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This is the story of my first gay sexual experience, it's completely factual and happened yesterday. I am 38.
I came out to my wife 2 years ago, a few months after we separated for the last time. She'd called and wanted to talk over coffee, and after I few minutes I could tell that she was trying to convince me to get back together. I knew I had to tell her the real reason I had left. I thought that she'd freak out, call me a faggot, who knew. She took it really well. In fact, I think it answered a lot her questions about our long marriage and since then, we have been great friends ..
We got married young, I was 19, and we were together for 18 years. In all those years, I never once cheated on her. I had thought about it a few times over the years, but I was so buried in the closet that there was no way I could convince myself to, not only cheat on my wife, but actually have sex with a guy. So, instead, I relied on a healthy fantasy life and a LOT of gay porn.
Having come from a fundamental Christian upbringing and being active in that religion up until my wife and I split, it was difficult moving past the 'brainwashing' I had endured for 36 years. I have only publicly been "out" for about 8 months. In that time, I had planned on finding a nice guy, getting into a relationship and having that be the guy that would be my "first" .. As a kid, I had messed around plenty with other boys, but that was limited to fondling, and mutual jack-off sessions. Nothing "really" classified as sex.
During the past 8 months, I have also joined a couple of online groups that were comprised of people like me, that had been in the same religion, were gay and were free from that fundie nightmare. I had even met a few in person, and had become very close friends with them, but of course, given my reservations, I kept landing squarely in the friend zone. One of those friends finally grabbed my shoulders one day, looked me in the eye, and said "Go. Get. Laid! Whore it up a little."
That was hard for me to even consider. I still had a "monogamous" mindset. I finally decided I would start trolling Growlr, Scruff and a couple of the other Bear centric sites. I am large hairy guy, and I love large hairy guys. I was shocked at the reception .. I was constantly getting messages from guys who wanted to "hook-up". Having never done anything, and being a little afraid of some things, I was a little too reserved, and frankly turned off by the "come over and suck my dick" or "I want to fuck you right now" messages. Most of them were from "chasers" too, which I just wasn't into.
Yesterday morning, I was sitting at my desk working, and I got a message. I kind of sighed a little, wondering what excuse I was going to come up with to not meetup with this guy. To my surprise, a delicious looking older bear was messaging me. He profile shot was awesome, and instantly interested me.
We exchanged the typical pleasantries, which was a nice change from the normal hurry up and fuck messages. I specified in my profile that I wanted to massage and maybe do oral. So he asked if I like to meetup and exchange massages, and "loads" .. I noticed he was from a city about 45 minutes away, so I felt comfortable flirting a little, since I didn't think we would meetup.
Turns out he worked in my city, so he was very close. I felt a pit form in my stomach .. What was I gonna do now? I heard the voice of my friend "Go. Get. Laid!" and gave him my address.
It was early in the day, and he was coming by after work, so I had all day to work myself into a frenzy... Was I really going to do this? What if he was weird, or tried to do things I didn't want to do.
Finally, the door bell rang. For a minute I considered pretending I wasn't home, but the excitement and thrill over powered it. I opened the door, and there stood before me a hunk of a bear. Curves in all the right places, and a beautiful goatee.. He came in and we chit chatted over a beer. I didn't really know what to do. I had told him that I had never done anything and this was all very new to me. So thankfully, he took the lead, and came over, stood in front of me, and began rubbing my chest and shoulders. Then he leaned in and kissed me. Our lips locked, and our tongues danced together to music that I thought only I was hearing. I couldn't believe it. I was kissing a guy, and not just kissing him, but making out! I was making out with a gorgeous, delicious stranger of a man that 5 minutes before I had never seen before.
We stood in the kitchen for what seemed like days, exploring each others bodies with our hands while our tongues continued their newly found pleasure. I had a sudden, irresistible urge to take off his clothes! I unbuttoned a couple of the buttons of his shirt, and my hands dove in to rub his chest. He had the most amazing nipples and I couldn't help but play with them. I realized if we stayed there much longer I'd have him naked in my kitchen, which would be awkward if my roommate came home.
We moved into the bedroom, and the whole time walking back to the bedroom I was in utter shock. Was I really going to do this? As soon as the bedroom door closed we locked lips again and I started removing his shirt. Once he was naked from the waist up, I took a moment to admire his amazing chest, with the nipple piercings, and thought .. This gorgeous man is in my bedroom and ready to pleasure me in ways I had never been pleasured.
He slid my t-shirt off, and resumed rubbing my chest and back. Meanwhile I grabbed his belt and unbuttoned his pants. I thought, this is it. Once the pants come off, there is no going back. I dropped them to his feet, and got to my knees to help him get out of them. While I was on my knees, I caught a whiff of him and my erection almost tore my shorts open. I stood back up and he started taking my shorts off. I couldn't believe how sexy it was to be undressing him and having him undress me. We stood for a moment in our underwear, and I was reluctant to take that last step, again, sensing my hesitation, he took the next step and I was naked. I hooked my fingers in the waistband of his underwear and started slowly pulling them down. I was on my knees again, and there right in front of me was this magnificent cock. Inches from my face. I was enthralled. It had been 22 years since I was this close to another cock.
