Hillary

When: January to February 1990

Status: Divorced, boyfriend, two kids

Occupation: Real Estate Agent

Meetings: 12

Age: 36

Well, I'll give you the same warning I gave you in the Kara entry: you can go ahead and read this without reading the previous entry I did on Caryl, but this will make more sense if you do.

Hokay, dokay then.I met Hillary, Caryl's friend, in May of 1989, shortly after I started dating Caryl in April of 1989.

The woman was totally adorable, and being the pig that I am, I wanted to boink her the minute I met her. Of course, dating a prospective poachette's best friend is a pretty big cock blocker.

Caryl wasn't the only roadblock to my potential happiness. Hillary had a boyfriend named Ted. I hated this chump the minute I met him. And for the rest of the entry, he will be referred to as Toolshed Ted to reflect my intense dislike of him.

Toolshed was pretty much your typical yuppie type of guy. He was a vice-president of loans or something at a bank, made lots of money, and really wasn't afraid to show it with his purchase of expensive shoes, clothes, and a black Jaguar. Awesome car, when it was actually runningSnicker.

Anyway, the Shed loved me for some reason. Maybe he liked the fact that I was this freewheeling freelance type of guy. Maybe it was because I was one the few guys he met that didn't want to immediately beat him to a pulp (well, I did, but I hid it well).

Anyway, Caryl and I started hanging out with them quite a bit starting in June. Caryl and I were pretty set in our relationship by then (such as it was) and she loved the idea of hanging out with another couple. So we'd go out to eat with them, watch a movie, shit like that. Besides, while I didn't like the Shed, I did like Hillary quite a bit. And Caryl seemed to like Toolshed quite a bit for some reason.

Hillary, though, really was kind of opposite, personality-wise, from Caryl. Caryl was the serious type with a low-key personality. She didn't have too much of a sense of humor. Hillary, though, was a riot. She loved to joke around and laugh, tease people, and get teased herself. She could give a joke and take a joke. With Caryl, you always had to be careful with what you said. With Hillary, you didn't. She wasn't as thin-skinned as Caryl.

So it wasn't too bad. We'd usually do these couples nights two or three times a month. It kept Caryl happy, and if she was happy, I got to fuck her more. Fucking is a good, good thing. And bullshitting with a pretty real estate agent was a lot of fun as well.

So let's spin this entry forward a few months, to New Year's Eve.The Shed and Hillary invited Caryl and I over to her house for a New Year's Eve party. Well, whatever your girlfriend wants, right? But I sure wasn't looking forward to an evening with Toolshed. And with Caryl there, it wasn't like I could do any recruiting.

Caryl had found something else to get pissed off about that day as well. When I got to her place to pick her up, she asked if I had gotten a cake she had asked me to get. Of course, I had totally forgotten. I didn't quite get the need for some stupid cake, anyway. The party was being catered (no, not by Cheri although that would've been awesome), so why bring food?

"Just a nice gesture, Ryan," she shrugged. Actually, it more of a sneer than a shrug.

We stopped by a grocery store so she could buy some stale-ass cake. When I pulled into a parking spot, she said, "Stay here, I'll run in," and slammed my truck's door. I remember thinking, "Man, this is fucked. I'm so sick of this shit."

Okay, that was it. I was dumping her bitch ass. I was swamped with some projects that day and forgot. Big fucking deal. Who brings some stupid cake to a catered party? Fuck. Should I have brought some hats and streamers as well? Maybe bring the punch bowl?

When you go to a wedding, do you bring the gown? When you take your car to have it's oil changed, do you stop by Advanced Auto Parts and get some Penzzoil?

Caryl came back and we drove to Hillary's in silence. She just stared straight ahead the whole way. I was really wishing that I had laid out the money for an ejector seat on the passenger side of my truck. All I would've had to do was push one button and I could've launched that chick halfway to San Diego.

