Our First Date

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Shy guy gets seduced by old woman.
2.6k words
4.27
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Kat and I met way back in 2012. I was 24 and she was 28.

It was online dating that connected us. We had texted for about a week before we setup our first date. She lived about an hour away, and I would come pick her up.

I was nervous, having only been with 4 women at that point. But I must have said something right to get this chance.

I had put on a button up shirt, and my best fitting jeans over a pair of cowboy boots, that I wore instead of dress shoes. I would have fit in at any hill billy wedding.

The hour long drive in my Dad's truck was not helpful to my nerves. But I told myself to be confident and have fun. Nothing to lose.

I finally pulled up to Kat's apartment and texted her I had arrived. A few moments later the door opened and she came out to meet me.

She was stunning. Way sexier than her profile pictures. She was wearing a low cut black top, with a short green mini skirt. To this day Kat reminds me of the stunned look I had on my face.

At 5'8" with long black hair, she was breath taking. 34DD breasts, itty bitty waist, and booty for days. Sir Mix-A-Lot would be proud.

She walked up to me with a smile, and reached out her hand to greet me.

"Hi Jack, nice to meet you."

"Wow, you are stunning Kat. It's a pleasure to meet you." I greeted her.

I lead her to the passenger door. "Would you like to grab dinner somewhere?" As I opened the door for her.

"Sounds great." She said climbing into the truck. Her skirt riding up her thigh, as she stepped up onto the running board.

We proceeded to drive around town, trying to figure out where to go. Little did we know how much time we would spend doing this very act over the next few years.

We settled on a dine-in chain restaurant. Got a seat out on the patio, and got to know one another. She could tell I was nervous, and she led most of the conversation, which settled me down.

She inquired about how much I dated. It must have been apparent that it wasn't much. I was 6' and 170 lbs with a slim build. Thick blonde hair, blue eyes and baby faced, looking 6 years younger than I was.

After we finished our meals and got the cheque I asked if she wanted to go somewhere else before we called it a day.

"We can go back to my place and have a drink if you like." Kat suggested.

I was startled. 'That's code for sex' I told myself. Certainly she is being polite. No one has shown that kind of interest in me.

"Sure." I said slightly too eagerly. "That sounds fun."

As we drove back to her place, I noticed she wasn't watching the road. She was just looking at me, and smiling. Her legs were crossed, and I could see her leg right up to her ass. The seat belt underneath her right breast, amplifying just how large and perky they were. Damn she was sexy.

I couldn't believe this sexy ass hottie genuinely liked me. I could feel my heart beat faster. This was exciting.

Once we got back to her place she waited in her seat for me to come around and open her door. She held out her hand for me to take. She suddenly needed assistance to evacuate the vehicle. I was only too happy to help.

As she got down she made sure to step square in front of me. Kept her head level and looking up at me with a mischievous grin. She was having fun.

Only for a moment though, just long enough for the thought of kissing her to come to mind. And she was gone. Leading me to her basement apartment. I couldn't help but stare at the that green skirt, and what was just out of sight.

She opened the door and called, "please come in," over her shoulder.

"This is my place" she said as we made our way down the stairs.

"It's nice" I said giving the room a scan.

"Been here long?"I asked.

I caught the glimpse of her roll her eyes and smirk. "No, just a couple months." She moved the subject forward. "Can I offer you a drink?" she said walking to the kitchen

I obliged, and we made cocktails.

"You do look like a child." She said, passing me a glass. "You make me feel like a predator, luring you back to my lair."

"Is that good, or bad?" I asked, unsure of myself.

"Well I'm having fun." She said, taking a drink. "Come on, let's watch some T.V."

She led us back to the living room and she sat down on the couch. I didn't want to be presumptuous so I sat down leaving space between us.

I believe she put on Big Bang Theory, or something along these lines. We talked briefly about what shows and movies we watched. But as we sat there, I could feel the tension. She was going to make me make the first move.

I gathered up my stones and moved over beside her, and put my arm around her. She turned her head to face me. A small grin on those full inviting lips. I leaned in and she met me halfway.

