8 comments/ 77023 views/ 26 favorites First Gay Experience By: Friske_one1 Me and a buddy decided to go see a rock concert at the Great Western Forum (that's what the Staples Center was called back then). I was 21 at the time, horny all the time and could never get enough pussy. So we go to the concert in our own cars since his brother lived nearby and he was going there afterward to hang-out for the weekend... no problem. So, after the show I decide to hit some bars in the Hollywood area instead of driving home. I walk into this one place and while leaning against the bar I feel a tap on my left arm... it was a barely passable but none the less hot older light-skinned black tranny. I was a bit taken back by the situation but it didn't seem weird at all to me considering the area I was in. We talked a pretty good while and she was actually pretty interesting... her feminine style and being older kind of turned me on. I was thinking maybe she could blow me later if I played it right. She said she lived within walking distance, so things were looking good. We had a couple cocktails and eventually I suggested we go to her apt... I was surprised when she said "Ok hon." We walk over and settled in with a wine and the radio going... I was tripping by now, this was really freaky hangin with a black tranny... but hey, she was fun and nobody knows me around there so I didn't care. She eventually sits next to me so I knew it was on... she touched my thigh playfully as we talked... noticed I was getting aroused and put her warm hand on my dick and squeezed. I felt waves of heat going through me and suggest we go into the bedroom... I was really hoping to draw the line at just a blow job. We go in there and in her best woman voice she suddenly tells me to take off my pants... so I pull them down and she says "No, take them off." I got this very hot tug inside that I was crossing the line and it really turned me on. She then pulled the bed covers down... she was grabbing a beach towel as I pulled off my shirt and was completely naked... she laid the towel on the sheets... my dick was half hard as I slid over on the bed... she positioned herself between my legs and began massaging my balls... then she put her finger in her mouth and got it wet, I was surprised when she rubbed a little then slid it into my asshole. I had done a lot of playing when I masturbated, sliding things up there, gradually bigger things... so my hole wasn't virgin, her finger went right in. She was holding my now rock-hard cock and began licking it, it was amazing watching her do it as I really hadn't had anyone yet who was good at sucking cock. I have an honest 7" and it is a great looking cock. She slowly started working her big soft lips over the head, slobbering on it and circling her tongue until it was sloppy-wet... she worked her way down to the base, it was amazing to watch. She seemed to really be savoring the moment... I had forgotten that her finger was in my ass until she pulled it out, it hurt a bit since it was dry by now. She apologized and wetted her finger again, this time the slobber was all over and running down between my cheeks. She kind of rubbed my hole a little and shoved her finger back in... kind of slid it in and out slowly as she sucked up and down on my cock. Felt good as I squeezed my hole while she did it. I got pretty caught up in the moment and reached down to feel her muscular leg, definitely man legs... was very strange. She was wearing this short skirt so I felt her inner thigh and slid my hand up a little to the edge of her panties... she said "You ever been fucked?" I replied no, I didn't quite know what to do at that moment so I just hesitated, not knowing whether to slide my fingers under the panties. She pushed her finger hard into my asshole and moved it around, then grabbed my hand and placed it on her cock and balls... I could feel the size and warmth of her half hard cock. I got an immediate jolt and felt my heart jump... fuck man, it was hot! I pulled her panties aside and felt her cock jump out... by now she had taken her finger out and moved up and over me with her legs spread so I could have access. I held and began massaging her cock until it was hard, it was big and real thick... I could see it in the dim light, kind of fat, tapering down at the base. She said "Hold on a minute hon" and got up... she took off her skirt and slid her panties off. I had full view of her big magnificent black cock. I knew right then that we were going to do some seriously nasty things. She then took all her clothes off as well. I looked at her and realized there was no more woman fantasizing, we were both totally naked and I wanted that fat cock in my mouth, secretly hoping she would coax me into it. She climbed onto the bed and kind of laid on me... I gently held her warm cock against mine and cupped her balls. She got up and straddled me as I massaged our cocks... then she moved up to my face and softly touched her cock head onto my lips... I parted my lips and licked the underside of it gently... the wetter it got the more I had in my mouth, I tasted the salty juice and felt the ridge with my tongue as the head slid in my mouth... pretty quickly I had as much cock in my mouth as I could... it was so warm and soft, I savored the experience and she was so gentle. It became insatiable as she stroked in and out while I sucked on her... I licked and worked the whole thing down to her balls until it was slobbery... stroked it while it was in my mouth. I felt her muscular ass cheeks as I sucked... slid my fingers along her crack, touching her asshole. I felt her cock pulsate in my mouth when I did it. It was scary that I loved sucking cock so much, but there was something really exotic about it with her. She said "Let me kiss that ass hon," as she laid back... I flipped around and got in a 69... went down on her hard cock again... she spread my cheeks and started licking my asshole, I felt her tongue go inside... I laid my head on her leg while she licked me and stroked her cock. She says "Hold on" and gets up again... she comes back with a small bottle of mineral oil from the bathroom, she says to lay