I have a happy personality
with a heavy soul
sometimes
it gets weird
Category: Uncategorized
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I know I am here building an even better life for myself, but this has been the hardest part of my journey, looking inwards at my insecurities and flaws. I am trying to stay humble and appreciate the journey. However, being vulnerable and showing my insecurities is harder than talking about the bad things I’ve been through. I wear my heart on my sleeve which usually leads to heartbreak in my case. I’ve allowed my fears to manifest themselves and control my life. My fears have held me back from amazing opportunities and love.
I not only daydream about falling in love, I also dreamt about hosting my own music festival one day. I want to host a music festival that helps undiscovered talent, become discovered. A festival that brings all different kinds of people together to share the one thing we all have in common; Our LOVE for music. Then someday, I will put myself on my own stage. I have held onto this dream for a very long time and its one of the things that got me through the dark times. My dreams are the light at the end of the tunnel.
I was once told by someone on a dating app, “Following your dreams is very important, I’m sure you will get what you’re chasing, just life will test you to make sure you want something bad enough”. It’s funny how I get life advice from a complete stranger on a dating app and it hits me right in the heartstrings. I really want to make my dreams come true, to host a big music festival and share my success with my friends, family and my lover. But some days I get discouraged and those dreams seem further away than I thought I was. However, my mom did not raise me to be a quitter, I must do the things that scare me in order to make my dreams come true.
My mom would always say to me, “Never give up on what you’ve started, stay focused on what you really want and all the hard work will pay off someday.” So that is exactly what I set out to do.
A smooth sea never set out for a skilled sailor. – Unknown
Am I Worthy of Your Love?
For as long as I can remember, I have always wondered if true love was real. I would daydream about the person I’d fall in love with, during class. I’d gaze out the window, wondering what they would be like. Would they be tall? Short? Would they feel the same sparks that I do? Will they be passionate? Will they know when to kiss me without saying so? Will they still love me in 40 years when I’m older with grey hair? Would they bring me flowers, just because he/she/they were thinking of me? Would we want the same things in life? But now the bigger question I’d have, could they accept my past?
True love is a strong and lasting affection between spouses or lovers who are in a happy, passionate and fulfilling relationship.
Unfortunately, I have my own self-esteem issues. It’s like, I feel that I am unworthy of love so I will push away any potential lovers by causing issues within the relationship that are not actually there. I come up with the worst case scenarios or expect the worst of my potential suitor. If I felt like they were going to leave me, I would double-down and become clingy. Losing myself trying to keep the person only to push them away in the process. In other past relationships, they couldn’t accept me for who I am at face value and when I would open up about my past or start to let my walls down, they leave. “I’m too hyper or too outgoing.” “I’m too intense” ” I’m showing too much emotion or not enough.” “I can’t be with someone who was a sex worker” or ” Want to get back into the game and I’ll be your pimp.” It felt like a never ending roller coaster of shame, loneliness and guilt.
No one but myself can change my self-esteem problems, abandonment issues and my actions. I have become aware of my wrongdoings to others and most importantly, the wrongdoings to myself. I carried so much shame from becoming an escort, dabbling in drugs, using peers to my own advantage, and the circus of men to just not knowing what the hell I am doing. But does anybody really know what they are doing?
The parade of men that I’ve let into my body must come to an end. Maybe writing about it will help me discover how.
I’ve always felt I wasn’t good enough, even before I left for college. It’s like I have this other voice in my head that whispers negativity into my ear. “You are not good enough.” “No one will love you.” “You are unworthy.” It’s as though my inner voice is saying the truth. Some days I can drown the whispers and other days the whispers become screaming. The voices become so loud that I wish I could escape my own mind. I always question why? Why me? I am a positive person, but am I really? Or is that just one of the masks I wear? Maybe I mask my insecurity with humor?
The game also took a toll on my self-esteem. I gained weight during my first year at college, clients could tell and they were vocal about it. ” You’re not thin enough, curvy enough, or too curvy.” “You’re not blonde enough or brunette enough.” “You look too innocent or not innocent enough.” As I tried to conform to all of the needs of these people, I began to lose myself. That is when I decided it was time to leave the game. It wasn’t until I finally started to form healthy friendships that showed me that I am enough and led me to my lover who shows me that I am Worthy.
They say, “You must love yourself before you can love someone else.” But what if, the love from your friends and lover is what you needed to learn to love yourself? What if they show you how to love yourself and the parts you hate. Can’t we be broken and still love?
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At the Condo where all the girls worked out of, I was oblivious to what the other girls were up too, which kept me out of trouble for the most part. Most days, I would be sitting on the living room floor with my books spread out on the carpet while I studied in between clients. Other days, I would be napping on the couch. During my first year, I didn’t spend much time at my apartment. I was either at school all day or at the Condo all night. I just wanted to have a “normal” college experience like the other girls in school while being able to pay my bills.
Outside of the condo, my world was lonely. I was either studying, in class or going to work. In the beginning I didn’t have time for a social life. But I was craving for some form of normalcy and not sure where to start. It wasn’t until I met my first college boyfriend, Spencer. Spencer was twenty three, tall with dark hair, blue eyes, quiet, awkwardly cute and in school to become a Police Officer. When I had met Spencer I was with my friend Aria at the time, and he was with two of his best friends in line at the college bookstore . Once we had locked eyes, he held my gaze long enough for him to come over to ask me out on a date. Without hesitating, I said yes, not thinking about the fact that I was still an escort and still had to work that evening.
On our first date, it started out by Spencer meeting me after class in the student parking lot to drive us downtown. Luckily, I had kept a LBD (Little Black Dress) and black heels in my backpack from work for the occasion. It was either the LBD or scrubs. Spencer was wearing a sweatshirt, with a t-shirt and blue jeans. So I may have been a little overdressed. We had dinner in the Byward market following a beautiful stroll through the trails behind Parliament Hill, where we talked to get to know one another. I was having such a wonderful evening until Spencer had asked me, “So what do you do in your spare time outside of school?” For a moment, I was speechless and it was like my heart fell into my stomach. Before I made the silence become too awkward, I responded with, “I babysit for a friend.” Not the best of lies, but I didn’t know what else to say, he would respond with another question about who I babysat for and I would come up with another lie after lie. Before I knew it, I was in a spider web of my own lies. I felt I couldn’t tell Spencer what I was actually doing outside of school nor could I tell him after all the lies I had spun. I was scared that if I had told him the truth that he would run for the hills and let’s not forget, he was also going to school to be a cop. But with the constant feeling of being alone and wanting some normalcy, I played along with the chaos I had created.
