Trudy Ch. 01: The Awakening

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First steps to cuckoldom and a freed wife.
5.1k words
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Part 1 of the 6 part series

Updated 06/08/2023
Created 07/17/2016
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So, I recently came to the conclusion that I am, or more precisely, wanted to be Cuckold.

My wife and I have been wed for over 25 years now, and to be frank sex has always been an issue... I won't dwell on her past, but we have had to deal with more than the usual phases of a relationship and marriage.

My own problems started long before I met my wife. You see I am your proverbial Mr average. Cock of just about 6", not to thick, but not a pencil dick either - average.

Unfortunately for me I discovered porn young, thanks to my dads stash of mags and videos that I found, and scoured at every opportunity. This led to feelings of inadequacy when I compared myself to the stallions in the vids and glossy pages and yep, you guessed it, from there it was a short slope to performance issues increasing my feelings of worthlessness. My confidence and self esteem now in tatters, my thoughts constantly focused on what my girlfriends at the time were obviously craving for, but I could not hope to deliver.

As a teenager I was engaged to another girl before meeting my wife... during split-up sex with this girl I asked her if part of the reason for the split was because I couldn't satisfy her properly, which she confessed was true. She admitted she fantasised about sex with other men, with big cocks fucking her for hours on end, whoring her. She even admitted fantasising about my Dad...! Looking back this was the beginning... something clicked in my head that night, and since then my fantasies always involved other men owning my partners cunt. I very rarely imagined myself fucking other women when I jerked off... which is still true to this day... why would I when I know they wouldn't possibly want to be serviced by such a fucking dweeb - its a false prophecy.

Anyhow, back to my wife and my marriage... our first time wasn't great, but as I said she had issues of her own to deal with and at that time was looking for someone to love and protect her, and not a stud. That I could do. And be under no illusion here, I deeply adore my wife... like some soppy arsed Mills and Boon novel, I never want to lose her.

We persevered, but sex was sporadic and infrequent, then kid number one came along and the old tiredness excuse crept in, followed by kid number two and sex became a memory.

When we did have sex it was like shagging a slab of meat for the most part... I did all the initiating, she never asked me for sex, ever. I did all the foreplay... fingers, tongues, lips, caressing etc. She never touched my cock... refused to give head... just lay there while I slipped it inside her, normally in the spoons position, and then shot my load in her twat before sloping off, spent, to wipe my cock dry in the bathroom.

We talked about making more of an effort and we both joined a gym and lost some timber in the hopes it would give us more energy and make us more attractive to each other again... and sex picked up for a wee while; though my performances did not... I could exercise the body, but not the demons in my head.

Then came the hysterectomy, and when, after giving her time, I did try to initiate sex, I got the cold shoulder, the legs clamped shut together, the turn over and covers up to the neck routine... you get the idea... "fuck off, I'm closed for business".

Then the menopause happened in her mid 40's... another drop in libido to cope with.

She is not 50 yet, and still hot to look at... making it even more frustrating; a bit like owning a Porsche without any keys, desperate to drive it full tilt, but not able to start it the bastard thing!

We talked some more. She said she just didn't enjoy sex, she could live without it - but despite my limitations I told her that I couldn't live without sex, that I refused to be in a completely sexless marriage, so for the sake of 'us' she said she would try counselling.

Her comments really surprised me to be honest, because when we did have sex, and she was in a rare receptive mood... horny for once, it was so apparent to me how much she wanted to be satisfied more; by the things she murmured, and how she pushed hard against me, or tried to pull me much deeper inside her so she could feel me, and how frustrated she was when I came up short... literally... she was clearly desperate for more, wanting satisfaction - not desperate to give it up altogether, as she'd said.

Wow... did the counselling work and then some. Well for two weeks anyway. She went from wanting to be an abstaining nun, to a raging torrent of hormones; a nymph.

She jerked me off for the first time, she even sucked my cock too for the first time - I was so buzzed out of my tiny mind, I started asking her about fantasies. She said she had none... yeah right... and asked about mine. So I told her about how many times I had got myself off lying next to her, while she slept, thinking about her being screwed hard by so many men, in so many ways, in so many different situations. All the guys were studs... huge cocks, last for hours, would fuck her delirious - obviously.