Hillary made the boo-coup bucks. She was a very successful real estate agent and didn't spare any expense for the party. The spread they had was awesome and I'm proud to say that I made a total fucking pig of myself. Hillary even put out for an open bar, complete with bartender. That was cool: I love Long Island iced teas and had quite a few that night.

And you should've seen the look on her face when Caryl gave her that fucking cake. It was priceless. "Oh, uh, thank you honey! You shouldn't have." Then when Caryl turned her head, she gave me this weird "why did she bring this ugly cake?" look.

I nearly busted up.The company was good. The food was great. And the drinks were awesome. So I had a pretty good time. I was also able to avoid Caryl.

Anyway, midnight came and went. By the time two rolled around, everybody had gone home. Well, except for Caryl and I. I wasn't about to drive and Caryl was also fucking plastered. She had graciously forgiven me by this point, not that I cared. Hillary offered us one of her spare bedrooms for the night.The four of us flaked out and chatted for a bit. We were all pretty wasted by then. Then Toolshed wandered off to bed. Not long after the Shed left, Caryl gave me a kiss and went to pass out. And that left Hillary and me all by our lonesomes.

So there we were, drunk. We start talking and Hillary shocks me (insert sarcasm here) with an admission that she isn't all into Toolshed. We talked some more and she kind of leaned back and looked like she was going to ask me a question.

"No, nevermind.....""What?"

She looked around and then looked back."You ever, you know?"

Yeah, that was specific.

"What?"Then she put her finger and thumb together and took a pretend hit of pretend pot.

"Oh yeah. Not often.""Got any? Here?"
"Sure. Hold on."

I went out to my truck and grabbed a joint. Then I grabbed another one. Yeah, I know, two weren't needed. But hey, I was a little fucked up. Despite my best efforts to limit my Long Island iced tea consumption, I had gotten drunk. My only excuse is that, well, Long Island iced teas are really, really good.I brought Jeff Spicoli's favorite plant in and she smiled. "C'mon, let's go out back."

Fast Times At Ridgemont High: one of the funniest movies ever.

"Whoaaaaa....."

We went out to her porch and sat down at the patio table. I lit Mr. Doobie and took a nice, long drag. Then I passed it to Hillary and she took a drag. We toked and talked for several minutes until we knocked off the joint.

"So, can I ask you something?"

"Sure."

"Why do you put up with her bullshit?"

We looked at each other and laughed. Because, folks, that's what you do after smoking pot. You laugh. At anything. I'd like to add that my legs felt like they were floating.

"Because she fucks like a porn star."

And we laughed some more.

"You know...she told me you guys weren't fucking. That you were waiting until you moved in together or got married or whatever."

"I'm not fucking marrying her."

"No shit? I know I'm shocked!"

"I've been fucking her since May. She even takes it up the ass."

Hillary laughed so hard she nearly choked."You musta loved how tight it is. Stick a lump of coal up there and it'll turn into a diamond."

We laughed some more. I don't know why Hillary was so down on Caryl. Maybe Caryl had been pulling bitchy shit on her as well.

Hillary getting ready to turn in for the night.

So we were laughing and then I whipped out the second joint. She laughed and said, "Fucking light it up, Spicoli!" So I did. And we smoked that one, too. And then EVERYTHING was hysterical. We were totally fucked up and loving it.

We continued to talk when I blurted out, "I think you're fucking hot. That okay to say?"

She laughed, "Yeah, is it okay to say I'd like to suck your dick?"

"Yeah, okay to say that I'd like to lick your pussy?"
"Yeah. Okay to say I wanna fuck you?"

Fuck. High or not, I had to decided if I wanted to just laugh this off or get a piece of this woman's ass. I really liked her and she was very pretty. But if we did, what would happen come sunrise? What if Caryl found out?

Then I realized that I had downed far too many Long Islands and smoked way too much of Mother Nature to even be asking myself such questions, let alone answering them. So why the fuck should I ask myself questions that I had no business answering? It was stupid and irresponsible to do that.

