Secret Lives Pt. 04

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Jen tightens her control and pushes my limits.
5.5k words
4.68
32.5k
20

Part 4 of the 4 part series

Updated 06/08/2023
Created 12/07/2017
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Note: Sorry it's taking me so long to post the remaining chapters. I'll try to be more punctual in the future. Also, remember folks, this is a work of fiction. I could've had the character bolt the door from the inside in Part 1, but it would've made for a much less interesting story. Anyways, enjoy. Feel free to leave a comment to let me know if you liked it, but if you feel the need to leave negative feedback, just know that I'm either not going to read it or I'll be laughing while I do at the person who just spent an hour reading a story they don't like. Constructive criticism is always welcome.

*****

I awoke in the morning to the sun glimmering through the bedroom windows. It had been a restless nights sleep as my bonds prevented me from rolling into my normal sleeping position and the butt plug constantly reminded me of its presence. I had only been awake a couple minutes when I heard the toilet flush in the ensuite bathroom and smiled as Jen walked into the bedroom, still dressed in her matching lingerie.

"Good Morning sleepy head!" she said as she bounced into the bedroom. "Time to get up and get cleaned so you can start on your chores!"

"You're awfully chipper this morning." I replied as Jen jumped on the bed, straddling me as her pussy came to rest against my cock with only the material of our panties between them.

"Well after an orgasm like I had last night, it was a good night's sleep! Now what's this? Someone have some exciting dreams last night and wake up hard this morning?" She said, lifting her hips and placing a hand on my cock, rubbing it through the thin material.

"Sleeping next to a woman like you would be enough to make any man hard!" I said, thrusting my hips up to try and maintain contact with her pussy.

She gave the shaft of my cock a quick squeeze as she ran her hand down it and began to fondle my balls. "Well maybe we should do something about this, it'd be a shame to let a good hard dick go to waste!" she replied, increasing her efforts on my balls.

Jen removed her hand and laid down on top of me, our breasts pushing together as she began nibbling on my neck. She ran her hands up and down my arms, still locked in their restraints. I wanted so bad to be able to run my hands down her back and forcefully grab her butt, but she was in complete control. She finished nibbling on my neck and moved down to my collar bone, much like I've done to my wife many times before. She kept slowly moving south, stopping on my breasts to give each nipple a quick peck through the material of my teddy.

"Man I wish I could actually feel how good that feels" I told her.

She kept moving down, kissing my belly through the fabric before having me lift my hips so she could slide the teddy up. She hovered her mouth just above the head of my cock as she slid my panties down, letting it spring free and hitting her in the lips. Without any words she wrapped a hand around my shaft and brought her lips to my head, slowly parting them as I entered her mouth. I laid back and closed my eyes, trying to forget about everything else and just enjoy Jens efforts on my cock. She bobbed her head up and down slowly while her hand jerked me off. The occasional slurping sound would escape her lips and she removed her hand, allowing herself to take more of me inside her mouth. Her hand drifted between my legs, grabbing the base of the butt plug and twisting it back and forth and pressing it further inside my ass.

"Oh my god that feels so good!" I encouraged her. The blowjob lasted for a few more minutes before my cock sprang out of her mouth with a pop. She slid her body back up mine and moved her mouth next to my ear, placing a knee on either side of my hips.

"Tell me how bad you want to fuck me." She whispered into my ear. "Tell me how bad you want me to slide my pussy down on your cock"

"Oh god I want to fuck you so bad!" Was my response.

"Not good enough. Tell me how many times you've thought about fucking your wife's sister. Tell me all the times you've caught a glimpse of me and wondered what it'd be like to fill my cunt with your cum."

"So many times I've fantasized about how good your body would look like naked." I began. I guess that was enough to get her started as she reached between her legs, moving her panties to the side.

"I've always wondered what it'd feel like to fuck you, to bury my cock deep inside of you." Jen grabbed the shaft of my cock and started rubbing it around her pussy.

"To bend you over and slide into you from behind, grabbing your shoulders and driving deep into you." Jen began to sit back, putting pressure on my cock as it pressed against the opening of her pussy, a little more pressure was all it took and the head of my cock suddenly slid inside of her. She paused there for a moment, with me just barely inside, as a smile crept across her face. I couldn't believe my dick was inside my sister in law, a fantasy I never thought would come true in a million years.

