Surprise Suprise

Story Info
A small winter drive turns into something bigger.
4k words
4.72
21.3k
33

Part 1 of the 2 part series

Updated 06/16/2023
Created 05/04/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The frigid Montreal winter was taking its toll on me. After three long months of frigid cold, I strongly considered packing up and moving to Florida. I had just finished my morning walk and thought my face was going to peel off.

Everything seemed so bleak and dull. Going to work on a Saturday morning in middle of a blizzard made it so much worse. It was the busiest time of the year for my small accounting firm. I guess I made a decent living, but it wasn't as exciting as I thought it would be.

After gulping down my coffee and eating my breakfast, I took a quick shower and headed back outside. I barely took the ten minutes to properly dress myself. I nearly slipped and fell onto my car. What a terrible day it was! This day was only going to get worse.

I couldn't believe the stupid car still ran. It was a 1998 Toyota Tercel that my grandfather gave me. I called it 'the tank', because the damn thing just wouldn't die. Even on the coldest winter mornings it would just go. I cleared the snow off the car, and off I went to work. I couldn't believe the heat still worked in this little shit-box.

The snow squalls made seeing out of the car nearly impossible. Why the hell did I go into work? I kept swearing to myself. Was it really worth it on a Saturday morning? The usual thirty minute drive took me over an hour. At least I had indoor parking.

Up the endless four flights of stairs I went. I sighed, thinking about the stacks of papers I would have to dig through on this miserable Saturday morning. I used whatever strength I had to push the office door open.

"Good morning." Her soft voice interrupted my miserable silence.

I was sure it would just be another miserable day at the office. Then I finally remembered the reason I got up every morning and went to work. She was the best secretary I ever had, and she was incredibly beautiful.

"Good morning." I muttered back at her, quickly walking past her desk.

She was the most beautiful woman I had ever seen in my life. Her long blonde hair and piercing silver eyes would make anyone look twice. Her slender six-foot frame would make any guy drool. She looked like a model from one of those magazines.

I had no idea why this attractive supermodel would be interested in working in my boring accounting office. But she always worked fast and never complained about work load. I got deep into my endless paperwork, and tried not to get too distracted. A light knock on my office door nearly knocked me off my feet.

"Come in." I said, not even bothering to look up from my endless paperwork.

She was wearing a beautiful red satin dress. It looked like she was going to be a bridesmaid at a wedding. I tried to too stare at her full breasts popping out of the top of her dress. I wanted that dress off so badly. I wanted to see her hot naked body. I tried not to stare at her chest as she leaned over my desk.

"I brought you coffee." she said, her pretty pink lips smiling wide open at me.

"Are you ok?" she asked me, sitting down across from my desk.

I pushed my pile of papers aside, and directed my attention to her. She crossed her long legs in front of her, dangling her big black stilettos just above the floor.

I told her about my recent divorce, and how my ex wife was trying to take the kids away from me. I told her how lonely it was it my cold empty apartment. I left out the part where I would nearly cry myself to sleep most nights.

She slowly sipped her coffee as I drank mine. She listened attentively as I dished out my endless problems. Her pretty red fingernails tapped lightly at the top of her white coffee mug. She left a small lipstick stain on the edge of her mug. I wish she would press those pretty lips against me. I wish I was that lucky coffee mug.

After a bit more small talk, she stood up off her chair. She leaned over the desk again, and hugged me tight. Her full breasts pressed against my button up blue shirt. I awkwardly wrapped my arms back around her. Her soft left cheek pressed against my right one for second. I could smell her strong perfume lingering as she slowly let go of me. She took both mugs, and slowly left the room. She turned back and smiled at me, catching me staring at her sexy backside. I don't know if it was on purpose or not but she rocked her hips side to side, really make her butt wiggle.

Well, back to the boring day ahead. If only I could ignore my raging hard on. If only I could ignore the lingering smell of her perfume. If only I could ignore the thought of grabbing her breasts. If only I could ignore the thought of bending her over my desk and making love to her from behind.

I reached down and gently caressed myself through the outside of my khaki pants. I couldn't wait to get out of the office and finish myself off. I couldn't wait to stroke myself up and down dreaming about her hot naked body. I was way to chicken to make a move. I figured she was just being a bit of a tease. Why would she want a balding middle aged accountant?

