Even Therapists Struggle Ch. 02

I groaned as I tried to keep my eyes closed against the morning light. "I don't remember it being this light in my bedroom. And why doesn't this feel like my bed?" It was the snoring that caused my eyes to snap open, mainly because the snores weren't mine. I shifted my position to see that not only was I not in my bedroom, I was also not alone. No, I was laying on Cameron, specifically between his legs as he lay sprawled across my crouch. The memories of last night, of watching the movie and then delving into other things... the memories of what we did and didn't do... flooded my brain and left me blushing.

But I wasn't unhappy. Maybe a little bit embarrassed, but the truth was out and I'd found a friend who liked me as I was, with my not-so-little kink and quirk, and I wanted to hold on to the fantasy that the moment would never end. Then my bladder woke up and all I could think of was "foiled again." I needed to figure out how to extricate myself from my position on Cameron without waking him. As gingerly as I could, I tried to slide off the couch and sneak off to the bathroom.

"Going somewhere?" A voice asked and I yelped, missed my grip on the couch, and fell to the floor. "Oh damn, Tristan, are you okay?" The voice was Cameron's and he quickly sat up and lifted me up off the floor.

"Yeah, yeah, I'm fine," I said quickly with my face burning with even more embarrassment. "I have to pee," I said no longer able to delay things. The fall and the subsequent bump on the floor had sent some messages through my system and I hurried to the bathroom to take care of business. I scrambled to my feet and ran down the hallway to my bathroom. I closed the door and did my little dance as I pulled down my leggings and panties, and before I was aware of what I was doing, I was sitting down to pee.

I finished up my business and felt a huge sense of relief. I returned to the living room to find Cameron making himself comfortable in my kitchen as he prepared waffles and hash browns. "How did you know?" I asked as I unconsciously started salivating at the sight and smell.

"Know what?" He answered as he used a fork to remove a waffle from the waffle iron. He placed it on the island and I sat down on the bar side. As he waited for the next waffle to finish, he poured me a glass of milk and spooned some hash browns onto a smaller plate for me.

"That waffles and hash browns was one of my favorite meals?" I said as I started cutting up the waffle and pouring the syrup. I started to raise a bite to my mouth when Cameron reached out and took my hand. I looked at him confused when he started praying over the food.

When he was finished, he gave my hand a squeeze as he turned back to get his own breakfast together. "I didn't know, but I'm glad to find out that it is because it's one of my favorites too." He sat down next to me, but not before giving me a kiss on the forehead which left me feeling warm and fuzzy.

"So," I said after finishing another mouthful. "First off, compliments to the chef." I gave him a nod and he gave a subtle bow. "Secondly, you said you wanted to spend the day together. Is that still true?"

"Mmm-hmm," he agreed through a mouthful of food. After swallowing he continued, "I want to know what kind of clothes you have in your wardrobe, then I want to live out one of my fantasies."

I raised an eyebrow as I looked at him. "What kind of fantasy?" I said, my voice dripping with skepticism.

"I want to take you shopping. Kind of like Richard Gere did for Julia Roberts in Pretty Woman."

I nodded, knowing exactly what movie scene he was talking about. "That sounds fun and romantic, but let's not forget, I'm not Julia Roberts."

"I know, I know," he said after consuming another forkful of food. "And I don't want you to be unless you want to. But we can go shopping and you can be helping me buy some things for my girlfriend," he said with a shrug. "It will be like I'm planning a surprise for her. I'm sure the staff at the stores won't make it an issue unless we do. " He munched on another forkful of food. "Plus, I have an idea. If and only if you want to, there's a specialty shop that I want us to go to. They might be able to help you with your look if you want them to. But even if you don't, I think there are a few things we want to get from there, just in case."

I ate a couple of bites of my own as I considered Cameron's plan. I couldn't lie to myself. The idea of going on a shopping spree, even a small one was like a dream, one that I never thought I would experience. I even had ideas of where I would like to do some shopping, but could I really do that with him? Could we really convince store employees that we were there shopping for his girlfriend? Or would they know it was me? And what was this other store he was talking about?

