My Best Friend's Girl

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It was such a bad idea.
5.6k words
4.18
46.5k
75

Part 1 of the 2 part series

Updated 06/10/2023
Created 08/31/2021
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All characters participating in any sexual activity in this story are WAY beyond the age of 18. Like 31 and 35 to be exact.

Warning: Anal, big dick and hetero sex is contained in this story. Maybe a BJ as well. Depends on how it plays out. Cunnilingus too, now that I think about it. Maybe some finger action. I'm not really sure yet. You know what? Let's just see what happens.

Hayden D. Linder

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I was at my buddies house catching the game along with several of our friends. My team was losing. But Roger's team was kicking ass! And he was drinking like it. His wife Merrideth mentioned he should slow down several times throughout the evening. But he'd been drunk most of the day and was too far gone by the time any of us realized it.

Roger and I had been friends since college. I'd even been one of the Groom's men at his wedding. Which was over ten years ago, now. Merrideth and I had met while they were dating and had become friends long before their wedding day. I always liked her. She's a good person. Lots of brains. And she is lovely. I mean, blondes with big boobs don't actually hold a special place in my heart. I like them, but I could just as easily go "gah gah" over a full figured redhead.

That being said, Merrideth was beautiful. Wavy blonde hair, blue eyes, C cup breast and an ass that was to die for. Today she was wearing a black pleated miniskirt. Black slip on flats and a white halter top with some kind of built in bra. I noticed because it showed off her perky nipples. God bless her.

Once the game ended that night Roger's inebriation became even more apparent. He was bragging loudly about how much Merrideth liked it in the butt. Judging by how red she became I understood someone should "gently" try to shut him up. I stood up to go over to him when some of the women had convinced their men it was time to go. This distracted Roger from his rant with,

"You guys aren't leavin are ya?" He asked.

"I'm afraid so,Roger." One of his work friends replied as he gripped his shoulder before following his wife out.

There were others leaving as well. Which seemed to deflate Roger's mood. I approached him and managed to convince him it was late and he had an early day tomorrow. He didn't. This was Saturday but he was far too drunk to realize that. It did make it easier to get him shuffled off to bed though.

"Thank you." Merrideth whispered to me as I made it back to the kitchen.

I shrugged to her. "He's an asshole when he's drunk. Most people are." I smiled.

The party continued for another hour before people started trickling out. Once I realized the party was over I grabbed a trash bag and began cleaning up the backyard. I had to grab a second bag to finish up. By the time I had the backyard in order everyone had left and Merrideth was staring at a large pile of dishes in the sink.

"I'llllllllll deal with it tomorrow." She stated as she threw her hands in an act of futility.

I laughed and took the two trash bags outside to the trash can. She was in the kitchen drinking a glass of wine when I returned.

"Thanks for taking care of the trash, Frank."

"Not a problem." I smiled as I grabbed a beer from the almost empty cooler. "Good party, huh?"

She rolled her eyes. "Uhhhh yeah."

I laughed again. "What?...Roger?"

"Yeah,Roger. I cannot believe he... ARGH!" She yelled in exasperation. I laughed again. "It's not funny." She whined. "What do they think of me? All of our friends heard him."

"They -think- he was drunk."

"God, I hope so." She said before taking another sip of wine.

"Although he -did- make you sound pretty randy."

"Would - you - shut - up." I laughed some more at her discomfort. "You're horrible." She commented.

I was still laughing as I sat down my beer and took some of the trash from the countertop to the kitchen trash can. I stated, "Admit it. You're just too hot for Roger to keep quiet about." Right before I slapped her ass!

I think the only reason she didn't deck me. As she slowly turned with raised eyebrows and a furious look on her face. Was because I held my clenched fists to my chest and had a horrified expression on mine.

"I am sooo sorry Merrideth. I don't know why I did that. I... I..."

It was her turn to laugh as she shook her head. "That was (not) OK. But your face..." She laughed some more. Eventually I got over my self repulsion and laughed with her. "What were you thinking?" She asked.

I shook my head as I thought about it. "Too much beer, for one." I pointed. "And... I guess Roger talking about your butt got me thinking in the wrong direction. And suddenly I was in "Standing in the kitchen with my girlfriend" mode."

