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Raging Robyn

Category: Anal Sex
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I turned a whole different shade of red as I pulled my card out of my wallet. Seventy-three dollars never felt so embarrassing and I was more than thankful that the clerk was a young, beautiful woman. Maybe she would understand; then again, maybe not and her judgment was withheld behind her professional smile.

I tried to talk myself down. I tried to remember that she was a clerk in sex shop. She had to have seen it all before. Surely seeing a man come in with his girlfriend wasn’t a far stretch. I just wondered how many men went into the store to purchase a strap on for their girlfriends.

I paid little attention to the clerk or the contents of the newly stuffed plastic bag. My focus was more to my girlfriend, Robyn. Robyn was just as red as me, but she managed to grin in a way as to communicate with the clerk in the silent fashion that only women can understand. Robyn and I were well into our relationship and were well into kink.

Robyn, until meeting me, considered herself a prude. I figured that prudish behavior would have been and absolute waste on a five foot, ten inch blonde with large breasts, a thin waste, and well rounded hips. We were in a snow resort town when I first met her, so her physique was hidden beneath jeans and a hoodie sweatshirt. Though dressed down, she was beautiful and I knew that I had to have her in my bed. I didn’t plan on her becoming my girlfriend, but I knew that I at least wanted to fuck her.

Her prude-like habits eventually caught up and it took a while for me to actually sleep with her. However, she was not completely adverse to oral sex. In fact, she down right enjoyed having my cock in her mouth.

One at a time, sixty-nines, from the front, from behind; oral was the only intimate exchanges that we shared for a couple of weeks. I didn’t mind. I loved the smell and taste of her pussy set atop her long, thin legs and gladly went down on her often. She, of course, returned the favor. She was able to take the full length of my cock into her mouth and slurp hungrily as I came in the back of her throat.

After a couple of weeks, Robyn and I had licked, teased, sucked, and came with the use of our mouths only. Then, on a cold, but glorious Friday night, she spoke softly in a way that made my hard cock twitch. In fine, Robyn fashion, she buried my cock in her mouth to the hilt and waited for the near-cum pause. Unexpectedly, she pulled her face away from my hard on and paused. “Ah, I was about to cum,” I protested as she looked up at me with her face just hovering over my member. My dick throbbed, aching to cum.

“I want you inside me,” she whispered. I’m not completely sure if she was able to finish the phrase before I scooped her up to me and flipped her onto her back. I had my dick in my left hand and guided the tip to her pussy. She was soaked and I knew that she wasn’t joking. I expected to simply slide into her, but it was not as easy as I had planned. She let me in on the secret that she had not been penetrated for a long time and she moaned with the slight pain of my hard cock pushing into her.

I buried my cock into her as slowly as my hips would allow. I could feel her pussy pulsate against me as she whimpered. I felt powerful looking down at her grimacing face, but I held still for a moment. I allowed her to adjust and waited for her signal that she was okay.

“Fuck me,” she exhaled in a carnal voice. I obeyed the request-slash-command and began to pump my hips forward and back. I started with slow, smooth, light strokes, but it was not before long that Robyn had her fingernail dug into my ass cheeks. She was allowing me to pull back until the head of my dick nearly fell out of her then she jerked me forward as to silently beg to be fucked harder.

I didn’t have to ask where she wanted me to cum before she whimpered, “I want your cum inside me.” She didn’t have to ask twice before I twitched and unloaded my loins into the depths of her hole. I pumped until I could feel that every drop had freed itself from my tip then I collapsed.

I came so hard that I failed to realize that she allowed herself to come with me. I had never had a simultaneous orgasm before and I wished I had paid more attention, but there was no lack for want and I certainly was not disappointed.

Robyn and I lay in a pile of flesh and sweat. Our bodies heaved as we tried to catch our breaths, but we couldn’t seem to pry ourselves from the other. It was the most intimate experience I had felt as a man in my early twenties. I wasn’t inexperienced is matters of fucking, but I was certainly new to feeling an actual love. I wanted more.

