Female Dominatrix Gets Guy to Anal Orgasm


image of realistic dildos product

“Chloe?” I entered the hotel room, closing the door behind me while wondering why she had turned out the lights. Her birthday clues had led me here to room 109 at Hotel Rogue.

The overhead light came on and I blinked several times at the woman standing before me. “Cat? What are you doing here?”

Cat was one of Chloe’s good friends; they had known each other since freshman year at college.  While in school, Cat was known as a smart, incredibly sexy girl who also knew how to party. “Work hard, play hard.” was her motto.  After college, Chloe and Cat stood in touch; I’d occasionally see her at parties and other celebrations.  Cat was a successful massage therapist who I heard worked with many high-end clients.  She was also incredibly hot eye-candy.

“Welcome.” Cat said while smiling at me. “Chloe left this for you.”

I took the envelope she handed me and eyed her. Something was off, and I swallowed nervously. She was standing before me wearing an extremely short robe that showed of her toned legs. She was tanned and fit, her arms toned in the short sleeves of her leopard print robe. Her long chestnut brown hair cascaded around her shoulders and her chocolate set brown eyes held a mysterious gleam.

I instantly felt aroused but was embarrassed.  I tamped down my burgeoning desire and pulled open the flap of the envelope. I removed the single card that was inside. It was a custom designed happy birthday card with a male bent over to blow out a birthday cake. It would have been an ordinary enough birthday cake except the man was naked and had a dildo up his backside. I scanned the words scribbled inside in Chloe’s recognizably neat handwriting.

Not because I say no all the time means you shouldn't get your heart’s desire. This on your special day, I offer you your special request. Cat will take care of your anal urges.

I glanced up in shock and stared at Cat. This couldn’t be real. But, the way she was smiling at me, I knew I had understood well the words of the card. 

Ever since I was a teenager and had uncovered that touching my ass was pleasurable, I had desired to introduce anal pleasure into my lovemaking.  But my girlfriend Chloe wasn’t really into it.  She’d finger my ass during a blow job, but her heart wasn’t there.  During one conversation about college, Chloe had mentioned something about how Cat had a reputation for giving her boyfriends anal pleasure.  I now realized why Cat was here.

My cheeks burned in embarrassment and I stared down at my size thirteen shoes. I shuffled my feet and frowned. If Chloe had intended this all along which judging by all the carefully thought out clues, she had, then it meant she had to have spoken to Cat about my fetish.

“Hey, there’s nothing to be shy about.” Cat approached me and cupped my face in her hands, raising my head. At my six feet, she was a couple inches shorter than me, but she was taller than the average woman. “We’re gonna have a heck of fun tonight. You’ll see.”

“I just don’t-”

“Do you know what I do for work?” she asked. “My expertise is getting guys to cum their brains out without touching their cocks.  Do you know how I do that?”

My heart began racing.  “I don’t know.” I replied.

“I get them to cum by pleasuring their asses and pumping their rectums until they spill.  Has anyone ever done this to you?”

“I… not…”

Before I could utter another word, she tugged my head down and captured my lips with hers. She kissed me, teasing my lips and playing a cat and mouse game with my tongue while her hands worked deftly at my shirt. I was so distracted by her kiss that I became aware that I was being undressed only when she pushed the shirt off my broad shoulders.

“You, follow me.” She hooked her fingers into the waistband of my jeans and gave a little tug. I hesitated, torn between wanting to run from this level of intimacy with someone aside from my girlfriend and my curiosity at what was so special about her why she was praised by those who knew her as an anal orgasm expert. The very thing I had been curious about for such a long time but pushed it at the back of my mind because Chloe hadn’t expressed any interest in the same.

She tugged again and I followed her, albeit nervously. I can stop any time, I reminded myself as I trailed after her to the large four-poster bed.

“Let’s get you out of these jeans.” She reached for my jeans and I was about to tell her I could manage on my own when I noticed what was laid out onto the bed. My mouth fell open, my jaw lax at the sight of the 12-inch flesh-toned dildo that lay on the bed beside a towel. Next to the dildo was a brand new bottle of lube. Fuck, I thought. All that bottle of lube still wouldn’t be enough to get that huge dick up my ass! She should know that, being the damn expert of us two.

