I can’t believe this happened. Crazy night takes a dirty turn with my best friend [MF]

Me and my friend, Jess are really close ever since high school. We’ve never crossed that line tho. I’m okay with that too. I don’t hold a flame for her. She is attractive as fuck though, objectively. She is slender, D cup, tight ass, long brown hair, amazing stomach, long legs.

We got together one night and went out drinking to catch up. One beer led to another, and soon led to some party drugs. We ended up coming back to my apartment and hanging out. Still doing lines and drinking.

She asked if she could crash at my place since it was so late and we were still up. She also asked if I had any sort of lounge/sleep shorts and shirt she could wear. We’ve shared a bed before so this wasn’t new. Although, this time I gave her a pair of soft lounge shorts that were maybe a size or more too small for her. When I handed them to her out of my dresser, and began to slide off her jeans and reveal a blue tanga. She slid the shorts up and they hugged her ass like boyshorts. Then she slid off her shirt and turned around to undo her bra, facing away from me. Her ass to me. We were talking about everything, and at some point she asked me where I go for porn. The conversation ended up with the two of us on my computer, me showing her my go to sites. Her asking about certain kinks, and then browsing together and picking what links, or videos to look at. I had brought up some amateur videos and we were watching some home made sex tape. Our conversation moving from the video to things we like during sex. Her preferred style of clitoral stimulation and my interest in kink.

Things moved on to me showing her the collection of dirty pictures and videos I had been sent from other girls. She complimented the different girls and was visibly impressed. She then showed me a collection of images she had sent and asked my opinion. Photos of her in panties and a bra, or naked. All remaining tasteful.

Then we started chatting about different experiences, and one i had told her hit a button. She asked for more details about this girl who had a particular fetish around Dd/lg.

I saw her fidget and shift in her seat as I told her the things I did to the girl. Then I showed her a couple photos of her. Getting more detailed. I remember her shooting up straight as I told her how I spanked the girls ass red and made her repeat whatever I said. Telling her how I shoved her panties into her mouth to gag her. About how I throat fucked her while I was stretching her ass with a plug. She then confessed how much she liked anal sex. I told her how I DP’d the girl with my own cock and a dildo.

She told me how hot she thought it all was and then offered up that just hearing about it made her wet. She continued telling me how she would get wet throughout the day from certain thoughts and such.

Then I had asked her is if she had ever tasted herself. She replied telling me, she did often.

Then as the video on the computer grabbed our attention, she asked if I was hard. I told her all this talk along with the dirty videos had made me. She gestured at my bulge and said some comment about how it was obvious. I asked her is she was wet, and she replied that her panties were drenched. She then told me how turned on she was, and that she wanted, no, needed to get off.

A thin moment of silence followed, with me cutting into it, agreeing. She then suggested that we both masterbate. Still high on drugs and drunk, things moved without much deliberation. Before I knew it she had her hand down her shorts and I had my cock in my grasp under mine. We started playing with ourselves.

I began to smell her and hear her wetness as she touched herself.

We seemed to be edging a bit. Not knowing if we should get off. We stopped for a moment and began searching for a new video. I saw her fingers glistening. She acknowledged her wet fingers and then laughed as she slid them in her mouth.

As we loaded another video our hands went down again and I saw her other hand begin to play with her tits. She asked if I wouldn’t mind if she removed her shorts and as I told her it was fine, i did the same.

Now the both of us had our shorts around our knees and while she played with her clit, I was stroking myself. She paused and took a moment to look at my cock, then complimenting me on it. Saying it was a pretty cock and a great size. We knew this was a fucking weird thing we were doing, but didn’t bring it up. She asked if she could touch it, and I shook my head in agreement. Her small hands wrapped around it and explored the shape. Then I asked if I could touch her. She paused and I felt this is where everything would stop because we had taken it to far, but then she shook her head and gave me permission. My fingers slid between her thighs and traced up her lips and to her clit. She gasped lightly as I did. Then she began to tell me what she liked.

