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This is a story from long ago, which was a formative part of my emergence as a slut. These are my recollections on how I came to love anal – I didn’t start out liking a cock in my ass but nowadays it’s one of my favorite sex positions.

It started in the early 1990s when I was a freshman student at a University in Canada. I’d moved from home in rural Ontario to the big city and I was living in the University’s coed halls of residence. I had a small room to myself in the female wing, but there was plenty of fraternizing between guys and girls, despite what any of the rules said.

I was studying computer science — at that time it was a vastly male dominated field, so I was one of only a handful of girls in amongst a sea of young men. When I say “young men”, almost exclusively the cohort was full of pimply, geeky boys who were mostly focused on computer hardware, software algorithms and the latest brand of cola. When they weren’t studying, they played lame computer games — back in the 90s Tetris was one of the highlights!

This was the time of grunge. You might remember the music — Pearl Jam, Nirvana, Tool — they were all on high rotation on my Walkman, but most of the guys in my classes were not really into music at all — just computers. However, the grunge fashion was ubiquitous. Unisex long hair, flannelette shirts, jeans and converse shoes — that was the uniform. My long, straight hair had a flat, greasy look to it, but that was the norm for the era. The majority of students at my University dressed this way — apart from the law students in more formal attire and the physiotherapy students in sportswear.

I was a virgin when I started university. My first few sexual experiences happened in my dorm room after dates or university functions. For that first year my romantic and social circles were confined to colleagues in my computer-science classes. There were a few alpha types in the class, and they were the ones that I found myself attracted to. But the alpha status was not bestowed owing to their physique or sexual allure. Looking back it seems ridiculous, but the top dogs acquired their position from their prowess at programming or knowledge of computer systems. Being one of the only girls in the class — and probably one of the only females that they ever spent time with — I was popular, and I could pick and choose my dates.

I laugh when I look back at the bad sex I had during that first year at University. At the time I didn’t know any better, but the bedroom action was so mediocre. To be fair, I guess the guys didn’t have much experience either.

The first time was with a guy called David, who is now a big-time Silicone Valley guru worth a mint. Back then, his claim to fame was the highest score on Leisure Suit Larry and the ability to code sorting algorithms in C better than anyone else. The University put on a function in week ten to celebrate the end of the first term of the degree. There were tons of free drinks and everyone got pretty wasted. A few guys expressed interest in me that night, but I chose David, who lived off-campus, to take back to my dorm room.

We got into the action pretty fast. He was hard straight away so I pulled his jeans and Y-fronts down and sucked his dick for about a minute. Then I lay back on my bed like a star-fish and he pounced on top. His cock poked around for a while trying to find my entrance, and I had to reach down and guide it into position. Thrust once, twice, three-times and with a groan he was done.

I asked if he wanted a shower, and he responded by asking if that was the right thing to do. I didn’t really mind, so I sneaked him down to the showers, he cleaned up and we returned to my room. I was still horny, and with some coaxing I got him hard once more. There was no explicit discussion, but it was understood that I was keen to fuck again, and I offered myself in doggy position this time, and traced a finger across my slit to demonstrate how wet I was.

David went for it, in a way that totally surprised me at the time. He placed the head of his cock directly onto my unsuspecting asshole and pushed as hard as he could. Of course, there was no way that it was going in – no lube and I wasn’t ready. But he tried anyway. It all ended in an argument, and David avoided me for the rest of our time at the University.

The next few sexual liaisons all came after dates and they followed a familiar pattern. A nice evening, back to my dorm, foreplay, sex and then at some point they’d try to surreptitiously jam their cock into my ass like I wouldn’t notice. Usually I’d react badly, but after a few times, I tried to let them have their way using a bit of spit as lube. But I was always nervous, clenched tight and the pain always became overbearing. The guys would react differently– some would get angry and storm out, others would be understanding and we’d just revert to regular sex.

Nowadays, everyone understands how important communication is during a sexual liaison. But back then communication was pretty minimal — it was almost non-existent in my encounters Beşiktaş escort — these guys didn’t really open up amongst each other, let alone with girl like me, who might as well be an alien!

