So I was DM’ing with a follower who has been chatting with me for a while. She was complimenting the retelling of my adventures with Beth many years ago, and she remarked on my particular success with oral sex with Beth. Frankly, I’ve always thought oral was a skill set in which I excel, and it’s because of the experience I had early on, thanks to one particular girl, Stephanie. So I thought I’d share that experience. This is the story of how Steph taught me to eat pussy.
So I was 18, just started my senior year in high school. I’d lost my virginity a couple years before that but didn’t exactly have a line of girls outside my door. I was a bit of a nerd and somewhat introverted, but I was fairly self-confident.
Steph was the older sister of my friend Troy. She was 19 going on 20 and in her sophomore year of college. I’d known her for a long time, since we had grown up in the same town. We had gone to the same elementary and middle schools, although I had moved away for my first two years of high school and then moved back – since she was two years ahead of me in school, we never went to the same high school together.
Steph was always attractive to me. She was blonde with brown eyes and wore her hair long. She had kind of a flat butt but nice tits, at least I had always thought so. When I was in middle school I told Troy that his sister was hot. And of course he punched me hard in the shoulder and told me that was gross. Back then, I jacked off thinking about Steph and looking at her yearbook photos. But let’s be honest – most of us guys at that age jacked off to just about anything and everything.
The year before, when Steph left high school and headed off to college, she was kind of a Plain Jane – didn’t wear much makeup and dressed in ordinary clothes. During her freshman year, she joined a sorority and really seemed to get into the college social scene. When she came back to town after that first year at school, she had transformed. She really paid attention to her hair and makeup, and she wore clothes that complimented her body. In short, I thought she was fucking hot. As I started my senior year of high school, Steph had moved up to the top of my jack off fantasy list.
Steph came home for a long weekend, I think it was in mid October. I was hanging out with Troy on a Friday afternoon. He and I were in his room playing video games and his mom came in to remind him about some chore he was supposed to do. So he insisted we pause the game while he did whatever it was. I went out to the kitchen to get something to drink, and Steph was there. She was wearing sweats and a t-shirt, no bra, with her hair tied back. Of course, I already thought she was hot, so I definitely wanted to say hi.
“Hey,” I said, as casually as I could.
“We’ll, hey there!” Steph replied. “It’s been a while.”
“Yeah, I haven’t seen you since you left for college,” I told her. My heart started pounding as I took a chance and said, “You look great! Must be all that studying.”
Steph narrowed her eyes as if she was unsure of my cues. “Thanks,” she said. “Yeah, studying.” I figured I had missed the mark. But then she said, “But what about you? You’ve grown up since then.”
I froze for a moment. “You think so?” I finally said.
Steph reached over and grabbed my bicep. “Yeah, you’ve been working out I see.” I swallowed hard. She’d called my bet and raised me two. I had to think fast.
“Well, I’ll have to compete with all those frat guys next year,” I said. I don’t want to get lost in the crowd, you know.”
Steph grinned. “It takes more than muscles to stand out,” she said suggestively. I really didn’t have this kind of game. I had no clue what to say next. She giggled. “You’re cute,” she said. “But don’t try so hard.” And looking down at my crotch, she said, “You won’t have to.”
That’s when I realized I was sporting a solid semi, very visibly bulging through my jeans. Steph walked out of the kitchen, squeezing my other bicep on the way past me.
I turned and, before she’d gone too far, I said, “so when do you go back?”
She paused and said, “this is my Fall Break. It just a long weekend. I go back to campus on Tuesday.”
I went for it. “So I applied to a few places, including [Steph’s college]. Maybe I could ask you a few things about it later? You know, help me sort out the pros and cons?”
She saw right through me as she flashed that same grin. “Sure, why not.” she said. “I don’t have any plans tonight. Meet me at Mackey’s at eight and I’ll help you out.”
I swallowed hard and said, “OK. See you then.” I felt my semi go more rigid.
Mackey’s was the local burger joint and general hang-out. I went home and showered up, then put on my “cool” outfit – well worn jeans, a plain white T, and my Doc Martens. I doused myself in too much cologne, grabbed my car keys, and headed out.
I got there just before 8 and found a parking spot. Mackey’s wasn’t very busy. I saw a couple of familiar faces as I got myself a booth and sat down.
I ordered a Coke and waited. And waited. And waited some more. By around 8:30 I was getting discouraged, figuring Steph wasn’t coming. At 8:40, I decided that Steph had played me and I was a fucking idiot.
