Experimental Anal

I’m proud to say that my husband, Brian, never ceases to surprise me; it’s fantastic that even after more than fifteen years together, he can still pull a rabbit out of his hat now and then. This true story is his latest “rabbit”.

A few weeks after my first story, “The Gift”, was posted to Literotica to mostly positive comments (for which I thank you, readers), unbeknownst to me, Brian decided to take a crack at it himself. One day when I came home from work he surprised me with this story he had written about events in his own life, more than twenty years ago. What surprised me even more was that it was actually good: by the time I reached the end, I was wet and practically attacked him sexually. The next day I read it again and had pretty much the same reaction.

Brian is a very smart man. Sometimes we make the mistake of looking at big strong guys like Brian and equating “big” with “dumb”, and yeah okay, sometimes it’s for good reason. It also probably doesn’t help that for a number of years Brian made his living running into places everyone else was running out of. In addition, he’s also very loving and kind, and a fantastic husband – which is the reason, in case you’re wondering, he knew he could write a story about his own sexual history and give it to me without worrying if I’d beat his brains in with a rock while he slept!

One thing Brian is not, however, is a writer, a fact he’d be the first to admit. At his request, I rewrote his story, clarifying this paragraph or that, embroidering or tightening up his prose where needed, and just tweaking it here and there. It’s a collaboration of both of us, then, though the gist of the story is entirely his; I merely edited it. (Also, I should point out that the clever and occasionally laugh out loud humor he sprinkled in here and there is entirely his own. What’s remarkable, I believe, is how he’s able to make the reader unexpectedly laugh now and then, all without taking one whit away from the eroticism of the story.)

Now for the disclaimer and we’ll get started…

Disclaimer: This is a true story of events that took place in 1988, and is as true and accurate as memory allows. Where necessary, license has been taken to fill in gaps, while still taking pains to preserve the original theme. Names have been changed to protect the guilty. My name’s Maryann. I carry a stethoscope.

Oops, sorry. Ahem. Must be picking up old “Dragnet” reruns…


“I’m…almost…there,” the young blonde gasped between panting breaths, as she rode me furiously.

I grunted in acknowledgment, but kept my eyes squeezed tightly shut. It wasn’t that I didn’t want to look at her. Far from it: her naturally blonde hair, green eyes, and big tits were a sight to behold. No, it was that I was afraid to look at her; one look at those firm yet bouncy tits and her nineteen-year-old body impaled on my cock, and I would lose it for sure. As it was, it was taking every ounce of self-control I could muster not to cum.

The eighty-plus year-old chair under me groaned and squeaked terribly with each thrust, threatening to collapse and dump our naked asses in the floor at any second. It was more than eighty years old, but it was hardly an antique; “antique” implies an image of furniture that has been delicately cared for or lovingly and painstakingly restored, and this chair wasn’t it. It was simply old. But for a twenty-two year-old part-time college student/full-time firefighter who worried from one month to the next how he was going to pay the rent, it was the best I could do.

That chair, for all of its danger of imminent failure, was my girlfriend’s favorite place in my little studio apartment to have sex. I would sit in the chair with my feet flat on the floor and Sandy would straddle me, facing me, with her feet on the floor as well. Then she would fuck me with a thrusting motion of her hips that ground her clit against my pubic bone. As long as I didn’t blow my load too soon (or the chair catastrophically fall to pieces), it was a nearly-guaranteed orgasm for her.

She squealed suddenly, wrapped her arms tight around me, and pulled me tightly to her, squeezing me so tight that for a few seconds I couldn’t even breathe. As I felt her tight pussy flutter around my cock, I mentally gave myself permission to cum, and instantly my condom filled with hot cum as I exploded inside her.

She relaxed slowly, releasing the death grip she had around my chest. I had rescued people from near-certain death who didn’t hold onto me as tight as Sandy usually did when she came. And if she were on her back, it was even worse: then her feet and legs got into the act, burying her heels in my backside like she was trying to merge our bodies together.

“Mm, that was nice,” she purred, with a small, contented smile. “Did you cum?” If not for the fact that we came at the same time, she wouldn’t have had to ask. Her pussy was tight enough to tell her when I came. As it was, with her own orgasm güvenilir bahis flooding her brain, that particular message got lost in the shuffle.