“Caaat,” I drawled her name uncertainly. “What the hell is that?”

She glanced to the bed and turned back to me. “The dildo I am going to use to bring you the greatest climax you’ve ever had?”

“But it’s huge. I can’t- there’s no way, it’s impossible!” I finally exclaimed after stammering away.

“Let me be the one to worry about that tonight, sweetie,” she remarked. “All you have to do is feel. Can you do that for me?”

She got me out of my jeans and I felt like a robot as I allowed her to undress me. I was completely naked before her but was not ashamed because I was well-built and fit. Despite my hesitation about what was on the bed, my cock stirred at the thought of how great it would be to be penetrated by the monster dick.

“Jesus!” I cried out in a strangled voice. “Don’t you have anything smaller? You know? Like half the length of that?”

“The bigger the better. I bet you’ll thank me profusely once you’re done.”

She walked over to the bed and returned with a cock ring. I hadn’t even seen it beside the dildo because my eyes had been focused on the monstrous size of it. I eyed the cock ring in trepidation. Cat placed both her palms against the solid walk off my chest and slowly weaved her way over the bumps and ridges of my hard chest.

“This will delay your climax,” she explained to me. “Because you’ll feel so fucking great that you won’t want it to end.”

She grasped my cock and slipped the cock ring into place. When it was securely fastened, she went onto her tippy toes and licked my bottom lip. “Do as I say. Is that understood?”

I nodded, wondering what the hell I had gotten myself into. She shrugged off the robe she had on and then indicated for me to lie on the bed. Staring at her perfect figure, the high firm breasts and small waist, in the sheer negligee she had on, I climbed onto the bed without a word.

“Get on your knees.”

I hesitated, thinking about how exposed I would be in that position. She trailed her hand over my leg, rubbing the back of my knee gently. How did she even know that I was sensitive there?

“I won’t do anything you don’t want me to do to you.”

With a groan and my heart thumping in my chest hard, I positioned myself onto my knees and buried my scarlet cheeks into the sheet. My body was stiff and, in all honesty, I was ready to flee at the first sign of discomfort.

Cat crouched between my legs and placed her palms onto my ass. If it was possible, I grew even more rigid. She didn’t comment but ran her hands slowly up and down my back in soft massaging motions. I felt myself relaxing, my back caving in. She continued down towards my butt, lightly touching me. Her touch got bolder, harder, squeezing and caressing the perfect hard cheeks.

She spread my ass cheeks and I started to clench automatically. “Easy there,” she murmured eying my pucker. “It’s just us two here.” I felt her saliva hit my tight opening dead center. She dipped her head and used her tongue to spread the liquid over the area. My thighs became taut and I gasped as she stabbed her tongue through my asshole. She licked the opening, fluttering her tongue around. She moved slowly and deliberately, licking upwards in shallow movements then spreading her tongue across the expanse of ribbed flesh.

“Oh fuck,” My groans filled the room. “Oh fuck, Cat.”

She licked down to my taint, teasing me as though reaching for my cock but made a retreat back up to my asshole. I groaned in frustration, the natural instinct to have my cock touched gripping me. It took everything in me not to listen to the call.

“You love that, don't you?” she asked.

“Yes!” I moaned.

I missed the velvety feel of her tongue when she eased back to pick up the lube from the bed. She squirted a dollop onto her fingers and returned to my backside.

I was already used to small items being inserted into my anus so it was just a matter of me relaxing. I took in deep breaths as she began probing my anus with her fingers. She started with the index finger, rubbing it around the outer edges first. Next, she dipped her finger just inside, down to the end of her nail. The deeper inside she pushed her finger, a stinging sensation followed. I stiffened at another finger she was attempting to introduce.

“Relax. Just take deep breaths,” she said softly, and she reached beneath me to grasp my balls. She rubbed them with the palm of her hands, caressing each individual ball. The new sensation shifted my focus as she ran her thumb down my seam lightly. I gasped then groaned when her second finger filled my ass.

