I met a 24-year-old College Cub a few years ago on a cougar dating site. His pictures were really cute – blond hair, blue eyes, average build. He seemed like he could hold a decent, educated conversation, which is important to me. He lived about an hour and a half away, and we only hung out twice, mostly because he was unreliable or wanted to show up at my place at midnight and stay the night when I had to work the next day.
Upon the first actual meeting, College Cub showed up with alcohol, which is more than what I’m used to. He was wearing sweatpants and a tshirt and looked a little sloppy, and he was much shorter than he alluded in his profile. We made drinks and sat on the infamous cougar couch to chat and get to know each other. He would be graduating college that year, and he worked in sales. He was definitely easy to talk to, and we seemed to enjoy each other’s company. A few hours later, we were all over each other… but he was definitely inexperienced and anxious.
I don’t mind giving a few directions, but College Cub had no idea what he was doing. I had to teach him everything… even to slow down when he kissed me, because he must have thought he was in a race. He didn’t know what to do with his fingers, so I gently showed him how to rub my special places and how to properly insert a finger without jabbing me like a cattle prod. He didn’t know how to use his mouth when he went down on my either, so I had to instruct him there as well. It was truly work and not that much fun for me.
College Cub’s dick was a little on the small side, which made it even more work for me in that department. A little short, and not thick, which meant riding him was going to take some extra skills. Finally, it was late, and he finished quickly.
We saw each other once more after that, and he remembered a lot of what I taught him, which was nicer than giving instructions while I was trying to get off. Once every so often, I’d hear from College Cub, and I’d spy on his Facebook page to see whether or not he was in a relationship and trying to pull one over on me – and he was. He was begging me to have him over, and I’d moved about 45 minutes from where I’d lived when I saw him prior, but he didn’t care. I told him I wasn’t interested, but he didn’t take that as an answer. Then I simply said I didn’t want to see him and to stay with his girlfriend. Still, he thought something was wrong with me. So… I ghosted him. But he kept up a conversation all by himself just fine for the next three days.
I’m a zero bullshit type of person, which is why I’m easy to get along with. I know what I want, say what I want, and most people appreciate that. Too bad I can’t say the same for other people.
After Army Guy’s little hissy fit over not getting his way, I was like WTF… we’d just had a conversation that neither of us wanted a relationship nor had time for one. We’d only been out ONCE on an actual date at that point and seen each other twice. I didn’t know whether he was taking things out on me that was happening at his house, but I certainly didn’t appreciate it, nor did I deserve it. That type of response will cause me to start building a wall and push me away for good. I felt that he was sabotaging what little was left, so he said he wanted to see me in person to talk about it, since texting can cause confusion.
When he arrived at my place, I was pretty tense from it all. We gave each other a long hug, and he apologized. (This is where I’m putting things together.) Remember earlier when I said his response was “she takes things too personal”? Well, now the story is she’s banging someone else at the house, and he felt disrespected. Okay, understandable, so why did it take him coming over to tell me that? I mean, if we’re being honest with each other here, so why not have this disclosure to begin with?
Army Guy is a charmer, and I couldn’t resist kissing him. But that’s really all I was ready to do. Then he started pawing at me and going a lot farther than I was ready for. I had to tell him to slow down a few times. I could tell he just wanted to fuck me and leave again… which is exactly what happened. Then I was pissed at myself for allowing it.
And then a storm hit – both literally and figuratively – and I was out of power for nearly a week. On a Friday he’d asked how I was doing, and he wanted to see me on Saturday. I thought that “maybe” he’d at least offer to bring me a hot meal, but I never heard from him until five days later. By then I was pretty stressed out dealing with my situation (junk food, no ice, cold showers, no sleep, zero power, feeling gross). I’d had way too much time alone in the dark to think about life and how I wanted to live it and what types of people I want in it, so I blew him off, because I was pissed. I was starting to feel like I was almost dealing with another Big Liar.
