Experimental Anal

byprincessmaryann©

I slid my mouth off of her nipple. "I want to stay in you," I breathed. "Get off for a second so I can put on a condom."

"Okay."

She raised up until my cock slipped free, slick with pussy juice from deep inside her body. She grabbed a condom, tore it open, and rolled it onto me. As soon as it was it was in place, she impaled herself once again on my shaft. With the threat of an accident removed, we were now able to really get into it.

I reached for the bottle of lube and set it beside me, then reached and grabbed her ass cheeks. I pulled them apart, hard, causing her to gasp slightly. I told her to put her hands there and keep her ass open. Then I squeezed some of the lube into my hand, coated the index and middle fingers of my right hand, and wiped the excess on the towel.

"You ready to feel my finger in your ass?" I asked her.

"Oh, yeah," she moaned. "Slip your finger in my ass. Please. Get my ass all ready for your dick."

I probed with my finger until I found the pink dimple of her asshole, then rubbed up and down, coating it thoroughly. That done, I put my finger against her pink hole and applied firm, steady pressure. She whimpered with both fear and frustration as the tight muscles of her sphincter refused to yield. She wanted me to do this; unlike Tina, she was a completely willing and cooperative partner, but still her body resisted out of a completely understandable fear.

"Just relax," I said soothingly. "If you need me to stop, all you have to do is say so." That was another advantage of me taking her anal virginity: like I said, it didn't matter all that much to me, one way or the other. If she asked me to stop, I would, unlike someone lusting wolfishly for her backdoor who might not.

"Okay," she said, closing her eyes and trying to force herself to relax.

I took her nipple back in my mouth and circled it a couple of times with the tip of my tongue. Then, unexpectedly, I bit down. Not too hard, but definitely enough for her to feel it.

"Oh!" she exclaimed in surprise, and as she did, her ass suddenly yielded to the pressure of my finger and it popped inside, all the way to the second knuckle. "Mmpf!"

Oh, man, was the inside of her ass ever tight! Her ass muscles had a firm lock on my finger, and the outer sphincter muscle that had been tricked into letting my finger inside now had a tight grip on it. The image in my mind was of a bouncer grabbing hold of someone trying to sneak in and saying, "Hold it right there, Mister."

"You okay?" I asked.

"Mm hmm," she said tightly, her eyes still squinched close. "I'm okay. It's just...different. It doesn't hurt, but it's a little uncomfortable."

I probed around inside her ass, not pulling my finger out or pressing it in deeper, just turning it and exploring this new alien environment it found itself in.

"I feel your finger moving around in there," she giggled.

"Sorry," I grimaced, and held my finger still.

"No, don't stop. I kinda like it, actually."

I explored a bit more, and pressed on the thin layer of tissue separating her ass and vagina. My finger could feel the shaft of my cock on the other side, and my cock could feel my finger pressing against it. That gave me an idea on how to make more room. I slid my finger back out.

"No!" she whined, surprising me a little. "Put it back? Please?"

"I will," I assured her. "I just want to do something first."

I lifted her off my cock, stood, and lay her out on the bed with her feet hanging off the side. Then I took her by the ankles and separated her legs as far apart as was comfortable for her. Finally, I got the lube and re-lubed my fingers.

I stretched out on my belly, between her legs, with my face inches from her pussy. One nice thing about Sandy (and Maryann, too) is that she was always eager to experiment sexually: one day I made the offhand comment that I had never yet had the opportunity to eat a shaved pussy. The next day was a 24-hour duty shift for me and she called me at the station around 8:00 at night just to chat. When I casually asked her what she was doing, her answer was, "Grooming", and she declined to elaborate. The next morning, she welcomed me back to my apartment (we didn't live together) with a hot breakfast and the gift of a perfectly shaved pussy. What I did with that gift drove her so insane that ever since, shaving her pussy had become as much a part of her morning routine as shaving her legs.

I licked slowly around her lips and probed her vagina with my tongue until her hips were in almost constant motion on the bed. Then, finally, I licked and sucked her hard clit into my mouth, and at the same time, pressed against her asshole with my index finger. This time, I was granted entrance immediately.

"Ahh," she sighed happily as her fingers played with her nipples.

I slipped my finger deeper in her ass, creeping along at a glacial pace, watching for any sign of pain or distress as I licked and sucked her clit, but I met no resistance as I slid my whole finger into her.

"Doing okay?" I asked.

"Doing wonderful," she said dreamily. "How deep are you?"

"My whole index finger's in you," I answered. "Think you're ready for a second finger?"

"Oh, yes," she purred. "Please."

I slipped my index finger out all the way, then put my two lubed fingers together and pressed. This time I met some resistance, but only for a couple of seconds. Unlike earlier with her on top and her pussy stuffed full of my cock, I got the sense that her ass was much more welcoming of my fingers. She jumped a little as if startled when my fingers entered her this time.

