBay to find a new outfit.
     A few days later, It arrived, and we immediately covered it with cum.
     The following evening, I asked her What she wanted me to wear. She told me to pick something, so I put on her sleeveless plunge top. Nervously, I looked at her. Surprise flew across her face and was gone. She said "well, there's a skirt to go with that..." So I put it on.
     She adjusted it until I was wearing it correctly, then had me turn around. She lifted the skirt, rubbed my ass, dropped the skirt, then pushed her lighter on the floor and giggled an oops. I put my ass as high as I could as I bent over to retrieve the lighter, and she gasped in my general direction.
     "NOW I see why you like the skirt," she managed to get out.
     I turned towards her and handed her the lighter. She threw it and surrounded my dick with her mouth. I stood perfectly still as I received the most passionate blowjob she'd ever given me, making it the most passionate blowjob that ever happened. 
     A new feeling had awakened inside of me, and I had to put it inside of her.
     So I did the only logical thing I could do. I grabbed her ponytail and pulled her head off my dick. She resisted, hard, but I overcame, grabbed her shoulders and pushed her back on the bed. Then I hooked my arms under her knees and pulled her close.
     My dick knew where to go, and I took the next five minutes slowly inserting it. She was dry when I started, but dripping wet when I bottomed out.
     Holding steady, I moved my lips to her ear, pushing her legs back as I did so. I asked her if she'd like her husband to be a woman, and she started to cum. She couldn't speak or move. All she could do was quiver against my hips and pulsars.
     Since the first insertion went so well, I followed it up with as many rough insertions as I could, moving around to hit as many spots as I could in a vagina that was increasingly voluminous. 
     2.3 minutes later, I dropped down on the bed next to her. We'd each had an orgasm, hers was still happening. We were both unable to move. So we did what you'd have done instead: we passed out.
     I woke up in the morning feeling great. I put my hands on my chest and the feeling was gone. I hadn't magically grown breasts overnight.
     We repeated the experience with her new outfit. ...on me.
     The next day, I spent a great deal of time trying to understand what I was doing and why. Even though I had embraced feminism and done any and every thing I could to abdicate my own male privilege, I was still subject to 38 years of conditioning telling me it was bad/wrong (badong) to be a woman with a penis. I stood for transgender rights, but I was uncomfortable with the idea those might be my rights.
     That evening, wrestling with my inner demons, I started the conversation my wife didn't even know she never wanted to have it.
     In the couple of years since then, we've both learned a lot about ourselves. We understand that I'm a crossdresser, and we share clothes. We understand that women and men can't be equal until I can put on a dress and breast forms and walk around in public in safety.
     Most importantly, we understand how awesome it is that we're together.

--And finally, here's this one. I couldn't tell if this was a bit spammy ("Dear 'Ms. Hamilton'") or not (used the correct, awkward acronym for blog), so I give it to you as is.

Dear Ms. Hamilton,
I greatly enjoy IBWMW and thought you may be interested in a short cartoon I made. "So, You Want to Be a Dom?" is about a man who wants to be a Dom, but doesn't actually want to be a Dom, or even know what one is:
https://www.youtube.com/watch?v=GehwctOX1GI

*****
So. 

"Desire presses ever forward unsubdued," said Freud. You can try to smash it down (note: this does not work) or you can leap right the fuck into it and see where it takes you.

Let me know which you pick.
xoxo
jill