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Exploring Anal

Category: Anal Sex
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I’ve always had a desire to try anal sex. I don’t know what’s caused this, but ever since I first saw it in a porno when I was a teen I knew I wanted to do it at least once. It’s always seemed like a very intimate thing. It takes a lot of faith from a woman to allow a man to do something like that since it’s so easy for him to hurt her. And he needs respect and honor that. This is not something where you just flip her over and ram it home. It has to be worked up to and taken slowly. For me, it is the ultimate in trust.

But I’ve never had the opportunity to fulfill this personal fantasy. Neither did I know how to broach the subject with Lisa, the woman in my life.

It started simply. We were laying together in a sixty-nine with her on top of me. Lisa’s mouth on my dick was simply driving me insane. I had never received a blow job like she could give. Absolutely mind-blowing. My tongue was flashing and flicking at her clit like mad in return. I slipped two fingers into her dripping pussy as I started to suck on her button because I know how much she loves that. As I worked my fingers in and out of her, my pinky managed to touch her brush up against her star. However, I think that the both of us were too involved in trying to get the other off to really notice and it was pretty much forgotten.

We made love several more times before anything happened again. Once again, it was during oral sex. My lips were wrapped around Lisa’s clit and I was sucking on it like she likes so much. My hands were playing with her nipples as I lapped at her. Too busy breathing to talk, she grabbed my right hand and pulled it up to her mouth. She put one of my fingers in her mouth, getting it wet before pushing my hand down to her pussy. I knew what she wanted so I slide it into her causing her to moan. After a few minutes, Lisa asked for more. I took my finger out and placed my middle two fingers against her and then pushed them both in, palm up so that I can hit her g-spot. She groaned again and pulled her legs up to her chest, tilting her hips up so my mouth can work her clit even better.

Unfortunately, my hand kept bumping into my chin so I had to turn it over and bend my wrist slightly so I can push them in deeply like she wants. Each time I pushed them in, my thumb touched her rose. I noticed it, but I wasn’t sure she did as her orgasm started. I pushed my fingers in as far as I could and sucked hard on her clit as she came. Her back arched up and her moans and sighs turned to whimpers and whines. Finally, she grunted hard and her body collapsed back to the bed, her hips bucking wildly against my mouth. Each time they came up, my thumb pressed against her ass. I felt it contracting and pulsing with each wave of her orgasm. It was right then that I realized I that I wanted to feel her ass around my cock. That night, we ended up fucking the hardest we ever had up to that point in our relationship.

After that night, each time I fingered her I would find a way to play with her ass with my thumb, or another finger. Each time, I would escalate slowly, ready for her to object but she never did. I went from just brushing her ass as I worked my fingers in to holding it against her the entire time. Then I went from touching her rosebud to pressing against it firmly. Soon, I wasn’t just pressing my thumb against her, but actively pulsing it, applying pressure and releasing it with each thrust of my fingers. I know that she had to notice what I was doing, but she never said anything about it during or after. Sometimes while I was eating her, I would get so into it, my tongue would slip below her pussy and flick towards her ass, but never actually touch it. She would gasp a bit and press her crotch against my mouth even harder. I figured that she just wanted my tongue on her clit again, so I would shift my attentions back to it. By now, each time I fingered her pussy, she would pull her legs up to her chest which would inadvertently allow me to play with her ass with ease. I would run my thumb around her rim before pressing against it. By the time she would come, my thumb would actually be partially in her ass. Not actually past the ring there, but it would definitely be relaxed to the point were only a little effort and a bit of lubrication would allow it to slip in.

Everything changed one night while we in another sixty-nine. My fingers were coated in Lisa’s juices from being buried in her quivering pussy. I pulled them out so I could slip my tongue into her entrance and gripped her ass cheeks with my hands to hold them open. My slick fingers rested on her star again. I automatically pressed my finger against her out of habit and it slipped right in to the first knuckle. Her head came up and let my cock slip from her lips. She turned back to look at me and asked, “What are you…?” but her question was cut off as she started to shudder. She moaned again and laid her head on my thigh, her warm breath flowing over my shaft as she started to pant. Knowing the risk I was about to take, I pushed my finger further into her ass. Lisa let out a throaty moan and I saw her get even wetter. Her legs gave out under her which cased her pussy to be pressed even more against my mouth. Too far gone to stop now, I wrapped my free hand around her waist just above her ass to hold her in place and attacked her with my tongue.

