This is part 4 of my story of becoming a man. If you haven’t read the previous parts I would advice to do so as this follows on from there
Things have been a little awkward between me and my sister after what we had done but we both tried to hide anything that happened from our parents. Clearly the warning from Tiffany had scared my sister to say anything.
Me and Tiffany was still enjoying our time together most afternoons and my sister hadn’t walked in on us again. Her practices was continuing normally and she seemed to slowly becoming more friendly towards me again.
About a week and a half after the day that I fucked my sister Tiffany showed up like normally but she wasn’t looking or sounding the same like she did other times. We didn’t rush to my room and strip down in a second. She placed her arm around me as we walked to the room a lot more slowly. Sounding serious as she did and stating that we need to talk.
When we get to my room she sits down on the bed and looks at me. I can almost sense that she wants to cry which is odd as I haven’t seen this side of Tiffany before. She swallows hard and starts talking. “Well Theo I have some big news. I found out I am pregnant, and I am pretty sure it is yours from that first night when you unloaded in me so quickly. There is a chance it can be my boyfriend but other than that night all other fucking with both of you have been with condoms. So I will become a mom and you a dad. But don’t freak out on me yet as I have decided that I will pass it off on my boyfriend and insist it can only be his and that a condom must have failed us one of the times. But to make him believe that though I will have to stay close and committed to him as he might be looking if I am fucking other guys. So today will sadly be the last time we can do this, at least for a good long while. But I absolutely love what we did and you will make girls so happy in future.”
Tiffany pauses to take a breath and I try and process everything that she has just told me. She is pregnant and it can be mine. I could be a father. Tiffany reaches out to me “Don’t look so shocked Theo. This can happen when people fuck around. I am not angry with you, I was when it happened but have gotten over that. I have another surprise for you though. Since today will be tbe last time I have decided that you can finally fuck my ass if you still want. Giving my anal cherry to the father of my child just seems right”
I have an excited look on my face as Tiffany removes her black skirt but surprises me when she also removes her top which she hadn’t done before. I am mesmerized as I see her in what I can only describe as the sexiest set is sheer and lacy black lingerie. She walks up to me and places her finger on my lips. “I will still not kiss you but you can also play with my tits as well today. And I hope you like the something extra I had put on for you”
I nod and agree that she looks amazing. And then the last training I would gwt from Tiffany starts. As she first shows me how to unhook a girl’s bra and makes me do it repeatedly until she is happy. Then finally she lets her bra go and drops to the ground. Showing me how to make a girl’s tits and nipples feel good. Realizing how many mistakes I had make with Scarlett when I played with hers. Soon Tiffany is moaning and her nipples are rock hard. Teasingly telling me I definitely know what to do when I have a girl as ready as she is.
I slide down and remove her panties that are already soaking wet. Knowing how to go from here in terms of eating that amazing pussy. She gets on her hands and knees and tells me to also lick and suck and play with her asshole to get it ready. Soon she is moaning through a big orgasm, I am not sure if it was bigger due to also playing with her tit or if it is due to what is ahead.
Tiffany then pulls her bag closer and stops me from grabbing a condom. Telling me condoms are anyway useless for a girl already pregnant and it also isn’t needed in a girls ass when pregnant or not. But that we will definitely need to lube up her asshole and my cock for this. She pulls out some lube and gets some on a finger that she uses to rub around her asshole when she is back on all fours and tells me to take some and rub on my cock and especially cockhead. I do as instruuand soon we are both ready. “Okay Theo I want you to get in position and to slowly push your cock into my asshole. It will be tight and might struggle a little but I don’t want you going to fast until you are all the way inside my asshole”
I agree and get behind Tiffany and for the first and probably only time line my cock up with her asshole. I press the head of my cock against her tight asshole that seems to fight against my cock invading her. I keep pushing and finally feel as the head of my cock slips into Tiffany’s asshole. She gives a loud squeal and tell me to hold on while she tries to prepare herself more and to settle herself. Finally telling me to continue pushing deeper but very slowly.
I slowly pushed and worked my cock deeper into her extremely tight asshole that seemed to want to push out my cock. Hearing as Tiffany gave small squeals and moans and groans but not telling me to stop. Finally I push the last of my cock into her asshole and feel my balls hit against her soft and wet pussy.
Tiffany smiles back at me iver her shoulder. “Well done champ. Damn that young cock is filling and stretching my tight little asshole. So I took your virginity and now you have taken my anal cherry. Go ahead and fuck my asshole but please remain gentle for now”
I don’t waste time and start sliding my cock in and out of her asshole and picking up rhythm with my balls hitting against her pussy with each thrust. I realize that she has a hand under her pussy and is rubbing and playing with herself while I am fucking her tighg asshole. Moaning louder and louder as we go longer and longer.
Sadly all great things has to come to an end though and soon Tiffany explodes in a body rocking orgasm. I feel as her asshole that was already tight locks around my cock like it is trying to squeeze it off. I can’t do anything else but let her tight asshole squeeze me and push me over the edge. Shooting a hige load into her used to be virgin asshole. We are both grunting and panting as I pull out.
Tiffany turns around and let my cock slip out of her asshole. She cleans my cock before getting up. Kissing me on the cheek before she dresses. Finally blowing me a kiss.
“See you around champ. You were great fun these past few weeks.” I watch as she walks out my room probably for the last time. But never to be the same again.
Hope you all enjoyed the story. I can continue with other adventures after sex stopped with Tiffany if any are interested.
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#Cheating #Pregnancy #Teen
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