Halloween Crossing

It all started off so innocently...

My wife Jo, tall, slim, blonde, aged 40 with 34DD tits and the sexiest big ass imaginable, works as a doctor. Her hours are long and arduous. She often comes home completely worn out. Only during the holidays does she tend to recover her sparkle. She is gorgeous, but recently our sex life has become a bit humdrum and mundane.

Then, about a week ago everything changed. She arrived home really excited, literally like a child on a Christmas morning.

"What's got into you?" I asked noticing her joyful exuberance.

"Well. You know I love parties?"

"Yes honey, you adore parties."

"Well, we've both been invited to a Halloween party this weekend."

"Great. Sounds fun. Where's it being held?"

"At James'."

"James'?"

"Yes, you know James."

"No, I don't know any James'."

"Oh sorry darling. He's one of the new junior doctor's I've been mentoring. He's got this massive apartment he's shares with a couple of the other juniors and he's invited tons of people from work - doctors and nurses."

"Like to see you in a nurse's uniform."

"Well, you're luck might be in."

'What do you mean?"

"Well, it's a fancy dress party."

"And you're going as a nurse?"

"A very slutty, tarty one."

"I'm liking the sound of this more and more."

Jo kissed me passionately on the lips, sliding her moist tongue into my mouth.

"What was that for?"

"Oh, I've been so busy lately and so tired. I know I can't have been much fun in the bedroom."

"That's okay. You're still very very sexy. And very very hot."

"And when we get home from the party I'm going to wear my slutty uniform for bed."

I took a sharp intake of breath. And felt my cock start to swell and rise and press hard against my boxer shorts.

"I'm just going upstairs for a shower darling. Shan't be long."

"Jo, before you go." My wife was halfway up the stairs.

"Yes?"

"What am I going to wear for this party?"

"Ah...the million dollar question."

My wife looked sheepish. Bashful.

"Now you've got me worried." I said.

"Well...oh please don't say no."

"No to what?"

"Well the theme of the party is the Rocky Horror Picture Show."

"And?"

"All the guys have to come dressed as trannies."

"You're kidding right?" My wife's eyes told me she definitely wasn't joking.

"You really want me to dress up as a woman."

"It'll be fun. I'll help you choose an outfit. And do you're make-up for you."

"Make-up?"

"You know just a bit of eyeliner, mascara and lipstick."

I could tell that if I refused Jo would be desperately disappointed. She really had been working awfully hard.

"Can we still go?"

"There'll be lots of slutty nurses there?'

"And tarty french maids."

"It's a deal."

Jo jumped into my arms and kissed me all over my face, lips and neck.

"You're the best husband in the world."

A FEW DAYS LATER

Jo and I took one more look at ourselves in the mirror. We both looked like sluts. Jo had kept her promise and was indeed wearing a dark navy nurse's uniform with three of the top buttons undone to reveal her ample cleavage (when I'd remarked she was likely to give some guy a heart attack, she simply giggled and said she'd be happy to give him mouth to mouth. She'd done the training). The uniform was also way too short, so that if she bent down even a little bit you could see the tops of her black fishnet stockings and even catch a glimpse of her satin red panties.

And me? Well I was dressed in a black bodice with pink trim, black stockings and black panties. Jo had put red lip gloss on my lips and a jet black bobbed wig. The accompanying size 9 spiked high heels were already killing me. Together we looked like something out of a cheap horror movie. But, when Jo had slid the stockings on me and I had pulled the panties on over them, I felt a thrill akin to an electric charge go through me and found an erection stirring so powerfully that I had to kiss Jo in case she thought the throb in my panties perverse. I felt confused. Troubled. I had never before considered wearing women's underwear - though obviously I loved it when Jo wore sexy lingerie to bed. Occasionally she would rub my cock with her used panties or use the delicate fabric to play with and stimulate my nipples - so maybe she knew something I didn't - at least not consciously - that is, that I had some suppressed longing to actually wear women's clothes. I dismissed these thoughts, reflecting that it was only natural to have these feelings. The ridiculousness of our attire coupled with the kinkiness of it would mean any guy would be a little turned on by wearing such an outfit - Wouldn't he?

"Come on my sexy lesbian. Taxi's arrived." Jo's voice broke my disturbing thoughts. I took one last look at myself in the mirror and made my way into the darkness of a cold October evening.

