Secret Lives Pt. 03

This is a continuation to Secret Lives Pt 2. I highly suggest reading the previous chapters as they set the stage for this part. This part is more of a development chapter and some readers may find it lacking in the sex department, but I feel it is important to the overall tone of the series.

I appreciate the feedback and please keep it coming. I am also looking for editors with some experience to edit my works. If you're interested, please send me some feedback with your contact information. Thanks and enjoy!

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CHAPTER 4

My eyes were wide as Jen started pulling items one by one out of the shopping bags. First item she pulled out was a light pink and lace thong. She handed it to me and I stepped through the leg holes, sliding it up my bare legs and around my waist. Jen grabbed the back and gave it a quick tug, seating the thong deep between my butt cheeks. I did my best to try and tuck my cock and balls neatly underneath the thin fabric, which elicited giggles from Jen.

She told me not to worry too much about being covered as she pulled out a nude body shaper that would help slim my waist and hide my "extra parts" as she called them. I stepped into it and struggled to pull it up as it was exceedingly tight. The body shaper hugged my body tightly and ended just above the bottom of my rib cage. Looking in the mirror, I could see it narrowed my waist, giving me more defined hip bones. Extra padding in the hips and buttocks helped fill out the areas I was lacking, transforming my predominantly male figure into a more feminine look.

"Nope, that won't do!" Jen exclaimed as one of her hands dived down the front of the undergarment while the other went down the back. Her front hand grabbed the head of my dick and pushed it between my legs, where her back hand grabbed it and held it up tight. She then used her free hand to tuck my balls back and up between my legs. Removing her hands, she was much more satisfied with the look. She tugged and pulled at the shaper to get it to sit high between my thighs and nestle between my butt cheeks similar to the thong.

Next, she reached into the bag and pulled out a light pink garter. She held it while I stepped in, moving it up and cinching it around my waist. Jen adjusted the waistband so it sat just above my hips and the four straps fell evenly on the front and back of my legs. She fussed with some of the lacey adornments on the garter, making sure it all sat flat and proper.

Her hands went into the bag again and pulled out a package of black stockings.

"I wanted to get pink to match your garter, but I think these will match your outfit better." She said as she ripped open the package and discarded the paper card they were wrapped on. She handed them to me and sat back as I rolled the sheer stockings up my legs. I am no stranger to wearing stockings, but putting them on with my newly hairless legs was like putting them on for the first time. The stockings had a thick lace band that hugged my thigh and matched the pattern of the lace on the garter.

A bra in pink to match the garter and thong, was next. Before putting it on, Jen stopped me and asked what happened to my boobs. I told her I took them off before the shower and could put them back on if she'd like. We grabbed the adhesive and the breast forms and she generously applied the glue to them. As I held them in place for the adhesive set, Jen pulled out a bra and panty set that matched mine and began to put them on. Once my forms were secure, I put my bra on and Jen led me to the bathroom.

Jen had me sit at the makeup vanity and proceeded to examine my face. She pulled out a set of tweezers and quickly shaped my eyebrows into a much more feminine form, then proceeding to cut and style my brunette hair into a more feminine cut . I was wondering how I was going to explain this to my coworkers but decided I could figure it out later. Once she was done she started applying a cover up to my face but became frustrated when the dark hair follicles were showing through even after just using the hair remover. She was rooting around in her makeup bag looking for something to mask it with when I told her I have something.

I grabbed my own makeup bag from the bedroom and pulled out a red lipstick, applying it to the darkest areas. I blended it in and then used a masking concealer to cover it up. The red of the lipstick helped hide the bluish hues of the hair follicles and the masking concealer made it all disappear. Jen applied the rest of the foundation to even out my face, then started on my eyes. The sensation of having someone else doing my makeup was exciting and I was having a hard time believing it was real. She curled my lashes and applied mascara and eyeliner, getting mad when I moved my eyelids too soon and smudged the liquid eyeliner, forcing her to redo it. After fixing my eyeliner she applied a light pink lip liner and lipstick to match the rest of my garments and quickly applied some blush to my cheeks.

