Posts Tagged ‘sex’
Before the door is even all the way open, I’m on you, slamming your upper back against the wall in the hallway. I’d been waiting for you. Heard your car outside and keys in the lock. Stayed half-hard all day, waiting for this moment where I could catch you off guard and suddenly, make demands and put forth my needs, use your body.
By way of a welcome home, I growl, “Hey, little boy.”
You whimper and melt into the wall, your knees sinking already, keys still in your hand. I shove you aside and close the door, keeping my forearm across your collarbone. Maybe you try to say hi Daddy, sometimes you do that, you’re supposed to reply audibly to me when I address you, but maybe your mouth says it without any sound behind it, maybe I’m keeping your voice clutched in my fist at your throat right now. You don’t need it. All you need to do is what I make you do.
I take a step back. “Strip.” I say first.
You do. I watch. You hang your jacket and slide your tee shirt over your head. Kick your chucks into the small pile of shoes in the hallway and unbuckle your belt. Click your keys back on to your keychain. The heavyness of the objects in your jeans pockets pull them to the floor without much effort and you let them slide off and step out of them. I stroke my cock, thick and hard already, through my jeans.
When we woke this morning I didn’t get the time I wanted to play with you. Didn’t get to slide inside you and sink into that place where our bodies pull and push in synchronicity, simultaneously out when you’re in, up when you’re down. I don’t understand how it is that we compliment each other so well, but we do. I pulled your hand under the elastic waist of my boxers and made you jerk me off while I whispered stories into your ear, my arm around you, hand gripping your arm or shoulder or whatever I could reach. Jerk it, boy, yeah like that. Harder. Just a little more. That’s just right. But you had to go to work. And I had work to do, too, though my work has less of a clock-in-clock-out factor.
I like missing you. That low pull of longing, of want, is enough to keep me focused and productive when otherwise I might be wallowing. I like wanting you. Always better than having too much and craving space.
I get my most important tasks done and pause through the day to fantasize, just enough to keep me hard but not enough to get off. I want to be wanting when you get here. Maybe the second or third time I do this, the vision forms to take you before you’ve even walked in the door. These scenes come to my mind almost fully formed sometimes, like a film I’m watching rather than something I’m creating. When I wonder what next to do, I just watch and listen for a minute, and it shows up.
You drop your tight white boy briefs next to your jeans and as you’re straightening up, looking at me shy with just a slight shiver in your shoulders, I lock the door behind you and I’m ready. “Down.”
You drop effortlessly, in one fluid movement, and I push your mouth to my zipper before you’re even situated. You lean into my hips and bite at me through my jeans. I lean against the wall and relax forward into your mouth. It’s a relief to have you home. It’s a relief to have your mouth here, wherever I put it. It’s a relief to have that control, a relief to know you’d do it, whatever it is, whatever I told you to do. I don’t need to execute that ability constantly—the knowing that it’s there is relief enough, most of the time.
Except sometimes, when I need to feel you supple and soft, feel you harden when you get it right and fall into the job I set for you to do. Just this. This is all you need to do right now, your mouth your tongue right there, your body relaxed and giving in, giving over, always giving it up to me.
You hum a little through your throat and I feel it vibrate against my cock. I feel the weight of the day, of the work, of the hate mail navigated and the dozens of hustling emails I sent with pleas, draining out of me. I pull up from the earth when I breathe in and try to feel myself empty, ohllowed out, able to be filled. You press the palm of your hand gently against my cunt, just enough for me to feel the pressure. Support, something solid for me to lean into. You catch the head of my cock in your mouth through my jeans and suck just enough for me to swoon. I unbuckle, unzip, pull it out while your hand kneeds my lips swollen and hanging like balls.
You suck me down slow and easy, slide it in, each inch slow until I’m all the way in your throat. “Swallow it down, my good boy, you know how I like it.” The thought of shooting, emptying out right here, pressed deep down into you, makes me shudder. I breathe into it and that rhythm, that rhythm takes me, moves me forward, the rhythm that starts in that bowl in my hips like a quake and starts moving me almost involuntarily, and I slide a little deeper into your throat and you open, open, open.
We writhe and rock and move together for a while. I let the pressure keep building, that pressure that started early this morning before you had to go to work, before we peeled ourselves out of the soft jersey sheets and made coffee and got dressed and were responsible. Or maybe it started when we met, or maybe it started long before we met, maybe it’s just something I have, that craving, that desire for taking and takedown. I watched you go out the door and felt that growl of want, not yet satisfied. What will satisfy me? Even when I get “enough” it isn’t exactly enough, it’s only temporary. I always want more. And you always give more.
“Enough,” I pull out, immediately feeling the lack, the emptiness where I used to feel held. “Hands and knees. Crawl.” I walk to the bedroom and strip, lay out the waterproof sex blanket over the sheet. I almost switch to the bigger cock but decide I want to fuck his ass, so I’ll keep this one on instead.
You’re breathing hard when you get to the doorway. You like crawling. Makes you feel controlled, it’s not something you would do without being ordered to. It makes you tremble and swell. I can see how you are pinkening between your legs.
I pull you up by the chain around your neck (“Up. Come on.”) and onto your stomach on the bed. Your open mouth is against the mattress, biting at the jersey sheet, arms twisted to hold you, ass up, legs splayed open, back curled. You know what’s coming. My thumb against your back hole and you moan and open even further. Your hole is so pretty and shades of rose (sometimes I really understand why erotica stories call it a “rosebud”) and I want to plunge in. I squirt lube right onto your hole, a generous line up my cock, and press . The head is the biggest and thickest, so pronounced on this particular cock, but you push back against me and moan Daddy Daddy and I can do it, we do it together. I go slow even though I want to plunge. I want to feel myself buried to my balls in you. Falling into you. But I restrain, and the tension between what I want and what I do feels palpable. I lean forward, hold my weight off of you while I slide in. Take a bite of your shoulder as my chest melts against yours, still holding my hips up. Slow, slow. Wait. And then you whimper and I feel your skin against the front of my hips and we’re there.
I sink against you. You hold me up.
1. What insight about polyamory/open relationships would you share with your younger self?
Don’t give more of yourself than you’re capable of giving. There have been a number of situations in my open relationship which have made me very uncomfortable, but I felt as though I shouldn’t feel that way for one reason or another, and so I would say I was okay with whatever the issue was and hoped that I would eventually become comfortable. I didn’t, and, in fact, it only got worse until it reached the point where I would consistently be reduced to tears and laden with anxiety. Both individuals have to develop and evolve together, and expanding the open aspects of the relationship need to be guided by the least open/comfortable person, not the most.
2. What has been the hardest thing about navigating multiple relationships, and how have you overcome that?
The hurting. It is inevitable that at some point both individuals in the open relationship will get hurt. Whether it’s jealousy, misunderstandings, insecurities, STD scare, or any number of other issues, being part of an open relationship exposes you to a plethora of tribulations and pain that will need overcoming. Overcoming being hurt isn’t possible — which is important to remember when considering your ROI vs cost — but you can address each issue as it arises (or before, if you can foresee it) to minimize future hurting.
