Sissy Boi

I stood up, kissed Ted passionately on the lips as he fondled my breasts removing them from my bra so he could squeezed my nipples. Then I bent over my desk again. I felt Ted's hands on my thighs and ass, then he moved my gusset aside and started penetrating me. It felt insanely wonderful and naughty. My phoned pinged. It was Dan. His reply was very revealing.: I was in a meeting when I received that! Anyway, Dr Hottie, I have to admit that I'm very tempted!! How's your morning going?

I was overcome with excitement by Dan's response. He would soon be my crossdressing sissy cocksucker. Gosh, I thought, I'd love to watch him suck Ted's cock. Ted's cock was now deep inside me. I hadn't experienced anything like this before. He was a sensuous and delicious lover. As his rhythm increased I texted Dan back: Very busy morning! Should be done soon!! Can't wait to go lingerie shopping with you later. I'll bring a pair of my dirty panties for you to wear, probably the ones I'm wearing now, which will be filthy by the end of the day.

I turned my head and enjoyed a French kiss with Dan as he neared his zenith. I loved his urgency, his cock was filling nearly every inch of my pussy. I didn't even feel guilty. I had decided Dan was going to be my cuckold, and if I had any doubts at all Dan's next response, assuaged them immediately: I love being your sissy xx Enjoy the rest of your morning.

I felt so happy and naughty at the point I responded by texting: Oh, believe me, my little sissy boi, I am! xx That's when I felt Ted's lovely cock tense, pulsate, and fire streams of cum into my pussy. The hot liquid felt amazing and instantly I grabbed one of Ted's hands and got him to rub my clitoris. I came in seconds - the orgasm hit me like a series of tsunamis - wave after wave after wave of pleasure. I had to put my hands over my mouth to stop me from screaming.

After Ted left to: "Same time, same place, next week?'

"It's in my diary, Dr Hottie, you sexy woman."

I sat in my chair basking in the afterglow of great sex. Sex with Dan, I thought, is now really nice, but sex with hunks is fucking off the scale.

Martina came in a few minutes later. She looked at my ruffled blouse and said:

"You didn't? You did?"

"Of course I did. He looks like Thor and he has a hammer to match."

We both burst out laughing.

"I'm going to try and get him over to my house for an orgy. Fancy coming? You can bring the other nurses."

"Including Clive?"

"Absolutely."

"What about your hubby?"

"Oh, we'll let him and Clive dress as slutty nurses and fuck each other's man pussies."

We laughed uprioariously again.

"You are such a naughty doctor."

"I know!"

LATER

By the time I met up with Dan at the shopping centre, I was feeling horny again. I kept catching the aroma of my pussy juices and Ted's cum in my panties, and it was driving me wild. I greeted hubby with a passionate kiss. We went first to Ann Summers, they had a new black silicon rampant rabbit that had rave reviews. Then I stunned Dan by asking, the make shopping assistant, Richard, for a hand picking out a strap-on.

"This," he said pointing to a very realistic looking seven-inch black veined dildo, 'Is our bestseller. It has six vibrating settings, a silky smooth shaft, and the soft leather harness can be worn easily over your panties.

"Sounds amazing, Richard," I said, very flirtatiously. "Would you mind coming in the changing room with my hubby and I and showing me how to put it on?"

"It would be my pleasure."

Dan looked both horrified and aroused. He was speechless, but the look in his eyes was one of bewilderment - at how terribly perverted his wife had become - and lust.

"Dan, darling," I said, as soon as the curtain was drawn. Would you mind undressing me and yourself?"

"Of course I don't mind," Dan replied, looking like he was in a stupefied trance.

There was an electric charge in the room now. Richard looked ecstatic as my sissy hubby, took off all my clothes including my bra and panties.

Once we were both naked I insisted Dan put on my cum-stained lace panties and my bra.

"If I'm going to fuck your man pussy hubby, you've got to look like a woman. Isn't that right, Richard."

"Well, of course it is..."

"Jo, my name is Jo."

"Of course it is Jo. When I fuck my boyfriend I always make him wear my wife's panties and bra."

"There you go, Dan. You've heard it from the horse's mouth." I winked at Richard and squeezed his ass. Dan didn't bat an eyelid.

I went in my bag and brought out a pair of pink ruffled panties. I asked Richard to put them on me.

"Happy to oblige, Jo."

"Oh darling, Richard's being so helpful, isn't he? Do you mind if he kisses my lips and feels my tits while he puts the strap-on, on me?"

"Not at all, Dr Hottie." Dan was completely lost in sissy land now. The power I had over him gave me such a sexual thrill that I decided I was actually going to fuck him with the strap-on while Richard played with my tits and ass.

The strap-on felt so naughty and once I was wearing it I felt a flood of pussy juices pouring out of me.

