Two Women, Two Weekends

[tomjones88]

Part 1:

True story, this. Names have been changed. It happened a few months ago.

On a cold April day in Chicago, I left campus at grad school, where I would soon be finishing classes, took the train to Lincoln Park and arrived at the back entrance of her apartment building.

Let's call her Katie. She lived alone in a 7th floor studio apartment and worked in marketing. She was new to the city and I got the impression she felt lonely here. As had I. We had met on the Internet. The first time we'd met had been the week before. She had sent me a picture of herself via text message before we even met, without me asking. No, it wasn't a nude picture; yes, I knew when I saw it that I would be seeing her naked in short order. Something about the photo--the way she was posing in a doorway wearing a cotton blouse and silk black pants, her height, her smile--made it clear that I would be able to make her mine by the end of the first date. That this was what she wanted.

We met and had lunch at a restaurant near the train. She wore glasses, unlike in her pictures (but the same can be said for myself). Her arms were thick and one was spotted with a birthmark. She liked talking about herself. About herself and fashion. She asked after we ate if I wanted to come over and watch some T.V. I'm not certain if she meant by this, "I want you to eat me out and fuck me twice on my bed, the first time diagonally and without a condom." But that's what I took it to mean, so that's what happened.

Her panties were damp from me fingering her before I entered her. She was the sort who looks in to your face the entire time. She didn't moan, she squeaked. She was the only woman I've had who said, "Daddy." She was the first woman I'd stuck my cock inside without a rubber on since I was nineteen.

Her thighs were thick and flubbed against my waist. Her vagina was gigantic. And yet, perhaps it was just me, perhaps I've just had enough sex by now, but it didn't feel that much different from if I was wearing a condom. A little more juice and a lot more skin.

I came inside her and we exchanged awkward pleasantries and I left.

After that first time, she sent me text messages about how much fun she had and how she wanted to see me again. It was a little strange. I'd never met a woman who expressed herself so randomly and provocatively. Her texts often went like this:
4:04PM Monday: So excited! Getting my nails done today. 5:20 PM Monday: I want to hook up again.
So when we made plans to meet that next week and she mentioned that she didn't want to bore me with her T.V shows, I decided to respond:
3:23 PM, Thurs: Honestly boring me will be hard because you're so attractive and I'm so fucking good in the sack so you won't be bored either.
3:24 PM Thurs: Sorry hun. You're gonna have to find someone else if sex is all you're looking for.
3:25 PM Thurs: Okay relax. I was joking.

Except that I've stopped giving a shit when women send me mixed signals. She wanted to play that game? I would see it through, and that alone would make her want to fuck me.
Which brought me to her door on that cold Spring day. I rang the buzzer but nobody responded. A tenant walked up the steps, unlocked the door and held it for me. Great, problem solved. I took the elevator to the 9th floor and made my way to her door. She opened it and I stepped in and the first thing she said was, "Take your shoes off." Because she was a clean freak.

About an hour and a half later she was on her back, saying, "Daddy." "Daddy." "Daddy." Because she was also a freak-freak.

She looked into my eyes, like I asked her to, and I pumped back and forth. I wore a condom. She'd said she didn't want to do it raw again, even though she was on birth control. Actually, she'd said that we should try not having sex this time we hung out. And yet here we were, on her queen sized bed, me staring down in to her brown eyes and her glittery face slick with a sparkly perfume and running my hand through her hair and swallowing the last vestiges of the sour taste of her vagina. She moaned in faint croaks and said,
"Fuck me,"
And I gripped a pillow and pumped harder and felt her thighs closing in on my waist, slowly but surely, inevitably.

That was Friday. I felt just strange after fucking Katie. It wasn't a real relationship for sure, and I was not looking for a real relationship. But it didn't even feel like a fulfilling fake relationship. I wasn't sure we had anything in common. I wondered if I would ever have her over to my place. The last girl who had spent the night, about two weeks before I met Katie, had been a disaster. I should never have fucked her. There was some trepidation I felt about introducing my home life to this woman.

The next day, after a long day of editing, I went down to the newly opened tavern in my neighborhood. I thought before I left, I don't care about hooking up tonight. I'm just going to have a beer and go.
So you can imagine that when I sat down beside a woman in a purple blouse, chatting with a man, that I didn't care at all about approaching her. But when she turned and asked me if I'd ever been here before, I wasn't going to just brush her off. So I told her that it was only my second time. And as she continued talking with me, I realized she was ignoring the guy beside her entirely. And it seemed that he wasn't particularly fazed by it, either. He just calmly sat there, sipping his drink.
When he went to the bathroom, I asked her who he was.
"He's my friend Paul. We just went to see this movie together. I don't think he wanted to come out here at all. I just made him come check it out with me."
Knowing that he wasn't her boyfriend, I saw a path in front of me, and I took it. We left the bar together, heading for another bar.

