Robin and Jimmy Olsen - Sissies Ch. 04

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Sissy former sidekicks finally finish date from part 1.
7.6k words
4.57
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Part 4 of the 10 part series

Updated 06/13/2023
Created 08/27/2011
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The Date Continues (finally)

*****

Just as Ollie and John began to wonder what was keeping their dates, they spotted the delectable pair of sissies returning from the rest room. When they reached the table, both men stood. Their politeness was rewarded by a brief kisses from the pretty lads. Each girlyboy also managed to run her hands across the crotch of her date and give each cock a gentle stroke!

Robin and Jamie looked at each other and giggled! Oh, the night held so much promise!

Robin sat down gently beside Ollie on their side of the booth. As she slid close to her man she moaned as the long thick butt plug tried to move around inside her ass. Jamie giggled again as she realized the reason for her best friend's distress! Her red lips glistened as her tongue moistened her lips. This matched the moisture in her panties as she leaked a bit of precum from her boy clittie, thinking about how her own ass would be filled before the evening was done!

The two sissies sipped at the fresh umbrella laden sweet fruity alcoholic drinks that had been brought to the table in their absence. But they were full of energy and dragged their dates up to the dance floor. Their table was towards the back and one side of the large room, so many of the guests of the upscale night club had not noticed them before this. But on the dance floor they drew many stares, and some under the breath comments of disgust! This was one of the trendiest nightclubs in the city but rarely did it see the sight of two blatantly sexual sissies wriggling and writhing against their dates on the dance floor. Robin and Jamie may have been dressed femininely, but it was still obvious that underneath they were male!

Some of the stares they drew were in disbelief. But many of the women were jealous of their overt femininity. And many of the men just wanted to fuck them! There were SO many hardons on the dance floor!

Looking at the two gorgeous sissies, it was hard to believe that just three years earlier neither had had a feminine thought in his head! They had been junior partners to the two most famous crime fighters in the world, using their fists and their wits to bring down some of the vilest villains of modern times.

As she gyrated wildly, Robin constantly ran her hands across the strong arms and ass of her date. As she looked in Ollie's eyes, she saw lust there. She knew that she turned him on, and she desperately wanted to be the best sissy she could possibly be for him. As she danced, her head spun and the lights in the room seemed to vibrate and thrum in time with the beat of the music. She knew that that was the coke spiking her brain! She was so happy she and Jamie had shared that snort in the powder room!

As she looked at Jamie, she was SO glad that they were both sissies. It had been so hard keeping her secret in the beginning, when she thought that no one would understand. Wearing panties underneath her Robin costume, and then wanting to be more feminine - shaving her legs and arms and arm pits, wearing small amounts of lipstick and perfume. Yearning to stroke the cocks of the villains she fought with Bruce, rather than punching them in the face! Wanting Bruce to look at her as something other than a chum! When these feelings began, and where they came from, she'd had no idea! But she had felt so lonely and miserable at not being able to be who he... she... really wanted to be. Not being able to explore her feelings had been SO frustrating. Until she had discovered Jamie in drag one evening in Metropolis!

As the dance music pounded heavily, Ollie pulled Robin close. Both of his hands grabbed her ass cheeks firmly and pulled the sissy hard into his groin. The tip of one finger pushed the ass plug hard into her asspussy! Robin could feel Ollie's hard cock pressing against her. He put his lips to her ear and said "I am SO much looking forward to sucking on you new breasts and fucking your ass!"

Robin kissed him quickly on the lips and then pushed herself away. She laughed in her best high feminine voice and then mimed jerking his cock while sucking him off. Ollie roared with laughter while everyone around them looked puzzled!

Robin turned the two of them so that they were facing Jamie and John, so that the four began dancing together as a group, rather than as two couples. The girlyboys took sips from their drinks which they had brought to the dance floor and placed on a side counter. The beat was heavy, the liquor was strong and the girls were horny! If anyone had been able to see under their short skirts, they would have seen two hard erect cockettes!

Robin was glad that Jamie was so happy this evening. She was glad that they were still best friends, despite the dramatic change in their circumstances. Robin had been so lonely in her torment and she knew that Jamie was feeling the same before they had discovered they shared the same secret - they each yearned to be feminine sissies, to be used as pretty playthings by strong virile men! But Robin had a much easier time of it, living in a large mansion with a large allowance from her guardian. Jamie on the other hand had just her reporter salary, which had recently been reduced because she was no longer really interested in that job. She had begun to resort to other ways to make some money!

