Jacki's Journey into Sissyhood Pt. 03

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Jacki's relationship with Laura and Steve begins.
6.2k words
4.69
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Part 3 of the 5 part series

Updated 10/30/2022
Created 12/17/2014
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jacki697
jacki697
356 Followers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming.

*****

I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I going to surrender totally to my feminine desires? Could I really give up my male life, based solely on sexual release? What would people think?

Well I had surrendered to them with Steve and Laura, and it had led to the best sex id ever had, as a woman!

With Steve and Laura I had felt really comfortable, like I could truly be myself. They had helped open up my eyes to new things, and I was comfortable with them.

Who did I have to disappoint? I was no longer married, and I sure didn't care what my ex-wife had to say. I had no children, no family to object to my lifestyle. Really there was only one other person that I cared about and valued there opinion.

My friend Sarah and I grew up together. She was quite pretty, but she was the Tomboy of the school and played basketball, softball and ran cross country. We were pretty close throughout school, and I was the first person she came out to as a lesbian. When I got married, she objected adamantly. Turns out she was a much better judge of character than I was. After my divorce we talked fairly regularly, and if anyone could understand my predicament she could.

I picked up my phone and dialed her number.

We talked for a while about normal stuff and laughed a bit, then I dropped the bomb. I explained that I had been crossdressing, I rambled on about my New Year's Eve tryst with Steve, the threesome with Laura and Steve, and then the offer itself. I ended my plea for help with, "I don't know what to do, I'm so torn, help me Sarah."

There was silence on the other side of the phone, I wondered if she was angry that she had been friends with such a pervert and I was about to be the recipient of insults and slurs, then Sarah spoke. "Do you want my honest opinion?"

"Yes," I replied meekly, bracing for the worst.

"I think you have already made up your mind to go through with it. Not to hurt your feelings but you always made a kind of crappy guy, but I always thought you'd be a beautiful girl. You told me to follow my heart, when I told you I was a lesbian; you need to follow your own advice. And you have my full support, I love you and always will. But once you transition I deserve pictures and an invitation to come visit."

I sat back in relief and astonishment, "Thanks Sarah, you're the best."

We hung up, and I felt like a weight had be lifted from my shoulders. I was a sissy, I wanted to be they're sissy.

I picked up my phone and texted Laura: "Hey, do you think you could come by Thursday. I would like to chat."

A few minutes later Laura texted back, "Of course, I'm so glad to hear from you. Someone was starting to miss you." A two pictures followed. One of her pussy, and another of Steve's erect cock.

I replied, "LOL, tell them I've missed them too."

The next day I went to my job and turned in my resignation. I then went to the post office and change my address and told my building manager of my move. I returned home and began boxing up my belongings.

Thursday rolled around and I was excited as I've ever been. I got myself up early and dressed in my red mini dress and strappy sandals. I tried my best with my hair and makeup, but I hoped Laura would bring hers. I patiently waited for 11 o'clock to come and Laura's arrival.

Finally the time came and I saw Laura pull up in her Mercedes and trek towards my door. I opened the door as soon as she knocked, and welcomed her in. She kissed me on the lips and said, "I love the dress girl." She looked around the apartment seeing the moving boxes and looked back at me in excitement. "So, it looks like you made a decision."

"If the offer still stands, I'm all yours," I exclaimed.

We jumped into each other's arms like a couple of school girls, dancing around in my living room.

"Well now that's out of the way, how about some fun," Laura said as she dropped her coat to the floor revealing that she wore nothing underneath expect high heels, a pair of sheer stockings and her strap on. She grabbed me and pulled me close kissing me firmly. As our tongues wrestled, I teased her nipple studs with my free hands. I broke the kiss and lowered my mouth to her swollen areolas, sucking them like a hungry infant.

"Let me see your sweet ass, Jacki," Laura demanded. I stood up and bent over the couch, and lifting the hem of my dress over my ass. Laura then pulled down my panties and had me step out of them, she then said, "here slut, stuff these in your mouth. I don't want your moaning to alert the neighbors."

"Yes mistress," I complied.

Laura the spread my ass cheeks with her hand and set to work on my hole with her mouth. Her tongue was every bit as talented as Steve's if not more. I bit down hard on my dirty panties as she licked my pussy. "Damn, Steve was right, you taste sweet."