Army Guy then claimed he’d been trying to call me for 3 days (LIE!!!) so I sent him a screenshot of my phone calls… showing just one call from him the day prior. Of course, he couldn’t argue with that, so he changed the subject. There were just too many red flags now. Between his nondisclosure of things and selfish pursuits, I felt I was being played. (Oh yeah, and did I mention that while he was giving me a massage once, he started telling me about a married woman that wanted to see him again? Not exactly the greatest timing, dear.) I also remembered that he’d contacted me six months prior to this arrangement, prior to his deployment, wanting to meet up. Putting two and two together again, I realized he had been living with this other woman, because he told me they were living together before he deployed – and when he came back, she’d been fucking her ex.
I sent him a text saying this thing between us isn’t going to work. I had no intentions of seeing him again, because I didn’t want to hear anymore bullshit lies, manipulations, and I certainly wasn’t going to allow him to treat me like I had a revolving door. I expected him to either agree or at least ask me why. Instead, he decided to make it ugly and act like a big fucking baby (BFB) not getting his way. Total turnoff!
The following day I awoke to text messages starting at 7 a.m. He was going ballistic: “thanks for breaking up with me by text like a 16 y/o.” Umm, okay. Then more insults saying I was a shitty lay anyway, blamed me for us not getting together, sarcastically said good luck with the panty business (although when he was getting his way he was FULLY supportive! 😉 ), called me inconsiderate for not telling him in person, blah blah blah. I honestly didn’t think it mattered how I told him, since this wasn’t a relationship to break up anything except a convenient lay for him.
I was in no mood to argue with someone that was acting like a BFB. In fact, while he was bombarding my phone with these shitty messages, I was reading them out loud to the Norwegian guy I’d hooked up with the night before. After the shitty lay comment, the Norwegian told me to tell him that I’m a great lay. So I did, then I blocked Army Guy for good.
I’m sure he’s still reading my blogs hoping for his claim to fame that he fucked a hot MILF/cougar and still probably jerks off thinking about it. Oh yeah, and he’s still following me on Instagram. 😉
On the date with Army Guy, I informed him of my blog and camming, which are completely divergent from my former career. He seemed really cool with it, supportive, perhaps wanted to participate. (Later on, he did participate in cam chat, making lots of viewers jealous. It was a huge turn-on!)
Anyway… back to the date. I was hot, horny, and ready to fuck. We eventually made our way back to my house, starting on the couch with a nightcap and a really heavy make-out session that didn’t take long to move onto the bed.
Army Guy went down on me, and I realized he’d had some practice since I’d seen him last. He was definitely better than before, although still needed some fine tuning, because he seemed a little too aggressive/excited. His fingers were a little rough, and I had to keep reminding him to slow down. Also, at times something about the angle of his tongue literally rubbed me the wrong way. (I’m sure that women reading this can somehow relate.) But I did manage to teach him how to make me cum. And oh my god… he had two fingers inside of me thumping while he was eating my pussy like he hadn’t eaten dinner earlier. I came hard, but I was ready to fuck, because his cock turned me on.
Army Guy had the perfect fucking cock. His dick was probably a good six inches AND thick. I really, really liked sucking him off. I got so horny doing it that I would almost cum, but we both wanted to fuck – and fuck HARD. My perfect position with him was straddling him while I rode him on top, my clit rubbing all over his shaft, then leaning down toward him and shoving my tits in his mouth and rubbing my clit on the area above his dick, his dick shoved all the way inside of me. Apparently, we both liked it a little rough in that department. (To be honest, just writing this is making me wet as hell!) I have some pretty good Kegel skills, so just by doing certain positions and tightening, we managed to both cum at the same time. He started sending me text messages saying how great the sex was and how he jerked off thinking about it, how horny he was and how he couldn’t wait to fuck me again. (Remember those words.)
I saw Army Guy two more times after that night. I honestly believe he didn’t just come to “see me”, because he wasn’t around for long: we had sex, and he’d leave. The first time, I just figured it was timing. I had already told him I didn’t want a “wham, bam, thank you ma’am” situation, and we both agreed we didn’t want an actual relationship. He expressed that he wanted to take me out on his bike and do actual dates. (I honestly don’t expect anyone in his 20s to want a relationship at all, much less with a woman probably closer to his mother’s age.) However, I do expect to be respected and not lied to. After all, I’m offering him my company and time, and allowing him in my home. (Plus, it wasn’t like he was the only guy trying to hang out with me, so I did have some other choices if I felt the need. I didn’t.)
