Anal Adventures

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Nothing makes me orgasm harder than when something’s in my ass. I’m not picky. A butt plug, a dildo, my own fingers, a pen. Whatever I could find, I’d use to stretch my hole and get myself off. Even thinking about stretching my asshole made me wet. I loved everything about it, the slight discomfort, the pleasure, enveloping around whatever object it was. It was a bit of an obsession of mine, an obsession that got me into some very interesting circumstances.

It started when I was in college. Nothing but time on my hands, and even though I shared a room with another girl friend, I found time to adventure. It started with my fingers, rubbing and circling around my puckered hole while I fingered myself, the tingling pleasure had me hooked. I’d then adventure to fingering my ass and pussy at the same time; the first time I filled both my holes I orgasmed so hard I squirted a bit. A bunch of firsts for me that night. Curiosity got the best of me and I moved to using multiple fingers, then eventually my dildo to fill my ass. Feeling my hole envelop around the head of the fake cock, before sliding it deep inside me was almost enough to get me off right there. When I’d slide it all the way out then jam it back in, it drove me wild, and the orgasms kept coming.

Of course having a roommate had its challenges. One time I was home alone in the afternoon, thinking I had the place to myself. I stripped to my underwear and started watching porn on my phone of girls getting their asses rammed by huge cocks. It was hot, and in no time I felt a wetness build. I stripped completely naked, exposing my small, perky breasts. My light brown hair hung almost enough to cover my now erect nipples, sticking out from my also small areolas. As I looked down my long, toned body, a small bush of brown pubes hid the rest of my mound from my view. I walked over to the mirror to see my tight pussy lips hiding between my legs. I turned, showing off my round ass. Thank goodness for sports growing up, my ass had always between round and firm. I bent over and spread my ass cheeks, showing off my slightly darker, puckered asshole. I gave it a slow rub, exciting myself to play with it later. I lubed up my dildo, ass, and vagina and hopped onto my bed on all fours, the phone in front of my face.

As I watched these women take these massive cocks in their ass, I slowly started to rub my clit, feeling it stiffen with excitement, turning me on even more than I already was. I pushed my fingers down my slit to my asshole, where I rubbed and circled it, teasing myself, before sliding a finger inside. I couldn’t wait any longer, grabbed my dildo, and inserted it into my ass. I slowly slid it all the way in, taking all 7 inches of the fake cock. I slowly slid it all the way out, then all the way back in, loving the head pressing and opening my asshole before taking its full length inside me.

I was hornier than ever and greedy for an orgasm. I picked up the pace with my dildo, now aggressively fucking my own ass with it. I used my other hand to continue rubbing my clit, burying my face into my bed. Fast and hard I rubbed myself, sending tingling sensations throughout my groin. My other hand didn’t stop, shoving as much of the dildo as far into my ass I could, almost removing it fully, before sliding it deep inside me as fast I could again. I was on the brink of an orgasm, and my moans blocked the sound of my roommate coming home. Intrigued by the sounds she came over to the room and opened the door. My orgasm had already started.

“What the fuck!” my roommate shrieked.

It was too late for me. I had yanked the dildo out of my ass, showing off my gaping asshole before it enclosed back to its normal, tightly puckered self. My legs shook as my hand continued on my clit, sending my whole body into spasms. I moaned loudly, as a wave of pleasure surrounded my entire body. My ass tingled, satisfied with being filled, my pussy throbbed with the excitement. I didn’t move off the bed, my ass was still sticking high in the air.

“The was really hot. I’ve never played with my ass before. Can you show me how?” My roommate asked.

And that was how I became best friends with my roommate. I did end up showing her the finer points of playing with your own asshole. We were open about it, and open of our bodies. She saw my asshole so stripped down and showed me hers. It was even tighter than mine, and her bare, pink, protruding pussy lips accentuated it, making it look even smaller. From then on, nudity and masturbation were normal around our room. We never closed the door to our bedroom, often watched porn together, masturbated together, and even just watched the other person play with them self. We were both straight, and agreed we didn’t want to try anything together, but it was nice to be so open and appreciate someone else’s body, and especially their love for anal play.

