My First Anal Sex Experience

Story Info
How I turned gay after finding out my girlfriend cheated.
1.4k words
4.33
7.3k
8
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Story of how I caught my first dick.

I never thought it would happen to me, but it did. My girlfriend cheated on me, and I found out in the worst possible way. A mutual friend saw her making out with another guy at a party and told me everything. I was devastated and couldn't believe that the person I loved and trusted would do something like that to me.

I confronted her, and she tearfully admitted to everything. I was angry, hurt, and confused. I didn't know what to do or how to react. I felt like my whole world had been turned upside down.

I met my girlfriend a year ago at the national library. She was the most beautiful thing I had ever seen. I approached her and we started off as friends. I'm actually the one who friend zoned myself with my approach. We went on to date three months later after awkwardly admitting that I like her and want her to be my girlfriend.

Our relationship started off at a high gear. She gave me butterflies and rainbows in my tummy every time I thought of her. I spoilt this girl like no man's business. We would go on a date at least once every two weeks and I would buy her gifts so often.

After a couple of months though she became distant and disconnected🥲. Even when I increased the frequency of the dates, things only got worse. I tried confronting her about it and she would give off a very disdainful attitude. I grew insecure over time and started calling her a lot often and would get a panic attack when I would find her phone busy.

During one argument with her she decided to open up and tell me that her attraction was fading due to the fact that I was too nice🥲. She mentioned it being a turnoff to her and that she doesn't feel like she's with a man when she's with me.

I promised to try and fix it but nothing changed. One night I called her and she didn't pick up her phone. She didn't return even after hours later. A friend of mine then called me around midday and told me about the incident. He even gave me the guy's details since he knew him.

In my anger and hurt, I started stalking the guy she had cheated with on social media. I wanted to know who he was and what he looked like. I found out his name, where he worked, and even his sexual orientation - he was bisexual. I couldn't believe it. My girlfriend had cheated on me with a guy who wasn't even straight. Yet she was telling me she didn't feel like she was with a man when she was with me.

I started messaging him, and we ended up talking for days on end. He was actually a really nice guy, and we had a lot in common. As crazy as it sounds, I even started to develop a desire for him. I found myself thinking about him all the time and wondering what it would be like to be with him.

Throughout our conversations I never mentioned my girlfriend. He asked me out after three weeks of talking. He mentioned wanting to help me explore my sexuality. I was down for that. After two months of talking we finally set up a date at his place.

I arrived at his apartment where he warmly welcomed me. We chatted for a little when he decided to break the ice by coming closer to where I was sited. He put is forefinger on my lips and then leaned over for a kiss. We both then went silent as we kissed and undressed each other. We then went to his bed. I mentioned being shy and that he should turn the light off which he agreed to.

We continued kissing in his bedsheets for minutes. After a 10 minute make out session he reached out to the corner of his bed to get lube and a condom. This was the first time I had touched his dick in the whole 10 minutes of making out. My goodness. This thing was huge. I started getting second thoughts about the whole thing which it was obviously too late for. If dicks were dogs mine was a greyhound and his was a pit bull. It was of average length but very thick and hard. I was laying on my back with my legs wide open thinking about all the events that led me here getting ready to be fucked by a stranger. My thoughts were quickly interrupted by bulging sensation on my butthole. It was all lubed up and ready to bury itself inside my guts. He slid it in slowly. Very slowly. It was the weirdest thing I'd ever felt🥲. It felt very invasive. I imagined this is what women felt when they are being raped.

When his monster cock was fully logged in, our chests together, my arms around him🥲 and my legs wide open side by side, he whispered to me, " you are my bitch now". I melted. My whole body shivered and I felt my masculinity leaving my body. If I looked at a mirror at this point I would expect to see a cute little girl. I did feel like a woman at this point.

His thrusts started off slowly and gained momentum with time. My butthole kept clenching from time to time but it relaxed eventually. If it could talk to me, I'm guessing it would ask, " what are we doing today?" I'm imagining its confusion because the act really felt weird and great at the same time.

As I laid down there being passionately railed ( oh yes he was making love to me. Medium tempo with long kisses on my neck ) all I could think about was my girlfriend getting dug out like this and how I finally got a piece of what she had. He has a monster cock. No wonder I got cheated on. Maybe my greyhound wasn't reaching all her right spots. Maybe she needed a bigger man. "Well I was with that man right now," I whispered to myself smiling devilishly at the ceiling.

After a good 8 minutes of being railed I felt his grip around me getting tighter. His monster expanded inside my guts. He was Cumming. He put his face to the side away from my face and made a nearsilent moan. You can only imagine what I was like being squeezed like that. At this point I thought to myself, " I need a boyfriend, so that we fuck raw." All those babies that were filling up in the condom, I wanted them exploding and flooding my bare ass. I wanted to know how it feels to be creampied.

I enjoyed seeing a man experience extreme pleasure and my hole being the reason for that. At some point it felt like he was experiencing a seizure. His whole body vibrated as he took one final deep thrust and paused inside. I laid there with my arms around his back🥲, legs in the air and with my booty spread wide open not knowing how to react. I could feel his cock pulsating🥲. My eyes were bulging out of my sockets during this ordeal. "Should I moan together with him," I asked myself.

Or should I go, "ohh yes! Water those buttcheeks Daddy." I stayed silent nonetheless. My eyes still wide open almost popping out of their sockets. I left him to moan alone. I left him to enjoy the last bit of my sweet watery guts peacefully. When he was fucking me, he was the man and I was his bitch as so he said. When he was cumming, I had to return the favour and be there for him at his weakest point. To hold him while he kicked his last thrusts. I dare not let a man who has fucked me so good fall off his bed.

He pulled his soft meat out of me🥲. His beaten up soldier fought a good fight but my ass won in the end. Yep. That big pit bull didn't seem so tough anymore after my lovehole had smothered it.

He sighed after a long pause with his head still on my chest. He got rid of the condom and got the both of us cleaned up. He shortly dosed off after that. I couldn't sleep on the other hand. I was thinking about how I've just let another man fuck me and how at some point I felt like he was the only man in the room.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymous6 months ago

He could of been fucked fucked 3 times a day like me from (bbc), I love a cum filled ass,from black or white guys,with 7" or more.

AnonymousAnonymous6 months ago

It was fine,but not enough fucking, he got fucked by the guy who stole his girlfriend, and he lowered himself to get fucked by his big cock and creamier. I love a guy to cum inside me, I take every cum load in my mouth and asshole, I love being cummed in, love the feeling of being filled up with cum, it feels even better the bigger the load. I let every big cock guy black or white cum inside me, no condoms,no pullout, love big cummerbund, I'd get fucked and cum filled 4 times a day, if I could,any takers.

ilikeskin69ilikeskin696 months ago

I liked ikt a lot...AL

Share this Story

Similar Stories

"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
Cuckolds Regret A man finds out cuckolding is not what he wanted.in Fetish
Blowing the Bully How can I stop a bully from tormenting me?in Transgender & Crossdressers
My Wife's Wife My wife makes me her wife with help from bff and lover.in Transgender & Crossdressers
What My Wife Doesn't Know Cheating / wearing lingerie / submission, then dominance.in Transgender & Crossdressers
More Stories