We kissed with closed mouths at first, but it quickly turned to a slobbery make out session. I had grabbed her by the neck, but was sliding my hand down. Kat had already moved her hand under my shirt, feeling my then much flatter stomach, effortlessly undoing the buttons on my shirt.

She pulled away to take a breath. But quickly pushed my shoulders into the couch, and straddled me. Sitting on my lap. She took my face with both hands, and planted her tongue in my mouth. I ran my hands down her waist, to her big beautiful ass.

Because of her positioning, her ass was even more pronounced than before. I easily slid my hands under that green skirt, and took two glorious handfuls of her butt cheeks.

She eventually pulled back again. Her crotch putting pressure on my now very erect dick. She undid the rest of my shirt and pulled it off of me. I slid her shirt over her head. She leaned in and started kissing me again, while I fumbled with her bra. Enough for her to give a chuckle.

"Squeeze and slide." She instructed.

Success! I freed her from booby jail.

As I drew the bra off her, I got my first glimpse of her beautiful tits. They were large, firm and all natural. They were heavy, as I took them in my hands. Squeezing, and massaging them. I leaned forward to take her left nipple in my mouth. I sucked, and drew circles with my tongue.

Kat had slid her hands between our legs and could feel my raging hard on through my jeans. "My my, someone is ready to go."

She said seductively.

"Holy fuck, you are hot." I said, leaning back into the couch.

She started to grind against me, and said "Yeah? You like older women?" With long, purposeful pumps of her hips.

She didn't give me a chance to answer before she buried my face in her tits again. Twisting her shoulders, so her jiggly breasts were slapping my cheeks. God damn, I was having fun.

She was making her way down. Humping me, but her tits were now by my belly button. She was smiling, and look pleased with herself. Running her hands down my body, until she was kneeling between my legs, and unzipping my pants.

The head of my dick pressed against my underwear, as my jeans opened up. Kat grabbed my waistband and pulled my underwear down exposing my hard on.

An amused look swept over her face. "Well this is a pleasant surprise." She said inspecting my 7" circumcised cock. Which was trying its best to grow just a little bit more.

"It's so pretty." She said giving it a little kiss on the head. My dick flexed at getting attention, and struck her on the chin. She shot me an "Oh yeah?" glare.

Like accepting a challenge, she began teasing me. Giving me tiny licks, or blowing on it. Seeing how close she could get, before making it jump.

After satisfying her curiosity, she ran her tongue up the bottom of my shaft, and closed her lips around the head. Her eyes shooting back up at me.

She was licking the base of my cock, with her lips around my head. Then started to bob her head up and down. Taking most of me in her mouth each time.

I shoved my back into the couch, and my pelvis up into this beautiful face. My hands grasped her head, and held her hair back.

She put her hand around the base of my cock, to hold me still, and continued blowing me. I had rolled my head back, enjoying the sensations, but didn't want to miss the sight of what was going on between my legs.

When she had had enough, she gave it another tiny kiss, and rested her breasts on my thighs, looking up at me.

"Holy shit." I said slightly out of breath. "That was incredible."

"Thank you" She said pleasantly. "You've got a nice dick."

I reached down and pulled her face up to meet mine. Kissing again, our tongues playing with each other. She softly bit my lower lip as she pulled away.

"Would you like to join me in the bedroom?" She asked.

"Definitely" I said, as we both got up and made out way to the next room.

"I never do this on a first date." She said, pulling me by the hand. "But you're so cute."

I wanted to be mad about getting called cute, but fuck. I just got my dick sucked.

"Me either." I said. Not that I had ever got the opportunity.

She turned and sat on the edge of the bed, and held her feet up. I took the hint, and slid her pretty green skirt and thong off. She had a sexy little landing strip. I put my hands on her knees and pushed her legs apart. Moving in so my body was against her, I asked. "Can I please taste you?"

"Yes, please." She encouraged me.