“That’s it,” she murmured, removing her fingers. She pushed them back into my body and I blowed shallow breaths in the effort it took me to remain calm. She played around with my anus, pushing her fingers deep then alternating rimming just the edge. She plied her fingers apart, pushing against my sphincter muscles. 

“Turn on your back for me.” she ordered with a kiss pressed to my ass.

I turned over gingerly onto my back to face her. She had a half-smile on her lips which made me look away in a little bit of embarrassment. When she was behind me and I couldn’t see her, it was a whole different experience.

“Hey, there’s nothing to be ashamed of,” she said reassuringly and reached for the 12-inch dildo. I watched her without saying anything while she lathered it up with a generous amount of lube. My eyes were focused on her long slender fingers enclosing around the wide girth of the dildo. She caressed the dildo as though it was a real cock. Watching her made my own dick throb with pleasure. 

I thought I was ready but when she crawled between my legs and asked me to raise my legs to bend at the knees, they began to shake a little. My body went still, clenched rigid when I felt the dildo rest against my asshole. I blew hard expecting her to rip inside me. Instead, she rested the cool tip of the dildo against my clenched anus and winded her way up my body until she was straddling my waist. She leaned forward, her eyes finding mine. I was deeply ashamed of my uncontrollable fear but could not seem to look away from her beautiful eyes. Without even saying a word, they spoke a lot. 

My heart was racing so hard and thumping against my chest that it moved rapidly beneath her. She lay on top of me, hear chest pressed to mine.

“Listen and feel the rhythm of my heartbeat,” she said softly and did not look away. Her face was relaxed, a small calming smile attached to her lips. 

At first, it was impossible to feel anything but how nervous I was. My heavy racing heartbeat clouded everything else. It didn't make it easy either that the dildo was still resting there between my legs, pressed up against my anus. I knew I could move if I wanted to but I remained. I wanted this at the same time I was terrified.

She ran her lips lightly over my neck. “I'll go slow.” Her words were so low it was hard to hear. “I'll be gentle with your ass at first.” She continued kissing my neck, using her tongue to draw patterns on my skin. “We will get you accustomed to the size and the feel of all twelve inches up your ass before we have some more fun. Sounds fair?”

I nodded but was still too immobilized to move. “I won't do it until you relax,” she said still using that calming voice of hers. 

I dragged a shuddering breath into my lungs and let it out slowly. I repeated the action several times and when I was almost totally calm, she kissed down my collarbone and chest. She found the sensitive buds of my nipple, each tug of her mouth causing a jerk in my pelvis. She had me moaning so much that when she replaced her mouth with her fingers and continued kissing down my body, I was relaxed. 

Her fingertips trailed over my hip bone and further down to grasp the dildo. I couldn't resist lifting my head to see what she was doing. She grasped the dildo with one hand, holding it by several inches to the top. 

She started off by rubbing the dildo across my pucker and through my crack. She did it several times, the touch starting light but then really digging into my ass with each passage over my anus. 

I moaned in anticipation and shifted my hips impatiently. At that moment, she paused the big, curvy head of the dildo over my anus and pushed. My muscles strained to expel the foreign object pushing inside my body. I lost some oxygen in my shallow breathing to ensure that I didn't panic and jerk away. As much as I was somewhat apprehensive, I also wanted to feel it all. 

I gasped when the dildo popped into my ass, the small move felt like I was ripping in two. With one hand, she pressed against one cheek, prying it farther apart from the other to give her more room to maneuver. She slipped her hand higher up on the dildo, in the middle and pressed it deeper into my ass. My ass stretched, the muscles protesting but eventually caving in to the thick, round cock she had filling my ass. Her arm steady and sure, she pressed deeper, pushing without deterrence. For every inch that the dildo filled my ass, she pulled back her hand up to the base to guide more of its length into my smarting backside.

There was no other way to describe how I felt but full. I could feel the wide stretch of my ass to accommodate the dildo. I stung a little from the invasion, but it was not unbearable; neither was it unpleasant.

“I am going to remove my hand,” she warned me. “Clench your muscles and keep it in place. After three.”

She counted to three and I clenched my inner muscles which gripped onto the dildo and hung on for dear life. She shifted upwards, between my legs to kiss my flat stomach. She used her tongue to lick beads of sweat that was forming on my skin on her way up to my nipples. 

