I couldn’t have been more vulnerable—naked literally and figuratively. My face was buried in the sheets, my ass in the air, hands parting my cheeks. A woman I barely knew was poised behind me armed with a strap-on cock. Her first thrust was a heartbeat away and my virgin ass was puckered in a knot. This was not what I signed up for.
Two weeks earlier:
He was always flirty and had a wicked glint in his eye but also seemed naïve and straight-laced. The kind of nice guy who liked to play at being naughty—at least that’s what I thought. We were working with a middle-aged woman on a charity project who was humorless and annoyingly prim. As the prude left the meeting he shocked me by saying, “That woman needs a good, hard orgasm, but I doubt she’s capable.” I couldn’t suppress a giddy laugh and was titillated by his inappropriateness.
Trying to be glib I said, “Are you offering?”
“God no,” I chucked. “I would be at risk for frost-bite. I’ll take a lifetime of self-abuse if she was the last woman on earth.” Her breath seemed to catch in her throat, unsure if she dared to respond.
With a puckish grin, she asked, “Do you do that often?” I paused and debated how much to reveal. My marriage was satisfying, the warm love that comes from years of shared laughter, children, and soon, grandchildren. Warm, but not hot. For a few years, I had become devoted to exploring every avenue of self-pleasure I could experience.
My wife spent most of the summer at our vacation home and there was plenty of time to bring out my secret stash of toys—my favorite being an expensive Aneros prostate massager. More than a year of experimenting had not yet yielded the “Super O” as promised, but it had brought an incredibly exciting new dimension to my sex play.
“Frequently,” he responded… sarcastically glancing down at his groin and lifting his eyes to meet mine. My pussy tingled as my imagination conjured a vision of this sweet and funny man gripping his erect penis, glistening with pre-cum, a look of exquisite anticipation on his face.
I crashed back to reality as he queried with a raised brow, “And you?”
“Frequently,” I croaked.
My husband and I were still very active, even passionate, but I recently found myself wanting more, needing more, craving exploration I knew he was unwilling to grant.
“I bet your sessions are as organized and elaborate as your event planning. Speaking of which, do you think our guests should enter from the front or would you prefer using the backdoor?” I was determined to see how far I could take this innuendo without her getting offended or frightened.
But instead, she seemed to regain her footing and her moxie. “I’m open to anything. Though I have found that most male guests rarely want their backdoor used for anything but an exit.”
“Not me,” I said soberly. “I have found a rear entrance to be a nice change of pace and use it routinely now. I’d welcome any lady guest who feels adventurous and open-minded.” With that, the spinster returned and our revelry was interrupted.
I couldn’t wait to get home, throw off my clothes and rub one off. I closed my eyes and imagined him sliding his finger into his ass…. First one, then another. stretching himself to the threshold of pain. The fantasy had my cunt swollen and wanting before I even started my nipple play. He was so different from any man I’d ever been with—men who though ass-play was gay and verboten. So he liked it in the ass? Maybe he’d like me to do the probing, and I don’t mean with my finger.
I’ve been the receptacle for cocks, fingers, tongues, and yes, I’ve enjoyed being stretched, slammed, and hammered in my various orifices, but just once I would like to do the violating. I wanted to experience that sense of control and domination I imagine a cock would provide me.
My mind drifted to an ad I’d seen on a porn page for a strap-on dildo. It held no fascination for me at the time… now it took on a sense of possibility and adventure. Would this man entertain my fantasy of being the fucker, instead of the fuckee?
I can’t believe this woman. An e-vite arrives in my inbox inquiring about my availability for another “planning session” and informs me she will be entering the location (a nearby 5-star hotel) from the rear and asks if I’m up to the “intrusion.” Is she asking what I think she’s asking?
I jotted down my acceptance, five days hence, and in the comment section included, “I will make sure the entrance you desire is prepared and ready to welcome you without reservation." It was a nice way of saying, “My ass is yours.” The thought of a prostate massage and exploring her most intimate zones is leaving my cock straining against my pants.