I thrust my hips up, trying to get deeper inside of her. She responded by lowering herself more. She was so wet there was very little resistance and I quickly bottomed out in her pussy. She sat there for a few moments, smiling as she squeezed my cock with her pussy and rocked slowly back and forth.

"Oh god your cock feels so good!" Jen said as she smiled. "Now, I'm going to use you as my fuck toy and you're not allowed to cum until I say. If you do, you'll be punished!"

"Yes Ma'am, I'll try my best" I replied. I honestly didn't know how long I'd be able to hold on. I had just entered her and already I could feel my orgasm building. Hell, I don't think she'd even have to move, just the warmth of her pussy and the naughtiness of being inside of her was driving me wild.

Jen started rocking faster on my cock, making it hit all the right places inside of her. Her pace quickened as she started raising slightly before slamming back down. She was biting her lower lip and her eyes were closed tight. I wanted so badly to reach up and grab her tits, play with her nipples while we fucked, but the restraints held tight. I could feel the cum starting to boil in my balls, wanting to be released into her gorgeous pussy. I had to close my eyes and try thinking of other things than what was actually happening to try and stave off my orgasm. I could tell Jen was starting to get close. Her moans were getting louder and movements getting more rapid and urgent. Her body collapsed on top of me and her lips landed on my mouth, embracing in a passionate kiss which did little to stifle her increasing moans.

"Oh god fuck me" she said, breaking our kiss. "Your cock feels so good, cum now, fill my pussy!" she screamed, losing control as she slammed down harder on my cock. That was all I needed to hear and as her body quivered and her cunt convulsed on my member, it erupted, pumping my seed deep into her pussy. Jen rode me for another few seconds before collapsing on top of me, panting hard as she started to come down from her orgasm.

Jen just laid there on top of me for a few minutes, her rapid panting slowly returning to a normal cadence while cock started to deflate.

"Wow, I needed that bad" she softly whispered. "I think washing the sheets is going to have to be one of your chores today, probably again tomorrow too!". Jen said as a mixture of our juices dripped out of her pussy, soaking my dick and the sheets.

Jen sat up and climbed out of bed. She told me to hang tight while she disappeared into the bathroom to get cleaned up. A few minutes later she appeared out of the bathroom and started to untie me. She led me to the bathroom and instructed me to get undressed and jump in the shower.

I took off my teddy and let it fall to the floor, which was rewarded with a sharp smack on my ass.

"You're just going to let the expensive lingerie I picked out for you lay on the floor? Pick it up and fold it nicely!" Jen barked at me. I did as I was told and piled all my stuff nicely on the chair. Jen took off her stuff too and handed the soiled articles to me to fold. She had me remove my breast forms and the butt plug before allowing me a few minutes of privacy to use the toilet. Once I was done she rejoined me and we got into the shower together.

Jen handed me a strawberry smelling body wash. I noticed that my "man" soaps and shampoo had been removed from the shower and only the feminine smelling stuff remained. We took turns washing each other but I was disappointed when she didn't pay as much attention to my cock as yesterday. After we were cleaned she rubbed the hair removal cream all over my body.

"You have to use this everyday for the next month. Over time it'll reduce hair growth and you can reduce the amount you use it." She said.

The cream caused my whole body to tingle but it wasn't too aggressive. After 10 min she rinsed it all off and we got out of the shower. We headed back to the bedroom where she had me put in my remote controlled vibrating butt plug with the cock ring. Next she repeated the procedure of locking the chastity cage on my cock. After our morning fuck session it was much easier to get the cage on and it was much more comfortable. With the ring from the butt plug behind the ring of the locked cock cage there was no way I could take either of them off.

Next we reattached my breast forms. She then pulled out a french maid outfit and had me put in on with a pair of white panties, stockings and a garter. The maid costume had a hasp that she fastened and locked around my neck. I put on my 2" heels as Jen grabbed the heel straps she had bought yesterday at the sex store. The cuffs fastened tight around my ankles and had a piece of material that looped from the inside of my ankle, passed under my foot in front of the heel and fastened on the outside of my ankle. It was cinched tight and then another small padlock secured them in place on each foot. I was beginning to realize just how much control Jen had over me. Without her key I couldn't remove my heels, French Maid outfit, or the cage and plug. She then led me into the bathroom and helped me apply a light coat of makeup, instructing me in different techniques of application. We both looked at my reflection in the full length mirror and were both satisfied with the image.

