Wear a short skirt or dress, the shortest you have. Nothing underneath. Bare legs. Bare feet.

The extent of force will be up to you. If you want me to enter unannounced, unlock the door to your apartment at 9:28. I’ll be arriving at 9:30.

If you want to let me in, keep the door locked, and I will knock. But we won’t speak. No small talk, no chit-chat. You can say things in character - however much you like. You don’t have to pretend you don’t know me, you can still ask what are you doing and you can say no. You can struggle.

But I won’t stop.

You have a safeword now. You’re going to have to use it.

For Datedyke, because she asked me for this story, with thanks for reading the early draft and commenting things like “Make my character more mean,” “Don’t say thank you,” and “Just take me down,” and for providing the details of her outfit, and picking out my tie. “Swift thrust of cock,” one of my very favorite lines, was written by DD, not me; and DD informs me that “Lea” is pronounced “Lee.”*

I’m dressed, plain black slacks and a black button-down, sitting on her bed, fidgeting with three ties in my fist I know will fit her desired houseboy fare. I bring them to her, gaze at her in the mirror as she applies something to her eyes with a fine brush.

“Either this silver, or this dark purple, or the dark blue with the white dots?” I offer.

“No no. This one.” She turns around fast and points, chooses the silver, the one she bought for me over the holidays. I nod and set the other two on the counter, start to tie the silver one. She glances at me in the mirror, aware that I’m watching her, narrowing her eyes a little, then finishes with the brush, tosses it into her makeup case.

She’s a little annoyed. She doesn’t like it when I watch her get ready. “Hand me those earrings, will you?” I see small diamond studs on the counter and hand them over.

“Not those,” she says. She’s beginning to get stressed. Three of her closest friends will be here any minute. It is my first time as her houseboy for a group.

“Those,” she points again and I see favorite pair of gold hoops. Of course. They match the black heels with the gold trim that she has on with her cocktail dress.

I fetch the earrings and she fastens them to her ears. I attempt to kiss her shoulders, neck, slip my hands around her waist, touch the curves of her hips in her sleek black cocktail dress. She shrugs me off, turns around, kisses me swiftly, dismissively. “Darling,” she says, “You look great. Really. I’m excited for the party.” And then she’s gone, running downstairs to check on the kitchen, fuss over food and drinks.

I sigh at my reflection, take a breath. Check my eyebrows, my teeth, my perfectly messy hair. I’m nervous, but ready for this, excited to be shown off, a trophy boy, look at my tricks. I want to please her. I adjust the dimple in my tie and then my cock under my harness strap.

The Oscars start at four and her friends have one of those pools where they’ve all guessed the winners and someone wins the whole pot. Lea gives me significant glances when the doorbell rings and I take coats to the closet, take drink requests, and practice my sweet “hi, hello” submission as they come in the door. Her friends are dressed up: The Cuban Genius, BB, and the Butch Daddy.

BB giggles at my predicament and hugs me, eyes twinkling, flirtatious, amused. The Butch Daddy eyes me like we’re fags and she’s cruising. I feel myself stiffen and try to relax.

Lea shines, says hello, hugs and smiles and laughter and greetings. She is subtly maneuvering this whole interaction, sparkling in her element; her earrings catch the light, glitter, and her makeup is flawless, soft. Her dress flirts around her knees, off her shoulders.

I serve martinis and cosmos, smiling and making myself as unnoticeable as I can be while I watch her. My attention is tuned fully into her body language, her eye contact, her hands. Not only for her cues at service, but to see her, to observe, to take in. I admire her like this. That external expert persona of hers is so appealing, I see her through her friend’s eyes, strong, poised, capable. I am blessed to see the soft parts, too.

Conversation flows, they catch up on jobs, girlfriends, America’s Next Top Model, the weather for upcoming kayaking, hiking. I try to participate, but Lea keeps interrupting me with glances and gestures every time I sit.

“Boy! More wieners!” she calls while I’m in the kitchen fetching a glass of water for the Butch Daddy, and everyone laughs. She’s been waiting to use that command. I bring the next plate of cocktail wieners onto the coffee table with a bow and a smile, as if I’m in on the joke.

Lea brings one up to her lips and leaves it poised. “Mmm, I love wieners,” she says, winking dramatically. Everyone’s still giggling; BB is giving me suggestive glances, the Cuban Genius mimics Lea’s movement of a wiener to her mouth and gives it a mock blow job, eyes low, looking at the Butch Daddy. I blush and try to laugh, adjust my silver tie nervously.

Lea takes inventory of the living room. “Refill BB’s drink,” she whispers loudly, for everyone to hear, and I take BB’s glass. He gives me a smug flirty smile. I mix his martini like he said, three olives, and I am careful careful careful not to spill in the long walk from the kitchen to the couch, and hand it to BB.

“BB likes his martinis dirtier than that,” Lea hisses at me as I resume my perch on the edge of the chair. “Make it right next time.”

I look to Lea in a glance, apologetically and to see her face, to see what’s under these commands, pleasure or embarrassment, gratitude or heat, but she’s already engaged back in her conversation with the Cuban Genius, laughing about something, talking about someone whose name I don’t recognize, who is that, who are these people I don’t know? She feels me looking at her and glances at me briefly, and for just a fraction of a second I see her features soften with deep appreciation, lust, care.

Then it’s gone; her body languages changes and she holds her near-empty cosmo up at me. “You’ve got another one of these ready, right? I shouldn’t have to even be asking you.”

I duck my head, go back to the kitchen.

A few minutes later she’s calling me, but I don’t recognize the call of “boy” fast enough, don’t hear her for a moment too long. Finally she uses my name: “Sinclair!” And I look up, caught off guard.