I looked in the mirror once she was done and was incredibly surprised at the figure looking back at me. I had done my makeup before but the results I achieved were nowhere near as good as hers. I started to believe for the first time that, with her guidance, I could be passable as a female.

We then headed back to the bedroom to finish getting dressed. While she pulled on a pair of jeans and a tight knit top, she handed me a loose black flowing skirt and white floral print blouse that, while loose at the top, hid the seams of my forms. The sight of the material of the blouse being formed around my "C" cup breasts was erotic. A pair of black patent 2" heels and a black jacket finished my outfit. She grabbed some jewelry from my wifes dresser and slid a bracelet on my wrist and did up a tight black choker around my neck. I was looking in the mirror and I couldn't believe the woman looking back at me.

"Too bad you don't have your ears pierced yet." Jen said as she dug out a purse from my wife's closet and placed the contents of my wallet into it.

"What do you mean, yet?"

"While how often do you see a woman out around town who doesn't have a pair of earrings in? If you don't want to attract unwanted attention, you have to get them done! Let's go!" And with that Jen grabbed my hand and started dragging me down the hallway towards the door.

"Woah Woah Woah, what are you doing???" I exclaimed.

"We got some shopping to do!" Jen retorted, "and we have to get your ears pierced!"

"I can't go out like this! What if someone sees me? A friend, a coworker? A neighbour?" I was shaking, I had always dreamed of going out of the house dressed en femme, but I can't actually do it!

"Look in this mirror. What do you see? Can YOU even recognize yourself?" Jen Asked

She was right. Staring back at me in the mirror was a woman, and a pretty good looking one at that. I couldn't get over the fact that it was my reflection.

"Well, no, I guess."

"Exactly!" She said, "what are you worried about? We'll take my car out and head to the other side of town. No one you know will be out this late on a weekday evening, and even if they are, all they'll see is two attractive women out shopping. I've heard you sing karaoke and I know you can easily throw your voice to sound more female."

And with that she grabbed my hand and dragged me out the door. It was a cool evening and the sudden rush of air up my skirt was as refreshing as it was shocking. As Jen dragged me down the driveway to her car, I scanned the neighbourhood, expecting people to jump out from the bushes any second and start ridiculing me. No one did. There was a couple walking a dog down the road and they just smiled and waved, then continued on their walk like nothing was out of the ordinary. Like there wasn't a man in drag standing in the driveway. I quickly walked to the passenger side door of Jen's car and got in, glad I wasn't trying to be this graceful in my 6" heels.

Jen sped across town. After a 45 min drive we arrived at our destination. The clock read 8:30, so she said we wouldn't have much time and would just grab a few essentials at the mall. She dragged me into a clothing store and headed for the casual wear area. She held pairs of capri's, skinny jeans, shirts, blouses, and sweaters against me. After selecting a few she grabbed me and bolted for the change rooms. I was getting ready to go in but was surprised when she followed me.

"What are you doing?" I asked, "you're going to get us caught!"

"Relax, women go into the same change room all the time! They'd probably be more suspicious if we didn't!" She said.

After quickly changing she decided on a pair of skinny jeans and a white v-neck top for tomorrow's outfit. We left the change room and she grabbed a pair of flats before heading for the checkout. The cashier rang up the clothes, gave us the total and asked how we wanted to pay. I stayed silent, hoping Jen would answer for us but was quickly growing nervous as her and the cashier just stood there looking at me.

"Umm, Credit please." I said, in my best femme voice, which slightly cracked with nervousness. Nothing seemed to alarm the cashier, at least no security guards or hidden paparazzi jumped out from behind the pillars. I pulled my Visa out of my purse for the first time and completed the transaction. Luckily the cashier never asked to see ID to use it, I hadn't thought about that when I told her credit and was very happy I dodged a bullet.

After we left the clothing store we put the bags in the car and started walking down the street. It wasn't long before we came to a small tattoo and piercing parlour. Jen grabbed hand and dragged me in. It was late and there was only one artist in the store who was sweeping the floor. Upon our entry, she placed the broom down and walked over to us, looking us up and down.