We finally managed to pull apart with a kiss. Where most couples go to clean up and turn on the television, Robyn and I lay next to each other. We were filthy from the fuck and didn’t mind. We exchanged pleasantries and I began to fall to the natural urge to sleep. I figured that would be the best way to get some rest for snowboarding the next day. Robyn, however, was a natural woman and had the natural burst of energy following orgasm. She was more interested in talking than sleeping.

“Jon,” she nearly whispered, “what’s the kinkiest thing you’ve ever done?” I found the question to be kind of weird coming from her. It nearly felt like a set up for a knock down, so I answered with a somewhat tame and sheepish grin. “I had a threesome once.” She chuckled a little then admitted that such a deed did not surprise her.

“Was it with a girl and a guy or two girls?” I kind of liked where the conversation was going, but I had to follow my nature to joke. “Actually it was with two guys.” Her eyes bulged out of her head until I started to laugh. She slapped me across the chest for being so boyish in humor. Then I answered honestly, “It was with two girls.” I still laughed a little as I asked if she had ever done anything like that, and I was a little disappointed of find out that she had not.

“So, my dear, what is the kinkiest thing you’ve done?” She had me hooked into the conversation. It would seem that horny-based conversation is more enticing that going to sleep.

Robyn smiled and admitted that she once had a sexual encounter in a public park. I was amazed at her exhibitionism until I found out that it was during the middle of the night with no one around. I still accepted her ploy to keep the dirty talk going. Then, her turn came again and the next question was asked.

“So, what kind of stuff do you fantasize about?” The question, though good in nature with the sense that she was looking to please me in the future, was still erotic to me. I began to answer, but stopped for the sake of embarrassment. “Promise you won’t laugh?” I questioned and she agreed. “I want to be fucked with a strap on.”

I expected her to burst with laughter, call me queer, or simply roll out of bed and leave. She didn’t. She just questioned lightly, “Really? I wouldn’t guess that would be something you would be into.” She was right in her assumption. I was a rough-edged man and I understood her thinking.

I had never told anyone that before and it turned me on to get it out in the open. I felt my cock harden a little as I said it aloud. I looked at Robyn and could see the gears turning in her mind. Her fingertips had found their way to my left arm and she stroked lightly as though she was turned on. “Have you ever done that before?” she questioned. I answered that I had not. I didn’t even know what started the fantasy, just that I had it for awhile and was waiting for a woman that I could trust with my secret. “Would you be interested in something like that?” I baited.

“I might be,” she cooed at me with a grin, “but I think we should work our way up to that.” She nearly sounded expert in her words. How would she know what to do or not to do? I asked if she had ever done anything like fucking someone with a strap on. She answered that she had not. Then she admitted, “I’ve never even been fucked in the ass.” My cock grew immediately hard again. “Can I be your first?” I wanted so badly to bury my member into her ass at that moment. “I think we can work up to that,” she answered.

Several weeks later, Robyn and I had gone through a series positions and oral exchanges that allowed us to experiment with each other’s back doors. I would fuck her doggy-style just so I could push my thumb into her ass. She would blow me with my legs over her shoulders so she could push her fingers into mine. We both felt as though we were getting to a point where we were ready to have the other inside our asses. Then the day came.

We got off work on a Friday at the usual time. She called me to make sure that I was going to be able to meet her at her apartment and that went without a hitch. I arrived at her place and she was ready to leave almost immediately. She had an evening planned for us and I loved being out with a good time girl.

Our first stop was a late happy hour. Several bears, a few game of pool, a couple of shots, and a few rounds of darts and we were ready to go. I thought that we would head back to her apartment and commence with continued love making and anal finger fucking, but she had something else in mind.

I didn’t recognize the area of town that we found ourselves in, but she was clearly up to something as we pulled up to the Midnight Book Shop. It was a coy name for a fuck store. I looked at Robyn and could only smile as we got out of the car. We were buzzed and a bit loose, so to speak. We were relaxed enough that we greeted the girl behind the counter and moved straight back to the dongs and dildos section of the store.

