Robin and Jimmy Olsen - Sissies Ch. 02

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Robin prepares for sissy date - Alfred beware!
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Part 2 of the 10 part series

Updated 06/13/2023
Created 08/27/2011
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Chapter 2

Robin prepares, Alfred beware!

The evening before the date in Part 1...

Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled by the idea of smoking. But then the big change had hit him and now he thought the sight of any smoking pretty girl, or girlieboy, especially himself, was damn sexy. And looking sexy NOW was all that really mattered - to hell with worrying about tomorrow!

As he sat at his makeup table, he admired his face in the mirror as he took another puff. He had not yet finished making himself up for his evening date, but even still, his dark painted eyes, his long lashes, and his brightly painted lips made his pricklet throb in his panties.

He/she knew that before he made it out the door this evening, he would go through two or three pairs of panties. Some would just be moist from leakage, but one or more would be because he could just not control himself when he was sissied up for a date and would spurt at least one load of cum into her silk undies.

He... she.. him.. her Pronouns were so difficult in his/her position. As Dick, he and Bruce had had a good partnership putting nasty villains in jail. But a couple years back, curiosity had led the orphan teen to put on a pair of panties that one of Bruce's many dalliance's had left behind. His immediate arousal had soon led him to wear those and other panties (including his then favourite pair from Selina, adorned with tiny siamese cats) especially while he jerked off in the late mornings after returning from a hard night of crime fighting.

Robin resumed feathering her short cropped black hair as she recalled that she had soon begun wearing panties under her pants at high school and even out on patrol with Bruce. She smiled as she remembered when she first began noticing the bulges in the pants of all of the villains and their cronies. She realized that they were getting sexual kicks from the fighting. And she was too! She became curious about those cocks. She started dreaming about being overpowered and those big strong henchmen discovering her panties - and then doing... THINGS to her.

But the change... ah, yes, his change in attitude... had happened one evening when one of Bruce's League buddies had noticed his panties and, when they were alone, had actually kissed him, and kissed him hard! Dick had been stunned, but had kissed back, even sucking on the man's tongue. The man had cupped Dick's groin and Dick's prickie had spurted wet cummies into his panties!

From that moment on, Dick had realized that he did not want to fight the villains any more., but he did want to fuck them. Or rather, he wanted them to overpower and fuck HIM. He needed their cocks. No, he CRAVED men's cocks.

Over the coming months he realized that he was a sissy. He had no desire to be a girl. He loved his pricklet. He loved having a strong man wrap his hand around his dickie and make him gush! And he had no need for a cunt... he already had a perfectly good asspussy for the men to fuck him hard and long - hopefully many times!

Of course, his dates did not want him looking like the rugged young hero he had been a year ago. They preferred a femmy sissyboy. And he loved pleasing his men. As he stood in front of the full length mirror, Robin admired her smooth hairless body, her long legs, her perfectly coloured toes and fingers. She was the perfect picture of a sissyboy, all dolled up with the allure of a young girl, but with the frame of a young man still very visible.

She had decided not to go to college, they did not offer a degree in FUCKING! Instead had used her allowance from Bruce to buy hormones. Her body and face had softened, her hips had flared, her titties had become small mounds and her libido... had soared. She had until recently resisted any surgical modification to her body - she was a boy, though a sissyboy for sure, but not a girl and had no desire to transition. But recently. Well.., recently her best boyfriend (yes, she had MANY man friends) had been generous and she had hated to say no. It had taken two months to recover, but she was ready for her first date with her... improvements.

Now she had to decide which of her many dresses to wear this evening. She had a double date tonight. Her favourite boyfriend was eager to see the results, and was taking her out to dinner and clubbing. They were being joined by her BFF Jamie, another sissieboy, from Metropolis, who she had not seen for those two months! Robin was excited - Jamie had said her date tonight was quite Super, and she was hoping that he/she had finally landed the man she had been drooling over for years - even before Jamie had realized SHE was a sissy too. Robin herself would not mind being stuffed full of that hero's cock!

Stuffed. That reminded her.

Robin opened the drawer in her bedside table and examined the contents. She giggled to herself. Once the only equipment she was interested in were weapons and motorcycles and Bruce's latest car or helicopter. But now, her interest was in what the drawer held - vibrators, handcuffs, nipple clamps (mmmmm!), a doubleheaded dildo (now THAT had felt SO good the last time that Gar had come and visited - or was that, had visited and CUM!) and... yes, there it was, the butt plug she was looking for.

