I still remember the night I first met Chelsea.
I was sixteen going on seventeen and it was late '07, during that throw away week between the end of Christmas and New Year's Eve. I was bored and horny, sitting up late at my computer signed into my profile on one of the popular social networks of the day.
What I wanted to do was find some chick willing to get naked on webcam so I could jerkoff and go to bed. But it was a slow night. I had more than a hundred "friends" in my friends list. Mostly girls around my own age. But hardly anyone was online.
I ended up settling for one of the handful of adult women on my friends list. MILFs were a fetish of mine, so I tried to friend a lot of women in their 30s and 40s. Most of them ignored me or gave me one variation of "Lol, I have kids your age" or another. But there was always that one in a couple dozen that would add me.
Kim was a chubby bunny in her mid 30's. She lived in some podunk little town in Ohio and worked in the office of the local high school. She was a BBW with reddish-brown hair and enormous tits. And she was into young guys.
We'd flirted quite a bit during text only chats but nothing serious. Tonight was different. When I asked her for a webcam chat she agreed without hesitation.
"Mmmm," she smiled into the camera. "Show me that hard young cock baby."
I got up and walked over to my bedroom door locking it, then unzipped my jeans and shrugged them off. I wasn't wearing any tighty whities underneath. Now naked, I turned back to the cam and slowly stroked my semi-flaccid penis as I walked back to my chair. I sat there in frame, stroking myself hard.
"Ohhh," Kim cooed. "I'd suck you dry if you were here."
"You any good at giving head," I asked her.
"I've never had any complaints from the boys I've given a blowjob too," she told me.
"Do you swallow??" I asked.
"Sure do sugar," she licked her lips. "I love the taste of cum."
"Fucked many guys my age??"
"Not as many as I'd like," she told me. "I have this fantasy of being totally naked on the shower floor of the boys locker room and letting the entire phys ed class run a train on me. I'd love to have a cock in my pussy, a cock in my ass and a cock in my mouth all at once."
"Wow," I laughed. "That's hot."
"Do you cum a lot when you orgasm??" She asked me.
"Usually," I replied.
"I just love when a guy creams all over me," she reached up and squeezed her tits.
"Take your top off," I said. "Let me see them."
"You love my tits don't you??" She smiled and pulled her shirt off, then unfastened her bra and dropped it to the ground. Her tits were massive. I sat and stared at her boobs and their large dark areolas and fat nipples. "I bet you'd like to motorboat these wouldn't you??"
"Sure would," I replied. "You should get totally naked and masturbate with me. I want to watch you."
"Oh sorry love," she shook her head. "I don't show my pussy on cam."
"Why not??" I asked. "I'm showing you my dick."
"It's just a rule I have," she said. "I never show my pussy on cam. You should come visit me. You can see it all you want. I'll be your whore. You can fuck me any way you like."
"That's a jip," I smirked. "I'm naked, you should be too."
She apologized again. I was pissed. I leaned forward and slapped a key on the keyboard and the cam on my end went dead. "Bitch," I muttered. A moment later she sent a text message "Sorry you feel that way love." I clicked another key and ended the chat altogether, then booted her from my friends list.