"What can I do for you ladies?" She questioned.

Jen inquired about ear piercings and I was quickly ushered into the chair. Before I knew what was happening she was disinfecting my ear lobes.

"So rare to see a woman without her ears pierced these days. What made you decided to finally get them done?" she asked.

I started to open my mouth to answer when Jen beat me too it.

"Well let's just say she's undergoing a few changes and she's a new woman now." Jen placed a heavy emphasis on the words "changes" and "new". The artist looked me up and down and a shocked look came across her face.

I quickly realized she was figuring out my secret and could feel myself turning red. I started to get up to bolt from her chair before the ridicule began when she reached up and grabbed my arm.

"Please don't go!" she pleaded. "I'm didn't mean to look so surprised, it's just I NEVER would have thought you weren't a natural woman until your wife said that and I caught a glimpse down your shirt and saw the edge of your forms."

I relaxed a bit in the chair, her comments starting to ease the tension.

"You're very beautiful and completely passable. Hell, I think you look more like a natural woman than I do!"

I examined the artist. She definitely had a kind of tomboy look to her. Her hair was cut short and her chest was on the smaller side, and her jaw had a slight squareness to it. She could probably pass as a guy with a bit of tape.

"I'm not his, her I mean, wife. My names Jen, I'm his sister-in-law. I'm helping get Krista ready for when her wife gets home from her cruise." The artist introduced herself as Tiffany, but asked us to call her Tiff. Her and Jen chatted for a few min about the situation we were in and I was quite relieved Jen decided to leave out the details of how she found me. After a few minutes, Tiff asked me if I was sure I wanted to go through with my piercing. I told her I was sure and a few min later, and a little bit of pain, and I was looking it the mirror at my new studs. Tiff gave me some after care instructions and apologized by being so taken back when she realized I wasn't a natural female.

Me and Jen walked out of the store, my ears still stinging and feeling heavy with their new jewelry. I have to admit, despite everything, I was on cloud nine. After years and years of hiding my fetish, here I was walking down the street with my hot sister-in-law, who just hours earlier swallowed a load of my cum with my wife's permission. Not only that, but I was just found out by a complete stranger who was more shocked that I wasn't an actual female than the fact that I am actually a guy.

We continued strolling down the street, chit chatting about random things and deciding where we wanted to go eat when we happened to wander by an adult store. Jen, as she is wont do, grabbed my hand and bolted through the door.

Jen led me to the first aisle, which was lined with dildos and vibrators on each side. She began to browse a vast array of toys, picking up seemingly every package and studying them. She had me go and grab a basket and hold it while she started placing a few items inside. Once she reached the end of the aisle, she had a varied collection of 4 or 5 dildos and vibrators. They seemed to all be somewhat life like to very realistic, and in the 6-8 inch range.

After she had a couple new dildos and vibes, we continued on. Next aisle over were the restraints. Jen repeated her process of carefully examining each one and threw a couple into the basket. She mentioned that I was already pretty well equipped but there were a few things we would need. She grabbed a wrist binder that had a loop to go around the captives neck and then two loops to fasten the wrists down the back. She also grabbed a couple rolls of bondage tape, a set of lockable heel cuffs, and a sex swing that hangs from the ceiling.

We continued around the store and she picked up a few more things. A couple of slutty outfits, a corset, a new set of butt plugs in various sizes, and a couple bottles of lube, to name a few. What surprised me the most was when she picked up a chastity device and placed it in the basket and a strapon Ultra Harness 2000.

We proceeded to the checkout where everything was rang up. I couldn't believe my eyes when the total came to over $1000. We paid and started the long walk back to the car. My feet were starting to ache a bit as I wasn't used to wearing heels this long or walking this much. Once we got there, we loaded the bags in we decided to grab a bite to eat as I was famished. It was actually quite nice being able to sit down and have girl talk with Jen. Our relationship up until this point had been quite cordial, but never went beyond small talk. We chatted about our work lives and about our love lives. She was currently single after coming out of a long relationship recently. I think even she was starting to forget that I was her brother-in-law, as she started telling me things like I was one of her girlfriends, although the bottle of wine we shared may of had some effect.

