The Scarlett Letters Read online

  Any bigger and that thing would be a baseball bat. I would run the other way if it came at me in a dark alley.

  He brandished it in one hand and said in a timid voice, “You want it to be bigger … and … and thicker? Uncle Harry can try.”

  “Maybe it would look bigger and thicker if you put those panties on?” I pointed to the frilly pink pair he had laid out.

  He wiggled into them, but let his penis hang obscenely out of one side.

  “Now the bra and stockings, Uncle Harry!”

  He took off his shirt and did as he was told, attaching his stockings like a pro to an elaborate garter belt that I would have struggled with.

  “Does it look bigger and thicker now, young Scarlett?”

  He posed from different angles.

  “Hmmm … maybe a little. I bet it would look even bigger and thicker if you put those heels on.”

  He sat down and put on a pair of massive, strappy red pumps. I had the absurd thought that they clashed horribly with his pink panties and orange bra. As though that was what was out of place in this scene.

  He strutted back and forth across the room. For all the practice he must have had in those shoes, he still walked with all the grace of a newborn giraffe, his legs moving at odds with the rest of his body.

  Next, we did a full application of garish makeup while he pretended to protest. I had never put makeup on a stranger or a man before and found the experience oddly intimate. Touching another person’s face and sitting much closer than you ever would in normal circumstances is odd. I was also hyperaware of the fact that his dick was still flopping around, now slightly less big and thick since our attentions were focused elsewhere. Totally normal working conditions, right?

  It turned out I did not have a future as a makeup artist, but he wanted it over the top, so my heavy-handed, smudged blue eye shadow was spot-on.

  He tottered back to a standing position from the makeup stool and strutted about posing, now in full drag.

  “But, Uncle Harry,” I whined, “you said this would make it bigger and thicker! But it isn’t! I want it to be bigger and thicker!” I stomped my foot angrily.

  He grabbed a towel from the bathroom, placed it on the leather table, and lay down on it.

  “Scarlett, tell me about the first time you saw a penis. Did it get bigger and thicker?”

  I was caught off guard. I guess I was now me Scarlett and not young Scarlett. The first time I saw a penis? I was drawing a blank. Living in France as a kid, things were pretty liberal. I don’t remember there being a defining penis revelation for me, but Harry was looking at me so intensely through his clumpy eyelashes that I felt obligated to make something up.

  “I was in a tree house with a boy named Seth, and he agreed to show it to me.”

  “Yeah? He showed you his penis? Just like this?”

  Harry had started “wanking off” as Dominic had put it. Now I felt the same pressure as I had in the past when asked to participate in phone sex. Talking dirty to someone who is beating it had always seemed really uncomfortable, but I figured I just needed to get on with it.

  “How old were you Scarlett? Was it scary?”

  “I must have been thirteen. I was so surprised. I didn’t know it would look like that. And then he started rubbing it. Yeah, just like that. And when he rubbed it, it got bigger and thicker. Much bigger and thicker than yours!”

  “Bigger and thicker?”

  “So much bigger and thicker.”

  I’ll spare you. It went on like this for a while with my story getting more elaborate and Harry’s movements more frantic. My elaborately made-up story would backfire in later sessions with Sissy Harry. I underestimated his ability to remember what I was describing since he was a little distracted. He remembered it word for word. He must have gone home and obsessed over my tale of Seth in the tree house.

  “Oh, young Scarlett! Tell me how disappointing it is! Tell me you want it to be bigger and thicker!”

  He rolled his legs up and flipped them behind his head in a move of remarkable flexibility. His back was still on the table and his knees nearly rested on either side of his head. He kept wanking, though, so I kept talking.

  “It’s so little, Uncle Harry. You told me I would see a real penis! Make it bigger and thicker!”

  With that last repetition, he aimed his dick down and came in his own mouth. He had swallowed it before I had even accepted what I had seen. I was shocked, but not appalled. I felt like I had just seen a really fucking crazy magic trick.

  “Thanks, Scarlett. That was fantastic.”

