I’m back. It’s been awhile since I last wrote and ang daming nangyari for the past year. I’ve had a lot of casual sex but only a few worth writing about. This story is about one of my firsts. The day my anal cherry got popped.
A little background: For the longest time, I didn’t want to do anal, ever. Feeling ko i wouldn’t cum. I mean, I usually only reach orgasm with clitoral stimulation. Mabibilang ko lang with penetration. So I don’t get the hype with anal sex. Until it fuckin happened to me.
I was on and off texting with my ex. We broke up years ago. Let’s call him Charlie. He’s a little bit older than me, late 30s. He’s 5’6″ tall, which is okay coz I’m petite. Moreno but not too dark. And boy, he looks really good for his age. Siya pinakagwapo sa mga naging bf ko. He looks like Paul Jake Castillo of PBB but with longish hair. He’s a bit on the thin side but he always smells clean. Seriously, he never smelled bad even after fucking. And this time, both of us are single again. Goody. I was so frustrated about how slow he is to ask me out, I finally did something: I sent him a picture of my boobs, technically just my cleavage. That should give him an idea, right?
C: Ang ganda naman ng view. Do you still have Saturdays and Sundays off?
H: Expound why maganda? Lol (Syempre I need my ego boost)
H: Yes, I still have the same schedule.
C: I mean maganda kasi relax ka lang. Asa bed lang and parang sarap na sarap humiga.
H: Ah, yeah masarap talaga pag off. Pero parang may kulang.
C: Ano kulang?
H: Ikaw. Hahaha. I’m getting impatient na with all talk and no action.
C: Hahaha. If gagawan ko ba ng action, tatanggapin mo ba ako? Baka kasi may iba ka ngayon.
Well, I did have a different guy those days, just a fubu, but it was getting tiring na. I need to get fucked by a different cock and my ex is the most passionate lover I ever had. I mean this guy would spoil me sexually and doesn’t really care much if i don’t reciprocate. Double whammy.
H: I’m almost embarrassing myself na, halos maghubad na ako sa harap mo and all you can say is baka may iba ako? Cute.
C: You’re not embarrassing yourself cause that’s not how I think of you. You know how I respect and love you.
H: I am embarrassing myself and kulang nalang puntahan kita. And on that note, I’m going to Makati, sa ***** in a bit. Sobrang hint na yan ha. And remember, I owe you lunch.
C: What time ka pupunta and what time?
The place is just 2 blocks from where he worked and I timed it so that I can be there during his lunch break.
Hmm lunch breaks seemed to be my thing..
Anyway, long story short, finished my errand by 1pm and told him I’m on my way to his building.
H: Nakakahiya sayo, pag nagkita tayo, puro pawis ako. My face is bare. I’m just wearing shorts and a t-shirt. Not exactly meet up ready.
C: Okay lang no. Mas okay nga ganyan. 🙂 We can have lunch dito sa may building lang namin if that’s okay with you.
H: That’s fine. I just need to go to the restroom first to freshen up.
C: May alam akong lugar kung saan pwede mag freshen up.
Just reading that made me wet. But I don’t wanna assume.
H: Hmm What’s the name of the place?
C: Wala yun. It was just a naughty joke kaso baka ma offend kita. Lika na para makakain na tayo. 🙂
Damn it, binawi pa. Time to take action kung hindi eh olats ako.
H: You know I rarely get offended with naughty jokes especially if galing sayo. I’m almost there.
C: Alright, I’ll see you in a bit. And pwede din pala tayo kumain dun sa lugar kung saan pwede mag freshen up.
Bingo.
H: Sige ka baka totohanin ko yan. (Pakipot pa kunwari ako)
C: Hahaha. It’s okay. Pwede naman ako out saglit. 😛
Oh the tongue.
H: Okay. Shit wala na ako masabi. Hahaha.
C: Okay? As in okay na okay or okay na..okay? 😛
Fuck, the tongue again. Sorry guys, medyo sigurista lang talaga to si Charlie.
H: Gusto mo bawiin ko? Or we’re you joking lang ba?
Internally I was saying, please say no. Please say no. My clit is tingling and I’m so turned on na with all the banter.
C: Syempre hindi na, you said yes na eh. And I’m not joking. Are you?
Hell, no I’m not joking, sa isip ko.
H: I’m not.
