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Anal Sex With My Lovely Friend

Anal Sex With My Lovely Friend sex story

There. Drain your balls in my big, tight butt.” She ordered. I lost it. A few more strokes and then it happened. What felt like a continuous stream of spunk loosed from the tip of my dick and I drove in all the way and deposited it deep in her bowels. Then spray after spray continued. I was dizzy with euphoria and still holding her tight.

Eve was always talking shit.  We met when she was dating a friend of mine, and from the first time we hung out she was always making stupid jokes at my expense, often embarrassing me in front of the rest of our friends.  I admit I hated her a little inside because she always seemed to know just what to say to make me look like a fool.  So when one night we were playing trivial pursuit, a game I knew I was good at, I decided to try and give her a taste of her own medicine.

Now I have to say, Eve was hot.  I never would have admitted it in front of her, but I thought it often enough.  She was one of those girls that had that crazy waist to ass ratio, you know, where her waist is super thin but bloomed into wide hips and a big round ass.  She was aware of it too.  She was constantly making references to her butt, shaking it in people’s faces, and lots of other obnoxious things that clearly said she knew just how amazing she looked.  

As the game got rolling it became obvious that she and I were the two contenders.  I was surprised, she had never let on to being a trivia buff, but this was my game and there was no way I was going to lose to her.  So when she got another question right, stood up and did a little dance, shaking that big ass and pointing at me, I started to get an idea.

“In your face Mike!  Am I gonna make you my trivia bitch tonight?!” She taunted.

“Whatever, I bet I could take you out in one to one, no problem.  You’re just getting easy questions.  You know I own this game.” I replied.

“Oooh!  You want to make a little wager on that, son?” She shot back.

“What do you have in mind?” I asked, seeing this unfold perfectly.

“If I beat you at one to one, you have to let me right ‘I am Eve’s trivia bitch,’ with a sharpie, on your back, and you have to walk through campus in a pair of girls panties.” She said as she grinned, some of the other girls at the table high fiving her.

“Ok, but if I win (I paused for effect) I get to fuck your ass.” I said smugly, knowing her ego would not let her back down.  There was a collective gasp from some of our friends at the table.

“Ok, bitch, you got a deal!” She said, so smug and self-assured.

“But Eve, what about Jason?!” Krista, one of our other friends asked, concerned.

“Jason will be fine.  I’m not going to lose.  I got this.  Besides, Jason will love to see the video of Mike’s walk of shame when he gets back.” She told her, with no hint of concern in her voice.  Jason, our friend and her boyfriend was doing a semester abroad and was supposed to be back in a little over a month from now.

“Ok, then.  Sounds like the terms are set.  Let’s do this.  I got an itch that needs scratching.” I said with a grin.

“Whatever, fuckboy.  We’ll see how itchy you are in a pair of panties later.” She said, laughing along with some of our friends.

The game began, and questions after question we went back and forth, on pretty much every subject.  Eve surprised me.  She held her own and i will admit to being impressed.  If one of us couldn’t answer a question, it would go to the other to answer.  We had set the end of the game at 50 questions and as we approached it the score was 25 to 24 with me ahead by 1.  At this point I knew there would be no walk of shame, but there was still my part of the bet.

The last question, “What is the regulation width of a Canadian hockey puck?”  Eve looked confident, and a little relieved when she heard it.

“One and a half inches.” She said, standing and extending her hand to me in an exaggerated act of respect.

“Incorrect, Mike?” Chad, our ref for the game said.  Eve looked absolutely panicked.  I felt light-headed.

“Wait, that’s the right answer!” She said in protest.

“No it is not.  Mike, what’s your answer?” Asked Chad.

“Well Chad, I believe the response you’re looking for is one inch.” I said with my eyes pasted on Eve’s face.

“That is correct!  Game to Mike!” Chad said with a cheer in his voice.

“What the fuck!  No!  There is no fucking way.  He cheated!” She said in outrage.