I buried myself deep into my paperwork for next couple hours. Finally, my otherwise uneventful workday was over. I quickly gathered up my remaining paperwork and threw on my winter jacket. I could still smell her perfume lingering in my small office. I walked passed her desk, but I guess she had already left for the day. It was weird she didn't say goodbye, but maybe she was in a hurry.

As I was about to exit the office building, I saw her sitting on the small bench in the lobby. She looked so sad, she was almost in tears. She explained that she missed her bus, and her taxi was already an hour late.

"I'll give you a lift." I suggested, trying not to stare at her perfect body.

She stood up and lightly kissed me on the cheek. She wrapped her long arms around my back and hugged me tight. I was a bit shaky being so close to her. I was always awkward with being affectionate. The hug earlier in the day was already a lot for an introvert accountant like me. She held my arm, and we made our way out of the building towards my car.

We both laughed as she awkwardly swung her long legs inside my car. She was so much taller than I was. My car clearly wasn't built for someone over six feet. She nearly smacked her head on the roof.

"I know it isn't much, but it works." She shrugged off my negative comment.

"It's better than waiting in the cold for two hours." She said, trying to adjust her seatbelt.

She had a good point.

Driving all the way across town in middle of a blizzard was quite the challenge. I kept sneaking peeks her thin beautiful legs. She was so tall that her knees pushed up against the glove compartment. Her dress slid back just enough for me to peek at her smooth upper thighs. I could see through the rear view mirror, that she was wearing red panties under her dress. I could only dream about what was underneath them. More importantly, I had to not get us killed.

Suddenly, the winter storm got really bad. I couldn't see out the front of the car due to the massive snow squalls.

"You can't drive in this." she declared, grabbing my arm.

"Why don't you come in until it the storm passes?" she suggested.

I got out first and opened the car door for her. As she came out of the car, we both slipped onto the icy sidewalk. She knocked me over, and fell directly on top of me. Our eyes met for a brief moment. I was thinking of making a move, but I chickened out. Why would she want me anyways? She was so far out of my league. She probably had a young stud of a boyfriend. She could get any guy she wanted. I was just being a gentleman, giving my hot secretary a ride.

She laughed and got off of me, pulling me up towards her. I had never met a woman in my life with the upper body strength she had. She grabbed my arm so I could get my bearings back. Good thing we were so close to her apartment.

She took my hand and led me inside her apartment. She undid her stilettos and hung up our winter coats. She took my hand and led me into her living room. The view from her 20th story apartment was incredible.

I marvelled at the spectacular view of Montreal's downtown skyline. It was beautiful even with all the blowing snow flying about. We were both still shivering from falling on the icy sidewalk. I was so busy checking out the view, that I barely noticed her handing me a pair of old jogging pants and a T shirt.

I figured the clothes belonged to an old boyfriend of hers. I quickly went to the washroom to change out of my cold damp clothing. I felt like such a dumbass for not making a move. Her gorgeous face and pretty silver eyes were inches away from me.

I glanced down at my hard-on as I changed into the dry clothing. I really had to do something about it. I considered rubbing one out on the spot. But that would for sure take too long. I really didn't want her to notice my ever expanding bulge. I got dressed and quickly went back to the living couch to wait for her. I was doing my best to hide my hard-on.

She came back out into the living room wearing a pink silk slip. Her choice of outfit really wasn't helping me lose my ever expanding hard on. Her large full breasts pushed through the sexy satin slip. I did my best not to stare at the faint outline of her areolas around her perky nipples.

I couldn't help but notice at how muscular her arms were. That explained how she was able to lift up my two-hundred pound frame. She sat down uncomfortably close next to me on the couch, and poured each of us a double shot of twelve year glen. We tapped our glasses together, and slowly sipped our drinks.

She leaned forward and grabbed the remote off the table, turning on her fake fireplace. Sure it wasn't an actual fire but it felt so warm. Or maybe it was the whiskey slowly seeping its way through my nervous body.

We chatted and had a couple more drinks. Turns out she just went through a pretty rough break-up with her long time boyfriend. I wasn't paying much attention to what she was saying. I was too busy trying not to stare between her sexy exposed thighs. Her little slip barely covered her red lace panties.

