Everyone on Craigslist can’t be a creep, right?
His post about introducing a woman to anal sex sounded very sincere. By the use of language, I’d gathered that this man was educated, thoughtful, perhaps even well spoken. If we’d met under other circumstances, we might find ourselves at the same end. But this was so much easier – I know what he wants, he knows what I’d like to try.
And he talked about the prep work, the foreplay, getting ready, moving slowly… and then not moving slowly, getting my ass used to his cock and then giving me that cock again and again until I came again and again. He sounded like he knew what he was talking about, and I wanted to learn from him. So I responded.
Here’s the part where my friends would say, “WHAT?!” I mean, I’d say the same in their place. I’d be worried about safety and their sanity. This guy could be anyone, he could do anything. Of course, the very thing I wanted him to do might be just the sort of thing they’d consider a worst case. So I didn’t tell my friends. I just made a plan that would give me a great out, invited friends over for a few hours after our date. If I was tied up and being tortured, better chance that they’d find me. If these thoughts are even entering my mind, why would I even consider doing this? How sex starved am I, anyway?
Pathetic, yes. But curious, and more so every day. I know my own body, and I know when I am getting a good stroke on, when my clit is fully engaged, when I am about to have the best orgasm, I’m feeling it in my ass. It’s vibrating, it’s pulsating, it’s practically fucking winking. I’m not inviting some clumsy one-night stand to stick it in. I’m not freaking out a potential new man with my ass-play curiosity. I wanted it, but I wanted it from someone who knew how to make the most of it. I wanted the king of ass fucking to fuck my ass. And that’s what I got.
Advertising on Craigslist made sense for him – get what you’re looking for, and you know there are women out there who are curious and more likely to respond to this type of invite rather than a heart-to-heart over wine and expensive dinner. The first time is a particularly tricky process, and you want to be focused on that. And we were focused.
He showed up at my apartment. Tallish, clean, neat looking. Jeans, dress shoes, button-down shirt and a sweater. Short brown hair, light brown eyes. Sweet face, nice nose, weak chin. Pleasant, unassuming, almost completely unremarkable. I wouldn’t look at him twice, not that there was anything wrong with him, just that he was completely ordinary at first sight. He told me his name, I told him mine. One more unremarkable than the other.
We talked a bit about cable providers, city views, my strange apartment building and pets while we got high (my supply – I didn’t want to get fucked up on some laced shit). I told him I was going to need to warm up some before diving right in. He asked me what I was comfortable doing – before I could start explaining, he had his lips on mine, and his hand under my shirt. Sigh. Exactly right.
We moved into the bedroom. He sat on the bed, I stripped to the waist, climbed into his lap and shoved my nipples in his face. He licked them and flicked them, alternating his talented tongue between my tits and my mouth. He had me squirming on his crotch almost immediately like a champagne room dancer desperate for a tip. I didn’t want this anymore – I needed it. He had my tights and panties off 10 seconds later, his hands massaging my ass cheeks, feeling my wetness running all over. “I am going to get fucked by a stranger in nothing but a skirt,” I thought, and audibly gasped.
“Is this OK?” he asked, pulling his tongue away from mine. “So good,” I answered, and climbed off him, onto my knees, beginning to undo his belt.
“I would like to take my clothes off,” he said. “Would you like that?”
“Mmmhmmm,” I answered. And remembering that this guy is here to basically eat my ass, fuck me however I like it and make me scream, I practically swooned.
He moved quickly and efficiently: The sweater came off, the shirt, the belt, the pants. His cock was rigid, long and cut, the head peeking out of his diamond-pattern boxers. It had an unusual shape – at least in my experience. It tapered down to the head – almost like a butt plug. This man was made for this job. He was so hard and I was so wet, it seemed stupid not to get a quick one in before focusing on the task at hand.
I can’t imagine any man can think too well with a raging boner, and if he’s teaching me the finer points of anal exploration, he needed some blood to his brain, so I offered up my mouth, sliding off his boxers, flattening my tongue for maximum surface area and running it from the base, by his balls up to the head, teasing the top, taking him quickly into my mouth and into my throat, as far down as I could go. My eyes watered, but I didn’t gag. I also didn’t want to do this all day.
He liked the oral attention, and I was happy to oblige, but happier to get that thing in another hole. I don’t know what came over me, but I popped his cock out of my mouth, moved up to his ear and whispered, “Please fuck me before you fuck me.”
