Jacki's Journey into Sissyhood Pt. 02

Story Info
Jacki meets Laura and is given an interesting proposal.
6.3k words
4.72
57.7k
49

Part 2 of the 5 part series

Updated 10/30/2022
Created 12/17/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
jacki697
jacki697
356 Followers

This is a continuation of: Jacki's Journey Into Sissyhood. Thank you for reading a continuation of that series.

*****

I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm draped across my shoulders and the large cock poking at my backside. I tried to slowly slide out from under Steve's arm, only to have him pull me closer and kiss my shoulder. "Good morning Jacki," Steve said sleepily as he yawned.

I took my free hand and grasped his erection, and laughed," It seems this guy has been up for a while now."

He chuckled back, "Yeah, well who can blame him he's next to such a hot piece of ass."

"He does have good taste in gurls I guess, and he tastes good too."

We both laughed for a minute and then I rolled over and kissed Steve good morning. "Well I'm guessing you will be leaving me soon," I pouted.

Steve glanced at the clock, "yeah I need to head out in a minute."

"You have time to do something with that erection," I questioned.

"I figured you're too sore for that this morning."

I answered, "Well I am pretty sore down there, but how about a blow job instead."

"I've never been a man to turn down a blow job."

I peeled back the blankets to reveal his stiff member cloaked in his boxers. I peeled down his boxers and set to work. This time I attacked his prick, quickly swallowing it and coating it in saliva. I used my hand one hand to work his shaft and the other to fondle his balls, while I bobbed up and down on the shaft.

"You are cock hungry little slut this morning aren't you," Steve asked.

I managed to gurgle out a, "yes Daddy," with his dick in my mouth.

He laughed me on and began to moan slightly as I continued milking a load from his cock. I then pulled his cock out of my mouth and began sucking on his testicles. He sighed through his teeth, "That's it you dirty girls, such Daddy's balls."

Spurred by his encouragement I rolled each testicle about in my mouth as my hand furiously worked his shaft. After thorough tongue bathing his sack I returned the attention back to his shaft and licked it from base to tip before returning it to my mouth.

After of couple of minutes I felt Steve's cock pulse, and I knew he was close. He smiled and moaned, "Is daddy's gurl ready for breakfast?"

Once again I murmured, "Yes daddy," as I worked his tool. A few seconds later, I felt Steve raise his hips and moan, "OH god, baby I'm cumming."

His cock then began to spasm and launch ropes of thick warm seed into my throat. I tried to swallow as much as could, but there was once again a lot to deal with. Some of his delicious nectar began to leak out.

I looked up at Steve as I released his cock and choked down the mouthful of his baby batter. As I swallowed he protested, "Looks like you made a mess, you need to clean daddy up."

I returned to Steve's crotch and began to tongue up all the spilt jizz from his cock and balls. Once he was satisfied he tapped me on the head and said, "Good gurl, you learn pretty quick."

"Thank you Daddy," was my reply.

"Listen I'm going to use your shower to get cleaned up, why don't you make me a cup of coffee for the road."

"I'd love too," I answered.

Steve disappeared into the bathroom and the water began to run. I scampered into the kitchen and began preparing his coffee.

About the time the coffee pot was done, I heard the shower shut off. I yelled through the door, "How do you take your coffee."

"Two sugars," was the reply.

I returned to the kitchen, and found an old travel mug of mine. Filled the cup then added the sugar and fastened the lid. As I finished up, Steve emerged from the bedroom.

"Great the coffees done." He walked up behind me and smacked my panty clad ass, which made me jump. He grabbed the cup, and said, "Thanks baby, I really got to run. Last night was incredible, and I've got your number so I call or text you later in the week Ok."

I nodded, "Ok sounds good." Steve kissed me once more and then was out the door.

I stood alone in my living room, still dressed in my babydoll from last night, and my wig, with a butt plug in my ass containing a wad of a strange man's cum in my butt. I probably should have been embarrassed with myself but strangely I was a little proud.

Before hand when I crossdressed it was simply about my sexual release, primarily achieved through me masturbating. However last night I hadn't even touched my dick. I had an orgasm, a powerful one, but it felt different. After my sexual release when I jacked off, I often lost my sexual desire and often felt ashamed. But my sexual release last night from my deflowering just made me hornier.