We left the bedroom and went downstairs where she told me I was to make breakfast. I prepared omelets and toast while she sat at table drinking a cup of coffee. Moving around the kitchen in a frilly french maids outfit and heels felt awkward at first, but I was getting used to it and starting to enjoy the feel of the material on my hairless skin. When the meal was ready, we sat down to eat. Jen filled me in on what our plans were for the day. First I was to do what she informed me will now be my daily chores. This included cleaning up any clutter and making sure the house is tidy, making beds, doing the laundry and making sure everything is folded and put away, dusting, and anything else she decides needs to be done. After the chores were done she said we were going to get ready and go out for lunch, followed by some shopping and stopping by her apartment so she could grab a few things. For the evening we were going to meet up with a few of her friends for dancing at a local club. The thought of going out with other people scared me a bit but she reassured me that everything would be fine.

After breakfast I cleaned the kitchen and started on my daily chores. Jen followed me around for a while, teaching me how to move more like a woman. The thing I had the most difficulty with was how to take a step. I never realized how much differently men walk then women. Jen showed me a few times how to walk properly; shorter steps, legs together, one foot in front of the other, rolling my hips as I stepped. It was hard to get used to and Jen decided I needed more encouragement to get it right. She retrieved a paddle she had bought and everytime I messed up, a hard swat on the ass was my reward. After quite a few spanks my progress must've pleased her and she relented.

For the next hour I pranced around the house, cleaning. I finished up and found Jen in the living room, watching TV. I informed her my chores were done. She performed a quick inspection and then led me to the bedroom. Jen removed the padlocks on the maid outfit and my heels. I started getting undressed while she picked out an outfit for me to wear. I was careful to put everything away neatly, heeding her instructions from the shower.

Jen handed me a white bra to match my panties and stockings and the jeans and v-neck we had bought the day before. Getting into the jeans was substantially different from my normal ones and they felt like they were painted on. The cock cage presented a bit of a challenge but with some effort we were able to get it to stay in place and not bulge in the front. The v-neck shirt was next and I was nervous about how deep it plunged. With some makeup, Jen was able to conceal the edge of my breast forms and blend them in to my natural skin. The same jacket and purse I wore yesterday and the pair of flats we bought finished the outfit. We left the house and headed for the mall. It was interesting to me how quickly I was becoming accustomed to leaving the house dressed as a woman. The fear of being found out was still there, but my heart was not racing as fast as it was yesterday.

We drove for some time before pulling up in front of the mall. Jen dragged me into the first store which was full of mostly casual clothing. I followed her around as she browsed. She didn't seem too interested in asking my opinion on anything and I was getting the impression that I was just her dress up doll. After she got an armful of stuff she led me to a dressing room and pushed me in.

"Start trying this stuff on, I'm going to go look for more. Come out when you've changed so I can see." she instructed as she walked away.

I undressed and grabbed the first outfit to change in to. It was a black knee high skirt and I chose a white blouse to go with it. I thought it looked a little odd with the white stockings I was wearing but it was either wear them or go out with bare legs. I exited the change room and looked around, but didn't see Jen. Worried about being accused of disobeying orders, I set about the store looking for her, finally finding her behind a rack full of sweaters. She gave her approval and sent me back to change into something else.

This scene repeated itself for the next hour, me changing, seeking her approval, then changing into something else. Occasionally she'd bring more clothes to the dressing room and take back what she didn't like. Once she was satisfied that I had enough casual clothes to start my wardrobe we paid and left. I was relieved and somewhat surprised that during the entire ordeal, walking through the store dressing in a myriad of women's outfits, I didn't catch a single look from someone that would lead me to believe they knew my secret.

The next store she brought me into catered more to evening wear. Adorning the walls and racks were various dresses, skirts, and tops all suitable for a night out on the town, as well as some clothing for more upscale events. Jen started repeating the procedure of grabbing anything that caught her attention. I watched as she grabbed an assortment of skirts and tops, including some very skimpy ones. A young saleswoman, probably in her early twenties approached us.

