Jerry becomes Jill Pt. 03: It Gets Serious

This is the third part of my story about how I became Jill. My relation with Rikki takes a serious turn and I learn more about what life with her will be like.

Each day Rikki gives me an article about a female led relationship. The article on Monday is about a couple in their thirties who are dating. The woman makes most of the decisions when they are in public and all of them at home. By Friday the articles are much more intense and involved and are starting to involve sexual aspects of the relationship.

Saturday morning Rikki is up early and when I go into the kitchen there is an article on the table along with a note. The note says "Enjoy the article. I have gone to the library to work on a paper and will be home in the middle of the afternoon." I get my breakfast and start to read the article which is the longest one of the week.

This article tells of a married couple where the husband works from home and is dressed as a female full time. In addition to his job he does all the chores around the house, laundry, cooking, cleaning, etc. He is kept in chastity when his wife is not around. There are indications that more happens but are no details in the story. The story arouses me and I start to stroke my little cock, careful not to cum.

After the article and breakfast, I get busy cleaning and do some studying. Around 3:00 Rikki calls and say, "Jerry I will be home at 4:30. Will you run a bath for me? Make sure you are freshly showered and wearing the outfit I left for you on my bed."

"Will do," I reply as I hang up the phone. I go to the kitchen and prepare a salad and casserole for dinner and then head to take a shower. I go by Rikki's room and pick up the outfit she has left for me. Instead of the normal panties and top, she left a crotch-less lacy gartered pink teddy and a pair of pink stockings. With these in hand I head to the shower.

I get my shower and notice it is 4:15 and go run Rikki's bath. Returning to my bathroom I start shaving when I hear the door open and Rikki come in. I finish putting on the hose, and teddy and head to the kitchen to put the casserole in a low oven. After lighting some candles and putting some music on I grab two glasses and a bottle of wine and go into the living room to wait on Rikki.

I don't have to wait long before she came out of her room and she looks spectacular. She has on over the knee black high heeled boots, sheer black pantyhose and a black leather bra. The bra has holes in the cup and her erect nipples are poking through the holes. In addition the view of her beautiful pussy through the panty hose has be getting erect. Her face is made up spectacularly with hair pulled back in a ponytail.

I say, "Rikki, you look spectacular and sexy!"

She replies, "Thank you and stand up so can get a look at you, Jerry."

After I am standing Rikki says, "You look sexy as well, but there is something missing? I know what it is come in to my room with me." She picks up her glass of wine and heads for her room. When I get into the room she is holding a pair of pink high heeled slippers in her hands.

I say, "You're kidding?"

Rikki responds, "No, I think you will look sexy with these and the outfit you have on. Besides I think you have the legs for these."

Realizing her mind was set and trying to talk her out of this would be a waste of time, I agreed and slipped into the slippers. Standing up and trying to walk in the heels turned out to be an adventure. Rikki gave me some tips that helped a lot and I was getting used to walking in them when the timer for the casserole went off.

I start off on my first long walk in heels with Rikki fallowing. She watched for a few steps and gives me a wolf whistle. She picks up the wine and I get the salad and casserole on the table.

We sit down at the table and enjoy a leisurely dinner accompanied by a lot of small talk about the week and what was coming up. When we finished I told Rikki I would clean up and she could find a movie to watch.

After getting dinner cleaned up I join Rikki on the sofa with a fresh bottle of wine. Rikki turns and looks at me and says, "Before we watch the movie we need to talk a minute or two. What did you think of the articles I left for you to read?"

"I enjoyed the articles. I don't think I would have a problem with a female lead relationship. In some ways I like it as I know what to I am supposed to be doing."

"You don't know how happy it makes me to hear you say that. I have another movie I want to watch with you and then we can talk more." With that said Rikki kisses me, starts the movie and cuddles up next to me.

I don't recall the title of the movie but it is about a married couple and opens with the husband arriving home. He quickly goes into a small bedroom and removes his clothes showing he is wearing pink panties, bra, camisole, garter belt and stockings. He then puts on a pink maids outfit and adds high heeled shoes with an ankle strap which he fastens and then locks with a small padlock. Then setting at a make-up table he rapidly does his make-up and adjusts his hair in a feminine style. All done he makes a very attractive maid, except for the hair.

When his wife arrives at home he meets her at the door with a drink. When she sits down he removes her shoes and massages her feet before going and starting dinner. While the movie has been going on Rikki has been stroking my leg and teasing my cock. The rest of the movie is much of the same until it is bed time.

The wife instructs her husband to clean-up and report to her room with his sleeping attire on. The camera follows him into his room where he removes and hangs up his clothes or putting dirty ones in the hamper. I notice that he has no body hair and his cock is locked in a chastity device. After a quick shower he slips into a lacy negligee, sprays on some perfume and heads for his wife's room. When he enters her room she is dressed in a flannel granny gown for lack of a better description.