I felt that I had been drinking too much recently. This was part of my resolution to only have one beer, initially. But I'd already decided to seduce her, so rules were out the window now. We sat across from each other in a booth at a nearby bar, she with a mojito, I with a Gin and Tonic. We talked and I did not look away from her light blue eyes. She told me, after an awkward pause,
"You make good eye contact." "Thanks. There's just something magnetic about you."
I then told her that I was thinking about how, if I wanted to kiss her, I would have to move all the way over to her side of the table because I couldn't just lean forward. She smiled faintly and kind of nervously giggled. I moved to her side of the table and kissed her. She kissed me back.

We walked down the deserted street to her apartment and she stopped, pulled me to her, and kissed me long and hard. Her tongue flicked over mine.

She lay on her bed and I crouched over the edge, my head between her legs, letting my swishing tongue open her vulva wider and wider. She tugged on my head. Her breaths turned into gasps and she pushed my face deeper in to her. I felt her wetness fold over the tip of my nose.

She sat on top of me and rode me. I helped lever her body up and down. Her tits were small and firm, but well rounded. They didn't look awkward or goofy when they jiggled.
We had already fucked once. Then we'd fallen asleep, then her cats woke us up, then we'd talked a bit and I'd stroked her body with my hand until I slipped it in to her panties. Now I listened to the rising, raspy ecstasy sounds coming from above me and I stared at her waist, dipping up and down above my junk and then up at her tits. That was when she made a series of a rapid, hyperventilating sounds, bucked her thighs around my waist and put her hands on my shoulders. I already had scars on my back from her digging her nails into it earlier and I hoped she wasn't about to completely lose control and do some damage to my shoulders.

She didn't. I moved faster. I worked my pelvis up and down. I wished I'd been looking at her face for her hyperventilation riff, so I looked into her face now. Her hair tossed in front of it and her eyes were squinted.

I would learn the next morning that this woman, who we will call Amy, was 39 years old. I am 29. When she was eighteen, she was listening to Alanis Morissette's breakthrough song, "You Oughta Know" on the radio and losing her virginity if she hadn't already, and I was only just learning about sex, more interested in trucks and soldiers, and hearing that song sometimes but not really understanding what was meant by "Every time I scratch my nails down somebody else's back..."
Twenty-one years later that same woman scratched her nails down that same boy's back and he felt it.

So here I was. Me and my two women. I went through the next day working hard on a film set and received this text from Katie:
3:00 PM, Sunday: "Want you between my legs."

[tomjones88]

I went through the next week wondering how long I should keep seeing them both and how to schedule it. I'd already told Katie--back when it was true--that I wasn't seeing any other woman, only her, even though she said she got the sense that I was "quite experienced" and told me outright that she felt I was hooking up with other women. I had to go back to her apartment for a practical reason anyway; I'd left my watch there. I would keep her around for a couple more weeks and then move on.

Amy, on the other hand, I wanted to keep things going with. I didn't want to date her and I didn't want to become too attached. But she and I at least had some things in common. We were both avid readers; she had a room full of books and she ran a book club. We were both in graduate school. She for clinical psychology, myself for film. I wondered if, when she saw me get out of her bed in my faintly shit-stained underwear, if she tried to psychoanalyze me.
Amy had been through a divorce. Katie was just this lonely woman.

I was just this sex-obsessed guy who only told himself he wanted a relationship.

The next weekend, I went to see Amy on Saturday. We went to a movie. She drove and I bought the tickets. We went back to her house and sat in her living room, playing never have I ever and listening to the Beatles on vinyl. One of her never have I ever questions was if I had ever had sex in a very public place. I thought a while about it. I thought about my ex girlfriend and I fucking on a mountain that was commonly climbed. But no, I had not.
We made out on her couch. I slid my hands under her shirt from the back and inched my fingers over her bra strap. I took a few seconds--it was one of the double-strapped kinds--bit I undid it. She shook the rest of it off. It got her in the mood.

She sat on my face and I smelled her body odor and licked horizontally at a good clip. I darted the tip of my tongue deeper in to her and out again. With my index finger I rubbed the edge of her vulva below my chin. Her hand gripped my hand and manhandled it up and down between her thighs. My chin got damp and her wetness soaked down my fingers and on to my hand and her thighs contracted in these muscle spasms that sent them caving over my head and retracting and her body lurched upward. Her vagina pulled back from my mouth and I got a view of the shiny red messiness of my work.

We had sex and she was sprawled over the edge, her head tilted back, facing the wall while my rhythm moved her forward and we actually fell off the bed and laughed about it.

Then sleep.

