The Time I Had Two Sex Dates In One Day | ❷

[ Previously on... The Time I Had Two Sex Dates In One Day | ❶ ]

Within an hour of leaving messages here and there, I was in talks with two potential candidates for some more fun. One was a hot Asian guy, who initially was a little aloof, but ended up dangling the possibility of a threesome with his hot Aussie boyfriend. Okay, how hot is hot?

Then after seeing the photo he provided, I didn't know what to say. I felt so insecure and out of place. He and his boyfriend certainly looks like the hot gay couple we all are intimidated by, and will never be a part of. Okay, not all of us but "some" of us. I remember thinking about myself at that point and wondered what will be my path.

The invitation to the threesome had a catch, was that I had to bottom for his boyfriend's eight inch tool. Jesus! Eight? And bottoming again? How am I gonna take that? I asked him how does it normally work for them and he says that even as a bottom, he doesn't like taking in his partner's dick, even though it took him a long period of training. So sometimes when the boyfriend is really in the mood to fuck and he's not in the mood to bottom, they would recruit a third. So technically, I will be used that night as a toy. That sounds kinda hot!

After weighing in on the pros and cons, I decided that I wasn't going to offer myself up for something I cannot deliver. I could have easily agreed with an empty promise and then showed up being difficult. So I painfully and unwillingly didn't push the deal through.

The second candidate in talks with me was a hot looking guy from Queensland who made the first approach. His face picture was very promising and I agreed to go over to his place later that night. He only had the apartment to himself until about 11pm so I had to ditch my writing and hurry over to his place down the street within the next hour. Two sex dates in less than 7 hours? That's never happened to me before. This should be interesting.

When I arrived, I hesitated between pressing the doorbell or texting him. I chose the latter. After waiting for a while, I wondered what took him forever to open the damn door. Then it hit me that I was at the wrong part of the street. I absentmindedly memorised the wrong unit number and had the three figures jumbled up in my head! Oh my God, thank fuck I didn't ring the doorbell!

Texting the guy immediately, I let him know that I am a couple of blocks away and will be there. As soon as I arrived, I was shockingly disappointed because I thought the "big" figure in the lobby wasn't him, but unfortunately it was. I did not see it coming tonight. The candidate does have a hot face, but he was for lack of a more elegant word of description, fat. He was a bigger version of an overweight Chris Pratt before Guardians of the Galaxy.

At that point, I told myself to either walk away or to really come clean with him that this wasn't going to work. Because number one, I felt deceived. I felt like he tricked me with a nice face picture but kept his overweight body a secret, and secondly, I really wasn't feeling any attraction to him. But being the weak, let's-try-not-to-be-an-asshole guy that I am, I didn't have the heart to reject him up front without giving him a chance. He was a friendly guy so I forced myself to shut up and go ahead.

So we adjourned upstairs to his nice apartment together. I relied heavily on my loquacity to do the work in diffusing any sort of awkwardness and to hide my incredibly anxious self. You know the part that felt betrayed and was going to yell "this is not working out" anytime.

The candidate is currently in an open relationship with a younger boyfriend, a banker who happens to be very cute from the way he describes his partner, and from the picture I saw in the living room. He was at work on a Saturday and is scheduled to come home by 11pm. I really don't want to be caught in flagrante delicto so I kept asking him what happens if his boyfriend walks in on us? Because even with open-relationships, "knowing" that your partner is having fun with someone else and "walking in" with your own eyes releases a very different kind of energy and emotional impact.

Apparently it didn't worry him and he kept reassuring me that it's okay as his partner knows he brings people home only when he's not around. That whole awkward episode I was worried about happened once a long time ago, but unfortunately that didn't go so well in the eyes of his banker boyfriend. But they've grown and worked on things.

Then, figuring out that I am not in any way responsible for his arrangements or required to be entangled into the complicated details of his partnership, I told myself as long as I stuck to playing my part as nothing more than a flimsy Grindr candidate, the rest wasn't any of my business.

