Erika's Story Ch. 05

This is the fifth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it.

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I awoke late in the morning, nearer to noon to find myself curled up next to Mary she had crept over to my side of the bed during the night and now had one arm draped over me and her right knee resting against my chastity cage which I was still trying to get used to wearing and was still a bit uncomfortable. I wondered what it was about my being in chastity that got Mary excited, was it the control over a man, was it just the idea of taking away my masculinity? I didn't really understand the allure of the chastity cage thing to be honest but she seemed to be into it so I guess I will give it a shot for her, after all the crossdressing thing wasn't really her thing at first either and now we were having a lot of fun with it. I tried to move a bit, and Mary opened her eyes and gave me a kiss on the cheek.

"Morning Love." Mary said yawning a bit. "How's my girl this morning."

"Still tired, I had a bunch of weird dreams and didn't sleep well, and the cage on my dick isn't the most comfortable thing to have when you are trying to sleep in I guess."

"Aww... is the cage making my girl cranky?" She teasingly said. " Just for whining about it, I'm going to make that cage really uncomfortable."

Mary reached under her nightie and pulled down her panties shooting me a wicked little grin. Raising up on the bed, she stood above me straddling me, and giving me a great view of her pussy and ass. Mary brought a hand up to her sex and gently started massaging it with two fingers. Her slowly bucking hips and fingers working over her pussy made my penis take notice and start to strain against the cage. She was going to tease me and torture me all weekend with this damn chastity cage. Mary was sure having fun being a little cock tease, knowing my cock was helplessly locked away. She started to lower herself onto my face. I always loved it when she sat on my face, being smothered under her weight with my mouth being used to pleasure her and my nose buried in her ass, barely able to breath was a little fetish of mine and she always came hard from it as well. This time was no different, she was really grinding herself into my willing tongue, I licked and sucked on her lips as well as I could with her grinding down on my face. My nose was buried deep in her ass crack, I could hardly breath which only made it more arousing for me. She rocked herself forward just a bit and positioned her ass directly over my lapping tongue. She had always loved it when I ate her ass, every since the time I had been a little drunk and decided to try out eating ass on her. She was my first for ass eating and I was hers, we discovered that we both enjoyed it well, at least after the initial shock of having a tongue in your ass wore off anyway. Her fingers were feverishly working her clit over as I probed her sexy asshole with my tongue. This continued for some time, her masturbating her pussy while I explored her beautiful backside until she decided she needed my mouth back on her soaking wet pussy. She reached down and started to massage my balls and play with my cage torturing me even further. I felt her body tense up and her thighs quivering around my head. She was about to orgasm. And then it happened, I felt a stream of hot fluid spray into my mouth and across my face. Did she just piss on me, did she squirt or something? I had seen porn with girls squirting, but Mary had never squirted before or anything like that. Mary's body went immediately still as she sat perfectly upright. She had accidentally peed in my mouth and on my chest when she orgasmed, the slightly pungent taste and her sudden stoppage had assured me of that. What was I suppose to do, I didn't want to freak out about it and make her feel weird about it or anything like that. I wiped my face off and decided the taste wasn't really that bad and decided I would just swallow what got in my mouth and not make a big scene about it.

"Oh my god babe ... I'm so sorry, I cant believe that just happened!" She said quickly spinning off my face, and sitting on the bed looking at me. "I have never done that before, I was just really getting into the face sitting and your tongue felt so good... oh my god I so sorry!" Mary looked like she was full of shame and about to cry.

"Its fine babe... It didn't really taste bad or anything.. Don't cry honey girl, don't cry."

I wrapped my arms around her to assure her I wasn't angry with her for anything. "It's ok baby, at least I know I gave you one hell of an orgasm, I honestly thought you were just experimenting with pissing during sex, and look some people are into that kind of thing and besides, now we can say we tried watersports." I said jokingly. "Honestly It was kind of hot you know me, I will try almost anything once I suppose."

