Jerry becomes Jill Pt. 05: July 4th

Jerry becomes Jill: Part 5: July 4th Week End

This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki.

The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done with classes about noon and I will be done at 1:00. When you get home get a shower and make sure your body is clean and hairless. When I get home I will give you your outfit for the evening. We have appointments at the beauty parlor at 3:30 and will be going to a party after that. Saturday we have an appointment with Dr. Brown and then a quite weekend at home."

I reply, "That sounds good, Mistress."

I get home shortly after noon on Friday and jump in the shower making sure I have no hair below my neck and I am squeaky clean. I finish drying just as Mistress arrives home from her class. "Jill where are you?"

"In my bedroom, Mistress," I reply.

"I'll be right in with your clothes and a surprise." Mistress announces.

A few minutes later she arrives with a stack of clothes and bag and after putting everything down she sits on the edge of my bed. "Jill," she says, "all the clothes you will need are in that pile except your pink high heeled sandals. But before you dress, let me take your cage off so you can wash you clit and cage. Use what is in the bag to douche that pussy ass of yours and I will be back to lock you up after I get changed. No playing with your clitty while you are free!" I walk over to Mistress who unlocks my chastity device, removes it and hands it to me to wash and dry. She then stands up and leaves to go change for the party.

I grab the bag and the chastity device and head to the bathroom. After washing my clitty and the device I look in the bag and see a four pack of Summer's Eve Fresh Scent douches. On the top of the box is a note to use two, hold for 5 minutes then repeat the process with the other two. I proceed to douche my pussy ass and enjoy the feeling of the douche running into my ass.

After I have finished I go out into my bedroom and start to get dressed. There is a pair of white thin knee socks and bright pink lacy anklets that I put on first. Then there is a pink plaid very shirt wrap skirt with a Velcro closure. The outfit is topped off with a sheer tie bottom blouse and the pink sandals. After I am dressed I realize there were no panties with the outfit and my ass and clitty peak out as I move. While I am trying to deal with this Mistress walks back into my bedroom and my jaw drops.

Mistress appears to be dressed identically to me except her dress is red plaid instead of pink and it is obvious she does not have any panties on either. She says, "Come here and let me get you locked up. Don't look so surprised. I may be dominating in our relationship, but in certain cases I can be submissive to other females as you will see tonight at the party. Now that you are locked up we need to get going to the beauty shop to get our hair, nails and make up done."

After spraying me with some perfume we walk out the door and head for the car. Fortunately most neighbors are either still in class or gone for the holiday weekend. Even with that we walk by a couple of female student who give us a disapproving look, at which Mistress raises the fronts of our skirts to flash the two shocked and blushing women. We both laughing as we are getting in the car.

Mistress drives to a beauty shop, where we park and go into the shop. It is a large shop with about eight attendants and a hostess. I notice there are several women in various stages of getting their hair or nails done. There is also another, what I assume, couple dressed similar to us, with the only difference being there skirts are pale and dark green plaids. As I am looking around I over hear Mistress say to the hostess, "Yes we are part of Ms. Liza's party and you should have instructions for us, I am Rikki and my partner is Jill."

A few minutes later the hostess takes us to our attendants, mine is Janis and I am lead to a chair. She starts in by removing my shoes and socks and giving me a pedicure and painting my nails a bright pink. While she is doing this she notices my encased cock and exposed testicles. She reaches up under my skirt as time permits and uses her nails to tease my balls. I notice that Rikki's attendant is occasionally reaching up under her dress.

After finishing my toe nails she moves on to my nails to which she adds extensions and paints them the same pink. She then does my hair in a school girl style and my make up as stylish hooker. As a finishing touch she opens my blouse and uses some make-up to darken my nipples and areoles so they stand out through the sheer blouse. After slipping my socks and shoes back on I get up and look at Mistress and she looks like my twin, right down to her nipples. I look at the couple in green who is just finishing as well and they are similarly made up and there is a couple in yellow dresses who is about half finished.

Mistress and l leave and she drives us over to "Bitches Grill" where we have dinner. It is relatively uneventful, except that a couple of the dykes in the bar try to pick us up, but Mistress puts them off rather easily.