Then things just got weird. Weird as in – for whatever reason (intuition), I felt the need to ask if he lived alone. (I don’t know why I never asked, but I did ask why he’d moved 45 minutes away from the last place he lived – and his answer was it was a better quality place. Okay, whatever, sounded plausible I guess.) He informed me that he did have a roommate. Again, I “felt” the need to ask if this was a girlfriend. His answer: “No, but she’s someone I used to sleep with.”
Okay, now things were starting to get into perspective. The more questions I asked at different times, the more I started noticing different answers or avoidance. Total bullshit. With the newfound information that Army Guy was still living with his ex, I started putting up my guard. I was tired of being the rebound girl and told him so. He stated that he and his ex had been over for a few months, but he was just trying to find another place to live. Okay, I’ve been through that myself, so I get it.
Then something happened with a text “miscommunication” that I’m unsure was an actual miscommunication at all. Apparently, he was angry at his live-in ex over something, and the answer he’d given me was “she takes things too personal.” Okay, no further details. Told him I was doing some blog writing, he says he’s excited about reading it until he asked me if it was about him. No, however, the beginning almost sounds like him (Tattooed Cub), but the physical description is different.
Unexpectedly, Army Guy gets pissy, and text messages go from zero to nearly psycho in two seconds saying, “Yeah I’m fat, he’s not? Terrific”. I’m like WTF… I never said anything to imply that. All I said was Tattooed Cub is heavily tatted, shorter in height, and bearded.
So he sends: “My night just did a fucking nose dive so I’m gonna go before I lose it,” and his messages didn’t get much better than that.
I had no idea what he was talking about. I said what do you mean? What happened? I thought something happened at his house. So how is this my fault?
His response: “Comes a time when it would be nice to see you write about the guy you are actually with and not all the ex hookups. Just food for thought.”
Really? Suddenly, I got the feeling that he was only in this for his own personal selfish gratification. Being in this career field, I can’t have anyone acting jealous (prior to this he claimed he doesn’t get jealous – another lie) and ruining my chi. It just can’t happen. Besides, I thought, I have been single 15 of my adult years, so he can back the fuck off and wait his turn for me blogging about him. I hope he’s reading this now.
A few years ago I met a really cute blue-eyed (yes another with blue eyes!) guy at a beer joint near my house. He seemed well spoken, intelligent, and mature for his ripe young age of 25. He’d served in the army, had just gone through a divorce, and was going to college. He told me about his time in the war in Afghanistan and had PTSD as a result of it.
We saw each other maybe a handful of times, always having sex, of course. It was okay, but once it got a little scary, because he thought that I liked to be choked while having sex (I don’t). At some point he had this really deranged look in his eyes, and I wasn’t sure if he was having a flashback or what the hell was going on. So I stayed away from him… for a while.
He contacted me a few months later and ended up staying the night after telling me he had tried working things out with an ex, which is why I hadn’t heard from him. (Go figure.) He had school the next day, I had work, but I couldn’t wait to get him out of my house. When I woke up with him there, I’d wished I had never allowed him over. I had started remembering that he was quick-tempered, and knowing he might have been mentally unstable, I knew I didn’t want to see him again. As I watched him leave, I told myself never again, and thought for a minute he looked sad and pathetic like Shrek trodding down my driveway.
I didn’t hear from him again for over a year, saying he was going to be deploying again soon, but at the time I was going on a date with someone else and not interested in Army Guy. Six months later, I get a text from him saying he’s back in town. I should have gone with my last memory of him leaving my driveway that one memorable morning, but gave him the benefit of the doubt, especially when he told me he was in a different state of mind than when I’d seen him last.
