His Sugar Baby Page 3

  “I understand, Ivor, but I have to ask. It’s not her fault I’m leaving. Think about it, Ivor. She’s been a good tenant these last five years.”

  He’s quiet. “That’s true, you two pay on time, always. No complaining from tenants or my guys at front desk. It’s just, Anne, the place is worth twice what you two pay. Your rent is twenty-five hundred. I could rent tomorrow and have forty-five hundred or five thousand by end of day. I keep price low for Frank, now you leave. Frank, he tell me I don’t owe him no more.”

  Shit, he’s already asked Frank. Which, if you owed Frank was the smart thing to do. I know what Robin makes down to the penny and what she has in her savings, so I negotiate.

  “Thirty-six hundred a month, she can pay that on her own for the next two months if she has to. She’s a smart, responsible, and quiet tenant. Wouldn’t you rather have her than some coked out trader asshole? Yes, she’ll need a new roommate to help with rent, but do you think she’s going to pick a crap roommate? No, she’s going to pick someone like herself or me.

  “We’re the only tenants beside Ms. Mayer, who isn’t leaving until she’s dead, you haven’t had to evict or who has come and gone leaving a mess you have to clean up. Remember, you couldn’t rent out an apartment for three months it was so messed up, when those three sorority chicks rented it? Our place is spotless, you’d only have to paint before putting it up for rent. Come on, Ivor, the tenant you know in Robin, or someone who cares more about the address than the home they made?”

  Ivor’s quiet for a long time. Then he says it like it hurts him. “Thirty-eight hundred.”

  I don’t hesitate. “Agreed. Thank you, Ivor.”

  He sighs, “I have to file eviction on that couple that moved in with the baby just five months ago. Business isn’t easy.”

  “Depends on who you do business with, Ivor. I don’t think I’ll be talking to you again before I go. Thanks, for everything.”

  “Goodbye, and good luck.”

  Checking the clock I figure the poor schmuck getting the root canal is probably in recovery. I call Robin who answers on the first ring. “What did Ivor say?”

  “Thirty-eight hundred a month. Don’t squeak, it’s doable. He says the place should be going for at least a thousand more. Yes, it’s a change from fourteen hundred a month, (I knew it was more valuable than what Frank was being charged. I just didn’t know how much. She didn’t know rent was only twenty-five hundred, sue me. I have an addiction to massages which is where the extra money went) let the new roommate offset it. They’ll be expecting to pay more than nineteen hundred.

  “Just, as a part of a promise to Ivor, no troublemakers. Find someone boring who won’t cause any problems. It’s what got him to say yes, us being quiet, boring, and how we pay our rent on time.”

  “You’re right, Ivor’s right. The place is worth much more than thirty-eight hundred. It’s just a shock to the system, rent going up five hundred bucks from one month to the next. Then again it hasn’t gone up once since I moved in, like it normally would have anywhere else I would have lived.

  “I’m also making much more than when I first moved in. You’re right I could offset the difference with the next roommate but you know me, I’m not good at keeping a lie going. Thanks for talking to Ivor. I wouldn’t have been able to get him to agree.”

  “Don’t be hard on yourself, this was business, and when it comes to business—stick with the facts. The fact is you are an awesome renter any landlord would love to have. I’d better let you go. I have more packing to do, and I don’t want to get you in trouble.”

  “Okay, see you tonight. I’m so making you spaghetti and meatballs and tiramisu for dinner tonight. Don’t snack close to dinner.”

  I promise I won’t.

  The flight was smooth from Boston to Chicago. I look around the Airbnb I’ve rented for the next two weeks, and hope I haven’t made a mistake. Not the condo, I’m on the twelfth floor in a nice-looking place on North Clark street. It’s an okay condo, if a little empty. It’s a one bedroom with only a bed in the bedroom and a small lonely looking couch, no other furniture in the whole place. I wonder if I’ve made a mistake picking Chicago. I’ve only received one positive response, and from the email alone the guy was clearly a weirdo.

