My Other Side
Another Fiction by John G. Edwards Copyright 2016 All Rights Reserved JO/EL Engineering Technical Publications
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I don't know why she doesn't like it, it doesn't hurt her, or anyone else for that matter. My obsession for crossdressing, is for her and some others, something like a fetish or deviant perversion. I don't see it that way, it's more like a compulsion, or something. I've been doing it since I was a small child, I mean what's the big freaking deal? I put on women's clothing and hang out at home and do whatever comes to mind. It's not like I dress and go around the neighborhood and cause any trouble, or anything.
Monica, my wife, just seems to hate it when I dress up. She says that I put on a better face than she does, who knew? And, my sexy lingerie is more expensive than hers and it looks even better on me then if she were to try it on, which she won't. We do share the same shoe size and that drives her nuts when I wear a pair of her high heels and navigate, that's walk around, in them I do it just as good as she does. Boy, does that really piss her off.
I do wear nylon panties and have ever since we met, and that's she's cool with. But, when I wear a tee-shirt bra, she feels like she's being robbed of her feminine side. When I wear a bra, it just makes me feel good. I'm a few pounds overweight and a bra does give me a very modest amount of shape and fullness, not to mention support. Not like it's a lot, I wear a 36a bra and I don't think she should be threatened by that, but she is, sort of.
I bought this bra on-line that said it was a Super-Push-Up and it has over an inch of padding and when I wear it I have cleavage and a nice looking set of small tits. She doesn't like that one, one bit. The girdles I wear are more to keep the man-thing in its place than anything else, not that I have a huge shlong or anything. I'm about, maybe, 6" when fully erect? But when its asleep, it is rather easy to keep hidden and well out of sight especially when I wear a couple of pairs of panties and then the girdle.
One night when we were staying in, I went and got dressed in a red mini dress, opaque black tights, and a pair of her red high heels with ankle straps. Underneath, I was wearing my black long-leg girdle, the one with the lace around the leg opening, and the lace could slightly be seen below the hem of my dress. I thought it was really a sexy look. I put on my Super-Push-Up and a pair of C-size breast forms which give me a mountain of tits.
I wore a medium foundation with some blue and purple eye shadows. I rimmed my eyes in a, somewhat wide, line of ultra-black liquid eye liner and swept the line back to give me a cat-eye look. The pair of false eye lashes I put on were colored with an ultra-black mascara. I little blush and I was set for the ball! Monica didn't have pierced ears, but she had a pretty good collection of clip-on's and I put on the biggest and boldest pair that she owned. Finally, some vivid red lipstick to cover my lips.
My wife does wear wigs once in a while and she must have about 8 or 9 different ones. I really like the red one with the A-line bob with blunt-cut bangs, so I put it on. Say what you will, I looked pretty damn good in the mirror. When I came out of the bedroom, Monica was watching the TV and had a pretty hard-core sex movie on. She didn't acknowledge me when I walked past the first time and went to the kitchen, but when I came back she gave me a long look. It was a look I wasn't familiar with, it was one of those that undress you piece by piece.
"You know Nathan, if you were a woman, you do look like a million bucks all wrapped up and tied with a bow," she said as she gazed at me.
I stopped in my tracks and wondered where this had came from, this wasn't her normal conversation when I came out in my female attire, "Uh... thank you?"
"No really, you look splendid tonight, you really do!"
Now I'm totally confused, "You like what I'm wearing Monica? Really?"
"Yes I do sweetheart."
Oh shit, I'm either really gonna get hammered tonight or she's toying with me. I thought I should go on the offensive and see how that plays out, "What exactly do you like?"
"All of it!"
"Thank you, but what part of all of it do you like best?"
"Where do you want me to start darling?"
Oh shit, she hasn't called me darling in months, "Start where ever. Your sudden positive interest in my dressing has my curiosity and my attention, darling" I figured this would start to set her off.
"Well, your choice of the red mini dress is excellent and I like the way your girdle shows, ever so slightly. Your hose and shoes were an excellent choice with the dress. By the way, did you shave your legs tonight? I don't see any hairs trying to escape."
She knows I don't shave my legs, "No dearest, I didn't shave my legs. Why, do you think I need to?"
"Your make-up is, as always, even better than I can do. Will you show me how you do it sometime?"
Now that's a first!
"I like the earrings that you chose, those are some of my favorites, as you know."
I knew she liked them, but her favorites??? As I stood there, Monica got up and approached me.
She took her hand and started rubbing my breasts and went down my sides past the hem of my dress and onto my legs. I have to admit, she sure was sexy in her approach and feel. "Do you like the way I feel dear?"
"I do, will you stay here for just a minute, I have to go get something?"
