Rohit’s New Life – Part II

This is Rohit from Cochin, narrating another true experience. The participants know who they are for the rest of the ISS universe, please enjoy; Feedback, both positive and constructive can be sent to [email protected]

Rohit woke up on Saturday morning feeling excited without knowing exactly why. He tried to sit up, but his left arm was pinned down by Preeti’s body. This was normal for a Saturday morning, since she tended to sleep at Rohit’s house on Fridays because his parents and his sister would go on their weekly visit to his grandparents in Thrissur something he avoided every week to be together with Preeti.

The reason he was excited suddenly hit him on Tuesday, Preeti had told him they were going shopping today. This had been right after a great fucking-session in which Rohit had been dressed in Preeti’s old school uniform and she’d fucked him with a strap-on dildo. It had been a very kinky evening very carefully and gently Rohit extracted his arm from underneath his girlfriend and made his way to the door.

He went down the hall for a shower, wondering what shops they’d be visiting and what they’d be buying for him. He knew it’d be girl’s clothes, but he had no idea what-so-ever what kind while he was pelted with water from the shower, images came to his mind thongs, skirts, saris, dresses, blouses, and every other kind of girly clothing-article he knew of in his mind’s eye, he was wearing them and examining himself in a mirror.

Rohit’s hand drifted towards his crotch as he thought of these things, and he began to stroke it absently. Thankfully, Rohit wouldn’t have to be sized-up for these clothes. He wasn’t much taller than Preeti and the extra height was just leg. He’d be dressed up when they went out, and he’d be using his best girly voice, which he’d been practicing in his spare time when he was trying anything on, Preeti would go into the changing room with him, under the pretext of helping one of her girlfriends find clothes that suited her.

Nobody would know it was actually her boyfriend. Rohit just hoped he wouldn’t see any of his friends in Oberon mall; that would be uncomfortable. The sound of the bathroom door opening snapped him out of his thoughts, and he realised that he was actually stroking his cock. He quickly stopped I’m in here, he called, thinking it must be one of his parents or his older sister. I must have forgotten to lock the door. Don’t worry, Preeti’s responded. “It’s just me nobody else is home.

Right, Rohit said, feeling like an idiot. His parents and his sister would be at Thrissur by now. I forgot that nobody would be in at this time. Preeti walked into the bathroom and looked around the shower curtain. Her eyes wandered Rohit’s body and she noticed his erection and excited about today, eh? She asked with a sly grin. Rohit blushed slightly. He was comfortable with being naked in front of Preeti.

He was comfortable with what had transpired on Tuesday at her place but for some reason, admitting being excited about the day’s planned shopping was slightly embarrassing. Instead of saying anything he just nodded. Well, we can’t have you walking around with a raging hard-on, now can we? Preeti asked, sounding amused unless you want people to know you’re cross-dressing?

Rohit shook his head vehemently. He didn’t want people to know that. He wanted his life to be without people automatically thinking he was gay, which he was certain most of his friends would do if they were to find out. Then you’d best make sure that goes down before we go out. She told him and wash yourself with this hair-and-body wash and use some conditioner, your hair’s long enough for you to not need a wig.” She added.

She left to have breakfast, leaving Rohit to wash himself as she told him to. He had to be able to pass as a girl in scent as well as looks, after all when he’d finished showering, Rohit went downstairs wrapped in a towel and made himself a bowl of cereal. He went to eat it in front of the TV where Preeti was eating her own breakfast and watching how I met your mother on Star World while he was eating, Rohit kept giving Preeti side-long glances.

She didn’t seem to notice, or if she did, she didn’t show it. He was starting to get nervous about today’s plans. He’d be out, dressed as a girl, and with Cochin’s weather, the skirt he’d be wearing would probably be stuck with sweat or be raised from a strong breeze to a strong wind. That would probably expose him to everybody in the vicinity. Rohit still couldn’t quite believe what he’d gotten himself into. He’d always known his girlfriend was kinky, but he’d never in a million years imagined.

She gets him to dress as a girl, fuck his ass and then take him shopping for some girly clothes of his own at the weekend. He enjoyed it, but he was still apprehensive about the entire thing. We’d better get ready.” Preeti told him, breaking his chain of thought. Sure, he said you are going to help me, right? Of course I am she told him and you’ll have to practice the hair and make up part yourself, but I’m sure you can dress yourself. She added teasingly.