"Anything I can help you find today?" She asked. I was about to tell her that we were fine when Jen interjected.

"Oh Yes! Krista here recently lost some weight and became a new woman. She's in need of an entire new wardrobe for nights out on the town."

My face went flush and I could only hope the concealer was working at hiding some of the redness. I could feel the young woman's eyes working me over, examining me from head to toe. Jen had a wicked smile on her face as she knew I didn't like the close attention this young woman was giving me.

"Well I would've never known! You certainly don't look like you were ever out of shape!" She said. I wasn't sure if she was being honest and couldn't tell something was off or if she just smelled a big sale and was willing to play along.

"Let's start with every woman's best friend, a little black dress." With that she led us over to a rack and started picking through them. "You're about a size 8 I'm guessing?"

Truth be told, I had no idea, but luckily Jen had left me an out.

"I'm not quite sure, I haven't really tried much on since I lost the weight. Jen here got tired of me wearing baggy clothes so she made me come out to buy new ones." I lied. A smirk came over Jen's face and I could tell she was trying not to giggle at the little white lie.

"Well, you can start with an 8 and we'll go from there, I'm Jess by the way. Here, let's see how this fits you. Come this way."

Jess led me to a changing room and sent me inside. I disrobed in the privacy of the change room and proceeded to slip in to the dress. It was a tight fitting dress with a halter top that left my back wide open, closing in again just above my hips. In the front there was a keyhole that ran between my boobs, exposing a bit of my bra. The bottom flared out and fell just around my mid thigh, exposing the tops of my white stockings and showing a bit of the garter straps.

Once I was changed I stepped out of the change room. Jen and Jess examined me closely before Jen scolded me for leaving my undergarments on.

"This dress is meant to be worn braless and what kind of slut wears white garters with a black dress? Take them off and me and Jess will find you a pair of heels to go with the dress." She barked. Jess looked shocked at her reaction and I was wondering if she was starting to suspect we were something other than 'Just Friends'.

I slinked back into the change room, nervous about removing my bra and stockings. What if someone noticed my legs weren't as smooth as they should be? What if the adhesive let go and my breast forms fell off? It wasn't like I had much of a choice though. I removed my bra and adjusted the top. The material was fairly tight fitting and the adhesive on the forms was strong, but without a back to the dress to support the forms and hold them tight, I was nervous. Next I removed my stockings and garter and adjusted the dress. I spun in the mirror and could feel the unsupported weight of the forms tugging at the skin on my chest. As I opened the door, Jen handed me a pair of gorgeous black 4" heeled sandals. I kicked off my flats and slipped my feet into them. Luckily they had a heel strap to help keep them on as I took a step, but I still almost rolled an ankle while Jen and Jess led me to a row of mirrors.

"Sorry, it's been a while since I've been in heels this high." I told Jess. She held my hand as I stepped up onto a platform in front of the mirrors. I spun around and looked at myself in the mirror. I really liked the dress and was starting to have more trust in the adhesive on the breast forms. Jess joined me on the platform and started fussing with the dress. She reached up and grabbed the material right around my tits to adjust the keyhole so it sat directly between them, brushing her hands over my tits as she did so..

"I hope you don't mind me saying this, but I would kill to have breasts like yours!" She said. I examined her a bit closer and she appeared to maybe be a B cup at best. "They're so firm and high. They look great in this dress." I smiled at her but couldn't think of any words to say other than "Thanks."

After deciding the dress was a good fit, Jess and Jen praded me around in even more outfits, a dark blue sparkly full length dress, backless again. A mid thigh black patent leather pencil skirt, tight fitting halter and strapless tops, a couple mini skirts. I was on cloud nine. I had never dreamed I'd be in a women's clothing store having two women fuss over me as I tried on skirts and dresses. They also had me try on different shoes to match each outfit. By the time Jen and Jess were satisfied and rang up the bill it came to over $1200. Before leaving, Jen asked if I could use a change room to change my outfit. She handed me a black pencil skirt and a blouse with a pair of 2" heels to change into. I wasn't sure why I couldn't keep wearing my jeans and top, but felt it best not to question Jen.

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