Within a few minutes on the couch, I started things off with a make out because had I given myself more time to think, I would have said goodbye. The make out and foreplay was good and you could see that he was enjoying himself. Disregarding his entire body which was out of shape, I loved the whole stubble and face. He does has a hot face.

     "God, you're my kinda kisser! Cum'ere," he said and we continued kissing. 

     "God, your boyfriends must have loved it every time you kiss them", he added.

     "Uh, I don't have a boyfriend."

He stopped the kissing immediately and looked at my face with an incomprehensible expression, like as if something just didn't click.

"Really? Why?", he questioned.

"Oh I don't know. I only came out 2 years ago, still getting to know the scene, haven't found anything concrete," I said nervously.
I can most certainly hear my inner self go: Oh God, why the hell are you telling your life story? Shut up. Shut up now.

Halfway through the make out, he took off his shirt and I cringed a little. Okay, I cringed a lot. But then I tried very hard to get myself to focus on thinking about him as a person as opposed to concentrating on his fat body all the time. Until this day, I couldn't quite comprehend how I did what I did.

[ Reminder: Sexual Content Ahead ] 

 - - -  Please STOP reading now if you're not comfortable  - - -

Anyway after a while, he was ready to move us into the bedroom, the very same bedroom that he sleeps in with his investment banking partner. All of a sudden, I didn't feel easy. Call me naive, call me a wimp, but I couldn't help but thought of myself as a surreptitious intruder to the sacred space that a guy and his partner sleeps in. The very symbol of their being together, of which I don't know if I will ever have the heart to deal with had it been me in this relationship.

Sticking to the decision of not wanting to over-thinking things that are not mine to be dealt with, I followed through with the program. So we adjourned into the bedroom where he and I shed our clothes and got down to business in bed.

Initially I thought the blowjobs, kisses and foreplay would be enough. However, it wasn't and he wanted to fuck me. At first I didn't wanna go through with it because I'm not a fan of being a bottom, then later on I thought: "Okay, he's a nice decent guy. And his tool was small too. I can do small."

When he entered, it burnt. I couldn't tell if it was from the previous penetration that happened a few hours ago, or was it because in general, I'm still not used to being fucked. While fucking me, he noticed my facial expression and asked what's wrong. I told him it burns due to the prior sex date I had a few hours ago and requested for him to just come quickly.

He smiled and said okay, while whispering additionally that he would like to see me again, and that the next round he does, he wants to be the fresh one to penetrate me and not have to be second. I just listened quietly to myself because I already know in my head that there wouldn't be a next time.

Once we were done, he let me take a nice shower in the master bathroom and even gave me a fresh towel to use. I appreciated things like this so much. Some guys just throw you out or bark at you.

After the shower, I didn't leave immediately because there was no way I was going to allow myself to miss my favourite part of the program, talking and interviewing the candidate about his life story. This remains and still is one of the most therapeutic segment I love doing while meeting guys on sex dates. There's something about this way of approach to sex dates that completely changes the meaning, depth and energy of exchange.

So the guy and his investment banker boyfriend have been together for almost a decade. They were from the same town and journeyed together to where they are today in this apartment. His boyfriend was my age which dug out feelings of inadequacy within myself. You know, the whole better looking and more successful thing. I know it sounds like a very naive thing to say, but yeah I do struggle with little things like that.

I asked how did the concept of the open relationship came about, when especially you've been in a relationship of ten years. "How does that work?", I remember hearing myself ask. So apparently, they are actually in the midst of working things out. 

In the recent years when the investment banker boyfriend was climbing the ladder and committed to working all the time in building his career, their relationship hit a rough patch as this guy felt really lonely and wasn't getting the attention he deserves. The candidate was a regular working class guy who was attached to a young banker who was not only more successful, but had to constantly work all the time.

     "Was it difficult to tell your partner that you wanted to now open up the relationship?" I asked.

     "Yeah it was. It was very hard," he replied smiling.

     "But how did you manage to do it and really really settle on an arrangement like this without hurting each other or making sure that both parties ARE effectively getting the necessary benefit out of it?"

