Posts Tagged ‘cougar

24
Oct
13

‘Brad Pitt’ got fat

I caught you up on the return of Pirate Bear, so it’s only fair to catch you up on the “return” of “Brad Pitt” after I ran into him Tuesday night. Saying that we “dated” would be an overstatement, but we had fun hanging out for awhile and I really liked him, so it was good to see him alive – even if I failed to recognize him at first. He’s packed on about 20 pounds since I last saw him in May, the golden highlights he’d picked up in Afghanistan are gone from his hair – now several inches longer – which puts it well past his shoulders, and instead of a tidy goatee, he’s now wearing a full beard.

When we met in February, he caught my eye because he was my type – cute, scruffy and casually sexy. That first day, he was wearing jeans & a hockey jersey and though we flirted a bit, I figured he was too young and pretty for me. When he gave me his number and expressed clear interest with his subsequent texts, I responded positively and we started a brief affair.

The “Young Brad Pitt” nickname came from conversation with my girlfriends. He was 29 when we hooked up and other than the fact that he has brown eyes, the first time he showed up at my door he looked like a 1994 version of Brad Pitt in Legends of the Fall. By the time I last saw him five months ago, he was looking like the scruffier Brad at the end of the movie – which is still pretty yummy. At that time, we were discussing the notion of moving our “relationship” from “occasional FWB/fuck buddy” to “dating” but he was really inconsistent. Sometimes we would text all night. When we were together he was attentive, complimentary, sweet and thoughtful. When we were apart, he sometimes would just drop out of the middle of a conversation and disappear. We had planned our first public outing with friends – a real date – and he essentially stood me up. He later told me that he’d been experiencing really bad panic attacks and PTSD as well as depression. I appreciated what seemed like honesty, but it didn’t change the fact that soon after he went full hermit and disappeared for nearly five months – until a few weeks ago.

The text progression on my phone shows my last text from him on May 11th, followed by a 2am text on October 9th asking how I’ve been and asking if I was at his neighborhood bar. I assumed that this was merely a closing time booty call query and was somewhat bemused. I considered not responding at all, but eventually did the following afternoon, saying that I’d been sleeping like a baby at 2am and that my formerly regular Tuesday hang-out had become pretty busy on those nights and I don’t go as often. He didn’t respond.

Interestingly, I had received a report from a girlfriend that he had been there a few weeks prior on a Tuesday night when I was off at a different place with my boyfriend. At the time I wondered if “Brad Pitt” had been looking for me. I also joked with her: “Did he get fat?! Tell me he got fat!” Well, he did. To the extent that this week, when I was out on the patio at said bar, talking to my same friend and she stopped, stared behind me and said “I thought that was D” I said “no, that’s T’s friend, B.” The person walking in the door looked familiar, but I didn’t recognize him as the guy that I’d been fucking for three months this past spring.

He was decked out like the Kevin Smith character, Silent Bob – complete with trench coat, beard, long hair and backwards Mooby hat from Dogma. I heard a couple of guys shout “hey, Silent Bob! What’s up!” A few minutes later, my friend had gone home and he walked out onto the patio, greeted some people, looked straight at me and said “hey, how you doing?” Even then, I still thought he was the other guy…for a minute. That’s how different he looked! I even went back into the bar for a second drink without speaking further to him – but as I passed and heard his voice I felt like an idiot! I came back out a few minutes later and sought him out – I mean, I didn’t want it to seem like I was pretending to ignore him or playing games. He said “hey, you never texted me back the other day!” I said that I had, then showed him my phone with the text. He then apologized, saying that his phone had been acting weird and texts were really slow – he said he hadn’t sent the text at 2am, but that he had sent a bunch of texts to his “karaoke buddies” earlier in the evening to see if anyone was going out.

