[fM] I met an older man online…

For or better or worse, the girls of my generation have had a much easier path to becoming “bad girls.” The internet has made it much easier to meet guys for dating—but it’s also easier for a random hook up, if that’s your sort of thing. For reasons I now forget I made the unfortunate choice of going to a college where the overwhelming majority of students were female, so it’s no surprise that I discovered cybersex during the first month of my freshman year back in 2000. My options were pretty limited, and I wasn’t interested in going dyke—though it made for some experimentation.
To be honest, even if I’d been at a school where the guys outnumbered the girls, I probably wouldn’t have been too interested. I’d had my fill of boys my own age when I was still in high school. Most of the guys at my school were only interested in cute, petite cheerleader types or trashy blondes who wanted to be centerfolds when they grew up. That didn’t describe me at all. I was never the Junior Miss America type.

That’s not to say I didn’t have some things going for me. I just didn’t fit the mold of a classic beauty. For one, I’m pretty smart, and I’ve never felt the need to dumb myself down or play the role of a submissive female who’s looking forward to a life of SUVs and suburban bliss.

Then there’s my looks. Instead of long blonde hair, I had short, brown that come just past my chin. My skin is pale and I have a great complexion, but I didn’t tan at all. I’m short—only about 5’6″, and I have an athletic figure with wider hips, firm ass, a flat stomach, and average tits.

Like I said, I did have some things in my favor, even if the high school boys couldn’t appreciate it. But I did receive a lot of attention from older men, even at a young age. It usually made me uncomfortable, but during my senior year I embraced it. I lost my virginity to a substitute teacher when I was eighteen. I think on some level he appreciated my mind, but for the most part he just liked the way I filled out my uniform and he might have had a fetish thing going on.

He wasn’t that much older than me—only 22. We snuck around for several weeks, and finally we ended up having sex on the futon back in his dorm room. After years spent fantasizing, sex pretty much lived up to all the hype. Tommy and I had sex about a half dozen times before he started to worry about his friends catching him with a high school girl. To be honest, I wasn’t that disappointed when it ended. I wasn’t in love with him or anything. We were just having a good time, and I was eager to continue that with other guys.

After my little fling with Tommy, I had a good idea where to find most of the local college boys. I had always been a bit of a loner, so I had no problem going to these places on my own. After school I’d check out the different shops and coffee houses. I even went to the campus bookstore. Guys weren’t exactly lining up to talk to me, but I got a decent amount of attention.

Tommy had always been fond of my school uniform. It was the typical thing—crisp white shirt, gray pleated skirt, knee socks, black shoes and an optional blue sweater or cardigan. Most of the time I’d wear that to the college hangouts. Usually, the first question a guy asked was my age. I’d tell them I was eighteen—even show them my license if they asked—and then they were interested. Over the next few months I met plenty of guys, but I was a little nervous about the scene. I avoided going to parties and putting myself in a situation that could be dangerous. By the time I went off to college I’d slept with three other guys and I was starting to feel comfortable with sex. But things didn’t really take off for me until I got to school.

I spent a couple of months playing around with cybersex. My roommate at school was the socialite type, to that left my plenty of time to experiment on my own. I even got into a routine. After Trisha left with her boyfriend, I’d go take a nice shower. Then I’d come back to the room wearing white silk dressing gown. Sometimes I’d wear panties, but often I was completely nude. I’d stay up to all hours chatting with men all over the globe, but it wasn’t until late October when I ended up talking with a guy in my city.

It’s been years, but I remember the night like it was yesterday. Trisha was going to a party with her boyfriend and wouldn’t be back that night. It was a Friday night and I’d had a big exam that day, so I was eager to let off some steam. As I stood in the shower shaving my legs I could feel myself getting excited. My rosy nipples were rock hard. I decided to shave my pussy for the first time.

I lathered up the area around it. I thought it might be better to trim first with scissors, but I didn’t have any with me. I went ahead with it anyway. I slowly slid the razor around my pussy lips. With each stroke I could feel my clit becoming more and more swollen. It all felt so naughty. Without thinking about it, I started toying with one of my nipples. I moaned softly to myself. By the time I finished the job my little clitoris was aching for a touch. I rubbed it briefly as I washed off the extra shaving lotion. It was so beautiful. I looked so shiny and smooth. I could see every engorged bit of my cunt.

