My Mom, the High End Escort Ch. 03

"The occasion I started escorting was really nothing special. After I stopped giving therapy, I found a job as an admin assistant in a hospital. It was long and boring work. I got friendly with this girl who was my colleague. She was young and quite good looking and didn't take her work as seriously as I did. She would often show up to work late and brag to me how much money she just made in her side job. Very soon she admitted to me that she was escorting on the side. One evening at a happy hour she asked me if I wanted to go meet a client later in her stead, since she couldn't make it.

"Now, that was a big move for me. I felt hesitant at first because I had always thought girls who prostitute themselves were below me. But the money was tempting, I had a daughter to feed, and I was freshly ghosted by a man I was dating that time. All those factors, plus a bit of alcohol, pressed me into making the decision that would send me down a slippery slope.

"But I fell in love with my new career. What I enjoyed most, apart from the money, was how much these men appreciated me. I see only a selected dozen clients and treat them with utmost care and respect. It was, in a way, just like therapy. I help them with their needs and problems and keep their secrets. And I have seen obvious improvements in them -- boys walking out feeling more confident, and married men going back to their family with a calmer attitude. I know society looks down upon all that, but it satisfied my desire to help people. All my clients love me, and they need me like children need their mother.

"I don't understand why there is so much stigma against sex work. I do it entirely out of my own free will. I am not trafficked, I don't use drugs, and I have no pimp. The ultra-feminists say that people like me are being coerced, that I don't know what I'm doing. How dare them to be so condescending? What moral right do they have to preach to others? They are preaching not to help me, but to feel superior themselves. No, thanks, I know exactly what I'm doing.

"People say it's immoral because I'm doing it for money. But why would taking money make it immoral? Teaching is great work, but teachers don't do it for free, and that doesn't diminish the nobility in teaching. Nursing is great work, but nurses don't take care of patients for free, does that say anything less about the nurses? There's nothing wrong with doing good work and taking money for it. How come instead, when sex and money, two of the best things in life, come together, suddenly it becomes something bad, something immoral?

"The traditional folks say a woman's sexuality is her glory, and she ought to cherish it. I agree with it wholeheartedly. I do cherish my sexuality, that's why I share it with people who need it. If you have something great, if you have the gospel, would you keep it to yourself, or would you share it with others? I don't know if you believe in salvation in the afterlife, but my vagina," She paused, looking slightly shy for saying a raunchy word like that, "is truly the salvation for men. And it doesn't happen in the afterlife. It happens in the here and now."

"And you know what else is better than giving therapy? All my patients keep coming back. They come to me, get their fix, and a week, two weeks, or a month later, they always come back to get their fix again." She winked, "It runs like clockwork."

I marveled at her confidence. It was a different kind of confidence from mom's. Mom took pride in exploiting men and controlling their desires and enjoyed feeling like a queen. Katie here derived her confidence from her ability to care and help, and from the gratitude of her clients.

"So..., do you still do therapy on the side?" I asked?

"All those spicy little things I've told you, and you ask me this?" She chuckled, the tiny wrinkles at the corner of her eyes suggested it was a genuine smile. "They say abrupt changes of conversational focus indicates insanity or ingenuity, and I'm still trying to decide which one is you."

"Actually, I still have two patients I'm seeing on my therapy side." She continued, "Of course they know nothing about my main gig, lest me getting reported. They are chill and have been working with me for years now. They've made great progress along the way."

"Would you consider giving me therapy?" I asked, hesitantly, "I think that may be what I need most, at this point, even more so than... you know."

"Hmm that's a thought." She quipped, pretending to be in deep thought. "You might indeed have a need for that."

"Let me take a closer look at you." She said, raising her hands in the air as if she was cupping my face in them. "18-year-old and fresh out of high school. Very shy and a bit skinny, but otherwise quite the eye candy. Not many acnes so it's not like you're not getting any. Sexual frustration is apparent, but the main issue is not, you know..., but something else. Tell me, is it girl issues or mommy issues?"

I was aghast at her reasonably accurate observation and very forward suggestion, "Guess I can tell you later, when we are..., you know."