She then looked at me, "are your ready baby," as she rubbed my ass. I nodded in approval. "Good slut."

Laura's dildo was positioned at my butthole, and with a gentle push she entered me. She fucked me slower this time savoring the fucking as she impaled me. I moaned through the panties as her strap on rubbed my P-spot. I began to rock my hips to meet her thrusts, causing the pressure on my prostate to increase. She could tell that her fucking had me close. Laura then withdrew her cock, leaving me open, then spinning me around and dropping to her knees, and taking my hardened clitty into her mouth and sucking me hard. In less than a minute I emptied my balls into her mouth. Once I stopped, Laura rose and brought her lips to mine, and we swapped my cum back and forth, before we each swallowed our share. We kissed once more before Laura looked at me and said, "Did you enjoy that sissy?"

I nodded, "yes mistress, I did."

"You might want to remember it, because it's the last blowjob you'll receive," she stated. "From now on when we play, you will not be allowed to jack your clitty. Your sexual release will come from anal play, and pleasing others. And since it's of no more use, we will keep it locked up. Your clitty shouldn't get hard because that's very unladylike."

I obeyed, "Yes mistress."

She reached into her bag, and fuddled around for a minute till she found a small pink plastic cock cage. It had two pieces, the first was a cock ring that went around the base of my testicles, and choked off the blood flow, while the second piece shrouded my cock and attached to the base with a small gold lock. Laura snapped the lock closed. The closing of that lock signaled the end of Jake, and the beginning of Jacki.

We took and shower together and washed each other, followed by drying each other bodies. I then applied lotion to Laura's body, and she did likewise. To my delight she had brought her makeup supplies and quickly did my face. "We will have time for instruction and practice later, I'm just going to fix yours quickly so we can get loaded and on the road."

"Sounds good, Laura," I replied.

She quickly finished my makeup and teased my hair to life. She finished with a dab of perfume on my neck and showed me how to dab it on my wrists. I rose from my seat so Laura could finish getting herself ready. "Oh, Jacki, look in my bag. I brought some things for you and me to wear. There is a red and blue plastic bag, the red is yours, bring me the blue bag sweety."

"I'm on it," I laughed.

I scampered into the kitchen. I had already grown somewhat accustomed to the chastity cage on my clitty, and it wasn't as uncomfortable as I initially believed. I quickly found the appropriate bags and returned the blue bag to Laura as she curled her eyelashes. "Thanks darling, now get your butt ready we have work to do."

"Yes ma'am," I said playfully.

Laura looked back at me in annoyance. She then just pointed with her free hand for me to go get dressed.

I laid the bag on the bed and began sorting through the contents. The bag contained a black pleated mini skirt, and blue long sleeve shirt, with a slinky neck, and a pink Victoria's secret bra and thong. I removed the tags, and slipped myself into the thong and fastened the bra around me. The band size was perfect but the cups were quite small, only an A cup. "How are my forms going to fit in this bra?" I enquired.

"Oh girl, don't wear those. I bought you some filler cups this morning, they are in the black box, in the bag," Laura replied as she sprayed her hair.

I returned to the bag and found the box, and slid the silicon pads into the cups. They fit snug and looked a little more natural. Next came the skirt, which fit snugly around my waist, and covered my ass and legs down to mid-thigh. I quickly slid the shirt over my head, taking care not to mess up my hair and makeup. Checking my appearance in the mirror, I looked hot. The clothes fit perfectly and the skirt was young and flirtatious. I then realized I needed shoes. "Which shoes do you think Laura," I yelled.

"Oh, what about those black pumps, that should be cute," she replied.

Great, those are already packed. I sorted through my boxes, till I found the one marked shoes and opened it. I fished through the box till I found them. I closed the box back up and then slipped the pumps on my feet.

"Oh Jacki, that looks so good on you," Laura exclaimed as she exited the bathroom fastening and ear ring to her ear.

"Yes, you have great taste in clothes," I replied. As I admired her white halter type dress. Her auburn hair was layered perfectly and her gold stiletto sandals showed off her ruby red toes.

"I do, don't I," she agreed. "So are you ears pierced, I hadn't noticed."

"No, unfortunately," I replied.

"Not a problem, we can take care of it today."

"I thought we were going to move my things today," I questioned.

