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Anal Rendezvous

Category: Anal Sex
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I was awakened that crisp autumn day in a most delightful way. A warm, wet tongue was washing my cock as a finger circled my asshole. Without opening my eyes, I went with the terrific feeling that spread through my body from my crotch. The cabin was toasty with my setting the thermostat to 75 when I arrived a couple of hours earlier that Friday afternoon. I spread my legs slightly to allow better access to my asshole and balls as the mouth began swallowing me to the base of my dick.

My hips moved rhythmically with the oral ministrations. I was really getting into it when I was stopped cold by something falling on my face. Fearing a spider had dropped from the open beams onto my cheek, I opened my eyes for the first time since the wonderful blowjob began to find myself staring into a wide open, very wet, clean-shaven pussy poised with a delicious looking brown eye even with my own eyes that didn’t belong to the mouth on my prick. Before I could say a word the pussy descended to my mouth and my nose jammed into the little wrinkled hole. I did the only thing I could do; I ate a very ready snatch. The pussy fucked my face at a feverish pace as my sack began to tighten in anticipation of shooting my wad. I would have uttered a warning that I was about to cum but found it impossible with the pussy jammed down on my face so I just let it go. The mouth moving up and down my cock stopped halfway and began to swallow. What a fantastic feeling. The pussy on my face was also about to cum. Reaching up, I shifted her forward and gave the earthy smelling asshole that had been pressed against my nose a rim job. She flooded my chin and neck with juices when I stuck my tongue up her ass.

As the leg swung over my head, I wasn’t surprised to see M still rubbing and licking my softening cock. I had expected her to show up at my cabin this afternoon. We had worked together for six months now and the sexual teasing and innuendoes had driven her to this place to see if I was serious with my unrelenting flirting. I was surprised to see J, another coworker that would occasionally listen to the constant sexual banter between M and myself. All week long I had been telling M I would be at the cabin this weekend by myself. I told her several times, in rather graphic detail, what she would be missing. This wasn’t the first time I had done this. In the past I had even gone so far as to give M a map with directions to my cabin at Big Bear Lake.

“I figured the only way I’d ever find out if you’re full of shit was to come up here. You better be worth the drive and the cost of a weekend babysitter,” M said giving my cock a tug.

M and I are about the same age, mid-thirties, and I describe her as Reubenesque. She’s probably fifteen or twenty pounds over what today would be considered her ideal weight. She has a beautiful face, blue eyes, and as I discovered as she spread her legs exposing her bare pussy, real blonde hair. Her fine, blonde pussy hair did nothing to hide a rather large set of engorged lips with her clitoris peeking out at the top. M divorced a year ago from a Harley freak after twelve years. She said the only way he would take any interest in her was if she chromed her tits.

J was leaning against the padded headboard still trying to catch her breath. She can only be described as statuesque. In her early thirties, she is 5’10” with a great set of legs and ass along with 36C tits. Also divorced, she is one of the quietest and most polite women I have ever met. I’m more than a little amazed to see her sitting naked with her legs splayed on my king-size.

“Thank you,” she said scooting up against the headboard and closing her legs. “Nobody has ever done that before.”

“That’s really the first time you’ve had your pussy eaten,” I asked incredulously.

“No, not that. You know, that other thing you did,” she replied turning crimson.

“And what might that be?” I knew she meant the tongue to her asshole but I was enjoying the moment too much to let her off the hook.

“Y-y-you know,” she stammered. “When you used your tongue on me down there. That’s the first time and I’ve never climaxed that hard before in my life.”

“My pleasure,” I smirked. “I’ll be glad to stick my tongue up your ass again but I don’t put my tongue anyplace that my cock doesn’t go. You might want to think about that.”

My dick was getting hard again just thinking about my favorite sexual activity. Nothing feels better than sliding into a tight, greased asshole and fucking J’s obviously virgin butt was making my hard-on dance. The sight of M slipping two fingers into her pussy sure wasn’t doing anything to make my dick go soft either. Finger-fucking herself, she slid the two glistening digits out and slowly over her now swollen clit. Her aroused love-button had to be nearly half an inch long. I had never seen a clit that big and felt an overwhelming urge to lick and suck it.