Exactly! I had NO business doing that! That would be stupid! Good thing that I came to my senses.

"I've wanted to fuck you since I met you."
"Take your pants off....."I somehow managed to get my pants off without falling face first onto the porch. Hillary wobbled over and leaned down and kissed me, shoving her tongue into my mouth. As we kissed, she reached down and rubbed my cock. It was already standing at attention.

Hillary got down on her knees and started sucking me. All was right with the world. I was drunk, I was high, and I was getting blown by a blonde I had wanted to get my cock into since I first met her.

Ah, 1990 would be a fine year indeed. I just smiled and let Hillary suck me. She took my cock out of my mouth and asked, "You liking this, honey?" "Oh yeah......"

A couple of minutes later, I was ready to experience my first wad-shooting of the year. I groaned and said that I was cumming. Hillary jacked my cock until I shot my load all over her shirt.I got up and and pulled my pants up and Hillary sat down. I took off Hillary's shirt and unhooked her bra. I had been drooling over those big tits since the day I met her.

I kneeled down and started sucking on her nipples. She sighed and unzipped her jeans and played with her pussy as I continued to suck her nipples. A couple of minutes passed by and I heard her whimper a little and softly say, "Honey, cumming....."

I kept sucking and felt her body jerk as she came.Pulled her hand out her pants and put her finger in my mouth and then pulled it out.

"Wanna taste more?"

"Yeah...."
"Yeah, I bet you do.....I want you to....."

We got up and went back into the house. She checked to make sure AssMunch Toolshed was sleeping, I popped in on Caryl and she was out like a light. I met up with Hillary in the hall and she grabbed my hand and led me into one of her spare bedrooms. We went in and she turned on the lights and locked the door.

A glass of wine before the fun starts.

We stripped down and stared at each for a minute (or hour, who knows?). Then we wrapped our arms around each other and started kissing. After kissing for a moment we realized--in our Spicoli'ed state, it took a bit for this realization to sink in: we'd better turn off the lights in case Caryl or the Shedster got up.

Hillary turned off the lights but we weren't completely in the dark; there was a nightlight in the room that allowed me to gaze at this gorgeous woman. Then she laid down on the bed and spread her legs wide, exposing her hairy pussy.It was already nice and wet and I wrapped my arms around her thighs and started eating her out. Hillary took her hands and spread her lips wide. Her clit was hard and I sucked, licked and kissed it. When I heard Hillary start to breath faster, I sucked it as hard as I could.

I heard Hillary say softly, "Oh Ryan....honey, I'm coming.....make me cum...." Hillary came and I got up. My face was soaked.I crawled up and we started kissing again. My cock was pressed against her pubic mound and she was running her hands up and down my back.

"Put that inside me, hon."
"Do you want me to put on a rubber?"
"No, I'm on the pill."

I lifted my hips up and slid my cock into Hillary's pussy. She was so wet that I just slid right in. We both groaned as I slid my seven inches into that beautiful woman's pussy.

I really don't remember how long we fucked. I remember that her hair smelled great, that we kissed the entire time, and how warm and wet she was. I remember her hands caressing my back, and her legs wrapped around mine and how her breasts felt pushed up against my chest.

All I wanted was to hold off cumming until she did. And thanks to that blowjob she had just given me I was able to. I kept fucking her until I heard her whisper, "I'm cumming...cumming....."

I kept sliding my cock in and out and she smiled and said, "Your turn.....cum in me...." I increased my pace and unloaded what was left of my reserves into her pussy. We kissed and I pulled out of her.

Caryl felt her pussy and said, "Shit!"

"What?"
"I sprung a leak, baby!"

We both laughed for a minute (or hour) and knew we'd better get to bed. I don't remember what time it was. Hillary left to take a shower and I went and tip-toed into the shower that was just off of Caryl and my room.

I steamed the bathroom up really good. I needed a nice hot shower and I needed to get rid of the pot odor on my clothes. For me, the hotter the better where showers are concerned.

