First Sex

After the magnificent evening in my car, Mary had to leave to go back to campus. She had classes that kept her pretty busy and I was working full time, so we didn't get to see each other as often as we would have liked. After our last encounter, I wanted that to change for obvious reasons.

She came back to town a few weeks later to visit her friends. They were meeting up at the gym later that day. I got off work around five in the afternoon and went home, took a quick nap and got a shower in.

Around eight I was on my way to meet her when she sent me a text saying they were finished. We decided to meet up where we worked.

I pulled my car around the side of the building and after a few minutes I saw her pulling in. She pulled her car up next to mine before making her way over. I've never seen a more STUNNING woman! She had on a t-shirt, basketball shorts, hair up in a ponytail and her face was glowing. She opened the car door with a huge smile on her face. She sat down in the passenger's seat before leaning over to give me a quick kiss. We talked for a while about how our day went, what we had been up to and how much we had missed one another.

It didn't take much longer before we were all over each other. Thinking back on it now, the first time we got intimate in my car was very slow, sensual even. This time around I'm not sure if we wanted or needed each other. Hands were groping everywhere. Every kiss was fierce and passionate. My windows fogged up in seconds from our heavy breathing. I remember during one kiss, her tongue was so far in my mouth when I pulled back to break the kiss, I could see it still retracting back into her mouth.

I moved my head down and began kissing her neck. She told me not to because she was still sweaty from the gym, but I was too turned on to go back now. I attacked her neck, kissing my way down to her collarbone then extending my tongue to lick all the way back up. She tilted her head back, gasping, as she ran her fingers through my hair. I moved both of my hands up her body until I found her breasts. They filled my hands perfectly. I pushed up on them, caressing, and squeezing them, as our mouths met again. This time she broke the kiss. She told me to move my seat back. I slid it back and pulled the lever up to let the seat fall back into the backseat. She had moved up onto her knees while I was doing so. I used both hands to pull her face back down onto mine as her right hand found the crotch of my pants. She tried to maneuver herself on top of me, but the stupid steering wheel got in the way. If my car was a little bigger, I have no doubt that we would have ended up having sex right there on the spot. Instead, she re-positioned herself and began unclasping my belt. I moved my right hand down to the front of her shorts, using my middle and ring fingers to massage back and forth, causing her to moan out.

One of my biggest regrets in life happened then and there. I remember her saying, "MMMMM....I'm so horny! You should come back to my apartment with me!"

I wanted nothing more than to bury myself deep inside of her. I've always had issues when it comes to over-thinking though. I always think about other people's feelings over my own. Thoughts like, "Does she really want to lose her virginity to a guy like you?" and "She wants to wait until she's married to have sex, you shouldn't take that away from her", all went through my head at that exact moment. I let my conscious get the best of me and told her I had to work early the next morning. I had the most BEAUTIFUL woman in the world wanting to have sex with me and I blew it. To this day, I still hate myself for that.

She seemed a little let down by my statement, but it didn't stop her from taking my belt off and unbuttoning my jeans. She pulled my boxers down just enough for my penis to come springing out. She reached out, taking my hardened member in her right hand. She sat back down in her seat, getting herself comfortable, as she moved over, taking me into her mouth once again. Unfortunately, the way she was now positioned, I couldn't really do much for her. I tried to reach between her legs, but my arm was only long enough to reach her butt. I ran my right hand over her right butt cheek, occasionally squeezing and caressing it, while she gave me head once again.

Our first blowjob was very intimate. I think she took it easy on me, but not this time. From the get-go she used her hand and mouth with a purpose. I remember seeing the top of her hand glued to her mouth as her head bobbed up and down my shaft. I leaned back, closed my eyes, and listened to the slippery sounds of her saliva being pressed between her lips and my penis. I think I lasted about a minute. Just like last time she went until the very last drop was gone.

We parted that night, me feeling like the world's biggest idiot. I just hoped I didn't hurt her feelings.

Luckily, she was gonna be on break soon and I would get another chance. This time I was gonna do everything I could not to ruin it.

She came into town and worked a few days. One day I was standing around, eyeing her, while she was sitting on her knees in a chair. Her plump, sexy butt was sticking straight out into the air. I texted her and told her to stop teasing me, causing her to look my way and break out into laughter. Work was fun that week. We would sneak off into closets, make out for a few seconds and then return to work like nothing happened.