"Honey," Laura stated, "who ever heard of moving in dresses and heels. A couple of Steve's workers are going to come by and take your boxes to the house."

"Oh ok, well that makes sense," I responded. "Well what are we going to do?"

Laura laughed as she touched my shoulder, "What girls do, we are going shopping of course."

"Are you sure I'm ready for that?"

"Yes, darling you look great," Laura assured me, "but even if someone does find you out, it won't be a big deal."

"Ok, if you say so."

The movers showed up later, and Laura instructed them about which boxes needed to go. And where they were to be unloaded. I got to check out the hunks that came to move the boxes. Laura caught me, "Pick up your jaw, girl, they are strictly off limits for you."

Once the boxes were gone, we got in Laura's car and headed downtown. First Laura had my ears and belly button pierced and bought me cute diamond studs for my ears and a cute rhinestone dangle for my navel. Then the afternoon was filled with dresses and shoes and lingerie. I have no idea how much money was spent on me but she spent a thousand dollars in Victoria secret alone. The last shopping stop was at Frederick's of Hollywood. Where she purchased several different items for me. One in particular she said was for tonight. It was a Red and Black babydoll, the front had a satin fly away design so that it exposed my navel, and in came with a matching red lace thong that was crotchless. Laura's trunk and backseat were completely full of shopping bags by the end of the day. I was completely exhausted, from putting on clothes and then taking them off, and the trying this and that on. But it had been a fun day.

"Laura I hate to be such a wimp, but are we about done for today," I pleaded.

"One more stop, but this will be some pampering, no more shopping," she promised.

We pulled into a small shopping complex, and parked in front of a nail and day spa. I followed Laura into the place, and it was kind of dead. A small Asian lady saw us come in and yelled, "Customer." An older lady came to the counter, "What can we do for you lady's today?"

"We both need manicures and pedis, and a full wax," Laura ordered. The lady at the counter the led us to our chairs. We sat down and the young Asian lady removed both our shoes and washed our feet. I was a little nervous and I guess she caught on. "Relax, this is supposed to be fun," the lady stated.

Laura laughed and pointed at me, "Don't worry she's a first timer."

The Asian woman looked at me again, and then nodded, "oh I see now." I looked at Laura with my not amused look. "She knows what I am now for sure, Thanks."

"Relax darling, you aren't the first sissy she's seen."

Moments later a small army of women came out of the back room carrying various totes. Before I knew it, there was a woman at my feet and one on each hand as my nails and feet were sanded, buffed and primed. One of the lady's asked Laura, "What color would you like."

"Red for the toes, French tip acrylics for the nails," she answered and nodded in my direction," and she will have the same."

With their instructions given, each woman set to her task. Before long they were finished and I stared down as my hands now bore long acrylic nails, and my feet were more feminine and cute with bright red nail polish. Laura, then motioned for me to get up and follow her into the back, "We aren't quite done yet."

She led me back to what looked like a massage parlor. Once inside she began removing her clothes, "what are we doing?"

"It's time for our body wax, you have to be naked for that to happen," Laura laughed.

I froze for a second, "I have to be naked?"

"Well of course you do," she chided.

"But she will see..." Laura interrupted "that you're a sissy, honey, she already knows, now relax and get naked."

Feeling a little defeated, I began to remove my clothes and lay them on the table neatly. I then stared and the table, which resembled part massage table, part gynecologist exam chair and part torture device. "How the hell to you get on this thing?"

Laura instructed, "Its easy lay on your stomach and lift your legs onto the leg supports." I followed her lead and it was surprisingly easy. I closed my legs to try and hide my caged clitty, like now was the time for modesty. Once I was settled, Laura yelled, "We are ready now."

On command the Asian woman accompanied by another came in and pushed a cart in-between the table. The little Asian lady came to my side of the table and asked, "Ready."

"I guess," I replied.

She then began spreading hot wax across my ass and applying cloth strips over the wax. With one swift motion she would rip the strip off of my body, taking with it the wax and 4 day old stubble. The first strip caused me to jump and yelp in pain. Which caused all the women in the room to giggle. That only added to my embarrassment. As she continued ripping the rest of the hair from my ass and the back of my legs, she began to spread my legs apart and wax the inside of my legs. This led her to the crack of my ass and taint which she laid bare in one fell swoop. After my crack was done, she tapped me on the ass and said, "Time to flip."

