Wine and a Casual Fling

It only took a few glasses of wine and 40 minutes of TV for the kissing to begin. Jess didn't use a lot of tongue, but couldn't keep her lips away from mine. As the intensity picked up I managed to slip down to her neck. She moaned as I sunk my lips into her. I was throbbing as my hands explored her slender body. Her top slid off easily, it was her bra I struggled clumsily with. Impatiently pulling it down in the front while I kissed her chest.

Her hands left the back of my head for just a second while she unhooked the clasp, granting me access to her beautiful 23 year old breasts. I teased and sucked while admiring her incredible body. She was easily the hottest girl I had been with. I could already tell she wasn't very sexually experienced, so I took the lead hoping to drive her more wild then she ever had been before.

Taking a break from her nipples for a moment I unbuttoned my shirt. Without hesitation Jess started teasing my cock through my jeans. I throbbed harder as she rubbed her hand against the fabric while enjoying the view of her bare breasts and flat stomach, leading down to her black leggings. I leaned back down to kiss her lips. We embraced passionately despite having met just a few hours earlier.

I kissed my way back down before reaching her leggings, planting my last kiss just above where the fabric began. I reached my fingers underneath the black fabric gently, pulling slowly to make sure if she was wearing panties they stayed on. As I pulled them down I revealed a weathered black thong and beautiful thin, yet toned legs. After throwing her leggings to the side I kissed the soft skin of her amazing thighs. I could feel her tense up as I started getting closer to her pussy.

Just a few kisses over the fabric before I was slipping her panties down leaving her completely naked. She had a thin landing strip right above her incredible lips. Her pussy looked wonderful. So tight and wet. It was clear not to many guys had made their way inside her.

Jess moaned when my lips met hers. She tasted wonderful, my tongue circled her lips and clit while my fingers slowly worked their way inside. I could still feel she was tense even though she continued to moan while her juices started dripping more and more from those sweet lips.

"I want to feel you" she murmured.

I gave her pussy one more kiss before emerging from in between her legs. She quickly sat up and started to undo my jeans. I helped her pull them off and let her slide down my boxers. She stroked my cock. The first few strokes felt good, and then her inexperience began to show through. As the discomfort began I stopped her.

"I want to fuck you" I said as I started leaning her back on the bed.

"Do you have a condom?"

I shook my head no and Jess jumped up to go and grab one. I got a beautiful glimpse of her ass while she walked out. She returned a few seconds later to me stroking my cock while kneeling on her bed. I put the condom on while she laid on her back and spread her legs. I positioned myself over her while we kissed and I teased her with the tip of my cock.

As I pushed inside I couldn't believe how tight she was. Her lips squeezed my dick as I slowly pushed further inside her. She moaned loud as the last few inches of my cock slipped inside. I fucked her slow, with long deep strokes for a few minutes before picking up speed. After a minute of fucking her hard she tapped out.

"I need a minute" she moaned.

"Whats wrong?" I asked.

"I've never had a cock this big before."

As the words left her lips I throbbed even harder. At 7 inches I certainly didn't have a small dick, but I had never been anyone's biggest either. I couldn't wait to get back inside her to stretch her sweet cunt a little further.

I laid on my back and when she recovered she climbed on top of me. My mouth on her nipples as she eased my throbbing dick back inside of her. I hated wearing the condom, but at the same time I probably would have exploded when she was on her back for me instead of still being in the game for round one.

She bounced up and down while my hands gripped her ass. Her cheeks felt amazing in my hands, I could resist giving them a few hard smacks. She squealed as my hand hit her ass. After a few more minutes of riding I wanted to be back in control. I pulled her close to me and we kissed.

"I want to fuck you from behind" I whispered in her ear.

Obeying my request she climbed off and got on her knees next to me. When I got behind her I spread her cheeks wide open, what a sight it was. Such a tight, beautiful pussy and asshole. I could feel her tense up again as I had her cheeks spread like that.