And frankly I didn't particularly care about my pleasure as much as I cared about pleasing Steve. It was a revelation for me. I don't know what he knocked loose inside of me with his cock, but I did know this wouldn't be my last gurly experience I was hooked.

The rest of the week went by pretty quickly for me. I was busy at work and had to work long hours. Thursday rolled around and I began wondering if Steve was ever going to call back. That evening I got off early than I had all week, I swung by the gym for a run, then came home for a little me time. I ran a bath and grabbed a glass of wine and set to relax. As soon as I got into the tub, my phone began to ring.

I looked at the number, it was Steve. I answered quickly, "Hi there, I was beginning to think you were never gonna call back."

"It's been a long week sweetie, but all is ok. How was your week?"

"Busy and long," I laughed.

"Well listen, I was wondering if you would like to come to my place for dinner tomorrow night."

"Sounds lovely," I replied. "Can I come and get ready at your place early?"

"Why don't you just get dressed at your place, I'm sure you have a cocktail dress or something you could wear then you could pack an outfit for later," Steve insisted.

I stammered back, "But I never, have been out before."

"Listen you could easily pass, plus it's not like you are going to be out. Just in your car till you get here. I really want you to come, I have a little surprise for you."

I finally reluctantly agreed, "Ok, if that's what you want. What time?"

"How about 9. I'll text you later with address." Steve said his goodbye and then was gone. I sat there soaking in the tub in the tub and sipping my wine. What had I gotten myself into, a week ago, I was just a curious crossdresser who wouldn't have dared to venture outside. Now here I was about to drive myself across town to a man's house to be his sex toy for the evening. Somehow that felt good, I felt proud of that.

The next day crawled by, as I was constantly watching the clock. I was able to get all my work done, and was able to scoot out of the office before 5. I stopped on the way home and filled up my car, so I wouldn't have to do it later, and then flew home.

I jumped into the shower and set to work with my razor. Shaving every nook and cranny in effort to remove any stubble, then washed my body thoroughly. I began my booty clean out process as well. After releasing my first enema, I sat to work on my face. I tried my best, yet alas I still ended up looking like a streetwalker. I attached my breastforms to my chest, then ran my second enema.

I then combed through my closet, trying to find something to wear. I finally settled on a green dress, it had wide shoulder straps that lead to a plunge neck cut with a pleated skirt, and was adorned with little polka dots. I grabbed a pair of matching green thong panties and bra. I quickly put the undergarments and applied my body lotion, before running my third enema. I was now clean down there and ready to finish my transformation. I stepped into the dress and drew it up my body. After some work I got the dress in place, and twisted myself around and was able to work up the zipper. Next came my white peep toe pumps. Lastly came my wig. Once finished I stood in front of the mirror and tugged and straightened until I was satisfied with my image.

I grabbed a bag from, and filled it with assorted lingerie, panties, stockings and my black patent pumps. I grabbed my phone to see I had a text message from Steve, "Make sure you bring your plug for tonight." I smiled and laughed to myself, "I guess he plans on filling me up again."

By that time it was 8:30, and time for me to get on the road. I looked through the blinds to make sure there weren't a lot of people out and about. It was dark now and not many were out, so I cracked the door and peered out into the breezeway. I looked both ways a couple of times, took a deep breath, and then made the break for it. I scampered to the car as quickly as I could manage in my heels. When I reached the car and closed the door behind me I finally let out my breath. I started the car and was off.

I followed the directions on my phone and made my way across town, and quickly made it to Steve's neighborhood. I hadn't ventured to this side of town before and was quite shocked at the massive sprawling houses that lined each side of the boulevard. This must be the nice side of town, check that the really nice side of town. I followed the GPS directions, and before long the voice told me to turn left, and then you have reached your destination. I picked up my phone and checked it again, "This can't be right," I thought out loud.

I was sitting in a private driveway, starring at a large wrought iron gate. Next to the window there was a keypad, and speaker. A rolled down the window and pressed the call button. There was a loud buzz, then the gates began to swing open. Guess this is the right place.