We chatted for quite awhile and he acknowledged that his PTSD and panic attacks had been really bad and he was trying to force himself to go out. Several times he mentioned trying to be healthier, wanting to lose 30 pounds and how he’d been riding his bike and working out. Okay, duly noted. We talked about his 30th birthday last month, how that really sucked for him and we casually chatted about movies, music and such neutral topics. When he asked what I’ve been up to I talked about work, my summer and the fact that I’m seeing someone pretty seriously – but that it’s a poly relationship. We briefly talked about that and it was interesting to gauge his reaction. Part of me wanted to know if he would still be interested in seeing me if I was seeing someone else. The fact that he made some noises about getting together again and that we exchanged some more texts yesterday seems to indicate a strong…maybe…

The rest of the maybe is with me. I’m so over the moon with my current guy that I’m struggling with the notion of being poly at all. I haven’t been dating for awhile and I took my OKCupid profile down – at least for now. I haven’t really been sexually aroused by another man since Whimsy & I got serious. I did make out with a new guy but then I called it off before it went further. It hadn’t felt hot or sexy – it felt awkward.

“Silent Brad” could be a different matter. I like him, we’re very compatible in bed, he has his own place and he’s not looking for a relationship. I know he can curl my toes and I’m attracted to him – because let’s face it, Kevin Smith is pretty hot too, right?

There’s a big part of me that just wants to be monogamous with Whimsy to see if we could be successful at that. I think we could be, but there’s another part of me that rebels at the thought of being one of his “harem” and waiting to see if he’s willing to take a risk with me. We’re really good where we are, but it feels somewhat weird that he is seeing other people while I am not. I’m not sure that this inequity is reason enough for me to date, but it’s something that feels out of alignment.

Meanwhile, my options are open as long as my relationship is.

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22
Apr
13

Embracing the Unexpected (firmly, with my thighs…)

Hoo boy! Apologies, friends & followers – I am so behind on blogging! I promise it’s because I’ve been dutifully collecting more material to write about! This weekend was a very unexpectedly good one too! I have enough words & ideas floating in my head for several blog entries. If only I could do a data dump via memory stick rather than my fingers I’d be better able to keep up!

Friday night found me home after work with no plans to speak of.  My intent was to avoid the pissing rain by staying in and catching up on some laundry, house cleaning & movies. It was cold enough that I was considering building a fire and about to thaw some soup out for dinner. Then, at 6:51pm, I was offered an opportunity to go see Prince perform at the Showbox theater at the Market – a very intimate (1100 capacity) venue and a very coveted ticket. The four shows he was doing there had been sold-out for months! The catch was? It was general admission and the doors were supposed to have been at 6:30 but were pushed to 7:00. I live about 15 minutes away and was well on my way to slack and sloth – with no makeup, a t-shirt, jeans & a hoodie. Well, I jumped on it hard! Within 8 minutes I had applied some eyeshadow, put on a “boobie shirt” and some cute boots with a little heel, ran a brush through my hair & was driving. I zoomed into Seattle with moderate traffic for a Friday evening, found excellent (if expensive) parking in a lot a block from the venue, grabbed a junky umbrella out of my car (because it was pouring,) and RAN! I was relieved to see that the line for the show still stretched around the corner, but was motivated to hurry because it was starting to move. I called my friend while I ran and she said that they were just under the marquee and about to be let in.

“Is that you with the pink umbrella?”

“YEP!”

ZOOM! I met them at the door, grabbed my ticket, threw the umbrella in the trash can and strode in to the theater for one of the most exciting, loud, energetic, interactive and ROCKING shows that I’ve been to! The Purple One was charming & engaging, full of humor and wit, dead sexy and had a fantastic, all-female band that rocked. Tight guitar licks swelled and it felt like a house-party jam at times. He did a nice mix of new stuff and yet gave a nod to his hits by opening with “Let’s go Crazy” and closing with “Purple Rain” after a subtle reference to the tragedy in Boston and our need to heal & feel good. Perfect.

My friends refused to take any money for the ticket which I later realized had a face value of $275 and was scalping for $500 easily. Jeez! What an unexpected treat! They said I could babysit for them sometime. DEAL!

When the show ended around 10:45 I was completely amped up and also famished, but my friends were anxious to get home to relieve their sitter, so we parted ways and I found myself full of energy, hungry and…in Seattle by myself with no plans. I realized that a (just friends) friend of mine was hosting karaoke at a bar I like about seven minutes away and decided to go there for some food, singing & company. Excellent choice!