But then she walked in. She had on the tightest faded jeans. It looked like she’d poured herself into them. They showed off her ass and a little bit of camel toe. And with the jeans she wore a tight sweater. Her tits looked amazing. And she had curled her hair and put on makeup. She looked amazing. I raised my hand so she’d see me, and she came over to the booth.
“Hey,” she said. “Sorry I’m a little late.”
“That’s OK,” I said. “I just got here myself,” I lied.
“Well, Troy was hanging around and I didn’t want to deal with him asking any questions,” Steph said. “I don’t want my brother wondering why I’m hanging out with his best friend. I’m sure you understand.”
“Uh, sure,” I replied.
So we ordered some food and talked for a while, mostly about people we knew in common, memories from when we were little, things like that. It was a really pleasant conversation, just a couple of friends catching up after a long time. I asked Steph about college, what her classes were like, what her favourite subjects were. And then we started to talk about the social scene.
Steph admitted she joined her sorority to have a go-to social calendar. “I didn’t want to miss out,” she told me, “and that was a way to ensure there was always something fun going on.”
“So I suppose there’s a party every weekend?” I asked.
“Well, sure there’s always a party somewhere, but we don’t have ragers all the time,” she replied. “A lot of the time we just hang out. My sisters are all pretty cool.”
“Sounds like a good plan to me,” I said. “Maybe I’ll rush a fraternity then.”
“It all depends on what you want to get out of it,” she said, grinning.
“There’s always the sororities next door, right? I suppose you’ve all got your pick of fraternity guys,” I said with a smirk.
Steph rolled her eyes. “Yeah, well there are always guys who want my number and all that. But most of them are more bark than bite.” She giggled. I didn’t understand what she meant, and she could tell. “Like 99 percent of these guys come around thinking that just because they’ve got a dick, I’m gonna melt at the sight of them, hop into bed and moan like a porn star.” The conversation had quickly turned from subtle to direct, and I must have blushed the deepest shade of red. “Don’t be embarrassed,” Steph said coyly. “Everyone is horny in college.” Under the table, she slid her foot up and down my leg.
I gathered myself as best I could, swallowed hard, and continued the conversation. “So what, the 1 percent are the guys with the big porn star dicks getting the porn star moans?”
Steph bit the tip of her finger and smiled. “Well,” she said, “from what I could tell earlier today, your dick is plenty big.” I blushed again, and could feel my bulge pressing hard against my pants. “That may open a few doors for you, but it won’t get you into the 1 percent.”
“I’ve been with girls before,” I stated. “I’ve got some experience.”
“Sure you do,” Steph replied. “And all those horned-up frat guys do too.”
“Well the girls I’ve been with seemed to enjoy it,” I said in my defense.
“You think us girls would tell you otherwise?” Steph shot back. “I’m sure that thick cock of yours was fun for them.”
“Okay,” I said, “are you gonna tell me the sorority secret? How do I get into your 1 percent?” I smiled but my heart was pounding. I’d never had a conversation like this, especially not with a hot college girl. I shifted in my seat as my cock was about to burst through my zipper.
“Hmmm…” Steph teased. She leaned forward on the table, subconsciously squeezing her tits together between her arms, and looked straight into my eyes. “You’re cute,” she said, “and clearly clueless.” I wasn’t sure what to do with that – a compliment and an insult at the same time? Steph just stared at me for a moment, thinking, with a grin on her face.
I was confused and deflated, and I was starting to lose what confidence I had.
“We’ll then,” Steph said. “I guess I can’t let my brother’s best friend head off to college unprepared.” And she went on to tell me about Zach.
Zach was a guy that all the sorority girls talked about. He was in his senior year and had slept with four of the girls in Steph’s sorority. They all said he was the best fuck they’d ever had. Steph had hooked up with him after a party.
“So he must be one of those porn star dicks then?” I asked.
“No,” Steph said. “His dick is actually on the small side. It’s what he does with his tongue. It’s amazing.”
I knew about eating pussy of course, and had tried it with my second girlfriend. I figured I’d done it right since she had seemed to like it.
“I had my first orgasm with Zach,” Steph said. “And my second, and my third,” she chuckled. Then she looked straight into my eyes. “That’s why the girls talk about him. That’s why he’s in the 1 percent.”
I didn’t know what to say. Steph sat there smiling like she was plotting some kind of scheme. After a long pause, she finally spoke. “I like you, and I know you’ve had a crush on me since middle school. You’re cute, in a nerdy kind of way. And like I said, I can’t let you head off to college unprepared.”