As I drove up the drive I noticed the size of the estate, the front lawn was expansive and expertly kept. The long driveway led to a large circle in front of a Spanish style villa, the front lights were on and a familiar figure stood on the veranda. I pulled up the circle and parked before shutting off the engine. Before I could manage it, Steve opened up my door and offered me his hand. I took his hand as he helped me exit. "I was worried you might have trouble finding the place," he remarked.

"No trouble, GPS took me wright to it actually. I've never been over this far. This is so beautiful out here."

He smiled and said, "Not quite as beautiful as you look tonight."

"Oh stop," I blushed as I retrieved my bag from the car.

Steve took my hand again and led me into his home. He opened the massive front door into a large front room, with high ceilings, travertine floor and bright plaster walls. On the far side of the room there was a large set of glass doors that looked out over a pool and garden.

"What do you think," Steve questioned as we walked.

"I'm thinking this is the nicest house I've ever been in," I laughed. "What do you do for a living again."

We talked as he guided me around his home, and he showed me no less than 10 different bedrooms. As it turns out Steve had become quite successful in the construction industry after his divorce and due to lucky investments he had turned that success into a large fortune. He only continued to work because he enjoyed it. "Must be nice," I commented.

As we walked the expansive halls, he turned to me and asked, "Enough of the tour, How about some dinner?"

"Sounds great," I replied.

Steve led me to a small formal dining room, with a small table set for three. I looked at Steve and nervously questioned, "Are we expecting someone else?"

"Well that's the surprise you see. My girlfriend Laura will be joining us in a minute."

I protested, "But I thought, I mean I'm not ready, I mean what if she knows, she could out me."

"Easy there darling, everything is going to be fine," Steve comforted. "Me and Laura have an open relationship, we are swingers. You do know what swingers are?"

"Yes," I nodded in acknowledgement.

"Well see Laura really wanted to meet you, after I talked so glowingly about you. She allows me to indulge in my sexual desire for sissy girls such as yourself, but occasionally likes to join in on the fun if everyone agrees."

I once again nodded in agreement.

"Listen after dinner, you make the call on whether or not you would like to stay and go further. No hard feelings either way, Ok."

I nodded Ok, and we began dinner. I was quite, and a little nervous but the flowing wine helped to relax me. Eventually the door opened, and in stepped a gorgeous middle aged women. Laura was about my size 5'6" or so 130lbs with long muscular legs. Her red hair framed her face perfectly and draped down onto her shoulders. She wore a gold sling dress, which hugged her figure. Like Steve she was in impeccable shape and her curvy figure was highlighted by her large DD breasts and firm hips and ass. She glided into the room, "This must be Jacki the gurl Stevey can't quit babbling about."

"Yes ma'am," I answered coyly as I extended my hand.

"Oh call me Laura," she insisted. "Stand up so I can have a better look," as she helped me to my feet. I stood deathly still as Laura walked around and examined me. She must have sensed my angst and touched me on the arm and said, "Relax darling, you are just trembling."

She turned to Steve and remarked, "I must say not bad, and like you told me with a little work she could be a stunner."

Laura then returned her attention to me, "Other than the makeup, the manly shoulders, atom's apple, and god awful wig, she could pass."

I thought to myself, "But I like my wig," as I twirled my fake blonde locks.

We resumed dinner and continued the small talk. I began to loosen up as the wine erased my cautiousness. After we were finished dinner Steve collected the plates and turned to Laura, "Why don't you propose our idea to Jacki?"

"Ok dear," she smile back at him.

"What idea," I questioned.

"Well we have a proposal for you," Laura added as she looked deep into my eyes. "Steve and I are in an open relationship, do you know what that means?"

"Yeah he explained it some, you guys can sleep around a bit."

"A bit might be an understatement dear," she laughed. "We lead a pretty active swinger lifestyle, we sleep around and do as we please basically. However Steve also likes playing around with sissy girls from time to time. I'm fine with his fetish, but I don't like the secretive and unsafe nature of some of his rendezvous. When he told me about you and your potential, we began to discuss the possibility of you becoming our sissy."

I interrupted, "What do you mean potential."

"Well sweetie, I must commend you on the work you've done by yourself. But to be honest you just look like a man dressing like a woman. Your makeup is all wrong and your figure although well disguised gives you away. But don't worry those are things that we can work on should you choose to."