As if reading my mind, M said, “I want the same thing J got and you better tongue fuck my ass.”

She didn’t have to ask me twice. I love the taste of pussy. Bringing my face to that sweet hole, I deeply smelled her sex, it was heavenly. Lowering my mouth, I caught her engorged clit between my lips and gave it a light tongue lashing, very fast and very softly. Her juices began to flow immediately; my chin was already soaked. I tried stroking her clit harder with the flat of my tongue but the contact was too intense for her and she pulled her pussy away from me. After a little experimentation I found she loved it when I circled her clit with my tongue while driving two of my fingers into her sopping pussy. After several minutes of this she was approaching orgasm. I suddenly withdrew my fingers and jammed my stiff tongue into her ass. I found out she was a squirter when pussy juice hit my forehead as she came. Her asshole slammed shut around my tongue and I had to leave it inside her butt until she relaxed a little. I moved right back up to her clit that was now trying to hide once again in the upper folds of her meaty cunt. Sucking it into my mouth, I grazed it lightly with my teeth. M tried to pull back again but this time I wouldn’t let her. I kept sucking and chewing her clit feeling it grow in my mouth. Her hips began to jerk spasmodically under my face. Her thighs clamped down on the side of my head but I could still hear her orgasmic scream when I pushed my index finger completely up her ass. She filled my palm with cum.

Her legs trembled uncontrollably as I lifted my soaked face. J was still leaning against the headboard but now her legs were spread wide and she was fingering herself and very close to another climax. I moved her hand out of the way replacing it with my tongue once again. My jaw was getting sore so I went right after it. Straight into her pussy, up her slit stopping to probe her pisser, and then direct contact with her clitoris. I did this a couple of dozen times with her moaning louder with each successive pass. I then went lower and included her anus. After a six or seven of these long licks she was cumming.

I left them on the bed for a hot shower to loosen the stiff muscles I now had in my neck and jaw. I did nearly all the construction on my little cabin and it has some rather unique features including the bathroom. It is mostly taken up by the shower. Enclosed on three sides by tiled walls, the fourth side is open to the bed area, which is open to the rest of the cabin. Six showerheads spray water from three different directions at two levels. A couple of minutes after stepping into the water set as hot as I could stand it, M and J joined me.

Two women soaping my body at the same time was a new and sensational experience, particularly when M stroked my lathered prick and J slid her soapy hand up and down my ass crack all the way to my balls. They traded places to rinse me off. J did the front first with the hand-held shower paying special attention to my cock and balls. Finished, she passed the shower to M and knelt taking my half-hard penis into her mouth. It didn’t stay semi-stiff for long as she swirled her tongue around the crown stopping occasionally to stick the tip into my piss hole as I had done to her. I felt M spreading my cheeks and groaned when the hot water hit my asshole. Now two hands were spreading my butt and I nearly came when M’s tongue invaded my hole.

They must have planned this because no sooner did M begin probing with the tip of her tongue J began fucking my dick with her mouth. I’ve had rim jobs before but never with a blowjob at the same time. When M started fucking my ass putting her tongue as far up my rectum as it would reach, I knew it wouldn’t take much longer before I shot my wad. I did everything possible to stretch out the incredible feeling but I couldn’t hold back when M slid her finger up to my prostate and massaged it. J swallowed repeatedly with my cock at the back of her throat not to choke on my massive load. This caused her to literally milk my dick and I had to lean against the wall to keep from falling.

After dressing, I asked the ladies if they would like to go into the village for dinner. I explained I had planned on grilled steaks tonight but had only brought enough for two. Turns out J is a vegetarian so I fired up the BBQ and fixed her a nice salad. My first real conversation with J was during our meal. She had been married for five years to a prude. Sex for him was strictly missionary position and only for purposes of pro-creation. She wasn’t a virgin when she married but had little experience. She confessed that after listening to M and I tease each other she would masturbate fantasizing about all the things we said we would do to each other. This is what brought her up to the cabin after asking M’s permission.

