Chapter 9: The Last Taboo

Introducing Kate left one last thing that I wanted my wife to experience: Her husband being fucked by another man.

Earlier in this piece and my ‘Introduction to... ‘ series, I’ve observed that having something in my ass does nothing for me sexually. I don’t dislike it, but it doesn’t turn me on, either. All I feel is a vague need to shit.

Even when something is scraping across my prostate, something most guys adore, I don’t feel any sexual arousal or stimulation. I desired to have my wife observe me taking a cock in my ass, but I doubted I would garner any pleasure from it. Getting a masculine male to fuck me would be purely for her enjoyment, not mine.

I turned to the internet again.

Wow, there are many more gay/bisexual curious men than I had ever imagined, and most of them are wannabes and tyre-kickers. Close to 98% of the men who have approached me wanting to get with my wife and I have never followed through. I believe they jerk off to the fantasy as you exchange messages, and when the fantasy pales, they stop responding.

Notes:I based Samuel from my ‘Tranny Babysitter’ series on the man I allowed to take my anal virginity. My first time indulging in man-on-man sex was very close to how I described it in ‘The Conclusion’.

There was no ‘Hannah’, obviously.

I was a truly gifted athlete. I won many national and provincial titles as a teenager. After I moved to Australia in my mid-twenties, I realised that AFL would have been my sport of choice if I had been born here. I’m tall, have an elite vertical leap, have excellent hands, and am a great ball kicker. Plus, I could run all day, every day.

In conclusion, I would have been Nick Riewoldt ten years before Nick Riewoldt.

However, my descriptions of how my AFL career in that series progressed were accurate. If only I had the mental toughness of my older brother, I would have been a sports superstar.

Back to the story...

Vicky, Anna’s and my sex life was awesome. I loved watching the girls getting it on. I loved fucking Vicky as Anna tongued her clit. I adored fucking Anna’s ass as Vicky went down on her.

My life couldn’t have been any better. I had two women who adored me and adored each other.

Despite a misstep with Albert, Vicky and I had chosen our submissives perfectly. However, there was one last thing I wanted my wife to experience before I could say that I had done everything possible to expand her sexual horizons.

I met a few men trying to find one I was sexually attracted to so I could let him fuck me in front of my wife. It was a fruitless exercise. The men I preferred more closely resembled Kate than John Rambo (randomly picking a hyper-masculine male).

Note:To this day, I prefer femmeboys to men. I love MMF sex, and my wife and I indulge in it regularly, but masculine men still leave me cold. However, there’s an exception that I’ll explain later in this piece.

Back to the story...

As a teenager, I had indulged in some crossdressing. I didn’t want to become a woman, but I loved the thought of becoming so feminine that straight males would want to fuck me.

I grew up in rural New Zealand. In the early 80s, as I turned old enough to have sex legally, I quickly realised that ‘there weren’t no pooftahs in rural New Zealand’, or so people would have you believe. Therefore, my crossdressing had to be a carefully guarded secret.

I’m very hairy, I mean Robin Williams-type hairy. In my opinion, hairy crossdressers just look ridiculous. I know, I know, each to their own. I don’t have any problem with anything anyone does to stimulate their sexuality as long as it’s legal, safe, sane, and consensual. If, being my size and as hairy as me, you find wearing lingerie sexually exciting, go for it and enjoy it.

I simply think it looks silly, probably because I’m only attracted to the feminine.

Winter became ‘tranny time’. During the winter, I wore long-sleeved shirts and long trousers, so the fact I was clean-shaven from the eyebrows down wasn’t noticeable.

Because of my nervousness about being outed, I never shared my crossdressing fetish with anyone. But whenever I was between girlfriends or depressed, I found myself bringing ‘Marie’ out of the closet again.

Because of my fit, toned body and exceptionally long legs, from the neck down, I look quite frankly as sexy as hell when I’m all dolled up. Add some breast forms and a painted cleavage line, and as long as no one looks higher than my tits, I’m fairly convincing.

