by Emily Bishop
“Fair enough,” I reply. “I am one of six, which I think I’ve told you already. Three sisters, two brothers. My sisters were always super competitive with me, since I was the youngest. Or maybe I was competitive with them, and they rose to the challenge. Tough to say, really. I’ve spent my whole life being the youngest child, which means I’ve never really felt good enough.”
I send my message out and hold my breath. It’s not something I’ve admitted to a lot of people, but I trust Master, oddly enough. I shouldn’t. I don’t even know his real name. That adds to the fun of it all in the end, though, doesn’t it? I see him replying and take a nice gulp of wine while I await his response.
“That must have been hard, living in the shadows of five other people. Are they successful?”
I laugh. Depends on whom you ask, really.
“In a way. For our small town, they are. They are married, they run a solid business, they have children they can provide for. Where I’m from, that is success. I can’t compete with that, so I know I can never really go back there and feel comfortable about it. My success lies here in the city, on my own terms.”
“Interesting how success can be defined in so many different ways. It’s all relative, isn’t it?”
“Yes,” I reply. “I suppose the ultimate goal is happiness, but everyone defines happiness in different ways. My sisters would never be happy living here in the city, working their way up the ladder. On the other hand, I could never imagine being content spending the rest of my days doing the same thing forever.”
“That sounds like a total nightmare to me,” Master agrees, and I toast an invisible glass in the air.
“Hear, hear. None of this means I love my family any less. They were a major part of my childhood and my upbringing. I wouldn’t be who I am today without them.”
“Yes, but that doesn’t mean you should feel guilty about not wanting to go back. It’s OK to be the black sheep, you know. They have the best-colored wool.”
I chuckle. “I’m not a black sheep. I’m just the prodigal child… who will never make it back, permanently, anyway.”
“I think that’s great. Family is entirely overrated.”
I am insatiably curious now. I open up the screen to ask him a picture-revealing question and type it in.
“What was your childhood like?”
There is a long pause before I see him type. I lean back and enjoy the warm burn as I drink my wine and it slides down my throat. When the phone beeps his response, I lift it back up to read.
“Terrible. My mother abandoned me on a street corner when I was ten. I was placed within the system, passed from one foster family to the next. What they say is true—it’s a nightmare going through that. So many families just want the money. Others think they’ll be able to love you, but when it comes down to it, they just can’t. It’s not in them to do it.”
Tears well in my eyes as I read. All I can see is a child, scared and alone on the corner of a New York street, wondering where his mother went. I want to hold him in my arms and take care of him myself, give him the childhood every kid deserves. I brush a tear aside and continue reading.
“I made it until I was sixteen, then got a lucky break. That friend I told you about, he and I got into some bad things—kids from the street usually do—but he wasn’t actually from the street. He was a rich kid trying to rebel. His parents eventually took me in and helped me catch up with my education. I wouldn’t be a success without them.”
At least there’s somewhat of a happy ending to such a dismal beginning. I write back with my heart in my fingertips. “Oh, M, I’m so devastated to hear you had to go through that. No kid should ever know the pain of losing a parent. Did you ever find your mother again?”
“I did,” he replies. “When I got rich, she found me and tried to get money from me for drugs. It wasn’t a pleasant scene. I got the chance to kick her out of my office, escorted by two large security guards. It was one of the most satisfying moments of my life.”
“Do you think you’ll ever forgive her?” I ask.
I shouldn’t be so blunt, but I can’t help myself. I want him to open up his wounds and let me heal them. He can put them in my hands, and I will cradle them away until he knows nothing but happiness.
“I don’t think so,” he says, after a while. “Part of me wants to forgive her. She’s my mother. She clearly has a drug problem. Who she is shouldn’t be connected to that. But she left me on a street corner, alone. I waited until midnight, when a cop drove by and asked me what I was doing. It wasn’t a warm day, either.”
Oh god, it’s even worse. She left him out in the cold! Now all I see is that little boy shivering, calling out for his mother. I grieve for the loss of his youth, though given his description of his mother, I can’t imagine it was all that great being with her in the first place.
“What about the foster families? Not one of them was kind to you?”
“Not really. There was a lot of mental abuse that went on. I had one foster mom who would pit me against my foster brothers so we’d compete for her affection. Whoever won the day would get a delicious, warm meal, and the others would get stale cereal. Another guy actually had us fight one another in the basement for who got to sleep in a bed and who slept on the floor. Pretty dark stuff, really.”
Tears stream down my face again. I can hardly bear to read his words. This poor man, that poor boy. Together they have suffered and become Master, the mystery behind my screen.
The man I’m very quickly falling for.
“I hope you’ve come out stronger at least. You beat the odds. You became the success that so many others couldn’t,” I say.
“Yes, I certainly have. I learned to close myself off at an early age, that love was used as manipulation. I guess that’s why it’s easier to open up here. Through this medium, manipulation comes a little bit harder.”
“I would never,” I say.
A question opens up on my screen. It’s one word.
“Promise?”