"Okay." A minute later she returned with her best perfume and put some on my neck behind and each ear and, and then onto my wrists. It was my favorite scent as well. I have never worn perfume before because it's expensive and I knew that she wouldn't approve and besides it would out me in the biggest way.
"Now, isn't that better dear heart?"
I closed my eyes and savored the smell and said, "Yes, it is much better." I opened my eyes and she was standing right in front of me very close. I was almost shocked when she leaned in and gave me a big wet kiss as I slightly backed up from her touch. As I collected my thoughts, I just couldn't fathom why this sudden change.
"Oh, I never thought that kissing you with you wearing lipstick could be such a turn on darling."
"That was pretty nice, huh? Can we do it again?" I asked and she quickly leaned over and gave me an even bigger and longer kiss while her hands were all over my body. I was knocked out at how it felt to have someone you love extend that kind of loving and touching to you. After several minutes she broke the embrace and asked...
"Darling, would you go get me a glass of milk and some chips, please?"
My euphoric moment just went poof! "Wha... What?"
"Did you like that?"
"What, the milk and chips bit, or..." Now I was truly and utterly confused.
"Come here..." she said as she pulled me in for another long languid kiss. Another couple of minutes later she asked, "Confused, are we?"
"Tremendously!"
"I think I understand why you dress up now."
"You do?"
"Yes, the video I'm watching kind of put everything into perspective for me."
"And..."
"Rather than object to your dressing, I should embrace it... and more."
"What's more?" I asked as she moved in and gave me another kiss, this time her hand was pulling my dress up slightly and her fingers started rubbing and teasing my man-thing.
"Oh darling, you need to be dominated. I understand now. I bet your mother started dressing you as a girl when you were young. That was probably a response that she instilled after your father died, huh?" Just how in the hell did she know this? She didn't like mother all that much and I know mom would never tell her anything about my upbringing. I stood there kind of reeling in my tracks because two truths had come home to roost. "Uh huh."
"Good. I think that there will be a couple of changes around here, starting this week."
"And just what will that be?" I asked as I wondered what she had in mind.
"I'll let you know later, but tonight I want you to enjoy your night sweetheart," she said as she gave me yet another kiss of epic proportions.
Monica pulled me down to the couch so we could lay down, only this time she laid on top of me. She held my face in her hands and said, "You are going to love it sweetheart!" and then started to feel me up. My legs were spread apart and my dress was pulled up so she could start dry-humping me. Her one hand was rubbing my crotch and the other was fondling my faux breasts. My willie was starting to awake and rise to the occasion. If I had real breasts, it would have been the most glorious feeling of a life time to have her on top of me.
After what seemed an eternity Monica pulled my girdle down to expose my tights and then again she started her sweet massage. A while longer she had me take off my tights and panties to expose my now fully erect penis. Without missing a beat, Monica went down on me like she never had before. My head was swimming from the ecstasy as I had the most massive climax I had ever experienced in my life. We were like a couple of rag dolls, limp from satisfying sex and draped upon each other.
Several minutes later Monica asked, "How was that sweetheart?"
"Oh my god woman, that was the best sex I've ever had, in my life!"
"Yeah, it was pretty good huh?" she said as her rapid breathing was now finally coming under control, "Do you want some more?"
"I've gotta catch my breath first."
"Save it for next week."
Not knowing quite what she meant, I was plenty tuckered out by this monumental event.
"Honey?" I want you to start dressing for me every day. Will you do that for me?" she asked with a big smile. "I never thought sex could be so good with you dressed up like this!"
I didn't quite know what to say, this was something that I had always wanted, but now that the opportunity was here I wasn't very sure about it. "Okay," I said reluctantly.
"Since you work from the house, could you be dressed for me when I come home?"
"Yeah, sure I guess."
"Good! Tomorrow is Sunday and I want you to dress in your Sunday best for me."
I had to think what my Sunday best would be??? "Yes, dear."
"That's a good girl!"
********** The next day I got up and took my morning shower and while I was enjoying the warm hot water, Monica stuck her head in and handed me my razor and asked me to shave my legs and underarms for her. I stood there holding my razor not knowing where to start, "Honey? Where do I start? I mean, I've never done this before... Will you show me how?"
"Finish with your shower and I'll show you sweetheart," she said with a big smile.
A few minutes later I had just turned off the water and Monica was waiting for me to step out of the shower and she had me sit on the edge of the tub with my legs hanging inside. She handed me some of her shaving cream and had me lather up my legs. I' was pretty sure I didn't need the shaving cream, but I went ahead and put it on my freshly washed legs.
"Okay, start shaving from your knees and down and then we'll move to your upper legs."