"Oh!" she cried out sharply. "That hurt a bit." It must not have hurt much, though, because she giggled. When she did, I could feel the vibrations of her entire body transmitted through the walls of her ass.

"Sorry. Let me know when you're ready."

It took a few seconds, but soon she was ready, and I advanced my fingers slowly and steadily. There was no resistance or painful reaction from her, and in just a few seconds, my index and middle finger were all the way inside.

"That's it," I said proudly. "Two fingers, all the way in. How does it feel?"

She thought for a moment. "You're not going to believe this, but it feels fantastic. I can feel your fingers stimulating my pussy and my clit, but it's indirect. I can't really explain it. All I know is I like it."

I played with her ass for a minute or two, as I licked and teased her pussy and clit. She seemed to be having a good time. After a bit, she looked at me and her eyes locked to mine in a very deep moment.

"I think I'm ready to feel a cock in there now," she said, smiling.

I withdrew my fingers and stood, and she sat up. I decided to swap out my condom and since the condoms were closer to her, she got one out. She sat with her legs crossed under her, and kissed the tip of my cock, licking away a drop of pre-cum. Then she opened the wrapper and rolled the condom into place. I took the lube and thoroughly covered it. She held out her hand for some lube, which I gave her, then she reached back and coated her ass with it. We both wiped any excess on the towel.

"How do you want to do this?" I asked. "You can get on all fours, with your head down, sort of doggy style, or you can lie on your back with a pillow under your hips and your legs on my shoulders, or you can do it like an enema: lie on your side and draw your knees up."

She decided the third option sounded best. She stretched out on her right side, drew her knees up close to her chin, and wrapped her arm around the back of her thighs to help hold her legs in place. She looked nervous, and I imagine I looked at least a little nervous myself. Her hips rounded, and her little pink asshole stared at the cock that would soon penetrate it.

"You ready?" I asked.

She breathed deeply a couple of times and then nodded. "Ready as I'll ever be."

I put my cock at her asshole, nestling the tip in the divot, and wrapped my fingers around the base to hold it there. Then I began to gently but firmly press forward.

"Gently...gently...aaaaah!!!"

After a few seconds of pressure, her ass yielded to my cock, and the entire head popped inside. Her wail could have woken the dead and it startled me enough that I almost jerked back and out. I wasn't worried about waking the dead. What I was worried about was scaring the neighbors into calling 911 and reporting that a woman was being murdered. I could just see myself wrapped in only a bathrobe, standing at the door, explaining that one:

"Murder? Oh, no, nothing like that. I was simply fucking my girlfriend in the ass for the first time and it must have hurt more than she thought it would, that's all." I don't know which would have been worse: telling them that, or them asking her to confirm my story:

"Yes, it's true, officers. Having a cock in your ass hurts like hell."

Worse still, in the year and a half I had been a firefighter, I had gotten to know several of the city cops, and a few I counted as friends. Whether it was my friends who happened to come to the door or not didn't matter: either way, it would only be a matter of hours - or days, if I was lucky - before nearly all the officers in the whole damn city would know. I think the only thing a cop loves more than donuts is a good story. I would never live it down.

"You okay?" I asked, not moving my cock a millimeter either way.

"HELL NO, I'M NOT OKAY!" she roared, panting. "I HAVE A DICK THE SIZE OF A FUCKING SUMMER SAUSAGE UP MY ASS! WHY DO YOU THINK I'M OKAY?" Then she giggled. "But if you pull it out of my ass, I will break my foot off in yours, okay?"

Okay, thanks for clearing that up for the neighbors so loudly, I thought: "Never mind, 911. False alarm. It was just a woman with a really big dick in her ass. You have a nice day, too, Dispatch."

"Okay," I said, realizing how close I had just come to a very hard to explain trip to the ER: "So, how exactly did you end up with a woman's foot broken off halfway up your large intestine? And don't say you fell on it."

She laughed, surprising me. What a bizarre sight we must have been: a pretty and petite blonde, lying naked on a sofa bed with her knees pulled up to her chin, her anal sphincter stretched like a pink rubber band around the head of a thick cock (for the record, "summer sausage" is an exaggeration), which in turn was attached to a big burly and similarly naked firefighter. "You see, it's like this...Nah, forget it. There's no way in hell to explain this one."

She lay there and concentrated on relaxing. "I'm okay," she said in a much calmer tone. "It's just that I wasn't quite expecting it to hurt that much. But you're in there, and I want to keep going, as long as you want to. Just give me a little time to get used to it."

After a minute or two, she asked for more, and I pushed into her a little further. Twice more she asked me to stop and wait for a few seconds, but before long, all six inches were inside. When she felt my balls touch her butt cheeks, she smiled proudly. "We did it," she said in a mock cheer. "Yay!"

