Written by Dan Styall

1 Jan 2010

In a previous posting, (see Andy and Helen are waving goodbye, dated 24th Feb. 2008) I referred to some of Helens previous activities.

This is a retelling of one of those occasions, which involved me, but preceded Helen meeting Andy, her present lover

If you have not read Andy and Helen are waving goodbye, then u may not know I am a Bisexual Cuckold Cross-Dressing Cumslut.

I have been Bi since I was a teenager, gradually becoming a Cross-dresser and Cumslut over the years.

So to begin.

I knew one of my close mates John, a seaman who spent 6 months of the year away, fancied the arse off Helen.

The thing was, Helen didn’t really think of him like that, however, I did.

I fancied my mate. Well I wanted to suck his cock.

We had been going to the gym together for years, so we were used to being naked with each other, but only in that straight way blokes have when they are in the changing room or the shower together.

Anyway one December, I was at his house.

John was divorced by then so he had his own place.

We were getting stoned, having a few beers, and playing games on his Playstation.

The golf game we were playing had amazing women characters erotic enough to get the conversation turning to sex.

He said one of the characters reminded him of Helen. I agreed there was a similarity.

Referring to the character he said he would love to see it naked and then slipped with he would really love to see Helen naked.

“Oh really” I said

“Oops” he replied “have I said too much?”

“Nope, I know you fancy her”

And then a plan hatched in my mind, maybe a way to get at his cock.

I told him I had a video of Helen almost naked.

On the video she was wearing Black Fishnet Hold-Up Stockings, and a Black Basque.

Slight problem was, the video was Helen being fucked, and not by me.

I wasn’t even there when it was videoed.

It was Helen and her then Fuckbuddy Wayne.

Wayne had simply pointed the camera towards the bed, and pressed record

I told him I would bring it next time

I will describe the video in detail on another occasion if anyone asks.

A week later I was back at his house

I was dressed normally, except I was wearing Black Fishnet Stockings, a Black Bra, and Black Lace Teddy underneath my jeans and t-shirt.

All invisible.

We had a few beers and then I gave him the video.

He sat back, as the view opened with Helen kneeling on a bed in her lingerie.

“Fuck she looks gorgeous “he said

Then the back of a naked bloke came into the shot.

He climbed on the bed, knelt behind Helen, gripped her hips, shoved his cock into her pussy, and gave her a hard doggy style fucking

The expression on johns face was hilarious; his mouth was open, his eyes bulging

He stuttered “Who is that fucking Helen? The lucky bastard, did you film it? You not mind?

“He is her Fuckbuddy and nope I was not present and no I don’t mind” I replied “I love her fucking other men”

And here is where the plan worked.

“Well I gotta have a pull” he said.

He stopped the video, and rewound it as he stripped naked

His circumcised cock was fully erect.

The first time I had seen him with a hardon.

Nice and straight, about 6 inches, with a nice purple bellend.

Here is where my plan veered off course somewhat.

“Cummon” he said “I aint sitting here naked, wanking, while you stay dressed. Strip off.”

“Oh shit” I thought.

I had my sissy gear on underneath, and I had not planned to show him.

Now I could have darted to the bog, and took them off, but he insisted I strip there and then

“Cummon,I know what your cock looks like” he said “No need to be shy now, Or are you bothered by seeing me having a wank?”

“No” I said “Your house your rules “

“Well gerrem off”

“Ok you ready for this” I said and stripped down to my Stockings, Knickers, Bra and Lace Teddy

“Fuck me” he said as I stood in front of him, red faced.

“You’re a fuckin’ Tranny too?” and then he said “You kept this quiet”.

“Oh yeh as if I would tell the world I am a Bi Cuckold Tranny”

“You say Bi?” he looked puzzled.

“Erm yeh” “Shit” I thought, I pushed the limits too far

“So you like cock?”

“Yes” I said beginning to shake

“You like wanking and sucking blokes?”


“You been fucked up the arse?”

“Once or twice, yes” I said.

“That’s good “he said “Cos I want to fuck you while I watch the video of Helen fucking.

” You fucked a bloke before?” I asked.

“Yeh “he said.

“When have you done that?”

“Usually when I am away” he said.

“Ok” I said “What do you prefer to do?”

“I don’t mind being wanked, sucked, and fucking arse, but don’t expect me to suck or wank you, cos I don’t do that”

“Fair enough “I said

“Ok what do want me to do?”

“On your knees facing the telly, so I can fuck you, while I watch her.

Dutifully I knelt down, bent over on all fours, and spread my thighs.

He spat on his hand, rubbed it into my hole, and then spat again.

I felt his cock pressing against my hole.

He was rubbing the head in the spit, and then he said “You ready?”

Before I could say no he rammed his cock right up me.

“Bastard” I thought.

It really fucking hurt.

I could hardly breathe and my ring was burning.

He pulled out nearly all the way, spat on his shaft again, and drove it back in.

John had one hand on my shoulder, holding me in position, whilst his other hand roamed over my arse and stockings.

"This is what Helens getting, how’s it feel?” he asked.

"Fuckin’ great" I replied as I began to push against his stroke.

John continued fucking me, while watching Wayne fuck Helen on the telly.

Onscreen Helen changed positions.