"Richard would you get my love juices from my pussy and lubricate my sissy hubby's ass with them."

"It'll be my pleasure."

Richard's hand was firm and assured. He told Dan to bend over and he then moved my cum-stained panties aside so he could lubricate Dan;'s ass with my pussy juices. It was so hot watching him do this I almost had an orgasm. Dan sighed with delight. And that delight turned to pleasure as I started fucking him with the strap-on. I felt like an out of control guy thrusting for all my worth with my big cock, and with Richard fondling my tits and ass with his hands and tongue, I felt an orgasm beginning to rise.

Dan was starting to groan and because there were mirrors in front of him and behind me, we could see each other's perverse expressions. I could also see Dan's cock leaking precum which spurred me on to more vigorous thrusting. With Richard now grinding his cock on my panties, which Dan could clearly see - but showed no signs of objecting to - I became wild with lust. I gave several more potent thrusts and as my own orgasm threatened I saw Dan actually ejaculate. That gave me such an unbelievable thrill that my threatened orgasm instantaneously swept over me.

As I withdrew the strap-on, Dan turned round and kissed me, and I realised it was time, here and for stage six.

STAGE SIX

Richard was clearly gagging for it and I couldn't leave him frustrated.

"Richard, would you like to fuck me or would you like my sissy hubby to give you oral?"

"Can I have both?'

"Why you naughty boy. Of course you can. What are you doing later?"

"Nothing, I finish my shift in an hour, I was going to go for a drink, but I'm open to offers."

"Good." I gave him our address and my phone number. We bought the strap-on and the new vibrator, and several other pieces of hot sexy lingerie and headed home.

I got the plastic container out the fridge and told Dan to meet me upstairs. Underneath his suit he was still wearing my lacy bra and panties.

"How do you feel about sucking a cock?" I asked, putting on a new blue basque, stockings, suspenders, and black panties I'd purchased at Ann Summers.

"I think I'm ready for it, Dr Hottie."

"Let's make sure. Don't want Richard to be disappointed now, do we."

"No, Dr Hottie."

"You are such a good crossdressing sissy boi." I opened my laptop. "Now, look at these pictures. I'm going to put the strap-on, on again. Then I'm going to pour your cum from this container, cum I collected when you ejaculated the other night, onto my dick and make you lick it off. You see, sissy hubby, you won't be a fully-fledged sissy until you lust after more than cock. So, be a good sissy boi, do as I say. Look at the pictures, really focus in on them and if you do, I'll give you a treat at the end."

The pictures were all of Ted, he'd given me permission to take them, so I could show Dan, the hunk that had fucked his wife.

"Focus on his sexy stomach, Dan, and those perfect abs. Now look down to his strong powerful thighs. Tear your eyes away from the bulge of his big manly cock in his boxer shorts - so much bigger than yours, right? Now look at his strong chest. Bask in how strong and sexy his arms look. Imagine being held by them as he fucks you. Keep looking sissy boi. Now the real trick, look at his gorgeous sexy face, imagine being kissed by him. Imagine seeing his face contort with pleasure as you suck his cock or as your ass takes his big dick. Now take in the whole thing. Wow, Dan, you are so turned on, your cock is the biggest I've ever seen it, and you haven't even seen Ted's huge cock naked yet. here you go, have a good long look."

The next image wasn't a still picture, but a video, a video of my hand stroking Ted's big fat cock.

"What do you think, Dan?" How hot is Ted?"

:"So fucking hot. His cock is so much bigger than mine."

"What would you like to do to it?"

"I'd like to suck it, Dr Hottie. I want his cock in my mouth and in my ass while I'm wearing your underwear. I want his com in my mouth, and ass."

"Would you like sloppy seconds? Would you like to eat Ted's creampie out of your naughty wife's hot pussy."

"Fuck, yes, Jo, I mean, Dr Hottie. Yes, I'd love that more than anything."

I asked Dan to click on the final few image. Ted had taken them in my office this morning and emailed them to me. It showed him taking me from behind, fondling my tits, kissing my lips and cum dribbling out of my pussy and onto his dick after he had fucked me. I knew this was the moment why I would either make Dan a real crossdressing sissy cocksucker or lose him forever. I needn't have worried. His response was immediate and frenzied. He took the container out of my hands and poured cum on the strap-on, on my tits and in even in my pussy. Then he devoured it.

"That's the hottest thing I have ever seen," he squealed.

"You like your wife being a hot wife then and getting fucked by loads of young, healthy, masculine, fertile men?"

"Yes, yes, yes, Dr Hottie," Dan said, his own cum now completely vanished apart from a couple of drops on the strap-on. When I pointed this out, he immediately went down on my dick again.

