An Observation about Libras

I’ve gotten intimate with a few Libras and I’ve found a pattern.

Libras like to arouse a man via his nipples with their lips and teeth. And they do it fantastically well. Enough to get a guy really hard without even going down. Talk about seduction.

I love it and it drives me nuts. A friend told me it’s just better to arouse a guy by giving head. Yeah, sure, that works too, but the sensation is different. I’ve had other women try to arouse me via nipples, but it hasn’t worked — perhaps because they were not Libras.

So Libra women out there, if you don’t do it, do it. And if you’re not a Libra, please prove me wrong about your sign.

The Oral Festish Sub

I’ve spoken about The Spanko already, but the Oral Fetish Sub, a 5’11″ beautiful Italian girl, homegrown in the Valley really brought out the Dom in me. The great thing about it was that it was never expected, talked about or anything. It just happened. It was natural.

She and I met on a website under the premise of friends with benefits. Before my first time with her, the only forewarning I had was that she liked to rip clothes off and fuck immediately, screw the foreplay until after (dessert before dinner).

Immediately, I knew this was rough and wild, lots of movement. For some reason in the middle of sex, I just blurted out, “do you do anal?” She said yeah and in seconds we were doing just that.

She liked it abusive. I found out by pushing the limit, seeing if she would retract or not. Chocking, check. Ass slapping, check.

Then came the true test. She liked oral later in sex and as she was going down on me on the bed, I moved her aside and laid her body down on her back with her head hanging off the side of the bed. I stood over and put my cock inside her throat, deep down, pushing it in and out, slapping her breasts, chocking her with my cock, making her gag. She loved it, I loved it. It was hot, period. Then we went into the shower, finished the night off.

In the mornings after I slept over, she loved to give head — it got her off when it got me off. Then I would drive home in morning rush hour traffic. Lucky for me, home and work was opposite of traffic, so I cruised with a smile on my face.

The Sex Site Girl

I only met one person when I tried out the notorious Adult Friend Finder. If you’re not a couple or a “Big black cock,” chances of meeting someone is tough. The naughty site, after all, is all about playing out fantasies. And here, women are the ones who call the shots.

One of them decided to meet me.

I was 24, she was 18. At that point in my life, I had had a lot of good sex, but I hadn’t had crazy sex until then. Not bad crazy, but as I look back on it, or in the moment, it is crazy good in a sort of funny way.

We were on the phone one night talking and she decided to meet right then — she was going to drive to my apartment from Culver City. She said there would no sex, just hanging out and I said that was fine. Of course, you know that never happens. We made out, I gave her head and then eventually, she goes, “I’m going to break my rule.”

She looked like Franka Potente from The Bourne Identity. Kind of punky, but with a baby face. That was hot — not to mention she had breasts worthy of magazine spreads.

We got naked, put the safe sex on and it was time. She wanted to be on top, so she could control the slow dance. The moment it all began, it was like she went on drugs and she started saying things she couldn’t remember. The first words after a moan: “It’s like you and me were meant to be inside each other.”

Dead serious. It was said in such a I’m-on-acid-and-live-in-the-1960s tone. I almost bust out laughing, but that wouldn’t be appropriate with someone I just was getting to know.

Over our summer of sex before she moved up to San Francisco, I gathered a good amount of quotes she would claim not remember saying. My favorite was when we, in pitch darkness, were going at it slowly, very passionately: “I love you,” she moaned, then a moment later, as she moved my body with all her force making me hit my head on the bed post, “I don’t love you, I don’t love you, I don’t love you.”

I remember a scene very much like this from a Red Shoe Diary episode on Showtime. The sex continued for a long time that night, became rougher, kinkier, but she said she never remembered saying and doing any of that.

The last time I saw her before she moved up north, we did not have sex. We made applesauce together and ate it.

The Spanko

I met a Valley girl on Match. When I say like-OMG-Valley, I’m talking Arleta, pretty hardcore, leave the Valley accent to Encino and West Valley Jewish girls.

Anyway, our first date (we met once at a mall in public beforehand), I come to pick her up and she lives with dad. I walk up to the address given, see two men in the garage. I call out asking if this was her home and he asked if I was picking her up on a date. I said yes. He looked at the ground shook his head and grabbed a wooden baseball bat and started walking towards me — fast.

He saw my deer-in-the-headlights moment and started cracking up. I laughed a sigh of relief. Soon enough, she and I are on our way down to a choreographed jazz dance show in Leimart Park. I took the whitest girl ever (who would refer to Arabs as A-Rabs, ugh) to a very black community.