“He didn’t see the cards, Eve.  It’s not cheating if he actually knows the answer.” Chad told her matter-of-factly.

She looked stunned.  I was soaking it in.  She couldn’t believe she had lost to me, but even more, she couldn’t believe that she was actually going to have to pay up.

“Well, Eve, I believe we will be busy for the rest of the evening.  Would you like to say your goodbye’s to everyone before we head to my room?” I said, completely unable to disguise my delight at her distress.

“No fucking way, i am not going anywhere with you.  This is bullshit and you know it!  I have a boyfriend.  I am not doing this.” She said resolutely.

Everyone at the table booed yelling, “sore loser!” And, “Eve doesn’t honor her bets!” Her face turned red and took on a worried expression.

“Mike, c’mon, this was just for fun.  You don’t really expect me to follow-through on it, do you?” She asked pleadingly.

“Eve, you would have already had me in panties making my trek through campus, and you fucking know it.  You made a bet.  You lost.  It’s time to pay up,” I said as i took a step and gave her a light smack on the ass.  She jumped, looking affronted.  I laughed.  “You have given me so much shit, embarrassed me, made jokes at my expense, and I have taken it all like a good sport.  Now it’s time for you to ‘take it all, like a good sport.’” I said with a glint in my eye, as the room erupted in laughter.  I stepped out of her way and gestured in the direction of the bedrooms.

Eve stomped her foot and then walked towards my room in a huff, as i followed.  I could here one of the other girls saying, “do you think they’re going to do it?” To which one of the guys sitting next to her replied, “she has to, a bet is a bet.”  Glad to know i had some support.

Once I got to my room I could see Eve standing inside already.  I went in and closed and locked the door behind me.

“Mike, you’re not really going to expect me to let you fuck my ass, are you?” She asked hopefully.

“Eve, you made a bet.  You were so sure you would win, and, honestly, I’ve wanted to fuck your ass since the day I met you.” I said

“What?  What the fuck, I thought you hated me?” She said looking at me puzzled.  

“I don’t hate you.  You’re a bitch to me a lot of the time, but you have your moments.  It’s just killed me to know that you have been dating Jason, because I know there is no way he is doing your ass justice.  He’s beta as hell, and I just can’t imagine him doing what the universe created that ass for,” I said, stepping forward and placing my hand on her butt with a light pop.

“And I suppose you think you’re ‘qualified’ for the job?” She asked in a playfully mocking tone.

“I might be, I might not be, but you lost a bet and it’s time to pay up.” I told her, rubbing what I realized now was one of the firmest asses for its size I had ever felt.  She was wearing leggings and I swore I was feeling bare ass beneath the fabric.  I was sort of mesmerized for a second, but came back to myself.

“You’re a dick for making me do this.  Everybody knows.  Jason will know before the night is out.  Why don’t we just call it good at you coping a feel and I’ll walk out of here.” She said as though it was the most reasonable solution to a problem that was exclusively hers.  Jason and I were relatively tight and I knew he had been fucking everything that walks while he was away.  He may be beta as fuck but he has never had trouble with women.

I gave her ass another, harder smack and said, in a commanding voice, “why don’t you just get up on the bed and show me that ass.  Don’t take the leggings off, just stick your ass in the air.”

“Fucker!” She growled as she did what I asked.  Her leggings were pink and went she got on all fours, then on her elbows, as she arched her back, I was stunned.  That ass was so big, and perfectly shaped.  Her small waist only made it seem so much more so.  The leggings were pulled super tight and you could faintly see through them.  She was wearing a thong that appeared to be white.  The leggings conformed to the shape of her pussy which looked puffy.  You could see her labia outlined perfectly.

“Damn,” I said as I got on the bed behind her and placed both of my hands on those two round cheeks.  Her ass seemed like it was just too big for the rest of her.  I gave one side of it a hard slap, leaving my hand there so it would sting a little.

