TRUE FIRST TIME TALES
Jeff's TaleRated: X ages 14
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I'd always thought I was so totally different as a teen. But reading the many stories here, I see that I wasn't all that different.
I grew up pretty poor, living in a trailer court in a middle-sized city in a western state. The thing about living in a trailer court is that the kids living in the houses in the neighborhood around it don't want much to do with the 'trailer trash' kids. So your friends are the other kids in the trailer park, for the most part.
I was raised pretty strictly, so I ended up pretty straight-laced and avoided the kids that were into drugs and were running around like animals. So my friends were the other kids that didn't do drugs or act like thugs. There were six other guys my age in the court, and Dan, Jess, and Mike were my friends that were also 'clean' kids and were in the same grade in school and we liked almost all the same things.
When we were really small, we'd taken baths together plenty. We'd seen each other in our underwear a lot during sleepovers. We weren't very shy as kids. We'd done the usual showing off and pretending to jerk it stuff, and we sort of knew what each other hand down there. We'd done show-and-touch, where we'd show each other our boners, and sort of jerk each other's dicks a little. Just kid stuff. We even stuck those Sharpie markers up each other's butts a couple times. And more than once we'd make a bet on something, where the looser had to suck the winner's dick. Not for long, and we didn't know how to for real, just kid stuff. And never as a group, always one-on-one.
By sixth grade, the four of us were pretty close. We weren't doing the show-and-touch thing as much. We were twelve, so none of us had much down there, and we knew Mike had the longest anyway. And I had the biggest nuts. There wasn't much of a reason to do that stuff anymore.
During seventh grade, I saw Dan and Mike naked again, in the showers in gym. I was curious and interested by now. Dan was like me, smooth and hairless and small down there. Mike, though, had some hairs and his dick was pretty big. He was way into girls, and started claiming he could squirt and such. Man, I wanted to see him cum so badly - and that was kind of scary. I started jerking off regularly as my dick and balls grew.
During the summer after seventh grade, I started really developing and getting really interested in sex stuff. And jerking off a lot. Jess too, but not Dan yet. So the three of us were into talking sex and girls and such. A lot. I wanted to do the old show-and-touch game again, but I was worried about what they would think of that now. We weren't little kids anymore, and I was having feelings about guys, so it was too weird to even think about bringing up now.
During eighth grade, I got to see Dan's stuff in the showers in gym as he got hairs down there and his stuff grew bigger and longer and more interesting. Mike's was still the biggest, and I still got to see it sometimes on weekend sleepovers dangling in his underwear. Geeze. Jess was pretty shy by now, and we hardly talked sex stuff anymore.
By now I was aware I was way into Jess, a lot. He was so hot. He had a narrow, lean, almost flat butt, but otherwise he had it all going on. Face, hair, bod, bulge, smile, smell, and the way he laughed and even acted. I was so into him. Jess was my crush, for sure.
He grew up with three brothers, one older, and twin younger brothers. And a sister. In a three-bedroom trailer, that mean all four brothers slept in the same room. The twins even in the same bed. Then his older brother took to sleeping on the couch. So Jess was used to sleeping through his two younger brothers' rambunctious activities. He could sleep through a tornado. We rarely stayed over at his house, ya know? When he stayed over with one or more of us, we could get away with doing all kinds of things to him while he was asleep. We used a marker to give him a moustache, beard, and thick eyebrows one time - and other such mean-but-funny things. He was so hard to wake up. We could even carry him outside and he wouldn't wake up. Many times he woke up in the morning to a surprise.
So, it was late in the summer, just before we started high school. Jess was staying over at my place. Mike was on vacation with his folks, and Dan was pissed at us for a prank we'd pulled on him. So it was just me and Jess. The hot Jess. The sleepzombie Jess.
We'd stayed the previous night at Mike's before he left for vacation with his folks, so I hadn't whacked one out for almost two days. I was super-horny. I tried to get Jess to talk sexy stuff, but he was way too shy about that stuff now. Nothing like MIke or Dan. I was almost as shy about that stuff now, now that I knew I was probably gay. I tended to stay out of the sex conversations so that I didn't give myself away, but I took part too, also so that I didn't give myself away. It was tough.
When Mike or Dan stayed over, they liked to sleep on the floor on a foam bed pad I kept in my closet. But Jess was cool with sleeping in my bed with me. We had since we were really little. I could climb over him and go to the john in the middle of the night and never wake him up. I could watch TV or listen to music or play video games and not bother him one bit.
That night, I was so super-horny, that I planned on playing video games until Jess fell asleep so I could whack one out laying next to him. I played for over an hour after he fell asleep, then I laid down next to him, pushed my underwear down, and started whacking off laying right next to him. It was the first time I'd ever dared to do that. I'd thought about it a million times, but this time I was so horny I went for it.
It was so hot and sexy to beat one off with Jess right there next to me! I wasn't worried he'd wake up at all. He might, to use the can, but ti would be a long while before he did. And he'd do that slow wake-up he does and I'd have plenty of time to cover up and such. So I stroked off as I looked at his cute sleeping face. I imagined kissing him, and us doing it to each other as we kissed.
I thought about reaching over and groping him. I didn't. I kept jerking it and looking at him, and thinking about kissing and jerking each other off. I was having a great wank, and was really into it. I was gonna blow a huge one. It was going to be awesome!
I stopped, though. I didn't want to blow off yet. Not until I at least got a brief feel of Jess' stuff. At least a good look. So I held my throbbing dick and worked up the guts to do it. It took a while, but I did it.
I slowly reached over under the light blanket until I felt his hip. Then I slid my hand up, and over some more, following the waistband of his tighty-whities, until I felt his soft, warm bulge.
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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.