  The problem was I had run out of time in Boston. Robin had found a new roommate who could pay the rent. I needed to leave. Although my checking account is a little fuller from Robin buying pretty much all the furniture in the condo from me, I’m well aware it won’t last long in the city.

  As I take in the view of the city, I’ve seen better views. It will do, for now.

  Chapter Three

  Checking my watch, again. I see it’s a full half hour later than the time the evening was supposed to begin. A woman late, I’m used to, but not on the first date and not a half hour. I look to see the driver, Eric, is not ruffled in the least. He’s reading a book. He might be used to waiting, I’m not.

  I’m also not used to hiring a car. Usually, I’m content to walk or grab a cab. The Town Car felt small when I got in, after a half hour it feels fucking claustrophobic. A cop comes by for the second time to hassle the driver for parking very illegally in front of the building. I’m about to get out and just pay the ticket when the door facing the sidewalk opens.

  She slides into the car in a huff and a whirl of long fake hair. “I can’t believe your driver didn’t get the door.”

  The scent of violets fills every inch of the car. I roll down the window to let the cop and driver know we are ready to leave. “As you might not have noticed, he was busy trying not to get a ticket. A half hour ago you said you’d be right down.”

  Her fake eyelashes bat up at me. “Perfection takes time.”

  I can’t take the nauseating scent of her perfume and put my window all the way down to get some air. “I’m not interested in perfection or fake hair or fake eyelashes. I picked your profile for a reason, you didn’t look like this in the profile.” Fuck, she’s crying. I don’t do tears. “This isn’t going to work out. Eric, take us back to her place.”

  “No, wait, please give me a chance. I can get rid of the hair and eyelashes. I thought it was what you wanted. Please give me a chance.” She’s stopped crying and she’s gotten the lashes off.

  We’re back at her place. Even though I’m pretty sure it’s a waste of time, I tell Eric to park. Her building is a five story that’s seen better days. The elevator moves begrudgingly up to her fourth floor.

  She fumbles with the lock. Inside it’s not as bad as the building. It’s almost homey, but there are too many shiny objects to make it completely cozy. The coffee table is mirrored, the clock behind the sofa is a starburst with rays that are tipped with little mirrors. A faux zebra rug covers the heavily scuffed wood floor.

  It’s only a few minutes before she comes out of her bedroom without all the makeup and hair and tight black dress. Skin free of makeup it’s easier to see she’s closer to my age than she admitted on her profile. Without the makeup she’s no stunner, but she’s pretty enough. The black lace bustier pushes up her real breasts front and center, she’s in a small sheer thong that shows off her bare pussy.

  “Is this better?” She asks hopefully.

  My cock answers, it’s an improvement. I decide to follow her lead, and sit down in the overstuffed chair facing the couch. This is what I’m here for, to find a woman willing to please at night and happy to leave me alone to work during the day. Maybe my conventional, suburban upbringing is more deeply ingrained than I thought, because it’s not enough for her to get my dick hard. I want to know more about the person who will be in my bed at night.

  “Maybe getting to know each other for this agreement is better done in private. Tell me something about yourself you didn’t put in your profile.”

  She’s annoyed, she doesn’t hide it as well as she thinks she does. “I don’t know, um, Joni Mitchell fan.”

  I’m annoyed now. My fingers drum the hard pleather, while I
debate walking out now or giving her a third and final try. Whether she’s being sarcastic or not, she’s finally getting that I’m serious. “What do you want to know? Usually everything a guy wants to know is in my profile. I do anal, I really like anal, my orgasms are more intense. I’ll suck your dick anytime you ask. I’ll do a threesome, or more if you want, men or women.

  “I can do kinky, my profile said open to kinky, but I’ll do almost anything, golden showers, give or receive. I’ll do BDSM if it’s what you need to get off. If you want I’ll call you sir or daddy and crawl around with nipple clamps. I’m not a fan of the caning and real rough stuff, though. Although I do love rough sex, some hair pulling and spanking makes me wet.”

