Knocking Up Teacher

Melissa Pamer and Tony Shin at NBC’s Los Angeles O & O has this story which has been all over the news around here:

A Redlands high school teacher accused of having a baby allegedly fathered by a teen student pleaded not guilty Tuesday to 41 counts of sex and oral copulation with a minor.

Laura Elizabeth Whitehurst, 28, was arrested July 1 after the mother of a Citrus Valley High student contacted school officials about the suspected relationship between her son and the English teacher.

She was charged Monday with crimes alleged to have involved the boy -- who was 16 when the relationship began, according to police -- and two other teen students who are now adults.

Later:

Authorities said Whitehurst had given birth June 18 to a baby fathered by the student with whom she had had a nearly year-long affair. The boy attended the baby’s birth, according to court documents.

Later:

Then, at least two other men came forward and said they had had sexual relations with Whitehurst in 2007 and 2008.

One of the alleged victims spoke to NBC4 Southern California, saying he never felt victimized but wanted to share his story so that others might come forward to tell police about their experiences with Whitehurst.

Finally:

Whitehurst is charged with 30 counts of unlawful sexual intercourse with a minor, and 11 counts of oral copulation of a person under 18.

If convicted as charged, Whitehurst could face up to 29 years in state prison, the District's Attorney's Office said.

So there's yet another criminal case that's hit the news lately about a young female teacher "having sex" with multiple minor male students. Unless the teacher is decidedly unattractive (this latest one isn't), one of the common responses to this is along the lines of:

Advice to a Middle-Aged Woman Re-entering the Dating Pool

It's titled "Jumping Back In" but is there still water in the pool? "Bella" wrote in to Dear Margo:

After a marriage of 20-some years, I am about to dive into the middle-aged dating pool.

Oh boy, is she in for some fun.

I suspect it will be very different the second time around, but part of me thinks it may be just like picking up where I left off.

The first one is right for two reasons: 1) the rules have changed, and 2) you've spent up one of a woman's most valuable dating assets - your youth.

Friends tell me, however, that it’s a whole new ballgame and difficult.

Yup!

Dear Mago metions baggage, then ends with:

But … chins up. The men you will be seeing are just as nervous as you are, and I’m here to tell you that you will get the hang of it.

Dear Margo is either oblivious, delusional, or didn't have the heart to tell this woman the truth. Some of the people commenting did, though.

There are two big questions that the letter writer should have answered by including the information:

1) What are you looking for in general? Free dinners and entertainment? Another marriage? Steady companionship? Sex? If she's getting alimony, she may not want to get remarried if she values the steady money over marriage.

2) Are you willing to try men significantly younger or older than you?

Almost all of the successful, desirable, dating heterosexual men around near her age are divorced or on a marriage strike and dating younger women. If she wants to marry or even date a man near her age, she's probably going to have to be open to dating men who can't afford to pay for her to have nice dinners and entertainment, never mind financially support her if they marry. If she wants those things, she will almost certainly have to go with a significantly older man. If she just wants companionship and doesn't care if the guy is "of modest means", then it isn't so much of a problem.

She'll also find it isn't a problem to get sex if that is all she wants, but it will be easiest to to be on the "A" list with guys who are younger (since women their age are dating older men) or significantly older. Guys around her age will probably have her on the "B" list.

Speaking of sex... there's no short supply of younger, hotter women than her willing to have casual sex with the men she'll want to date. Most men these days expect it by the third date, if not before, and a lot of women consider themselves rejected if he doesn't try for it by then (if those women aren't taking the initiative themselves).

Those are the brutal, harsh realities.

If she wants to marry a successful man near her age who would make a good husband, her best hope is going to be to find a divorced man whose wife threw away a perfectly good husband, yet he hasn't been turned off to marriage. If he has no minor children, that will be the best scenario. He'll likely be paying alimony to his ex-wife, though. (If he was widowed, she won't have an ex to deal with it all.) To snag such a man, she's going to have to compete against those younger women I wrote about above. The does not mean she has to jump into bed with him – if he thinks sex is for marriage or only for steady, exclusive relationships, he'll appreciate it if she keeps that boundary in place. She should play up her advantages over those younger women (if she has them) – a better understanding of how to keep a man happy (did she learn from her ended marriage?), better earning ability, more experience in social graces, etc.

Enjoy!