Lucky for me, he knew exactly what I meant, and had me on my back, my skirt up around my waist, and two fingers deep in my cunt while he slid on a condom. He was talented with those fingers, so talented that I came the second his dick hit its mark. “AAHH!” I screamed. He smiled and kept pumping. “Do… it… fast. Please…. We don’t have much time,” I begged him. He got up on one knee and gave me the pounding of a lifetime, moving hard and fast in and out while his thumb massaged my clit. I was coming over and over and my asshole was spasming. “Touch my ass,” I squeezed out between moans. He lubed up his right ring finger with my juices and slid it right in. “You’re already coming in your ass,” he grunted. “This is going to be so good.” Two more pumps till he shot and pulled out. I felt some kind of loser abandonment for the 30 seconds he disappeared in the bathroom to ditch the condom and wash his dick. “Don’t move,” he said to me before he left. I stayed put.
When he returned he explained. “I’d rather you didn’t clean up. Your pussy is so juicy, we can use that to get your ass ready. It’s nicer for me than eating lube. Is that OK with you?”
Lying on my back, my legs flopped on either side of me, my skirt still on, pulled up to my breasts, and still feeling aftershocks? I was in no position to complain.
“Let’s talk about positions,” he said. “It is easier from behind, but if you are not comfortable with that, we can start just like this.”
“I love it from behind,” I told him. “Should I stand up?”
“If I do this right, you won’t be able to stand up – your legs will go weak.”
“Ha! I like the cockiness,” I said. “I’m not cocky. I’m a realist.” He’d already made me come twice – hard – so I thought he was probably on to something. I got on my bed, on my hands and knees, completely at the mercy of a stranger. I never felt more excited in my life. I could have cleaned up three times over and still had enough lube for 10 rounds, my cunt was producing juice like a Florida orange farm.
He came up behind me, put his hands on my breasts and massaged them, my nipples still hard from all of the excitement. I started swaying my hips, completely involuntarily, like some kind of cat in heat. “Open your ass for me,” he said, pinching my nipples. I spread my cheeks with only the slightest hint of shame. The weed, the orgasms and the overwhelming want knocked 30 years of programming right out of me.
“Look at that tiny tight hole,” he said. OK, that was a little creepy, but the ad did say he was interested in virgin asses, so that’s his thing. Fair enough. “I’m going to fuck that tight little bud.”
“Yeah,” was all I could manage. I certainly meant “yeah,” but I didn’t know what else to say, and the man was clearly hypnotized by my unplowed ass, so I could have sang the Battle Hymn of the Republic and he wouldn’t have noticed.
“I’m going to make love to your tiny pink hole with my tongue,” he said by way of narration. Again, a little creeped out, but zoning out his choice of language was in my best interest. His hands came away from my breasts and rested on my hands, so we were holding me open together. He was shaking with anticipation, or maybe that was me. Either way, the shaking was minor enough that he had no problem getting his tongue all the way in with one big thrust.
“Aahhhhh!” I screamed. It felt incredible, and not in an entirely positive way.
“I wanted to shock you ready,” he said, and moved back down, his hands now on my thighs, his tongue working slowly around my ass. He slipped a finger into my cunt, and rubbed my clit with my own juice. I jumped again, and he put that same finger at the entrance to my ass, rubbing around the edge and slipping in just to the first knuckle, moving in circles.
I’ve got what feels like an index finger in my ass and a tongue swirling all around the now more open hole, and I already feel full. “How is a cock getting in there?” I wondered. His finger popped out and I felt so empty. I gasped. “Fuck, this is going to get addictive, isn’t it,” I thought, making a mental note to order some toys STAT.
He lubed himself up with more of my unending well of wetness, told me I could take my hands off my ass. “I’ve got this now.” I bent forward, with my head on the bed, my hands holding my breasts and my ass in the air, hungry for more.
He returned that index finger to its rightful home, and started moving it with more purpose, opening my ass up. When the middle finger started to work its way in, I was all in. I wanted a third finger, I wanted a cock, I wanted it all.
