It's Complicated

Carla let me borrow some of her clothes and helped me with my makeup, I opted to not wear the wig, instead styling my own hair in a more feminine style, It actually looked nice," you are going to grow that out," Carla half asked and half told me." I like long hair," she kissed me on the cheek.

Breakfast was at a small diner not too far from her house, we chatted about how much fun we'd had last night, until Steve showed up and then laughed about how I had completely owned him, both holding out our pinky fingers, I'm sure the other people in the restaurant thought we were crazy. The salon Carla used was in the same shopping center, while I kept my hair longer than most guys, there wasn't enough for a man-bun, the stylist made some suggestions and cleaned it up a bit, giving me bangs and even adding some subtle highlights. The result was a very cute cut that could be feminine, or if I combed it right, androgynous, in other words, perfect. I had never had a manicure or a pedicure before, enjoying both immensely and choosing a soft pink for my nails to match Carla's. When they were done, even without makeup, I was either a slightly masculine woman or a very feminine man. I chalked it the whole makeover up as one more thing Carla had introduced me to that I hoped to enjoy many more times.

"So, your, um, friend, he doesn't work at all anymore," I asked as we headed back to the car.

"He might if I let him, but I don't like it anymore, I mean, it feels good, but it feels wrong, girls don't do that."

"Sometimes they do, I had a roommate in college whose girlfriend used a strap-on on him, he said it was pretty intense."

"So, you're saying you want me to fuck you like you did me this morning?"

"I don't know, I'm just trying to get a feel for the rules, I guess, but from the way you enjoyed it, I wouldn't say it was out of the question, I don't think I've ever even heard of someone having an orgasm like you had, and that kind of excites me. To be honest, if somethings going to go in me back there, I think I'd prefer it be you than some toy, but as long as you're involved, I think I'd be willing to try it either way."

"We'll see, but don't get your hopes up, he's going away as soon as I can afford the surgery anyway. Then you can please me in all kinds of ways," she smiled a big smile," and I'd like that a lot."

"I'd like that, too," I smiled thinking about the long-term implications of what Carla had just said and wondering if this girl I had just met might truly be 'the one,' so where to next?"

Carla pulled out her phone, "let me see if she's ready for us, I think you're going to enjoy this, too," she dialed a number,' Hi, it's me, are you ready? We can be there in about fifteen minutes. Great, we're on our way." Carla directed me into a residential neighborhood to a big two story house in a cul-de-sac, the woman that answered the door was Francine, she was Carla's Mary K consultant and was going to be giving me a crash course in what my colors were and how to properly apply my makeup, we talked about when it was appropriate to go heavier and when it was best to stay light, she even had suggestions for how a few light touches here and there could be beneficial in 'guy mode.' I bought everything she suggested and with her expert assistance, had completely done my own makeup twice before we left.

"Micki, you're lucky, you know, your beard is not very heavy and you shouldn't have too much of an issue with it showing through but, if you are even thinking about going down the same path as Carla, I'd suggest electrolysis anyway," she smiled and gave me a big hug," you are beautiful, by the way," I certainly felt that way and from the look on Carla's face, she agreed.

Francine was right, none the men in my family had much body hair and me being blonde enhanced that effect, my beard was light and spotty I only needed to shave twice a week at the most, the hair on my arms and legs was almost unnoticeable; I had shaved my legs this morning anyway, Carla had even helped. I had been shaving the small tuft of hair on my chest for years.

"Grab us a table," I put my hand on Carla's arm as we entered the restaurant," I need to make a pit stop.

"Ok, but hurry, I'm hungry, and lunch is my treat," the look on her face reminded me of the way my dad looked at me when he took the training wheels off my bike and I rode it by myself for the first time, great affection mixed with a large amount of pride, Carla's little girl was becoming a woman. I smiled at how it made me feel. The two ladies in the rest room smiled friendly smiles as I entered, choosing a stall and taking care of business, I washed my hands and decided to refresh my lipstick, not because it needed it, but because I wanted to watch myself do it in the mirror, it all felt so natural.

Carla had gotten us a booth along the window, "Having fun, yet," she joked as I slid in across from her.

