It was already late. The alcohol in my blood slowly lost its effect. Not the best night-out I´ve ever had, partly because somewhere along the way I lost all my friends I came with, but the main reason was my habit of spending my cab money on drinks. This time though nobody could borrow me some since I there was nobody I knew.
I got my jacket and left the club. Luckily it was fairly warm that night, so even though it sucked walking two hours home I would survive. Still I decided to at least ask the cab company on my phone how much a drive home would cost. Too much. Maybe two blocks away? No way, still too much.
“Hey! You okay?” A brunette woman with short, styled hair stood next to me and smiled. “Where do you live? Maybe we can share?”, she asked me. I stared at her in a rather rude way. “Sorry I didn´t mean to eavesdrop on you. I just…” “No, no, no”, I interrupted her, “it just wasn´t my night to be honest. Not your fault.”
Honestly she just brightened it quite a bit. Of course it wasn´t just her generous offer to share a cab, she was a beautiful woman. Her hazel-brown eyes looked at me but my eyes rather wanted to focus at her body and the gorgeous way her outfit accentuated her small breast showing a good amount of cleavage and her tight summerdress presented her perfect waist and hips. Her legs were also barely covered as her dress loosened up into a wide skirt-like fashion ending in the middle of her thighs.
“Oh good!”, she laughed at me, “I thought I made you uncomfortable just now.” “Oh definitely not! I´m glad you approached me!, I tried to remember her question from before, “oh, eh I live west from here. two or three blocks behind the western market square.” “Well no wonder you seemed down. That´s quite the walk, especially at night.” Looking around she seemed to evaluate the situation. “Lucky for you, I live in the same direction. How much is it to your place? 30$?” “Haha, no. More like 40$ or 45$. Problem is I got only 15 bucks left.” “Poor boy”, she joked, “sucks for you, heh?” Not sure how to react I simply nodded and tried to laugh it off. “I think it would be better if I called them, don´t you think?”, she suggested breaking the short silence. “I might have annoyed them a little, yes.”
While we waited for the cab to arrive we continued joking around and chatting a bit. Her name was Emily but just when I asked what she does for a living, the car arrived. “You sound a lot better now”, she said as we opened the door. Both of us sat down in the backseat. “Taking a girl home seems to be quite the mood boost!” Before I could answer anything the driver asked me: “So, where are we going, sir?” “Oh, yes…”, I stuttered, trying to sort out my thoughts, but ultimately giving him my address. Emily smiled at me and her big eyes occassionely reflected the street lights. She looked absolutely stunning! But my thoughts quickly ran wild. “My apartment is a mess.” or “I´m totally unprepared!” was all I could think about. My worried face must have made her uneasy. “I could also just tell the driver to drop me off at my place.” She paused for a moment. “I mean, I didn´t really ask, sorry.” “Oh no, no, it´s just that my place is a mess right now! Totally unfit for such a pretty girl.” Out of nowhere she darted over and kissed me on the cheek. “Thank you!”, she laughed nervously. Without a second thought I leaned over grabbed her hand and kissed her deeply. We stared awkwardly at each other. It was clear that neither of us usually are this quick with those things. But something must have sparked a fire inside Emily because she moved my hand on her thigh and then tried to hide her embarrassment. “You are pretty cute”, I whispered to her which made her blush. After a bit of awkward silence and plenty of nervous peeks to the driver I slowly inched my hand up, bit after bit. To be honest I really wasn´t sure what I was doing and especially if I was reading the situation well. To my surprise she opened her legs a bit and guided my hand under her dress and glanced at me, long enough to see her nervousness. I kept inching closer and closer to her privat parts but didn´t quite muster the courage to actually touch anything, so instead I stroked the inside of her thighs. Emily seemed to relax a bit and now stared seductively into my eyes. Captivated by her new found confidence, I didn´t notice her hand moving towards my crotch until it was already there. Moving up and down with her hand she lightly caressed my already hard bulge which transitioned into massaging.