“Uh, Okay,” I said, not sure what would come next.
Steph leaned over the table and kissed me. “We could have fun together,” she continued. “How ‘bout I show you what you need to know?”
“Um, yeah,” was all I could say. My head was spinning. This hot girl I’d crushed on was gonna do what- teach me how to eat pussy? With her pussy? This is not how I’d thought this night would go, but was this better? I just couldn’t think straight. I was nervous and excited and anxious and so fucking turned on.
“Let’s get out of here,” Steph said. We both drove back to my place. My parents were home so I went in first and then Steph came around to the back door. We went quietly into my room. She was giggling. I was sweating nervously.
We sat down on my bed. Steph held up her hand, with two fingers together pointed downward and the tip of her thumb peeking through in between. “Show me your technique,” she said.
“Huh?” I said.
“Pretend my hands are a vagina,” she said. “The lips are my fingers and the clit at the top is my thumb. Show me what you do.”
This was weird, I thought. But whatever, I licked between her fingers, up and down. She showed me how to move my tongue slowly up and down, to move it around in between her fingers, to use light pressure and make circles around her thumb-clit. After a while it started to seem silly. She could tell I was feeling awkward.
“Here,” she said. “Let me give you some inspiration.” She stood up and stripped off her sweater. She sat back down, grabbed my hand, and put it on her breast. She worked my hand around her hard nipple. Then she had me try again on her hand. I closed my eyes and pretended it was real. I did what she’d shown me to do, taking my time, using light pressure, working my tongue all around. My eyes were still closed when she leaned in for a kiss, moving her hand away from my mouth and replacing her fingers with her tongue. We kissed for a long time, as she swirled her tongue around mine. She pulled back and offered her hand again. I demonstrated again, this time inspired to do it well. After a few minutes, she stood up and unhooked her bra. Sitting back down on the bed, she again came in for a deep kiss. As we explored our mouths, she brought my hand back to her breasts, guiding me to massage them as she liked it done.
Steph reached out and felt my crotch. My dick was rock hard inside my jeans. She rubbed it while we kissed, then pulled back. “Kneel down,” she instructed me. I looked at her, puzzled. “You’re ready for your first test,” she said. I knelt facing her beside the bed. Steph slid her jeans down and stepped out of them. Sitting on the bed, she spread her legs in front of me. She rubbed her pussy and pulled up on it to expose her clit. “Now just do what you did before,” she said gently.
I moved right in. I licked up and down, moving my tongue side to side. I circled her clit, then moved back down to her opening. I pointed my tongue and twirled it into her opening then flattened it and stroked her whole vagina with it. She made soft morning sounds and encouraged me as she said, “yes, that’s it. That’s good,” and guided me on how to give her pleasure. We did this for a good 20 minutes, and I discovered just how wet a pussy can get. In the limited sexual experiences I’d had before this, I would have shoved my dick inside the girl and started fucking long before.
It felt amazingly good as she got wetter the longer I continued. And her pussy tasted sweet. My mind was racing and my heart pounding every time she gave me encouragement. I was enjoying her feedback, knowing that it felt good to her. Finally, Steph gently pushed me back, and then pulled me upward without saying anything. I got up off my knees and stood in front of her. She unfastened my belt as I lifted my shirt off over my head. She unbuttoned my pants and kissed my stomach softly. She lowered my zipper as she looked up at me, and then slid my pants down. My cock sprang out, hard and throbbing. She smiled and said, “Wow! It’s even thicker than I thought.”
Steph opened her mouth and slowly took me in. She held herself about halfway down my shaft while she swirled her tongue around my dick. It was warm and wet and oh so good. She moved her head back and forth, curving her to tongue to stroke the underside of my cock. I’d never felt a sensation so intense before. After a long day of fantasizing about her, with her stroking my leg and talking to me and showing me how to please her, I didn’t last long. After just a couple of minutes, my knees started to get weak. “Oh god,” I said, and I exploded into her mouth. Steph kept sucking as I shot my load, pump after pump of cum shooting into her mouth. She pulled back, looked around and saw my wastebasket, and spit my cum into it. “Um, I’m sorry,” I said.
“Don’t be,” she said. “But next time tell me when you’re close.”
“Next time?” I asked.
Steph smiled at me. “You didn’t think this would be your only lesson, did you?” I smiled back.