"I'm not ready to go out dressed yet. But if you're willing to hold my hand, metaphorically, while shopping, I think we could go with the girlfriend ruse."

A wide grin spread on Cameron's face. "This is going to be fun." He surprised me by leaning in and kissing me even though I still had food in my mouth. Still, no tongue this time, so I guess it was okay. "Just do me one favor."

"What's that?"

"Can you please wear some panties for me? And a camisole if you have one?" My eyes went wide at his suggestion. "I just really like the idea of you, presenting as you normally do, but wearing a little something underneath that's special and just for me. Pretty please?" I was not prepared for the puppy dog eyes that he hit me with and I started to giggle as I shook my head.

"Just for you," I said as I leaned over and gave him a peck on the lips. "But first, I think showers are called for." Cameron's eyes brightened. "Solo. Solo showers," I added quickly. We had moved so fast on some things, but there was still space to slow things down, at least a little bit.

An hour later, we were both showered and dressed. Cameron was still wearing his clothes from the day before, but I had been able to pull on a new outfit. As requested, my undergarments consisted of a pale pink camisole and boyshort panty, while my outer clothes consisted of a pair of jeans, a sweatshirt and tennis shoes. The jeans always felt stiff on my shaven legs and the lack of friction from the panties made me wear a belt.

"You ready?" Cameron said as he stood by the door.

I took a deep breath and said, "as ready as I'll ever be." Cameron opened the door and I paused on the threshold. "You know this is the first time that I will have ever left my place wearing any type of women's clothing."

"How are you feeling? Are you still okay with this?" Cameron asked as he grabbed my hand and turned me to face him. I looked at him and saw the questions in his eyes, and all I could do was smile in return before I quickly gave him a kiss.

"I'm nervous and a little scared. And if you weren't with me, I doubt that I would do it. But..."

Cameron reached out and lifted my chin before leaning in and giving me a much deeper kiss. "I'm with you every step of the way and I promise that I won't let anything happen to you."

With that reassurance, we left my place and headed down to Cameron's Lexus SUV. Like the consummate gentleman that he was, Cameron opened the door for me and I blushed. I prayed no one would see it and think something untoward was happening. But as I slid into his car, I thought about everything that we'd shared in our conversation, and I had to ask why did I care what anyone else thought? It wasn't their life, it was mine. And right now, being doted on by Cameron made me feel good and special and appreciated.

As Cameron got into the driver's seat, I looked at him with a smile and reached over to take his hand. He smiled at me and squeezed my hand before asking questions. "Are you okay? You looked a little gobsmacked when I opened the door for you. You thinking about what people will think about you or about us?"

I nodded. "Yes, those exact thoughts and fears were definitely what I was confronted with. And while I'm trying to remind myself that other people's opinions only matter as much as I let them, I know that those fears and anxieties aren't unfounded. And the more we do, the more I realize how much I'm going to need your support, because i can totally see freaking out at some point."

"Hey, hey, hey," Cameron said as he stroked my hand. "If I see you freaking out, I'll get you some place safe. And while we're out, I won't let anyone hurt you. The emotional stuff, we'll deal with that together."

He gave my hand one more squeeze before lifting it to his lips and kissing the back of it and returning it to my lap so he could start his car and drive. We talked about our families and dating relationships as we drove and generally grew more comfortable and familiar with each other. I was surprised when he pulled into the back of a strip mall, seeing stores that I never knew were there.

"Where are we going?" I asked as Cameron put the truck in park.

"Do you see that shop right there? WIITWD?" He pointed to one of the shops towards the end of the strip. "Being transparent, it's an adult bookstore and I have a friend that works there." My eyes started to widen as my mind raced through the possibilities of what he might want to do with me in this place. "I'm not going to ask you to do anything creepy like go to a glory hole or anything," Cameron said quickly, sensing my rapidly increasing fear. "I just thought it might be easier to get your measurements professionally done here before our shopping trip. Aaaaand if you want to pick up a few things from here for later, I won't complain."