Now that the webcam chat was over I noticed I had a new private message waiting. I was tempted to ignore it. It was probably just some teenybopper sending me that oh so original first message "Hey, whats up??" But on a whim I clicked on it.
I saw a picture of an average looking girl with magenta colored hair and blue eyes along with a message introducing herself as Chelsea and asking if I wanted to chat on webcam.
I grabbed my jeans and put them back on and then pulled on a shirt for good measure and told her yeah we could chat.
A moment later I was staring at two girls. One was Chelsea and the other was named Maegen. Maegen was Chelsea's best friend and she was absolutely gorgeous. Tall, chestnut brown hair, soft brown doe eyes and curves in all the right places.
We sat and chat for about an hour. I found out the girls lived one town over. I also discovered that Maegen was a world class bitch. She was hot and she knew she was hot and she demanded that you acknowledge her perfection. When I got tired of her "I'm so cute" routine and began ignoring her in favor of Chelsea, she got pissed.
"You're probably a fucking perv or something," Maegen complained. "I bet you're a total creeper. We shouldn't even be talking to this guy."
Chelsea rolled her eyes and told Maegen to chill, but she wouldn't. She kept bitching, so Chelsea finally snapped on her and they argued. Maegen stomped off to the bed and flopped across it to watch TV while Chelsea talked to me alone. She told me to just ignore Maegen and that we should talk again soon. We did the next night and every night after that for the next year.
Chelsea was fourteen and on home studies. She said there had been an "incident" at school involving herself and a certain male teacher. The school had elected to tidy up the mess by quietly shuttling the teacher to a new job in another school district, while Chelsea was given home studies. She didn't mind she said because school was bullshit and she learned more on her own. I was a home studies kid myself.
I found that Chelsea was incredibly smart. She was into some deep philosophical shit that went right over my head. She liked to study the concept of morality and question why certain things were taboo in one culture and perfectly fine in another. She considered herself a hedonist and liked to tell me life was too damn short to inhibit yourself.
Chelsea was the first girl I knew that admitted to watching and enjoying porn. We'd exchange url's to porn videos online and even watch them together while chatting. She also had no problem getting naked on cam. She was chubby but not yet what I considered fat. She had a nice set of tits for a girl her age and a cute round ass just made for smacking. She'd masturbate for me sometimes, jamming three fingers inside her pussy and fingering herself furiously, moaning and arching her back slightly as she lay on her bed. When she would finish she'd show me her slippery glistening fingers and suck on them.
"You really need to taste me," she'd tease. "I taste good."
"I bet you do," I'd tell her, grinning from ear to ear.
Nothing was taboo for Chelsea. We'd discuss our personal fetishes and sexual fantasies and no matter what I'd tell her, she never judged me or thought it strange.
"I think it's hot that you have incest fantasies about your mom," she told me. "A lot of guys do. They're just too chickenshit to admit it."
She asked me to sneak into my mom's bedroom one day and steal a pair of her panties. So I did.
"Smell them," she told me. I brought the panties up to my nose and inhaled. "Can you smell her pussy??"
"Oh yeah," I nodded, my dick getting hard.
"I bet you'd like to taste her pussy wouldn't you??" She asked. "Or have her give you a blowjob."
I thought about my mom and imagined myself face fucking her. Or maybe I'd bend her over and fuck her in the ass, I thought. She'd moan and groan just like she used to when I was little and heard her and my dad having sex. I remembered all those nights of lying in the dark listening to the bed springs squeak and mom's moaning in the next room, my cock sticking straight up in the air. I wrapped the panties around my hardon and masturbated furiously. Chelsea sat and watched me on cam, with her hand between her legs. When I came, I covered those panties in jizz.
"Taste it," Chelsea told me.
"Eh," I frowned. "I don't know..."
"Taste it you chickenshit," she smiled. "I want to watch."
I sighed and dabbed some cum on a finger and gingerly tasted it. "It's salty."
"Eat more fruit," she laughed.

It was March '08 before Chelsea agreed to a face to face meeting. She picked a mall in her hometown and named a time and day. I had my mom drive me there and drop me off. I saw Chelsea wasn't alone.
"This is Jennifer," Chelsea nodded at the obviously lesbian girl beside her. Jennifer was short and leanly muscular. Her hair was shaved down to a barely there dark peach fuzz and she'd cut the arms off her T-shirt to show her heavily tattooed arms. I didn't know if they were real or temporary. She had on baggy camo pants and shitkicker boots. She held her hand out. "Whats up??"
I shook her hand and we three entered the mall. We spent about three hours wandering around Spencer's, GameStop, and even went into Victoria's Secret where I bought Chelsea a few things. We finished up at the food court.
"Jennifer is my lesbo lover," Chelsea smiled at me over her strawberry milkshake. "We have sex sometimes."
Jennifer grinned and ran a hand over her head, as if slightly embarrassed by the admission.
I felt a slight surge of jealousy, then thought that was kind of hot.
"She's also my cousin," Chelsea added, winking at Jennifer. This time Jennifer laughed and blushed slightly.
"Cool," I said, stuffing my last bite of corndog into my mouth. I didn't know what else to say.
Chelsea and I shared our first real kiss outside in the parking lot, while Jennifer hung back waiting.
"Get on cam soon as you get back home babe," Chelsea told me. "I want to model the stuff you bought me."