I answer in the affirmative, and both our images get a little less blurry. I can tell now that he has very broad shoulders. He might even be wearing a suit in his picture, which makes sense, given his profession.
I think Master might turn out to be the complete package. Brains, a good soul, and a handsome face.
Could I really be so lucky? Another ding. My heart skips a beat.
“Now let’s talk about sexting. Feel up for a little action tonight?”
My throat goes dry. Here we go.
Chapter Eight
Booker
My legs are crossed, my bare feet up on my wide glass coffee table. I stare out at the expanse of New York from my penthouse suite and grin.
We’ve shared enough intimate facts about one another. Now I want to see if she’s willing to be intimate in a more “physical” way. This has to be one of the safest options for her. As a virgin, she gets to maintain that part of herself, all the while experimenting with the idea of delicious, mind-blowing sex.
What could be better?
She responds, and to my surprise, I hold my breath as I look.
“I might be willing to give it a try,” she says.
My dick stirs at the thought. Tonight, I’m going to get an orgasm, and if I’m lucky, so will she. It will be my job to bring her there. I bet she doesn’t even know how to describe sex. Let’s find out, shall we? I tap away on my keypad.
“I will tell you that the fact that you’re a virgin is a major turn-on,” I confess.
“Why?” she asks.
“I don’t honestly know. There’s something so enticing about showing you the ropes, teaching you how great physical pleasure can be. At the moment, I can only do that from a distance, but I think I can do an effective job, if you’re game.”
The problem with this medium is the long pauses after meaningful statements. I don’t know if I’ve scared her off or turned her on. I can only wait for that little symbol to come up so I know she
has something to say. So that I know she hasn’t deleted the app and walked away from online dating forever.
Am I playing too risky, doing this? Should I be more focused on getting to the end part of the app, so I can say that I’ve used it effectively and then I can work on any final glitches before we release nationally? It seemed prudent to open the app up only to New Yorkers as a trial, but now I’m wondering if it will apply to people all around the country. Then again, Angel isn’t from New York, and she’s managing just fine.
My thoughts are interrupted by her response.
“I’m game, but you’re going to have to lead me, here. I’m not familiar with this on a lot of levels.”
The thought of being her first has my pulse beating a little faster. I lean back into my sofa and get comfortable, ready for a good time.
“First things first. Get comfortable. Are you dressed in comfortable clothing?”
“Yes,” she says.
“Great. On my end, you’re wearing a black lace bra and panty set with a pair of nice high heels. What am I wearing?”
“Boxer briefs, and nothing else.”
I chuckle. “Not much left to strip down, is there?”
“For you, either,” she says.
“I’m going to start with you first. I’m going to pleasure you, show you how it’s done, and then you can try and pleasure me. It’s safe to try out dirty words, if you want. I’m not adverse to them.”
“OK,” she replies.
“I’m going to kiss you now. First your lips. I bite the bottom lip before I leave a trail of kisses down your cheek and make my way to your collarbone. I slide your bra strap down so I can taste a little more of your shoulder.”
No response.
“This is the part where you tell me how that feels,” I say.
“Oh… sorry. It feels really, really good.”
I laugh out loud at that one. She’s got some work to do, but I’ll walk her through it.
“Good. I sit back and unclasp the back of your bra.”
“I toss it across the room and save you the trouble,” she replies.
Mm. Not what I was going to do. I was going to take things a little more slowly. I instantly wish we were doing this in person. My hand could have stopped her from doing that. Nevertheless, she’s now naked from the waist up in my mind’s eye. Originally, I imagined her as a blonde, but as the fantasy plays out, I realize that she looks much more like my assistant, Sasha. Her hair is a fiery red, and her eyes are green and filled with lust.
Well, I suppose I’ll just go with it. Sasha is a beautiful woman, after all, and I have nothing to go by as far as looks go with Angel. I suppose I’ll allow my imagination to stick with what it knows.
“Good. I slide my tongue along your collarbone until I reach your breast. I sink my mouth over your nipple and suck on it. I want you to pinch your nipple while you imagine it. I want you to touch yourself. Are you touching yourself?”
“Yes,” she replies.
“Good. Now I’ll move to the other one, and so will you. I run my tongue around your hard little nipple first, then suck on that one, too. Give it a good pinch, because I’m nibbling.”
“That feels so good,” she says.
OK, she’s getting the hang of it. This is a good thing. I pull my cock out from my pajama pants. It’s at half mast, so I start to stroke it a few times, then return to my phone.
“I’m going to press you onto your back now and blow on your nipples to get them nice and hard. Now I’m dragging my tongue down over your stomach, farther south until I reach your panty line. Are you watching my path?”
“Yes,” she says again.
It’s all the confirmation I need.
“Good. I take your black panties in my teeth and slide them all the way down your legs, over your heels. I leave the heels on. You’re naked before me now. What is the status of your pubic hair?”
“A landing strip.”
“Sexy. I’m ready to land. I pull your legs apart and expose your pussy to the cool air. I lean down and blow on it, all the way up and down your slick little slit. How wet are you?”
