A/N: Oh snap! Back from the dead, it's the adventures of prostitute Ambrose! Sorry that it's taken so long for a new tale. I was going pretty good with once a week updates on my main story, so I never really had time to get one in for this story. But since I'm taking a break from my other story, I'd be a jerk to not update this one! Now the one slight warning I have is that the story will shift from first person to third person at one point. I hope you all don't mind and that you enjoy the story.
Mr. Ambrose and the "Frigid" Woman
"I love all my boys, but you are definitely my favorite," I groaned as I stretched out in bed.
It had been about two months since Jon came to live with me at the mansion. He had already brought in more income than I could have ever dreamed. I barely had to do any real advertising for him. Clearly the Ambrose name, which he chose to continue to use, carried a lot of weight.
"There's just something about you, darlin. You seem to be able to understand exactly what someone needs and how to give it to them." I rolled to the side and propped my head up on my arm. He lit up a cigarette and sunk back down into the bed.
"It's a blessing and a curse, really," he sighed as he exhaled. I laughed at his shameless cockiness. I would've been irritated by it if he wasn't as professional as he was and if he wasn't so damn good at his job.
"Well, that was a very enjoyable break, but I need to get back downstairs and start working on this week's budget. Thank you very much, Mr. Ambrose." I leaned down and gave him a kiss on the cheek.
"Anything for you, Mama."
As I came down the stairs into the large foyer that doubled as the lobby for the brothel, I noticed a petite young woman staring at the pictures of my boys on the wall. I could tell from her body language that she was very nervous. When I reached the bottom of the stairs, I stopped and watched her for a moment. She spent a good while in front of each boy's photo, but when she got to Jon's, I noticed her linger there a little longer and I could hear her sigh rather loudly.
"He's a handsome son of a bitch, isn't he?" I asked suddenly, making her jump.
"Oh. Um...yes. He is, uh, ma'am," she answered. Her voice was quiet and weak. Now I was wondering if she had somehow wandered in here by accident.
"Honey, I hate it when people call me ma'am. Please, call me Big Mama." I held out my hand as I approached her. She tentatively gave me hers. Her handshake left much to be desired. "Is there something I can do for you today, sugar?"
"I don't really know. Am I allowed to say that I'm just looking?"
I laughed at her honesty. "I suppose you could, honey, but I've never had anyone come in here just to browse. Everyone has a specific reason for showing up, whether they have a particular fantasy they want to explore or they're just lonely. You must have a reason for stepping over the threshold of that door."
She lowered her head and twiddled her thumbs. It looked like something was right on the tip of her tongue when a door to the left swung open and a handful of the boys came up from the gym. I couldn't help but sneak a peek at their sweat drenched bodies. That particular sight always got my heart racing. I shook off my excitement and turned back to the young customer. Her face was as red as a ripe tomato and she was standing in a different position than before. I assumed that seeing the boys had made her nervous.
"Are you okay, honey? Why don't we go into my office where we can talk privately without all those pesky boys interrupting us." I smiled warmly at her and beckoned for her to follow me.
"Now tell me what your name is, sweetheart," I said as I shut the door behind me.
"Rachel, ma'am. I'm sorry, I mean Big Mama."
Despite the slip of her tongue, I liked this young lady. I found her innocence quite refreshing, especially in my line of work.
"I'm going to cut to the chase, Miss Rachel. Are you a virgin?"
To my surprise, she laughed.
"Not in the least! I'm 24 now and I lost my virginity when I was 17. So definitely not a virgin, Mama. "
"I can't say I'm not surprised. You seemed so timid and uncomfortable out there in the lobby, especially when the boys came through. I just thought that may have been the case."
"I'm just nervous to be in a place like this. That's all. I'm a virgin when it comes to the sex industry," she explained, a small smile on her lips.
"Well, we all have to start somewhere, honey. So now that we're in private, why did you decide to come here today and what can I do to help you fulfill that need or desire?"
"Umm…well…the truth is…" She continued her sentence, but her voice became so quiet and mumbled that I couldn't make out what she was saying.
