I doubt any single women under 40 read erotica online today. Amazon has cornered the market on limitless reading at a low price. And people who are just looking to connect with others are more likely to use a dating app or Reddit.
But that wasn’t the case in the early 2000s. Before the social networks took over, there were places online where people would go to write and share their interests with like-minded strangers all over the world. And every once in a while a real connection would form. I met people from journaling sites and music blogs. But I made the most intimate connections from writing erotic stories.
Ivy and I started chatting in the fall of 2002. At the time I was writing a lot of melodramatic young love erotica. It’s what appealed to me and I didn’t see a ton of it online. Ivy read a couple of my stories and sent me a short note saying she’d enjoyed them.
There was nothing flirty about the first message. I thanked her, like I would anyone else, but didn’t think much about it. I rarely received feedback on my stories and even when I did there wasn’t much back and forth.
Ivy wrote back and asked a little more about my stories. She wanted to know if they were real. She commented on the common themes of young love. She asked if I was really a romantic or if that was just the stories.
At that point in my life, I had met two women through writing. But I was still skeptical of the majority of people online. Too many people were posing as women and using obviously stolen pictures from porn sites. It didn’t take a reverse image search to figure that out.
But Ivy was different. She was drawn to the romantic aspects of my stories more than the sex. She was flirtatious but in an affectionate way. Unlike the obvious posers, she didn’t try to jump into sex chat or tell me that she was a runway model who couldn’t resist sex with strangers she met online.
Our correspondence moved beyond talking about stories. We started talking about our lives. Ivy asked if I used an instant messenger. Like everyone else, I used several in 2002 to keep in touch with friends.
At the time I lived alone in a small town three hours away from most of my friends. I spent a lot of time online on weeknights. Ivy was working her way through community college and she lived with her mom in the middle of nowhere. We ended up chatting almost daily.
I could tell that Ivy had a crush on me. It didn’t matter that she lived several states away. She often mentioned the lack of options in her town and how she didn’t want to settle. She had dreams of moving away and going to law school, but waiting tables full time only allowed her to take a couple of college classes a semester.
I couldn’t help but be wary. I knew I was Ivy’s escapist fantasy. I didn’t know what she looked like. I’d never even asked. And everyone knew that people online were prone to misrepresentation. She’d told me that she was a promising gymnast but before she got too curvy. It seemed like an exaggeration.
But I couldn’t help liking her. She was sweet and naive but also witty and had an interesting outlook on the world. We could talk about politics or pop culture or nothing at all for hours. I was in my early twenties and had gone through a string of purely superficial relationships. It was easy to be drawn to someone who offered something more.
Ivy was shy. She had dropped hints about wanting to talk on the phone. But she never outright asked and I was content to pretend I didn’t notice her hints.
That changes when we started talking about sex.
“I’m so glad you shared your stories,” she typed. “Or we would have never started chatting.”
“I know,” I responded. “I’m glad you liked them. Although I never expected someone to only be interested in the characters and not the sex.”
“I never said that,” she answered. “I liked the characters and the sex.”
“You never mentioned the sex.”
“I thought that part was obvious since they’re dirty stories,” she said.
“What did you like about the sex? Did it turn on you?”
“Of course it turned me on,” she said.
“What did you do then?” I asked.
She paused for several seconds before answering.
“You know,” she answered.
“Tell me,” I wrote.
“Why? You know.”
“I want to know all about it,” I wrote. “Maybe you can even tell me on the phone. If you prefer.”
She didn’t answer for a couple of minutes. Then she typed her phone number.
“If I call will you get shy?” I asked.
“Yes. Of course.”
“That will be awkward,” I answered.
“I promise to tell you what I want to hear.”
I told her to give me a few minutes and logged off the messenger. I took my phone and moved to the bedroom. I was nervous. What if she sounded like a grandmother? Or a man?
I dialed the phone. Ivy picked up on the first ring.
“I have to be quiet,” she said. “My mother is sleeping.”
I looked at the clock. It was close to midnight. I knew if I hesitated we might spend an hour avoiding the reason I called.
“Tell me what you liked,” I said.
“About the sex?” she said quietly.
