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Emma’s Dilemma

Category: Anal Sex
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My adolescent sexual experiences, beyond some clumsy groping under tops and skirts at the movies once or twice, were confined to my solo routine until going off to university. My first true lover was my dorm-mate Jane, who was as naïve and adventurous as I was at that time, and though she didn’t have the same desire to have me play with her ass, she was always very considerate of my needs. After college, I was fortunate to meet another considerate woman, much older than I, who introduced me to a new world of pleasure with her vibrators and anal beads.

I had occasional male lovers scattered throughout this period of my life, but rarely was I treated to the same consideration that I was with my female companions. Try as I may, those men who were amiable to a bit of coaching could never hold off their own climax one getting their dick past my sphincter. I had all but given up on trying to develop a lasting sexual relationship with a man, and then I met the man who I’d eventually marry, Todd.

Todd was a strikingly attractive man, who was noticed by every woman in every room he’d enter. Tall, slim, with an athletic physique, well dressed and finely manicured. He had no trouble finding a willing woman whenever he desired. Lucky for me, he had an affinity for redheads, and was available when we were introduced. Don’t ask me why, but in the beginning, I uncharacteristically played a bit hard-to-get, showing enough interest to keep him sniffing around, but for the first time ever, I took the physical progression rather slow. Todd’s since told me that this was one of the things that he found most attractive about me. Getting laid for him was never much work prior to meeting me, and I made him go the extra mile before he got to see anything beyond a kiss goodnight. Now I’m not about to sit here and tell you that he didn’t get to see the goods before marriage, but by the time we first slept together, we were committed to one another emotionally, which is something that I’d not experienced with a man, ever.

Our early sexual relationship was tremendous. Todd always focussed on making me cum, usually by licking and sucking my firm clit, or by finger fucking me with his dick inside of my pussy. He has a beautiful thick cock that fills my pussy and stretches me so divinely. In the beginning, that full sensation provided the right equation to rock my world every time he’d touch my clitoris. By the time I started thinking that I was needing to bring some anal play into the mix, I’d become self-conscious concerned that Todd would be put off by my quirky fetish. I opted not to tell him, deferring that bit of pleasure for my more private moments. We were married almost a year when I began to notice that I was having difficulty reaching orgasm with Todd, no matter what he’d do. It was time to act.

Todd often traveled on business back then, and would occasionally be able to bring me along when our air miles would allow. This trip was taking him to a ski resort out west, and I wasn’t about to miss out on this opportunity. In preparation, I packed my vibrator, beads, scented oils, and went out to buy some new lingerie. If I’d be able to work up the courage, this would be a trip that neither of us would ever forget, and if I’d chicken out, at least I’d have some alone time with my toys.

I still remember marveling at the amount of snow that was down on our drive from the airport to the resort. We just don’t see that much snow here on the East Coast. We checked into a quaint little log cabin, with a private balcony that overlooked a beautiful emerald lake. Having not had much to eat on the flight, we pretty much dropped out luggage and made our way back to the main lodge for dinner. We had to rush a bit through dinner that evening because Todd had arranged to meet a few of his West Coast colleagues for drinks. He returned with me to our cabin to quickly freshen up, and then was off to his meeting. With not much else to do, I proceeded to unpack our clothes and get a fire going in the fireplace to take the chill off of the cool mountain air in the cabin.

As the evening wore on, I began feeling anxious, going over in my mind how I’d ever be able to broach the subject of my fetish with my husband. Curling up in the large brown armchair that sat in the corner of the cabin, I flipped on the television, and began scrolling through the movie selection. In a matter of seconds I was flipping through the ‘adults-only’ menu, reading the tantalizing titles and teasing descriptions, and then it hit me. One of these movies would be just what I needed to bring up the topic with Todd. We’d watched porn together on a couple of other hotel stays, and it never failed to bring about some ‘healthy’ discussion. I frantically scanned the descriptions for a show that profiled some anal action, and was not disappointed. Not leaving anything to chance, I decided that a preview was appropriate, and hit the ‘select’ button on the remote.