The cold helped to ease any last remaining stirrings of excitement. Twenty minutes later we arrived at a gated community of apartment blocks that had been developed for middle class professionals on the outskirts of the city.

We entered the main lobby of the reception area and apart from the security guard I was relieved to see no one else hanging about. In the lift Jo squeezed my ass and pressed her tongue into my mouth. She hand't been this frisky for months and I wondered what had got into her. She was clearly excited at the prospect of a wild evening out together. But even at that point I had no idea how wild it would become, nor how it would change me.

The elevator doors opened on the top floor. Before we even exited we could hear the cacophony of music and reverie coming from our final destination. We shared one final kiss before Jo reapplied some lip gloss to us both.

"How do I look?" I asked.

"I don't think you'll be short of offers." She joked.

"You neither Nurse Slutty."

The party host, James - dressed in an outrageously short maid's costume with pink fluorescent stockings and matching lipstick greeted us at the door. He kissed Jo on the lips and me on the cheek. I was a little taken aback but already was starting to relax. I'd feared I would be the only guy dressed as a tranny, but I would have been the odd one out if I'd arrived looking like a 'normal' guy. Every male at the party was dressed like a tart - some as slutty nurses, lots of french maids too, there were a few cheerleaders and several Frank N Furters.

As the party progressed everyone started dancing. At times due to the subdued lighting it was hard to tell if the person opposite you was a guy or a girl. But by now the alcohol had taken effect and I was starting to enjoy myself.

Every now and then I'd spot Jo and give her a little wave before another guy (?) whisked her off her feet for another dance - Jo loves dancing. There was also lots of touching and groping going on, but again - though it was definitely inappropriate (and again you couldn't tell whether it was a male or female doing it to you) - it wasn't entirely unpleasant or unwelcome.

In fact the longer the evening wore on, the stranger I started to feel. I made my way to the bathroom and stayed there for about five minutes just trying to get myself together. I wasn't drunk and no one had slipped anything into any of my drinks, but I felt a paradigm shift in the way I was looking at the guys at the party. Some looked ungainly and still very masculine in their outfits, but a few really looked the part. And that's what was troubling me. Jo and I - as far as I know have never been unfaithful to one another - of course you see other attractive people everywhere - but our marriage was sacrosanct. I had no desire to cheat on her. But I was definitely disturbed by my slight feelings of attraction and even lust towards these pretty men in their nurse's uniforms and french maid costumes. I made a decision there and then that we needed to leave before this Halloween party really did turn into some Rocky Horror Picture Show nightmare.

But as I came out of the bathroom, one of the guys dressed as a cheerleader - short red pleated skirt, red stockings and wearing only a pink bra filled with what looked like some silicon gel greeted me.

"I've been waiting for you to come out,' he said, rather flirtatiously I thought.

"Yeah, sorry about that. I was in there a while."

He ran his tongue along his pink lip-glossed lips and surprised me by taking one of my hands and placing it under his skirt until I felt his cock twitching in his panties. I was initially too shocked to say anything, but he and I both noticed I was doing nothing to remove my hand as his cock grew larger in my hand.

"Listen," I finally said, "I'm not like that. Flattered though I am."

"You do appear more than a little interested." He simply replied.

Still I kept my hand there paralysed by the range of emotions going through me. His cock was pulsating now and as the guy moved in closer I caught a glimpse of Jo over his shoulder. She was pressed up against the kitchen door snogging twenty-something James. They looked like two sassy lesbians and any jealousy was quickly dispelled when I felt the top of my bodice being pulled down and my nipples being kissed by this guy.

He paused for a moment pressing himself against me now and asked: "Do you want me to stop?"

By now Jo was facing me. She looked me straight in the eyes as James was unbuttoning her nurse's uniform and sliding his hands up her thighs. I was shocked to find I was getting turned on by her behaviour and this guy's physical presence. She smiled seductively and at that moment I suspected I'd been set up. But now I felt powerless to prevent whatever was going to happen, especially when another guy came over to me - one of the guys dressed as a slutty nurse - and started kissing my neck. I just caught Jo winking at me before these guys dragged me off to the nearest bedroom.

Now we were alone I began to sober up a little - the room was well lit with a large king size bed taking up most of the space. If I was going to escape I would have to do it now. But as I looked around the room I saw that there were several drawn pictures of men in lingerie with big hard cocks staring back at me. One picture showed three guys - all wearing stockings or fishnets - on a bed their legs and arms entangled with each other - two of the guys in a 69 position the other licking one of the guys' ass. My head began to swim again and when the guy who had been kissing my neck placed his lips on mine any lingering resistance broke.