back and put my feet on her shoulders. She squirted the oil onto my asshole and massaged it on my ass cheeks... then she slid her finger back in my hole. I pulled my cheeks apart to take what she was giving... she then moved closer and rubbed her warm cockhead on it, kind of working it in... I was fucking hot for it by now. I squirted some oil on my cock and balls and began massaging and stroking, then I squirted some on her cock. Pretty soon we were both pretty oily and rubbing our cocks together. I loved the way it felt with her cock between my cheeks. She told me to turn over on all fours, it was hot to feel the slippery oil between my cheeks... I stuck my ass up and arched my back... she spread me and squirted more oil in my asshole, working her fingers inside me, I could feel the cool air on my hole when she pulled them out. She pushed her fingers all the way in me and worked my hole... her fingers felt very big but I was so oily it didn't hurt at all. By now I was moaning like crazy and begging her to fuck me. Her woman voice and sassy black attitude were really turning me on, she was asking how I like it and do I "want her cock inside me"... YES, YES!... she reached around and squeezed my oily cock and stroked it for a minute, then I felt what I thought were her fingers again in my asshole, I suddenly realized that it was her COCK as I felt my hole stretch... she slowly worked it in as I pulled my ass cheeks apart and groaned. It felt huge but it wasn't uncomfortable, the pain of it felt so good I wanted more if it... I could feel the fat part of her cock slowly go inside, I could feel it pulse as she flexed it. Then it kind of slid the rest of the way in pretty easy. I felt the warm thickness of her cock slide deep inside me... felt her black scratchy hair rubbing against my ass and became breathless knowing the whole thing was inside me... it was fucking incredible. I was groaning loudly and begging for it... she pulled back and shoved it back in, grinding on me... it felt like her cock was in my stomach... pulled it back, almost out and all the way in... I thought I'd explode, the burn was insane. She fucked me steady as I submitted to her completely... she squeezed my cheeks and ran her hands all over me... long strokes for what seemed like 30 minutes, she only stopped to squirt more oil on her cock. I cupped and squeezed my ass cheeks around my hole, holding her oily cock as it went in and out... I arched harder and spread my cheeks for her as far as I could, occasionally holding her balls while she flexed inside me. She forced me down onto my stomach and laid on me, the domination was a real turn-on... I put my legs together and clenched my cheeks while she ground her cock in my ass. My hard dick wanted to be free so I stopped her, she got off and laid back... I sat on her cock slowly facing her until it was all the way in... I clamped down on it while I stroked my dick until I was on the edge. It felt magnificent rocking on her fat cock and milking it with my asshole. The look on her face was amazing, she was really enjoying what I was doing to her. Without pulling her cock out I laid on my back as she followed... spreading my legs and put my feet on her shoulders, she hesitated a second, seemed to enjoy watching me stroking my own cock.... grabbed my upper legs and pushed them back, spreading my ass as far as it would go... I held her balls as she buried her cock in me. She was fucking hot and groaning as she worked me, grinding hard with my legs back almost over my head... I begged some more while she fucked me... that scratchy hair felt awesome against my hole. I could tell she was gonna cum and I was so overcome I grabbed her head and pulled it down to my mouth... we kissed and sucked each other's tongues, she began making short moaning noises as she wrapped her arms around me squeezing, I wrapped my legs around her... then felt her cock flex hard inside me with an upward push... I felt it pulsate and shoot inside me as she groaned loudly. She ground against me and twitched and moaned, her cock still pulsing... then relaxed slowly... started kissing me softly, we licked tongues and kissed for a while as she stroked in and out a few times. She told me I was one of the hottest ever and it excited her that she could show me about fucking. She slid her cock out and milked it, cum dripped onto the underside of my still hard cock and balls. I reached down and slid a couple fingers in my slippery hole, it felt soft and slippery like a pussy, the cum was running out. She got up and brought a warm wet towel and began wiping the oil off my cock... said "You're gonna get the best blow job you've ever had now hon." She began softly licking my cock again until it was rock hard and slid her fingers in my asshole. I clenched my cheeks against her hand as she pushed... I wanted her whole hand up my ass. She sensed I kept wanting to kiss her so she came up and put her tongue in my mouth. I wrapped my legs around her and said I wanted to fuck her, she didn't answer, only saying I could play a bit...she climbed up and turned around with her beautiful big ass over me, I spread her cheeks and softly massaged her still oily hole... slid a finger in as I held her soft cock and balls... she seemed to enjoy it and let me have my way. I pulled her down and licked her hole, mashing my face in her crack. She began stroking and sucking me again with fingers in my ass... I came pretty fast, she went all the way down and stayed until I stopped pulsing... she didn't spit so evidently she swallowed it all. So, we both shower and say good bye with some soft kisses... she was standing naked before me at the door, so I get on my knees and start licking and squeezing her beautiful cock until it was half-hard... I said I'd come back and look for her again... she just said "Maybe I'll see you hon"... I stood-up and I left her apt. I fantasized about that experience for a long, long time. Since then I've enjoyed cock but nothing will ever come close to that black tranny I met that night... the hottest experience of my life. First Gay Experience Hi guys, this is a short story about my first gay experience, I