This is part 3 of my story of becoming a man. If you haven’t read part 1 and 2 I would advice to do so as this follows on from there
Things have started getting exciting and fun between me and Tiffany. She shows up most days after school and her pants or skirt along with her panties are gone within moments. Same with my pants and underwear. Despite this sexual games being an almost daily thing I still haven’t seen her bra or her tits and at this point I am not sure I will.
On the flip side though is my oral skills are getting better each day. Tiffany is barely directing me any more and allows me to eat her out how I like and we have also started doing it in more positions than just her straddling me face. Even though I like it I also like eating her out while she is in different positions. A few days ago when she was on her hands and knees I even liked over her tight asshole that gave her a fright. Telling me that no one has ever touched her asshole. Not even her boyfriends. As I played between her pussy and asshole she said she was considering maybe trying some anal stuff with me in future but not yet as she wasn’t ready for that.
As part of eating out Tiffany and giving her regular orgasm she was returning the favor. Some days she used her hands. Twice now she had even used her mouth on my cock like I use my mouth on her pussy. And some days she allows me to fuck her pussy but always insisting on using a condom and putting it on herself. Not that I can complain as I was having regular sex with a sexy older girl. And with her help I was starting to last longer than just a minute or two and was even able to fuck her long enough a few days back to where she had an orgasm on my cock pounding her from behind.
All the fun me and Tiffany are having though is about to hit a a snag. Just more than two weeks on during a Tuesday afternoon everything started as we normally do. Tiffany arrived at my house moments after me. I lead her in and we made straight for my bedroom. We never think about closing the door as it is never needed. Today Tiffany was in a short skirt again similar to the one from our first night and was actually wearing the panties from that first night. She even allowed me to remove them today. She got on all fours on the bed and I quickly started licking up and down her sweet pussy.
As we started neither of us heard the front door opening. Scarlett is home early, her dance class is canceled for today. She walks towards her room and walking past my door she freezes with her eyes wide open seeing a girl definitely older than myself getting on my bed and pointing her naked ass in my direction. And watches how I start to lick and suck on the girl’s pussy. Mesmerized by the sight she starts watching what we are doing instead of making her presence known or walking away.
I am not aware of anything happening behind me with my sister as I do what I have been doing now for a while. And that is making Tiffany moan loudly and to get her to an orgasm almost to cum all over my mouth. And like I did the last time Tiffany was on all fours I tease and lick and play with her tight and basically untouched asshole now and again. Causing her to squeal and moan out in pleasure even more than what she was doing already.
Behind us my sister couldn’t stop watching with her hand sliding into her own pants and playing with herself without thinking about it. Jealous of this girl that I was able to get into my room and that I was eating out. With a good few questions about it.
At the same time Tiffany is moaning louder and louder as her orgasm is building and as my finger touches her asshole she explodes in orgasm. And like always I try and lick up as much of her delicious juices as I can. Tiffany turns her head to me to and start to mention me touching her asshole but as she turns her eyes catch a glimpse of Scarlett. She flips over and almost naturally start to cover herself. “Theo looks like we have a problem. Look, your sister”
I turn and I am shocked seeing my sister standing in the doorway with her hand inside of her pants. She blushes almost as red as her hair and starts to stammer unable to form a proper word. Tiffany finally relaxes and I see that evil little smile that I had gotten used to by now. She jumps up and runs towards Scarlett and grabs her hand and pull her into the room and onto the bed with her. Scarlett looks around like a deer caught in headlights. But Tiffany seem to enjoy this and have some sort of plan in mind for my sister. Asking her “So did you like what you were seeing. How your brother was eating me out and making me moan. Did you wish he was doing it to you. All you have to do is ask and you can have some fun as well”
Tiffany doesn’t really wait as she starts undoing my sister’s pants and starts pulling them down. Quickly Scarlett grabs it as they start sliding lower and gives me a glance at her panties. Stammering as she looks at us. “No, wait. We … we … we can’t do this. That …that is my … my brother”
Tiffany again gives the naughty and evil little laught, and I know she won’t take no for an answer and that my sister is about to find out. Tiffany slaps Scarlett’s hand away and yanks down her pants down her leg and fully exposes my sister’s red panties that she is wearing as she throws the pants across the room. Tiffany places her hand under my sister’s chin and looks in her eyes as she says. “You are a little girl and about to get more lucky. Your little brother here is one of the best if not the best pussy eater in school and you can enjoy that in your own home. And it isn’t like he is going to fuck an incest baby into you. He is just going to make you cum like you haven’t before. And besides I can see a huge wet patch in those panties. We both know you want this. Now be a good girl and slide those panties off and ask your brother to eat you out and make you cum”
Scarlett looks unsure between me and Tiffany. Like she is trying to decide if she should do this or try and leave. The longer she takes the more impatient Tiffany gets and she reaches out and grabs her panties and pulls them down. I am looking straight at my sister’s pussy now. It looks smaller and tighter than Tiffany’s pussy and another huge difference is there is a triangle patch of red hair matching her head just above her pussy. Tiffany’s eyes clearly focuses in on it as well as she runs her fingers through the patch of hair. Squealing in excitement as she does. “Oh this is so cute. I have never done a landing strip but this looks so cute. Maybe I should try it as well sometime.”
