My First Time Having Anal Sex


Hey there. I’m Ricky. I am a twenty two year old male. In case you can’t tell by my username and the title of the story, I LOVE and CRAVE getting fucked in the ass. I am heterosexual and have no sexual desire to get my ass fucked by men. I prefer to get my ass fucked by a woman with a strapon, any sex toys and anal sex toys, and transwomen. Some people have asked me why I don’t want to get my ass fucked by men but I like getting my ass fucked by transwomen. It’s simple. It’s because I consider transwomen to be women.

This is my first sex story. It’s based on a true story about my first time getting my ass fucked by a woman with a strapon. I hope you guys enjoy it and please, let me know what you guys think.

My First Time Having Anal Sex

By Ricky

I am sitting at home, by myself. I’m watching Pornhub on my Xbox One. I heard someone knocking on my front door. I got up and walked to the door. I took a peek through the window to find one of my closest and bestest friends was here to visit me. Her name is Shiana Crawford.

Shiana has huge natural breasts, long dark brown hair, an incredibly sexy ass, a sexy pair of legs, and the prettiest green eyes that I have ever seen.

I opened the door.

“Hey, Shiana!” I said excited.

“Hi, Ricky!” Shiana said.

I let Shiana inside my house. She was wearing the shortest jean short shorts that were showing off her sexy ass. Black converse shoes, a white tank top, no bra and a black lace thong. I could see Shiana’s tits perking through her tank top.

Shiana is one of my closest and bestest friend that I have ever had. But we weren’t just best friends. We were best friends with benefits.

Shiana and I have had so much sex together. We’ve done so many kinky things together. Shiana literally craves sex. She has a ton of fuck buddies and has had all different types of sexual activities. A lot of her sexual activities involve making herself feel like she was the ultimate slut.

Shiana loved being treated and feeling like a slut while having sexual intercourse. She actually once told me that she loves being everyone’s cum dumpster. Shiana has been gangbanged, had a group of guys cum all over her body, a bukkake in other words. She loved getting all of her holes fucked and filled. She has a really big cum fetish, as well as a bunch of other fetishes.

For whatever reason, I was Shiana’s favorite fuck buddy and best friend with benefits. I once asked her why I was her favorite and she told me that it was because I knew how to use my dick. I asked her why and that my dick was pretty average sized. She smiled and told me that the size of the hammer doesn’t count and what does count is the pounding the hammer gives. That made me feel good about myself and boosted my confidence.

I let Shiana inside of my house. Shiana was carrying a duffle bag. As she walked past me, I stared at her sexy ass. She turned around and gave me a sexy smile on her face.

“Whatchu staring at, Ricky?” Shiana asked.

“Your incredible ass,” I said.

“Well, you can see my ass and my whole body in all of its glory here in a little bit, okay?” Shiana said.

“Okay,” I said.

Shiana looked at my TV and noticed that I was on Pornhub. She looked at me and gave me a sexy smirk.

“Looks like you were having fun,” Shiana said.

“Yeah, but now that you’re here, we can have fun together,” I said.

“Well, that depends. When will your mom be home?” Shiana asked.

“She’s staying at my step-dad’s place for the weekend, so we’ll have the entire place to ourselves. We can have as much sexy fun time as we want,” I said.

“Fuck yeah. I want you to try something Şerifali Escort new for me. Nobody that I have sex with will do it willingly. But, maybe you will if you’re comfortable with it,” Shiana asked.

“Well, what is it?” I asked.

“Okay, try to keep an open mind, okay?” Shiana said.

“Alright,” I said.

Shiana smiled at me. She has the prettiest smile that I have ever seen and has perfect white teeth. Shiana removed her tank top. Her huge boobs flopped as she removed her tank top. She slowly unbuttoned her short shorts and slowly took them off. My dick started to get hard and was bulging through my jeans. She took off her thong, revealing her perfect and amazing hairless pussy, and threw them at my face. I smiled and laughed.

“So, what is it that you want me to try with you?” I asked.

“Well, it’s in my bag,” Shiana said.

“Okay,” I said.

Shiana smiled at me.

“Close your eyes and turn around, Ricky,” Shiana said.

I covered my eyes with my hands and turned around. I heard some faint noises.

Shiana has a beautiful and sexy voice too. She talks in a way that says “I am the biggest and sluttiest whore. I want your dick inside of me”. She’s a person that I can fucking vibe with. She’s one of the most chillest people that I have ever met. She’s so open and honest. I can trust her with anything, including my life.

