TRUE FIRST TIME TALES
Elijah's TaleRated: X ages 17
I can't remember my first time, but I do remember my first time with a friend.
I grew up being babysat by my uncle. He was my mom's youngest brother, about ten years older than me. I can't remember the first time with him. I had to be less than seven, because we moved from an apartment to a house when I was seven, and it was already going on, though it was still kind of new. So maybe it started when I was about six. He would have been about fifteen or so, I guess. It's kind of embarrassing to say, but I really liked it. I mean, it felt great. And, yes, I was sucking him off, too. I don't remember him ever not having pubes or not cumming. I knew it was really naughty, and we'd get into huge trouble if anyone found out.
We did it whenever he babysat me, which was almost every weekend. My folks went out for dinner or to play cards with friends, or whatever. They'd be gone a couple hours or more, and we'd spend most of it on my bed doing it.
When I was about twelve, and he was like twenty-one or so, I didn't need a babysitter anymore. So I'd ride my bike to his house, telling my folks I was staying at a friend's house overnight, but I'd be at my uncle's place instead. I really liked sex with him. He never fucked me in the butt. He did play with my prostate with a finger or two, but he had a huge dick and it would probably have split my hole wide open. He had someone else he did that with. I met him, and saw him at my uncle's place quite a few times, but we didn't tell him we were doing it too. It was our secret.
By the time I was finally shooting semen of my own at thirteen, my uncle had taught me a lot of things. He showed me how it was way better when you took your time - the longer you did it for before you came, the better it was when you came. He taught me about abstinence for a day or two, or even more, to build up a big wad. There were weeks I didn't cum all week, so that when I did it with my uncle I'd fucking lose my ever-loving mind when he finally let me cum after edging me a few times. He taught me about getting really close, then going really slow, and making my body work to cum, making the explosion even more powerful when it happened. He taught me how to play with my prostate and how to play with his. He taught me how to suck a cock like a hundred-dollar whore - changing it up, changing speed, changing style, using hands too, playing with nuts, prostate play, stopping and starting, using your tongue everywhere, all those good things. And he'd told me a lot about girls, too. He showed me magazines and told me about how they worked, and what they were like. I probably knew more about girls and their parts than some married men. He didn't know I was gay then. I didn't either. I didn't know until later.
When I was fourteen, we moved again. This time it was to another state. Man, I hated that. I cried alone in my room. My uncle tried to make me feel better about it, and told me to find a guy my age to do it with. I liked guys, and figured I was gay, but I was really shy and I knew I wasn't going to find some other gay guy. Not easily, anyway. This was the late seventies, and being gay was something you hid. Yeah, I knew I was gay by then.
So there I was, 1978, fourteen, starting high school, living in a new state, going to a new school, shy, introverted, gay, and alone. Hours and hours away from my uncle and any hope of sex.
Well, it was hard. I made a few friends, eventually. By the time I was seventeen, and in eleventh grade, I had a couple good friends. We talked about girls and sex and pulling our puds, like I guess most guys did. I saw naked guys in the showers in school every day. I fantasized about them every night when I jacked off. I even had a major crush on a couple guys. I really liked the athletic blond guys - tanned and muscular and studly. I was a small guy, short and skinny.
I missed being sucked off something fierce. Jerking off was okay, but nothing like having an experienced older guy sucking you off with a finger up your ass massaging your prostate. I got good at doing it myself, though. I could go for over an hour, slowly stroking and massaging my inside nut, stopping before I came a couple or more times, and eventually blowing a nice, huge wad. I loved laying on my back, my butt and legs on the edge of the bed, so I could cum into my mouth. Usually thinking about my uncle or one of the hot guys at school or one of the guys I saw naked in the gym showers.
I had just turned seventeen. I had an old car, like most of my friends. I was small and timid, so I wasn't athletic or on any sports teams. I wasn't really smart, so I wasn't on any academic teams or anything. I wasn't doing anything other than going to school and working part-time at a fast food restaurant.