The razor glided across my legs as if the razor was an ice skater on ice. The hair shed itself into the tub and slid down the drain with ease. I rubbed my hand over my knees and lower legs and boy were they smooth. Monica had me stand up and showed me how to start the denuding process of my upper legs. I didn't know how high I should go and I stopped at where my pubic hair started.
"No honey, you have to shave your privates too, not just your legs. Do you want me to do it for you?"
I shook my head yes. Monica started removing most of the hair with a pair of scissors.
"Careful!" I said with a bit of nervousness in my voice.
"Yes, darling..." Within five minutes my pubic hair was just a memory. Monica had her smart phone handy and took several pictures of my hairless lower half and what was left of my manhood, so to speak. "Now, doesn't that look much better darling?"
I reached down and felt my nude penis and balls and they did feel very smooth and vibrant to the touch. I had a raging hard on at this point.
"Oh, let's not let that go to waste darling," said Monica also reaching in and copping a generous feel. She got up and pulled me up so we could go to the bedroom. She got her jar of Vaseline and gave me one Jim-Dandy hand job. After we were thru, she asked, "What are you going to wear darling?"
"I don't have much in the way of a Sunday dress sweetheart."
"I've got that yellow summer dress, let's see how it fits you, it's from my frumpier days, you know?" She went to the closet and dug around and found the dress. It had cap sleeves and needed a small crinoline to make the skirt sort of stand out a little bit. The dress was in one hand and the crinoline in the other, she held them up for me to see. "What do you think sweetie?"
"It might fit."
"Well, give it a try. I think you should wear some white pantyhose too and I've got a pair of white ballet flats that will look cute with them."
"I'll try on the dress first, okay?"
"Sure, here..."
I took the dress and remembered that it had a series of buttons in the back and I used to have to help Monica button it up. I stepped into the dress and pulled it up over my arms. My arms were bigger than Monica's, so the sleeves were pretty tight. She went around to my back and she started buttoning up the white pearl-like buttons. The dress became tight real quick, but I just fit... barely!
"Sweetie, I think this will need a little bit of alteration to make it fit just right. Let's get it unbuttoned so you can put on your white bra, black wouldn't look so good, you know." Monica started un buttoning the dress and let it slide down to my waist so I could go get my white 36a bra. When I came back she stopped me at the door, "Honey pie, get your forms too." I stopped and turned around to go get the breast forms. I put the bra on and then inserted the rather large forms, they certainly filled out my 36a!
Monica helped me to put on the dress once again, this time it was terribly tight across my bust line, "Honey, I think this is way too tight."
"I think you are right, take out your forms, you will need to get some smaller ones." The dress fit reasonably well when I took the forms out, but there was just a slight pucker around the breast line. As I stepped into the crinoline, it caught on my foot and I nearly fell down.
"Careful!" Monica pulled the heavily starched fabric up around my waist and adjusted it so it held the skirt away from my legs by about 6", or so. In a juvenile sort of way, the dress looked very cute. She handed me a pair of white pantyhose to put on along with the white patent leather flats. The effect was a thing of beauty to see. All that was missing was a wig for my head. Monica had this long blonde curly wig that she wore to a Halloween party once with this dress and it made her look like Bo-Peep, now I looked like Bo-Peep too!
"Oh aren't you something to look at sweetheart!" Click went more pictures. "Oh shit, I forgot the bonnet!" Once the bonnet was on my head, I indeed look just like little Bo-Peep! Click, click, click...
Oh shit, if any of these pictures ever made their way to the internet, I'm finished! We spent the rest of the day doing chores around the house and I fixed a nice dinner for us. I had just put the last dish and pan into the dishwasher when Monica said, "I want some ice cream, how about you dearest?"
"Yeah, sure let me go change first."
"No, I can't wait that long. You drive and stay in the car while I go in. Take off your bonnet though, you might look kind of silly wearing it. Oh, and go put some more lipstick on."
I just stood there blinking my eyes in disbelief! "What???"
"Oh, come on Nathan, I can't wait so let's get going. NOW!" I jumped as she raised her voice, but went to go do my lips. If there was any silver lining it was the fact that our garage was connected to the house and I could use the opener to open and close it pretty quickly. Within a few minutes we were off to the ice cream store.
Once we pulled into the parking lot it was full of cars with people also wanting ice cream. There was an open spot right in front of the store and I pulled in. I was feeling like I was going to get caught crossdressing in public, I was a nervous wreck!!! Monica went in and stood in line and would turn around every once in a while to give me a wink as I sat nervously in the car with the engine still running. When she got her order she turned around and pointed at me and the girl behind the counter waved at me. I thought I was going to shit!
Once Monica was back in the car I asked her what all that was about? "Oh honey, I told her that I was out with my girl friend and to give you a wave, why?"
I didn't say anything for a few minutes trying to show that I was pissed.