Katie giggled, "Oh my god. I wish all men were adorable like you. Indeed, why don't we take a step further? By this point I'm sure you don't have serial killer vibes, and you are a bit too shy to be a cop. Oh sorry -- one more thing. Are you comfortable to talk about the donation now?"

"Sure..." I said. Part of me wanted to leave, since all my life I had never saw myself as the type to pay for hookers. But up against this gentle, attractive woman in her early 30s who also seemed to understand all my problems, my hesitation didn't stand a chance.

"That'll be $750 for an hour." She said.

"Excuse me?" I tried my best to not exclaim loudly in a Starbucks.

"$500 for the woo-hoo, and $250 for the therapy. They'll be performed together, but still charged separately." She explained.

"Alright." I agreed meekly. The price was a bit outrageous for a student, but what she said made sense, and my mouth was already watering, so I could do nothing but agree to it.

"Sweet deal. Are you ready to move on from here?" She took the blue scrunchie out of her bag and tied her blonde hair back into a ponytail, before taking her sunglasses out and putting them on.

"Yes, I am." I answered eagerly.

*** ***

We arrived at her apartment, namely also mom's secret nest. The furniture was all put back in their place, with all the right decors and appliances on top of them. There was no sign of the crazy orgy that just took place the night before yesterday.

Katie took off her Chelsea boots and put them down by the door. She then took her socks off and tucked them into the boots, revealing her beautiful pale feet on the floor. She invited to sit on the couch, before heading back to the kitchen area herself.

"Tea or coffee?" She asked.

"Tea..? I guess." I said, not expecting such an everyday question from an escort.

"Good choice. Tea calms you down, while coffee excites you, often quite unnecessarily." She quipped.

A moment later, she sat in the armchair on the left side of the couch with her back to the window wall, and placed the tea set on the coffee table in front of me. She then poured one cup for me, before pouring one for herself.

"So, fill me in. What's the reason for you to come here and seek help today? Besides, obviously, to fuck me." She said with a giggle.

That gave me an instant hard-on, but I managed to tell her my story as calmly as possible. I told her about mom's sexual engagement with Mr. Svenson. I concealed mom's escort part of the story as much as possible, since it would otherwise more than likely expose her identity, which then meant mine. I framed it as an affair of mom's that I happened to witness while following her, after she ditched me at my birthday. I did not tell her about mom's gangbang, since that would equally give her identity away. It took a good 10 minutes for me to tell, because I kept stuttering, stumbling, and backtracking my story out of discomfort about the topic.

"Let me rephase." She finally injected. "You saw your mother, a single mom, having sex with another man, and you have very strong feelings about it."

"Correct." I said.

"First, I am very sorry to hear about it. I am a single mom myself, and I know how devastating it could feel. But I want you to know that you are not alone. Many children with single moms have suffered from the same. Fortunately, there are proven ways to deal with it. It is a difficult situation, but we can work on it together." She grabbed my left hand with both her hands and held it on her lap, her eyes full of care.

"So, let's go over the feelings. What were the feelings you had when you saw it? Tell me about them one by one." She asked.

"Anger." I said. That was my first feeling.

"Good." She said, "Anger at what?"

"Anger at my mom's betrayal." I said, my teeth started to clench, "Also I'm angry at myself."

"Being angry at oneself over thinking or reacting a certain way is a second-order feeling. It's more complicated. We'll go over it later. Let's focus on the first. Why do you say it's your mom's 'betrayal'?" She asked. I admired the calmness and clarity of her tones.

"Because she left me at my birthday to have sex with this unworthy man." I answered, feeling a bit emotional.

"Children get ditched and broken promises all the time. Although it is a very valid for anger, they don't, in general, react as strongly as you. I hope you can see there's more to your anger, and I would wager the key lies in the word 'unworthy'. Let's keep that in our note for the moment and move on. What else did you feel besides anger?" She asked, holding my hand tighter onto her lap.

"Fear." I listed, "Fear of abandonment."

"Good. This is a valid feeling, very common among children from single parent households. I'm glad you could delineate it that clearly." She said, "What else?"

"Jealousy." I added.

"Excellent!" She exclaimed, her blue eyes shinning with excitement. "We are getting closer to the root of it. Keep going for me. What else did you feel about it?"