C: So.. 🙂
H: So.. hahaha. I’m near Ayala na.
C: Hahaha. Shall we?
You can’t imagine how horny I am already at this point. That’s how hard this guy turns me on.
We finally meet, this is the first time in 5 years so we’re both nervous. My heart skipped literally the first time I saw him again. Both of us kinda laughed kasi parehas kami tense. He’s still so handsome and fuck sobrang namiss ko siya. He was wearing a white buttoned long sleeved shirt, black slacks and black leather shoes. If you read my last story, I’m usually into bad boy type of guys. But this guy makes business casual really sexy and I imagine wearing that same shirt after he fucked my brain out.
So we finally got into a cab, and within 10 mins, we stopped in front of a motel. He checked us in, paid and finally we got inside the room.
I told him I’ll just freshen up, as planned. He laughed and took off his shirt and got comfortable in his white undershirt and navy blue boxers. I don’t know how he does it, but he makes tshirt and boxers super sexy for me.
After I peed, washed face and my pussy of course. I made sure na malinis ako just in case he eats me. Then I came out, sat on the bed and we start talking. How he was. How’s work. Random stuff. And after I don’t know, maybe 10 mins, he started to move his body near me. Finally.
We started kissing. At first it was tentative, really slow, lips and tongue meeting like we have all the time in the world. Then it started getting harder, hungrier. Tangina sobrang sabik ako sa kanya. He got on top of me, his hands getting busy. He took of my shirt then my bra. His hands unbuckled my belt and pulled my shorts down my feet. I kept on kissing him kahit na nararamdaman ko yung init ng kamay niya sa boobs ko, sa tiyan, then on my right thigh. I moaned kasi nakakakuryente kamay niya.
He finally touched my pussy, rubbed his hand on top of my black panties. Slowly up and down, up then down.
“Charlie.. fuck ang sarap ng ginagawa mo.”
“Masarap ba? Basa ka na nga eh.”
“Kanina pa ako basang basa sayo.”
His eyes were so intense. Without saying a word, he started kissing my neck down to my cup C boobs. Inisa isa niya, parang sanggol kung sipsipin niya mga dede ko. While sucking on my right boob, his right hand started to remove my panties slowly. Then he started to lightly touch my thin pubes (I shaved just the day before, buti nalang). Then I can feel him trying to part my labia using his fingers, hanggang sa dahan dahan niyang pinapasok yung isang daliri niya. I was so wet his finger didn’t have a hard time pushing inside.
“Ang init mo Hannah. Sobrang na-miss kita.”
He started finger fucking me. Slowly at first, timing sa paghalik nila sa lips ko. I parted my legs, welcomed his assault sa pussy ko. His right thumb was rubbing my clit, everytime he pushes his finger, then two. Tangina I wasn’t even sure anymore ano ginagawa niya but it was fuckin amazing.
“Charlie ang sarap! Aaaah putangina ang sarap niyan!”
I was moaning so loud, wala na akong pakealam if may makarinig sa akin sa kabilang room or sa hallway.
Fuck fuck fuck fuck fuck. Yan lang nasabi ko in between my moans.
Charlie was relentless. He finger fucked me like his life depended on it. He alternated between kissing me and sucking my nipples. I felt him trying to mark my boobs, just above my left nipples. I felt just a little bit of pain when he sucked on my skin. He wants to mark me like he wants to own me. In no time I was cumming on his hand, my body tensed so hard, and my release was mind numbing.
When I looked at him, he slowly licked his fingers, the same fingers which just fucked me to kingdom come.
“You’ve always taste good, kahit noon pa. Ngayon ako naman.”
He took off his boxers, went up my body, sat on my chest, his rock hard cock in front of my mouth.
He has an average sized penis but from what I can remember, man, he definitely knows how to use it. He has a bit of pubic hair but ang bango pa din niya. I tried to lick the head first. Parang ice cream, dinidila dilaan ko yung ulo. Then I started opening my mouth to take the head first, tapos dahan dahan niyang pinapasok titi niya. He was looking down at me, both his hands sa may headboard, and he was moving his hips slowly, fucking my mouth, in and out, in and out. Tangina I’m so turned on with how he looks at me, so intense, his hair falling down his cheeks. He tried to deep throat me, I can hear him moan while I try my best not to choke.