"I'm sorry, honey, you're going to have to speak up," I pleaded.
"The truth is, I've never had an orgasm. I'm able to become aroused enough, I think, but I've never been able to orgasm for some reason. I've had plenty of sex, especially in this past year. I've been slutting it up, trying all sorts of different partners, searching for what is apparently my white whale. Coming in here today is my last ditch attempt before I visit a doctor to see if something is physically or mentally wrong with me." She let out a long sigh, like she had been holding all of that in for a while and it felt good to finally get it out.
"Is that all? Oh honey, don't you worry, I have the perfect gentleman to help you out with that pesky problem."
About a week later, it was time for Miss Rachel to finally capture that elusive orgasm. Or at least give a fair fight for it. That morning I had given the boys their daily schedules as usual, but I told Jon to hang back for a moment.
"What's up?" he asked.
"So I blocked you off for the entire day. I have a special assignment for you, my love."
"Oooh, a special assignment, huh? Like a challenge? You know I love testing out my…abilities."
"Oh yes, love, this will definitely be a test of your abilities," I replied. "Your customer for today is Miss Rachel. This lovely young lady has never had an orgasm before."
"I call bull shit."
"I'm fairly certain that it's legitimate. If she had been lying, she wouldn't have been so physically distraught when she came in last week. Her body language told me she was genuine."
"Huh. Poor thing, then."
"Don't you dare go feeling sorry for her. I doubt she's going to feel comfortable and sexy with you pitying her, honey. She said that she's been with many partners, but still no orgasm. She's on the verge of going to see if there's a medical or psychological reason behind it if you and her aren't able to get her to come tonight. I booked her for the whole day because I'd like you to spend time with her and get to know her. It seems like she's a timid girl overall, so if you were to just go in for the kill, I think she would be very intimidated. She should be relaxed and confident when it's time for you to do your thing. I gave her my word that you would do everything you could to help her out with this…" I placed my hand on his cheek. "…so don't fuck it up. Now go get ready. I told her to be here at 10am to meet you." I walked around him and smacked his jean-clad ass as I went by. It's good to be the boss sometimes.
Not entirely knowing what to expect from this woman, he chose to wear a pair of nice black slacks and a crisp blue button up dress shirt. He figured it would be a safe bet to go with the clean well-dressed look rather than his preferred slacker look. If this chick turned out to be cool, he could always change later, but most of his customers tended to enjoy a more formal look from him.
He went outside to smoke while he waited for her to arrive. When she pulled up and got out of her car, he approached her and held out his hand.
"You must be Rachel," he mumbled over his cigarette before he spit it on the ground and stubbed it out. She stood frozen, staring at his hand. "You okay?" he asked.
She shook her head and accepted his hand. "I'm sorry…it's just that she didn't tell me it was going to be you."
"Oh? Is that a bad thing?" he laughed.
Her face clearly reflected the embarrassment that she felt. "No, it's not a bad thing. I've just…um…I've seen your picture on the posters and I've used it to…you know…fantasize…" She was barely audible on the last work, but he knew what she had said and he wasn't about to make her repeat it.
"Why don't you come take a walk with me, Rachel, and let me get to know you a little bit. I like to talk with my customers ahead of time so I can get a feel for them."
They had been walking in silence for a few minutes, enjoying the fresh morning air. Rachel had her head down, still feeling nervous standing next to this man whom she had tried to pleasure herself to once or twice. He could tell that she was uncomfortable, so he motioned to a nearby tree and they went to sit down.
"So tell me about yourself. I want to know how I can get you off." He took out another cigarette and offered her one, but she turned it down.
"I'm 24 and until about nine months ago, I had been in a long-term relationship. I had been with the same guy for about five years. It was a pretty good relationship, emotionally, but sexually…I don't know. Big Mama probably told you this already, but I've never had an orgasm before." He nodded as he took a drag of his cigarette. "With Brian, that was my boyfriend, we had sex often and it always did feel nice, but I could never climax. I'm ashamed to say that I ended up faking orgasms. He could never tell. Out of guilt, I finally admitted it to him after years of doing it and that's what led to our break-up. Since then, I've been having all sorts of random sex, trying to figure out how to get myself to come. I haven't had any luck, so I figured I'd see a "professional" before I saw a professional."