With the dishes in the washer, I asked if they would like to go to Big Bear Lake Village for a drink and some music. M responded by grabbing my crotch and saying with a leer, “I have other plans. I want to see if this works as well as your tongue.” I’ve always believed in giving a lady what she wants and unbuttoned my jeans so M could slide her hand down my pants before pulling her close and kissing her. Our tongues played first inside her mouth and then mine as she stroked me to hardness.

Breaking away from our lingual duel, M pulled my sweatshirt over my head. Trailing kisses and bites down my chest, she stopped at first one nipple and then the other to suck them into her mouth to tease with her tongue. Licking my navel, she tugged my jeans and jockeys down to my ankles. My cock sprang up tapping her under the jaw. On her knees, M’s hands glided back and forth on my shaft with a feather-like touch. Continuing to stroke me, she moved one hand to cradle my balls in her palm and began to gently roll them. M licked the pre-cum from my tip before I pulled her up and began walking her backwards to the bed while tongue kissing her once again. I had completely forgotten about the pants and shorts wadded at my ankles and nearly fell but M held me up. Have you ever been in an intense situation only to have something happen so ridiculous that you can’t help but break up? M found it hilarious as I tried to pull my legs from my pants and even funnier when I had to sit on the floor to finally take them off.

Taking me by the hands, she helped me to my feet and led me to the bed. I started stripping her taking my time to stop and fondle her hardening nipples through the flannel shirt she wore bra-less. Impatient, she pushed my hands away and was quickly naked. Whatever my plans for this session, M had her own. Pushing me down onto the bed she took a 69 position. We took it slow and easy wanting this to be just a preliminary. It wasn’t long until M turned around and lined up my dick with the opening of her vagina. She eased down taking me slowly but without stopping until she had it all. Moving back up my shaft at the same pace, she held just the head inside and changing the angle slightly, slowly slid back down. She did this repeatedly. Up and down tantalizingly slow with a little shift every time at the top. M kept this up until I felt her own little hard-on touch mine. With her big clit in contact with my slick shaft, it wasn’t long before she picked up the pace. Slamming down and hesitating to grind our pubes together, it didn’t take long for M to orgasm. My balls were soaked with her cum as I slid my hand between our union and lightly stroked her clit; she came again immediately.

Stopping to catch her breath, M stayed astride me impaled but without moving. She turned so her ample ass was now facing me without her drenched pussy leaving my still rock hard prick. I now had an excellent view of her dripping snatch moving up and down me. Her little, pink asshole opened and closed as she rode me. Wetting my finger with the combination of our juices that dribbled from her, I waited until her chute opened and slid my finger in. M moaned pushing her ass against my hand. Satisfied she wasn’t experiencing any trouble; I withdrew my finger and slid two in without difficulty.

Figuring M was no anal virgin, I removed my fingers and was about to go for three when she took my cock from her pussy and placed the head against her butthole. It was quite a sight to watch the head of my dick stretch her sphincter as she lowered herself. She took the head very slowly until I felt her muscle ring snap around my shaft capturing the mushroom end. M surprised me by dropping to take my cock up her ass all at once. My drenched balls were halfway into her cunt as she began wiggling her butt. I’m not sure what was making me hotter; the feel of her tight asshole fucking me or watching my dick moving in and out of that hot hole. With her legs trembling from the strain, M leaned back shortening the strokes. This position also gave me the opportunity to fondle her once again exposed clit. M climbed toward another climax and I wasn’t far behind her. The spasmodic ripples of her shitter canal as she was gripped by her most intense culmination yet sent me over the top. Even after cumming twice already today, I shot load after load into that wonderful fuck hole. M milked me with her asshole until my cock softened and slipped from her.

With my help, M rolled off me to lie on her stomach. With her legs spread, I sat and watched my spunk seep out as her pink rosebud continued to open and close from her anal climax. My attention was drawn by the sound of another orgasm a few feet away. J was just going over the top as she sat in my easy chair. Naked from the waist down with her feet on the cushion and her legs spread at what seemed an impossible angle, she sawed three fingers in and out of her wet hole. Juice ran from her down to her brown asshole and between the moans I could hear the sucking sound produced when she pulled her fingers out. J quivered all over as she reached her zenith and screamed as she removed her fingers from that clean-shaven cunt to push her middle finger up her butt. Riding the miniature organ, she stroked her clit with her other hand and came again.