I leaned against the shower wall for a second and let the hot water run down my naked body and over my newly exposed sex. I wanted to touch myself and I couldn’t wait. The bathroom was quiet. It was late on a Friday night and all the other girls were out for the evening. I gave in to temptation and started rubbing my little clit. I was nervous and excited at the same time. I slipped a finger inside myself and bit my lip so I wouldn’t cry out. Leaning against the shower wall, I finger fucked myself intensely eager to get off. It seemed to last forever, but in reality it was only a manner of seconds until the waves of pleasure caused me to shudder. I’d gotten quite adept at pushing my own buttons.

I stood there for several minutes, just savoring the afterglow. Then I dried off with a towel. I slipped into a pair of silky, lavender panties that felt like heaven against my freshly shaved box. Then I put on my dressing gown, gathered my things, and headed my room to log on.

I popped into a chat room under the name I was using back then: CowgirlSexT9.

As usual, I received about twenty instant private messages. I had never figured out an easy way to pick a winner, so I just responded to the most interesting screen name.

KingofShadows: a/s/l

CowgirlSexT9: 18, female, Charleston

KingofShadows: Small world. I’m in Charleston, too

KingofShadows: So are you looking for a good time tonight? What’s your name?

CowgirlSexT9: You can call me whatever you like if you can do me a favor tonight?

KingofShadows: What kind of favor?

CowgirlSexT9: Make me come really hard.

I always found the way people talked during cybersex to be kind of silly, but I played the game like all the rest. But I didn’t waste time with foreplay and banter. I came to the rooms to get off and I didn’t need a guy to feed me a pack of lies about his life history and what he looked like. I just wanted to talk dirty. If he wanted to pretend to be 26 and ripped with a 9 inch dick, I didn’t really care, as long as he was imaginative and focused his attention on me.

KingofShadows: You know, I could probably do a lot better job of that on the phone. Do you ever have phone sex? If you let me call, I can tell you exactly how I’d like to wear that pussy out with my big fat cock.

CowgirlSexT9: I don’t think that would be a good idea. You might want to stalk me.

KingofShadows: By the end of the night, you’ll be begging me to stalk you.

I thought about it for a second. I had grown kind of tired of cybersex. There was only so many ways a guy could promise to lick your pussy. I looked at my cell phone. It’s not like he could trace the number, I decided, and this might add a bit of fun to it all. I made a quick decision.

CowgirlSexT9: I don’t want to give you my number, but I can call you. My number is blocked so you can’t ID it.

He gave me his number.

KingofShadows: My name’s Dante, by the way. Call quick. I’m already hard.

I logged off the computer and turned the lights down. I went to my bed and lied down on my back. I was already excited by my new adventure. I picked up the cell phone and called Dante.

“Hello,” he answered in a deep voice.

“This is your internet friend,” I said in a sweet voice. “You have a sexy voice, but do you know how to use it?”

“I know exactly how to use it, Cowgirl. But I’m a lot better at using my cock. You’re not some innocent little high school girl looking for adventure, are you?”

“No,” I responded. “I’m in college. All grown up. And all alone in my dorm room, aching to get off.”

“Well, I can help you with that,” he said. “Tell me Cowgirl, are you a virgin?”

“No I’m not, Dante.”

“Have you ever fucked an older man?”

“That’s all I’ve fucked,” I said.

“How much older?” he asked.

I could have lied, but I didn’t see the point. “The guys I’ve fucked have all been in their twenties.”

He laughed. It was a deep, sexy laugh and it excited me.

“I said ‘an older man.’ Those are just boys. How many of those boys have you fucked?”

“Four,” I responded honestly. “And what are you calling a man? How old are you, Dante? How many women have you fucked?”

I could almost hear him smiling over the phone. “I’ve been with a lot of women. I stopped counting a long time ago. That’s a child’s game. And I’m 32 years old and positively salivating at the thought of teaching such an innocent child how to fuck?”

“I’m not that innocent,” I protested, perhaps a bit too quickly. “I didn’t just fuck four times. I stopped counting, too, but it was at least 30 times. Maybe a lot more.”

He laughed again. I realized I had sounded pretty silly. I decided to calm down a bit. His laughter was mysterious and sexy to me and I wanted to see where things would go.

“I apologize,” he said with another laugh. “You’re obviously VERY experienced,” he said sarcastically. “So what are you wearing?”

“What an original question?” I said, also sarcastically. He laughed again.

“Ah, I like your quick wit, Cowgirl. Tell me, do the boys your age appreciate your brains?”

I didn’t answer.

“Tell me what you’re wearing,” he said again. “Tell me what you look like. I’ll start. I’m about six foot two. I’m in good shape. I’m mixed race—white and black—with short hair. I’m wearing nothing but my boxers. My cock is a hard eight inches. Is that big enough for you?”

I offered a sarcastic laugh.

“It’s amazing how all the guys on the internet have a big dick and a good build,” I said.