“Yes, I did. Thanks for asking.” That was something I always appreciated about Sandy: if I said no, she would have either stayed on me for as long as it took or gotten off and sucked me the rest of the way. My wife, Maryann, is the same way, but I felt it displayed remarkable maturity for a young woman not yet out of her teens.

I put my hands under her ass, lifted her off me, and carried her over and laid her on the sofa. She giggled; it was always a big turn-on for her when I swept her into my arms and carried her effortlessly. It made her feel light, she said. Sandy had an extra ten pounds or so that she could bear to lose, but she was hardly fat. Like a lot of young women, though, she thought she was too heavy and saw every tiny imperfection in her body whenever she looked in the mirror. After depositing her on the couch, I got a paper towel, disposed of my condom, then cleaned myself up with a washcloth. Once I was done, I came back in the main room (since it was a studio, the whole idea of a living room or bedroom is somewhat vague) and cuddled with her, both of us naked.

Neither of us said a word for probably five or ten minutes, though Sandy did hum some tune that either she came up with or one I simply didn’t recognize. It didn’t matter, though; what mattered was that she was humming. It was a habit of hers that I doubt she was even aware of: she always hummed after an especially good orgasm. I felt proud of myself.

“I was just lying here thinking,” she said in a dreamy, somewhat disconnected voice. “I wonder what it feels like to do it in the butt.”

“I imagine it hurts. I expect it hurts a lot, even,” I laughed.

A lot of guys would have responded very enthusiastically at the mere hint of anal from their girlfriend or fuck buddy, but I didn’t. I knew it happened, I had seen it in magazines and porn flicks, and I knew that while it was far from common, it wasn’t all that uncommon, either. I knew that some guys really got off on fucking a woman in the ass, but then again, some guys got off on being pissed on or having their balls subjected to things resembling medieval torture devices. And those things definitely weren’t for me: unless I’m on fire, do not piss on me, and if you bring some of those extreme S&M gadgets even into the same zip code as my balls, I’d better be dead first, or you might be. Similarly, as far as I was concerned, the asshole was exit only and I had no particular interest in putting my cock in a hole that might already be occupied, if you know what I mean!

“Maybe,” she said vaguely, shrugging.

“If you want to know what it feels like, ask your friend Tina,” I pointed out.

“Tina doesn’t count. We both know Keith’s an asshole, no pun intended.” Keith was Tina’s boyfriend. Sandy spit out his name like it was poison.

She was right: Keith was an asshole. I had once counted him as a friend, but not for some time. Though he had never done anything to me personally to end our friendship, Keith ran hot and cold: one day he could be the best guy in the world, gregarious, friendly, and give you the shirt off his back. The next, he might steal your wallet or television and ignore you like you didn’t even exist. After one too many rides on the “Keith roller coaster”, I couldn’t be friends with him any longer. I like roller coasters, but only the physical kind, at an amusement park; emotional ones I want no part of.

A couple of weeks ago on a boring Saturday afternoon, Keith and Tina had tried anal for the first – and according to Tina, last – time. She had been willing to experiment, letting Keith very carefully insert a well-lubed pinkie finger in her backdoor, just to see what it was like, but that was as far as she was willing to go, at least initially. If it went well, she might eventually go all the way at some point in the future, but not that day.

As it turned out, Keith had other plans, and after a minute or so, had followed one finger with a second one. And while Tina didn’t much care for the second finger, she didn’t really protest, either. A few minutes later, when his cock replaced his fingers, she had complained, but at that point it was too late: he was already inside her tight ass.

Though it hadn’t been rape in the traditional sense, and he did at least go slow and use plenty of lube, she had not exactly been a happy camper as her ass opened to this unwelcome and uninvited visitor. What’s more, he was fairly plastered at the time, so he didn’t cum right away, and his cock was in her backside for a while. I wondered why she didn’t pull off of him and then kick his scrawny ass to the curb (maybe with her foot up it), but when I asked Sandy that question, she ignored it.

Sandy rolled over on the sofa so she could look me directly in the eye. “You remember when I told you about it and you asked me why she didn’t stop him after he entered her?