3. What has been the best thing about being open/poly?
I won’t lie, the sexual variety has been pretty fantastic, but I suspect that’s the more obvious benefit, so instead I would say the resilience of our relationship. My mate’s brother once asked him, after discovering that we were open, if he was worried that I might leave him for someone I was having sex with. His answer was, “No, because if our relationship is so bad that it can be ended by good sex, then it wasn’t good in the first place.” Because we’ve expanded our sexual experiences as a couple to involve other people, we’ve removed an emotional weak point that is often exploited in traditional couples.
4. Anything else you’d like to add?
- Don’t sleep with your roommate(s).
- Never compromise your morals, convictions, or safe practices for anyone.
- Remember that the health and emotional wellbeing of you and your mate is paramount.
- Don’t use an open relationship to fill the gaps in your current relationship, or to transition to a new person.
- Don’t have sex with a lot of people just because you can. An open relationship isn’t an invitation or an obligation to be promiscuous.
- Don’t use an open relationship as a way to compete with your mate sexually. If you’re having vindictive or equalizing sex, you’re gone astray.
- Always be completely open with your mate. This will save you so much strife.
- Always play safe.
- Remember to put your relationship first, and playing with others somewhere down the list.
- Be mindful of playing with people who are, for one reason or another, emotionally vulnerable. Don’t play will people who will get attached, or angry for one reason or another, or jealous, or otherwise be unable to handle being part of your open relationship. This will take some practice, but trust your gut and learn from your mistakes.
- An open relationship isn’t accountable to anyone but those in it with regards to what you’re comfortable with. Just because other couples or individuals are comfortable with something, that doesn’t mean you need to, or that your open relationship is somehow inferior to theirs, even if you never become comfortable with a given practice. Whatever you and your mate are comfortable with in any given moment is what’s right for you, and there’s nothing wrong with that moving more or less open.
This story contains Daddy/girl language, rough sex, and lots of body fluids. This has been your trigger warning.
“Will you pause it for a minute? I have to pee.”
Kristen gets up from the couch and I grab for the remote, hitting pause on the second porn flick we turned on tonight. We’d shared a bottle of wine. I knew she was bleeding, since earlier in the first film, unimpressed by one of the girl’s one-finger banging techniques, I shoved three into her to illustrate that cunts can take more.
Well, maybe not all cunts. But hers, obviously.
She was wet, and moaned a little, making a little mewl of protest when I slipped them out. My fingers came away with just a little blood and I wiped them on her leg. Read More
Do y’all remember the Sugarbutch Star stories? It was a series where readers sent in a scenario and I wrote up the story. This is the last of the 5 stories from the 2008 “contest,” the others being Eileen, Matt, Green-Eyed Girl, and Maze. This story idea comes from blkndblue.
Warning: This story is long, about 18 pages. Click the “read more” at the end to read the final scene (it’s worth it, promise). I figure it’s a good way to kick off a (happy, sexy) new year.
Thanks to Dacia & BB Rydell for help with edits!
Sugarbutch Star: blckndblue
THE PINK DRESS
Emily emerges from the dressing room slowly, suddenly shy, though I’ve seen her naked in dozens of compromised positions. She fidgets with the dress, her hair, sucks in her stomach, but her eyes are lit up and she’s biting back a playful smile. She wants to wear this dress. Her inner three-year-old princess is aflame. “What do you think?” Emily asks; but the question isn’t really about my preference. She wants me to want it so she has permission to wear it. Then she doesn’t have to want it for herself; she is absolved of her own desires. I want to her to have permission to want anything on her body that she is drawn to, regardless of its gendered implications.
I finger the skirt of the baby pink dress, its satin fabric, abundant for its near-full skirt. She looks amazing in the plunging neckline in a gentle scoop, which shows off her round breasts generously. Sleeveless, it gathers at the waist where a thick white band wraps around, tying in a ribbon at the back. It could have been a bridesmaid’s dress, or a prom dress, or maybe someone’s fancy party dress. She’s been eyeing this dress in the window display, and today was the day it came down. She asked them to set it aside for her.
“So?” She is trying so hard to be patient. The words come out in a rush. “Do you like it?”
I come up behind her as she looks in the full-length mirror barely visible behind racks of gently used clothes. I wrap my arm around her waist, pull her gently back to me as she sighs, then smooths the skirt down.
“I think it’s perfect,” I say, my lips next to her ear. “No question.”
“Really?” She’s not sure I mean it, but she wants me to. “But it’s so … femme.”
“Yeah, it is,” I say.
“But, I’m not femme!” She argues.
“What do you mean? Of course you are,” I say.
“No, I mean …” she struggles for the words. “I’m not high femme. I hate that term. I almost always wear jeans and tee shirts.” We’ve been dating for on and off for a few years. We both have primary partners, but we make time to play and go on dates. When she dresses up, she adds heels and lipstick, rarely anything more. She has some impressive lingerie, but seldom wears dresses. She wears power suits for her professional office work, where she has to keep control and is in charge of a dozen people’s activities on a daily basis. She spends a lot of time looking put together, climbing the corporate ladder, and fighting the male privilege in her office, and she’d rather kick around in something comfortable and durable when she has the option.
“I know that’s what you prefer, and it’s perfect—your ass looks great in jeans,” I counter. “Look, you’re twice the femme most self-identified high femmes are. You’re at home in your body, awake in your skin, not judgmental about your own waistline or anyone else’s. And you have your circle of femme friends without gossip or backstabbing. If that’s not high femme, I don’t know what is.”
“Yeah, but you have to say that.”
“And I want to. I know the dress is a stretch … but it’s amazing on you. It looks like it was made for you. Doesn’t it?” I ask the passing sales girl. “Doesn’t it look like it was made for her?”
“It is, like, so cut perfectly for your body,” the girl, probably barely twenty, replies. “It makes your curves look even more curvy. It’s practically, like, perfect.”
“Yeah. Perfect,” I echo, and Emily grins at herself in the mirror.
“It is, isn’t it. Yeah. Okay,” she kisses my cheek and zips back into the dressing room, and buys the dress.
The date is my idea, and a surprise. I enlist her friend Sam, a gay boy also known as Serena, who does a fierce drag queen act and has every feminizing, over-the-top accessory one would need. We’ve been out drinking and galavanting dozens of nights in the past few years. Sometimes Emily and I go see him perform. Last time, he did a Judy Garland number with an incredible outfit from the forties that made him look like a black and white movie star.
“I could never do that,” Emily must’ve whispered to me five times that night, but the spark in her eyes told me that she wanted to. I knew Sam would love to see Emily all dressed up.
