Every Hole Has a Purpose

As one grows older, memories fade. However, some remain, and when thought of, they can make our bodies and minds react in ways that could make us blush. Some have those effects on me, especially the thoughts of my sexual "firsts." While reminiscing about these times, one in particular remains fresh in mind.

Trevor had been a good friend of mine for years. Never had I imagined being sexually involved him...ok maybe at times a bit curious, but to act upon my curiosity was something entirely different. We occasionally rounded the local bar, All Stars. I was never a huge fan of that place, but it was popular residing place for my friends and Trevor. Less did I know, I would become a fan of that place soon enough.

One night, while I was attending college, a group of us went out. Somehow we ended up at All Stars. I was completely bummed, since I wanted to go dancing. The idea of sitting at a bar surrounded by walls covered with flat screen TVs playing a variety of sports, did not seem intriguing at the time. As my friends split off in different directions throughout the dimly lit place, I sat at the bar drinking my beer aimlessly staring at the screens; I was bored. Another beer ordered and half-way down, when I had been startled by a big masculine arm wrapped around my chest, almost yanking me from the stool.

Trevor was behind me, laughing and obviously already feeling a pretty good buzz. He grabbed another stool and pulled it next to me. As we had always done when we met up in town, we chatted and talked about school, jobs, and pretty much whatever else kept the small talk going. Trevor was not the most gorgeous guy on earth, but not a complete waste either. He was tall, very tall, with dark brown hair, lighter colored eyes, and moderately built. He was never one who took anything too serious, humor was one of his best attributes. His buddies had left for another local tavern, in chase of some young college freshman. I asked him why he stayed at the bar and was surprised by his response. He chose to stay because he had seen me sitting at the bar. I joked with him thanking him for feeling sorry for me. He insisted he didn't, but that he enjoyed hanging out together when we had the chance. I blew it off, and ordered more drinks.

A few hours went by and I had a heavy buzz going on, Trevor did too. Throughout the night we joked, and flirted back and forth, finding reasons to get closer, I know, so cliché. At one moment, we had headed out the back doors of the joint, where the back landing was located. It had tables and chairs scattered around it. This site was merely used for "smokers." Trevor and I would light up and smoke together; there was something about alcohol that makes you want to smoke.

As the night continued on, our flirtations became more direct, and I remember my curiosity starting to creep up. I was awkwardly turned on by him, not in such a way that I wanted a relationship. I did want him alright, but in bed!

I tried hard to shake off the horniness that took over me, but Trevor had made it so hard, with all his flirting and ass grabbing. He would occasionally joke and talk dirty to me, but for some reason, this time, I wanted him to act on it. I am sure it was the alcohol, now looking back, but never would I regret where the night led.

Closing time came too soon, as it always does when you are out partying, and neither Trevor, nor myself were ready to end the night. He mentioned we go back to his place and keep drinking. I highly doubt I needed any more alcohol, but at that point, there was no stopping me. We had paid our heavy tab, and headed out the door. Trevor's buddies had shown up to give him a ride home. Because I could not drive, Trevor insisted I come home with him. I didn't exactly with him.

When we arrived at his house, I was a bit shocked when his friends backed out of the driveway. I had assumed, they too, were going to join in on the "after-hours" drinking at Trevor's place. Even though I had been surprised, a small part of me was almost giddy they had left.

Trevor and I made our way inside. I stood in the kitchen as he made some drinks. Hard liquor was never a good idea with me, but at that moment, I wasn't thinking clearly. We drank and listened to music while we sat on his couch. Our conversation wasn't much of any particular topic, but my horniness was increasing. Maybe it was the mix of alcohol and the long dry spell of sex that was making me so excited. As our banter went on, at some point we ended up making out on his couch. Just kissing him made me so wet as my pussy tingled and throbbed in my jeans. We pulled away from each other after minutes on the couch and headed down the hall to his bedroom.

We had barely made it through the threshold of his doorway, before he started to aggressively undress me. He whipped my shirt off, bra included, and threw them to the side. I was stunned and could hardly get his jeans unbuckled before he had made his way to my pants. There I stood, half naked in front of the one person I never would have imagined sleeping with. But it was game on, no backing out now. I wanted him more now than I had ever wanted anything.