"Absolutely, thank you for this, all of it, last night was wonderful; this morning has been magic, I'm not sure what I'm going to do about work tomorrow," I laughed.

"You really need to stop thanking me, I'm having as much fun as you are, it reminds me of when I got to where I could try to really be me for the first time, I remember the nerves, the excitement and then when it clicked, wow," she mimicked an explosion with her hands." Do you think they would object to Micki showing up every now and then, some companies are pretty accepting these days," Carla raised an eyebrow and cocked her head to one side?

What I had thought was a joke was now an issue, what ifI could dress at work? How far could I go and what if Micki became the new normal," I, I don't know," I could feel my brow furrow.

"Did I say something wrong," Carla reached across the table for my hand?

"No, I just have been so caught up in the moment, ever since I met you at Tanners, it has all been about the 'right now,' immediate gratification, I never stopped to think about going back to the real world."

"Who's to say the 'right now' isn't the real world? Are you happy? Are you having a good time? Are you comfortable? Do you like who you see when you look in the mirror?"

"Yes, to all of that and I love who I see in the mirror, but I also like being Mike," I paused," and you want a boyfriend, right, not a girlfriend?"

Carla laughed," But this isn't about me, it's about you, it's about you being true to who you are," she took a sip of water," I know a little bit about that, remember," her smile was so disarming," and Mike or Micki, I don't care, it's the person inside all of it that I fell in love with last night. When you stood up to Steve and told him to stuff it, I knew then that I had found my fairy tale, that's why I let you have me this morning," she picked up her menu and hid behind it.

I sat in silence for a few minutes, letting it grow, soaking up what Carla had said, letting her words sink in, I could feel the tension building across the table, "Simmons, Michael Travis Simmons," I finally said, "If you're going to be my girlfriend, you should at least know my full name."

The menu came down slowly, a weak smile was overshadowed by the anxiety and fear in her beautiful green eyes "Are you sure, I will understand if you say no, really, are you sure you want someone like me, are you sure you want a..." she couldn't finish the question.

I thought about everything that had happened, how it had felt when I met her, how it had felt when she told me her secret, how it had felt when I had protected her from Steve, and how it had felt when she had let me take her, there was nothing bad or wrong about any of it.

"Carla, yes, I want you, who or whatever you are" I winked and picked up my menu," and, to be honest, I fell in love with you when you walked into the diner last Friday and started stealing my fries, and you did warn me it was complicated."

The anxiety and fear vanished from Carla's eyes, we ate a quick lunch and went back to her house, leaving a trail of clothes from the front door to her bedroom, falling onto the bed and into each other's arms, our passion surged, Carla's hands went straight to my crotch while mine explored the wonders of her beautiful body, sliding up and down her long arms and across her back, sliding down and caressing and then grabbing her perfect ass as I kissed her full lips, sharing moans of growing sexual tension with her. Carla pulled away, reached into the nightstand and produced a bottle of lube, I rolled onto my back as she slathered my cock with the slick liquid, "now your turn," she handed me the bottle and got on all fours showing me her rose, coating my fingers I began to spread the lube around her hole before slowly pressing my fingers into her aching desire, one, then two, then three, my fingers slid easily in and out of her as her moaning grew. I tried to turn her on her back, but she resisted," I don't want you to see me like that," she protested.

"Carla, I love you, all of you and I want to kiss you and see your face while I make love to you, I want to fondle your breasts and suck on them while I fuck you, he's only one small part of you and I love him, too, I want you all."

She slowly rolled over spreading her legs and pulling them up to her shoulders, trying to hide her full erect cock with her hands. I leaned down and kissed her sweetly as I positioned myself at her gate, sliding slowly inside her as she relaxed.

I started to move in and out, slowly at first , then faster and more aggressively, watching her tits bounce up and down with each thrust and feeling her cock against my stomach, she wrapped her legs around my waist and clenched her ass as she began to shudder, her own warm juice covered her stomach and breasts and I erupted deep inside her.

