Straight to the Bottom Pt. 03

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I (straight) lose my anal virginity. Uh Oh.
8.8k words
4.7
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Part 3 of the 3 part series

Updated 06/09/2023
Created 01/17/2020
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Part 3: The Date with Destiny

Winter was slowly dwindling away. It was now months after my Frozen facial courtesy of Brian. I couldn't completely 'let it go'; even after all this time. I haven't heard from Brian since then-- and I was thankful for that.

I needed him out of my life. The thought of what he and I did together set my mind ablaze. Most nights my mind was engulfed with thoughts like:

'What if someone finds out?'; 'I wouldn't have sucked his dick if I wasn't a little bit into it.';'I wouldn't have sucked it if I was sober.'; 'Am I gay?'; 'He could have told his whole college by now!'; 'What if someone finds out?!'

--Ahem, you get the gist.

Besides that, my spring semester at home was pretty boring overall.

It came to an equally boring end a couple days ago...

Now I had no classes, and so much time on my hands, so much time to think...

When I think about what Brian and I did --it sends me into a sexual conundrum (see thoughts above). It doesn't help that I haven't gotten 'lucky' with girls this semester; or much at all. My last sexual encounter was getting splattered in the face with freshly squeezed guy cum.

(Let's just say, if my life's sexual activities were a small pizza pie with six slices—Brian just slapped his thick dick down on two slices! -- My pizza is only two-thirds straight now! I don't even know what a two-thirds straight pizza is -- White pizza with broccoli probably...Anyway, I'm depressed...or hungry.)

Everyone else is getting laid at school. Except me.

I want to be with a girl to just. -- I'm just ready to move on.—

Whatever, I'm going to bed...

...

ZzZzzz

...

The next day I awake in a daze. I was officially on spring break, so naturally I play video games all day.

...

ZzzzZZZzzz

...

The day after that I hang out with some friends. It's pretty fun but I call it an early night and head home. It was nice to get my mind of of Brian for awhile.

That night, that ordinary night, I lazily ready myself for a shower in my room when --

My phone BUZZES --

It-- it's a Snapchat notification -- from BRIAN!

Wait. no.

No, No, No! Brian is not messaging me after this long...

Why would he??

My head begins spinning as I open the app and read Brian's message:

"Hey man! What's been going on? How are you??"

--I shut down the app and toss my phone on my bed.

I don't touch my phone for awhile.

This. Is. Not. Happening.

Basically, I don't want to message him back. I don't even want to imagine him! -- When I do, I think about how he's treated my mouth like it's his own personal sex toy. I think about what I let him do...and what I let myself do. It just feels so...I don't know; exciting. -- But the bad kind of exciting; like any Michael Bay movie. But for some reason...I long for some kind of relief from this situation with Brian. I've already done too much with him to not message him back, I reason.

My mind then tells my trembling fingers to message him back something cool:

"Yo, what's up?"

Groan I suck. (foreshadowing)

Then Brian messages:

"Yoo, I'm back at my parents house in town for a bit. They ain't gonna be home this weekend and I'm just gonna be smokin and chillin if you wanna stop by sometime!(tongue out emoji)"

I panic.

I mostly want to message back and tell him to go fuck himself. I want to just delete him from my mind and forget I did any 'gay thing' at all! But -- I know that's naive. If I wanted to forget it, I would.

I thought I had this all out of my system, but I feel a lot of things are left unsaid. I must be messaging him right now for some reason, I reason.

But could I actually like 'go to his house'?!

- No way! You're straight. He for sure, 100%, is gonna try and fuck you or something!-

My heart is beating so fast and my teeth are chattering in bed as I go through my mental breakdown. Then—my heart sinks as I receive a picture snap from Brian in chat.

I can already see what the picture is -- Cock. (8in)

"You're gonna need a bigger phone!" -- Jaws (1975)

—I open Brian's message fully: it's a fucking dick pic! A picture of his hard and veiny shaft out of his sweats. I stare at the picture of his cock for awhile, not knowing what to do next.

--I think how long and big it looks. I can't believe I let him stick that thing in my mouth. I can't believe it fit...Ahem anyway...

I don't reply.