Robing remembered when she had first discovered Jimmy's secret. Bruce and Dick, as he was known then, had gone to Metropolis for some big charity benefit. Something earth shattering had come up and Bruce had run off without him, to help the Big S and the rest of the League. Left on his own, Dick had decided to pay a surprise visit on his friend Jimmy. To make it a true surprise, he had put on his Robin costume. He had been wearing his then current favourite pair of tight blue silk panties all day and left them on under his Robin shorts.

Robin had swung down from a neighbouring building onto the fire escape that ran up the side of Jimmy's building and had climbed to the window of Jimmy's kitchen. It had taken him only a moment to fiddle with the feeble lock. He had silently crept into Jimmy's apartment. He had brought along a couple of beer and some chips. But these he dropped to the floor in shock when he entered Jimmy's living room, shouting "Surprise!"

Jimmy was surprised!

Robin was surprised!

The superintendent of Jimmy's building was surprised!

Robin was stunned to see his best friend wearing a stuffed bra and panties with stockings and high heels. The tip of Jimmy's hard cock was sticking out of the top of her panties.

Jimmy was wearing eye shadow and bright red lipstick, though the lipstick was smeared. Part of the lipstick was on Jimmy's cheeks, but a large amount was also on the dick of an older fat man on which Jimmy's mouth had been bobbing up and down when Robin entered!

"What the fuck!" exclaimed the fat man, his hard cock now free and waving about! "Who the fuck are you supposed to be!"

"No! No no no no no! Oh this can't be happening!" cried Jimmy. "You can't... you can't see me like this!" Tears began running down his face as he ran from the room. Robin heard the bedroom door slam shut!

"Get out!" Robin yelled at the man. "Pull up your pants and get the hell out of here!"

"I'm going, I'm going! But I'm taking this with me!" the man said angrily, grabbing three twenty dollar bills off of the top of the tv set! "Tell him... tell her I'll be back next week!" he said just before he slammed the door behind him!

Robin remained where he was for a couple of minutes, letting his breathing and heart rate return to normal. He could hear sobbing from down the hallway. He picked up the beer and chips and put them in the kitchen, then made his way down the hallway. He lightly tapped on the door, asking if he could come in.

"Go away!"

"I can't. I'm your friend. I want to help you!"

"After what you just saw! You still want to be my friend? Aren't you disgusted? Oh, my life is over! Now everyone will know!"

"I'm not going to tell anyone about this! Trust me. I AM your friend. And ... and I know what you are going through!"

"How can you know? How can you have any idea how I feel?"

"If you let me come in, I'll show you!"

"What do you mean?"

"Can I come in? If you let me in, I'll show you why you can trust me. Honest. Jimmy, you and I have been best friends for a long time. I guess we've had secrets from each other. But maybe it's time to be honest!"

"O.. Okay, you can come in. But.. But I look a mess"

Robin opened the door and entered. Yes, Jimmy did look a mess. His eye makeup was running down his face. His lipstick was spread across his cheeks and chin. Precum was smeared across one cheek. He had kicked off both heels. Both stockings had runs.

But somehow... someway... for the first time in his life, Robin looked at his friend and thought he looked... well, sexy!

"You... you said you were going to show me something!" sobbed Jimmy, tears still running down his cheek.

Robin stood in front of his friend and undid his belt. He then lowered his green shorts to reveal the blue silk panties that he was wearing underneath!

"What? Why are you wearing..."

"Because I'm like YOU, silly! I like wearing girly clothes! I like wearing makeup and being pretty!"

"You do?" asked Jimmy, incredulously. He stopped crying.

"Yes, and I fantasize about being overpowered by the crooks we chase. And being forced to suck their cocks, and having them fuck me up the ass!" said Robin. "I guess you've gone further than me!"

"You've never...?" asked the red headed man.

"Oh, I've kissed a few men. One strong archer in particular. But I haven't... I haven't been brave enough to do anything more. Yet."

Jimmy grinned at his friend. "I haven't been brave. Just desperate. I... I like dressing up. I love being feminine. But clothes and makeup cost money. So... so I've had to resort to taking money from strangers for a few favours, if you know what I mean."