“Okay. Turn around, Ricky,” Shiana said.

I removed my hands from my eyes and turned around and faced Shiana. I looked in her eyes. She was smiling at me. I started looking my way down her body and saw that she had a huge black strapon attached to her body. I opened my eyes and mouth open wide because I was surprised.

“Whoa! What the fuck?!” I said loudly.

“Okay, remember. Try to keep an open mind, Ricky. I would really appreciate it and would love it if you let me fuck your ass with my strapon,” Shiana said.

“No fucking way! That thing is huge!” I said loudly.

“Please, Ricky? You don’t know what you’re missing out on! Trust me, having anal sex is amazing. You’ll love it! Trust me. And, I promise that I’ll be gentle with you,” Shiana said.

“Shiana. I love you. You’re one of my best friend’s, but I can’t do that,” I said.

“What can I do to talk you into letting me fuck your ass with my strapon?” Shiana asked.

“There is absolutely nothing you can do to talk me into that,” I said.

“Okay, tell me why you don’t want to get fucked in the ass?” Shiana asked.

“Because, it’s kind of gay. It would be painful,” I said.

“Okay, how is it gay? It would only be gay if you got fucked in the ass by a dude. And painful? I’ll use my anal numbing lube if it helps,” Shiana asked.

I said nothing. I was speechless.

“Here. Sit down and talk to me,” Shiana said.

Shiana and I sat down on the couch. She put her right arm around my shoulders.

“Listen, it’s not gay, okay? You can still be straight and like getting fucked in the ass. I understand that you’re nervous. But, please note that I would never do anything to hurt you. I care about you, Ricky. Which is why I am asking you to try it. Let’s try it, okay? And, if you don’t like it then we’ll never do it again. I pinky promise,” Shiana said.

I looked down at the ground and just thought about it.

“Okay, Shiana. I’ll let you fuck me in the ass with your strapon,” I said.

“Yay! Okay, you’re going to have to clear your body out. Here, use this water enema. Just fill it up with water and insert the tube deep inside of you. Flip this switch and fill the inside of your body fill up with water and dump all the water out. Repeat until there is Şerifali Escort Bayan no more you know what,” Shiana said.

Shiana handed me a water enema. I went to my bathroom and got naked. I filled the enema up with water and inserted the tube as deep as I could go. I flipped the switched. Water started filling up my body. It was actually kind of turning me on. The feeling of water filling the inside of my body felt really good.

After I cleaned the inside of my body, I walked out of my bathroom and see Shiana lubing her strapon with lube. I don’t know why or how, but I started to get even more turned on. I was surprised that I was getting excited for this.

Shiana was sitting on my couch, applying anal lube on her strapon. She looked at me and we stared into each other’s eyes. She gave me her famous sexy look on her face.

“Are you ready to get your ass fucked?” Shiana asked.

I smiled as my dick got long and hard.

“I think I am. I’m not going to lie, Shiana. But, I’m actually getting very turned on from this. I don’t know why but I think my ass is aching to be penetrated by you,” I said.

“Sweet. I’ll get the anal numbing lube,” Shiana said.

Shiana walked to her duffle bag and opened it. She started searching for the anal numbing lube.

“So, how big is your strapon?” I asked.

“It’s twelve and a half inches. Thats not all it does,” Shiana said.

“Jesus, thats big…wait. What else does your strapon do?” I asked.

“My strapon can also ejaculate fake cum. I can cum inside of you, on your face, and in your mouth,” Shiana said.

“Holy shit…..does it make me gay that I want you to cum inside of my body?” I asked.

Shiana looked up at me with a surprised look in her eyes.

“Are…are you sure that you’re down to do that?” Shiana asked.

“Yeah. I mean, you said I should keep an open mind and be willing to try new things,” I said.

“Okay. Fair point. I’ll fill my strapon up with fake cum,” Shiana said.

“Sweet,” I said.

“Shiana pulled out the anal numbing lube and a bottle full of fake cum. She takes apart her strapon and fills it with fake cum.

Shiana looked up at me and smiled.

“What?” I asked.

“I think you’re being very brave for doing this. Not everyone I know is willing to try new things with me in the bedroom,” Shiana said.

I smiled.

“Well, I’m actually very excited to try this. And very turned on,” I said.

“Hah. Well, are you ready to get your ass fucked?” Shiana asked.

