Swiping On My Best Friends Dad

Having no plans on a Friday night has left me here, mindlessly swiping on multiple dating apps in my pajamas while lying on my bed eating stale cookies.

I live alone in my one-bedroom flat with my cat, Sam. I try to go out on the weekends since all I do is work through the week. After a string of failed relationships, I have made it clear in my bio that I'm just looking for fun.

I'm 28 with daddy issues, so my age preferences are 30-45. I've worked through what I can in therapy, but reminders still linger in attraction to older, emotionally unavailable men.

As I swiped on looks alone, I ran across someone who caught my eye. His first picture was of him standing next to a large boat, more like a yacht. He seemed to be at least 6 feet tall, he had a head of thick jet-black hair and a beautiful smile sat on his squared jaw. He has a full beard that's well taken care of. It was salt and pepper in a way I found attractive. His blue eyes seemed to pierce through the camera. Muceles peeked from under his green polo, and his legs looked toned in his khaki shorts.

He looked familiar, but I could not place why. Even his name seemed to ring a bell. Tom Johnson. I swiped right and then went to his bio. It was plain, "45, bioengineer, avid adventurer, reader, and movie fanatic."

Good enough for me. I continued scrolling through his photos. The last one hit me with full force as I knew why he looked familiar. My best friend's dad. Jessica Johnson's dad. Rich Jessica, only saw her bioengineering father on the weekends because her mom divorced him when Jessica was 15, Jessica. He was never home and I only met him a handful of times when we were younger.

Damm. Suddenly, I received a new message. I went to the messages tab and...fuck, it was Tom, he matched with me. Does he remember me? It's kind of weird that his age range is someone his daughter's age, but then again, my age range is someone her dad's age. Granted, he's young. He and her mom had Jessica at age 18 right out of high school.

I opened the message.

"Hello, Sarah." That was all it read. Do I reply? Do I block him? Do I tell Jessica? She hasn't seen him in over 3 years.

I felt... dirty. Would Jessica even ever know? Last year she moved 2 hours away for her job. It's all harmless... right?

"Hi, Tom, how are you?" That was my reply. I wasn't going to let on like I knew him.

A few minutes later, I got an answer.

"I'm well this evening. Quite lonely on this chilly Friday night. How about yourself?"

Right to the chase with his comment about being lonely. Who would have thought Jessica's dad was a fuck boy.

"The same. I was lying here wondering what I would get into this weekend."

Was I trying to go down this road? It doesn't quite feel wrong but it doesn't quite feel right either. Tom is a handsome, rich, intelligent man, it would almost seem wasteful to pass up this opportunity.

"Sarah, you seem like a fun, interesting woman. What are you looking for here?"

Straight to the point. I am honest so I reply, "I appreciate the observation. To have a good time. What about yourself?"

"The same. How about we meet up for dinner at the Ritz?"

I hesitated. Am I going to go through with this? Can I go through with this? I looked back at his picture and stared for a minute. Damn, he's fine alright.

"That sounds lovely. Just give me a time."

I did it. I sent it. My stomach fluttered. I wonder if dinner would lead to a room.

"7 pm tonight?"

It was 5 p.m. right now. I wasn't sure how he would get us a table this late but I didn't ask questions.

"See you there."

I hopped out of bed dropping crumbs on the floor that I didn't have time to sweep. I rushed to the bathroom, threw off my clothes, and stepped into the shower.

I washed my hair and touched up my legs and underarms with a razor. I made sure my vagina was kept up, so I just tidied my landing strip. I washed my body with my favorite coconut soap.

By the time I got out and dried my hair, I had 45 minutes, which would seem like enough time to some, but my lion's mane needs some work to not be frizzy. I have a mop of caramel-colored hair that's super curly. I apply a handful of products in and out of the shower. I diffused my hair with the dryer so it maintained its curl.

After some time I finally got it decent enough to worry about everything else. I applied a light layer of makeup. Nothing too flashy. Tinted moisturizer, eyeliner, mascara, and a mauve lip. I feel it goes well with my jade-green eyes.

I flung open my closet and stared. I hate picking out clothes. I pulled down two different dresses. One was black with a sheer sparkly overlay and the other was the run-of-the-mill little black dress. It was the easiest and still sexy.

I decided on the simple black dress and my emerald green kitten heels for a pop of color.