After dinner we order dessert and while we are waiting for it to get to the table Mistress opens her purse and pulls out two nearly identical butt plugs along with a tube of lube. One has a hose and a hand inflator attached and the other doesn't. Mistress lubes the plug with the inflator attached and stands up and carefully inserts it into her anus. She hands me the pump bulb and says, "Pump me up." I start squeezing the bulb and can tell from the look on Mistress' face the plug is inflating and getting uncomfortable.

After about a dozen pumps Mistress tells me to stop, unscrew the hose from the plug and give it to her. The plug has a valve similar to a tire and holds the air in the plug. Mistress attaches the hose to the other plug and lubes it before telling me, "Jill stand up and bend over." I do this and Mistress raises my skirt and slowly inserts the plug in my anus and pumps it up before detaching the hose.

I stand up and it feels like I need to go to the bathroom and I am stretched to near exploding. Several of the customers have been watching and notice that when our desserts arrive I set down gingerly. While we are having desserts this tall voluptuous blonde walks over to use and speaks to Mistress.

We learn her name is Trisha and she expresses an interest in getting to know us better. Mistress explains that we are on a tight schedule but would be interested. Trisha reaches in her purse and gives Mistress a card and says, "Call me when you have time."

Mistress replies, "I will be sure to do that."

After we finish dessert we return to the car and Mistress drives us about ten minutes out of town to this beautiful large mansion. I am just getting used to sitting down with the plug in my pussy-ass as Mistress pulls the car to a stop and gets out. I get out of the car and follow her to the front door of the mansion where Mistress rings the doorbell.

After waiting a few minutes the door is opened by a beautiful tall maid in an extremely sexy maids outfit. She is wearing five inch black spiked heels and sheer seemed black stockings the top of which are peeking out below her short dress. The dress is held out by a lacy ruffled petti-slip. The black dress has a sheer top through which the maid pierced breasts are clearly visible. Over the dress she has a small lacy apron. Her face and hair are done like a $1,500 an hour escort. I can't stop staring at the beautiful vision before me.

The maid then says, "Good evening ladies, please follow me."

We follow her into the parlor where we see the other two couples from the beauty shop already there kneeling on the floor. The maid points to two small mats on the floor and says, "Please kneel on the mats the same as the other guests, with the women on the left."

We go to our mats and kneel with our knees wide spread and our hand on our knees with the palms up. Our heads are bowed with our eyes on the floor. As short time later the maid returns with a tray of drinks. She says, "Sissies take a pink glass and drink the contents, Sluts take a yellow glass and do the same. The maid waits until we finish and collects the empty glasses before she leaves.

We return the waiting position and as we wait my sexual desire starts to increase, I wonder what was in the drink. There is an itching in my crotch and my clit is trying to get hard. My hips are thrusting trying to get some relief. I steal a glance at the others and they all seem to be dealing with the same horniness. We wait in the position for some time before a door to our right opens.

In walk two ladies followed by the maid. The first of the ladies says, "Sissies and sluts you can look up now."

I look up and recognize Ms. Liza, from her boutique, Dr. Brown and the maid, although the maid has changed and is dressed much like I am only in lavender. Ms. Liza and Dr. Brown are dressed similarly with knee high spiked heeled boots, black stockings, sheer open bottom gartered teddy. Both of their hairy pussies are on display and their erect nipple show through the teddy.

Ms. Liza and Dr. Brown seat themselves side by side on a sofa in front of us and Ms. Liza starts to speak, "Good evening sluts and sissies. You are all new to one of our little parties, but I think you will enjoy yourselves. You all know Dr. Brown and myself, I am a Dominatrix and Dr. Brown is my partner. She is submissive to me but dominate to the rest of you. The maid here is my sissy husband, Gracie, who will be joining in the fun. By the way the drink you had contained sexual stimulants that will make you all extremely horny for the next several hours.

