My Chauffeur for the Canadian Woman in Distress

I hit the road, cruising north on I-95 through New Jersey, the cold January air whipping past the Escalade as I headed toward New York. Three days of meetings and property tours in Trenton had been productive, and I had just one last client to visit outside of Boston before I could head back to Montreal.

I love driving, and it allows me to drop in unannounced on properties owned by the REIT, keeping our property managers on their toes. The radio announcers warned of a powerful snowstorm moving into the region from the Midwest, but I wasn’t particularly worried – I’d probably be close to Boston by the time the snowflakes started to fall, and the Escalade was a real snow machine.

I glided into a rest area, pulling up to a pump as the usual herd of road warriors congregated in front of the fast food restaurant. I spotted a young woman holding a cardboard sign that read “Canada” in large block letters. She wore a puffy parka and ski pants, but I could tell she was probably in her early 20s and about five feet tall.

“Bonjour,” she said, her voice soft and melodic. I turned around, and she smiled. “I couldn’t help but notice your license plate. Are you on your way back to Quebec?” I asked her name, and she replied, “Eve. Nice to meet you, Robbie.”

We struck up a conversation, and I learned that Eve was a French Canadian/Native American mix, with high cheekbones, a complexion, and eye shape that hinted at her mixed heritage. She had a friendly face, and I found myself drawn to her. We exchanged stories, and I discovered that Eve had hitchhiked down to Key West, but had been on her way home for a week.

“I’ve been very picky about the people I take a ride from,” she said, smiling at me. “You’re an example of that. I don’t think a well-dressed guy driving a huge SUV is going to be a problem.” I smiled back, and we continued to chat as we drove through the snow-covered landscape.

As we passed through Hartford, Eve dozed off, and I let her sleep. I woke her when we merged onto I-84, and asked if she was okay with a stop for a bathroom and some food. “Sure Robbie, but I’m buying, okay?” she said, smiling at me. I pulled into a restaurant, and we sat down to eat.

Eve was petite, with delicate hands and a fluid motion that really got my attention. I asked her how tall she was, and she replied, “I’m 151 cm. Brown hair and brown eyes as you can see. I’m probably about 50 kilos if you must know, but that might change depending on how much I eat right now.” I stopped the Q&A session, and we ordered our food.

“What do you do for a living?” Eve asked, breaking the silence. I explained that I bought, managed, and sold commercial properties for a REIT. She asked about my family, and I told her that my father was from the U.S. and that he’d met and married my mother in Montreal. She seemed pleased when I told her that I was close to them, and that they lived in Brossard.

“Do you have any siblings?” Eve asked, and I shook my head. “No, I don’t have any brothers or sisters.” She nodded, and we continued to chat, exchanging stories and getting to know each other.

As we finished our meal, I glanced over at Eve, feeling a connection that I couldn’t quite explain. I smiled at her, and she smiled back, and I knew that this chance encounter might just change my life forever.

“I have to say, I’m really glad I picked you up,” I said, smiling at Eve. “You’re a very interesting person.” She smiled back, and I could see the spark of attraction between us.

“I’m glad I got a ride,” Eve said, her voice barely above a whisper. “I was getting a little worried.” I nodded, and we continued to chat, the snow falling gently outside as we drove through the night.

As we merged onto the Hutch, Eve yawned, and I asked her if she was tired. “Yeah, I’m a little tired,” she said, smiling at me. I nodded, and we continued to drive, the snow-covered landscape passing by in a blur.

“Do you want to take a nap?” I asked Eve, glancing over at her. She nodded, and I pulled over to the side of the road. We drove in silence for a while, the only sound the gentle hum of the engine.

Eve was asleep, and I let her rest, my eyes fixed on the road ahead. I was lost in thought, my mind replaying our conversation and wondering what the future held for us.

As we passed through the snow-covered landscape, I felt a sense of excitement building inside me. I had a feeling that this chance encounter might just lead to something special, something that would change my life forever.

Eve’s words hung in the air as I sat in stunned silence, trying to process the depth of her pain and vulnerability. I knew I had to tread carefully, to be genuine and honest in my response. “Eve, I believe you,” I said softly, my eyes locked on hers. “I think you’re an incredible woman with so much to offer, and it’s heartbreaking to hear that you’ve been treated poorly in the past.”

She sighed, her shoulders sagging as she looked down at her hands, which were clenched together in her lap. “I just feel like I’m running out of time,” she whispered, her voice cracking with emotion. “I want to find someone special, to love and be loved in return, but it feels like that’s just a fantasy for me.”

