Gary Takes Her Ass

“You sure this won't hurt?" Jenny asked again.

"Absolutely. All you have to do is push back, like you are trying to go, and relax. Things will be just fine. I slide in a little, let you have time to get used to it, and take it easy. You'll love it." At least he hoped he wouldn't hurt her. He had used enough K-Y. If she were too tense, it would hurt. If she relaxed and wanted to enjoy this, it wouldn't.

"God I hope so. I've heard about this enough."

"Girlfriends huh?" Gary said as he moved closer and smeared the lubricant all over his hard and ready cock.

"Yea. A few said there was no way that they would ever let a guy up there, and there were a few who said it was really kinky and they loved it - now and then when they were feeling really nasty or wanted to give their husband or whatever a real treat. Some even claimed they got off doing it."

"And you were just dying to find out who's telling the truth?" he moved closer.

"Well, sorta," she said, waiting for him to either enter her ass and thrill or her, or for the pain. She wasn't sure what to expect. She had her virgin ass up in the air, waiting. Her chest was on the bed. "Mostly I just hope I like it. I hope I can cum. It sounds so nasty." Thank God, this guy wasn't hung like a horse.

Gary had only met her a couple of hours ago in the motel bar. They were driving in opposite directions and were just here for the night. He had seen her at a table off to the side, almost in a corner and had asked to join her. At first, she was hesitant, but had quickly changed her mind. There had been the usual chitchat, what's your name, where are you going, and so on. Somehow, spouses and sex had come up, and right now, he didn't remember how, but it had eventually gotten around to not only sex, but also anal sex. He loved it, she had never done it, and her husband wanted nothing to do with it. She had professed a real desire to try it. Sometime later, he had asked her to his room, and somewhat to his surprise, she had accepted.

They had started with the usual preliminaries. Being a typical woman, as she got undressed, wished her body looked a lot better, her boobs were a little bigger, and she weighed a little less. And, she hoped he wasn't huge.

Gary, being a typical man, was happy to have a woman willing to get into bed with him, and as she undressed, was even happier with her body; one he thought was just about perfect! And, of course, wished he was in a little better shape and was hung a little better.

"I hope you like it too." He was right behind her now, and placed the tip of his hard slick cock firmly against her crinkled little anus. Slowly he increased the pressure on it, watched the swollen head flatten a little against her resisting anus, and then watched the lust-swollen cock head slip - almost surge - inside her as that puckered little entrance to heaven relaxed. He just put the head in, just penetrating her tight little sphincter, and stopped. She was tight and it felt so damn good! "There," he said, "I'll hold it right here till you get used to it." He felt her sphincter give his cock-head a good firm squeeze. If he hadn't been pushing slightly, she probably would have forced it out. He needed the rest too or he was going to blow his load way too early. Anal sex with a complete stranger, who really wanted it in her ass, was just way too hot. This was the stuff of dreams!

As the cock tip had touched her, she started pushing back, just like he had told her. She was surprised to feel him slip in there so easily, and it didn't hurt - well, not much anyway. It was a little different, and she was glad he had stopped, or it might have hurt. She felt really stretched back there. Jenny lifted a hand between her legs and felt her pussy. This had her dripping wet! Oh, she had been wet and ready for him when they had a short session of missionary sex, but now she was really turned on as he penetrated her virgin ass. A finger started to slowly massage her hard clit. So far, this was great. That initial little pain had quickly subsided. Now, it felt good having Gary's cock in her ass. Now she wanted more of it. She felt relaxed, it wasn't hurting, and she was ready for some more of him. She wanted to feel him - his hard cock - sliding in and out of her ass. She wanted to be fucked in the ass!

After letting her have a few seconds to get used to something in her backside, Gary began to push again, and slid most of his cock slowly into Jenny's tight little ass. It seemed like she had relaxed now and things would be just fine. He took it easy on her as he started to slowly move his hard cock in and out of her tight little butt. He slowly withdrew until just the swollen head was inside her. Then, he pushed it all the way back into her. He could feel the soft velvety tip just touching the end of her rectum. He just loved the sight of his cock moving in and out of her ass. And, that smooth feeling of being inside her ass, yea, there was nothing quite like it. This was really "doing the nasty!"

Jenny was surprised at how good this felt - and how wicked and nasty it was too! She started to moan a little as Gary started going faster. Her finger started going a little faster over her clit. She wasn't going to last long like this! She wondered if she could time it so that when he started filling her ass with his hot sperm she could cum too. It sure felt like she was going to cum, and it wouldn't take much to send her over the edge. She had already cum once tonight, and she was ready for another good one.