Sheesh... after I wrote all of this I remembered having written something like this before. Previously:

A Question for the Ages

An Unmarried Woman

She Might Have to Go Older or Younger

Is It OK For Her to Ask For a Date?

She Might Have to Go Younger or Older

It's not easy for a 50-something woman in this position. MISSING OUT IN WYOMING wrote in to Dear Abby:

I am a 54-year-old woman who, after a long marriage and unavoidable divorce, is ready to date.

Sorry you went through that. The divorce could have been avoided by choosing wisely and treating kindly. Choosing wisely, thought, can be difficult if someone hides who they really are before you marry them.

I work out daily, am active in my church, take classes, and socialize with women and married couples. I'm in excellent shape and am told I'm attractive and fun.

All good things.

There are few available men my age (or a little younger or older) and almost all of them seem to be looking for women in their 40s, 30s or even 20s.

This is true - that there are few available men, since almost all people get married. A heterosexual man that age is likely to be married or remarried, or divorced at least once.

Here's the heart of this letter:

Why are men my age so unwilling to date women their age?

The short, brutal answer is: Because they don't have to. Men tend to gain money, power, and fame, as they get older, and that makes them more desirable to women. The more of these things a man gets, the more and hotter women he has available to him. Sure, women appreciate hunks, but the bottom line is that the kind of women these men want (young women who will provide sex for little effort/time/money invested) are usually going to choose the guy with money/power/fame over the younger, hunky guy who is living paycheck to paycheck. These men have those women available to them, and they are going to pick those women before picking you.

"Hotter" for most men often unavoidably means "younger", because men are visual creatures who prefer tighter, perkier, less damaged/aged female skin.

When these men get older, they may look or a woman who will be able to take care of them in their old age, but for now, they want sex with hotter women. A lot of them have been married before and it isn't what they want right now, or, even if they are looking or a wife, they want her to be hotter and deferring to his age and experience.

They don't want another friend. They don't want someone with whom they can discuss politics or deep subjects. They want a younger, hotter, fresher body.

I write all of this as a guy who, during my wayward younger years, thoroughly enjoyed the company of a woman your age. The older women I dated were attractive, sexy, and a lot of fun and could carry on an intelligent conversation. But I wasn't looking to marry any of them, or travel with them, or anything like that. It was conversation, perhaps a movie, perhaps dinner, and most definitely about fornication.

Am I destined to spend my life without romance?

There is probably a man your age out there who is right for you and wants you. Maybe you've ignored a few of them already because they are "boring". Chances are, though, he'll be of modest means because the guys your age who are better off do have the option to go younger. If it really is romance you want you'll increase your odds if you are willing to date men significantly older than you or to play the cougar by seeing younger men… who can't find women their age because they are dating the men your age. If you want a husband it is going to be difficult, but not impossible, to find someone your age; it will be nearly impossible if you expect him to be much better off financially than you.

Dear Abby responded:

I can't speak for "all" older men, but many of them in our youth-obsessed culture look for women considerably younger because it helps them fool themselves into thinking they are younger than their years.

That might be the way a woman thinks, but not the way a man does. It really is as simple as younger generally = hotter. Yes, there are unattractive 20 and 30-somethings, but few women have hotter bodies at age 54 than they did at 34 or 24. Like it or not, a man's ability to attract someone in the dating world tends to increase as he gets older (to a certain limit) and a woman's tends to decrease. This is one of the big reasons why marriage "protects" women and is advantageous for women.

When you're 54 and you’re with your husband of 20+ years, he has that love and bond and history and experience and memory and vows with you. Your body turns him on in part due to these factors. That isn’t the case with the unmarried men who are strangers to you, who will have a more difficult time being turned on by the mere sight of you across the room. It is easier for them to be turned on by looking at that 20 or 30-something they don’t know either, and that makes them more likely to approach that other woman rather than you.

You are physically, socially and intellectually active, so stop allowing yourself to be marginalized and consider dating men who are younger. It worked for Demi Moore.

Not a bad suggestion.

Hot For Teacher

WONDERING IN WYOMING, a teacher of ten years, wrote in to Dear Abby:

One student I've kept in touch with recently admitted his romantic love for me.

This is not unusual, thought I tended to look at my teachers as... teachers. I don't recall thinking much about their personal lives at all. I was there to learn from them, they were there to teach me.