She instructed me on how to move my fingers and the speed . If it wasn’t for the drugs I would have been in shock over everything that was happening. After a few moans, back arches and shudders, I began to slide one, and then two fingers into her. She spasmed as I began to find a rhythm. I stopped and pulled my fingers out and then brought them to my lips and licked her juices off of them. She had this sweet taste that made me say “mmmmhmmm” reactively. She pulled her hand away from my cock and then brought it back between her thighs. My own hand finding my cock and beginning to stroke it again.

She had known from my stories I had a small collection of toys, so when she asked about it, I wasn’t surprised. She asked what I had, and if she could see them. I stood up and walked towards my bed, retrieving a bag from underneath it. She followed me, both of us shedding our shorts. As I stood there looking at her, I took a good look at her pussy. It was hairless and compact. Her mound was the same milky complexion. I told her she had a pretty pussy. She blushed and asked if I meant it. I reassured her I was being honest, and told her it tasted good too. I was unaware that I was also still stroking myself too. As I opened the bag, I stepped aside to let her browse. Inside she found bondage tape, a hitachi wand, a suction cup dildo, a regular dildo, two but plugs, a gag, lube, and some restraints. She asked what I liked using the most. I told her it was the hitachi and the plugs. She told me she had never used a plug but was always curious. I was quite for a moment before I asked if she wanted to try it out. She didn’t look at me and instead was quite for what felt like forever. She asked if I had any hygienic materials for clean anal. I told her I did, and then she said she would like to try them out, but only if I would. This was the first real shock. But with everything going on, I agreed without hesitating. We took turns cleaning ourselves and prepping. When she was away, I wondered how far this would go. As we layer on the bed, we both began to apply lube to our assholes. She was a litttle more novice and I gave her some tips on warming up. She asked if it would be weird if I helped her fit it in, and I told her it wasn’t, and that I was just helping facilitate her fun. I told her to get on all fours and raise her ass up. I continued to lube her up, then slid in a finger, and eventually another. She gasped and grabbed at the sheets. Telling me how the stretching felt good. I began to ease the tip of the plug around her hole and pushed gently, rocking it in and out barely a quarter inch in. Soon, i had an inch inside her and kept pulling up and sliding back. Her ass hole stretching for it. She moaned and purred as I did. When her asshole gaped ever so small, I spit into it. She reacted asking what the FUCK was that and I replied, saying, I always wanted to do that.

I finally got the entire plug in and continued pulling it out and pushing it back while she shivered.

She turned and smiled at me, letting me know how good it felt. She then sat up and rocked on it, then telling me it was my turn. My plug was a size bigger then hers, but at 6’3″, it was appropriate. I had already told her at some point that evening I also liked anal play. That’s how this “if you do it, I’ll do it” came to be. I began to push mine in and she watched as I did. She told me gay guys would probably love to watch me do this. I was making quick progress when she told me it was her turn to help and instructed I get on all fours now. As I did I felt her grab the base and gently move it up and down. She was being incredibly gentle, not having done this before. I helped guide her force and motion. She began pulling it out and making me gape as well, then returning the favor as I heard her spit into my ass. I told her she could be a little more aggressive or rough with it. She laughed and made a comment about how good I was at it. As she shoved it completely in for the first time she followed up with a swat on my ass cheek. I yelped from the surprise and asked what that was for and she told me she had always wanted to but was always on the other side of the swatting. She confessed she preferred receiving instead of giving after trying. I had circled back to how much fun it is to spank girls and she told me how good that sounded. Without saying anything, I had her across my lap, ass up. I began to swing and she moaned, and whined as I did. I felt her dripping onto my thighs. My cock was hard and pressing into her stomach. I hit her what felt like a 100 times. Her ass was bright red and she was panting and sweating from it. She slid up and acknowledged how hard I got from it and mentioned how I enjoyed it just as much.

