The Time an Illegal Cab Driver Fell in Love With Me

Years ago now, probably about 5 or so, my friends and I somehow found this cab driver who is not really a cab driver. JJ is his name and illegal cab driving is his game. He is not a licensed cab, but he will drive you around in his truck for whatever price you think is fair. We used him a few times and then I lost my phone, and subsequently, his number. I had forgotten all about him until last year when I went on a date with this Sons of Anarchy, Opie-looking motherfucker. If you’re a fan of the show, (Obviously you are. You have good taste. You read me.) you know that Opie is hot. I call this man a motherfucker because we had a great date that lasted about 6 hours before we even made out (including leaving hickeys on my chest), and then texted me to make more plans and then completely disappeared. Thank god I didn’t offer him a nice seafood dinner first 😉 since he NEVER CALLED ME AGAIN! Dorothy Mantooth? Anyone? Yeah, you’re laughing. So anyways, Opie told me about this guy who he’s been using to drive him around when he goes out for drinks and it rang a bell. Same guy! I couldn’t believe he was still kicking around.

5 years later and there I am on a Friday night ready to go home and looking for a cab and this guy in a red truck yells out his window at me, asking if I need a ride. I ask if his name is JJ, and it is! So I hop on in and tell him I remember him from years ago and give him my address. On the way we get to talking and by the time we get to my house, he’d gotten deep into telling me about his entire life history. I’m a nice person, and especially so when I’m drunk. I’m very sympathetic, so I lent him a listening ear. He has lots of trouble with his ex and the custody battle he’s going through with her. I listened, offered some drunk advice, and tried to leave a couple of times, but ended up spending roughly 45 minutes in his truck outside my house listening to his woes. I told him everyone needs to vent sometimes and needs someone to talk to. In my drunken state, I didn’t mind that it was me. He gave me his number and suggested I give him mine so he knows when I’m calling him and he’s sure to answer. Sure, why not? I mean, he’d have it the first time I call him anyways. I eventually get out of his truck and go into my house (after first stopping at the neighbour’s party and spilling a glass of red wine on his new beige carpet). As I’m getting ready for bed, JJ texts me, thanking me for listening. And then asks me if I’m single. Uh oh. I don’t know how old this man is, but my guess is late 40’s, and he’s not my type at all. So I say, I’m seeing someone. He asks if he makes me happy and I say yes. He says he’s glad and good night. Phew, dodged that bullet!

Just kidding! As if it was going to be that easy! JJ texted me the next morning to say hello and wish me a great day. Then he tried calling me. I did not answer. I finally texted him back later in the day as I was getting ready to go to a concert. He asked if he could stop by if I was home and let me read those papers we had talked about the night before. I vaguely remember some talk about papers and I have a suspicion they related to his custody battle. But I was busy getting ready and had a friend coming over so I told him another time. He told me to have a good time at the concert and call if I needed a safe ride.

After the concert, my friends and I went out and I scored myself a tall, handsome out-of-town farmer for the night. Or rather, he scored me because I’m always the catch in any situation. He aggressively pursued me most of the night, and really won me over when he didn’t want to tell me he was 35 because I might think he’s too old for me. He thought I was 25-27, bless his heart! When we left, there weren’t any cabs around, so I called JJ and told my new beau for the night he was going to have to pretend to be my boyfriend. JJ dropped us, plus my bf’s friends off at the hotel they were staying at. You’d think that even if he suspected this man was not actually my boyfriend, having him drop me off with 4 men at a hotel might mean my interest in him was non-existent. But it didin’t. (Just to be clear, there was no gang-bang. But there was lots of fun between myself and the farmer. The friend he was sharing the room with was kind enough to disappear for an hour or so before coming back to go to sleep. But he definitely saw me naked in the morning when I chose to walk to and from the bathroom in my birthday suit while telling him “Don’t look at me, swan!” It’s just nudity.) Now back to my JJ story. So, I get home and have a nap and wake up to a text waiting for me from JJ, asking if I have time for tea. I tell him no, I have Easter plans. So he texts me the next day to ask me for tea. Tea and a massage. WTF?! Massage? Getting creepy. I tell him I’m working 12 hour shifts all week, but if he would like, I could meet him for tea the following week on one of my days off. He tells me he thinks I’m shrugging him off. He wasn’t completely wrong. I usually don’t even make time for my real friends when I work those shifts, let alone a lonely man I met on the weekend and was nice to! But I just tell him that I work long shifts. His response was:

I understand but u need to live too. could there be time for us. I’m not giving up on finding someone to give all my love to.