After having the same experience a bunch of times, I thought that I’d better get on board and ‘put out’ when it came to anal. Nowadays, you can go online and work out how to do these things. Back then, the Internet was only just starting, and we didn’t have the volume of porn or channels of advice that are available now. We didn’t even have online shopping!

One weekend, I travelled downtown to a dirty sex shop and bought lube and a small dildo. I felt so nervous visiting the store that I wore sunglasses and a hat through the whole transaction to keep my identity hidden. So totally different to my modern-day self where I’m happy to publish all of my sexual activities out to the world on high-definition video!

Over the next few weeks, I explored the pleasures of my ass in the dorm room with the dildo and my fingers. It took nearly a full week of masturbation each afternoon to get a finger fully inserted into my tight ass, after I discovered the secret that too much lube is never enough. Once I got to that point, the dildo followed fairly easily. Compared to my pussy, my ass brought a new set of indulgences — the pleasure really came from stretching myself open, and the sensation of something slippery sliding outwards from the hole was really exciting. When I was fingering my ass, I discovered that my pussy leaked like a faucet, and the sensitivity of my ass was enhanced if I played with my cunt at the same time. It became addictive, and I’d rush home at the end of class each day to squeeze in a dildo session before dinner time.

Eventually, I was ready to try out anal with a real cock. By then I’d decided that the guys from my class were not the way to go. Of course, the composition of the dorms extended beyond computer science students. There were plenty of human movement and physiotherapy guys who were pretty buff, but I didn’t trust them either.

Instead, I formulated a plan.

I thought that I could use the experience and knowledge of a gay guy to teach me the pleasures of anal.

Unfortunately the times were not as accepting as they are now, even in the University community. I didn’t know a single gay guy at the time. As it turns out, I actually knew plenty, but they were all in the closet. Lots of my classmates have come out in the years since, but back then it was completely taboo.

But everyone knew about gay bars or at least the idea of gay bars. They were at the heart of jokes and homophobic teasing in daily banter. I knew that there would be at least one somewhere in the city. I decided that I’d dress up as a man, visit a gay bar, pick up a gay guy and go back to their place for some anal action. Easy right?

I did my research (but no Internet back then!). The back pages of the city newspapers had cryptic ads that I worked out, and I cycled my bike into the city for some reconnaissance trips. I identified a large black door and blacked out glass windows in a building on the borders of the central business district. At night there would be a couple of suited bouncers out front and muffled music coming from within. I never stayed long or late enough to see anyone go in or out, but I was confident that I’d found the location.

I picked a Saturday night away from examination times and assignment deadlines for putting the plan into action and I got everything ready ahead of time. I was fortunate to be slightly built and fairly thin — actually everyone seemed to be back then. My boobs had not filled out by that stage and my hips hadn’t suffered the middle aged spread that came later. So I think I did a pretty good job dressing up as a male. I wore my regular attire which was the unisex grunge uniform, but I donned a really tight singlet underneath to keep my tits compressed. I rolled up a sock and jammed it into my panties for a generous cock-sized bulge — some bait for my fishing expedition, so to speak.

My face still had the soft skin of a female with a rounded jawline, but I also had a plan to deal with that. Another thing that’s changed in the intervening years is the nature of grooming. Maybe it was a more innocent time or perhaps it was my social circles of liberal University students, but I don’t think anyone really waxed down there. Which turned out to be quite fortuitous because I used some scissors and some makeup glue and I was able to create a little stubble on my face from my pubes. Honestly, I think it looked just like most of the guys in my class.

Before heading out that night, I played with my ass for about a half hour with the dildo and the lubricant. Eventually I progressed to my fingers and managed to get myself stretched open enough to fit two fingers into my asshole. I wiped away the lube from the surface of my ass, but I knew that there was still plenty inside of me. Then I caught the bus downtown and walked the last mile to the club.

I didn’t Beşiktaş escort bayan know entirely what to expect when I got there, but I thought that I was pretty well prepared. I’d planned out the evening but I did forget one crucial detail. The bouncer on the door asked for my ID as proof of age. Shit! My ID would clearly show that I was a girl. I held my breath, showed him the card and he asked, “Are you sure you’re in the right place?” I nodded, and he stepped aside and just let me through. A stroke of luck!