As his tongue entered my mouth I felt longing, desire for him. He looked so incredibly sexy in his female nurse's uniform and gorgeous black stockings with a red line up the back of them. Unable to resist a moment longer I danced my tongue with his giving in to these new delicious sensations. It was like being hit by a tidal wave. My response heralded a new sense of urgency.

Suddenly all three of us were on the bed. The first guy lifted my panties and started kissing along the length of my cock. It felt amazing. The other guy was still kissing my lips but when he saw how I responded to his friend he lifted the hem of his uniform and offered me his own cock. He was wearing a pair of black lace crotchless panties and the effect of seeing his hardened cock spring free of these made me yearn to take his throbbing member in my mouth.

Everything that was happening was completely new territory for me. But as the first guy continued to give me oral wave after wave of pleasure created a desperation to have a cock in my own mouth. The first taste was okay - I felt little beads of pre-cum drop on my tongue, then slightly bigger salty drops. Undeterred I greedily began deep throating this guy driven by an insatiable hunger for my own release.

I could feel the first hint of an orgasm building in me now as the first guy's mouth and tongue circled my cock. Then Jo walked in with James. She was no longer wearing the nurse's uniform, but looked ravishing in her fishnets, black panties and matching bra. James, however was dressed only in his panties and stockings. Jo must have removed his maid's outfit.

For a moment it was like being the proverbial rabbit caught in the headlights. My wife had walked in on me having/giving oral sex with/to two guys all of us dressed as slutty tarts. But instead of being angry, she simply turned to James and said:

"Told you this would work."

"What are you going to do to him now then?" James asked.

"Turn him over boys."

I'd gone from powerless to helpless.

"James."

"Yes."

"Have you still got some of that sexy new lubricant I brought over last week?"

"Yeah. In the drawer."

"Would you mind getting it out for me darling?"

James came over to the bedside table and removed a durex play lubricant and handed it to Jo. She rubbed some on her hands and the tips of her fingers.

"Okay boys - Simon, Kelvin. Remove his panties. James kiss me for luck. James pressed his lips against my wife as Simon and Kelvin slid my panties off. My heart was racing - there were so many sensations coursing through my body. I felt a little jealousy rise up as Jo and James - no more than a couple of feet from me - played tonsil tennis. But when Jo started fingering my ass with the lubricant all jealousy vanished.

Jo kissed me once lingering for ages before she said to Simon:

"You first gorgeous, give it to him good and hard and proper."

I couldn't believe what I was hearing but Jo now started to flick my nipples - which she knows drives me crazy - as Simon climbed on the bed and after giving my anus a quick lick started pressing his cock against my ass. The mixture of Jo flicking my nipples, Simon's stockinged legs rubbing against my stockings and then Kelvin replacing Jo underneath me by licking my nipples was driving me insane.

Then I felt Simon's cock enter my ass slowly inching forward. At first it felt really lovely, new, peculiar, but in a good way. But the further inside me he went the more uncomfortable it became. And then it was painful, really painful. But Jo once more intervened darting her tongue into my mouth. This allowed Simon to complete his engagement. Much of the pain melted away. Jo's lips were replaced by Kelvin's and as Simon started gently thrusting I felt my own cock raging with pleasure. I'm sure it had never been so hard. It was pulsating with pleasure as was my ass.

Kelvin moved aside and joined James kissing my wife's breasts right in front of me and fingering her pussy after moving her panties aside as Simon's thrusts grew more powerful and urgent. Jo was sighing with pleasure. Now she lay down beside me and as soon as Kelvin removed her panties she beckoned James to enter her. The young junior doctor kept his silky panties on but lifted the top of them so his cock could fill my wife's pussy. It was so kinky, so hot, so damn naughty and such a turn on that I couldn't resist reaching out and stroking Simon's panty clad firm ass as he began moving and thrusting inside my sexy wife. Jo was so tuned on by this that she lifted herself up just enough so she could french kiss me.

Then I felt Simon's hands grab my ass as his urges became more primal and ardent. This was it - for the first time in my life a guy - albeit a guy dressed as a sexy nurse - was going to cum inside me. I watched as Jo - recognising Simon was close - arched her back (Kelvin was now kissing her tits) as James sensing both Simon's fevered thrusts and my wife's longing drove harder and faster.