The show was as cheesy as they come. Poor character development, horrible attempts at delivering dialogue, actresses with obvious boob-jobs, and actors with more ink than body hair. Everything you’d expect from hotel-grade porn. The only thing saving this flick was the techno-style music replacing the typical old 70’s funk overlay, and the rapid sequence to the anal penetration. Watching the action, one super close-up after another of giant erections pressing into tightly puckered portholes, I recall becoming quite aroused myself and beginning to imagine what my husband’s thick cock was going to feel like sliding into my hole. It was all just a bit too much to take, and judging by the time, Todd would be finished with his meeting soon. I decided to run myself a bath and soak for a bit before getting ready.

Undressing for my bath, I caught a glimpse of myself in the bathroom mirror. My puffy pink nipples were fully erect, and my little titties had become engorged, appearing larger than normal and feeling full and heavy. I could feel the moisture against my inner legs from the crotch of my panties as I slid them off, and I slid my hand over my swollen mound, squeezing in response to the ache now residing between my legs. I reached back and rubbed a finger over the tiny folds at the entrance to my anus, pushing my dry digit beyond its resistance briefly. It was going to take something of much greater girth than my finger to help me along on this occasion, but I knew that my patience would be rewarded if I could just keep up the intensity of my desire long enough for my husband to return. I slipped into the hot water and continued to fondle myself, teasing my pert tits and parting genitalia. I must have been deep in fantasy, for I failed to here Todd until be shouted from the cabin’s main room.

Upon entering the bathroom, he’d already removed his tie, and was unbuttoning his shirt. “There you are” he stated, as if he’d been frantically searching for me for hours.

“Here I am” I responded, running a handful of warm water teasingly up my torso and over my breasts. “Care to join me?”

“I thought you’d never ask” he said, rolling up his shirt-sleeves, “but there’s not a lot of room. Why don’t you just lay back, relax and let me bathe you”. With that, he knelt on the floor next to the tub, taking the puff from ledge beside my head. He proceeded to lather me, paying extra attention to the areas of my chest and pelvis, heightening my excitement even more. I sat forward, allowing him access to my back, then up on all fours so he could pay more attention to my firm, round behind. I remember so wanting him to just plunge a finger into my tight ass as he passed the foamy puff over my ass, continuing down the back of my thighs, but alas, it would take more than a wish. After he was done washing me, I suggested that he go put another log on the fire while I rinse off in the shower. He obliged, and I proceeded to stand and quickly shower in order to join my lover in our mountain retreat.

Exiting the bathroom in my fluffy robe, I’m met by Todd standing in front of the TV, remote in hand, watching a nude couple ecstatically fucking on the screen. “You were watching some interesting programming while I was gone” he muttered, without taking his eyes from the spectacle on the screen. What I hadn’t realized was that once a movie had begun, the television would automatically return to it when turned back on. The scene Todd was watching was alternating from a view of the actors’ faces as they fornicated doggy-style on the hood of a hot-rod, to a close-up of the actor’s huge dick impaling the silicone-injected actress’s ass-hole. As ridiculous as it felt to do so, I knew that I had to act now to seize the moment and make something of it, while minimizing the embarrassment of just being caught watching porn by my husband.

“Looks like fun” I blurted out.

“Really?” Todd replied, almost shocked by my comment.

“Mmmm, really”.

“I had no idea you’d like to try it” he said.

“There are a lot of things that you don’t know about me” I shot back, with a sly grin on my face. This was going alright so far.

“Oh really” Todd retorted, slowly moving toward me, “like what”.

“Well that’s for me to know, and you to discover” I replied with a giggle.

“I see, well let’s just see how far you’re willing to go with this little fantasy of yours” Todd grunted as he picked me up and threw me to the bed. He pulled open my damp robe, and kissed me passionately while groping at my tits, squeezing them with his full hands. Trailing his kisses to my neck, his hand slides down my belly to the tuft of trimmed red pubic hair that I keep over my pubic bone in order to be able to say that I don’t shave my pussy entirely. As his finger enters my slippery vagina, he whispers hotly in my ear, “So you really want your husband to fuck you in the ass huh?”