She put her glass down, leaned towards me, planting a soft kiss on my lips.

"Do you feel better?" she asked me, gently caressing my thigh.

"I do now." I replied, kissing her back.

I could taste the whiskey on her moist tongue. I caressed the side of her face and kissed her more passionately. We gently bit each other's lips back and forth. I leaned forward and started to kiss the side of her neck just under her left ear.

She leaned forward and reached between my legs. It became clear she wanted a lot more than soft kissing. She gently caressed my chubby cock through the outside of the joggers. I tried to reach between her legs but she pushed my hand out of the way. She spread her legs a bit and gave me a quick peek at her red lace lingerie panties. She quickly closed her legs and reached inside my pants. Ugh, what a tease this one was.

"Can I taste you?" she whispered in my ear.

Before I could answer, she got on her knees in front of me. She pulled the joggers all the way off and threw them down on the floor. My chubby little soldier was rock hard ready for duty. Her warm soft tongue took long strokes back and forth on the tip, making me my moan with pleasure. I reached forward gently pinched her hard nipples through her slip. She slowly teased me in and out of her mouth.

Her saliva dripped all over my hairy swollen balls. I caressed her long blonde hair and pushed her further forward on me. She stopped blowing me for a second and quickly stroked my saliva drenched cock. She leaned up and kissed me, I could taste my cock all over her pretty pink lips.

She stopped blowing me and stood up in front of me. She grabbed my hand and guided it between her long legs. I couldn't wait to touch her wet pussy. She pushed my hand away, and she turned around.

She smiled back at me and pulled her panties down under her butt, enough to expose her perfect ass. It was so smooth and muscular, but somehow so feminine. She reached back and spread her cheeks apart, showing off her tight little hole.

I tried to lean forward to grab her ass, but she pulled her panties back up. She turned back around and sat next to me on the couch. She leaned down into my lap, and continued slowly blowing me. I grabbed my cock and slowly teased it in and out of her mouth. She pushed my hand away, and she gagged hard on my throbbing cock. I pushed her head down in place, and held it there for bit.

Holy shit! She was really good at this. I never got head like this in my entire life. She was so good at having me deep in the back of her throat. I did a few more times until she gasped loudly for air. She leaned up for a kiss, dripping her saliva all over my bare chest.

I slid my hand inside her slip gently played with her nipples. They were getting harder and harder as we kissed. She slid it halfway off exposing her perfect breasts. I gently chewed on her exposed nipples as she stroked me up and down.

She pushed me away got back on her knees again. She looked up and smiled at me as her saliva dripped all over my swollen cock. She slid my saliva drenched cock between her breasts, pushing me in and out of her mouth. I was going to explode all over her breasts and mouth.

She stopped blowing me and sat on the couch next to me. She spread her long thin legs wide open. I finally got a good look at her red lace panties.

"Do you want to taste me?" she asked, fondling her naked breasts.

I couldn't wait to taste her dripping wet pussy. She grabbed my hand and slowly guided me up between her long perfect legs. She was shaking so much something was wrong. Up until now she seemed to really enjoy our sexy night together. Maybe I was taking it too far.

"Are you ok?" I asked her.

She pushed my hand back, and covered up herself up.

"There's something I need to tell you." She said, tears started streaming down her pretty face.

She pulled me tight against her and kissed me softly on my lips. Our warm naked upper bodies pressed together. I wanted her so bad but I didn't want to take it too far. She pressed her tear soaked face on me. I could feel her warm salty tears rubbing against my cheek.

"Would you accept me no matter what?" she asked, looking deep into my eyes.

"Of course I would." I replied.

I was doing my best trying not to stare at her exposed breasts and fully erect nipples.

She guided my hand up her thigh I couldn't wait to touch her wet pussy. I was still confused as to why she was crying. I got a very big surprise when I reached between her legs. I leaned forward and kissed her more passionately, squeezing my body against hers.

"You really don't care?" she asked me, fighting back tears.

She lifted her slip all the way up over her head, and removed it completely. She spread her legs wide open. There was a big bulge between her smooth legs under her red lace panties. I reached inside her panties as we kissed. I stroked her up and down, slowly making her harder.