“I could send you a picture,” he responded, “but that would hardly prove anything. So tell me about you.”

“Okay,” I said. I was used to this part. “I’m about five six, good tits, flat tummy, plump ass. I’m white—very white—with wavy, chin length, hair and blue eyes. I’m wearing a silk dressing gown, light purple satin panties, and tonight I just shaved my pussy for the very first time.”

Again, I could almost hear him smiling over the phone. “I guess I should say ‘Amazing how all you girls have big tits and shaved pussies’, eh? But I’ll believe you, Cowgirl, if you touch that shaved pussy and moan for me.”

I liked the way he was commanding me, so I obeyed. I slipped two fingers into my panties and ran them around my pussy, lingering at my clit. I moaned into the phone.

“I’m touching my pussy for you, Dante. Do you like that? Are you touching your cock?”

“Not yet,” he answered. “I’m not ready for that yet. Is your pussy wet?”

“Mmmm, yes,” I said to him. “VERY wet, Dante. Doesn’t that make you want to jerk off for me?”

“Yes. Yes it does,” he said. “But not yet. I want you to put your phone by your pussy and let me hear you slide your fingers in and out.”

His naughtiness made me hot. I lifted my hips and slid my damp panties down to my knees. I put the phone speaker next to my shaved box and quickly started to pound away at my pussy. The wet sounds of my fingers sliding in and out were very clear. I brought the phone back to my mouth.

“Did you hear that, Dante? Does that make you want to come?”

“Yes, I heard it,” he said. “And it does make me want to come, but I never jack off.”

“Never,” I said doubtfully. I started to put playfully. “Not even for me? You won’t jerk that big black cock for me, Dante?”

“No,” he said. “But I’ll come put it in you tonight, if you want.”

I laughed at him.

“I don’t think that’s going to happen, Dante. I’m not in the habit of meeting guys off the internet for sex.”

“But aren’t you at least curious about what it’s like to be with a real man?” he said.

I laughed again.

“Maybe I am,” I said.

“How about this. The night is young. You meet me at a place of your choice. A place in public. If you don’t like me you can always leave.”

I caught myself actually contemplating his idea. I touched my clit again. I was extremely horny and I hadn’t actually been with a guy since the middle of the summer. The idea was appealing. If I played it right, I could have him stand out front of a public place and sneak up on him. If I didn’t like what I saw I could always take off before he even knew I was there.

“Alright,” I said. I’ll do it. I told him a place and we agreed to meet in half an hour. As I dressed I started to think this was insane. I didn’t really have to go. He couldn’t even call me back for not showing. But my libido was getting the best of me. His voice was so sexy and I WAS curious. I pulled my panties back up and put on a matching bra. Then I put on a white, low cut sweater that showed off my cleavage and a brown, pleated skirt. I grabbed my purse and rushed up the street to meet him.

He was already standing in front of the restaurant. He hadn’t lied about his appearance. He looked to be about thirty. He was obviously at least part black. He was wearing a black leather coat and a white, ribbed shirt that showed off an incredibly muscular body. His jeans hugged his taut little ass. I was debating approaching when he saw me.

“Cowgirl,” he shouted across the street.

I was caught, so I went over.

“So did I lie about my appearance?” he said.

“No. Did I?”

“No,” he said. “Not at all. Wavy hair and nice tits.” He leaned down and put his lips close to my ear. “And I hope to find out about the panties soon.”

His boldness was exciting to me. I looked around and saw that nobody was looking. I grabbed the neck of my sweater and pulled it down just a bit so he could see my bra.

“Lavender,” I said. “And the panties match.”

He put his arm around me and I let him.

“We could go into this bar and I could drink and you could have a Coke,” he said. “Or, we could just skip this and do what we really want.”

I was turned on, but I tried to play it cool.

“You’re awful cocky,” I said.

“Maybe,” he responded. “But I’m guessing you’re just as horny as I am.”

“Look,” I said, “It’s not going to happen like that. I may like sex, but I’m not THAT easy.”

“OK,” he said with a laugh. “We can do it your way. Let’s go inside.”

We went inside and Dante asked for a private booth. We were seated in a back corner. He ordered whiskey for himself and soda for me. I thought we’d make small talk for a bit, but I was wrong.

“So tell me about you,” Dante said.

“What do you want to know?” I said. “I’ve told you my age. Do you want to know my major? My hobbies? My hometown?”

“Don’t be silly,” Dante said. “I want to know if you really know how to fuck or if it’s all just a child’s game on the internet. You can tell me the truth. I don’t mind. I actually have a great interest in educating those who are willing to learn.”