"Arousal." I continued, my voice wavering from uneasiness. "I hated what I saw, but my body could not help but get excited by it. I came to it. I felt like a freak."

"Let me tell you, that what you felt and the way your body reacted to it, are a hundred percent normal. You are not a freak. Anything else?" She said, calm as ever, stroking my hand lightly with hers.

"Shame." I added timidly.

"Indeed, shame, the mother of all negative feelings!" She marveled. "Just like anger with yourself, it is a valid, but more complex feeling. But let me assure you, when we have worked out all the other feelings together, shame will have worked itself out. Have no worries. That's it? Anything else?"

"Yeah, I think that's... it." I concluded.

"Very good, young man. You have shared with me anger, fear, jealousy, arousal, and shame. Among them, anger and fear are rather direct, while the other three are more complicated. I think we are ready to move on to the next stage of therapy, where we can address these issues one by one in a more intimate manner. Ready?" She stood up softly without waiting for my reply, my left hand still in her hands.

She turned around, holding my left hand in her right hand, and headed towards the bedroom. I followed her through the door, and my feet felt the switching from hard wood floor to carpet. But a strong urge took over me, and I pulled on her right arm where we were holding hands and turned her around. I then placed my right hand on her left shoulder and pressed down.

*** ***

She instantly got the cue. Silently, she went down on her knees with an understanding smile on her face, the hem of her tea dress spreading on the floor like a blue lotus. She let go of my hand that was still in hers, and deftly untied my belt buckle with both hands. She then reached her hands in beneath my underpants, and pulled them down together with my jeans, her hands feeling a bit cold on the hot skin of my butt. My raging boner popped out like a rooster entering the fighting ring.

"Mmm." She hummed, her blue eyes squinted lightly into a smile. "Yum." Instead of taking my cock in right away, she held it with both her hands and pressed it against her face, as if it were her favorite barbie doll.

My eyes were wide open, half in awe of her innocent demeanor, half from burning desire.

"My boy can't wait." She giggled, opening her thin lips and took my whole cock in her mouth with one slurp.

The sensation of being in her mouth was supreme. Her body temperature seemed to be a bit lower than most people, and even the inside of her mouth gave me a cool sensation, which only made my pleasure my intense when contrasted with the fiery hot skin of my cock. Her tongue swam around the tip of my cock like a soft minnow, sending waves and waves of electric currents up my nervous system. She then took her lips off my penis, kissed its tip gently, before sticking out her tongue to play with it. The whole time she did not break eye contact with me for a single second.

Had I not tried to hold myself back the hardest, I would have cum there and then. Seeing my intense look, her face turned into a broad smile, and she spoke.

"How does it feel to see a gorgeous mature woman on her knees like a little lamb servicing you? I bet I've blown your 18-year-old ego as hard as your cock. I would gladly do it anytime for you, but right now we are still in therapy, and we would have to be in more comfortable positions to keep talking about the issues. Therefore -- would it please you to take all your clothes off, and lay down in the bed? Oh yeah -- put a pillow on the headboard and lay against it, so it'll be easier for us to talk." She said.

Yes, it would please me. I gladly did what she bid.

Katie crawled onto the bed, still in her blue dress and ponytail. She approached me from down under, and took each of my balls in her moist mouth, before lifting up her face and appearing right above my raging cock, her hands grabbing my thighs, and her soft breasts lightly rubbing against my inner thigh.

"Here's the rule of the games. My job is to blow you and ask you questions, and your job is to answer them while maintaining an erection. Think you can do it?" She chuckled?

"That I don't doubt." I didn't think it would take me any effort to maintain my hard-on. I was more worried about having enough focus (and blood in my brain) to be able to answer the questions.

"Let's go. A moment ago, you mentioned jealousy. Why were you jealous seeing you mom having sex with another man?" She asked, and before I could formulate an answer, she pressed her head down and buried my cock deep into her mouth.

"Emm... I guess I was jealous that mom would leave me high and dry to fuck these men when it should have been --"

"You?" She suggested, opening her mouth to let my cock out so she could talk.

"In a way, I guess..." I murmured.