My friends would ask me things about sex with girls. Because of all my experience with my uncle, I knew more about sex than my friends did, so I got a reputation as a real sex encyclopedia. Of course I'd lied and said I'd had a girlfriend where I lived before, and that was how I knew so much. So I had a reputation and was asked a lot of questions. I liked it. I loved talking sex stuff with my friends. I would imagine them hard in their pants as I regaled them with tales of sex with my girlfriend - how I'd do it for a long time, stop and rest a bit, and go again, before I'd cum. How I'd make her squeal and squirm and almost beg me to finish her off, and drive her crazy. How she couldn't get enough of my dick. How she could suck me for over an hour before I'd cum so much she couldn't swallow it all.
Well, one of my friends was over one Friday. My folks had made friends too, and were out playing cards for a couple hours. Evan and I were playing Atari, and having a pretty good time. Talk turned to girls, of course. So I talked the talk, to cover for the fact that I'd rather suck a cock than suck a tit.
Evan said something about how he wished he could shoot a big load, like the guys we'd all seen in the few porno magazines we'd sometimes seen when a friend or another got one from somewhere. I mean, those mags usually made it look like the guy had blown a pint of jizz, you know? So I told him that it was probably just airbrushing to make it look like they came that much. He said he figured that too, but still, he didn't shoot very much when he got off. I asked how much he squirted. He said he barely squirted more than a few drops, and he didn't even squirt. He said when he came, it sort of just dribbled out a couple drops, that he never squirted.
All the lessons my uncle had taught me were at my disposal, so I asked him how many times he jerked off in a day. He said three or four times a day. I was like, well, there's your problem. I told him he had to let his balls build up a supply of jizz. I told him cumming that many times every day left his balls pretty empty. I asked him if he came the most when he jerked off the first time every day. Of course he did. So I told him to not jerk off for a day. He laughed and said he couldn't go a day without jerking it off. So, I said he should stay the night, and not jerk it off, and stay around all day tomorrow, and not be alone, so he couldn't jerk it off. Then tomorrow night, stay over again, and not jerk it off again. And then on Sunday, he should stick around all day and not be alone, and not have a chance to jerk it off, until he got home that night. I told him if he did, he'd have a huge wad and it would feel better than ever.
Well, I talked him into it. Or trying to, anyway. So we avoided sex talk the rest of the evening. My parents were cool with him staying over, so he did. Being gay, and wanting to anyway, I told him to sleep in my bed with me, so he couldn't sneak a quick, quiet jerk-off. He agreed with a little convincing. When we crawled into my bed, he kept his pants on, and I convinced him to let me lay up against him so he couldn't sneak his hands into his pants during the night. So we laid facing each other, talking, until we fell asleep.
He got up in the middle of the night, and I wouldn't let him go to the bathroom alone. I went with him, telling him I wasn't going to let him jerk one off. So I got to see the tip of his dick. Nice! It was nice and plump and had a nice shape. And, yes, it was hard. He even admitted he would have jerked it off if I hadn't woken up and went in there with him.
When we got back into my bed, I had him face the other way, and I put my arm over his hip and my hand into the pocket of his jeans. He was like, "Ummm, I really won't do it. You don't have to do that." I told him I was going to make sure and kept my hand where it was. I could feel the heat in his pocket. Damn was my dick hard! I laid there and thought about how to keep him from jerking off until he left Sunday night. And how good an orgasm I was going to have after he left Sunday night. Two days dry, being hard so often from having my hand in his pocket tonight and probably tomorrow night, and seeing his dick every time he went to the bathroom, and all that. Oh, it was going to be a big one!
So, next morning, we go to the john together. We were both hard, and we laughed about it. I was just daring enough, and horny enough, that I pulled my entire dick out so he could see it. Totally boned up, too. He kind of laughed and did the same. He had a nice one! At least six inches, probably closer to seven. Nice big head, curved edges, the shaft curved up and to his right a lot. The hole in the end was a big, wide, open slit. I could even see the red color inside there. Man, I could have jerked one off right there in front of him! I so badly wanted to drop to my knees and suck that thing off while he groaned and moaned and begged me to stop. But my folks were home and up, I was sure, so I just pissed along with him and talked about anything normal and usual.
