Anal Angel

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Man discovers his wife's friend anal secret with benefits.
3.3k words
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My wife's best friend is Trudie. She's around 43 years old, wears her hair short and bleached blond, almost white! and whilst not a page 3 stunner is attractive with a toned figure and gorgeous eyes. She's divorced, her husband of 22 years as he suddenly decided he preferred tender younger flesh and carried off his PA. That was over three years ago and surprisingly Trudie has remained single and to our knowledge never taken a partner or boyfriend.

We regularly invite her over for dinner and we all get on well. Sometimes I flirt with her, and sometimes she flirts back. It's all innocent banter, I'm happy in my marriage and even though our sex drive is on slow to stop my wife and I are content with our life. Besides, I couldn't afford a divorce lol!

That's the background, now here comes the really amazing bit. It was around 6 months ago my wife and Trudie had taken themselves down to London to the O2 arena to see a concert and they'd decided to make a weekend of it by staying over. That was fine by me.

So Saturday evening I bought home a takeaway and settled down with a few beers to enjoy my own company. As the evening wore on inevitably my thoughts turned to porn. You may recall I mentioned our sex life is slow stop, and I'd developed a habit of downloading porn from the web. Such activity doesn't include my wife, she's rather missionary straight laced about sex and I've never gathered up the courage to suggest it to her.

So by midnight and after probably a few too many beers I'm surfing though page after page of fornication. I don't now how you feel about porn? For me it fills a need, and yes I've wanked myself stupid watching it (haven't you?). But deep down you just know the people are actors and real life is seldom blessed with so many insatiable wanton women and well endowed studs. That endless sex session has probably been spliced together over 3 or more sessions.

Which is why I signed up to adult contact site. Seeing all those real women was far more stimulating and whilst I'd never availed myself of any of the services I've wasted many a lustful hour scanning the ads and picture galleries.

And so it was that evening, only this time I elected to watch a short movie clip.

Being a lover of all things anal I'd selected an appropriate clip. It was pretty much straight to the action, camera focussing close up on a woman's hand gently moving a butt plug in her ass.

I started to get those familiar stirrings in my loins as the woman slowly and anally masturbated herself. The clarity of the video was immense, every slither of anal juice coating the butt plug could be seen. She'd pull the plug, leaving her asshole gaping and twitching, then she'd push it back through the closing gape, moaning softly as she buried deep inside her rectum.

This extreme act progressed for around 5 minutes with the woman finally turning to face the camera as she raised the butt plug to her mouth and licked it salaciously clean.

I almost fell off my chair.........it was Trudie!!! That bleached white hair was un-mistakable, I continued to watch transfixed in utter amazement. Then it was over. Five minutes that shook my world. I sat for a minute or so not believing what I'd seen, then I replayed the clip over and over each time looking for some visual clue to confirm my revelations. But none was needed, the more I watched the clip the more I was convinced it was my wife's best friend.

I went back to check her profile. She went under the pseudonym "Anal Angel", all the still images in the public gallery did not include a head shot. At this point I hadn't scanned the private gallery having gone straight to the movie clips, of which here were eight. I noticed she didn't offer escort or phone services just web cam. At this point it's hard to describe my feelings.

I've known Trudie for many years she was for all intense and purposes a regular woman. Seeing her performing with such extreme intimacy had shaken me to the core. But what was I to do with this information. Sharing it with my wife was out of the question it would expose my furtive online activities.

I began to wonder how I could ever see Trudie in the same light again, how would I re-act next time she dropped by, has she shared her secret with anyone....my wife even?

All these thoughts kept me occupied for the remainder of the night and then midst the alcohol and the lust I formulated a plan........

I woke the next morning convinced I'd have to let Trudie know what I'd seen. That was the easy part, but I was struggling to pluck up the courage to speak to her outright. Then it dawned on me, well, I thought it was an inspired idea at the time.