She lay on her back, putting her legs over Waynes shoulders, as he buried his cock deep in her again.

John said "C’mon lets do this properly, on yer back“.

I flipped onto my back, and lifted my stockinged legs over his shoulders.

His cock was soon buried back up my arsehole.

John tried to match tempo with Wayne.

I knew that this bit of the video, where Wayne was fucking Helen on her back, lasted just over 8 minutes.

During the last couple of minutes, Wayne was really pounding fast and hard at Helens sloppy cunt.

I didn’t know whether John would be able to last till the final couple of minutes, and if he could, would he be able to match Waynes frantic fucking.

More importantly, could my sore arse take it?

So here I was, lying on my back, with my stockinged legs over the shoulders of my mate John, who was fucking me, hard up the arse, as he watched a video of my wife Helen, being fucked by her Fuckbuddy.

John was doing his best to match his stroke, and speed to Waynes, as he fucked Helen on the screen.

I knew that Wayne would be shooting his load up Helen shortly.

I wondered if John would follow suit, and shoot his load in me.

On screen Wayne began the climb towards orgasm, and began pounding Helen quicker, with harder deeper strokes.

John matched Waynes tempo, and I could feel the twitching of his cock inside me, that said he would be filling my arse fairly soon.

John's face began to contort and he gripped my shoulders tightly as he pounded into me,

He gave a grunt, pushed his cock deeply into me, and let his cum fill my arse.

On the telly Wayne was shuddering, filling Helens pussy with his cum.

"Now you know exactly how Helen felt” said John as he slipped his softening cock out of me.

John slapped his cock on my arse a few times, to unload the last few drops of cum.

He said “cheers that was great, we must do it again soon.”

“Deffo” was my answer as we dressed.

I left his house excited, horny, somewhat embarrassed and with a sore arse now leaking cum into my undies.

It was Boxing Day before I told Helen that John had fucked me.

I informed her that John had fucked me, whilst we were watching the video of her being fucked by Wayne.

I also confessed that I had been wearing stockings, a bra, and a black lace teddy.

At first she was none too happy that I had shown John the video.

After a few hours of thinking about what I had told her, she decided it was horny. So she ordered me ring John, and tell him to be ready for me and her, as she wanted to watch a repeat performance.

We arrived at Johns, and as soon as were inside he told me to strip, and was soon naked himself.

Helen lay on his couch, and bared her breasts, commanding us to "Get on with it then".

John fucked me in various positions.

Helen watched, and played with herself.

As John fucked me Helen stripped off.

She told John not to shoot inside my arse, as she had another idea for a finale.

She told me sit on the floor, and for John to stand in front of me, with his cock in my mouth.

I was in heaven; I now had my missus naked, as I sucked my mates cock.

Helen then stood behind him, pressed her breasts into his back, whilst reaching round, and grasping his nice hard cock.

She wanked his cock in my mouth, as he reached behind, and fingered her.

As John grunted he was cumming, she pulled his cock out of my mouth, and sprayed his cum all over my face, like she was using a hose to water the garden.

My face was covered in his warm, sticky cum, it felt fantastic and the smell of warm cum was gorgeous as it dripped down my face.

Helen let go of his cock, knelt down, and began to lick some of the cum from my chin.

After we cleaned up, dressed, kissed, and said goodnight, Helen told John that it was one of the horniest things she had seen and done, and that she hoped for a repeat session.

Well, as it happened it, was about a fortnight later after Helen and I had been for a little late night dogging, with absolutely no luck.

On the way home, as we passed Johns house, we noticed his lights were still on.

Helen said she fancied another little show between me and John, so we gave him a knock.

John answered in just his dressing gown, “Hello you two” he said “What brings you here at this time?”

Helen told him she wanted to watch me sucking his cock again.

“Suits me fine” he replied “I was just going to have a wank”.

In his living room I stripped down to my usual stockings and bra.

John and I stood closely together facing each other, wanking each other slowly, as Helen watched from the couch.

“Never mind playing with each other” she said “I want to see you fuck his face” she said to John

So I then knelt in front of him, and swallowed his cock.

While I was sucking and swallowing him, Helen stripped off.

She stood over my kneeling body, facing John and told him to fondle her breasts, as I gobbled him.

As he groped her tits, he slipped some fingers into her wet pussy.

I stopped sucking his cock, and told Helen I wanted to watch him fuck her.

They lay on his couch, John behind her.

She drew her knees up to her chest.

I watched her face, and knew the moment he entered her.

I could see his cock inside her, through her parted thighs.

He began to fuck her slowly, at first as I watched.

After a few minutes, I put my head down and began to lick her pussy and his cock as it slid in and out of her soaking minge.

I began licking his balls and sucking them, leading to John to informing us he was near to cumming.

She told him not to shoot inside her, but to fill my mouth instead.

It wasn’t long before John pulled out of her.

He shoved his cock deep into my mouth, and squirted.

It felt like he was shooting his load for ages.

I swallowed some, and then he pulled away.

He rubbed his cock over my face, squirting over my face and chin.

He finished by shaking his cock, and wiping the last drips of his cum on me.

We cleaned up, dressed, and said goodnight.

We have not repeated the experience since.

Helen, however, has had many more fuck sessions with other guys.

More episodes to come if anyone is interested.