With her cheeks spread I pushed my cock back in slowly. I looked so good sliding into her. She moaned as I pushed even deeper than I had so far. I didn't waste anytime building up speed. My cock rammed deep inside Jess. The sound of the bed hitting the wall and my balls smacking against her were almost as loud as her moans. Jess came like she never had before. Her lips squeezed my cock as her body tensed and her juices flowed down her leg.

It wasn't long after Jess's orgasm began to subside that mine took hold of me. I couldn't take the grasp of her lips any longer as my cock began to twitch inside her, shooting out my warm cum. I didn't stop fucking her until the last drop of cum fired out of me.

I collapsed over her for a few moments to collect myself before pulling out of her. We both cleaned up before grabbing more wine and returning to her bed.

A few more drinks and another TV episode was all it took before we started making out again. This time conveniently already naked. The kissing was relatively short lived as I could tell Jess was ready to get fucked again as she was dripping down my fingers.

She jumped on top of me and grabbed my cock as we continued to kiss.

"Should you get a condom?" I asked, eager to be back inside her.

With her hand lightly stroking my cock she took a moment to responded.

"Should I?" she asked puzzled.

"Its up to you, I know you're not on the pill."

"Can you fuck me just a little bit without one? I've never felt that before."

Without saying a word I pulled Jess onto the tip of my cock. Easing into her slowly. She moaned as I slid in inch by inch, throbbing inside her tight pussy. She rode me slow, God she felt so much tighter without a condom on. I couldn't believe how good she felt.

She felt it too, it only took her a few minutes before she came for me. When she collapsed onto me I slid my hands from her hips up to her shoulders, re-positioning my legs so I could take control. Before her first orgasm could subside I was fucking her into a second one. It only took about another minute for her to cum again. Her body tensed and I could feel her dripping down my cock.

It was her second orgasm that triggered it. Her sweet lips tightening harder around my cock set me over the edge. Not thinking I continued thrusting into her. My lips sucked her neck when my cock fired its first rope inside her. Jess yelled as my hot cum shot deep into her pussy. She moaned each time I released another blast of cum between her sweet lips. I grabbed her as and pushed her down on my cock while I fired the last rope.

We kissed as my cum leaked out of her cunt.

"Fuck" I whispered. "I shouldn't have done that."

"It felt so good though" Jess moaned. "There's always plan b."

The next morning we got her the pill which luckily worked successfully. Our fling lasted another month or so and mainly consisted of nights filled with few glasses of wine before stripping each other naked and fucking in Jess's bed.

Positions remained the same as they were the first night, we had good, but overall non-adventurous sex. There was however one night a few weeks later she let me take things furthest she ever would.

We had just finished our first round of the evening. It was a shorter round than usual as I was particularly horny. I fucked her harder than usual before exploding inside her. After cleaning up we decided it was time for more wine. I slipped into my boxers while Jess put on only a T-shirt which was long enough to reach down to her thighs.

I followed her into the kitchen as she turned the lights on before standing in front of the counter to pour more wine. While she poured I ran my hands up her sides and began kissing her neck. She put the bottle down and I could hear her moan slightly. I was quickly getting aroused as I kissed her and explored her body with my hands. Pressing up against her ass with my cock.

I pulled her shirt up so my cock could rub against her bare ass. As I got harder I thrust my cock between her cheeks, still kissing her neck. While dry humping her ass crack felt great for me I knew it did nothing for her. Eager to please I knelt down and began to kiss the back of her thighs. Working my way up, kissing and biting each side of her ass before spreading her wider and sinking my tongue into her pussy.

The second my tongue hit she pushed back on my face, letting me get further inside her. Fucking her with my tongue while she started rubbing her clit. What I did next she didn't expect. My tongue slipped out from between her lips, sliding slowly up between her cheeks as I reached her tight asshole. She tensed up, but she was already so close from rubbing her clit she couldn't pull away.

As my tongue traced around her asshole she screamed as she came. I throbbed as it happened, I had wanted to do this since the first time I fucked her in doggie. It was short lived but I was so fucking turned on. I started stroking my cock as I got up. Surprisingly enough she turned her head enough to kiss me while I continued stroking. When I leaned forward she kissed my neck hard as I started to cum. My cock sprayed all over her ass. Streams of cum dripping down to the kitchen floor.