What I wore: denim shorts, white t-shirt, bikini for wakeboarding, and (later) leather shorts, transparent white lace top
What he wore: board shorts, t-shirt, hat for wakeboarding, and later, light blue chinos and pinkish-red button up shirt, suede loafers
Contains X-rated content. (I have been doing a lot of depraved things).
Just to be clear, this date is named ‘The Venture Investor’ to distinguish from ‘The VC Tinder‘ but they are basically different wordings for the same position. The Venture Investor’s tagline also explicitly stated that he was a venture investor. I matched with him a few days and he said that our travel plans matched, that he would be in Sydney this week and that he would also be in Burma during the time I would be there. I replied saying that it was fate, and that he agreed.
I don’t normally decide before meeting someone if I’m going to hook up with them, but the Venture Investor was gorgeous with great dress sense, and had a look that reminded me of Christian Bale, my ultimate celebrity crush. The Venture Investor was a British expat living in Singapore, and was coming to Sydney for a few days vacay. He asked if I wanted to meet up the day he arrived in Sydney but I had plans that day, so we decided to meet on Friday during the day instead. Venture Investor’s profile said that he was looking for a wakeboard buddy, and he suggested that we go wakeboarding, and then at night I should show him around Sydney. I agreed to wakeboarding, (despite never having been) without giving it any thought.
On Friday at midday he picked me up from my place and we went to the wakeboard park which wasn’t too far away from my house. We chatted a little on the way there, but I didn’t feel any sort of instant click, which is what I’m always looking for. Venture Investor said he’d been living in Singapore for a year and a half and might be moving to California next year for work. Before becoming a venture investor/capitalist, he had been an investment banker. We didn’t have great chemistry, but Venture Investor was gorgeous. I’d been steadily stalking him on Facebook for the past two days prior, and he had photos with a ton of girls- I took this to mean he was a total fuckboy, and was probably good at sex (I wasn’t wrong).
The day involved a series of mishaps, me being clumsy and falling off the board numerous times, and by the end of the session, my arms felt like they were about to fall off. After we finished up, Venture Investor asked me if I was coming to the city, I said I would, but that I wanted to take a shower first- he asked where and at first I said ‘at my place’ but Venture Investor then asked what he would do while I was in the shower. I then asked if I could shower at his place after grabbing a change of clothes from my place, to which he said yes to. When we got back into the car, Venture Investor reached over and grabbed my hand and started holding it. After I took my hand back and placed it in my lap, he then reached over again and put my hand on his leg. He asked if I liked cuddles, to which I said yes to. I started massaging his muscular leg while driving. He also reached over and began fondling my breasts and stroking me inside my underwear proclaiming that I was ‘so smooth’ (I just love being given vulgar compliments).
Shortly after, Venture Investor guided my hand to his penis, and asked if I liked giving hand jobs, I said I didn’t mind them, and proceeded to give him one while we were driving back to his hotel. We hadn’t driven very far yet when I began to question if I should be doing this with someone I hadn’t known very long yet, and Venture Investor then said he didn’t want to pressure me into anything and that he could drop me home if I wanted. I said no.
As we continued driving, Venture Investor asked if I liked giving blowjobs, I said I hadn’t given one since I had gotten my braces on a month ago, and he asked if I wanted to try. I like having the D in my mouth so obviously I obliged. While I was leaning over Venture Investor reached behind and rammed two fingers into me. I only stopped because we were pulling up at a traffic light. Venture Investor asked if I had done that before, and I said no, he said it was his first time too, and that I was very naughty. He then said “I know you liked it because you got very wet. What else do you like?” I didn’t respond to this question, but continued giving him a handjob in the car as we were driving. When I didn’t stop giving him a handjob, Venture Investor looked over at me and said ‘you do like that dick’ (yes, yes I do).
Venture Investor reminded me of Whiskey Tinder and Fake Lawyer Tinder in the way that he was so confident and liked to talk dirty and say vulgar things. While we were still driving, he asked me if his cock was big enough for me, that he was very horny after receiving the BJ, and that my braces hadn’t affected my ability to give good blowjobs.
While we were still driving back to his hotel, Venture Investor began a conference call using my phone and proceeded to say that he was ‘so annoyed about having to do the conference call, and that he wouldn’t say anything’.
We got to the hotel around 7 and when we were trying to go up to his room, the key didn’t work. A bunch of other people’s keys didn’t work either, so we tried to go into the fire stairs and go up from there but instead got locked inside. Venture Investor was fuming and saying ‘this f*cking hotel’. After we’d gone to reception and gotten two more keys, Venture Investor looked extremely happy and turned back and smiled at me after power walking up to the hotel room. When we got inside, I grabbed my things and hopped in the shower. I had already completely undressed when Venture Investor knocked on the bathroom door and tried to come in completely naked (yup,he did the Naked Man) I pushed him out and said that I wanted to shower alone, and he slapped my ass, and said that I was “so shy”.