As I was about to step into the shower, I had that horrible feeling that I needed to stick my face in the toilet. Yeah, all that food decided that it didn't like the combination of Long Island iced teas and mutha nature.

Shall I try to describe the sounds of me barfing? Or have I already divulged too much? Okay, I'll move on.

After my shower, I was still pretty fucked up. I decided to run my clothes in the dryer for a few minutes with a dryer sheet. I just wrapped the towel around my waist and walked to the laundry room. I tossed them in and turned on the dryer.

A few minutes drying, and the smell of miss Mary Jane would be gone. But my New Year's Eve odyssey wasn't quite over.

I leaned back against the dryer and entered a semi-conscious state. I wasn't awake, but not asleep, either.

I was jerked back into reality when I heard Hillary come in. She just smiled, walked over, got on her knees, and unloosened my towel. She then started blowing me again.

"Hills, it isn't going to get hard again, honey."
"Bullshit. You watch. I want more."

I don't know how she did it, but her mouth and tongue got Mr. Happy up again. I took HIllarys towel off and had her bend over the washer and started rimming her ass. She just groaned and started playing with her pussy.

I turned her around and licked her pussy for a minute and then she had me lay on the tile. Tile's not my favorite surface for fucking, needless to say, but you have to deal with the cards you're dealt.

Hillary crawled on top on me, lowered herself onto my cock and started fucking me fast and hard. This was definitely a quickie. A couple of minutes later, she came. She kept fucking me until I came--and believe me, there wasn't much to shoot. I had to dig into my emergency reserves.

We got up and she kissed me and said, "We gotta fucking get to bed, honey."

I got my clothes out of the dryer and we snuck down the hallway. We were both naked and really didn't think that getting caught that way would result in anything but two big blowout fights. I watched Hillary's ass as she went back into her room and then quietly put down my clothes and slid into bed next to Cake Woman.

It took about two seconds for me to pass out. The next thing I remember was Caryl nudging my shoulder and saying, "Honey, time to get up. It's 1:00."

Whoa.

I staggered out of bed and took another hot shower. After I dried off and got dressed, I walked out to the kitchen. Hillary had laid out a bunch of leftovers for a New Year's Day brunch. The four of us were pretty hung over and there wasn't a lot of talking going on as we ate. Hillary shot me a couple of, "Heh. We fucked last night." looks, though.

After lunch, we thanked Hillary and Toolshed and I drove Caryl home. Then I went home and passed out again until the Rose Bowl game.

Hillary and I kept seeing each other through January and into February.On Valentine's Day, I had given Caryl some cheap-ass, fake diamond heart pendant I bought from some kiosk at the Montclair Plaza. It was like sixty bucks (and I still felt like I spent too much on her) but was romantic and all that. I also got her some nice roses to go along with the pendant.

I didn't really mind shelling out the clams because it made Caryl happy and kept her from bitching. And not only that, I got some serious sex that day. Caryl was all turned on by my incredible thoughtfulness and really heated up my bedroom.

She enjoyed that pendant for less than a day.

The following day, Hillary stopped by for a little playtime before showing a house in Riverside. As usual, she was awesome. We fucked twice and after we were done, Hillary hopped into the shower. After she got dressed, I walked her out to her car.

Usually, I'm pretty discreet. At least, I try to be. But Hillary and I were always so attracted to each other if we even kissed, we'd keep kissing. There was never a quick kiss goodbye.So we got to her car and she smiled at me and leaned over and kissed me. I kissed her back. And we kept kissing. And kissing.

She laughed, "I gotta go!"

"So go."

Then we resumed kissing.After a minute, Hillary pulled away and said, "Oh shit...."

I turned and saw Caryl marching towards us.You remember how in the Kara entry, I mentioned that I couldn't even paraphrase what her mother said when she caught us? Same thing here. I don't remember too much of what she said, just how angry she was.