     "Well it had to come to this because he couldn't compromise on his crucial period in his career and I needed something in which he currently can't provide due to the nature of his work. So the conversation was tough and he didn't take it well but in the end it was fine. He knows I sleep with people and he sleeps with other people too. Although I think he doesn't use this privilege a lot and as much as I do because he's away and working all the time. But him and I are very strong together. He's family to me and I'm family to him."
     "Really?"
     "Oh yeah. We went through a lot together. I supported him, he supported me. I would say that even if him and I didn't work out in the end, he will still be a part of my life and will always be my family. Do you ever get that?"
I looked at him with a 'hello' expression and he automatically smiled and remembered I've never been in a relationship.
     "Oh yeah I forgot you uh...", he responded smiling.

     "You guys have a very nice apartment here." I added while looking around. "The space feels so personal."

     "Thanks. The rent is expensive too. If I am not with my boyfriend, I probably wouldn't be able to afford a place like this. I do have a job I'm enthusiastic about but I don't make as much money as him."
     "Are you okay with that though?"
     "Yeah. My boyfriend, well he's exceptionally bright and intelligent. Like really bright," he said.
    "Oh my God, you know my childhood best friend, the one I'm currently staying with says the same thing all the time regarding his bosses and other people he's met in the industry. He's an investment banker himself, and I've always kinda told him that due to the cut-throat way he works all the time, I have this impression that he's quite successful.

However he shocked me by telling me that that is not true because he's actually still way at the bottom of a corporate banking ladder. I remember asking him too what did he mean by 'really smart' when he uses that kind of adjective to describe his bosses and his other banking peers. For he does make it sound like they have this level of intelligence and smarts that is unimaginable. He says he can't quite put his finger on it or give me the answer I wanna hear, but based on how one works at the banking office, you really have to be at the phenomenal top of your game. Which I guess sounded quite logical if you're in such a competitive cut-throat dog-eat-dog world industry."

The big guy went on to tell me about how his boyfriend was devastated initially when every major financial institution turned him down upon graduation. Then in the midst of feeling low, the number one crème de la crème of investment banking unexpectedly called and took him in. The rest as we know it was history. I sat there like a small unexposed bird listening to the success of high flying eagles.

I know it probably shouldn't affect me or come to be any of my business, but hearing us talk about great career success and "real world smarts" excavated great feelings of inferiority within myself. I've mentioned before that I've always felt that I am not equipped with the right smarts. that are competitive enough for the real world that we live in. Academically and professionally.

Even back in my days at whatever I did, I was an easy C student. In everything that I do, somehow the C easily and conveniently finds its way to me. There were only a handful of moments I unexpectedly performed well, and even that required immense training. So if we're not A material, neither are we one of the Fs who become millionaire entrepreneurs. Where does my fate lie God? I pondered deeply.

     "But you know what they say about investment bankers, which includes my boyfriend from what I observe since we were together, is that they are extremely intelligent and competitive in a lot of things, but sometimes they can be complete fools when it comes to life," he added.
     "Really?"
     "Yeah, they can be. Don't get me wrong, they're exceptional, highly competitive smart guys, but sometimes when it comes to life, they're clueless."

I chuckled amusingly with heightened curiosity at his claim because although I'm not saying it's completely true, but I do feel this sometimes with my childhood best friend. I admire him greatly for the great survivor and resilient banker that he is, but it has struck me many many times over the years that I really do come from a different world when it comes to soul-searching.

Him and I went on to chat about a few more things on the couch before he noticed the phone vibrating suddenly in his pants. It was his bright and highly intelligent investment banker boyfriend calling. He was downstairs and was waiting for his current boyfriend who was with me to buzz him up because he didn't have a key. 

"Okay, I guess that means it's time for me to go," I said while smiling. "Thank you for having me," I added. "No thank you for coming," he answered. The big guy apologised for having to kick me out but I assured him that I certainly don't feel that way at all, in fact I really enjoyed the conversation we had in the apartment. It gave me a lot to think about.