Simon hands flicked my nipples now as he powerfully increased his tempo.

"Oh fuck. Yeah." He started to scream.

"That's it Simon. Fuck my hubby, darling. Fuck his little virgin ass right in front of me and James drive your big cock deeper into me."

That was all the encouragement both guys needed. Simon gave one more long penetrating thrust and then it happened. It was like an explosion going off in my ass. A lovely, weird thrilling explosion. Several pulses like little aftershocks followed the main eruption. Then as Simon started to calm and withdraw slowly from me, James screamed out:

"Fuck Jo, I'm coming. I'm coming. Yes. Yes. Oh fuck...yessssss."

It was such a sensational experience watching my wife's reaction to this well-toned sexy looking guy fill her pussy with his cum. Simon was now basking at the foot of the bed watching, as my wife was, trickles of his cum cascading down my legs.

"Oh fuck that's is such a turn on." Jo said. She hadn't had an orgasm yet and was clearly gagging for one. As was I. As was Kelvin.

It was then that Jo lifted Kelvin's little cheerleading skirt. She seemed pleased that he was wearing crotchless lace panties.

"Mmmm very hot. Now get your cock inside me and make me cum while I suck my sissy little hubby's cock."

It didn't take long for Kelvin to hit full speed and take Jo to the edge of oblivion. His movements were skilful. And I loved the way he would run his tongue along Jo's nipples and use his hands to rub underneath her tits - something she absolutely loves. But Jo was only teasing me with her tongue and however desperate I was to go over the edge clearly she wasn't going to allow me to...just yet.

This was driving me nuts - especially as it was so hot watching Kelvin in his little cheerleading outfit fuck my wife.

"Oh Jo I'm coming you fucking hot gorgeous naughty woman. I'm coming."

Jo released my cock from her mouth and I immediately joined Kelvin in sucking her tits just as Jo started bellowing.

"Fuck Kelvin. That's it. Right there. Right there my sexy cheerleader. Fuck me in front of my sissy hubby. Fuck me Fuck me. Fuck...me."

They climaxed almost simultaneously - Jo first and Kelvin a fraction afterwards.

It too only a few moments for Jo to recover her composure.

"Now sissy hubby - my little cocksucking hubby. My now bisexual cock loving hubby. Lick my pussy. Go on. Lick your wife's cum filled pussy. I want to see Kelvin's and James' cum in your mouth, on your tongue. dribbling down your chin before you put your little cock in my pussy."

I obeyed immediately. I was frantic. Like a man possessed with a hunger he's never known before. Soon I had cum all oner my lips, nose and chin. And all in my mouth and on my tongue. Jo even insisted we share a cum-filled kiss. It was sensational.

"Okay you're ready for your reward now my little bisexual, crossdressing hubby. James...take my hubby from behind while he does me. Fuck his ass James. Please fuck my hubby in front of me."

"Your wish is my command nurse naughty." James said.

As I entered Jo, James entered me. He needed no lubricant of course - my ass was still full of cum.

It was the most amazing experience of my life. Fucking my wife's still cum filled pussy while the young stud James rode my ass and fucked me for all his worth.

I didn't last long - and we were close to a three way simultaneous orgasm. James just beat Jo - it was thrilling feeling him cum inside me after I'd watched him fuck my wife earlier. Jo was next responding partly to James' screams of delight and partly to my own cry of:

"Fuck Jo I'm cumming. Thank you for letting me watch you get fucked by these sexy trannies but thank you most of all for turning me into a sissy cuckolding, cock sucking, cock worshipping tranny. You can fuck...oh yeah...fuck...mmm...whoever you want...yeah...aargh...fuck... from now on. Oh fuck I love wearing panties and stockings"

LATER

At home we fell into a deep sleep in seconds. I awoke to find Jo had gone to work. But she had left a short skirt, red fishnets, pink satin panties and a black and ivory basque from Victoria's Secret on the bed for me with a note:

"I'm in charge now sissy hubby. Have these on by the time I get home. I'm going to be full of cum and I want you to eat me out my little cock sucking tranny. Do it well and I may take you out to a nice little club I know where men want to fuck women hard...especially little sissies like you. And maybe they'll let you fuck them provided you let them fuck you naughty wife first."