  He got up and I was a little worried he was going to try to give me a sweaty hug with penis fingers and semen mouth, but he didn’t.

  We had about ten minutes left, so I quietly sanitized the room while he cleaned up his face and got changed back into average-dude clothes. He went into the bathroom, and I let Caterina know we were finished a little early and were headed down. As we parted ways at the bottom of the stairs, he gave me a hug and slipped a $60 tip into my hand. Then he looked at me earnestly and said in such a vulnerable voice, “It isn’t really small, is it?”

  “No, Harry,” I said with a reassuring smile. “Biggest and thickest I’ve seen in a while.”

  And by a while, I mean ever. Or at least so far.

  I suspected if I stayed in this line of work long I was going to see a startling array of male genitalia.

  * * *

  Caterina buzzed me back in the front door and I was greeted by Erin, Raven, and Dominic all standing around the desk with shit-eating grins on their faces.

  “He came in his own fucking mouth!” I blurted, and they dissolved into laughter.

  “I wanted to warn you, but he loves getting a reaction out of new girls! Did I not tell you he cleans up after himself?”

  Erin had the most contagious laugh, and she was smiling at me like I was one of them now. I felt giddy.

  We kept breaking into new fits of laughter as I straightened my outfit in the dressing room and met the three of them at the patio table for my next client debrief.

  Raven offered me a cigarette and shrugged when I declined. The other two each took one.

  Apparently all the cool kids smoke.

  “You have Yoshi next. He should be pretty tame after last session’s fireworks,” said Raven.

  “I hate that fucker,” muttered Erin.

  “C’mon, he’s not that bad. A little gross and grabby sometimes, but manageable,” argued Raven.

  “Okay, time-out,” I stopped her, still trying to process the last hour. “What the fuck is Sissy Harry’s deal? I guess I was expecting more textbook stuff: guy was spanked as a kid, now he likes to be spanked. But how the hell do you explain where that shit came from?”

  “Why do I like licking assholes?” asked Raven, and I started to laugh before noticing she was totally serious.

  “It’s rarely that simple, Scarlett. The brain is much more interesting than that. You’ll learn to go with it. Around here, we see less cause and effect, and more patterns … guys who are into the same shit, weird as it may be. Stinky feet, repeated specific phrases, toenails painted a certain color. It makes sense after a while.” Raven shrugged and took another drag.

  “Do you think he actually shows his dick to little girls?” I asked, voicing something that had been nagging at me for most of his session.

  “I don’t,” said Dom. “I think he comes here to play out a specific fantasy, but I don’t see any reason to assume he’s taking it any further than that in the real world. I’m into fantasies of nonconsent … rape fantasies,” he said with a wicked smile, “but you don’t need to worry about me accosting unsuspecting women in public. I like my partners to enjoy themselves. Fantasies for most people are just that. Even if they act them out, it’s with consenting participants.”

  Would I ever be that comfortable talking about my own fantasies? I had to admit the image of Dom bending me over had a certain appeal, but it was the knowing look in E
rin’s eyes that made my stomach flip. The idea of being the one with the power was tantalizing.

  “A little like anal sex, then?” I asked. “The idea of it is super hot, but I really don’t want a dick in my ass.”

  “Speak for yourself!” laughed Raven.

  “Scarlett, your client is here,” came Caterina’s voice from the intercom.

  Raven stood up with me.

  “Don’t stress about Yoshi. He only plays for thirty minutes. He’ll say a bunch of stupid shit and probably try to touch you inappropriately, but just hold your ground and you’ll be fine.”

  8. YOSHI

  I went to meet Yoshi feeling amped up with a combination of nerves and excitement. Each of these new clients had the potential to be a fascinating adventure into the human mind. Some of them might even let me explore my own.

  Yoshi was waiting in the interview room, so I went in and introduced myself. He was an Asian guy who was roughly my height and was wearing blue scrubs. He didn’t seem lecherous if I overlooked his roving eyes, but we weren’t exactly in church so a little leering didn’t seem out of place. We set boundaries for touching: he couldn’t touch my breasts, but some light spanking was okay. I didn’t really have a good sense of what he actually wanted to spend half an hour doing, so I didn’t know what to ask or set as a limit. He kept just saying he wanted to get to know me … which sounded ominous.

