The same Saturday that she had reached out to Wyatt with a little waving emoji, she of course had kept chatting with other guys online (Clearly she needs a hobby). But in continuing with her dating apps, she matched with one of the hottest guys she had seen. He was tall. He was broad. He was 45 and had a great smile. We’ll call him Greg.
Greg was enthusiastic and eager from the second they started chatting. He had this youthful excitement about him. Everything she said seemed like a breath of fresh air to him. But it wasn’t long after starting their conversation that he turned things towards sex. She was fine with that. It wouldn’t be the first time she dirty talked with a guy online. But it was the way he phrased the questions, how he asked them… For a guy as hot as he was, he seemed to have no game whatsoever.
He wasn’t smooth. He was clunky, if that makes sense? She got the distinct impression that she had way more sexual experience than he did – a feeling she wasn’t used to having. As they touched on to more and more sexual topics, she uncovered that his personal life was far more complicated than she could have expected.
Turns out he was married. Well, separated, not divorced. And still living in the same house as his (ex)wife, after having ended things two years prior. He explained that they were continuing to live as a family unit in order to keep some semblance of normalcy for their two children. A noble thought, but kids aren’t stupid. What an awkward living situation for that entire family. He also expressed that he knew his (ex)wife was seeing someone because she had been going to “yoga” for six hours a session every couple days for over a year. He, however, had still yet to meet anyone of any significance.
Holy. That was a lot of pressure on her, all of a sudden. To be the first person someone dates while dealing with something like that, it felt heavy for her. Still, he was so sweet, and she kind of felt bad for him. Also, let’s not forget how hot he was. He was super friggin hot, keep that in mind. So she continued chatting with him while trying to keep his expectations low. He had openly expressed several times how excited he was to have matched with her, and asked more than once, “so you’re willing to give this a shot?”
Give what a shot? Dating? Starting a real relationship while you still live with your wife? The only thing she was willing to do was meet for a drink and see how the night went. She felt like he was way more in to this than she was, but again, she felt like he had just been out of the game for a while. She found his innocence somewhat refreshing and charming, if also a little clumsy.
They had realized that they actually both lived in the same end of the city, which was rare. Usually people were at least a half hour’s drive from her. This guy happened to live right up the street. Because they lived so close, he got himself caught up in this fantasy of meeting up for a quickie in his car. She had told him that there was no way she was hooking up in a car the first time they met, if ever. She had done the car-hookup-thing in her early 20s and she knew from experience that there was no way she was getting off in someone’s backseat. She was at a place in her life where her sexual pleasure was her priority. Gone were the days of faking it for guys just to stoke their egos. Thus, no car sex.
This presented a problem for their hypothetical future sex life. She lived with her parents, he lived with his wife and kids. If there were anything sexual to happen between the two of them, it would have to take place when no one was home at his house (which was rare, he said), or at a motel room as he so chivalrously suggested. He seemed exhilarated at the thought of being like teenagers again. She, however, was less than thrilled.
He continued with all sorts of fantasies that he’d clearly been obsessing over throughout the past two years. She was flattered that he was so in to her and so excited to try all these hypothetical sexual activities with her. But again, she tried to keep his feet on the ground and his head out of the clouds. She told him not to get his hopes up and that there would very likely be something that would happen to prevent things from really going anywhere between the two of them. Her dating experiences had apparently left her glass-half-empty. He replied that he was a natural optimist and that he had a good feeling about her. That was refreshing to hear, actually. And it made her feel less nervous about meeting him, which seemed odd considering she felt his expectations were so high.
She finally got him to cool it on the hypotheticals and to commit to actually meeting up. They agreed to meet for drinks at 8pm that Friday at a bar close to both of their neighbourhoods. She was skeptical about how optimistic he was about everything, but she was still willing to see what he was like in real life.
The rest of her weekend was uneventful and boring. She worked out, got stoned a bunch of times, watched Netflix. Really livin’ the life. You can imagine how excited she was, then, when she randomly got a text from Kyle on that Sunday. “Hey you!” It read. “I know it’s late, but I was wondering if you were free to hang out this afternoon?” She one hundred percent did a happy dance in her kitchen.
