Sissy Powers Ch. 01

I smiled, looking at Clara resting her head on my chest, the way she usually does in the morning. But something felt different...

Wait!

Everything from earlier in the day came rushing back all at once, and I realized why these wake-up snuggles felt different: Clara's beautiful face was resting on my impressive bust!

Clara laughed at feeling me jerk in surprise. "Hey sweetheart, how are you? Did you just realize you've still got these sexy, perky tits?" she breathed, nuzzling into my chest and causing my nipples to harden. I nodded, smiling sheepishly.

"Well let me just tell you, babe, that you have nothing to worry about!" she enthused. "I realized something, too, when I woke up a few minutes ago. Wanna know what it was?" she asked, smiling mischievously up at me. Again I nodded, before deciding to just accept and try to get used to my new voice.

"Yeah, Clara, what was it?" I almost whispered, hearing the new, pleasant tone of my words.

"So you know how we just shared those amazing, dripping wet orgasms together, and you said you'd probably never cum that hard before?" I smiled fondly, feeling the remembered tingle in my pussy and moaning at how excited just her words got me.

She moved to straddle my waist, looking into my eyes as her hands slowly crept up my sides to caress my breasts again. I arched my back slightly, not yet sure how exactly to move this new body for optimal pleasure but knowing for absolutely certain that I wanted as much contact from her on my tits as possible. "Well, baby..." she purred, starting to fondle my tits and making me moan breathlessly at the pleasure, "that was just playing with these big, fun titties..." her hands moved so that the thumb and index finger of each hand were surrounding my sensitive nipples, "we haven't even played with your pussy yet!" she moaned in the most seductive voice I could imagine, pinching and twisting as she stared into my eyes and licked her lips.

It was like fireworks went off inside of my brain. "OH MY FUCKING GOD!!!" I screamed, my nipples sending wave after wave of pleasure through my entire body. I shuddered and arched my back wildly, curling my toes and feeling every muscle in my entire body seize up. So much fluid was gushing out of my pussy, coating my inner thighs and dripping down to my ass. After that initial outburst, I was rendered speechless, whimpering and moaning through the most powerful orgasm of my life for the second time in just a few hours.

Clara was amazing. She caressed, and squeezed, and rubbed, and pinched in the perfect way, keeping me right at the peak of pleasure for what seemed like hours but was probably 2 or 3 minutes. When I finally started to come down, she cupped my breasts with her soft, warm palms and leaned down to kiss me.

"Did that feel good, baby?" she breathed. I nodded meekly, not trusting my voice to make a sound if I tried to speak.. "Good, because I love you and I want you to feel so good."

"I - I want you to feel good, too, baby" I whispered, my voice cracking at first.

"I know, and there is plenty of time for that, trust me," she said with a smile. "But first, we should really get some food before we both die...."

I giggled my agreement, and we both stood up. Making our way to our respective dressers, we soon discovered a conundrum: Nothing fit me anymore. My old clothes were too big (I had had a fairly well-muscled torso and my new, feminine shoulders kept sliding out of my shirts) and when we tried, Clara's were too small (she's about 5'1" and a B cup and my 5'7" frame and bigger bust size stretched her clothes to the point of obscenity). Laughing, we decided on sweatpants and a sweatshirt for me and that our first stop would be the mall to buy me some clothes. I would be braless, but the thick Cornell University sweatshirt I was wearing should be plenty to hide my nipples.

Clara can't drive, and my license showed a picture of Leo (a man), so we decided to take an Uber. The two of us sat in the back whispering and giggling to each other for the entire ride. Clara was certain the driver kept checking me out, but I insisted it was her. We eventually agreed that he was probably just distracted by the sexy lesbian couple both rocking "I just got fucked" hair, and before we knew it we were getting out of the car in front of the mall.

"Thanks for the ride, sir!" Clara called to the driver before grabbing my hand and pulling me inside of the building. First stop: Victoria's Secret! We made our way quickly to the store, and I could feel the eyes of most of the men in the mall on us - and in particular on our asses - the whole way there. Is that what it felt like being Clara all the time? I shook my head, deciding to take this as a valuable learning experience.

Before I knew it, we were in front of the store. Now, I love buying sexy bras and lingerie for Clara and watching her try on clothes whenever we go shopping, so I have been inside of Victoria's Secret many times before. What I wasn't used to was being greeted with a friendly smile and wave, instead of a cautious greeting and being sized up for "is this guy a creep or a boyfriend" vibes. "Hey ladies!" a perky 20-something salesgirl chirped to us, coming over and smiling, "how can I help you today?" I froze, unsure what to say. Do we come clean? Or just pretend all of my clothes were destroyed in a fire? Luckily, Clara seemed to have thought this out ahead of time. I'm glad I'm with such a smart girl!

"Hey, so we need your help," she whispered, gesturing for the salesgirl to come close. She did, and leaned in to keep our conversation private. "My girlfriend here just moved in with me, and... well... she was raised by hippies and never really owned a bra before." The girl arched her eyebrows and smiled at us, looking me up and down quickly.

