Standard apology in advance for typos on mobile. This happened a few years ago and I’ve been dying to explore more ever since.
I was in my early twenties at the time and feeling unusually lonesome after a long, dark winter in Canada. As a tall, daily gym-goer, it wasn’t particularly difficult to attract the attention of women, but for about 6 years prior, I had been thinking about what it would be like to be with another man. The thoughts and fantasies first started coming to me like a snap out of the blue in university while on a trip abroad. I found myself only now asking myself what taboos had held me back in the past, however, and decided to see if Craigslist could help me satiate my desires (back when it still existed).
I put up a fairly timid post asking if there would be any guys around my age who might want to help me explore my curiosity slowly and discretely. I heard back from the usual plethora of thirsty guys but what caught my attention was a young, 19-year-old student home from university who seemed out of my league to the point that I thought it could be a catfish. A little bit like Zack Efron, with a swimmer’s body. After messaging for a week or so and spending nearly the entirety of that time hard in my pants at work, in the car, etc., we decided to meet up on a Saturday after skiing with my friends.
I got home around 4 and the sun was just starting to set, which felt a bit reassuring that no one would see him show up at my place under the cover of night. I remember wearing sweatpants so that, in my mind at least, they would be easy to slip out of quickly and I wouldn’t get tired up.
He knocked on my door and came in as we both stared at each other a bit nervously. He had much more experience with this sort of thing than I did so we exchanged greetings, talked a bit about how I had been wanting to try this for a while and what we might want to do. I told him I was up for trying pretty much anything as it had been a fantasy for years. I lead him to the bedroom where I had my bed neatly made, perhaps out of nervousness and he asked me to sit on the edge, slightly guiding me with his hands. I remember thinking how I had never been touched by a guy in a sexual way like this before and his hands felt much more firm than I had been used to with women.
As I sat there, he leaned in and before reaching my face, tilted my head sideways and went to kiss me neck. I felt his stubble prickling on my skin like I had never felt before but it also tingled my skin and my stomach immediately began buzzing. Blood started rushing to my cock and there wasn’t much hiding my erection bulging in my pants.
He spun me ’round then lifting me off the bed into a bit of standing position at the edge of the bed as he took his place lying down, propped up by the pillows and the wall. He then took off his shirt and pulled me in close to him. For the first time, I brought my lips to his body and kissed his chest. It was warm and harder than the skin I had been used to. I had an insane amount of butterflies in my stomach thinking, “I’m going to go for it.” I slid my hand over his pants, up his thigh and for the first time, over his growing bulge and gave it a squeeze. I distinctly remember tracing the shape of his cock through his pants trying to take notice of exactly how it felt after having fantasies for so long. I then unclasped his button, slid his fly down and shuffled his pants and underwear off so I could see what I was working with.
Oh my God, I thought. For the first time in my life I was seeing a cock hard in real life. As it spilled out of his pants, I thought he was enormous and wondered if they were all this big in person or if he was just surprisingly big. I reached my palm out and grabbed his probably 7 or 8 inch circumcised dick for the first time and thinking it was so much warmer and softer than I expected it to be. While he was rock hard and it had resistance, the skin felt surprisingly smooth and silky.
I rubbed him back and forth for what felt like 5 minutes but was probably more like 30 seconds. I then kneeled on the bed, hovering over his lap and thought, I NEED to know what this feels like in my mouth. As I lowered my mouth onto his girth, I again thought it felt incredibly soft and warm on my tongue. It didn’t really taste like anything but it was a remarkable sensation in my mouth. I slid my tongue all over his cock from the base to the tip and then slid my mouth down to his balls to take them into my mouth as well. Despite being a first timer, I was able to take most of him into my mouth since I’d practiced on a toy a few times in the years leading up to this. He moaned and let out a “that’s impressive.” After stroking him and sliding my mouth up and down his shaft for what again felt like several minutes, he pushed me back and and slid my sweatpants over what was perhaps the hardest my dick has ever been. He took my uncut cock into his hands and started stroking me as I still had my hands on him.
He shuffled down slightly and positioned his mouth over my cock and I flipped around so that we were both lined up with each other’s manhood. He then took me into his mouth as I continued to bob up and down on him. To this day, us 69ing is still the most memorable moment of this encounter as we shifted into our sides and started gliding our mouths all over each other’s hard cocks. This was probably the thing we did for the longest and, to this day, it is some of the best head I have ever had.
“Do you want to have sex”, he said next as my heart started to race. “Mmhmm”, I mumbled as he was still in my mouth. I flipped back around and climbed on top of him so that I would be in a cowgirl/boy position and thought, “I want to try frotting!” As he got a condom ready, I took both of us in my hand at the same time and grinded up against him forcing my weight into him while rubbing us both simultaneously. This was one of the hottest things I had ever done, I thought.
As I eased off of him, he slid a condom on and I shuffled forward a bit to line up with him better. He poured a generous amount of lube on his hard shaft and I sat back to take him inside me. We tried for a good 5 minutes to get him inside me but as we fooled around and he tried to slide inside me, we couldn’t quite get it in. To this day, it is still my biggest regret as I had been dying to know what it felt like to have a man pumping inside me. While we couldn’t quite get him inside me, I grinded my hole over his hard cock, bucking faster and faster as I went. Even on the outside, his cock felt so good against my hole.
As I kept going, he muttered “I’m going to cum”, and a few seconds later let out an extended moan as he pushed himself hard against my ass. Even if it wasn’t filling me up, I was so turned on knowing that I had made this happen for him.
After he finished, I shuffled off of him and to his side as he slowly started sliding his hand over my cock again. I wasn’t close to cumming but his touch felt so good regardless. We lay there for another few minutes before agreeing that it was an amazing first experience and that we’d have to try anal again in the future.
As he got dressed and headed out, I quickly put on some porn and finished myself off and leaked cum all over myself. As I checked my email after finishing up, I saw I already had a message waiting from him.
Source: reddit.com/r/gonewildstories/comments/g0uc52/first_time_giving_head_exploring_my_sexuality
That’s a hot story! Thank you for sharing it! ?