  My cock deflates as she lists what she’s willing to do. Considering how hard it got when she went on about how much she loved anal, I’m not sure why. All I know is I want to get out of here. Maybe she sees it because she’s pulling off her bustier.

  Her tits look even better than her picture, they are also very real. She’s on my lap shoving them into my face faster than I can say, nice tits. “Is there something you want me to do? I’m open to anything to make you happy. I’ll suck your dick every hour on the hour if it’s what you want me to do.”

  Damn it, my cock is interested in getting sucked every hour on the hour. Then she sticks her hand down my pants and with a deft twist of her wrist takes my cock from thick to hard. Shit, my hand goes around her wrist. “I didn’t bring you up here to fuck you.”

  “Of course, you did. You have to try me out before you buy. I’ve been looking forward to fucking you. I thought it’s how we would finish the evening. Then again, why not start with dessert?”

  In a move that screams former stripper she slides down my legs, taking my pants with her then sucks my cock all the way down her throat. I have every intention of pulling out, and getting out of here. I do, except fuck she took my cock down her throat. I’m impressed as hell.

  It isn’t easy to get my cock sucked, what most men bragged about women backed away from. I’m over nine inches long and so thick I can’t get my hand around my own cock. Most women have a hard time sucking my cock. This woman, shit, I can’t remember her name for certain, knows exactly what she’s doing. She also seemingly enjoys it, her eyes up at mine, taking her time.

  Her hand is in the small triangle of her thong. “I can suck you deep anytime you want. You can use me anyway you want. I’m yours to make you feel good every night. I’ve been doing this a long time, I know every trick they don’t teach the good girls. I’m not nearly as expensive as the other women on the site. I’ll know my place. I’ll be ready to fuck at your say so.

  “This can be good for both of us, baby. I’m clean. I have a doctor’s note and everything for tonight. You can fuck me bare, no condom. I had my tubes tied years ago for another sugar daddy. Damn, I can’t get wet and I want you to come inside me. Let me grab my lube. I’ll be right back.”

  I look at her front door. Now is the time to go if I was going to go. She is exactly what I’m looking for. My cock is still aching for release though. I stay where I am.

  She’s back down on her knees again, coating my cock in lube. “As long as we are using lube I want you fucking me up the ass. I can’t wait to have your long thick cock up my ass.”

  Her hand wraps around me, guiding me into her ass. The first few inches she moans and her hand on my thigh tightens. Then I’m in and she sits down with a long groan. “Yes, you feel awesome.”

  I’ve had this sex before, more often than people would believe. With my bank balance, women go out of their way to be with me. Whether it’s simply to be seen with me, or to climb into my bed hoping it will get them more of me and my money.

  More women than I can keep track of have fucked me while I just lay there and didn’t do a single thing. When it first happened I lay there out of shock. After they congratulated themselves on how good they were, being the asshole I am, I left with a shrug telling them I’d had better. Then, when it happened again, I lay there curious about how far the woman would go, what they were willing to do. The answer surprised me, pleasantly.

  Her loud moans have my full attention as she bears down on me, fucking me so vigorously I’m getting tired just watching her. Then she stops, rolling back and forth on me, all of her weight pressing me deeper inside her. She keeps up the almost painful clenching of her ass, then moves her legs from outside my legs to inside them. Now I’m deeper inside her. She moans every time she lands on me. Damn, it’s almost painful. I’m about to pull her off when she comes. Damn does she come. Her whole body is shaking as she lets loose a high-pitched wail. Even counting down to the time she was finished, watching a woman come with such abandon is sexy as fuck and I find myself coming too.

  When she collapses on me, I wonder how long before I can move her off. She moves before I find out, rolling off me with a breathy moan. “That was awesome. See Grant, wasn’t it good for you? It can be like this all the time. Let’s go into the bedroom where we can get comfortable. I have some toys you’ll like playing with.”

  “Sure, give me a minute. I’ll be right there.” I wait until she’s in her room before I stand, buttoning my pants. The sound of a vibrator comes out of the room. This isn’t going to work.