"So... you need the whole 'buying your first bra' experience? Like a fitting and everything?" she surmised, and I nodded bashfully. "Not a problem at all! I'm used to doing this with preteen girls and fitting them for like 30A bras, this should certainly be an interesting experience!" she quietly explained, looking excited for this novel interaction.

We headed back into the fitting area and, once inside a closed room, I was instructed to remove my sweatshirt. "Oh, damn honey," Heather - I had glanced at her nametag once I stopped staring at the floor - said in mild shock. "Um... You can keep your shirt on for this, you know..."

"We haven't moved her things over from her parents' house yet, okay?" Clara interjected, looking flustered. "Can't you just measure her topless?"

"Well yeah, of course, I just... sorry, yeah!" Heather stammered, flushing slightly. I was confused, until I saw why they both had started to look a little... tense. My nipples, which were still soooooo sensitive, had responded to the slightly chill air in the store by hardening into little half-inch nubs, pointing straight at Heather. "You're really beautiful, you know," Heather said shyly, before grabbing her measuring ribbon and stepping behind me.

"Yeah, I know, but she's taken," Clara said possessively. I was confused again - Clara had never minded me being flirted with by other women when I was a man - but then I realized why: She thought I was being turned on by Heather! I caught her eyes and tried to convey to her that I was just chilly, but she didn't seem to be picking up my signals.

"Okay, look, it's cold in here okay!" I exclaimed a bit loudly, causing both of the women in the room with me to chuckle.

"Ohhhh right, you're not used to that yet because... um... you just moved from down South," Clara said, understanding dawning on her face.

Heather smiled, looking reassured but not at all less nervous. "Okay, here we go, let's just..." she said, starting to circle my bust with the ribbon. "Wow, damn girl, you're one of the lucky ones, huh?" she said in awe, and I wasn't sure which of us she was talking to. "So the band size is a 32, I think, like you could wear a 34 or a 36 but then you'd have lots of boob spilling over the edges of the smaller cups..." she stepped in front and circled each tit in the ribbon, nodding to herself as if her assumption had been correct. "Yeah, so I'd have to recommend a 32DD, if I'm being honest. She must be quite the handful, huh?" she impishly asked Clara, smiling at her own wit.

"Oh, you have no idea..." Clara almost moaned, and I felt my pussy start to drip at the thought. "But anyway, so what do you have in that size in-store?" she asked, snapping out of her horny daze.

"Oh, right, duh!" Heather said apologetically. "So that's a pretty unique size, meaning we'd have to order a lot of what you might want, but we have a few things!" She rushed out of the fitting room, returning a minute later with a few boxes. I tried on and liked the feel of a plain beige one, a gray sports bra, and a lacy black push-up. When I had put on the black one and turned to show Heather and Clara, the salesgirl let out a low whistle.

"Are those things going to smack you in the face when you walk?" Clara giggled, and I looked down, immediately seeing her point. My big, perky tits looked huge in this bra, going up almost to the level of my collarbone.

"Um... so, like we could try adjusting the straps," Heather suggested meekly, looking flushed again. I nodded assent and she moved behind me, tightening and loosening straps until my tits rested at a more natural (though still pretty obscene) height. "Okay, well that's the best I can do for now!" she laughed, smiling at both of us apologetically.

"We'll take it, if only so we can get all of our car repairs and plumbing done for free," giggled Clara, and Heather broke into a huge smile at the thought of some poor man trying to control himself at the sight of me.

Heather picked up an iPad and we spent the next 20 minutes browsing the collection before settling on another 5 bras to order. They would be in the store in a week, and we could pick them up any time after that. "Here's my card, and, uh..." she trailed off, looking shyly at her own feet, "I work from 3PM to close, if you want to come in then. I'd love to, uh... help you girls some more," she said quickly.

Clara took the card and smiled at her. "We'd love to, Heather. Thanks for all of your help!" She smiled at the salesgirl, then looked at me and saw me standing there uncertainly. "Leah, sweety, before we go..." she let the sentence die on her tongue, glancing pointedly from me to Heather and then to my chest, still in the excessively slutty push-up. She cocked her head to the side, motioned feeling me up, glanced at Heather again and nodded, smiling. She was okay with me letting Heather feel my tits! I blushed like crazy, and my eyebrows shot up almost to my hairline. Clara laughed, and mouthed "do you want to?" I nodded a very exaggerated yes, then mouthed back "are you sure?"

Clara seemed to steel herself with determination. Maybe she thought I should get more experience than just one other woman feeling me up? "Hey Heather, it seems like you've been kinda, well... turned on by my girlfriend's tits, huh?" she asked point-blank, then blew a kiss to me while Heather's head shot up to look at me.

"No, I - I - I... Well... uh..." Heather stuttered, looking like she had just been caught with her hand in the cookie jar.

"It's okay, sweety, I am too," Clara said reassuringly, and Heather looked at her with confusion evident on her face. "In fact..." she breathed, moving her hand to my right breast, "I don't think I can wait until we get home to play with them again..."