Now if you will all stand up and put the mats over there next to the wall. Now you sissies line up there in front of us while the sluts sit on the floor in front of Dr. Brown and me." We all move to get the mats put up and my fellow sissies and I line up in front of or two Mistresses. As we stand there I notice that we all are struggling to keep our pelvis still.

Ms. Liza says, "I think it is time for some entertainment. Sissies count off, one through four, Gracie is number 1, I am number 2 and so on. Now I am going to put some music on and I want you to start dancing together, 1 with 2 and 3 with 4. These will be slow dances so make it interesting."

The music starts and Gracie takes me in her arms and we start dancing. We both try to get some relief rubbing out caged clits against the others. Gracie turns my face to hers and kisses me slowly at first and then inserting he tongue into my mouth. The kissing gets us turned on more and our humping becomes more exaggerated.

This continues until the second song ends when Ms. Liza says, "OK sissies, switch partners, but before you do remove your blouses." With our blouses off, we all are looking at each other's breasts and comparing. It is obvious that Gracie has the best breasts at a C/D cup with large pierced nipples. The other two sissies' breasts are nice B/C cups while mine are the smallest at an A/B cup. The music starts again and we begin dancing with or new partner.

We are dancing with one hand playing with our partner's ass, rubbing our breast together; French kissing like mad and thrusting our chastised cocks against our partners trying to get some release. We looked like and were a horny group of sissies. As a second song ends it is a good thing that our clits were locked away or we would have been on the floor fucking one another. A quick glance at the women showed that we were having an effect on women as their pussies are all exposed and they are lightly rubbing them. Each of their pussies appear to be wet, some more than other.

Ms. Liza says, "My, what a horny group of little sissy sluts you are. Take off your skirts and pair up with the partner you have not danced with." With that the music starts again and we start dancing although now we are basically nude with only our heels and socks on. We are kissing, sucking on breasts, rubbing each other's asses and playing with our partner's chastity. Each of us is painfully erect inside our chastity devices.

As the music for the second song of the set starts, I glance at the women and it is quite a scene as well. Rikki is naked from except for her shoes and stocking and is on her knees in front of Dr. Brown with her head buried in Dr. Brown's pussy. As the music stops all the women turn and look at the four of us sissies standing there madly thrusting our clits into the air, in frustration.

The women smile and tease us about our frustration, before Ms. Liza says, "Sissies, go stand in front of your Mistress. Mistress you are to remove their chastity device. Sissies you are not to touch your clits or you will be severely punished." Once the chastity devices are removed we line up facing the ladies each of supporting an erect cock none of which are very large, in fact all added together barely make one decent cock.

Ms. Liza then says, "Gracie, which of the sissies do you like the best?" In response Gracie points towards me and says, "I think Jill is sexy," which makes me blush. Ms. Liza then added, "You pair up with her while you other two pair up. We are going to have a contest. Each pair is to get into a 69 and you are to try to make your partner cum. The sissy cums first will be punished the one who comes last will win a prize. Additionally any sissy who comes in less than 8 minutes will be punished. While you are doing that we girls are going to get ready for the reward and punishment"

With that Gracie and I get in a 69 position on our sides and wait for the start signal. As we wait I can feel Gracie's breath teasing my cock and it is all I can do to keep from thrusting forward trying to get relief. Finally Ms. Liza says, "Start sucking you horny sissy sluts." I take my first cock into my mouth and start licking and sucking it as I know I would want to be treated. Gracie takes mine in her mouth and starts teasing.

We all make it past the eight minute mark, but one of the other pair comes shortly after that. About two minutes later I cum followed in quick order by the second girl in the other pair with Gracie coming last. We all stand up facing the women, still support erect clits, while the women who are each rubbing their pussy.

Ms. Liza says, "Thank you sissies for the entertainment. Diane you lost so let's get you set up for your punishment. Gracie you were the winner so which of the ladies would you like to service?"

Gracie replies, "Ms. Rikki if you please."

"Good," replies Ms. Lisa adding, "I will take Jill to service me, Jane (the other sissy) you will service Dr. Brown and finally Judy, (who was Diane's dominate partner) you will service Tina the other dominate, but not get any relief yourself."