"Oh ok I see what you mean, I definitely could use some help and assistance in some areas, also what did you imply by our sissy," in enquired.

Laura smiled and said, "Well we, Steve and I, were wondering if you would consider moving in here with us. We have a pool house that you could stay in, rent free and I could help further your feminization. Steve would pay for everything, you wouldn't be out anything but your time. During the day I will coach you, and at night or special occasions you will share our bed. The only stipulation would be that you would live as a woman or stay in dress the entirety of your stay with us, and you will take no other lovers, male or female, without clearing it with us. How does that sound."

"What about my job, and stuff, I can't be expected to be in dress in front of my co-workers," I questioned.

"We had already considered that. If I'm correct, you told Steve you worked as an accountant, am I correct?"

"Yes that's right," I replied

Laura looked pleased and said, "Well I run a small personal training business here, just a couple of clients really, and Steve could always use an extra hand keeping up with things. You could work from here essentially. We would set up a savings account in your name and deposit your salary into that. As I said before you wouldn't need to touch that account during your time here, as Steve would pay for everything else."

I pondered over the situation in as I sipped my glass. I then asked Laura, "That's a very tempting offer, but I have another question. It's fairly obvious what Steve would get from this arrangement but why would you agree to it."

"I thought you'd never ask honey," she joked. "Well, I guess I would start with that I have a dominant side that I've kept pent up over the years. Steve, has a dominant personality, and two doms in the classroom don't exactly mix. So inside of the bedroom, you would be my outlet for that energy. Outside of the bedroom, I could really use a girlfriend to go get my nails done, layout by the pool with, go shopping with. It's been difficult for me to make friends because A, women of my age are either jealous of my body, or aren't excepting of my lifestyle; and B, younger women just try and undermine me with Steve so they can get at his money."

"Have you ever done anything like this before," I questioned.

Laura answered, "No not with a sissy, we tried with a younger woman but it ended in flames. That's when a swinger couple we know suggested training a sissy. Karen, our friend, has been sending me things about how they recruited and trained theirs. It peaked my interest, so Steve and I decided to try it."

"I see," I added as I pondered the information I had been presented with. "It's a lot to take in, I have to say that your offer does intrigue me but I'm unsure if it's for me."

"Oh darling, No, we didn't expect you to make the decision tonight. This is a big decision for you, take your time and when you're ready let us know. No hard feelings either way, yes or no, Ok."

I sighed a breath of relief and nodded Ok.

"Enough of this talk, let's have some fun, why don't we," Laura insisted as she stood up grabbing her wine glass.

"Yes lets," I agreed grabbing my glass and joining her.

We clanked our glasses and downed them. Laura grabbed my overnight bag and my hand in the other and said to me, "Let's take this party elsewhere."

She led me down a long darkened hallway, as the click clack of our heels echoed off the tile. Eventually we came to two large wooden doors. Laura opened the doors, and turned to me and laughed, "And this is where the magic happens."

We stepped into a softly lit bedroom, with a giant 4 post bed that dominated the center of the room. It was the largest bed I'd ever seen, easily able to accommodate 10 people. Laura led me to the side and into the entrance to their dual walk in closets. On the either side of the corridor that separated the closet there was a sitting area with a mirror. Further down the corridor it opened up into a luxurious master bath. Laura tapped me on the ass with a firm hand and said, "Take a seat and let's get started." She motioned to one of the stools in front of the vanity's I sat down as commanded and Laura drug her stool close to mine.

"Now off with this dirty wig off, and see what I have to work with," she remarked as she removed my blonde wig and let it fall to the floor. I kept my hair usually cut close, but I had missed a couple of haircuts and my brunette hair was longer than usual. Laura ran her fingers through it saying, "Yes, yes this will look quite cute when I'm done with it."

Laura handed me a wet washcloth and instructed me to scrub my makeup off, while she gathered some things. I found out later that before she had met Steve, Laura was a hairdresser and cosmetologist. So I was in good hands. When she returned with scissors and blow dryers and all types of hair product. She then set herself to cutting, clipping and shaping my hair into a more feminine style. Afterward she began applying makeup to my face, she brushed and blended until she was satisfied with the final look. She spun me around on my stool and said, "Now that's more like. How do you like it?"

jacki697
jacki697
356 Followers
12