After showering I came out and found Venture Investor sitting at the table, still naked, still on the conference call. I had put all my clothes on at this point and was hoping we could ease into it slowly. This was the first time I had had sex with someone new without drinking alcohol prior and I was feeling nervous. Instead, Venture Investor came over and started taking off my clothes, and pushed me back onto the bed. He pushed my head down and I started giving him a blowjob. All the while, he was still on the conference call. I recall hearing information about how food ordering services are the second thing that consumers spend money, hence they should invest in that.
I hadn’t been giving him a blowjob for long when Venture Investor pushed me back down. He hadn’t made a move to get any sort of protection so I asked him if he had a condom. He looked a bit uncomfortable and said “no, do you?” I said no, and was about to say we could run down and get one but instead he spread my legs and started having sex with me. He had a good sized penis, but wasn’t as big as Whiskey Tinder. He had a great, muscular body with almost no hair on his chest. His room also had a mirror on front of the bed- totally appropriate for the occasion. He enjoyed putting me on top of him and thrusting and watching us in the mirror. Venture Investor was very good in bed. It was the roughest sex I’d had in my life. He completely dominated me. I’m very sure he wanted to do anal as we were doing reverse cowgirl at one point, and he was touching the rim of it, making it wet by licking his fingers. I wasn’t going to have another wrong hole incident so I batted his hand away as he was doing this.
Also, the whole time we were having sex, he was in the conference call. At times when he needed to talk, he’d make give him a blowjob again, would stroke my hair and kiss me on the head as I did so. He also tried to take pictures, which I said no to. He liked spanking me, hard and was talking throughout, calling me baby and asking if I liked his cock (the answer was a resounding yes). At one point, while I was on top, he put his hands around my throat and started choking me. I started to get a little frightened thinking ‘is he trying to kill me? Am I going to die in this hotel room?’ However, he didn’t do it hard, and when I moved his hands away, he said ‘oh, you don’t like it’ and removed his hands (I regretted doing this). I was surprised that I liked it, and began doing it to him. After this, he threw me down on the bed, and started thrusting into me, very hard and choking me. Hands down, the roughest and wildest sex of my life. We tried many different positions, and I’m very sure that Venture Investor watches a lot of porn because of all the things we did.
But it didn’t end there. He turned me around and started thrusting from behind, pulling my hair and spanking me, asking if I wanted him to come now or fuck me more. Obviously I said fuck me more, so he said to suck him off for a little bit so he could fuck me longer. At this point, he started speaking in the conference call again (YES, the whole time we’d been having sex, he’d been on the conference call). While I was giving him a blowjob and he was speaking in the call, he started going soft, but went hard again after he’d finished speaking (No, the conference call was not over, he just finished talking).
We started having sex again, but then he said that he was going to come on my face and then pushed my head down to his penis while he started jacking off strenuously. After a minute or two, he came on my face, and it was thick and gluggy and there was a large amount of it. A good deal of it actually ended up in my eye, which I wasn’t too happy about, I would rather that he had come in my mouth. He then gave me a towel and said he’d clean me up, he had missed his aim and it had sprayed on several parts of body including my thigh, which he was extremely careful to wipe off.
Venture Investor is the dirtiest boy I’ve ever had sex with, but I quite liked it. We finished having sex, and he still wasn’t finished on the conference call. He finished the call shortly after that, but then spent some time working on emails, then said he’d take a shower and we’d go to dinner.
I was not keen on going to dinner. While he was getting ready, Venture Investor claimed that he looked fat in the picture I had taken of him at the wakeboard park that day (he did not look fat). He probably had the body of a sculpted Greek god. The way that Venture Investor had sex reminded me of one of my favourite movie characters, Patrick Bateman. I asked Venture Investor if anyone ever said that he reminded them of Patrick Bateman, and he said ‘yeah, loads of people. I used to get it more when I worked in investment banking though’.
Knowing that lots of people also confirmed my thoughts made me realize I had totally just banged the real life Patrick Bateman (and it was depraved and wild, just like the real Patrick Bateman would be). I asked him if he was always so rough, and if he always came on girls’ faces, to which he asked if being rough was bad, and that he did always cum on girls’ faces (totes watches too much porn).
We went down shortly to have dinner, but I couldn’t wait to get away. The awkwardness of having to eat a meal with someone who just came on your face. While sitting through dinner awkwardly, I asked Venture Investor if he hooked up with all the girls that he met from Tinder, to which he looked alarmed, and said no. Then he asked “do you hook up with all the guys?” I replied that I didn’t, and he said “good.” He murmured something about it being risky having sex with no condom, and that he “didn’t usually do that.” Then he said: “I’m counting on you!”
I was glad to get away, and Venture Investor called me a taxi and then said ‘well, goodbye my small friend. Text me’ and kissed me on the cheek.
On a side note, my Tinder hookups seem to be getting wilder and wilder. First getting my toes sucked, then getting choked and getting cum on my face- I wonder what’s next.