I took another slobbery kiss. Before making my trek down her sexy body. Kissing and sucking as much of it as I could, before nestling my head between her legs. A little kiss on either thigh, before I ran my tongue up the length of her labia.

My tongue making its way into her warm wet pussy. Oh she tasted good. Just a tiny hint of pennies. I was licking her like I was trying to empty a pudding cup. Moving my nose around on her clit.

Kat had been supporting herself with her arms extended behind her. But with an, "oh shit." She fell back and grabbed me by the hair. I took this reaction as approval, and got comfortable in my position.

I made my way up to her clit, probing my tongue around until I found the little bud of pleasure. As soon as I pressed my tongue on it, she pulled my hair, and her head flew back.

I continued licking, and sucking. She was rolling her hips, and grinding my face, as she held my head in place. She was so hot. So confident, and so direct. She knew what she wanted, and was directing me with her body.

My jaw was getting a workout. I hadn't had the opportunity to practice in a while. I slid my middle finger in her. Fucking her, and bending my finger in a "come here" motion, as I pulled it out. Another "Oh fuck," of approval.

I picked up the pace and intensity. She was shoving her pelvis into me aggressively now. Trying to suffocate me. I was so hard, and dripping with precum.

Suddenly she squeezed her thighs together, and her entire body clenched as she grabbed the sheets in her fists.

"Oh Goodddd!" She howled. I kept my finger firmly in her, and just sucked, as she continued to convulse. Until with one last shaky contraction, she pulled my head up and said "Fuck me."

As I retrieved a condom, and was opening the package. She had moved up onto the bed and was touching herself.

"Where did you learn to do that." She asked in an impressed tone.

"The internet." I said, matter of factly, putting on the condom.

"Thank you internet." she said as I took position over top of her. She gave my dick a squeeze, and felt the condom. Then guided me into her very wet pussy.

I was somewhat grateful for the condom. She was so tight, and I was already so worked up, that the condom was dulling my senses just enough to last longer.

I propped myself up on my arms and looked down at Kat as I thrusted inside her, over and over. She was rubbing her clit, moaning, and groaning. Matching my speed as she moved her hips.

"Fuck Me! Harder!" She pleaded.

I was stuffing my cock in her, as hard, and deep as I could. Moving my hands to her hips, and my body now on hers.

"FF UU CC KK!" She stammered between thrusts.

Until I felt her vag tighten up, squeezing my dick. She arched her back and let out a scream as she came again.

My dick was even more engorged, as I felt myself go over the point of no return. All my muscles clenched, as I slammed every inch of my cock into her pussy. I could feel the cum travel up to my cock, and erupted deep inside her. Filling my condom with cum.

I laid on top of her as we continued to have after shocks. Feeling her pussy throb, as I'm sure she could feel me do the same.

Finally I rolled off her, and on to the bed beside her. We laid there for a while. Enjoying the afterglow, and catching our breaths.

"Wow. You were incredible." She said panting.

"Oh my god. No. You are." I rebuffed.

"I need a smoke." She said getting up.

I didn't, but got up with her anyway. I disposed of the rather full rubber. She put on a bathrobe and I got half dressed. We went to the kitchen and she lit a cigarette under the fume hood.

She inquired again about my sexual history and seemed shocked it was so few. She was by far the best I had been with.

It was getting late and I needed to get home for work the next day. She was let down by me insisting I couldn't stay.

"I will text when I get home, and call you tomorrow." I said reassuring her.

"You're not going to call me" She said defiantly.

This was silly. "Of course I'm going to call you." I said. Why wouldn't I call her? I want to do this again.

She gave me an, "uh huh," and rolled her eyes.

I stayed for another drink, before getting dressed and ready to go.

I gave her a kiss and a hug, and we said our goodbyes.

"I will call you." I assured her, making my way to the truck.

She waited for me to roll out of sight before turning back.

I did text her that night. And called her the following day to set up our next date.

She isn't sick of me yet.

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EastCoaster1EastCoaster1about 2 months ago

4 stars for this enjoyable tale of 'first time' together.

Nicely done.

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