"What if I told you the panties your wearing are the ones I was wearing when Ted fucked me in my office this morning. What would you do."

"I'd do this," Dan kissed me powerfully overwhelmed with desire and then slipped the panties off, sniffed them and licked the gusset over and over and over again.

"What an absolute crossdressing sissy you are now Dan. But you better put those panties back on, Richard has just arrived. It's time to suck some real cock my sissy faggot."

Richard was barely in the bedroom before Dan pounced. He ripped off his clothes and as I kissed Richard and he, in turn, played with my tits, Dan sucked Richard's cock like a professional. Watching my sissy hubby's little panty clad ass bounce up and down as he gave Richard oral thrilled me so much that I forced Richard to stroke my pussy, not that he needed much persuasion. Within minutes Richard exploded in my hubby's mouth. Dan was like a man who had eaten or drunken anything in days, he greedily lapped up every drop.

Dan then gave me cunnilingus as we waited for Richard to recover. Once he had, Dan again kissed his cock until it became stiff and hard and ready to penetrate me. Dan was rubbing his cock for all his worth as he watched another man fuck his wife for the first time. Richard was nowhere near as good as Ted had been earlier, but then he was ten years older, and he didn't last long, obviously turned on by the fact he was fucking another woman whose hubby was watching and clearly loving every minute of it.

As soon ar Richard climaxed Dan had his first proper cream pie and watching my darling hubby feast himself on another guy's cum pouring out of his wife's pussy sent me over the edge. It was so hot and naughty.

When Richard left, Dan and I had our best sex ever. I kept saying to Dan: "Repeat after me...I love men, I love cock, I love cum in my ass and mouth. I am a crossdressing sissy gay boi and I love watching hunky guys fuck my wife when I wear her panties, bra and stockings. I love men, I love cock, I love, I am gay."

STAGE SEVEN

I could easily have skipped this stage. Dan was now addicted to cock. So stage seven was over in less than a day. I sent Dan a picture of me sucking Ted's cock - which drove him insane - and then a ton of pictures and captions of both men and women doing likewise. My favourite one showed a naked wife kneeling behind her naked husband, she was rubbing his cock, he was sucking some hunky guy's big stiff cock and his wife was saying to him:

THAT'S IT, KEEP SUCKING HIS COCK YOU SISSY FAGGOT. I KNOW YOU LOVE IT. MAKE HIM CUM IN YOUR MOUTH FOR ME. YOU LITTLE BITCH!

Dan loved it. He texted back:

I love cock, I love cum, I love men. My wife has turned me into a gay crossdressing sissy faggot boi and I love it xxxx

Then, to seal the deal, I sent Dan another picture of me sucking Ted's cock. A close-up shot then showed my face and Ted's glorious cock. Underneath I texted:

YOU'RE NOT STRAIGHT ANYMORE SISSY HUBBY. STRAIGHT MEN DON'T WANT TO SUCK COCK LIKE THEIR WIVES xx

Dan's reply said it all:

TEACH ME HOW TO SUCK COCK LIKE YOU DR HOTTIE xx

I will, I thought, and plenty more besides!

STAGE EIGHT

Two weeks into the experiment and Dan wanted cock as much as he wanted my pussy. I was over the moon. I brought Ted home, dressed Dan in the same outfit he had worn for the Rocky Horror Show, I dressed likewise, and then Ted and I took firm control.

"Dan, you want to suck Ted's cock with me tonight. Don't you?"

"Yes, Dr Hottie. Yes, I do Ted."

"Dan, you are my crossdressing sissy cocksucking faggot boi."

"I am your crossdressing sissy cocksucking faggot boi."

"Admitting how gay you are in front of Ted and I turns you on."

"It really does Dr Hottie. I am such a sissy faggot Ted and I love wearing my wife's bra, panties and stockings."

"On your knees faggot. I'm going to put Ted's cock in your mouth. Open wider, wider still. That's it. Good sissy boi. now start sucking Ted's lovely big cock for me. Don't stop until you are full of his cum."

Watching my once straight hubby suck Ted's cock, the same big cock that I had sucked, the same big cocked that had fucked me in my office less than a week ago, was indescribable. To be so close to witness Dan eagerly sucking Ted's cock dressed like a slut was amazing.

As Ted got close, I joined in, sucking Ted's balls, as he prepared to unload into my hubby's mouth. We both felt Ted tense and the he shot his mother load into Dan's mouth.

"Every drop, sissy boi. No spillages allowed."

Dan lapped it up again like a pro.

"Hey, enough. Save some for me my naughty little faggot."

Dan apologised and inserted Ted's cock in my mouth. We passed it back and forth between our mouths until we felt Ted go hard again - one of the advantages of being in your twenties, rather than in your fifties like Dan.