I suggested we watched some porn... we watched threesomes, we watched a husband being cuckolded by a black guy with the biggest member I had ever seen (so far) - making the cucks wife squirt like a fountain. We had the best sex of our marriage that night, and all the way through I was asking her to pretend I was someone else... asking what she would do if a stranger managed to find his way in to bed with her, and she mistook him for me in the dark, only realising it wasn't me when his huge cock thrust deep in to her pussy... would she let him carry on? Would she let him use her? And you know what... she said yes... that she wouldn't be able to control herself at that point and would fuck him even though she knew it wasn't me.

Now do you see what I mean about her? The conflict, the polar opposites, a tormented, tortured woman. On the outside uninterested, and even anti-sex mostly, but when she's fully aroused, and her guard drops you see inside her soul and find a passionate, seething mass of lust locked deep within, struggling to break free. Despite the revelation that she would have let the stranger continue to have her, I managed to last way longer than usual, helping the cause... she climaxed hard with my cock still inside her; a very rare event.

As I said, this lasted every night for a few weeks then out of the blue she cut me off at the knees. She asked me not to talk about fucking other men, she didn't like my stories, hated them even, and did not want to hear them any more. It was wrong for a husband to have such thoughts, and she only went along with them to make an effort following counselling. Her "bipolar" personality kicking in again.

She was lying. Only words can lie, but the body can't. I saw how swollen her tits got and how her erect her nipples were when I told her my stories; how her skin flushed pink with excitement and how wet her cunt got, as I described the fantasy guys dicks and what they did to her. The things she said, her moans and gasps as I spoke, lending approval to my desires.

She really wanted to stop I suspected, because she wanted these things to happen to her and it scared her shitless. My fantasies had woken something inside her, stirring her emotions in to a broth of confusion and doubt, ashamed and embarrassed by the lust coursing through her... it was all new and hedonistic... and despite our problems, I knew she deeply loved me, as much as I idolised her, and she didn't want to cross the line for fear of the repercussions, of losing me.

So we went back to normal. She let me fuck her now and again to keep the peace, it was now a chore, a duty - and because that's how it felt, then it would be over in a few minutes - get your rocks off honey, but don't disturb me in the process!

She could stop me telling her about my dreams, but she could not stop me dreaming. Most nights I would play with myself while my thoughts were deep in wonderland; visions of so many men claiming my wife... while I watched. It grew to obsessive levels, I started watching cuckold porn videos nightly, reading stories of couples experiences on-line, and generally wanked myself dry most days wishing it would happen to me.

It was then I decided on one final last ditched attempt to draw out the real woman. One night I opened a cuckold story on my Ipad and proceeded to fondle my penis as I read... knowing that the good lady was not fully asleep and would guess what was going on. After I came, I went to the bathroom to wipe the cum away as usual, but this time left my Ipad on the bed with the porn story still open.

Sure enough when I came back she was reading the story, and was a bit flustered when I caught her. I laughed. But she kept reading.

When she was finished she asked if I imagined that the couple in the story was us, and if I really wanted something like this to happen. I told her it was all I thought about. I told her that despite what she said before, I knew that she wanted it too, but was scared to admit it to herself and me because of the fear of the unknown. I explained that her petite, big titted, peachy arsed body deserved to be properly taken and her wetness filled with a throbbing shaft to make up for my inadequacies. I wanted this for her so much, as an expression of my love for her, reassuring her we could handle it and that we'd actually be stronger, closer as a couple. Yeah, I would get a kick out of it, but this was more about her being pleasured, and letting her inhibitions go and giving in to her base carnal desires. She so deserved to experience a real man treating her like his bitch.

... she bit her lip, then blurted out... "oh my god, I can't tell you how much I want this, you were right it scared me before, I thought you were messing about and if I admitted to you that I actually wanted to do it, or to try it at least, that you would be appalled by me. That we would be over."