He asked me out on an actual date, so I said sure, why not? Army Guy picked me up on his motorcycle, and we had a really amazing time. I’d forgotten what it was like to be on an actual date with real, stimulating conversation. Plus, his eyes were mesmerizing, and I was really attracted to him much more so than I was the first time I met him. His kisses made me wet, and I knew we’d be fucking by the end of the night.
Tattooed Cub was the first (and only) cub of my time to seriously hang out with me. We never went on any actual “dates”, and I always hosted, but it was nice to have someone to have a meal with, watch a movie with, or (of course) make out with. We lasted off and on for a few months, but he seemed really unreliable, which ruined it. He worked a lot, which was great, but every time he’d make plans, he’d either have to cancel, or he’d be so late I was ready to go to sleep. A few times his excuse was that he’d fallen asleep. I began to wonder if it was more than just work keeping him busy. It got to the point that I had to tell him I was no longer going to make plans with him if he was going to stand me up. That was pretty much the end of that.
Every few months, Tattooed Cub sends me a text asking how I am and telling me how much I turn him on. But… BUT!!! I noticed he was obviously dating someone, then blowing me off, then coming back to me. That doesn’t exactly work for me. He has a girlfriend now, and although I’d love to hang out with him, I’m not going to be “that woman” shagging taken men on the side. But I still do get wet thinking about the fun we had while it lasted. 😉
After I’d stopped seeing Blue Eyes, I was out dancing with my friends one night and bumped into a really cute dark haired, tanned and toned-bodied guy with beautiful blue-green eyes that appeared to be in his late 20s or so. It turned out he was going to school with the intentions of becoming a doctor, which was a plus, because I am highly attracted to intelligent men. We exchanged numbers and began a texting relationship for a few weeks. As it turns out, he was only 23. Yikes! He stated he had no problem with older women.
I wasn’t a big texter at the time, so it was a little annoying for me to have an entire conversation that didn’t consist of actually speaking. We sent some photos back and forth to each other (innocent) at first and then came the dick pics. It was difficult to tell by the angles if it was an accurate depiction of his manhood. I’m a very detail-oriented person, so I notice EVERYTHING, and I could tell he was a nail biter. Yuck.
Med Student begged me to come to his place a few times, but I was hesitant. Finally, we agreed to meet somewhere and hang out for a little bit before I gave in. He was renting a really nice house in an area I couldn’t have afforded on my own. He had a roommate that was sleeping when we arrived, which I was glad, because I hate those awkward situations when it’s only a hookup. His bedroom was a frigging mess with clothing strewn all over the place, bed unmade, poor lighting, bare walls. I had to remind myself of his age, because when I was his age, guys then lived in about the same circumstances.
We’d both been drinking, which took the edge off, but in no time we started kissing, and I was impressed. I absolutely LOVE kissing, and I find it a HUGE turn-on. His lips were nicely shaped, soft, and inviting, so it didn’t take long for us both to get hot and horny. He just about tore my dress off to get to me. I was surprised not only at how well-endowed he was but at his bedroom moves. I went down on him, sucking the head of his dick like a Tootsie Pop, teasing him just enough to make him want to enter me. I was soaking wet and ready to roll. He thrust himself inside of me, fitting perfectly, sliding in and out, my clit rubbing against his shaft just right. We flipped over, me sitting up and riding him, scooting back and forth for more clitoral stimulation. I could tell he was probably close to coming, as was I, so I stuck my tits in his face, brought my legs together and squeezed my pelvic muscles tighter. I always like to kiss while I’m fucking, because it makes me cum harder and faster, so I grabbed his bottom lip with my teeth and locked lips. Within seconds, we both came at the same time. (I always think that’s hot!)
I spent the night, and in the morning we had a quickie before he had to drop me back to my car. It wasn’t the last time I’d be seeing Med Student. 😉
These are two questions I am asked quite frequently, so here it is…
I will begin with the latter, because it’s such a fun and hot-ass story to recall. A few years ago while I was going thru my breakup b.s., I was going out a lot. (Basically, sowing my wild oats, so to speak.) Once I realized that younger men were attracted to me, all I wanted were younger men and had no interest in any my own age at the time. Of course, going out frequently means you’re going to run into a lot of 20-somethings, since that’s usually what is single and also sowing their wild oats.