As the evening came to an end, Spencer drove me back to my apartment building, walked me to my door and as he kissed my cheek goodbye, I asked him, “Would you like to come in?” The kiss from my cheek went to my lips, pushing the door open behind me, making our way to my couch as we were taking each other’s clothes off. Next minute, I’m straddling Spencer while making out with him until I said, “We need to stop, I think we’re going too fast,” as I start to get off of Spencer and begin to redress myself. Spencer responded with, “is everything okay?” “Yes everything is okay, I just want to wait until I’m in a relationship before I have sex.” I said. I had said that to Spencer because I wanted some form of control, maybe because I felt my life was out of control. At that moment, Spencer stood up from the couch in his boxers and asked me, “would you be my girlfriend?” I said, “Yes!” Without evening thinking, yet again.
I took Spencer by the hand, walked him to my bed and began to undress myself, again. I had Spencer lay down on the bed, put the condom on and I began to ride his cock. Spencer instantly began to moan loudly, shallow breathing, pressing his fingers into my hips and said, “I’m going to cum, I’m going to cum.” “No, no, no, not yet,” I responded just as Spencer orgasmed letting out a loud groan and said, “I’m so sorry, but that felt amazing.” Unsatisfied, I got off of Spencer, I handed him his pants and I had put a robe on. Spencer got up to use the washroom and while he was in there I was beginning to regret what I had just got myself into while trying to hold the tears back. Spencer had come out of the bathroom saying, “Well I should get going, I have an early class tomorrow and I have a long drive home.” For some reason, I was relieved. I walked him to the door and as he kissed me goodbye, he said, “See you at school tomorrow, girlfriend.” I felt sick to my stomach.
Closing the door behind him, I walked back to my room taking my robe off, I laid on my bed and began to touch myself sensually. I wasn’t thinking of Spencer either, I was thinking about my next shift at the condo and the money I was going to make. As I played with my breasts and rubbed my clitoris, the thoughts of the empowerment I got as an escort brought me to a satisfying orgasm.
Now I know it was unorthodox to have a boyfriend while I was an escort, however, at the time I was trying to fill a void inside of me and I thought Spencer was the answer. Spencer may have wondered how I paid for things all the time if I was just babysitting but rarely questioned me beyond that. We didn’t know each other well and rushed into a relationship. I don’t know why I thought I could have a “normal” relationship with him when I knew the relationship started on a lie. It was selfish of me at the time, however, I was a young woman who made mistakes.
The Condo
As time went on, every day except for Sunday’s I was working at the condo and attending school in between. I was lying to my family and friends at school as well as my new “boyfriend” Spencer. The more clients I had and money I was making, the more lies I spun. It also put a target on my back by other working girls. It also didn’t help that our driver, Damien, would sleep with every girl that worked at the condo. Except for those who are not into scrawny, arrogant and misogynistic men. Not only was Damien married, he would try to pursue me while he was engaging in a romantic relationship with another working girl, Samantha. I would always turn down Damien’s advances, but he would swear up and down that one day I was going to give in and fuck him in his tiny sports car.
When there are six or more other girls working and only two rooms to use, other girls tend to get jealous of those who are getting “calls” back to back. When all the girls are making money, everyone is happy but when work is dry, girls get bitchy. During the week I would work mostly with Rain, Bella, Samantha, Cherry, and Destiny. On the weekends there would usually be more girls because weekends usually were busier. Sometimes, women from Montreal and Toronto would be working at the condo as well. Weekends I worked with Cherry, Rain, Bella, Alice, Samantha, Destiny, Paige, Harmony and of course Damien would be there when he wasn’t driving girls to their outcalls. We had a full house, with clients coming and going every hour. I would be so busy at times that I wouldn’t even have enough time to eat or fix my makeup. I would finish up with one Jon and I would have a line up of others waiting in the building lobby until it was their turn.
I was also developing a close relationship to Bella, Cherry and Rain. The four of us would always try to work on the same days and we would get ready together in the Master bedroom. Working girls like Samantha would gossip to her “bestie” Alice and Paige, and giggle in the corner like school girls over Damien. Samantha loved patronizing other girls, especially those she deemed to be her competition. Samantha never took a liking to me. In fact, it felt like she had this urge to sabotage me as Kendra and Annabelle. I never understood why she would set out to undermine me, she didn’t even know me. Unfortunately, I was not her only victim.
The House Mother
Rain was Native Canadian, 5’10 with long, black luscious locks, dark brown eyes and pouty lips. She was Forty years old who had perky double D boobs with hourglass hips and tanned skin. Her bright smile and perfect teeth could literally light up a room. She had an outgoing personality with a contagious laugh. Rain was the woman who ran the Condo, she had been an Escort for four years, the same as Bella. Not only did she pay for the Condo, she also would take our photos, run our website and make sure us girls stayed in line. Rain and Bella were thick as thieves.
In her personal life, Rain worked for the government and had kids back home part time. Bella and Rain would get their kids together on their days off…when they had days off. The weeks she didn’t have her kids, she practically lived at the condo to not only work but to also make sure the girls didn’t burn the place down or be raided by the SWAT team. When Rain wasn’t with a client or at her other job, she would be on her laptop working, running errands, or helping one of the girls while taking phone calls. Rain was a very busy woman leading the epitome of a double life and she held it all together so well. Well enough that I was in awe of her…
The Home Wrecker
Samantha was from Ottawa, 5’8 with long bright pink hair, ocean blue eyes and a smile that resembled Miley Cyrus’. She was nineteen years old and had fake double D boobs, an obvious spray tan, with a flat tummy and a tiny perky butt. Her looks alone would have men swooning over her, however, her squeaky, loud voice and a narcissistic personality would detour men away… So you’d think, men loved her, they would bring her gifts all the time, so she’d say and she was friends with Alice, Harmony, Paige and Cherry.