Mary relaxed a bit after my reassurances, and I went out to the fridge to get something to drink and get the taste of her piss out of my mouth after our little sex adventure. I was sitting in the chair in the living room when Mary came into the room carrying her yoga mat and dressed like she was going to the gym. She had no makeup on and her hair was just pulled back into a ponytail, but she always looked so sexy in her tight little yoga clothes. She turned on YouTube and queued up a yoga video, I was looking forward to watching her bending and stretching in front of me.

"Well what are you waiting for?" Mary asked.

"Waiting for my sexy ass woman to put on a yoga show." I replied.

"I don't think so... not today, if you wanna be a girl this weekend you are doing yoga with me." Mary said with a grin on her face. "You think I stay in shape by sitting on my ass all day, and besides it will be good for you to stretch out a bit and tone things up."

What the hell, I guess ill give it a try. I had never done yoga a day in my life, but I guess she was right I could stand for some toning and firming. I went into my suitcase and got out a pair of grey leggings and a tight light blue camisole top, It wasn't really yoga gear but I didn't really have the right outfit. Giving my hair a quick comb I put it into a ponytail and headed back to the living room for my first yoga session. Mary had two yoga mats arranged on the floor and was waiting for me.

"OK baby yoga is exercise, but it is also a kind of meditation... follow along with the video and just do your best. Mary smiled reassuringly at me. "I put on a beginner yoga session, it shouldn't be too hard on you... I promise."

For the next thirty five mins I busted my ass, twisting and bending in every way imaginable. A barrage of downward dogs, and child's poses, warrior poses and so forth. I tried to pay attention to the breathing like the video instructed but my arms were shaking and my ass and legs felt like they were on fire. The video ended with me on my back hands outstretched with a rhythmic breathing.

"That was a beginner lesson?" I asked once my breath slowed.

"Yup, that one was easy peasy... you are just not used to doing things like that. I try to work out 5 days a week either jogging or some home yoga, a girl has to watch her figure you know."

"Well I will keep that in mind, now if you don't mind I'm going to take my sweaty ass to the shower."

After the afternoon yoga session, the hot water felt good on my tired muscles. I took the time to give the legs a quick shave and let the hot water relax me a bit. I tried to shave my pubic area the best I could with the chastity device getting in the way on some bits. I rinsed off and stepped out of the shower and found a pink fluffy towel waiting for me on the sink with a little post it note with a heart drawn on it. Aww... Mary must have snuck in and left me the love towel while I was shaving.

I patted dry and wrapped the towel around my waist and shaved my face and brushed my teeth.

Entering the bedroom Mary had laid out three bottles of lotion on the bed.

"Remember to lotion up every day and especially after a shower." she said pointing to the lotion on the bed, one is for the body, one for face and one just for around the eyes."

"The eyes are not part of the face?" I asked.

"The eye one helps prevent wrinkles silly... Oh and girls don't wear a towel around the waist and walk around with their tits hanging out." She said readjusting my towel. "Ok baby... lotion up and put your makeup on, I'm gonna hop in the shower."

Mary gave me a little kiss and headed off to the bathroom. After giving my body a full coating of the fruity lotion and applying the face lotions, I sat at the vanity and focused on the makeup. I got to thinking, this would be the first day of my life that I was going to be in girl mode all day and not just a night time dress up jack off session at home or maybe some hot sex with Mary. What would it feel like to wake up every morning and put on makeup and get all dressed up for the day? I supposed about fifty one percent of the population would say it was boring and just the daily grind, but for a crossdresser it was a really cool experience. Would I want too be a girl more then once in a while, what would it be like to have this be my daily routine? I suppose that would make me transgendered or transsexual or something, whatever the difference between the two were, if there was a difference I wasn't actually sure about that kind of stuff. All I knew is that I loved the sexy clothing and the makeup and all the girly shit I had been experiencing I loved it all and it seemed to be progressing, I wondered where would it all end. That thought frightened me a bit and I tried to push it out of my mind and focus on how happy I was and how I was glad Mary had given this to me, I would have to do something special in the future to try to make her as happy as she was making me. I sat down at the makeup table beside the bed and figured today I would keep my makeup light and casual since it was daytime and we were hanging around the house. I always had to pay special attention to my face in order to make sure I didn't have any beard shadow showing through. however, I kept the eyes to natural tones with a little gold color, and just some lip gloss to finish off the daytime look. I had just finished up my makeup when Mary bounced into the room and dropped her towel.