“You did well, but there’s lots more I want to show you.”
We got dressed and I walked her outside. “This was fun,” she said, and kissed me on the cheek. Let’s do it again tomorrow night.”
She got in her car and I watched her drive away. I was buzzing from everything that had just happened. I went back inside and laid down on my bed, and I could still smell and taste her pussy on my lips. I wondered if I’d given her an orgasm. I probably had, I thought, but I wasn’t sure. I didn’t actually know how to tell.
The next day was interminable, the longest Saturday of my life. I cleaned up my room and took a fresh shower, told my parents I was going to bed early and laid there waiting for Steph. My dick was already half hard in anticipation of her arrival when I heard her car door close out on the street. I let her in the back door and we sneaked quietly to my room.
“Hey,” I said.
“Hey,” Steph said back with a smile. “Last night was fun.”
“It was,” I replied. I hesitated, afraid to ask the question I really wanted to know.
“What is it?” she asked me.
“Well,” I said. “Uhh…”. She looked puzzled. “Did I give you an orgasm last night?”
She laughed gently. “You did really well, but no. And that’s okay.”
“I don’t really know how to tell,” I admitted.
“You’ll know,” she giggled. “Trust me.”
Steph gave me a long kiss, then had me start with her hand again. I was eager to demonstrate what she’d shown me before.
“Now, when you’re circling the clit, put your lips around it and suck gently.” I did as she said, taking a few tries to get the hang of it on her simulated pussy. “Good,” she said finally. “That’s like throwing gas on the fire.”
She pulled me back in for another kiss, slow and deep and sensual. “The next part won’t work on my hand,” she said. Steph had me get undressed while she took her own clothes off too. Damn she looked hot. I was already hard when she said, “Okay, come here.”
She laid us both down on the bed, then guided my hand to her pussy and helped me stroke it with my fingers. Slowly and gently she pressed my middle finger into her wet opening. “Turn your hand this way,” she instructed, and showed me how to position my hand palm-up to stroke the top inside of her vagina. “Feel that?” she asked.
“I think so,” I said sheepishly.
“That’s my g-spot,” she told me. “Do that while you’re using your tongue.”
That was my cue. I knelt beside the bed again and dove right in. Light touches, gentle licks, swirling tongue, and then a soft sucking on her clit. Steph inhaled when I did that. “Oh yeah,” she said. I kept going, repeating the technique. I could tell how much she liked it. After a few minutes I brought my hand into play. I slid my middle finger in, palm upward, hoping to find that g-spot. I stroked gently as she’d shown me while I continued with the mouth techniques. I could feel her clit swell larger and saw her breathing quicken. I increased the pressure from my tongue and the suction from my lips. It was beyond her earlier instruction, but I slid a second finger into her wet hole and stroked. Steph reached down and put her hands on the back of my head. “Oh yes!” she purred, and I kept going. Another few minutes into this symphony of lips, tongue, and fingers, and Steph’s back arched. Her thighs clenched and she tugged on my hair. She made an incredible sound, part moan and part stifled scream. Shivers ran through her legs as it seemed like her whole body shook at once. I carried on for about 10 seconds, and then I pulled back.
“Wow,” Steph said, breathing hard. “You’re a quick learner!”
“Was that…” she cut me off.
“Yeah,” she said breathlessly. “That was.”
I’d brought her to orgasm. It was incredible to witness it. I had actually seen and felt the pleasure course through her body. And I saw it on her face as I looked at her then.
Steph laid me back on the bed and stroked my hard cock. She knelt above me and sucked on it again, much like the night before. I felt like a stud, having just witnessed her orgasm, something I helped her to achieve. It didn’t take me long before my balls tightened up and I knew I was close. “I’m gonna cum,” I told Steph. She bobbed up and down a few more times, then pulled off and stroked. I shot my load up onto my chest and stomach, pumping several times while she milked my dick.
Steph collapsed next to me. “That was awesome,” she said. We cleaned up my mess, got dressed, and kissed. “There’s still more you need to know,” she told me.
“Well so far you’re an excellent teacher,” I said.
We made plans to meet again the next night. Same arrangement, same anticipation. Steph arrived and gave me a deep kiss again. “Hey,” she said. “I’m thirsty. Can you get me some icewater?”
I happily went to the kitchen to get it, and I came back to find Steph already naked and under the covers on my bed. I gave her the water, she took a sip and set it in my nightstand. “Get naked and get in here,” she commanded me.
