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  • Paul's First Assfucking Pt. 01

Paul's First Assfucking Pt. 01

My name is Paul, I am 40, tall, athletic, handsome and masculine. My girlfriend Michelle, is a cute 21 year old college senior with long black hair, a slightly curvy body and big boobs with sand dollar like nipples. We have an amazing sex life and often fantasize about threesomes and foursomes. Usually, I am very dominant sexually with her and the other women I get with (our relationship is open). But, I have long fantasized about getting with other guys. In these fantasies I both give and receive hard anal sex. Michelle and I are so open with each other that I share my homo-erotic fantasies with her. We even bought her a strap-on and every few weeks, we reverse roles and she gives me a good, hard ass fucking. But still, I had yet to get with a guy and really wanted to try it.

One day, I was by myself having a drink at a local wine bar and I met Garry. He too was tall, athletic, very handsome and masculine. We were having a great conversation and I told him about my girlfriend, mentioning that we are into threesomes. He perked up and I just went for it and directly asked him if he would be into a threesome with us. He said very enthusiastically yes. So I got his number, had him send me a picture and showed his picture to Michelle. She was into the idea. So we arranged to have Gary over to my place for a drink.

The day before our meet, I sent Gary a text saying be ready for AAAnything, hoping he would get the hint to prep his ass for anal.

He got the hint saying, "I hope you like a tight asshole, I know I do."

For me and Michelle's part, we both prepped our asses for anal. Michelle usually doesn't like anal but for this occasion she thought it could be hot to get double penetrated. So, I spent about an hour, licking, fingering and anal plugging her ass to get it ready for penetration. After, I cleaned myself out, I left my ass alone. I wanted it to be tight if Gary took my anal virginity.

I put fresh candles around my apartment and little dishes of coconut oil in key places. When Gary arrived around 7:00, my place had a very, relaxing sexual atmosphere. I got us three glasses of wine and we all sat on my couch, Garry in the middle. I went right into talking about sex and asked Gary if he had ever been with a guy before. He responded that he was straight but really liked sex with the right guy and had previously had two long term male fuck buddies. I joked that maybe, I could be his third fuck buddy. To this he just gave me an intense look, grabbed the back of my head to pull me in and kissed me hard.

I was engaged in my first make out with a guy and it was fucking intense. Our mouths were both very wet and our tongues explored each other freely, our hands wandered from each other's chests down to our dicks and asses. We were instantly both hard. From what I could feel outside his jeans, Gary's dick was quite large. I soon found out just how large because Michelle took off both our pants and boxers and began going back and forth sucking our dicks.

Gary's cock was cut and beautiful. It was thick enough so that Michelle hardly had to tighten her lips around it. It was about 8 inches long. When Michelle sucks my cock she struggles to get all 6.5 inches in her throat. With Garry's cock, she wasn't able to get about two inches down.

So Garry roughly commanded her, "Put my whole fucking cock in your throat".

Being naturally submissive, Michelle took Gary's huge dick all the way down her throat but after a few seconds came up gagging.

I couldn't resist any longer and took Michelle's place sucking Gary's cock. It was smooth, hot and tasted so fucking manly.

After licking and sucking for a few minutes, I got on my knees, looked up into Garry's eyes and said, "What do you want to do stud?"

Gary replied, "I want you to take my whole cock down your fucking throat."

I was determined to outdo Michelle and proceeded to push my head down until Gary's whole cock was in my throat, I too was gagging and came up drooling all over Garry's massive cock. But I went right back to work, sucking and licking my way down to his balls. Garry propped his legs up which allowed me access to his sexy asshole. I eagerly licked it, slobbered on it, sucked it and tongue fucked it. I fucking loved Gary's butthole. It tasted sweet yet manly, like a mix of coconut oil and sweat. In the meantime, Michelle licked and sucked my asshole.

I heard her say, "I'm not going to stretch you out with my fingers Paul. I want you to be really tight for your first real cock."

I pleaded with her, "Please just put one finger in so I am a little stretched out."

She replied, "No baby, take Gary's big dick like a man. His cock will stretch you out. And if you act like a sissy, I'm gonna tell him not to use any lube."

Secretly, I was happy that Michelle was forcing me to take my first real cock like a man and I also knew that if it hurt too much, I could get her back later by ass fucking her without lube.

After a few minutes of me sucking Garry's ass and Michelle sucking my ass, Garry asked me "Are you ready to take my dick in your sweet little asshole?"

I looked him in the eyes submissively and said "Yes honey, I want you to fuck my asshole. Make me take your big cock like a man".

I then laid down on the couch with my legs back towards my head. My pink asshole was exposed for Garry. I diddled my tight little butthole and stared wide eyed at Gary's huge cock. I honestly wondered how he would fit it in. Garry looked at my sexy fuck hole intensely and jacked himself off. Meanwhile Michelle sat next to me and ran her fingers through my hair. Apparently she was going to help me take Garry's massive cock.

She then looked me in the eyes and asked, "Are you ready to take that big, beautiful cock baby?"

I responded, "I think so... but it's so much bigger than your cock Michelle, do you think I can handle getting pounded by it?"

Michelle said, "I know you can take it baby. You are going to give Gary so much pleasure and I think you are going to love it too. I love you so much I am going to be here to help you."

I asked Michelle, "But my asshole is so tight, how's he gonna fit his dick in?"

She replied, "It's not loose yet baby but Gary's a stud and he'll force himself in then loosen your shithole up with his big cock." She then turned to Gary and said, "Force your giant cock into Paul's tight little asshole! Turn him into a real man."

