When I was about sixteen, I did what most other horny young boys did: I searched naughty, sex-related websites. During my conquests, I came across numerous adult chat sites. I created a profile (ModernRomeo), listing me as an 18 year old male, on my favorite site. I started talking with women of various ages, working on becoming competent at cyber roleplay. I was finally able to virtually live out a number of my fantasies. About a month later, I did a roleplay with KatieBelle34. Her profile said she was a 34 year old divorcee. I played an innocent young boy (which was very easy for me to do), and she played an experienced older woman. We continued this scene for nearly an hour. By the end, my fingers were sore from typing, but I was rapidly stroking my dick. The last message she sent to me was: "Thanks baby ;) I had the most wonderful orgasm." This sent me over the edge, and I sprayed cum all over my hand. I logged out and cleaned up, thinking sadly that I wouldn't talk with her again, since part of the allure of these sites is in meeting new, random people. The next day, I came back from school horny and ready to roleplay. As I logged on, a message popped up. It was from Katie (her actual first name). She asked me if I wanted to roleplay again, and what time I was free. I quickly replied that I was free all night, and waited anxiously for her reply. I was right about to start getting ready for bed when a message from her popped up on my computer. "Sorry, I was busy today. Tomorrow?" I sent her a message, saying, "Alright! How about 5?" She did not reply for an hour, and by that time I was in bed fast asleep. But when I woke up, I saw what she said. "Sounds good. I can't wait to show you all sorts of ways to please a woman!" Needless to say, I was so horny during school I could barely focus on my classes. I got home, sprinted to my computer, and started watching porn until she logged on. Again, we had an amazing roleplay that (I imagine) left both of us panting after our orgasms. We talked quite often, sometimes roleplaying three or four times a week. But one morning, after an extremely heated session, I awoke to a message saying: "Here's my number babe. Text me the next time you're horny ;)" Well, I got horny right then and there. But I didn't want to get too turned on before school. Luckily, it was a Friday, so I would have the entire weekend to myself. I put her number in my phone as "Katie", and I went off to school to fantasize the entire day. After the last bell rang, I sent her a message. "Hey, its James." (I had given her my real name.) She replied almost instantly, saying, "Hey James! I was looking forward to your text!" We started off having a nice conversation. I found out she was a secretary (and was texting at work), and I told her I was a student. She asked if I was in college, but I grudgingly admitted that I was only 16 years old. She did not reply for a couple of minutes. I began to think that she never would. But she said, "It’s all cool. I have a thing for younger guys anyways ;)". We started talking about where we lived. After I sent my city, she said, "No way! I live just like 30 minutes from there!" Its a small world, I guess. That night, we texted each other a steamy roleplay involving me sneaking into her house. I orgasmed fairly quickly, because in my horny state, I could vividly fantasize it actually happening. I continued to text her throughout the weekend. That next night, instead of roleplaying, we decided to swap pictures. The first one I received of her was a headshot, showing her brown hair and eyes, and her smiling face. I sent one back. She said, "Aww! You look so cute ;)" I took another of me, shirtless, and she told me she liked my body. I hoped for one from her, but I didn't expect to get one. But I opened her next message to see a perky pair of C cup breasts. I kept repeating how amazing they were, and how I would love to suck on them. Her next message was a picture of her, still topless, sucking on one of her fingers. She then asked to see more of me. I took a picture of my dick, which was standing completely erect, and sent it to her. Katie replied, "Mmmmmm. That gets me horny. I'm going to play with myself to that picture tonight." As I read that message, I nearly blew my load right there. But she had saved the best for last. I opened her next message to see a picture of her playing with her pussy. It was captioned "I'm thinking of you James." I sent one of me stroking my cock. With that, we each had our separate orgasms. I went to bed, tired, but excited for the next day. However, compared to the last, it was a slight disappointment. We still had our steamy roleplay, but didn't send any pictures. I went to bed, not expecting the things that would happen to me next week. The beginning of the week continued as normal. Well, as normal as I could be while texting a sexy older woman. We sent a couple more pictures, but nothing extremely exciting happened until that Thursday night. After our usual roleplay, she started talking about meeting in person. "I really want to see you ;) are you free this weekend?" "Yeah, I think. I mean, my