The anticipation is killing me. My thoughts border on violence. I will be gentle at first, but I intend to drive that dildo to its hilt. He doesn’t know it, but he’s the only one getting fucked. I have no interest in betraying my marriage vows. He will not kiss me, fondle me, or shove his dick in me. This is about me taking what has been taken from me, often without regard for my needs or desires.
If he’s lucky, I’ll let him watch me finger myself. I slide a third finger into myself as I imagine the relentless thrusting I intend to give his behind. As I thrust forward on to my fingers I imagine how that dildo will feel against my clit and the explosion that will come. His imagined moans and slight whimper send me cascading over the edge to a moment of mini-madness and release.
She’s asked if she could bring a friend and included a picture of a fucking strap-on dildo!! What the fuck?! She wants to split my ass with this massive fake cock? It’s twice the size of my Aneros and I can barely accommodate that! And yet, I’m intrigued, even fascinated at the prospect of being submissive and surrendering to this incredibly brazen bitch, whose demure exterior shrouds a need to dominate. Is this something she’s done before? Will she take care not to abuse me? I’m going to find some industrial strength lube, just to be safe.
I can feel my panties soaking as I approach the door to the room. I gently knock and it opens with him standing in just a bathrobe. He’s stunningly handsome and smiles a gentle smile. “You look lovely,” he says, and reaches out for an embrace. But I place my flat palm firmly on his chest and look sternly at him.
“We are not making love today friend. I’m here to give you the fucking you want and deserve and you’re my playground, not the other way around.”
I thought my cock was going to pop. Her intensity and power was the most erotic sensation I’d ever experienced. She backed me up to the bed where I obediently sat.
She slowly disrobed, businesslike, enjoying my discomfort. At the same time, the robe had fallen open and she could clearly see that while I was uneasy, my cock was not. Her breasts were those of a twenty-something. I struggled to determine if they were natural or enhanced. The nipples were large and erect.
She turned her back to me and dug into a large bag. I was relieved to see the cock she extracted was not the mammoth ass ripper she had sent in her text. It wasn’t small, in fact, it looked like a replica of my own organ. But it was only slightly larger than the squirming butt plug I used when my wife was away.
I stood before him and teased my own nipples. I wanted to tempt him with what he couldn’t have. Expertly I slid the dainty harness holding my cock over my legs and ass and cinched up my weapon snugly against my cunt. I grabbed it with my right hand as I pinched a swollen nipple with my left.
Then I slowly gyrated my hips while massaging the base of my dildo against the flesh of my pussy. His cock was so hard, a Tiger couldn’t scratch it. “Are you ready to lose your cherry sir?”
He nodded, licked his lips, looked down at his dick and retrieved a rivulet of pre-cum on his finger and put it on his own nipple. As he began tracing circles around his tit, I slapped his hand away and pinched his nipple hard, making him jump, but maintaining silence. I then took a drooling stream of pre-cum myself and popped it into my mouth. “Take off your robe and roll over.”
I did as ordered, shedding the robe and laying on my stomach. She dragged her breasts across my legs and she began mounting me from behind, ultimately sitting on the ass she was eagerly waiting to invade. I heard some oil being squirted into her hands and she gently began massaging my back and shoulders. I began breathing deeply, forcing myself to relax, knowing any tension would make this an exercise in pain instead of pleasure.
Her hands were firm and as she worked her way south on my back, she rested the cool cock between my ass cheeks. Slowly she slid backward, tracing a finger into my ass crack where that cock had just been. Another squirt, and warm lube tricked from the small of my back into the chasm hiding my entry. My cock was on fire and I gently humped the mattress beneath me. Before her arrival, I had prepared myself for her by cleaning my canal completely. I then injected my own lube into my ass in preparation for the invader.
