Erika’s Story Ch. 03

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This is the third part in Erika and Mary’s widening exploration of crossdressing, if you have not read the first couple chapters I encourage you to go back and read those first. also, thanks for the feedback I have received and please continue to rate and leave feedback and comments so I can continue to evolve as a writer.


I lay in bed with my loving girlfriend Mary in my arms as she gently rubbed her hand over my chest. Mary was tracing the seam of the nightie I was wearing with her finger as her mind drifted around in a post sex haze. I had just pumped a load of cum down her throat while dressed in a cute little purple nightie and panties, and now was wondering where things would take us from here. Wearing panties and lingerie seemed like it would certainly happen again, and with regularity after what had just happened, but I found myself wanting more. Where did I want to go with this crossdressing thing of mine? I knew I wanted to dress fully as a girl and be as passable as possible, I had dressed up before and always gotten a rush out of seeing myself as a girl and pretending I was what I saw in the mirror. Where would this end, how far would Mary be interested in taking all this?

“We never did order that Pizza.” Mary said, bringing me out of my thoughts.

“Well, whose fault is that?” I asked. “I barely got in the door before being assaulted and drug into the bedroom.”

“I know, I’m such a horny little slut.” She said with a smile. “Tell ya what, I’ll pay for the pizza this time.”

Mary picked up her phone and ordered us some pizza as I rolled over and sat up at the edge of the bed. Looking down at the sexy purple material covering my body, and the pink nail polish on my toes, I started to feel a bit of shame and tucked my dick back into my panties. What was wrong with me, was I gay or something? Normal men don’t dress up as girls, was I some kind of pervert? I got out of bed and started to take off the nightie, hoping that putting my boy clothes back on might help me feel like more of a man.

“Pizza is going to take like an hour… where you going babe?”

“I thought id put my boy clothes back on so we can watch some netflix tonight.”

“Why would you have to get dressed to watch TV on the couch.” Mary asked. “Besides, I might want to snuggle up with you during the movie, and its kind of hot when we are both all silky and sexy.”

“I like the silky feel too honey, I really do… it’s just that sometimes when the excitement of it is over, I start to feel a little ashamed of myself for liking it so much if that makes any sense.” I paused for a second. “I mean honestly, what would people think if they knew about this stuff, what kind of man does this?”

“What is this, 1950?” Mary blurted out with a bit of a laugh. “Men can be whatever they what to be these days, the old time stigma of masculinity and sexuality just isn’t the same as it used to be babe, if you wanna play dress up with your girlfriend sometimes then who the fuck is really going to give a shit?”

“You’re right.” I said feeling a lot better.

“Besides, its just the two of us playing around with a little kinky sex right?” Mary reassured me. “Honestly with a little work I think I could help you look like one sexy little slut!”

“Sexy little slut?” The cock in my panties taking notice of the way she said that.

“Hell yeah you could make a really pretty girl with a little makeup and a lot less body hair.”

“Well how about you give me a makeover after dinner and we can see how pretty you can make me.”

“That would be some much fun, It will be like I’m back in high school when my girlfriends and I would give each other makeovers!” Mary said excitedly. “You go shave everything from the eyebrows down and I’ll get things ready for our girls night sleepover.”

Mary was right, it wasn’t the fifties, a guy could izmir escort do or be whatever he wanted these days even if it included him being a girl. I stripped out of my panties and nightie and headed off to the bathroom to do a little hair removal before dinner. I had shaved my legs before, so I knew how amazing it felt to have shaved legs, I also knew how difficult it was to get to some spots.

I turned the water on hot and gathered up a new razor and some girly shaving cream from Mary’s linen closet before stepping into the steamy shower. The hot water felt amazing and helped relax me from my earlier anxiety over my crossdressing. I think I was now resolved to go ahead with where ever this was going to lead. With that I kicked up my left leg onto the edge of the tub and applied the shaving cream. One long pass with the razor, and there was no going back, pass after pass the hair was removed and with it I was starting to look forward to the makeover more and more. After a great deal of effort, I was pretty confident that I had gotten every hair and rinsed off the remaining shaving cream. Looking down, I could see my body was transformed. I wasn’t the hairiest man on the planet to begin with, but when you are completely hairless somehow you just immediately look more feminine. I decided I had better get out and shave my face before I ended up jerking off in the shower. I gave my face a careful shave and left the bathroom walking into the bedroom almost as hairless as the day I was born. I found Mary rummaging around in the closet pulling out a smaller box and seting it on top of a larger box in the corner.