Once it was fully erect I got on the bed and Dan dutifully and tenderly fed Ted's cock into my mouth. By now I was in danger of losing control. The thought of Ted, young, athletic, nubile Ted fucking me in front of my crossdressing sissy hubby, was driving me crazy with desire.

It was lovely to have Ted's big cock in me again. He was such a fulfilling lover. Stroking and licking my tits at precisely the right moment, then kissing my lips and inserting his tongue as we both edged closer to the precipice. Dan couldn't resist spanking Ted's bottom, cheering him on as if Ted was a thoroughbred racehorse.

"Oh Ted, you fucking stud. Fuck my wife with your big fat cock, pleasure her, fulfill her every desire. Give her the mother load."

I loved what hubby was saying and joined in.

"Yes, Ted, fucking me you gorgeous hunk. Fuck me in front of my sissy faggot. Show him how a real man does it."

Dan loved that.

"Yes, Ted. Show me how a real man fucks my wife. I beg of you fuck her and then give me sloppy seconds."

Ted and I thrilled to Dan's words and we climaxed simultaneously. It was thunderous, an earth-shattering experience. There was no going back now. I wanted loads of hunks to fuck me while my gorgeous sissy hubby watched wearing my underwear and, I wanted Dan to watch get fucked in the ass. But that would happen at the weekend. Now, as Ted withdrew, Dan feasted on Ted's huge cream pie. He didn't even pause for breath gobbling it all up and giving me another orgasm. Afterward, Ted rubbed Dan's cock, another first for Dan, until he exploded on my tits. Then the pair of them licked it all off and the three of us shared sloppy cum kisses until we fell asleep in each other's arms, satiated at last.

STAGE NINE

For the weekend I finally organised the orgy I'd promised Melissa, the Polish nurse. The majority of those invited were men - including Clive and Ted. When I invited Raquel and said she could bring Angus, she was over the moon.

At just after six on the Friday evening, Dan and I started getting ready. As he was going to be "serving" people all evening I figured it would be best if he dressed as a slutty maid. I laid all his sissy clothes out on the bed for him: long black fingerless gloves, a feather duster, sheer seamed purple stockings from Ann Summers that had an incription near the ankle that read - SPANK ME; a black balcony bra with a white lace trim with matching suspender belt and a new pair of satin purple panties. The black spiked Jimmy Choo high heels I placed next to mine.

We got in the shower together and kissed each other all over. Then we shaved each other's legs. I wanted Dan to feel like a real woman tonight so I shaved his ball sac too. Fortunately his chest is hairless. Then, because I was feeling even naughtier than usual, I shaved my pussy. We dried each other and once I'd done our makeup and put Dan's brunette wig on, I gave him a present.

"What's this?" He asked.

"Open it and see."

Dan opened the box.

"An ankle bracelet. Oh, thank you Dr Hottie."

"It matches mine. We'll put them on over our stockings so we both look and feel like tarts," I was dressing as a slutty nurse.

We then got dressed, went downstairs, and Dan prepared the drinks and nibbles as we waited for our guests to arrive. Dan looked stunningly hot in his French maid's costume, the starched uniform barely reached his thighs. The guys were in for a treat.

Melissa and Clive arrived first. They were both dressed as female vampires and looked so hot. They were wearing long, brown laced thigh length boots with black stockings, black panties and a scarlet red bodice. It was quite the site. Incredibly daring and effective.

Then the guys started to arrive. Ted was, not surprisingly, dressed as a Greek god. Roger, a very handsome mature back surgeon came dressed as an airline pilot, he looked edible. Three rugged junior doctors - Alan, Nigel and Frank came as personal trainers. Finally, Raquel and Angus arrives. Angus, like Dan, was dressed in a slutty French maid's uniform, but unlike Dan, his way made out of shiny patent leather. I couldn't wait to watch him and Dan fuck each other. Raquel, naughty sexy minx that she is, was dressed as the sluttiest cheerleader you've ever seen. Outrageously short skirk, pink panties, stockings, and a half-cut bra that left nothing to the imagination. She could easily turn a straight woman gay. In fact, Melissa's eyes were popping out of her head.

Dan and Angus served the food and drinks, and everytime they silled even the tiniest drop they were spanked by the recipient. Melissa, who I'd told about my new strap-on asked if she could get things underway by fucking Dan with it. So we all watched and cheered as she forced Dan to bend over the settee while Melissa fucked Dan fiercely. Watching Melissa's big fat arse go back and forwards as she fucked Dan's man pussy got me really aroused and soon Ted, Roger, Alan, Nigel and Frank took Raquel and I onto the rug and started kissing our lips and fondling our tits. Clive and Angus were playing with each other's balls and spanking each other.