"Oh come off your high horse Nathan, you wanted to dress as a woman didn't you? This is all part and parcel of that wish, understand?"
********** The next day was Monday and Monica was off to work kind of early and said that she would be home late because she had some things to do. Before she left, she had laid out my clothes for the day for me. There was a teal colored rayon pencil skirt and a white long sleeve cotton blouse with scoop neck. A pair of wine-red opaque tights and a pair of black 2" pumps were also sitting there. The red A-line bob wig was also sitting there ready to crown my glory.
Monica came over and gave me a kiss goodbye and reminded me that she would be a bit late this evening. I got up a few minutes later and got started with my day. I had a report to write that would take about four hours and then it had to be filed, and then I was done for the day. Around noon I got a call from Monica, "Hi sweetie, how's your day going so far? Listen, I need you to go to the hardware and pick up a few things for me, I've got a trip coming up and I need a few things, can you do that for me?"
"Sure." I took down the list, six small luggage pad locks, some blue duct tape, a roll of plumber's tape, a few feet of small link chain cut into one-foot lengths, and some nuts and bolts that would fit the chain links. Somewhat a strange list, but hey, what did I know about her trip and what she needed, anyway. When I got home I decided to make myself an early dinner and then make a salad and put something in the oven for Monica. I decided to get into my guy stuff as I had worn the female outfit all day and it was time to wind down somewhat. It was just about 9:00 when Monica got home and she was loaded to the gills with packages.
"Hi sweetie, how was your day, kinda long by the looks of it," I asked as I tried to give her a kiss.
"Yes, it certainly was... where's your dress?"
"I finally took it off around 4:30 so I could fix dinner, why?"
"I've been shopping and bought you a few things, but right now I'm famished, what's for dinner?"
I went to the kitchen and got Monica's food and dress her salad, "You went shopping for me?"
"Yes, I wanted to get you a couple of things before I left on my trip on Wednesday."
"Really, what did you get me?
"All in good time sweetie, all in good time. Oh, this chicken is delicious!" About a half hour later Monica was finished with dinner and went to get the packages, the majority were pink. "You know darling, I said things were going to be different from now on, well I went out and bought you some new things to wear for me." I just sat there listening intently. "First I bought you some new breast forms. These should fit a little better than the one's you have. Here, give them a try why don't you?" She said as she handed me the two forms. They were much heavier than the ones I had, by a mile. "These are more anatomically correct for shape and weight. Don't you just love them? Go put your tee-shirt bra on and let's see how they fit."
After putting on my bra, Monica placed the forms in the cups and tried to put them into place, but was having trouble. "This bra is too small for you, sweetie. Here, try on this one here..." she said as she pulled out a lace and satin black shaping-bra. I changed bras and then she was able to fit the forms as they should. The bra was a 36c and the forms fit in perfectly.
"Wow, this bra gives me a lot more shape and a different look, huh?"
"I most certainly does sweetheart. Here's another bra just like it, only in nude, give it a try." I quickly switched bras and found that it fit just like the black one - perfect! Next, Monica pulled out several pairs of tights in a rainbow of colors and a few pair of sheer pantyhose. Next, was a big surprise... a black brocade under-bust corset, I couldn't believe it! A real corset, I had always wanted a corset because I thought that they were the most sexy under-garment you could ever wear! "Oh Monica, for me?"
"Yes sweetie, you deserve some nicer things now." The word now, has me worried!
"Let's have you look at some of your other things before you try it on. Here you go!" she said as she handed me a somewhat oversized pink bag that had black stripes.
I pulled the dress out, it was a black with white accents, French maid's dress. Also in the bag were a pair of 4" patent leather high heels with some sort of strange straps, and an apron that matched the dress. At the bottom of the bag I found the matching cap. I was excited, but very curious as to when I would ever wear something like this??? I gave Monica a somewhat bewildered look.
"Oh sweetie, you are going to look fabulous in this, don't you think?"
"I... uh..."
"Here, these go with the outfit..." Monica handed me another pink bag, this one had several pairs of fishnet stocking and a garter belt to hold them in place. My wife handed me several more packages and I found that she had bought several more dresses and lingerie that she liked the style of. Not my favorite, but this was for her, not me. There was one small box and I was told that was for later, much later.
Monica had me strip down to my bra and panties so she could help me put on the corset. It was more complicated than I had imagined and took several minutes to lace completely. And to think women wore these at the turn of the century, and every day they wore them! My god! She had sort of a hard time getting the ends to meet in the back, but said that we would get there eventually. I would no doubt have to lose some weight. I could hardly breath and had to take shallow breaths. I now understand why women would often faint while wearing a corset.