I looked over at Laura and she just gave me to roll over motion with her finger. I reluctantly rolled over with my back on the table. When the little Asian lady caught sight of my caged clitty, she giggled, "it's so cute," as she touched it. I gave her a go to hell look, and she apologized, "Sorry, we continue." After what seemed like an eternity, she finally said, "All finished, thank you, "and quickly cleaned up and exited the room. Laura had been finished for some time, and just been watching and giggling at my discomfort. I removed myself from the bench and used the provided towel to clean myself of wax residue, and begin to dress.

"So Jacki, how was your first wax," Laura cackled.

"If my skin wasn't so damn soft and smooth, I'd be pissed at you." My skin was incredibly smooth, unlike it had ever been. As I stroked my baby soft flesh, my clitty began to expand in its cage, straining against its confinement. For the first time it became uncomfortable, and I got dressed to keep my mind of it.

Laura paid our bill and we exited from calls from the salon girls, "Come back to see us."

As we exited into the twilight of the late afternoon, this was the first time I'd had to really admire their work. My hands no longer had a manly appearance, and I was already aware of the longer acrylic nails, "these are going to take some getting used to," I remarked.

Laura smiled back, "as are lots of things, but you look really hot now. Steve will be pleased with our work." I smiled back and we piled into the car and headed home.

Today had been exhausting, yet thrilling experience. Laura had not only pushed my boundaries, but pushed me directly into the deep end of sissyhood. Yesterday, I was a normal guy with a crossdressing fetish, today I was a cockloving sissy, waxed, primped, and locked in chastity by my seductive mistress and daddy. Oh, who was I trying to fool, I thought to myself; I'd always been a sissy at heart, I just didn't know it.

I laughed a little at my realization, Laura noticed, "What's so funny over there, Jacki."

"Oh nothing, just reliving some of today." I answered.

"Well this is just the beginning honey," Laura chided. "I better call Steve and let him know we will need his help with all these bags."

She dialed the number and hit send as we pulled into the drive and she entered her code into the keypad. Laura told Steve to meet us at the garage to help with the bags. The gates swung open and we made our way down the drive toward the house. Laura steered the car around the house and into an open stall in their six car garage. To the right sat a bright red Ferrari, I commented, "Pretty car."

"Oh that's Steve's, he likes to drive the ridiculous thing to the beach, so all the young girls hit on him," she retorted. "He will probably want to take you for a spin in it."

As the garage door began to close behind us, Steve appeared and opened up my car door. He offered me his hand and helped me from the car, "Wow you girls look amazing. I love your nails Jacki, very sexy."

I smiled and said, "Aww, thanks Steve," as he wrapped me in a hug. He released me from his embrace and caught me glance at his red sports car. He remarked, "I'll have to take you for a ride, Jacki."

"Easy there cowboy, we have too much accomplish, to get our guest settled in, before the party tonight," Laura interrupted.

Steve looked at her in disappointment, "Another time then."

"The trunk is popped, bring all the bags from the trunk and car into the pool house, I'm going to show Jacki around Ok," she instructed. Steve nodded in acknowledgement and I followed Laura into the breezeway that connected the main house, and the garage, to the pool house. As we made our way towards the pool house, Laura chuckled, "What did I tell you about that car." We both shared a laugh at her quip.

We reached the pool house. Laura opened the door and guided me in, "Welcome home." I walked in to a large room which was setup, as a living room/kitchen/dining room. The space was well done and expertly decorated. The travertine floors of the main house flowed into the pool house, and the furnishing was of all the same quality. "Wow this is really nice, this won't take much getting used to."

Laura smirked and continued the tour. At the back of the living space, a set of double doors opened into a large bedroom. In the center sat a king sized, canopy bed, constructed of dark wood. The room was filled with a matching bedroom suite. To the side of the bed lay all of my boxes and belongings the boys had brought from my old apartment. We walked through the cardboard boxes into an opening. On one side there was a bathroom, with a large soaker tub, and walk in shower; to the other side a small sitting area with a vanity mirror, and a large walk in closet. Laura led me into the closet, showing me where I could put my dresses, skirts, blouses and lingerie; drawers for bras, panties, hosiery, and a shoe rack for my heels.

jacki697
jacki697
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