parents are home..." "Don't worry. I can pick you up. If you're interested, that is...? ;)" "Hell yeah! But I have to be back by 12." "I'm busy until 8 on Saturday, but I can pick you up at 9?" "Sounds great! Where are we going?" "My place, of course! It’s an apartment, so don't be too loud ;)" "Okay see you then!" The last couple of days were hell. I was constantly horny, imagining myself ravaging a beautiful woman. To tell you the truth, I don't even remember going to school that Friday. But, soon enough, the Sun began to set on Saturday. I told my parents that I was going out with some friends, and as I had expected, they told me to be back by 12. I had to look my best for this. I put on my nicest pair of jeans, with a light blue button up shirt and a belt. Lastly, I sprayed myself with a small amout of cologne. All I saw was a pair of headlights turn into my driveway. I opened the door and climbed down my front steps, hoping that my erection was not visible through my jeans. The car was a nice red mustang, and I opened the passenger door and sat down inside. Katie was sitting inside, smiling at me. She looked stunning in a short black dress. Her breasts looked as though they wanted to break free of their restraints. "Hey James," she said in a sultry voice. "Hey." I replied lamely. She reversed the car, pulling out of my driveway. I finally gathered enough courage to compliment her. "You're looking...beautiful." I smiled at her. She pulled the car to the side of the road and looked at me. "Are you nervous for this?" I let out a little laugh. "Maybe a bit." She smiled. "It'll be a lot more enjoyable if you just relax. We don't need to do anything that you don't want to." "Alright. That sounds good." "So," she said, turning her head slightly. "Do you want to learn how to please a woman?" I stared back at her and nodded. She started the car, and continued driving. "Now, the single most important thing is foreplay. You need to make sure that your woman is horny and ready in the bedroom." She reached over and grabbed my wrist. She placed my hand on her silky thigh, and I felt my cock twitch in my pants. "It's best to start with soft touches, and to avoid the pussy. Women like to be teased." She gave me a little wink, and placing her hand on mine, began to move my hand up and down her thigh. She sighed, and spread her legs slightly, moving her second hand back to the steering wheel. I started to lightly stroke her other thigh, sliding my hand under her dress, but making sure not to touch her pussy. My fingertips brushed against her lacy panties, and made their way back down her thighs to her knees. Katie made a left turn, and then said without looking, "Are you just gonna keep that other hand on your lap?" I slowly moved my second hand up her smooth dress to feel her breasts. Even though she was older, they still felt firm under my probing hands. Gaining confidence, I slipped my hand into her cleavage to fondle her nipples. Katie started getting flushed, and she made a right turn. My hand, seemingly of its own accord, slid all the way up her thighs to lightly rub against her panties. I could feel my fingertips getting wet. I started to massage her pussy through her panties, and I heard Katie sigh with pleasure. I began to move my hand to the waistline of her panties, tempted to slip inside. But, all too soon, Katie turned into the parking lot of her apartment. She turned off the Car, and quickly turned to kiss me passionately on the lips. "Let's go inside," she whispered. We got out of the car, and she led me by the hand into her apartment building. No one was there to see us, and Katie started leading me up the stairs. The sight of her ass swaying back and forth as she climbed the stairs made my cock strain against my jeans. Katie's room was on the second floor. She fumbled around in her purse, pulling out a key. The lock clicked, and she walked inside, turning on the light. I followed inside. There was a TV on a table, with a couch and chairs surrounding it. The kitchen was modest, but modern. I didn't get to look at much else as she led me by the hand into the bedroom. We both sat down on the bed, and she turned to me and said, licking her red lips, "Do you want to learn how to please a woman?" In response, I leaned in and kissed her. She moved a hand behind my head and started passionately making out with me. My hand found its way back to her thighs, and it slowly began to slide up. As my fingers reached her panties, Katie leaned forward and whispered in my ear. "You're doing great James. But I'm going to show you what it's really like." Katie pushed me down onto the bed and straddled my body. I could feel her warm pussy grinding against my jeans. She leaned forward and started kissing up my neck to my ear. I felt teeth as she nibbled lightly on it. Her hands were roaming everywhere, undoing buttons wherever they went. My shirt was tossed onto the floor, and my belt soon followed. She kissed all over my body, rubbing her hands against my chest. In one motion, she pulled her dress over her head, leaving her in a lacy purple bra with matching panties. Her hands found their