My friend was delightedly surprised to see me. I had sent him a hasty text earlier about Prince and he was suitably jealous and also wanted all the details. My food was excellent and satisfying and the crowd was extremely receptive and enthusiastic for karaoke. There were also a lot of good singers and a fairly short rotation, but the energy of the crowd made me feel like a goddess every time I had a mic in hand. I was still flying high (and also slightly deaf) but planned to leave before the adrenaline waned and fatigue hit. Around 12:30 when I made noises about shoving off my friend protested and insisted that I stay. Then I sang some more, people asked to sing with me and the rotation of singers got shorter…okay, twist my arm!

Around 1:30 my friend’s boss who owns the karaoke business showed up to collect him and the equipment. He is also someone that I consider a friend and we were sitting and chatting when my phone chimed to indicate that I had a text. Thinking it could only be my ex hubby texting me at 1:45 in the morning, I was very pleasantly surprised to see that it was my long-lost “1994 Brad Pitt” whom I hadn’t seen since February but had periodically exchanged some wicked-hot texts with! Normally, I am the one who initiates contact with him, so this was unexpected to begin with, but what he said was that he would be at the club we met at on Tuesday – an invitation to get together again. Also unexpected! Tuesdays at that bar are karaoke nights as well and that’s how we met. The host on Tuesdays is “the boss” that I was sitting with right that minute, so I sent a response saying just that:

“Funny, I’m sitting here talking with XXX right now. He says the theme for Tuesday is ‘work’.”

An immediate response followed wondering where I was, I told him and about my most excellent night & he responded with stuff like “gotcha beautiful” which made my heart and crotch leap because I really enjoy this guy a lot but had basically written him off because he’s so inconsistent. Sometimes he goes out and is an attention whore, sometimes he holes up like a hermit, sometimes he’s chatty & even dirty, sometimes he’s non-responsive or monosyllabic. Also, he’s very young and beautiful, so there’s a little bit of an insecurity issue. Ugh…well, not exactly. I feel perfectly sexy and comfortable with him for the most part, but the reality is that he is smoking hot and must have lots of other opportunities. Realistically, I don’t expect to hear from him often, but am glad when I do. Does that make sense? I’m not putting myself down, I’m trying to express the reality. I do the same thing myself – I have men that interest me more than others for various reasons. But I had sent this guy a really direct & raunchy text last week saying how I wanted to get “growlfucked” and to ride his beard and he had just responded by saying that he was sick and not expressing any particular degree of enthusiasm for the idea in different circumstances. Anyway, unexpected…

Given this background, I decided to be slightly less direct, but I messaged that I was still “totally amped” and he offered that I should come to his place, saying he would be more than happy to have me sit on his face if I wanted. Oh yessssss…..

So this guy’s official designation using my system of initial & age would be P29. However, when talking to my friends & they say “now which one is he?” I say “Young Brad Pitt” or “Brad Pitt in Legends of the Fall” because, yeah…it sort of works. He’s heart-poundingly yummy and I’m sort of stunned that I’ve had sex with him three times and slept overnight with him twice. The fact that we’ve talked a lot, watched a movie while snuggling and that he took my hand while walking me from my car to his door the other night? *sigh*

We met on Valentine’s Day of all things stupid and possibly ironic. I had thrown together an impromptu “anti-Valentine’s Day” outing for myself and four other single friends to go to this dive bar that I enjoy. It was karaoke night, lady’s night and they were doing some Valentine’s-themed pub games that were fun. I brought a huge box of gourmet chocolate that my client had given me and shared it around the bar. It wasn’t very busy, but the fairly light crowd was really engaging and lively. P29 caught my eye for a couple of reasons – one, because he was alone and clearly there for the singing. This is something that I do fairly often, so I guess I just sort of noted the kindred spirit. Two, he is sort of my “type” – longish hair, beard. But he was wearing a sort of loose jersey & baggy jeans that night and didn’t look insanely hot. We spoke a couple of times – once out on the patio while smoking. He was a little stand-offish and slightly dark. We joked about Valentine’s Day and he said something about not being good with women and I said “I somehow doubt that you have a problem in that area” – something that just came out of my mouth because he was dead pretty, you know? Scruffy, but lovely. I swear I wasn’t really flirting with any intent at that point. Just being conversational, really.