Samantha loved talking about herself and being the center of attention. She would always be boasting about her “fabulous” life with her boyfriend living in his parents basement. She would also go on about how perfect her body was and how she will never need to get work done. However, it was clear that she had work done on her boobs. Normally, I would just leave the room when Samantha would start talking about herself.
When Samantha was not the center of attention she complained about anything and everything.. “I am having such a horrible day, my boyfriend didn’t want to pay for my new tattoo,” she would say as she was coming into work. Or she would say things like, “OMG, why is Destiny getting another call, I’m hotter he should have picked me.”
One of the rules of the condo is; to not be seen by other girls’ clients. Samantha would break that rule everytime by standing near the door so the clients would see her as they left. She would say things to the clients like, “Hey there, you like what you see?” “You should fuck me next time, I’ll show you a way better time than the last girl.” Actions like that would piss us girls off and Bella was one to never hold back. “Who the fuck do you think you are, poaching other girls’ clients?” Bella would say to Samantha. “Oh I didn’t know I wasn’t allowed to do that,” Samantha said. She knew better but would act ditzy when being confronted.
Samantha would work four or five days a week and every time she would come into work, she would always have some tragic story that had happened to her to explain away her behavior or for the attention. One story that sticks out was the time she came into work “crying”, telling all the girls including Lisa, “I got pregnant by a client!” Alice, Cherry, Rain, Paige and Harmony ran to her saying, “OMG are you alright?” “What are you going to do?” Lisa had even called Samantha saying that she will help her raise the baby because it’s a part of the PK family now…For the rest of the night Samantha had the girls’ attention while Bella and I kept our distance. Bella and I didn’t believe her story, considering she goes on about her bb (bare back) sex with her younger boyfriend.
A few weeks had passed, Samantha showed no signs of being pregnant nor brought it up since. So Bella decided to call her out on it. “Hey Samantha, how is the pregnancy going? How far along are you now?” Bella said to Samantha. “Oh I lost the baby yesterday,” Samantha replied. As Bella rolled her eyes, she snarked back, “Oh well that sucks, at least you didn’t get pregnant by a client.” You could tell Bella could see right through Samantha’s lies, however, Bella didn’t feel like entertaining the situation and walked away while flipping her hair off her shoulder. Samantha did not like being called out by Bella so she started to act out by crying and lying to the other girls that Bella was bullying her.
Though Bella had a reputation for being cold towards the other girls and known for having a disapproving attitude, Bella was no bully to Samantha. Bella was very forward with her feelings, especially if she didn’t like you or if she felt you were lying. A few more days had gone by and tension at the condo grew insufferable amongst the girls. With Bella and Samantha fighting, Damien berating me with sexual advances, and non stop clients six days a week, I was falling behind in school. The girls started to take sides and cliques began to form, the Condo was never the same after that.
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My second ‘Jon’, who plays a big part in the story, we call him Blindfold because he loves to be blindfolded while we tease and fuck him. He wanted the full “GFE” Girlfriend Experience, which involves french kissing, heavy cuddling, full service; sex, etc.
Blindfold loved meeting the new girls, so of course he booked me.
As I greeted Blindfold at the door, he was tall, curly brown hair, blue eyes and dressed respectfully with a collared shirt and dress pants. When I brought him to the room, he handed me $200 right away when he only needed to pay $140, he said to me, “keep the tip and get yourself some sex toys for the next time we play together.” I blushed and said, “thank you.”
I handed him a black silk blind fold Bella had lent me, walked him over to the bed, began undressing him and kissing his body. I started by slowly sucking his penis while I could hear him moan. It kind of turned me on. I happily sat on his face until I came. Then I put the condom on, slid down and began to ride him hard and fast as he sucked on my nipples until I could feel him coming in me, he let out a loud moan while lifting his head up from the bed. My heart was racing, I was breathing heavily, not just from the sex, but from the empowerment I got from pleasuring Blindfold.
While we were cleaning ourselves up and getting dressed, Blindfold insisted on seeing me again very soon. He asked, “would you do an outcall?”, I wasn’t sure if I was ready for that, but the words, “yes, I’d love too”, came out of my mouth like verbal diarrhea. Blindfold kissed me good guilefully as he said good bye and left.
The Girlfriend Experience
The second encounter I had with blindfold was my first outcall. Blindfold had called me about a week later after our first time together to book the afternoon with me where he would pay for three hours of my time. He requested that I wear a short tight dress with heels and my hair up in a ponytail.
The day started out by Blindfold picking me up at the condo in a black Mercedes and he was wearing a plaid blue blouse with black dress pants. As I got into the car, he greeted me with a kiss and said, “I love the red dress you are wearing”, “I also got you a gift”, as he handed me a black gift bag. Inside was a big, bright purple, vibrating dildo and $800 in an envelope. He said to me, “I want to watch you play with yourself with the dildo while we drive to our destination.” I looked at him questionaly, asking, “wouldn’t anyone else see?” He responded, “let them.”
So I took my panties off while Blindfold started to drive away from the condo, turned on the vibrating dildo and started playing with myself. As I’m moaning and bringing myself to orgasm, I look over at Blindfold to see he had undone his pants to stroke his cock while turning the car onto a dirt road that led into the woods. When I realized we had left an hour out of the city, I turned off the vibrator, asking, “where are we going?” he responded, “somewhere no one can see us so I can bend you over my car.”
He pulled into an empty lot behind a bunch of trees and parked with not a house in sight for miles. At first I was nervous, considering I didn’t know this man nor did I know where I was. I thought I had got myself into a bad situation until he had handed me a condom and asked, “would you like to have your way with me Kendra?” At that moment, I was turned on, Kendra was activated and I looked at Blindfold seductively, and said “it would be my pleasure.”