And tonight, with this pink dress, he’s going to help. I enlist Sam because Emily doesn’t have the femme things I need, and I can’t afford to buy them all. I meet Sam around the corner and pick up the fluffy underskirt that’s used to puff out full skirts, called a crinoline.
I knock on Emily’s door, and she throws it open. “I’m here to pick up the dress,” I say, after kissing her hello. She fetches it from her bedroom, still in the thrift store’s lavender-colored paper bag with their logo on it, and hands it to me across the threshold.
“Thank you. Now, you remember what I told you? What’s the plan?”
“First, I’m getting my nails done across the street. Then I’m going to go to Sam’s at 5pm to get my hair and makeup done. Then I’ll come meet you at your place, and bring the bra and panties.” I know she doesn’t wear the white bra and panty set with the lace trim often. I like that she saves it for me.
“What time, at my apartment?”
“Good. Perfect. Don’t be late,” I add. As if she would be. She shifts her weight from foot to foot very slightly and I can see her ears beginning to flush pink.
I tuck the box with the crinoline under the arm that holds her dress in a shopping bag and draw her to me with the other, smiling as our faces get closer, drinking in her skin and hair and the sweet way her body fits.
“I won’t. I promise.”
“Good girl,” I say, and kiss her.
At seven twenty-eight, she knocks on my apartment door. I greet her with more kisses and lead her into the bedroom before she sets her purse down. Some of the things are laid out on the bed: the crinoline skirt, white thigh-high stockings, a white garter belt, and her new pink dress, which I had dry cleaned and pressed just this morning. I see her hand flicker slightly as she reaches out and touch the dress, then pulls it back and makes a fist.
“Are you ready for tonight?” I take a seat in the small armchair in the corner of my bedroom and I take a sip of the glass of water I’d poured just before she arrived, with extra ice so she can hear the clink of it in the glass. She nods. I notice Emily picks at her nails, then stop when she realizes she is probably chipping her nail polish. She must be nervous. The icy liquid is cool in my mouth and I feel it run down my throat. Her chestnut hair is mostly a silhouetted shadow, but I can see it is piled on top of her hair in spirals and curls in a way that is much more complicated than she would usually entertain. It reveals the curve of her neck, which swoops into her collarbone and, later, will lead right to her cleavage.
“Did Sam send you with jewelry?” I ask.
“Get it out, and put it on the top of the dresser.” I cleared it in anticipation. She goes to her bag, removes a couple small boxes and a tiny clutch purse, then arranges it all so each are neat and not touching, then goes back to standing, shifting her weight from foot to foot and looking around the room.
“Take off your clothes,” I say. “Slowly. Fold each piece and put them on the bed.” She starts with her v-neck grey fitted girly tee shirt, quickly pulling it over her head. “I said slowly,” I say, and she pauses, moves a little slower. She folds the thin fabric easily and places it on the bed, then steps out of her low, simple black flats. She’s not wearing a bra; she often doesn’t, not encouraging the curve of her breasts to be shown off. Her bare skin glows in the lamplight. She pulls down her tight blue jeans and steps out of them, folding them a little thoughtlessly, but I don’t tell her to slow down again. She slides her plain black cotton underwear down over her legs and adds it to the pile. She fingers the worn grey tee shirt and looks at it longingly, then glances at the lingerie laid out on the bed and moves her hand to touch it, smiling as her fingertips make contact, her face relaxing.
She stands again, naked this time, crosses her arms in front of herself, then drops her arms and holds one wrist with her hand. After a moment she straightens up, and clasps her hands behind her back like she is presenting herself to me, a blank canvas. She shifts her weight from foot to foot, drops her hip, but tries to stay still. She bites her lip.
“Very nice,” I murmur from my corner. I uncross and recross my legs, ankle to knee, and pick up the cane from next to my chair. I can see her nipples, even in the shadows, hard and dark. “Get the bra and panties out of your bag, lay them on the bed.” She does. “Now, get dressed. Start with the garter belt.” She takes a breath and turns to the bed, picking it up and sliding it up her legs, securing it in place.
“Now the stockings,” I say. “And the bra. Leave the panties off, for now.” She dresses quickly, fumbling a little with the clasps and the delicate fabric, sitting on the side of the bed to fasten the stockings to the lace. “Now the petticoat.” She looks at me a little questioning, then realizes I mean the white crinoline skirt, and pulls it in a flourish from the bed to step into it.
“The dress,” I say. She pulls it over her head, evens it over the petticoat, and does her best to tie the white bow behind her back. With the extra layers of under the skirt, the pink dress is even more stunning than it was in the store. “And the jewelry,” I say, as she admires herself in the mirror hanging over the dresser. She takes a step closer and puts small two-stone droplet earrings in; they’re delicate, just an inch or so long, hanging just enough to move when she does and sparkle when the light hits them. She reaches for the matching necklace and raises her elbows to buckle the clasp behind her neck. Her fingers tremble and it takes her three tries to hook it correctly.
Emily steps back and looks at her reflection, buzzing, hardly containing the thrill of happiness at her own reflection. Her smile is as big as I’ve ever seen it. She turns her head, then shakes it to see the sparkle of the earrings, tilts her chin down to see her fancy hair-do, fluffs the skirt out to the side, and finally twirls, watching the dress in the mirror and laughing, giddy.
“Come here,” I say. She turns her head to me and takes short, quick steps across the room to where I am sitting next to the window in her stockinged feet. She notices the cane I have been stroking.
“Is that for me?” she asks.
“It’s for your ass. For later.” I set it on the table with my glass and reach out for her waist, pull her on to my lap. “Very nice,” I say, stroking the skin on her arm, the the slick fabric of the top of the dress, brushing my fingers against her breasts and nipples. I offer my mouth for a kiss and she wraps her arms around my neck, opening her mouth, gently kissing back. “You look gorgeous.”
“You really think so?” she bats her eyelashes. She looks like a sunrise, peeking over the horizon, breaking the dark, reaching up into the sky. She still looks like herself—just polished up a little, enhanced, prettied.
“Really. Very much.” We kiss again and I get lost in her lips, her tongue, the way her hands grasp gently at my neck and shoulders. I let my hands trace her stockings, wander up under the many layers under her dress. “Do you like the crinoline?” I ask.
“Oh yes,” she breathes. “Is that what Sam gave you?”
“Yes. On loan.”
“It’s so … pretty.”
“You’re pretty, sweetheart.”
She smiles shyly, kisses me again.
“Did you like getting your nails done, and your hair and make-up done?”
“Yes! It was really fun. More than I thought it would be. I thought it would be weird but it makes me feel fancy. And important. And … ” she lowers her voice, her eyes a little and brings her hands up to straighten my tie, pinch my collar between her fingers. “And I knew I was doing it for you. That you would like it.”
“Mmm. And you did a very good job getting all ready for me.” I find the patch of skin at the top of her stockings, her sweet smooth inner thigh, and rest my hand there gently.