I got on my knees in front of her and pushed her panties aside. She reached down and took it out of her panties. I started slowly sucking her up and down, while toying with her clean shaven balls. Her crying quickly turned into soft moaning. She pushed my head down between her legs. She pushed into me and slowly expanded in my mouth.

I could barely fit her inside my mouth. Truthfully, I was a bit jealous it was much bigger and thicker than mine. It was easily double the size of mine.

She reached down and pulled it out of my mouth, teasing it all over my face and lips. Finally, she grabbed it and shoved it in and out of my mouth. Now I was the one gagging hard on her. I reached up and pinched her nipples hard while I sucked her off. She pushed my head so hard on her I could barely breathe. I almost got it all the way inside my mouth.

It was my first time with someone like her. I couldn't believe how much I enjoyed it. I was never with a guy before, but somehow this felt less gay. I guess that's because she look more like a woman than a man. I guess because on the surface nobody could even tell. Since I was a teenager I would touch myself dreaming about being with a hot chick with dick.

She pushed my head away, and turned around grabbing onto the couch. She pushed her lace panties around her thighs, and stuck her perfect butt. She pushed her ass forward into my face. I got the idea and started slowly licking her little hole. I grabbed her ass-cheeks and spread them apart, pushing my tongue further inside her.

"I guess you wanted some pussy." She said, as I licked her tasty hole.

I tried to push my finger inside her, but she pushed me away. She turned around and slipped her panties all the way off. She pushed me off knees and flat onto the floor. She squatted down on my thighs and faced me. Her breasts pushed against my chest, and her long blonde hair fell on my shoulder. She kissed me on the lips a few times, and got up to grab something. But not before she grabbed both our cocks and rubbed them together a few times.

"I'll be back, I need to grab something." She said, shoving her panties deep in my mouth.

I couldn't take my eyes off her naked body as she walked upstairs to get something. She purposely took her time walking to her room. She turned back and smiled at me, rocking her sexy hips back and forth.

She finally came back from her bedroom. She walked slowly towards me, stroking her large member back and forth in front of her. She spread a warm liquid up and down on my hard cock. She pulled the panties out of my mouth with her teeth. She shoved her cock as far as it would go into my mouth while she jerked me up and down.

She pulled herself out of my mouth, and squatted down on me. It took us a few tries, and a lot of lube. She squatted on me, and I held myself in place. I finally slid inside her tight asshole. She pushed her long muscular arms against my chest, and pushed her ass down on my cock. I reached between our bodies and stroked her, as she pushed further down on me pressing her ass against my swollen balls.

I stroked her faster and faster as she rode up and down on my throbbing cock. She rocked her ass back and forth on me, harder and harder. I grabbed both her ass-cheeks while she rode me, but she was going so fast I couldn't even hold on. I bit on her hard nipples and her cock rubbed against my belly as she slammed her body hard between my thighs. Just as I was going to finish, she got off me. She got on all fours, and begged me to do her from behind.

I readily complied and teased myself in and out of her. She turned and moaned as I pushed further inside her, grabbing her sides with all my strength. I couldn't believe how much she liked getting it from behind. I grabbed her long hair and shoved into her. I nearly fell over as I exploded inside her. She quickly turned around and sucked me off, stroking herself as she sucked me dry.

She pushed me on my back and grabbed the small container of lube. She pushed my legs hard up against my chest, and flicked her tongue in and out of my hole. She slid one finger in me, two, and then her thumb. She pushed her cock deep in my mouth while teasing her fingers in and out of me. I was terrified, there was no way I would be able to handle her.

She pushed her entire body against mine. Her breast dangled on my face as she tried to push herself inside me. She must have realized I was in pain, because of how much I was squirming..

I went on top of her and cautiously squatted down.

She added a bit more lube to her massive cock, and I slowly slid further down her. I leaned forward and kissed her soft pink lips. I pushed my chest against her perfect breasts. She grabbed me tight and my head fell next hers. I was experiencing pleasures I never felt before. She slowly pushed inside me. She reached up and spread my ass-cheeks apart, squeezing me with her strong hands. I couldn't believe how deep she was going in me. I leaned all the way back, and rode her up and down. I was only able to get her halfway inside me, but it felt amazing.

12