Anna's Confession
Copyright© 2025 by LeoB
Chapter 1
Biography Sex Story: Chapter 1 - My BFF (best friend forever) Anna flips our World upside down - and we enjoy it.
Caution: This Biography Sex Story contains strong sexual content, including Ma/ft ft Mult Consensual BiSexual Heterosexual True Story MaleDom Rough Spanking Gang Bang Group Sex Interracial Black Male White Male White Female Oriental Male Anal Sex Analingus Cream Pie Double Penetration Exhibitionism First Oral Sex Petting Voyeurism Size Small Breasts
I kinda liked how men suddenly began looking at me. Something was different. And literally all of them did it. Teachers, my Dad’s colleagues and friends, even all of my friend’s Dads.
My apologies, I should have introduced myself. My name is Leonie, I’ve just turned 15 a week ago and I’m living in a flat in Berlin with my parents and my little sister Marlene. Anna, about 7 months older than me and my BFF, started all this. Exactly two weeks ago, we were having her at our place, for a sleepover, after having spent most of the day in our “Schrebergarten”. A small garden plot surrounded by many others, forming a big area, pretty much in the center of Berlin. Its community, for us at that time, consisted mainly of friendly old men, some with a wife and some without. Really, nothing to think or even worry about. Both of our direct neighbors have witnessed us growing up. Reinhold (64) und Gerda (61) Malcharzyk, who owned the garden to the left of our front door had been there even before my family got hold of this parcel. Uncle Jürgen (67) on the right-hand side replaced his predecessor shortly after Anna and me were born. He seemed to celebrate a lot with his friends, and we really loved how he made us laugh. His company made both of us feel every single time cozy, yet secure.
We were already in bed, as usual chitchatting before we would go to sleep. Then she began telling: “Leo...!?”- her voice, suddenly sounding so serious hit me hard. “Something happened today! Good and bad at the same time somehow and I totally don’t know how, but I need to tell you!”
“I love you Anna, you can tell me anything! Never ever would I judge you! We are sisters, silly girl – don’t you ever forget that again!” – I told her, encouraging my BFF to finally confess everything that had happened. She had left her bed and was now nervously walking back and forth right in front of me. The story she was telling me now changed everything. “O-o-kay! After we split up earlier today – when I was cleaning up the rest of the garden while you were responsible for the house, I suddenly heard Uncle Jürgen’s dark voice: “Anna, my blonde little Angel! Great to see you again after that truly horrific winter! You really seem to blossom faster towards perfection every year, honey!”. Her Performance to mimic Uncle Jürgen right in front of me as she was telling and showing me everything that had happened during this exceptional encounter, hit me. Her body, although shuddering from discomfort of what she was about to tell her “best friend forever”, did not manage to stop her. “I had noticed him way before he seemed to be even sure about wanting to approach me!”-she recalled, further explaining: “He was watching me! I caught him staring at my ass while I bent over to pick up something!”-she explained. She went on how she suddenly heard him saying: “I give you 1000€ right now, if you show me your asshole!” “How about you give me 500 and I promise to seriously think about it right now?!”-Anna relentlessly replied. “Ok, sweetheart, here you are! 500€!”-Uncle Jürgen quickly agreed. He asked her if she could show him her cute little asshole. “What are you offering Mister?”-she questioned, sounding as innocent as somehow interested. “A man’s soul ... and another 500€!”. “With him making jokes like that and me feeling so good enjoying his company in that very moment, the naughty voice in my head was finally taking over!”-Anna tried to explain. “I bent over, ... a-and, yea, and I pulled down my panties just below my ass and began to show him what he was craving for!” – she told and went on acting right in front of me, “Like this!”. She stood slightly bent forward maximizing a hollow back, presenting her cute virgin unshaved holes. “But instead of him panting about the sight he went: “Young miss! I must order you to shave and cleanse yourself in preparation for our next encounter! But first, come to me please Anna, my little dove! Come to me moving backwards ... I do not want to miss a single second of this view!” Making sure that the most intimate zone of my body was always visible to him, I started to slowly move backwards. As soon as I got in range, I felt his hands on my ass – petting and playing with my cheeks, slapping them - eventually pulling me closer to the fence. “This ... is wrong..., O-onkel Jürgen! Nothing yet happened, that we couldn’t forget!”- I told him, though it sounded like I had spoken to myself instead. “Right OJ?!”- I asked for his confirmation, desperately trying to wake him up by using the nickname I had chosen for him when I was 6. He didn’t respond. Instead, I felt him firmly grabbing my thighs - pulling me to the fence. With his hands on my ass, spreading my cheeks, something warm, wet and incredibly smooth was softly touching my asshole. He was licking my ass and I loved it. “Uhhhm! Awwmh!”-I moaned as silently as I could while his tongue dug deeper in my cute little butthole. “Anna, my little honeybunny, no one will ever find out! And you keep your virginity as long as you want! You know ... I-I’m ... in love ... with both of you - for so many years now!? Never would I do you any harm!” I heard him pleading. “2000€ you get next time young lady if you comply to meet me again! But ... please make sure to shave your cute body and clean your ass! For that you just need to-!” “I know how to do that, OJ! But first, what about the cash you owe me today ... like ... right now?!” “You ... you’re totally right, Anna! I have to apologize ... be back in 30 secs max!”