The French maid's uniform was very cute, but my short hair was completely at a loss to make any sense of anything. I put on the garter belt and high-cut panties and then the fishnets. Monica pulled out a black bob cut wig and placed in onto my head. I sat down and she helped me put the high heels on, "Honey where is the stuff I had you get for me at the hardware?" I thought this was an unusual request right now.
"In the kitchen on the counter." I sat there trying to figure out the buckle. When Monica came back she had the pad locks in here hand. I looked at her trying to figure out what she needed them for. She just smiled at me. Monica bent down to fasten the ankle straps and took one of the locks and clicked it shut to lock the shoe to my foot along with a small length of chain that she fastened to my other foot when and locked it. I looked at her with another bewildered look and she just smiled at me. "What's that for?"
"For you, dearest."
"Okay, but what for? I don't understand why you have to lock shoes to my feet! The chain?"
"All in good time sweetheart, all in good time!" she reminded me as she sat the other locks on the coffee table. "Stand up and turn around for me sweetie." I did as I was told and hobbled around. She stopped me when my back was facing her. She picked up another one of the locks and clicked it shut around the color of the uniform to lock it to my body. Now, I was getting very nervous in a big way. What did she mean by locking my shoes together and the dress? "Stand still." After some shuffling in another bag Monica placed a ball gag over my head to told me to 'open-up'. Once the ball gag was secured, I heard another lock click shut. She spun me around so she could have a look. "Oh, don't you look so precious!"
I tried to say something but nothing intelligible came out but Monica gave me a kiss, well she kissed the ball anyway, and then my cheeks. A couple more pictures followed. So, here I am dressed in this French maid's outfit wearing high heels that are chained together so that I have to hobble, and then there's the ball gag. What next, is she going to chain my hands together, or what? Yep, that was next, then came a pair of handcuffs!
Monica pulled down my panties and had a field day with Mr. Man Thing and it didn't wake too long and I was about to climax. "Not yet sweetie!" she said as she stopped. I was then blindfolded and led very slowly to the bedroom, how much more humiliation was there going to be this evening I wondered??? I'm glad Monica was there to help me because I had never walked in 4" high heels before and was the task was quite a bit for her to handle because she had locked my feet together. Reaching the side of the bed she sat me down and helped me into bed at which point she placed a condom on me and mounted me from above. All I could do was lay there as she had her way with me. The blindfold kind of made it easier for me because I couldn't see what she was doing, but I could feel her hands all over my body. "Do you like that, my little French sissy slut?" After what seemed like an hour we both came to an exciting climax.
"Wasn't that exciting my darling little sissy?" With the ball gag still in place I couldn't say anything. "I have one more surprise for you dearest." A couple minutes later Monica was sort of playing with Mr. Man Thing, but I felt something that wasn't quite right. She was fitting something around my balls and penis and once again, another damn lock. I tried to reach down to feel what it was but she was straddling me backwards and I couldn't. I could feel that my penis was caught in something, but what???
Monica finally got up and I immediately reached down to feel below, when I did I couldn't believe that she had put me into chastity. I started to cry. "Oh honey pie, don't cry this is only going to be on for a short time. Sit up and I'll take the ball gag out and the other stuff off."
I tried to sit up, but she had to help me. Boy was I glad to get the ball gag off, my jaw was already sore from having my jaw jacked open for so long. I was drooling and could feel the streams of saliva flowing down my cheeks. The shoes came next, then the handcuffs, and finally the dress. I was never so glad to get out of a dress in my life! Once the corset was loosened I slipped out it and returned to normal breathing. I took a huge breath and was instantly rewarded with lots of cool fresh air. Once I was completely undressed, I was waiting for the cock-cage to come off, but it didn't. I must have looked like a sad puppy, with my tear-filled eyes.
Monica got ready for bed, came in and kissed me good night. "Thank you for such a wonderful evening sweetheart!, I love you so very much!" She rolled over and went to sleep. I rolled in the opposite direction and sobbed myself to sleep thinking about how she called me here 'little French sissy slut'. A couple hours later nature called and I went to go take a leak, and a leak is all it was. My chastity device allowed me to pee, but not cleanly, because my cock was squished between a couple of plastic discs and the plastic cage. All I could do was sit and dribble. I tried wiping myself, but that was useless. This sissy slut would have to figure out how to take a piss, and soon!
When I returned to bed, Monica cuddled next to my back and hung her arms around me and immediately felt me to see if I still had the device on. I tried to pull away from her, but it was no use because I was caught between her and the fat-cap on the waterbed. She held my cock cage until I finally dozed off to a fitful night's sleep.
********** The next morning I got up before Monica and went to the other bathroom to go pee and clean myself off when I took my shower. This was going to be a bitch, I could tell. Monica came in and jumped into the shower with me. "Good morning darling, sleep well?"