“What’s in the boxes?” I asked inquisitively.

“Oh nothing much babe, just a surprise for later.” Mary said, stepping away from the boxes. “Here, we got some cum on your panties earlier when I sucked that cock of yours, you will have to make due with these until they get washed.” Mary handed me a pair of her panties, a darker purple pair with a little bow in front and ruffle detail around the waist. “They don’t really match the nightie, but I think they are close enough and besides, you will look cute in them.”

The doorbell rang and Mary threw on a robe hanging behind the door and went off to pay for the pizza. I stood there holding the panties and nightie and my penis started to swell, I figured I better get that stuffed into the panties before it got too excited. One leg then the other I stepped in and pulled the panties into place, then put on the nightie. Walking over to the mirror in the corner of the room I gave myself a long look. From the neck down I looked like a flat chested girl, and I liked how I looked. My stomach let out a loud growl reminding me of the pizza in the other room. I grabbed a pink robe off the back of the door, and went out to eat dinner with my loving girlfriend.

I entered the living room to find Mary sitting on the couch opening the pizza box and placing it on the coffee table. We watched an episode of the Simpsons and finished off two thirds of a pepperoni pizza. With a belly full of pizza I reclined on the couch and kicked my feet up onto the coffee table. Mary followed my example and laid down, resting her head in my lap. We both relaxed for another episode of the show, me rubbing her lovingly and her running her hand up and down my smooth legs. When the show ended Mary announced that it was time for the makeover and took me back to the bedroom sitting me down on the stool in front of her makeup table.

“Well Erik, what kind of look did you have in mind for tonight?”

“I figured I would let you decided what would look best, you are the expert when it comes to makeup, and If we are going the be girlfriends maybe you should call me Erika instead of Erik.” I replied.

“Sounds good Erika, I have some Ideas anyway, not sure how I’m going to make escort izmir the hair look girly but ill do my best.

Mary proceeded to give me a detailed lesson on how to do my makeup. First she explained how moisturizing your face on a regular basis is essential if you want to have good skin. After applying one of her moisturizers to my face she showed me how to use an orange concealer to offset the residual color on my facial hair and the darker areas under my eyes. Mary then applied the foundation but was a little annoyed that it didn’t really match my skin color and said we would have to pick up the right shade when we were out next. Next came a lesson on highlighting and contouring my face and how to blend it all together to create the look she was looking for. Moving on to my eyes, she showed me how to do a Smokey eye look that she claimed makes a girl look like she wants to fuck. A little work on the brows and light pinkish lipstick and gloss and she was finished with the face.

All this attention was really nice, having her pamper me like this made me feel really cared for. As for the Hair, Mary went to work and did a bit of magic with what she had to work with and did it into a side swept pixie cut and put a little gel in it to spike it up a bit and give it texture. Honestly I thought the hair looked a bit lesbian for my style and decided that I would get a really nice wig as soon as I got home.

Mary added a necklace and some clip on earrings to complete the look and was finished with the makeup.

“Well Erika, makeup and hair are finished lets get you dressed.”

Mary went over to the dresser and got out a bra and garter belt that matched the panties she gave me earlier and some silky nude stockings. She then went to the closet and got a black dress out and laid it out on the bed.

“The dress and bra should fit you pretty well they are from a few years ago when I gained a few pounds.” Mary explained. “Now you put this stuff on, I will wait outside the room so you can reveal Erika to me all dolled up!”

I slipped off the robe and nightie I was wearing and looked at the dress on the bed in front of me and couldn’t believe how much fun I was having. This morning, I thought showing Mary that I had got my own panties to wear was going to be a big step on our journey into crossdressing and here I was all made up about to reveal my other side to her in full. I really was a lucky guy to have a girl in my life that was so understanding and accepting. Not wanting to make her wait forever, I started to get dressed. First was the bra, I put my arms through and twisted them behind my back to fasten it as I had done alone many times before. I stuffed a sock into each cup and adjusted it into place, It was still a bit snug around the band but it would work. Then came the garter belt, I fastened it in the front and spun it around into position. Carefully I worked the stockings up each of my freshly shaved legs and secured the four small fasteners to the tops. The dress proved to be a bit more difficult, I stepped into it and put an arm though each hole but it zipped in the back and I had no idea how I was going to get it zipped up by myself.