was 18 when this happened, I'm now 20, he was 40ish. As a sexually frustrated teenager I was desperate for some action, at this point in time I was a virgin, so hadn't quite explored my sexuality. I was on various swingers sites to try my luck, but couldn't arrange a meeting with anyone, I think most of them thought I was a little too young. Anyway my mind started to wonder, maybe having sex with a guy wouldn't be too bad? I found myself looking at pictures of guys, reading various things about gay sex. I looked around for a few ways I could meet other guys for sex, I came across a few websites and signed up. When I signed up I had a look around at the guys in my area, but didn't really know how it all worked. After a few hours of being signed up I checked my messages and I had a few messages from a few different guys, I was very nervous about this incase people found out. When I was going through my messages I came across a guy who caught my eye, he seemed like he was genuine, older (which I was looking for) and he could accommodate. He had already sent me a message, we exchanged a few messages and swapped emails. I questioned my intentions, and questioned if I wanted to actually go through with this. A few days on I received an email from him, asking me if I was ready, I bit the bullet and told him I was, he told me his address and that was that. I showered myself and made sure I was clean and walked towards his address, I still didn't know what to expect, I hadn't seen any pictures of this guy and had no idea who he was, as I walked to his door I got really nervous and walked away, I sent him an email asking him if he could open the gate so I could let myself in the back (I didn't want to be seen). I went down the alley as went to his gate, then sent him another email telling him I was out back, he popped his head out of the gate and asked me to come inside. I walked inside his house, still extremely nervous, and sat down on the couch. After a few mins chatting I let him know I was nervous and still didn't know if I was going through with it. From nowhere came a little excitement on my part and I asked him if he wanted to go upstairs, he agreed and led me to his room. As I got into his room I was still a little nervous but excited at the same time, he stripped down as I stood there, and lay on the bed. He could see I was nervous and asked if I wanted him to blindfold himself, I agreed. He lay there with a blindfold him butt naked, I knew i had to take this chance to try something new. I stripped down, and he said do whatever I like and then he asked me to put my cock in his mouth, at this point my cock wasn't hard in the slightest, but I was excited as I'd never had a blowjob before. He started sucking my cock but it didn't seem to do a whole lot but none the less I still reached for his cock, he was a lot bigger than I was, he was about 7.5' and he was rock hard. I grabbed his shaft and it felt quite weird, like something I'd never felt before. Before I knew it we were in a 69 position and he was taking my cock in his mouth, I knew I had been waiting for a long time to taste cock and this was it. I leant down after stroking his shaft for a while, I wrapped my lips around it and it was a strange sensation it felt right though. I tried to take as much of it in my mouth as I could but could only get halfway down, it was pretty wide. After sucking his cock for a few seconds he started to pre cum, I was never a fan of cum as I've tasted me own a few times, so I asked him if I could put a condom on his cock before I continued sucking, he agreed and I got back to it. We continued as we were for a few more mins, then I got the urge to want to stick my cock in him, I asked if he was ok with that and he moved to the end of the bed. This was all completely new to me because I was a virgin and never fucked anything, at this point I had maybe a semi at best, certainly wasn't fully hard. I put on the condom and lubed myself up and pressed my cock against his hole, to my surprise it went in pretty easily. I started to pump my cock in and out, but I was very very disappointed, it didn't really even feel good at all, there wasn't much of a feeling if I'm honest. I continued to fuck him for a few more mins but I was extremely bored and it wasn't doing much for me at all. I asked him if he was ready to switch, he agreed. I thought it would be a great idea for him to be lay down on the bed as this would give me full control over how deep he was. I lubed him up and went down and pressed his cock up against my arse, it just didn't want to go in. He stepped in and said it would be a better idea if I lay down on my back with him on top, I agreed. I lay back on the bed and he took off his blindfold, i looked at his cock and realised that this could hurt a little, it was rock hard. I just lay back and let him do the work. Before this I had only used my mums dildo on my arse a couple of times, so I was pretty tight. He positioned his cock over my hole and pressed his head against it, it wouldn't go in straight away, he pressed against it and the head went in. It was a little painful when it went in but the guy knew what he was doing, he took it slow. He left his head inside a little and just left it there, he waited a few seconds and started to push in a little more. The more he went in it hurt more, I looked up and I could see he was really enjoying my tight arse. The more he pumped the better it felt, after a minute or so I was in complete ecstasy it felt absolutely amazing, every little move he made it gave me a little more pleasure. As he was fucking my I came all over myself, I had never came this much, my cock was pumping and i didn't even touch it. Seconds later he pulled out and pulled off the condom and came all over my cock and balls, His warm cum mixed in with my cum, it was amazing! After this we got up, I showered and left. This is a true story and the first one I've written, hope you guys like it and I plan on writing some fantasy stories. To any guy that's considering trying gay sex, do it! Just make sure the guy knows what they're doing and you'll be ok. And I do hope to meet him again! Thanks.