When I got inside, there were plenty of guys in the club, but no one looked like me. Grunge was the fashion at University, but obviously not in the gay scene. You might remember that this was the era influenced by George Michael, and that’s what this crowd looked like. Lots of clean-cut hairdos, white tee-shirts and plenty of blue denim.

I found my way to the bar, leaned back and surveyed the scene. There was a bar around two sides of the venue, a large dancefloor in the middle, and an area with tables and stools off to the other side. Guys were standing along the bar or at the stools watching the action on the dancefloor. Back at University social events my friends generally danced in in a loose circle of six to ten people, but here it was much more intimate. Gay couples were embracing, kissing while they danced, or in provocative threesomes, with the lucky guy in the middle enjoying caresses from the front and the back. There were no females to be seen.

I identified a cute guy with a longneck beer standing alone at the bar away from the serving area. He was leaning back, with his elbows on the counter and feet crossed at the ankles. He had a clean-shaven, handsome face with a nice physique and his attire was the club standard: white tee and blue denim jeans.

If I hesitated, this was never going to happen. I drew my breath, walked up and sidled closely beside him, pressing my back against the bar and said “Hi”. He looked at me suspiciously, but he replied with a “Hi” in a friendly enough way. I mustered courage and went straight for it.

“Do you want to fuck me in the ass?”

Reflecting now, the “in the ass” part was redundant for one guy approaching another. And I’m not sure it was the best pickup line. But in another stroke of luck, the approach was successful. He replied, “Sure,” placed his beer on the bar and took me by the hand. He led me towards the exit and I thought he was going to take me home, but he veered at the last moment and pulled me into the restroom.

Wow! I’d never seen a restroom like this before. The fit-out was more even glittering than the rest of the club. It had an expansive common area with high mirrors and long counters with washbasins along the wall. There was even disco lighting going on. But the thing that struck me most was the guy bent forward over the counter getting fucked in the ass while two men watched on.

My new friend who had led me into the bathroom looked back to me, and in a turn that even surprised myself I said, “Like that.”

I voluntarily walked to a part of the counter without a basin, around 6 feet away from the guy getting anal and I faced the mirror. I undid the button at the top of my jeans and pulled the pants down over my butt, just enough to expose my asshole. Then I placed my two hands on the counter and waited for his move.

I looked ahead to the mirror so I could see him behind me, but before paying any attention to me, he sauntered toward the group already having sex, and reached for a nondescript plastic squeeze-pack sitting on the countertop. He squeezed a liberal amount into his hand, and returned to a position behind me. He did not make eye contact as he was transfixed, looking down at my behind. I felt a slippery hand massaging the inner cheeks of my ass and running back and forth across my sensitive hole. I was nervous, and I could feel myself clenching tight, but still it felt nice. Then I felt the pressure of a finger, gently, but relentlessly stroking and pressing, stroking and pressing.

He had located his finger nicely, and massaged for a short while before he looked up at my face in the reflection of the mirror. “OK?” he asked, and I nodded once. Immediately with a smooth drive, I felt the finger plunge through my ring and I gasped as he reached inside of me. His other hand positioned on the cheek of my ass and his finger began to rhythmically slide in and out of my hole. Deep inside, then right out and I could feel my anus close right up, before he opened me again with another stroke.

He continued with the stroking for some time and I became completely comfortable with it – in fact, I was getting as horny as hell. Looking to my left, the guy getting fucked in the ass was moaning in delight, and his head was turned in my direction. The two onlookers had pulled their cocks out of their pants and they were gently jerking off while they watched the action. It didn’t take long before I wanted more – I could feel my pussy aching and my ass was longing to be stretched and filled. And my new friend Escort beşiktaş complied.

His finger withdrew and his eyes went back to my ass. My body obscured the view, but through the mirror I could discern that he was taking his cock from his pants and rubbing the lube up and down his member. I felt the sharpness of a fingernail as he sought to locate his cock, and then the pressure of his smooth head against my slippery ass.