A couple of days later I was in Birmingham and called into one of the porn shops. There was an amazing array of toys, all shapes sizes and colours. I spent some time looking around and finally a chromium anal dildo caught my eye. It was just what I was looking for, obviously a sex aid but a pretty upmarket one at that. Purchase made I left.

I parcelled it up and enclosed a short hand written note about having witnessed her online video and hoping she'd appreciate the gift that she'd surely find a use for. Foolishly I signed it before popping into the post office.

No sooner had I posted it I began to regret it. In the sober light of day it was a stupid act from a frustrated guy. What on earth was I hoping to achieve?

The next few weeks were quite anxious weeks. I telephoned Trudie on three occasions, having summoned up the courage to admit to her what I had done, but each time the phone just rang out with no option to leave a message. My anxiety was exacerbated by the fact more than three weeks had passed since I had mailed the package to Trudie and I was concerned there had been no reaction, of any kind! Suddenly I again doubted my judgement and felt regret at what I had done.

A couple of more days passed, then I received a phone call.

Trudie's voice was measured but calm, "I think we'd better talk don't you, so come round to my flat tomorrow afternoon OK?"

I agreed. She hung up before I could respond. She'd had obviously recognised my number from her missed call list, so there was no denying the deed any more.

I left it late into the afternoon the following day before I summoned up the courage to call round to her flat. She greeted me with a stern look before showing me through to the lounge. I noticed a half drunk bottle of red wine on the coffee table. Bit early I mused, but if anyone should be drink it should be me, in order to steady my nerves.

Trudie must have read my thoughts, "Can I get you a drink? I'm having wine?"

"Bit early in the day isn't it?" I replied.

Trudie shrugged, "I'll get you a glass."

I shuffled from foot to foot and was feeling decidedly uneasy, the alcoholic bravo of a few weeks ago had longed passed and I queried what the hell I was doing here. I sat down in an attempt to calm my nervousness.

Trudie brought in a second glass and set it down on the table, and then placed the new unopened anal dildo alongside it.

"This is why I needed the wine, it's not easy for me knowing what you've seen," she added.

I squirmed a little in my chair, she was right it had been a stupid foolish act on my part. I was about to reply but she continued.

"What were you thinking when you sent me this?" she asked.

She picked up the sex toy and gestured with it in my direction, "I didn't take you for a pervert or a crazy porn voyeur," she added.

"Takes on to know one," I said

"What?" She seemed surprised at my accusation

"Well come on how many women do what you do?" I sensed I was becoming bolder by the second. "I mean it's hardly mainstream activity is it and to be frank it was pretty hardcore!"

Now it was Trudie's turn to feel uneasy, her face reddened slightly and she flicked her hair I continued.

"Besides I thought the gift appropriate all things considered," I took a long gulp of the wine then rather bravely added.... "Perfect ass!"

"Look what I do in my own time is personal to me, I don't need any lecturing from a pervy guy who watched porn online. You're only here because you're a friend and husband of my best friend. Although right now I'm not sure what sort of friend you really are?"

Trudie regarded me closely for a moment then picked up her glass and downed the contents in one. She refilled the glass then looked mischievously at me. "When you saw me?" she paused "Were you wanking?"

I was at a total loss for words. She smiled "I bet you bloody were," she said.

She picked up the dildo from the table, twisted in her hand and raising it to her face proceeded to study it closely, slowly turning it.

"It would really fill me up," she said continuing to examine the plug, "and would need rather a lot of lubrication initially," she added.

She opened the box removed the clear plastic packaging and taking out the chromium toy lifted it to her face gave it a much closer examination.

I watched her now a little unsure of where I stood on this matter. I was guilty as charged but was she annoyed or secretly pleased. Then the ice began to thaw....

She opened he mouth and wrapped her lips around the dildo, slowly sucking on it, then withdrew it and placed it down on the table, but this time the silver cock glistened with her mouth juices. I recalled her lewd performance from the other week.

"Maybe it would be easier if you helped me," she suggested.

