My First Gay Handsome Boyfriend

I wanted to share this experience because it's something I find myself returning to, even years later, after many boyfriends. I cant help compare all boyfriends to my first and they often fall short of my expectations. Some of the small details have escaped me over the years but most of it is how I remember. Here's the story;

My high school years were not memorable. I was the stereotypical quiet Asian student with good grades, few friends and unless we had a project together, you probably wouldn't remember me. I had a one girlfriend only because several of my friends tried to hook me up with a classmate, but I knew I was into guys probably since around my junior year and my relationship with her never materialized into anything significant. I often watched gay porn at home and the celebrities I had crushes on were all in general, older guys. Even when I would touch myself, it was always a man that I would fantasize about, for as long as I can remember. Still, I did my best to hide my sexuality in high school and instead, I stayed focused on grades and getting into college. High School came and went, and I remained a virgin, although I did fool around with a casual girlfriend at a party. Nobody suspected I was gay, I think.

College was much more instrumental in my development into a grown man. I didn't have to deal with peer pressure and my new friends were all undergrads from my dorm. I became much more comfortable with my sexuality and even mustered the courage to tell several of my friends. However, it was also sadly true that I had yet to even hold another man's hand or go on a date with a guy, let alone sleep with one. I was too timid to ask cute guys at school if they were into guys and since I was only 19 at the time, I wasn't able to enjoy the gay bar scenes in nearby San Francisco.

The only thing I could think of was of course, the internet. At the time, there was no Grinder, Tinder or Bumble. The only such site known to me at the time was Craigslist and I was familiar with their personals section as I've browsed and fantasized about hooking up with a man before.

On a cold December day, I finally decided that I would give dating a try and posted my first ad on Craigslist. My ad was posted on the men-seeking-men section and had the headline "Inexperienced Asian male, 19, looking for fun and more". So much for being original. The actual ad was a bit more provocative. I included my stats and what I was looking for (dating and intimacy) and attached of photo of myself in underwear.

Within an hour of posting the ad, I was bombarded with a plethora of responses. Most were cock pictures along with something to the tune of "let's play. 44 M, DDF. Can you host?"

I wasn't ready to meet someone for sex right away and my ad clearly stated that I was looking for a man to date and possibly be my first boyfriend. I was looking for someone to teach me how to be intimate and someone who was respectful of the fact that I was a virgin. The night passed without any substantial responses, only a bunch of cock pics, and I remember thinking "maybe this isn't for me".

The next day I looked through my email and found one that caught my eye. I have to admit, it was his photo that caught my attention at first. Unlike most of the other responders who sent variations of their private parts, this one had a full body picture with face, of a very sexy, shirtless, physically fit man in his 40s with masculine features and some gray in his hair. His chest was hairy but it seemed like such a natural look for his muscular body. The text stated that he was recently divorced and was looking to explore his bisexual side with someone who would enjoy his company. His name was Dan and he said he was interested in biking and wine and was into Asian males. He explicitly said he was not looking for a one night stand, but a relationship that could allow for one or two dates a month to start and see where it goes.

I obviously responded to him, because this story is about Dan, but I don't remember exactly what I said. I think I was so nervous and excited at the same time and I would guess my response was along the lines of, "thanks for responding. I would love to get to know you more and I think you are extremely sexy."

Dan responded right away and immediately, we hit it off. He was very respectful of my inexperience and he suggested we meet for coffee first as a meet and greet. This calmed my nerves a bit because I knew I wouldn't have to feel pressured to do anything if we weren't a good match. We decided to meet for coffee near my University and exchanged phone numbers.

When I arrived at the coffee shop, Dan was waiting for me at a table inside. I recognized him right away and felt relieved he that resembled his picture. Instead of a handshake, he gave me a hug which I thought was really nice. He kept complimenting me on the way I dressed and asked to see my ring which I bought as a fashion accessory from Japan. I must have been looking nervous because he asked me if something was wrong. "Not at all. I'm just worried you won't like me".