Garry didn't need any further prompting, he put more lube on my ass and pushed his 8 inch cock up against my tight little fuckhole. Rubbing it around the entrance, Gary's big dick felt really hot and I was trembling with anticipation. Garry knew that I was a virgin and saw that my sphincter was closed up and tight but correctly read my body language that I wanted to be treated roughly. He jammed the head of his cock in, then rammed the rest of his massive member in with brute force.

As his big cock stretched my asshole to its limit I screamed with a mix of pain and pleasure, "Oh my god, your cock feels so hot and big, I don't know if I can take it. Please be gentle baby."

Thank god we were using plenty of lube because Garry did the opposite of what I asked. He roughly pulled back his cock so only the head was in then pumped his whole member powerfully all the way into my bowels. His strokes were slow but very long and strong. Enough so that each time he pumped in, my whole body was being shoved and my head was getting pushed against the backrest of the couch.

Michelle stared intently as Gary's cock shuttled in and out of my asshole. She helped by bracing my shoulder and holding my hand.

She continued to stare at Gary's dick pounding my ass and said, "Garry's cock looks so beautiful pumping in and out of your asshole! Oh my god baby you are being fucked by another man's cock and you are taking it so well!" Michelle then asked me, "How does it feel to get fucked by a real cock?

I responded "It's so sexy. Gary's cock is really big and he's fucking me so hard. I can feel it in my bowels. It kind of hurts, but it still feels really beautiful too. I love being fucked so much."

After saying this, I half expected Michelle to ask Gary to be more gentle with me but instead she turned to him and said, "I know Paul's a real man and he can take it harder, why don't you give him a really hard pounding."

Gary grunted, "Fuck yeah".

He doubled the speed and strength of his thrusts and began pounding my little poop shoot for all he was worth. He was fucking me like an animal, growling, dripping sweat and spitting on our dick/asshole connection. It felt really fucking intense, a little painful, but amazing. I couldn't do much other than hold on tight to Michelle's hand and shout out obscenities.

I said, "Shit! FUCK! You are such a stud, keep pounding my little asshole, I love it, I love your big cock!"

Michelle continued to brace me all the while staring mesmerized at Gary's cock jack hammering in and out of my shithole. She was biting her lower lip and her nipples were erect. She looked as horny as I have ever seen her and I'm sure she would have been rubbing her pussy if she hadn't been helping me take Gary's giant tool in my asshole.

She told me, "I can see Gary's big cock pounding in and out of your asshole baby. He's pulling out to his sexy head and pumping all the way in and his big, heavy balls are slamming your ass. He's stretching you out so good. Your asshole is getting so loose you could probably take two normal sized dicks at the same time. I'm so proud of you Paul, you're taking it like a real man."

Then for a brief moment Michelle made intense eye contact with Garry and challenged him, "Show us what a stud you are, pound Paul's ass harder and get rough with him".

With that, Gary put both his hands around my neck and choked me. I loved it and loved it even more when Gary came in and kissed me hard. When he came up from our kiss Garry maintained intense eye contact with me, looking at me in a loving but very dominant way. MIchelle, while still holding my hand began tung kissing Gary.

She then suggested, "I bet you could get your cock deeper and pound Paul even harder if you took him from behind."

Gary roughly pulled his dick from my ass and forcefully turned me over, using my neck and head for leverage. He pushed my head down and moved my hips so my ass was in the air.

I heard him say, "God Paul, your asshole is so stretched out and open. It looks so sexy."

He proceeded to aggressively tongue fuck my asshole for a few minutes. His ass was in the air and Michelle took the opportunity to lick and suck his studly butthole and cock. Then without warning Gary grabbed my hips hard and pushed his cock back into my bowels. He began pounding me even harder than before and he was so deep it felt like he was moving my stomach around from the inside.

Michelle held my shoulders and asked, "Do you like the rough pounding you're getting baby?"

I responded, "It's so fucking beautiful. Am I taking it well?"

Michelle said, "Yes, you are taking it like a real man, I love you so much and am so happy I am helping you get fucked."

She once again turned to Gary and said, "Paul's a stud and I think he needs it even rougher."

Then she grabbed my neck really hard with both hands, choking me. This drove Garry wild and he began jackhammering his cock in and out at lighting speed. He grabbed my hip really hard with one hand and with the other hand slapped my ass red. This relentless pounding continued for over 15 minutes. During this time all I could hear was heavy breathing, moans and Michelle grunting lots nasty little obscenities like "God Dammit, Fuck!, Shit!, POUND HIM!, Fuck Him!".

I think Michelle wanted to taste some cum because she took the dirty talk to the next level and shouted, "Fuck, Garry you're a stud. Fuck Paul's sweet asshole like there's no tomorrow. Fuck him so hard he falls in love. Drain your balls into his intestines."

At this point Garry's body stiffened up, he grabbed my hips with all his strength, pushed his cock as deep as it would go and began pulsing his beautiful baby batter deep into my bowels. MIchelle saw Garry cumming and choked me so hard I could hardly breathe. I could feel shot after shot of Garry's beautiful seman flooding the depths of my ass. He must have cum for a solid minute and emptied half a cup of man chowder into my bowels.

After he was done cuming, he pulled his cock out my ass hard, turned me around so I was facing him kneeling and forcefully shoved his still hard cock all the way down my throat. He firmly held my head in place even though I was gagging. I could feel the last of his sperm draining from his cock and balls into the back of my throat. After a couple of minutes of gagging me with his massive dick, he softened up, took his cock out, laid down next to me, lovingly looked into my eyes and softly kissed me with his sexy tongue.

Michelle opened my legs and sucked up the large amount of cum oozing out of my now very loose asshole. After she got all she could, she kissed me, spilling a sweet mouthful of baby batter into my mouth. I savored Paul's wonderful sperm then greedily swallowed it all up. Michelle cuddled me from the back and a I cuddled Gary from the back. The three of us drifted off to sleep for a little while.

To be continued...

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