way to the button on my jeans. They were pulled off slowly, as Katie looked into my eyes and winked. "Do you want to do this, big boy?" She purred. "Ye...Yes." I stuttered out. She licked her lips again, and kissed down my chest to my waistline. She grabbed my boxers with her teeth and began to pull them off my body. As soon as they cleared the top of my cock, it sprang up. Katie finished pulling my boxers off, and she kissed back up my legs. She paused at the tip of my cock, looking down at it and then back at me. She opened her mouth and slowly began to suck it. I moaned loudly, seeing this lovely brunette blowing me. Her hand slid down my torso and gripped the base of my shaft. I began to feel my orgasm building. I warned her, but she just winked at me. Exhaling sharply, I shot my hot cum into her mouth. Katie swallowed it all without missing a beat. She licked her lips and kissed her way back up my body until she reached my ear. She whispered, "One thing I love about young guys is that they're always up for a second round." Katie climbed off of me. "But first, it's your turn to eat me out." She lay back on the bed with her legs spread. I crawled between them, kissing up her thighs. My hands grabbed her panties and slowly pulled them off her long legs. Her own hands unclasped her bra and tossed it onto the ground. She grabbed the back of my head and guided me to her bare pussy. "You need to focus on the clitoris. That's where most of the...OH!" She squealed as I began to lick and kiss her pussy. "Oh yes! Keep it up! A little harder and faster. Oh that’s it!" Katie began moaning loudly as I continued to eat her out. I slowly slid my fingers up her thigh. As I licked her clitoris, my finger started to slide into her pussy. "Oh James!" she moaned. I kept eating her out. She took very good care of herself, and she didn't taste bad. After a couple of minutes, I started to enjoy the taste. My tongue flicked faster across her clitoris, and Katie grabbed the back of my head and started humping my face. "James! Yes, that’s it! Oooooooh...I'm cumming!" She thrashed on the bed, moaning. She lay there, panting, for a couple of minutes before sitting up. Katie looked into my eyes, and I saw unbridled lust. From a table beside the bed, she pulled a condom. Biting her lower lip, she slowly opened it. Katie pushed me back on the bed. She crawled between my legs, and put the condom in her mouth. She leaned forward and, using only her mouth, put it on my hard cock. Her soft hands began touching my balls as she rose off my dick. She licked her lips, and leaned forward for a kiss. We passionately kissed, and I ran my fingers through her soft hair. My other hand slid up her belly to fondle her breasts. She leaned forward. "Are you going to be my young stud? Are you going to fuck me with your huge dick?" She climbed on top, placing her entrance on the tip of my cock. She started grinding against it, moaning and whispering dirty things into my ear. "Fuck yeah. I want to take your virginity. I want to be your cougar. Fuck me, James." She slid onto my shaft, engulfing my cock in warmth. I moaned loudly, enjoying the sensation. She lifted her hips, then pushed back down, riding me. My hands moved down to her waist, and I began pulling her onto me, fucking her pussy. Katie leaned forward, kissing me on the lips. "Now....mmmmmhhhh....spank my ass." She moaned as she rode my dick. I hesitantly raised my hand and let it fall on her ass. She growled. "Come on! Like you mean it!" I started spanking her ass as she thrust down onto me. We both were moaning and writhing on the bed. My other hand moved up her torso to fondle her breasts. I started lightly pinching her nipples, which caused her to moan louder. We continued fucking until Katie switched positions. She lay on her back, and I crawled between her legs. "Grab my legs and put them over your shoulders." I lifted them up, and positioned my dick at her pussy. I slid the tip up and down her entrance, then thrust my entire length into her. Katie began to moan loudly. My hands started to fondle her breasts. I began to feel another orgasm building, and started fucking her faster. She moaned out, "Oh hell yeah!" She orgasmed, pushing me over the edge. We collapsed back into the bed, completely spent. We lay there, holding each other, until I looked at the clock. 11:34! "Oh shit!" "What is it, babe?" "I need to get back!" I quickly dressed, and headed for the door. Katie pulled on a tight shirt and yoga pants. She grabbed her keys, and we left for the parking lot. In the lobby of the apartment building, an old man looked between us, and gave me a knowing smile. We climbed into the car, sharing a quick kiss, and she drove off toward my house. I kept watching the clock, and we reached my driveway at 11:58. I jumped out of the car, and turned to face Katie. "Sorry I have to go so quickly." I laughed dryly. "But make sure you text me!" Katie winked at me, and reversed out of the driveway. She whispered out of her window: "I'll see you soon stud!" If you enjoyed this story, positive feedback would be appreciated! A part 2 could come if you enjoy this one!