Anyway, some of my other single girlfriends were also going through the same ordeal as me, so we decided to take a trip to Florida to get the hell away from our problems for a week. One night we decided to watch a band, and even though I “thought” I had gotten over band guys while in my 20s, this one was amazingly talented, cute, and happened to flirt with me. Guitar Guy and I talked a few times, were both fully attracted to each other and learned we were both Leo’s (and we knew what that meant). He had blue eyes and an amazingly hard physique that I wasn’t used to having in front of me. So we decided to take a ride in his SUV once his band packed up for the night, and before we even left the parking space, we couldn’t stop making out in the front seat. It was getting late, and the area was well lit with cops circling everywhere, and we knew we had to leave. However, we couldn’t go back to either of our places, because we both were staying a distance and had early morning plans. Instead, we parked on a dirt road near some houses by the beach. Neither of us knew where we were.
It started out in the front seat with some hot-ass passionate kisses… the type that makes you want to keep going, keep tasting them and feeling their soul and becoming one…. Guitar Guy had shoulder-length hair that made me hotter when I ran my hands through and pulling it, pulling him closer to me, biting his lip and tasting the salt on his neck. I wanted him inside me now. (His dick was much bigger than I’d suspected, so it was no disappointment at all; in fact, quite a nice hard surprise. 😉 )
Guitar Guy suggested moving to the backseat, which had more space but papers and crap all over the back. Neither of us cared at that point anyway. But the pause made us both started asking each other questions in no particular order…. Are you safe? Yes. Do you have a condom? No, do you? No. (More conversation about that went by.) By then we were both naked and still all over each other and didn’t want to stop. Can you get pregnant? No. How old are you? 21. Ohmygod, he’s a baby! How old are you? Old enough to… nevermind!
But that didn’t stop us at all, because I was straddled on top of him, windows up, motor off as to not attract any passersby or cops. The windows were steamed up so much we couldn’t see out of them. It was a HOT summer night on top of it. I rode him up and down, both of us sweating so much we were sliding all over each other. I came so hard my entire body was pulsating. He started to cum, pulled out, and we both were drenched in all of our bodily fluids, even in our hair. It was one of the most amazing, memorable sexual experiences I’ve had in my life. I would totally do it again, of course!
As of the first question, the only answer I will give about my age is this – I am over 30 and 40-ish. No need to give away all my secrets, right?
Most men cannot keep up with me, especially older men or even men my own age. Perhaps it’s just the area in which I live that the selection is poor. When I discovered younger men were attracted to me around my 40th birthday, I started exclusively dating younger men. I did not seek them; they came to me.
My first cub was a cute 30-year-old ex-military guy graduating from college that I’d met at a club while I was going through my breakup. He had beautiful blue eyes and had a model look about him, but he wasn’t very much taller than me. (I’ll just call him Blue Eyes.) Surprisingly, Blue Eyes had a huge dick, so I stuck with him for a while. I’d never been with anyone so much younger than I. We had a lot of fun that mostly involved drinking copious amounts of alcohol in a darkened living room and lots of making out and fucking. It wasn’t a lifestyle I wasn’t used to. As time went on, I grew bored of the excessive drinking in the dark on beautiful days. It just wasn’t for me.
Blue Eyes ended up moving to another state but we do keep in touch, as he sometimes gets sent back near my area for work. We hooked up about six months ago when he was in town – this time it was wintery weather, but we still did his routine of drinking and fucking in a darkened hotel room. It was really hard for me to get into, and things felt different than before. Sex was not the same as I’d remembered. I can’t pinpoint exactly what it was, but the sex wasn’t as exciting. A few years had already passed since our initial meeting, and I was in a much different frame of mind from when I’d first met him. I mean – he didn’t even cuddle with me afterwards, which is always part of the benefit of an old friend, right? I had driven about an hour to see him, but felt a little disappointed when it was all said and done.
There were a few things about him that turned me off, but I’ll save that for some other time.