Gary had turned out to be a good lover. The first, he paid a lot of attention to her boobs, sucking on one long nipple and pinching and twisting the other nipple just exactly as she liked it. He had complimented her body and seemed enraptured with her boobs. He made her feel like her boobs were the greatest ones he had ever seen. It was like he had been her lover for years. Then he had gone down on her, leaving her boobs and kissing his way down her flat tummy to her well-trimmed little bush. She didn't have to ask him to, and didn't have to blow him first - which was just as well, as she really didn't care much for blowjobs.

Some friends of hers had claimed that they liked blowjobs and that cum tasted okay; she thought the stuff was awful. She didn't mind sucking on her lover a little. The precum was okay, and even a little sweet. It was the actual cum that about gagged her. Usually she blew the guy until he got close and then finished him off with her hand, holding the cock tightly as her lover started to cum, making the sperm squirt high into the air. A few had wanted to cum on her face, but she wasn't crazy about that either.

Gary really knew how to please her. He had gotten her close to cumming, and then teased her several times, almost letting her cum, but stopping short of letting her finish. Instead, he had turned his attention to the rest of her sex, letting her aching clit calm down. He sucked and teased her inner lips, licked her where she peed, and pushed his long tongue into her sopping wet sex opening. Finally, a finger slowly and carefully pulled back the hood of her clit, leaving the swollen wet little pink protuberance fully exposed. His talented tongue had then carefully caressed it, sending her over the edge. She first moaned, then screamed, and then soaked his face for him as a reward for his efforts. After that, she had eagerly spread her sexy legs for him, letting him fully enter her. She was so wet and ready that he had slid slowly all the way into her on that first long delicious thrust. There was always something about the feeling of a nice hard cock sliding into her the first time, that feeling of really being filled. They had happily screwed away for a time before he had suggested that she turn over. She knew what was coming next.

"On all fours, or flat on my tummy?" she had asked. While she was new to this, she had seen enough porn movies to know that it was done both ways, and sometimes even missionary.

"Let's start out on all fours," he had told her.

Now he was fully inside her ass, having his way with her, and she loved every minute of it. Slowly she had let her knees slip out behind her until her tummy was down on the bed. She just kept her bottom thrust up in the air, pushing back against him, making it easier for him to penetrate her tight little ass. Her finger was on her clit, going faster all the time, adding to the thrill that his hard cock was giving her bottom. Jenny slid a finger into herself and found there was really very little separating her pussy from her rectum. She felt his hard cock moving in and out of her ass. She wondered what it would be like to have two men at the same time, one in each place going at it - two men having their way with her. Just about then, she heard him groan.

"Oh.... Jenny," he groaned, "I'm gonna cum in your ass! I can't hold off any longer!"

She felt her own orgasm start to wash over her just as she felt the first throb of his cock in her ass. He had stopped trusting for just a second, perhaps in a vain effort to hold off a little longer, as that first spurt of hot pearly-white sperm shot up from his balls and erupted deep in her waiting ass.

Gary resumed thrusting, more like pounding away at her ass, as squirt after squirt of his thick hot cum sprayed out of his cock and landed deep in Jenny's tight climaxing little ass. He hadn't had a cum this good in a long time. Yea, there was just something special about anal sex - being in a woman's ass. He heard her moans turn to more of a shriek as she began to cum.

Finally, he had collapsed on top of her just as her orgasm was subsiding. Neither spoke for several minutes. They just lay there, his cock still deep in her bottom, in that forbidden tight little place, as they caught their breath.

"Was it as good as you thought it would be?" he finally asked, still nearly breathless, as he withdrew from her and rolled over next to her.

"Yea, maybe better. I had a great cum. I wanna do this again."

Sarah's First Time

I had been married for around ten years when my then wife, Sarah, got a job as a police officer. She'd started out as school teacher after graduating from university, but couldn't land a permanent job and decided to have a go at something a little different.

It was a little difficult adjusting to her new life style as Sarah had to work shifts, including night shifts, and as a consequence we had less quality time to spend together.

Fortunately this did not have a detrimental effect on our physical relationship and we had just begun to introduce toys in to our love-making which helped prolong our sessions. The first toy I bought was a massager that was phallic shaped, made of smooth white plastic and was cold to the touch. It was about seven inches long.