With that being said Ms. Lisa takes Diane over to a box that has clear plastic in the bottom and three sides. The fourth side is wood, and looks like the head grab portion of an old stock. The opening on the side of the box is padded and covered with rubber. The top of the box has a toilet seat attached to it with a clear funnel like toilet bowl. The top is split so the funnel can be slid in from the front. On one side of the box is a push button marked "FLUSH" and at the lower front corners are eye-bolts.

Ms. Liza walks up to Diane and inserts some soft putty in her nostrils forcing her to breathe through her mouth. She then removes the funnel bowl from the box and secures the discharge end of the bowl in Diane's mouth, sealing it so that she must take air in through the funnel. After attaching cuffs to Diane's wrist, Ms. Liza has her lie down and secures Diane in the box, clipping the wrist cuffs to the eye bolts. She also clips the wires from the flush button to Diane's testicles.

Ms. Liza then announces that, "The play/reward time will continue until each of the women have donated their urine to Diane's punishment. Diane are you listening? When a woman sits down on the toilet you are to plug the funnel with your tongue until the flush button is pushed, then you can open and swallow their gift to you. Judy, you have to be the first to use the punishment toilet. Let's have some fun."

With that those of us assigned to pleasure the Dominate women move between their legs and start to pleasure them. After about ten minutes Judy stops and walks over to the toilet, lifts the lid and sits down. We can see through the clear sides and funnel as she release her pee the funnel fills. When she finishes she reaches down and press the flush button. This release an electrical current to the wires attached to Diane's testicles giving her a strong shock. She opens her mouth to scream but it is cut off by the flow of pee running into her mouth.

The playtime continues for nearly two hours before the last woman pees on Diane. My neck was stiff and tongue sore for the five orgasms I had given Ms. Liza during that time. My face was drenched with pussy juices. We stop and put our skirts and blouses back on and thank our hosts for a wonderful evening. As we are leaving Ms. Rikki turns to Sarah and says, "We will see you at 11:00 in the morning."

When we arrive back at the apartment building about 1:00 AM and hurry into the apartment since we both have dried or drying cunt juice all over our faces. When we get in the apartment without any incidents Rikki says come shower with me and let's get to bed. After washing each other in the shower, Mistress invites me to join her in bed, which I gladly do.

Once we are in bed Mistress turns to me and says, "After tomorrow you will have to wait a week or two for you to get any relief. Would you like me to get you off one more time to night?"

I reply, "Yes, Mistress, but why?"

"Turn over and enjoy this. I will explain more in the morning. Set the alarm for 8:00," replies Rikki.

After setting the alarm I roll on my back and relax as Mistress takes my cock in her mouth and gets me hard. I am expecting her to finish with her mouth or hand, but instead she climbs up and me and slowly slide my hard cock into her wet hot pussy. After riding me to a powerful orgasm she climbs off and swings into a 69 position so we can clean each other before falling asleep.

The alarm goes off and we are both out of bed and headed for a shower. As I am leaving Mistress says, "Jill all you need to wear are socks, loose panties, sweat pants and sweat shirt."

After our showers and getting dressed while we are eating breakfast Ms. Rikki explains, "Besides the normal check-up we are visiting Dr. Brown today to have your body pierced in several places. None of it will permanent, but it is what Dr. Brown and I think is appropriate for a sissy such as you are becoming. I hope you will approve of the results."

"Thank you Mistress, I am sure it will be perfect," I reply.

Shortly before 11:00 we leave for Dr. Brown's office. As we pull up I notice that the sign says closed but there are two cars out front. We park and walk up to the front door and knock. A few minutes later Dr. Brown opens the door and leads us to a treatment room where there is another person waiting. Dr. Brown introduces the other female as Dr. Lamb an anesthesiologist. Dr. Brown then ads, "Jill Dr. Lamb is also involved in a female lead relationship and is going to put you to sleep so the piercings can be done. But first I need to get some blood samples and measurements, so get undressed so we can get started."

Once the measurements and samples are taken Dr. Brown says, "Jill, get up on the table. Rikki, if you are going to help you need to get a gown, cap, gloves and a mask on."