I didn't wear a bra with this dress. I usually don't need one. I only have a small B cup on my petite frame. I have a long torso and legs which helped me out in sports when I played in high school and college. I slipped on a pair of black lacey panties, the dress, and my shoes. My stomach flipped again as I grabbed a black leather jacket and my keys.

I finally found a parking space in a garage a block from the humongous building. I had never imagined I would be inside of the Ritz-Carlton for any reason.

I stepped into the modern-designed lobby. There were so many people in business suits and dresses. Everyone seemed so important. I began to get nervous and could not pay attention to people's faces to see if he was there.

"Sarah?" I heard my name behind me.

I turned to see Tom sauntering toward me with a large smile plastered on his face. He was taller than I remembered, which is nice. I'm 5'5" and like men taller than me. He was sporting a well-fitting navy suit and grey loafers.

"Yes. Tom?" I asked, still trying to pretend I had no idea who he was.

"You look lovely." His voice was soft but deep. He stuck out his hand. I looked at his hands. They were masculine and large, veiny with long fingers. They looked well manicured and I imagined them around my throat. I shivered internally. Maybe I'm too horny for my own good?

I've never given my date a handshake but here we are. However, it wasn't a handshake. He took my hand and put the back of it to his lips in a light kiss. I felt my face redden. I was unsure why this made me blush. It was very... gentlemanly.

"I believe they have a table ready for us," He took my hand again and led me to the entrance of the restaurant.

A waiter brought us to our table toward the back of the restaurant, it was quiet and the ambiance was romantic. As soon as we took our seats Tom ordered champagne for the table. It was some French name I had never heard of. It was pretty attractive hearing him say something in French, even if I didn't know what he was saying or if he pronounced it correctly.

"Sounds like a fancy bottle, " I chuckled as I clasped my hands in my lap and fumbled with my fingers.

"I took many years of French in college and am quite biased toward French wines, " He laughed. It was velvety and brightened his face.

I couldn't help but notice similarities between him and Jessica. She's a beautiful girl so I'm not surprised. She has her father's eyes and electric smile. I was hoping I could separate Jessica from him, especially if we end up fucking.

The waiter brought the champagne and poured our first glass. I ordered a salad, it was loaded and topped with salmon.

The champagne was strong and semi-sweet. He kept filling my glass and I appreciated that because after glass number 3 I didn't feel the slightest bit anxious.

We had a great conversation about our jobs and books we enjoy reading, and he spent at least 20 minutes explaining why Star Wars is a cinematic masterpiece for its time.

This man was just a big nerd- and I liked that because he's also a smooth talker, it was an attractive contrast. We dodged any conversation about families or people we may know. Jessica's face kept popping up into my mind every so often but I would chase it away the best I could.

We had long finished our food and were halfway through a second bottle of champagne and conversation about water conservation when he put his hand out on the table for me to take, which I did.

"I try to be open with my intentions-" he started as he cleared his throat. My stomach rolled nervously. I'm unsure why, at this point. I was extremely comfortable, more than tipsy, and very interested in him- "I have a room here if you'd like to go up? More than a room, one of their suites."

I took a long gulp of wine finishing my glass and then a long drink of water. I hope he didn't think I was going to say no. His smile dropped ever so slightly as I swallowed.

"I'd love to," I said finally. His face brightened again as he released my hand and stood up.

I followed suit and slightly wobbled on my feet as I stood. He chuckled and put his arm around my shoulder.

"You're not too drunk, are you? I wouldn't want you to be misconstrued or unable to consent, " His face looked worried.

I searched his icy blue eyes for a moment. He seemed genuine. There was also a hint of excitement in them that physically aroused me.

"Oh, I very much consent," It came out a little too eager which made me want to face-palm.

He chuckled again and squeezed my shoulder. We got into the elevator and he pressed 8. I felt jittery inside as we stepped off the and he stopped at his room. The doors to other rooms were not close together so I only could imagine how large this suite was.

He pushed open the door and the cool air hit me. The room was bigger than my apartment. A king bed, a large couch, a kitchenette, a huge dresser, a massive bathroom that had a shower and a separate jacuzzi tub. There was so much floor space. There were a few lamps throughout the room which were switched on continuing the ambient lighting.