Thinking things through, I decided it was time for Marie to reemerge. I hoped that, dressed as Marie, I could allow a masculine male fuck me.

Note:I’ve never understood why men find it so difficult to admit they like dressing up as women and playing the feminine role. I do understand the fear of being outed and becoming an object of ridicule. I had someone I worked with show my Marie Facebook profile to everyone in the office.

Luckily, my workplace was very supportive, and that person got in trouble, not me.

Back to the story...

I wasn’t sure where to start, so I joined some groups on Fetlife to see if I could find some men with similar predilections to me to chat with. The people in these groups were incredibly supportive and offered plenty of sound advice. Most of the advice was to keep my fetish hidden from my wife because it would end my marriage if she found out.

Note:The above is sadly true, and is why suicide amongst transpeople is so high. Upon beginning their journey to their true authentic self, the poor girl often loses their support group. Their wife leaves, their kids don’t want a bar of them, their friends disappear, plus their workplace often becomes a living hell.

Be kind, be supportive and be generous with these people. They’re amongst the gentlest and most beautiful friends you will ever have.

Suppose you’re not sure whether someone in your vicinity is a male or female. In that case, I want you to follow these steps: Remind yourself that it doesn’t fucking matter, and it’s none of your fucking business, and move on!

Back to the story...

I never considered not bringing my wife along on this new journey. However, I kept it hidden for a time as I created a wardrobe for Marie, learned how to do my makeup correctly, and learned to walk and talk like a woman.

Note:As described in my Tranny Babysitter series, I never managed to sound like a female newsreader, but I can still do a damned impressive Bea Arthur.

Back to the story...

Once I was satisfied I was as feminine as a large masculine male could make himself, I visited Arpi at ‘The House of Transformations’ on the Gold Coast and had some glamour shots done.

Arpi describes herself as a femmeboy, and she has professionally done film and stage makeup for years. As a result, Arpi is an expert at feminising a male’s face. You can see what I mean by looking at Arpi’s web page gallery.

Downloading the photos Arpi had taken, I took a deep breath, then called Anna and Vicky over. Arpi had done her work so well that it took the girls five or six pics before they realised they were of me.

“Jaysus, John!” My wife exclaimed. “You promised life with you would never be boring, but fuck me!”

My heart sank as I thought I’d erred badly by bringing this into our lives.

Before I could say anything, Vicky asked, “Do you want to transition to female? I could probably handle that, but your cock needs to keep working!”

Gawd, I love that woman.

Laughing, I reassured Vicky that this was a persona that I had created so I could experience playing the feminine role during sex. I further explained that I wanted her to feel the rush I felt when she and Anna got it on.

Anna spoke, “I think this will be a hard limit for me, Sir. I have no problem with your dressing as a woman, but having you in a submissive role as we have sex will be too weird for me to handle. So I prefer to be left out of any sex play you have as Marie, please.”

“Are you happy to be seen with me dressed as Marie in public?”

“Yes, Sir. I think you make quite a pretty woman. It’s not that you’re feminised that I’m struggling with. It’s you being submissive that I can’t contemplate.”

I hugged Anna and smiled, “It’s just as well that I didn’t want you to be part of Marie’s sex life then, isn’t it?”

Anna returned my hug gratefully.

“What happens now?” Vicky asked.

“I’ve been put on to a couple of websites where bisexual and crossdressing men can meet. I want to troll through and find a masculine male that would like to come and fuck us both.”

“Definitely not boring,” MsV muttered. Then, speaking louder, she said, “I’m not sure I want this. Will you go and get dressed as Marie? Then I’ll see if I can make love to you when you’re she.”

I won’t bore you with the details here, but for me to completely transition from a hairy masculine male to a reasonably respectable woman takes almost 90 minutes.

I do not, in any way, as a complete package, pass as a woman. But the sentiments expressed in Tranny babysitter hold true. If you stick your ass out, keep your shoulders back so your tits stick out, and perfect that hip sway walk described, ain’t no heterosexual man looking at your face!