I laughed and said I knew... that I am always right. I explained about the signs that her body could not hide, despite her lies and fake indignation. Like a poker players 'tell'.

She asked me to explain more about being a cuckold... we watched more informative video compilations, explaining the subtle differences and preferences... and the terms hotwife and bull... what we liked and didn't like, and if we agreed to try it, what the rules were.

I wouldn't take another mans cock, not my thing.

I would do a bit of cleaning up.

She would do bareback, depending on who it was.

No neighbours, or people we knew... it had to be a stranger.

Not in our home.

Never on her own. I always had to watch... for now.

Preferably spontaneous hook ups... bar/club etc rather than arranging a meeting online like a doctors appointment.

Well endowed a must, any colour of skin was fine by her... she had always wondered what a black cock felt like (I'd guessed right there too!)

Cock sucking was ok... now it involved a fucking monster dick off course it was

She did not want anal with such a huge cock and a hitherto unexplored region

Cunny licking and fingering etc no problem.

So we talked in to the night... and oh yes fucked long, slow and hard... both pretending I was her new bull.

It was obvious really. The answer was go on holiday. Where better to meet lots of hunky well endowed strangers in clubs and bars, or the beach all looking for some holiday adventures of their own.

We rented a villa in the south of Spain... the Costas. Secluded insofar as not overlooked (private with its own pool) but not far from beach or town.

It did not take long... three days to spot a a good looking white chap of roughly our own age on the beach, with ample cock nudging his shorts out of shape, four days to 'bump him to him' and get to know him, and then the next day I became a cuckold, officially.

We were in a hotel bar, one of those complexes open to all. She had dressed to impress... low slung white linen dress, showing off her braless cleavage in all its shapely, seductive glory and short enough to provide glimpses of her silky, knicker clad pussy from the right angle.

We spotted the guy we'd seen at the beach. We knew he was staying at the hotel as we followed him back from the beach the previous day, and noted he sat outside for a while reading a book on his return, room key on the table. We gambled he was a creature of habit and went back the next day. Score.

We sat behind him. Another piece of luck, as I noticed he read cop thrillers. That was my in. When he went to the bar, I followed and mentioned his book as we waited for the drinks... when we got back to the tables I introduced my wife to him. Immediately his eyes looking down on to her tits squeezed in to that dress.

His name was Jack. Widower of a few years. Cancer. Holidayed by himself and admitted after a few more drinks that he really came to have sex with as many women as he could without the complications that you get from the dating circuit at home.

As the drink flowed, Jack and Trudy (oh yes, thats my wife's name) were flirting outrageously... at one point his hand flopped to her knees, his fingers nonchalantly sliding between them and gently squeezing the soft flesh on the inside.

When Jack went to the loo I asked Trudy if she wanted him to fuck her... and she simply nodded, sheepishly. I suggested we try for the next night, as Jack may be slightly impaired by all the drink and although she pouted a little she agreed... mainly because the thought of a full service rather than an inspection was rather more appealing!

It was now or never... so I came straight out with it. When Jack came back I said... "How would you like to meet up again tomorrow evening, and fuck my wife for me... while I watch."

He winked and said "I thought you'd never ask". To our surprise Jack suggested a small, secluded cove on the beach he knew rather than a hotel room or our villa... neutral ground, but also more memorable and more about what holiday sex should be, he said.

Just as the sun was dipping on the horizon the next evening, we met Jack and followed him to his secret cove. Trudy wore a loose smock in keeping with the beach date, without a bra, but kept the silk knickers in place, as she felt it more erotic for him to have to undress some of her assets during foreplay... revealing her intimate area to him like a present.

Towels were laid down on the sand for Jack and Trudy, and I sat off to the side on a large rock, watching intently.

They were both sitting side by side, when Jack leaned in and kissed Trudy on the nape of the neck and then nibbled her earlobe, before moving around to kiss her gently on the lips, his tongue playfully teasing Trudy's in to a response.

The kiss became more passionate, breathy, and as it did so Jacks hand wandered up inside the smock and cupped a breast, his forefinger and thumb pinching the nipple between them until it was rock hard.

