There are many things
I feel I can't say
in the fear
I will push you away
knowing the pain
we have been through
I still hold back
cause I feel for you
tell me I'm wrong
and you're just scared
cause what you feel
is really there
Tag: sex
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Let me start off by saying, the lifestyle I used to live is far behind me and I’m in a healthy relationship now with someone who accepts me and my past. But I still go back to remind myself that any situation, good or bad, is an opportunity to grow. I wouldn’t be here without my mistakes (which I am still sort of embarrassed to be writing about.)
Back when I was a sex worker some of the men I have encountered were married but I never asked questions because they were either paying me and or I was oblivious and naïve. But sometimes I feel I subconsciously knew that they were not the man for me or that there was something shady going on. I could also tell when a man has taken his wedding ring off to pretend he is not married… There is a damn tan line.
For instance, I met this guy just by asking him if I could “bum/buy” a smoke off him. Of course I got one and his number in the process (he insisted). Instantly I knew in the back of my mind that I didn’t have time for this guy and that I had bigger fish to fry. I had just moved to Toronto for Event Planning. But again, he insisted that he wanted to get to know me. He sweetly talked me into drinks by brushing my hair out of my face when I was talking and I fell into his dick sand hard.
Dick sand is like quicksand but with dicks. It’s when a girl meets a guy and instead of standing firmly on solid ground knowing who she is and how she feels about herself she instead quickly starts to sink into dick sand. It’s where you lose the ability to know what you like and instead you like and do everything the guy likes. You start merging into the female version of the guy by liking what he likes, not allowing yourself to have your own personal interests or opinions. Initially losing yourself in the dick sand.
A reference from one of my favorite movies, (How To Be Single).
Did I also mention he was very sexy. Luke was tall, athletic, dark green eyes with slick back, thick blonde hair. but never be fooled by a pretty face. I wasn’t entirely oblivious to the signs, I could feel that something seemed off but I couldn’t piece it together. I honestly was just enjoying the attention this man was giving me. We will call him Luke.
Luke wanted to take me out for drinks when I was done school and of course I agreed. A hot guy and free beer, what could possibly go wrong? While out for beers, in the span of an hour, he bought me a bunch of beers and shots, you could say we were having a good time. Until he had to leave abruptly. He bought me another beer, paid the tab and left. I didn’t hear from him for 3 days. His excuse, he was “sick.”
I didn’t hear from him for a few more days, until I decided to message him to go out for drinks again, but this time I ended up being tipsy. He paid for beers and shots, yet again. Prior to us going out for drinks, I was feeling off guard. A funny feeling you could say. However, it was fun being able to go out for some drinks and let loose. And I didn’t even have to pay for it. Considering I had been working my ass off in school non stop for four months, a little fun couldn’t hurt right?
I did however tell him about my working girl days and it seemed to be a turn on to him. I don’t know why I told him, maybe I knew deep down it didn’t mean anything. We ended up going back to Union Station where he works as a project manager to “hang out”. You can already guess where this one is going. We ended up fucking on a conference table at Union Station. He definitely had me hot and bothered but in the back of my mind it wasn’t what I wanted. But it takes two to tango and I went with it for the whole two minutes. Did I mention I was wearing pants that day. He starts to aggressively kiss me, calling me a “dirty girl,” and pushing me down to my knees to suck his cock.
“You like sucking that big cock don’t you”, he says as he pulls my hair, with his cock in my mouth, I look up and nod my head.
But in the back of my mind, I didn’t.
After a few minutes on my knees, he pulls me up, rips my shirt off and takes one of my boots and leg pant off. He fucked me fully clothed before I could put a condom on, yelling “oh fuck baby, I love your tight pussy baby”, then came inside of me and instantly began to get dressed.
As soon as I went to the bathroom, I felt ashamed. Why? In that moment I couldn’t tell you why. I am usually up for the thrill for a story. But this time felt very different. He treated me like an escort and I didn’t even get paid for it. He ended up leaving again right away. I didn’t hear from him for days. Which was to be expected.
We ended up bumping into one another again at Union Station on my way to class and he asked me out for drinks. This time I paid… Which was stupid on my part. This time I was a bit more than tipsy. Bumping into him threw me off. I had a bad feeling but for some reason I still went. Maybe it was my low self esteem or maybe I was lonely.
We ended up going back to his office where I had mentioned to him that it seems that he is only bringing me to his office to fuck me again. Which was exactly the case. But me being more than a few drinks in and him sweet talking me, by grabbing my hips, kissing my neck really softly, and lightly touching my pussy, I gave in. He even asked if I wanted to have sex… after we were already undressed and I had deepthroat his cock. At that point I didn’t care. You could say I lost some of my self respect. We ended up fucking all over the conference room. When he asked me “baby can I cum in you”, the mood seemed to change. I also dislike being called baby by men who is not my lover, I’m not his baby. He then bent me over the conference table and began to drill me from behind briefly and didn’t end up coming. Neither did I. Both times I had slept with him I did not have an orgasm. So not worth it.
Right after he “had to go” but decided to take the same train as me to stay at his parents. But while we were on the train, I had a feeling something was wrong but I just kept ignoring it. (Don’t ever ignore your intuition). When he went to get off the train, he said “I’ll text you later baby”. Ya right. Which I was right. He never messaged me. I ended up calling my best friend bawling, telling her how I felt ashamed. She told me, maybe it is my intuition trying to tell me something. A day or two later I was thinking about how I didn’t even know his last name like the Carrie Underwood song. Going back into my phone records, I noticed he had called me back when we first met which showed his last name. I decided to look him up to find out he had a wife and kids back home…
Yup you heard it right. I got fooled yet again by another pretty face. It’s not like it hurt as in I had feelings for him but it hurt to know that he has a family at home and I was so naïve to not even acknowledge the signs. Let me tell you that this whole situation hit me hard. Harder than any other dick sand I had fallen into. I felt I lost myself briefly to this guy who I barely knew. I didn’t know how to react, how to feel, or what to do. Do I confront him? Do I tell her? What am I supposed to do? My friends say I should have messaged his wife, but I feel that is going to do no good, it will just cause a whole new problem. But then again, she is being cheated on by “the love of her life” and may not even know it. I mean I would want to know but then again, having some random woman messaging you won’t make the situation any easier.
I ended up telling my aunt about what had happened because it began to bother me in what I should do, and her advice was just what I needed. My aunt is very straight forward and won’t sugar coat the issue. I decided not to message the woman, I do not know her, her situation nor do I know what I’d be setting myself up for. It could either put me in danger or blow up in my face. So to save face, I just brushed it off, learned my lesson and moved on.
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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.