“Tina türkçe bahis would kill me if she knew I told you this, so you have to keep it a secret, okay? But the reason she didn’t stop him was because after it stopped hurting, she liked it. She liked it so much, in fact, that she came with his cock up her ass. She sort of stifled it and kept quiet, cause she was mad at Keith for taking her like that, after she had said no. But she came, and even though it was a huge surprise, she said it was unlike any orgasm she had ever had. She couldn’t describe how it was different, just that it was.

“I asked her if anal was something she would ever do again, and her answer was, ‘Most definitely. Just not with Keith.’ She said she never wanted to see him again, let alone do anal with him.”

“They’ll be back together in a week,” I sighed, shaking my head. I was wrong about that: it was actually nine days, not seven, before they reunited. Counting the couple of weeks that had already passed, that made it around twenty-three days, which I’m pretty sure was a record for them. And while I don’t know this for certain, I don’t doubt they went right back to him fucking her in the ass.

“So, why all this interest in anal all of a sudden?” I asked. “Are you just talking or are you thinking about doing it?” I wasn’t exactly subtle. When one of your favorite parts of the job is knocking big holes in things with heavy tools, it sort of affects your outlook on life and does away with subtlety.

She hemmed and hawed a bit, making imaginary doodles on my chest with her finger, staring at my chest instead of looking at my face. “Kind of,” she admitted, blushing. “If you wanted to. You’d have to use lots of lube and go really, really slow and be patient with me…”

“I’m not Keith,” I interrupted, a little annoyed at what seemed suspiciously like a comparison of the two of us.

“Oh, I know!” she said quickly, kissing me lightly all over my bare chest. “You’re not like Keith at all: you’re a very good and patient lover.” She paused and continued to kiss me.

“Let me put it this way: I’m never going to ask you to put your dick in my butt,” she cooed. “But if you said, ‘Sandy, I want to fuck your ass,’ I wouldn’t say no.” Having finally gotten the words out, she looked me in the face and smiled.

I wasn’t quite sure how to respond to that, though my cock seemed more certain than the rest of me. It began to get hard. When Sandy felt it poke her in the belly, she wrapped her hand around it very loosely and slowly stroked it, the look on her face not changing at all.

“Sandy,” I said quietly, “I’ll hurt you, no matter how much lube we use. You know I will.”

I was Sandy’s second lover. Her first had taken her virginity barely a year before, just about a week after high school graduation. That guy, however, must have been hung like a mouse. My cock, at six inches isn’t especially long, but it is unusually thick. Think of R2-D2: not very tall, but solidly built and robust. When Sandy and I started having sex, it was almost like I took her virginity all over again. Our first two or three times doing it were fairly negative experiences for her: even though we used plenty of lube and I patiently took the time to make sure she was good and ready, it hurt quite a bit. After the first time, I was sure that was the end of any relationship we might have had. Obviously, though, it wasn’t.

“Do you remember the first time we had sex?” she asked softly.

“I remember you didn’t have a real good time,” I said. That was putting it mildly: when I finished, she actually had tears in her eyes from how much it had hurt.

“No, you’re wrong,” she said. “I had the best time of my life. You’re right, it hurt, and as I was laying there taking it, all I could think was, ‘I hope this is over soon’. And yeah, if that had been all, we probably wouldn’t have dated again, or if we had, it’s for sure we wouldn’t have had sex again.

“But do you remember what happened after you were done? You got rid of your condom, then came back and went down on me. Didn’t say a word, just crawled between my legs and went to town. That was the first time anyone had ever eaten my pussy, and I couldn’t believe how good it felt. By the time I made you stop, you’d been at it for nearly an hour and I had cum four or five times.

“More than that, though, I was impressed that you cared enough to make sure I was satisfied. You had cum already; I figured when you came back from the bathroom you were going to roll over and go to sleep, just like Tim used to. But you didn’t, and I decided right then and there that if you were that patient and considerate a lover, then I didn’t care how thick you were. Either I’d get used to it – which I did – or part of foreplay would include me taking a couple of Advil or Tylenol,” she giggled.

