23/07/2020
Wendy the First Night to Change My Life
Grew up on the street and I learned to survive. However, that did not allow me to develop relationships or have time for girls. Now the fact I was poor and homeless did not help in allowing me to meet girls or girls to be interested in the kid wearing someone else’s throw always. I had come to accept the fact that I was not someone girls would have any interest in. I was use to be discarded, rejected, and unwanted.
In high school I was on the football team, and basketball team, had no friends as that was baggage I could not afford. I needed to work two jobs, study, and survive. Little time for frills like girls or parties. I was a tall lanky kid, always looking for my next meal and a place to put my head at night. I was in and out of the social safety nets so many times I had rope burns from the nets I seem to weasel out of. My scares were on the inside more than the outside. I learned to do what I had to do to get people to allow me onto their sofa.
I was naturally shy when it came to girls so I was a virgin all through HS and University. In university there were two young girls who I thought had an interest in me. One Diane the other Ashley. However, they were both using me to get to other guys on the basketball team. I could not fault them, I did not really think they wanted to hang out with a guy who lived in the locker room?
My scholarships were a result of my work ethic and burning desire to survive. Still, naturally shy, when it came to girls, I left that part of my life to my fantasies and dreams. Neither I could afford. All of university I remained a virgin. Lame, I known. What kind of guy can't get laid in university?
One-night senior year I decided it was time to lose the V-Card, and I decided the only guaranteed way was with a hooker. Just riding around with guys on the team they introduced me to the girls on St Catherine. I had no idea what an impact these girls would have on my life. It still never happened until years later.
You see while in high school and University I was living with some rich kids. I was a bit of a cocky kid. I had very little in my life but my dreams. One father who I worked for had a business that was failing and he thought he would put me in my place. So, he told me and his son to take over this company during the summer, until he could close it down.
I moved into the plant sleeping in the lunch room. The staff knew the place would be closed but here was this young kid who was working in the plant with them making bras, and ladies bathing suits. I worked on the floor learning to cut and sew. I learned about the distribution side of the business and the finance side. I was in school and I did not need much to live on. So, my salary was nearly nothing. I lived on KD, and sandwiches. I was there all time except when I was at school or in practices or at games.
On the sales side we needed people to see our work so we learned that business. No one knew us or were interested in what we had. We could not afford models. But I knew of the girls in classes. My partner in crime was rich and hot in school, he had a ton of girlfriends. He thought it would be fun to get these beautiful girls to be models. All the beautiful girls wanted to be high fashion models. So, we hired them to come in and walk around in these bras, bathing suits.
It did not take long and the girls in University figured out this was not a real modeling job. So, they dried up but I thought why not see if the girls on St Catherine might have an interest. Now carrying on the story, I could not afford to drink nor did I have a desire to drink I was the designated driver. On those nights with the guys they would have me drive on the track so they could yell at the hookers. I kind of had an idea of where there may be hookers. Matter of fact I was gaining a knack at picking out the ladies. After my last shift at work I would drive around town looking for hookers. My idea of what I would find was based off movies, Matter of fact the movie “Risky Business” was out and “Pretty Woman had just come out. So, I hit the street. I found a few for $20.00. Yup for $20.00 they would walk around in our underwear as we expanded into ladies’ panties. These young ladies were hot. Buyers who were all guys started to take up our invites. Plus, we would give the girls free underwear.
The word got out and these buyers were coming by often and now were ordering more. We moved the showing from our office to nice surrounding at some of the nice hotels.
One night, a buyer had just placed a nice order and Wendy who was the lady who suggested we move the showings downtown and was modeling that night. Showed me the light. We were at the plant and after the showing while Wendy was getting in her street clothes. Asked if he could see the plant. I thought cool. Not much to see but ok. I took him back to the cutting floor and the warehouse. It was not much to show and we were back in the offices. I asked Wendy if she was ready, I was going to take her back downtown to where her full-time job was. She smiled at me and told me she was fine.