She nodded. "We probably are too relaxed around each other to be drinking." I shrugged and nodded in reply. "Plus - it's not like you'd know what to do with it if you got it." She ended with a condescending smile.

Now, this is the part where -most- men would come up with some macho bullshit about what they could do to her backside. Which would've turned her off. Because she would see it as being a little pathetic. But Merrideth, by this time, was one of my oldest friends. She was intelligent, beautiful, charismatic and a genuinely good person. So I instead opted to...

(LIE.)

"Yeah, you're probably right, actually." I half cringed with a nodd.

"What?"

"I've uh... never done that before."

"Oh, bullshit!"

I laughed and shook my head. "I really haven't"

"You're like Roger's supermodel best friend. And you expect me to believe no woman out there has ever let you poke her in the butt?" I shook my head again. "How... Why!?" She almost yelled.

I gave a shrug, again. "I think they may be a little intimidated."

Her left eyebrow rose as her right eye half closed. She looked skeptical. "Really." She stated.

I laughed and nodded. "Look, a couple of months ago I was dating a girl named Amy. Things were going well. We're back at my place and start easing out of our clothes. I take my shorts down and he springs out....Next thing I know, she's thrown on her sweatpants and is sprinting for the front door. I chased after her. She didn't bother to put her shirt on until she was streaking across my lawn. I yell, "Why're you leaving?" To which she replies, "I - do not - want - to die!" Merrideth was bent over laughing by this point. "And I'm just standing in my doorway with my dork sticking out. Like an imbecile."

It took a minute but Merrideth got control of her laughter. "Oh my God." She wheezed. "Oooohhhhh." She exhaled as she caught her breath. "That happens a lot, does it?" She smiled.

"Not usually that bad. But, yeah. Women can get a little shy once I drop my pants."

"Uh huh. OK, let's see this magic penis."

"Excuse me?" I laughed.

"Come on. {Show me the mighty schlong that allllll women fear.}" She said in a deep foreboding voice.

"No." I laughed.

"Hey!" She pointed at me. "You slapped my ass. You owe me. Now whip it out "tripod." She said with air quotes.

"Alright." I sighed. "But he's not exactly excited right now."

"PuhLease. You're a dude. He'll get excited the minute he hits fresh air."

She wasn't wrong. I was wearing sweat shorts so all I had to do was pull the elastic band low enough to free my cock and balls.

"Holly shit, Frank!" She gasped.

She was fixated on it so she didn't see my smug nod. She stepped closer, hesitating on what to do while she stared. I watched for several moments until I saw her gently reach out and take hold of my cock. I forced myself to stay silent as she slowly slid her hand down the shaft.

"I can't grip it. It's too thick to fit in my hand." She said as she gave me several soft squeezes.

"You can see why some women might be a little fearful of it. Right?"

"Ha ha. Uh yeah." She nodded as she bit her lip.

After a few minutes of her gripping and squeezing me, I asked, "Do you have any suggestions?"

She paused before nodding in reply. "Ummmm, well, I mean, you'll need lubricant. Uhhhh..." She released me and walked to one of the kitchen drawers before returning with a bottle of baby oil. After she uncapped it, she ran a line down the shaft of my dick. She recapped the bottle and set it aside before returning her hand to stroke the oil around every inch of him. "This should make it easier to get in."

"Alright." She looked up for the first time since she saw my cock. "But you have GOT to be gentle, Frank... You could really hurt M... someone with this thing." She was still stroking and staring as we talked.

I slid my left hand under her skirt, up her thigh and gently squeezed her right ass cheek.

"I always have to be gentle and slow with this guy." I replied as I squeezed her ass again. She licked her lips before biting her bottom lip again while nodding. "Do you think you could handle him?" I asked as I eased my hand deeper into her cleavage to give a good firm squeez of her ass.

"I..." She shook her head. "I'm not sure."

"That's alright." I said. Then I turned her and walked her the few steps to the kitchen island. I could feel her shaking with nervous tremors before I leaned her forward.

"I can't believe I'm doing this." She said.

I eased her skirt up and out of the way. "It'll be fine." I whispered back as I slid my right hand into her crack. Rubbing over he anus and on to stimulate her pussy. She kicked off her flats before slowly spreading her feet farther apart. Resting her elbows on the island, she whimpered. I continued to rub her crotch. She was starting to give me a few timid moans. But I kept gently rubbing her until her hips gave a few small easy bucks.