I stood back up again before I completely lost it and we stood naked together and began exploring each others bodies with our hands. I kissed down his neck and check and engulfed his nipple in my mouth, while he moaned loudly. I was new at this, but I could tell that he was definitely going to want me to work those nipples. I slid my hand down his stomach and found what I was searching for. His huge cock dangled, waiting for me to bring it to life. I cupped his balls, and stroked his cock a couple of times and he brought me back up to eye level and led me over to the bed.
My brain froze again, but only for a split second. I was finally getting comfortable. The mix of nervousness, and excitement was melding into an overwhelming anticipation for what was going to happen next.
We lied down on the bed facing each other and began kissing again. Our hands exploring every inch of each other. My hesitation completely gone, and the ecstasy had taken over. I started exploring his body with my kisses, moving slowly down his chest, stopping to work his nipples some more, I could tell by his moaning that he was loving it, but my mouth had other things in mind. I had fantasized about having a cock in my mouth for as long as I could remember, and my moment had come. I slid down and stared at his amazing cock for a split second before I engulfed it in my mouth. My brain, exploded. It was so much more amazing than anything I had ever imagined. The smells, the flavor, the feeling of this man's engorged cock in my mouth was pure ecstasy. I would have been happy to spend the rest of my life sucking, licking and enjoying that cock. My nose buried in his pubes, feeling the head of his cock hitting the back of my throat, and his prince albert piercing knocking against my molars. I pulled my head off sucking as hard as I could while I did.
Having watched a lot of porn, I always saw them bobbing furiously on the cock, so I needed to try that. I started pumping as fast as I could, while my hand roamed up his chest and began violently twisting and pulling at his nipples. His whole body flailing, twitching and squirming while he moaned and moaned. I could tell he was loving it, and knowing that I was causing that level of joy was enthralling! I never thought I would be able to properly suck a man's cock, but as I did it for the first time in 38 years, I felt like I was born to do it.
After a few minutes he grabbed me and pulled me up to him and in a rage a passion we mauled at each other and our tongues intertwined. He flipped me over and ran his hands down my back and I felt his face dive into my ass, and then a feeling that I never thought possible washed over my body. I had no idea what he was doing for a minute, I only knew that I never wanted it to end. His tongue was pushing through my crack and entered my hole. I wanted to squeal with joy .. his tongue shot in and out, in an out, in and out and with each entry I thought I would explode cum all over the bed. His hand slid between my legs and found my cock. He stroked it, and rubbed me all over.
He flipped me back over and dove down on my cock and it disappeared into his mouth .. his tongue worked my shaft and sent shivers up and down my body, I was close. I could feel my cum welling up, but there was no way I was letting this end. I pulled him off me and he came back up to my mouth and we kissed. I could taste my own cock, mixed with the flavor of his in my mouth. The flavors blended together in an orgasmic mixture of experience and naivety.
He laid down on his stomach and I straddled him. I grabbed the massage oil from the night stand and began massaging his back and shoulders. My erect cock was resting in the crack of his ass, and with each stroke of the massage my cock would slide deeper while I fucked his crack. I dripped some of the oil onto my cock so it would slide easier. I could tell he wanted me to fuck him, but I just wasn't ready for that, but I pushed hard against his hole, and I wanted to go all the way, but just could bring myself to do it.
When I finished massaging him we kissed some more, I needed a moment to clear my head and let the waves of pleasure subside a bit. We explored each others bodies again and I needed to have his cock in my mouth again. So I dove down for seconds and worked his cock like there was nothing else in the world that mattered. My hand slid between his legs and I rubbed his taint while working working my way to his ass. My finger felt his hole and without even thinking I shoved it all the way in. Meanwhile my other hand worked it's way up to his nipples and, by now, I had figured out that he liked it rough. I tugged and twisted at his nipples and finger fucked his ass, while my mouth and tongue explored every inch of his delicious cock.
He writhed in pleasure. I thought he'd buck me right off the bed. I could tell he was close, but I wasn't stopping until he made me. He grabbed me with both hands and pulled me up to him. His passion overtaking him, he kissed me roughly. I loved the feel of his beard as he pawed and kissed me all over. He worked his way down to my cock and took it all in and began pumping furiously. I was on the edge, and couldn't hold it anymore. I warned him that I was going to cum. I held it as long as I could, and screamed "I am going to cum!" and it just made him go harder. He wanted all I could offer him. I blew my load all over the back of his throat and I could feel him swallowing. I thought he would swallow my entire cock. I screamed in pleasure as load after load exploded from my cock.
When he finally pulled off, my cock was so sensitive I didn't think I could stand anymore. I fell into an orgasmic stupor as he cuddled up to me and lied on his back. I took both my hands and worked his nipples while he furiously jacked his cock. The harder I pulled and twisted the more he moaned and his body started convulsing as he blew his load. He moaned and squirmed and twitched for over a minute as he came.
This man, my first, so amazing, so patient. I felt as though I had known him my whole life, and in that moment all that I had wanted in my life, all that I had denied myself because of shame and religious guilt washed away and was replaced with the most content and satisfied feeling I ever experienced.
I had only known him for a little more then an hour, but I will never forget him, or that first time.
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