Tuesday, July 28, 2009

My First MILF

Two disclaimers on this one.

1. I do not encourage sex with anyone other than one's spouse. You can read some of my reasons in a previous entry. You can read some other points worth considering here.

2. Yes, I'm writing about sex again. If this is a problem for you, skip this entry.

This is about my first real girlfriend – I wrote some about this relationship in this message, mostly talking about what was wrong with the situation. This entry, however, is more about why I was in that situation and what I got out of it.

If I had encountered her causally in my routine life, such as at the supermarket, simply having her walk by wouldn't have caused me to do a double-take and drool. She wasn't ugly by any means, and she did have a nice pair, but she was older and carrying some extra weight. The idea that an older woman would get involved with a 19-year-old guy was the stuff of the rare fictional TV show, like an episode of Soap I caught being rerun.

Not that I was a model. I was rather nerdish in my appearance, though I got of lot of aerobic exercise.

But between the e-mails, the phone calls, and the visits, I fell in love. She was a flirt and gave off this aura of sexuality.

I had a history of befriending people significantly older than me, including a female (with whom I have never and will never have that kind of relationship). A lot of it had to do with a shared hobby and that I was not the partying sort, and so I was not out partying with people my age.

So there I was with this flirty woman as a pen pal of mine, talking and writing back and forth, and me as a horny 19 year old who was thinking I was way behind when it came to my interaction with the opposite sex, and very shy when it came to those matters.

She started showing up in my fantasies. Eventually, I found an opening in our phone conversation and I told her I'd been having thoughts about her. In the context of our conversation, it was clear that they were sexual in nature.

There it was... on the table.

There was a pause on the other end of the phone.

That pause was killing me. I think I most expected dismissive laughter and a statement along the lines of "Me? Ha, that's funny. Cute. Say, did you see that fire on the news tonight?" Some form of rejection was coming – I was almost certain of that.

Instead she said, "I've been having thoughts about you, too."

WHAT?!? A dozen different substances must have flooded into my bloodstream at that moment. What did this mean? Would she dismiss the idea as a silly mutual crush that could never mean anything? At least she had some feelings for me.

Then she said "This means it is inevitable."

It was a lie, of course. I could have backed out. She could have backed out. Or, we could have met in public for a stroll and a serious talk about the issues we faced. Instead, she made plans to come to my place two nights later. Due to circumstances I won't bore you with, she ended up coming over the very next night instead – which was just as well, as one day of total distraction was more than enough.

And so it began, with me about as nervous as I could be.

I had had no idea this woman was attracted to me, and had been since the first time she'd caught a glimpse of me in person. In retrospect, one could ask how blind I could have been to miss the signs, including the time we were hanging out somewhere and she wanted to see where I lived. But I had very low self esteem when it came to women, and that evening when she wanted to see my place, we were with a couple of other people, one of whom sounded like she would come along - and my place looked like a disaster anyway. So I deferred to another time. There had been at least two occasions in the past – meaning my teens - when I was sure some girl was interested, but she wasn't. In one of those situations, I ended up getting punched in the side of my head by a dude I didn't realize was the boyfriend. (In retrospect, he was suffering more than me, being in a relationship with a girl who would flirt so much with other guys right in front of him.) So, I was overly cautious.

The feelings had been bubbling up. Just before the turning point, I had stayed over at her place, on the couch. I had thoughts about something happening, but with her daughter also in the apartment, I didn't dare try anything. She told me after everything started that she, too, had considered approaching me in the middle of that night.

On that one fateful night she came to my place. Her daughter, knowing her mother much better than I, questioned where she had been when she returned home later in the evening. When she told her daughter she had been at my place, her daughter, who had a boyfriend mere weeks younger and I, asked, "Were you good?" Her mother's expression gave her away. So her daughter was first to know.

I went to her place the next night, where her daughter was not happy to see me but was being taken out by her boyfriend... and it was constant after that.

At the time, I was a full-time student and I was working mostly Fridays through Sundays, holidays, and some short evening shifts. So I would usually go to her place Friday nights after my shift, leave from there for my shift the next day (or sometimes return home for a few hours), return to her place Saturday night, repeat the cycle, and then return home Sunday night – unless there was a Monday holiday.

I would also go over one night during the week, because the weekends were just too far apart.

She would often be out driving from client to client, and so there were times she would stop by my place during the school day, when I would be home between classes. Those were always pleasant surprises.

It didn't take me long to realize a few things about her:

1. She loved performing oral sex; she wanted me to ejaculate into her mouth and she enjoyed swallowing. Either that, or she was really good at faking it. I figured this out before I could even suggest or hint at it, let alone outright ask for oral sex. She went there on her own without any prompting on my part, and stayed there, persisting. I remarked, in a tone that was half asking and half surprise, that she wanted me to finish there, and she affirmed.