“Less than 20 secs later he was back paying his bills. I have 1000€, Leo!”- I said. “And I really think I wanna go back to him for 2000€!”
“It’s so hard to believe Onkel Jürgen wants to fuck at all, even fuck us, for cash! But ... but then again, I somehow love him too for so long and would anytime prefer to have my first time with a guy that I really like, instead of losing my virginity to a clumsy boy, who would cum after a few secs, leaving me unsatisfied and in shame!” “So you’re saying you gonna come with me?!?”
“Think so, yeah ... but can we please do the preparation together?” “I love you Leo and by the way I love OJ too, somehow, just like you said. We should not eat much until Friday, keep cleaning our asses and shave our bodies, he told me!”
Today was Wednesday. We had enough time to learn how to fulfill Onkel Jürgens tasks.
We couldn’t think straight and suffered enduring school. The idea of getting so much money for doing something as forbidden and naughty as this excited both of us. Constantly thinking about it kept our pussies wet, when finally on Friday school was out. My dad picked us up and was heading straight to the garden. He knew we were gonna help Jürgen clean his house. The training suits we were wearing suggested nothing sexy at all. Yet, they were hiding our cleaned, shaved, and creamed naked underage bodies. “See you later girls!”-my father said as we were leaving our garden in order to approach and enter Onkel Jürgens property.
The door opened as we were closing in. He gave both of us an intense hug not at all hiding that he already had a hard on. As soon as he closed the door he said: “You told Leo? Anna, does she know what this is about?”
“Hey!!! Hello Onkel Jürgen!! I am right here!”-I jumped in. “You could have asked me directly instead! And what the hell are you thinking?!?! Of course, Anna had told me everything!”
Seeing him stunned by these words - unable to respond – I knew I had to keep control of that situation. This awkward “moment of zen” ended, when I began to explain, that both of us liked the idea of getting so much cash by trying those things out with men we really liked – men who cared for us since we were 6years old. No immature boy who would simply treat us badly after he had finally taken our virginity, like we had heard it so many times, was standing a chance to get even close to us.
“2 times 2 is 4! So 4 Grand for you it shall be! No problem!”-he stated seemingly having recovered from his stun. His face, eager to show honesty, seriously failed at doing so.
“If this is really no problem Onkel Jürgen, can you just pay in advance, please?”- I said.
“Okay, I’m gonna get the cash, but I expect you two cuties to let me see everything as soon as I’m back!”
We were explicitly presenting our hairless holes to him when he came back. Doggystyle next to each other we were kissing as he said: “Ladies, ive got the cash! Both of you get 2000€! Anna can you do me a favour and hold your 2 grand with your mouth?!” We giggled upon this idea and Anna said: “Mmmh ok OJ, but that’s really weird?! Why do you want me to?!”
“Just do as I say my, please, little dove!” he said and put the money in Anna’s mouth. “Leo, would you please do the same?!” We giggled again. “Sure, why not?!” I opened my mouth and felt that stack of 200€ notes, which I was supposed to keep between my lips.
Anna and I began tickling each other with the cash we had in our mouths when we felt his hands touching our cute buttocks. With his fingers now busy touching and playing with our holes, he said: “Did you two angels do what I had asked, Anna? Did you tell her? Did you prepare?” “She told me everything!”-I jumped in. “And for your info ... we did exactly what you had asked! Check it if you want!”
“I like that idea, Leo!” his hands were now all over my ass. Playing with my cheeks, he eventually spread them, and I felt something soft, warm and wet pushing into my pussy. His tongue was fucking me, sometimes even hitting my hymen. This was when I couldn’t help moaning deeply, obviously enjoying what he was doing to me. He pulled his tongue out of my virgin pussy and was now licking my asshole, grunting every time he pushed it in. “You do like that, right Leo? My tongue in your cute little butthole!” he commented, provoking me. “Hmm-mmh – yeah!” I moaned, indeed enjoying his tongue ravaging my tight tiny ass. “But Anna also told me that we would get 2000€ each for our gentlemen’s services! So, I keep wondering, if you payed us as promised. Because, I really wanna feel your cock inside me, if you do!”-I replied. “Here you are, my cute little angels, 4000€!” – he said and presented the money. “Mmmh, Anna, my little dove, would you now please comfort my cock?!”