Rohit took their plates into the kitchen then they both climbed the stairs and went back onto his room. Preeti went through a drawer where she hid some of her clothes for whenever she slept over. It saved her having to bring a change of clothes with her. Two changes in this case. Rohit thought to himself. She brought out two pairs of panties; two skirts and a couple of plain tops for them both to wear. She handed him the panties.

Then a skirt and top before going back into the drawer to get herself a bra. They got dressed quickly and Rohit waited while Preeti did her make-up. When she’d finished, she motioned him to sit in the chair she’d just vacated and she did his. Nothing extravagant, but enough to ensure nobody recognised him as a boy. Then she did their hair; straightening it and ensuring that it made them both look sexy, and in Rohit’s case, like a girl.

Preeti handed Rohit a pair of stockings and pulled a pair on, herself. When he had them on, she picked a pair of shoes for him and then they went downstairs. She put on the shoes she’d brought with her the night before and grabbed her handbag. They were ready to go out and Rohit was extremely nervous to say the least. An hour later, Rashmi and Preeti were crossing the NH 47 to get to the entrance of Oberon Mall.

Preeti had noticed that Rashmi looked worried and only one thought passed through her mind when she had first noticed it: cute. Many people turned their heads to get a second look at the two of them. This was what Rashmi was worried about; that somebody might notice she wasn’t actually a girl. Luckily, she hadn’t seen any friends from college. If she had, she’d have probably passed out from fear of discovery.

They reached a clothes shop exclusively for girls and went inside. It was beautifully set-out. Unlike the unisex or men’s shops in Oberon Mall, everything was in a specific location. Underwear was hung along one wall on hooks and on a few small stands just in front of the wall. There was a wall exclusively for shoes and then there were skirts, dresses, blouses, stockings and tights, trousers and even hats in their own little, neat sections.

Welcome, ladies! The woman behind the counter said, enthusiastically, how may we help you today? Oh, we’re just looking for some clothes for my friend, here.” Preeti said, without even a hint in her voice to insinuate that Rashmi was actually Rohit alright, what sort of thing you are looking for? The shop assistant asked and some nice clothes.

Preeti told her and something that suits Rashmi, here and I think we have something she’d look very baeutiful in the shop assistant said smiling at Rashmi. She motioned them forward and they walked towards the changing rooms. They stopped half-way down the shop and the woman grabbed a few items. They went further and she grabbed a few pairs of frilly tops.

I’m grabbing you things that go well, together. I hope you don’t mind me picking a few items to try. She said not at all any help you can give me is welcome. Rashmi replied. My name’s Ambili and the assistant said nice to meet you, Ambili and Rashmi said as they’d been walking, Ambili had grabbed more things for Rashmi to try. They reached the back of the shop and stopped. You can wait here, if you like, Preeti. You don’t need to keep an eye on me.

I remember our deal Ambili said with a wink at Preeti. She pushed Rashmi into one of the booths and pushed her down. You’re very sexy, Rashmi she said or should I call you Rohit? You know? Rohit said, reverting back to his own, male voice, how? Ambili chuckled Preeti and I are friends. She comes in here to shop every so often and we built up a friendship. She came in on Wednesday and told me something naughty had happened.

I wish I was there to watch, and maybe join in a large grin was on Ambili’s face by this point and Rohit was seething silent anger towards his girlfriend. She’d told him this was to be a secret and then she’d gone and told this woman all about it before you two were dating, Preeti and I were actually exploring each other. Ambili continued with her monologue, ignoring Rohit’s obvious anger.

She’s told me quite a bit about you when we’ve had lunch together and we both think you’ll like me at that point, Preeti popped her head around the door and Rohit’s head snapped around so he could glare daggers at her and sorry, Rohit. I had to tell her. She’s not you’re average girl. She said apologetically anyway, she falls under the category of one of your fantasies.

Rohit was baffled, he had plenty of fantasies every guy did. He was running through them all when Preeti spoke again about the agreement, Ambili. She said and Ambili’s head snapped around. Preeti smiled anything goes. I was a bit reluctant, but go for your life. Thank you, Sweetie Ambili said and Preeti left, closing the door behind her. Ambili quickly locked it.

Rohit was still going through all his fantasies or rather the fantasies that were relevant to the situation he was in. Lesbian seemed to be the obvious fantasy but then, there wasn’t another girl in the room unless his alter-ego, Rashmi was involved. Rohit’s mind was racing when Ambili answered which fantasy it was.