I could feel her ass muscles rippling along my shaft and told her how good her ass felt. "Guess I'd better enjoy it while it lasts, since Mr. Happy's never going to get invited back."

"That's not true," she pouted, playfully thrusting out her lower lip. Then her voice changed, becoming much more sensual. "Actually, now that you're inside me, it feels pretty damn good, to tell you the truth. It still hurts a bit, but I kind of like it. I don't think I'm going to cum, at least not this time, but you're more than welcome to do what you need to do. I know you'll take care of me later; you're good for it."

She gave me a look that was pure lust and licked her lips hungrily. "So how about it, big boy?" she breathed. "You want to fuck me?"

I began thrusting in and out of her slowly, carefully, and not moving back and forth more than an inch or two at a time, but as she relaxed more and more she drove me on with cries of "Faster!" and "Deeper!" and before long I was fucking her ass almost like it was her pussy. I watched her face carefully, not wanting to hurt her, and watched for any sign of pain or distress that would tell me to slow down or stop. But she kept her eyes locked to mine the entire time, and her lustful smile never wavered a bit.

It wasn't long before I felt the familiar tingle in my loins that told me my orgasm was near. She detected the change even before I told her.

"Oh, yeah, cum in me, baby," she hissed. "Cum in my tight little ass. I want to feel your cock jerk inside me. Give it to me." She kept up a constant barrage of dirty talk, encouraging me as my orgasm got closer.

"You know what I want you to do next time you fuck my ass?" she said.

"What's that?" I panted.

"I want you to do it without a condom. I want to feel all that hot, gooey cum shoot up in me, all up in my colon. I want you to give me an anal cream pie. You want to do that, baby? You want to mark my ass as yours with your cum, to say 'this ass belongs to me'. I want you to do that. I want you to claim my ass. Will you do that for me?"

That did it. I slammed my cock deep inside her one last time and felt my cock spasm inside as my cum shot into her body. The fact that it didn't make it past the end of the condom was immaterial. As far as I was concerned, I was filling her backside full of my hot cum.

As soon as I thrust into her and froze that last time, she opened her legs slightly and diddled her clit furiously. She was so incredibly wet that it sounded like a child splashing in a mud puddle. Before my own orgasm was finished, hers began.

"Oh, God!" she cried. "OhGodOhGodOhGodOhGodOhGoddddddd! Unnh!" Every muscle in her body seemed to constrict at the same instant, including the muscles inside her ass, and as hard as I fought to remain inside that beautiful ass, I was forced out.

After a few seconds her muscles released their tight, frozen state, but the assault on her body wasn't over. Ironically, the first time she got pounded in the ass was also the first time she discovered she was multi-orgasmic.

"I'm still cumming!" she cried, sounding panicked, nearly terrified as her second orgasm began before the first was completely finished. There was a horrible, almost inhuman screech as her lungs fought to suck in air, struggling against muscles that were trying to force the air out of her. Without bothering to dispose of the used condom, I climbed onto the bed and held her tightly in my arms.

Then a third: "Oh, God, why am I still cumming?" she cried.

Mercifully, the third was weak and brief, and was the last of them. When it was over, she was collapsed and exhausted on the bed like a pile of boneless flesh that lacked structure of any kind. As she lay there immobile, occasionally she would jerk as an aftershock hit her. I simply lay there and held her, waiting for her to recover.

It took five minutes or more for her to be able to move or even respond, and then five minutes before she was able to say anything more coherent than gibberish. When she finally came to her senses, I tilted her head up to look at me and smiled.

"So...was it good for you, too?"

==================================

So, what do you think of Brian's first foray into the world of erotic fiction? He hasn't asked, but I'm just curious what you thought. Before you criticize him too harshly, I should probably point out that once upon a time he made his living climbing ladders with one arm while carrying full grown adults in the other, and he used to routinely bench nearly five hundred pounds. Y'know, just saying...

No, I'm only kidding. Brian IS a very large and very strong man; that much is true. But he is also a gentle giant who would not hurt a fly. Literally. How do I know? Because as I write this, for the third day in a row a little black, hairy spawn of Satan is having a grand time buzzing around me, and Brian has not interceded on my behalf. I, however, am not nearly so merciful toward insects, and my patience is at an end.

Come here, you little bastard...

Report Story

byprincessmaryann© 5 comments/ 51028 views/ 8 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

Previous
2 Pages:12

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartal1969, MyChem and 6 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by kzchopper04/20/14

That's love AND adventure!

Two lovers who truly care about each other broadening there their horizons is both erotic and wonderful. Thanks for sharing!

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous04/19/14

good story

That was honestly, in my opinion, one of the best first time anal stories. It reminded me of my first time. Not quite because we didn't start with fingers we just went straight to it. Just like Sandy Imore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 5 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel