LR: Cougar on an Airplane

Entropy4 · #1 09-16-2007, 11:20 PM

I had just spent four long, hot days in Miami. At the end of my trip, I was clearly disappointed -- I found the stories of South Beach and the club scene down there to be wildly overrated, but then again, I was probably bitter because I didn't fuck anything better than an HB7 while I was there. I originally went to Miami in hopes of chasing and getting more ass than I ever had before, but ironically, I would get my best lay in the process of leaving Miami.

I should note that at this point, sarging was the furthest thing from my mind. I hadn't showered, had only slept for about three hours, and only eaten a shitty sandwich for breakfast. I know gurus say "always look and feel your best," well, I wasn't even close.

I get to the gate and plop down in a seat waiting to board. I look around and actually see a few hot girls. I always like to check out girls who I'll be flying with, because if you're lucky enough to sit next to them, they are an easy sarge. I saw a few hotties, HB8's and HB9's. One had her back to me standing near the check-in counter: slim, athletic body, gorgeous tan, nice rack; although I could not see her face, her body was an easy 9.

I get on the plane, and lo and behold, I'm sitting next to the chick I had checked out, but I notice when I look at her face: she's old. Not like, OLD old, but she's definitely MILF-territory, mid to late thirties. Regardless, I proceed to pass out next to her with my iPod going. I was asleep so fast that I don't even remember take-off.

Couple hours later I wake up and HBCougar is watching some movie on her laptop. My iPod dies so I lazily sit there and stare at her screen. I decide to open her by commenting on the movie. It's some cheesy thriller from the 80's with young Kurt Russell and Ray Liotta apparently fighting over some hot chick. I watch for a good 10-15 minutes until the apparently evil Ray Liotta is trying to rape the babe, but then Kurt Russell shows up to rescue her and they end up fighting a bloody battle in the chick's kitchen. At this point, the plane edges downward and there's an announcement to prepare for landing. The stewardess comes by and asks HBCougar to turn off her laptop. HBCougar shuts down the movie and takes off her earphones.

I'm still kind of in a haze, and although I'm definitely attracted to HBCougar (any of my friends will tell you, I've grown to LOVE older women), I'm still not committed to sarging her.

Me: "Damn, now we'll never know if the bad guy wins or not."
HB: "He ends up getting beaten up by a frying pan, I've seen it before."
Me: "I haven't. I'm disappointed, that looks like an awesome movie." (said very sarcastically)
HB: (laughs) "Yeah, right."
Me: "Was that Kurt Russell?"
HB: "Yeah, when he was like 15. I just bring these cheesy movies around because I travel so much, I get bored on airplanes."

At least she's engaged and actively pursuing a conversation with me and I'm actually semi-conscious. It's at this point that I begin sarging her with purpose.

Me: "What do you do?" (Wow, awesome start Entropy4)
HB: "I'm a sales rep."
Me: "Selling...?"
HB: "Online advertising, I meet with clients all over the US and Europe. We have over 600 clients in the travel and tourism industry."

Awhile back I was talking to an older woman in her 30's and we were talking about why 30-something women and 20-something men hook up so often. She gave me a great nugget of wisdom. She said that dating in your 30's often revolves so much around your career and status that a lot of the fun is drained from the relationship or interaction. Women begin basing attraction on success and wealth as much as they do on personality and emotion. She said that women in their 30's love the excitement that guys in their 20's bring -- the guys just want to have fun (and sex), and these women miss that, so they are often drawn to them. So anyway, this woman is going on about her job, about how much she travels, her clients, what she sells, etc. Fuck that, welcome to MY reality.

Me: "Oh... my... God!"
HB: "What?"
Me: "You're responsible for all those fucking pop-ups ads on my computer, aren't you? I hate you." (I playfully push her away from me.)
HB: (laughs) "Don't hate me, we don't do pop-ups."
Me: "Oh, thank God... I'd have to stop talking to you.
HB: (laughs)
Me: "So, you're in Boston for business?"
HB: "Yeah, a meeting tomorrow morning, then I fly back out tomorrow night."

At this point we're landing in like 2 minutes and asking for her number crosses my mind, and I suppose I still have some limiting beliefs because I just figured me going out with her wasn't plausible. Stupid me, because she's giving me some eyes now, I notice she has no ring on her left hand, she gives me IOI's by re-initiating the conversation.

HB: "Where are some good places to eat in Boston?"
Me: "Umm... Boston has great Italian food. You should check out the North End, lots of good Italian food there."
HB: "You don't have any specific recommendations?"
Me: "Uhh.... no, not really."
HB: "Well then, what good are you to me?" (smiling)
Me: (laughs) "Apparently not much, I guess I don't eat out much."
HB: "Well then, what about bars? Where could I get a martini tonight?"
Me: "Depends, where are you staying?"
HB: "The Fairmont in Copley Plaza."
Me: "Oh, I know a ton a good places around there."

I said this with the idea to set it up so that she would ask where -- giving me the chance to take her out. But she trumped all this.

Why I Fucking Love Older Women, Reason #1: They are REALLY aggressive.

HB: "Well, you should come out and show me around, get a drink with me."
Me: (caught a bit off-guard, trying not to stutter) "Yeah. That'd be great."

She gives me her number and even corrects me when I mess it up. I already had an entry with her name, so my phone popped up a big red 'X' with "WARNING" under it telling me to change the name of the entry.