"No wonder she booked you with me," he said with a smile. "I won't promise you that I will manage to make you come, which is honestly something I never thought I'd say, but I will promise that I will try hardest and that we'll have a lot of fun together. Sound good?"
She nodded and finally gathered up the courage to lift up her head and look him in the eyes. Those brilliant blues smiled back at her and she could already feel herself moistening.
"So how do you normally meet men, Rachel? It seems like you're nervous about fucking a prostitute, so I'm thinking that we might do a little bit of roleplay to help make you more comfortable."
"I tend to hang out at bars and bring guys home from there," she replied.
"Perfect. I want you to go home and relax. Around 8ish, come to the bar at the corner of 7th and Main, and we'll see how things go from there." He took her chin in his fingers, angling her face up to his, and leaned down so that his lips were almost touching hers. "I'm really looking forward to getting to know you." She let out a shaky breath and leaned back, dropping his hand, and smiling. He never got tired of eliciting that reaction from people.
Rachel sat at the bar nursing a glass of Pinot Grigio. She had been sitting alone for only about fifteen minutes, but it felt like so much longer. She tilted back her head and finished off her glass, feeling the warmth of the liquor flow through her body. She looked at herself in the mirror behind the bar. She hadn't dressed too fancy, but she did use a curling iron to give her hair a few soft waves and she wore a little black dress that she honestly hadn't worn in ages. She smiled at her reflection. Dammit, she did look pretty tonight.
The bartender leaned down slightly to get into her field of view, bringing her back to reality. "A drink from the man at the end of the bar," he said, smiling and nodding his head to the left as he placed a fresh glass of wine in front of her. She thanked him and then cautiously glanced to the side. Her face immediately burst into bright red.
He slid up onto the stool next to her and leaned against the bar. "Well hello there," he said smoothly. She began to giggle profusely. "What's so funny, cutie?" he asked.
She turned to look at him and she immediately stopped laughing. He was wearing a well fitted black suit, but his hair was disheveled like he just got out of the shower. It was a strange combination of looks, but it still managed to make her lose her breath for a moment.
"It's nothing. Were you the one who bought me a drink?" He nodded as he took a sip of his own glass of whiskey. "Thank you. That was very kind of you."
He set the glass down and wiped his bottom lip with his thumb. "You're welcome. I'd give you some lame pick-up line, but I don't think that'd work on you, right?"
She laughed and slowly ran her fingers up and down the stem of the glass. I'd probably need about three more of these before a cheap line would work."
"Bartender! Three more Pinot Grigio's, stat!"
Her shoulders hunched over as she laughed. She sat back up and wiped away a tear. "You are just too cute. I'm Rachel. Pleased to meet you." She smiled genuinely and held out her hand. He took it in his and placed his other hand on top.
"You can call me Dean, sweetheart."
"Do you often let strange women take you back to their place?" she gasped out after they broke away from a long, breathy kiss.
"Only when they laugh at my lame jokes and fit perfectly in my lap." He squeezed her thighs and she let out a short yelp. She had been careful to not fully seat herself in his lap because she was afraid of what she might do in the cab if she were to feel his pelvis against hers.
The car finally pulled up to the curb and they pulled themselves away from each other long enough to pay the driver and exit the car. Rachel collected herself and smoothed down her dress. She didn't want to make a scene when she went up to her apartment. She stood in the lobby, calmly waiting for the elevator when Dean came up behind her and wrapped his arm around her waist. Her heart started beating fast again and her breaths became shorter.
"How long is it going to take for this damn elevator to get here?!" she cried out.
"You sure are eager. I like that." He pinched her bottom and she quietly whimpered.
"You are so not helping right now."
"I wasn't trying to," he chuckled.