Cameron smiled a crooked smile at me and I couldn't help but smile back gently. "Nasty boy," I said.

"I have my moments," Cameron said with a wink as he led us toward the building and held the door open for me.

"Hello and welcome to 'What It Is That We Do,'" said a voice from behind the counter. Ah, now the cryptic name of the store makes sense, I thought to myself as I tried to identify the source of the voice.

"Hey Chantelle, it's been awhile." Cameron walked up to the counter and stuck his head over.

"Well as I live and breathe!" Chantelle exclaimed as she popped up to see him. A grin spread over her face in her porcelain colored skin. She had a head full of red braids that looked fairly natural, over a fit figure with small breasts, wide hips, and an hourglass figure that would have men staring... like I was. "If it isn't our local man of mystery. How have you been? And more importantly WHERE have you been? We haven't seen you at the club in over two years."

Cameron ducked his head a little. "I've been around, just focusing on trying to get my life right. And you know, after Layla, I just needed some time to recover and get my head straight."

Chantelle nodded understandingly. "We tried to tell you that girl wasn't right for you, but you just had to f around and find out for yourself." She came from behind the counter and gave Cameron a hug before glancing past his shoulders and seeing me. "And who is this?"

"Tristan," I croaked. Clearing my throat I tried again. "Tristan. My name is Tristan."

"Nice to meet you Tristan," Chantelle said, grabbing my hand and pulling me into a surprise hug. "Are you here with Cameron?"

I nodded, not sure what to say about the status of our relationship.

"Don't worry hon," Chantelle said as she grinned at me. "There is no judgment here. Just pleasure, and maybe a little bit of pain." She winked at me as she smacked her own ass.

"Easy Chantelle," Cameron interjected. "Tristan and I were hoping to do a little shopping and we needed to get his measurements."

"And I'm guessing you don't mean measurements for men's clothes, right?" Chantelle said with a knowing smile that had my caramel-colored skin take on a deeply red undertone from my intense blushing. "It's okay sweetie. You're not the first crossdresser that has crossed our threshold. We cater to a wide variety of kinks and interests. I'm happy to take your measurements and I can keep them on file if you all want to order anything from our website. What's your style?"

"What?" I said as my head spun from the torrent of Chantelle's words. "Style?"

"Mm-hmm," She said as she sized me up visually. "Sissy? Street? Princess? Girl next door? Goth? Little? Or something else entirely."

"Oh," I said as I tried to kick my mind back into gear. "Umm, girl next door I guess."

Chantelle nodded approvingly. "I can totally see that for you. Tell you what, let's step back into the changing room so I can take your measurements, and if you want, I can set a few things aside for you that I think you might like."

"Well, we are supposed to go shopping after this," I stammered.

"Perfect. You guys go do your 'Pretty Woman' thing and then swing back by here on your way home." Chantelle grabbed my hand and started leading me towards the changing room. "Man the till, would you Cameron? And if there's anything you like, just put it to the side and I'll hold it for you." The last I saw was Cameron giving us a nod, and giving me a wink and blowing a kiss before the door to the changing room closed.

"Okay," Chantelle started. "I'm going to need you to strip down to your underwear so I can get the best measurements." She took a measuring tape from a nearby drawer that I hadn't noticed. "Have you been doing this long?"

"On and off for a few years," I said as I shrugged out of my sweatshirt, kicked off my shoes and nervously shed my jeans. "But only at home and never fully."

Chantelle nodded as she approached, smiling as she saw my camisole and panties, motioning for me to put my arms up so she could measure around my bust. "Girl, I understand. I've heard that same tale so many times that it makes me sad. But you've got to get out there, and you've got a good one there with Cameron."

"Umm, yeah," I said as she measured my hips and waist. "How do you know him?"