It had been just over a month since she had spoken to Kyle. The last time they had seen each other, the sex wasn’t as mind blowing as it usually was, and he napped almost the entire time she was over. Yes, she was fine with it, but it was definitely not what she had hoped for when she had gone over that day.
And now, here he was, texting her after so long and asking her to drop everything she was doing (which was fuck all) to go over to his place to have sex. Did she want to? Abso-fuckin-lutely. But there was no way she could maintain any level of integrity if she jumped at it as soon as he poked his head back in to her life. She waited a while before replying with, “Oh wow, hey. Sorry, I can’t tonight. Another time, with a little more notice ;)” She felt like she had handled that pretty well. It was made it clear she was still interested, but that she wasn’t at his sexual beck and call. He replied with “Sounds good” and a kissy wink face.
Fuck. Yes! she thought to herself. Kyle was back in the picture.
That Friday as she was heading out to meet Greg, he texted her asking if they could meet at 8:45 instead. His (ex)wife had let their son have a friend over, and he was volun-told to drive the friend home at 8:30. She was annoyed, but she always tried to be understanding when it came to kid stuff. She told him “no worries” and decided to do some errands before meeting him, which she had originally intended to do the next morning. Still, she was at the restaurant about 20 minutes earlier than he was. She went in and got a table, people watching and sipping her water as she waited for him.
Finally, she saw him walk in. He was so tall, she could see the top of his head over the partition between the entrance and a booth. He wore a nice salmon coloured button down, tucked in to a nice pair of jeans, complete with some very classy brown loafers. You knew he was a dad, but he was a hot dad. He turned and saw her leaning out of her booth like a damn fool. She laughed and waved as he headed over to her.
He sat across from her and smiled, not saying anything. “Hiii!” she said as she gave a dumb little wave. He blushed and looked down, softly replying, “Hi” back. What the hell?! she thought. He’s so shy!! She wasn’t used to guys being so… submissive, for lack of a better term. But really, it’s true. She was used to guys being strong, masculine, take-charge types. Not shy, introverted, blushing types. She tried to start a conversation but for everything she said, he’d just laugh sweetly and smile blankly back at her. Eventually she literally resorted to whipping out a 20 Questions list on her phone just so they’d have something to talk about.
The game worked. He opened up about himself like where he was from originally, how he had a twin, and oh, how he was in a horrific car wreck when he was 9 and spent like 7 months in the hospital – y’know, casual first date conversation. It seemed like any time he did speak, he said something more surprising than the last. Soon she found herself opening up about funny sexual experiences she’d had just so she could control the conversation again.
This was the stuff he was interested in. He listened intently as she regaled him of her sexual escapades since becoming single. Even some stories from her past like her mortifying high school grad trip to Mexico (which we skipped over in the blog. It’s not in here, and it never will be), or the time she and her ex “swung” and swapped partners with another couple. She elaborated on how the guy from this couple was so hot but unfortunately had a small… unit. She gestured with her thumb to humourously indicate his small stature.
They chatted over several beers and, you guessed it, a shared plate of nachos, before Greg actually got up the nerve to ask, “Hey so… think you might wanna go make out somewhere?” Where? she thought to herself, realizing it would likely be in his car. She weighed her options and decided she was fine to just go make out, but knew she wasn’t going to have sex. But like, she REALLY knew it this time. She definitely wasn’t going to have sex with this guy in his car.
He paid their bill and escorted her out of the restaurant and towards his BMW convertible. She was surprised to see he drove a Beamer. Her experiences with guys who drove Beamers had been less than pleasant, to say the least (ie: Beamer Boy, Chapter Two). She couldn’t deny it though, it was a nice fucking car. She got in and they started driving out towards the country in search of a dark side road on which to pull over so they could fool around. Did she think about the possibility of her getting raped, murdered and chopped up in to little pieces? Why yes she did, in fact. Clearly, though, she felt the risk was low, so she took her chances.
While driving out there he confessed that it had been about 3 years since he had had any physical contact with anyone. For the last year of his marriage, he and his wife didn’t have sex, and then for the following two years living together, he still hadn’t gotten himself any action. She knew he hadn’t dated, but no sex whatsoever?! She was surprised, but that explained a lot about how awkward he was.