My response was:

I do live, on my time off. And I thought it was tea as friends. You shouldn’t give up on finding the right person to give your love to. But it’s not me.

I think that was fairly straightforward without being unkind. He has not messaged me since. I broke up with my cab driver.

The Mathematician Cook (Not Meth)

Over the past couple of months, I have really started to enjoy going out on weeknights as opposed to the weekends. Sure, I still have fun on the weekends that I go out, but there’s something special about a Tuesday night drunk.

On one such night, I ended up at one of my favourite pubs, McNally’s. It was karaoke night and the place was packed! Partly because it was karaoke and partly because another bar in the city had closed for the night in order to finally get around to having their Christmas party, and had chosen that venue. On one of my trips up to the bar, I smiled at a man I thought was cute and said something along the lines of “Hey. Sup?” Along with a reverse head nod. Classic. And it worked. He was part of the Christmas party and invited my friend and I to go along with them back to their bar to have after hour drinks. Obviously our answer was yes. We played some pool, had some drinks, and a general good time. My phone died, and my friend’s phone died. She needed to go home and borrowed the mathematician’s phone to call for a ride. And then left. With his phone. This is important for later.

Gradually everyone we had come with left and it was just Math and I left. We made out in the bar for awhile and then decided to lock up and go to his place. I did sleep in his bed mostly naked, but not much happened. We did not have sex, or anything even close to it. Although I’m sure he was wondering what the hell I was doing in his bed in just my thong if I wasn’t going to have sex. I wondered the same thing myself when I sobered up.

So, it’s the next morning, he has to go into work, and I have to go home. He doesn’t have a car, my phone is dead, and his phone is presumably still with my friend. He went to check if his roommate was home so we could borrow his phone and call a cab, but no luck. So he told me to just wait there and he would walk to work and call me a cab from a payphone on the way. So there I am sitting upstairs in his roommate’s livingroom waiting and waiting and waiting. No cab. And there’s just old food containers and cash laying around everywhere. Trusting bachelors. But I do suddenly hear movement. Turns out his roommate WAS home, he was just sleeping in a different room. His roommates comes out into the livingroom wearing a t-shirt and a small towel wrapped around his midsection. He was holding it closed. Which was fine when he initially walked by me to grab something from the livingroom, but when he turned around to leave, suddenly the part of the towel that did not quite close was level with my face. Awkward. Finally the cab came and I got to go home.

I retrieved Math’s phone for him and returned it. He asked me out. I said yes. Things I learned on our first date included these facts: He has a math degree and is ridiculously smart. He had wanted to keep going to school to become a professor. Instead, once he got his degree, he kept on at his parttime job as a cook at a local bar and has been there for the past 15 years. He doesn’t have a car because he doesn’t drive because when he was younger, he got a DUI and when the time came when he could get his license back, he just never bothered to go through the steps needed to get it back. He lived with his mother for awhile to save some money, but for the past coupe of years has been living in his friend’s basement. On the plus side though, he did open doors for me, paid for supper and drinks, and is kind of funny. And he’s awkward, but in a cute way. I do have a bit of a soft spot for awkward weirdos. I was sick so he didn’t kiss me goodnight, but he did give me a hug.

Date number 2 was a movie at his place. We cuddled on the couch and he rubbed my leg, my arm, my back, ahh, just like that! Just kidding, it was normal cuddling. He stroked my hair. But never made more of a move than that. Even when we parted ways, nothing. I was really starting to get on the fence about this guy. I mean, he’s a nice guy, has some good qualities, but wasn’t making a move, and the whole lack of ambition thing wasn’t sitting well with me.

Date number 3. Now, if you are a long-time reader of mine, you already know that it is pretty unusual for me to agree to anything past a second date if I’m not feeling it. He intended on taking me bowling, but didn’t do any research into it, and it was a league night and we couldn’t get a lane. So we played free pool at the bar he works at, and he drank employee priced beer. Oh, he’s also a big drinker. Sure, I drink, but I’m not into getting off work and downing a couple of schooners of beer and then going home and drinking from my box of wine. Or “cask” if you’re fancy, like my mom. In fact, I think at one point he referred to himself as a functioning alcoholic. Not as a joke. Anyways, he did kiss me goodnight that night. Not a great kiss. He uses a bit too much tongue right off the get-go. I mean, what’s the rush?! There’s plenty of time for tonguing.