"Kyle" is now in his 20s and on his own. As his teacher 10 years ago, I'd never have dreamed of this happening.

You should have been warned about this.

What's difficult is I think I reciprocate those feelings. I never expected the man I connect with most to be a former student, but Kyle is an adult and I know him as such.

She goes on to express her hesitation as well as her openness to this being the love of her life, asking if it would be inappropriate to follow her heart.

Wyoming is generally not the place I think of when I think of attractive women. I'm sure there are some there. But the most attractive young women tend to gravitate to the large metropolitan areas, especially the warmer ones, because there are more men with money, power, and fame to compete for her affections, and more opportunities for her to show off what she has. Think Los Angeles, Dallas, and Miami. Anyway, Kyle has an attraction, but it could be some unrealistic fantasy, especially a teacher-student fantasy, and his infatuation may give way to disillusionment. Or, maybe he's genuinely and deeply drawn to her. Hopefully, it is the latter.

If she's been teaching for ten years, then she's probably at least 32. She doesn't explain what grade she teaches, but Kyle is, at the oldest, 28. A wife being four years older can certainly work. Now, if he's 21, then the long-term prospects aren't so good.

I don't see any moral problem with her dating him. Dear Abby agrees, though warns that she should expect gossip and should be prepared to relocate. Good advice.

I'd bet money (if I was a wagerin’ man) that some male teachers and coaches in WONDERING's area are married to former students.

The girlfriend I had the longest relationship with (before my wife) was starting her teaching career when we first started dating. She had an amazing body. No matter how conservatively she dressed, she couldn't hide her DD breasts, and at least once, jealous female students falsely accused her of flaunting them. The funny thing was, that girlfriend failed to accept that she had a great body. She was teaching middle schoolers the first year, and she asked me if she should make male students work at the chalkboard. It took me a second to get the real meaning of her question, but once I understood, I advised her that it would be best to let the students stay in their seats. At that age, boys are getting erections all of time with little rhyme or reason, but her presence was plenty of reason. Those poor boys didn't stand a chance. Even if they cared more about the caboose. Or legs. She was all good.

So, ladies and gentlemen... did you have a crush on any of your teachers? Or whether as a student or adult, do you have any experience with a situation like this? Would you tell the letter writer not to do it?

Go Older, Young Man

Another great guy overlooked. H.P. IN MIAMI BEACH wrote in to Dear Abby:

I am a 20-year-old male who finds it awkward talking to women my age. I do OK approaching older women for conversation, but become tongue-tied with someone under 25. I would like to meet someone special and develop a relationship with her, but at this rate it's not going to happen anytime soon.

You shouldn't be looking to meet a woman like that for at least another five years, or until you achieve your dream (or are on your way to doing so), establishing yourself professionally.

The women your age are dating older guys, or stuck in dying high school relationships, and probably don't care about the same things you care about, so the conversation is usually lacking. You said you are OK with older women. That's where the good, uh, conversation is. My advice would be to date some older women. Notice that is plural. Keep multiple plates spinning- don't allow it to become an exclusive boyfriend/girlfriend situation with any of them (and no women with minor children). And you know what? If you do that, I suspect younger women will start to show an obvious interest in you.

Dear Abby told him to smile and goes on to plug something she wrote.

If you want to get to know someone, walk over and say, "Hi, I'm 'Hal' -- what's your name?"

That can work as parties where you know a lot of people. But if you’re somewhere, like a restaurant that has a bar, you can wait for them to come to you if you look like you are waiting for a friend.

Shady Siblings?

An anonymous American female in her 50s wrote at Dear Cupid:

I have a suspicion that my boyfriend is having an incestuous relationship with his sister.

Okay, well, stop seeing him. There's really not anything else to do. If he is, then you don't want to be with him. If he's not, then you're too suspicious for him. Or perhaps he’s too close (in a platonic way) with his sister. Be glad he's your boyfriend, not your husband.

Before I met her, she was always very jealous of me which I found very odd.

That can happen with any siblings.

We finally met and she actually lives with us temporarily.

"Us"? So you're shacking up with him? (It gets better... I've read ahead some.) Is this your place, his place, or are both of your names on the place? If it is your place, kick him out. If you are renting, move.

We went to dinner with my son and she sat between my boyfriend and me and they talked low to each other the whole night.

They were being rude. Manners are more important than morals?