“Soaked,” she writes.
“Sounds delicious,” I type. “I’m going to taste you now. I lick your clit and circle it with my tongue before I slide my tongue down the length of your dripping wet pussy. Angel, you taste so good.”
“I want your tongue inside me,” she says.
Good girl. Now she’s catching on.
“Happy to oblige. I slide my tongue into your tight little pussy. I slide it in and out. I’m fucking you with my tongue. How does it feel?”
“I want more.”
“I slide my tongue back up to your clit so I can finger you. I hold up my middle finger for you to see then press it against your opening. I slide it in, nice and slow, until it’s deep inside you. What do you want me to do next?”
“Another finger, and don’t stop licking my clit.”
“I press the flat of my tongue against your sensitive little bean. I slide my finger in and out of you until it’s nice and slick, then I pair my ring finger with it and stretch your pussy to fit both of my fingers. I want you to ride my hand. I want you to fuck it. Spread your legs wider so I can fill you even more.”
My dick is rock hard now, just imagining fingering and licking this woman. I give it a few strokes as I close my eyes and allow myself to enjoy the experience, then turn back to the phone.
“I’m going to fuck you now. I remove my fingers and bring you to your hands and knees. I’m going to take you from behind. I press my dick against your pussy and slide in, one inch at a time, until I’m all the way inside you. I want you to rub your clit for me while I fuck you.”
“I’m rubbing it. I’m going to come.”
“No, you’re not. Not until I give you a good fuck first. I’m going to slide my dick in and out of your pussy. I’m fucking your brains out now while you slap your clit and rub it between your fingertips. The only sound you hear is my balls slapping against your ass as my dick sinks into your body and back out again. I want you to tell me what you’re doing right now.”
“In real life or in the fantasy?”
“The fantasy,” I say with a small laugh.
“I’m enjoying the sensation of you filling me all the way. I can feel your dick pressing against my g-spot as you fuck me, and I submit to you. I want you to fuck me harder, with everything you’ve got. Nice and hard.”
“I pick up my pace then. I’m fucking you as hard as I can. I slap your ass.”
“I like that.” She’s only using one hand now. She must be.
“I bet you do. Now I want you to come for me. Rub that clit a little more. I want to watch you when you come.”
“I’m almost there,” she says.
This is the tough part. I can’t really tell where she is at when she answers again.
“Oh my god, that was amazing. I actually came just now.”
“Good. Ready to give me a turn?”
“Absolutely. Ready?”
“I was born ready,” I say.
“Good. Now lean back. I want to lick my juices off your cock.”
Wow, she’s a quick study. I wonder if she’s ever done dirty talk before. She’s pretty good at it.
“OK, I’m back.”
“Good. I take your whole dick in my mouth and sink all the way down until my lips reach your base. I can taste myself and your precum, and it’s delicious and sexy. I slide back up the length of you, then head back down. I stick out my tongue so that it can glide along your dick as I guide my mouth up and down your cock.”
“Yes. Let me fuck your mouth, Angel.”
“Take my hair in your hand. Have your way with my mouth, as you need.”
My imagination goes wild. I can see my fist wrapped with strands of glorious russet hair as I fuck her little mouth, my dick sinking into the warm heat. My hand pumps up and down my dick as my imagination runs the gamut. “You’re pretty good at this, for a
beginner,” I write between pumps.
“Thanks, now shut up and fuck my mouth.”
“Stroke it. Stroke the bottom while you lick my head.”
“Happy to. My hand wraps around your dick as my tongue toys with your head, and I stroke you. Spit on your hand so you have the lube you need.”
Can’t say no to that, can I? I spit into my hand and return it to my cock as I stroke at a quicker pace.
“I want you to come. Where do you want to release?”
“In your mouth,” I write back. I tilt back my head and bask in the fantasy, where Angel/Sasha’s mouth overtakes my dick as I sink into her.
“I remove my hand and take your dick in my mouth again. I want you to fuck me until you come.”
“OK,” I type. My breath is heavy as I pant, my hand working furiously on my cock, pumping up and down in a maelstrom. I’m so close. I imagine her little mouth working its magic, sucking a little harder.
“Oh, fucking fuck,” I hiss through my teeth. My load erupts from my dick and spills onto my hand.
I lay back and breathe for a moment. A box of tissues sits on my coffee table, and I take one and clean off my hand before I pick my phone back up.
“That was outstanding,” I type.
“You finished?”
“Yeah, did you?”
“Yeah,” she says.
“Great. I like to give my partners more than one orgasm though. I think it’s time for one more session for you.”
“You’re quite a generous lover,” she says.
I grin at my reflection in the window, my limp dick sitting out of my pants.
“Yes. Yes, I am.”
Chapter Nine
Sasha
My body is putty.
I sit back, languid and relaxed, my phone in one hand, my fingers stroking my clit with the other. I’ve already finished once with his masterful texting. I have no idea how he’s going to pull it off again.
I can’t wait to find out.
The phone dings, and I’m pulled from my short reverie. My stomach flutters with anticipation as I read the text.