“I like doing what you say.” It lets her mind rest, she’s explained to me, and is a relief to trust enough to follow orders instead of second guessing and being in charge of everything.
“I know. And I have a few more things to do before we go to dinner. Are you ready?”
“Yes.” I toss her a questioning look and she corrects herself. “Yes, sir.”
“Good.” I take a breath. “I’m going to warm you up for the evening. I want to give you something that will serve as a reminder that this body—” I shift my hand quickly and palm her pussy, making her gasp, then quickly attempt to maintain her composure and keep her eyes open, looking at me, “—this pretty little body of yours is mine to play with tonight.”
She nods, quick, tiny movements of her head, and her eyes flicker with a hint of nervousness.
“Are you worried?”
“No, sir. I know you will take good care of me.”
“That’s right. Good.” I move my hand away and she breathes in, her thighs quiver. I lean in to kiss her again, bring my hands to her waist and then up to cup her chin, neck, the back of her head, careful not to mess up her hair. She relaxes, her mouth softens. She tastes like cream.
“Get up and bend over my lap. I’m going to make some marks on your ass before we go out.”
She delicately places herself over me with more care than usual, though we’ve been in this position many times. She doesn’t want to muss herself. This chair is perfect for over-the-knee spankings, with wide, low arm rests. Her stockinged tiptoes just barely reach the floor. She arches her back automatically, presenting her ass and slit to my right hand.
I caress her neck and shift my arm to cradle her collarbone and begin peeling up the layers of her pretty pink dress and petticoat. The peach of her ass is perfectly framed by her stockings and garter belt, the layers pushed up to her hips. Softly, I bring my hand to her thighs and ass and begin caressing.
“So nice,” I murmur into her ear. I start with some rapid tap-tap-taps with my fingers tight together on the sweet spots on her ass, the ones that make the flesh shake and that makes her muscles relax. She sighs, keeps breathing, keeps filling her lungs and breathing into the increasing sensation. She’s done enough yoga, we’ve played with enough sensation play—she knows how to open.
I keep going with light taps and occasional full-handed gentle swats until I can see a pink flush starting, just a hint. She loves being hit; she snuggles down into it as if I was reading her a bedtime story. I increase my swing, raising my arm higher, and give her a few open-palmed, but not too hard yet. Her skin is fair and it is easy to leave long-lasting marks, easy to bruise and break capillaries on the surface of her skin.
Which is exactly what I want.
I continue, warming up her ass until it is bright and hot, flushed and red, beginning to show some darker parts where it will be easy to leave marks. She moans, sinking into me, humming with pleasure. When we are both warm, when my shoulder feels like it is loose and liquid and easy, I raise my arm high and let fly a few hard wallops, pausing in between, but just for a moment, to let her react. Her body shudders and I feel her tense, then relax, over my lap. I can feel the impact of my hand through her and onto my thighs, can feel her growing heat and intensity. I let my hand down again, and again, allowing gravity to pull me, sucking up the power she’s handing over while I have her upturned and stunned, ready to take more.
I lean down so my mouth is by her ear again. “You are doing so well. Your ass is nice and red and starting to bruise. I’m going to get my cane out now.”
She manages to move her neck slightly, twists her head and looks up at me, and nods just a little. I grip the cane from the side table and it feels hard, solid in my hand. It slices through the air with a hiss and I love the way it extends my arm. The last time we used the cane, she told me every time she sat down, she thought about what I’d done and how I’d used her. That it made her wet to have to act like she could sit normally, when really it was excruciatingly painful. That’s how I want it to be tonight. Something to take away from the terror of being so femme, over the top femme, in public. Something to distract her.
The first hit with the cane is a little off, and not too hard. She gasps but does not squirm. The second is two centimeters toward her thighs and harder. Immediately a light stripe appears. She jumps a little and lets one arm drop, grabbing on to my pant leg, as she lets out her breath in a long thin stream through her teeth. The third, quicker now, is at a different angle, crossing the first two. She sucks air back in and lets out a laugh, bubbling like champagne, thrilling and tickling my nose. Good. She’s warm, dropping into that blurry area past the sharp pain and into sensation.
The next dozen or so are more rapid, in succession, some lighter and some fiercely hard and biting. She takes it well. She gasps and begins squirming, but not away, not off of my lap, just to wriggle and shake off some of the building energy. I fall into a pattern of hard-hard-quick-quick-soft-caress where my eyes glaze and my cock hardens. I can see her slit becoming wet, swollen, as pink as her sweet round ass cheeks.
The striping is beautiful, thin welts rising on bull’s eye circles where my hands bruised her first. I can already see some small places where my handiwork reveals itself.
I lean low against her ear again. “It’s going to hurt for a while when you sit,” I say, as a slide the cane away and bring my hand to her singed bottom. It is so tender and sensitive, like stretched skin over the frame of a drum, reverberating with every touch.
She moans. “Thank you, sir.”
I bring her up onto my lap again to hold her for a minute, her ass already uncomfortable. Sitting at the restaurant is going to be excruciating. I stroke her hair and neck, offer her some water and she takes it. She snuggles against my chest, lets me sooth her, then rocks a little on my lap and I realize she is searching for my cock.
“Looking for something?” I ask.
She falters, remembers herself. “No, sir.”
She nods, tries not to look disappointed.
“I have one more thing for you before we leave. Ready?”
She nods again, brings one hand up to her mouth to bite one finger, a childish gesture of nervousness.
I almost laugh. “Nothing bad, sweet girl. This is a present. A surprise.”
Her eyes light up as she slips off my lap. I go over to the closet where I stashed the bag, then sit on the bed, patting the bedspread next to me. She shuffles slowly over the thin carpet in her stockings, smoothing out the skirt of her dress and walking slowly because her legs are still weak from being bent over my lap and beaten. She brings her hands behind her, to touch her ass, as she walks, and I can tell the muscles are already sore.
I hand her the bag. She gives me a shy smile and pulls the shoe box out of the plain white shopping bag. Her eyes widen. She realizes she only brought the flat black shoes she came in.
“Oh!” She exclaims when she opens the box. They took me a few days to find: the exact pink shade as the dress, with a small strap over the arch of her foot, delicate white trim, and a tall, thin four inch heel. She pulls them both out and pushes the wrapping aside on the bed, holds them flat in her hands, grinning. “May I?”
I slip off the bed to kneel in front of her, holding my hand out. She blushes—adorable—and hands the shoes to me, offers me her foot so I can slide them on, one at a time.
She laughs, and twirls. “I feel like these are fancy shoes from my fairy godmother, and I’m Cinderella!”
“You look amazing,” I say, standing up, and offer my hands to help her stand. It may take a minute to get used to them. I take her in my arms again and she melts into me, offering her mouth for more kisses.