Then when we got to my son's house from the restaurant my bf went to the bathroom. She ran in the house to the bathroom door banging on it for him to let her in. When he didn't she stood outside the door till I walked by then she left.

It is quite likely that she wanted to use the bathroom before he did, or she likes bothering him.

Later I heard them talking about sex.

Adults sometimes do this.

The next morning she went up to him and said in a low voice "I thought you were going to show me something" and he said he couldn't cause my son had to get up early and get in the bathroom.

If they're talking about having sex with each other, then they aren't doing a very good job of hiding it from you, could they? Don't you think they would?

Since she's been in my apt I've come home several times to the bed in my room messed up in the same way it would be had my bf had oral sex with me.

Is your boyfriend a complete idiot? He must be, if he is doing someone (sister or not) in your bed and not cleaning up. (Of course, later, she says they grew up highly religious and sheltered, so it is possible that the sister could have a "secret" relationship and could be using the writer’s bed either because it is bigger or just to be rude.)

Also I know she's been using my shower but she doesn't know I know.

So what?

They are 25 and 28.

Ah-HAAAA! Now, you can read past entries here and know that I have enjoyed being a younger man to an older woman. But really... she has these two 20-somethings, who are probably close in age to her son, living with her, and she's taking the relationship seriously with the guy?

I've been using a tape recorder but so far have nothing.

That could be illegal. She added later:

Ok for those who think I'm being too suspicious, I overheard her tell him she's still so tight down there because she's a virgin as if he knew first hand.

Well then we know they at least aren't having intercourse. This kind of talk may be strange, but it still isn't a smoking gun.

Is that something a sister would say to a brother?

Some. My wife's virgin ears used to be assaulted with her siblings talking about their sexual activities. Only not with each other. I think. See below.

And also I know from checking her things in her bathroom that she has been grooming herself and it looks like for the first time from the looks of things. Why would she do that?

Swimsuit?

He also made a joke one day that he liked young, hairy girls supposedly talking about the cat but I don't think he was talking about the cat.

Are you on meds? Should you be? He might also like Greek food, and didn't the Greeks have a story...Oeidipus Rex...about incest?

Also, every time I've suspected something happened, he's always wanted sex with me that night which tells me something during the day really turned him on.

Hmmm. Often, a guy who has had an orgasm earlier in the day will be less inclined to want sex later that same day. But then again, he is in his 20s. The writer also thinks it is a matter of the brother giving the sister oral sex and, apparently, not getting a release until later, with her.

She was abused by her dad growing up and her family life was horrible.

So there could be some messed up behavior as a result.

Well, there's no smoking gun, just a cumulative circumstantial case, but it doesn’t matter. The current situation isn't right for you, whatever it really is.

I could made a good case that two of my wife's siblings are doing it. I'll call them Robert and Alice.

A least one classmate gave Robert sexual favors as a going away present when the family moved to another region of the country. He was only 13, so he got started early. He ended up staying in that other region of the country when the family moved again so that he could complete high school and go to college in that area. This means that Robert didn't see the rest of the family much, including Alice (who is younger), during some crucial years. Siblings who mature apart from each other sometimes experience sexual attraction.

Robert and Alice have both messed around with the same girl.

Though he has sex with them, Robert keeps his women at a distance, and that seems to be fine with them for a while - they'll take what they can get before they or he moves on. Alice bounces from boyfriend to boyfriend rather quickly, and I’m fairly certain she is having sex with very few of them. Marriage doesn't appear to be in the near future for either of them.

After Robert moved back home, Robert, Alice, and my wife's other sibling moved out of the parental home together to share an apartment, then moved back in, and then Robert and Alice moved out together again. They have since moved together again to yet another rental. They have a history of "partying" together. I've noticed they will do horseplay with each other and share the hot tub. When the family is gathered for the day or the evening often with some friends, they will often go off together even though they can hang out together back at their place. It isn't because they are shy, either – they are very outgoing.

The other sibling refers to Alice as Robert's wife (to Alice's protests), and Alice does act very protective of Robert, even though he is older and can handle himself. For example, she'll badmouth his girlfriends if she thinks they have wronged Robert. On social networking sites, Robert has sometimes sent out updates referring to "we", inclusive of Alice.

So... in either case, what say you? Are the siblings in either case too close? Are they that close?