The ice had been broken. The two friends sat for two hours talking about their new found feelings. Robin took off her costume and borrowed a nighty from Jimmy. But she was uncomfortable when Jimmy called her Dick, and asked to be called Robin. It was a nice feminine name, she thought. The two lads got Jimmy washed and cleaned up. They each put on a light bit of makeup and fresh panties from Jimmy's large stash. They shared beers as they reminisced about how each had begun to get feminine urges.

By the end of the evening, they were holding hands as they sat across the table from each other. Robin realized just how cute her new girlfriend would be when she got better with her makeup.

Robin scrubbed his face and redonned his heroic costume, though underneath he still wore the black panties Jimmy had given him. As he left, he and Jimmy shared a long slow lingering sissy kiss. The first of many to come.

As he left through the kitchen window, he knew that their relationship had changed, and grown stronger. They were no longer just best friends, now they were Best Friends Forever!

And now, here on the dance floor, the two sissies were enjoying their unfettered femininity with two hunky men who loved them - or at least, wanted the fuck them all night long, and for a sissy, that was even better than love!

Robin could tell that the two men were losing interest in the dancing and were ready for the more physical part of the evening. She loved teasing Ollie, but she knew how grumpy he would get if his cock was left waiting too long. She told the two super hunks to return to the table and settle up the tab, while she took Jamie by the hand and the two girlyboys went outside to the smoking area.

Jamie fumbled in her purse for her cigarettes. She had enough to drink, on top of the line of coke, that she was just the tiniest bit tipsy. There were a few other women standing around smoking, glaring at the two pretty boy tramps. Robin and Jamie lit cigarettes. They were momentarily enthralled by the sight of their lipstick on the filters. Robin pulled out her compact and lightly touched up a bit of foundation and reapplied her lipstick. She fussed with Jamie's short hair a bit.

"You know, these things are really terrible. They are going to kill us!" said Jamie smiling, as she blew out another stream of smoke.

"Not me," laughed Robin. "I'm expecting to die in bed with three cocks stuffed in my body cavities and a gallon of cum all over my face and suffocating me to death!" She took a last drag on her cigarette then ground it out beneath her expensive shoe. She looked deep into Jamie's eyes and pulled her face towards her. She kissed her best friend hungrily. Both sissies opened their mouths and shared a long lingering smoky kiss!

"I almost forgot, I have something else to show you," Robin said as she dug around inside her small purse. "This arrived today!" Robin handed her new drivers license to the redhead.

Jamie let out a gasp! "You did it! You really fucking did it!" She let out a squeal and hugged her friend tightly.

"Yes, my name is now legally changed. Now Alfred HAS to stop calling me that wretched Dick name. He is so prim and proper he'll have no choice but to call me Robin. It's my legal name now."

"Miss Robin Cumspurter! Hmm... I wonder if I should change MY name. Olsen is so boring. I've had it for twenty-three years. Maybe it's time of a change. Hmm... Jamie Cumspurter. We could be sisters!"

"How about Jamie Wanker? Jamie Tightass?" suggested Robin mischievously. "Or Jamie Cumsucker?"

"I like that... Jamie Cumsucker!" Jamie sighed "Jamie No-Tits is probably more realistic though!"

"Don't worry girl. I'm sure the hormones will work, eventually! And you can always buy a pair like mine! Oh Ollie is going to be SO thrilled when he gets his hands on these babies!" Robin opened a couple buttons on her blouse to remind Jamie of her brand new cleavage!"

"If I'm going to buy myself a pair, I'd better get out on the street corners a few more nights each week!" Jamie sounded dejected as she flicked her own cigarette away into the dark.

"I'm sorry, Jamie. I know it is hard seeing me with tits! But I also know you are happy for me! Let's see if we can cheer you up, eh? What do you say to taking our men back to the rooms and getting thoroughly fucked!" She took Jamie's hand and squeezed it tight. The two feminized lads wiggled their asses back inside to the exit where the boys were waiting for them.

Ollie drove the rental car to the hotel. It wasn't a fancy hotel, but it wasn't a dump either. As they drove, Robin stroked Ollie's cock through his pants. The archer's cock was strong, solid and rigid. She was tempted to unzip his fly and suck his cock as he drove, but she knew that it would be difficult to get back into his pants when they reached the hotel.