“Don't let the dildo slip out,” she cautioned me before latching onto my nipples which were sensitive and budded from arousal. Goosebumps pricked my flesh and had me shivering from the lapping off her tongue against my nipple. I clamped my eyes closed and clenched my teeth as I did my butt cheeks. Intense feelings of pleasure streaked through my body over and over and I felt like if I lost control the dildo was going to pop right out.

I didn't want to disappoint her.

As though aware of my thoughts, she stretched a hand down between my legs to grasp the dildo. I released my gasp then and allowed my body to relax beneath her. 

“Now let's have some fun,” she remarked with a mischievous smile and slid down my body once more. She reached for the lube and dribbled some more of the liquid down my crack. She wiped her fingers into the lube and rubbed it over the rest of the dildo that hadn't made its way up my ass. Yet.

Resting between my legs once more, she pulled the dildo out slowly while twisting in a counterclockwise motion. She left only the head inside me and jiggled it back and forth before plunging it deeper inside me. I felt like my ass was being cleaved into two with the huge size of the dildo. 

“How does that feel?” she asked me. 

To answer her, I moaned at the large circular motion she made with the dildo halfway up my ass. I opened my mouth to speak but before I could utter another word, she repeated the action but this time from opposite direction.

“How about we get it all in?” she asked.

I nodded because I was speechless. She pulled back an inch then pushed in two inches deeper. She continued doing this while continuing smaller circular motions. Each time she pulled back, she pressed deeper and deeper. The inches filled me more than I thought it could. I calculated in my head. Nine inches. Ten inches. Eleven inches. And then I felt the full twelve inches pressed up deep into my asshole, her palm splayed over the end and holding it in place.

“Suck in a deep breath,” she advised. 

I did as she said sucking a deep breath and she pushed on the dildo even deeper up my ass.

“Fuuuuck!” I exclaimed. She didn’t remove an inch of the dildo but kept pushing it up the end against my pucker. She twisted the end slowly into a 180-degree semicircle then repeated from the other direction. I groaned and raised my legs slightly, tilting my pelvis a bit to give her better access to what she wanted to do to me. 

Cat grasped the end and slowly inched it out of my ass fully. 

“Oh sweet!” she exclaimed. “Look at that gape.”

I felt empty and open, my pucker wide and ready to receive back the dildo. 

She dipped her head to thrust her tongue as deep inside my ass as it could do, licking the inside before pulling back. Holding the dildo this time by its base, she slid the girth back inside of me and I moaned in contentment at the feeling of fullness once again. She slid the dildo all the way up into my ass just as before and pulled out again. 

She continued sculpting my asshole with the dildo before she started to do slow, shallow pumps, easily pushing about half of the toy in and out of my ass. I could feel my anus slackening with each thrust, every thrust becoming easier and bringing more pleasure. The slow, shallow pumps turned into faster shallow pumps, rimming the edge of my ass only but hard and fast.

She pressed a hand to my stomach and filled my ass with the dildo again while twisting and turning like a doorknob. With her hand pressing into my belly, I was amazed to have the sensation that she could feel the bulge of the dildo as it filled me.

“That's amazing,” she said on a satisfactory sigh. She removed the dildo and plunged it deeper inside me again. “I can feel your ass filling up with this cock. See, in and out. In and out.” She pressed harder into my stomach and this time my eyes bulged because when she sliced through my pucker with the dildo, the pressure was exquisite of her hand depriving me from space that the dildo was already consuming. I was amazed that she could feel what she was doing to my body. Her face was full of pleasure and I realized that she enjoyed doing this to me.

“How do you like that, hmm?” she asked me.

“So fucking much!” I gasped when she surprised me by switching from a fast, shallow thrust to a quick, long, deep stroke. She drove me into a frenzy of unexpected strokes, making it impossible for my brain to predict what was coming next. Her strokes were fast and quick, two times shallow then one time deep. One time shallow and two times deep. Two times shallow and another two times deep. 

Sweat beaded down my temples, and I was blowing so hard like I was running out of oxygen. 

“Faster and harder?” she asked me.