Mistaken For a Cougar

HAPPILY MARRIED MOM IN OHIO wrote in to Dear Abby:

I'm an athletic, youthful-looking 58, and my son, "Barry," is 24.

Good for you.

We go out alone for dinner quite often because my husband (Barry's father) doesn't enjoy eating in restaurants.

Good.

My problem is the angry stares my son and I get from younger -- and older -- women who mistake me for a "cougar" out on a date with my "cub."

There's nothing you can do about it, other than calling him "son" loudly enough in conversation so that these other people hear you (of course they might still assume it is a date and be even more hostile). If you are in public, you have to deal with the public. Or choose restaurants with booths that have more privacy.

The other night when I left our table to use the restroom, a woman approached Barry, told him he was "disgusting," and asked, "Why don't you date girls your own age?"

Really, what is disgusting about a younger man having dinner with an older woman? If you think that is disgusting, is it also disgusting if the sexes are reversed? If you say it is disgusting because it must be about sex, then don't kid yourselves – most dates these days are about sex.

As far as the second sentence, I can think of several responses...

"Because they do rude things, like approach strangers trying to enjoy a dinner with a parent and insult them."

"Because they're too easy."

"Older women know what they are doing."

"Because I want to talk about meaningful things like the world situation, and it is very hard to find an unmarried 24-year-old-or-younger woman these days who pays attention to such things – watching MTV doesn't count."

"She likes me for my personality/body/staying power in bed, not my wallet. She has her own money."

They won't be likely to know what to say after that.

He informed her that I was his mother, but even if I wasn't, it was none of her business.

You're right.

Another time, a girl Barry's age asked him why he was out with "an old hag" and said, "How can you want her over me?"

He could have said, "I don't have to choose. Meet me later." But then again, after she called his mother and old hag, why would he want her?

But something else comes to mind... why would this woman's son tell her these things? If someone called my mother an old hag while she was in the restroom, I wouldn't tell her that when she came back to the table. Maybe he's making it up?

This happens every time we go out.

That's suspicious. Or you are exaggerating.

Interestingly, young men who have commented thought it was "awesome" that Barry could be out with a cougar.

Exactly.

It's only the females who have a problem with us.

What, are you telling me men and women are different, and sometimes it is women that make life difficult for other women, especially when it comes to relationships? Naaaah.

Sounds like jealousy on the part of these other women. Dear Abby agrees.

I've written before about some of my experiences with significantly older women. My wife is five years younger than me - the only serious girlfriend I ever had who was more than a year or two younger than me. It wasn't like I wasn't attracted to younger women. I just don't think they were as attracted to me. I had a habit winning women over with my personality, my humor, my voice, my conversation. Younger women (meaning early 20s) are about partying and money.

Sometimes, when I was out with the older women, people would react - but that comes with the territory. It is a little more accepted these days.

Cubs Check In

Dear Abby printed her follow up on "cougars" – responses from men in what they see in older women. Some of the situations stretch the prevailing concept of "cougar/cub", but it's all woman-older-than-the-man. Here's my entry discussing the previous column on cougars.

SAN DIEGO READER wrote:

Abby, cougars are nothing new. They're simply out of the closet.

That may be true, but I think there are more of them now.

WILLIAM IN MARYLAND wrote:

Older women are more established and more interested in fostering personal relationships.

That’s true in some cases. In other cases, the guy isn't looking for a relationship. He's looking for some fun with someone who either can't get pregnant or knows how to prevent pregnancy – someone with experience who won't ask, "Where is this relationship going?" like a woman his own age might.

STILL GRIEVING IN KILLEEN, TEXAS wrote:

On my 25th birthday, I met a woman who was 10 years older than me. We were both just looking for someone to have fun with. Six months later we were married. We were still together 45 years later when she passed away. I wouldn't trade our years together for anything because we were friends and able to talk about anything to each other.

How sweet, and very beautiful.

If you find someone you are comfortable with, don't let the calendar get in your way.

That's where I disagree. Comfort is a necessity. But it is just one. Age matters, especially if someone wants to have children. For example, these women getting pregnant by geezers are most likely setting things up in a way that will deprive the children of their father.

JOHN IN GRAND MARAIS, MINN. wrote:

"'Cougar' in New York" answered her own question when she said, "I am a caring, fun person who loves music and dancing." Women like her are attractive at any age.