From there, my love for anal grew. I started to try new toys, often sharing them with Beth, my roommate. That way we could try more things, pushing our limits together. By the end of third year, we had quite a collection; long and illegal bahis thin dildos, short and wide ones, butt plugs of all shapes and sizes, vibrating plugs, anal beads. We tried it all, often challenging each other to stretch our assholes out more. My favourite time was when I got a new butt plug, that was wider than any we’d ever tried. I let Beth try it first, as she lowered herself onto the plug, taking the gurth inside her, but stopping at the base. No matter how hard she tried, she couldn’t get her asshole fully around the base of the plug. It was too wide for her. She cleaned it off and I tried, as Beth watched me try and fit it inside my ass, stretching myself out slowly to try and envelope my hole around the base. After a few attempts, I was able to feel my asshole widen enough to envelope around the toy, then tighten around the small neck of the base. It felt so full inside me, and I felt so accomplished I was able to fit it in. I slowly slid the base out, having to stretch myself fully to remove the plug. Once around the base, I quickly pulled out the rest of the toy. My asshole gaped open before slowly returning to normal, almost winking at Beth. She jealously congratulated me on my abilities

“Practice makes perfect,” I winked at her.

I enjoyed showing off my ass, especially when I was stretching it. Being so open around Beth definitely increased my self confidence. I wore skimpy bathing suits in the summer, wishing I could wear ones small enough to see my asshole, but I don’t think the public would be ready for that. I quite enjoyed wearing butt plugs in public though. Something about doing something so naughty, in front of an unsuspecting audience added to the thrill of it. Not to mention it felt pretty good to walk around feeling stretched out.

My favourite thing to do was go to an action movie by myself, wearing a vibrating plug. I’d sit somewhat alone near the back, then turn the plug on, and the gentle vibrating noise was drown out by the movie. It was essentially tickling my asshole in public, and I loved it. It got me so wet, I usually had to turn it off and rub one out in the bathroom. One time when I was at the back of the theatre I slid my hand down my pants and rubbed one out right there. I don’t think anyone saw or heard, but what a wet orgasm I had. Having to leave the plug inside me after, and feeling my wet panties push against my groin, by the time I got home I was ready for another go. With the vibrating plug in me I had no trouble making myself squirt. I was smart enough this time to sit on a towel. Another great anal orgasm.

The first time I did anal with a guy went better than expected. Luckily I’d been playing with my ass for a few years now, and was used to stretching it open to accommodate all sorts of objects. It was my last semester of college and I went to a house party to blow off some steam. I met a random guy there who I thought was cute, and after getting to know him after some drinks he invited me back to his dorm. Knowing exactly what I wanted that night, I asked him,

“Are you into butt stuff?”

A big smile came across his face and he replied “I’ve never tried it, but always wanted to.”

That settles it then, it’d be the first time for both of us. We grabbed a drink for the road and went back to his dorm. He didn’t have a roommate which made things easy. We started making out, which quickly led to undressing, which quickly led to me on my knees, his cock in my mouth. He got fully erect as I teased the tip with my tongue, before taking his cock in my mouth. His pubes were trimmed, his balls shaven, and his cock was about 6 inches long. ‘I could fit his whole shaft in my mouth, so my ass should be able to do the same’ was my thought. I stood up and made my way to his bed, laying down with my legs spread open. He returned the favour and went down on me, licking my clit, before driving his tongue inside my vagina. He switched back and forth between the two, making me visibly wet and horny. He then pushed his head further into my crotch, his tongue now able to graze over my asshole. His wet tongue circled around it, as pleasure spread throughout my ass. I couldn’t wait any longer.

“Lube yourself up and fuck my ass already!” I told him.

He wasted no time spreading lube all over his cock as I turned into the doggy style position in front of him. He pressed the head of his cock against my tight ass. I relaxed as he pushed more, my hole surrounding the head of his cock, before he slowly slid himself in further, his shaft slowly penetrating deep inside me. It filled me up so good, feeling his warm, stiff cock inside me. He slowly slid it almost out to the tip, before sliding it back in, my asshole now tightly gripping his shaft.

“Fuck you fill me up,” I exclaimed.

“You’re ass is so tight!” he replied back.

I smiled as he kept slowly sliding his cock in and out of my ass. Wanting to also get off and sensing this might not be a long endeavour, I started rubbing my clit as he continued fucking me. The pleasure of my clit and asshole both being used was sensational. He started to illegal bahis siteleri speed up slightly, driving his cock deeper into me than before. It drove me wild, as I furiously rubbed my clit.