“Fuck yes!” I begged.

I wanted it all. I wanted to feel all that wonderful cock filling my ass, ramming me hard and fast.

She poked a finger around the loose folds of my anus and caused me to shiver. Dripping more lube onto the dildo, she positioned the toy against my ass and using both hands plunged it deep inside.

“Fuuuuck!” I exclaimed in surprise at the thickness stuffing my ass. She didn't give me any time but changed over to one hand once more and started to plunge the dildo over and over into my ass.

“Turn over for me and lie flat on your stomach, Adam,” she instructed. “I'll hold the dildo in place.”

I had to take a few seconds to regain my breath before I turned over onto my belly carefully. She twisted the dildo in my ass with my movement, robbing me of my ability to breathe. 

“Spread out your legs so your toes point to the two bottom bedposts.”  I quickly adjusted. “Good… now stretch out your arms and hold on to the sides of the bed.”  My arms were barely long enough to reach over the sides of the bed, so I grasped the sheets.

“Great.  Now just relax and take a few deep breaths with me.”

I began taking deep breaths and relaxing my body on each exhalation.  Meanwhile, Cat was stroking up and down my back with her hands.  I felt my body sink into the bed and fully relax.

“Let's work on that orgasm, now. Just stay relaxed and scream into the pillow if you need to.”

With that, she nudged my legs further apart to settle between them and gripped the end of the dildo. She withdrew and grasped the toy with both hands. My cry was muffled by the pillow when she plunged the dildo without mercy deep into my ass. Pulling back, she retreated only to plunge deeper again. Within the space of a second, she was plunging and retreating, the dildo still clutched in both her hands.

She instructed me to hold my butt cheeks apart without even stopping and I reached behind me to do as she asked. Without the interference of my cheeks, I could feel the sensation of the huge hard silky surface of the cock sliding vigorously in and out of my ass. She reached beneath my legs to caress my testicles and returned to using one hand, held at the base of the cock to ensure its full length was stuffed up my butt with each thrust. She was breathing as hard as I was and the bed was shaking as she put her weight into each plunge she made into my ass. 

“Holy fuck!” I shouted, pressing my face to the sheets in time to muffle the sound. She did something with her hand, angling the cock as she thrusted it inside me and it hit my prostate, jerking my body. She did it again and again, the huge head of the cock working to massage my prostate over and over. Delicious sensations tingled in my spine and swelled to an epic proportion. My body jerked, tightened and stiffened from the huge twist and plunging motion of her arm. The muscles in my ass quivered and tightened around the cock, squeezing and squeezing until I thought I would burst from the fullness. My contracting muscles threatened to push the dildo out of my ass which Cat allowed to a certain degree before she pumped it back inside. In and out. In and out. Vigorously, she pumped me to a climax, through the stiffening of my body. I scrambled for the pillow above my head and just managed to dump my head into it to muffle my shout as my cock spilled its juice, milked from the inside with the dildo hitting my prostate. I came hard onto the soft crisp bed sheets, harder than I’d ever experienced from a climax before.

Several seconds passed in which I lost sense of everything. I collapsed against the bed, my breathing shallow as I tried to make sense of the epic proportion of the climax. 

“I’m going to remove the dildo now,” she told me, stroking the middle of my back. She sounded please but it could not be as pleased as I was. “Relax just as you are.”

I was too mellow, my limbs too watery for me to even stiffen as she slowly pulled the dildo from my ass. I felt a great pressure as it was being pulled out. Even after the toy was fully out, I could still feel my anus opened.  Cat rubbed her fingers over the edges.

“Everything will be back to normal in a bit,” she assured me then planted a kiss in the center of my back. “You’re welcome.”

A smile tugged at the corners of my lips. She was right. This was the best damn orgasm that I’d ever had.



Story Recommendations For You...


thumbnail of wand massagers product

I collapsed on the tattered green couch in the family room and kicked off my heels. I pulled out my ...

thumbnail of realistic dildos product

Pain throbbed behind Miranda’s right eye. She pinched the bridge of her nose. This was not happening...

thumbnail of realistic dildos product

My name is Lisa and I want to share an awesome experience I had with my best friend, Greg. We were n...