When I pull away I take the delicate white panties still laid out on the bed and offer them to her. “Put these on, we wouldn’t want you getting your dress any more wet than it already is. Freshen up your lipstick and let’s go to dinner. Are you hungry?” Her lipstick is smeared from kissing me, and she hasn’t noticed. It’s probably on my mouth. I quickly wipe my mouth in the bathroom mirror and when I come back in, she’s sitting on the bed to step into her panties, pulling them up over her shoes and stockings, leaving them on the outside, so they can be the first thing that comes off later. She stands and picks up the tiny clutch purse she laid out on the dresser, checking her make-up in the dresser mirror. I slide my suit coat over my shoulders, watching her twist the lipstick up and pucker her lips. She would never do these things on her own, but she is flushed and giddy and thrilled, ready to go.
Kristen and I spent the weekend in Chicago, in part to attend a concert, and in part because tomorrow, December 13th, is our third anniversary. This story does not involve daddy/girl play specifically, but there is once when she calls me Daddy. Because that’s what she does. It does involve some rough sex. Just a warning.
While Kristen showers, I put my cock on under my boxers, leaving my tank top on. She emerges with the white hotel towel wrapped around her, hair wet and dripping onto her shoulders. When she sits onto the bed I stand between her legs and pull her towel open, then grab her hand, lifting her to stand.
I pull her to the hotel’s floor-to-ceiling window that looked out onto the Chicago river, Lake Michigan, and a dozen other skyscrapers nearby to our hotel, leaving her towel on the bed. I take each of her wrists and press her hands into the cold glass, feeling the outside freezing temperature through the thin barrier.
“Leave your hands there,” I say. I press into the back of her body, kissing her neck. She shivers, a ripple up her spine, and I feel it. “I’m going to take you down. You can stop me anytime, but you’ll have to safeword out. I don’t care if you cry or fight me.” She’d been emotional all day, it is possible she’ll cry. And I’m guessing she needs the release.
So do I.
She nods. “Red?” She doesn’t have a usual safeword aside from yellow and red.
“That’s fine.” I reply. “Okay?”
She nods again. I kick her legs open, press harder into her, and drag my hands along her naked body, the curve of her ribs down to her hip, then over her ass, and I plunge two fingers between her lips, hard and right deep into her. She gasps, arches her back a little to push against me harder. I pull my fingers out and spit on them for lube, inadequate but better than nothing, and work them back in. Pushing deep. Fingering her g-spot and cervix and reaching around with the other hand to touch her clit.
The first time she comes, she drops her hands from the window, tits still pressing into it, cheek against it, her breath fogging up the glass. “Who said you could drop your hands,” I growl at her, and she raises them back up to shoulder height, moaning.
“Come for me again.” I work my fingers inside, mouth on her neck and next to her ear. “You see all those windows out there?” She opens her eyes, looking. We’d remarked the night before that we could watch the TV in the person’s apartment across the way. It wasn’t close enough for much detail, but shapes and people surely.
She swallows. “Yes.”
“Wouldn’t take much for someone to notice you here, getting fucked, getting played with. My little toy. Pretty girl, you think someone is watching you right now?” She comes again, twice more, shuddering against the window, torn between wanting to press into it to hold herself up and pulling away from its chilling temperature.
I want to get rough with her. I know it’s easier to do that—for her; she can take more—if she’s already come a few times, hence the warm up. I want it quick, urgent, and dirty.
I pull back, twist her shoulders to swivel her body around. “Down,” I said, pushing on her shoulders. She almost stumbles down onto her knees on the scratchy hotel carpet. I pull my cock out, the big one I like to fuck with, my favorite, the one that is a little too big for blow jobs, especially in her tiny mouth, even considering her skill.
But right now, I couldn’t care less.
I feed it to her, sliding it onto her tongue. “Put your hands behind your back.” She doesn’t need to be doing the work, this time. She is just a hole. She closes her lips over the head but not much deeper. “Get it all wet.” I pull out and rub it against her mouth. She swallows, works her mouth for more saliva, and opens again, and I push inside, deeper this time.
“Come on, you can do better than that. Take it. Take it down, good girl. Let’s see what you can do.”
She tries, but it isn’t enough. I grip her hair at the base of her neck and push, trapping her between the pressure from my hand and my cock. I thrust in a little deeper each time. I can see the teeth marks in the saliva on my cock. I almost tell her to stop using her teeth, but I don’t really care. I can’t feel it, anyway. If she needs to regulate that way, it’s fine.
I push too deep and she gags, closing her mouth, twisting away so I’m not lined up anymore. “Come on,” I urge again. “You’re fine. Do it again.”
She parts her lips and I shove in. Deep again, more, in and out, until she gags again. I give her a moment and touch my cock back to her lips. “You’re not done yet. Again.”
She looks up at me and swallows, hands still behind her back. “Stick your tongue out,” I say. She does, and I slap it with my cock, four, five times, then shove it in. She closes her lips and sucks, and a jolt of something goes up my spine.
“That’s good. That’s my good girl. That’s right.”
She sucks it well and I grip her head again, forcing it in deeper, holding her against my cock at the deepest point until she recoils. “Breathe,” I remind her. She gasps, regains her breath. I slap her tongue again, slap her cheek, and shove it back in.
I’m hard and thick, pulsing, in her mouth. I can smell the come on her thighs, dripping. Her cheeks hollow as she sucks and looks at me with pleading eyes.
I pull out and shove her again. “Down.” She flattened onto her belly, twists, on to the carpet. “Hands and knees,” I say, kicking at her thighs. “Crawl. Go.”
She moans and picks herself up, slowing moving the short distance from the window to the bed. I shove my heel into the flesh of her ass, knock her off balance. “Keep going.” I get a few kicks in with my bare foot, light and easy, but I feel it reverberate through her. She has been so quiet so far, dropping so quickly into that space of submission and giving over, barely talking, and I suspect this—making her crawl, kicking her—will just exacerbate that. But she is in it, feeling every touch and every inch, showing me everything with her eyes and the flushes on her skin.
“Up,” I say, and she slowly moves to stand, faces away from me, and I shove her, bend her over the bed, hand finding her hole again, spreading her lips open with my hand and positioning my cock. I spit down between her legs, into the crack of her ass, as low as I can, and make circles with the head of my cock to rub it around before pushing inside her. I pull her hips up as I thrust. “Arch your back. Give me that hole.”
She pushes back into me just as I thrust and I get that angle, that tension, that friction that I love, that shoots energy right up through my core and into my heart, throat, and up and out, back into her. I reach around for her clit while thrusting and I thrum it and she comes again, I feel her tighten around my cock but she doesn’t push me out. But the bed is not quite the right height, my knees are bent and I’m pulling her hips up to me, and I need another angle.
I pull out and pushed her legs together. “Turn.” She does, quickly. I shove her back onto the large king hotel mattress and grip her thighs, pushing them apart as I climb onto the bed between her legs and palm my cock, rubbing it against her slit again.
She moans and arches her back. Her cunt is pink and swollen. I spit again but she doesn’t need it, she’s wet and dripping with come.