I couldn’t decide whether to laugh or be offended by his tough talk. I ended up giggling a bit.

“You’re awfully full of yourself, aren’t you? Does this tough teacher routine work a lot?”

He just smiled at me for a moment as the waitress brought our drinks.

“You’re free to leave if you wish,” he said. “But I want to broaden your experiences.”

I never honestly thought about getting up. I know I should have been offended. Or maybe just frightened. He could have been a real creep. But I’ve always been a curious girl and I just couldn’t help myself. I could always leave later. I just sat there.

“Have you sucked a cock?” he asked.

“Of course,” I answered. “Plenty of times.”

“Are you good?”

“They always get off,” I answered.

“That doesn’t mean you’re good,” he said. “Do you enjoy it?”

“Sometimes. I like getting them off.”

“You should love it,” he said. “You should savor the moment. You’re in complete charge of a man when you have his cock in your mouth. Women are too willing to think of it as a submissive act when they really hold all the power.” He paused and sipped from his glass. “Have you ever fucked a woman?”

“Um. No,” I stammered.

“Have you considered it?”

I decided there was no point in lying. “Yes, I’ve considered it. I’ve found girls attractive. I’ve stared at girls in the bathroom. But I have no idea how to come on to another woman.”

“What do you like in a woman?” he asked. “What turns you on? Don’t hold back.”

“Well,” I started, “I kind of like girls who are different from me. Not little perky girls or anything, but curvy girls. Girls with big tits and soft bodies. And I like ethnic girls. I think they’re pretty. I think about touching them, sometimes. I think about them touching me.”

“Good,” he said. “Now we’re getting somewhere. Have you been fucked in the ass?

“No,” I said. I was loosening up quite a bit. I was also getting turned on again.

“Have you had group sex? More than one guy?”

“No,” I responded.

“Have you fucked in public?”

“No,” I said again. “Not really. I’ve done some pretty heavy petting and kissing. And I gave a guy a hand job at the movies once.”

“Have you watched other people fuck? Would that excite you?”

“Yes,” I said. “I’ve done that. They didn’t know or anything. They thought I was asleep. I was in the room when they came in really late and did it. And it did excite me. It turned me on and made me a little jealous.”

He kept on with the questions. He asked me if I’d fucked married men. He asked if I owned sex toys or porn. He started listing positions and asking about them. He asked about bondage. He went through most any reasonable sex act in the book, and many that weren’t so reasonable, and I had to answer negatively to most of his questions. By the end of the interrogation I was really feeling like a silly, inexperienced school girl, when only a few hours earlier I had felt deceptively wise. I was also feeling turned on. I couldn’t help myself.

Finally, he seemed to tire of asking questions. We sat silently for a few minutes until he’d finished his drink. He called the waitress over and paid.

“So what now?” I asked.

“What do you mean?”

“Well, you must think I’m pretty silly now,” I said. “I guess I’m exactly what you called me earlier—just a school girl. Must be kind of a let down.”

He flashed that tempting smile at me again.

“I’m not let down at all. In fact, I only have one question left for you.”

“What’s that?” I asked.

“Are you going to prove to me that you’re really wearing purple panties?”

I thought about the question for a second. I looked around. We were all alone back in the corner.

“Do you want me to show you here?” I asked tentatively.

“No,” he said. “I don’t want to show me. I want you to put them in my hand so I can look on my own.”

That seemed like an easy enough request. My skirt was long enough to cover my dignity if I took off my panties. I started to get up and go to the bathroom. He took my arm.

“No,” he said. “Not in there. I want you to take them off right here and put them in my hand.”

I was surprised. That wasn’t what I was expecting at all. Still, it didn’t seem too bad. I looked around again. There was nobody around who could see into our booth. I poked my head around the corner and saw that our waitress was occupied elsewhere.

I went for it. I lifted my hips just slightly and reached under my skirt. The panties were little and tight and I had to wiggle them off my ass. As soon as I did I could smell my own scent. The panties themselves were drenched. I slowly slid them down to my knees, then shifted my legs back and forth until they fell around my ankles. I reached down and pulled them over my shoes and off.

I balled up the damp, lavender panties and discretely passed them across the table, though there was still nobody around. I expected him to sneak a peak and then hand them back, but that’s not what he did at all.

Dante took the balled panties and brought them to his nose. He inhaled.

“I can smell your pussy. I like that.”

I was starting to blush already when he laid the panties out on the table. I think my face turned bright red. I quickly looked around the corner to make sure nobody was coming. When I looked back, my wet little panties were spread out on the table.