J had left the cabin as M and I made it to the bed earlier. I had not heard her return but the fact she had and I failed to notice didn’t surprise me. Taking a small vibrator from my nightstand drawer, I approached J still in the chair with her legs splayed. Her eyes were closed and had no idea I was there. Kneeling before her now exposed Y, I turned the vibe to a medium setting and placed the tip to her winking brown eye. Startled, J jumped back into the chair closing her legs. Smiling, she slid back down to the edge of the cushion to allow me maximum access to her holes. Lightly flicking her clit with my tongue, I circled her anus with the vibe stopping occasionally to moisten it with pussy juice. As her hips slowly began to bounce on the seat I fucked the slippery vibe into her butthole a little at a time. Slowly I fed more into her stretched hole until she had all five inches. J went nuts when I twisted the control to high and rocked the toy from side to side. Trying to lift her clit away from the contact I held her in place by sucking her entire pussy into my mouth. The vibe was held in place by my chin and I could feel the movement throughout my mouth. With my tongue now an appendage to the vibrator I placed the tip at the base of J’s button. She came instantly and I sucked and swallowed her musky cumjuice. Allowing J to scoot back into the chair, the vibe shot out of her ass hitting me in the chest coming to rest on my flaccid cock.

Turning a deeper shade of red than her present cum thrush, J jumped from the chair and nearly ran to the bathroom. Picking up the vibe I saw several small shit streaks contrasting with the white plastic. I grinned at the thought of having just fucked the shit out of her. There was no way my dick was coming back for another round this night but I knew I was going to slip it into her virgin hole the next day.

When I heard the toilet flush I joined J in the bathroom for another shower. We sensuously washed each other but that was as far as it went. They couldn’t have gotten my dick up with a crane at this point. With just robes on, J went to M intending to wake her but I held up my hand to stop her. She was sleeping in the position I had left her and my cum was still oozing from her obviously well fucked rectum. Her pussy was now covered in the jism and a puddle had formed where it was still dripping to the sheet from her second set of lips. I knew M had to get up so we could change the sheets but seeing her like that was an extreme memory I wanted to savor. If J hadn’t been there I would have captured the moment on video. I finally motioned J to go ahead and as M stumbled into the bathroom we put on fresh linens. I banked the fire and we fell asleep that night with M on my right and J on the left. I woke a couple of times to feel naked pussy, ass and tits all around me. I could get used to this.

The ladies woke the following morning to a cup of coffee waiting for them on each nightstand and the smell of bacon and eggs cooking. They finished their morning duties by the time I put breakfast on the plates. They ate like it had been a week since their last meal and I ended up cooking another half pound of bacon and four more eggs.

“Nothing like clean mountain air to stimulate the appetite,” M said.

“More like good mountain fuckin if you ask me” I countered.

She threw a wadded up napkin at me. “What’s on the agenda today?” J asked. “Other than the apparent,” she added.

“I thought we might go on a hike and catch a few trout for dinner tonight. They’re usually biting down at the lake this time of year and it only takes 45 minutes or so to hike down there,” I said.

I could see M wasn’t going for this idea right away. “Are you out of your fucking mind?” “First, I don’t fish. Never have and don’t want to. Second, my ass is still a little sore from that meat of yours. You two go ahead if you want but I’m staying here.”

J objected to M staying alone when this was supposed to be her weekend but M said, “Don’t worry about it. I can use the time to recuperate and if I didn’t want you here, believe me, you wouldn’t be here.”

J and I grabbed the tackle and left for the lake with M lying on the sofa reading my copy of the latest King book. I set a slow pace afraid J wouldn’t be able to keep up in the thin mountain air but this proved unnecessary. The woman was in great physical shape explaining she power walked five miles nearly every day. We stopped at a bait shop near the lake so J could get a one-day fishing license. Within a couple of hours we had both caught several fish over the limit releasing all but six. The walk back took longer with us halting occasionally for a bit of kissing, petting and teasing.

