Jacki's Journey into Sissyhood Pt. 04

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Jacki makes new friends as they get ready for a party.
6k words
4.62
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Part 4 of the 5 part series

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

The next couple of months with Steve and Laura were incredible, and the happiest of my life. I felt like I had found my place with people who genuinely loved me. I spent my days sharing their life and nights sharing their bed.

Under Laura's tutelage, my metamorphosis continued. I was on a strict diet and exercise routine that helped me drop my weight and shape my feminine figure. Laura was pleased with my progress, as I was able to drop 20 lbs. We were now exactly the same size. My daily routine of squats and lunges, had fattened my ass and widened my hips much to Steve's delight.

As the warmer months came, Laura and I would lay out by the pool and work on our tans after workouts, and we continued shopping and pampering ourselves to our hearts desire. My hair began to lengthen and due to mine and Steve's pestering, Laura died my hair a light blonde. She resented but after time, agreed I looked better as a blonde.

Laura and I became closer as the days past and 6 months in we were nearly inseparable. I came to know her better than I had known anyone, she became family. I learned that she had a son from her previous marriage, who was in the military, and she hadn't seen in over a year. I learned that she was known as a queen of spades in swinger lingo, and only fucked black men at parties. Steve was the only white man she had sex with.

My feminization then went stagnant, I was unable to diet and exercise away the rest of my manly frame. Laura tried every trick that she knew, but to no avail. So she contacted the other swinger mistress she knew for advice. The answer was simple, estrogen supplements.

Laura gathered all the information she could and presented me with the options. "If we you wish to go further, this is the only course I'm afraid," she summarized.

"This is a big decision, there is no turning back after this is it," I sighed

"I'm afraid so Jacki," Laura said.

My friend's advice to me about my indecision to move in with Steve and Laura popped into my head at that moment, "you were never much of a guy,..., you might make a pretty good woman."

I contemplated my response, and then smiled at Laura, "we've already come this far let's do it."

Laura exploded into excitement, and we embraced one another.

The next day I began supplements and injections. The first month was difficult, my moods, weight, and sex drive fluctuated wildly. I wouldn't eat for days, and then I stayed hungry constantly. My body ached all over, even my hair hurt. My nipples became extremely sensitive and my caged cock became numb.

By the beginning of August my body began to adjust. My weight and mood normalized as did my sex drive. The transformation of my body was the amazing part. The hair growth on my head accelerated while my body hair growth slowed dramatically. The manly muscular shoulders, arms, and chest melted away. My hips widened and my ass got fatter. To my delight, my nipple puffed out as I formed small breasts that filled my bra cups. Steve really enjoyed the budding tits to play with, and I adored how they shook and bounced as he fucked me. The estrogen supplements also relaxed my voice, to a feminine tone, and softened my facial features. I truly began to look like a mid 20's woman.

I now got no more long inquisitive looks from women while I was out with Laura. They now only viewed my as another woman. I also began drawing attention from men of all ages, who I would catch eyeing me everywhere I went. Being the flirt that I am, I would tease them, by flashing them a view at my panties when I uncrossed my legs or bent over. Laura would just roll her eyes, saying," you're insatiable," and laugh.

The supplements shrunk my clitty down to the point that the cage no longer fit. Laura resorted to just tying it up with a cute bow, as it no longer would get hard. Most of the sensitivity of my clit and been totally drained except for the small cock head that stimulated me when it was rubbed. My orgasms had changed as well, they were even more intense than they had been before, and lasted much longer. My tiny cock no longer spurted cum during climax, but instead only dribbled clear liquid.

By late September, all traces of the male I had been, were erased. I now appeared to be a real woman, with only my little nub to remind me I wasn't.

The first day of October came, and while we were working out Laura stopped me. "I have a question to ask you, Jacki."

"Sure, what is it," I answered.

"Steve and I have been considering, when might be a good time to introduce you to the lifestyle."

"What do you mean the lifestyle," I interjected.

Laura responded, "The swinging lifestyle, the club we belong to,.., you know." She continued, "Anyway, I didn't want to bring you in till I felt you were ready. Now physically you are ready, you look stunning and I'm sure the women and men alike would love you, and you would be quite the hit at our parties. But I wondered whether YOU were ready."

