A Collection of First Times

"No," he said. "Get on your hands and knees. I want to fuck you doggystyle."

His business-like, no-bullshit tone instantly turned me on. I didn't care at that point if he could fit in my mouth or my pussy, I wanted him inside me. I scrambled onto my hands and knees and he climbed back onto the bed and kneeled behind me. I felt his hand pressing on my low back and I instinctively arched my back, exposing my upturned ass and glistening pussy to him some more. With the other hand, he began rubbing the head of his monster cock between my slippery labia.

"Stay just like that," he said.

When he was satisfied that he had lubed up his cock with my pussy juices, he lined the fat mushroom tip up with my tight opening and pushed inside me until he bottomed out. I grunted and almost passed out from the intense sensation. He then gripped my hips tightly, pulled out halfway, my pussy lips clinging to his shaft, and then thrust back in again. He bottomed out again. This time I could feel the head of his cock banging against my cervix, he was so deep inside me. I winced and tried to tuck my pelvis under for some relief.

"Uh uh..." he scolded and placed his hand on my lower back again, forcing my back to arch and angling my pussy up so I could accept more of his huge dick. "I want to see if you can take it all..."

It sort of hurt but I had never been more turned on... Here I was, buck naked and panting on my hands and knees, with this strange man mounting me from behind, fully clothed except his bare cock, giving me the deep dicking of my life.

He fucked me doggystyle for awhile, grunting and occasionally forcing my back into a deep arch, my tight opening accepting more and more of his huge slab with every thrust. I had never been so stuffed full in my life, I could practically feel him in my uterus. The pressure was insane.

"Oh fuck," he moaned after a few minutes, "I'm stretching that little pussy wide open and your little asshole is winking at me..." I was praying that he wasn't going to try and stuff his giant cock up my virgin backdoor when I heard him suck a finger into his mouth. I felt him run his wet thumb over my crinkled, exposed anus while he fucked me, then slowly, he slid his finger into my butthole, plugging the tight orifice with his thumb.

The pressure in both my cunt and my asshole pushed me over the edge and I howled in orgasm like an animal in heat, begging for mercy, but his cock and fingers kept fucking away. Finally, through a haze, I heard him gasp, "I'm close... where do you want me to blow my load?"

I managed to pant hoarsely, "Cum on my face... I want you to pull out and jizz all over my face..."

He groaned when I felt his thumb slide out of my still-spasming asshole, and when he pulled his slick, swollen cock from my stretched cunt, I swear I heard an audible pop. It felt like my once-tight pussy was gaping open from the insane fucking I just received.

"Get on the floor," he growled, stroking his throbbing cock with his fist, the shaft still soaked from my juices. I scrambled to the floor and kneeled as he stood over me, jerking his monster dick until he blew his equally gigantic load all over my face.

He shouted and whimpered as he came and I kept my eyes closed as he painted my face with blast after blast of warm semen. His cum was more clear and liquid than Harley's and it was all over my eyelids and the bridge of my nose and dripping down my lips by the time he finished. He reached for the washcloth by my bed and wiped his huge load off of my face. I was just relieved he hadn't busted that gigantic nut inside me. He was so deep in my cunt he would have knocked me up no question.

John-Paul silently put his softening cock away and began packing up his equipment. He promised me copies of the photos and then left. I took a long bath and soaked my sore pussy, trying to recover.

The photos turned out great, and though he texted a few times, we never met up again after that. I think I was happy at just keeping that a one-time event. I didn't think I could handle his monster cock on the long-term.

***Andy: my First Butt Fuck***

Andy and I first started talking on a dating website but then he lost touch and I didn't think too much of it and moved on. I had plenty of distractions. In addition to the normal dating websites, I had joined a fetish site. I had become more and more curious about having anal but while I had had fingers and butt plugs up my ass, I will still technically an anal virgin.

I had posted some anonymous pics of my spread ass, my asshole plugged with a shiny jewel butt plug, and was constantly receiving comments and propositions from the guys on the site. Some of them were tempting, but the one I responded to the most was from this one guy who seemed cute and funny, who told me he'd love to take my anal cherry.

We started texting and things got super flirty and then super dirty. He told me how much he'd like to fuck my cute little asshole and how good it would feel. He knew how to press all my buttons. We finally exchanged face pics and that's when I realized it was Andy. He immediately recognized me too.

"Holy crap," he texted me, "this is too good to be true. I was interested in how pretty and smart you were, but I thought you were super wholesome and felt bad exposing you to my dirty side. Now that I know you are into butt sex, you're irresistible to me. We have to meet."

I was reluctant at first, and then finally gave in. Before our first "date" I lubed up my butt plug with vaseline and carefully inserted it into my tight asshole before I left.