Ivy had a soft voice with just a hint of a northeastern accent.
“You said you would tell me what I wanted to hear,” I said sternly.
“But you know,” she said.
I waited quietly.
She started to recall a story I’d written about best friends becoming lovers.
“I was so caught up in the emotion,” she said. “And then the sex started. I liked how he took control. But he was still tender. He was affectionate. But he was also in charge.”
“And how did you react to that?”
“It turned me on,” Ivy said.
“And what happened when you were turned on?”
“I got wet,” she said.
Her voice was getting meeker and breathier at the same time.
“And what did you do then?” I asked.
“I touched myself. And I imagined I was her. And you were doing those things with me.”
“Did you cum?” I asked.
“Yes,” she said quietly.
“More than once?”
“Not that day. But I have again since.”
“To the same story?” I asked.
“Yes,” she said. “At first. But then we started chatting.”
“And then what happened?”
“I realized the character is kind of like you. But not exactly,” she said.
“So you couldn’t get off to it anymore?”
“I don’t know if I could have,” she said. “But I didn’t want to.”
“Because I started making up my own fantasies. About me and you.”
“Do you do that a lot?” I asked.
“Yes,” she answered.
“When was the last time?”
“Yesterday,” she said.
“Fuck,” I responded. “That’s hot. I’m hard just thinking about it.”
“Are you?” she asked. “I’m very wet.”
I was wearing nothing but basketball shorts. I rubbed my hard cock through them.
“What are you wearing?” I asked.
“Just a big white t-shirt and panties,” she said. “Pale blue panties. Bikini cut.”
“Are they wet, Ivy?”
“Yes. They’re soaked.”
“I want to hear you cum,” I told her. “For me. Right now.”
“Should I take my panties off?” she asked.
“Are you naked?” she asked.
I slipped off my shorts. I was in bed completely naked and told her so.
“How do you touch yourself?” I asked.
“I’m using two fingers. I’m sliding them in and out of my pussy. I wish it was you.”
I wrapped my hand around my swollen cock. I had to fight the urge to get off quickly. I wanted to savor the moment. And I wanted to hear Ivy cum.
“Do you touch your clit?” I asked.
“Yes. I use my thumb. Do you wish you were here?”
“I do. I want you, Ivy.”
“I wish you were in my hot cunt,” she said. “I can’t stop moving my hips. Fucking my hand.”
“Keep going, Ivy. I wish you were here on my hard cock. Bouncing up and down.”
“You like it,” she said. “I have really big tits.”
I didn’t know if she was telling the truth and I didn’t care. My cock was throbbing. I squeezed my head to keep from humping.
Ivy was breathing heavily. She moaned into the phone
“I need you,” she said. “I need you in my pussy.”
“Would you let me cum in you?” I asked.
“Yes,” she answered. “Yes, yes, yes. Please cum in my pussy.”
She stopped talking. I could hear her moaning and gasping for air.
“I’m going to cum,” she said. “Should I cum?”
I stroked my cock faster.
“I’m cumming with you,” I answered.
We both moaned and panted into the phone. We came almost simultaneously. I came all over my stomach while Ivy moaned my name.
“Do you still respect me?” she joked afterward. “Do you think I’m a slut?”
“I respect you even more,” I joked.
We talked for a few minutes. It was late and we were both spent. Finally, we said goodnight.
There was no going back from that point. I tried. I knew she had feelings for me that I couldn’t reciprocate.
Talking to her online had become a part of my routine. I missed her when we didn’t chat. Every time I saw her on messenger she’d ask me to call. I’d avoid the topic. Then we’d get into a conversation and I’d end up steering it toward sex.
“You mentioned you’re curvy,” I wrote one night. “And on the phone, you said you have big tits.”
“Too big,” she wrote. “They make me look silly.”
“Why is that?”
“Because I’m barely five feet tall and 34dd. I have a hard time finding a bra that fits. I can’t wear a lot of blouses with buttons and pullovers make me look fat. I’m not fat by the way. I’m cute. And very fit.”
“You sound sexy,” I wrote.
“I don’t think so,” she responded. “Maybe some days. I think I’m just cute. Too short. Too busty. I’m not what guys want.”