I thought for a minute about my response as I finished my set, "Two months ago I would have said no. But I've been becoming more interested in what you guys do on those nights. And I love you two, but I've been wanting to kind of, well you know, experiment a little."

Laura smiled and laughed and then wrapped me in a sweaty hug before kissing me, "I thought you might say that, I've noticed you flirting with boys at the mall on our shopping trips."

"I learned from the best," I retorted and returned her kiss. "I have to ask, why are you bringing it up now?"

Laura replied, "Well for the last several years Steve and I have hosted the club's Halloween party. Steve thought it might be a good coming out party for you."

I squealed, "I love Halloween parties, I mean this would be my first as a girl, but heck it has to be even more fun as a girl."

Laura laid out the agenda, "well in order for you to be able to attend the party, we need to get you approved by a 3 members, and get your medical check-up."

"Well what are we waiting for," I said, giving Laura a wink.

The next couple of weeks, Steve and Laura took me to dinner with 3 other couples they knew. I met each of them and we talked and chatted. They asked me questions about myself, and what I liked to do and so on. There was never and hanky panky, well except what happened with Laura and Steve afterwards, just dinner and drinks.

The week before the party, at dinner shared the good news. "The McConnely's, Stewarts, and Conners all said yes, Jacki's on the list."

We all cheered and toasted the good news. Laura chimed in, "I'll call Tara, and get her an appointment for tomorrow so she is locked in."

The next day, was a normal morning. Laura and I woke up and did a quick yoga session, before going for a run. We made it back to the house, and Laura told me, "Go get some clothes together, probably a cute top and skirt, and come take a shower with me. I'll do your hair and makeup and we can head to the doctor's office."

I did as I was told picking out a cream colored mini skirt, a sleeveless pink top and my pink peep toe platforms. For underwear I picked out a white lace pushup bra and thong. I then joined Laura in the shower and we washed each other.

I played with Laura's nipple studs as we cleaned ourselves, "Laura, I think I'd like to have mine pierced as well."

Laura looked back at me in astonishment, "Well I guess we could do that after your doctor's visit today," as she fondled my breasts sizing them up.

I smiled back at her, "yes lets."

We exited the shower and got ourselves dressed and headed downtown to the doctor's office.

Laura and I arrived early to the office. We were greeted by a cute young blonde receptionist, named Courtney. She was quite bubbly and commented on how much she liked my hair and how cute my outfit was. I thanked her and she told us that Dr. Conner would be with us in a moment.

The door to the office and Dr. Conner stepped through the door and called out, "Jacki." I immediately recognized Dr. Conner as part of one of the couples we had dinner with. Dr. Conner was in her mid-30's, a brunette with shoulder length hair, and a short woman in stature; no taller than about 5'2" or 3". I remembered from our dinner that while she wasn't blessed with a large chest, she more than made up for it in ass.

"High Laura, it's so good to see you again," she said as the two women embraced one another. "And nice to see you again Jacki, I was hoping I might see you again. When Laura called me last night I got all excited."

We embraced and I said, "It's wonderful to see you again to Tara."

Tara led us to an empty exam room and began the usual checkup procedures. Once they were completed she had me stand and turn for her. "I must say Laura when you told me your plan, I didn't think you could pull it off. But she looks as much like a girl as Courtney does."

Laura commented, "Yes she has been a breath of fresh air."

Tara then turned to me, "Jacki, take off your top and skirt and sit on the examination table please."

I complied and stripped down to my underwear. I sat down on the table and Tara extended two foot stirrups. "Just rest your feet here sweety."

I put my feet into the stirrups so Tara could examine me. She removed my thong and handed it to Laura leaving my clit and ass exposed. Tara played with my shriveled cock, "Does it get hard anymore," she asked.

"No not since I started the supplements," I answered.

She then took a long cotton swab, and inserted it into my ass, swabbing my anus. She placed the swab in a bag and sealed it.

Tara looked me in the eyes and patted me on the thigh, "And that's that, you can get dressed sweety."

I dismounted the table and began to redress, as Tara and Laura talked.

"So are you and Steve ready for next Saturday," Tara asked.

Laura responded, "We are getting there, we will really start prep this week."

"It must be nice for you having Jacki this year, to help," Tara added.