Near the end of the week, she invited me to her apartment to watch a movie. She knew I was a big nerd when it came to movies, so she told me to pick one I thought she would like. I told her I would be there, and I would bring a few just to make sure. The date was set.

I tried to plan everything out. I wore a t-shirt and some Adidas jogging pants, with the whole idea of them being easy to remove. On the way to her apartment, I stopped at a gas station nearby and bought some snacks, sodas and condoms. When I got to the apartment I hid the condoms in a different pocket of my bag, just in case she noticed them.

She had three of the nicest roommates I've ever met. I had met them all a few times in the months we spent together. I noticed immediately as I walked in that none of them were home. The other thing I noticed was what she was wearing. She looked BREATHTAKING! She was in a red shirt and a pair of jeans, both tight in all the right places. I thought to myself, "Had she planned this just as much as I had?" Maybe, but I might've been over-thinking again.

We went straight to her bedroom, her locking the door behind us. I walked up behind her, wrapping my arms around her waist. "This is for teasing me at work!"

She responded by pushing her butt back into my crotch. I took that as a good sign, so I moved my hands up and began fondling her breasts. She ran both her hands up and clasped them behind my head. She turned her head to the right, leaning back to give me a nice, long, tongue kiss.

A few minutes later, I opened my bag and pulled out a handful of movies. We decided on watching The Boondock Saints.

We pulled her futon out, climbed onto it, and laid down. My back facing the wall and hers in front of mine. I laid my left arm over her waist and propped my head up with my right arm, while she laid her head onto a pillow.

She would routinely turn and kiss me every so often. It got hotter and heavier with each kiss. I'm pretty sure she wanted me just as much as I did her. Eventually, she turned completely away from the movie to face me. I looked deep into her eyes for a second before we gave each other our best kiss yet. Her tongue blasted into my mouth. I tried my best to massage it with my own. I felt the tip of her tongue touch the inner sides of my cheeks numerous times as we rolled them around for what seemed like forever. We eventually had to break to get some air. Now was my chance. I kissed her on the cheek before I moved down to the left side of her neck. I used the same method as before, kissing my way down and licking my way back up. She ran her fingers through my hair as I made my way over to do the same to the right side.

On the last pass I went up to nibble on her right ear lobe. I moved myself up to my knees, pulling my shirt over my head. She ran her hands over my chest and stomach before pulling me back down. I began kissing her collarbone, moving my way down to her chest. I used my right hand to pull her shirt down, just enough to see a little bit of her black bra. She continued running her hands through my hair while I pulled the bra down a little as well, exposing her left nipple. She moaned out as I traced my tongue around her areola a few times before taking her erect nipple into my mouth. I pulled the other side down as well, sucking on her right nipple the same way I did the left.

Up until this point she had given me two blowjobs and I think I had gotten her off once. I wanted her to feel as good as I did those two times, so I concentrated on her breasts. I was using my right hand for balance, so I used my left to go back and forth, groping both of her delectable breasts, squeezing them while flicking my tongue out over one before moving to the other.

Eventually, I found my way down to her stomach. During our heavy make out session her shirt had ridden up. I kissed all around her belly button before moving down. My hands moved down, finding her belt. I unclasped it, pulling it off, while getting up and moving off the futon to my feet. I dropped the belt to the floor and made my way down onto my knees. I reached up, unbuttoned her jeans, and pulled them off onto the floor. I leaned forward, planting soft kisses over her thighs and her panty covered vagina, causing her to let out a soft gasp. She watched me hook my fingers over the top of her matching black panties, sliding them off as well.

I kissed all around her vagina before running my tongue in one long, slow lick from the bottom to the top. I made my way to her clit where I began flicking my tongue out over it but noticed she tensed up more when I simply put my whole mouth over her mound and used the flat part of my tongue to massage it. I could tell I was doing something right when she started running her hands over her breasts, playing with her nipples.

I had always wondered why people liked to give oral sex. When that first drop of wetness seeped out onto the tip of my tongue, I was hooked. She tasted FANTASTIC! I couldn't get enough. I moved my face down a little and pushed my tongue as far as I could inside of her, causing her to groan even louder. I continued eating her out for a few more minutes before sliding my middle finger inside her. I moved it back and forth, slowly, while I continued lapping away at her clit. To my surprise, I felt her right hand push my head away.

I stopped and looked up. "Am I doing it wrong?" I asked.

Breathing heavily, she said "No, absolutely not! I just want your dick inside of me!"