Trevor was in front of me with only boxers on, and a raging hard on. I had never seen his cock, but was certain it was of decent size from how it felt in his jeans during our groping session on the couch. I was so excited to get his cock in me, that I threw myself on the bed making myself ready for him. He had climbed atop of me, kissing my lips, neck, and chest. Teasing as he sucked on my nipples, turning them into hard little buds. My pussy was throbbing with a sensation I don't recall every feeling before. I feeling of undesirable need, maybe.

Not to sound "slutty" but I had had my fair share of sex before this encounter. It was always the same, lame engagements; almost always missionary or me on top. I had never really expected anything different. I had always known I had a bit of a freaky side, but too shy to expose it. On this night, I was perfectly content with the usual positions. I had just wanted to get laid.

As Trevor laid over me, I had used my legs to work his boxer shorts down his flexed legs to his ankles, exposing his thriving cock. It was hard to see in the dark, but there was some part of me that was eager to get a glimpse. I could see his tight purple head standing tall up his belly; the little sneak peak causing my pussy to thump and feeling my lace panties becoming damp. I gripped his firm dick in my hand and played with the tip, rubbing my thumb over his moist slit. He began to moan deeply in my ear sending chills throughout my body as I gently began to pull his cock closer to me. My panties were still on, and I was trying to figure out a way to slide them off without having to let him go. Before I could figure out a solution, Trevor had taken his hand and slid the underwear to the side, exposing my trimmed wetting lips. Once he moved the lacey cover aside, I eagerly guided his dick inside of me.

After a few tender thrusts, he began to pump his hard rod in and out of me. I could tell my pussy was really wet by the ease of his dick rocking back and forth. For a few moments, we fucked on the bed, working me closer to orgasm, just never quite getting there. I moved my hips and twisted side to side underneath him matching each ramming thrust, trying to prod myself closer to climax.

I was slowly beginning to sober, and almost whined when he stopped and pulled out. I couldn't fathom what was going on or why he would stop. I only prayed it would start again. I had asked him shyly what he was doing, and he told me in a low sexy tone to move to the edge of the bed. I did just that; a little nervous about what was going on. He walked around the foot of the bed, and opened his night stand drawer and pulled something out. I couldn't tell what the object was, I assumed it was a condom (thinking to myself, well that would have been a good idea about 10 minutes ago).

He suddenly grabbed my legs and pulled me closer to the edge of bed and had me lay down. Grabbing my calves, he pinned my legs up and supported my ankles on his shoulders. Already, this position was entirely new to me, I was turned on and nervous, not knowing what was happening or about to happen. His rough, masculine hands skimmed down my legs and then under my ass. His fingers locked around the top seam of my thong and he began to slide them up my legs, then off. His hands traveled back down my legs, causing my body to respond with goose-bumps. He ran his finger along my tingling clit, swirling in circular motions causing my clit to swell and throb. Him playing with and touching my pussy felt so good; any attention to my pussy was amazing. Eventually his thumb took over my clit, applying more pressure to the sensitive bud, as he slid two thick fingers into my dripping pussy. While he was finger fucking me, he reached over to the drawer and grabbed a small white bottle. I tried to watch him, but his fingers were making me crazy, and my ability to focus had been lost. As he pushed me closer to orgasm, he pulled his fingers out and inserted something hard and solid, not his dick. Before I was able to ask what it was, the vibrations hit. All I could muster was a bunch of "oh's" and "oh Gods." The vibrating toy had felt amazing, yet still nothing could have prepared me for what was next.

As the vibrator assaulted my pussy, sending tingling sensations to my clit, I felt something cool on my ass. Trevor increased the speed on the vibrator, and when the intensity kicked-up; he slid a gel covered finger into the pink rim of my ass. I pulled back, as he told me to relax. I tried my best to do so, but I was not at all experienced with anything going in the back. I had been trying to focus on what Trevor was doing, but the distraction of the vibrator kept pulling me away with each transitioning pulse. Trevor kept his finger in place, and very slowly pumped my ass with his digit. Honestly, it felt incredible; it was tender at first, but hey, it's easy to adjust to the size of a finger.