I did as I was told, got undressed and slid into the bed. She rolled toward me and we started to make out. She grabbed my dick and started to stroke it. Without saying anything, Steph pulled the covers off of us. She straddled my face and leaned down to take my cock in her mouth. I instinctively started to eat her pussy. It was my first 69. Steph wiggled her hips as she went to town on my cock, sucking and stroking and bobbing up and down. I grabbed her hips and thrust my tongue into her wet hole, the slid back to her clit, licking and flicking and sucking as she’d taught me. She let out a low moan, which vibrated around the head of my cock. She reached down to fondle my balls; the sensation of everything she was doing at once was almost overwhelming. I leaned a bit to one side to reach my arm around her leg, and pressed my fingers into her cunt. I pumped them in and out while I sucked harder and licked faster. Steph pulled off my cock and stroked me with her hand. “Oh my god,” she said, and her abs clenched. She shook and twitched and ground her pussy into my face. After a few seconds, she collapsed onto me and then rolled off. She turned around and nestled up beside me.
“That was amazing,” she said. “You’re really good at this.”
“You’re a good teacher,” I said honestly. “I can tell what’s working from how you react.”
We laid there for a few minutes, Steph slowly stroking my dick, keeping it semi-hard. I was aching to cum, but also wanted to give her another orgasm. Finally, she said, “there’s something else I want to try.”
Steph reached over for the glass of water. She took a big drink, including some ice cubes, and then spit a big cube out of her mouth. “Open up,” she ordered, and popped it into my mouth. “Zach did this to me, and I want to see if you could do it too.”
Steph had me go down on her again, this time with the ice cube in my mouth. She told me how to put it against her clit and then pull it back and warm her clit with my tongue. I didn’t this a couple of times, having to get a fresh ice cube in between. She enjoyed it as I played with cold and warm and kept up my techniques with tongue and lips and fingers. She seemed to get close to another orgasm, but never got over the edge.
“Come up here,” she said finally, as she pulled me up to the head of the bed. I knelt over her as she pulled my cock into her mouth. After a couple of minutes, I pulled back from her.
“I’ve got a different idea,” I said. I reached over into my nightstand drawer and pulled out a condom. I looked at her and said, “you ok with this?”
Steph nodded and said, “yeah.” She reached down and started playing with herself as I opened the wrapper and rolled the condom down my dick. I slid down to lick her pussy first, giving her a few flicks and sucks and tasting her wetness. I knelt between her legs and slid into her slowly. Steph inhaled sharply as my girth stretched her out. I pressed harder and slid the rest of the way in. Steph bit her lip as I started to thrust, using slow strokes on the way out but firmer thrusts back in. She moaned softly as I picked up the pace. I hit a steady rhythm, sliding out and pounding back in. On each thrust, Steph made a humming noise. I picked up her legs and pressed them back toward her head, allowing me to thrust even deeper. “Oh god,” she said, as I pounded her pussy with each thrust. “Oh god!” she said again, louder, as I sped up even more. Our bodies were slapping together and the bed was starting to creak. Steph pursed her lips, “mmmmmnnnnngghhh,” she moaned, trying to keep the noise down. The walls of her pussy tightened around my dick as I kept up
my thrusts. Her hips began to buck and her legs began to shake as she looked me right in the eyes. I could read her pleasure in them. Finally, I exploded into the condom, rapid pumps and twitches quickly filling it with cum. I grabbed the base of it and pulled out while my dick twitched for the last few times.
I collapsed next to her. “Holy shit,” Steph said. “That was incredible.”
“Thanks,” I said. “I’ve been dreaming about that for years.”
We laughed a little and laid there, hot and out of breath from our exertion. “I’ve never been fucked like that before,” Steph said.
My ego ballooned. “Not even by Zach?” I teased.
“Not even him,” Steph said. “You’re going to make a lot of college girls very happy.”
We stayed warm under the covers for a while until Steph got up to go. She invited me to visit her at school, and I planned to. Over the next few months, I drove down to see her five or six times on weekends. She took me to a couple of parties and I met many of her sorority sisters. Word got around the sorority about my talent – that’s another story altogether. But always Steph and me spent time on my lessons. She showed me some more new techniques, but mostly she was just good about telling me in the moment what to do and not do. It’s Steph who I credit with showing me how to really please a woman, something I still appreciate today.
Source: reddit.com/r/gonewildstories/comments/ybq5a5/she_taught_me_oral_mf
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