“Just one more question,” I said.

“Of course! Ask away!” Shiana said.

“How bad will it hurt?” I asked.

“It’ll hurt at first. But the more we do it, the more your body will be used to it. Since this is your first time getting your ass fucked, I’ll apply anal numbing lube on your ass and inside your ass. That and I’ll be gentle,” Shiana said.

“Okay. I’m ready. Let’s do this,” I said excited.

Shiana stood up and walked closer to me. We started French kissing with an intense passion. She slowly started stroking my dick as we walked our way into my bedroom. I gently squeezed both of Shiana’s huge boobs.

“What position should I be in?” I asked.

“I would get into the doggystyle position. It’ll really hit you in your g spot,” Shiana said.

I got on my bed and into the doggystyle position. I stuck my ass out. Shiana moaned quietly and groped my hairless ass.

“You have the cutest ass ever,” Shiana said.

Shiana opened the container of anal numbing lube. She scooped up the anal lube and applied it to the outside of my ass. She scooped up some more lube and gently shoved her fingers Escort Şerifali inside my ass and rubbed the lube all over the inside of my ass.

Shiana grabbed her strapon and put the tip on the rim of my ass.

“Are you ready?” Shiana asked.

“Yeah, I’m ready. Do it,” I said.

Shiana gently and slowly but forcefully instered her strapon in my ass. Thanks to the anal numbing lube, I could barely feel it. I moaned quietly.

“Am I hurting you?” Shiana asked.

“I can feel it a little bit,” I said.

“Okay, Ricky. I’m going to go a little deeper, okay? Let me know if I need to stop,” Shiana said.

Shiana gently started pushing her strapon deeper inside of me, causing me to moan a little louder than before. Shiana slowly and gently started thrusting me causing me to moan even louder.

“Do you like it?” Shiana asked.

“Yes, I am. Can you fuck me a little harder and go deeper inside of me?” I asked.

“Sure,” Shiana said.

Shiana pushed her strapon deeper inside of me and started thrusting me harder. I started moaning constantly and loudly.

I have never felt such an amazing feeling of sexual pleasure. I was actually craving this. I wanted more.

“Oh, fuck yeah. Your strapon feels incredible! It’s like nothing I have ever felt before! Oh, yeah! Fuck my ass!” I moaned.

“You like my big black cock, you filthy slut? Yeah, take it nice and deep,” Shiana said.

I started to grab my blanket as I started to moan even louder than before.

“Shiana, fuck me faster,” I begged.

Shiana smiled as she started fucking my ass faster causing me to feel an intense feeling of sexual pleasure. I was moaning very loudly.

“Yeah, take my big fat cock! You like my big fucking dick?” Shiana asked.

“Yes, ma’am! Oh my fucking God, this is amazing! Fuck me as faster, harder and go as deep as you can!” I begged.

Shiana grabbed me by my waist and forced her strapon all the way inside of me. She started fucking my ass faster and harder than before. I was yelling and moaning very loudly as Shiana was fucking me.


Shiana just kept fucking me and fucking me and fucking me until I started to feel something. Something that I have never felt before. I could feel it in my legs. My legs started to shake violently.

“Shiana, what am I feeling?” I asked.

“You’re going to have an anal orgasm,” Shiana said.


Shiana kept fucking me so good until I had an anal orgasm. I screamed with an intense feeling of sexual pleasure while she was still fucking me.

“Shiana, I want you to fucking cum inside of me! I want you to fill up my ass with every single drop of your cum!” I said.

Shiana thrusted me a few more times until she forced her strapon deeply, all the way inside of me as she came inside of me. She pulled her strapon out of my ass. My ass was oozing and overflowing with fake cum.

I laid down on my bed and Shiana laid down next to me. We French kissed for a few seconds.

“So, how was your first time having anal sex?” Shiana asked.

“That was fucking incredible. I’m down to do it later,” I said.

“Well, I’m glad that you enjoyed it, Ricky,” Shiana said.

“Can we do this more often?” I asked.

“Sure, I’m down!” Shiana said.

“Fuck yeah,” I said.

Shiana was the first woman to fuck me with a strapon. It was an eye opening experience and since then I have had a sexual desire to get my ass fucked. I have been more open to trying new things that involve me getting my ass fucked.

Since Shiana fucked me in the ass with her strapon, I’ve done strapon gangbangs, double anal, deep anal fisting, anal creampies, and much more.

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