I reached out, my hand hovering over hers before I hesitated, unsure if I should touch her. But then I remembered her words, her plea for honesty, and I took a chance. My hand gently covered hers, and she looked up at me, a glimmer of hope in her eyes.

“You’re not just saying that, are you, Robbie?” she asked, her voice barely above a whisper. I shook my head, my heart pounding in my chest. “No, Eve, I mean it. You’re an amazing woman, and I’m flattered that you’d even consider me.”

She looked at me for a long moment, searching my face for any sign of deception. And then, slowly, a smile spread across her face, a radiant smile that lit up the dark room. “Thank you, Robbie,” she said, her voice filled with emotion. “Just knowing that someone believes in me, that someone sees me as worthy of love and respect… it means everything to me.”

I felt a surge of emotion, a deep connection that went beyond physical attraction. I wanted to hold her, to comfort her, to tell her that everything would be okay. But I also knew that I had to respect her boundaries, to let her come to me when she was ready.

“Get some rest, Eve,” I said softly, my hand still covering hers. “We can talk more in the morning, okay?” She nodded, a small smile still on her face, and slipped out of bed, leaving me alone in the darkness.

I lay there for a long time, my heart still racing from the intensity of the moment. I knew that I’d made a connection with Eve, a deep and meaningful one. And I couldn’t wait to see where it would lead us.

As I drifted off to sleep, I felt a sense of peace wash over me, a sense of knowing that I’d found someone special, someone who saw me for who I truly was. And I knew that I’d do anything to protect her, to love her, to be her rock in the midst of life’s challenges.

The darkness seemed less intimidating now, less lonely. I was no longer alone, thanks to Eve’s presence in my life. And I knew that nothing could ever make me feel more alive than the thought of her by my side.

I woke up to the sound of my phone buzzing on the nightstand. I reached over to silence it, only to see a text from an unknown number: “I’m in room 314. Come find me.” My heart skipped a beat as I read the message, my mind racing with possibilities. And then, without hesitation, I tossed off the covers and got out of bed.

I made my way to the elevator, my heart pounding in my chest. I had no idea what I’d find in room 314, but I knew that I had to see Eve, to be with her, to explore this connection that was growing between us.

As I stepped out of the elevator and onto the third floor, I felt a sense of excitement, a sense of possibility. I knew that I was taking a risk, that I could get hurt. But I also knew that I had to take a chance, to see where this journey with Eve would lead me.

I lay there in silence, giving her the space she needed to express her true thoughts.

“I’m scared of being hurt again,” she whispered, rolling toward me. I slid my arm under her head, pulling her close as she wrapped her hand over my chest.

“Hold me, Robbie,” she whispered, her voice barely audible.

I held her tightly, feeling her warmth against me as she snuggled in. She was incredibly soft and small, and I knew I’d just been given a priceless gift – her trust. I’d known her for less than a day, but I believed I’d found someone who shared my goals and values. I listened to her breathing, waiting for her to drift off to sleep.

Later, she gently stirred, wrapping her arms around me. “Wake up, sleepy head,” she whispered, her voice husky with sleep.

“Shower time,” she murmured, sliding out of bed and heading toward the bathroom. Her hips swayed enticingly as she pulled her t-shirt over her head, and I couldn’t help but watch.

“Do you need a written invitation, Robbie?” she teased, a mischievous glint in her eye.

I rose from bed, following her into the bathroom. She’d already taken off her sweatpants and was reaching for the shower, her body glistening with water droplets. I caught my breath, my eyes feasting on her naked form.

“I want to feel you against me,” she whispered, her arms wrapping around me as she pulled me close. Her breasts fit perfectly under my chin, and I could feel my cock straining against my boxers.

“Let’s take these off,” she whispered, her hands reaching for my waistband.

I hesitated for a moment, but her eyes sparkled with encouragement. I let her push my boxers down, and we stood there, our bodies pressed together.

Eve swayed her hips, creating an incredible friction between us. I wrapped my arms around her back, feeling her warmth and softness. When she turned around, she guided my hands down to her breasts, and I couldn’t resist squeezing them gently.

“Touch me,” she whispered, her voice barely audible.

I ran my hands up and down her body, feeling the incredible curve of her waist and reaching down to explore the dark tuft of hair above her vulva. She was exceptionally soft, and I felt myself tightening as I moved toward the point of no return.

When I stepped backward to slow things down, Eve turned toward me, her eyes sparkling with mischief. “What are we going to do about this?” she whispered, her hands running up and down my cock.