Robin's date had a prodigious cock, a thick truncheon. She could barely get the head of his dick into her mouth and it had taken them several long attempts before he had managed to slide his dick into her back passage the first time.

Robin grabbed a bottle of lube, stripped off her panties and lay on the bed. She quickly brought her legs up and put her feet under her shoulders. For years he had been a circus acrobat, before the accident when Bruce had taken him in, and for years after that he had been an extremely well trained hero. Due to the hormones she was taking, Robin no longer had the body mass or strength necessary to fight villains (Bruce had his new partner Tim to help him with that now) but she was still extremely limber!

Despite the hormones, and despite calling it a pricklet, Robin's penis was still a nice six inches long when erect, and his cockette was instantly erect as soon as he used two fingers to push some lube up his bum hole. As he worked more lube into his asspussy with three and then four fingers, Robin's eyes rolled back and he groaned from the sheer pleasure. She was tempted to add her thumb and sink her entire fist into her ass, but she had done that only once before and she knew that if she started fisting herself, she would continue for a long time and would not be ready when her date arrived to pick her up.

Reluctantly, she removed her greased fingers and reached for the butt plug - and it was a LARGE plug, since it had to prepare her for a good ass reaming later that evening. As the tip of the plug pushed against her anus, she pushed back and shivered as the fat end slowly slid inside of her. It was not an easy penetration and she had to saw it back and forth, in and out, several times before she felt the widest part slide past her anal ring, and then her anus snapped shut and only the base remained visible. At the same moment her excited dickie exploded and she creamed all over her chest and up onto her chin.

She lay back for a few moments to rest. She used a tissue to clean up her cum. She rose from the bed and pulled a robe around her body against the chill, but did not put on panties. Why make messies in another pair. Dear Alfred was already SO embarrassed at having to wash so many pair.

She lit another cigarette.

As she once again set about deciding on a dress for the evening, she felt the comfort of the wide buttplug in her ass. It definitely gave her back end an extra wiggle as she pranced about the room.

She gave a slight jump, and a soft moan, as there was a knock at the door. She tied the sash of the robe tighter and went through to the sitting room of her suite and opened the door. It was Alfred, of course, holding an official looking envelope on a tray.

"Master Dick," said the butler, trying to look straight ahead, "A letter arrived for you by special delivery."

"Oh Alfred! How many times have I told you to top calling me that name," said Robin, as she took the envelope from the tray and eagerly began to open it.

"I realize your discomfort sir" said the butler, "but you must realize my discomfort as well! I helped raise you into a fine young man from when Master Bruce brought you to his home at the age of 12, until now, eight years later. I am SURE that some time soon, you will come to your senses, and..."

Robin rounded on Alfred. "Come to my senses? Alfred, this is not just some phase I am passing through. This is my life! I finally realized that I am not a boy... a man... like others. What you knew of me... that was a lie. I love Bruce, and you, for taking care of me and raising me as best you could, in the only way that you knew. But that was NOT the life for me. THIS... " she said, revolving gracefully and raising her robe so that Alfred could see her dark stockings. "This is me!"

"Alfred... my name is Robin, not Dick. You can think of me as a girl if you wish, or as what I truly am... a sissyboy. But I am not a boy. I have realized that I have one purpose in life, and that is to make men happy. And to make them happy in the best way that I can... by servicing their cocks!"

As she said this, Robin leaned forward and stroked Alfred's cock through his pants. In spite of himself, he was hard. Robin knew that Alfred was always hard in her presence.

Alfred jumped back, flustered. "Really Master Dick! This is most unbecoming!"

"Stop calling me that! In fact, you can no longer call me that. Look... this letter. It is from Bruce's lawyer. You know - the one I have visited several times, in private if you know what I mean. He has sent me the official paperwork for my name change!"

"Name change,sir?"

"Yes... look... my first name is now officially "Robin". It is no longer that vulgar "Dick" name. You now must call me Robin." She flourished the official papers at him and he squinted closely.

"Oh dear," he cried, startled. "Oh my god. Master Dick. How could you do that!" Alfred had noticed that she had changed not just her first name, but also her last name. And the name she had chosen...!