The second I got home I locked my bedroom door and got on webcam. Chelsea had been waiting for a while.
"Jeez," she said. "Took you long enough."
"Sorry," I told her. "Mom stopped at the grocery store."
Chelsea got naked on cam right in front of Jennifer and me both and modeled the sexy blue teddy I'd bought her, followed by the half dozen pairs of sexy panties. By the time she was done I was rock hard.
"Baby," Chelsea leaned into the camera. "Jennifer and I are horny. You want to watch us fuck?? We're gonna have sex."
She didn't have to ask me twice.
I watched them take their clothes off. Jennifer surprised me, she had a lot bigger tits than I thought. Once she took off her sports bra, a pair of gorgeous boobs bounced out. She didn't have a bad little body on her at all. I watched her and Chelsea kiss and crawl onto the bed where they lay cuddled up kissing and moaning slightly, their hands roaming each others bodies. Finally Jennifer slid down between Chelsea's thighs and began eating her pussy. Chelsea sighed and ohhed and made little whimpering sounds, writhing around as Jennifer's fingers and tongue sent little electric jolts all through her body. After about twenty minutes they traded places and Chelsea began eating out Jennifer. Unlike Chelsea, Jennifer wasn't clean shaven. She had a bush of dark hair but it didn't seem to bother Chelsea at all. They finished by kissing some more. I'd managed to cum three times while they had sex. It lsted about an hour.

My second face to face meeting with Chelsea we were alone, just the two of us. We went to see a movie and she gave me head in the back row of an all but deserted theater. While waiting for my mom to pick me up, Chelsea snuggled up to me.
"What did you think about the show me and Jenn gave you??"
"I loved it," I told her.
"Me and her have been fooling around since we were little," Chelsea told me. "We used to finger each other in the bathroom at school when we were in jr high."
"Nice," I kissed her forehead.
"I want to watch you fuck my mom," Chelsea said casually. I thought I misheard her and asked her to repeat what she said. She did.
"Why??" I asked.
"I just do," she shrugged. "I think I know how to set it up too."
She told me her idea. I wasn't sure about it. But she promised me a threesome with Maegen if I did it. I remembered how hot Maegen was and despite the fact she was a bitch, I desperately wanted to fuck her.
The next weekend I arrived at the mall and then followed Chelsea's instructions on how to find her house taking the local busses. It took about 45 minutes.
When I arrived I saw her mom standing in the doorway of the living room staring at me as if she hated my guts. If Chelsea had told her the story she told me she was going to tell her, I knew why.
"Mom," Chelsea said, "this is..."
"I don't want to know," her mom said. "Let's just do this and get him out of my house and I never want to see him again or hear about you having anything to do with him."
Chelsea looked at me, barely hiding a smile and nodding.
What Chelsea had done was tell her mother that she had bought some pot from me but didn't pay for it. So now I wanted sex or I'd have some girls I knew beat her up. Knowing her mother wouldn't let her provide the sex, she volunteered herself.
Chelsea's mom wasn't a bad looking lady. She was dyed blonde and had the same nice rack that seemed to run in the family. She had a little bit of a pot belly, but I didn't mind.
I started to follow her into the bedroom when Chelsea kicked me hard. I winced and stared at her, she mouthed "take me with you!" and I remembered.
"I want Chelsea to watch, just so she knows how serious this is," I tried to act tough and didn't even convince myself.
Her mom balked and before I could speak, Chelsea asked her if she'd rather she got beaten to a pulp?? Her mom sighed and threw her hands up.
So I fucked her mother in the missionary position on a bed while Chelsea watched, hiding her smile behind a hand placed over her mouth. When I was done I pulled my pants back on and went home.

"I fucking love you," Chelsea smiled at me on webcam after I got home.
I took a bow. "My pleasure."
Chelsea and I talked a while about Maegen and she told me she had already set up the threesome. It turned out Maegen had liked me a lot that first night and she'd been hurt that I didn't seem as interested in her as I was in Chelsea so she'd lashed out. But she really did like me.
I wasn't sure of that, but didn't say so. Chelsea gave me Maegen's cell phone number and I called her and we talked. She seemed ok with everything.
The three of us got together at my house for once, one a day when I had the place to myself and we had our much anticipated threesome. It was amazing. In fact, afterwards I found myself falling for Maegen. Our phone chats started taking more and more time away from my webcam sessions with Chelsea.
In the end I dropped Chelsea and her increasingly taboo fantasies in favor of a more normal relationship with Maegen. Chelsea called us both every name in the book and then some. For a while I was afraid she'd somehow get me in trouble for some of the things we'd done together (trust me, I left a lot out). But she seemed to just ignore us afterward.
Maegen and I dated off and on through just last year when she got pregnant and had a baby with another guy. I told her she'd make a good mom and I'm still her friend. As for Chelsea, she's still on the Net. Maybe she'll hook one of you guys next.