"Oh it will be, I know she is excited for her first party," Laura replied.

"It won't be her last I'm sure," Tara giggled. "So I took off for next Friday, and I was going to take Courtney to the salon, for mani pedis and a wax before Saturday. Why don't you and Jacki come along and we can have a girl's day."

Laura answered, "That sounds like fun, and we're there."

I finished dressing and we exited the room. "I'll get these to the lab ASAP, and I'll email you the finalized list this afternoon, see you girls Friday."

"Sounds great girl," Laura chimed.

After the doctor's visit we made our way to the tattoo parlor, where the same pink haired girl, named Roxy, waved us back. "What will it be today, ladies?"

"I need to get these done today," I said pointed to my tits.

"Not a problem," the girl said, "what do you think Laura, bars like yours or rings?"

Laura replied, "I think bars would be best."

I took off my shirt and bra and handed them to Laura, before sitting down in the chair and leaning back. Roxy returned with a bowl of ice and snapped on her latex gloves. "Now, I have to use the ice to get them hard and numb them up."

I nodded ok and we proceeded. Once Roxy was satisfied that my nipples were sufficiently numb and erect, she picked up the needle and looked at me and said, "Here we go."

In a quick motion she drove the needle through my nipple. Pain shot through my body and it caused me to bite into my pink glossed lip in order to keep from yelling out. The other nipple wasn't any easier but in short order my nipples bore stainless steel studs just like Laura's. Roxy placed two gauze pads over my throbbing nipples, and instructed, "Change these out before you go to bed, a little bleeding is normal. You can use ice to help with the swelling and pain. Keep them clean and wash them with this antiseptic wash. Oh, and Laura tell Steve not to tug on these for a couple of days, like yours."

Laura laughed, "I'll have to tie him down."

Roxy handed me a stack of gauze pads and a small bottle of antiseptic wash. I didn't think I could stand putting on the bra, so I just slipped the shirt over my head. We left the shop and headed home for the day.

I got home and immediately took off my shirt, and I spent the rest of the afternoon with ice on my pierced teats, trying to subside the pain. I did get to show them off to Steve when he got home, and no surprise he loved them. Thankfully the pain had mostly gone by the next day, and was completely normal by Sunday afternoon. Now every moment stimulated me sexually, any brush against my nipples just got me hornier. No wonder why Laura was always randy.

The next week was quite busy for Laura and me as we made plans for the weekend's festivities. It was unseasonably warm for October with temps rising well into the 80's. Laura and I even broke out our bathing suits, to work in.

Laura had studied the guest list and there were over 100 confirmed couples and almost as many singles. Steve had some of his worker's help us with unloading trucks and helping us with decorations. There was plenty to keep us busy, not to mention we still needed costumes.

Before we knew it, it was already Friday. Due to proper planning and a lot of hard work we had the majority of the prep work done. Today us girls would relax and meet up with Tara and Courtney for some pampering.

Laura and I woke up, and decided to get a work out in. It was some dang hot that we cut our run short and walked back to the house. "Im so sweaty, I'm sticky," I said as I rang out my top.

"Hey why don't we shower off and lay by the pool," Laura proposed.

"Oh that sounds fantastic," I replied. "Hey, why don't you call Tara and invite them to lay out with us."

"That's a great idea," Laura remarked.

"I'll go jump in the shower first, come join me when you're done," I said as I peeled off my workout clothes.

I let the cool water run across my body as I waited for Laura join me. I was running my fingers through my hair when I felt her nipple rings on my back. Laura's hands reached around my body and tweaked my nipple studs, causing me to moan, "Don't get me going if we don't have time to finish."

She laughed, "unfortunately your right, Tara and Courtney are on the way actually."

"Well that's great," I replied. We quickly washed off our bodies, then lit in to getting ready. Laura sat out a shiny gold bikini with tie sides for me and her leopard print pumps. I slipped everything on and began brushing my hair. She appeared in the mirror, wearing her zebra print bikini with the push up top, and her black wedges. She watched me brush out and start to dry my chin length hair, "why don't we try something different with your hair for tomorrow night."

"What did you have in mind," I asked.

"Well your hair is long enough now for me to blend in extensions, but instead of blonde, why don't we make you a redhead like me," she suggested.