We lay there and without promoting each other, we began to touch ourselves again. I felt bold now and grabbed our drugs and placed a line on her tit, she didn’t seem to mind. I then snorted it off and the residue that was left I brought my tongue too. I licked around her nipple and then gave it a slight nibble. I asked if she wanted one and when she said yes, I put a small amount on the tip of my cock. She gave me a sideways smile that said “really, really?” But she didn’t protest and snorted it off, then I saw her tongue move down and lick the leftovers. I told her I wanted to show her another toy and when she agreed I brought out the hitachi. I plugged it in and told her to lay still. As I traced up her legs with it she giggled and twisted. I brought it between her thighs and she immediately started twitching and withering. I asked her if she liked it and she could barely respond. I stopped and pulled back. She arched up and told me to keep going. I told her the teasing was the fun part. She grabbed me and told me she needed me to keep going and that it would be my turn next. I obliged and set it against her clit. I then told her to lay still and grabbed the bondage tape. I wrapped her hands around the headboard and began to turn up the speed. She was beginning to scream now. She kept apologizing for being so loud. I grabbed her panties and gagged her with them. I could see in the back of her mind she was registering how insane this was. She began to shake and bounce as I moved the wand around. She spat out her panties and let out a long moan and her plug exapanded and then slid out of her ass while she came.
She was breathless, sweating and still sensitive for ten minutes or so. I undid the tape and she laid there grazing her chest. After a moment, she told me that even though this whole thing is weird and crazy, she wouldn’t forget me. She then slunk down and began to lick the tip of my cock. She began to dance her tongue around it and then slide me almost all at once inside her. I felt her gag slightly as she pushed herself down. Then coming up just to continue repeating that over and over until she was panting for air and spit was dripping down her chin. She asked if I wanted just for her to go down on me or if… she trailed off, hoping I’d understand without her having to say it. I shook my head saying I’d be willing. Her legs straddled my hips and she hovered over my cock. One hand grasping at it, while leading it into her. Her pussy was so wet that I practically glided in. She let out a breath of air as she sat down onto me completely. She began to rock back and fourth and I let my hands grasp at her chest. Unsure if this was on the table or not, I began to suck and bite are her nipples. Her moans made it clear that it was welcomed. I grabbed her waist and flipped her down so I could be in top. Bringing her legs up, I began to rail against her. Then one hand slid up her chest and neck and I began to grip and squeeze at her throat. She shook and bit her lip as I did. I brought the wand back and held it over her clit as I slid back and fourth into her. She began to build and tense again.

Soon she had come again and as she lay there, eyes rolling back she asked if I wanted to go in the other. I shook my head quickly and she grabbed the lube and began to pour it down her mound and over my cock and let it drip down her ass. I began to position myself outside her and then she moved onto all fours. She said she’d push back and to have me not push in until she was ready. Five minutes of pleasure and painful moans later, my cock was deep inside her ass. Her hole stretched and tight. I began to thrust back and fourth and she would moan and yelp, wincing and gasping as I did. She asked if I liked dirty talk and told me she did. I began to tell her how tight her ass was and how hungry it was for my cock. I made her tell me how badly she wanted it. She asked me to be meaner. So I spanked her and told her to tell me how much her slutty little asshole wants my cock. She begged for me to go harder and to cum inside her ass, telling me she loves it when she gets used and how wet she gets from being a little slut. I began to pull her hair as I felt myself about to cum. I told her I was going to fill her ass with me and she screamed out telling me how much she wanted that. As I did, I felt myself explode. For a minute after I felt myself cumming and rocking until I slipped out and saw my cum drip down into her pussy and then the bed. I grabbed a bit with my finger and then brought it to her mouth. She licked it off, and then did the same thing to me, saying it was only fair, asshole. I told her we tasted good. We lay there for the next hour resting and cuddled up. Around then she asked what had we done, and I replied that it was no big deal and we just got a little carried away. We agreed to not cross that line in the future, but we did agree that for the night and until we left the bed to leave and go about our day, we’d have fun. We spent that night fucking like rabbits after that, and the next morning we did the same. Afterwards we have been behaved and avoided acting weird around each other.

Source: reddit.com/r/gonewildstories/comments/606ucn/i_cant_believe_this_happened_crazy_night_takes_a