We played video games and messed around with stuff all day. We stayed away from sex talk or anything that might remind him he hadn't jerked off for probably the longest time since he'd first done it. We had lunch, we drove to the arcade, we stopped at Burger King, went to the mall, met up with some friends, just had a pretty normal day.
During the day, I got this awesome idea. I mean, it was a whopper! I wondered if I could pull it off. Literally. So I planned and plotted all day long, almost. I really thought that maybe I could talk him into it.
That night, he wanted to go home and get some clean clothes. Alone. Hah! As if! I knew he'd whack one out the instant he got home, so I went with him. He got clean clothes, and was going to take a shower. I talked him out of it. I told him I knew he'd beat off in the shower. He really wanted a shower, though. He didn't have a shower in his room, so I wasn't going to be in there with him at his house. So I talked him into showering at my place in my room.
Back at my house, I got clean clothes, and we showered together. He didn't want to, not at first, but I told him he'd showered with guys at school for three years. So had I. And if he wanted to see if he could cum normally instead of only dribbling, he couldn't jerk it off until tomorrow night. He finally agreed to take a quick shower together.
Oh man! Evan had a nice body! Trim and lean, and slightly taller than me, which was no big deal because I was on the short side of average. Nice big dick, nice big balls, a nice patch of pubes, a hint of a coming treasure trail between his navel and his pubes, just a hint of hairs between his big brown nipples.
We both had major boners. We hadn't cum for over twenty-four hours now, so no big deal. But even if I'd cum ten times in the last hour I'd have had a major boner right then, showering with Evan alone in my bathroom. His body, all wet, shiny, that erection and those nice hanging balls, and nice, round, firm, smooth ass... oh man!
So got dried off, got dressed, and hung around in my room playing video games. When he had to use the john, I went with him.
When we went to bed, we rolled onto our sides, and I put my hand into his pocket again. I could have blown off a wad just laying there like that!
I worked on my plan. I figured out what he'd say, or what he'd argue, and I did my best to come up with plausible answers and reasons. I fell asleep thinking about my plan, a major boner in my pants.
The next day we hung out at the usual places and met up with the usual guys, and had a pretty good time. We went back to my place, and got a massive surprise! My folks said they wanted to get dinner at a restaurant they liked, then go play bingo! They rarely played bingo, but were going to today. And after going to dinner first. They would leave at five and not be home until almost ten. They gave me ten bucks to order a pizza delivered. Hell yeah!
Not long after they left, we ordered the pizza. After we'd devoured it, Evan said he should get home soon. I told him he just wanted to get home so he could jerk off. He laughed and said, "Yeah, so?" So I told him I had an idea. I told him my idea. He thought I was insane. Or kidding.
"I'm telling you, man, if you want to see if you can squirt off instead of just dribble, then this is how," I said, giving him my best stare-down expression. "Every time she gave me a hand-job, it was way better than anytime I jerked myself off. It's just way better when someone else does it. You don't know what their hand is going to do before it does it, so it's a surprise, so it feels WAY better."
"But it's so gay, dude."
"Gay is not liking girls. This is just a hand-job between friends. It's not gay."
It took some talking, but he finally agreed to let me jerk him off, doing it slow and using some stuff my 'girlfriend' had shown me. I promised it would be so good he'd lose his fucking mind. I told him that if he didn't squirt if he let me show him what my 'girlfriend' did, then he had something wrong with him.
He made me promise to not tell anyone. I made him promise that too. Like one of us would ever tell anyone back then. I mean, in 1978 if you told someone you'd jacked off a guy, you'd be ruined.
So he asked how we got started. I told him to lay on my bed and just let me do everything. As he laid down, I told him I'd be right back. I went to the kitchen. Mom had this stuff called "Pepper-Oil" that she used to cook some desert stuff with, like cookies and such. Basically, it was cooking oil with a little peppermint oil added to it. It was really slippery and tasted better than just cooking oil. I liked using some of it sometimes for lube when I jerked off. Using it, I could still lick my hand clean of my jizz and it wouldn't taste bad at all. Plain cooking oil gave a nasty flavor, but this stuff added a bit of peppermint flavor instead. Plus it had a slight warming/burning sensation to it, too, which felt really great on my dick. I came back with it. He asked what it was and what I was going to do with it. I told him. I also said, "Plus this way I won't get your jizz on my skin, just on this oil, so it won't be so weird."
