Hannah’s First Anal

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I had been married for around ten years when my then wife, Hannah, 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 Hannah 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. Hannah 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. Hannah 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. Hannah 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 Hannah 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 Hannah 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 Hannah’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 Van Escort lips before easing the first half inch into Hannah’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 Hannah 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 Hannah 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 Hannah 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,” Hannah 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.

Hannah 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. Hannah’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 Hannah’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 Van Escort Bayan G-spot.

Hannah 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 Hannah 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 Hannah’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 Hannah’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 Hannah’s hot vagina.


The introduction of toys in to our bedroom had the effect that Hannah 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 Hannah 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 Hannah 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. Escort Van 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 Hannah’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?” Hannah asked, seeking clarification.

“Yes,” I confirmed.

“Erect?” she asked. “Yeah, erect or else it wouldn’t go up there,” I explained patiently.

Hannah 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 Hannah 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 Hannah. 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 Hannah 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 Hannah gasped and then moaned as I ever so carefully pushed in again.

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

“Oh yes,” Hannah 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.

Hannah 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 Hannah. 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 Hannah 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. Hannah 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 Hannah’s new found curiosity might go.

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