I recall introducing her to this toy. It was a mid-week morning and I woke to get up for work at around 7am. Sarah was on two days off -- her weekends rarely coincided with mine. I got up, used the bathroom and then my wife did the same. When she left our bed I slipped the massager under my pillow as she didn't know I'd bought it, though we had discussed it passing some weeks before.

Instead of dressing for work I slid back under duvet. Sarah soon joined me. Neither of us wore anything for bed and I moved towards her. She had her back to me as I cuddled in to her and started kissing her neck and my already erect penis pushed in to her bottom cheeks.

As I continued to kiss her neck I let my hands slide down and over her breasts and then tweaked her nipples which stiffened under attention. Sarah was about five foot four inches, a size 10, and had 34B breasts. Considering she had given birth to two children she was in good shape, kept fit and at 28 had taken to shaving off her pubic hair which was dirty blonde like the hair on her head.

I let my hands move further down her body until they were between her legs and I soon parted her lips and got a finger in to her tight pussy and searched out her clit which I stroked in to its own mini-erection.

Being well practised at pleasing each other Sarah knew not to return my attentions at this stage and simply rolled towards me so she was on her back. Raising her knees a little and opening her legs allowed me to get a couple of fingers a little deeper in to her and I then began kissing her from the neck, over her breasts and down her flat stomach. I moved down the bed until I could plant my mouth squarely on her open pussy and my tongue soon went to work, licking and kissing her clit before sinking as deep as I could get it in to her vagina, tasting the sweet mustiness of her growing excitement.

I would usually lick and finger fuck her to orgasm before letting her climb on to my dick and ride me until I came. However, my mind was drawn to the massager under the pillow and I stopped my oral caresses, moved quickly up the bed, retrieved the massager and took it back below the duvet with me before Sarah got a glimpse of it.

Going back to work with my tongue to ensure she nice and wet I gently manoeuvred the massager until the tip was near Sarah's open lips. I then stopped licking, turned the massager on and gently placed the tip just on her labia. The motor was surprising powerful and the touch of the cold plastic combined with the deep vibration made her jump initially.

I gently played the massager over her lips before easing the first half inch into Sarah's vagina. I held there just letting the vibration run through her and then asked her if it was nice.

"Yes," she purred in reply and I pushed it a little deeper in to her and then gently withdrew it almost to the point that it came out.

My efforts were met with a moan and gaining confidence I repeated the motion, pushing the massager a little deeper before pulling it back almost out again and then in again a little deeper and a little quicker.

I built up a rhythm and was soon fucking Sarah with the massager, careful not to push it in too far as I didn't want to risk any discomfort for her given the fact the massager was hard and unforgiving.

Within a very few minutes Sarah was starting to thrash around and I knew her climax was approaching and when she came she let out a muffled scream, pulling the duvet over her face as she shocked herself with the outburst.

As her orgasm subsided I slowly withdrew the massager and couldn't help but give the end a little lick to taste her juices which really had been flowing.

I moved back up the bed and my cock was rock hard. I lay on my back and Sarah straddled me, grasping my shaft and guiding it straight in to her vagina. She then rode me very hard, and I marvelled at her bouncing breasts as she bounced up and down.

My own excitement had built rapidly as I had fucked her with the massager and it didn't take long for me to shoot my load in to her just as she reached her second orgasm, even more intense than the first and which left her in a crumpled heap beside me.

"Did you enjoy that?" I enquired when we got our breath back.

"Yes, it was a nice surprise," Sarah replied.

Over the following months I bought her several more vibrators and dildos and our sex life, which had already been good, got even better.

The second toy I bought was a more conventional vibrator, skin toned with a soft outer coating. It was perhaps again no more than seven inches long but the last third was bent to aid G-spot stimulation.

We tried this one evening after being out for a couple of drinks. It was late and we went up to our bedroom in the pretence of going to bed.

Sarah was wearing jeans and a t-shirt. She'd taken her t-shirt off and was walking around in her bra and jeans. I told her I had a surprise for her and when she asked me what it was I told her she'd have to wait and see.

We began kissing and I eased her backwards on to end of bed and then undid her jeans and slid these and her skimpy panties down her legs and discarded them. Sarah's legs were over the edge of the bed and I knelt down and gently kissed up her on one knee and then ran my tongue up the inside of her thigh, across her pussy and down the other inner thigh, stopping at the knee. I repeated this a couple more times before concentrating a little more between her legs and licking her clit until it was standing proud and her hole was well lubricated as her juices and my saliva intermingled.