I slid my hands up to the waistband of her white cotton bikinis and pulled them down to just below her ass. Using my thumbs I eased her cheeks apart before nestling the head of my dick against her anus.

"OK.OK.OK.OK." She whispered while her head was nodding like she was trying to convince herself it was going to be alright.

Slowly, I pushed against her. I felt her start to move forward. Lifting up on her tiptoes. "Ah.Ah.Frank?" I released her cheeks.

Slid my hands to her hips to hold her still while I continued to apply more pressure to her rear. She began to shake even more. Her sphincter had barely begun to spread for me. I continued to pull. Her sphincter felt like a 1 inch thick elastic band. The far end was barely starting to spread. While the back had been forced open by the girth of my head. We were still a long way from the largest part of my head spreading her open. But that didn't change that she had a very large amount of cock up her ass right now.

I allowed my cock to slip back almost all the way out. Before slipping it back in and pumping gently against her very resistant little hole. This caused several worried moans to erupt from Merrideth. As her ass was collapsing and re-stretching. I caught her peeking over her right shoulder. I pulled her a little harder against me. Allowing even more of my cock head to force her opening even wider. Her mouth fell open but she couldn't look away. I began to give her semi hard pulses with my cock. Bouncing her against the head. These elicited small squeaks and more whimpers from her.

After several minutes of this she hung her head. I stopped the bounces and pulled her cheeks out of the way again before applying a lot more pressure. I felt her little ass spread open even more. Merrideth gasped out a cry as she looked back at me in fear. I eased her cheeks back into place but kept up my steady pressure on her backside. Rubbing my hands up her back I shushed her in an attempt to keep her calm. I could feel the thickest part of my cock's head was almost in. Once it reached the middle of her sphincter it would only need a small nudge to finish.

I slid my hands up to grip her rib cage as I pulled her back against my chest.

"We're almost there." I whispered.

She gave me a dewy eyed nod as she bit her lip again. I stepped her forward to force her stomach against the edge of the kitchen island. Once I knew she couldn't squirm away. I kissed her behind her ear and started nudging deeper into her delectable ass.

"Oh fuck!" She yelled. Then, "Ung." She grunted as I felt her anus suck me in. "OK...OK..." She was nodding again. "Frank just takeOOOHHHHHhhhhhhhh...." Her head fell back against my shoulder.

She thought I was giving her time to adjust but?.. I had started easing up her ass the moment I slipped in. It only took her a few moments to realize and go limp from the fullness of it. I eased into a good hard push against her as I bottomed out. She groaned when I moved my hands to grip her breasts and pull her tight against my while my hips dug into her. I held that position for a few moments before slowly pumping in and out of her.

I felt her body quiver as the first small orgasm went through her. It was all I could do to keep from giving her long hard strokes. To calm my urges I took a deep breath and let it out before bending her forward over the island again. Gripping her hips I slowly slid my full length back and then eased back in.

"Ohhhhh, fffuuuuuck me." She moaned as she lay her forehead on the backs of her crossed hands.

I kept sliding deep long slow strokes in and out of poor Merrideth in an attempt to keep my baser desires at bay. I think she could feel it. Because it wasn't too long before she looked back at me. She was breathing through her mouth from the strain of it all. But she kept licking her lips like she was dehydrated. Her lidded glance made me want her even more.

My arms were shaking from the self enforced restraint. And I soon discovered she had noticed. Her right hand slid up my right forearm. Feeling the quaking that coursed through my muscles.

"Shit, baby. You really needed this. Didn't you?"

I nodded as my strokes became a little faster. She slipped her hands to the edge of the island for support. Then looked back at me as she arched her back. Pushing her ass back at me. I pulled her hard against me. Hard enough to make a loud slapping noise as my hips hit her rear. She yelped out a groan while I held her tight against me. Every millimeter if my cock felt like it was in a tight grip.

I forced myself to breathe. Then slid out of her before driving back in for another ass slapping connection. I watched her ass quake from the impact as she moaned louder. I slid out until the back of the head was touching her sphincter. Then slammed back into her. Which got me another groan. I kept fucking her slow and hard for several Minutes while sweat poured down the both of us.