Once back at her place later that night, dad’s asleep, we start fooling around. Soon I get uncomfortable, she’s just lying there like a dead fish, I didn’t know what to do, it was weird.

Later, talking over IM, I find out she’s pretty submissive and this was my first true sub date. Actually, she was the spank-me sub kind. Hrmmm, I’ve never done that. And she was a virgin, too — like she wasn’t interested in sex. Spanking made her cum. So I tried and failed miserably. I was too light, then too hard. She said using a hair brush works. She wanted me to make her cry and I was all very new to this (young 20s and she was 19).

In the end, it didn’t work out after a bunch frustrating make out sessions that showcased my lack of apparent spanking skills.

Two years later, I had a moment of spanking inspiration, so I called her up, said “come over.” She did, we got naked, I bent her over my lap and spanked. I was a little better, but I don’t think I can force myself to sit there and spank someone sexually like you see in shots from the 1950s.

Don’t get me wrong, a good spank during sex in the moment when appropriate is awesome. But the pre-planned spank session is just not in me. I can be extremely dom with subs, but in a sexual in bed nature, not on the chair with no sex in sight.

It stings a little. She’s a classic next door neighbor brunette, slim, bountiful breasts, great lips, especially when she went down that one time — quite the tease.

I look back and am thankful someone was there to break my erotic spanking virginity. Now I know I don’t need to go back.

I’ll keep my spanking for “those moments,” thanks very much.

The Cougar

She found me on MySpace back in 2006 when I was in my mid-twenties. “Hola!” The subject line read — she’s originally from Chile. “Saw your pics….liked them…”

The e-mail was innocent enough, but this 35-year-old woman’s profile photos consisted of one headshot and four close up shots of her huge breasts in various t-shirts. The pieces were coming together.

We continued to e-mail back and forth on the site, usually late at night, occasionally catching each other on instant messenger. Without saying it directly, we were always reading between the lines, flirting and teasing.

It took about a month before we actually met. I was dog-sitting for a friend in her neighborhood. I let her know and she eventually made a visit past midnight. We greeted, hugged, chatted and eventually my head was in her lap. She massaged my head and I made it up to her voluptuous breasts. We kissed, continued to feel each other and she unzipped my pants, to check me out. Then she asked if we could go upstairs.

Being at my friend’s house, I hesitated. But it was a naughty moment and a dirty thought, so I gathered some clean sheets and made up a bed on top of his. We kissed, got naked and it wasn’t long before she straddled above me, lowering herself onto me.

There’s something about meeting someone in real life for the first time and then having sex that night. It’s just… so… raw, naughty, exciting.

That zeal for the moment made me so hard, so long-lasting, we did it intensely four times in a row with the only rest between to slap on a fresh condom.

It was the first time I talked dirty — probably ’cause it was a dirty (but not filthy) night. As we went doggy style, I would pull her hair, she would moan and then start speaking in Spanish.

Un-fucking-forgettable.

Care to chat? Leave a comment and follow me on Twitter at @Arrow405

The Virgin

There was that movie about kids back in the 90s, it opened up with a guy talking about fucking virgins and then moved to a scene where he convinced a virgin girl to have sex with him. It didn’t interest me, I never finished the movie.

The whole breaking a girl in thing is weird to me — I just have no desire.

Back in my last year of college, I befriended a freshman girl and then met her East Coast roommate. Soon, the roommate and I were hanging out a lot, dating, kissing, fooling around all that jazz and then one night…

“Should I get a condom?” I asked, shooting two birds with one stone.

“Yes” she replied, wide-eyed, but confident.

I prepared, straddled her, spread her legs apart and right before it happened: “wait, I need to tell you something.”

Yes, she was a virgin. Oddly exciting, but not really. I really wanted to get it out of her. “Are you sure this is what you want? Are you really, really sure?”

Of course she was, it was her first year of college. In 2002, a virgin at 18 is a late-bloomer. We fucked in my bed and when I came, she asked what was wrong.

“Nothing,” I smiled, everything was quite well.

We continued on to round two, but being her first time, she was getting worn out down there. We moved on to the shower for a break, tried positioning ourselves in there for more fun, but that shower was built for midgets, so to the bathroom counter we went. She leaned over, I fucked her from behind. She then sat on the counter and I stood and fucked her from there. Once again, she was getting a little sore down there.