Robyn, a little uninhibited, picked up a dong the size of her leg and waved it at me. “What do you think?” She was playful and it made me laugh a little as I said, “Yeah right.” Then the shopping turned a bit more serious as we came to a series of boxes. All of which were labeled with goofy names like “Love Harness” or “Super Strap”. We, being a couple of novices, had no idea what we were looking for until I saw one that might accommodate us both.

The box was sexily illustrated by a beautiful woman wearing a black leather harness. The flesh colored cock poked out from her as she stood in front of the man with his hands on her shoulders. I picked the box up and looked at the details. The dildo was a girthy seven inches long, but it was connected to an inverted six inch dildo. It was like a his-and-hers package held together by leather straps. “How about this one?” I questioned Robyn and she commented that it looked great. With that, the decision was made. Robyn was going to fuck me in the ass to fulfill my fantasy for the first time.

The embarrassing purchase was made and we made an excited journey back to her apartment. I wondered what it would be like to be penetrated with something that large and my dick hardened inside my jeans. Robyn must have been looking at my crotch because she began to rub me through my pants. She could see how horny I was and I think that she must have been equally horny or a little drunker than I was.

I was driving, so she was able to open the newly purchased package without distraction. She pulled out the harness and held it up. She looked like someone brought Christmas early and I was pleased with her excitement. Then, I was able to see how drunk she was because she pulled the double dong out of the box. “Hmm,” was all she muttered before she placed the larger of the two dongs into her mouth. She pushed it in all the way and pulled off. “You’re bigger.”

Her matter of measuring made me even harder. I hated her for a second for doing something so arousing at a time that I couldn’t just take her. “It hardly seems fair,” she continued, “yours is bigger than mine.” I laughed at that, but she was trying to make the point that it wasn’t fair that I would hurt her more than she would hurt me.

We arrived back at her apartment and dashed to her bedroom. It was very late in the night, but we didn’t mind considering the buzz and excitement. It took no time before we were standing at the edge of her bed. Our naked bodies pressed to each other in the sexuality of the night and I couldn’t wait to get to business.

“Did you want to fuck me tonight?” she questioned. I thought the question was absurd considering my erection, but I answered in the affirmative. With that, she dropped to her knees and took my cock into her mouth. Her head moved in and out as her mouth slid up and down my shaft. My dick throbbed with excitement and I had not been that turned on for as long as I can remember.

I thought for sure that Robyn was just drunk enough to strap on the new toy and have her way with me, but she had different plans. A cold sensation ran over my dick and I looked down to see that she was dripping lube onto me. “What are you up to?” I asked as if I didn’t know what the semi-liquid was for. She began to jack me off with my dick at her face level. Then I looked down to the placement of her other hand. She had reached a handful of lube to her rear and was rubbing a generous amount over and about her ass. Suddenly, I heard her moan her distinct sound and I knew that she had pushed her finger into her ass. “How many fingers are you using?” She admitted her use of her two fingers then I felt her let go of my prick and reach up between my legs.

“Are you ready to fuck me?” It was a question that a woman normally reserved for her man, but I was the one making the inquiry. “Not tonight,” she answered. “I want you to fuck me.” She moaned again then said, “Three.” I loved that she was able to get three fingers into her drunken ass and I couldn’t wait any longer.

I reached down and pulled her hand away from my ass. “Stand up and get on the bed.” She did so, but lay on her back. “Roll over for me.” I was in charge and ready to fuck her.

Robyn was obedient without reluctance. She initially lay flat on her stomach, but lifted her lower body onto her knees without further direction. I had fucked her from behind many times, but never had I guided the tip of my dick to her asshole. My cool, lubricated tip touched her rectum and she jumped just a little. She was scared, but accepting. “Please go slow.”