Entering the cabin by the backdoor, J and I stopped dead in our tracks by the unmistakable sound of a couple involved in some very hot sex. Tiptoeing out of the kitchen, I was greeted by the sight of M sliding a huge vibrator in and out of her vagina while watching one of my porn DVDs. J and I watched silently as M brought herself closer and closer to the top. Motioning J back into the kitchen I held my finger to my lips and started taking her clothes off. J got into it right away by returning the favor. Both quickly nude, we entered the living room and stealthily approached M. Almost to her, M scared the hell out of us with a shriek as she went over the edge. J yelped in surprise and M knew we were there. Without missing a stroke she continued fucking herself. The vibrator she used was at least a foot long and five inches around. There was no way she could keep it from rubbing against her big, protruding clitoris. Calling me over with a wag from her finger, M took my hand and placed it on the vibe. My dick was rock hard as I began fucking her fast and deep with the plastic. J didn’t waste time moving in front of me to begin licking my hard-on. It wasn’t long before M was cumming again and her juices were squirting. She had been considerate enough to place a doubled towel under her ass to catch her cum. I was appreciative that I would only have to clean the chair J had been in last night and not the couch. I’m not sure how many times M got off but I can tell you that she has an amazing capacity to cum.

She finally pushed my hand away and the huge vibrator made a popping sound as it left her hole. With the big tool gone, I could see she had also inserted a slim, wireless plug into her asshole. This she left in place as her pussy creamed and creamed. Figuring M was done for a while, I pushed J off my dick and helped stand. I could tell by the wet spot on the wooden floor where her pussy had been that she was ready.

Directing her to the bed, I bent her over with her palms flat on the mattress and slid my cockhead the length of her slit coming to rest at her anus. J spread her feet opening her slit and I repeated the rubbing several times just so she would get used to my dick being at her shitter. Squatting slightly, I entered her pussy in one smooth thrust. Now I don’t consider myself large in the cock department, I’m about eight inches with average girth, but my dick couldn’t have filled her up more. If this wasn’t the hottest, tightest pussy I had ever been in I sure couldn’t recall any better. Her ex-husband must have been a pencil-dick if he wasn’t fucking this every chance he got.

Only the thought of getting into her smaller hole kept me from fucking her like this until we both got off. I don’t think she had ever tried this position because she had a small one after only a few strokes. Thinking this was as good a time as any, I withdrew and placed J on the bed with her back to me. Lifting her leg a little, my dick found her vagina. I spoon fucked her for a while and used my fingers to spread some of her juices to her backdoor. Pulling out, she pressed her ass against me looking for what I had just removed. I moved my cock that wonderful inch and gently pressed against her anal ring. I doubt I had half an inch in when she gasped, “Stop, it hurts. Take it out! Take it out!”

Damn, to be so close. Reaching around to rub her clit, I backed off. Whispering in her ear I said, “I can make this the best you’ve ever had if you’ll trust me and do what I say.”

Rolling over, she looked at me with damp eyes softly saying, “You promise it won’t hurt because I thought that was going to tear me apart?”

“That was my fault. I should have spent more time getting you ready. That won’t happen again and I promise it won’t hurt if you help out.”

J said nothing for several seconds before nodding her head and asking, “What do I need to do?”

Taking a feather pillow, I folded it over and said, “Lift your hips.”

Doing as I asked, I slid the pillow under J’s butt bringing the hole I so badly desired off the bed. From the nightstand drawer I brought out a small, liquid filled bottle that looked like a little throw away douche and a seven inch black vibrator. Positioning myself to eat J’s pussy, I inserted the douche tip into her asshole and gave a little squeeze. Pulling the bottle away, some of the clear liquid followed and I scooped it up with my finger putting it back. The room began filling with the essence of strawberry.

“What is that stuff? It’s making me feel tingly down there.”

With my finger softly rubbing her butthole, I dipped my head to lick her before answering, “It’s my own special formula but you’d probably freak if I told what’s in it.”

“Only if it’s like some weird shit made from ground up monkey balls or something like that. It’s not, is it?”