Unfortunately for me we were already at my complex. While trying to appear normal Emily gave him the 42$ he demanded, even though it was plain obvious what we just did. “Plainly speaking, you make me very horny!” I blurted out and as I still watched the car drive away, she turned to me. “You are soo mean!” A bit puzzled I wondered if I said something wrong. “YOU teased me the entire 20 minutes we drove here and now have the guts to tell me, *I* made *you* horny?!”, she shouted at me in disbelief. Angrily she started pulling down her panties. “I mean…”, she continued to step out of them, “look at this!” handing them to me. Fueled by her anger she pushed me into the door and gave me a deep kiss which I gladly returned. I was caught off guard and didn´t find any words, so instead I grabbed my keys and opened the door holding it open for her.
“On which floor is yours?” “Second floor, right door”, I answered as if she had commanded me. After the first few steps I learned why she insisted on going first. Our difference in height revealed a perfect view of her bottom under the dress. With each step her dress would fly a bit to the side and I was presented with a beatiful display of her private parts. Surprisingly something shimmered between her cheeks which made me even more curious of what was under there. It was obvious that she had noticed my staring as she started to deliberately shake her booty more with each step revealing a silver buttplug with an amethyst-like crystal in the middle. I was completely lost in various fantasies in which I buried my face under her skirt and if Emily hadn´t stopped walking at my door I would have missed it.
To my relief the hallway was relatively tidy and gave me time to come in and head for the kitchen. “Do you want something to drink? Emily?” Silence. I step outside the kitchen in the hallway to look around and discover that my bedroom door is open. “Emily? Are you there?” “Right here!”, comes out of my bedroom in a playful voice. There she lies completely naked except her *jewelry* between her cheeks.
“Don´t you feel overdressed?”, she asked trailing down her own body with her hands. I did. Even my shoes were still on that I quickly remove. Next I stripped off my shirt. “Come on! Show me!”, she pointed towards my groin. “You know, I didn´t really get to experience your skills regarding *´undressing´*, even though I really wanna see how good you are!” She started giggling: “My deepest apology, professor! Will I be graded for it?” “Oh you will simply be rewarded or punished, depending on your talents, my dear!”, I answered barely containing my laughter. She sits up on the edge of my bed reaching for my pants. Gently she rubbed my obvious erection through them, then quickly grabbed my butt. “I´m sorry, sir. I just could not resist!”, she said innocently. Without hesitation she unbuckled my belt. “I can´t promise this won´t affect your final result.” Seemingly she didn´t care because she focused on opening my pants and pulling them down in a hurry. Not even waiting for me to step out of my pants, she greedily started pulling on my boxers.
With anticipation Emily stared at my crotch and finally freed my member of its fabric prison. “It has such a nice shape”,she uttered eyeing my naked body up and down, “just like the rest of you!” With care she started massaging my balls and with the other hand played with my tip. She kissed it teasingly and lick the head, which made my dick jump a bit much to her amusement. A bit embarrassed I ordered her to stop teasing me and start sucking. I almost regret that decision. She was a goddess at pleasing with her mouth. The way her tongue caressed the sensitive underside while her lips and her hand stroked the shaft was to die for. Never in my life will I ever get to know someone better than her. As I looked down I could see my dick slowly disappear in her mouth and reappear glistening in her saliva. My entire body was paralyzed in pleasure each time I hit the back of her throat.
From deep inside of me my orgasm started to build up faster than I wanted to. I wanted to live in this moment forever but I was at her mercy and when our eyes met I knew she wouldn´t show me any. I got closer and closer. “If you keep up like that I will come!” But my pleading remained unheard. Mercilessly she picked up speed until it was impossible to hold back anymore. With a moan I grabbed her head with both my hands and hold her while I erupted inside of her mouth. Several ropes of cum shot out and each time she skillfully milked every last drop out of me. “That was incredible!”, I sighed in relief, but she just smiled at me devilishly. I sank down to the bed and laid myself next to her.