He must have known I adjusted to his little surprise because before I could stop him, he inserted another finger; this time, a bit faster. I clenched up, and yelled out at him in pain as the small constricted hole was stretched. I was frustrated with the fact that he just smiled at me instead of pulling his fingers out. He squeezed out a small amount of lubricant down towards his fingers, and slowly lathered my ass hole as his fingers slid in and out. The vibrator pulse and speed changed, causing distraction; helping me to relax. After, the initial sting of his insertions, the mix of the vibrator in my pussy and his fingers in my puckered ass started to feel magnificent.

For what felt like hours, he worked and stretched my ass. I heard the bottle being squeezed again, but the sensations I was feeling had me lost in a whirlwind of pleasure. Trevor told me he wanted me to focus on the vibrator and relax. At that moment, I told him ok, not knowing what he had planned for me.

I hadn't noticed he pulled his fingers out of my ass until I felt the tip of his erect cock poke my sensitive void. I clenched up and told him no, he had responded saying "trust me and relax". I tried to argue with him, but again the vibrator speed increased and pulsed inside me. All I could think was, what the fuck is happening. Distracted with the buzzes in my pussy, he pushed his cock a bit further, again I yelled. The pain I felt was awful. The tightness of the hole and size of his dick did not meet well. Trevor stopped, still not pulling his cock from my ass. He grabbed the gel and added more around my burning rim. The cool moisture eased the stinging for a moment. As more lather was smoothed around his cock, he started to slowly, very slowly, push his dick further in my ass.

Never had I ever imagined or wanted to perform anal sex with anyone. My only thought on it was is was disgusting, and I would never want to feel pain like that during sex. Why would anyone want that?

More lotion, and further insertion was what I got. No relief. The pain increased as the thickness of his dick filled my ass, inch by inch. I tried to breathe slowly, but my lips had gone dry and the air I inhaled burned my lungs. My eyes had started to water, I wasn't crying, but looking back now, I think my body was truly reacting to the discomfort. I just remember being terrified of how would feel coming back out.

Again, cool gel was rubbed around my ass, easing some of the discomfort. Once he had stretched my hole long enough with his cock, he started to pull back out. The ripping sensation almost had me screaming out. I begged him for more lubricant, which he added. He gradually began to pull back more; this time the pain was not so bad. Although he pulled his shaft back, he left the tip of his cock inside my sore ass. Graciously adding more lube to his cock, he started back in.

The burning sensation remained as my tender hole adjusted around his member. He continued to grind his dick in and out of my hole. As the vibrator, still placed nicely inside my pussy, throbbed away, the sensations of the two holes being assaulted began to feel good.

Trevor's thrusting speed increased as my ass began to relax around his dick, allowing it to glide in and out more freely. As my ass was becoming more acquainted with his large round thickness, I started to move with him. Enjoying the pressure and occasional sting his dick made in my ass. Leaning forward over me and stabilizing himself on the bed, he drove his dick harder and faster into my rear. The pain and pleasure was sensational, sending tingling vibes throughout my core. The vibrating continued to oscillate my clit and pussy, as his pulsing cock pumped in and out of me. I gripped the edge of the bed to steady myself as I began to writhe all over the bed. Trevor placed his hands on my hips soothing my movements. The pain of his thrusts heated my hole, yet the lube alleviated the friction just enough that eventually my small little cavity was able to fully consume his long broad shaft.

The exotic pleasure I was feeling was all I felt. My insides beginning to quiver and tingle low in my belly. He continued to drive his slick cock in and out of my ass as my body absorbed his size with ease after each thrust. My pussy was so wet the vibrator started to slip out at I uncontrollably tensed my lower core as I inched closer to orgasm. The feel of his balls smacking against my spread cheeks only added to the foreplay. Gripping the sheets, my body jerked and shivered with electricity as I exploded into orgasm. The vibrator came out, followed by the release of my creamy cum. I felt my juices trickle down to my ass where his dick was moving about, adding to the lubricant. Once Trevor realized I had climaxed, he immediately follow with his own, shooting his large load into my ass. My body was still shaking in waves, increasing when I felt his dick push far up my ass and release. The increase in pressure his cum caused inside my hole sent me straight into an aftershock orgasm. As our bodies slowly recovered, he pulled his cock out of my tender little hole. I had no words to offer, only heavy breathing. Once we were cleaned up and dressed, I left and drove home with a smile on my face; sore, but smiling.

Never would I have thought the best orgasm I would ever experience would come from having my ass assaulted, less introducing me to one of my most favorite ways to fuck.