I keep my cock in my hand and thrust in and out of her, shallow, a few times. She opens her mouth, hands above her head, fists reaching to grip the sheets, pushing against the headboard. I slide closer to her, in the deep V of her legs, pull out and slap her cunt with my cock, aiming the ridge of the head right at her clit. It works, and she comes quickly, come spraying as I keep slapping. I see it splash onto her breasts, onto my boxers. Good thing the hotel towel is under her. She convulses, thrashing against the bed.
“That is so good. So good baby girl, you feel so good.” She whimpers, crying out as I get harder, releasing and open but not in a big dramatic display. “That’s my girl. Come for me again, come on pretty girl—right on my cock, do it for me. Come on.” And she does, almost on cue, thrashing between me and the bed. I take her wrists into one hand, push against her, keep fucking. I’m close, working my clit against the harness strap as much as I’m working into her.
“Thank you Daddy, thank you Daddy,” she manages. Her low sweet voice sends a jolt through me.
“Open your mouth.” I release her hands, though keep my forearm on her shoulder, holding her down, and slide three fingers into her mouth. Her tongue is wet and soft. “Come on, do it. Suck me down. Take me in to all your little holes so I can fill you up. Come for me again. Come on, do it.” She does, mouth open around my fingers, body rattling, legs kicking on either side of me, gasping. My cock stays inside and I work it. “That’s not enough,” I growl into her ear. “Again. More. Come on, I know you can do it.” She comes again, bigger this time, yelling out, spine undulating. “Good, yes, that’s what I wanted, very nice. That’s my girl. That’s my little toy to play with, my little holes to fuck. Such a good girl.”
She quiets and I pull up to slap my cock against her cunt again, making her come a few more times before I’m done with her, pulling back.
I didn’t come. I am still dressed, wearing the boxers and tank top I slept in. She barely touched me. But I’m as satisfied as if I came twice (a rarity), content and buzzing as I lay down next to her and gather her into my arms.
We kiss, curl into each other. When she gets her voice back, she takes a minute to tell me what she liked—”I liked it when you kicked me, made me crawl,” “I liked being against the window,” “I liked coming over and over for you,” “I like when you tell me what to do”—which she knows I like to hear as part of my aftercare. Lessens my top guilt. I hold her close and stroke her skin.
We lay together a while as our bodies quiet and calm, then I strip and get into the shower. Later in the day, doing one last sweep over the hotel room before we leave, I notice her handprints still on the window, and a lip print where her face was pressed up against it. Usually I hate leaving the oils of my hands in prints on glass, too aware of janitorial jobs that must clean up after carelessness, but this time, it’s so pretty, I can’t bring myself to wipe them away.
I’m starting to write a new column on SexIs Magazine, this time it’s an advice column called Mr. Sexsmith Says. The first one came out today, about stone identity and butches, and they’ll be published every other week.
I have a pretty decent stack of index cards from my workshops, as well as some unanswered questions from emails and from the Ask Me Anything Sugarbutch anniversary thread, so I already do have a lot of fodder for this new column.
However! I still get questions pretty frequently, and now that I have a place to put them, I invite you to ask me about things you’d like to know. No seriously, ask away. I can’t promise to answer all of them—I have no idea if I’ll get two or two hundred, so you know, I’ll have to do some experimenting here—but I will do my best.
So now there’s a sugarbutch.net/ask-me-anything URL, and a place specifically to submit questions. Please feel free to ask away.
It started with an email with the subject line “butch at your service,” and an offer for a blow job. And I thought, hm. Well, you know, I do like those. But I’m not usually attracted to boys. So, we’ll see.
Then at Summer Camp, rife made a point to say hello. We chatted a bit, attended similar workshops. I was surprisingly affected by his energy, his tender sweetness, the way he was clear about what he wanted and owned his desires but still bashful and shy, submissive. I watched him blush and bruise and cringe, and take it, when the person he was serving for the weekend gave him some punches on the arm, and I felt the urge come from down low to see if I could make him respond to me that way.
I’m not usually attracted to boys, but I was attracted to this boy.
The next day, chatting, he said shyly, “What’s your schedule like? I would love the opportunity to play with you.” He wasn’t looking at me when he asked that, and had trouble sometimes maintaining eye contact when we spoke. When I came near him, his voice dropped, quieter, and so did his eyes. His mouth curled at the corner with the slightest little lines of dimples.
I said, “I don’t know my schedule yet, and I need to check with my girl, but I would like that.” Kristen and I had agreed that I could do things to practice skills before she came down and joined me at Summer Camp for the weekend, but that if I was going to be doing any fucking, I would wait until she arrived, and she could be there to witness.
I could tell he was experienced as I watched him get hit for fun, make dates, talk about his adventures at the dining table, and play. I kept my eye on him as I continued teaching and attending classes, and later picked up Kristen at the train station, telling her that I thought I would be interested in playing with him. “He’s really cute,” she said after they met. “I can see why. I don’t have to be involved, but it’s fine with me if you play. I’d like to be there.”
I kept seeing rife all day, but hadn’t quite figured when we could play. In the morning we circled each other and didn’t talk, but I saw him looking at me, and he saw me looking back. The quiet attention got me hard. I made a point to go up to him and grip his upper arm, and whisper in his ear, “Good morning.” Later, I found him at dinner the next night and asked about his evening plans. “See me at the Cigars & Chocolate event,” I said, “and we’ll go do something after.”
He came in after I did, with his crew of folks, and I saw him scan the room looking for me. I got my boots done by a talented bootblacker, smoked a cigar, learned about ashtrays. When the place started thinning out, he came over to me. He and Kristen and I headed up to the barn, which was empty: one big room with a concrete floor, some platform bleachers on one side, and a mat and bondage trestle of sorts in one corner. Kristen sat herself on the bleachers. rife picked up a few unlubricated condoms from the bins laid out on the safer sex table.
I took hold of his unsnapped black shirt lapels, his binder and the skin of his stomach exposed underneath. He inhaled. I pushed with my fists to move him around a little, feeling our legs move together in a dance, feeling how he followed. Immediately he fell in to my direction.
“Anything I should know?”
He didn’t look at me, keeping his chin low and shoulders in a little bit of a shrug, letting me move his body around the room. “Bruises are fine. I like barriers. I’d like to suck your cock.” We said a few more things in negotiation that I can’t quite remember. He was direct and clear, but quiet, keeping his head curled down. I think this is when we kissed. Perhaps I asked if kissing was okay first. Then he asked, “Can I call you sir?”
I grinned. “Yes.”
He shifted his weight and started backing me up, moving me. I followed. “Where are you taking me?”
He stopped at the mat and trestle. “I’m a masochist, but not for concrete floors.” I found the pole of the trestle and leaned against it, pulling him to me and opening his knees a little with mine, finding his mouth again. He shuddered, body pliable, giving in easily and smoothly. There wasn’t a lot of kissing—so intimate with someone I don’t know—but we kept our heads close, him curled into my shoulder while I kept a grip on his body.