Blindfold had stepped out of the car, walked over to the passenger side, opened the car door for me, took my hand and walked me over to the hood of the car and asked, “what would you like to do to me Kendra?” I told him to sit on the hood of the car, as I straddled him to put the purple silk blindfold I had bought the night before for the occasion. He seemed to like it because he had a very hard boner so I started to grind on him saying, “do you want me, I’m really wet right now.” He seductively said, “please fuck me Kendra, fuck me hard.” I undid his pants, put the condom on, turned around and began fucking him cowgirl style. Before he came, he stopped to stand up, bend me over the hood of the car and fucked me doggy style while pulling my hair back.
We were moaning and fucking so loudly that it was a good thing we were in the middle of no where. He had a fantasy and I delivered. I made him come so hard that I had him begging me for more. Unfortunately for him, our time was almost up and he needed to take me back to the condo. As we arrived back at the condo, I told Blindfold that I would call him in a week to book our next appointment, and he excitedly said, “I can’t wait to play with you again, Kendra.” I kissed him goodbye as I rubbed his boner that never left and walked seductively back into the building.
The Orgy – may not keep this
A week later Blindfold had booked another appointment with not just me but four other girls for a Friday afternoon for three hours at the condo. He had got a big promotion at work and wanted to have an orgy to celebrate. He had also bought all of us girls black gift bags with sex toys, lube, condoms, and lingerie he wanted us to wear as well with a $400 tip inside of an envelope. He also brought us fruit and veggie platters for lunch after the orgy. I had never been in an orgy so this was new for me. My palms were sweaty from being so nervous, I had no idea what I was about to get myself into.
After us girls got changed into our lingerie Blindfold had chosen for us, Cherry started by undressing him, while Bella was tying him up, I was putting on the silk purple blindfold on him while the other two girls, Alice and Harmony were lighting candles. Alice was 5’10, thin with adult braces and straight brown hair. She had a nasally voice that made your ears bleed and an obnoxious attitude that you couldn’t bear to listen to her talk about herself non-stop. I had noticed not many girls liked her, however, clients seemed to like her, so she had that going for her. Harmony on the other hand, was eighteen years old, petite figure, 5’4 with bright purple hair. She always came to work with multiple suitcases with makeup, outfits and shoes. She was a sweet, hyper woman who loved smoking her weed and drinking Smirnoff.
Bella took the lead by sucking Blindfold’s cock, Alice came over to sit on his face while fingering Harmony. Mind you, I only knew Bella at this point so I was a bit awkward and not sure what to do. My lingerie consisted of white leather, crotchless panties with a matching cupless bra. Cherry had come over to me and said excitedly, “I’m Cherry, you must be new. Lay back and let me lick your pussy to relax.” I had no words and just did as she said.
Cherry was my height 5’5, twenty six years old, thin with perky boobs,natural bright, fiery red hair and a perfect round bubble butt with hourglass hips. Cherry had a bubbly personality, outgoing, sassy and a giggle that made you smile, however, she had this mysteriousness to her that intrigued me and for some reason, I felt safe when she was around. Everyone seemed to have a liking for her. She was wearing pink leather, crotchless panties with a matching cupless bra just like me. The other girls were wearing the same thing as well, just different colors.
While Cherry was eating my pussy out, Bella had begun riding Blindfolds cock while he was still eating Alice out. Alice and Harmony were making out and Harmony was fingering herself. It was very hot in the room, fucking on a king size bed and everyone moaning. Cherry was really getting into eating out my pussy, she started fingering me until I squirted all over her face. I didn’t even know I could do that. I gasped with embarrassment, as Cherry giggled and said, “there is no need to be embarrassed, it was my pleasure to make you Climax.” Then, Cherry begins to direct me over to Blindfold, Cherry says, “Kendra is wet and ready to fuck now!”
Bella gets off Blindfold, as I begin to swap out the condoms and start riding his cock. Cherry sat on his face and started kissing me. Alice and Harmony were scissoring at the end of the bed, Bella went over to the chair to play with herself while she watched us all fuck eachother.
Making out with Cherry was hot, I had never slept with a girl either, but I liked it. Cherry started kissing my neck and sucking my nippls as I’m still grinding on blindfold. Alice and Harmony sounded like they were cumming as well as bella. All of the moaning and sensations that was going on, made me orgasm again with the help of Blindfold fucking me and Cherry on the cusp of cumming herself. As we all reached our climax, together, Cherry lightly chokes and kisses me as she moans into my mouth. We were all like cats in heat, it was a sultry orgy and Blindfold had never been more satisfied that he tipped us $200 each.
After we had cleaned up and changed, we all met in the kitchen to enjoy the lovely lunch and bubbly Blindfold so kindly provided us. I was so sweaty from the sex that I didn’t bother putting clothes on but a robe. Which I guess turned Blindfold on by watching me eat strawberries in just a robe, that he walked over, grabbed my hand, placed it on his boner and whispered in my ear if I’d like to go for round two with just him. I nodded, took his hand and walked back to the bedroom while the girls watched us close the door. He handed me another $200 for me to just lie on my back and let him lick my pussy until I orgasm. My vagina was so tender but felt so good that I grabbed Blindfold’s hair and pushed his face more into my pussy as I came on his face. I had let out a loud enough moan that the girls were cheering on the other side.
As Blindfold stood up and wiped his face, he said, “this has been the best day of my life, thank you.” I smiled as I was still out of breath from all the orgasms I had and said, “let’s do this again.” Blindfold was thrilled as he got dressed, kissed me goodbye, left the room to say goodbye to the other girls while I stayed laying on the bed.
Cherry had come into the room to lay on the bed with me. We looked over at one another and began giggling like teenage girls. In that moment, it was the start to a beautiful friendship and lots of paid duos.
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Sometimes I feel being naked is a bad thing, too much over sharing. Being naked doesn’t have to be sexual, being naked is okay, I have nothing to hide and I have no means in which to hide. I want to feel free, so here I am, naked for you. I have kept so many secrets for so long. Somehow, I was capable in detaching myself from feeling wrong and guilty. I was able to compartmentalize my personal world with being a sex worker and was able to operate in both worlds. Until I couldn’t. To start, I want to tell you about Kendra.
When I was deciding to become Kendra I remembered I could be whoever I wanted to be. I didn’t like myself very much, so becoming somebody else was easy.
