First Time: a Night to Remember

It started out as a really boring day for me. There was nothing to do, so I headed to the local Wal-Mart to walk around. That really didn't help things for me as I was still bored as I walked out of the store.

I was half way to my car when I heard it. "Josh, is that you?", asked the voice of a woman.

I turned around to see her. It was Jane, a friend of my Mom's form years back. I had known her and her family for years. For being in her very early 40's, she still looked damn good. She was tall at a little over 6 feet even with medium length blonde hair. She was nice and skinny with a great tan. To tell the truth, I had always had somewhat of a crush on her.

I stared at her for a few seconds before answering her. She was really hot. She had a nice pink tank-top and some really tight jean shorts, exposing her long sexy legs and beautiful ass. After staring at her perfect body for a few seconds, I responded to her, "Jane? How are you? I haven't seen you in a while."

She smiled and said, "I'm okay. I haven't seen you in a while either. Listen, my girlfriend was supposed to pick me up and bring me back to my place, but she just called my cell phone and said she's having car trouble. Do you think you could give me a ride?"

I was planning on going right home and just relaxing, but she was impossible to turn down. She looked at me with little puppy-dog eyes and said, "Please." She looked so sexy as she said it.

Being the nice guy that I was I said, "Ok, sure come on". She just smiled at me as she caught up to me and started walking along with me to my car. I let her get a little bit ahead of me as I checked her out from behind. She may have been 40 years old, but she had a body like a 20-year old.

As we got to the car, I went to the driver side to open my door. Suddenly, I heard a clearing of the throat and turned to Jane. She looked at me and said, "Are you forgetting something?"

I smiled as I walked over to the passenger's side of the car and opened the door. She looked at me and stared into my eyes. She smiled so sexily as she said, "Thank you very much." She then winked at me and licked her lips ever so softly as she bent down and got in the car. If I didn't know any better, I'd think she was flirting with me.

I got in the car and after a couple of seconds, we were out of the Wal-Mart parking lot and on the way to Jane's house. I sat in the car, driving in silence. I really didn't know what to say or how to react to the way Jane looked at me. Was she coming on to me? Was I overreacting? I wasn't sure.

As I continued to drive, I kept one eye on the road and the other on Jane's sexy, tan legs. They looked so gorgeous. It took everything I had to not take the eye on the road and put it on her legs. Jane suddenly broke my trance. "Umm...So Josh, are you seeing anyone these days?"

"No, not now.", I said, sounding a little rattled. I wasn't sure if Jane had noticed me staring at her legs or not. I just tried to down-play the whole thing.

"Oh, so you must be pretty lonely some nights. Not having a woman to satisfy your wants and needs. I bet you get so horny every night, wishing you had someone to make you cum whenever you wanted it. Am I right?"

I was totally shocked. I was now totally sure that she was coming on to me. If I played my cards right, I could be a very happy man at the end of the night. I though carefully on how to respond, not knowing what to say without sounding like a complete dumbass.

What I ended up saying wasn't exactly the smoothest thing however. "Umm..I...Uhh."

I looked at Jane quickly then back on the road. I started to tense up as Jane slid a little closer and put her hand on my knee. She leaned in and blew gently in my ear. My dick instantly started to stir in my pants.

Jane leaned in even closer and whipered in my ear, "Listen, I saw you looking at me. I know you'd like to have a little fun wiht me, wouldn't you?"

I swallowed hard and nervously replied, "Yes, yes I would."

Jane moaned very softly. So softly that I barely heard it. She whispered in my ear again. "I knew you did. And guess what? You can have all the fun with me that you want. I mean ALL THE FUN you want. Tell me something: Have you ever had sex before?"

My face got a little red. I was somewhat embarrassed as I replied, "No."

"Mmmm...Well, I would be very honored to be your first. Have you ever had your cock sucked?"

My dick got even harder in my jeans as I struggled to keep my car on the road. I cleared my throat and said, "No I havent'."

Jane moaned again and said, "It would be an honor for me to suck your cock. Would you like that?"

I started getting butterflys in my stomach and my dick started twitching like crazy. "Yes, I would", I said, trying my hardest to keep my cool.