Judging the time was right I stepped to my bedside drawers, took out the new vibrator and got back between Sarah's legs so I could gently work it in to her, the small motor making a quiet but continuous buzz as I inserted it and gently worked the end towards her G-spot.

Sarah moved further up the bed with the vibrator half way in her pussy and I lay beside her and eased the toy a little further in. To my surprise Sarah moved my hand and took hold of the vibrator herself and worked it further in so the curve caused the head to contact her G-spot. I watched as she moved it around so that the vibrations hit the right spot and she drew her knees up and lay back flat on the bed to ensure I could see what she was doing.

I kicked my own jeans and boxer shorts off and my erect tool pressed in to Sarah's thigh as she began to masturbate herself now with the toy and as she did this I leaned towards her and sucked and chewed on her stiff nipples after pulling her breast out of the top of her bra.

As her excitement built I twisted my body so my groin was near Sarah's head and my own mouth found the top of her shaved pussy and I let my tongue flick out to her clit as she began to orgasm.

Before her climax had subsided I got between her legs and shoved my cock in to her as soon as she had let the vibrator fall out. I was so close to coming after watching her fuck herself and it was all I could do to ram her hard for a few fast, deep strokes before pulling out and then pushing in again for some slower, controlled strokes. Then back to some harder fast thrusts before withdrawing again and then entering slowly, pushing all the way in and then coming out again slowly.

I could not keep my self-control beyond a third set of hard, fast strokes and soon my sperm was spurting out in to the depths of Sarah's hot vagina.

.........................

The introduction of toys in to our bedroom had the effect that Sarah usually had several orgasms each time we had sex. Before using toys I would always try and finger and suck her to orgasm before sticking my cock in her and allowing myself to fuck her until I came. Sometimes she would have a second orgasm, but she would reach this stage more often if she had the added stimulation of a vibrator or dildo up her during foreplay.

It was also noticeable that Sarah enjoyed playing with herself and accepted that giving herself an orgasm was very stimulating to me as I loved seeing her fuck herself until she came. However, she also had a growing curiosity in general over sex and as her inhibitions reduced she would let me stimulate her G-spot to the point that she would squirt all over me, though this level of stimulation could only be achieved with my fingers were proved much more suited to applying stimulation to the exact area required.

This new found curiosity was taken to a new height one Thursday morning. It was around 6:30am and Sarah had been working the night shift, 10pm to 6am.

I woke when I heard her car pull up but I drifted back off to sleep and didn't hear her come in to the bedroom and undress.

I did wake as I sensed her crawl in to bed and snuggle up to me -- I had my back to her and I felt her stiff nipples stick in to me. I guessed it must have been a cold shift.

A hand then snaked round, over my stomach on to my flaccid penis. Deft fingers gently eased my foreskin back and it wasn't long before the blood began to flow up my shaft and an erection soon followed.

"Busy night?" I asked.

"Yeah, quite busy. I was tied on one case most of the night, out trying to arrest a bloke for buggery. What is that?"

I was a little taken aback by Sarah's apparent naivety but explained, "It's anal sex, either a man on a woman or a man on a man. I thought you would have known that ."

"You mean a guy sticks his dick up a woman's arse?" Sarah asked, seeking clarification.

"Yes," I confirmed.

"Erect?" she asked. "Yeah, erect or else it wouldn't go up there," I explained patiently.

Sarah then released my erection and rolled over to face away from me. I rolled so that I could snuggle in to her and as I did this she reached behind her back and started masturbating me until she was happy I was fully hard. She then eased back towards me, lying on her side as she was, and bent forward at the waist so I could shove my cock up her pussy which was already wet and warm.

I thrust in to her, groping her hard nipples as I pounded away, my hairy groin impacting on her smooth, rounded bottom.

No words passed between us as without foreplay we were just fucking and without too much pre-intercourse stimulation I felt like I could keep up a good rhythm for some time. However, without warning Sarah stopped bucking back towards me and before I knew it she pulled my shaft out of her soaked pussy. Keeping hold of my manhood she leant a little further forward, ensured my foreskin was pushed right back then guided to tip of my penis to her anus.

I froze, not really sure what she was doing.

Carefully she rested the tip of my penis on her puckered start then encouraged me forward and in to her virgin passage. No lube, no prep, just the moisture of her pussy to ease it in.