Kendra is a very seductive, sexy, manipulative woman. She loves having control over powerful, rich men. They are like her cat toys. She feeds off them when they give into her. The more you fall for Kendra, the stronger she gets. She loves to come out and play. Kendra gets off by destroying men or women who find themselves on the wrong side. Revenge is her sweetener and control is the whiskey she puts into her coffee. The more control she has, the more control she has over me. She can seduce you with her eyes and make you do anything she wants. It scares me, how I could create such a seductive monster but I love her just as much as you will. You want to hate Kendra but you can’t help but be intrigued.
Kendra was my protection. I created her to protect who I was, how I felt and how I acted. I had no choice, without Kendra, I would have been swallowed up whole and lost who I really was. Though, turning myself off and turning on Kendra, did exactly what I didn’t want.
In the beginning it was easy, it was like acting. Kendra was the “girl next door”, everyone wanted a piece of her. She knew exactly what you wanted before you even took your pants off. She knew how to touch you; where to touch you; what to say, and how to set the mood. But as soon as the session was over and the Jon would leave, I would become myself again. So I thought… Half a year had passed at this point and I was beginning to lose sight in who I was and why I was here. When I say I was beginning to lose myself, I was becoming what I was creating to protect myself. Kendra has no empathy, she’s a manipulative, smooth talking goddess. When Kendra wanted something, she got it. She would use her looks to seduce the men and her personality to entertain them, Kendra was the sweetest bitch you had ever met.
The first time I ever allowed myself to become Kendra was after my first day. My first day was horrifying. I ended up in the bathroom after crying my eyes out as my phone is ringing that I have another appointment. I was not prepared and the next Jon was not prepared for me; an inexperienced working girl. At this time I was blonde, weighing at 140lbs, 34B and only 18 years old. In most people’s eyes, I was still an innocent girl. A baby, the other girls would call me.
BELLA
While I was crying in the corner of the bathroom, Bella comes in, tells me to get off my ass and come to the kitchen where she handed me a shot of Havana Rum. I barely drank at this time, so it was new for me. 2 shots later and a buzz, she asked me if I felt better, and in my mind I wanted to say no but I knew that wasn’t the answer she was looking for so instead I told her I was fine. It wasn’t until someone I knew when I was 12 found me on Backpage, that I needed to be someone else; literally. Bella decided to take it upon herself to mentor me; in how to be a bitch, not to feel and not be me. This was the beginning of Kendra; a seductive monster.
Bella started by giving me a makeover, she did my makeup to the point where I couldn’t recognize myself and I ended up chopping off my long hair and going blonder. Next, she dressed me up in 9 inch heels, fishnet tights and a small, tight black dress that if I were to bend over you could see my ass. She told me: separate what I wear and what Kendra would wear. Bella ended up taking me shopping to buy Kendra a new wardrobe, lingerie, heels, panties, and new sexy dresses. She then began to prepare me for the evening of work. She told me I needed to be a bitch and to leave my feelings at the door, she had also warned me to be careful of the other working girls. They seemed so sweet and well groomed. Not a hair out of place, nails done, their makeup was perfect, and they smelled sweetly intoxicating. There were 4 other girls working that night as well as Rain, the woman of the house. She was like the mama bear of all of us girls, she was older but the sweetest person there. Her and Bella were very close unlike the rest of the girls. We may all be there for the same thing, money, but the girls always had a hidden agenda. I didn’t know this, yet; I was pretty naïve and influenced easily. After Bella finished giving me a makeover, she hands me another shot of Rum, says that it will take the edge off and now it’s time to play the game.
Bella was the most beautiful, petite Latina woman I had ever met; long black hair, dark eyes, long fake nails, and a perfect fit body. Bella had been in the game for 4 years at this point. She had a routine when she would come into work, she would change into her little black dress, sparkly heels, do her makeup, then pour herself a Havana Rum, 3 ice and Coke with lime. She didn’t smoke nor did drugs, just drank. She was unlike the other girls that worked at the condo. Bella was a smooth talker with a sexy Spanish accent but she was also a bitch, one of the sweetest. She was someone you wanted to have on your side and not against you. She usually kept to herself when it came to the other girls, but for some reason she took me under her wing. Bella made the most money out of all of us girls and had the most regulars. Bella was like taking a taste of a forbidden fruit.
I was always curious as to what she was like as soon as the door closed, until one day I no longer needed to be curious as we were paid for a duo.
The Perfect Escort
Working at the condo with Bella was never boring. As I previously mentioned, she would always show up with a big bottle of Havana Rum and loved to play sexy Latin music, I could never understand what they were singing about but I could tell you, it made my hips want to move.
Ever since, Bella helped me out on my first day, she would always invite me into one of the three rooms with her to get ready for our night. Mind you, we didn’t always work nights, however, weekends were the money makers… and when we would get drunk guys wanting to fuck but can’t get a boner due to all the whiskey and coke they snorted up their noses; that’s when things get freaky.
After Bella would finish getting ready, she would help me with my hair and makeup. Half the time I couldn’t recognize myself considering I always wore minimal makeup. She was always so pretty even without all the makeup. The way her Spanish accent, long black hair that would cover her boobs like the little mermaid, and sexy little black dresses she would wear could turn you on instantly. I wouldn’t say I was into Bella, more like I wanted to be like her.
Bella was disciplined, poised, always made sure she was paid upfront, full amount and made sure they knew the rules before we began. She was the full Girlfriend Experience. She would bring her own candles, massage table, massage oil, lube, toys, and different outfits. She wore this gold diamond chain around her hips and pelvis that accentuated her tight curves. Bella was what you could call, “The Perfect Escort.”
I will admit, I was nervous about my duo with Bella even though I wasn’t going to be having sex, all the client wanted was for me to watch while Bella played with him.
This client was one of Bella’s regulars and he wanted the wildest things. He came prepared, a dog leash, money, condoms, and Havana Rum for Bella. He paid $400 upfront for both Bella and I for a one hour session. We took a shot in the kitchen, went to the bedroom, closed the door and the session began.