"Not like that, if that's what you're thinking," she said as she got down on her knees to measure the length of my legs. "In case you hadn't figured it out, I'm a lesbian. But i met Cameron a few years ago at a local fetish club. I was there with my partner, Demetria, and Cameron was there with Layla. We all hit it off and became fast friends. At least Cameron, Demetria and I did. Layla was always kind of standoffish and that made us suspicious. Step," she said as she pulled over a foot sizing device. "After awhile, Cameron just disappeared from the scene. And now, here he is with you, and he looks happy."

I smiled nervously. "We haven't really done anything yet. Just talked and..."

"And you got to feel his soft lips on yours while his strong hands caressed you, making you feel safe and sexy?" I blushed as Chantelle described our night knowingly. "Well, like I said. He looks happy, happier than I remember seeing him. And you look pretty happy too, even if you are a bit nervous."

I hunched my shoulders. "Yeah, this seemed like a good idea at home, but now my nerves are really starting to tingle."

Chantelle reached over and took my face in her hands. "It's going to be fine. Don't worry about anyone else other than that man in there. Just let yourself be in a way I don't think you ever have before. Go, shop, give his credit card a workout," she said with a giggle. "If you want, you can come back here and change, give him a brief fashion show, and I can give you a makeover. You have a pretty face and it won't take much. But a little makeup, maybe style your hair a little, and I promise you'll turn plenty of heads."

She let me go and I started pulling my clothes back on. "We'll see. If I haven't had a nervous breakdown before then, I'm sure we'll be back. The fashion show, well, we'll wait and see."

"That's fine," Chantelle said with a sly smile. "Just in case, I think I've got a special ensemble for you."

We exited the changing room and found Cameron engaged in conversation with another customer. "... I haven't used those, but I know people that have and they swear that it sets the body's systems on fire, in a good way." Cameron looked up and saw us. "You know what, here comes one of the proprietors of the shop. Let me turn you over to her capable hands and she can tell you everything you want to know."

He slipped out from behind the counter and I couldn't help but take how handsome he was in his pants and untucked button down shirt with his sleeves rolled up. "Here," Chantelle said, interrupting my thoughts of wanting to see what Cameron looked like again under his shirt. I knew, but I was appreciating him from a deeper perspective now. I looked down and saw that Chantelle had handed me a piece of paper. "It's my phone number. Call me anytime. And for anything, well except for the naughty stuff. That's all you and Cameron." She giggled and winked and, for the umpteenth time, I blushed.

Chantelle gave Cameron a quick peck on the cheek as she passed by him, whispering something in his ear that made him look at me and left me feeling uncomfortable because I didn't know what she possibly could have said. Still, when Cameron came over to me and said, "ready to go?"

"Yes, I think so." My voice held my confusion even as I waved to Chantelle who made the thumb and pinkie sign for call me.

Walking out of the store, Cameron rested his hand on my lower back protectively and I wondered what was up. "Cam, what did Chantelle say to you? I mean, I know it's private but the way you looked at me kind of changed and now I'm nervous and I don't know if we should be doing this anymore and..."

Cameron grabbed me by the shoulders and turned me to face him. The anxiety in my eyes was slowly pushed away by the gentleness in his. "She said to take care of you because you're a good person. That, and she slipped me this."

He reached into his pocket and pulled something out that, as he moved it into my line of sight, made my face burn from blushing. What he had in his hand was actually two things. The first, a small bottle of lube. The second, a small butt plug with a green jewel on the end of it. "Put that away. Someone will see it."

Cameron slipped it back into his pocket. "No one's looking, trust me." I looked up and around and saw that the nearest people were down the walkway from us and walking in the opposite direction. "She just thought that we might want to use it later."

"Oh God," I moaned. "I mean, she's cool and all. But I don't think I was ready for anyone else to know what MIGHT happen, especially before I made the decision."

"Then I'm sorry," Cameron said with genuine apology in his voice. "Can we just forget about that and go on with the rest of our plans? Pretty please?"

I tried not to look at him. I really did, but my eyes were drawn to him like a tractor beam. And on his face, he had his puppy dog eyes on full display. I pressed my hand to my forehead. "You know, you can't use those puppy dog eyes forever. I will get used to them."