"Answer me truthfully. Do you want to have your mother the way a man would have a woman?" She asked solemnly, her right hand holding tightly onto my manhood as if it were a ceremonial mace.

"I mean, yes, we all have the Oedipus Complex." I hesitated, "But it's just that I've never considered it a serious possibility."

"Why not?" Katie pressed on.

"Because... She's, my mother?" I asked, a bit incredulous with her straightforwardness.

"Young man, you are a good kid. There are many good things I can say about you. But you don't seem the type to care about adhering to cultural norms." She teased, circling her tongue around the tip of my cock, building up my pleasure.

"It's not that. It's just we are all animals of habits." I was buried deep into my thought, "The whole time growing up I saw her as my mom, and I was told to date girls my own age, get married with one of them, and have a family. I never saw being with mom, either permanent or short fling, as a realistic possibility. Of course I drooled over her body like every other teenage boy would, but I never considered it seriously. Do you get what I'm saying?"

"Yes. I understand." She pushed my cock out of her mouth again and answered. "Do you want to be with a girl your own age?"

"No." I answered instantly. "Never." I cupped her pretty oval face in my hands and looked her in the eyes.

"I thought so." Katie giggled. "Oh boy you are making me all tensed up. Let me relax myself for a sec." She sat down briefly, stretched her arms, and took off her blue tea dress and tossed it onto the floor. She took off her white bras, sent her pristine perky tits bouncing like a pair of white doves. She took off her white knicker, giving me a sneak peek of the golden landing strip of her pussy, and the pink lips underneath. She then took off her scrunchie, letting her blonde hair fall loose onto her shoulders and now bare chest.

She dived down onto my cock again. Getting oral pleasure from her was one heavenly affair already, but the sensation of her soft golden hair falling and brushing onto my dick and balls was also indescribable. It made me feel so warm and fuzzy that I reached out my hands to caress her face and hair. She gave my member another good minute of licking and sucking, before stopping to ask me again,

"So, you acknowledged that you wanted to be in these men's place. Does that make you feel insufficient?"

"Yes and no." I answered, trying to find the best way to enunciate my thought. "You see, some of these men are not that great. Some are disgusting. I don't see them as more manly to me, and I don't see myself as inferior to them, but that only makes me more angry."

"So what you are saying is," She paused in the air, suddenly so serious in her face and tone that she stopped giving attention to my cock for the first time. "Your mother is being such a skank that she would fuck anything that moves, but not you, and that hurts you more than anything else."

"Yes!" I exclaimed; my voice pumped up by the humiliation brought by her remark but also renewed arousal. "Yes. Yes! That's exactly how I felt. I was so angry with her, and disappointed at myself. I thought maybe I'm not good enough, and if I were good enough, she wouldn't reject me."

"You are letting these imagined thoughts and scenarios torment you." She said, after some consideration. "First, she hasn't rejected you yet. Second, even if she did reject you, it wouldn't have been because you were not good enough for her. Third, even if it were because that you were not good enough, you may still get good enough for her someday."

"How do I get good enough for her?" I asked, totally missing her more important points.

"Are you seeking self-improvement?" She asked, resuming her fellatio on me.

"Yes, always." I answered, not without pride in my tone.

"Uh-uh" She shook her head, voice muffled by my cock still in her mouth, her blue eyes looking into eyes. "Don't" She moved her mouth off my cock. "Here's some advice from a more mature woman." She teased me with her tongue, "Do not seek self-improvement. It's just an excuse to not live in the here and the now."

"Then how am I supposed to get better?" I asked, incredulous.

"It happens naturally." She answered. "Think about it, did you do anything to grow to 5'11"?"

"Well, it's just 5'10"." I corrected her, "and no, I didn't do anything for it."

"And, did you do anything to grow such a beautiful cock and such delicious balls?" She moved her tongue down my shaft to tease the cavity in between my balls, before sucking my left ball into her wet mouth.

"No, I didn't." I got her point.

"See? The best things in life happen naturally. If you think about it, our primate ancestors did not do anything to evolve into human beings. They just lived, and it happened. Thinking about self-improvement will make you rigid, and prevent you from being absorbed into the moment. All you need to do is stay healthy and reasonably happy, and just enjoy." She gave the tip of my cock another gentle kiss.