She inclines her head quickly to mean, come here, with that look on her face of hard exasperation and displeasure. She’s sitting on the arm of her couch, it makes her feel taller, and I approach. “No, here,” she says as I stop, pointing at the space next to her.

“Take your cock out,” she says.

[Read more →]

1. Fuck a girl’s ass with a strapon (is it still called pegging if it’s two women, or is pegging unique to a woman strapped on fucking a guy?). I’ve done plenty of ass-play, but somehow the women I’ve been with have never actually been comfortable enough with it for me to be strapped on. I have, however, fucked a guy this way, once upon a time.

2. Stingy toys, like a cane. I’d like to leave some marks. I’ve used a cane before, actually, but I don’t own one, and I’d like to experiment to feel more comfortable with it

3. Receive - and give - a cutting

4. Role-play out in a bar, pretend we don’t know each other and pick each other up. I suppose that has a lot of variations (resistance, convincing).

5. Sex in central park, sex in every girl club in new york city (the bathroom, the back room, the alley, the deserted dancefloor, wherever), sex at work. After hours, in an empty office, wherever. I’ve done that, actually, though not at my current job.

6. Play with knives. And yes, I think I’d like to be the one holding the knife, although that could be negotiable.

7. And, last but not least, recent events have told me that I need to practice my flogging & rope bondage.

A few weeks ago now, I asked Callie what it was that we haven’t done together, sexually, that she would like to play with. In some ways there is a lot we haven’t explored yet, many things she and I have brought up between us that we have not or have barely began to introduce: knives, rope and bondage, spanking, flogging, fisting, 69, role play, force, sensation.In response, she brought up force. I have told her that I like some resistance, so she asked: “How much can I resist?”

Asked me that with that teasing harlot little-girl voice of hers that she gets when she starts to want. That lilt that reveals desire and submission and a test of the waters to see if I want what she wants.

Oh, god.

“A lot,” I answered. Oh, a whole lot. “You’re pretty strong, actually, I think you could hold your own against me.”

“So why would I be resisting?” she asked. “There are lots of reasons why attraction or sex or seduction would be conflicted … it could be forbidden, it could be naughty, we could dislike each other … ”

I never quite thought about it like this before - or, never needed to think about it like this. I don’t need a reason, an explanation, behind my own actions during sex. I’ve never much been into role playing - I’ve written before that while I am into sensation, Callie is into power. And this is just how her mind works: she needs to keep it occupied, otherwise it will wander, create scenarios, work on overdrive continuously.

Role playing has rarely come into my sex play, and is almost never in my fantasies. So, I told her some of this.

At the same time, there are some places in sex that I’d like to go, things I’d like to explore, like force and other power dynamics, and sometimes I am just too damn sweet during sex for my own mind to let go and really get raunchy, or mean.

I feel guilty - I get afraid of taking things too far, of hurting her, of being too much, too strong, too overwhelming, somehow crossing that line into … exploitation.

And some fantasies, no matter how much I am interested in them or that they turn me on, I feel so guilty about, I’m afraid to touch them.

Like, for example, force. If it’s just she & I rolling around on the bed and she’s resisting me a bit and I’m holding her arms above her head or bending one behind her back, it’s still just her & me, and it’s about sensation, being present, playing with our bodies. But thinking about pretending to be in a situation where I am playing a role that is going to take advantage of her, I lock up.

I mean, that’s not nice. In fact, I think it is completely wrong of someone to do. I think that’s pretty easy to understand.

I hesitate in the force-power play even without the fantasies, when the roles are added in there - especially socially or emotionally charged roles - I feel blocked.

But underneath that guilt, I want to play with some of these roles and power dynamics. I am definitely turned on by it, just a bit scared of it too.

Another thing Callie has mentioned in passing that she likes is age role playing, where someone is much older or younger than the other person. So we talked about this; it’s another area where I feel a lot of guilt. Imagine a scenario where I am an older guy, and she is a young girl, teenaged, fifteen - I would never want a girl to be in that situation, why would I want to play the part of someone who was taking advantage of her? Especially in a society where that happens all the time?

And Callie said: “Well, if you don’t fetishize little girls, then it probably wouldn’t work for you.”

Yes, true. I don’t fetishize little girls. I don’t see them as sexual - not even teenagers, either, though their sexuality is often oh-so-explicit.

But I do fetishize Callie. And I’m do believe that we carry around every age of ourselves inside, teenagers and pre-teens and little kids, even some older and wiser versions in our psyches somewhere. What was she like as a teenager? What kind of power did she have over older men?

I’ve seen photos of her from her childhood, and definitely found myself thinking that I was attracted to her fourteen-year-old self in a way that made me very uncomfortable. I felt like a bit of a pervert … but I am also very curious.

Here’s the second part of this process of guilt and fantasies for me. I feel like there is a conversation that needs to be had before ever playing a fantasy through about the why behind the fantasy. What is this pulling on for you? Were you ever in this situation? Why is it sexual, why is it appealing? I really want to know that stuff, to clear the air and our minds of whatever is being pulled on inside of us in these scenes, because I don’t want to do any damage.

I know sometimes people play out sexually experiences that happened to them. Looking at that list of the scenarios I came up with, the ones that turn me on the most are the ones I was involved in, or nearly involved in - and they are also the scenes I am the most terrified of.

But I think those scenes can also be replayed and re-created in ways that are healthy and ways that create opportunities for growth and healing. I am so, so interested in those moments, in those scenes.

Sex can be a powerful healing force.

So, we talked about this. Why force, why the attraction to being a young girl (or exploiting one), why is power sexy.

This feels like a whole new level and interaction and way to approach sex and role play for me, and for Callie & I together. We haven’t done this yet, but we’re talking about it (a lot) and beginning to plan some scenes.

Favorite scenario from yesterday: I’m a security guard, and I catch her stealing lingerie.