“I want you,” I wrote.
“Come get me.”
“Describe yourself some more.”
She didn’t have a digital camera. They were still rare back then.
“Call me,” she wrote.
I couldn’t resist.
“Describe yourself,” I said.
“Five foot one,” she said shyly. “Hourglass figure. Big ass. Big boobs. Small waist. Muscular legs.”
“Fuck, you sound sexy.”
“Green eyes,” she continued. “Dirty blonde hair. Shoulder length with bangs. Perfectly round face. My nose is too small.”
“I’d have a hard time keeping my hands off you,” I said.
“You wouldn’t have to.”
“What are you wearing now?” I asked.
“That’s not what I asked.”
“Gray sports bra. Pink cotton panties. A t-shirt and pajama pants.”
“Are you wet right now?”
“I’m wet every time we chat,” she said.
I took my cock out and the dirty talk escalated. I climaxed listening to Ivy pleasure herself.
“I’m not joking,” she said after. “You can have me for real. Come get me.”
I quickly became addicted. We talked a few nights a week. Sometimes for four or five hours with each of us having multiple orgasms.
I knew I had to fuck Ivy. It seemed insane to drive several states just to get laid. Ivy obviously wanted it to lead to more, but I couldn’t see myself in a long-distance relationship. But I needed to find out if she lived up to my fantasies in person.
Ivy kept mentioning a weekend when she would have the house to herself. She didn’t want to come to me. The romantic in her wanted me to come to sweep her off her feet.
I wasn’t thinking about romance. And that made me conflicted. I didn’t want to take advantage of her feelings. But I was dying to fuck her.
I took a Friday off from work and drove eight hours. The entire time I questioned what I was doing. It felt ridiculous. I had no desire to get involved with someone so far away. And I could have found meaningless sex closer to home.
But I couldn’t turn around. We were long past the point where she’d be hurt if we never met.
I fantasized about walking through the door and carrying her straight to the bedroom. But I was in my mid-twenties and not nearly as confident with women as I am now. When she opened the door we hugged. We were both bashful. We talked about my drive up.
“We should go get dinner,” she suggested.
“Or we could just go to bed,” I said with a smirk. Definitely not smooth.
“No,” she said with a stern look.
For the first time, it dawned on me that sex wasn’t a given. Ivy was smitten with me. But that didn’t come with any guarantees. She wasn’t looking to just fuck. She wanted romance and seduction.
And she deserved it. We’d been talking for months and at times I’d taken her for granted. Especially when we were talking dirty. But she was an intelligent, interesting woman and the reason we’d spent so much time talking was that she made me smile, and laugh, and want to impress her.
And she was gorgeous. She reminded me of Kristen Chenoweth. She was small with blonde hair. Her skin was fairer and her tits were bigger. And she was quiet and thoughtful instead of boisterous.
Her black sleeveless shirt dress had a red rose pattern. She wore it with a white cardigan and platform sandals. Her hair was down. Her attire and shy demeanor gave her a church girl or librarian vibe. I couldn't believe she was single and willing to pursue a long-distance romance. Either the guys in her town were insane or there was nobody who met her standards.
We went to a small Italian cafe nearby. It wasn’t fancy, but it was charming. I ordered a light meal. I didn’t want to be sluggish after dinner. I wanted a bottle of wine to help us relax, but Ivy wasn’t 21, so I had to settle with just a glass for myself.
The newness of the situation didn’t last for long. Soon we were talking like old friends and flirting like any couple on a date. Ivy insisted on dessert and slid close to me in the big booth while we shared tiramisu. I put my hand on her bare knee just below the hem of her dress. She didn’t stop me from slowly rubbing her thigh.
“You’re naughty,” she said.
“I told you I wouldn’t be able to keep my hands off you.”
“And I told you that you wouldn’t have to,” she said with a smile. “I want you to take me home and make love to me.”
We finished our dessert and I paid the bill. It was a short drive back. Ivy kept her hand on my thigh the entire time.
“I spent my entire paycheck on new underwear,” she said.
“You didn’t have to do that.”
“I know. So you damn sure better appreciate it.”