“You could have at least slowed down.”, I tried to explain her but she just moaned: “What´s the fun in slowing down? I think I finished you pretty good!” Her arm repeatedly bumped into me and when I sat up to look what she was doing I could see her touching herself. “Oh what a naughty girl you are!” “Oh come on! I´ve send you to heaven with that blowjob just now. I´m the best girl ever!” “Don´t you think you can talk to your teacher like that, miss! I´m gonna take you with me!” “Then show me.”
Feeling challenged I made myself comfortable between her legs and started kissing her inner thighs. “That´s not fair.”, she protested, “I didn´t tease you like this.” I got up to her face and whispered to her: “You wasted your chance. Poor girl!” All while tracing lines with my finger on her body. Kiss after kiss I made my way downwards her body, only stopping at her nipples which I ever so slightly licked, making her squirm. With all she got, she tried to push her boobs towards me hoping I would properly touch her. But her pitiful attempts were in vain as I pushed her down into the mattress. Eventually I arrived back where I started, between her legs where a throbbing wet mess eagerly waited for me.
I decided I teased her enough and pressed my lips against her clit, firmly placing a kiss. A sigh of relief escaped her. With my tongue I started lightly moving up and down her slit. It was something I did more for myself than for her. I wanted to taste her honey and savored every bit of my delicious meal. Every movement she made got me more and more excited again. But before our second round I felt like she deserved some good licking. So I moved back up to her clit and started to circle around it with my tongue. Slowly I increased the pressure and I could feel her arousal build up more and more. Wanting to proof myself I inserted two fingers into her and massaged her g-spot much to her surprise. Judging by her soft moans it was a welcome surprise.
Every now and then my fingers bumped into her buttplug giving me evil ideas. “You wouldn´t have any particular ideas with this, would you?”, I asked while lightly pulling on her buttplug. “Honestly I had no plans at all for this evening. I just went with the flow and ended up in your bed”, she shrugged. After a brief pause she said: “But… if you´ve got lube and of course some protection I definitely would never stop you from doing anything with me. I´m all yours!” “Ok how about we remove this bad boy…”, I teased her while already pulling on it, “and replace it with something more lively… like my cock.” Before I even finished my sentence the buttplug was already half-way out and Emilys eyes were closed, clearly enjoying the moment. Very, very slowly I removed it from her pretty hole until it almost plopped out. Holding the plug in my hand I was surprised at how large it was and mentally compared it to my manhood. It must have been nearly double the girth of mine. Hinting at it: “You must be deeply relaxed if you can take such a massive thing.” I only received a giggle as an answer. “Quit messing with me and for gods sake take my ass!” She seemed surprise by her choice of words but seemed not to care too much but rather positioned herself on all fours. Meanwhile I rushed to get the condom on and searched the drawer for my lube.