Eventually, I made it back to the playroom. Anna sat shaking her head. Vicky asked me to stand still in the middle of the room as she looked me over.

“And Marie is quite submissive, is she?”

Using my ‘Bea Arthur’ voice, I replied, “Not really, but it’s role play, and as you know, I’m pretty good at that.”

“What was that?” Vicky exclaimed. “Where did you learn to sound like a woman?”

“YouTube videos.”

Anna was still shaking her head.

“You okay, little one?” I asked.

Anna answered, “Yes, Sir. I’m just stunned at the transformation. You look quite sexy, especially from behind, with your tight, shapely ass and long-toned legs. As long as I don’t look at your face, I could easily believe you were a woman.”

I laughed, “Then I’ll have to wiggle my ass like a right slut and keep the boy’s eyes on it, won’t I?”

Vicky laughed, too, “Go on then, show us your ass wriggle walk.”

I strutted across the room, placing my heel only slightly in front of my toe.

“Damn,” Vicky said. “Hang on, let me try that.”

Anna decided to join the fun, and we all practised hip swaying across the floor.

Vicky took my hand and placed the back of it against her pussy. She was warm to the touch.

“Take me to bed, baby, please.”

I picked her up as effortlessly as I did on our marriage night and carried her to our bedroom. Anna followed us.

“Just us,” Vicky told her, to Anna’s pout.

All I took off as I made love to my wife was my control brief. A control brief does precisely that. For women, it gathers up the loose skin and holds it all in place. For men, they allow you to tuck your cock and balls out of the way, and they stay there.

With it on, there was no way to use my penis.

By the time we finished, I needed to drop my wig off at the hairdresser’s to be straightened out and remodelled. And we both needed to wash our clothes as I’d smeared makeup all over us.

Cuddling me close, Vicky said, “Okay. I can definitely play with you dressed like this. It’s quite fun, truth be told.”

I squeezed her tightly to me. I nearly sobbed because of how happy she made me.

“Do you really think you can let a man fuck you dressed like this?”

I both shrugged and shook my head, “I don’t know, babe. But I want to try at least.”

“I don’t need this, John. You know that, right?”

“I think you do, Chubby. Knowing I will do and try anything and everything to make you happy is important.”

Vicky slapped my arm, “You do make me happy, you big oaf. You don’t need to let some random guy ass fuck you to keep me that way.”

“Okay, I admit it. I want to feel what it’s like. What it feels like to have a cock cum in your ass. What it’s like to be the receiving partner in a sex session.”

“That’s better, that I understand. The boys are due home soon, and I don’t want them to see you like this, ever, okay? So go and get showered and changed, and we’ll have a look at these websites.”

We didn’t have any luck at all on any of the websites we tried. Running ads where we invited people to come and play didn’t work either. Oh, we got 1,000s of replies, but few genuine ones.

Most, it seemed, would put up with some play with me so they could fuck Vicky, but few wanted what we wanted. We wanted the man to primarily be there to fuck me. As a reward for doing this well, he would get to play with MsV, too.

Trolling through the replies, MsV said, “This is a waste of time. I doubt any of these pricks have even read the ad, let alone our profile. We need to try something else.”

“We could try a gay bar,” I ventured.

“You’d let someone pick you up at a gay bar?”

“Looks like it might be the only way. Unless you want to try a gay beat?”

“Hell, no! We’re done if I ever find out you’ve been to one. Do you hear me?”

I grinned, “Yes, Ma’am.”

Vicky glared at me, then dissolved into laughter, “You’re such an asshole, sometimes.”

Dressing as Marie, we tried The Sportsman Hotel first. Unfortunately, the clientele there is more gay than bisexual, and I didn’t get approached by anyone to whom I felt attracted.

For the next three Friday nights, we tried The Wickham. There were more men I felt were suitable for my needs, and I chatted with quite a few, but no one took the step of asking me home.

About halfway through the third night, I was sitting at the bar by myself. Vicky was in the loo.

Dropping my woman’s voice, I asked the barkeep, “So what does a girl need to do to get fucked in this place?”