I felt myself getting close, but Eve’s gentle touch and sweet words kept me from cumming. “Don’t hold back, Robbie,” she whispered, her voice husky with desire.

I didn’t have a choice, and I clenched my teeth as I came, shooting cum between her body and mine. Eve kept moving back and forth, pressing her body against mine, and I felt like I was flying.

She pulled away, a smile on her face. “That’s for last night, Robbie,” she whispered, her voice barely audible. “That’s for being a decent human being.”

She took my hand, leading me into the shower. We spent almost a half hour exploring each other’s bodies, washing every inch of skin.

Later, she guided my hand down between her legs, and I gently pressed a finger against her clit. She closed her eyes, moaning softly as I continued to touch her.

I could feel her getting close, and I inserted my finger deeper inside her pussy. She shuddered twice, let out a gasp, and came. I felt the incredible strength of her muscles as they contracted and clamped down on my finger.

I realized I’d never kissed her, and I stood, pulling her against me and kissing her deeply. We were both dazed, and after drying off, we returned to the bed and snuggled under the blankets.

“That was something,” I whispered, pulling her close and giving her another kiss.

“Do you think I’m sexy?” she asked, her voice barely audible.

“You’re insanely sexy,” I whispered, my lips grazing her ear. “I’m turned on by the feminine shape of your breasts, and large, natural breasts do that.”

“God, they’re not that big, Robbie,” she whispered, laughing. “It depends on the bra and the time of the month.”

I took a nipple into my mouth, teasing it with my tongue. Eve began to tweak her other nipple, and we both felt a rush of pleasure. Her nipples swelled to their fully erect size, and I was amazed.

“Robbie, I’m really attracted to you too,” she whispered, her voice husky with desire. “I hope I’m not hurting you.”

I told her exactly how I felt, and she smiled, her eyes sparkling with mischief. “I want to feel you against me,” she whispered, her voice barely audible.

I told her everything I was thinking about, and she listened intently. “My cycles are always 30 or 31 days, and I’m willing to take that risk if you are,” she whispered.

“I’ve been tested,” I whispered, my voice barely audible. “I’ve always used condoms, so I’m pretty sure I’m okay.”

“Well, nothing here either,” she whispered, her voice husky with desire. “My ex always refused to have sex without a condom, even just before, during, or right after my period.”

We talked for a moment, and then Eve pulled the blanket down, looking at my cock. “Well, I guess I have your answer, don’t I?” she whispered, her voice barely audible.

Eve turned and swung her leg over me, putting her pussy directly over my face. I was mesmerized by her scent and the wetness from her earlier orgasm, and I pulled her downward so I could taste her.

She was incredibly clean, and I gradually worked my tongue inside her, trying to concentrate as she continued to touch and squeeze me. She made a few “oh” sounds and pressed her pubic bone against my chin.

Without warning, Eve took my cock into her mouth and sucked gently, running her tongue around the tip. She squeezed my balls as she started to move up and down my cock, and the sensation was incredible.

She paused, releasing me from her mouth. “Let me know before you’re going to cum, okay?” she whispered, her voice husky with desire.

I felt myself getting close, and I touched her, letting her know what was going to happen. To my surprise, she didn’t stop, and I felt myself slipping over the edge.

Suddenly, Eve raised herself off of me, turned quickly to face me, and pressed her vulva against the base of my throbbing cock. I gasped as she put her entire weight onto me, and I involuntarily raised my knees against her ass as the first contraction of my orgasm began.

“Not yet,” I whispered, my voice barely audible.

When I recovered enough to open my eyes, I was treated to the sight of Eve’s breasts above me as she continued to press against me. She was looking down with a strange look at my cock, and when I followed her gaze, I realized that a large string of cum had managed to make it past her defenses onto my stomach.

Eve reached down and collected what she could, bringing her hand back to her mouth and tasting what she’d found. She leaned over and kissed me deeply, and I was excited by the knowledge that she tasted herself in the same way that I tasted myself.

“If you move before I have a few minutes to recover, I’ll probably cum very quickly,” I whispered, my voice barely audible.

Eve continued to press against me, and I reached up to gently cup her breasts, feeling their warmth and weight. They did have a hang to them, and this really turned me on. I told her so, and she smiled, her eyes sparkling with mischief.

My heartbeat slowly returned to normal as I gently massaged her breasts, trying to calm the intense passion that had taken over our bodies. Eve finally raised her hips, her movements light and teasing as she rubbed her vulva against my cock. As blood circulation returned, I hardened, and she started to bear down, swaying her hips from side to side.