I remember Caryl going off, swearing at us, calling us names, slapping me (fucking bitch), and ripping her pendant off, throwing it to the ground and smashing it with her foot (well, technically, her shoe). And I remember her calling Hillary a slut and me a cheating cocksucker. Then she stormed off.I was pissed. I could've returned that pendant and gotten my money back.After she tore off in her car, Hillary and I looked at each other.

"You okay?"

"Yeah. Not the first time I've been slapped."

"Bitch. Never a reason to hit someone, I don't care."

"She'll run to Ted, you know that don't you?"

"Yeah."

"Deny it. Tell him you stopped by to ask me a legal question and gave me a hug and Caryl flipped out."

"Yeah....okay...."

"Call me later."

"Okay."

Hillary straightened herself up and went to show that house. I went back into my apartment. One or two of Caryl's nails caught me and I had a couple of deep scratches. I just chalked it up to an occupational hazard.

Then I laughed. I had finally gotten out of the relationship. Sure, I destroyed a friendship and shattered Caryl's emotional well-being, but hey, I was out of the relationship, baby!

Actually, as for destroying that friendship, it wasn't really that dramatic. Over the course of our time together, Hillary had mentioned that she didn't feel as close to Caryl as she had several years earlier, when they met.

I think Caryl was just a high-maintenance person. That was Hillary's major complaint and it was mine as well. Caryl got pissed at everything. I mean, shit, she was pissed over a fucking cake.A FUCKING CAKE!

Of course, she went straight to The Shed and tattled us on like a fucking five year-old child.But here comes the most awesome part: The Shed didn't believe Caryl! Not one word! Toolshed called me a couple of days after The Explosion and asked, "Dude, you aren't fucking Hillary, are you?"

"No man, I wouldn't do that to you. You're my friend."

"Dude, your girlfriend is crazy. She's accusing you and Hills of having an affair.""Ted, Hillary stopped by the other day. She just had a legal question is all. As she started to leave, she gave me a thank-you hug. Caryl saw it and went ballistic."

"Thanks, man. Sorry I even had to ask. I always knew there was something weird about her."
"Hey, we're buddies. You can ask me anything you want, you know that."

Bwhahahahahahahaha!

Suck on THAT, Caryl!

Anyway, Hillary and I ended it after getting caught by Caryl. Sure, Shed didn't believe Caryl and we had gotten away with our affair. But there were other considerations: Hillary's kids.

Hillary's ex was great about paying child support. But after their divorce, he moved back to New Jersey and wasn't around all that much for her kids. For all of his annoying qualities, Mr. Shed was great with her kids and they loved him. So while she ran a little hot and cold with her feelings towards him, she wanted him around.

And that made sense. About a year after we ended it, Hillary and Shed got married.

About a week after the incident, Caryl left a message on my answering machine. It was pretty much more of the same. I had ruined her trust in men, I was an asshole, she had trusted me, I had betrayed her....BLAH, BLAH, BLAH, BLAH......

I have no clue about what happened to her. I've done several searches for her and haven't been able to find out what happened to her. Maybe she got married and changed her name. Who knows?

Maybe she went to work selling cakes.

I've always felt bad about Caryl catching us. Her faith in men was shaky after her divorce, and I certainly didn't end up helping her in that regard. I didn't set out to fuck her over, but I didn't do anything to prevent it, either. I don't have many regrets, but the way it ended with Caryl is one of them.

I was a pretty shitty boyfriend, I admit it.

It's been over twenty years since that day I five on the upside from Caryl. I deserved it, even if Hillary didn't think so. But had I broken up with Caryl, I never would've gotten to fuck Hillary.

So, Caryl, I'm sorry I hurt you. But hey, you gotta break a few eggs if you're gonna make an omelet!

Huh. Maybe I don't feel all that bad after all.

So what happened to Hills? Well, we never really saw each other after that day. She still lives in southern California, is still in real estate, and is still married to the Shed, that I do know.

For Hillary's pics, click here (members only).