Cameron grinned at me. "I know. But until you, they're one of the best tools I have." He nudged me gently with his hand on my back, moving me in the direction of his car. "I have some ideas of where we could do some shopping and not be bothered. And no," he said with a quick hand up to stop my inquiry. "They're not hidden stores. Just not in a mall."

"Okay," I said as I climbed into his car through the door he opened for me. "I trust you... for now."

"I'll take it," Cameron said as he shifted the car into drive and whisked us away to our next destination. We continued to talk and laugh as we drove until he pulled us into another parking lot in front of...

"Dress Barn?" I looked at him incredulously.

"Have you ever been in there?" I shook my head no. "They've got some pretty nice things. Classy and stylish. And the sizes are built more for people that aren't shaped like stick figures. And my dear, you have junk in your trunk that deserves to be well taken care of."

I rolled my eyes. "Perv," I said teasingly as we got out of the car. As we walked in, I noticed that there were only a couple of other customers which suited me just fine. Looking around, I saw some dresses that were just my style and I walked over to them, nervous that someone might approach me and call ME out as a perv. I barely heard Cameron across the room talking to one of the salespeople and explaining that "... my friend is trying to surprise his wife with a few things. Here's my card. Just ring up whatever he wants when we're done." He leaned over and whispered something in her ear that made her eyes widen slightly. They shared a few more whispered words before she gave him a reassuring pat on the arm. The salesperson, an attractive Black woman in her 40s or 50s (it was hard to tell because, well you know, Black don't crack) gave me an understanding look as she headed towards the register then accompanied Cameron over to where I was standing.

The salesperson spoke up first. "Hi, my name is Danielle. Your friend was telling me that you were looking for some things for your 'wife.' I'm happy to help you in any way you need. Just raise your hand and I'll come running." She smiled warmly and I couldn't help but appreciate her friendliness. "Do you know her sizes?"

"Believe it or not, I do," I said with a laugh, primarily to mask the fact that I was still having feelings from getting my measurements from Chantelle earlier in the day.

"Excellent," Danielle said with a clap of her hands. "Then I'll leave you to your shopping. But if you need anything at all, don't hesitate to call." She gave another smile then moved off to another section of the store leaving Cameron and I staring at each other.

"See anything you like?" Cameron asked as he looked through some of the dresses on the rack in front of him.

"Yes," I said slowly as suspicion caused my eyes to narrow at him. "Did you tell her about me?" I hissed.

Cameron stood firm, looking me in my eyes which caused me to be taken aback. "I did. Believe it or not, I've seen her before at a fetish event. So when I shared that our paths had crossed before, she understood. She's an ally and she knows how to be discreet. So if you need anything and I'm not right here, today or any other day, she'll be able to help you out."

I blinked in surprise. "Really?" I peeked over his shoulder and saw Danielle watching us. She gave me a subtle wink before turning back to her register. "Why would she do that? I mean, I'm not complaining. I'm just surprised."

"Because of all your experiences with other women?" Cameron asked gently and I nodded. "Well, you just needed to meet a different class of woman... or man." He grinned at me and I blushed.

Not knowing what else to say, I picked up two of the dresses that had caught my eye and showed them to him. One was a denim minidress with spaghetti straps and a flared waist. I knew it would look cute with the right top underneath, I just had to find the match. The second dress was an army green, satin dress that looked like it would stop around my knees. It buttoned like a t-shirt at the top, but had a sash for a belt that gave it a more stylish look, and pockets.

Cameron took the dresses and looked at them admiringly. "These are both beautiful and I think that the woman in your life would both appreciate them and look stunning in them." He smiled as he kept the game going, even if it was only for the two of us. I did my best not to blush as I continued perusing the racks.