I parked in front of the small, old farmhouse where Ivy lived with her mother. We were both nervous and excited.
“I’ve never spent a weekend alone with a man,” she said.
I knew she wasn’t a virgin. She’d ended a long term relationship the summer before we started writing one another. But her past experiences were with boys her age. Rushed experiences when her mother was out. I didn’t plan on rushing anything.
We walked inside. Ivy locked the front door behind us. I took her hand in mine.
“You’re beautiful,” I told her.
Ivy blushed. “That’s not true,” she said. “I’m cute. I have a doll face. I don’t have the cheekbones to be beautiful.”
“You’re delusional,” I said. “You’re incredibly attractive. You have an amazing body.”
“Is that what matters to you? Am I just a pretty girl to fuck?”
“Of course you’re more than that, Ivy. I wouldn’t come all this way if you weren’t. You’re witty and interesting and kind. Your mind is as sexy as hell.”
Her face lit up with a big smile.
“I want to kiss you,” I told her.
Even in heels, I was almost a foot taller than her. I had to lean over to kiss her full lips.
I wrapped my arms around her waist and pulled her close. She moaned softly when my tongue parted her lips.
She took my hand and led me down the short hall to her room.
The room was tidy with a big queen bed in the center and an overstuffed chair by the window. Her walls were covered in posters from the late nineties indie rock bands. She draped scarves over the bedside lamp to give the room a romantic glow. She lit incense.
I sat on the chair waiting patiently. I wanted everything to be just as she wanted. My cock was hard just from watching her athletic body gracefully move around the room in her short dress.
She slipped off her shoes and cardigan. Then she came to me and took my hand. We were face to face. I stared into her beautiful green eyes.
We kissed. I pulled her body to me. She straddled me on her knees. Her dress was pushed up. I touched the smooth, pale skin of her thighs. She shivered as I moved upward. I could feel the heat from her pussy.
“Touch me,” she whispered.
I lifted her dress. She wore black silk panties. I ran my hand between her muscular thighs. Her panties were hot and wet.
“Is this how you touch yourself when we talk?” I asked.
“At first,” she said. “But I’m usually in bed.”
“And then what happens?”
“I take off my panties.”
I rubbed her pussy faster. Ivy squirmed and moaned.
“Unbutton your dress, Ivy.”
She nodded and opened the top few buttons. Her full tits were held tight in a silky black bra. I held her tight with one arm and kissed her neck and cleavage. I pressed harder on her pussy with my other hand. Her body responded to my touch.
I slipped two fingers in the leg of her panties. I penetrated her pussy for the first time.
“I can’t wait to put my cock in you,” I said.
“You can right now,” she answered.
“Not yet. You’re going to cum for me first.”
Ivy let out a disappointed moan. She slid a hand in her panties and worked her clit while I fingered her. She drove her hips into my fingers. I recognized the signs of her orgasm. Her whimper was even hotter in person.
“Cum for me,” I said. “Cum for me so you can have my cock.”
She fucked my hand with her tight pussy. She rubbed the hell out of her clit. And it happened. She wrapped one arm around my head and buried my face in her big tits as she climaxed.
“Take me to bed,” she pleaded. “Make love to me. I’ve dreamt of this for so long.”
I cupped my hands beneath her soft, round ass. She held on as I stood. I laid her down on the bed.
I straddled her. I took my time opening every remaining button on her dress. All the way to the hem. She looked amazing with her dress completely open. Her pale flesh a sharp contrast to her silky black lingerie.
I kissed her lips. Slow and deep. I kissed her neck. Her cleavage Her soft stomach. I skipped down to her inner thighs.
I stood up and grabbed her panties. I pulled them down her shapely legs. Her mound was perfectly smooth.
I took my time undressing. I knew the anticipation was driving her wild.
She sat up and slipped her dress off her shoulder. She unclasped her bra. Her big tits were impossibly perky. They defied gravity. There wasn’t enough space for a pencil between them.
I kissed my way up her legs. From her knee to her inner thigh. I ran my tongue up her pussy. I flicked her clitoris.
“You’re driving me wild,” she whined.
I swirled my tongue around. I pushed two fingers back in her hot little cunt. I pulled out and held them to her lips. She tasted herself eagerly.