In the morning, we talked about this and that, our studies, the difference between male and female brains, movies and I randomly announced to her;
"Also, I want to have sex with you."
She giggled again. I stroked her breasts with one hand. I moved down her belly.
Under her white sheets, the sunlight streaming in, her vagina got the wettest it ever got in my mouth and I even heard myself slurping against her juices. Her hand gripping around my head again. Her fingers tightening as she moaned. Her moans like jagged cliffs; up suddenly, peak, valley. Up again.

Her legs caved over my head, grazing my ears. I let her recuperate for a moment then came up from the sheets with her cum stamped all over my lower face and one of her pubes jutting off my lip and I kissed her and she kissed me back. In my experience, women do not care if they taste their own fluids. They just do not. It's a hang up men have.

I said to her,
"I really want to do you without a condom."
She looked insecure. She didn't know how to respond.
I said, "It's okay, I'll get a condom."
She laughed and said, "Yeah..."

The sex we had was good. I lay on top of her and told her to look me straight in my eyes. And she looked into my eyes with her blue eyes and said,
"Fuck me."
I kept fucking her.
"Harder. Harder."
I turned it up a notch.
My comment had no impact on the intercourse. But as I lay on her bed, waiting for her to return from the bathroom (I imagined her vagina needed some cleaning up) and let my dick go limp in the jizz-filled condom, I wondered if I shouldn't have said what I said.
She re-entered. Saw me all awkward and naked and laughed.

During breakfast, I put a tab of butter in her microwave to complement the rolls we were making. We didn't think about the fact that these tabs of butter are wrapped in tinfoil. Her microwave made sparks and she yelled,
"Stop it! Open the microwave!"
I was flustered and took too long to open it. But I did. We laughed about it. I kissed her goodbye when I left. I didn't know it yet, but that was the end of my fling with Amy.

Five hours later, I showed up at Katie's. I had a large box of condoms in my backpack. I figured I should just go all out if this was going to be my life for the foreseeable future.
I knew the moment I saw her that this would be our last time. She was sort of in a surly mood. We actually left the apartment, finally, and had a picnic. We chatted about random stuff.

She announced at one point that she'd decided that we wouldn't have sex this time. For a couple minutes I resigned myself. Then I stopped. Of course we would have sex.
I had gotten not much sleep at Amy's and I'd already gotten laid twice in less than eighteen hours. Why not round it out?

So when we sat on her couch and I sat close to her and stroked her shoulder at one point, after a joke and let my hand slide down to her leg, she said,
"Okay, you can touch my vagina if you want."

And that's what led to the image I have of my mouth approaching her vagina as she lay diagonally on her bed, my fingers already having worked her, and seeing a thin bit of white goo streaking her lips. Some guys would run for the hills; I was undeterred. I licked her up and down and side to side for the next few minutes. Then I put on a condom and entered her.

"On a scale of one to five, how good does this feel?" I asked her as I lightly pumped back and forth, my body separated from her's by several inches.
Surly mood still active, she said,
"Three."
I pushed deeper in to her and lay down on her chest and moved faster. She said,
"Five..."
I had the most amazing orgasm I'd had in a while that time. I don't know why it was with Katie and not with Amy, but it lasted forever and I made noise. I cupped my hand around her cheek and bore my face down in to my pillow. I kept sliding in and out of her as I blew my load, making my orgasm even crazier and she whimpered and I felt a contraction of female thighs for the third time that day. I felt exhausted from the taste of cunt and the feeling of orgasms.
After I left, she was apparently in a much better mood, because she texted me,
4:34 PM Sunday" "Thx for coming over! Safe travels!"
And I had already decided not to call her again. It took me some time to realize that "safe travels" was maybe her announcing the same thing.
The next day, I woke up stiff. My neck was cramped from eating so much pussy. The day after that I had a sore throat. Amy said she also had a sore throat. I didn't see how I could have given it to her. I read something about how women with yeast infections can pass it on to their partner and it can turn in to a new infection for them and I remembered the white goo on Katie's vag lips and thought, "Oh..."

A week later, Amy texted me and said she was feeling better. She also said:
3:54 PM Wednesday: I've thought a lot this past week and realized that I'm not ready to start dating anybody. A relationship ended in January. It was a rough winter. It was fun hanging out for a bit and getting to know you. Good luck with everything!

I don't need to go into anything after that. I don't need to go in to my half-sincere pleas for us to meet up again or my snarky dismissal of her when she refused. I don't need to go into the fact that I felt that box of condoms was a waste. I don't need to go in to how I pounded gin that next day and did not remember falling asleep and woke up with a headache that was the opposite of an orgasm.

All I need to do is move on. If this is a phase I'm in, then I'm just going to get through it.