Today marks a special milestone for me, a rite of passage in any young woman’s life. It’s a day I’ve always dreamed about… the day I first fucked a man with a strap-on dildo. Ah, life is sweet.
What? Did you expect me to talk about virginity? Or how about my wedding day? I could talk about both. I lost my virginity on the first date with my first love. My wedding day never came because my fiancé of seven years left me last year. Now that we’ve gotten that out of the way, on to the good stuff…
My manager Lucy always takes care of me; she steers clients looking for a curvy girl with an ass to die for in my direction. Tight Tim was one of those “ass worship” clients. To be fair, Tight Tim worshiped his ass as much as any woman’s. Lucy told me to get dressed in a nurse’s outfit and meet him in the Scarlet Dungeon.
“Nurse?” I asked. “Doesn’t he want medical?”
“Yes, he wants medical [role] play. He prefers Scarlet because it’s more comfortable for him.”
Okay, I think, so Tight Tim thinks ahead. There’s a leather bed as opposed to the examining table in the medical scenario rooms.
I have an advantage in this session with Tim. This is not a “meet,” in which Tim would meet with every dominatrix in the house separately for two minutes each. This is better; Lucy convinced him to already choose me for the hour. The two minutes I’m taking to talk to him is to negotiate the terms of the session and what I am comfortable doing — in other words, deciding whether to choose him as a client.
I put on my black peep toe heels without stockings because I’m feeling lazy today. In the first few weeks as a domme, I would roll up my black thigh high stockings, lace up the waist cincher in between my black lace bra and matching panties, and pile on the studded leather bangles each and every time I met with a client. Eventually, I learned to simplify and adjust my dress routine to the situation. Nowadays, I have to be really convinced it will help in my favor before I lace up any corset.
I walked to the Scarlet Dungeon and knocked. Tight Tim was sitting on the leather bed pushed up to the mirrored wall. I crossed the room in wide, confident strides as befitting a domme session, instead my short, soft steps for a client looking for a submissive. I always shake hands, to be professional and also because I’m going to be incredibly intimate in a few minutes.
Tim tells me he wants a sensual (read: be nice) domme session with nurse roleplay, including but not limited to rectal exams, anal probing, penetration with thin dildos (vibrator a plus), ass worship like brown-nosing, and the words which make my eyes light up with joy… strap-on action.
“Cherie, are you comfortable with all this?”
I say, “Yes” and think, “Fuck, yeah!”
I do the requisite disclaimer that any ass worship is done with panties on, and we shake on it.
I return to Lucy’s office and get all the accessories. Lube and a box of gloves are must-haves for every session. Next are the butt plugs, vibrators, and dildos, which are all thin as he requested (hence, my nickname for him). It takes time to find a dildo small enough that will fit in the strap-on opening (most need larger dildos). Finally, Lucy throws in the secret weapon: a vibrating prostate massager. She says he’ll climax right away if I need him to. Perfecto.
When I open the door to the dungeon again, Tim is standing naked except for a pair of socks. I entered with a basket of goodies in my arm. I laid two towels on the leather bed and instructed Tim to lie down on his back. I’m used to bullshitting fairly often so I acted as if I’ve done this everyday.
Truth be told, I don’t know what I should start with first so I improvise on the spot. Ass worship means I would have to take off my white, button-front pleather dress so starting with that would defeat the purpose of the costume. Stalling for time, I asked him if he has any health concerns today. He said no. I spouted some nonsense about this being a good day for a check-up and a thorough rectal examination.
I turned on the smallest vibrator and moved the tip gently from his shoulder, down his arm, to his thighs. I said that it was best for my patients to be comfortable and know what to expect in my rectal examinations. He was very happy with my bedside manner and this kind of dialogue.
The rest was mindless small talk while I inserted butt plug after plug. I talked about how I probably should have gone to medical school because I liked medical role play so much. I asked him if he ever found any nurses attractive during his doctor’s visits. He said occasionally. I told him he would have to think of me every time he saw a nurse after today, so he smiled at the dirty thought. Imagine, having to suppress an erection every time he sees a nurse because he would associate anal stimulation with a nurse’s uniform.
The talk was mostly for me, since he seemed so quiet and passive. I wanted to make sure he was enjoying my finger or any toy I inserted. I know from experience that you don’t know something will hurt until it goes too far, too quickly. I wanted to make tip and get repeat business so slow was the name of the game. I kept the first butt plug in for a few minutes, to loosen him up. Then came the thin vibrator, which looked like a bright blue unicorn’s horn. I took the longest with that toy since Tight Tim was moving his ass up and down (a good sign).
Next was the thicker butt plug so he would be ready for my strap-on. Tight Tim lived up to his name. No matter how much I used my fingers to shoehorn that plug in, his sphincter pushed it right out. Oh, well. You can’t insert everything.
Now, the moment I was waiting for. I pulled open my dress in one motion and turned around so Tim could worship the famed ass with his hands. Lying face-down limited his movements so I didn’t need to do much. I showed him the dildo, which was pliable and had a nubby tip. My only regret was that the vibrator piece had a dead battery so I wouldn’t enjoy it as much as Tim.
I wished I had a drum roll or theme music blaring when I was fastening the strap-on around my thighs. I climbed on to the bed, dropping my heels to the floor. I brought the prostate massager close to his waist, along with the lube.
Something about pulling his buttocks closer to me felt right. This was better than losing my virginity; this was taking something and claiming it for my own instead of handing it to someone else. I did not get caught up in the power relations between us. This was so much simpler. I was going to penetrate this man upon his request and make him climax in five minutes or less (which was the end of the session). I was going to fuck him and try to be good at it even for the first time.
Like any first time, I learned a lot. One, thin dildos bend like a bitch so even one wrong movement and it pops out so I needed one hand to hold it in. Two, if I’m fucking downward, my knees will give out so I had to pretend like I’m doing squat reps. Three, give him room to lift his butt up to jerk off (but I knew that). Four, save all the energy for quick, consecutive thrusts at the end until you hear the big moan.
I smiled at my reflection in the mirror for a quick second before I pulled out of him. Seriously… if my exes could see me now. Damn, I looked good. A mental snapshot had to suffice. Another day, another kinky activity to mark off on my bucket list.
Ma Cherie (@CherieDAmour) is in the market for a boy/girlfriend, kinky sex partner, willing slave, and sugar daddy, though not necessarily in that order. When not working as a dominatrix, Ma Cherie is cruising online dating sites, hitting up fetish parties, and regularly pleasuring herself. Unironically, her favorite song is “Kiss With A Fist.”