I had fucked several women in the ass before and I knew that the best way for her to accept me into her hole was for her to back into me. I told her the same and she began to push back until my head plopped into her ass. She paused as though she was stuck. Then she moan as if to cry, but did not pull away.

I felt her ass clenching tightly and I remained still. I loved the idea that I was effectively taking her anal virginity and I loved it even more as she pushed herself all the way onto me. Her ass cheeks pushed into my hips and I instinctively lurched forward. It was too much too fast and she whimpered for me to wait. I could still feel her clenching tightly and I waited until she relaxed to say, “Okay.”

“Okay” was all I needed to hear. I ran my hands the length of her smooth back from her shoulders to her hips. I gripped tightly into her hips and began to push forward as I pulled back on her. She exhaled deeply with the first few thrusts before I felt her relax completely. “Fuck me,” she moaned. I began to pump harder and faster with the idea that she was enjoying being fucked in the ass.

It was not long before I was hammering away at her ass. I pushed forward with a continual slap of my hips against her ass. The lube that coated us both made my dick slide in and out of her hole with ease as I piled into her over and over. Robyn had since moved her hand to her pussy and was digging at her clit.

Her asshole bore down tightly as she came and the sensation of continuous contact with my nervous tip was too much. Her orgasm subsided just as mine began to pound through my body. I grabbed into her hips tightly and thrust forward as my cock spurt cum into the depths of her ass. I continued to fuck her sloppily until I wasn’t able to breath and my upper body collapsed to her back.

I kissed her between her shoulders and slowly pulled my still hard cock from her ass. She allowed herself to fall from her knees and lay flat on her stomach once more. “Oh my god,” she huffed in an audibly pleased voice. I was just as pleased. I always enjoyed fucking her mouth and pussy, but there was just something raunchy about hitting the glory hole.

The glow wore off after a few moments and we decided that it would be best to wash up after this go around. We walked each other to the shower and proceeded to clean one another lovingly. There was still romance after a good anal fucking and it was pleasant. Robyn was particularly touchy and connected and I enjoyed her company as such.

We returned to bed and fell into a hard and deep sleep.

The next day was fun. We had lunch with friends and smiled constantly as to show that we had a dirty little secret. We went out for drinks that night and whispered lightly to one another about things to come. We allowed time to pass in the bar before I finally had enough waiting. It was well into the night and I wanted to go back home. I wanted to fuck Robyn in the ass again. She was sitting at the bar when I went to voice my wants to her. In a sly, but less than discreet fashion, she reached down the front of my pants and felt my swelling prick.

“Let’s go.” We tabbed out and made way back to her apartment. In the same quick fashion, we found ourselves without clothing and aching for each other. I lubed up my cock, but this time I reached around to her ass for her. I pushed a finger into her ass, but she protested. “Not tonight, baby,” she stated as she put her hands to my chest. “Lay on the bed.”

I did as I was told and waited for her to climb onto me for a ride. However, she had a different plan. She walked to her closet and returned with the box that contained her cock. I involuntarily began to rub my hard on. I was so excited that I shivered a little.

Robyn reached into the box and withdrew the toy. She had put it together and tried it on while I was asleep earlier that day. It turned me on to think that she had been planning this all day long.

I watched excitedly as she held the harness out like a pair of panties and stepped into it. She slid the leather straps up her legs then spread her feet apart to give the smaller dildo access to her pussy. She hummed a little, pleased sound as the rubber dong entered her. Then she tugged at the straps and buckles until the unit was secure to her body.

Robyn sauntered toward me with the rubber cock bouncing back and forth. She stood at the edge of the bed in full view. She wanted me to get a good look and absorb the sight of her. I reached out as though I had no control over my hand and began to rub lube up and down the shaft.

“How do you want it?” Her new extension seemed to give her a sense of empowerment as she gritted the question. I was baffled as I didn’t really think the fantasy would go this far. “Doggy-style I guess.” I didn’t know how to answer and I don’t know where Robyn’s take charge attitude came from, but she retorted, “Well get on all fours then.”