I was a little worried about how to leave the building without having to go through the whole bumping into his boyfriend thing. Call me a hypocrite for going ahead with this sex date in the first place, but I am actually concerned about not wanting to put me and his boyfriend through any awkward scenario during my exit.

The candidate told me that he will go down himself and get his boyfriend five minutes after I have left so as to avoid the aforementioned scenario. I was to descend and exit on my own. I thought it was a good plan and agreed.

As I took the elevator down and walked out to the forecourt of the building, there he was, the good-looking and successfully bright investment banker boyfriend on the other side of the gate, waiting to be let in. He was handsome, dressed in casual Saturday work clothes and engrossed at the contents of his touch screen phone. I couldn't fathom with clarity if I felt envious, inferior or ready to accept that I might just never be on the same platform or level as some people.

My intention was to quietly press the gate release button and walk away quickly. However, it hit me that I couldn't find the damn button and I spent the next two minutes pacing up and down the forecourt like a fool, looking for the release button that will free the magnetic locks on the gate to let me out. The banker boyfriend was still looking down at his phone and didn't notice I was there. Please let me find it before he looks up! Please let me find it before he looks up!

    "You gotta press the green button on your left right by the pillar", says the boyfriend as he finally looked up from his phone. The successfully bright, intelligent investment banker has spoken. I mouthed the word fuck to myself in the dark.
     "Uh, thanks. Couldn't find it", I responded.

I rolled my eyes internally at myself for the blunder I staged when I was trying so hard not to embarrass me in front of the hot and bright investment banker who probably now thinks I'm stupid. God I wanted to shoot myself in the toe. 

When the gates finally opened after I pressed the button, I walked out and we held the gate for each other as he walked in. We passed one another and I said: "Have a nice night." I think he mumbled a reply, I think he didn't.

As I walked out, I was very conscious of the energy that was emanating from my body. I wondered deeply at that point if he knew who I was and which apartment unit did I just come down from. Because just when you always assume people don't have a clue as to what is going on, they know. They always know.

Right from the moment I made a turn after my exit, my head and heart was just inundated with a million emotions, thoughts, dreams and worries. For some reason, even I myself couldn't understand how my own head works and the infinite ocean that it is. I think I teared up a little firstly because of how I felt about myself earlier, and secondly, for the hopeful visions I still harbour for myself in hopes that someday, they will find its way to me, just like how it has found its way to many and have made them successful.

On my way to the bus stop, I found myself on Oxford Street and decided to take a detour to Stonewall. It was after all the last Saturday I will be spending in this city so I wanted to seize the opportunity to enjoy every last bit of my privilege and right to walk into a gay bar because I never do so back home openly and would definitely miss everything here.

As usual the bar was packed and the atmosphere, as gay and alive as ever. I bought myself a pint and sat at a corner to take it all in. I observed everything. From the drag shows to the hot guys and their hot gay groups, the fearless twinks to the good-looking bar tenders. It's been three years since the first time I walked myself into a gay bar on my own in 2011. On one hand I was grateful for being able to now sit in a bar and own my truth as a different man, on the other, I was a little sad that despite putting myself through so much running around, I was still alone and didn't seem to fit in with the crowd. Feeling a little tired and overwhelmed, I finally picked up my glass, downed the remaining beer that was left and headed home.

The Time I Had Two Sex Dates In One Day | ❶

After feeling a little shaken from the previous happenings, I woke up to a jostling Saturday morning where the living room of my friend's apartment was about to play host to a simple breakfast gathering of seven. I was feeling a little empty and completely not in the mood to be around a crowd so I excused myself and went to the bathroom to dwell on my morning ritual.

While on the toilet seat, I checked my Grindr and saw that a cute guy with an approximate distance of 118m has left me a message. Okay, let's talk and see where this goes. Within 15 minutes, we've established via WhatsApp that he was going to touch base again within an hour to see if the hang over dissipates and if he can get himself out of bed to meet for a short coffee then head back to his place for fun.