His hands shifted to each of my hips, he looked up, and then I felt that familiar pressure of a cock against my asshole. Except this time there was no pain, and only a gentle resistance. He pushed forward while I pushed back and the head just slipped in and I felt my ass close up as the ridge passed through my tight ring.

In and out. Back and forth. It was heaven. Even better than the best pussy sex I’d ever encountered up until then. A nice smooth tempo, and I could feel myself stretching each time he pushed in just a little bit deeper. I was starting to fall into a trance, but I did detect that the two voyeurs from the adjacent session had moved closer and now turned their attention to me.

The thrusting started to become harder, and the speed a bit faster, and I could hear his breathing become louder, when I looked up to see a couple more men had gathered around to watch. My friend was watching my face in the reflection of the mirror, when he jolted with surprise. A more heavily built guy in jeans with bulging muscles and a tight white singlet came up from behind and placed a hand on his shoulder.

I had no idea about the social hierarchy within the gay community, but this new guy was clearly dominant. There were no words exchanged, but my friend withdrew his cock from my ass, and buttoned up his pants as he backed away. I remained stationed in the same posture, and the big guy took his place. He unbuttoned his pants, and pulled out a cock, but I could not see it from where I was positioned. “Lube!” he announced, and one of the spectators handed him the squeeze tube. He lathered it on his cock, and then I felt him position himself against my asshole.

Immediately I perceived that his cock was much larger than the last one. I was worried that it would be a repeat of the anal experiences I’d had back in the dorm, but in an environment where I had no escape. But my fears couldn’t be further from reality. The cock firmly pressed against my asshole while his hands each caressed the cheeks of my ass and pulled me gently open. I closed my eyes and I could feel him guide me into a swaying action, and I soon felt relaxed all over, especially in my sphincter. With his unyielding pushing and me pushing back, his cock stretched my yearning ass and slipped inside. I felt a pang of discomfort, but it was overwhelmed by the satisfying feeling of being filled. It felt so good once it was finally within me, like the satisfaction of inserting the last piece of a jigsaw puzzle — to the power of one million. And it kept going. Back and forth, opening me up more and more. I could feel him inside me, moving around in my cavity, probing the edges, pushing up against the walls of my cunt. I didn’t realise it, but I began moaning in pleasure, and when I and opened my eyes again, there were even more men gathered around in a circle watching.

The big guy reached around my waist and fumbled down the front of my pants. He was feeling for my cock, but of course there was none. His fingers groped around desperately — I reached down to grab his wrists to get his hands out of my pants. I suddenly felt nervous and didn’t know what would happen if I was discovered as a girl in disguise.

But he was much, much stronger. He grabbed both of my wrists, lifted my hands and pressed them against the mirror in front of me. Gruffly he instructed, “Hold these,” and two of the voyeurs approached, one from each side, and held me by the wrists, keeping my hands pressed hard against the mirror.

The big guy pulled my jeans harshly down to my ankles in one swift sweep, and the sock fell out that I’d been using as padding. He reached between my legs and roughly groped my hairy pussy. “Ha! We got ourselves a girl here fellas!” he announced.

Somehow even more guys appeared to circle around me. I don’t know where they had come from. Through the entry door, fire exit, out of cubicles, who knows?

I was really nervous at this point, and my mouth suddenly dried up. The big guy leaned forward and placed his mouth against my ear, while he looked directly into my eyes through the reflection of the mirror. “What are you doing here girlie?”

“I want to get fucked in the ass. I want to know how you do it.”

The big guy smiled in obvious enjoyment and relief and looked around. “OK boys, who wants to fuck a girl in the ass?” The crowd cheered and I heard a few volunteering “Me!”

He turned me around and said, “But I’m finishing my turn first.” The voyeurs released my wrists and the big guy lifted me off the ground and placed me onto the countertop. He pulled my crumpled jeans and panties from my ankles and leaned me backwards with my knees together held up at his chest height. He reached to the tube of lubricant on the counter again and applied a dollop to his cock. Then he placed his cock against my ass, smiled and looked me in the eye while he pushed the head against my puckered hole.

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