“Nothing like that. It’s actually synthetic motor oil made in Japan that’s a 100% vegetable derivative. It’s much safer than a petroleum product and really reduces friction. The strawberry you smell is just a little added extract. That’s what’s causing the tingly feeling. You still okay with this?”

“I guess. I’m not sure I like Pennzoil up my ass though.”

I ended the conversation by putting my mouth to other uses. Once her hips began rocking, I slipped a finger in her ass feeling no resistance. I immediately withdrew and made it two fingers. J’s only reaction was to moan as I finger fucked her anus. I kept this up until she came once more. I let her catch a little breather but left my fingers where they were. I tongue fucked her pussy and slipped out of her ass. Squirting my magic lube into my palm, I rubbed it all over the vibe. J stopped moving and clenched her butthole tight when the cold plastic touched her.

“I don’t think I can take that. It’s too big.”

“You said you’d trust me and help. If you just relax you’ll find out how good this can be.”

I watched the wrinkles disappear from her brown eye as she relaxed the muscle. Again my face dipped to her waiting pussy. It took a while for her to respond with the tip of the vibe at her asshole. I concentrated on bringing her to climax lapping at her swollen clit and probing her piss hole with the tip of my tongue. My lingual endeavor was paying off when I felt the vibe slip a couple of inches into rectum. I held it in place and twisted the end to a gentle vibrating setting. I let J take in more at her own pace. I turned it up to medium when half was in. Her anal ring was now stretched as far as the tapered vibe was going to open her up. I worked solely on her clitoris now alternating between my teeth and tongue. With a loud grunt she was cumming and her shit hole sucked the rest of the vibrator in. Pulling my face away, I pushed her legs back until her knees rested on her tits. Only an inch of the seven-inch vibe was visible. I languidly fucked her leaving only the tip in before pushing back in to the speed control. Her pussy opened with insertion and closed during withdrawal.

I knew she could take me now with little problem. I’m only slightly larger than the vibrator now buried in her ass. I took J’s hand and placed it at the end of the vibe to hold it in place. Positioning myself over her upturned pussy, I eased my cock in. She came as I bottomed.

“Oh my God,” she cried out. “I’m so full. Fuck me, fuck me, fuck me.”

I couldn’t stay there long. Her vagina was that much tighter with her ass filled and the vibrations were about to drain me. Reaching under, I pulled the vibe from her and quickly withdrew my cock from her pussy to replace it. I took my time getting the head in and J lay very still. I knew I was dilating her a bit more and didn’t want to hurt her again. She relaxed a bit and I slipped right in. I waited as her canal enveloped me. Feeling pressure from head to base, I began fucking at a leisurely pace. It was as good as I knew it would be. J was matching my rhythm. I was close, very close. Wanting J to cum the same time I did, I rubbed my thumb over her clitoris. My tempo picked up with both my cock and thumb and J stayed right with me. It was a near perfect union. I felt as if J and I were becoming one and I have never experienced anything like this before. The pleasure is so intense it is almost painful. I hold back, hold back, hold back, J is cumming now and her canal clenches me. I can let it go now but her anal ring is so tight around me I cannot cum. Her orgasm is incredibly intense but thankfully short. Her muscle is relaxing its hold and cum pours from me in one long, continuous blast. I know she can feel it splashing against her cavity and she cums once more halting my release. Loosening much faster this time my seminal fluid now shoots in jets like normal. With the last, long spasm I feel myself slipping away. I awaken to J shaking me, asking me if I’m okay. My cock is still in her ass but shriveling fast. I believe the French call it “Little Death” and it’s another new experience. My prick came out with a sucking sound and that beautiful asshole was the last thing I saw before falling into a natural sleep.

A steady rain was falling when I woke later that afternoon. The place was quiet except for the usual noises of the cabin. I called out to M and J but received no response. I found a note on the kitchen table:

Had a GREAT time but I’m fucked out.

See you Monday, M

It had probably been the best weekend of my life but I wanted to see if J could make me feel like that again. I shrugged it off figuring it was a one-time thing. The second note was on the mantle:

I had to leave with M. We left at 1:00, I’ll be back by 5:00. I’m fixing dinner tonight so prepare for a trout vegetarian feast, and you know what else, J

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