As soon as my tongue touched her clit, she just exploded. She started to cry out but it was cut off almost as soon as it started. Lisa’s breath cut off in her throat and she went rigid. I could feel the strain in her body as her orgasm swept through her. Her ass contracted wildly around my finger. I started to worry about her passing out as she kept coming so hard so I released the pressure on her clit and eased my finger out of her ass. Doing this was like breaking down a dam. Her pussy literally flooded my face and mouth with juices. Lisa’s breath rushed out of her in a loud “Unnnhhh…” Her head fell to my thigh again and she began to tremble uncontrollably. I heard her trying to say something, but it all came out unintelligibly, lost in the gasping and shaking. Finally she stopped and collapsed in a boneless heap on top of me like someone let all of the air out of balloon. Sweat covered her as she lay panting on my body, exhausted beyond the point of movement. Her orgasm that night was so intense and powerful; we were unable to do anything else that evening. It was all she could do to turn around on the bed to lay her head on the pillow. Normally, she’ll lay her head on my chest or we’ll cuddle with me spooned behind her after sex and go to sleep like that, but not tonight. She’s asleep almost immediately and I just lay there, not sure of what tomorrow would bring.

I woke up the next morning to her leaning on her side and looking at me. I stretch and yawn and smile sleepily at her. Lisa doesn’t smile back. She sat up, crossing her legs in front of her and her arms over her chest and looked at me. “Can we talk about last night?” she asked in a serious tone of voice that you really don’t want to wake up to. Ever.

Not quite sure what’s going to come from this, I tentatively answered. “Okay.”

“You know, I’ve wanted to talk to you about what’s been going on.”

I gulped guiltily and prepared for the worse. “Really?”

“Yes. I didn’t know exactly how to bring it up, but after last night I feel like we need to now.”


“Well, I’ve noticed that you’ve been touching and playing with my ass as we have sex recently. At first, I thought it was just coincidence but I finally realized that you were doing it on purpose. Am I right?”

“Yes,” I said, getting nervous about where this is heading.

“Can you tell me why?”

I took a deep breath, trying to stall while I attempted to get my thoughts in order. My brain raced around as I tried to find a way to salvage the situation. Well, no way to go with this but with the truth. “Honestly?”


“Well, I’ve had a fascination with anal sex for a long time. It’s something that I’ve wanted to try but I’ve never known how to bring up the subject. You’re right. I’ve been doing it on purpose. The first couple of times were pure accidents. When I realized what I was doing, I know I should have stopped. But I couldn’t. I knew that if I did, I’d never get to do it again. I convinced myself that you had to know what I was doing and was letting me continue. I think that last night I went a little too far. I’m sorry.”

“What did you think I would say if you asked or even told me of this?”

I sighed again. “Well, I figured you’d tell me I was nasty or disgusting and never let me near you, let alone your ass, in any way, shape, or form again.”

“So you just decided to keep it to yourself and continue to take liberties with my body, even though you figured I’d object?!”

I knew that tone of voice. I started to mentally review who I could call to stay with for a couple of days until she calmed to the point were I could attempt to start making up to her. “Yes. I’m sorry.”

“You should be after last night.”

“I know. I am.” I started to get up and get out of bed.

“You’re not going anywhere. We’re not done yet!” With that Lisa jumped up in front of me and shoved me back down onto the bed.

“What’s going on!? What do you mean ‘We aren’t done yet,’?” I demanded, sitting back up on the edge of the bed.

Lisa stood there, hands on her hips. “What I mean is; you aren’t going anywhere just yet. We’re not done, because you’re going to do that to me again!” With that, she stepped forward and straddled my lap. Her arms slipped around my neck as she leaned in for one of the hottest kisses we’ve ever shared. Her legs wrapped around my waist, ankles locked together behind my butt and her knees up along my sides, and I could feel her grinding her already soaking pussy against me as she rolled her hips. Our kiss finally broke and I was still lost in the shock of the situation. She looked me in the eye, kissing me every couple of words and told me, “I don’t think… I’ve ever… come… as hard as I did… last night. Your finger… in my ass… was… just… incredible… and your tongue… in my…pussy… at the same time… was too much.”