HB: "Uh oh, your phone is warning you."
Me: "Yeah, it's telling me 'Don't call this woman, she's bad news'."
HB: (laughs real hard) "I need a phone that smart."

We fluff a bit more and I ask if she knows anyone else in Boston. She says she has a friend here, but "he has a girlfriend now, so he said he can't see me." I am SO getting laid tonight.

Few hours later, I'm in a swanky restaurant bar on Newbury Street with her and her co-worker. Her co-worker is married and a bit younger than her, a pretty blond from NYC. I tell them that I just spent over two weeks away to go to Texas and Miami. The co-worker asks me how I used up so much vacation. I respond, "It's pretty damn easy when you're unemployed."

I took a risk here, but I'm glad I did it. My only insecurity going in was that I'm unemployed and they may take me for a deadbeat or just some immature kid. I threw it out there and owned it and they got a good laugh. I very maturely stated my reasoning that I'm fresh out of college with no debt, few bills, and I didn't see a point in jumping into a career right away. They accepted my reality because I did, and it was smooth sailing.

Next came the age-guessing game. They asked me straight-up, but I toyed around with them first. Eventually, I give in and it comes out that I'm 23. HBCougar looks over at her co-worker and says bluntly, "I'm a sicko." Turns out HBCougar is 35.

I have a couple beers in me and my game is clicking on all cylinders now. I start directing the conversation about places we've all visited before, and meanwhile I egg on HBCougar with playful "old lady" jokes. At one point she says:

HB: "You know, technically, I'm old enough to be your mother."
Me: "Technically, you could be calling me 'Daddy' any minute."
HB: (laughs, stunned look on her face) "What makes you think that? I only talked to you for 10 minutes on an airplane!"
Me: "Yeah, but I can tell, you're a woman interested in quality, not quantity."

Next came one of those lines women say now and then that are the biggest compliments any aspiring PUA can hear.

HB: (pauses) "It's kind of scary to see so much confidence in a guy your age."
Me: "It's not a bad thing."
HB: (looks me in the eye and smiles) "Definitely not."

I get up to go piss to give the women some time to converse. It's about time to bounce and I think I've won the co-worker over and HBCougar is definitely attracted. When I come back the co-worker says she's going to go back to the hotel while we go somewhere else -- this is girl-code assuring me that I'm in. I suggest a venue-change to HBCougar and she agrees.

We go to a hotel bar. It's a nice calm atmosphere with a lot of older business-types at the bar. We sit down at a table/booth, me in the booth, her in the chair across from me.

HB: (looks around) "Do you feel a bit young in here?"
Me: (laughs, pointing to old people at the bar) "Do YOU feel young in here?"
HB: (laughs) "Yes, actually I do."

We fluff for a bit, and my dumbass self takes like 10 minutes to realize that her sitting across from me is a logistical problem for kino-ing purposes. But luckily:

Why I Fucking Love Older Women, Reason #2: They know what they want, and they don't bullshit.

HB: "So, when are you going to ask me to sit next to you?"
Me: "Uhh.... yeah, I was actually just thinking about that."
HB: (gets up and sits next to me) "What took so long?"
Me: "Umm... I guess I was thinking of how to bring it up."
HB: "You're going from sharing an airplane with me to a bed with me in six hours, then you'll probably never see me again; just say it."
Me: (stunned) "Uhh... yeah... I was getting there, I guess."
HB: "You're cute."

Entropy4 · #2 09-16-2007, 11:22 PM

We start kissing and kino-ing hard there in the booth. Soon, some young professionals come and sit at the table next to us. They look as if they're in their late 20's and are very drunk. One guy is very friendly and starts giving HBCougar a lot of attention in front of me.

Drunk Guy: "So looks like things are going well for you two, this your first date or like the 10th?"
Me: "Like 12th or something. This is nothing new for us."

HBCougar LOVED this. She started playing along and made up some story about how we're a long-distance couple and she travels to Boston between business trips every few weeks. I created some elaborate story about being in law school and considering moving down there with her after I graduate. It was hilarious. She loved it. And she loved me for playing along. "Law school... nice touch," she said later. I said, "I wanted him to ask how we met, so I could tell him on an airplane."

The bar closes and we head back to her hotel room. The room is fucking posh. At this point, it's pretty clear what's going to happen:

Why I Fucking Love Older Women, Reason #3: They're great lays.

Wow, this chick was awesome. I was in her room for less than 10 seconds when she just shoved me onto the bed and climbed on top of me. I'm usually not so big on foreplay with a lot of girls, but I could have gone on for hours of foreplay with her. She was just so sensual, responsive and playful. It was fucking awesome. Then of course the sex came, and as with other 30-something women I've been with, her technique was immaculate and she had some new positions I hadn't seen before. She moaned a lot and talked filthy, which is something I rarely get from girls my age. Very nice.

So even though she told me I wouldn't be sleeping there, I slept there. The next morning we talked briefly and I told her anytime she's in Boston, I would love to hear from her. She seemed a bit skeptical at first, as I think her previous Boston hook-up was flaky or a drama-queen or both. But I told her for me it was no bullshit, if she comes in, I'm her boy-toy for the night. She liked the idea and said she'd be in touch. I rode home at about 7:30am. She sent me a text about 30 minutes later thanking me for the night and saying she couldn't believe she's going to an important meeting on only four hours of sleep. This afternoon she sent another text saying her meeting went well and that I'll be hearing from here next time she's in town.