Having found it I place myself behind her and squeezed a bit of lube directly onto her hole. “Uhhh cold!”, she shudderd, but I didn´t care and continued by placing my thumb directly at the entrance to her butt. Gently I pushed my thumb inside and massaged her inner walls to spread the lube. Emily seemed to be very much enjoying it, letting her head fall into the bedsheets so she could circle her pussy with her fingers. I took my time massaging her insides and added another squirt of lube, this time spreading it with my index and middle finger essentially fingering her butt. Some soft moans escaped Emilys mouth again telling me that she was ready. With the excess lube on my fingers I lubed up my dick aswell before resting its tip at her entrance. “I might be relaxed but please take it slow.” “Just tell me when I can start moving, ok?”, I answered her while entering her. The view was fantastic. I like how my dick spread her butthole open and pushed inside her. Over the course of a minute I shoved my entire dick balls deep inside her, occasionaley interrupted by her asking me to stop, so she could get used to the sensation. Everytime I stopped she contracted her muscles a bit and firmly grabbed my hard on. Even though anal sex often gets overhyped it truly was a life-changing experience for me. Never before have I felt such tight grip around my best part and thanks to the lube everything went smoothly but the hottest part was the connection I felt with Emily. I had a pretty good feeling with her from the start but the amoutn of trust between us grew which each inch deeper. Trying to enjoy every second of it I used her hips to retreat a bit from her deepest spot. Her hole was so tight it felt like she didn´t want to let me go and I didn´t want to be elsewhere aswell. The urge to push back in overwhelmed me and for the second time my hips thrusted into hers seemingly deeper than before. Not wanting to finish too soon I paced myself but eventually my instincts overtook me and I picked up speed. Emilys face clearly showed that she was enjoying it at least as much as I was and the rythm at which she pleasured herself matched my thrusting. “Oh.. I´m..mhhhmm… getting close”, was everything she managed to say. “Don´t worry I won´t hold back.” I had to breath. “I can feel mine building up too!” It didn´t take long for noth of us to come. With merciless thrusts I pushed as deep into her as I could while I could feel her orgasm. Her muscles once again clenchend around my dick sending waves of pleasure through ultimately bringing me over the edge aswell. Emily shook with her entire body as I finished with a few rough thrusts. After the inital wave of pleasure subsided we both tipped over the side. “You are amazing!”, I complemented her panting heavily but she just grabbed my arms around her, so I hugged her. We took our time to relax and my penis softened still inside her.
After tidying up the mess we made, we cuddled into sleep. The next morning I woke up spooning her. Trying not to wake her I looked at the clock but I was soon greeted with a “Good morning!”. Emily must have been awake longer than I was. I was smiling at the thought that she would rather be my little spoon than to sneak out of my apartment while I slept. “Morning my little freak!” “What earned me that title?” “Oh I could have been a murderer but you still offered me your butt.” “Haha…”, she answered sarcastically. “Honestly…”, I hesitated a bit, “those jokes were just a strategy to mask my nervousness.” She turned around and her facing me. “I could still tell.” She kissed me on my forehead, “that´s why I chose to come with you!” “You forced yourself onto me!”, I joked but Emily didn´t think it was very amusing, “that´s why I´m gonna force yout to stay for breakfast.” Emily glanced over to the clock. “You know… I wasn´t exactly honest with you yesterday. I´m actually a visitor in your city… and my hotel is at the airport.” “Oh so saying we could share a cab was a scheme to lure me in?” “Yes! And I´m afraid I can´t stay for breakfast. I need to catch my flight. I´m sorry.” “Don´t worry! One-night-stands usually don´t stay for breakfast, do they?”, I tried to sound less disapointed than I actually was. “I hate to ask but could you tell me how to get to my hotel?” I proceeded to tell her the way and gave her some bus money at the door. “That makes us even I guess!”, I tried to joke again. She thought for a second. “I really liked our little adventure last night and to be honest I like you too.” Before I could say anything she headed for the busstation.
One week later I still think about her a lot but I have no telephone number or anything to contact her. As usual on a friday after work I open my mailbox for the usual bills, but today there is only a red envelope. Excited I took it and rushed up the stairs and read it:
*Dear _____,*
*I apologize for not being honest once again. One week ago I was checking an apartment I planned to move into. I just did not want to disappoint you if I had not gotten it but I did which is why I am writing you.*
*I will need a helper to move next saturday. Maybe you have got some time? Also you owe me a nice breakfast. So how about you come here to help, stay the night and then we can have some pancakes in the morning?*
*0127 16872* *Call me and I tell you the address!*
*Love*
*Emily*
*PS: I know you have a thing for backdoors, but you should check out my frontdoor for a change ;)*
Source: reddit.com/r/sexystories/comments/gor6ch/anal_a_wholesome_hookup
Well done! Love butt stuff stories!
Damn that was great