Later, having heard his amazing voice, I asked him if he wanted to sing a duet with me. He declined, saying that he was feeling a little bit selfish and solitary. Later, he approached me and apologized saying that he had recently returned from a long tour in Afghanistan and that he was struggling with re-entry a bit and feeling somewhat overwhelmed. We chatted a bit about that and then he added that part of why he didn’t want to sing together was that he was feeling like he was “off” that night and not sounding good. Whereupon I had to tell him that he was an idiot. 🙂 Later, perhaps after a few drinks, he asked me what I was thinking of singing and I suggested “Don’t go Breakin’ My Heart” by Elton John & Kiki Dee. He agreed to sing with me and it was pretty darn good and also fun. Later as all my friends but one left and the singing rotation got shorter, we cheered each other and chatted a bit more. At one point, he turned to me and said “So, XXX, what kind of work do you do?” and I had my first little tingle of recognition that he might just be chatting me up. Hmmmm…

At closing time, about five of us were mingling outside chatting and making goodbye sounds. P29 had told me about another karaoke venue that he frequented and on a whim, I gave him my personal card & said he should let me know if he wanted to sing together again or whatever. About that time, the karaoke host that I knew casually a bit but not well, indicated that he had missed the last bus and asked if anyone could take him to a different bus stop. My remaining friend volunteered me and when I heard where he lived, I offered to drive him home.*

*I feel the need to insert a safety note here – this is someone whose employer I know and I knew by first & last name. He’s also gay and I felt completely at ease driving him home.

Anyway, I am so glad that I drove the karaoke host home because it was the catalyst that launched our friendship and I enjoy him tremendously (he’s the host that I mentioned meeting up with after Prince as well.) We’re close enough friends now that I’ve been to his birthday party, we’ve had a road trip and he’s met my kids. So yes, super happy to see him home safely, but it cut off any potential continued conversation with P29 and I really didn’t expect to hear from him again. Once again however, I need to embrace the unexpected, because just as I was leaving THE VOICE’s place, I got a text saying “I didn’t think it was fair that I had your number and you didn’t have mine, so this is me.” We then proceeded to message for another hour or so – nothing big, just two people chatting at 4am.

The next day I think we exchanged a few messages – that was a Friday. On Saturday we somehow managed to text all day long while I was cleaning house and attending to errands. Nothing really flirty or anything – just friendly & conversational – much about movies, TV, singing. I was watching Breaking Bad on Netflix for the first time and we spent a lot of time on that subject. Later, he went out to sing and I was a little bummed that he didn’t invite me to join since I had let him know that I didn’t have plans. Oddly, however, he continued to text me while he was at the bar & throughout the evening. Finally, around midnight, he sent an adorable text that said: “So since I have some alcohol in me now and less fear, were you hitting on me the other night because that’s the vibe I was getting but my people skills are off since getting back.” My response went like this: “Generally speaking, yes. But I legitimately wouldn’t mind singing, chatting, etc. either.” (SEND) “But yeah, I gave you my number because you seemed interesting, sexy and what the fuck? I’m a single, grown-ass adult. :)” (SEND) “But I am also gifted with a very pragmatic sense of reality in that I am aware that I am a certain age and a certain flavor.” (SEND) He indicated an interest in the hanging out and said he wasn’t looking for anything remotely serious but was disappointed when I gave THE VOICE a ride home because he wanted to talk a little more and at least make out with me. The he followed that with “And I could care less about age and usually prefer a woman with some meat on her bones.”  I told him that I was pleasantly surprised to have heard from him and that I’m usually not so forward with morose men in bars. More conversation about expectations followed and he mentioned getting together to sing or for movies the following day (which we had discussed previously.) Finally, I just went for it and asked what he was doing right that minute. It was 12:45 by that time, but we’d been essentially flirting all day and he seemed to have tapped into his direct & flirty zone, so I went with it. I said that he should come over then and stay for movies the next day. He agreed.

