One’s first time doing something can be an awkward, flailing situation. My first time alone with a guy certainly contained those elements, in addition to so much more. At the ripe age of 28, I decided to give myself the experience that I had clearly forgotten to have during college.

Manuel was a bit over 5’ 10” with a muscular build and good looks to match. While I can’t consider myself as someone that is attracted to men in the same way as I am attracted to women, the experience alone was something that got me aroused. He dwarfed me in every way: height, width, and the horse cock he had under his pants shown to me before the actual meetup. In person, the thing was insane.

The day of, I drove over to his apartment, and we took the elevator up. We had casual conversation mixed with some drinks before I suggested an ice breaker to relieve some of the tension. A simple game: players take turns asking each other trivia about themselves with two answer choices. If the answerer is wrong, the asker strips a piece of clothing off them and vice versa if they are correct. With three lives (shirt, pants, underwear) and a 50/50 chance, it’s designed to be a short game.

I was in the lead, Manuel stood before me, shirt off and had just gotten an answer wrong so I claimed his pants as my prize. I may have grazed my hand against his bulge as I removed them (I’m allowed to cheat at my own game). Another article of mine down, just two strangers standing in their underwear. Manuel answered wrong yet again; I had him. I slipped off his underwear and out bounced his thunderous cock, an absolute weapon. Naturally, I took my remaining article off in solidarity. As the loser, I offered him a consolation prize of my mouth on his cock, and he obliged. I took what I could in my mouth and as far back as I could, stroking the shaft with gusto and never forgetting about his full balls. I couldn’t get much down and I could feel myself choke so I opted to slink further down and suck on his balls while continuing to stroke his steel column. I jammed my knuckle just above his asshole to give his prostate some pleasure as my mouth continued to do the work. His moans telegraphed that he was enjoying himself quite a bit.

After some time, he felt I had earned some relaxation and had me lay on my back. He remarked about my boundary of not kissing (I don’t kiss guys) and kissed down my chest and nipped at my nipples. He took my cock in his mouth and took it deep. Manuel knew exactly what he was doing and I enjoyed his warm breath reverberating down my shaft. I knew I wanted to fuck but was concerned that my inexperience with guys was going to get in the way. Spoiler alert: it did.

I donned a condom and applied a generous amount of lube to it; Manuel got on all fours and presented his hole, yet my semi-drunk cock could simply not stay hard. The combination of nerves, alcohol, and a distinct change in my usual sexual exploration left me soft in all the wrong places despite my desire burning. I resorted to teasing his hole from behind while he stroked his ceaselessly hard rod. I had him flip on his back, hoping the change in angle would help. Manuel obeyed and I began teasing his asshole with my finger while he continued stroking. I once again tried to penetrate his tight, chiseled ass but I couldn’t get there. I tore the condom off and apologized as I took both cocks in my hand and began stroking. He did the same and before long, we began blowing our loads on each other, Manuel taking most of the cum all over his cock. I left feeling mixed but knew I had the rest of my life to try again.