The Jon had put the leash on and had Bella walk him around the room like a dog, he would even beg on his knees to suck the end of her heels. She would make him deep throat them while saying, “you like deep throating my shoe, is your cock getting hard?” ‘Jon unzipped his pants and began jerking off.
After, she would make him beg her to fuck him. He would get on his knees, kissing Bella’s feet while she would look at him with disgust and say, “get up you dirty pig and bend over”, as she would put a big black strap on on and begin fucking him hard in the ass.
I had racing thoughts, wondering how did that not hurt while trying to focus on not showing my true emotion…mortified. Every so often Bella would look over at me and ask the Jon if he liked me watching him be humiliated and with an eager loud “yes!!!” he would ask her to give it to him deeper. I won’t lie, it kind of turned me on watching him climax. Within minutes he was ejaculating everywhere and Bella looks over at me with a seductive grin. I realized that day that the sound of moaning and watching someone climax really gets me wet.
-
I will be honest, I didn’t do much research before becoming an Escort. Despite the risks and criticism, after meeting Lucy, I just knew what I had to do in order to make it on my own. All I did was type in google: “Ottawa Escorts.” A bunch of escorting companies had come up, I looked at all of them and came across an intriguing one. Pink Kitty. I called the number that was on the website, and this woman with a soft but stern voice had picked up. For a second I thought I had called the wrong number.. Until the woman introduced herself as Lisa and strummed out numerous questions such as; “what is your bra size, hair color, weight, ethnicity and what were my restrictions?” “RESTRICTIONS… what do you mean?”
Restriction; the limitation or control of someone or something, or the state of being limited or restricted.
Meaning if I had any sexual restrictions. I had said, “Not that I know of, why should I?” She immediately responded, “You’re perfect for the job, when can you start?”. My immediate thought was how could this woman know I’m perfect when she hasn’t even met me, all she has are a few photos I sent her from the summer past.
The next day, a driver named Damien showed up at my door to take me to the Condo where I would work. Damien was thirty six years old, 5’4 with dark brown depleted eyes and modish clothing. His hair was always slicked back and greasy looking while wearing Dior Sauvage cologne. He was egocentric with psychopathic tendencies. If Damien took a liking to you, he would be this charming man, hanging on your every word as if everything you were saying was important. Many were fooled by his charm, however, I was not.
My first day was rattling; I’ve never felt so nervous in my life. I realized that I would be selling my body to pay my rent, pay for food, and overall to live. I kept asking myself if it was worth it, is it worth lying to everyone about, but I also kept in mind this is only temporary… so I thought in the beginning.
When I walked into the condo, it wasn’t what I had expected. I was expecting what I had seen on television and movies where they hangout at glamorous clubs and hotels. Drinking expensive champagne and wearing Louboutins. Instead, girls were on the couch watching movies, some girls were cooking food, some doing their makeup and others were taking a nap. Clothes were everywhere, most of the girls were wearing jogging pants or pjs. As soon as they got “a call” a.k.a a Jon/client they would immediately transform into this Barbie. What I mean by “Barbie” they would look like the male fantasy; perfect hair, perfect makeup, their nails were done, they had fake eyelashes, some had extensions, big boobs, super skinny and to top it off each one of them smelled amazing. They would be wearing top line lingerie and louis Vuitton heels wrapped in a silk robe to answer the door and take them to one of the rooms.
Damien took sexy photos of me to post on Backpage to promote me. I was wearing a leopard print lace slip I had since high school, with black heels that one of the other girls had lent me. I had light makeup on and my hair was straightened.
As I answered the door, the Jon immediately tried to french kiss me as he’s forcing himself into the door. I said let’s wait until we get to the room and exchange “gifts” money.
Our rates were $120 for half an hour and $140 for an hour. Lisa would take 40% and $150 for the room per day you work at the condo. Unless you have a bunch of clients, you don’t make as much as most people would think.
Once we had got into the room he was aggressive, asking me to do things I’ve never done nor would I want to. Like “BB” (Bare back, no condom), anal, “CIM” (Cum in mouth) “BBBJ” (Bare back blow job). He had thrown me onto my back on the bed, taken my panties off, ate my pussy out while I stared at the ceiling waiting for it to be over until he flipped me onto my stomach, slipped the condom on and popped a nut within a minute. Pulled up his pants and left. I was traumatized. Mortified even. However, I had other calls lined up for me and at that point, there was no turning back.
-
As the summer before college was coming to an end I was becoming anxious about moving out on my own. Not because I was afraid of being alone in a big city; I was worried about how I was going to pay for my bills. Where would I get a job? Would my employer be flexible with my school schedule? How am I going to work and still go to school for eight in the morning until at least seven or eight at night? Do I really want to work at Mcdonald’s again? My parents would also ask me the same questions everyday and try to convince me to go to community college. “It would be cheaper and you can live at home,” They would say. But over my dead body, I was going to stay in my hometown and go to Community College, so I started to stress out.
With moving day looming around the corner, I had saved just enough money to make the move to Ottawa, to pay the deposit plus first and last month’s rent. I had just enough money left over to buy a week’s worth of groceries. That was still not enough but it was a start.
Sitting out back with my family behind my parents’ apartment building, a woman in a red Massarotti drives in the back to park. She had long dark hair, styled like Betty Page’s, with big brown eyes and she smelled like Chanel #5. As she got out of her car to walk over to us in her Louboutin heels and black little dress, my dad shouts, “What is a woman like you driving a car like that in the ghetto?” She giggled as she approached us. “I’m Lucy, I just moved into the building. As for the car, my Sugar Daddy bought it for me,” she said. “SUGAR DADDY? What the hell is a Sugar Daddy?” My dad yelled while laughing.
Sugar Daddy; A rich older man who lavishes gifts on a young woman in return for her company or sexual services.
Lucy pulled out a chair and sat at the table with us before answering my dad’s question. “Anyone have a beer?” Lucy asked. Immediately my dad, uncle and cousin all handed her a beer.
As Lucy took a swig of her beer, she said, “I’m an Escort and my Sugar Daddy takes care of me.” Everyone at the table just stared at Lucy in disbelief. My dad on the other hand shouts, “WELL HOLY SHIT, GOOD FOR YOU GIRL!”