I say “fucked” a lot here because that is what it was. No passionate love-making or even sex, it was an 18-year-old girl who wanted to party… and well, fuck.

She wasn’t a hussy and actually, she met a guy soon after who she dated for about 5 years. They moved to NYC together, but last I heard, she is single again.

I’m still not interested in virgins and I presume at my age, meeting a woman of similar years would not be a virgin (if she is, then we are just entering weird territory). And for me breaking in a young 18-year-old again — probably not going to happen, and that’s fine with me.

7 Tips On Meeting Older Women (And Where To Find Them)

The Sexiest MILF on the Planet, Brenda James

On my last diary post, a commenter asked for more on older women, specifically where to find them.

I personally believe potential cougars and MILF partners are everywhere and that it’s more about taking a situation to that level.

So before I get to the question of “where,” let’s list some basic tips:

Older Woman How To

1. Scout’s Motto. Make sure this is what you want – that it is a fantasy you really want played out – and be prepared for an amazing time when it happens. Don’t get soft on her.
2. Game Over. Many older woman are done playing the coy games we do in our twenties.  Be honest about what you want because she will be direct about about her desires.
3. Listen. On that note of directness, listen to her words because she is still a classy woman who will expect you have some brains to read between her obvious lines.
4. Play. She’s not flirting or initiating conversation to waste her or your time.  Flirt back because there’s an endgame that will leave you satisfied.
5. Respect. If she has children, you must understand that she may not want you at her home, or at least when her kids are home. Don’t be pushy, be patient, it’s worth it.
6. Foreplay. It may or may not happen (sometimes, she just wants it… and right now). Go with that flow and give your all if in foreplay mode.
7. Endurance. She’s likely at a sexual peak unlike any before.  It might be a long, but awesome night.  You’re young (that’s part of the attraction) so make sure you’re hard for long enough! Expect to do it multiple times in a night.

Now, on to where to find a frisky kitty woman.  There’s no one answer to this. Here in Los Angeles, cougar dens, as they call them, can be found in suburbia.  Think The Southbay, Agoura Hills/Thousand Oaks, Orange County, Pasadena. That may sound a bit stereotypical but in my experience, the divorced women living here are feeling a bit sheltered so it’s your job to spice up her life.  Still, MILFs are everywhere:

• Online: Whether it be MySpace or Facebook, does she list her self as single and looking? Does she have other younger guys as friends? If on a dating website, does she directly say she likes younger men.  Did she look at your profile? Remember, older women will be more upfront than younger women in most cases. If she’s flirting, follow through because, remember, she’s done with games.
• The grocery store (or any store for this matter), art galleries, coffeeshop: Does she look your way often, make eye contact, did she throw you a smile? And if she asks you a dumb question about where the soy sauce is, the door is definitely open for you to engage.
• At bars, on the casino floor, social situations: Things should be fairly obvious in these situations, but the drinking makes people more flirty  than usual, even if she’s not looking. But hey, in places like that, live it up, be yourself and have fun as that’s what a woman will find attractive.
• On the sidewalk.  In all cases like this, it doesn’t hurt to throw a smile in when you make eye contact. You would be amazed how little people do this and how much such a small gesture can open things up.

Got questions, comments?  Ask, let it be known, etc.  You can also follow me on Twitter at @Arrow405.

Above photo of Brenda James via her website.

The MILF

I was 21, she was 39.

I met her up at a Mexican restaurant over margaritas in Northridge. If only we were the same age and she didn’t have two kids, we could have been a couple.

Our second “date” was at her place. She made me pizza with Trader Joe’s dough, she kicked my ass at Scrabble, I played some piano for her. Then the clock struck twelve and it happened to turn into St. Patrick’s Day. I smiled and jokingly said, “kiss me, I’m Irish.” Under her breath, she went, “finally,” and leaned over.

We made out on the couch, but soon were on the floor. I massaged her back as we kissed and that made her hot (she said so). She took off her shirt, but we soon made our way to her bedroom. She lit candles and I went down on her, writing the alphabet with my tongue, eventually getting deeper, making hips swerve unintentionally.

Soon, that moment came, it was a beautiful moment too. The condom was on and I was on top of her. Outside, I was confident, inside myself, I was ecstatic. I was about to make love to an older woman, a woman who was funny, who looked like Sela Ward combined with Sheryl Crow, a woman of great intellect and adventure — I was her first young guy, as she was my first older woman. The moment I was inside of her, I said to myself, oh my god, this is actually happening. It was amazing.