We shared dinner and some pretty bland conversation. He was cute but there was something about him that just wasn't my type. But when he pulled me into him and kissed me, begging me to let him come home with me and play with my gorgeous ass, I decided I'd give him a chance.

We made out some more on the subway on our way to my apartment, his big hands grabbing handfuls of my ass. Each time he squeezed one of my cheeks I could feel the metal plug throbbing in my tight asshole. He pulled me into his lap and held me tight. When the train car emptied out, I slipped his hand under my skirt, into the leg band of my panties and brushed his fingers over my pussy and asshole. When he felt the jeweled plug his eyes widened and I smiled. We kissed passionately until we reached my stop, him gently toying with the metal plug under my dress.

When we made it into my apartment, he wasted no time: he bent me over the foot of my bed, lifted up the skirt of my dress, peeled down my panties and spread my cheeks. He groaned in appreciation at the sight of my virgin asshole, plugged with the jeweled plug.

He slowly grasped the edges of the plug with his fingers, and began gently tugging on it. He pulled it out halfway and my hungry asshole sucked in back in like a pacifier. I groaned at the intense sensations. After a few minutes of teasing, he pulled the butt plug all the way out and then knelt behind me, burying his face between my butt cheeks.

As he hungrily rimmed my throbbing starfish, lapping noisily at the tight ring, he grabbed my hands and guided me to hold my cheeks open for him. I spread my ass wide for him and he slipped his tongue into my anus and began fucking my tight hole with his tongue. I gasped at this new sensation.

After a few minutes of french kissing my backdoor, he pulled away and started stripping his clothes off. I got a glimpse at his erect cock as it sprang into view and while it was a normal length, it was really meaty and girthy, and very thick with a pronounced tip. I think he saw the worry on my face and said, "don't worry, I'll use a lot of lube and go slow."

I peeled off my dress and bra and climbed onto the bed, and while I searched in the nightstand for a condom and some lube, Andy climbed behind me and started kissing and nibbling on my ass cheeks.

"You taste so good," he moaned. I passed the condom and the lube back to him and he began preparing my virgin asshole for his imminent invasion. I crouched down with my ass high in the air and he gently spread my cheeks, squeezing lube in a huge dollop right on my brown eye. He then started working the lube into my tight hole with his fingers, inserting one, then two of his thick digits. I was glad I had been wearing the plug all evening so I was already a little stretched out.

When he finally got two of his thick fingers into my lubed butthole he began scissoring them open and closed, trying to stretch my backdoor open some more. He clearly was no novice at this.

After a few minutes of stretching me open, he slowly withdrew his slippery fingers from my chute and unwrapped the condom. I turned over and watched him roll the rubbery condom over his thick shaft and then it snapped. His cock was so thick he had ripped it. I didn't have any large condoms. We agreed that he could fuck me bareback if he didn't cum inside me. I watched him lube up his thick shaft and I rolled back over onto my tummy while he mounted me from behind.

He pressed his fat cock head right up against my balloon knot and then pushed. The pressure was so intense, I started breathing deeply and clutching the sheets into my clenched fists. I couldn't believe I was having butt sex with a guy who had never even fucked my pussy. After what felt like minutes of pressure my asshole gave way and I actually felt the ridge of his mushroom tip as it popped into my tight anus. He groaned. "Oh man, that feels so good, open your ass for me a little more, baby."

I was panting and gripping the sheets when I felt his thick cock slide a couple inches deeper up my butt. It felt like I had to take a giant shit, it was so intense. "Oh yeah, that's a girl... good girl..." he groaned. I shivered and moaned as the last few inches of his erection pushed into my no-longer-virgin ass.

He withdrew slightly, adjusted and then slid back in again. As intense as it felt to have John-Paul fucking my tight pussy with his monster cock, this was a whole other level of intense. Andy continued to slowly pull out a few inches and then push back in to try and get me used to the strange intense feeling of his cock stuffing my butthole.

When he could feel me relax my grip on the sheets slightly, he suggested I get up on my knees so he could get a better angle. I raised my ass in the air, keeping my upper body flat on the bed and he pulled out all the way to reposition himself.

One of the disadvantages of his "in and out" technique was he was forcing air up my butt every time he pulled out and pushed in again. His thick shaft only added to the pressure. So when he uncorked his cock from my ass, all of the trapped air came out with it as he pulled out, my poor asshole making this loud, involuntary fart sound. I was mortified.

"That's totally normal," he assured me, "Trust me, it's par for the course. In fact, hearing all of the buttfucking noises kinda turns me on... If you ever let me cum up your butt, there's nothing I love more than watching a girl push my cum out afterwards. The trapped air makes all of these little cum bubbles... It's so fucking hot." Andy got up onto his knees and grabbed my upraised ass by the hips.