Escort; An escort gives companionship and time to the client. There may or may not be any sex involved.
Lucy ended up sitting with us for a couple of hours swapping stories and shooting the shit. Later when I went inside to grab everyone more beer, Lucy came into the building behind me. Turns out, she was living across the hall from me. Too nervous to ask her anything, I quietly went back outside with the beer.
Later that night when I was in my room, I watched a movie that was airing on cable TV called “Walking the Halls.” It’s a movie about a girl who graduated high school, wanting to go to an Ivy league University, however her parents couldn’t afford it. Similar to what I was going through. However, the girl decided to become an Escort to pay for school. Falling asleep right after the movie, I had forgotten all about it.
With only a week left until I moved, my parents were really on my case about how I was going to pay for rent and food while at school. One morning I was getting ready to head to my last day of work at Mcdonald’s. My parents and I were fighting and yelling cause I had no idea what I was going to do, I just knew I didn’t want to be in Kingston anymore. As I slammed the door behind me while still yelling at my parents, there stood Lucy in front of her door across the hall. “Can I give you a ride to work,” she asked. “Sure, that would be great, sorry if you heard us yelling,” I responded. Lucy didn’t seem phased by it as she walked in front of me to her car. I had never been in a sports car before until that moment.
During the ride to my work, Lucy had mentioned that she had overheard the fight with my parents and that I’m going to be financially strapped when I move. She had also mentioned that I too could get into her profession to pay my way through college. THAT’S IT! It was like a light bulb went off in my head. It was kind of like a sign. So the next time my parents asked what I was going to do, I told them not to worry and that I had it covered. I told them, a friend from Military Band Camp lived in Ottawa and could help me get a job there. This was the moment where I made my first lie about the double life I was about to lead. At least it got them off my back for the moment.
-
It was a cold winter day, a week before Christmas break. I had skipped class for the first time to meet up with my then boyfriend, Cody. I would of had second period, however, Cody’s parents wouldn’t be home so he thought it would be perfect for us.
We had only been dating for two weeks and before that, Cody had another girlfriend, Billy. Before that, he had been with two other girls. Cody was only two years older than me, in his Senior year, with the sexual appetite like Mr.Grey. Cody was taller than me, athletic build with washboard abs, and dark blonde hair with a military haircut. He had the lightest blue eyes that you could get lost in. Stare into his eyes for too long and you may just lose yourself in them.
The night before, I had shaved my vagina for the first time because three weeks prior , Cody had told me I was hairy and needed to do something about it. Cadets had finished for the evening and Cody had asked me if I wanted a ride home. Then he was with Billy. But I couldn’t resist. Before dropping me off, Cody had parked his car a few blocks from my place. I had only kissed one other person in like the 8th grade so I didn’t really know what was going on. Cody unbuckled his seat belt then reached over to unbuckle mine. My first thought was, why does he have no scent? Usually guys smell good or wear some form of perfume. Their own scent girls can’t get over and want to steal your sweater because it smells like them; kind of scent. However, Cody was allergic to perfumes and many other things, so I don’t think I’d be stealing any of his sweaters anytime soon.
Just as Cody took my seat belt off, he intensely kissed me. I was stunned and before I could say anything, he was kissing me again. I felt my vagina get warm and tingle as I leaned into him more, kissing him back. He caressed the side of my face to my breasts. I could feel myself getting turned on and my panties wet. I had never experienced that feeling before and it felt good. As Cody’s hand worked its way from my breasts to my belt, I stopped him and said, “Wait! What about Billy? Isn’t she your girlfriend?” He responded back, “Yes, but I’m leaving her, I want you.” As he began to unbuckle my belt and kiss my neck, I couldn’t resist though I knew it was wrong. His lips went from kissing my neck making their way back to my lips. Kissing me intensely as his fingers slid under my panties. Touching me, sliding his fingers back and forth on my wet clit. When his lips left mine, I had let out multiple moans telling him not to stop. “Keep going, Oh Oh OoooH, I think I’m going to cum”, I moaned. He whispers in my ear, “Cum for me, cum on my fingers”, and so I did. As I grasped onto his shoulders, thrusting my hips more onto his fingers, the sensation was intense, I could see stars in my eyes and then I had my first orgasm.
Panting, I rested my head on his shoulder as he took his hand out of my panties and I began to buckle up my pants. I sat back into the passenger seat all flushed, trying to process the orgasm I just had and then I remembered that he still had a girlfriend. Cody looked over at me and asked, “So how did that feel?” I blurted out, “Amazing!”, with a huge smile and blushed cheeks.
Before I could even ask the question, “So what is this?” Cody stated that he had a suggestion for me, if I could shave before we had sex. I blurted out, “What about Billy?” He responded, “I’m going to break up with her at school tomorrow.” Was that supposed to make me feel good? That he was choosing me? Cause if so, I felt the complete opposite. I felt sick to my stomach, I had become The Other Woman before I even lost my virginity. But he was so good looking, he wanted me, and that orgasm…
Driving the few blocks to my house was pretty quiet, Cody pulled over a few houses down so my parents didn’t see me getting out of a boys car. Before I got out, Cody leaned over, kissed me on the cheek and said he’d come see me after school the next day.
The next day, Cody called me after fourth period to tell me he was not far from my school and wanted to come pick me up so we could talk. I could feel my stomach sink and my mind race. What did he want to talk about? Did he break up with Billy? Did he change his mind or did he tell her that he cheated on her with me? So many thoughts were running through my mind while I waited for Cody to pick me up. As Cody drove up to the front of my school, my heart began to race, I could feel myself sweating but I also felt a little turned on. Thinking about the night before was making me flushed in the chest. I had to tell myself to take deep breaths before I got into the car. As I got into the car, before I could put my seatbelt on, Cody gently grabbed both sides of my face and kissed me like they do in the movies. I could feel that warm tingle again. For a moment, I forgot about everything.