  Yoshi took care of payment at the desk and asked for a five-minute warning before the session was over. We went back to a small room next to the dressing room called the cell. It had a kind of futuristic, metallic prison feel to it, but there was a cushioned table on top of a cage, so I jumped up and sat on it. The room was close enough to the desk that there was no need to formally start the session. The desk Mistress could hear when we started. I didn’t know it at the time, but anyone in the dressing room could also easily hear what went on in the cell.

  He came and stood next to me and took my hand. I wanted to pull it away, but decided it was harmless enough. I could put up with it for now.

  “Oh, Scar-rett … you been killing me. I been looking at your picture online. How many time you think I get off to your picture today already?”

  “Ummm … twice?”

  “Eight time. Eight time I get off to your pictures, Scar-rett!”

  “Oh. Well isn’t that charming?”

  How the fuck is one supposed to respond to that?

  I pulled my hand away and tried to keep the disgust off my face.

  He then undressed. Before exposing his genitals, he made me play the numbers game again.

  “How big? How big you think it is, Scar-rett?” he asked with an eyebrow wiggle.

  I sarcastically responded, “Two inches,” without hesitating.

  I don’t like playing the guessing game with cock size. You never win no matter how you answer, so I just don’t try. Put me in a silly situation and I’m going to mock you.

  “Oh, Scar-rett! You so bad! You so bad! Why you so bad to me, baby? You know I just want to please you, lick you pussy all up, make you squirt, Scar-rett.”

  Lovely.

  I didn’t feel even slightly guilty when he revealed his three-inch cock. I’m sure it wasn’t often that he managed to exceed expectations with it.

  Yoshi sniffed the air like a dog on the hunt. He started at my feet, carefully smelling each toe.

  “Next time, Scar-rett, you let your feet get real stinky. I like to smell you, baby.”

  Sure thing, baby.

  I began to get really uncomfortable when he hovered inches over my lady bits, still sniffing.

  “Oh yeah, baby. I smell your pussy juices. I want to lick them all up. Why you not let me lick your pussy, baby? I lick it so good for you.”

  “Because that’s against the rules, Yoshi.”

  I didn’t want to be there anymore. He wasn’t doing anything that bad and wasn’t saying anything worse than I hear from strangers walking down the street on an average day. But it felt dirty. On some level it seemed better that at least I was getting paid, but on another I think that may have actually made it worse.

  He sniffed his way up to my chest and hovered over my bra.

  “Oh, Scar-rett … one day you let me suckle your titties. They look so nice.”

  “Thank you,” I said, faking a smile.

  He lifted my arms above my head and smelled deeply over each armpit.

  “Scar-rett, you showered today, you bad girl.”

  With no warning, he licked my armpit, so I squirmed away.

  “No deodorant next time. It ruin your scent. I like you natural. I want to taste you, Scar-rett.”

  I had only been using my new name for a matter of days, but suddenly I was sick of hearing it.

  He had me roll over, and he flipped my skirt up to reveal my ass. He lightly spanked for a few minutes, but what he was mostly doing would better be described as playing with my ass, making it jiggle. He kept trying to hold the cheeks apart and smell my lady bits through my thong, repeating his filthy comments. When I thought I couldn’t take any more, there was a knock at the door and Raven said, “Excuse me … this is your five-minute warning.”

  “Thank you!” I replied with a little more enthusiasm than was really necessary.

  The significance of the five-minute warning became apparent when Yoshi stepped back and started to jack off. I was oddly struck by how sweaty his upper lip got. He was leering at me and panting intensely.

  “Oh, baby. Oh, yeah, baby.”

  He was going to ejaculate on the floor like a fucking animal if I didn’t do something. I grabbed a hand towel from a stack in the corner and tossed it to him with seconds to spare.