He started to stand up, took off his shirt. He kneeled between my legs, hooked both his arms under my knees and without using his hand, moved his hips to guide his cock to my pussy.
He slowly entered me. I can feel his cock slowly pushing inside. My vaginal walls can feel his warm manhood, still slippery from being so turned on nung sinusubo ko siya. He started pumping. Strong, rhythmic pumps, pabilis ng pabilis. His face was so intense. He was just looking at my eyes habang tinitira niya ako. I tried to look only at his face pero may humuhugot ng paningin ko. Tiningnan ko pano pumapasok at lumalabas yung titi niya. How wet it was with my juice. When I looked back at his face, he was also looking at my pussy. I can see sa mukha niya na sobrang turned on siya sa nakikita niya. I saw him close his eyes, his face tensed, then he moaned out loud and came.
Sobrang pawis niya para siyang nag marathon. He hugged me while still on top and kissed me sa neck. I can feel his heart still beating so fast.
“Ang sarap mo. But give me 5 minutes.”
“What do you mean 5 mins?”
Di na ako kinibo ng loko. Parang nakatulog sa pagod. He’s already on his late 30s so understandable if need niya kontin pahinga hihi.
After a few minutes or so, I felt him move and started kiss me again. He kissed my neck, my breasts, my tummy. Small kisses. Then I felt his hands, like he’s trying to turn me over. Oooh doggy style, my favorite.
Dumapa ako, on my elbows, with my butt right up there. His still half erect penis trying enter my pussy, while also trying to move his cock up and down, his penis touching my clit up to my anus and back down. I was still so wet, yung ulo ng titi niya yung ginagamit niya para kumalat yung pinaghalong tamod niya at yung cum ko. Nung naramdaman ko na tumigas na yung titi niya, I felt him trying to push my asshole. Bigla akong kinabahan, oh my does he want to fuck me in the ass? I turned to him and asked:
“Gusto mo itry?”
“Ang alin?”
“Gusto mo ako ifuck sa pwet?”
He hesitated. Then finally asked: “Okay lang ba?”
Omg. Tangina, my recent ex tried to do this before pero dahil malaki titi niya, I stopped him kasi masakit na, even if i try to relax myself, nararamdaman ko pa din sakit.
But I thought now, maybe I can do it now kasi his penis is prolly just the right size. And boy was I freakin right.
He tried to wet the tip of his penis by pushing it inside my pussy first, tapos dinagdagan niya ng laway. Then he started pushing at my ass. At first, ayaw pa bumukas ng tumbong ko. He might have thought I was tensed, kaya habang sinusubukan niya ipasok titi niya sa pwet ko, he put his hand on my clit and rubbed it slowly. I started relaxing, ang galing ng mga daliri niya. He alternated between rubbing my clit and finger fucking me, then i tried to do deep breathing myself. (I read somewhere that doing it will help relax my anal muscles)
Then finally, napasok niya yung ulo. I tried not to freak out and just focused on how fingers are turning me on. Then he started pushing the rest of his cock inside. A few centimeters at a time, hanggang sa napasok niya ng buo. And man do I feel full. I feel like a pervert for some reason and it helped turn me on some more.
Then he started moving. He moaned so loud and di niya mapigilan sarili niya na sabihin, “Tangina ang sikip mo”
He moved slowly at first and honestly, dahan dahan din tumitirik mata ko. He stopped playing with my clit, both his hands are on my hips, trying to regulate his pumps. I was moaning and maybe he thought nasasaktan ako. There is a bit of pain, but when I finally relaxed, fuck, it was like a religious experience.
When he started going faster, the build up was entirely different compared if sa pussy. I really can’t explain the sensation. Bawat pasok sa asshole ko, the sensitivity was incredible. I can feel his whole penis going inside and out. Para kaming na-dedeliryo. I was moaning really loud but i had my face on a pillow kaya it’s muffled. After a few more pumps, pabilis ng pabilis and I felt that he was trying to cum na. I want to come with him. I put my right hand and rubbed my clit roughly. I want to cum so bad. Basang basa mga daliri ko. Maybe him seeing me rubbing my pussy pushed him to the edge. I heard him shout. Nararamdaman ko yung init ng tamod niya. I followed him. I came so hard, my pussy just kept on pulsating kahit na tinanggal ko na kamay ko.
I still get wet everytime I think about that day.
FYI, it was his first time too.