I held my breath and did not dare move. Her anus was so tight I thought if I pushed in any deeper I would hurt Sarah. Only about an inch of my seven was in and I felt like it would be impossible to go any further.

As I lay there Sarah pushed gently backwards and as she did this more of my shaft disappeared in to her and eventually I was nearly fully engorged.

Tentatively I started to pull out and Sarah gasped and then moaned as I ever so carefully pushed in again.

"Are you sure about this?" I asked before moving again.

"Oh yes," Sarah gasped.

She placed her hands on her bottom cheeks and eased them apart to loosen the pressure a little on her anus. I grasped hips and then gently withdrew before pushing in to her again, a little faster than previously, but not roughly.

Sarah moaned and one hand disappeared from her anus to play with her pussy as I began to build up a rhythm of deep, slow strokes.

The sensation was at first a little weird. It was so, so tight and I was worried it would hurt Sarah. However, my concern turned quickly to the fact my own excitement was suddenly growing and I thought I would not be able to hold back from squirting very, very soon.

I tried to clear my mind and just enjoy the sensation and started to pump in and out a little faster and a little harder. The increase in pace was met by an increased rate of small moans from Sarah as she continued the finger herself.

Suddenly I felt I was on the edge of blowing my wad and so I withdrew all the way from her anus. Sarah rolled on to her back and, opened her legs and I sank my cock in to her pussy fucked her with a hard and fast urgency that brought her to a climax just as I erupted in to her.

I fell back on to the bed and drifted back off to sleep, dreaming of how far Sarah's new found curiosity might go.

Ready to Try

There was nothing that could really prepare my ass for Ed's cock. I spent the weeks prior to our meeting playing in my own tightest space, fingers, plugs and vibes of varied sizes. I thought my ass was ready for deep tight fucking, but not so.

I had not anticipated Ed's penis would get that rigid.

I thought flesh would have had some give but his cock was as stiff as an iron bar. It actually boosted my self confidence that the man I wanted got so hard at the thought of fucking me, especially fucking my ass!!,

I looked down at his dick, veins bulging, glistening with a mixture of saliva , precum and my pussy juice. It curved upwards and to the left, the shaft deeper red than when soft, darkening to an almost angry purple head.

I Iay on the bed with a couple of pillows under my ass, so that it was provocatively presented to Ed.

I felt him slip his finger into my little pink brown crinkly star...immediately my ass gripped his finger but relaxed as he gently screwed it in and out, loosening that tightest of channels.

There was little that could have prepared me for the sheer fullness that his cock endowed on the tightest of my holes

.

I had tried to prepare the way with various combinations of fingers, vibes and plugs....I thought my ass was ready for some tight, horny shagging, but no!!

I looked at Ed, gripping the base of his shaft, guiding his purple head towards my twitching ass hole...my expectation was so intense....his tip slid into my opening, he stopped and waited.." Push a bit more" I gasped

He did and the pain was sharp and intense..." NO, no " I cried. Ed immediately stopped, withdrew a little, and tenderly asked if I wanted to continue.

"Oh yes, but very slowly" I said, just a bit at a time.....I desperately wanted to be filled by his rampant cock. I wanted him to be where no-one had ever been before.

Slowly he put a hand on my ass cheek and the other guiding his cock to its tight hot target .."Are we ok to try again KD" he said

"Yes, gently" I murmured.

His purple tipped cock again started to spread my tiny brown star, a wave of pain washed over my lower torso, I breathed very deeply and pushed my ass further onto his cock

.

The pain is began to subside, giving way to a warm velvety feeling as my passage began to be filled.

The whole of his cockhead was in, and I felt light headed. Ed pushed again and I let out a sharp cry of pain...it was surprising to me because my blue vibe was bigger than Ed's swollen tool!!

"Just slow down Ed" I gasped as my ass clenched and my mind raced.

I took more deep breaths. Breath, grip, let go...I soon got a rhythm which dissipated all trace of pain.

Ed was on his back, me ass skewered on his cock, looking into his eyes . I felt filled, not only physically but emotionally.... I've never experienced such a feeling of physical intimacy.

Now I'm rising and falling on his stiff cock....pulling up and grinding down...him moaning, eyes like slits unable to disguise the sheer ecstasy of my tightness.

My pussy lips, engorged with blood drip my juices onto your belly. You being in my ass makes me so wet....my fingers find my labia, eagerly exploring hole and clit...this is sensuality gone wild...I want you in me, always...me dripping on you"

"Fuck my ass Ed, please fuck my ass!!"