Jane chuckled a little bit as she moved away from me and sat back in her seat. I instantly felt my dick start to go limp. I was worried that she was just teasing me. That she made me look like a fool. Her next words proved me wrong. "Mmmmm, I'm so horny. I haven't been fucked in weeks. My pussy is aching. Is there anything you want to do about that? Don't be shy, sweetie.", she said sounding very sexy and caring and at the same time.

The way she said this and the way she sounded calmed me down greatly. I started feeling a little bold as I answered her question. "Well, I'd like to eat your pussy over and over and then fuck the hell out of it. What do you think of that?"

The instant I said that, I felt totally stupid. I had those thoughts about several women, but I always kept them in my head. I never said them out loud to a woman before. I wasn't sure how she'd react. I sounded alot bolder than I actually was. I was scared to death. I wasn't that bold. I was nervous as hell, but I was more than ready to "have some fun" with Jane.

"Oh yea, that's what I wanted to hear. I'm going to make your first time one that you'll never forget. I promise you that, Joshie.", she said as she started petting my knee and my dick started to grow yet again.

About this time, Jane's house came into my vision. I slowed the car down and parked into the driveway. I shut the car off and stepped outside as Jane did the same. We both walked up to her front door. She topped to open the door, then stood in the doorway, blocking me from getting in. She grabbed me, pulled me in, and planted a soft kiss on my lips. She slipped her tongue gently in my mouth and ran it over my tongue and teeth. My dick grew even more in my pants as I started to run my tongue along hers and her lips. Her mouth tasted very good and my dick was feeling all sorts of things.

Jane then drew her mouth from mine and said, "There will be plenty of time for that later. Now, I want you to take a shower and get that cock all nice and fresh for me. Then, I'll take a shower and get this pussy of mine all nice and fresh for you. I want us to have the best of eachother. What do you say?"

It took me all of one second to answer, "Definitely." She pointed the way as I headed into the bathroom, took off my clothes, and jumped into the shower.

I shouldn't neglect to say that Jane was known as the "town slut". She'd been with a lot of men. She seemed to be proud of that fact. But, I also shouldn't neglect to say that that fact didn't bother me one bit.

While I was in the whoer, my head was spinning. I was sure that this was a dream and I'd be waking up shortly. I mean, I wasn't really going to fuck this hot woman that I'd like for years, was I? She wasn't really coming on to me, was she?

As I finished washing myself, including my rock hard dick. I heard a noise. I opened the sohwer curtain to see Jane walking in the bathroom with a devilish smile on her face. She walked right up to me and ran her hand across my cheek. She then leaned forward into the shower a little bit and turned the water off. As she leaned back out, Jane stopped and wrapped her hand around my hard dick and gave it a quick pull. It took everything I had not to cum right there. Her hand, her touch, was so soft and gentle. It made me want her even more.

I guess Jane could sense how I was feeling because she leanded in and whispered into my ear, "Not yet, big boy. Why don't you come on out and dry off. Wait in my room while I get cleaned up. Then, when I'm done, I'm gonna fuck you like crazy!"

Her dirty talk turned me on even further. I did as I was told and went to pen the bathroom door. Suddenly, I was stopped by Jane's voice. "Josh, here take these", she said as she tossed me her little pink panties. As I caught them, Jane spoke agian, "Here's a little present from me to you. Now, go and enjoy these while I take a quick shower. Then, I'll be out before you know it and we'll have a great time."

I opened the door to Jane's room and saw a nice, clean room. The main part of the room was her king-sized bed. I jumped up on it and slid up on one of the pillows, laid back and relaxes. I took the panties that Jane gave me and brought them up directly to my nose. I inhaled a large scent of pussy and instantly my dick started aching. I wanted that pussy so bad I could taste it. It smelt so sweet. I then took her panties and shoved them directly in my face. The aroma of her pussy drove me wild. As I pressed her panties to my face, I felt something strange. Something wet. It hit me instantly: Jane was wet. She was horny! For me!

That thought drove me wild as my dick grew even larger. It was twitching all over. I tried to calm myself down. I kept telling myself to relax and don't cum right away like an idiot. Take it all in and enoy the night. This was the chance of a lifetime, grab hold of it. I was definitely prepared to do just that.

For the next couple of minutes, I layed back on the bed and just relaxed myself. My dick started to go down a little bit and I was feeling more in control of the situation. That feeling quickly went away in a matter of seconds.