While my brain was still trying to sort through what just happened, my cock decided to go ahead and react first and worry about the details later. It responded in the only way it knew how and sprang to life, going from limp to rock hard in the space of a handful of heartbeats. Lisa noticed and started to gyrate her crotch directly on my stiff member. Small moans escaped her as the motion of her little dance caused me to brush against her clit every now and then. She grabs my hands and places them on her firm, tight little ass cheeks and leans in for another hard kiss. As Lisa’s tongue forced its way into my mouth, she pushed herself up slightly and reached between us. Her hand found my partially slick rod and pumped it expertly a couple of times before she aimed the tip at her entrance. She lowered herself down and settled around my cock with a sigh. Once she had engulfed the length of me, my brain decided that my cock made the right decision. “Mr. Penis, I concur with your assessment of our current situation and I pledge my full support to your valiant cause. Ok, Mr. Body, it’s time to get involved!”

Since all of me was now on the same page, I finally snapped into action. I tightened my grip on her ass, my fingers sinking into the firm flesh and I held Lisa tightly to me. I started to kiss her back just as hard and hungrily as she was me. I wriggled my hips enough that she got the idea to uncross her legs from behind me and I fell back, drawing her down with me. I then lifted my ass up off the bed in order to lay on it properly. That had the side benefit of forcing the tip of my cock deep into her pussy and causing her to gasp.

When we got settled, Lisa pushed herself up onto her knees above me and leaned forward onto her hands. She started to rock back and forth, fucking herself on my cock. Her eyes closed and she started to moan and sigh as she increased her force and tempo. She looked down at me and opened her eyes. There was a glimmer in her eyes that I’d only rarely seen. I knew that this was going to be a wild ride. She arched her back, pushing her breasts out and into my face. Lisa bent her arms just enough that I could take them into my mouth and suck and lick on her nipples. When I clamped my teeth down on them, she gasped and increased her efforts. “Oh yesss,” she groaned. Lisa paused for a moment and grabbed my hands. Pulling them from where I was playing with her tits, she placed them on her butt. “I want you to play with my ass.” I squeezed my fingers into the flesh of her ass as she starts moving again. This only seemed to spur her on even more.

After a few moments of this, Lisa reached behind her and grabbed one of my hands. She brought it around to her mouth and started to suck on my index finger, getting wet and coated with her saliva. Pulling my finger from hr mouth, she smiled mischievously at me and placed my hand back on her ass and between her cheeks. “Do it. Please, do it now,” she whispered breathily.

I slid my slick finger down her ass until I could feel the pucker of her anus and circled my finger around it. She stopped pumping up and down on me and lay down on my chest. As I rimmed her star, I felt her tremble on top of me. I lifted my knees up which forced her legs further apart and pushed her up my body slightly, allowing me to reach her ass better. Lisa wanted even more so she reached back and spread her cheeks further apart. I began to press my finger into, felt it move past her ring with a slight bit of effort. Her breath pants out of her with little whimpers. “Are you ok?” I asked, concerned for her.

“Yesss,” she hissed out. “Oh God, yes! Your cock… in my pussy… feels… so… good… and your finger in my ass… is just incredible,” she managed to get out in between panting breaths. Lisa then began to gyrate her hips, bucking and rolling them. The action caused both my cock and my finger to shift around inside of her. That only got her more excited. “Please fuck me. Oh God, please. Fuck me. Fuck me.” Each repetition got more and more desperate than the last.

Using my free hand, I pushed up on her hip. She shifted her knees, lifting herself up off of me. I started to slowly thrust up into her. Each time I was rewarded with a small little whimper or gasp. I began to increase my pace which only caused Lisa to whine louder. “More, more…” she started to beg. I responded by slowly working my finger in and out of her ass. A tremble started deep within Lisa. Her head fell to my chest and she started to cry out in one long, continuous throaty moan.

Her orgasm hit her just as hard and unexpectedly as it did last night. Usually, Lisa gives very clear signs of an impending orgasm. A flush spreads across her upper chest. She’ll clench her jaw tightly, most of the time to the point where it’ll actually pop. But this one just came out of the blue. Her body shook and quivered as wave after wave of her release shattered through her. I could feel her pussy gripping at my pistoning cock, trying to milk my come out of me to go along with hers. Her ass clenched around my finger, too. The muscles of her sphincter pulsed around my finger as I continued to push it in and out of her ass. The second that the thought of replacing my finger with my cock entered my mind, I erupted inside of her. My grunting mingled with Lisa’s as we both rode out our climaxes.

After that night, we managed to work a bit of anal play into our lovemaking on a regular basis. The extra stimulation would heighten Lisa’s orgasms to new levels. Her favorite became me fucking her from behind while slipping my finger into her ass. She would become almost animalistic like this, grunting and driving herself back against me hard. She would just go absolutely wild.