“Will you call me a faggot?” he asked quietly into my neck. I didn’t hear, asked him to repeat it.
“That’s what you like, huh, dirty boy.”
“Yes, sir,” he breathed out.
“Unh, god you’re so sweet,” my hands went to my belt, zipper, untucking from my harness. “Are you ready to suck my cock now?”
“Yes,” he didn’t move. I didn’t ask him to do it, but if he was ready.
I fingered the back of his head, his short and soft hair. “Do it,” I growled in his ear, and he dropped to his knees, in a flash had a condom in his hand, rolled it onto the tip and pushed it down the shaft with his mouth. I felt a surge of power and pleasure roll through me, up my legs into my core, as he sucked me in. I fumbled to tighten my harness, moved my hands back to his head.
He took the length of it down easily, his tongue gentle and persistent as he sucked. I leaned into the trestle, aware that Kristen was getting a show, that she doesn’t usually get to watch me receive from afar. I fingered his neck, cupped his jaw, touched his lips with my fingers and he sucked them into his mouth.
After a moment I broke away and leaned down to kiss him, his mouth wet. “You like that, faggot? Sucking my cock?”
“Yes, yes sir,” he managed, gasping a little.
“You’re good at it. Do it again,” and I slid back onto his tongue. “Mm,” I groaned. His hair was almost shaved all around except a wide mohawk patch on top, which I grabbed hold of to work in and out of his mouth, gently. Kind of.
“That is so good,” I leaned down to kiss him again. My cock was throbbing and hard. “You got me all hard, sweet little faggot.”
He swallowed and whispered up to me, “I want you to throw me down.”
“You do huh.” He was on his knees, thrown off balance with not very far to fall when I gripped his upper arms and pushed him to the floor. No fighting at all, just letting my weight take him, grounding him down into the mat. His eyes closed, he bit his lip, curled his small sweet body as he rearranged himself, getting his legs out from under him, and I worked a knee between his thighs. I held his shoulders down and reached between his legs, a little surprised he wasn’t packing, finding the heat and feeling my own cock harden in response, jutting out from my hips.
Small sounds from his mouth as he groaned and pushed against me, testing the feeling of being trapped. I gripped his sports bra and ace bandage binder in one hand over his chest and worked the other hand between his legs, over his jeans, and could feel him bucking forward, wanting more. “That feel good on your dick, huh? Getting hard for me?” I asked. He panted. I realized I didn’t have a glove.
“Stay right here,” I said next to his ear, pushing my body on top of his, my arms holding me up on the mat. “I’m going to get a glove. Put your arms over your head.” He did. “Stay like that. I’ll be right back. You alright?”
He nodded, quickly. I didn’t want to get up but wanted a hand down his pants, wanted to feel him, and trusted that staying in this position I’d ordered him in would only deepen his submission. I stood and took the ten or so steps to the supply table, picked up a glove and some lube packets. I looked at Kristen as I went across the room, but in the dark shadows it was hard to decipher her expression. Upset? Okay? Turned on? All three? I trusted she would tell me if she needed anything.
When I returned, I let myself look at rife a moment before bringing myself back down to the floor. His body quivered a little, waiting for me, arms still extended over his head, one hand in the other. “Hi,” I said as I knelt next to him, my eyes scanning over his black button down shirt open, his tight stomach, smooth skin. I ran my hand along the skin that was exposed and pushed at his body again, felt him groan and shudder in response.
I unbuckled, unzipped his jeans, fast, eager, and pulled them down on his thighs, not past his knees, left them high to give some restriction to his legs and thighs, and then pulled on his hips. “Turn,” I said, impatient. “Over.” He did, flat until I pulled his ass up to kneeling, his elbows out in front of him to catch his body weight as I pushed him down into the mat. My gloved fingers easily found his hole and slid in, one then two, then out again and along the whole length of him, feeling how smooth and supple, testing his responses. He was sensitive, back arching at the slightest change in pressure or speed. I slid my fingers back inside, turned my hand over and worked his g-spot, massaging, and he moaned.
Tearing open a lube packet for my cock, I smeared it onto the length and pressed myself behind him, sliding in awkwardly but fully. My jeans and his jeans were in the way, mine not pushed down any farther than his, our legs tangled, the angle wasn’t quite right. I couldn’t get that good drive, all the way in and out, but I wanted him to feel me behind him for a while, taking hold of his hips and pulling him back onto me. His back and neck arched, spine curled. I managed a building rhythm for four, five, six strokes, pushed my hips hard into him, held him to me, shuddering a little as I felt myself diving into him.
He kept breathing hard, mouth open and drooling on the dirty mat. I gripped his hair again, pushed his shoulders down. “That’s it, good boy,” I murmured, thrusting still, opening him up, my hips pulsing. “Fuck.”
I switched to my hand again so I could better feel his muscles, his responses. Fingered his clit and his back rippled. Thrust in hard and he smashed his cheek into the floor.
“You’re dripping wet,” I growled into his ear. I slid my arm under his chest and pulled him up to his knees. There was a puddle on the mat beneath him, another damp place where his mouth had been on the mat. We knelt next to each other, his knees apart, jeans bunched under his calves.
He nodded in response.
“Yes sir, I’m wet, sir.”
“You didn’t tell me you do that.”
“I’m sorry, sir.”
“No, I like it. I just didn’t know.” The sleeve of my sweater was damp, but I couldn’t tell if it was from him or from sweating. I kissed him again, his mouth open and chest heaving, lips swollen as I ran my tongue on them. I brought my left hand up to his jaw and held him there as we kissed deeper, then slid two fingers into his mouth. He sighed and moaned, swallowed them deeper, bent his head back to open his throat, kept them deep, then slid them in and out.
“Oh, that’s good, faggot. Sweet boy, that is so good.” My own muscles shuddered in response throughout my body, thighs contracting, and for a second I thought I’d fall over. I kept my mouth next to his ear. “Touch your clit with your other hand. Come for me again. Will you?”
He nodded, eyes lidded and mostly closed, and he slowly brought his hand between his legs. I could barely see what he was doing but could feel his body respond, tightening, his stomach crunching in as his hips tightened and thrust, just a little.
“Is that good? Does that feel good?” I teased in his ear. He swallowed and I felt his throat contract around my fingers. “I like being deep in your throat like this. You suck cock really well, little fag. Does it feel good to touch down there? Are you going to come for me again?” I kept going, pushing a little with my voice and my fingers, until his body convulsed and he squirted again, falling against me. “Oh that’s nice, good boy,” I murmured, running my hands along his body as he quieted.
“Is that enough, or do you want some more?”
He straightened up and looked at me, a little sly. “I could … take a little more.”