I became quite nervous, uncertain of how I should now respond. This has all been a stupid idea, for all my voyeurism I never actually intended to act out any of my fantasises in real life. The fear of discovery and the complication that may arise has always dissuaded me from any of that action, But now..........

"Well?" quizzed Trudie, who was now gently moving her hand up and down the wet cock toy simulating masturbation.

I was completely lost for words thoughts were racing through my brain get up leave, do as she wishes, apologise, Christ! Where do I go from here.

Trudie stood up sex toy in hand,

"I need a pee why don't you have a think then when I come back you can tell me what you've decided?"

She left the room leaving me in a confused state, obviously the alcohol had clouded my original judgement when I embarked on this action, but she'd retaliated assertively and was clearly in control of events. I sat waiting, she seemed to be taking a while, probably on purpose to increase my uneasiness.

After what seemed like an age but in reality was probably just ten minutes she re-entered the room. Wow! She changed.... now standing before me in lace bodice, stockings suspenders and stiletto heels, anal dildo still in hand.

"Perhaps this will help you make up your mind," she continued "Your very own real life show, yes."

I stood up, fuck it what the hell! how could I refuse? As she came close to me I placed an arm around her waist, and caressed her thigh above her stocking top with my other hand.

"The answers yes," I replied nervously.

Trudie looked me in the eyes, "Let's get this straight before we start, I'm not going to let you fuck me, just watch my little show as an appreciation of your gift. If you want to wank, because that's what you do, then that's OK with me."

I found myself nodding in agreement and thanking her!

She gave me gently kiss on the lips then taking my hand led me out of the lounge and down the hall to a room at the far end.

It was a room full of surprises, against the opposite wall was a large low bed, draped in black sheets. To the side was a small table with an array of sex toys, dildos, chains, butt plugs, lube tubes, speculum, anal wands and more. The window was blacked out and set upon two tripods were two video cameras, each at a different angle and height. Studio lighting was by means of two rectangular soft box lamps mounted on tripods. Whilst on the walls hung a variety of graphic photograph. First impressions were were shots of Trudie herself. The whole room was very impressive and wouldn't have been out of place on porno shoot set.

She crossed to the bed and taking a remote from the other bedside pressed a switch. The lamps flicked into use and the room was bather in a warm red glow from ceiling spot lights.

She didn't waste any time and mounted the bed on her hand and knees, shaking her her delightful arse to get me attention, as if needed! She gazed over her shoulder and with a mischievous smile moved one hand between her thighs, rubbing herself slowly at first then a little more energetically. She pulled her panties to the side and I watched as her fingers caressed her pussy, she moaned tracing her fingers between the fleshy folds and back over her dark anal rose.

"Like what you see Tom?" she asked as she turned over onto her back, spreading her legs wide.

She pulled out her breasts from within her bra and whilst rubbing her herself with one hand used her other hand to pull and twist at her nipples.

I was transfixed, every bit a porn star, her legs spread wide clothed in black stockings, suspender belt, and stiletto heels, all the time her body writhing upon the bed from her touching herself.

Trudie was becoming very moist as she became more aroused, her fingers now eagerly probing her cunt. She watched me standing at the foot of the bed.

"See see how wet I am, how my fingers are covered with my juices."

I was speechless just totally absorbed in watching my wife's best friend wantonly bringing herself off in front of me. Someone with whom we'd shared many an evening meal with now lewdly masturbating herself for me. I was beginning to sense that familiar feeling in my loins and became aware that my ever stiffening cock was clearly making an impact on the front my pants.

"I know you're excited," she teased as she plunged her fingers ever deeper into her vagina.

"Why don't you come a little closer, you won't want to miss anything," as she tempted me with the prospects of more voyeur delights.

I moved closer my eyes fixated on her hand as she played with herself.

"Hmm I feel so slutty knowing that you're watching me here in person and not an anonymous voyeur online." Trudie's eyes never left me as she expertly played with her clit.

She circled her anus with her finger her moist fingers sliding effortlessly between her legs. Her breathing was beginning to labour and she reached out with her other hand for the chromium cock shaped dildo.