"No."
"Oh, sweetheart don't be so grumpy. You can take a nap this afternoon when you get finished with your work." When I finished with my shower I went to go dry off and found that my clothes were laid out for me, once again. Today it would be a navy-blue cotton house dress and matching pantyhose and a pair of 3" black leather peep-toe high heels. I looked very stylish wearing the black patent leather belt and I was told that I should have my toenails painted by the time Monica returned home from work because we had someplace to go right after she arrived. My 36c bra and breast forms and another pair of high cut bikini panties were also laid out for me to wear.
"Darling, I picked up some new vitamins the other day for us, would you please take them?" A quick kiss and she was off.
I did take a nap in the afternoon and it felt wonderful, but my cock cage wasn't the most comfortable thing in the world to have to wear. I tried on my panty girdle, but that made it even worse. Monica had an open-bottom shaper that I would have to find and see how that fit. I did need something to make my waist a bit smaller for all my new clothes.
That evening when Monica got home she hustled me out to the car and off we went. This time we were out and about with me fully dressed and fully made up. The black bob wig made me look very sheik, to say the least. We wound up at a local tattoo and piercing shop about a mile away from the house. I looked at my wife once again with that now familiar questioning look. "What?"
"We are going to get our ears pierced together. Isn't that exciting sweetheart?"
I had no thoughts about getting my ears pierced. "I'll watch you get yours pierced, okay? Mine are just fine!"
"Oh, don't be a baby. Come on lets go in."
I got out of the car, still in my female attire, and was wondering what the hell am I doing, here... and now...? I turned around to get back into the car, but Monica had driven and had locked the doors and I had no keys. Shit!!! We walked in and Monica asked for Drew. Who in the hell is Drew and how does she know him?
"Hi Monica," said a well tattooed biker looking guy that must have weighed around 250 pounds.
"Hi Drew, this is my friend I told you about."
"Welcome little lady, I understand you are going to get your ears pierced tonight?"
"I think there's been a mistake here."
"No mistake Natalie, we're here to get our ears pierced," said Monica in a very authoritarian voice.
"No, I think you are mistaken."
"No I'm not, now sit down! This isn't going to hurt you one bit."
Drew stepped in and I sat me down in the high director's chair.
"Drew, you can do mine first so that Natalie can see that is doesn't hurt." Drew came around and got Monica prepped and within a couple of minutes she had pierced ears. Monica didn't even flinch when the piercings were being done, in fact she just giggled. "See, Natalie no pain, it's a snap!" I looked at Monica's new gold balls and she now looked just like every other woman with pierced ears. Maybe this won't be so bad after all.
Drew cleaned my ears and made several marks on both of my ears, I wasn't sure why he did this. As Drew got near me, I could smell oil and grease on him and I wondered if this ear piercing business was going to come out ok. He place the piercing gun onto my earlobe and told me to take a deep breath. When he pulled the trigger I felt pain like nothing else on this green earth and I fainted. When I woke up, I had nine piercings in each ear, five in each lobe, three on the top front of each ear, something called a triple helix, and a small beaded ring on the flap of skin just outside of the ear canal called a tragus piercing. I must have been out for a while for him to get all these done.
What I wasn't expecting was how my chest hurt, especially my nipples. It was like someone had put some of those big paper binder clips my tits. Man did it hurt, but the pain in my ears had my full attention right now. "Oh, sweetheart, you look so beautiful with all of your piercings. Drew, can you do triples for me?"
"You bet, Monica!" And before we left, Monica had triple pierced ears.
"Are you feeling okay Natalie?" asked Drew with a concerned look on his face, You really passed out on us, there."
"Yeah, okay... I think. I've got a real piercing pain in my tits, however."
He smiled and said, "That will pass in a few days." And then, he winked at my wife.
"Come on dearest, we've gotta run. Thanks Drew, we'll be seeing you again soon, I sure!" said Monica as she drug me out the door.
Our next stop was a local discount shoe store where we spent at least an hour trying one all kinds of shoes. High heel, boots, pumps and flats and an odd pair of flip-flops. Monica bought me five pairs of shoes and a couple for herself that I was not to ever wear. I was truly surprised that no one made any comments to or about me when we were shopping. It was as if no one cared. Fully made up, I pass for a pretty convincing female. Amazing! My nipples were still kind of on fire and I would have to take a look at them when I got home to see what's up with that!
We dashed into a local Italian bistro and had a salad and a slice of cheese pizza. It was delicious. When we finally got home Monica made me stand for a photo-shoot of my newly pierced ears, 18 piercings in all. I don't know how women stand for that kind of torture, all in one shot. I did get several compliments on them at the bistro. I guess it will be kind of cool having so many choices of different earrings to wear, but I don't want a bunch of junky looking stuff. Mostly hoops and studs or maybe different colored stones. Diamonds would be very nice!