2. She truly liked sex. A lot. Love or no love. She didn't just like it as a way of bonding, or taking a relationship somewhere, or for use as a bargaining chip. She liked sex for sex. In fact, she said the often-used saying that "men use love to get sex and women use sex to get love didn't" apply to her – she would have a tough time having to choose between love and sex if there was such a dilemma.

However, she did, according to what she told me, go without sex for the previous five years, save for a single clumsy encounter months before we started up with a drunken guy I happened to know. From some of the other stuff she told me that she didn't have to, I have no reason to believe she was lying about her five years of celibacy, which roughly would have been from the period her daughter was 11. As her daughter was having sex by 15 or 16, this woman probably reasoned that setting a good example wasn't doing any good.

3. She was multi-orgasmic. This probably has something to do with point 2.

4. She had no hesitation about tasting herself anywhere on me.

As a result, it was common for me to enjoy the pleasure of cunnilingus until she had at least one orgasm, then engaging in intercourse and more kissing, and then finishing the session with her performing fellatio on me.

It was a good sex life – getting it at least three times a week, often more, even if it meant sacrificing an hour of sleep when I wasn't going to get nearly enough sleep as it was; the regular, enthusiastic fellatio with her swallowing at the end like it was the best thing she'd ever tasted; the things she would say.

Oh, the things she would say. Did she ever know how to lie to a man. Things like:

1. "You're so big."
2. "It is perfect; it's beautiful - I just want to stare at it."
3. "You're reaching me in just the right spot – we fit together so well."
4. "You are the best lover in the world."

That last one was definitely a lie. Even I wasn't naïve enough to believe that one. She was my first, after all, and by her own accounts, she had been with many guys. I'm sure she must have had a lot of better sex.

Still, all of this does wonders for a young guy's ego. He feels like he is a higher achiever of some sort, because he is able to keep the interest of an older, more experienced woman. In reality, it is usually a sign that something is wrong with the woman.

Her ex-husband and father of her child, who was totally out of the picture as far as I could tell, had been many years younger than her when they got pregnant and married – something like her in her later twenties and he maybe 19 or 20. She said they intentionally got pregnant first, because there was some question about his fertilization ability.

What was the deal with her and younger men? She linked it to her past.

She claimed to have been abused by her father, including sexually, though for years she had suppressed the memories. If it was true, it would certainly help explain some of her tendencies. She was actually married briefly as a teenager to get out of the house because her father almost killed her. She wasn't attracted to men who reminded her of her father – which, by that age, was men her age.

She called Dr. Laura to discuss the situation. I think Dr. Laura's show was still local back then, and the nature of the calls were somewhat different than they are now. I didn't hear the call, but she reported back that Dr. Laura told her that she was doing much the same thing to me that her father had done to her.

I can remember dismissing that with pointing out that I was a willing participant and I sure didn't feel like I was being abused.

I honestly thought it was about more than just sex. After all, we'd started out as friends. We struggled with the future. I was still of the mistaken belief that relationships like this were supposed to last as long as you didn't feel like murdering each other. I think she had originally figured she'd take my virginity, give me a makeover, have a short fling, and move on. But I (or the regular sex, or both) grew on her. That's why it lasted for a year and a half.

Not that the only alternative was doing the same thing with someone my own age, perhaps with a classmate, but I think I was better off going through this with some woman old enough to be my mother instead of some nice young college girl. It is for the best that I didn't knock up some girl who "accidentally" forgot to take the pill or poked holes in condoms, or take her virginity, or marry her because she was the first woman interested in me, or to lose her to some older guy who could legally buy alcohol or shower her with money. That was another good thing about the relationship – yeah, we bought gifts for each other, but she didn't expect me to otherwise spend money on her – which was good, because I didn't have any. She was practical in that regard.

Thankfully, although there were upsetting moments where it looked like we were going to break up, in the end I didn't experience a devastating break up with this relationship. It just kind of faded away when being grandma became her priority. We were still in contact daily, but she wasn't inviting me over, or coming to see me. When I finally moved on, and she figured it out, she was upset, but we hadn't seen each other in so long and we didn't have any actual commitment. I was surprised she was upset. A few months later, she called to apologize for her reaction and we were on friendly terms after that.

Some things I learned (and perhaps could have learned another way, or didn't need to know to have a good life):

I was not made of woman-repellant.
I was capable of sexually satisfying a woman.
A lot of women show attraction to a man if he is already seeing someone.
Some women do enjoy fellatio and swallowing.
I didn't have to spend loads of money to have a girlfriend.
Breakups aren't the end of the world.
Age differences seem to disappear in the playful throes of passion.
Dating older women can be a lot of fun.
Dating mothers means dealing with their child(ren), which can be a pain.

Speaking of dating mothers – although I subsequently dated some other older women over the years, only one was a mother. It was a brief fling and I didn't deal with her kids at all.

So now you may understand a little more about where I am coming from.

Although I had a lot of fun, my best advice now would be: Don't try this at home – or anywhere for that matter.

1 comment:

  1. sth_txs9:30 AM

    I'll make sure to play my violin tonight in your honor.

    ReplyDelete

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