She was clearly enjoying the feel against her clit, which she pressed tightly against me by tipping her hips forward at the end of each stroke. I could feel her excitement growing, and I knew it was only a matter of time before she would be ready for me.

Eve stopped, moved forward slightly, and placed her lips directly over the tip of my cock. I could feel her wetness as she pressed downward, her lips parting slightly around me. I was just a small motion away from being inside of her. She paused, her breath catching in her throat.

“I’m right here if you want me,” she whispered, her voice husky with desire.

I pushed forward, but I had to pull back when I missed her entrance, and she slid along my shaft. As I pushed forward again, she leaned forward, tipped her hips, and I was inside of her. Eve pushed against me until I could go no further, and then squeezed my cock tightly with her powerful muscles.

“God Robbie, you are touching my cervix when I do that, and it feels fucking good,” she gasped, her body trembling with pleasure.

After several minutes, Eve’s breathing became ragged as she pumped her hips more and more rapidly against me. I could feel her getting closer to her orgasm, and I was barely able to hold back.

“No, Robbie… …No… …just keep going…” she pleaded, her voice barely above a whisper.

She pumped even faster, and I could no longer help myself; I released stream after stream of cum inside of her. “I can feel that… …holy shit… …holy shit…,” Eve gasped, her body convulsing with pleasure.

Her orgasm was intense, and I knew I was in trouble. My cock remained hard, but it felt white hot from the incredible overstimulation. I didn’t know if I could take much more.

But then, something changed. The pain started to turn into pleasure once again, and I began to meet Eve’s heavy thrusts with thrusts of my own. After a few more minutes, she was panting heavily and clearly just moments away.

“Oh God…” she whispered, her body trembling with anticipation.

Tremors went through Eve’s body as her pussy convulsed in orgasm, and my cock was squeezed to the point at which she could no longer move up or down on it. Her orgasm gradually faded, and she collapsed forward into my arms, my cock still deep inside of her.

Her breathing slowed, and she rolled off of me. “That was incredible…” she whispered, her voice barely above a whisper.

I mumbled something, still trying to catch my breath, and looked down at my cock, which was covered in cum and Eve’s juices. It was still standing at attention – something that Eve noticed a moment later.

“Jesus, you’re still hard Robbie,” she said, a smile spreading across her face.

She turned and swung her leg over me, placing her cum-filled pussy just above my face once again. A drop of cum dripped from her onto my chin as she took my cock into her hands and squeezed it.

When Eve lowered her head and began to use her tongue to lick me, I pulled her down and sucked on her lips, pressing my tongue inside of her and tasting our combined juices.

We kept at this for a few minutes, and then I told Eve that I didn’t think I could cum again. “Twice in one morning was a world record for me, anyway,” I joked.

Eve raised her head, took my cock into her hands, and tried to point it toward my feet, but it was no use. “Well, let’s not waste this, ok?” she said, a mischievous glint in her eye.

She got off of me, turned, and remained on her hands and knees. “Just put it inside of me again for a minute, ok?” she whispered, her voice husky with desire.

I moved around behind her and entered her again, not sure of how it would feel. But as I started to move in and out of her slowly, I was surprised to find that it felt damn good. Her pussy was slick, and we made a wet sound every time we pressed against each other.

“Harder, Robbie,” she whispered, her body trembling with pleasure.

I began to enter her more rapidly, pushing in as far as I could and pulling back until I was barely inside of her. Eve met my thrusts, lowering her head to the mattress and presenting her pussy so that I could really go deep.

I stopped for a moment, ran my hands along her waist, and followed the flare of her hips until my hands were on her ass. I spread her slightly, and then buried myself into her as far as I could, searching for her cervix.

“That’s it, Robbie… …right there…” she whispered, her body convulsing with pleasure.

I could feel her cervix lightly against the tip of my cock each time my pubic bone pressed against her. After a few minutes, a tickle deep inside of my balls told me that something might be pending.

I increased the speed of my thrusts as the tickle became stronger and stronger. Eve was making low moaning sounds and shaking her head from side to side.

The tickle suddenly turned into a jolting spasm, and I shoved myself inside of Eve as deeply as I could as my cock twitched and injected whatever sperm remained in my balls into her. The unexpected intensity and sharpness of the orgasm caused me to grunt loudly, and I pulled out of Eve when it faded, rolled to the side, and lay on the bed, completely drained.

Eve smiled and lay beside me, her body still trembling with pleasure. “I think you owe me an orgasm, Robbie,” she whispered, her voice husky with desire.

I pulled her close, and the smell of her hair filled my nose. It was Jasmine – a scent I had only ever associated with memories of our first time together.