I was surprised at the style and quality of the clothes. They were inexpensive but still of high quality and it felt like they would last awhile. Plus it seemed like the styles were versatile, going from the office to happy hour without too many difficulties. Although I had been crossdressing in some regards for years, even accumulating a small yet decent wardrobe, it had only been recently that I had stopped trying to dress like a fetish princess and started to wear clothes women might wear on a daily basis. It's like my identity was changing and I was becoming more than a caricature of womanhood, and instead really leaning into and embracing more of the experience of being a woman. And now, being here shopping with Cameron, I had taken yet another step on the path of legitimacy. I mean, I knew I'd never be a full woman, and I wasn't sure if that was even what I wanted. But at least I was honoring my love for all things feminine by trying to be "real" rather than just a fantasy version.

"Hey," Cameron asked, interrupting my thoughts. "You okay? You looked like you were somewhere else for a bit."

"Yeah," I replied with a smile as I reached out to touch his arm. "I'm just... happy." I dipped my eyes. "I know it may not make much sense but being here, with you, in this store, it makes me feel warm inside. Like I've been wrapped in a cozy blanket, only it's on the inside of me." I risked a glance up at him then quickly turned back to the rack of skirts on my right. "I probably sound silly or stupid."

I was surprised when I felt Cameron's hand on my arm, and when I turned to look at his hand, he slid his hand up under my chin to raise my eyes to look at him. "You don't sound silly or stupid. You sound like you're breaking through a barrier or a cocoon. I don't care whether you want to live as a woman full time, or just have this be something that you do from time to time. I just want you to be happy and I hope to be a part of that."

My breath caught in my chest as I saw the earnestness of Cameron's words in his eyes. He was serious. He wanted to be with me! And he seemed to not care what form I took. I blinked a couple of surprising tears away as I nodded at him. "You are. I can't do this without you."

"That's only because I'm footing the bill," Cameron teased, earning a punch in the arm from me.

"Looks like you two are having a good time," came another voice. Cameron and I looked to see Danielle standing nearby smiling at us. "I think you two are really sweet together, and obviously sweet on each other."

My shoulders hunched and I blushed with embarrassment as I prepared myself to be ridiculed yet again. The stress and the memories of past rejections had me so tense that when a hand reached out to touch me and I automatically threw my hands up in defense.

"Hey, hey, it's okay," Danielle said in a soothing voice. "You're safe, with Cameron and with me." I sniffed away a tear before mustering up the courage to start to look up at her. When I did, I was presented with a soft, sad smile. "Sweetie, I don't know who hurt you, but I think that what you're doing is beautiful. Risky and brave, yes, but also a wonderful thing because it's allowing your spirit to grow and blossom and bring more love and joy into the world."

"You... you know?" I asked timidly, afraid to fully say the words to someone besides Cameron. "How?"

"Hon, you are certainly not the first man to come in here with a desire to explore their feminine side." Danielle grinned at me. "But I do admire that you came in with a friend who supports you and doesn't look like he's trying to take advantage of you." A dark cloud passed over her face and I wondered what all she had seen in the memories she'd called up in that moment.

Gently, I prodded. "Sounds like you might need to talk. I'm happy to listen," I said with a smile which Danielle returned.

"I just may take you up on that. And honestly, I'd love to see you when all is said and done," she said, giving me a once-over as she tried to imagine what I might look like in some of the outfits Cameron was now carrying. "I'll give you my number when I ring you up. So if YOU ever need to talk, or go out with dressed up, you know you'll have someone else besides your man to lean on."

Danielle leaned in and gave me a sisterly hug that I snuggled in to. "Now," she brushed a near tear from her eye. "You and Cameron, go finish your shopping. I'll meet you at the register."

Cameron turned to me as Danielle briskly walked to another part of the store to straighten some clothes up as she waited for us to finish. "Are you okay?" His question was full of concern and I could only smile at him.

"I'm just surprised and happy," I grabbed Cameron's hand and gave it a squeeze. "Come on, I think we've got what we need from this store. Time to go shoe shopping!" I laughed as Cameron groaned. Still, he kept on smiling so I knew he wasn't terribly upset about it. After all, he was going to be the primary beneficiary of this particular excursion.