Yes. Well, I'm not really sure how many straight American males really like recreational dancing for the sake of dancing. Guys tend to use dancing as an excuse to rub up against women they don't know, or go along with dancing to please a woman they are already with. Now, if she likes to dance for her man in private, that's another story entirely.

It's the lack of older men who can keep up with them that makes "cougars" available to younger guys!

It's not so much that the older men can't keep up with them. The older men are working or are with younger women or are doing other things - things they want to do. They don't want to dance.

With very few exceptions, no, an older woman is not as hot as a woman who is a fit 18-25 years old and hasn't had kids. Men are visual creatures who need to be turned on to function, and like just about all males in the animal kingdom, men are expected to do the pursuing. So female physical beauty matters more than male in the dating game. That's nature. Wrinkles, fat, sag, scars, stretch marks, spots, and other skin problems take their toll and make a difference. HOWEVER, older women can be more attractive overall because of their experience, personality, social skills, understanding of men, kitchen skills, bedroom skills, knowing what they want, and independence. And when it comes to an established marriage, a wife who keeps herself somewhat in shape and presentable and treats her man right is going to be much more attractive to him than some young flirty tart with all the right curves.

It's a free country. Unmarried adults are free to date other unmarried adults, whatever their age differences – and others people should not harass them or disparage them doing so based solely on the age difference. Now, if one of them has minor children, I would discourage dating anyone of any age. But that's another blog entry. If my mother or sister started dating a younger guy, it wouldn't bother me.

Cubs and Other Cougar Partners

I'm not talkin' wild animals. Dear Abby checked in on the cougar issue. The follow-up for this one is still on the way, I think. It will be interesting to see the responses.

"COUGAR" IN NEW YORK wrote:

I am a 59-year-old woman who has been dating men in their 40s.

Good for you.

At first, I refused because I thought they were too young for me and people might laugh.

People might be jealous and envious, too.

Since then, I have decided that as long as they know from the beginning that I'm not looking for a serious committed relationship, I'd be happy to go out.

Good policy.

Abby, why do you think younger men are attracted to older women?

Dear Abby responded:

If I were to hazard a guess, I'd say it's because many older women are independent, self-confident, worldly and not looking for commitment. Those qualities can be very attractive if a man isn't looking for commitment either.

Yeah, pretty much. If a guy is just looking for someone to be on his arm, and doesn't want the bratty drama of someone closer to his age or significantly younger – someone more likely to "fall in love" or get an idea that this will lead to a lifelong commitment – then it can be a good thing. An older woman, in addition to being more socially adept when the couple encounters other people on their date, is more likely to recognize when she is developing an attachment that she shouldn't and take corrective action. Often, she keeps up on current events and can talk about them, unlike a lot of younger women.

If a guy is just looking or sex, older women bring experience, a lack in inhibition, and more of an ability to be discreet.

Either way, she is less likely to be financially needy – in fact, she may actually reverse the money dynamic and pick up the tab and buy the guy gifts. There’s the risk – that the older woman will attract a gigolo.

Also, just like with gals, it makes a young guy feel like he's somehow superior to his peers if someone older and more accomplished/established is interested in spending time with him. Usually this notion is self-delusion.

I wrote about my first relationship with an older woman in this blog entry.

As far as I know, the oldest woman I was ever involved with was in her 50s. If she was older than that, well, then she looked young for her age. I was in the waning years of my 20s at the time. As far as I know she was childless. We spent about two weeks together, and she definitely knew what she was doing and how to please a guy. We both knew at the time that we were not going to be a couple. We didn't live anywhere near each other, and that wasn't going to change. She reported in one of our last contacts that she'd married a guy closer to her age – a guy who had been in her life as long as I'd been in contact with her. She'd previously presented their relationship as platonic, but for all I know she was married to him all along... though I doubt it and I hope not.

Yes, in general, younger women are physically more attractive to men than older women. However, that doesn't necessarily translate into a good date or good sex. So while women are out there dating older men and thus not available for guys their age, some guys their age will happily pass the time with the older women. It can work for dating. It rarely is a good idea when it comes to marriage.

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 than 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.

Going Intergenerational and Blending Families

Let’s check in on relationship problems via an advice column, shall we? "Non-Cougar in Calif." wrote in to Dear Margo:

I am 29. My love is 55.

Okay.