He gently eased Trudy backwards so she was lying down, and then slid off her smock above her head revealing her mounds of swollen flesh beneath, as well as the silky underwear covering her shaved pussy. His head dipped immediately, greedily licking and gently sucking each nipple in turn... a snail trail of spittal visible where he went.

I was transfixed... jealous as hell, but spellbound... my cock was like a truncheon in my shorts and I had to set it free, caressing it in my hand as I watched Jack work Trudy's orbs like a master baker kneading bread.

I saw his left hand wander down to the inside, top of her thigh... his fingers parting her legs slightly, creating access to the promised land.

His fingers teased, and stroked around her clit in circles through the cloth of her underwear, and I could hear Trudy mewl like a kitten as he did.

He slipped a finger inside the gusset edge of the briefs and instantly felt her wetness, his finger probed deeper, parting her cunt lips and flicking at her clit poking from its hood... Trudy's back arching upwards as he did.

He slid two fingers inside her and finger fucked her for a few seconds before deciding it was time for him to get sucked off and stood up abruptly, urgency etched on his face.

He towered above her as he dropped his shorts, and removed his shirt, his massive erection pointing skyward... 10" at least and as thick as a towing hitch on a car... he reached his hand out to Trudy who took it and raised herself up to her knees... her lips level with his balls, his bulbous tip rising past her head.

She dutifully took hold of his cock and lowered it horizontally to her waiting mouth... firstly flicking her tongue around the eye and then the base of the tip, before licking it from bottom to tip and back again... and finally encircling her lips over the end of his ram rod. She was not used to sucking cock as I have said, never mind one so huge, but she took as much as she could... practically face fucking herself, impaling her throat on his dagger... but then she froze... the reality of what she was doing, the realisation of what was to come overwhelmed her and she backed off his cock and murmured... "I'm sorry... I don't think I can do this after all... "

My heart sank... I had already blown my load the moment I saw my wife take another mans cock in to her mouth... and was desperate for the final act...

Jack looked seriously miffed, but remained good natured... he announced he was off for a swim in the cold water to 'calm his cock down' and would leave us to talk.

After he went I sat next to Trudy, still in her panties, but otherwise naked and asked why she stopped... 'It just hit me, what was going to happen, that wonderful huge cock was going take me right here on this beach right in front of you and I felt so guilty... I wasn't brave enough to do it... I am so sorry... I promise we can try again... I just need more time and maybe some dutch courage."

I told her she should go and explain to Jack and apologise for getting him aroused like that and then stopping, wasting his time... so she sidled off to the sea to find him, not bothering to replace the smock. I sauntered behind her.

Jack was a way out, swimming up to his neck. Trudy called him to her, but he just beckoned her in... she walked out up to her waist, the waves lapping at her pussy but she would not go any further as it was bloody cold - her erect nipples giving testament to this. Still Jack beckoned her in, and as everyone does in these circumstances, started splashing her with water for being a spoil-sport.

She turned to wade back to shore and Jack gave chase... splashing as he went, making Trudy try and run faster, Jack gaining all the time.

As they reached knee depth, the sand sloped sharply down beneath the breakers; and this angle, coupled with the water dragging at their legs and the childish pursuit, caused Jack to stumble behind Trudy just as they reached the edge of the beach. He reached out a hand instinctively trying to break his fall, but only succeeding in grabbing the back of Trudy's briefs. As he went down, he pulled her knickers down around her knees, causing Trudy to stumble forward too. It seemed to happen in one fluid motion... as their momentum continued their forward movement on to the beach, both now scrambling on their knees, Trudy's panties were pulled all the way off her body, with Jack left holding them in his hand.

At the same time he looked up, and gazed straight in to my wife's slot... seeing rivulets of sea water running down between her buttocks and dripping from her cunt, glistening in the moonlight.

My heart skipped a beat.

Before she could do anything Jack took his opportunity and positioned himself behind her, his legs inside hers so she could not bring them together... doggy style.

She could feel his semi erect manhood pressing in to her arse cheeks... and she panicked again... 'No Jack, please don't" she said...

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