The barkeep was an older gentleman I had wrongly assumed was gay—attracted to the masculine, not as I presented.

He replied, “Ask the right man to come home with you.”

Shocked, I straightened up, “You’re saying you’re the right man?”

In his smooth cultivated voice, Mark (by his name tag) said, “Maybe. I like how you look and would gladly take you home to fuck. But what’s the deal with the woman? Is she a ‘fag hag’ hanging around you hoping to score a gay guy?”

Further surprised, I answered, “That’s my wife and co-dominant play partner.”

“You’re not dominant though, are you, Miss?”

“Not dressed like this, no. But usually, you know?”

“So this is a role play, play time type thing?”

“Kind of. I’ve been working on expanding my wife’s sexual horizons. Having a man fuck me is next.”

“Is your wife included in the play?”

“As long as you remember that your primary task is to take my anal virginity, then, yes. All holes on both of us are available.”

“You’re an anal virgin?”

“With a real cock, yes. My ex-wife used to delight in using her strap-on on me, but I’ve never had a real cock up my clacker.”

“How long ago was that?”

“Was what?”

“When your ex-wife was ass fucking you?”

“Oh. Fuck. Years. And years,” I qualified.

“Have you been using any toys?”

“Yes. I can easily take my biggest plug. Well, when I say easily ... With a little effort, you know?”

“How big is your biggest plug?”

“It’s bigger than my cock. I carry around seven thick inches.”

“Come with me.”

Surprised at his sudden dominance, I meekly followed him around the corner to the staff loos. Checking that they were empty, Mark ushered me into a cubicle and then sat in front of me.

“Pull your skirt up and take your cock out.”

I did as instructed. Mark held me in his hand and then took me in his mouth. I was terrified, but my cock’s brain, the one that controls most of us males, went, “Hmm, blowjobs are always welcome’.

Letting me out of his mouth, Mark said, “Good girl. I think I want in. Can you wait until my shift finishes? Then you can both come back to mine. Nobody’s home, so that will work.”

Gasping with desire and my cock throbbing, I asked, “What time does your shift end?”

“1.00 am, about two hours from now.”

“Okay, we’ll wait.”

“Bring your wife over so I can check that everything’s hunky-dory, okay?”

With a grin, I replied, “Yes, Sir.”

“Get used to using that, honey. If you’re going to be ... what’s your girl’s name?”

“Marie.”

“If you’re going to be Marie when you’re with me, then I’m Sir to you, okay?”

“Yes, Sir.”

Note:I’m not submissive. I’ve never felt the desire to submit to anyone. The biggest cause of friction between Mistress Eliza and myself was that I wouldn’t submit to her. However, I loved the kinky sex we were having. Therefore, I put up with the ‘other bullshit’ so I could continue to fuck her and her submissive Becca.

It’s widely held that no one is 100% submissive nor 100% Dominant. We’re all a switch to some degree. I was a switch for as long as I knew I was playing a role. Once the role was over, i.e. my partner had cum, I immediately returned to my usual persona.

Back to the story...

Following Mark back into the bar, I found MsV standing, looking around.

“There you are,” Vicky said. “I wondered where you’d gone.”

“This is Mark,” I told her. “He wants us to come home with him tonight so we can play. Mark, this is my wife, MsV.”

“Pleased to meet you. I have to get back to work. Come and sit at the bar, and we’ll chat as I serve.”

Mark walked briskly back behind the bar. I went to follow, but Vicky pulled me back.

“What happened there, and why do you have a hardon?” My wife asked.

“Mark took me into the staff loos to see if I would let him blow me.”

“Obviously, you did.”

I blushed, “I think he might be almost as good a Dominant as me. He just took charge, and I couldn’t say no.”

“Okay. And you’re happy to do this?”

“That all depends on you, my love.”

“He’s very cute. Most gay guys are.”

“I don’t think he’s gay. I think he might be an ‘equal opportunity letch’.”

“Meaning?”

“He’ll fuck whatever is available. Men, women, and anything in between.”

“Like you.”