When she looked in the back seat, she saw that John and Jamie were locked in a long passionate kiss, their tongues duelling. Jamie did have her hands inside John's fly and he was groaning as he pressed his cock hard into her palm. "Get a room, you two!" she shouted at them, and then added, "Oh wait, we have got one!" and giggled again. She squeezed Ollie's cock hard and he almost swerved into the path of a car coming in the other direction.

At the hotel, they took the elevator up to the room that all four would be sharing. The girlyboys each had a small overnight case containing makeup, nighties, a small change of clothes and a couple of toys.

John had no bags at all, despite having flown in from Denver just for the evening. That puzzled Robin until she realized that he had not flown by jet and would be able to return home in less than an hour. She knew that Ollie's large bag contained his working clothes and collapsible bow, which he never travelled without!

The room was large and had two king-size beds. Once they were in the room, the sissies gave their dates brief kisses, then took their bags into the bathroom together, where they spent a half hour helping each other change and look even more boyishly pretty! Jamie's boy clittie was constantly erect and oozing precum as the two stood side by side at the counter, applying their night time makeup. It did not help that Robin would regularly reach over and stroke her arm or stand behind her so that Robin's own small pussy stick would poke against her thigh!

Jamie loved the attention of men. She creamed her panties when a big husky man looked at her with lust. But she also loved her fellow sissyboy, Robin. She looked forward to the times when just the two of them would lie on a big fluffy bed and kiss and cuddle, which soon turned into sucking each other's delicious and oh-so-pretty dickies! Sometimes one would even fuck the other. Neither had a very large clittie, but Jamie thought it was so beautiful to be lying on her back, her legs in the air, and having her wonderful sexy Robin's cockette embedded in her ass, and slowly sliding in and out of her. It was so divine to have her BFF's cock in her ass and tongue in her mouth at the same time. She did not know what she would have done if she did not have Robin to share this adventure with!

When the sissified boys were just about ready, there was one last important task. Robin leaned over the counter and flipped up her nightie exposing her bare ass. Jamie got behind her and grasped the base of the butt plug in the dark haired sissy's ass. Robin pushed with her ass muscles and Jamie pulled. It took a few moments, but finally the plug slid out of from between Robin's cheeks. Jamie was surprised at the size of the monster. While six inches did not seem like much of a length, her friend has been walking around and dancing vigorously with this buried in her ass all evening. And it was thick!

As Robin remained bent over, Jamie used a soapy cloth to wash around Robin's asshole. It remained gapingly open. Jamie could see several inches into the depths. "Ollie's cock is so fucking huge, I HAVE to prepare like this or he will never fit inside me!" purred the sissy wonder!

Jamie gave her friend's ass a few loving kisses before pulling her nightie down. Jamie would have loved to stick her tongue into her friend's nether pussy. The two girlyboys could have spent many hours tonguing each other's love receptacles but they had two hunky men waiting for them in the other room!

When the two young chums minced their way out of the bathroom their dates were waiting for them expectantly. Both Ollie and John were naked, but each was on a different bed and underneath a single sheet. Male prudery dictated that it was not proper to be overtly naked in front on another man unless one wanted to be deemed to be homosexual. And neither man had any interest in other men. Of course, delectable, pouty-lipped, perfumed and painted sissies with small dicklettes did not count as men!

Robin sat on the edge of Ollie's bed and let her nightie fall open, giving the bearded boyfriend his first look at her new titties. Ollie smiled broadly as he drew her head down to his for a deep hard kiss, while his hands began to toy with her new round boobies.

Meanwhile, Jamie let out a squeal of delight as John grabbed her by the arm and dragged her onto the bed and into his arms. She mashed herself against his body and he drew her into a deep hungry kiss. "By all the Martian Gods, sweet Jamie! You have teased me all evening with that sexy ass, and those beautiful green eyes!" John lay her on her back and his heavy body drove the breath out of her momentarily as he lay upon her. His hungry tongue invaded her mouth and he rained sweet tender kisses on her eyelids and her cheeks. He nibbled on her ear lobes. She panted as he kissed her smoothly shaven chin and neck. She pressed her groin upwards against his, her cockette firmly rigid and leaking juices as her lover's own hard firmness rubbed against hers.