It turned me on to have her bossing me around like that and I did not hesitate to get on my hands and knees. I felt her climb on the bed behind me and wedge her knees between mine. I shivered again thinking that she had already shoved the dildo into me. “Relax,” she cooed as I realized that she had inserted a finger into my ass. Whatever shyness or prude habits she once had were gone. I felt myself relax to her finger and I thought that I was ready.

Robyn moved the tip of the dildo to my ass, but her inexperience with having a cock caught me in the end. The head of the fleshy dildo pushed into me too quickly and I jumped forward. “Slowly,” I pleaded with a reversal of roles. Robyn decided it best that I push back onto her the way that she had done onto me.

I slowly moved back against the dildo until I felt the rim of the head make way past my rectum. I felt spread open more than I ever had before and had to give myself a moment to relax. Robyn stroked my back in a soothing fashion as I inched down her rubber cock. I moaned and sucked air through my teeth as I allowed my self to slide up and down the shaft. I had not made it all the way down before I pumped myself onto the dildo lightly. They were not long strokes; just long enough to loosen me up and spread the lube generously.

Suddenly, I felt my ass open wide and I slid, slowly, down the length of the shaft until it was buried inside me. I felt myself still pushing back even though my ass cheeks had met Robyn’s hips. “Okay,” I quivered begging to be fucked. Robyn allowed her hands to move from my back to my hips. Nearly every detail was the same as it was when I took her anal virginity. Robyn’s first withdraw was long and slow, but her first thrust shoved the full cock back into my ass with a thud of her hips. I felt the rubber dong bury deep into me and groaned as a second thrust came.

My arms buckled and my forehead met my forearms. I looked down the length of my body and saw that precum was pouring from my hard on. My dick was slippery and wanted to be touched, but I restrained for fear of cumming too soon. I looked further down and was able to see Robyn’s knees and thighs between my spread legs. I watched as her muscles flexed each time she pushed into me.

Before long, Robyn was into it. She was more into it than I had anticipated. She jerked back on my hips in contrasting rhythm to every push of her hips. She was slamming into me harder and harder with every thrust like I was no longer attached to my hole.

I felt like my cock was going to explode, but I didn’t want to cum and ruin the sensation. “Baby, can I lie on my back and watch you fuck me?” Robyn slowed her thrusts and slowly withdrew from me.

“Are you having fun?” she questioned as she pulled at my hips for me to roll over. I told her that I was with a smile up at her. I spread my legs to straddle her from beneath and she seemed to have an instinct for being the fucker as well as the fucked. She reached down to my knees and pushed them upward until my legs were bent and my ass was once again exposed.

Robyn wasted no time in getting her cock back into my ass. “Is this okay?” she asked to make sure that the position was not painful. I told her that I was okay just before she lifted my legs onto her shoulders. She returned to pumping in and out with the change of position. I was able to get a good look at the top of the harness that ran over her sexy hips. Her tits bounced each time her hips slammed into my ass. Her stomach muscles flexed and heaved between thrusts and breaths.

The sight of her, the sensation of her fucking me, the idea that my fantasy was fulfilled was too much for me to handle. I reached down and wrapped my hand around my cock. I jerked and stroked quickly until I came.

My cock twitched with the slick touch of my hand. It was the hardest orgasm I had ever endured. I let out a wide mouthed moan of ecstasy, but the angle of my legs being over Robyn’s shoulders must have been the source of my surprise. The first spurt of cum landed into my agape mouth. I was taken aback for a split second, but swallowed the tiny bit of cum as the second and subsequent blasts of come fell to my chest and stomach.

I came until I milked my cock dry. Robyn had stopped her thrusts to watch the show then she let my legs down and leaned down to kiss me deeply with her cock still in to the hilt. The wonderful sensation of being fuck, a rubber cock in my ass, and the deep kiss of the woman that I loved more than any other I had ever known was more than enough to leave my fantasy completely fulfilled.

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Jakke wrote

Wonderful story I felt like I e I was him