“Oh, you could, huh.” I could hit him, I thought, but I loved how sensitive he is to touch. Loved how he curls in response, gives in, takes it. I loved watching him come. I pushed him down again, on his back this time, pushed his jeans a little further down, and slid my fingers down his cunt again, still dripping and wet everywhere. I slid two fingers in easily and held his chest down with my forearm, then gripped his binder again, pulling at it, leaning my weight into him.
He held my wrist, groaned. “More,” he managed to say, and I slid another finger in, pushed harder in and out, twisted my hand so my thumb was up on his clit and pinky finger was below his hole, and thrust in. I anchored my hand above his shoulder so I could go in harder. He twisted under me but couldn’t move away from my grip, my knees holding his thighs apart.
“Is that what you wanted? More?”
“Say thank you.”
“Thank you, sir,” he whispered, just barely audible, in my ear.
“Thank you, sir!”
“Again,” as I thrust harder inside, fingering his g-spot, felt him tightening.
“Thank you, sir! Thank you, sir thank you … ” He trailed off, coming again, pushing my fingers out, and I didn’t let up, flicked his clit as he continued shuddering, mouth open so I slid my fingers back in, working them in and out, fucking his mouth and feeling his tongue swollen on my knuckles. I cupped my hand around him for a moment, then tapped and started slapping, which got a moan from his mouth and more convulsing from his stomach and hips, so I kept going, slapping, and I felt him squirt again, wetness dripping from my hand. Probably I was saying other dirty things while I touched him, I don’t remember. This time I got to watch more directly, and that’s what I wanted. I watched his muscles ripple and settle, ran my hands up under his shirt, clamored up next to him to feel his body along mine.
“You smell like a boy,” I said, his musky scent so different than what I’m used to. He laughed, and had this smile on his face by then, a grin, ecstatic and giddy, and I wanted to kiss him, slap his face, get him back on his knees. The hunger was still palpable, I wanted more. I also figured he had other plans, didn’t want to take up his whole night, and knew I should check in with Kristen. He sat up, pulled his shirt and tangled binder off. I tugged my jeans up, took my sweater off, my button down shirt underneath totally soaked through with sweat. I gathered the condom and glove, ripped lube packets, brought them over to the other side of the room, and grabbed some wet wipes for the mat. He took them from my hand, “Let me, I made the mess,” with that shy little side smile with the lines, dimples, at the corners of his mouth, and we composed ourselves to go back out into the dark night.
He walked Kristen and I back up to our room and went off to find trouble. It’s been an interesting experiment, for Kristen and I to play with other people, and we have been talking about it openly and being interested and careful with each other about it. That’s kind of another post I have brewing, how we are dealing with our particular version of monogamish openness. And don’t worry, Kristen wasn’t left out—she had her own adventures during Summer Camp weekend.
What was your first time strapping like? What advice do you have for strap-on virgins? My butch just placed the online order for her first cock, and I have no idea of what to expect.
Go slow. Use lots of lube. LOTS of lube. More than you think you might need, especially at first. It’s just a little messy, which is always better than having not enough. DON’T use silicone lube, as it’ll screw up your silicone toys.
Talk to each other, be as vocal as you can—even “ooh yeah ooh yeah” type of vocalizations will help give cues to each other about what feels good and what is not quite working.
Don’t be afraid to slow each other down or stop. It might just click and work and be amazing, but you also might want to just do it as something to try and to play with, at least for now, so don’t expect one or both of you to get off, especially not at first.
If you’re not used to penetration during sex, you might want to mess around with getting yourself off (or her getting you off, using her hands on your clit I mean) while she’s inside, but without much in-and-out motion, at least for now, while you’re getting used to the feeling of her cock.
The typical porn positions are the best, in my opinion, which is why they are so frequently used—missionary, and doggy style from behind (in various incarnations, like leaning over the bed, or with your head down on the bed instead of on all fours). In missionary, also try it with her sitting up on her knees, with her thighs under your thighs, that is often a really good angle.
Don’t be afraid to touch it, kiss it, lick it, suck it—that stuff can be really hot, though that can also be kind of delicate, so see how your girlfriend feels about it. Sometimes it seems to me, as the strap-on wearer, that I am expected to be the one who does all the action once I put it on, but my point is that you can do things, too. If you aren’t sure if she wants you to touch it (or kiss it or suck on it), ask. “Would you mind if I …” “Wow, I didn’t expect to want to … , but I do, please may I?”
Personally I think just about any sex act is all the more hot with someone saying what they are doing (or want to do), regardless of what it is. Maybe that’s me—I really love language.
Most women can’t come from penetration alone, which I assume the two of you know, but just a reminder that you both might want to start practicing touching your clit while she’s fucking you, either with your hand or, if she can reach comfortably, with hers. It takes some practice to be able to fuck with a cock and use your hand at the same time, but it’s possible! And worth figuring out how.
And from her side … it is possible to get off while strapped on, but that might take some time and practice. For me, I like the harness to be VERY tight, tighter than is all that comfortable around my hips, because I like to be able to feel every stroke against my cunt while I’m fucking. I like the stimulation of a one-strap (g-string style) harness better than a two-strap (jock strap style) harness, but that seems to be the minority opinion, so your milage may vary. She can try adding bullet vibes or butt plugs or the We-Vibe to increase stimulation, though I find those are more distracting than helpful. But if she really likes a vibration on her clit or something in her ass, that might be just the push she needs to be able to fuck and come.
Other than that, in my experience, to be able to come while strapped on, just following the sensation—when you find a spot that feels good, rub up on it, over and over, and see how far that can take you.
Consider anything you do in playing with it an experiment, and collect the data of that experiment. Did it work? Would it work better if one variable was different? Would you try it again? Or was it a complete fail and did not feel good? Gather the data and figure out what you like and don’t like, what was luke-warm and what you might try later if things were a little different.
Did I mention lube?
And … the first part of that question was, what was my first time strapping on like? Well, to be honest, my first time strapping on was to peg a guy, my boyfriend of about 5 years that I was with in high school. I bought a strap-on when we broke up, and I came out as a lesbian, and it was a tiny silicone thing that was very hard silicone and black and narrow. I do still have it, actually, I keep thinking it might be a good size for anal sex, but then again, now that I have the Spur why would I use a cock that was so hard?
We then went cock shopping together and bought a cock that was roughly the size and shape of his, which was what I pegged him with. It was fun enough to peg him, but it also made me realize that I was (really really for sure) a dyke and wasn’t that into it.
I did fuck my first girlfriend with a strap-on, but we were more of the I-do-you-you-do-me type of couple, so we took turns. It took quite a few more years before I felt like I had a cock that was mine—really not until I ended the relationship with my college girlfriend and started dating femmes exclusively. Which I have widely chronicled here!
It’s been a long journey to claiming my cock-centricity and cock confidence. Actually, I teach workshops on Cock Confidence now, in case you’d like to attend one—I’ll be doing it next at Good Vibrations in San Francisco in August.
Anything else y’all would recommend? Any other tips for first-time strap-on users?