"Alfie... for that is what I am going to call you from now on... Alfie, you may not like that I am now a prancing, mincing, cock-gobbling sissy boy, but you have to accept that I am who I am. No villain has cast a magic spell on me or slipped me a chemical cocktail. Believe me, Bruce has run every test he possibly can on me and has told me that no one has influenced me! I am this way because I WANT to be this way.

"You may no longer call me by that name. My name is Robin. You can call me just Robin, Miss Robin, Mistress Robin, or any form you want. You can call me by my new last name...."

"I would never do that!" cried Alfred in almost terror.

"But my name is now Robin. And you have to get used to WHO I am and WHAT I am!"

Once again Robin, ran a hand along Alfred's groin, but this time he did not pull away. He flinched, but did not move. Her hand rested there.

"Look at my face." He did. "Do I not look happy to you"

"Yes, you do," he replied

"I have a pleasant face, don't I? Is it not a cute face, a pretty face? My makeup brings out the green of my eyes, doesn't it?"

"Yes it... it does. If yours was the face of a girl, I would find you comely, Miss.. Miss Robin"

Robin slowly ran her hand along the girth of Alfred's cock. It was not small.

"You can think of me as a girl if you want, Alfie. I don't mind. I am not a girl. I am a sissy. A boy who wants nothing in life more than to please a man... or rather to please a man's cock." She gave the butler's cock a squeeze, and Alfred moaned.

"Look at my eyes Alfie. Those eyes adore you. They have always loved you for taking care of me." Robin lowered herself to her knees and her hands began to loosen Alfred's belt.

"Look at my lips Alfie. They are painted red to thank you for all that you have done for me." Robin lowered the butler's pants and then his underwear. Alfred was shaking as his cock was exposed. But he did not step away from the young trollop, nor did he resist her as she grabbed his rigid rod with both of her hands.

"Look at my hands Alfie. The nails are a bright red so that I may wrap them around your cock and give you pleasure." She ran her hands up and down the length of his rigid tool.

"Look at my pretty pricklet Alfie." She pulled back the bottom of her robe so that her extremely rigid penis was exposed. "It is hard for YOU Alfie, showing you how much I love you and how much I want to please you!" Robin moved her head forward and she tenderly kissed the tip of Alfred's cock. Her tongue swirled around the head once, twice, and she was SO eager to take the older man's cock deep into her mouth

But Alfred pushed back on her forehead. "No! Master Dick! I mean... Miss Robin. Not... not your mouth," the butler hoarsely croaked. "This is so new to me... you... you DO look so lovely. But not your mouth. Please!

Robin pouted. A tear came to her eye, and then her heart leapt as Alfred finished... "Not.... this time."

"Alright Alfie. But there are more ways to skin a cat, so to speak," she purred. Robin spat twice into her hands, and then a couple times more onto the head of the servant's cock and ran her hands along the rod, slickening it with her saliva.

With one hand holding the base of his cock firmly, the sheboy temptress firmly jerked the stiff prick with her other hand. Occasionally she would release her firm grip to run her hand up and down the tip of the cock, stimulating the underside of his glans.

"Oh my, that feels SO good," exclaimed Alfred, his legs shaking.

"Look into my eyes, Alfie." the prissy sissy said softly. "Look at how pretty I am. Look at my red red lips. They want to suck on your cock SO SO much!"

"Oh Miss Robin. This is so very wrong!"

Robin began to jerk him faster, her hand swirling around his knob end!

"How can this be wrong? I LOVE making your cock so very hard. And it seems to like what I am doing! Do you like what I am doing?"

"Oh yes, very much so, Miss Robin!"

"Do you prefer to think of me as a girl, Alfie? Or do you like sissy boys?

"A ... a girl miss!, " he moaned. "Oh fuck that feels so good!"

"Have you ever had sex with a boy before Alfie? Have you ever been kissed by a man?"

"Ohhhh... miss!" Alfred's legs were shaking quite a bit now. "I'd.. I'd rather not say."

"Tell me Alfie. Tell me or I won't finish you off!" The sissy let go of his cock!

"Oh no miss. Please don't stop! It was in the army..." The former teen sidekick spat several times onto the butler's dick and resumed stroking him. "I was young, barely out of my teens and drunk. My bunkmate and I returned to barracks one night... Oh, damn, that feels so GOOD miss!"

Robin had begun to swirl her hand around and around his glans, as her other hand pumped his shaft. She was SO going to make this old codger explode! She thought!