That's when he put his hands to my face and told me how nice I looked and that he would love to see if we could "get to know each other more". There's something about a first meeting with someone and being able to keenly recall the sights and smells of that moment. To this day I still remember being very attracted to Dan's masculine fragrance, which I smelled on him when we hugged.

"I'd like to get to know you more too, Dan. I think you're my type as well". The words just naturally came out of my mouth without much thought. He told me there was no pressure at all to do anything and asked if I'd like to continue our conversation at his place, since it was nearby. I wasn't naive. I knew what he was inviting me for and I wanted him. He was exactly my type and everything felt so natural. He wrote down his address and after about an hour and a half, we decided to meet back at his place.

Dan lived in a nice apartment nearby and I remember it being much warmer than the coffee shop. He greeted me in his t-shirt and jeans and I could see that he was built very well. About 6'2" and 220. He asked to take my jacket and as he removed my coat, he gave me a kiss from behind on my cheek. All I could think was "this is really happening". It was a very enjoyable feeling of nervousness, full of anticipation. Dan, on the other hand seemed relaxed and casual about things. He grabbed my hand and asked if we'd like to hang out on the couch.

Our conversation on the couch became more sexual in nature. He asked if I liked gay porn and whether I had a preference. I told him I watched my fair share and most of the guys in the movies looked like him. He asked me if it was ok if he moved closer and I said yes. The flow of things felt so natural to me and it was hard to believe that I had just met him in person just a few hours ago. Before we knew it, he was sitting behind me with his hands wrapped around my tummy area as I was holding his hand over my t-shirt as we talked about my college classes, what I was looking for in a career, and of course my love life. "So, you've never even kissed a guy before?" he seemed to doubt me.

Feeling suddenly slightly embarrassed about my virginity, I hesitated. "I just haven't been able to.." and that's when he moved in for our first kiss. I closed my eyes like they do in the movies and tried to make sure I was doing everything ok. I've kissed a girl before in high school but Dan was so different. He was so much more in control and I just felt so secure and vulnerable at the same time in his arms.

His other hand remained locked with mine as it pressed against my tummy the entire time we kissed. "How was that?" he whispered to me. I let my eyes do the taking and I must've been telegraphing that I wanted more because he moved in again, this time for a much more passionate kiss. His tongue gently brushed on mine and I let out a subtle moan that let him know I was enjoying his kissing. His hand decoupled from mine and found it's way underneath my shirt which sent a whole new tingly sensation up and down my body. It was at this point that I noticed I had a pretty good erection under his pants which I could feel pressed up on my lower back.

I too, was pretty turned on at that moment and if he had reached for my pants button and slipped his hand in my underwear, I would've let him, but that's not what happened that day. "I think we should stop here. I'm really enjoying your company and I don't want to ruin anything," he told me, to my disappointment.

"Yeah I agree", I lied. He asked me if we can meet again on the weekend and let me know that if I wanted, I could even spend the night. I told him that sounded great and I would definitely be interested in doing that. I was pretty horny and worked up at that point also, so I probably would have agreed to meeting in his car for sex but he was a gentleman and even walked me out his apartment. I left feeling disappointed but more sure than ever that Dan was the man I wanted to be my first.

The next few days were torture. All I could think about was Dan and all the things we would be doing over the weekend. Should I masturbate a few times before our date so I wouldn't cum prematurely? What would I wear? Was I really ready? We stayed in touch the rest of the week via email and I told him I would love to spend the night. It was really going to happen. We flirted as well and I told him how much I enjoyed kissing him and being in his arms but much of the tone was still vanilla.

The weekend came really quickly and I started prepping for our date early in the day. The showers at my dorm tend to get occupied in the late afternoon so I started picking out my clothes and grooming for Dan around noon. He had mentioned that he enjoyed watching TS porn and thought feminine guys were sexy so I tried to be as fem as possible. I shaved my private areas and left a small little landing strip like the girls in the movies do and even plucked out 50-100 hairs to give it that perfect tailored look. I also went and bought some women's perfume at Ross (of all places, but college kids are broke). I gave myself a thorough cleaning with my dildo that I bought about a year ago. I didn't even know about cleaning kits back then so that was the only method I knew of.