“Fuck me harder!” I begged of him.

He picked up the pace more now, thrusting his cock into my ass fast and hard. His balls slapped against my pussy, adding another dimension of pleasure, as I still rubbed my throbbing clit. My asshole was used to the size of his cock now, and I was loving the feeling of him pushing deep inside me. Although I’ve used thicker toys before, I’d never fucked my ass this hard with a dildo, so his cock was doing wonders for me. I could feel his cock throbbing inside me, and I knew he was close.

“Fill me with your cum,” I again begged of him.

“You’d like that wouldn’t you slut,” he said back.

I loved it. My asshole was a slut for his cock. He kept thrusting hard inside me. I moaned in pleasure, as his cock stiffened and he fucked me one last time, pushing his cock as deep into my ass as he could. His cock throbbed, as I felt his warm semen shoot out inside me, in multiple spurts. The feeling of my cum and cock filled asshole, along with my fingers on my clit pushed me over the top, and I orgasmed hard. My whole body flexed, especially around his cock, as I was rocked with a wave of pleasure throughout my whole groin. A few more small spasms passed through me, as I kneeled there, overjoyed with pleasure.

We paused for a moment before he slowly slid his semi soft cock out of my ass, as a strand of semen followed, keeping our parts connected. He stayed knelt behind me as I felt his cum slowly drip out of my ass and make its way down ass and drop off my vagina or down my leg. What a feeling it was. I clenched my ass and got up, cleaning myself off, and found my clothes to redress, apart from my underwear which I left off. He dressed as well, and by the time his shirt was on I gave him one last kiss and headed towards the door.

“That was amazing by the way. You have a great ass,” he said.

I turned back to him. “I know,” I said back with a smile.

With that, I left, walking home with a small amount of semen still leaking out of my ass and down my leg. It felt great, my asshole felt nicely stretched and used, but leaving me wanting more still. By the time I got home I had a wet spot form in the ass of my jeans. I really was an butt slut. I got home, undressing again, and I spread my ass in the mirror to look at my hole. It was still wet, and slightly red after the pounding it took, but it still looked as tight as ever, as I stared at and adored my own asshole. I couldn’t wait to tell Beth about my night.

From that night on, I would always ask guys to either fuck my ass, or finish by cumming in my ass. I almost loved it more than cumming myself. Almost. I moved after college to get a marketing job in a big city. I didn’t really date anyone, but there was one guy I met at a yoga class that I casually hooked up with. He was into all sorts of stuff, and his long, thin cock made anal fun.

I was crouched on top of him, controlling how fast I took his cock in my ass. I opened my legs to give him a great view of my pussy, my lips were waxed bare but my mound still had hair. I rode his cock, his shaft filled my hole and my needs, as I rubbed my clit. There was nothing better than anal and masturbation, and at the same time always set me off. I started to bounce on his cock, taking it deep inside me, in short, quick bursts. I felt an orgasm was close, so I rode his dick harder, taking his whole length with every fuck. I rubbed my clit furiously, pushing myself over the edge. I stopped riding with his cock fully inside me. I leaned back as a wave of pleasure hit me. I kept rubbing my clit as I felt myself cum, squirting my juices all over the guys body. As I orgasmed, my hips writhed and his cock tensed, still deep inside me, extending my orgasm as I squirted my cum again. I slowly played with my clit as my orgasm faded. His cock was still deep inside my ass. I looked at my wet mess covering his body. His eyes were wide with bewilderment.

“That’s the hottest thing I’ve ever seen. I think I need to shower though.” He said.

I sheepishly laughed, admiring my hot mess one last time. What an orgasm. I sucked him off in the shower as an apology for squirting all over him. Everybody won in the end.

Once I got settled in the big city, I had my own apartment, a steady job, and my drive for anal pleasure was more than ever before. I missed having Beth to share experiences with. Plus we split what toys we had in half, so I had a few I had to replace. I bought a long dildo that had a suction cup so I could do anal from any wall or surface in my apartment…and I tried nearly every one. I bought a small and large butt plug set; one I could wear to work, the other I could wear and stretch my ass out around the house. Plus with the few toys I kept; the vibrating plug and anal beads, I had plenty of options. My longing to have my ass filled meant I used one of the toys every single day. I was addicted, canlı bahis siteleri and loved every second of it.