“Yes.”

“Let’s go chat and see where this leads.”

Mark was cultured, extremely sophisticated, intelligent, and well-educated. He worked at a bar because he liked the job and loved talking to and meeting new people.

Note:I met Mark when I was a few months short of my 49th birthday. Mark was almost ten years older than me. For most of Mark’s working life, he’d been a flight attendant.

“It was awesome,” Mark would say. “The ‘trolley dollies’ (his name for the female attendants) all assumed I was gay because (in a terrible lisp), we all are, right? And they would happily undress in front of me. But, boy, did I shock them when I shoved my stiff cock in their faces.

Most of those sluts sucked it like all good girls should, though.”

Mark preferred transgirls, but his sexual proclivities ranged widely. Unfortunately, Mark died of a brain aneurysm four days after his 70^th birthday party.

Back to the story...

I watched, amused, as Mark turned his considerable charms onto my wife. He soon had Vicky eating out of his hand.

“So, tell me, you slut,” Mark lisped at Vicky. “How much fun are you going to have watching me fuck your husband’s ass?”

Laughing at his audacity, MsV replied, “Lots, I hope. Assuming you’re not a two-pump chump, Mister Mark?”

“Darlink, after your husband begs me to stop, I’m going to fuck you until you have to beg me to stop as well. Then, now that I would have warmed up, I’m going to fuck your husband again until he collapses from exhaustion.”

Laughing delightedly, Vicky said, “Gotta love a man with confidence! But talk is easy. It’s actions that count.”

“They don’t call me ‘Action Jackson’ for nothing. Well, they don’t, but I wish they would.”

Mark’s last name was Seymore, so it’s no wonder they didn’t.

“You know, Mistress Victoria, I believe you were a sweet innocent Christian girl before your man whore over there turned you into a raging slut.”

Vicky glared at me, and Mark laughed delightedly.

“I see I hit the mark immediately. But, honey, your man didn’t tell me a thing. I just guessed.”

Vicky still stared daggers at me.

“Oops,” Mark said. “Vicky, John and I weren’t gone long enough for him to tell me anything much. I was truly only using a little intuition and people reading skills to guess.”

“I’m not a slut,” Vicky muttered.

“No, honey, you’re not. You’re just an earthy girl that has learnt sex is fun. And, great sex is even funner. I’d bet hundreds of your girlfriends wish someone would teach them as your husband has taught you. You both should be very glad of the other.”

Vicky squeezed my arm, “I am. Without John, I’d probably have married the accountant chasing me, had six kids, and been eight foot across the hips.”

I hugged my wife, “I’ve been the lucky one, babe.”

Mark laughed, “Enough of this gawkish sentimentality. My shift is done. Time to go home and fuck!”

Mark usually caught the train into town, so he walked with us to my car and then directed us to his home.

Arriving at Mark’s house in Clayfield, I commented, “I obviously chose the wrong career, look at this place!”

“Oh, darlink,” Mark replied, lisping again. “You’d have been very popular on the overnight trips as well. You never know. You may have even scored the trolley dolly’s favourite, a pilot.”

Mark showed us inside, then upstairs to his bedroom.

“I have three housemates, but they’re all off on flights at the moment, so we don’t need to worry. You two can make as much noise as you want as I fuck you into nirvana.”

Mark dropped his trousers, and his solid 8-inch todger sprung into view.

“Now, which one of you sluts wants to suck this first?”

Vicky pushed me forward. Nervously, I knelt before Mark and wrapped my hand around his thick shaft. I wasn’t worried about being able to deep-throat Mark. Once you can accept a cock over your gag reflex, how much longer than that a cock is doesn’t matter as it’s past where you gag.

I was worried because Mark had had many male given blowjobs, and I didn’t want to look like a rank beginner, even though I was.

Mark was at least an inch longer than Kate, the only other cock I had sucked. Plus, he was much thicker, so I wondered if his extra girth would be a problem. I needn’t have worried, though. Mark’s thick cock slid over my gag reflex and down my larynx without a problem.