"Would you mind doing the lotion for me honey?"

I plunked out a gob of lotion into the palm of my hand and rubbed my hands together to warm it up for her before starting with her legs. Mary had great legs, very tan from her trips to the tanning salon and she was very diligent about the shaving, there never seemed to be any stubble. working my way up, I worked my hands over her curvy little bubble but. I wish this damn cage wasn't on, I would have fucked her right there, It was torture touching her and having her exposed ass inches away and not being able to have her. Another glob of lotion and I reached around and massaged it into her front, paying extra attention to her more then sufficient D cup breast. I finished with her back and shoulders lingering on her tense neck muscles, and finally a gentle kiss on her neck below the ear.

"Thanks honey, that was delightful. Mary said with a loving smile. "Now get dressed while I do a quick makeup job."

I wasn't sure what we were going to do the rest of the night so I decided to keep it casual and went with a pair of black legging the had cute laces running up the sides and a long green sweater top that would be plenty long to cover the obvious bulge from the chastity device. By the time I was done dressing and styling my wig, Mary was done with the makeup and was getting ready herself. Looking at the clock I saw that it was already mid afternoon, time certainly flies when a crossdresser is immersed in her femininity. Mary finished dressing and directed me to head out to the living room.

"Ok babe, You have done such a good job learning how to apply your makeup that I thought tonight we might work on hair styling. It would be awesome if you could learn how to braid my hair for me."

"Ok sounds fun, how hard can it be." I said.

"Don't get cocky kid! My girlfriends and I used to practice braiding our hair all the time during sleepovers back in the day, that and talk about boys."

"Did you just make a star wars reference?" I asked slightly turned on that such a beautiful woman could quote Han Solo.

"Sure did babe... the force is strong in me now sit your sexy ass on the couch and pay attention."

Mary turned on the television and selected a basic braiding tutorial to watch. I paid close attention and in a few tries was able to braid Mary's long hair pretty effectively. The next video was a little more complicated with a braid on each side that met up in the back and worked into a bun. After a multiple attempts I was able get Mary's approval and we moved on to the next hairstyle. This went on for several hours and Mary seemed to be loving all the attention and having her own personal hair stylist, and I must admit it was fun to learn something new. I would have to practice on my wig on my own time so I could get good and surprise her by doing both her hair and makeup in the future. After a while my hands started to get tired from all the braiding and I took out the braids and brushed Mary's hair out for her, Stoke after stroke she seemed so happy to have me brush out her hair and pay so much attention to her and her needs.

We had salads for dinner since neither of us felt like cooking and Mary felt like we had been eating to much take out crap lately.

"We have to watch our girlish figures, what is the point of the yoga if we eat a bunch of pizza?"

She was right of course, I could handle losing a little weight and eating healthier was never a bad idea I suppose. I wasn't overweight or anything like that, but I did not really get any exercise either, and had never been muscular of toned. Maybe I would actually give a little diet and exercise a go and tone up for once, at the least I would look better in a dress when I was done. Finishing my salad, I was left unfulfilled and still a bit hungry but I guess that is the feeling I had better get used to if I was going to get in shape.

After dinner, Mary asked me what I would like to do. I honestly had no ideas, I guess my plans for the weekend were pretty much just play dress up and fuck so after that I had no ideas.

"How would you feel about taking a walk in riverside park downtown?" Mary asked.

"You mean outside... dressed as a girl?" I said, my voice quivering.