I look at the clock and see it is close to midnight. It's believable I will be asleep. I can't deal with this right--

My phone buzzes once again.

It's another picture message from Brian. However, this picture takes me much longer to comprehend than the simple 'dick pic'.

-- This picture is dark and somewhat fuzzy and out of focus. It looks like someone kneeling outside. I then recognize my clothes. Then, I recognize the parts of my face not covered in jizz...I then remember the moment: right after Brian came on my face at Winterfest months ago.

In an instant it all becomes clear:

- That's ME in the picture...with cum on my face! -

I thought I remembered Brian putting something in his pants that night after the facial (other than his drained cock).

Sigh.

Surprisingly, I find myself not that angry at Brian as I realize he took a picture of my cum-covered face without me knowing. I'm more angry at myself. I got myself here.

Mentally and emotionally drained, I lie down on my bed and sink into defeat. I feel so...gay. I fought for so long to forget about what I did with Brian, and now there was proof of it.

My phone buzzes.

Brian: "I've been thinking about you a lot since last time. What are you doing this weekend?"

Me: "Fuck you. Have you shown anyone that picture?"

Brian: "No, not yet.(tongue out emoji)"

A quiet rage possesses me. I can't think.

Buzz Buzz

Brian: "I really wanted to show my friends I went to Winterfest with. No one knows you. But I held back :)"

Brian: "Do you got a boyfriend yet? Lol."

My rage and confusion boils over inside me. I feel sick. It's as if I'm at the top of a roller-coaster looking down—knowing any second I will drop.

Me: "Are you fucking serious? Delete that picture now man."

Brian: "I will! I couldn't help myself. You looked pretty cool covered in my cum."

And now the drop. I'm gonna throw up!

Me: "I thought you said you were straight??"

Brian: "I am straight. I like girls more than guys."

Me: "That's not how it works."

Brian: "I don't think you know how it works either lol. Did you see the picture? lol"

Me: "I was drunk and high. Delete the fucking picture."

Brian: "I will. Just want to talk in person. You left in a hurry last time. Did you want to come over my place tomorrow and make sure I delete?"

Me: "No, not really. I do not want to see you, dude."

Brian: "I don't think you are serious. I know how much of a sissy you are for my cock."

I step back from my phone and go to the bathroom. I need to think. A supreme rage overtakes me. Fuck him!

- But is he right though? - Shut up, he is not!

After a couple minutes I head back into my room, target my phone, and see that I have two unread Snapchat notifications from Brian:

Brian: "Come on, I can't stop thinking about that mouth. It's SO satisfying. Don't be mad man, I was only joking. I don't think you're a sissy. Let's just finish this thing. I know you want to."

Brian: "Hello? How about we make a bet?"

'Bet'. Even the word now sends me into a mental breakdown. I can't make another bet with him!

I notice now that my cock is painfully and shamefully erect. Ah! Everything is happening so fast! I reply in a hurry:

Me: "Lol. No thanks man."

Brian: "Come on! Lol. If you come over my place tomorrow and talk, I will delete the picture right in front of you."

Me: "I don't trust you. And what happens if I don't come over? This isn't a bet, this is blackmail."

Brian: "Nah man, I'll never show anyone. Fine, no bet. But if you don't come over I guess you're okay with me keeping it to my spank bank? Lol."

What is going on?! Too much is happening! My boner stretches my underwear painfully. I don't know what to say, I just want to stop talking. --

Me: "Fine, whatever. I'll come over and you delete it. You can talk to me but I'm not staying long.

Brian: "My parents won't be home all night. I'll be home smoking and chilling most of the night. Wanna stop by around nine? I can smoke you up and apologize and you can see me delete the pic. My address is [REDACTED]"

Me: "Fine. I can't be long. I can do nine."

Brian: "Cool, yeah, def need to talk in person. Seeya then!"

I shut down the app and lay completely still on my bed. I feel as if my mind hasn't caught up with the present. For a few peaceful moments, I am happy. At least it is over. I feel almost numb to it all; resigned to what the universe has in store for me.

Then, my mind catches up with the present: I don't know what to think first! The fact that Brian took a picture of me post-facial? OR the fact that I'm pretty sure I just agreed to go on a-a --

DATE: It's the Next Day.