"Make yourself at home, " He laughed. "I'll be right back," He went into the bathroom and closed the door. I was unsure what to do. Should I surprise him by being undressed? I enjoy the other person undressing me so I decided against that.

I took a seat on the couch and tried to look calm. I took a mint out of my clutch and swirled it around in my mouth. Soon enough he appeared from the bathroom. I bit into the mint and chewed it quickly. Mints help everything before sex.

He had removed his blazer and was wearing a grey button-up. His shoes were also removed. I noticed his feet were big...wonder if the saying is true.

He put his hand on my bare shoulder after he turned toward me. "You're very beautiful, Sarah." He smiled. "I enjoyed talking to you as well. Beautiful and intelligent." He rubbed his thumb over my collarbone which gave me goosebumps.

He moved his hands to the sides of my face and pulled his face to mine. His lips were plump and his breath tasted minty as well. His tongue swept my lips and I parted my mouth for him as he pushed harder into me. His hands went to my hair and then began to slide down my back. I wrapped my arms around his neck and my nerves calmed. I just became more aroused and felt a tingle in my pussy and wetness surface around my lips.

His kissing became more aggressive and one hand moved to my thigh. I moaned into his mouth on accident. My eagerness was palatable. He pulled back inches from my lips as he laughed. I blushed slightly and looked away.

His hand continued up my thigh and his lips traveled to my neck and he nipped across my collarbone causing more moans to escape my throat. His hand was squeezing my thigh and he was close to my ass. His other hand was tangled in my hair as he continued to kiss and suck across my neck.

He pulled away again ever so slightly, "Sarah, tell me what you like," He whispered. I looked at his eyes which had changed to a hint of deviance.

I wasn't sure what to say, I wanted anything at this point. I breathed heavily as his fingers crept to my panties.

"I...like it pretty rough. You can bring out my daddy issues." I giggled.

"There's something about girls with daddy issues, " He laughed as he put his hand over my mound causing me to catch my breath. His fingers trailed around my bikini line and he teased me over my panties as his mouth was inches away from my face. He wasn't kissing me anymore but intently looking at my face with a devious smile.

I was so turned on I could scream. He abruptly pulled his hand from under my dress and I gasped. He chuckled as he stood up. He took my hands and brought me to my feet. He brought his hands to my shoulders and slipped the spaghetti straps off my shoulders. He pulled my dress down halfway uncovering my tits.

"Mmm." He breathed as he moved his lips and hands to my boobs. He began to knead and pinch at them causing my knees to buckle slightly. He attended to each one with his mouth and fingers. My nipples puffed with each small tug and they ached for more.

I was breathing heavily as he pushed his body against me he was now kissing me again and his hands moved down my hips and onto my thighs. I caressed his chest and fumbled to unbutton his shirt. It fell open to show his toned, lean, body. I leaned forward and kissed his chest. I ran my hands down his sides and over his prominent erection. I could feel his girth and his cock dance under my touch. I squeezed his rock-hard member. He slowed his movements as I grabbed his belt.

He held out his hands stopping me. I gave him a puzzled look but his facial expression didn't change as he pulled off his belt in a swift motion that was slightly intimidating. He gave a small growl and grabbed my arms. I squeaked at his forcefulness. He quickly wrapped the belt around my wrists and pulled the leather strap tightening my hands together.

"Oh, " I gasped. This started a fire in my stomach that stretched to my wet sex. I was quivering with anticipation. My hands were now bound in front of me. He pushed me gently to my knees and began undoing his trousers.

It was slightly intimidating not being able to use my hands for help on his cock if needed but it presented as a fun challenge. I had yet to see what he was packing. He slid down his boxers and trousers and it was bigger than I had felt over his pants. His erection sprang forward almost hitting me in the face. His bulbous head glistened with precum. I wasted no time taking him into my mouth. I trailed my tongue around his tip and flicked around his glans. I opened my mouth wider to take more of him in. He quickly hit the back of my throat causing me to gag. He advanced further forcing me to open my throat. My eyes began to water profusely. I focused on my rhythm and my tongue. He grabbed the back of my head and moaned.

"It feels so good, Sarah." He cooed, "What a good girl."

How did he know I liked to be praised? Does it come along with the daddy issues? I moaned and it vibrated his hard cock. I began increasing my speed. My gagging was embarrassing but it should be flattering for him. I was able to keep going for a few minutes before my jaw began to lock up and sent shooting pain through my neck. I kept my cool but my pace slowed.