"Oh, um... Well... I can give you two some privacy here..." Heather said, not believing what was happening.

"What if we don't want privacy?" Clara purred, taking Heather's hand and guiding it to my other breast. "What if we want to play?"

Heather gulped, and looked towards the door in fright. "But, I'm at work..."

"Yeah, and we are buying like $200 worth of bras, right? You're just helping us make sure they're what we want for Leah here, is that okay?" Heather nodded silently, licking her lips by instinct.

"I think that bra is way too slutty to wear out of here, don't you Leah?" Clara addressed me for the first time in a while.

"Yeah, I don't want those creepy guys out here staring at me, this is just for you baby..." I said, catching onto her game.

"Well, just for private," Clara corrected. "Either way, you'll need to change before we go and keep shopping, and who better to help you get changed than Heather here?" she suggested, winking at me.

Heather gulped, and looked to me for agreement. I smiled and nodded, my pulse quickening and my pussy nearly dripping with anticipation. "You know, Leah here can usually cum just from nipple play..." my girlfriend whispered in the salesgirl's ear before leaning back and removing her own shirt. She unfastened her bra while looking at Heather and almost moaning "I bet you want to rub your tits against hers, right?"

Heather's neck looked like a spring, it was bouncing her head up and down so hard in an excited nod. "Well then, you should take your top off..." Clara suggested, leaning into me and pressing our tits together. "Oh, it does feel so good, I love you Leah."

"I love you too, baby," I moaned out, the stimulation making my legs shake in anticipation. Over Clara's shoulder, I saw Heather practically rip her blouse and lacy bra off and move to join us.

Clara heard her soft footfalls approaching and pulled back, putting her hand on Heather's back and guiding her over to stand in front of me. She pushed us together, and I felt our nipples make contact before the mounds of soft flesh compressed slightly as we both let out moans of pleasure.

"Tell me how sexy my girlfriend is, Heather," Clara moaned, and Heather stopped panting for just a second.

"Oh my fucking god, this is amazing!" she gasped, moving her hands up to squeeze my boobs from the side and push them more firmly into hers.

"And I get that whenever I want... " Clara bragged, smiling at me. "I love you, Leah!" she whispered. I told her I loved her, too, and she beamed at me. "Now, Heather, are you going to make my girl cum or do I need to do it?" she asked sarcastically.

Heater's hand shot towards my crotch, but Clara quickly grabbed her wrist and pulled her hand back to my tits. "Nuh-uh-uh, not so fast. Maybe if we meet up outside of here one day, but for now, play with her titties until she squirts."

Heather's eyebrows shot up in shock. "She can really do that?" Clara just nodded, proud of my eroticism. Heather, breathing heavily, set to work massaging my tits and tweaking my nipples, pushing me closer and closer to orgasm. Finally, while she was twisting my nipples wickedly, Clara smiled over her shoulder and winked at me. That was all it took to send me over the edge, and I fell hard.

"OH MY FU -" my scream was cut off by a pair of panties being shoved in my mouth by Clara. Heather continued her ministrations until my orgasm died down, and when I was back in reality we all started laughing.

"Good thinking, babe!" I complimented, waving the panties.

"Yeah, seriously, thank you," Heather let out between gasping laughs, "I would lose my job for sure!" We all hugged and agreed to meet up sometime soon to continue the fun, and then Clara and I went to the register to pay for the merchandise. I was back in the comfy beige bra and new, Victoria's Secret sweatpants (the ones I had worn were soaked), and once everything was rung up Heather shooed us away.

"Seriously, guys, don't stress!" she admonished us. "I'll use my employee discount, and consider this me paying for our first date...?" she trailed off, looking at us hopefully. Clara caught my eye quickly before smiling at my obvious amazement.

"Heather, honey, thanks for the clothes! I'll text you soon, okay?" she promised, and Heather beamed.

We left the store happy, and the rest of our trip was relatively calm. We bought me an entirely new wardrobe, from sweats to professional pants and blouses to an elegant evening gown. Clara told me to wait for a second and ducked into Good Vibrations, the sex toy shop, on our way out. She returned with a mysterious bag and wouldn't let me see what was inside. Finally, we were dropped off at home by the Uber we had called and all of my new clothes were put away. We both sank back into the living room couch, exhausted but happy.

"Pretty good trip, I'd say!" Clara enthused.

"I totally agree!" I smiled, "and that was..."

"Fucking hot? Yeah!" Clara cut me off. "I don't know what it was, I just wanted to see you blow that girl's mind and get off in the process. Speaking of, I am pretty tense after this morning and that..." she trailed off suggestively.

I smiled hugely, looking at her with obvious excitement. "Want to see what I bought?" she asked. I nodded eagerly. Clara reached behind the couch we were on and pulled the bag up, setting it on the coffee table of the living room. She pulled out a new vibrator, a new dildo, and finally, with much showmanship... a double-ended dildo with a disk in the middle.

"We'll work up to that one," she assured me, seeing the excitement in my eyes layered with the fear at having such a huge plastic cock inside of me.