“My point is, yeah, if you do me in the ass it’s going to hurt, and it’s going to hurt more than it would with somebody smaller. But the fact is, what happened with Tina’s güvenilir bahis siteleri got me curious, and that means at some point in my life, I’m going to get fucked in the ass. It could be twenty or thirty years from now, but it’s going to happen. And I want to do it with someone I know cares enough not to just go ‘drilling for oil in my lower colon’, which is how Tina described it. I don’t want to risk my first time being with someone like Keith, because even if he’s smaller than you, it’s going to hurt more if he just up and drills me,” she concluded.

“So, it looks like Mr. Happy here is ready for another round,” she smiled. “Only question is, would he like my hot little mouth, my soft and tight pink little pussy, or would he like to, ah, explore some ‘virgin territory’?”

All my former hesitancy about anal disappeared in an instant. A pretty girl was asking me to not only take her ass, but to be the very first? If I said no to an offer like that, I was pretty sure that was more than enough cause to have my “man card” revoked. Not to mention the fact that later in life, looking back on this moment, I’d never forgive myself.

“I was thinking I might like to stick this hard cock up your pretty little ass,” I smiled.

“My pleasure,” she said, smiling ear to ear.

To keep from having to run around collecting what I needed later in the midst of intimacy, I asked her to retrieve a towel, the bottle of lube, and some condoms from the bathroom. The sofa was also a bed, so while she hurried off to get what we needed, I removed the sofa cushions and pulled out the bed frame.

We climbed into the bed and started kissing, lightly at first and all over each other’s faces and necks, then progressing to deep kissing as our tongues teased in and out of each other’s mouths.

She asked me to sit on the edge of the low bed with my legs over the side, which I did. She straddled my thigh as we made out. I could feel the heat and slippery wetness of her pussy as she pressed her vagina against the bare flesh of my thigh. Soon nearly the entire top of my thigh was coated in her slippery juices, and her nineteen-year-old pussy went skating, sliding forward and back as her hard clit was pressed between the weight of her upper body and my leg.

As she ground on me, I moved down over her neck and to her breasts. They were large for her age, already 38-D, firm, and with extremely suckable nipples that seemed to get hard at the slightest touch. I placed my mouth over the right one, and she arched her back severely, thrusting her tits forward, as she pressed my face into her chest.

“There you go,” she cooed softly as she continued to grind away. “Suck Mommy’s nipples.” Apart from that one thing, she didn’t have any particular Mommy fetish that I ever noticed, but she loved to have her sensitive nipples sucked. And when they were sucked, she liked to pretend she was breast-feeding a baby. It was a little odd, sure, but if that turned her on, I was more than happy to do it. Maryann and I both came to a conclusion long ago, long before we met: if there’s something that turns you on during sex, as long as it’s not illegal or disgusting (don’t ask me to take a crap on you, for instance), go for it; it won’t bother me a bit. And if I can help, just ask.

I suckled her tight little pink nipple, making nursing sounds with my mouth, as she tenderly stroked the back of my head. I knew that each suck was sending little jolts of electricity through her, straight to her pussy. It wasn’t long before it got a reaction out of her.

“God, I need you inside me,” she hissed through clenched teeth, and before I could say a word she raised up, moved her hips over, and lowered herself onto my cock.

“Ohh!” she cried as I sank into her to the hilt. “I feel so full.” Having me inside her no longer hurt, and her reward for having borne up under the pain of those first few times was a pussy that had adapted itself perfectly to the size and shape of my cock. When I was in her, she fit me like a glove. It was an intense sensation for her, feeling stuffed full of my cock. I had room, lengthwise, to fuck her as much as I wished, but in width, it was a snug but not uncomfortable fit that she compared to “a favorite pair of shoes” or “the feeling at the end of a large and sumptuous dinner when you have eaten just enough to feel pleasantly full yet not uncomfortable”.

She stroked me in and out of her slowly, raising herself forward and up until the head of my cock was just barely inside, pausing for a second, then sliding back down with excruciating slowness, only to repeat the process, as we each savored each other’s bodies. We had to be careful: condoms were the only form of birth control we used, and I wasn’t currently wearing one. Pregnancy was a huge fear for us both: though the sex was fantastic and we enjoyed each other’s company, we were both realistic about our relationship. We weren’t getting married, we weren’t “always going to be together”, or any of that. We were both simply a pleasant and pleasurable distraction for one another, a stopover along the road to whatever life had in store for us as individuals. The last thing we needed was an unwanted pregnancy to upset the apple cart.

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