I never 'acted' on that boner the previous night. I just need to get through today, which has so far felt like one of the longest days of my life. The clock seems to know of my upcoming 'talk' with Brian and is apparently having the time of its life messing with me.

I don't even remember what I did that day...Eventually though, I remember staring into my mirror:

What am I feeling? - Scared.

What am I wearing? - Cozy stuff.

What's not gonna happen? - Gay stuff.

What time is it now? - 8pm already!

Almost time for the date? -Yes, but it's not a date.

You sure it's not a date? -Yes I'm sure!

You talking to yourself? - Uhhh...

You should prep your 'straight' asshole. - Fuck you!

Are you gonna tell them or am I? - It looks bad for me, and besides, they don't need to know.

It's about honesty. - Ugh, fine, whatever.

(Sigh. Okay, so honesty time: Ever since Winterfest, the showers I took at home were...'different'. It was like something switched in my head. Most days I would let loose in the shower; jerk off without judgment. Now comes the part where you don't judge me. Ahem, I didn't play with just my dick in my showers...I would soap up my fingers and play with my virgin hole; spreading and fingering myself as I jerked off. I learned quick that I loved the feeling of cumming with fingers stuffed knuckle deep in my butt. I didn't try to anal-yze this much at the time. Again, I didn't judge myself. It was just masturbation, and that's not gay. One rule though was that I could not think about Brian. Even though each time I shamefully kind of wanted to, a little. Don't judge! Anyway...now you know.)

--Ahem, it was now less than an hour from my 'meet up' with Brian. I decide to take a shower (Remember, don't judge).

I get undressed and hop in the shower. After I get wet, I quickly decide to do something I never do: I sit down during the shower. I'm not sure how long I sat and let the steamy water hit my upper back. I felt safe, it was nice. I then broke my one rule -- I thought about Brian, and all the shit he's done to me.

He's such an asshole!

I sat up some and pushed myself forward until my hands touched the porcelain floor.

Brian has used me and tricked me at every encounter!

I was now on all fours and soon let my head rest and positioned my rear up. The warm water sprayed around my porcelain white butt cheeks as I reached back some and rubbed my wet balls and played with my dangling little flaccid cock. It feels good and relaxing to just lie like this. My body was moving on it's on though, doing whatever felt best (again, there is no judgment in the shower). I began soaping up everywhere, but paying special attention to my innocent backdoor.

Tremble

The shower bulls-eyes my virgin-ring. I arched my back and leaned into the showers steamy stream. Curious, I leaned down more, stopped playing with myself, and spread my ass-cheeks apart. I moaned as I felt a pit in my stomach grow and grow until finally I thought intensely about Brian. I thought about his cock and what It would feel like inside of me. Then—I couldn't breathe! I was judging myself! I almost cried as I realized how hard and aroused I was with my cheeks spread wider than ever before. My cock pulsing under me as I squirm around. I know what I want to do next...I wet up my finger and slowly penetrate my exposed asshole. My one wet finger became two as they explored deep and around the inner walls of my ass. I tried to open myself up more and more as I thought about how Brian's cock stretched my mouth.

His cock would destr--

Moan

I then sunk my fingers deeper into my ass than ever before. I started fingering my hole slowly as I felt the alien pain of anal penetration. I felt so funky and strange. Suddenly, my cock begged for release. I quickly removed my fingers from my trembling asshole and jerked my confused cock.

AHH!

I shudder and moan as multiple long and heavy ropes of cum squirt embarrassingly into the damp shower floor below.

It takes me a while to collect myself and rise from my submissive position. I then think about the hold Brian has over me. He's invaded my mind and highjacked my sexual identity!

I dry off after that experience and get re-dressed. It was getting later now. The panic in my chest rose throughout the day as the sun descended. I look out the window of my house and see only darkness. I don't know how to feel anymore. I hope seeing Brian again will help shed some light.

It was now close to 9pm. Brian messaged me and told me he was home. I got dressed and looked in the mirror. Staring at my reflection, I realized I wasn't afraid to see Brian...I was afraid I wanted to.