Now we were out on the west Island and I knew she did not have a car. At this point the buyer said he was staying downtown and he would drive her. I looked at her and she smiled. I looked at hm and he smiled. It was clear there was more than just my business that was transacting that night. I would come to learn that this now was becoming common business practice.
Our business grew and grew. As I got older and neared the time when school would be complete. We sold the business. I got into property management with a mentor. We bought up old small shopping centers and came up with a new concept. For all time sake before I traveled to Europe for my first trip. I found myself walking a street near St. Catherine on night. By a dark doorway I noticed a figure in the shadow. She asked me if I was looking for company. I stopped as her body caught my eye. A beautiful hot body in a short skirt and legs that went on forever.
Then out of shadow a face I would never forget. It was Wendy! She was still working the street. She smiled and said, “Greg, it has been a while.” I smiled back and asked her if she was still working. She looked at me kind of side ways and said “Yea!” We chatted for awhile on the street as cars went by and a young college guy hanging from the windows who yell out profanities. She asked me if I want to get a coffee.
She asked me what I was doing and I told her I was going to Europe and I told her about the mall business and a few of the retail stories I took over. She asked me if I had a girlfriend and now it was my turn to look at her side way only to say I do not have time. She asked me when the last time I got laid. I turned red and she grabbed my hand telling me she was going to fix that. I did not know what to say.
She pulled me on to the street and we walked to the little hotel she was using. I was embarrassed as we walked in and walked by the older man at the front desk. He smiled as Wendy winked at him and we walked up the stair. Wendy told me not to be nervous.
She opened the door and we walked into the room that smelt a musky scent. It was an old hotel and I was unsure what to do. She took off her top. Although I had seen her modelling the bras and the bathing suits. I realized I had never seen her naked. She removed her bra and her breasts were so well formed. She took off her panties. Her bush was full as she walked to me.
Wendy then commented. “It is more fun when you get undressed as well.” I felt foolish as I took my shirt and pants off. Not knowing what to do with my underwear and my socks. I dropped them as she laid back on the bed. I got to the edge of the bed she could see I was hard under my underwear.
“Let me help you with those.” She pealed them off and my dick stood straight up. “Oh, my Greg you are very well endowed.” Maybe she was trying to build my confidence but she told me I should consider doing porn. I felt good as I slid in next to her.
Wendy went on to tell me she often wondered what I was like. She thought I was good looking. She knew I was distant. We talked and the fact we were naked seemed to make it easy to talk to her. She knew I did not have a girl friend. She seemed disappointed that I was going away. But it was an opportunity I could not say no too. Our talk was both light and comforting, and rather than being the voice of a stranger, it came across as the voice of an old friend. We chatted easily, asking the obligatory questions one would want of a new acquaintance, both of us laughing at the similarities we seemed to share on nearly every subject. Besides being the same age, we came from matching backgrounds, had the same tastes in music, movies and food, and had matching outlooks on life. Our views on religion, politics... It became almost comedic how much we actually shared and our conversation flowed for hours.
I held her close and I realized I had never had anything so intimate before. This simple gesture of her touch was soft, yet firm, and sent a buzzing through my entire body.
We talked about many things, yet soon found ourselves in a comfortable silence as I looked into her eyes and, sensing the invitation, slowly lowered my mouth to hers, connecting our lips in a lingering kiss. Her soft tongue lightly sought out mine, and as they danced against each other, I felt her body melt into mine. It was the kind of kiss I'd always longed for, easily the greatest first kiss of my life, and we continued for what felt like minutes. We both pulled back at the same time, each looking at the other, before embracing again, our mouths hungrily meeting. Her full pink lips were like heaven to me, tasting like an exotic fruit, her tongue soft against my own. I found my hands roaming her back, lightly grazing her supple behind as she pulled me tighter against her.
We finally broke apart, our breaths coming quicker, my heart thumping in my chest. She giggled like a nervous teenager, shyly meeting my gaze as I held her close.