Ambili removed the pallu of her well-ironed, red salesgirl sari, revealing lovely mounds. She proceeded to undress right there in front of him. She had brilliant legs and Rohit could also see she had a magnificent, round ass. There was something out of place, however, but before his brain registered it, Ambili was pulling her panties down, as well when she stood up straight again, Rohit could see a rather large cock between her legs.

Ambili was a Transsexual, the type u see in temple, but never guess they have a cock. Rohit had had fantasies of fucking a shemale for years. He thanked Preeti in his head with extremely humble apologies for being angry at her. He cock was responding to the amazing woman before him by the way, I figured I ought to tell you why Preeti has that strap-on. Ambili said. “It was so she could return the favor to me.

We usually only ever did anal, and she liked to fuck my ass every once in a while. Rohit’s cock was fully hard by the time she’d finished and he was dying to get a piece of her. He felt very restricted in the panties Preeti had given him earlier that day. Ambili smiled as if reading his mind before kneeling down and sliding her hands up his thighs slowly and seductively.

Her hands reached the waistband of Preeti’s panties and her fingers hooked under them. She pulled them down, stopping only so Rohit could raise himself of the changing booth’s bench so she could take them off once Ambili had pulled the Panties over the shoes Rohit was wearing, and she bunched them up and put them next to him. Rohit noticed that the beautiful Transsexual woman was looking at his cock and licking her lips.

She stared at Rohit’s cock while she gently pushed his legs open. When they were open a decent amount, she leaned forward and licked up his shaft, causing Rohit to grunt with pleasure. I want you to use your girly voice, not your every-day voice,” she told him with a smile, before diving back to licking his hard shaft. Rohit released a small, girly moan of pleasure this time, as Ambili wanted when she got to the head of his cock, she swirled her tongue around it like a pro.

Rohit had to stop himself from screaming his assent. Ambili noticed this and picked up the discarded panties. She balled them up and pushed them into Rohit’s mouth so he wouldn’t have to hold his moans back as much when that was done, Ambili slid his entire cock into her mouth. Rohit’s pleasure was so much that he almost screamed into the panties in his mouth. He was having his cock sucked by a shemale, he was in heaven.

Ambili started sliding her mouth up and down Rohit’s cock, swirling her tongue around the head when she reached it. He could hardly hold back from cumming, and even with his best efforts, he’d cum soon, anyway as the thought hit him, he felt the familiar sensation in his balls that told him ejaculation was on its way. He couldn’t say anything, because of the panties in his mouth and he was feeling too good to take them out.

Suddenly, Ambili stopped sucking him and looked him in the eye. She gently pulled him down off the bench and onto the floor where she straddled his head and got back to what she’d stopped. It was only then that Rohit realised she’d been stroking her own cock without hesitation; he removed the panties from his mouth, raised his head and started sucking her cock, like she was his. They were now both sucking each other and moaning into each other’s cocks.

Suddenly Rohit came moaning into Ambili’s cock as he filled her mouth with his cum. She was milking every last drop from him as she continued to suck before he finished cumming her own orgasm started warm cum shot into his mouth and he struggled to swallow it before the next spurt came. He swallowed furiously, as he might do with a glass of water in summer after being outside for several hours eventually, their orgasms both stopped, and Ambili stood up, shakily.

That was amazing, she said and we’ll have to do more another time. She pulled her panties and started wearing her pavada, blouse and finally, her red sari, and when she was fully dressed she’d regained her composure. She no longer looked as if she was about to collapse. Rohit followed her example and took the panties he’d been wearing off the floor and pulled them back on. They were damp with his saliva.

Shall we go and get those clothes paid for, ‘Rashmi?’ She asked with a grin and a wink. Rohit just nodded and then followed her out of the changing room where they met Preeti. Have fun? She asked with a wide smile on her face. Yes, thanks Rohit said in his best girl-voice. I finish work at six if our plans or still on tonight, Preeti Ambili said.

Sure, Ambili Preeti responded and she then turned to Rohit and said you don’t mind having dinner with me and Ambili do you, Rashmi? We’ll do something fun afterwards too and of course I don’t mind Rohit said, still using his girl voice. I’m sure it’ll be a lot of fun. Rohit had no idea what Preeti had planned or Ambili for that matter. He was sure it’d be fun, though, and he already had his suspicions as to what the plans were.