I sat on the edge of my bed at his hips, and put the bottle of oil on the table by my bed. I asked him if he was ready. He was sort of smiling, but he looked really nervous, too. Scared, too. He nodded once. I will always remember that one, firm nod. It was like he was agreeing to being beaten up or something. So serious and scared.
"Okay. Remember, I'm going to make it last a long time. I'm going to rub you all over, sort of like foreplay, to build up to things. Okay?"
He nodded once again.
I lifted his shirt and pulled it off over his head. I got the bottle of oil and poured out just a bit into the palm of my left hand, and the rubbed both hands together a bit, and then started rubbing his chest. Oh, man! My dick was so hard it almost hurt! I had to wiggle my ass on the bed a bit to make it less painful. I rubbed his chest with the oil, paying a lot of attention to his nipples. I told him how a guy's nipples can be as sensitive as a girl's. He said it felt kind of good. I rubbed them between my fingers and thumbs. He snickered and grinned. "Feels nice, huh?" I asked. He nodded again.
I loved rubbing his chest and sides. I mean, his smooth body felt so good. And it felt good to make him feel good, too.
After a few minutes, I reached down and unfastened his jeans. I could see he had a major boner going! Cool! I pulled his jeans down, and off his legs, and put them on the floor. Man, his dick was pushing up a big tent, and he even had a little wet spot! Excellent! I knew that meant he was turned on, so I felt more relaxed and at ease as I began rubbing his thighs with my oil-slick hands. He actually sighed a little. Cool! I watched his dick bounce in his tighty-whities every few seconds. And I saw that wet spot grow a little bigger every few minutes as I rubbed his body from shoulders to thighs, all around his briefs, but never touching him there.
"Feeling turned on?" I asked, almost shaking with nervousness.
"Oh yeah, dude!" he laughed.
Man, he was really cute all embarrassed and turned on!
"Can I take your underwear off now?" I asked.
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If privacy is a concern, pick up a pre-paid card at WalMart, a grocery or convenience store. Many come already loaded with various amounts from 5 to 100 bucks. Some don't and you just take the card to the cashier or service desk and load cash on it. You can use the pre-paid gift-card style card once then throw it away. Or you can get a reloadable and use it just like a credit/debit card online or in person and then reload it. Reloading it with cash continues the anonymity.
You can use either a debit or pre-paid card at (Shopify) who also accept PayPal, GooglePay and ShopPay as well as regular credit cards.
Be sure to register your pre-paid card online with your private email your significant-other/wife/family etc. don't know about so that purchase receipts and reports do not go to an email they know of. Unless you want paper receipts and statements sent to your home, be sure when you activate it online at the provider's site that you request no paper bills or statements. Most gift-card style pre-paid cards won't ask for or send anything to your address anyway as you're just going to throw them away after spending the pre-loaded amount.
Keep it where no one will find it, or you can not worry about that, and if it is ever found by your significant-other/wife/family etc. just explain that you keep a pre-paid card for emergencies or in case your primary card(s) are rejected or not accepted somewhere. You can also say it was given to you as a gift or a prize or in return for a favor (ride to work/home etc). Many employers, retail stores, and online stores give pre-loaded debit cards as prizes, perks or rewards.
I suggest a VISA instead of a Mastercard, as Mastercard tends to ban or refuse to process payments to places/sites they don't approve of, while VISA has yet to do something like that. I've also had Mastercard payments refused for no reason they will relate to me as the buyer and as the recipient.
A good online anonymous payment method is Privacy.com
Another anonymous online payment method is BLUR
Your credit card likely has an anonymous service as well, called Virtual Card or something similar. You log in and set up another card number which you can use online. This new number is linked to your card, and you can request that purchases with the new number do not show up on your usual statement and that you not recieve paper mail statements. The way it works varies depending on your bank and card provider.