We danced in bed, against the wall, screaming hard, riding on top. At one point, in a moment of inspiration, I grabbed the candle and spilled the candle wax over her breasts. She yelped, but it was hot, more than literally.

Then we spent an hour on the floor, 69ing, passionately.

After three hours of tantalizing sex, we came to a rest, tired, satisfied and in amaze. She said she was surprised and wasn’t expecting that great of a time and endurance and I was happy I could please.

The only sad part was no morning sex, she had to kick me out that same night. Her ex was coming over early in the morning to drop off the kids and there was no need for this kid to be there when that happened.

I drove home that night on the 101, still hard as a rock, thinking about what happened. That moment, when I first entered her — it was beautiful. Will I ever feel that again?

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Care to chat? Leave a comment below and follow me on Twitter at @Arrow405

I’m Arrow, Veteran Online Dater

I have a penchant for online dating. That’s not to say I meet women in real life–I would say half of my dates are from real life, the other half virtual–but there’s something fun about the whole online thing.

The anticipatory butterflies are worth it for one. That might sound hellish for some, however, the highs and lows they carry can be quite the ride. In your mind, you always hope for the best, whether it’s a date or something that should clearly be read between the lines. But as all things online go, things are not always what they seem.

A few examples to illustrate.

The Good: A date in Agoura Hills with a woman my age a few years ago when I was in my younger 20s. I drove out there, we went for food, a movie and came back to her place. We began to fool around and at some point I slipped in that I’d always wanted to pleasure myself in front of someone. I’m not sure why I said that, but I somehow knew she would be receptive. She was more than that, she was extremely excited. She cuddled aside me to watch from my perspective while occasionally nibbling on my ear. I came as she watched and she was soon wet, fingering herself. I went down on her, bringing with me her rabbit. She tasted sweet, unlike any other woman I’ve ever been with (her secret was her kumquat intake as she had a tree in the backyard). Her hips erratically moved about and she moaned until she came. Although she brought out a condom just in case, we were both satisfied and never had sex.

The Bad: Sometimes things don’t work out so well. After speaking online with a young hippie college girl with dreds for a few weeks, I made the trek out to Claremont to meet up with her. From the moment I saw her, it just felt uncomfortable. Her photos were not what she was in real life and honestly, I was not attracted, even if I tried. I attempted to be courteous and hang with her for awhile, but I lied when we were in her dorm room, saying I had never done this before and couldn’t go through with it. Eventually I left and the 60-mile journey to home was my mission.

Years later, I met an older woman online and convinced her to meet with me that same night. Eventually, I made it over to her Santa Monica home around 2 a.m. Needless to say, when she opened the door wearing elastic-band tiger print pants (I’m sure they felt comfortable), I knew this was bad news. Her photos were from a different era, that’s all I’m saying. Since I made the trek out, I decided I would hang out for awhile, but that may have been the wrong move. Another wrong move, let her give me a massage. I mean, hey, I love massages, who is to give a good one up? But the problem was is that she got weird and began to claim my back was “so muscular and hot.” That was kind of odd. I said I had to get going and she tried hard to convince me to stay. I couldn’t wait to get home.

The Odd: I met a beautiful and booksmart Mexican lesbian from San Bernardino who was wanting to test out men… again (she had only one previous experience). We planned a day for her to come visit me and she literally wanted to have the “knock on the door, let’s just fuck” experience. I gave her a tour of the apartment and apparently that was too much dilly-dallying–she asked if we were going to “fuck or not?” Yes, ma’am. I got naked and she didn’t, as she wore leggings with a hole in the right spot. She was submissive, making me do all the work, but luckily, she did give some signs of life with her moans, a clue that things were going somewhat right (as far as I could tell for a lesbian). When it was done, she kissed me goodbye and said “thank you for giving me faith in men.” I never heard from her again.

Over the years, I’ve learned how to spot and avoid the bad and unneeded odd eggs. Nothing’s full proof, though. This summer, I kept on coming across a profile of a woman who by all appearances and words, seemed quite quaint. Definitely cute and smart, but I was hesitant to contact her because I thought she would be too straight-laced and boring of a person. Still, she was online at the same time I was once and our chat went well. After we met, it was obvious that I was colored a creamy white vanilla compared to her. I’ve never met someone so out-of-control hyper and wild than her. It was a mix of crazy good, dramatic bad and odd behavior.

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Care to chat? Leave a comment below and follow me on Twitter at @Arrow405

Image from Remko van Dokkum.