But not so fast – my new friend had other plans. He removed his hand, replaced just the index finger of the one hand, added the index finger of another and slowly pulled my ass open another millimeter at a time. This sounds like torture, I imagine, but it felt like heaven. He moved his fingers deftly around the circle of my ring, lavishing each exposed bit of skin with persistent attention from his tongue. He moved his mouth quickly and forcefully, and with my ass in the air and a stranger attacking it with two hands and a mouth, I came, pinching my nipples and calling his name.
But we’d only just begun. He shifted, moving up my back and whispering in my ear, “You’re almost ready.” I felt beyond ready, and his cock resting on my ass felt like a metal rod, but he was the expert on readiness, so I took his word for it. And then he was gone.
Just for a moment. He returned with the lube he’d promised he’d bring, and began massaging my asshole with the warm, slick substance. It was slippery, but thicker than the lube I had encountered in my minimal experience. One finger slipped in pretty easily and he swirled it around, deeper in than he’d gone before. I swear, I felt the sensation it in my clit, in my nipples, in my teeth. He replaced the finger with a thumb as he rotated in larger circles, faster and with more force. I started rocking as if I was riding a dick. I was afraid I’d come again. With his other hand and his teeth, he ripped open another condom, slipped it on and had that arrow head at my asshole in 2 seconds flat. “This is really it,” I thought. “No turning back now.”
He worked in the head slowly but very surely, like squeezing into the tightest jeans, only the tightest jeans were a hole in my body I’d never let anyone in before. I had my head resting on my arms, his hands holding my ass open. When the head was in – and believe me, you know when it’s in, feels like a key opening a lock, only with a hot poker, I made a deep and low sound I’d never uttered before, a mixture of relief and rapture. “You OK?” he asked. “Oh yeah,” I answered. “It feels so good.”
“It’s going to get even better. Hold on.” He pushed his cock in further. If I thought I felt full before, this redefined the word. About halfway into my ass, he halted. My breathing, shallow and short, was not good enough for him. “Lift up your head,” he ordered. “Hold yourself up with your arms. Take deeper breaths.” Oh my God. The deeper the breath, the more of him I could feel inside me. I swear he was in my belly and up my spine and in my throat. This was fucking unreal.
“You like this, don’t you?” he asked.
“I love it,” I responded.
“I know. I am going to make you come so hard, and then I am going to come, and you are going to thank me.”
Normally, I’d want to punch a guy for saying something like that, but I just wiggled my ass in response. He took the hint and pushed all the way in. I saw stars. I cried out. He held still, all the way in, for two minutes that felt like 10 hours. “Are you ready?” he asked. “Fuck me now,” I gasped.
And he started moving, slowly at first, his hands moving up from my hips to my breasts, holding them, squeezing them. Now I understood when people described the feeling as a burn – it definitely felt like a burn, but ohh, what a good burn. A slow burn that heated up every cell in my body. I could not shut up, groaning and grunting with each move. He started moving faster, his hands slipping down to my hips, pumping quickly now, his balls slapping me. My head spinning, I dropped my forehead down, my arms collapsing onto my breasts, nothing up but my full, fucked ass, with that damn skirt flying from the forceful motion. “Rub your pussy” he said. “I…. can’t!” I answered. “I can’t move.”
He took one hand from my hip and moved to my cunt, slipping a finger in while his thumb rested on my clit. I felt like a bowling ball – the world’s luckiest bowling ball. “Can you feel me?” he asked, wiggling the finger inside me. My answer is hard to pin down, but if I had to spell it, it would look something like “Aarghmmnn” followed by a sharp cry of release.
I have never come so hard. Still riding the wave of that insane orgasm, and with my head still down, I pulled my hands from my breasts and put them at my side in an attempt to pull my upper body into a more upright position. The hands he’d slowly removed from my cunt now holding my hips so tight I knew he’d leave a mark, he began pumping with renewed focus. First fast and shallow, then deep and slow, then fast and deep and hard and oh fuck, I was coming again and this time he was too. The sound of his orgasm escaped from his throat, and not dissimilar to a seal being beaten, it was not attractive. But the feeling of his pulsating dick shooting cum? I could feel the shoot , even in the condom, my ass was pulled so tight around him, so sensitive and raw and hot . That was like a victory.
He pulled out, tossed the condom in the general direction of the trash and fell on top of me. I rolled over, wrapped my legs around him and yes, I thanked him. While my body vibrated, my asshole spasmed, my nipples ached and my cunt continued to leak, I whispered my gratitude in the ear of the ordinary stranger.