"Spread your ass for me again, baby," he whispered. I reached back and spread my cheeks. "Nice," he said, and lined his fat cock up with my open ass again.

This time he pushed in a little faster, pushing more air up my butt, and when he pulled out, another little fart sound escaped. He got into a more regular fucking rhythm and each time he pushed his fat cock up my ass and pulled out again, my poor asshole helplessly protested with a small farting noise.

After a few minutes of this, my embarrassment started moving into arousal, and the perverse squelching sound of him fucking my butt began turning me on. The intensity of his thick log stretching my poor little hole lessened and I started enjoying the sensations of being stuffed full.

"Oh God, your ass feels so amazing wrapped around my cock," he moaned, "I bet I'm stretching out that little virgin hole nice and good..."

After a few minutes, he pulled out to admire his handiwork. I felt incredibly empty as his cock slid out and the cool air hit my open hole. "Oh man, your little asshole is gaping so wide..." he said, and reached for his phone. "Spread your ass, baby, I want to show you how much I opened that virgin asshole up..." I heard him take a few photos of my gaping hole as I splayed my cheeks open for the camera.

On the fetish website we had talked about how much I was turned on by the idea of a guy making my tight knot gape with his dick, since it seemed so sexy and dirty to me. But no matter how hard I tried, I couldn't really make that happen yet with my little butt plug. When he passed me his camera and I got my first view of my poor used butthole, I could feel my pussy juicing. My little coin slot was now a wide open gaping hole, about the diameter of a half dollar, the edges red and wet with lube. Even in the picture I could see my shaved pussy glistening with my excitement.

He went to mount me again, and I stared at the photo, holding the camera with one hand and reaching my other hand underneath me to play with my pussy while he boned my ass. The sensations of playing with my clit while I was getting my buttfucked were exquisite. I came in a hard little burst, my asshole clamping down on his fat pistoning cock.

"Oh man, your little asshole is wringing out my cock..." he moaned, picking up the pace. Cumming had loosened me up a bit, and he started buttfucking my poor ass in earnest now.

"Here, pass me my phone," he said, and I passed it back over my shoulder, then pressed my hands against the bed, pushing myself up until I was on my hands and knees. "I'm gonna make a movie..."

I heard him press record then felt him get up on one knee so he could get a faster fucking angle. "That's right, baby," he moaned, "now fuck yourself on my fat cock."

I pushed back against his hips, his thick shaft splitting my ass as it went inside. I enjoyed the control and got into a slightly faster rhythm as he filmed the action. Then I felt him grab a fist full of my hair and pull my head back, impaling me further on his fat cock. I grunted as he bottomed out in my ass, his heavy balls nestled against my wet pussy lips. Then he began pulling me on and off his cock using my ponytail as a handle. The sounds of his grunting, his hips hitting my bottom and the squelching and farting of my poor stretched asshole filled the air. He reamed my bunghole like this for a few more minutes, showing off for the camera and gripping a big hunk of my hair and then he dropped the phone on the bed. With his free hand he started spanking my ass as he continued to ride me.

"You like that?" *smack* "You like me riding your little virgin ass?" *smack* "Are you a good little butt slut?" Andy grunted as he continued spanking my sore ass and pounding my dilated hole. My asshole was burning and my red cheeks were stinging from the spanking but I was having the time of my life. It felt so dirty to let a practical stranger take my ass like this. I grunted and moaned in pleasure as he humped his fat sausage into my butthole again and again and again.

"Gonna cum..." he groaned and pulled out of my gaping asshole. With a few more tugs on his thick, wet cock he came all over my upturned ass and open hole. I felt the first two volleys as they hit my skin and then some more drips as he milked the final drops from his balls onto me.

He grabbed his phone and clicked one final pic of his masterwork, then grabbed a kleenex from my bedside table, and wiped his jism from my asscrack. When he was done cleaning me up, we collapsed into a big heap, and he held me, cuddling me until we both fell into an exhausted sleep.

The next day my ass was so sore and bled slightly, and I didn't shit right for days, but it was worth it. I guess I went a little wild that first time. Not many girls would try to take a cock that thick up their butt on the first try.

Andy texted me the final photo he took: my cum-covered ass gaping and sore and looking thoroughly well-fucked. I logged onto the fetish site and posted it on my profile. "No longer a virgin" was the caption. It got 600 likes the first hour.

After that first buttfucking experience I was hooked. I had a bunch of willing partners, but Andy came over and plugged my ass with his fat cock on the regular. The best part was letting him cum up my slick chute after a good fucking and then farting it out of my abused asshole onto his belly. But that's a story for another time...