This is my favorite part in what’s essentially a three-parter of an entry & becoming very long, I realize. He offered to bring food, mixers – very polite. I gave him my address & he headed over. I heard him pull up earlier than I expected & went to answer the door. OH MAN!  I mean, my God, this guy was cute with his scruffy hair & beard in the bar, with the hockey jersey or whatever. But what showed up at my door? I pretty much needed to mop my floor because I think I squirted right then & there. Wavy light brown hair with blonde highlights pulled back into a neat ponytail. Gorgeous distressed leather jacket over a dark dress shirt & black tee. Jeans that hugged all the right spots and beautiful, broken-in, leather cowboy boots (but not the gross kind that are too decorative.) He was seriously beautiful and I was going to make the sex with him. OH> MY> GOD!

So yeah, that we did and it was also unexpectedly amazingly excellent. I mean, I figured it would be good and nice and pleasant and maybe even fun. I didn’t expect someone that young to take command like he did, to be as oral as he was or to be so complimentary or responsive. He was very generous and kept saying my name and telling me how beautiful I was or how much he loved this or that. I was surprised to find that when it was my turn to give him some oral – after enjoying some beard-soakingly-good cunnilingus and analingus – that he wasn’t actually hard. Of course I knew that he’d been drinking a bit, but still, it was unexpected. Turns out, he just needs a rough touch. He likes it very physical and he growls in appreciation when you hit it right, which apparently I did. He’s a grower not a shower and I was quite happy that his little mushroom sprouted into a fine specimen of manhood to match the rest of him. We had some really exceptional sex that was downright fantastic for first-time stuff and here’s young Brad Pitt under me apologizing because he came too quick and it had really been awhile. Dudes, he did not come too quickly and he was a genius with mouth, tongue, fingers and beard. Crikey. So delicious was he that I had to have him again around 8am and then then I asked him to settle a bar bet by telling me how old he was. By this time I already figured he was a little bit older than I had originally thought, but yeah, he’s 29. I still qualify as a cougar I guess. 🙂 Later, he slept until nearly 1 – while I occasionally watched him because his serene face was simply beautiful to look at. When he woke we actually watched the movie that had more or less been sex pretense – that was nice. We cuddled and kissed a bit more too – again, not typical morning-after behavior, right? But that was the last time I saw him for two months. Yes, there were messages – some very raunchy and sexy, but we didn’t re-connect until Friday.

Well, Saturday morning, I guess. By the time I got to his place it was around 2:30am. I asked if I could bring anything and he said “just you” and he directed me to a lot where I could park overnight and until 5pm the next day. Oh, okay. I guess I’m staying over, huh? YAY! I was having trouble finding the lot he’d directed me to, so I pulled over & sent him a text. The knock on my passenger-side window caused me to let loose a Jamie Lee Curtis-like scream and a string of swear words and there he was, chuckling and telling me that I need to relax. But how can I relax when you look delicious in that cowboy hat and…oh yum. He hopped in and directed me to park then insisted on paying the fee because I was his guest. Nice. Walking to his place he took my hand. Also nice. Hi, how have you been? 🙂

Continuing our “unexpected” theme I have to kick myself in the ass for my preconceived ideas. I expected his place to be a tiny little walk-up apartment. Not so. Brand new building, beautifully decorated, him on the 5th floor. Granted, his place was a complete mess, but it was beautiful and the best part was his gorgeous king-sized Tempurpedic mattress and leather headboard. He said that after years of sleeping in crappy quarters that he splurged on the bed and that it was amazing. It was. He was.

I was sore from standing during Prince and he helped me take my boots off and massaged my feet. Then he guided me down on the bed, climbed on me and started massaging my back and shoulders. Of course, the least I could do was insist on getting naked so that he could do a more thorough job – which he did. Soon we were both naked and making out like crazy. I was reminded how much this man loves to eat pussy in very short order. Seriously, it was all about me and he ate like a starving man. No polite clit-licking this – we’re talking noisy, sloppy, full-face slurping interspersed with comments about how delicious I was. After I soaked his beard a few times I had to take an opportunity to taste myself on him and clean up his face. I am in fact pretty delicious – especially on his lips. When I took a turn giving him some oral attention – remembering that he likes a rough touch – he insisted that I should sit on his face while sucking his cock because he wanted more of me. God. Damn.