As much as I loved having my ass fucked, I didn’t like finding someone to do it. If I kept going out with the same guy, one of us might get too attached and want a relationship; I was enjoying my time not having a partner and wasn’t ready to settle down. On the other hand, finding random guys to hook up with was tiring. Having to go out, meet someone, learn about their life, make sure they’re not a serial killer, go back to someone’s house, then it’s always awkward until you start fucking. It wasn’t appealing either. I just wanted someone decent to fuck my ass and be on their way. The sex shop I frequented provided that answer for me.

First off, the staff at the shop were always great. Most were women, so shopping wasn’t as intimidating or awkward; plus they were super knowledgeable, and never judged your kink. They were holding a workshop one night that I decided to go to on ‘How to improve you and your partners orgasms.’ Lots of couples showed up, but there were quite a few single people as well. They demonstrated a few toys, for him and her that can improve orgasms; cock rings and prostate massagers for him, vibrators and butt plugs for her. They did a live demonstration with a couple as well, going over certain blowjob techniques for her; tongue vs mouth motions, deep vs shallow sucking.

They were your average looking middle aged couple, but it was hot to see them openly naked and pleasuring each other in front of an audience. His short, thick cock leaked pre-cum as the sex expert continued to give tips and suggestions. They then went over oral techniques for him; tongue movements on the clit vs vagina, sucking vs licking. He buried his tongue in her while the expert talked away. They then went over how to make the wife squirt by fingering her; the hand techniques and tempo needed to achieve this. I had no problem in this department, but watching the expert slide her fingers in the wife’s pussy, then furiously finger her vagina, causing her to squirt on the floor in front of everyone was a major turn on. I was not only wet, but jealous of her for orgasming in front of an audience.

At the end of the night, I stuck around, meeting everyone that was there, talking about our turn ons and what we were into. It was thrilling to find a group of such sexually open people. I got around to meeting the couple that was part of the demonstration. They were into just about everything, and loved having any sort of sex on display. They informed me they have a monthly swingers party/orgy at their house and I should attend the next one. It definitely peaked my interest. I could definitely get my ass fucked there. I added their info into my phone then met the owners of the shop who were talking with the resident sex expert. They were a lovely middle aged couple, that put off an easy going/hippie vibe. The expert, Cindy, was a large breasted, sophisticated looking older woman. I got to talking, thanking them all for putting on such an open and fun event, and before I knew it I blurted out that I’d love to volunteer myself for one.

I shocked myself a bit, putting myself out there, but they said they were always looking to host shows, and asked what I was most interested in. I said I loved anal and they decided they would host a toy demonstration with my ass as the display piece! I was beyond excited, nervous, and wet at the idea of it. They decided to do it the following week, then asked in detail what I was comfortable or uncomfortable with. After some discussion we made a plan for the demonstration, then I thanked them again and left the shop.

I barely made it home without having to masturbate in public I was so horny. The thought of my ass being on display in front of an audience turned me on more than I ever thought. I then thought about the orgy at the couples house the following week. I was on my back, rubbing my clit hard, squirting over a towel in no time at the thought of it all. It was going to be a very exciting month indeed.

I could barely focus on work for the following week I was so excited. The day of the demonstration I left work early to head home. I got ready, thoroughly cleaning my asshole, then showered and ate some food. I was a bit nervous, so I downed some wine as well, hoping to loosen up not only my nerves but my ass as well. I headed out to the shop to arrive early before everyone else got there. They had all the toys laid out for me to see; there was metal anal beads, increasing in size from a grape to a golf ball. There was a u shaped silicone vibrator so you can fill both your holes. There was a spade shaped butt plug with a furry tail, there was a silicone, small, fist shaped dildo, and a large, realistic looking black dildo that had a remote with it. I was beyond excited to try them all out. We decided in order to make it more fun, I would be bent over a large cushion they had so just my bare ass and pussy stuck out to the audience, while the rest of me was covered with a light sheet. I couldn’t wait to start, I stripped fully naked, showing off my perky breasts and freshly trimmed mound. I made sure my pussy lips were bare and smooth though. I climbed up on the table, sticking my bum up and out for all to see, then they covered me and I waited while people arrived.

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