“Honey… do you mind giving me a hand with this zipper.” I called out.

I dimmed the lights and turned my back to the door so she wouldn’t be able to she me well and ruin Erika’s big reveal. I heard her open the door and step inside. A moment later I felt her hands on my hips for a second before she worked the zipper up.

“Thanks babe, I wasn’t going to be able to get the zipper by myself.”

“No problem… girls help each other out with this kind of stuff when they are shopping or whatever all the time.”

“Ok, I will keep that in mind for the future.” I said chuckling. “Now close your eyes and I will turn around and let you get a izmir escort bayan good look at your new girlfriend Erika.”

Mary had done my makeup and hair, and had helped me into my dress but now as I turned around for my loving girlfriend to see me on full display… I found that I was terrified and at the same time, my cock was rock hard in my panties.

“Ok open.”

“Oh my god baby you look fucking amazing… If I hadn’t been fucked by you a hundred times I wouldn’t really know your were not actually a girl!” Mary exclaimed, looking really surprised. “Look at yourself in the mirror baby, you look fucking perfect… well maybe not that hairstyle but we can work on that.”

I actually had not seen myself yet and turned to the mirror and could not believe how well my makeover had gone. I had dressed up before, but Mary was so much better with makeup then I ever was that the illusion was amazing. Hopefully thanks to her makeup lessons she had given me tonight I would be able to duplicate this miracle. Standing in the mirror looking back at me was the visage of a woman I would have never believed I could become. The makeup was flawless, the dress, the stockings, everything made me feel sexy and just took my breath away.

I turned to Mary and wrapped my arms around her and gave her a big hug holding her tight so she would neve get away from me.

“Oh… the surprise, I had almost forgot!” Mary said, going over to the 2 boxes in the corner from earlier and placing them on the bed. “Open them up Erika, its a birthday present for you.”

I opened the boxes up and inside was a bunch of women’s clothing. I saw bras and panties, leggings and skirts, a dress or two and bunch of different tops and camisoles.

“What is all this stuff?” I stammered

“Its all my old clothes from when I gained weight, I put it in the boxes in the closet after I lost the weight again, but I figured they would be abut the right size for you to wear when we have more dress up nights.”

I didn’t really know what to say, but I knew my cock was hard as diamonds. I grabbed her and pushed her down onto the bed. Hiking up my dress around my thighs, I got on top of her and began to nuzzle at her neck leaving lipstick kisses on her as I went. Biting her earlobe a bit and grinding my erection into her I couldn’t take it anymore.

“Do you want your girlfriends cock inside you baby?” I moaned into her ear

“Fuck yes, I want you to fuck the shit out of me baby!”

With that I got her up on her knees and roughly ripped her panties down her legs exposing her pussy to me. There wasn’t going to be any foreplay tonight, there wasn’t a need for any of that, we both needed to FUCK tonight. I hiked up the front of my dress and pulled my hard cock out of the silky panties. I placed the tip against her sex and rubbed against her slightly. She was wet as October, and with that I thrust into her balls deep in one motion. Mary did a half cry, half moan as I bottomed out in her. I began pumping in and out of her at a brisk pace. My hands were on her hips forcing her backward onto my dick even harder. Mary began to cry out. “Fuck me Erika…fuck me hard!” I could feel her body tensing up on my cock as her orgasm swept over her. Thank god I had received a blowjob earlier in the day or that would have sent me over the edge as well. Out of exhaustion, I slowed down at bit getting myself near an orgasm and then backing off a bit. Mary had now gotten her second wind and was moaning in rhythm to each thrust. Speeding up, I gave her pussy a pounding and she climaxed onto my cock for a second time. This time I was panting and out of breath and the feeling of her muscle spasms milked the cum out of me, squirt after squirt found a home inside of her welcoming hole. We both collapsed on the bed and lay there completely spent. Me dressed as a woman lying beside a beautiful girl who had my cum leaking out of her

As we drift off to sleep holding each other, I think to myself, what an amazing day. I was excited to see where our relationship would go from here.

Thank you so much for reading my story and please leave a comment and rate this story so I can see if people are enjoying it.

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