I would lather soap on my dildo and insert it into myself and rinse out with water and fingers. Repeat, repeat, repeat until I was comfortable enough to let Dan put his fingers or cock inside me if he wanted to. The thought of it all was just so overwhelming and exciting. I had such a big crush on Dan. I didn't own any feminine panties at the time and I don't think I would have had the guts to wear something like that on a first date so I wore the cutest boxer briefs that I owned which was a red and green Xmas themed underwear. Finally I sprayed my girly perfume once around my chest and once inside my pants and I was as ready as I could be! I decided not to release my cum before our date because I wanted to save it all for Dan.

When I got to Dan's apartment, I could tell he too, had spent a little time getting ready for our date. He casually gave me a peck on my forehead and told me how excited he was to see me. He took me by my hand and led me upstairs where he had some wine waiting for us. Being only 19, I didn't have much experience with wine, just like with guys, but I took the glass and we talked and flirted on the couch. Every now and then he would compliment me on how cute I looked and kissed me on the cheek with each kiss moving closer and closer to my lips. He took my wine glass out of my hands and leaned in for a long, passionate kiss. I could feel his tongue pressed against my lips and I let him know just how much I wanted more by opening my mouth and letting our tongues get tangled. Exactly what I was waiting for. "I was thinking about this all week" he said as he pulled away from kissing me.

This time I leaned into him and put my hands around his robust neck and kissed him as I put my tongue into his mouth. We probably kissed for 10 minutes while he rubbed my bare back under my shirt. I let him take my shirt off, exposing my completely hairless body. Dan and I had such contrasting bodies. He was wide, hairy and muscular with a little gray mixed into his hairs. I was pale, soft and hairless and weighed about 100 lbs less than him. He gently lay me down on the couch, slowly kissing every inch of my upper body, including my pink nipples and even my recently shaved underarms. I had my arms wrapped around his muscular bare back and occasionally rubbed his hairy chest with my palm, whenever he would sit up and take a break from kissing me, admiring his muscles and running my fingers through his chest hairs which felt completely foreign.

He seemed to instinctively know the locations of all my sensitive areas. My neck, my nipples, underarms and around my belly button, where he spent a little more time. Dan continued to kiss me below my tummy and he unbuttoned my pants, continuing lower and lower until he was kissing me just above my hard 5" cock. I had spent a good amount of time shaving and shaping my pubic hairs into a little landing strip for Dan but suddenly I felt embarrassed about letting Dan see me down there. I felt myself blushing but Dan being the gentleman that he was, he didn't even give me a chance to think about anything else and removed my underwear and put my cock right into his mouth and gave me my first blowjob. It was too much to handle. I started breathing so heavily and even felt my eyes tearing up from the overwhelming emotions. He was the opposite. Calm, in control, and almost mechanical as he just pressed his hands against my belly and bobbed his head up and down. Dan saw the tears running down my cheek and he asked me if I was ok. I told him (and I remember this so vividly) "I'm just so happy to be here with you"

He continued to bob his head up and down for maybe a few more minutes and I just lost it. I felt my body tense up and all of my sensations came to an explosion that was released into his mouth. My speech was reduced to incoherent moans as Dan slowed down and I felt myself blush immediately, realizing what just happened. He pulled me out of his mouth without a trace of cum and said to me, "you didn't tell me you were going to cum"

I didn't know what to say and felt terrible about it. I thought he'd be grossed out and our night would come to an end. "I couldn't help it.."

He probably saw how insecure I looked and immediately we embraced in a long hug, which was very reassuring. I never felt more safe and protected than being in Dan's arms in that moment.