One night after going down on her, Lisa pulled me up for a searing kiss. One of her favorite things after oral is for me to rub the head of my cock against her clit while we kiss. She always pulled her legs back and apart whenever I did this, spreading her pussy open. Sliding my cock against her like that coats the head of my shaft with her juices, getting the both of us ready for the penetration to come. This time, however, on one of my downstrokes, she pulled back on her legs a bit more than usual and the head of my cock brushed against her rosebud. Both of us froze and groaned at the same time. I think for the first time, both of us confronted the next step at the same moment. We were still frozen in place, each waiting for the other to approve or object first. Again, I was surprised as Lisa made the opening move. Biting her lower lip and still staring me in the eye, she rocked her hips back down, pushing her ass against my cock.

Since I had been working my thumb on her ass when I was eating her, she was still somewhat relaxed. The slick tip of my cock started to ease past her tight little ring. Slowly, gently, I kept pushing, even though my blood was boiling. I had to restrain myself from just ramming my cock all the way home in one hard thrust. Just as the last part of my head was about to slip into her, Lisa winced and cried out in pain, “Stop, stop! It hurts!” Apparently, there just wasn’t enough lubrication to prevent it from hurting.

I immediately stopped and withdrew what little of my cock managed to penetrate her. I lay next to her and held her apologizing the whole time. “I’m so sorry. I didn’t mean for it to hurt, baby. You don’t have to do this for me. I’m sorry. I don’t want to force this on you.”

“Don’t be sorry. I thought it would go in like your finger. Well, I knew it would be a bit more difficult, but I didn’t imagine that you would just feel so, so… big. Your cock felt so much bigger than it does in my pussy. It’s just not going to fit like that. Don’t take me wrong, I want to feel you in my ass as much as you do. The idea of it’s just so hot. But we’re going to need something to help before we can go any further.”

“So if I we had some kind of oil or lotion or something, we would be having anal sex right now?”

“Mmm-hmm,” Lisa almost purred.

I cupped her face with both hands and kissed her hard and fast. I reached into the nightstand on her side and handed her her favorite vibrator, a butterfly-shaped clit stimulator. “Don’t go anywhere! You stay right there and keep yourself busy. I’ll be right back…” I jump up and start throwing on whichever clothes came first to hand. That explains why I was in the drug store five minutes before it closed wearing flip-flop shoes, a pair of dress slacks and one of Lisa’s pink baby doll t-shirts with cute little kitten on the front and getting bizarre looks from the cashier as she rang up the bottle of “intimate moisturizer.” As I waited for the officer to finish writing out my ticket for speeding and running that red light, all I could thing about was getting back home to Lisa.

I started stripping down before the front door was closed. Clothes went flying everywhere in a flurry of tugging, pulling and unbuttoning. With bottle in hand, I finally managed to get back to the bedroom with only one barked shin and two stubbed toes. Lisa was still laying in bed, her legs through the straps holding the little vibe in place as it was still buzzing slowly on her clit. I could tell by the way she was laying there and just kind of blissfully rubbing her hands over her body that I had just missed an orgasm. “Mmm, just in time. If you were gone any longer, I would’ve had to finish myself off for the night.”

“Well, I’m here now. So tell me, how do you want to do this?”

“Mmm, how about like this?” Lisa rolls over and pushes herself up onto her knees with her arms crossed under her head, lifting her ass up into the air and giving it a little wiggle. My already hard cock jumps at the lovely sight. “I see you approve,” she cooed at me.

“Yes. Yes I do.”

I clambered up onto the bed behind her. My hands went to her ass, stroking over her cheeks and along her legs and up her back. I leaned over and placed kisses everywhere I could. “Are you ready, my love?” I ask. Another little wiggle of her ass gave me my answer. I grabbed the bottle and squirted a little of it onto my fingertips. I touched my fingers lightly against her rosebud. “Ohh, it’s cold,” Lisa gasped, but she didn’t pull away. I slowly started to massage and spread the slippery stuff over her backdoor. Her sphincter was still relaxed from our earlier attempts and her orgasms while I was gone. With very little effort, my finger started to slide into her ass. Lisa gasped at first and I both felt and saw the shiver run through her body.

Soon, I was fucking my finger in and out of her ass. “More. I want more…” she sighed after a few moments. I withdrew my finger and added more of the lubricant to my fingers. With an additional little drizzle on her ass, I started to push two fingers into her. Another moan escaped from Lisa as I started to pump them in and out. “Oh God, I need your cock in my pussy. Now!”