"Yes outside honey, it will be dusk by the time we get there, but it has plenty of lights so we will be safe after dark. I thought it would be a safer way for Erika to get out and explore the world."

"I don't know about going outside dressed as a girl, what if someone saw me?" I replied kind of terrified at the idea.

"What difference would it really make if someone saw Erika, they are just going to see a pretty girl and her friend in the park. What about the pizza guy at the door last night, he saw you and had no idea about the cock between your legs."

"Look baby I'm not trying to force you to do something you don't want to do, I just thought if you wanted to take your crossdressing seriously and have the freedom to be out in the world however you wanted as a man or woman then this might be a fun little walk in the park for you."

I'm not sure I ever really thought it was possible to go outside as Erika, It was always a fetish to dress up as a woman and jack off or recently have sex with Mary. Being out and about as Erika did sound like it might be fun, I wondered what it must be like to have cool night air blowing on your hairless legs or up your skirt, But I was a little bit terrified at being spotted by someone and recognized and a guy pretending to be a girl. The thoughts spun around in my head for a few moments before I gradually decided that the chances of getting caught were pretty slim, and besides if someone did notice that I was a male, then fuck them.

"Ok honey I will take a walk in the park with you, but you are driving, I'm so nervous I would likely crash on the way there."

"Excellent!" Mary said excitedly. "I was hoping to be able to get you out of the house this weekend but wasn't sure you would go for it. Don't worry Erika, I will be right beside you, if anything happens I will do the talking."

"OK baby... I trust you." I uttered, still nervous as hell.

I was more or less dressed appropriately for a walk in the park I just had to slip on my purple sneakers and I was ready to go. Mary went out the door first, the setting sun still shone brightly for the moment in the open door. Mary gave me a little nod of encouragement for me to enter the world and I willed my feet to take me forward. I stood by the railing as Mary locked the apartment door. I was in the sunlight completely exposed for the world to see me, luckily there was nobody around. My heart was in my throat as we began going down the stairs to the front door, before getting to the door we had to pass by the mailboxes for the apartment complex and a someone was there getting his mail, in between me and the exit.

I didn't know the guys name, but I recognized that he was the guy who lives across the courtyard from Mary's apartment. I would have to walk right past him dressed as Erika, I wasn't even out of the building yet and this trip was fucked! Mary must have sensed I was losing my confidence and took my hand and positioned herself between me and the guy at the mailboxes as we passed. I held her hand tightly as we passed and kept my head down, in three seconds it was all over, but my heart must have beat twenty times in that amount of time.

We had made it to the relative safety of the car and I got in quickly. Still having a hard time believing I was doing what I was doing, Mary pulled away from the apartment building and headed to the park. Riverside Park was only about a three miles from the apartment but we would need to drive through downtown to get there. I rolled down the window and let the cool night air whip around the cabin of the car cooling me off from the near panic attack I had just had. We were only a few blocks from the park when we hit a red stoplight and was forced to stop. A second car pulled up right beside us at the intersection, sitting in the drivers seat only a few feet from me looking through his open window was a man a little older then myself and he was looking right at me. I didn't know what to do, should I duck down in the seat or roll up the window, look away maybe? Don't be a fool I thought, that would be really suspicious and weird. I matched his gaze and tried to smile a bit and look natural. The man returned a smile and kept looking at me. Just then it occurred to me that when a girl makes eye contact with a man and gives him a smile then it might be a signal to the man that she is interested or flirting or something. I had never been on this side of the exchange before and slowly started to realize that this guy might be flirting back with me. The whole encounter was awkward as hell and I was glad when the light changed and Mary drove off as he turned the corner.

The encounter may have been awkward and weird as hell from my perspective, but it did help my confidence thinking that a man not only wouldn't see though my illusion but would actually find me attractive.

By the time we had got to the park, the sun had set over the river and the lights along the path were starting to turn on. I could see a handful of people up and down the path, but was starting to feel like I could actually do this.