"He... he sucked.... sucked me and then convinced me to put my dick up his arse. It was just the one night, and I have never touched another man since. But I have always thought that his arse was tighter than any pussy I have ever been in!"

"Oh Alfie, asspussy is the BEST kind of pussy! For you, AND for me!"

"Oh, Miss Robin, you should not say such things. If you must be a girl, you should be prim and proper!"

"You can say that Alfie, with my hands on your dick! With your knees knocking and your cum boiling in your balls!

"Oh, Miss Robin. I'm going to cum!"

"Where do you want to spurt your jism, Alfie? In my mouth?"

"Oh,... nnn..nno miss"

"On my face then! Do you want to cover my nose, and lips and my dark eyes with your cream!

Robin's hand was now pistoning furiously on the butler's rod. Alfred's face was a bright red from the strain. His breathing was ragged, and his legs were shaking tremendously. With her other hand, Robin opened the sash on her robe, and let the robe fall to the floor, revealing her body, naked except for her dark hose.

"Or would you like to cum on my new tits, Alfie?"

"T..tt....tits, miss?"

"Look Alfie! I have glorious tits!" It was true! For the past two months, Robin had kept her chest hidden from Bruce and Alfred as she had healed. Her best boyfriend had paid for breast implants, and Robin now had two delicious B-cup mounds on her chest - a girl her size could have much larger breasts, but these were the perfect size for a sissy prissy cum-sucking girlieboy!

"They are beautiful miss! Oh yes, let me cum on your tits"

"I would be honoured Alfie. Honoured to have you be the first to anoint my new boobies with your cum!" Robin renewed her jerking and the butler's knees began knocking.

"I'm cumming miss... I'm cumming! Oh god, here it comes"

"Spurt for me Alfie! Blow your seed on me. Cream my titties"

"Oh yes Miss Robin.. Here it comes... Oh God, why won't it come!"

The sissy jerked him furiously. "Look into my eyes Alfie. Tell me how pretty I am. Tell me you want to FUCK me! Tell me you want to ram this cock up my boy pussy! Tell me what my new name is!"

"Oh yes, Miss Robin... You are such a pretty girl. I have always longed to FUCK such a pretty girl!"

"My full name Alfie.... what is my full name?" Robin licked the drooling precum off of her hands.

"Oh god Miss... I want to FUCK your asspussy. I want to FUCK Miss Robin Cumspurter!"

And Alfred's dick exploded! He jetted gob after gob after gob of thick creamy jism onto the sheboy's chest! Robin pumped him vigorously and used the tip of his dick to swirl the jism around, even rubbing his glans across each of her nipples. She shivered in delight!

As his orgasm subsided and his breathing returned to normal, Alfred watched as the young boyslut swirled his cream around her chest, massaging it all over her new breasts (Master Dick now had breasts! How horrible!).

Embarrassment over what he had just done flooded over the butler. He stammered his apologies, pulled up his pants and hastily ran out of the room, almost tripping twice.

"Alfie, wait!" cried the sissy after him!

But, he was gone.

Had she scared him off? Was he going to go to Bruce and complain about the young ward's behaviour again? Time would tell.

In the meantime, much as she loved having her chest coated in Alfred's cum, she knew she was going to have to wash it off immediately. She knew that her date tonight would not take kindly to dancing with her when she smelled of another man's jism.

Now, what dress was she going to wear tonight?

The morning after the date

Robin heard a light tapping at his door. He opened his eyes to see his bedside clock. It was two in the afternoon. He wanted to burrow back under the covers. He was still SO tired from last night.

He had drunk too much, had done some coke, and then had sucked and fucked his boyfriend until the wee hours of the morning. Speaking of which his ass was SO sore. If he checked, he would probably find it was still gaping open. He squirmed and changed position, his silky nightdress feeling so delicious against his soft skin. Although it did stick in places - places which were blotched with her boyfriend's dried cum.

The sissy settled under the covers again, though not to sleep right away, but rather to reminisce about the previous night. His pricklet grew hard as he remembered bouncing up and down on his date's incredibly thick dick. He purred in delight.

The knock repeated, louder this time. With a small huff, he realized he was not going to get any more sleep. He sat up in bed, fluffed his pillows, pulled his nightdress into shape, covering his new titties (oh, his boyfriend had been SO pleased with his new boobies!).

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