Date number 4 never happened. He asked me out again and I said yes, but I cancelled it a couple of times. Actually, I cancelled every date we made and rescheduled it. I was never excited about seeing him, I didn’t get butterflies, and I didn’t think about him when we weren’t together. All bad signs. Anyways, I had cancelled our date and tentatively rescheduled. But I never let him know for sure and went out that night instead. When I got home, I sent him a message and he was still up so I caught a cab over. My thinking was that, maybe, we just needed to have sex. Maybe that was the missing piece and it would get me off the fence. Well, it sure did get me off the fence, but not in the direction he would like. Keep in mind I was drunk. The sex didn’t have to be amazing. It didn’t even have to be good. I would have settled for adequate (pfft, no I wouldn’t have). But it was bad. I don’t want to go into too many details (I know you don’t believe me, but I really don’t. He’s still a nice guy), but suffice to say I was not a fan and will not be repeating that little adventure. We might be friends. I’m going to leave that in his court. I’m not one to force friendship onto men. It’s cruel to spend time with someone who has feelings for you when you don’t feel the same way, just because you enjoy the attention and their company. It’s selfish.

Anyways, onto the next! I have a couple other irons in the fire, so stay tuned!

The Air Canada Pilot

St. Patrick’s Day, 2014. I was at one of the local pubs enjoying myself, forgetting about the funeral I went to earlier that day. I was on fire that evening. My milkshake was bringing ALL the boys to the yard! One of these boys (I guess I should call him a man. He’s in his early 40s) was a pilot for Air Canada, just in town for the night. Shorter than I, but very handsome. He struck up a conversation with me and I gave him my number. The friend I was with pulled me away to meet some other men, but the pilot had texted me almost immediately after. He also found me before he left to say goodbye. I was tempted to leave with him, but there were just too many other men left to flirt with. We spent the next week or so texting and I learned a lot about him. My conclusion has moved from my previous assessment of all pilots loving having their balls licked to all pilots are a little kinky. I shall explain.

This pilot enjoys lots of anal play, male and female. A previous girlfriend of his enjoyed fucking him with a strap-on. He also enjoys women’s underwear, specifically big, white granny panties. And while he likes seeing them on women, he really would like to wear a pair himself. He’s been too afraid to go and buy some of his own. I don’t really understand that. I mean, he lives in Toronto, he could go anywhere for them, no one would know him, and even if someone asked, he could say he was buying them for his girlfriend. He asked me a few times if i would go shopping for him. I refused. Not because it turned me off (I don’t particularly care either way about this fetish), but because I was not willing to go out and spend money on underwear for someone I hadn’t even slept with yet! And at one point during our texting, I had to tell him to stop talking about underwear, and if he expected to get anywhere with me, he’d better start making the conversation and sexy talk more about me, and less about what his fetishes are. Men these days!

When he flew back into town, we made plans to get together. His flight got in late so I invited him over for a drink at my house. I should also mention that before he got in, I made it clear to him that I would not be promising him anything and he had better not have any expectations of how our time would be spent. And if we did have sex, it would be very vanilla to start. In other words, although I do sell strap-ons, I would still not be able to review one after he left. He was ok with that. Unfortunately, I didn’t really get to take him for a spin. I had some yeast infection symptoms and started treatments that afternoon. TMI? Whatever, you knew what this was when you started reading me! We had a drink and he made his move. Because of our height difference, it felt like I was a mountain he had to climb. A mountain he was quite eager to reach the summit of. He kissed me, long and deep, and he smelled soo good! It was getting hot, and then, suddenly, what’s that? Is that…3 tongues in my mouth?!? Fuck, Walter, get out of here! Me, the kinky pilot, and my dog is not my ideal threesome. I bribed him with a treat to go away and we got back to business. The dog, I mean. I bribed the dog. I asked the pilot if he wanted a pair of my satin panties to play with. Obviously he said yes. So for awhile I watched him stroke himself with my pink satin and lace panties, fascinated. I’m pretty open-minded about whatever turns other people on. I blew him while he fingered my panties. But he wouldn’t cum in my mouth. He said it wasn’t fair because he couldn’t make me cum. Apparently he’s a kinky gentleman. Not enough of a gentleman to turn down the blow job in the first place, but hey, you can’t fault a dog for being a dog.

He hasn’t been back in town since, but his schedule does have him back through in May, so maybe I’ll take him for a full spin at that time. If it ever gets to a strap-on point, I’ll be sure to let you know 😉

PS. I’m currently talking to a pilot for Sky West. Purely for research purposes into what else pilots are into.