I could see her camisole top was soaked. I knew if I didn't pause, I was going to give in and blow my top way too soon. I was still coherent enough to know that Merrideth's ass was a once in a lifetime opportunity. And I wanted to savor every single moment. I slammed into her one more time before sliding my hands up her back to massage her shoulders. Merrideth gave a satisfied hum before slowly wiggling her ass against me.

I pulled her up against me again and kissed her behind the ear once more. Her hair had become heavy with sweat. I brushed it out of the way to get a tastier connection to her sweet neck. She surprised me by turning her head toward me to slip her tongue into my mouth.

I took a moment to slip the straps of her top off of her shoulders and down until she pulled her arms out. She moaned into my mouth when I squeezed her sweat covered breasts. She started giving slight bucks with her hips when I gently tugged her nipples. I held her nipples just hard enough to keep a hold of them. She broke our kiss with a gasp when I lifted to heft the weight of her magnificent tits.

"Not too hard." She whined. I lifted higher. "Ahhh, please?"

"You want me to stop?" I whispered as I tugged her breasts a little higher.

She bit her lip and nodded a reply with her eyes squeezed shut. I kissed her again. "Then start thrusting back at me." I whispered again.

She forced herself into a bent over position. Placing her hands back on the edge of the island for leveredge. She made sure to look back at me as she slowly pushed back at me. I had released her nipples when she bent forward.

Now, I grabbed her delicious hips again and gently pulled her back to meet me as she thrust. My urges had abated, for the moment. So we spent several long minutes pumping against each other with mild steady thrusts. She suddenly locked up and moaned as her ass quaked. It was all I could do to keep from picking up the pace. Merrideth stopped moving. Breathing hard into the countertop of the island.

"Oh my God." She breathed.

I took a few thrusts to build up to a slight ass slapping action. Merrideth gasped and moaned every time I bottomed out in her. When she groaned loud and spasmed another orgasm, I started pumping into her even faster. Her ass quaked with every impact. Her moans came sporadically but her grunts grew louder with every smack. It all became too much for me as I threw my head back and moaned with her.

I don't know why this affected her, but when I looked back down she was looking back at me with gritted teeth. Forcing her rear back at me with determination. I began pulling her against me as fast and hard as I could. For her part, Merrideth was pushing back at me as hard as she could muster. Until I felt my balls churn. From the look on her face, I could tell Merrideth felt it too. We kept slamming against each other for a few more moments before my cock surprised me and blew up inside of her.

Merrideth quickly looked forward. "OH!" She gasped in a yell.

I pulled her tight against me as the first round launched into her. Then pulled back before ramming myself back in for the second round to shoot off. She gave another exhausted gasp. It felt too good to be inside of her so with every round that came after that. I pulled her tighter against me as I shot off. I didn't count how many there were but they were glorious. We stood there, sweating. Merrideth with her right cheek resting on the island while I dripped on her floor.

After several minutes of trying to catch my breath, I took off my shirt to dry myself off. I would have dried off Merrideth... but she looked really good covered in sweat.

I pulled my cock out until only the head was still in her. Which is when she moaned a sad kind of whimper. I leaned forward and kissed her. Then eased the rest out of her to the sound of,

"Ohhh. Oh. Ah."

I went to the sink and used a dish towel and soap to clean up. Once I had the cloth cleaned and re-soaped I walked over to her and washed her thighs. Which garnered me a satisfied moan of approval from Merrideth. I washed her hoochey, cause it was all kinds of sloppy. Which got me a very satisfied moan. And last I cleaned up her glory hole before throwing the rag on the floor. Someone would wash it in the morning.

With that I cradled Merrideth in my arms and carried her to the guest bedroom. I took off her sweaty clothes and tucked her into bed. While I went back to the kitchen to collect her shoes, my wallet and phone and made sure I wasn't forgetting anything.

With that done I came back to the guest room and locked the door. I stripped off my clothes and spooned Merrideth before passing out.

I woke in the morning to Merrideth resting her head on my chest.

She looked up at me and said, "Well that was fucked up."

I nodded. "Uh... yeah." I sighed.

We stared at each other a few moments before we heard the door to the Master bedroom open and close. A moment later we heard a few taps at the door to our room. I held Merrideth tight which made her look at me. I put my finger to my lips to sign her to be quiet.

"Merri? You in there?" We heard through the door.

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