“Ow, fucker, you don’t have to do that so hard.” She exclaimed.  I rubbed my hand roughly across the mound of her pussy, doing a few quick circles applying pressure where i knew her clit would be.  She gasped.

“You said my ass.  That’s not my ass, jerk!” She said with a slightly strangled sound of protest.

“Sorry, my bad,” I said, returning my hands to her ass.  I dug my fingers in a little, which required some work considering how tight the leggings were and how firm her ass was.  “Why don’t I get these off of you, we have work to do,” I told her with a laugh in my voice as I reached up to her waist and began pulling the tight leggings down along with her thong.

What I saw next was breath-taking.  As the leggings came down, once her ass was free, it just settled, spread open because of the position she was in.  What caught my eye instantly was her bald pussy, just as puffy as I had thought it would be, and right above it the most prominent, puckered asshole I had ever seen.  It was large and pinkish brown.  While I stared at it it winked once, involuntarily.  I think she realized I was staring and felt self-conscious.  

“What, you never seen an ass before?  Put your tongue back in your head!” She said in a challenging tone.

“I’m not sure I can do that,” I replied

“Oh yeah?  Why not?” She asked.

“Because then I couldn’t do this...” I said as I lowered my face to her and stuck my tongue right in her butthole, wiggling it around.

She gasped and said, “Fuck!  You’re just going to eat my ass?  Just like that?”

I hummed my response as I did just what she accused me of.  I placed both hands on her wide hips and kept working my tongue, loosening up her butt and getting it all wet in the process.

“You Jerk.  You’re really going to do this aren’t you?  You’re just going to take it like it’s a prize you’ve won!” She said indignantly, but with an obvious hitch to her voice as i continued to plunder her ass with my mouth.

I removed my mouth with a little pop, and slid a finger into her wet butthole, sliding it in to the second knuckle.

“Ever have your ass fucked before?” I asked, slowly pumping my finger in and out.

“None of your business!” She said, with a tone that betrayed how turned on she was getting.  I could see visible moisture on her labia.  I just casually ran my hand over her pussy, rubbing circles over her clit.  It was wet alright.  

“Hey!  The bet was for my ass, not my pussy, stop doing that,” she said, again with the obvious sounds of arousal in her voice.

“Your choice, I just thought it might help you be a little more prepared when I put my cock in your ass.” I said in a teasing voice.  This was too much fucking fun.  She just made a grumpy sound in response, while i slipped a second finger in her butt, continuing the slow pace of penetration.

“Fuck!  Be gentle!” She said, not sounding at all like she was in pain.

I withdrew my fingers and stuck my tongue back in, deeper this time.  She gasped and gave out a little moan.  While I did that I worked her leggings down, then removed my tongue for a minute while i pulled them the rest of the way off.  She cooperated without a sound and settled right back into her prior position with her butt sticking up.  I stared at her for a second.  My work on her asshole had made it swell a little.  That combined with the moisture from my mouth made it shine.  The effect was amazing.  Her butthole looked big and swollen between those two perfect globes.  Her pussy was at least as wet too.  It was the hottest thing I had ever seen.  I quickly removed my underwear.  My dick was already hard.  I climbed off the bed and went around to the side she was facing.  The way she was position it was easy for me to simply walk up, my dick bouncing right in front of her face.  

She looked at me incredulously.

“Get that out of my face, I didn’t say I was going to suck your dick!” She said with an almost bratty tone.

“Ok, I can just put it in dry then I guess.” I said teasingly, not moving.

“Fuck!  Fine!” She said, reaching and grasping the base of my cock, giving it a couple strokes.  “You would have to have a big dick.  Why couldn’t you have had a little one?  How the fuck is this going in my ass?!”  She asked, before she put her mouth on my cock and started moving up and down the first third of it.  She was a little stiff at first, but within a couple strokes she relaxed and it felt amazing.  She was still trying to act put out, but I couldn’t help but notice she was wiggling her tongue back and forth on the underside of my dick just beneath the head, while she sucked up and down.  This was a trick I had never experienced before and it quickly began to drive me a little crazy.  She was looking up at me with angry eyes as she did it.  It was making me want to thrust my hips.