When the elevator finally arrived, they stepped in, and as soon as the door shut, Rachel jumped up onto him and proceeded to devour his neck. When they reached her floor, she quickly hopped down and cleared her throat.
"I like to pretend that I'm a classy lady when I'm in public," she said as she led him down the hall to her apartment.
"And what are you in private?" he asked as he took off his sports coat.
She unlocked door and stepped inside, grabbing his tie and pulling him in. "I like to think of myself as a playful rogue." The door clicked shut behind them and she quickly began working her fingers over the buttons of his shirt. "I'd tear this right off of you right now if I didn't think I'd be charged for damaging the goods."
He laughed as he loosened his tie and slipped it over his head. "I wouldn't charge you for it, but I'd be stuck without a shirt." They both stumbled forward toward her bedroom, kicking off their shoes in the process.
She finally managed to open up his shirt, pressing her sweaty palms against his warm tight flesh. "I'm pretty sure no one would be complaining. I mean, have you looked at yourself lately?"
He didn't answer. He just picked her up, his hands cradling her ass, and carried her into her bedroom. He placed her down on her bed while they exchanged breaths, their tongues lightly touching one another so that they could just get a hint of what the other was drinking that night. He pulled away from her and started to remove his belt.
"Take that damn dress off before I rip it off of you." She laughed and he stopped and stared at her. "You think I'm joking, sweetheart? I have destroyed many dresses over the years. If you like yours, you'd better get naked right now."
She bit her lip and swallowed hard. She had never been bossed around like that before. Most men had just done the usual sex run-down. A little bit of foreplay, then penetration, sprinkled with the typical stock dirty talk. There was something about Dean being a bit aggressive that made her feel more turned on then she ever had before.
She watched him strip down completely, not moving an inch to follow his lead.
"So you want to play this way? Is this what you like?" he asked.
"I never knew before, but apparently. The threat of you getting aggressive is getting me going."
"Oh really, is it now?" He slowly walked up to her and leaned down, wrapping her hair around his fingers and lightly tugging back. "I'll keep that in mind." He lightly grazed his bottom teeth up her neck, eliciting a whimper from her.
Just as his mouth was about to reach her ear, he pulled away and let go. He grabbed a chair and fell back into it, crossing arms behind his head and propping his feet up on the bed. The sight of him fully stretched out like that was torture to her. "But why?!" she whined. "I hate begging, but I really want you to fuck me right now."
"Patience, sweetheart, patience. I'm here to try to help you discover your orgasm, remember? I'm a man of my word, so let's try something. Have you ever been able to come from masturbation?"
"No. I don't really masturbate much because of that." She looked honestly disappointed.
"Well, Rachel, I would like you to touch yourself for me. I want you to lift that skirt up, pull those panties down around your ankles and make yourself feel good."
She complied quickly and gently touched between her legs with her fingers. She was much wetter than she thought she'd be. In all honestly, she was wetter than she had ever been with anyone else. She rubbed her two fingers between her slick lips, lightly teasing her clit as they passed by. After a moment, she stopped over her clit and began to rub slow circles around it. She sank deeper into the bed sheets as her body started to tingle with pleasure.
"That's it. Keep that up." He sat up and leaned forward, his arms resting on his thighs. "Do you know just how hot it is to watch a woman pleasure herself? It's the most beautiful thing in the world. How does it feel?"
She took a few deep breaths before she answered. "It feels really good. But this is what I'm used to. A very nice plateau feeling, but never an actual orgasm."
"Hmm." He rubbed his chin with his hand as he thought. He stood up and moved over to her side. He knelt down and started to nibble at her neck, leaving more bites than kisses. He pushed her head to the side, exposing more of her neck and collarbone for him to devour. "How does this feel? Whenever I try something, I want you to tell me how it's making you feel. Communication is going to be important here."
She nodded with a look of slight pain on her face. "The biting feels good. I think my neck is very sensitive."