  Opening my wallet, I find the cash I brought for dinner. I bring my card, too, but if I want dinner over easy and fast I like the ability to toss cash. I brought three hundred for dinner, she wasn’t worth three hundred. I drop one hundred on the table then leave without a sound.

  In the car, I tell Eric to take me home. Back to the drawing board on this.

  ***

  Feeling like I earned it, I order down for a steak and fries from the Ritz Carlton room service I have access to in my building. While I wait for my dinner, I log onto the sugar daddy site. Despite there being new women on the site, none of them appeal in the slightest. It isn’t until I’m halfway through dinner and on page twenty two that she finally appears.

  Out of a sea of blondes she’s only the fourth woman to have dark hair. Her hair isn’t just dark, it’s the color of a raven’s wing, long and silky running over her very impressive breasts. They could be fake. I really hope they aren’t, they fit her body in a way that screams real. Her body is a feast of curves. Unable to keep my eyes from roaming over her picture again and again, committing every inch to memory my hands clench at the idea of holding them.

  Her face is an oval of perfection. I’m sure she’s not wearing any makeup, her clear pale skin doesn’t need it. Wide grey eyes below full black brows give her a look of intelligence I hope I’m not projecting out of desire. She has high cheekbones, no makeup is needed to highlight them. A small pert nose is over a wide full mouth ripe for kissing. Her half smile reminds me of the Mona Lisa, brimming with secrets. I want to know every one of them.

  In the other profile pictures, many of the women are wearing sexy lingerie like something out of a catalog. She is wearing what some women might sleep in, a black stretch camisole and silky black pants. Her breasts, full and high under the camisole, make my cock ache. Against her pale skin, what she is wearing is enticingly erotic.

  Clicking into her profile, I barely glance at her stats, five foot six, and thirty years old. She looks younger by at least five years, though. Her profile is short and to the point and makes me smile as I hit save on the page.

  My favorite color is clear, I enjoy long walks on the beach and think mean people suck. Seriously, though. I know I’m supposed to be old enough to know what I want to do with my life, but I haven’t figured it out yet. I’ve been a sugar baby before, yes it really was just until I got my degree. I got my degree and thought I’d left all this behind. I was wrong.

  After five years in the day job world, using the degree everyone told me would make my life better, I figured out I hated accounting. While I try to figure out where to go from here I’m looking for a sugar daddy to maintain my living expenses. For me, the most important basis of an arrangement
is respect.

  I bring up another page on my second screen then begin what I love doing the most, digging into the web to find out everything I can on Anne Thomas. I’m sure it’s the illegality of it that usually gives me the rush of adrenaline, now it’s the idea of digging into who Anne is behind her profile. I’ve found what I want, I want Anne. Now I need to know everything about her to get her.

  The surface search is interesting as much for what I don’t find as what I do. She doesn’t have a single social network account, no accounts for pictures of her lunch or selfies with duck face, no tweets about mean people, no Facebook account, not even a professional account like Linkedin. Hell, even Alice has a Facebook account. I had to help her set it up so she could get updates on her grandkids. Anne Thomas gets points for that alone. While my company maintains a Facebook page, I don’t have one.

  Only an hour in I’m able to confirm her honesty about her degree in accounting and two jobs for different accounting firms in Boston. She hasn’t worked, though, in almost four months. There’s an attempt for unemployment she was denied. I’m curious about her move to Chicago from Boston.

  Then I find it. She had been a hooker, an actual hooker, for at least a year from what I can tell. The tax form listed the company as a modeling agency, only the modeling agency was a front for an escort service. For a long time all I can think about is how many men she’s fucked, and how she had fucked them.

  I look back at the profile of Anne Thomas. With a click, it disappears. I’m up, restless. I’m pissed at Anne for being so damned appealing then taking it all away by being something different than what I had expected, what I want her to be.

  The view from the window of my office has always been my favorite in my whole condo. Right now, I don’t see it. All I see is Anne’s profile picture. Every word of her profile runs across the back of my eyelids like the code I write.