I moved behind Lisa and aimed my rigid dick at her cunt and slid home. Both of us groaned as I filled her incredibly wet pussy. I could feel the buzzing of her toy through her body and all the way up my spine. Lisa pressed her hips back against me and arched her back even further. “Yessss. Just stay right there and move your fingers,” she whispered. I complied, giving her what she asked for. With my free hand on her hip pulling her back against me, I pressed my shaft as deep into her pussy as I can and started slowly fucking my fingers in and out of her ass. Lisa began to tremble beneath me and let out a low, continuous moan. I paused every now and then to add more of the lube, all the while using my fingers to open her up even more.

“Oh God, I think I’m ready,” she finally gasped.

“Are you sure?” All I get in response is a weak nod, a breathy “Uh-huh,” and a grind of her hips against mine.

My heart started banging away like a triphammer as I pulled my cock out of her dripping cunt and my fingers out of her ass. I grabbed the bottle one last time to squirt more of the gel into my hand and started to coat my dick. I placed my head against her star on more time and gently pushed. Both of gasped as I easily slid into her. I had to pause to catch my breath once my head slid past her ring; I was panting so hard and fast that I was starting to get lightheaded.

There was a constant litany of “…ohgodohgodohgod…” from Lisa until my hips pressed against her cheeks. At that point, she began to tremble again. A hand came back and grabbed my hip, holding me in place. “Don’t move. Oh please don’t move yet. Just stay right there…”

Not a problem. I knew that if I started moving, I was going to cum right then and there. The feeling of her ass around my cock was just unreal. Her heat was like nothing I had ever felt before and the way her body clamped down on my cock was intense. If staying still for a second or two was going to make this last that much longer, I was all for it. No way did I want this to be a “one stroke joke” situation.

Lisa pushed herself up onto her hands and looked back over her shoulder at me. “Now. Please. Give it to me. Please…”

With my hands gripping her waist, I started to ease out of her ass. The way her body clutched at me was almost like, now that it let me in, it doesn’t want to let me go. It was the tightest, most incredible thing ever. It was nothing like I had imagined it to be. It was way more, just, everything. I got lost in the sensations almost immediately as they overpowered my brain. Only two things kept me somewhat anchored. Trying not to lose control and cum too soon, and trying not to lose control and end up hurting Lisa and never getting the chance to do this with her ever again. I was concentrating so hard on me that I didn’t notice that she had been pushing back, meeting me stroke for stroke for a few minutes now. My awareness expanded long enough for me to recognize the look of sheer lust and desire in Lisa’s eyes. That look and her thrusting back at me were her ways of asking for more since she couldn’t get enough of a breath to do it verbally.

With clenched teeth, I began to increase the tempo. Lisa’s eyes closed and she smiled before letting her head hang down as she, too, got overtaken by the feelings. I gripped the leg straps that were holding her little butterfly vibrator against her clit and used them for even more leverage, trying to push as much of my cock into her ass as possible. I could still feel it buzzing away every time I drove into her as my balls would press against her just dripping pussy. Soon, I was pumping in and out of Lisa’s ass like I would her cunt. I was pulling her back by her hips, thrusting into her hard. Both of us were grunting and sweating from the effort.

The telltale signals of my impending orgasm began to let themselves be known. I could feel the tension and pressure building at the base of my cock. My balls were starting to tighten up and draw close to my body. Each time I thrust into Lisa became shorter and sharper until I finally came.

My cock literally exploded inside her. It was the hardest, most intense orgasm I had ever had. I fell forward and had to hold myself up with one hand on her hip and the other on the bed to keep from collapsing on top of her. My dick was pulsing and throbbing over and over in her ass. It felt like my whole body was pouring out of me through my dick and into her ass.

The force of my release must have set off Lisa as well. While she had been trembling and quivering the whole time, something inside her seemed to come loose. She grunted and cried out loud and her whole body began to shake. I could feel her ass start to spasm and clench down around my cock. Her body was clamping down so hard I thought that she would squeeze it off at the root.

Our bodies both gave out from the sheer intensity of the whole experience. I withdrew from her and both of us collapsed to the bed in a tangle of limbs. We were so exhausted we didn’t even cover up before we fell asleep. I woke up the next morning to find her up before me again. “Can we talk about last night?” she asks me, this time with a big smile and mischievous glint in her eye.

“Oh really?”


“What about?”

“How about ‘When’s the next time we’re going to do that again?’ for starters?”

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