I pondered the offer, and wondered how I'd look like as a redhead. "I actually kind of like the idea we will look like sisters that way."

"More like mother and daughter," she laughed.

"A very kinky mother and daughter at that," I added.

We finished getting ready, and Tara and Courtney arrived. We poured some wine and prepared to catch some rays.

We talked and laughed about girl stuff mostly. Courtney and I really hit it off, as our personalities seemed to mess well. As it turned out, she was in a similar situation to me. She was a sugar baby for both Tara and her husband Greg. She had been living with them for 2 years, since they had introduced her to swinging. She had been working her way through college as a bartender when Tara had hit on her and talked her into coming home with her. Saturday would mark her 4th party with the couple. She said she would help me out at the party, so I didn't get overwhelmed.

"Well aren't you two just hitting it off," Tara laughed.

"Best friends forever," Courtney smirked. Courtney and I then locked our pinkies together.

That in sighted laughter from Laura and Tara.

Tara then spoke to me, "Jacki, why don't you show me to the pool house bathroom babe,"

"Sure thing," I answered. We both stood and Tara and followed me into the pool house.

I led here into my bedroom and then pointed her towards the bathroom. The next event caught me totally by surprise. Tara walked right up to me and kissed me firmly on the mouth, pushing her tongue into my throat. I recoiled, "Dr. Conn,.., I mean Tara what are you doing."

"Awe, Jacki I didn't really need to use the bathroom, I just needed a reason to get you by myself," Tara moaned.

"But Courtney and Laura, I mean Laura might not want us to be doing this," I stammered.

Tara reassured me, "Oh no it was Laura that suggested I try you out girly, I think she wanted to try out Courtney as well." We then looked out my bedroom window towards the pool to see Laura and Courtney making out and rubbing each other through there bathing suits. "See they are having fun let's have some fun of our own," she asserted.

She then grabbed my head and pulled our lips back into contact. Her lips were plump and soft, and her body was softer than Laura's toned figure. We stood at my bedside with our tongues intertwined as we groped each other's body's. Tara then untied the sides of my bikini and let it fall to the floor, followed by removing my top. She fondled away at my cocklette while looking me in the eye, "I was kind of worried that we might to busy tomorrow night, and I wouldn't have a chance to play with you. You're all I could think about since your doctor's visit."

Tara then kissed me again, before turning her attention to my nipples. She licked and sucked at my buds and tugged at the metal studs with her teeth. Her simultaneous stimulation of my nipples and cock head made my eyes roll back, and my knees go week in pleasure. She sensed my ecstasy and stopped here stimulation, "get on the bed Jacki, Im going to take you for a ride."

I climbed on the bed, and caught a glance of outside. Courtney and Laura were now completely naked; Laura's face was buried in-between Courtney's legs, tonguing her pussy.

I laid on the bed watching the love scene unfold, as a now naked Tara joined me on my bed. She carried her black tote and emptied its contents onto the bed. Among the suntan lotion and lipstick, there was a strap on harness, with a small clear glass dildo attached. It was only about 6 inches long, but the head bore a large orb that was wider than the shaft. The smooth shaft was dotted with raised pink hearts. Tara strapped the device around her waist as she said, "This is Courtney's favorite, and I thought you might like it as well."

She bent down and kissed me hard biting and pulling at my lower lip with her teeth, "Now on your back baby, let me see that pretty pink hole."

I complied with her requests, and flipped to my back and invited her in. Tara moved into position and then lubed up her crystal wand, before leaning in to mate the tip of the glass rod to my orifice. The cool glass made my hole recoil in an attempt to get away. I hadn't been subject to a fucking in almost a week, and my hole had tightened so it took a minute for Tara to force herself into me. Due to her persistent pushing, my anus finally yielded to her demands, allowing the sphere of the dildo tip to pop home.

The suddenness of the of my opening cause pain to shoot through my body, "Oh Shit," I cried. My cries of pain caused Tara to bury the rod into my body, and laugh, "Damn that little hole is tight."

I tried to smile back at her, as my pain waned. Thankfully the coolness of the glass not only caused a powerful stimulation to my p-spot, but also soothed my pulsating asshole. I bucked my body in acknowledgment that I was ready. And Tara began slowly fucking me.

jacki697
jacki697
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