"Wow...", she said, echoing my own thoughts aloud, "That was perfect!"
I put my arm around her, keeping her close as we continue as our kissing turned erotic, passionate, our hands straying over each other as our mouths plied against one another. Without realizing it, my hands had moved to her breasts, lightly cupping them as my thumbs brushed against her nipples. She responded immediately, moaning slightly into my mouth as her nails dug into my shoulders. I wanted to touch all her body but restrained myself for multiple reasons. Still, even barely caressing her perfect breasts had caused a stirring in my groin, making me hard almost immediately. I would have been embarrassed, however I figured that at our current angle, it was not as though she would have noticed.
She placed her hand on my leg and pressed against my throbbing hard-on.
"Oh...!", she made a surprised noise, her eyes widening slightly.
"Sorry...", I said sheepishly, "I can't help that you turn me on."
She didn't say anything, but I saw a small smile play across her face I mean, I wasn't a porn star, but I do have quite a large member.
Our kissing quickly turning heated. Almost without words, I was now blatantly massaging her luscious breasts, occasionally focusing on her hardening nipples. She moaned in appreciation, making soft cooing noises in response to my touch. The noises alone caused my cock to stiffen, and she in turn wiggled her bottom, pressing into me and making my balls ache from the built-up pressure.
I gently kissed her neck, I slid my hand up her firm thigh to her naked hip. My breath caught as my thumb pressed against her hip bone, her skin soft beneath my palm. Her tongue had been flicking against my own, her upper body pressing against my right hand that was on her breast, both our breaths now coming in ragged fits.
I began to fully squeeze and play with her naked breasts, unmistakable moans escaping her mouth as I licked my fingertips and then rolled her nipples between them. Her mounds were firm against my palm, filling my hand as I gently played with them. I became ridiculously turned on, more so than anytime I had ever been with this kind of action.
"You're really turned on, huh?", she asked, looking pointedly at the growing dick begging to be touched some more.
"Yes," I said, figuring it should have been obvious, "Your body is amazing."
"Most guys don't notice my breasts, they seem to focus on my butt.", she openly lamented.
I thought that was too bad if other men hadn't realized just how perky and nice her breasts were and asked her if my attention had turned her on as well. Instead of answering, she spread her legs apart.
I turned my attention to her bushy pussy. She had puffy lips, and a very pronounced labia, protruding like a butterfly preparing for flight. It was a gorgeous pussy, and I trembled as I moved my hand between her legs. I touched the outside of her lips first, grazing the inside of her tender thigh as I rubbed my fingertips across her delicate folds. I paused briefly, then slid my index finger into her slit, not yet penetrating her. She was incredibly wet, and my finger was instantly moist as I pressed up and around her pronounced clit. Her reaction was instantaneous, her body nearly convulsing as I began to make deliberate circles around her hood.
She was now loudly moaning as I worked her pussy, alternating between her wet interior and her swollen clit. I resisted the urge to bury my fingers in her, instead focusing on teasing the exterior of her soft pussy mound. I pulled my hand back, placing my two fingers in my mouth in order to taste her juices, rewarded by the sweet taste that filled my mouth. I licked them, wetting them in order to now slide them into her, then placed my hand back between her legs. She was kneading her own breast as I finally buried my finger inside her tight hole, feeling the suction as I slid in and out of her. I continued to move back and forth, sometimes pulling out to focus my touch on her clit, making small circles around it that seemed to make her quiver.
Occasionally reaching up to massage whichever breast was free, both of us seemingly on the edge of a climax. My cock was in actual pain from being so hard, I couldn't remember ever wanting a woman as badly as I wanted Wendy right then. Although she never orgasmed, I had her on edge, stimulated for over an hour.
I picked her up and she wrapped her legs around me, our mouths working feverishly at one another's as I lay her down on her bed. Kissing down her chest, I pulled first her left, then right nipple into my mouth, biting down gently on each as I suckled. She moaned her approval, her nails pressing into my upper back.