He moved back and pulled his dick out of my mouth with a "pop". He wrapped his hand in my hair and gently pulled me to my feet. I yelped and smiled to let him know I liked that.

He smirked and pushed me back into the couch. I landed against the soft cushions and he moved over top of me. He grabbed my face between his thumb and index finger. He kissed me passionately and continued the kiss as he pulled my dress down and it slipped to the floor. His strong hands gripped my taut hips as he moved between my legs. He kissed up and down my thighs making me moan slightly. He moved the crotch of my panties over and ran his tongue over the length of my slit parting my glistening lips. He quickly found my clit and gave a few short flicks making me squirm. "Oh," I breathed.

He suddenly stopped and pulled back, I again looked at him in confusion. "What do you want me to do?" He asked with a smirk.

My head was filled with lust which made me erratic. "I want you to eat my pretty pussy, " I whispered as I beckoned him with my tied hands.

"Yeah? You do have a pretty pussy." He purred. "Say please."

I bucked my hips in defiance. I liked to play a little too. "Please, sir," I said, my tone a whine.

"Mhmmm, " He slapped the outer part of my ass/hip causing me to yelp. I giggled as he dove his face back between my legs and easily found my clit. His tongue worked diligently around my folds and he suckled on my nub. My hips bucked and swayed but he pulled me deep into his mouth and held onto my ass cheeks pulling me up off of the couch. He slid off my panties and threw them behind him.

I felt an orgasm swelling inside my stomach burning hot within my insides. It rose to a crescendo and then burst.

"OH FUCK!" I wailed as he sucked harder. I felt my insides contracting as my breath became more ragged. My hips bucked as I rode out the pleasure.

He pulled away and chuckled, his mouth and chin wet with my juice. "Mmm, now to the other good part, " His cock was so hard and fully at attention as he pulled my legs back opening up my pussy.

He shoved his cock into me forcefully. I let out a loud moan. "Yes, fuck me." I sighed.

"I bet you love this big dick filling you up." He grinned but a look of concentration and primal lust quickly fell back over his face.

"Yes, sir I love your big cock please fuck me harder, " I was becoming so intoxicated with the endorphins. I wanted him to do whatever he wanted to me.

He grabbed the belt and pulled my arms up over my head. He was pushing into me so my legs stayed up in the air as well.

"Call me Daddy," He grunted as his thrusts became harder. The couch began moving beneath us.

I was a bit caught off guard by this request. Jessica's face popped back into my mind. A very unfortunate time as her daddy was balls deep inside of me. He was playing off my kinks though that were somehow quite easy to determine. I quickly forgot all about Jessica as he began thrusting harder still. He pulled more aggressively at the belt tightening around my wrists. He moved his free hand to my throat and wrapped his long fingers around me. He applied a good amount of pressure.

"Thank you, Daddy," I choked, stars dancing behind my eyes.

"Stand up." He pulled out of me as I stumbled to get up, I needed to get him back inside of me.

He spun me around and pushed my back down so I was bent at the waist and my hands grasped the back of the couch. He quickly pushed back into me and grabbed my hair. My head pulled back and I saw his gaze on me as he pounded my quivering cunt.

"You have such a tight little pussy." He said as he slapped my ass cheek hard. "I want you to cum for me, " He said almost demanding.

"Yes, Daddy!" I wailed as I focused on the sound of our bodies slapping together, his eyes locked on mine, and the insatiable feeling of a full pussy being hit in just the right spot--amazing. I enjoyed dirty talk and needed more to be pushed over the edge into another orgasm, "Keep talking to me." I urged through gritted teeth.

"Do you like being told how much of a slut you are? Fucking someone you don't even know in a hotel room. Someone almost 20 years older than you?" He drove so hard that the couch moved another few inches. I felt like he was hitting my cervix. I tried to put my ass more into the air for a different alignment. It didn't go unnoticed.

"Oh, do you need a different position? Can't take it?" I could hear his smirk. He pulled me up and spun me around to face him. He kissed me sloppily on my lips before picking me up.

I put my arms over his head, I wanted to be untied but I wasn't going to ask. I wrapped my legs around him and he quickly impaled me with his upright cock.