Once the photo shoot was finished I went in to take off and wash my face, and put on my house robe. I took off my bra to see what all this pain was about and I almost fainted again. My nipples had 1/2" captive bead rings hanging from them. "Monica!!!"
"Yes dear heart?"
"What's this?" I asked as I point to my pierced nipples.
"Oh, don't you look the cutest with your nipples pierced? Oh honey pie, I just love them. Won't they be such fun to play with? Would you like to get them double pierced, or something?"
"No, and HELL NO!!!" I almost screamed. How do you take them out?"
"It takes some sort of tool to take the rings in and out, and you know neither one of us is tool minded," she said with a laugh.
I Touched the rings and tried to slid them around in my nipple. Ye oww, what a mistake that was. You could just feel the metal as it slid through my nipple, it wasn't a good feeling, that's for sure! I just stood in front of the mirror shaking my head, but my ear piercings did look pretty cool after all. Once again, I had a restless and fitful night's sleep. I had to lay on my back all night long and I'm not used to doing that. My nipple piercings were slightly into the areola and not directly in the nipple itself and I had to wear a bra all night to keep the blankets at bay so that they didn't get caught and pull.
About a week after Monica made her business trip, she came home one night and said she had a surprise for me. She told me to take off my panties and hose. After lifting my skirt out of the way, Monica unlocked my cock-cage and let me out. What a relief! My poor penis was all shriveled up and looked half dead. Slowly, Monica took my shriveled little pal and put him into her mouth and started bobbing her head back and forth until he came to life. He's alive!
"We'll take up where we are leaving off in the bedroom sweetheart."
"Oh. Monica, you just don't know how good it feels to be out of chastity!"
"I have something new for you tonight, I bought it on my trip. I can't wait to show you after dinner! Let's get ready and go to celebrate your freedom. Honey pie, will you do my make-up tonight? I would like to wear something exotic that you would like to see me wear."
I was so excited to be unlocked I could almost pee my panties! I took Monica into the kitchen and had her set at the breakfast bar on one of the high stools so I could do her make-up. I applied a cobalt blue eye shadow to her lids and a teal color to the upper to the brow line. I used a black eye crayon to give her weak looking eye brows some real definition. I lined around her eyes with a teal eye liner and filled in her water line with a black eye pencil. Monica had very long lashes and all I had to do was apply some navy-blue mascara. I chose a deep berry red lipstick for her and it gave her sort of a pouty-lip look. A little blush and her face was a thing of beauty. I changed her studs for a set of graduated golden hoops that were 25mm, 30mm, and 35mm in diameter. "Ok, what do you think?"
"You are truly a master at make-up Natalie!"
"Thank you. I think you would look really cute with a nose piercing, what do you think?" I said as I held one of her studs next to her nose so she could see.
"That would be kind of cool, huh?" All of a sudden Monica took one of her small studs and pushed it thru her nose like it was nothing and then put the backing on. The ball was slightly large, but she carried off the look quite well.
"Wow, don't you ever feel any pain at all?"
"Nope! Let's go eat."
I had changed my bottom studs for a pair or 75mm diameter hoops and I really liked how they looked hanging from my ear lobes. I could feel them swing against my cheek as I walked, it was a delicious feeling! My nipple piercings were slowly getting less tender, but I could still feel them without any problem.
After diner we came home and jumped each other as the front door closed. I had such pent-up desires that had to be satisfied and so did Monica because she too went without sex for the same time period. We undressed each other and just stared at each other for a couple of minutes. "Do you what to see your surprise sweetheart?"
"You know I do sweetheart."
"Let me go get it, then." Monica came walking back into the room wearing a black heavy leather harness with a 12" dildo attached to it.
My eyes widened. "What's that for? Or, better yet, who is it for?"
"For you my darling, for you and only you."
"You want to butt fuck me, is that it?"
"Yes I do, very much so my darling."
"Our sex is getting kinkier by the day is seems like Monica."
"Yes, but you do enjoy it, don't you?"
"Yeah..." 'kind of' I said under my breath.
Monica reached over and grabbed a big jar of Vaseline and started lubing her manhood and then told me to stand up and bend over at the waist over the foot board so she could pack my behind with the lube. I really did like it when she would finger my ass. There is just something that is very special when a woman does that to a guy. She kept me bent over and slid the phallus between my legs and up towards me waiting posterior. Slowly, I mean very slowly, Monica pushed her way in.