I watch as Scarlett blushes bright red again and tries to hide her landing strip and her pussy from our view. I can’t deny that seeing my sister’s pussy is making me excited and I am eager to taste her and compare how she tastes to Tiffany. I hear as my sister mumbles again in embarrassment. “Please don’t. We have to stop. I am a virgin and don’t want my first time to be with Theo”
I can see in Tiffany’s eyes that this excites her even more. Like being able to see me do first with my sister would be a dream come true for her. She reaches out and quickly pulls my sister’s top off and then the matching red bra. I can see her cute tits and her nipples sticking out. I had thought maybe Tiffany’s tots would be the first I see but no it is Scarlett’s. Tiffany isn’t done either. “Oh so if you are a virgin we will do this properly and tick off the boxes in order. First you two will kiss. And I don’t mean a peck on the cheek or lips. I want to see tongue and it better last a good amount of time”
Again Tiffany doesn’t wait. Making clear this is a command and not a question. She grabs my arm and pulls me over Scarlett. I look into the green eyes of my sister and can see some fear. But I am more scared of when Tiffany snaps at me and lean in and plant my lips on my sister. This is my first kiss as well and I know I am awkward. With our lips locked I think about the movies I have seen when lovers kiss and open my mouth and try to get my tongue in my sister’s mouth. She seems hesitant but finally opens her mouth a little as well and we start kissing more like lovers. I feel strange as our tongue touch and move together but I try and keep it going until I am sure that Tiffany is happy. What neither of us realize is that Tiffany had pulled her phone out and was recording how we were kissing. Both of our first kiss and it was brother and sister kissing.
I don’t know how long we were at it but neither wanted to stop and get yelled at. Eventually I hear Tiffany sounding more happy. “Good. Now suck those little titties and nipples of your sister. What are they? A’s or B’s? Definitely smaller than my full C’s”
I break the kiss understanding what Tiffany wants me to do but not understanding why she is talking about letters. But clearly Scarlett does as she is bright red again as she mumbles it is A’s. All while I do what Tiffany said and wrap my lips over Scarlett’s right tit and nipple and started sucking. Clearly an awkward one as I again don’t have any experience about making a girl feel good by playing with her tits or nipples. On Tiffany’s commands I switch between tits and start doing more like sliding my tongue over her nipples and playing with the tit and nipple I am not sucking. Scarlett has her hands over her face and looking away shyly as she can’t believe me as her brother is sucking on her tits and nipples. Another first going to her brother and not a boy she likes. But she can’t help but give a small moan eventually.
After a while of sucking and playing with my sister’s tits and nipples Tiffany directs me to eat out my sister. I smile excitedly as this is the part I know I am good at. I smile down her body and open her legs more. Seeing her sexy and tight looking pussy. I waste no time as I started showing my sister the skills I had learnt with Tiffany over the last few weeks. I lick and suck and work her pussy. My sister tastes out of this world and if I thought Tiffany could get loud, despite being embarrassed my sister is moaning even louder. But she is still unable to look down at what is happening as her little brother was doing this to her. All the while this works out for Tiffany as she keeps recording what me and Scarlett is doing.
As both me and Tiffany can hear Scarlett’s orgasm building and approaching I feel Tiffany undo my pants and drop them. Exposing my hard young cock. She grabs one of the condoms and slips it on me in a second. She then whispers in my ear so that Scarlett can’t hear. “When she cums I want you to fuck your sister. Don’t wait, don’t ask her. Just push that cock in and fuck her like you do me.”
Tiffany then steps back to record and watch what happens next. It doesn’t take long for Scarlett to have a screaming orgasm and coat my face with her juices. I then get up and between her legs. I line up my cock with her pussy and push inside. I feel like something is stopping me and just push harder until I can get my cock deep inside of my sister. I hear as she screams in pain and looks down at me with her eyes huge as I start sliding in and out of her pussy. “What the fuck Theo. Stop. Oh fuck you asshole. You fucking stole my virginity you prick. Stop! Stop!!”
I don’t stop and use my body and hold her so that she can’t get away as I pound her as deep as I can. Scarlett looks up at Tiffany for help not realizing this was her idea. “Please stop him. I don’t want this. And why are you recording us. This isn’t normal, he is my brother” Turning to me she continues her rant but I do realize she isn’t actually trying to escape from under me “Please Theo think what you are doing. I am your sister. Mom and dad would kill us if they knew what we are doing. This wasn’t supposed to be how I lost my virginity”
I can hear how Scarlett is crying but soon there is also small moans between it as she still asks us to stop but less often. Thanks to Tiffany I am able to already last a lot longer. Fucking my sister harder and deeper. I then look into her eyes as my orgasm finally approaches and slam deep into her pussy as I started to cum. Feeling how I am filling up the condom with all my cum. Exhausted I pull out of my sister and like I had seen Tiffany do almost daily I slide the condom off and bring it to the lips of my sister. Tipping it over so that the cum will flow into her mouth. She gags a bit in surprise but in her defeated position she actually swallows a good amount of my cum. She is in tears and crying even more now that we are done.
Tiffany lowers her phone as she is done recording. She looks so happy at what had happened. She stands over my sister in a dominating way. “Oh is the little slut crying after her first fucking. Don’t lie to us, you loved this and actually wanted it. You loved that your little brother was your first. And if you think for a moment that you are going to tell anyone what happened between me and your brother or what you and your brother did I will send the video to everyone at school and your whole family and everyone will know that you are a brother fucking incest slut that lost her virginity to her little brother.”
Tiffany flips her hair and turns to get her things to dress again. Sure she had made her point. I can see the tears in my sister’s eyes as she nods and just looks at Tiffany. Watching her walk out like nothing odd had happened.
I try and comfort my sister but she doesn’t seem interested in it. After a while getting up and looking for her clothes before she stumbles to her room. Unsure what will happen between us now that I had fucked her. But what is clear she tries to act normal and doesn’t say anything yet to our parents when they get home. Wondering if there will be anything to follow after what happened this afternoon.
Part 4 will hold a big surprise for Theo leading to some wanted and some unwanted changes