He slowly ran the tip of his tongue from her collarbone up to her ear. He bit the tip of her earlobe and whispered, "I'm going to fuck you right now. That's what you want, right?" She nodded quickly, her mouth pursed shut so that no stray moans escaped. "Now what I want you to do is continue rubbing that cute little clit of yours while I thrust, got that?" She nodded again.
He grabbed a condom from his sports coat, crawled up between her legs and lifted them so that they were resting against his hips. He rolled it onto his fully hard length and teasingly pressed the tip against her entrance, rubbing it in circles.
"Are you trying to fucking kill me here? Just shove it in, you jerk!"
He quickly brought his face down to hers, one of his hands lightly wrapped around her throat. "Do you want to say that again, but more politely this time?"
"No because I really like your hand around my throat like this," she sighed.
"You dirty girl. You really are a bit of a rogue, aren't you?
He slowly pushed his cock between her wet folds, letting out a low grunt as he did. He started off slowly, eventually gaining speed and settling into a steady rhythm. Rachel quietly moaned his name when he squeezed her throat a little tighter. Her fingers were moving much faster now and he suspected that she may be close.
"How are you, babe? Can you come for me?"
"It feels good. Really good. But I don't know if I'm close or not. I don't know how to tell." He could tell that she was beginning to get frustrated.
He let go of her throat and gripped tightly onto her thighs as he began to thrust much faster and harder. He thought perhaps something a bit rougher and deeper might help her get over this plateau.
The minutes continued on, but the results were still the same.
"I give up! This just isn't working! There's something wrong with me and I don't want to waste your time anymore." She covered her face with her hands and let out a muffled yell.
"I'm not giving up on you yet. We can do this."
"How are you so sure?"
"Because I'm Dean fucking Ambrose, and I'm damn good at my job. Now do you trust me?" She sighed and said yes. "Okay, you are clearly in your head about this. I want you to just relax. Don't think about the orgasm. Don't think about anything. Just let yourself go. Get on your knees and turn around."
He held her tightly against his chest and eased her back onto his cock. He guided her hand back to her clit and began to slowly thrust up into her. He pulled her body up and down in time with his thrusts, making sure to go as deep as he could. He used one hand to cup her breast, softly running his fingers along her hardening nipple. He buried his face in her hair and listened to her soft moans. For two strangers in a very strange situation, it was quite romantic.
Eventually her moans became louder. His instinct told him to thrust faster and harder, but he held himself back and continued the slow, deep grinding motion. He started to bite at her neck when he felt her body tightening. He knew the familiar signs. He had seen them hundreds of times before. He kissed her ear and moaned, "Let yourself go, Rachel. I want to feel your pussy tremble."
Her orgasm was oddly silent. She held her breath as it swept over her. He knew by her facial expression and how her walls tightly gripped onto his cock, though, that it was a deep full body orgasm. He held her there for a moment while she let the feeling slowly fade away and her heart beat return to normal. Her eyes slowly fluttered open and they looked glossy with tears.
"Are you getting emotional on me?"
She sniffed and wiped away a tear with the back of her hand. "Sue me. I've been waiting to feel this for years and now I know that I don't have a medical or psychological problem. I'm a bit emotional right now."
He smiled and kissed her temple. "Congratulations." She laughed and pulled herself off of him. She then turned around and reached out to give him a tight hug. She leaned back and a sheepish grin appeared on her face.
"What?" he asked.
"Umm…would it be possible for me to have another one of those?"
He laughed smugly. "Sweetheart, I can go all fucking night."
The next morning as Dean groggily stumbled back into the house, an early morning cigarette hanging between his lips, I peeked out from my office door and smiled at his disheveled look.
"Long night, my love?"
"Challenge accomplished, Mama," he said with that cocky grin that I adored.
"I knew you could do it. I'm guessing that you both really enjoyed yourselves, hmm?"
"Yeah. It was actually a lot more fun than I thought it would be. How do you know, though? Is it my hair? Cause my fucking hair is always like this."
"Yes, that is part of it," I said with a wide wicked grin. "But also because she's already booked you for three more visits."