"This is what you want to see, you want to see me fuck my own arse you bad boy."

She pushed the tip of the dildo against her dark rose of her anus, a little grimace on her face showed her intent, as she pushed harder against the tight ring of muscle.

I watched intently as she her rose slowly gave up resistance as she pushed and slowly I saw her open up and the tip slipped inside her. She uttered a gasp followed quickly by a low pleasurable moan as the dildo slid home.

With the dildo deep inside her anus she ceased the pulling on her nipples and now used her hand to finger her self once more. She continued to masturbate while she twisted pulled and pushed on the large dildo.

"Don't you like what you see, you're not wanking?" she teased.

I did indeed like what I was seeing. I was acutely aware of my now rock hard cock tenting the front of my trousers and I was itching to set it free and join her in mutual masturbation, but for some reason of conscience I was fighting the urge whilst relishing the lewd spectacle in front of me.

Trudie moaned louder as the glass plug her anal sensations rushed through her body.

"Oh fuck this so good, so much better then fucking for the camera," she hissed. "I want you see me for the anal slut I am."

I figured she wasn't long off orgasming and I felt my early resistance beginning to subside as I watched.

It was no good I couldn't hold out any longer I unzipped my pants and yanked my cock free.

"Oh yes babe, that's so horny," croaked Trudie as I pulled on my cock.

Egged on by Trudie I pulled furiously on my cock watching her writhe in front of me, her stocking legs spread wide apart her cunt red and swollen from her fingering and the sight of her hand fucking her ass only made my experience more intense. I reckon it was two minutes, no longer, before I shuddered into an enormous ejaculation. My cum exploded from my cock flying thought the air and splattering Trudie's thighs and abdomen.

She let it a little scream as my hot sperm hit her, before her body bucked and she orgasmed in a series of spams and screams. She fell back on the bed I could see tiny rivers of cum dribbling down her thigh and little pools on her abdomen. She gazed at me and gave a dirty smile.

"That was fun, it's been a long time since I saw a man cum."

"Yes it was....thanks," I added

The dildo was still inside her and she reached between her legs to withdraw it. She gently pulled it out and for her brief moment I saw her gape before the brown ring of muscle closed in.

I watched transfixed as she raised the chromium cock to her face. It glistened with her was juice and she ran her tongue over the length of the shaft, before taking the slimy head full into her mouth to suck on.

Once clean of her juices she slowly turned it around in her hand, regarding it closely and if inspecting a precision instrument.

"Hmm thank you for your present, a nice fit for me, don't you think so?"

"Yes," came my hoarse reply.

"I suppose you'll be watching more of my videos in future babe. I really think you should, then you'll get to know what a dirty little anal angel I really am. Who knows you may be invited to another live showing if you're lucky."

I nodded, and tucking my sticky shrinking cock back into my pants replied

"Yes that would be wild and maybe I'll but you a bigger one next time!"

She smiled and licked her lips.

"We'll see, now I think you better be getting back to that wife of yours, I promise not to tell, if you don't."

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allitnilallitnil4 months ago

Feels real except for expressing dilemma about cheating on your wife. Unless you don't consider that cheating. I mean you only watched, you never laid a finger on each other. I guess only time and a few more stories will tell. Secretly I want to read how you get involved with making a video with Trudie and your wife ends up seeing it because she's anal curious too. But she doesn't tell you, she just gets it on with Trudie and then they arrange a threesome with you - and you definitely end up being pegged by Trudie while you're fucking your wife's ass for the first time. Fair is fair...

jafo81jafo814 months ago

More I think you did well on this one

AnonymousAnonymous4 months ago

Yes..need a editor but I like the storyline. I hope you write more. This could develop into quite a series. And surely, the wife ultimately gets involved. Good luck.

PunjiPunji4 months ago

The making of a good story is buried in the typos, grammar mistakes and spelling errors. My advice is to get an editor and repost.

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