Every now and then, if you’re lucky, you’ll find yourself in a sexually charged situation so cinematic it makes you feel like you might be in a movie. The first time it happened to me was when the blonde, lithe, former volleyball player I was dating at the time was laying on the bed of my small New York apartment, beckoning me in a black lace thong, her finger and silhouette lit only by the moon. I wondered for a second, how a chubby guy like me ended up in a scene from a movie I would’ve jerked off to when I was younger. A new bar was set. I came to her and we came together, on each other.
The second time this happened was with a man, a stranger who had reached out to me on Facebook because they were a friend of a friend and saw my profile and felt something. At this time I’d hooked up once or twice with a man but it wasn’t really routine at this point. It’s still not, but maybe I’ll get there one day. This man was out of every gay fantasy I’d ever had — perfectly chiseled, tall, a sweet (i.e.: non-threatening) smile… he had reached out asking if I’d like to get coffee. We chatted a bit and I eventually agreed. I was excited. Excited to explore his body and excited to breed a little more intimacy in my gay sex. That didn’t stop me from going to one of the lingerie shops on Hollywood Blvd and picking out a cute jockstrap to wear just in case things went there — I walked past the browsing exotic dancers to the men’s section where I found a very cute zebra print jock that showed both sides of me off well. It was a rush. I felt like one of them in a sense. The sexual borders I knew vanished for the day. I was lingerie shopping for a date with a beautiful man, which bred an internal camaraderie between me and the women in there. I wanted this all to feel comfortable and it was starting to. The same level of comfort two women seem to have when exploring each other’s bodies for the first time. Softly stroking another pussy doesn’t seem to, in any way, threaten their confidence when it comes to riding a cock. I wanted this. To be able to worship a man’s cock and take his load before making a woman writhe and moan with every gentle, deep thrust of my cock the next day.
I woke up the next day, jerked off twice to get through my morning meetings with a clear head, slipped on my jock, a cute pair of chinos and a linen button down shirt and headed down to the coffee shop for my first date with a man. It was surreal. He was there. He had a skateboard, and a sleeveless hoodie, which allowed me to feel his biceps as his arms reached around me for a hug. We got coffee, discussed our mutual friend, what we did for livings, what we were watching on TV, all while we took in each other’s bodies. He likes “big guys” he told me. I told him that was perfect because I liked muscular guys. I was too nervous to make the first move, and so was he. The fact that his apartment complex has a hot tub came up, but then we called it. He had plans, I lied and said I had more work, and we agreed to “do this again.”
I sped home and slowly stripped down, closing my eyes, imagining his hands in place of mine, as I explored my body, running my fingers over my zebra-printed bulge and straps hugging my ass cheeks. Thought it was my third time that day I still had more left in me and the fantasy of this guy alone was enough to drain me entirely.
Later that night we texted a bit and made a date for Thursday after work. That’s promising. We made sure to time box it. This time I had a dinner and I assume he was lying when he said he did too. I wondered if I needed a cute swimsuit. I assumed the hot tub might come into play, but it was a shared space so I didn’t want to be too bold, but I also wanted to be authentically me.
Back to the lingerie shop, past the shoppers to the men’s section. Luckily they had options. One was a sexy orange Gregg Homme thong. I figured I had to work up to that. I opted for a similar designed speedo from the same company. I tried it on at home that night and thought about going for a fourth O but decided against it. I wanted to save it all for him.
I thankfully had enough distractions to keep me occupied for the two days until Thursday. Granted, I did spend an hour each night edging myself to “How To Have Gay Sex” videos on PornHub (there are fewer things hotter than watching two Filipino men demonstrate a variety of positions from the Kama Sutra). I woke up Thursday, made it through the day, slipped on the speedo followed by the same pants and a breezier shirt, and grabbed an Uber to West Hollywood.
Source: reddit.com/r/sexystories/comments/qkoy60/mmmf_pushing_my_bicurious_envelope_part_1_of_2
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