After a long time in this configuration, he let me know when it was time for one of my condoms and I put it on him with my mouth while he moaned. I let him choose the position and he opted for me on top. We did that for a good long while with lots of feedback from him again but in my enthusiasm, he fell out at one point and we had a little trouble getting him re-situated so he flipped me over and started going to work on my pussy & ass with his mouth & fingers again. I think I finally just died and went to heaven because eventually I came in a torrent and laid back and said “shattered” which made him laugh and say that he was glad I enjoyed it.

Now, with older men, I’ve witnessed a fair bit of embarrassment if not frustration if they are unable to perform. Not so with P29. He calmly and with good humor said that his dick was being stubborn, cited the many drinks that he had had earlier and seemed nonplussed by it. I stroked his body & played with his nipples while he sucked air in his teeth and then said that I was more than happy to try to offer further “encouragement” if that’s what he wanted, but that I didn’t want to pressure him if he didn’t think he was up to the task. He said he liked what I was doing and didn’t feel pressured and would let me know if he couldn’t. So…I set to work with my mouth in a way that he immediately responded to very favorably.

One more unexpected moment – if, at my age and level of experience someone does something unique that I’ve never had anyone do before? That’s very surprising. This guy? Full of surprises. Simply being as genuinely oral as he is is a surprising and unusual treat. The ass-play is also a bit of a unique treat – particularly because I enjoy a little bit of play but am not really a fan of a full-on butt reaming. This guy is really great at giving direction – both verbally and non-verbally. I’m usually a little bit dominant, particularly with someone new and this was only our second time being together so it was fascinating that he was able to lead and direct me so well. The “oh, hey – that’s different” moment came when I was sucking him off and he once again asked me to get into a 69 position with me on top. Seriously – he didn’t just want me to blow him, he wanted me to sit on his face while doing so. I was doing some of my best work and would sometimes ease up on the full business in order to concentrate on the tip. If I did this for very long he would wrap his leg around my head and gently push my head back down his length to take him deep. He did this twice and I thought it was both athletic and also clever – he never had to use his hands that were so busy elsewhere.

Eventually, I managed to even distract him from that task which he was enjoying so much. When he came it was loud and very long with full body spasm and ongoing shudders and many a “holy shit” “oh fuck” and such uttered. I responded with his line that I was glad that he enjoyed it.

He was quite clear about having me stay over, but didn’t seem interested in fooling around in the morning but he did insist on walking me to my car like the gentleman I am discovering him to be. We’re supposed to be meeting tomorrow night but it’s very loose & casual. That’s what I struggle with where this one is concerned. I don’t want to make a big deal of things, but I would like to be able to plan and enjoy time together. I guess I fear that I am just a drunk booty call – which I’m not completely opposed to considering how good the sex is. However, I like him as a person as well and wouldn’t mind having that comfort level to say “hey, do you want to do XYZ?” without feeling like maybe I was imposing. Frankly, the fact that I feel that way pisses me off for a couple of reasons. One, he’s never been anything but nice, kind, generous, complimentary, gentlemanly and honest with me. I like that, but I have also had him be non-responsive to texts or respond minimally. It’s frustrating. I feel like this may be one reason that I am more suited to a polyamorous model for relationships. I love it when I can say “yeah, I had a date Friday” to someone that I am involved with and have it not be a weird thing. It’s very liberating. (It’s also a future blog topic!)

Which leads me to tomorrow – when I’m meeting someone new for happy hour at 5pm and hopefully still meeting up with P29 around 9pm. In any case I will bring an overnight bag and my handy-dandy non-latex condoms just in case. And maybe I’ll take a vitamin too – 29-year-olds are exhausting! 😉

07
Apr
13

that whole “cougar” thing? totally legit!