As Cody pulls away he says, “I broke up with Billy today”, “oh, are you okay?” I responded back. “Ya, it wasn’t working out anyways, besides I want to be with you”, he said. I had that stunned look on my face again. Why am I so awkward? I kept thinking. Cody giggled at my facial expression, started driving and said he was going to take us somewhere private. Cody pulled into an empty parking lot behind the YMCA, unbuckled his seatbelt and told me to get into the back seat with him. Staring into his eyes, wondering why he wanted me, Cody stared back into mine and asked me if I wanted to be his girlfriend. “Yes, yes I will be your girlfriend,” I gleefully said. Cody had a grin from ear to ear, moving closer to me he placed his hand softly behind my neck while gripping some of my hair. He looked deep into my eyes then kissed me passionately. We began to makeout intensely, caressing each other’s bodies. Cody’s hands began caressing my breasts, working his hands down to my hips where he picked me up to straddle him. I could instantly feel his hard boner as I thrusted my hips into him, kissing him deeply. It was so hot my panties were soaked. As Cody started to kiss my neck, he lightly bit my ear and gave me this tingling sensation and shivers all over my body. He could feel I was turned on, his hands on my hips thrusting me into his boner more while gently moving his lips from my neck down my collar bone to my breasts. OMG. It felt so good. Too good. As Cody started to unbutton my blouse, moving my bra over to lightly suck my nipples. I had let out a moan, thrusting into him deeper while running my fingers through his hair.
Then it hit me! “Wait!! Stop!! I’m a virgin!!” I yelled. I pulled away as I began to blush and feared I had ruined the mood. Cody smiled while giggling, saying he knew I was a virgin. How?! My unshaved vagina gave it away. He seemed to be more turned on by the thought of me never having sex before; his hands were running all over my body while thrusting into me. We continued to make out as I dry humped his hard boner. We weren’t even having sex and the windows were all fogged up as if we were. It was so steamy, reminiscing about it turns me on.
The rush of young love, the intensity you feel towards one another, exploring each other’s bodies for the first time, and finding secret places to explore each other sexually without the interruption of parents. Ya… It was fucking hot, like Fifty Shades of Grey hot with more nudity.
However, we didn’t have sex that night. I told Cody I wanted to wait and so he did…. For two weeks. Which brings you back to where we started. The day I lost my virginity. I’ll be honest, I wasn’t ready for my first time. I wanted to wait till I was at least in love or married. I wore a purity ring for christ sakes! But that was not how Cody rolled.. He didn’t want to wait any longer, insinuating that he would leave and that he doesn’t not not have sex in a relationship. I remember feeling worried that he would break up with me. My first relationship ever and I get dumped two weeks later? Every girl’s worst nightmare.
Cody had picked me up at school after first period to drive me over to his place, which was out of town. I had never been more nervous in my life. I didn’t know what to expect, except for what I’ve seen in movies or porn. I was pretty quiet for most of the drive. I was wearing my winter boots and jacket over my white lace dress. With a white bra and panties to match. I had decided to curl my hair and wear red lipstick. I thought white was fitting for the occasion… 😉
As we pulled up to his big country house, with a swimming pool, hot tub and fifty acres of land; my heart began to race. Once Cody parked the car, he got out first and came over to open my door for me. He takes my hand to guide me, at first I thought we were going into the house, but instead we were headed to the garage. Cody opens the door, we walk in and there’s a mattress on the floor, a sex playlist on the stereo, candles lit and lube on the bed. It wasn’t my first wish to have sex for my first time in a garage but it’s not like I was going to tell him and hurt his feelings. He said it was so we could have more privacy in case I’m loud or his parents come home early. So I went along with it.
Cody takes my coat off and walks me over to the mattress on the floor and tells me to just relax. I stayed quiet thinking he must know what he’s doing considering he’s been with three other girls before me. As he begins to kiss my neck from behind and unzipping my dress I couldn’t help but think about the other girls he has probably done this for. I thought my first time would be special and I’d feel special. With my dress falling to the floor, I could feel Cody’s hands running all over my body while taking my bra off. He begins to french kiss me while running his hand down my panties and began to rub my clit. I moaned. His kisses made their way to my breasts, lightly licking and sucking my nipples. God I love my nipples and breasts being played with, something I didn’t know until that moment.
I started taking Cody’s belt off, unbuckling his pants, letting them drop to the floor. He stopped rubbing my clit for a moment to take his shirt off. Ugh he was so hot, the abs and bubble butt ass. He took my hand and grabbed his cock between his boxers then whispered in my ear, “My cock is so hard, I want you.” I had never seen a penis before nor had I touched one, but it sure turned me on. As I lay on my back, Cody gets on top of me to kiss me, then my neck to my breasts. I lightly moan as he continues to kiss down my body to my panties, he could even wait to take them off and he started licking my pussy right through my underwear. I moaned again and again until he ripped my panties off, spread my legs and started to lick my pussy more. I started to moan louder. It felt so good, I never thought I’d love a guy going down on me. He had spread my vagina lips apart to suck my clit even deeper and my screams of ecstasy got louder. Throwing my legs over his shoulder, my hands running through his hair, thrusting my pussy more into his face, he looks up at me with those big blue eyes, paused and said, “cum for me baby, cum all over my face,” as he continues to lick my wet pussy, I orgasmed in his mouth. When he came up for air, he french kissed me while saying my pussy tastes so good and that he loved that I took his advice; my vagina was hairless. Again, it wasn’t the most romantic setting, but at least he was trying, right?
Cody took off his boxers, kissed me again and asked if I was ready; “uh huh,” I responded. He proceeded to put on a ONE branded condom and he begins to have sex with me, I cry out not in ectsy but pain. He whispers, “That’s your cherry popping.” I could feel tears running down the sides of my face as he kept going, letting out a loud moan as came inside the condom. That’s it? That’s what sex is? That fucking hurt, I thought to myself. Cody hands me a towel and directs me to the shower. I get into the shower to notice blood everywhere. I started to cry silently in the shower not sure if that was normal or not. Or if he noticed the blood too, I hoped not.
Once I got out of the shower and got dressed, Cody said he would drive me back to school. The ride was once again quiet and it felt like the molding of his penis was inside my vagina. As I stared out the window, I felt different. Like I lost something. But I also felt sexy, like I was finally a woman in a way.