I reached up, first placing a pillow under her head, then grabbing the other as I licked and kissed my way down her torso.
"Lift your hips.", I told her, sliding the pillow underneath her ass, giving me a better angle from which to lick at her pussy.
I slid to the base of the bed and settled her legs on my shoulders. I kissed at the inside of both her thighs before zeroing in on her heated area. She was glistening in anticipation, her lips swollen and dripping the sweet nectar I had tasted earlier. Without hesitation, I licked her from the base to her clit, a slow steady movement that filled my mouth with her taste. My hands rested on her stomach, and I used my thumbs to pull apart her lips, giving me access to her steaming wet hole and throbbing clit. I lapped at her, lost in how wonderful she tasted, slowly circling all of her as she cooed her appreciation.
I increased the pressure of my licks, focusing more on her clit as I tried to build her to an orgasm. I wanted her to flood my mouth as she came, and I worked fervently to trigger her release. I slid a finger into her, finding her G-spot and pressing against it as I licked. Occasionally I pulled back, pulling her entire labia into my mouth, sucking on the soft skin and working my tongue like I was French kissing her, then once again going back to her swelling clit. After nearly an hour she could take no more, pulling me forcibly up her body.
"Baby, I have to have you inside me!", she begged, locking her eyes onto mine before kissing me, her own juices now being willingly tasted by her as our tongues danced together.
Wendy broke our embrace and she went to get a condom. “Tools of the trade.” I was not sure what she had there then she knelt to place it on my hard cock. Now with me suited up she pull me on top of her.
I leaned up, placing the head my cock at her entrance. Teasing her slightly, wetting myself with her juices, I then slowly pushed my cock into her. My eyes never left hers as I worked most of my member deep inside her, finally stopping when I felt the bottom of her about six inches in. She felt like a soft velvet glove, firmly milking me as I throbbed. We both groaned at the sudden pleasure, treasuring our first connection, joined finally in the most intimate of moments as I was buried inside her.
I pulled back gently, then pushed again into her. She moaned, and her hands slid down, taking my ass into her grasp. As I began to slide in and out of her, she guided my pace, slowly increasing the rhythm of our coupling. With each thrust she became louder, pleading for me to take her over the edge she had been at for hours now.
"Baby! Oh my god that feels so good! You feel so good inside me, ooooooohhhh!", she was panting, pulling me harder into her.
We rocked back and forth for nearly twenty minutes, a frenzied passion overcoming our bodies as she quaked beneath me. Sensing that she needed one final push to reach a climax, I leaned up, pulling her legs up to her body. I began thrusting harder, burying my full cock inside her at a faster pace. Her face froze in ecstasy, then she released a high-pitched scream, violently screaming incoherently, her head shaking in a wild "No!" motion as I fucked her deeper and longer than I knew I could. Finally, her hands gripping my arms, her legs spasming against my own, I felt her pussy tighten around my cock, the unmistakable throes of an intense orgasm racking her body.
I continued my pumping, her first orgasm rolling into a second, her juices spreading all over my cock and balls. I felt the pressure building inside me as we both reached an orgasm together, stars exploding behind my eyes as I released into her. I felt my come fill the condom in her cavity, emptying my entire load as my body shook. She gave one final cry, then began laughing, the emotions overcoming her in the end. I stopped, gently resting on her body as she covered my face in kisses.
"I've never been fucked like that," she breathed hoarsely into my ear, "Never baby, oh my god..."
I leaned back and smiled at her, spent from our lovemaking. I slowly pulled myself out of her, lying down next to her and pulled her against my chest. Our breathing quieted down together, and she nuzzled against me, drifting off to sleep for about an hour. She awoke me telling me we had to leave. We got up dressed. On the street once more. I looked in my wallet and I had $20.00 dollars and handed it to her. She smiled took it and I never saw her again. I think that was the way it should be and would be my whole life.
My first event was only the beginning. I had no idea where this would take me.