I got to my feet, making my way over to my bag. I slid myself out of my pants and boxers. I pulled out the box of condoms I had brought. I had never used one, so I was a little nervous about making an idiot out of myself. I ripped one open, feeling the outer ring, hoping I would put it on correctly. Luckily enough, it slid down right over me. I turned to see her watching me, now completely naked. She was MESMERIZING!

I climbed back down on the futon, maneuvering myself in between her legs, as she spread them wider for me. I felt the warmth emanating as my penis spread the lips of her vagina, allowing me access. I felt the wetness as the tip of my rock-hard shaft slowly entered her. Her walls contracted tightly around me, enveloping me as I pushed my full length inside.

I remember blurting out "OHHHH..... MYYYY.....GODDD!" as my whole penis disappeared inside of her.

She moaned "OHHHHHHHHH..........BABEEEEEEE!" as she took me up to the hilt, me fitting snuggly inside.

I put my hands on the bed on each side of her head as I slowly began thrusting in and out of her. I was afraid of getting off too early so I went as slow as I could. She didn't seem to mind too much. Her eyes closed while I continued rocking my hips back and forth. I started picking up the pace a little at a time. She started licking her lips and eventually her mouth was fully open, showing me her sexy "O" face. I felt the familiar tingling down in my testicles. I wanted her to enjoy every second of this. I knew I wouldn't last much longer so I leaned back, pulling out of her.

"I want you to be on top." I told her.

She opened her eyes and gave me a quick kiss. I moved off her, then she made her way to her feet as well. She wrapped her arms around me, and we began making out once again. While kissing an idea popped into my head.

"Bend over for me!" I begged.

She placed her right foot on the railing of the futon and her hands on the back. I bent my knees and came up from under her. I found out right then that doggystyle was my favorite sexual position. From our very first kiss I had wanted to bend her over and do this. She had the perfect bottom - athletic, toned and also very curvy. I put my hands on her hips and thrusted as fast as I could. Our bodies slapped together in pure ecstasy. With every thrust I made I heard a whimper. I would've loved to empty myself, but my legs got tired pretty fast. I stepped back, allowing her to stand back up. She turned to look at me, giving me that beautiful SMILE once more.

I got down onto the futon and she positioned herself on top of me. The sensation of me entering her again was almost too much. She put her hands on each side of my head and began rocking her body up and down. Her breasts looked amazing, swaying around as she moved. When she bounced up it always felt like I would come out of her. I never did. She was a master at this. The tip of my penis always stayed inside her and then when her body came back down, I would feel her wetness splash on my legs, as she took my whole member back in her. I played with her voluptuous breasts as she rode me to near completion.

We were both so lost in the moment we never heard the front door open or shut. One of her roommates came home and asked if anyone was there. Thankfully, Mary had locked the bedroom door but that's when I noticed the squeaking of the futon. I was so scared her roommates would hear us.

As I was thinking that Mary had stopped moving. "I want you to get back on top of me!"

Mary got to her feet with me following. The condom I was wearing dripping from her wetness.

"Do you think your roommates will hear us?" I asked.

"I don't care if they do," she laughed.

I had once again got too far into my own head. This beautiful lady had just taught me that I worry too much.

I watched her grab a blanket off the bed and lay it onto the floor. "Now get down and finish. I know you've been trying to hold it in," she laughed once more as she lay down on the blanket.

With renewed energy, I got down onto the floor. I kissed from her vagina up to her breasts and all the way back to her mouth. I moved my body in between her wonderful thighs and entered her for the last time that evening. She brought her legs up even more, placing her ankles on my back as we went back to kissing. I picked up the pace, until I was, to my thinking at least, pounding her pussy. She moved her hands to my sides, and it felt like with every thrust, she was using her hands and feet to push me in even deeper inside of her. All that was audible in the room was the slippery, squishy sounds of me fucking her and her little moans.

"OHHHH.....SHIT.....BABE.....I'M.....ABOUT.....TO.....CUM!" I whispered.

"DON'T.....STOP.....PLEASE.....DON'T.....STOP!" she answered.

And just like that I erupted, filling the condom full inside of her. I tried to keep thrusting, but the sensation was so overwhelming. We both relaxed for a bit before I pulled myself out of her. The condom itself was almost overflowing with cum. I threw it away and made my way back down next to her. She placed her right arm over my chest and gave me a kiss on the cheek, as I lay there, wondering how this INCREDIBLE woman wanted anything to do with me.

If this night could have never ended, I would be totally cool with that.