“Oh yes” I exhale as he plunges a second digit into my snatch. Pulling his fingers back out, I feel him slide one down to my anus, rubbing my secretions around the opening. He then brings the second one down, and timidly begins working it into my anus. I bend a knee up to allow my lover better access, and push myself down to meet his advance, sliding his finger into my ass to his third knuckle. “Mmmm” I groan with delight as he begins to withdraw his probing digit, adding the second which had briefly penetrated by wet pussy just seconds earlier. I gasp as his two thick fingers push past my sphincter and into my rectum. Delirious from the sensation of my lover filling my hole, I barely notice that he’s gnawing on my rubbery hard nipples, and that I’ve begun almost instinctively fingering my own clit. Todd begins working his two fingers rapidly in and out of my anus, and opens his mouth wide to draw almost my entire breast into his mouth. I can feel myself nearing climax, and I begin craving for my lover’s cock to penetrate my hole. “Fuck my ass, Todd” I moan, “I need your cock in my ass”.

Todd withdraws his fingers, and releases the latch on my breast. He rolls from the bed, standing at its side to remove his pants. I take advantage of the brief interlude, and grad the massage oil from the bedside table, where I’d strategically placed it earlier. In my haste, my finger catches the connecting string of my anal beads, which I end up extracting from the drawer along with the oil. Todd looked stunned at the sight of the beads dangling from my hand. “Something else for you to find out about hon” I blurt out, and clumsily shove them back into the drawer. I quickly pour an ample amount of oil into my hand, and replace the bottle atop the bedside table. Kneeling up on the bed, I bring my lubed hand to my rear, and smear the oil into my ass liberally. Turning, I’m met by my lover, his hard-on raging from his loins, appearing to throb before me. I take my oily hand from my ass, and stroke the length of Todd’s shaft, letting the oil drip like honey onto this tight scrotum.

I roll to my back, lifting my legs up to my husband’s shoulders. I clearly recall wanting to make sure that I could see my lover’s eyes as he entered my ass for the first time. Todd grabbed my legs at the middle of my thighs, and pulled me to the edge of the bed. Leaning forward slightly, he rested his weight onto one arm, grasping his thick tool with the other to guide it to its target. The visual of Todd’s hulking body pushing my legs back toward my chest to gain access to my ass was delightful. His oil-slicked cock pushed almost effortlessly into my hole, and we moaned almost simultaneously with his initial stroke. With his dick inside of me, he straightened his back, once again grasping my thighs, and began to pump his hips rhythmically. His hips made a hollow spanking noise as they met the back of my up-stretched thighs. I grabbed his hands, and yanked them hungrily to my tits, pulling Todd slightly forward in the process, stretching my hamstring muscles almost painfully.

With the intensity of Todd’s pounding increasing, and his hands now working my swollen breasts, I bring my hand to my snatch, and begin feverishly working my aching, stiff clit in a circular motion with my fingers. This was it! This is what I’ve been longing for, craving for so long. My husband’s broad penis was probing deep into my ass while my fingers were manipulating the hypersensitive shaft of engorged tissue poking its head from under the puffy folds of my labia. Todd’s massive hands squeezing the excess blood from my firm tits with their puffy, silver dollar sized pink nips protruding up in front of my face. This was what I needed to cum with my husband, and cum I did. With Todd still pumping his member into my rectum, my vaginal muscles began to contract wildly, spasming uncontrollably for what felt like minutes.

I regained my senses just in time for Todd’s climax. With a loud grunt, he pulled his slippery erection from my ass, and began pumping his fist over its swollen head as it hovered over my still widely parted cunt. His face strained as the first rope of sperm shot from his cock onto my tits and belly. One pump of his fist, and the second load of juice spilled from the end of his dick onto me. Another two quick strokes, and a third splash of jiz lands on top of me, mixing with my pubic hair. Todd continues pumping his fine prick, milking more cum from his shaft, dripping it onto my mound, grunting and groaning with each stroke. Sine we’d began sleeping together, I’d never seen him cum like that. His hard-on begins to slowly dissipate as he squeezes the last of his milky juice over his fingers and onto my pussy. He rubs the fleshy underside of his prick, now hypersensitive, over my cum-soaked labia, smiling down at me proudly from above. I reach for the end of his now semi-flaccid tool, dabbing the last bit if cum that’s oozed from his shaft. I bring my finger to my mouth, and extend my tongue to meet it, tasting my lover’s sperm as I slide my finger down the length of my tongue.

Todd lowers my legs gently to his hips before crashing down on top of me on the bed. We laugh and kiss and embrace, remarking that we should have tried this a long time ago. He still to this day believes that this was my first anal experience. Come to think of it, there’s a lot that he doesn’t know about me.

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