Cougar.

I’m not sure when I first heard the term, but I think that it started “trending” sometime after MILF – maybe in the mid-2000’s? Certainly Anne Bancroft is the most iconic cougar I can think of, but her tryst with a college-age Dustin Hoffman in “The Graduate” must predate the term by at least 35 years. Also, since Mrs. Robinson & Benjamin were a “May-December romance” made in Hollywood, Hoffman plays a 21-year-old, but at the time that the film was made, he was 30 years old and only six years younger than Bancroft in real life. Well, that’s fiction for you, but the general idea of an older woman seducing a college-age man has long been the stuff of fantasy. Much the same is true of the older man and the nubile, young piece of tail, right?

If you look it up online, “cougar” seems to commonly refer to a woman over 40 who “preys” on younger men who are typically in their 20’s. Personally, I find that the term seems to be morphing into a new definition where “cougar” simply means a fuckable older woman. Maybe we have Courteney Cox to thank for that, but I don’t think that the word carries as much of a negative stigma as it may have five or ten years ago. If I mention my involvement with a younger man, many of my friends will say “oh, are you a cougar?” I don’t think that anyone means it in a bad way or is suggesting that I am “preying” on some poor young fool.

When I first made my profile on Plenty of Fish, I had a lot of advice from a single female friend of mine who is also in her early 40’s. I spoke to her right before I launched my profile and she said “now you’re gonna have all the young guys hitting on you.” I was more than skeptical. I scoffed. She told me to wait & see – that the young guys love older women because there’s less drama. While I continued to be unconvinced, I thought about it a little bit more. Getting past my body image issues and general insecurity from not having dated in 20-some years, I could understand the appeal. Older women aren’t looking to settle down, get married, make babies, have someone pay their bills or take care of them. Most women over 40 are capable of taking care of themselves. Most older women don’t have the degree of angst, drama and maintenance that often comes with a woman in her 20’s. They don’t require a boyfriend to be available to them 24/7. They don’t get jealous if every minute isn’t spent with them. We have our own homes without roommates so we can “host” sexual escapades. Best of all, older women are experienced in the sack, near their sexual peak and generally love to be physical. Many of us can’t even get pregnant, so that’s a bonus too. Yes, these are all generalizations, but they are also generally true and I can certainly see the appeal. Still, I didn’t think that any young guys would be hitting me up. But my friend’s “wait and see” didn’t have to wait long.

I was driving home from one of my first meet-ups with a POF guy. This was the guy that I felt was “just friends” and who had only been separated for a couple of weeks. When my phone dinged telling me that I had a text, I assumed that it was my “safety friend” messaging to make sure I had made it home okay. It wasn’t. It was the 23-year-old son of some friends of mine who just happened to be texting me at 12:30am to see what was up. Huh. That’s odd. This is a kid I’d known since he was about 13 and would consider a friend of the family. He briefly dated my niece so I knew that the kid had a little bit of a kinky/exhibitionist streak from what she had told me. Because of that, I was slightly prepared for him to be a little risqué or flirtatious. He had, on occasion, messaged me on Facebook to chat from time to time as well, but sending a text – particularly so late, was new.

When I got in the house, we continued our conversation via Facebook chat. I mentioned that I had just come from a meet-up with someone and he asked how dating was going. I said it was very new and weird since I hadn’t dated in about as many years as he had been alive. He asked if I was doing online dating or how I was meeting people. He then made a comment that it was too bad that “my generation” didn’t just do what his does – hang out, hook up and chill. I said I had no idea what my generation does because it was all new to me. Then he said that if I wanted to do that with him sometime he’d be down.

What?

Wait. What? Back it up…did he just…what? Please, blog followers, imagine me sitting in front of the computer, in the dark, at 1:30 in the morning, literally YELLING at the screen “Shut the fuck up! Did that really just happen?” I was sure that Ashton Kutcher (a one-time cougar fan himself,) was going to jump out at any minute and tell me that I was being punked. Then my text notice bleeped again – with a photo from this guy. It’s him. Nearly naked – his bare torso covered with tattoos and his bedroom eyes staring pleadingly. The text said “could you handle looking at this?”