After driving for about ten minutes, they found the perfect spot to pull over. They both pulled their seats forward before crawling in to the back. Immediately his hands were all over her as if he were a frantic airport security person patting her down for contraband. He tried to grab her boobs but couldn’t fit his hand between her and her bra. She graciously whipped it off, keeping her shirt on, to give him better access. She was so used to the guy being in control during her sexual encounters, it felt awkward when he didn’t take charge. So she did.
She started kissing him and getting things going. He was even an awkward kisser. He felt her up for a while, as her hands remained away from any of his parts. He moved his hand down to her legs, so she moved hers down to his. He then tried to rub her over her pants, basically grabbing a fist full of her “fupa” in the process. She stopped him and just flat out said, “It’s not gunna happen. Not for me. But just relax, I’ll help you out…”
She wasn’t sure what came over her, but she just knew that this guy needed a night of fun. At least one moment’s pleasure to break through the shit storm that was his life. She started to rub him over his jeans and found he was already quite alert. He unzipped his pants and pulled them down just enough for her to get a grip. She was very taken aback by how little she had to work with. In that moment it made sense to her why he drove this kind of car. Clearly he was compensating. How could this giant man have such a small package?! On top of everything else he had to deal with?! This poor man!!
She kept going for a few minutes, finding it more and more difficult to get anything going. “It’s not gunna happen…” he finally said. “What do you mean?” she asked. Surely he would be able to get off after not having done this in so long. Well, in fact he did.
“Well,” he clarified, “it’s not gunna happen again, I mean…” Turns out that within seconds of her starting, he came. She had felt something on her hand, but it was dark and there was so little of it she didn’t think he possibly could have finished already. It was then that he grabbed the only thing he could think of, his disposable mask, to wipe up her hand and himself.
In her head, she was dying laughing. It was the mask wipe up that pushed it over the edge for her. But she kept her composure, especially when he began to apologize profusely for finishing so quickly. Truly, though, she was unbothered. It was actually nice not to have to do that for as long as she usually would have to. And even after all that, she felt like there still could be something there. He was so kind and honest and sweet and he clearly thought she was the bee’s knees. Maybe she could still work something out with this guy.
He drove her back to the restaurant where her car was parked, and told her he’d text her later. They kissed goodbye and she got out of the car. She drove home, washed her hands immediately, then went out to the garage to smoke a joint before bed. As she puffed away, he texted her. “Hey! Hope you made it home ok. I had an awesome time tonight. Thank you :)” She replied saying she had a nice time too and joked that she was happy to help. It was then, though, that he ruined everything.
“Am I bigger than a thumb?” he asked her.
Oh. Em. Effing. Gee. In that moment she wanted to just crawl in to a hole and die. She had forgotten she had said that, and of course when she said it she had had no idea how small he was! Not wanting to shame him any further than she unintentionally already had, she replied “Yep!” but didn’t elaborate. Then he texted, “Do you think you’re going to like it?”
She wanted to throw up in her mouth. Never had she been so turned off in her whole life. All of a sudden she realized what it must have been like to be on the other side of her own insecurities as a teenager. It was so unattractive! She didn’t want a guy to ask her if she was going to like his dick, she wanted him to tell her she was going to love it! And yes, most guys that do that are equally as unattractive. But when it’s the right guy, a guy she had chemistry and a connection with (a guy like Kyle, for example), being told what to do or what she would like, was one of the hottest things a guy could do.
Up until that point she hadn’t fully written Greg off. Even though he was as small as he was, she was trying to be optimistic in thinking that there were other ways he could please her that didn’t involve his… little soldier (trying to think of clever euphemisms for the word penis is harder than you’d think) [ha, “harder”… penis… never mind..]
But yea, after that, she was completely turned off. She waited 10 minutes trying to think of something kind yet clear that she was over this. She was stoned and couldn’t get her thoughts straight so she just sent out another “yep”. He liked her comment and she tossed her phone away from her. Fuck. At that point she was pretty sure Greg was so in to her that he was already planning their wedding. Now she had to figure out how she was going to get out of this…