Carla relaxed her legs and I fell on top of her burying my tongue deep in her mouth, kissing her passionately, slowly moving my attention to her ear and then to her neck, I left a trail of kisses along her collar bone and into the valley between her breasts. I took my time exploring them both, noticing that they were completely natural, her hormone therapy had done a good job, kissing and suckling one while my fingers teased and pinched the nipple of the other, I took turns, alternating my attention from one glorious mound to the other until I could hear Carla starting to moan again, then ever so delicately, ever so slowly, I moved down her stomach.

"Micki, please," I heard the faint protest but I couldn't , wouldn't stop, the salty tastes of her release showed me the way to the prize I was looking for, across her stomach to her belly button, I stopped and played with it for a few moments, teasing it with my tongue and then kissing my way past her waist to the base of her cock, I could feel her hard against my cheek and I stopped, looking up at Carla, I could see it in her eyes, the mixed emotions, but mostly the fear, I kissed the base of her cock just above her balls, and then the tip, gently licking the precum seeping from her member as I laid it gently on her stomach," Ok," I said, raising above her and looking down at her extraordinary beauty," He's really quite nice," I reached out and touched 'him,' "but I understand."

Carla opened her legs, "she's really nice, too, and she's hungry," Carla laughed as she pushed me onto my back and climbed on top of me, I watched as she lowered herself onto my throbbing erection, reaching up and fondling her perfect breasts as she lifted herself and then thrust me deeper and deeper into her aching hunger, I could feel her shudder as surges of her orgasm coursed through her body, I was not far behind and soon filled her with another load of my juice, she collapsed on top of me resting her head on my shoulder," I do love you Micki, I really do."

"Then let me help you," I could feel her erection between us," let me please you again, when 'he' is gone, I will gladly eat your pussy, but for now, 'he' is here. I've never done it before but let me at least try, I do know what it feels like to be in that condition, after all."

Carla lifted up and looked down at me, I could see the reservations in her face, "it's not going to change how I feel about you, I promise, if anything it will make us closer," she rolled over on her back and closed her eyes.

'He' was not too big but not small either, about average with a nice full head and a slight curve, I considered him closely as I tried to figure out how to do what I had promised, I positioned myself so 'he' was right in front of me and took 'him' in my hand, it felt familiar but different, leaning forward, I licked the tip as I had before and this time I swirled my tongue around the bulge. Being careful of my teeth, I slowly slid 'him' in my mouth and, using my tongue, guided 'him' deeper and deeper.

Focusing on the slight musky taste and the feeling of fullness, I soon found I had 'him' completely in my mouth and decided that I was enjoying the feeling. Cupping Carla's balls in my hand, I started to move up and down on the now slippery shaft, thinking about what the girls I had enjoyed had done to me and doing my best to imitate them. When Carla started moaning and fondling my cock, I knew I was on the right track and got a little more aggressive, pumping 'him' in and out of my mouth faster and faster. Carla surprised me when she came, there was not much, but I recognized the clench and then the release, followed by a small shudder and a sigh, the salty taste in my mouth told me I had achieved what I had set out to do.

"Thank you, that was actually nice," Carla smiled at me," now lay back and let me show you how a real woman takes care of that," I readily obliged.

My god, I thought Carla's ass was heaven, what she did to me with her mouth was almost indescribable, using her tongue and lips she kissed and caressed and sucked, using her hands to massage my balls while she held me deep in her throat and then using them to stroke my slippery shaft as she took one aching orb and then the other in her mouth, Carla brought me to the brink time and time again as I moaned loudly, begging her to let me finish and hoping that she would continue to torture me with the pleasure she was giving me. Then it happened, I was so focused on her mouth I didn't notice her putting the lube on her fingers, the cool liquid felt nice in my crack as she reached for her goal, first one finger and then two slipped inside me, she bent them forward, finding that spot and pressing gently as she drove my aching cock deep into her throat, I'm pretty sure the neighbors heard my scream as I convulsed and shook under the power of the most incredible orgasm I had ever experienced.

Carla brought her lips to mine, sharing just a taste of her reward with my eager mouth," Please, no, leave them there," I whispered as she started to pull her fingers from my hole," it feels so good."

Carla started moving them in and out," so you like this, don't you?"

"Yes, very much, it feels so good, I understand why you like it so much," she kept thrusting her fingers into me faster and harder.