What the? Okay, okay…I guess I didn’t misread that.

The next message from him contained an apology for being so forward and said that he hoped that he didn’t make me feel uncomfortable. I finally managed to find some words and type a response saying that I was pretty stunned but not uncomfortable. He went on to say that he was looking through my photos and came upon a particularly voluptuous one of me in a certain dress and that I was really hot. He said that he wouldn’t mind fucking me in that dress. Okay, yeah. Message received. That was pretty direct. Yikes.

My mind was scrambling. I was still dying to have sex at that time and here was a young hard-bodied guy who was offering it. However, this is also someone that I still imagined riding a Razor scooter around the neighborhood. I know this kid’s parents and siblings, he knows my kids and my ex and he once slept with my niece. I could certainly imagine, but I couldn’t possibly imagine…!

Finally, I said thank you. I told him that his was the best offer that I had had in about six months and I really appreciated him being so sex-positive. I joked that I couldn’t imagine having sex with him and then looking his mom in the eye. He said “well, don’t tell my mom.” Jesus. He was tempting, to be sure, but I wasn’t willing to risk friendships or have my kids be the butt of scandalous jokes just so that I could get laid. We had a sweet, brief flirtation and ended the conversation…at least for then. We did exchange some dirty texts a few weeks later, but nothing that would have rocked the gossip network in the town I used to live in.

I still doubt that his mom would approve…

But wait! There’s more!

That particular week had been a tough one for me, emotionally. My ex and I had been going through the worst of the nastiness that goes with separating. I was finding the online dating scene to be daunting and a little bit weird. I felt detached from everything that I had once held dear – my home, my family – even my dog.

So I went to the casino. And I met this guy. And I will blog about him later. He was S46 and twice the age of the guy who made me my first official cougar offer. S46 bought me dinner and got my number and boy, wasn’t I having a better week with all this attention?

The next night, I was on Facebook again and received a message from a totally different 23-year-old. This guy is also the son of friends, though I haven’t known him since he was a pup like I did the other young guy. This guy would send me “pokes” on FB almost daily, but I never thought much about that. Some folks do that stuff. That particular night, however, he was more chatty than usual and I found myself once again on the receiving end of some serious flirtation with a very young guy. This one wasn’t as smooth or direct as the other, but he finally managed to get around to telling me that having sex with an older woman had always been on his bucket list. He followed that with “which reminds me, incidentally, I haven’t seen your new place yet. Heh.”

Holy shit. Have I just had three guys hit on me in the course of four days? And were two of them under 25? Yep.

I told this guy that he was the second 23-year-old to “hit me up” that week and that I told the first that I would keep it in mind, but wasn’t sure about fucking my friends’ kids. He then asked if I had come up with a policy about fucking my friends’ kids yet because he wanted to fuck me. Well jeezo man.

Admittedly, I was much more intrigued with youngster #2 and even went so far as to call his bluff a few times over the next few weeks of text messaging, flirting and a little bit of dirty talk. Mostly I think he enjoyed the texting and suggestive talk. He never took me up on it – even when I offered to pick him up. In retrospect, I’m glad. Months of no sex may have impaired my judgment. As it turned out, I started having pretty regular sex within a few weeks of the 23-year-old spree, so I am glad that I didn’t do anything foolish or embarrassing.

In general, while I would consider any adult, I’m not particularly interested in most people under the age of 30. The youngest that I have slept with in the past 6 months was S28 and he was pretty lame in the sack. P29 was gorgeous, fantastic, generous, dirty & delightful and I would see him again in a hot minute! R30 is both sweet and amazing in bed and someone that I am currently seeing. I’ve turned down offers from “men” as young as 18 and dated as old as 48. The average age of my post-marital lovers is 38, however – with only about 1/3 of them being older than I and two younger than 30.

So yes, I guess I am a cougar, but I’m not an ageist and I am willing to consider all shapes, sizes, races and ages…just maybe not my friends’ kids, huh?

 




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Quickies with the Risqué Divorcée!

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