“God!” I said as I put one hand behind her head and started to gently fuck her mouth.  She didn’t protest, but just kept doing what she had been.  The longer this went on the deeper my thrusts started to get.  When I felt myself start hitting the back of her throat she drove her head down, taking my dick all the way to the back.  She was deep throating me.  She only had about half my dick in, but as I felt her tongue and throat working, more of it started to go in.  It felt amazing.  

Suddenly she pulled her head back, her mouth popping off my cock, and looked up at me with spit all over her mouth and chin.

“Is that wet enough?” She asked, with a neutral look on her face.

“Uh...yeah.” I replied slowly, moving back around to the other side of the bed.  I was so hard it fucking hurt.  She gave some of the best head I had ever had.  It was goods she stopped when she did.

“You better be gentle!” She said, the challenge back in her voice.

“We’ll see,” I said with a teasing tone, climbing up and positioning myself behind her.  God, it was a sight to see.  Her butthole looked so puckered and wet, just screaming to be penetrated.  I laid my cock against her ass for a moment and I saw what she meant.  I always thought of myself as above average, but I was so hard it looked bigger and thicker than usual.  It looked exactly like the dick an ass like hers required.

I placed the tip against her anus and applied just a little pressure.  It was so wet it sort of slid off, and much to my surprise, slipped downward and sunk right into her pussy.  Seeing what was happening I didn’t stop it, and slid almost completely in.

“Fuck!” She exclaimed.  “You fucker, you weren’t supposed to take my pussy!” She said sounding like she was trying to act pissed but had been caught off guard by me going almost balls deep in her bald, wet snatch.

“Sorry, it slipped.  Your asshole is really tight!” I said apologetically.

“Take it out!” She said, pushing back against me a few times in succession.  This had the effect of pushing me the rest of the way in, then back out, in a pumping motion.  She could either be trying to push me back, or she could be fucking me back, I couldn’t tell.  

I put my hands on her hips, gave a couple of thrusts really deep in her pussy, and asked, “are you sure?”

She sighed dramatically, then said, “Fine, just fuck it for a minute, but don’t get carried away!”

“OK.” I replied and I dug my fingers into her hips and drove my cock in all the way, pounding her pussy a few times, slowly, just savoring how wet and smooth it was.  I couldn’t hold back.

“Hey.....” she said, trailing off as I started to fuck her with the full length of my cock, my groin bouncing against that big ass.  Her pussy looked like a small bun with a big hot dog in it.  She was so tight, but she could take almost all of me.  I would hit bottom only on the occasional thrust.  

“You better not cum before you fuck my ass, loser!  I told you for just as minute!” She said, sounding like she thought she was in charge.

I went balls deep in one sudden thrust, just holding it there as she gasped.

I said, “alright, I just got carried away for a minute.” And slid my cock out really slow.  She shifted her position, bringing her knees further underneath her ass which had the effect of making her butt pop up towards me like some kind of offering.  I just stared.

“Are you going to fuck my ass or what?” She asked, almost sounding plaintive now, like she was saying, “c’mon, you promised.”

I didn’t hesitate.  I positioned my cock right at her butthole and applied pressure, holding it in place, as it started to slide into her ass slowly.  When the head was all the way in I was already going crazy.  It felt so good.  I slid a little more in slowly.

She wiggled her hips back and forth and said, “fuck that’s a thick cock.  It’s like my ass wants to hold on to it.”

I pulled back a little and then pushed forward again, her ass yielding a little more.