With tears still running down my cheek from the overwhelming sensations, both physical and emotional, he asked me if it was ok if he kissed me again. I couldn't find the right words and just nodded my head my head, "yes". I always thought I'd be in flight mode after ejaculating because that's how I felt when a girl would make me cum, but Dan was different. I wanted more. I wanted everything. I wanted to share every inch of my body with this man and feel him in places nobody had been before. I wanted Dan inside of me.

We made out for the next 15-30 minutes. His pants came off too in short time and I had his 8" cock in my hand as we made out. He was so much thicker and bigger than me, and I was flattered at how turned on he was. I was no longer embarrassed about squirting in his mouth and I actually found myself being a little frisky. "Is it ok if I sucked your dick too?" I asked him as I looked at him right in the eyes. "Please. I really want to."

"Of course baby, I want you to so bad", he admitted.

It would be my pleasure and in the back of my mind, I decided that I would be swallowing him too if he came in my mouth. I wanted Dan to be my first swallow and there was no man in the world I'd rather share that with. My eagerness probably showed because from the moment I asked to suck his dick until I had him completely in my mouth was a mere 15-30 seconds. I went right after it and I have to admit it didn't feel like my first time. I'd practiced many times in the shower with my toys and despite Dan being on the larger side, I avoided letting my teeth come into contact with his erection. After about 10 minutes of sucking his dick, my jaw was getting a little tired and again, like the gentleman that he is, he noticed me struggling to keep going and pulled me up back up to his chest and hugged me and wrapped his arms around me as if to show his appreciation for my efforts. I was ready to swallow his semen but he had other plans. While we were embraced in a close hug, I felt his hands move slowly down to my anus. At this point, I was all his. He could do anything he wanted to me and I was ok with it.

He gently massaged my hole with his fingers and I moved my hips back and forth uncontrollably and in tandem with his finger movements. He reached over to the coffee table and grabbed his lube and put a good amount on his palm. I have to admit the sensation of cold lube felt really good on my butt as he continued to massage me. I whispered to him "put it in" and he gently kissed me on the cheek as he pushed his finger inside of me. It didn't hurt at all and he lay me on my back once again, this time spreading my legs and bringing my knees closer to my chest. His muscular shoulders held my legs up in place, one on each shoulder, spread wide open as he penetrated me with one finger at first and then two. Still zero pain. I was letting out some moans and he seemed to know what he was doing. He pressed up with both fingers and gave me a sensation I've never felt before. He explained to me that was my prostrate and it might make me cum again. He kept wiggling his two fingers inside of me, sometimes pulling completely out and pushing back it. I was so proud of cleaning myself out earlier in the day also, as there was no embarrassing moments. With my knees nearly touching my ears, Dan put my soft cock in his mouth again, this time fingering me at the same time. I knew I was close again and found the strength to tell him this time, "I don't want to cum in your mouth again...do you want to fuck me?"

I wish the story would end with him barebacking me but he reached for a condom and I was perfectly fine with it. I took the condom from him and helped him put it on his hard cock. I was already on my back with legs spread so all he had to do was scoot up and press his dick onto my hole. He looked me right in the eyes and told me how perfect I was. I told him how happy I was for him to be my first and to take it slow.

His cock felt nothing like his fingers. For one, it's definitely warmer than fingers. It's also quite larger. While his fingers went in really easily, his cock caused me a little bit of pain but he was very respectful about it. He put it in millimeter by millimeter, always asking if I was ok and kissing me every now and then to let me know that he was enjoying it too. With one final push, he put his entire cock into me and gave me the most passionate French kiss where his tongue filled my mouth so much that I couldn't even moan. He held both of my hands and I whispered to him, "I feel like I waited all my life to have you inside of me"

Tears started running down again but I told Dan it was just because I felt so emotional. He thrusted faster and faster which completely took my breath away. It was an overwhelming sensation, sort of like feeling like having to go to the bathroom, mixed with the intimacy of getting penetrated by a man. I didn't have a means to compare sex styles yet, but Dan loved putting his cock all the way inside and then pulling it out completely and repeating that at a relatively fast pace. For a beginner, it was very intense.