She talked about how she's been having trouble satisfying her sex drive now that she doesn't have a steady relationship. She's been meeting guys for random hookups, but was complaining that most of them only cared about getting themselves off and didn't want to take the time to learn about what she liked and wanted. She finished that thought by saying "Well, at least I have you as my sex slave for the next 10 days."

"I can't do that Jen, I can't cheat on Sarah, especially with her own sister." I replied.

"Oh silly," she said grabbing for her phone, "you think I'd use you as my slave without Sarah's permission? Read this".

She slid the phone across to me. Displayed on the screen was a series of emails between her and Sarah. In one of the emails, Sarah laid out some ground rules. To my surprise, it was all things that we must do, not a single Don't was listed. In the last line of the email, Sarah told Jen she was free to use me however she wanted and that if she was on a cruise with her secretary, I should be able to have fun too and she'd rather it be with Jen than some stranger.

I was trying to wrap my head around the change in Sarah. She had always seemed quite protective of me and now she was giving me permission to sleep with her sister? Well, more accurately, she was giving her sister permission to do whatever she pleased with me.

We finished our meal and headed back to our house. Once there, Jen helped me carry all the bags into the house. We set them down in the living room and she declared it was fashion show time. I grabbed a bottle of wine and a couple glasses out of the kitchen and joined her in the living room. After I filled out glasses, she held it up in a toast to my new persona and the next 10 days.

She tore into the bags and started pulling out the outfits from the adult store as I undressed. I was standing before her naked as she produced a teddy with a matching g-string. The sheer material felt wonderful as I slid it down over my body and she helped position it over my breasts. I pulled the g-string up and she made sure to seat the strap firmly between my ass cheeks again. There wasn't much material to hide my cock but she didn't seemed too concerned about it.

After twirling around and modelling it for her she had me try on a few other outfits. Finally she pulled out the corset. I've always loved the look of them but had never tried one on.

The one she had picked out was black satin with red trim. She loosened the laces and held it up. I stepped forward and she wrapped it around me and started doing up the buckles in front. Once they were fastened I turned around and she started lacing it tightly. As she pulled harder and harder I could feel it begin shaping my body, constricting my diaphragm and making it difficult, if not impossible to take a deep breath. She finished the lacing and tied them off. I ran my hands over the corset and was amazed and how well it pulled in my waist and forced the extra skin up, making it fill out the cups of the corset even more. Jen admired her handy work for a while an before pulling out a small black box from the sex store bag.

She opened the box and pulled a plastic contraption out of it. It was a clear plastic with a pink tint to it and was shaped like a small cock. She pulled me forward and proceeded to put a plastic half-ring around the base of my cock behind my balls. Another small plastic piece was placed around the top, completing the ring. A plastic stud was pushed through the small plastic piece from behind and a spacer was slid over it. Next she opened a condom and placed it just over the head of my cock. It was then fished through the cock shaped piece. She held it up to my cock and pulled on the condom. I was surprised as my semi erect cock disappeared into the plastic piece and a hole in the back of it was slid over the stud. She then grabbed a small padlock, put it through the stud and locked it. She let my cock go and I could feel the added weight. Jen explained the purpose of the new chastity cage she had just locked on me. It would prevent me from getting an erection or getting myself off until she removed it. I examined it closely and could see she was right. My cock was straining at the unyielding plastic and could not grow erect. The sensation wasn't painful, but mildly uncomfortable. She explained she wanted to make sure she was in full control and I couldn't get off without her permission.

To finish my outfit she pulled out a pair of black thigh-high stockings which were held in place by a garter belt. A pair of black and red boy cut panties finished the look. She pulled out a butt plug from the bag and had me bend over while she lubed it up and worked it into my ass. It was roughly the same size as the one I had in earlier and slid in fairly easily. She asked me to go fetch my platform heels from the bedroom to finish the look while she got changed. I struggled to get the heels on with the corset making it almost impossible to reach over and do up the buckles, but with some difficulty I got them done up and headed back to the living room. While I was gone Jen had undressed and was now wearing a black and red teddy.