“Raise your hips!” I didn’t mean to bark the order. It just came out that way. Tentatively, he shimmied back to elevate his ass. It smelled of soap and lavender. Had he douched? Taken an enema? His attention to cleanliness aroused me even more. He was thoughtful, and mindful that this was a first for me too.
I watched as the lube trickled to his anus and took my pinky and gently teased it. He sighed a deep sigh and my finger entered him smoothly. It was swapped for my index finger, and then the middle—his deep breathing allowing his ass to yield and stretch to my touch.
I twisted and gently massaged the lumpy walnut I encountered within. His prostate was firm and swollen. As I pushed a small tendril of clear cum oozed from his dick peeking out beneath my hand. My nails were trimmed to ensure there was no discomfort. As his hole relaxed further I withdrew my fingers.
I could see him peeking at my cunt from between his legs and I gave him a show—pushing my phallus aside and inserting my fingers into my dripping quim. I then took the moist glob from my pussy and smeared it on his ass. I wanted him to smell like a woman, to smell like a musty cunt. Slowly I stood and rested the tip of my cock against his waiting ass/cunt.
I focus on my cock, my breathing, the dripping of cum onto the sheets, anything to relax me and take my mind off the reaming I fear I will get. The tip touches me. The lube makes a comforting squish and it enters a fraction of an inch. I can’t help but moan. In my years of ass play and increasingly inventive masturbation, I’ve dreamed of reversing roles with a lover. I feel her hands grip my thighs and pull my ass towards her. The penetration feels extreme, I whimper reflexively but I take the dildo deeper into my channel.
She withdraws and gives an awkward thrust. The lube I had injected is released onto her dick and she gasps as the entire shaft embeds another three inches. She withdraws and with a scream fires her hips forward while drawing mine back and the cock disappears entirely into my moist ass. I find myself wishing she could ejaculate into me—that she could feel the joy, power and release of steaming hot semen shooting into the most sacred spot a human possesses.
Take that mother fucker! Eat my cock. All of it. I reach for his chest and pinch his nipples as hard as I can. I want him to feel pleasure and pain collide in exquisite bliss. As I thrust, my pussy is getting a rubbing from the dildo’s base and I can feel my climax build. I wish I had balls to slap against his ass. I want to leave him an oozing, slimy mess, but I have no jizz. His moaning is rising in pitch and so is mine.
I can’t contain my climax any longer and to my surprise, for the first time in my life, I spurt, squirt and ejaculate on myself and fling droplets of my fluid onto and into his ass. It was an eruption thirty years in the making. The quaking, docile girl who let men pound their meat into her had just achieved the nearest thing to manhood and feminine release in a flood of emotion, passion and girl cum.
It felt like someone had thrown a cup of warm water on my balls, belly and behind. The sensation of her ejaculation sent me reeling. My muscles seized on that cock and drew it even deeper inside of me and in that instant of maximum penetration, my prostate convulsed and shot a load onto my chin, face and arms. My juices mixed with hers and I opened my mouth to try and catch as much of this delicious nectar as I could.
I was spent. I squealed as a second wave of pleasure unexpectedly and sent one last jet of cum onto my victim, who was taking his free hand, scooping up our mixed mess and greedily jamming his sticky fingers into his mouth. With a burst of breath, I disengaged from him. I stared intently at his quivering anus, still pulsing from his pleasure and lube trickling from his deepest recesses. A tiny majestic spot of crimson gave witness to the fact his virginity was now mine. In spite of myself, I bent down, stuck out my tongue and began cleaning him.
It was the sweetest surrender. I wanted more intimacy, my power back, but she was stern in her denial. Is this what they feel? An emptiness when it’s over? Was I used? This is why my wife and former lovers craved cuddling after. It was a voluntary violation, pleasurable, but a violation nevertheless.
I rolled over and penetrated her eyes the way she had penetrated me. They looked electric and strong. The dildo hung beneath her, now impotent. She unsnapped it, threw it to the side. Instantly, her features softened and she said, “Would you hold me for a moment?”
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