So I got ready and headed to the corner coffee house to catch up on some writing while I waited for his text. I had a very strong feeling that he might stand me up, but it didn't bother me at all even if he does because I was so engrossed in my backlog, and my journal is more important than any date. So in the end, he never touched base like he said he would.

I stayed and continued to write when another profile from Grindr who previously wasn't willing to give me his number, spontaneously left me a missed call and a voice message asking if we could meet for coffee. I called him back and within 40 minutes, I took the bus and met him in Darlinghurst, one of the most exciting gay neighbourhoods in the city.

For the past month, Grindr along with the other gay apps have unconsciously become my new social network obsession where I'm constantly on it all the time. It was so weird to think that when I was cruising very hard during the week, nothing comes up. But the minute I let go, and try to use the Law of Attraction to envision a sexually satisfied version of myself, where the energy I'm feeling says: "I'm having, I have, or have already had", these encounters just start popping up spontaneously at an unexpectedly fast rate. This method was proven to work in the post where I wrote about my sex date with a broadcasting executive.

Forty minutes later as I descended from the bus near my destination, I NEVER thought fate will physically let me cross paths with "Frenchy", this insanely hot French jock I've been trying to woo for weeks on Grindr. He lives about 80 metres away from my unit but have never for once replied my damn messages. 

Oh my God, that's Frenchy! Frenchy! The hot guy we've been after. What do we do now what do we do now? Should we go say 'Hi'? Damn it, how do we get his attention? How can we approach this fragile situation sensibly without destroying our shot? Oh my God, think, think damn it!

Within that few precious seconds that we crossed paths, I tried to get him to look at me. Come on look at me baby. Look at me. Regarde-moi damn it! Unfortunately, he wasn't aware of it and continued walking across the street to the opposite bus station. I deliberately changed my route so that I can give myself an additional ten seconds to think about what I'm going to do.

He was wearing an extremely tight maroon t-shirt with faded jeans, complete with music ear plugs which makes getting his attention an obstacle. Jesus, he is so hot. By the looks of it, he was on his way home from a work-out session at Fitness First. I watched him as he positions himself on the bus stop bench and stared into his phone.

At that point, I was really confused with my dilemma. I was late for my meet-up with the guy from Grindr, but yet I couldn't let go of my chance with 'Frenchy'. Bumping into him has catapulted me into a state where I was ecstatic, scared and torn. Torn between if I should take a left to walk away, or screw being late and take a right to invest an additional ten minutes to try and get his number at the bus stop. Come on come on M think! I stood on the side of the pavement for a good five to ten minutes in order for my mind to reason itself. 

Right Side:

"M, what are the odds that fate has arranged for you to bump into the guy you've been hunting after in order for you to walk away? You are NOT going to get another opportunity to cross paths like this again! Grow some balls and take the risk." 

"But what are we gonna say? What if we look stupid? What is our excuse to approach him? What if going up to him actually expedites rejection and ruin everything?"

Left Side:

"M, you are late for a date. With a guy who has concretely asked you out and arranged for a meeting nonetheless. This IS the present situation. Not the 'what-if' you are fantasising with 'Frenchy'. And yet, here you are thinking about whether if you want to go for somebody else? Is this fair to the present guy that is waiting for you?"

Right Side:

"No it's not fair. But neither it is to ask me to give up on this! I've been trying to get his attention for weeks." 

Left Side:

"It's okay. Just do the right thing and go meet your date now. Forget about 'Frenchy' because if he is interested in meeting, wouldn't he reply your messages in the first place? Take a hint. Look if you truly are destined to talk to each other, the universe will give a second chance to allow that to happen again. So let's go."

Right Side:

"What? What?! What a bunch of bullshit? Wait, let me thi..."

So I walked away, which I know sounds extremely stupid right now while writing it in black and white, but I made a choice based on what I thought was the right behaviour, and I can't change the past. Looking back, one might think that I would have drew on the missed opportunity lesson learnt at Starbucks and Midnight Shift to never let another opportunity pass me by this time, but unfortunately I didn't.

