So back when I was an early teen, my cousin Randy introduced me to masturbation. Actually he introduced me, my brother and a few of his friends to masturbation. It started out after a family get together, having dinner at my aunt and uncles house. Us kids would go upstairs and of course, my sisters would hang out with my cousin Susan and we'd end up in my cousin Randy's room.
On this occasion, my cousin closed the door and produced a couple of Playboy magazines. Having never seen a naked woman before, this certainly sparked our interest. Once our interest were sparked, so did our cocks and so did this thing called masturbation. It was really innocent and involved pictures of naked women, unscented oil and some hand towels.
Eventually it turned into jerking off with his friends and me wearing his sister's panties. My brother and I learned the art of stroking our cocks until we shot loads of our cum. Sometimes we'd do this with some of his friends and because I had been crossdressing since I was in grade school, I started wearing panties to these jerk off sessions.
It was kind of weird because none of my cousins friends were freaked out by me wearing panties and neither was my brother. He had caught me many years earlier wearing a pair of my sister's panties and, I guess, was like whatever.
My cousin's friends were like, so long as we are stroking our cocks and cumming, we could care less. It was at one of these jerk off sessions that my cousin dared me to give him a blow job. I think about it now and realize how crazy that had to be. Here's me wearing a tan pair of nylon panties with my cock rock hard, with a pre cum wet spot in them and my cousin is daring me to give him a blow job.
His buddies were like whatever, they were stroking their cocks over pictures of naked women and wanted to see what a blow job looked like so it was me, the kid wearing the panties, who would take one for the team.
I remember this like it was yesterday, me wearing the panties, crawling across his bed on all fours, reaching up and taking his cock in my hand, not knowing what to do with it but getting instructions from my cousin. "That's it, now slowly kiss it," he said. "That's it, now slowly lick it. Now put your lips around the top of it." Again, I had no idea what I was doing but for some weird reason, I was getting really turned on by this.
That and his precum tasted SO good. As I slowly put his rock hard head in my mouth, there was a commotion in the hallway outside of my cousins room. That was our sign to stash the Playboy magazines, the towels, the oil and put our clothes on. Once the door opened, we were just looking at Mad magazines and nothing more. That was the closest that I had come to giving my first blow job.
A few years later and my brother has a stash of his own Penthouse and Playboy magazines. Since we both shared the same bedroom, I knew where these were and jerked myself off to them on several occasions. One night, I came home and caught him stroking his dick to these magazines.
We are both in high school at this point and I am still wearing women's panties whenever I can. I gaze at his hard cock and, for some reason, I start to get hard myself. I certainly wasn't GAY because that's not even a thing where we grew up. He quickly pulled his sweat pants up and we kind of pretended that we hadn't seen this.
That night, I really started thinking about his cock and it got me hard, really hard. For some reason, I really had to see it again and suck it. Again, I had no reason why I had to do this but it was driving me wild. I knew he was awake so I asked him if I could suck his cock - just out of the freaking blue, that came out of my mouth!!
He was like, "No fucking way! Are you a fag or something!" I told him that I wasn't but I really, REALLY, needed to suck his cock! In hushed whispers, I pleaded, I begged that I needed to suck his cock.
Again, I had no reason why but I needed his cock in my mouth! FINALLY he agrees to just a blow job, nothing more. I slid off my bed, got on to my knees and crawled over to his bed. He sat up, threw his legs over the side of the bed and was like, "This is SO fucking weird! I can't believe I'm doing this!"
I put my hands on his thighs and start rubbing them up to his underwear. I slowly pull down his tighty whities and out pops his soft cock. He leans back as I slowly start to lick his cock. I reach in and start to play with his balls, his cock slowly starting to get harder. With one hand still on his thigh, I use the other to grab his semi erect cock, kissing and licking it like it was a popsicle.
By this time, my own cock is hard and as I put his cock in my mouth, I slowly reach down and start stroking my cock. My precum is starting to flow so I wipe some of that up with my fingers and put it in my mouth. Again, I have no idea why I want to suck his cock and no idea how to suck cock!!
By now, he is fully rock hard and I am sucking his cock like my life depends on it. He gave me one piece of advice that I remember to this day, "Watch the teeth!" I am bouncing up and down on his cock with my mouth, my spit is drooling all over it!! I pop it out of my mouth every now and then, licking it like it's hard candy!
Eventually he puts his hand on the back of my head, forcing my mouth deeper on to his rock hard cock. I began to feel his thighs tighten up, his stomach starts to twitch and this blow job only starts to turn into a cum swallow.
He grabs a hand full of my hair, forcing me even further down on his cock and I feel him explode in my mouth. I had no clue that this "blow job" was going to come to this point but again, I wanted this just as much as I wanted to suck his cock.
I feel his load hit the back of my throat and I pull my mouth off of his cock. Instead, I open my mouth and let him shot his load into my eagerly awaiting mouth. I feel him bucking, his cock spasming, his salty and sweet tasting cum filling my mouth, loving the taste of another guys cum. As he slowly starts to go soft,
I keep on sucking, trying to get every last drop of cum in my mouth! He is twitching, moaning and trying desperately to get my face off of his cock. He grabs my face and says,"This is it!! This will NEVER happen again! Never!!" I looked up at him with my cum drenched lips and said, "I understand."
He pulled up his underwear and rolled over back into his bed. I got up and hopped back into my bed, still with a raging hard on. I pulled my covers up and slid my bikini briefs - once in high school, I never wore anything other than guys bikini underwear or panties - down until they caught around my balls.
I was still savoring the load of cum in my mouth as I started jerking my own cock. Pretty soon, I was feeling the muscles in my stomach and thighs start to tense, and twitch and my toes start to point. I pulled the covers down, cupped my hand and shot my hot load into my cupped hand. Again, for some reason, I lifted my hand and drizzled my cum into my mouth, licking every last drop of it off!
The next day, my brother and I got up, had breakfast and walked to school... never speaking about what had happened the previous night ever again. To be sure, we had our fair share of girlfriends in high school and after that but he was straight as an arrow sexually. Me, on the other hand, who knew!
That and he never got bent about me wearing women's panties. On two different occasions, he walked in on me getting dressed and saw me wearing panties. The first time, I was in my late teens and was wearing nothing but a pair of pink lacy nylon panties and grabbing a shirt. Part of me wanted to cover up the fact that I was wearing these but I was like whatever.
He looked at me, looked at my panties and said, "Hey, get dressed or we are going to be late!" Didn't even phase him. The second time, I was in the living room when he walked in and I wearing a blue nylon string bikini, grabbing my freshly washed clothes from the couch.
Again, I didn't cover up and had a conversation with him about family plans for the weekend. He just understood that that was who I was. Though he never caught me wearing thigh highs and a garter belt or pantyhose but hey, I couldn't give away all of my secrets!