"Do you want more? I can give you more if you want it."

"Yes please, "I practically begged.

Carla pulled her fingers from my hole and rolled over to the side of the bed, returning with a huge dildo, it had to be at least eight inches long and half again as thick as my own cock. I watched eagerly as she spread lube all over the shaft, "Are you ready," she asked? I just nodded opening my legs as far as I could in anticipation of what was to come.

It was amazing, the dildo stretched me open as she worked it deeper and deeper inside me, taking her time to not go too far too fast, it hurt a little at first, but the pain quickly turned to pleasure and I could feel something rising from deep inside me, similar to what it felt like when I got excited and hard but different, this was an energy, almost a warmth that was spreading down my legs and up through my body and out int my arms, Carla worked the massive dong in and out slowly driving it deeper and deeper until I could feel it base against my cheeks.

"That's my girl," Carla kissed me," do you like that? It feels good doesn't it?"

"Oh, god yes," I muttered as she started moving it in and out, fucking my aching hole with a growing fierceness, periodically thrusting it as deep as it would go and getting a muffled scream in return. The energy, the warmness I was feeling was changing, becoming more and more intense, I could feel it surging through my body, getting stronger until it was almost unbearable, I reached for my cock, wanting to bring the coming orgasm faster only to have Carla slap my hand away, rebuking my efforts.

"Girls don't do that, remember, you're just going to have to wait," she continued pumping me with the toy. Finally, my body could take no more and a series of spasms spread from my aching ass through my torso, arms and legs, I couldn't stop shaking, I had thought the orgasm from Carla's blow job was intense , when the tremors and aftershocks this one left subsided, I couldn't move.

Carla laid next to me holding me close and leaving her toy deep inside me, allowing me to enjoy the fullness as she ran her fingers over my sweaty body and smothered me in a million small gentle kisses. We lay together for a while, kissing and caressing each other before we took a shower. I got to fuck her one more time as we showered, I fixed my hair and did my makeup as she fixed me a very nice dinner, we mostly just smiled at each other eating in silence as thoughts of our afternoon floated through our minds.

Carla loaned me a skirt and top to wear home, kissing me hard as I got in my car," I think you should move in with me," she leaned in my window and kissed me one more time," think about it, ok," and I promised I would?

All the way home, I thought about the weekend, what had started when we met Friday afternoon and how quickly it had become the passionate afternoon of mind-blowing sex, and then the idea of moving in with Carla, which both excited me and terrified me at the same time.

"Excuse me, miss," my next-door neighbor Joe and I had bumped into each other on the stairs, he had no idea who I was. I looked back when I got to the landing and caught him taking one more look, the hungry smile he gave me sent a small tingle up my spine, from his position, I was pretty sure he could see my panties up my skirt. I smiled to myself as I unlocked my door. It had been a long weekend, even though I had already had three showers today, I opted to soak in a hot tub to think things through, I wasn't sure what I was going to do about work in the morning, what was I going to wear, would it be Mike or Micki that showed up, and then there was the whole Steve issue to deal with. Whatever happened, tomorrow was going to be interesting. By the time I crawled in bed, I was completely worn out, emotionally, and physically; I slept like a baby.

Monday morning found me refreshed and ready to face whatever came, I was sore from my tryst with Carla, her toy had literally gone places I had never thought would ever be explored, the dull ache in my hips and butt would remind me of that wonderful experience all day. I made myself a cup of coffee and pulled the Mc Phearson file out of my briefcase, looking it over one more time and reviewing my analysis and proposal to make sure I hadn't missed anything too obvious. Happy with what I had done, I rinsed my coffee cup, put the papers back in my briefcase and went to get dressed.

I found that I could just tousle my hair to get the effect the hairdresser had intended, choosing light makeup, a little eyeliner but no mascara or lipstick, leant me toward putting on one of my bras, and It became obvious that Micki was winning. Deciding I should at least try to be a little discreet, I put on my standard dark grey pinstripe suit, slipped on my low heels, grabbed my briefcase, dropped my lipstick and mascara in my purse just in case and hung it on my shoulder, and headed out the door.