Welcome to the first segment of The Straight Boy Diaries. The place where I take you into the taboo world of my sex life, and the men who linger in there. I used to blog about my sexual encounters (not clients obviously) back in the good old days and decided to start blogging about it again. WARNING these posts are not for the faint-hearted. Things will definitely become explicit and detailed so if that ain’t your thing, logout now. I am not going to blog about past relationships as such because I believe that’s too personal and completely unnecessary, but what’s the harm in talking about the one-night stands and random encounters I have? Well, apart from ever getting laid again of course.
Disclaimer – I will not be mentioning any names of the men that I’ve had for obvious reasons.
I don’t know how many parts there will be for this one as we ended up spending more than one day together, so we’ll just go with the flow and whatever will be, will be. I was coming back from a short work trip from Dundee and decided to spend a couple of nights in Aberdeen and make some extra cash before finishing my tour. When I was checking into the hotel I was greeted not only by the reception woman, but also a crazy old lady (and when I say crazy I actually mean crazy).
When checking into hotels it’s always nice to lay low, don’t stand out from the crowd, check into your room quickly and swiftly. but Rhonda (the crazy woman) wasn’t going to let this happen too easily. She clocked that I was a transsexual and brought it up in conversation when I was waiting for the reception to hurry up with my room number, but by the time they got me checked me into my room it was far too late. I had already met a new friend. Rhonda. hmm, i actually wonder what Rhonda is doing with herself nowadays.
As I was walking through the corridor and into the lift I noticed Rhonda staggering behind me. She was talking to herself one minute and then trying to hold a conversation with me the next. Just my luck, as I opened my room door I noticed she was staying in the room directly across from me. It was a complete nightmare – and my new bestie didn’t know how to take the hint.
Once I’m in my room and settled she wont bother me though, or so I thought. Literally EVERY 10 minutes she would come to my door chapping me up, literally ignoring my “I’m a bit busy at the moment, come over later” and making it completely impossible for me to work. There was no way I was risking taking a client into the room and having this chick chapping on the door. Could you imagine? It would literally scare the shit out of them.
I accepted the fact that I wasn’t going to be able to work (well for that night at least) so what does a lonely bored transsexual do when faced with an annoying crazy woman, a bunch of cash and nothing to do? Hit the bar! (and boy did I need it). It’s funny because although this happened a while ago I still remember exactly what I was wearing on this day. An oversized cardie, white booty shorts and white trainers (and I just got a spray tan a couple days before so my tan was on ‘fleek’). As I was approaching the hotel bar I could hear a bunch of men talking and laughing, and me thinking I looked hot I knew this was gonna be an interesting “drink”. Just little did I know how interesting it was really going to be.
As I walked into the pub I noticed 3 guys sitting at one table, one of the boys nudged another while they all had a look at me, and of course, at the bar sitting there was non other than my new bestie. At least her attention wasn’t on me any more and she was more focused on the three guys. One minute she was crying, next minute spitting on the floor and then randomly out the blue she stood up off the stool and stole 1 of the guys jackets. Maybe she was cold? Even though it was the middle of July – but at least she broke the ice for me.
It wasn’t long before I started talking with the guys, me being the whore I am I love male company. They just think differently to us woman (and trans women). Their banter is much better and you can’t beat an occasional flirt too. They were obviously contractors because they were still in their work gear, which isn’t anything odd because I used to work at this hotel for a good year (before I got thrown out – that will be for another blog post) and most of the people who checked in were contractors and people working away from home.
One of the guys, shaved head and looked like he was made of steel (turns out he was on steroids but who am i to judge? Miss coke snorting, binge drinker myself). His voice was so deep you could imagine the floor vibrate. I ordered a bottle of Rosé wine and tried to communicate with Rhonda who at this point was apologising to the barman who was on the floor cleaning up her spilled drink and spit. The three guys asked me over to their table to join them. Hmmm.. Should I go over and chill with the men, have banter and get wasted? Or end up on the floor with the bar man cleaning up Rhonda’s spit? I’m guessing you already know what I decided to do.
About 20 minutes into the conversation I noticed one of the guys give another one THE look. If you don’t know what THE look is, it’s basically when a guy thinks you’re a CIS woman and then suddenly notice that you’re a trans girl so in other words, he clocked my T. I knew in the next 5 minute I would have to bring it up in conversation not for them per say, but just to make myself feel more comfortable. “Oh by the way, I’m transsexual, I said, as the three of them sat there and looked at me, and then one of the guy’s gave another that ‘I told you so’ look. They’re was about 0.5 seconds of awkwardness but then once the initial shock was over with things became more relaxed and the drinks kept going.
I was getting quite tipsy at this point (tipsy enough to not notice that Rhonda had disappeared) and the guys were all sound. But there was something about the shaved headed guy, he had that “bad boy” vibe and we all know I love a bad boy. He then asked, “so what are you doing here?”… I casually told him that I was in the city for work and gave him that look with a cheeky little grin and he knew exactly what I was talking about.
Things were going normal, well as normal as they could in these circumstances but wasn’t until me and the shaved headed guy went out to smoke when things became a little interesting. As we stood there I could tell he was attracted to me just by the way he was looking at me and asked what my plans were for the night. I told him about the tricky situation I was in with work and Rhonda so I was free to do whatever (and/or whomever). He asked if I wanted to join him later that night up in his room to, and in his words “party”. He offered to buy the drink so as you could tell I was very tempted. A hottie and alcohol is always a mix for a good time (or in my case a good time and an interesting blog post).
He told me he would tell me things that night, or course I responded by saying I’ve got a good few stories to share myself but he interrupted me and said, “yes maybe so, but the stories I’m going to tell you, they aren’t good ones.” I remember he looked at me with this weird stare when he said it too. Of course I brushed that comment off my shoulders and called his bluff (you know, the typical Brooke thing to do). It’s funny now looking back to how naive I was, and i don’t think I was quite ready to hear what he was so willing to tell. Little did I know then, that a year later I would be writing about him, in my own straight boy diary, he was my Mr. Debt Collector.
Well I think I’m going to finish part one here because my fingers are sore from typing, but are you enjoying this so far? If you want part two share this onto your social media and your feedback is always welcome.
Until next time, double kisses.