Suddenly, the bedroom door opened and in walked Jane. She took my breath away as she stood directly in front of me, totally naked. My dick instantly sprung back to life and grew at record pace. Jane had a huge smile on her face as she came towards me and kneeled down on the bed.

She leaned into me and gave me a soft kiss on the lips, then took her tongue and ran it over my lips. I took my tongue and met hers with several strokes. Her tongue felt so good and I couldn't wait to feel it on other parts of my body. She then moved away from my face and moved over to my dick. She grabbed it in her hand and stroked it a couple of times. My eyes rolled back in my head at the feel of her touch.

Jane smiled at me and said, "Do you know how long it's been since I've had a hard cock in my mouth? Mmmm."

I laid back and moaned softly. I started to buck my hips up and down, wanting Jane to stroke my dick faster.

She must have senses what I wanted because almost instantly, she stroked my dick up and down very fast in her right hand. While she did that, she took her middle and index fingers on her left hand and rubbed underneath my balls.

The sensation was incredible. I started breathing heavy. I knew I was going to cum. I was going to screw the whole thing up.

Suddenly, Jane took her hand off my dick. She looked up at me and said, "Relax, Joshie. Just lay back and enjoy this. If you cum now, don't worry about it. I don't mind taking all the cum you got tonight."

Her words of assurance seemed to calm me down greatly. I wasn't that worried about cumming now. But, was determined not to cum until the last possible second. I wasn't going to blow my load several times. I only wanted to do it once. I wanted to take everything Jane had to offer and then shoot my cum all over her.

Jane looked back up at me and asked, "Are you ready for this?" I nodded, assuring her that I was more than ready. "Mmmm, this the best part", Jane purred.

My dick grew another inch as Jane lowered her open mouth closer to my dick. Her hot breath on my dick felt magnificient. But, not as good as it was going to feel in a couple of seconds.

Jane looked directly into my eyes and winked at me. God, that was so sexy! I wanted to fuck her so bad at that moment, but I more than happy to settle for what she did next. She stuck her tongue out and flicked it gently back-and-forth over my piss-hole. It felt incredible!

Jane kept licking over my hole several times. I moaned softly and it was very hard not to cum. The tip of my dick was itchign due to Jane's soft licks. I yearned to stop the itch, but trused that Jane would take care of it soon enough.

And, take care of it she did. She opened her mouth wide and brought it down the entire 6 1/2 inches of my rock-hard cock. Then, she wrapped her lips around it and slowly came up. My eyes were shut tight as Jane's tongue made contact with the underside of my dick. She then sucked the rest of the way and let go of my dick, making an audible "pop" noise.

Jane had a small string of saliva on her chin, but she quickly took care of that with one stroke of the tongue. I looked and realized that Jane was only partially on the bed. So, I decided to scoot up all the way to the headboard, allowing her to get up fully on the bed.

Jane did just that as she got up on her knees and in between my legs. She smiled at me once again as she grabbed my dick. Jane lowered her head, stuck out her tongue and licked from right underneath my balls. She brought her tongue up over the middle of my sack to the bottom of my dick and up the shaft ever so softly and slowly. She was using just the tip of her tongue, tickling every last inch of my balls and cock. She then brought her tongue up to my head and licked across the bottom back and forth.

Jane then took her mouth off my cock and looked up at me. "How does that feel, baby?"

I moaned loudly, "Mmmmm, god baby that feels so good. Suck it some more!"

Jane chuckled at that comment and said, "Yes sir."

She then wrapped her lips around my cock head and started bobbing up and down the length of my pole. The feeling was undescribable. I was trying to keep my mind off of cumming. I tried to think about anything except what was going on at the moment. That was very hard to do as Jane kept bobbing up and down on my cock. But now, she also took her right and and massaged my balls over and over.

I think she was almost willing me to cum, but I wasn't going to oblige her. I wanted to hold out for as long as I oculd. She took her mouth off of my dick once again. But, this time she wrapped her mouth around my left nut. I instantly shot forward as the sensasion was incredible. I honestly thought that I had cummed, but I didn't. I was very proud of myself.

Jane kept my nut in her mouth as she ran her tongue over it repeatedly. I started feelign more comfortable and bold. I decided to talk and open up a bit more.

"Yea, baby. God, suck me. Suck my cock. God it feels so fuckin' good!"