“Do you want me to eat your pussy, Ivy?”
“I want you to fuck me,” she pleaded. “You promised. I need you inside me.”
I couldn’t hold out any longer.
I spread her legs. I rubbed the tip of my cock up and down her wet slit. I leaned forward and eased into her tight pussy.
I thought she’d climax right away. I squeezed my cock. She wrapped her legs around my back and locked her ankles. She pulled me deeper.
Her pretty green eyes were locked on mine. We kissed. I started to thrust.
Ivy kissed my neck. She moaned my name. She buried her nails in my flesh. I fucked her nice and slow at first.
“Do you like me in your pussy?”
“Yes,” she moaned. “You feel so good. I’m yours. I belong to you now.”
I drove my cock into her. I couldn’t take my eyes off hers. She moved her hips my thrusts.
“I’m going to cum,” she panted. “I’m going to cum for you.”
I felt her pussy contract on my hard cock. She dug her nails in. She cried out and came for a second time.
I sped up. I felt like an animal. I needed to cum. She could sense it.
“Nobody has ever fucked me without a condom,” she whispered. “Be the first. Cream in me. Cream in your pussy.”
I lost control. I fucked her with everything I had. My cock spasmed. I unloaded inside her pussy. Shot after shot of hot cum.
“That was the best sex I’ve ever had,” she said later.
We were under the covers. Iris had changed into flannel pajamas that should have been a turnoff, but she was still adorable. I was nude and hoping for another session.
I knew she was being sincere. Although I didn’t consider beating out a couple of college freshmen to mean much.
“Is this just this weekend?” she asked.
It seemed a little soon to be asking that on our first night together.
“I haven’t thought about it,” I lied.
“It’s okay if it is,” she said. “I invited you here. I wanted this.”
She ran her hand up my bare thigh. She found my cock and rubbed it.
“I just want a warning,” she said. “I think that’s fair. We don’t have to talk about it now. We can still have fun. We can have a lot of sex. But be honest with me before you leave.”
It was hard to focus on the conversation with her hand on my dick. I was getting harder.
“Honest about what?” I asked. “What kind of warning?”
“If this is just a fling,” she answered. “I can be an adult about it. Just tell me if I should stop myself from falling for you.”
Twelve hours earlier that comment would have freaked me out. I was open to seeing where things went, but I didn’t expect much. I wanted to take things slowly.
But a lot had changed in a few hours. I’d been ignoring my own feelings. I was afraid of the complications that go with a long-distance relationship. I wanted to keep my options open close to home where it would be easier to get involved with someone.
I couldn’t keep my defenses up. I didn’t know what would happen. But it no longer scared me.
“I promised to be honest with you, Ivy. And I want to see where this goes. Wherever it goes.”
I pulled her close and kissed her. A slow, sensual kiss.
She flipped the covers back and kissed my thighs. She licked my stiff dick.
“Mmm,” she moaned. “You taste like my pussy.”
She wrapped her lips around my dick. She worked head with her tongue. Ivy had bragged about her ability to suck cock, but most women do. She quickly proved it wasn’t all talk. My entire body was tense. I had to be in her again.
“I need you, Ivy.”
“Then take me,” she said.
I sat up and kissed her. I told her to get on her knees and grab the headboard. I moved behind her and tugged her pajamas down. Her pale, plump ass was amazing.
Her pussy was soaking wet. I held her hips and entered her from behind.
It was a hard, quick fuck. My thrusts were slow and deliberate. Each one rattled the bedframe. Ivy cried out with pleasure.
“Make me cum,” she said. “Make me cum.”
I fucked her like a piece of meat. Her cries echoed off the walls. She was so close. We came almost simultaneously. I filled her pussy again. She worked her clit. A minute later she was cumming, too.
We collapsed in a heap. We couldn’t stop kissing one another.
“Fuck, you’re beautiful,” I said.
We kissed again.
“Maybe you’re the one who should promise to warn me,” I said.
“That’s ridiculous,” she said. “I’m yours.”
I fell asleep looking forward to finding out if that was true.
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with this note attached, it has been posted without my permission.
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