“Fuuuuuck.  That’s big.” She said, with no hint of her prior smart-assed tone.  I started to gently pump in and out, reaching over to my nightstand and grabbing the tube of lubricant there.  I squirted it liberally on my cock when I pulled back, doing that for a few strokes as I felt the lube work into her asshole and my thrusts started to become a little smoother.  A little deeper.

“Yeah, thanks, that makes it easier to take,” she said breathlessly as I dropped the tube of lubricant and put my hands on the sides of her hips.

Now that it was a little easier, but no less tight, I started to pump a little more aggressively, driving my cock about 3/4ths of the way in.  It felt so fucking good.  Her but made the occasional squelching sound, and i think she might have farted on my dick once, but it was sort of lost in all the sounds coming from the pumping.

“God, Mike.  That feels so fucking good.  Can you give me a little more?” She asked.

“A little more?” Not understanding what she was asking for.

“A little more of your cock.  Can you fuck my ass deeper?” She said breathlessly.  As she said this my mind just exploded.  I moved my hands up to her slim waist and grabbed ahold of her as I drove my dick into her ass, all the way to the balls, in one smooth stroke.  There was no resistance.  She took all of me, and in a few moments I could hear the slapping of my groin against her ass.  

“Fuck yeah!” She said, “pound my ass!” And that’s just what I did.  It was still so tight, but she took my thrusts, driving her ass back at me with each one.  If we kept this up didn’t know how long I was going to last.

“Mike, fuck, I’m gonna cum.  You want to cum with me?  You can cum in my ass.” She asked urgently.

“Fuck yeah,” I said, feeling the tension start to mount as my cock got even harder.  

“Pound my ass and cum!” She said and then cried out with her own orgasm.  Her butthole clenched on my dick, then released in a rhythmic motion.  I couldn’t hold back any longer.  Between one thrust and the next my dick twitched, the muscles inn my groin contracting, and I let out a stream of semen into her bowels.  Then another, and another.  I don’t think I had ever cum so hard.  With one last thrust I released the last of my load, spent and euphoric.

I slid slowly out of her butt as it made a little squelching sound and immediately expelled a big blob of my spunk.

“Oops!” She said, “you came a lot, huh?  Would you mind getting me a towel?”  I staggered off the bed, dizzy, incoherent.

When i came back she took the towel I offered, draping it over her ass before she rolled over and laid down on my pillow.  She patted the bed beside her.  I clumsily climbed up and laid down next to her.  She smiled at me, like she was the winner after all, then gave me a quick kiss and rolled over so her back was to me.  I scooted in behind her, molding my body to hers, and placing an arm over her.  Neither of us said a word as we drifted off until later that night....

We both passed out almost immediately, but I woke up what seemed like hours later, and, for a moment, I was shocked to see Eve snuggled against me, until I remembered what had happened.  Still, I couldn’t believe it.  It seemed like some crazy fantasy.  God, her ass was amazing! 

Just as I thought that she passed gas, just a cute little fart, and moved in her sleep slightly.  Why was that so hot?  I felt myself starting to get hard again, and within a few minutes my dick was poking her backside, unavoidably.  I tried to go back to sleep, just enjoying the feeling of her being spooned up against me, but it wasn’t working.  Then she passed gas again!  This time followed by a bubbly sound that I knew had to be a combination of my cum and the lube we had used.  This thought did me in.  My dick was rigid, and owing to the position we were laying in, lodged itself right in the crack of her ass.

Involuntarily, I started to move my hips a little.  Her but felt moist and my dick was just sliding back and forth between her cheeks.  God she smelled good.  Her skin was so soft.  My hips started to move a little faster and I felt her awaken with a little start.

“Mmmmm.  Somebody’s knockin on my back door,” she said with a giggle, wiggling her ass against my cock.  

“Sorry, I just woke up like this.  I think your ass and my dick have formed their own relationship.” I said with a chuckle.

“Well, they had quite an introduction earlier, I don’t think we should stand in the way of their love,” she said, with some heat, the laugh still in her voice.  