Using the entrance of Stonewall, a popular gay bar on Oxford Street as a landmark, I finally met up with my Grindr candidate and adjourned to a nearby coffee house for a drink. He looks better in person than in his profile picture. The features that really stood out was his incredibly scruffy jaw and his blue eyes. As soon as I saw him, I knew we were going to end up in bed together. He is not young, but neither is he too old.

He was an Anglo-Australian and the conversation with him really had every potential to be enjoyable and interesting. However, I was clearly not in my element that afternoon and I couldn't bring myself to concentrate. My heart and mind was just completely scattered all over the place firstly because of my missed opportunity with 'Frenchy'. Secondly the gay café we were in was just flooded with hot beautiful gay guys I salivate for, and thirdly, our outdoor table was right in front of the balcony unit of the German man on rebound who might catch me with another man. Wow, three issues? I thought you were just a simple guy?

Throughout the entire sitting, I was feeling very anxious and all over the place. Then, the candidate says that we should go back and chill at his home. Oh thank God, let's move. Maybe the sooner we have sex, the faster I can blow off some much needed steam that is contributing to my nervous scattered self.

The weird thing is that I feel the term horny is not what this is called, because I associate horny with being able to just fuck your brains out to solve the problem. I would have to say that hunger for a make out and physical passion with another man is a more accurate description of my situation. Although it might be the same to many.

[ Reminder: Sexual Content Ahead ] 

 - - -  Please STOP reading now if you're not comfortable  - - -

So we arrived, and a casual tour of the place conveniently turns into a make out in his room. The kiss was good, the cuddles were good, everything was so far so good.

"God, you are so sexy do you know that?", he says to me in between sealing our lips together. "God, I love your scruff", I murmured in reciprocation and he chuckled in amusement. My heart giggled at its own attempt in trying to create a little bed entertainment.

Then I went down on his competently-sized tool and he moaned in absolute ecstasy while trying to stick a finger in to play with my ass. "Are you clean?", he whispered? "Yes I am", I replied. "So, you cleaned yourself before you came to see me. You must be expecting to get fucked", he teases.

"Uh, no. I just like being clean. Has nothing to do with wanting to be fucked", I answered as a matter of factually with an underlying tone that seems to suggest that we won't be doing anal today. He asked if I liked being rimmed and I told him I love it! 

I had a moment in my head where it hit me that guys who firmly identify themselves as Tops love putting their lips to asses. Nevertheless, as long as I don't have to do it on others, it's fine. So we alternated between me giving him a blowjob and him rimming me. It got to a point where we were passionately in the 69 position. The friction of his scruff and flickering of his tongue when he rimmed me was good.

After a while, I was starting to get bored and asked if he wanted to come. "Not yet. I haven't gotten around to fucking you", he says. "Uh, there will be no fucking today", I said. 

"Aaw, why? Why? Come on", he pleads softly almost in a whisper. I shook my head and stayed strong in my decision. Then, being the "pleaser" that I am, I couldn't help but gave in after a while. The whole thing wasn't too bad, but I remember telling him to get it over with quickly because I haven't found my joy in being a bottom. He did wanted to help me "like" it with many different positions, but I was just really not in the mood.

When we were done, we took a shower and got dressed. He was headed to the Opera House for some kind of performance and I was just gonna find a café on Oxford Street to continue putting my backlog of thoughts into writing. I waited with him at the bus station until his ride came and we said goodbye. Apart from that, it was nice to get a text from him later asking me how I am.

Later on at a café, I bought myself some tea and sat down to write at a small corner, relying on the miserable power plug that is sustaining my low battery device. As you can imagine, I was also heavily distracted on the gay apps on my phone, which reminded me very much about my Facebook addiction when it first came out. My excuse was that I am in Darlinghurst on a Saturday night and I would like to increase my chances of getting in touch with more guys. I alternated between writing and cruising.

[ To Be Continued... The Time I Had Two Sex Dates In One Day  |  ❷ ]