We were friends first, and then it turned into a real relationship.

Let me guess... you are an "old soul"? Of course you were friends first, but only because you were attracted to him and he was to you. If you hadn't been attracted to him in the first place, he would have ended up in the "only a friend" zone, never to get out.

When we met, it was supposed to be "Friends with Benefits," but as the years went by we developed feelings for each other, which led to a relationship.

Funny how that happens. See - "friends first" - right.

I have a 5-year-old and he has a 16-year-old.

Oh heck no. Wrong! You should both be focusing on raising your children.

I've said that maybe I want more children, and he has said he’s open to it.

As "guy" as my first language, let me translate what he means: "I don't want more children, but I want to keep fornicating with you, so I will not give you a definite 'no' because this way, you'll keep fornicating with me."

But with our huge age difference, I am questioning it. What are your thoughts?

Raise your child. You'll be 42 when you child is raised. If you want to adopt then, find a man closer to your age who always wanted to adopt, marry him, and adopt. It is a bad idea to get pregnant by a 55-year-old guy who has a 16-year-old and doesn't want more kids. When you also consider that you already have your own child to raise... forget it.

I speak from some experience when dealing with age differences and prior kids in dating, although in my case she was the only one with a kid (who was, like this case, 16), and was the older one in the relationship. Throughout my rebellious time, I had relationships and flings with a few older women. One of those pairings had the same age spread as the letter-writer's, though I was 19 and she was 45. It is even more problematic at those ages, and with the male being the younger partner.

Mind you, I didn't know this woman was 45 at first.

In the days before most people had their pictures online, there were these dial-up electronic bulletin board services – some of them for a hobby or interest, and others for socializing. This one was for socializing in my metropolitan area, and you'd see someone's first name, their age, their gender, and their sexual orientation. I started talking with, among other people and usually in a "group setting”, a woman I thought was 29. It was never dirty, mind you, even when it got flirty. Just joking around and talking about whatever. When I took a serious look at her stats again, she was listed as 39, and I wondered why I had started chatting up someone so much older than me, not remembering that the stat previously said 29. Why all of this happened this way and how I eventually found out she was 45 is rather a boring story and not important to this post. The two important things to remember is that when I got heavily involved with her, I thought she was 39, and she later told me she was 45 after some math didn't make sense to me.

Originally, she had thought maybe I would be good for her daughter. But her daughter was a troubled brat. And shewasn't interested in me anyway. So, the elder woman of the house began to flirt with me big time. Dysfunction much?

Me, I was wrong. Wrong wrong wrong. Wrong for getting involved with a much older woman, wrong for getting involved with a mother with a minor child, and wrong for fornicating. Not to excuse my sins, but rather explain a little bit... I was almost completely inexperienced with dating, naïve, felt affection-deprived, and had an inferiority complex. I was ill-equipped to resist the flirtations of a (very) experienced, available older woman, even if this was before the whole "MILF" thing made it to pop culture. I was also living on my own, away from my family, by myself. That makes messin' around really easy.

We carried on for a year and a half. We didn't keep it a secret. Our friends and family and even a lot of our coworkers at our respective workplaces knew. We struggled from time to time with the age difference and the morality of the whole thing. It fell apart after her daughter gave birth. Grandma did't want to deal with the drama of her new-mother daughter fighting with her, and ditching me gave them one less thing to fight about. About 7 or 8 months later, I stumbled cluelessly into another relationship with a woman who was only two years older than me. Grandma later found some new 18 or 19-year-old guy for a while, and we were on friendly but distant terms until we lost contact after moves.

It wasn't all bad. We didn't really fight with each other, as we were too busy defending our relationship to others. She fed me well – meaning home cooked meals that helped me to lose weight. Between those and the – ahem – regular exercise (minimum three times a week, every week), I didn't even have to try to lose weight – it just happened. I slimmed down to an ideal weight. She showed how to behave with more confidence, and she gave me a makeover so I wouldn't look so much like the nerd I am. I was certainly not as bad off as I would have been if I had "fallen in love" with her daughter instead.

But out of all the things wrong about that relationship, at least we didn't marry, as that would have been a mockery, and I didn't get her pregnant. That would have been horrible for the child. Also, I didn't have a child to expose to a situation that was really all about having sex without marriage or a realistic hope of getting married and having it work.

Thank God for His mercy and forgiveness.