I pulled my hips back slightly, reaching down with one hand to redirect my cock, then gently pushed back with my hips.  There was resistance for a minute, but then it suddenly gave way and I sank about halfway in to her very wet ass.  Oh my god, it felt good.  

“Ooh, wow, I guess she was ready.” She said with a hitch in her voice.  I used my arms to pull her close to me, holding her tightly, my face on the back of her neck, then started to pump my cock in and out slowly.  She farted on my dick a couple times, expelling the air and liquid I’d driven In there a few hours before.

This made her laugh and say, “she’s taking to you.  I think she appreciates your attention.”

“Mmmmm,” was all I replied, as I kissed the back of her neck and started to pump a little deeper.

“I love how you hold me tenderly while you fuck my ass,” she said with a little giggle, the sounds of her arousal obvious in her voice.

She was driving me crazy.  I kept the same slow pace, but on my next stroke drove in all the way and just held it there for a bit.  She gasped slightly and when I didn’t pull back right away she groaned and started to wiggle her butt.  

“Fuck that’s deep.  Fuck, fuck!” She said urgently.  I gave it a second more and then drew back slowly.  This seemed to undo her as she went boneless in my arms.  “Fuck yeah!  Fuck my ass!” She said with a kind of surrender, and only then did I start to pick up the pace, driving a little more forcefully.  My groin was making popping sounds against her but when I could feel her orgasm take her.  Her rectum clenched and released rhythmically on my dick and she let out a little more gas, farting on my cock as she came.

I lost control a little, feeling my own finish building, I started pounding her ass in earnest.  God it was so tight, but she could take all of me, and so I gave her all of me, with every stroke.  

“You got bigger, are you going to cum?” She asked breathlessly.  I just grunted a reply, keeping up the assault on her ass .  Then I felt her squeeze down even tighter on me!

“There.  Drain your balls in my big, tight butt.” She ordered.  I lost it.  A few more strokes and then it happened.  What felt like a continuous stream of spunk loosed from the tip of my dick and I drove in all the way and deposited it deep in her bowels.  Then spray after spray continued.  I was dizzy with euphoria and still holding her tight.  

“Fuck that was a lot of cum!  Hey!  Do you think if I pushed it would launch your dick out?” She asked, laughing.

“I’m still really fucking hard, so I’m thinking you just push some cum out.  I don’t think anything could push my dick out right now, it’s parked.” I said feeling the narcotic sensations of afterglow.

“Ooh, fuck, that’s hot the way you said that,” she said, wiggling her ass against me.  “Wait...” she said, and then I felt the push.  I was so deep in her butt still it just felt like pressure, but after a second a bubbling, liquid sound came out as a mixture of lube and cum shot out around the sides of my dick.  When she stopped pushing the sound just sort of whined out and made us both start laughing our heads off.  As we started to settle down, I gave her ass a couple of strokes really slowly and then pushed back in to the base again.

“Fuck, nobody has ever fucked my ass this good.  I could get used to this.  Your cock is just a little bigger than I can handle, though, so it might take some practice to be able to take it this deep when I’m not already relaxed down there.” She said

“Wait, are you saying we’re going to do this again?  With no trivia?  What about Jason?” I asked.

“Are you kidding?  Do you think I don’t know that Jason has had his dick in everything that even looks female over there?  That fuck could not go without pussy for more than a day or two before he became unstable.  I’ll talk to him.  He’ll be fine.  You were right, though.  He never fucks my ass, and if we didn’t do this again I would be thinking about it constantly.  So....uh.....what does this mean, are you down?” She asked somewhat self-consciously.

“Are you kidding?  I could never get tired of your ass....hey, that kind of has a double meaning...” I said with a laugh, squeezing her a little tighter to which she responded to be letting out a breath and relaxing in my arms.  Best game of trivial pursuit ever!!

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