I get in my car. I was like a zombie. I didn't think. I didn't even listen to music during the drive. It would've been a delightful silence if my teeth weren't chattering from nerves. Soon though, I arrive at Brian's house. It's pretty big and royal-looking. I quickly leap out of my car and speed-walk towards Brian's door. An old decrepit lion statue stood watch out near his front steps. It somehow looked more priceless the more I noticed it's various cracks and deformities.

My nose is inches from the door now. My teeth finally stop chattering.

Silence.

Then, I see the front door pull inwards, and then, Brian. (About him: He was scruffier than I remember. Tall and well built. He looked like he could break me in half. He was wearing sweats. Shit.)

He cheerily greets me and welcomes me inside.

--Awkward for minutes--

He leads me around his parents house some. He seems so excited to see me that I keep forgetting to hate him.

"Did you want to smoke?" Brian said as he sat on his living room couch and lifted a dense joint.

We smoke some together and I eventually kinda forget why I'm even there. We start talking about school and stuff and eventually he starts playing a movie on his huge TV.

'Detective Pikachu' plays

Brian keeps talking to me as we smoke and the movie starts up. He still seems super excited to see me. I don't know why I feel so nervous being around him.

I eventually get too high and wrapped up in the movie.

Then—near the middle of the movie --

"So did you get lucky this semester?" Brian asks in a playful tone.

"Nah, nothing." I reply somberly.

"That blows. Oh!"—He turns to me with a huge grin— "Did I tell you I finally hooked up with Alison?!"

(Context: Alison is basically our only mutual friend. Her and Brian go to the same college. I knew her for most of high school. She is also one of the hottest and nicest girls I've ever met. I've had a light crush on her for years...but so has every guy, I'm sure. She had a boyfriend of like five years. Then she was single for a bit. Then she had another long term boyfriend and they recently broke up....I can't believe Brian hooked up with her.)

I stare at him for a while: Looking for the lie somewhere on his face...but I don't see it.

He's telling the truth.

—I'm feeling so many things in a moment: high, aroused, mad, disappointed, impressed...jealous.

'Detective Pikachu' continues to play

"No fucking way!" I say astounded.

He proceeds to tell me in detail what happened: Basically he's the luckiest guy in the world. The story he tells is too dull and believable not to be true. But basically he was just at the right place at the right fucking time. He also proceeds to tell me in detail how they fucked: How her body felt. How her pussy felt. How wet she got. How he came on her back. How his toes curled...

Fuck him.

—If you would recall, Alison is basically the kindling that started this gay forest fire in my life. She was the reason me and Brian met. Talking about Alison got us both hard that first night of the 'Bet'. SHE was the fucking reason we started that BET; which I ultimately lost. The bet that sent me here -- into this gay conundrum.

Fuck her.

He fucked her? And he's tricked me into blowing him? Twice! Why do I keep forgetting? Why am I sitting here watching a movie with him??

I thought I was cool with being maybe 'bi' or something. But months of no contact after he fucked my mouth (twice!) has sent me back into straight rehab. I was gonna forget all about him. I don't know anymore. All I know is I feel pissed and like some submissive sissy.

I also remember feeling like a chump here: He gets to go to college and fuck the hottest girls and live away from home and have fun?
Meanwhile I commute and get a facial? How fair.

"Hey." Brian says.

—I'm snapped back to reality.

Brian places his hand on my leg.

Gulp.

"Sorry I sent you that picture last night by the way. It was just a joke." he says sincerely.

"Yeah, delete it." I try to growl.

Brian giggles.

"After the movie, I promise. -- It's just funny you know, that we did what we did. And you're just the coolest and chillest person. And really fun to mess with....Its so hot to think about. Is it like that for you?" He says, meeting my eye.

His hand moves towards my 'Pikachu'.

I gulp hard. I look down at his hand, which is now resting on my upper thigh.

"Yeah kinda. I feel pretty shitty about it sometimes too." I say; shaking with nerves.

"Don't." Brian barks with a commanding tone.

"It was just hot for us. That's it. I wanna do things with you. I do wanna do it again." He adds with forceful clarity.

Fuck. Why am I surprised and yet not surprised at all?

—I gulp hard again.

Suddenly; I feel months of pent up anger and sexual confusion start to boil over in me --