  He wiped himself off, dropped the towel on the floor, put his pants back on, tossed $100 on the table, and left without saying another word.

  Raven came in and pointed out latex gloves and sanitizer in a metal cabinet in the corner.

  “Cleaning equipment over here, Scar-rett.”

  I smiled and gave her an exaggerated shudder. I put the gloves on and wiped down the table and anything I thought he may have touched. I grabbed the offending towel and Raven directed me to the laundry room, where I dropped it straight into the wash and threw my gloves in the trash.

  “We’ll wash everything with bleach at the end of the shift,” Raven explained.

  I kind of wished someone would wash me with bleach as well, though it was brain bleach I needed more than anything. One more session to go. Surely it couldn’t be any worse than that.

  9. HARVEY

  I didn’t mention how repulsive I had found my session with Yoshi to Dominic or Raven, who were waiting to talk me through my next session in the dressing room.

  “Harvey is going to be your challenging one today,” she said as she dipped a boot into what looked like a bucket of mud and started rubbing it in.

  “He’s into heavy spanking, but he’ll know that you’re new and that he’s supposed to keep it light. Have you ever been spanked before?” Dom asked as though it was the most natural thing in the world to be asking me. Because it was him, I wanted to play it cool, lie, and give him a saucy answer, but I refrained and told the truth.

  “Not really. Maybe the occasional slap on the ass during doggie.”

  “This might be kind of intense for you then, but don’t be afraid to speak up. Harvey will push you as far as you’ll let him go, so it’s up to you to stop it from going too far or you’ll get hurt. Tell him if he’s getting too hard and keep in mind that you can always use the safe word if you need him to stop.”

  “What’s the safe word?”

  “It’s mercy. Shit, that should’ve been one of the first things we told you. Sorry about that,” he said, giving my shoulders an apologetic rub. From anyone else, I would’ve taken this as flirting, but he just seemed like a man who was used to touching half-naked women all day and it was part of how he interacted.

  “Mercy. Got it. Sorry … Raven, why are you doing that to your shoes?”<
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  “I’m about to play with Alex. He’s into anything gross. I get my boots filthy and make him lick them clean.”

  “Right. And he likes that?”

  “Loves it.” She laughed.

  “Focus on Harvey, Scarlett … your time for having men groveling at your boots will come.”

  I wasn’t going to deny that it sounded bizarrely appealing.

  “So communicate if he’s getting too heavy and use the safe word if necessary?”

  “And make sure he doesn’t sneak any heavy implements into the room with you. It’s his favorite move and he’ll hit you with something way too heavy when you aren’t looking or at the very end when there isn’t much you can do about it. He’s a great regular to have if you can manage him … but he’s really fucked some girls up who didn’t keep him in line.”

  “Sounds like a party.”

  * * *

  When he arrived, Dom and Raven were both in sessions, so Erin went into the interview with me. She let me do all the talking, but when I said I was a light player, she interrupted, looked at Harvey without the slightest hint of a smile, and said, “Light, Harvey,” and held eye contact with him for long enough that it was awkward.

  I was grateful when she came back to the implement wall with us and picked out the correct tools for the job since I didn’t have a clue. Into our bag went two slightly bendable leather black paddles and a red riding crop. It was disconcerting looking over all of the implements and choosing what someone was going to hit you with. I said this to Erin and she smirked.

  “Keep that feeling in mind when you start topping. Most girls think the scene starts when you get to the room, but if you do it right, this is where it really begins. There is power to be had from choosing for them and making them quiver in anticipation or from making them choose the method of their beating.”

  When Harvey went back up to the desk to pay, she put her hand around my waist, and against my ear said, “Don’t let the fucker get the better of you. You’ve got a spine. Use it.”

  Erin made me so uncomfortable. When she said things like that I wanted to tell her to fuck off, but she also seemed genuinely concerned, which made my heart race. She had been a bitch to me when I started, but another part of me wanted to admit it was kind of funny. Muddling all of this was her irresistibly appealing androgynous charm. I could still feel where her hand had rested on my hip. And I suspected she knew it.