The first inch was the most painful as she spread my sphincter with her 1" diameter rubber dick. Once she was in that first inch, the rest went in with little effort and to a depth of about 10", without any problem. She just stood there for a minute before she made any further moves. Slowly she pulled out and then went back in and she placed her hands on my hips. She gave me a gentile squeeze and started the rhythm of love. She had to stand on her tippy-toes to get enough height and I told her to stop and put on a pair of high heels. She came back and once again pushed herself into my waiting bottom and it was much easier because she had already stretched me out a little. She regained her momentum and started to quickly and forcefully slip and slide in and out of my bottom. She took one of her hands and grabbed one of my breasts and gave it a good squeeze and when she did my nipple piercing reminded me that it was still there in a big wave of pain that shot thru my body. Each and every time she did this I got closer and close to an orgasm. This coupled with my prostate getting hammered eventually drove me to a massive climax and I collapsed over the foot board with Monica following me all the way down.
I was pretty well spent but Monica had different ideas. She took the belt off and cleaned the dildo and handed the harness to me and said, "My turn sweetie!"
I fumbled around putting the harness on, but on it went. I packed her ass with the petroleum jelly and went about making my entry just as she had do to me. Once I got started she was screaming for more and took my had and placed it in her snatch and showed me where to start rubbing. The noise she made should have woke all the neighbors, especially when she had her climax. My god, this belt was amazing. Once she was finished she pushed me away and we both fell fast asleep on the bed, only to repeat the whole ordeal once more. When I awoke the next morning I was back in chastity. I almost had to laugh, but I was feeling bad for myself that I wasn't able to use my own cock to satisfy her. This would be my story for the next several months.
I guess it was about three months on when I noticed that my breasts were getting kind of itchy and my nipples were starting to hurt again, but it was different this time. They were starting to get sort of puffy and each breast was kind of swollen. I told Monica and she wanted to take a look, "Mmm, nice increase in your breast size, don't you think sweetie?"
"Well, yeah, kind of, but what's causing it?"
"Have you noticed any other changes?"
"Yeah, now that you mention it... my skin seems to be getting softer and my facial hair is not what I used to be, here look?"
"You're right! Isn't that great? What about your hips?"
"They have gotten wider too, isn't that strange?"
"No, not really. Are you having trouble lifting things?"
"Yeah, but I thought maybe I was just tired, or something."
"Yeah, it's that something..."
"What are you talking about Monica?"
"That something is called hormone replacement therapy, or HRT."
"Yeah, and what does that mean?"
"You know those new vitamins you've been taking for the last few months?"
"Are you saying that vitamins are doing this?"
"Yes, I am."
"How's that possible?"
"Because you have been taking estrogen and androgen blockers, not vitamins," she said with a smile.
"I don't understand that medical stuff, so spell it out for me please... Why would you want to give me estrogen?"
"I'm changing you into a female."
"You what???"
"The estrogen is replacing the testosterone that the androgen blockers are blocking and that's why your breasts, hips, and the rest of it is happing to you. You do like it, don't you sweetie?"
I just stood there dazed as if some had hit me with a brick up the side of my head. I didn't know what to say. My breasts were getting larger and I now wore a 36b bra full-time without any problems filling it out. And it's true, the hair on my legs and face were getting pretty thin. My bum was another problem, but not so much, as I wore a dress practically every day now. Did I like it? Yes, sort of... no, make that a whole lot! "Yes I do, but I wish you had told me of your plans."
"Well, speaking of plans... what do you think about making the final journey?"
"What journey are you talking about?"
"The ultimate journey sweetheart!"
"And that would be where to???"
"Into womanhood. Your final journey is to get a sexual reassignment and become a woman!"
I just hung my head to think. Did I truly and honestly want to become a female? I hadn't used my dick in so long that I now wondered if I ever wanted to again. The thought of having a vagina was really intriguing and I would have to give that some real thought. I did like my breasts and would like to have larger globes because they are so fun to play with. My double nipple piercings have made them more sensitive to Monica's tender touch. "Honey, I think I would like to make the final journey!"
"Good, you have an appointment for next week to get a bilateral orchiectomy and they will remove your testicles and scrotum to give you a nicer appearance. Having all that extra skin hanging about after they remove your ball is just too awful to even think about. You will love it! At that point you can have your sex changed to female on all you legal documents and drivers license. And, in about six months after that you will and I will fly to the orient and you will get your final surgery out of the way. You will leave the United States as a lady boy and return as a functional female, all except for having children that is."
I had to sit down and I started to cry because I was so overjoyed. From this moment on I would look forward to changing into something that I had always wanted, somewhere in the far recesses of my mind. I think mother would approve and be most happy for me. I think I will go put on some of my best make-up, my best outfit, and my tallest high heels and walk down the streets feeling nine feet tall! I can't wait to get to my other side!!!