Jane did as she was told. She took her mouth off my nut and placed it back over my cock. Jane bobbed up and down on my dick some more. She already had her tongue running up and down my dick. I got even bolder as I placed my hand on the back of Jane's head, encouraging her to suck faster and ahrder.

She didn't disappoint. She wrapped her lips ever so tightly around my dick and bobbed up and down very fast. I didn't even need to fuide her. She knew exactly what I wanted and she had no problem at all giving it to me.

Jane kept thi up for at least 3 or 4 minutes. It seemed like forever and that was ok with me. Every last second felt like heaven. I was totally shocked that I hadn't cummed yet. However, I did make that pact with myself not to cum. I am convinced that a "higher power" was with me, helping me not to cum.

Finally, she took her mouth off my dick. There was a little bit of precum starting to ooze out from the tip of my dick. Jane saw this and got the biggest smile of all on her face as she darted her tongue out and licked up all of the precum.

Jane wiped her mouth off a little bit and then straddled my chest. She bent down and again gave me a kiss on the lips. Our tongues explored eachother's mouth as I allowed my hands to run all over her naked back. Her skin felt so smooth and silky.

Jane broke off the kiss and said, "My my, you are one stubborn man. You know that? I want your cuma nd you won't give it to me. Why not, baby?"

I replied honestly, "I wanna save the best for last baby. So far, you've made me feel excellent. But now, if you don't mind, I'd give anything to taste that pussy."

Jane almost purred as she rubbed her hands all over my chest. "You want this pussy? You want this wet Pussy?", she asked in the sexiest of ways. I just nodded and said, ''Damn right."

"You want it? You got it, baby!", Jane said as she got off my chest. I got up and got off the bed as I allowed Jane to take over my spot at the head of the bed. I got on the bed in her old spot and straddled he rchest. I bent down and licked her sweet lips once over. I then went down a little further and grabbed her small A-cup tits in my hand. I squeezed them gently, bent down and licked over her nipples on both tits. I heard Jane take a deep breath and start to relax.

I decided to go straight to the main course. I moved down her body and stopped at her stomach. I kissed and licked her stomach over and over as I felt it up. Her body was fantastic. She had a great stomach, but what I wanted was down a little bit farther.

I slid my body down the bed a little way and then opened her long, tan legs. I lowered my head and came face to face with with Jane's beautiful pussy. I hadn't ver had sex or eaten a pussy in my life at this point, but I'd seen plenty of them on the internet and in videos. I've seen pussies of some of the hottest women I've ever seen, but they didn't compare at all to what was in front of my face.

Jane was in her early 40's, but she was in fantastic shape. Her pussy was an absolute thing of beauty. She had a little strip of hair right above her pussy lips, which I loved. Her cunt itself looked so delicious. I could also see a little bit of dampness on her lips, which turned me on even further. I never imagined I could make someone like Jane wet. It runed me on even more than I already was.

I put my face ven closer into her pussy and inhaled the sweetest scent. Her pussy smelled so sweet and moist. I stuck out my tongue and licked from the top of her slit down to the bottom and back up to the top quickly, getting the taste of it. I took the index and middle fingers on my right hand to open up her lips and to reveal some nice pink pussy.

I used my whole tongue to get a big taste of her pussy. I licked her insides in long, large strokes as I reached up and gently rubbed her clit with my left thumb. Jane started to squirm on the bed and moan softly. it was music to my ears. I then took the tip of my tongue and licked the sides of her pussy lips gently. I then brought my tongue to her clit and licked the very tip of it ver so gently.

With the touch of my tongue on her clit, Jane isntantly moaned out, "Ohhh fuck yes!" She then took her great hands and rubbed them in my hair, uriging me to keep going.

I was more than happy to oblige her. I took my tongue and ran it up and down her clit very fast, flicking it over and over again as Jane was moving in all directions. I grabbged her waist and held it still as I wrapped my mouth around her little clit. I sucked in and my mouth was tightly wrapped around her hard clit. As soon as I did that, Jane gasped and moaned loudly, "Oh shit! Mmmmm yea! Suck my clit! Eat my pussy!"

I kept my lips wrapped around her clit as I stuck out my tongue and brushed it hard against her clit and licked it over and over, keeping my vice grip on her clit with my lips. Jane was moaning very loud as she started grinding her pussy into my face, giving me more of her clit and her wet cunt brushing against my chin.