“Yes, that’s purple,” he said. He smiled wickedly. He was obviously delighted by my discomfort. He balled up the panties and stuffed them in his own pocket. “Okay. I’ve harassed you enough for one night. Let’s get out of here.”

We left the restaurant and went outside. There was a bit of a breeze and I could actually feel it coming up my skirt and teasing my wet pussy.

“Your first new experience with me,” Dante said. He’d asked me earlier if I ever wore a skirt without underwear. I’d said no, of course.

Dante offered to walk me to the car and I accepted. I wasn’t exactly comfortable with him yet, but I was a lot more uncomfortable walking alone. I’d parked just a couple of blocks in the lot of a business. They had signs saying “no parking,” but I’d been parking being the building and out of sight on evenings and had never received a ticket.

As we turned the corner around the building, Dante put his arm around my waist. I didn’t remove it, even as he slid it down and started to grip my ass. He slowly lifted my skirt until I could feel my ass cheeks hanging out. Then he placed his hand firmly on one of them.

“Are you sure you’re not cocky?” I asked with a wink.

“Calling myself cocky would imply that I’m confident in an ability that I may not have. That’s not the case here.”

I let him keep his hand on my ass cheek. Even though we were behind a building with nobody near, there was still a thrill to what was happening. I felt exposed and I liked it.

As we approached my car, Dante took my hand and spun me to face him. One hand was around my body and still touching my bare ass. He leaned forward and used his body to pin me against the side of the car. Our eyes locked for just a second before he spoke.

“We can start your education tonight if you’re ready.”

My heart was racing a bit. My brain was screaming “No,” but it was loosing a fight with the fire between my thighs. Impulsively, I leaned forward and kissed Dante. He responded with an intense hunger, biting at my lips and kneading my ass with his strong hand.

He spun me around rapidly and told me to put my hands against the trunk. Then he jerked my skirt up. I glanced back over my shoulder and saw him just staring at my bare ass. He put a hand on my back and pushed me forward until I was leaning over the trunk with my butt in the air. He took one finger and slipped it into my soaking wet pussy.

“So you’ve never been fucked in public, right?” he asked.

“No,” I responded.

“Well you’re about to be.”

In the distance I could hear the sounds of traffic, but the only sound that mattered to me was the one that Dante’s zipper made when I heard it going down. I tried to turn and see his cock, but he placed a hand on the back of my head and pushed it down against the trunk of the car. Then he tangled his fingers in my curls and pulled gently.

Dante slowly ran his cock up and down the crack of my ass for a few seconds. Chills ran up my spine. I was dying for him to enter me. Fortunately, he didn’t make me wait long. I felt the head of his cock pressing at me a moment later. Then he forced himself in.

For a second I could just gasp. His cock was HUGE. I felt so STRETCHED and FULL.

“You like that, Slut?” he said. “You like my big cock in you, don’t you?”

All I could do was moan. Dante pulled back gently on my hair again. With his other hand he slapped my ass. I squealed just a bit.

Then he started fucking me.

Dante didn’t waste a single stroke. There wasn’t a moment of teasing. From the first thrust he was burying that big cock in me. I wiggled and groaned as he fucked the hell out of me. The shocks on my damn car started squeaking as he banged the hell out of me. With each monster thrust he gave a slight tug on my hair and a firm slap to my ass.

I tried to thrust back into him and show him I wasn’t just a dead fuck, but he had total control. His big dick plunged into me again and again and all I could do was moan his name. Dante didn’t say much either—he just kept giving me that sweet bone.

It seemed like no time before I felt myself overwhelmed. Every muscle below my waist began to spasm and I felt my cunt gripping his hard cock and attempting to milk it. Again, I cried out his name as my orgasm took me. Dante just fucked right through it.

He didn’t pull out until my orgasm was over. I turned to watch again and this time he let me. His cock was ridiculous—easily the biggest I’d ever seen. He laid the head against my ass cheek and gave it a few jerks.

“Ohhhh!” he grunted as his monster exploded, sending hot come across my ass and onto my brown skirt. When he was finished I stood up and we shared a short kiss.

“Thank you for a wonderful night, Teacher,” I said.

“Hopefully the first of many,” he responded. He started to walk off. Before turning the corner he turned back. “I want you to come to my place for dinner tomorrow,” he said.

“I can do that,” I responded quickly.

“Good,” he said with that wicked smile. “I know my wife will be thrilled to meet you.”

Before I could ask anything else he was around the corner and gone. I rushed home to my computer, hoping there’d be an instant message waiting for me.

Source: reddit.com/r/gonewildstories/comments/9b8m6u/fm_i_met_an_older_man_online