The wife orders him to remove the negligee and lay down on the bed, where she ties him spread eagle to the bed. After putting a blind fold on her husband she strips off her gown and pulls a small cart with some toys on it up to the edge of the bed and sits down. She starts to stroke his thighs and tease his balls watching him trying to get an erection in the tiny chastity cage. After a few minutes she takes the chain from around her neck that holds the key to the cage.

She carefully removes the cage without touching his cock. The wife reaches over and teases his balls some more while pouring warm oil on his cock. She then warms him not to cum until she gives him permission. She climbs on the bed and swings a leg over her husband's head.

As she settles her already wet pussy on his mouth she says, "You have 10 minutes to get me off and don't come until I tell you it is OK."

The husband starts licking and sucking on her pussy as she grinds it his face and starts stroking his cock. She works hard on making him come before she gives him permission. Doing his best he brings his wife to an earth shattering orgasm. As she subsides from this and returns to stroking his cock he explodes without permission.

After they calm down she says, "You came without permission, you know the consequences." To which he replies, "Yes, Mistress," and with that he gets up and goes to the bathroom to clean-up. When he returns he is locked back into his chastity cage. This is followed by a diaper and rubber pants. He then puts on a children's looking short frilly night shirt and climbs into bed.

When he does his wife secures his wrists to his thighs and his ankles together as the movie ends.

Rikki says lets go to bed and we can talk in the morning about the future. With that we head to bed where I bring Rikki to two orgasms orally and she relieves me orally as well. When I wake up in the morning Rikki was gone and I got up and went in the bathroom. As I stepped out of the shower there was Rikki dressed in this beautiful black lingerie outfit all made up. She says, "Good morning sleepy head. When you get dried off put the outfit I left on the bed for you and join me for breakfast."

I finish drying off and go to get dressed and find an outfit similar to Rikki's only pink and put it. Then I join Rikki at breakfast. She has scrambled eggs, waffles, bacon and orange juice waiting. As we finish eating Rikki says, "Let's talk about our future."

"Great, I want to hear what you have in mind," I reply.

"What did you think of the movie last night?" asks Rikki.

"It was interesting. It opens a whole new level in a female led relationship. I think it would be interesting to explore some of these different levels of a FLR," I replied.

"I was hoping you would respond like that and I would like us to go together see how thing go?" questions Rikki.

"Yes, Rikki, I would love to try that what do you have in mind?" I ask.

"Well first of all let's talk about school. I will finish up my masters the summer after next. If you take some extra classes and go to summer school you can have your B.A. at the same time. You are already in the business school and I would like you to get a degree where you can get your CPA and also handle investments. That way you will be able to work at home. I have enough friends that you will have a good business. What do you think?" asks Rikki.

Thinking about it for a minute and seeing that this might lead to me being a work at home female dressed male and that excites me, so I reply, "I think that will work, Rikki."

Rikki then goes on, "I have a few rules that we will start with and we can add to them as time and the need requires." She then hands me a paper with the rules on them to read.

1.I will make all decisions for us both here at home and when we are out together."

2.When we are out you will refer to me as "Mam" or "Ms Rikki." Here in the house it will be "Mistress" or Mistress Rikki."

3.You will only wear panties and camisoles under your male clothes when you leave the apartment. In the apartment you will wear panties, camisoles and high heels, unless I instruct otherwise.

4.You will keep your body free of hair below your shoulders and allow the hair on your head to grow into a unisex style.

5.You will be responsible for meals if we eat here and for cleaning and doing the laundry on Saturday morning.

6.Sleeping attire will be of my choice and feminine. We will sleep in separate rooms except when I wish otherwise, typically over the weekend.

7.You will show any of my friends the same respect you show me.

8.If we are out together, unless I take your hand, you will walk 2 to 3 paces behind and to the right of me.

9.You are to keep you toe nails painted bright pink at all times.

After I finish reading them Rikki asks, "Any questions? If not after breakfast we will through way all of your male underwear and pajamas. We will go shopping this afternoon to get you feminine replacements."

We finish breakfast and Rikki gives me a brand new pair of sexy pink lace panties and camisole to wear and we get to work on going through my clothes. As we do this Rikki also throws some of my regular clothes out as well saying, "These are too masculine for my little sissy slut, we will have to replace them with something more a little more appropriate."

After we finish the clothing chore we get dressed to go shopping. It is Sunday so stores open later and we head for Victoria's Secret to arrive just as the store opens. As we are walking in Mistress says, "I'll make the choices for us."

To which I reply, "Yes Ms Rikki."

Entering the store we are greeted by a sales women probably in her late 40s very sexily dressed who asks, "May I help you."

Rikki replies, "Yes, we are here to get some lingerie for my boyfriend. We are looking for panties size 7, small to medium camisoles, stockings, and sleep wear. They will need to be in pink, yellow, light green or light blue."

The sales lady says, "This is not a problem I will be glad to help. Let's start with the panties," she says as we move towards where the panties are located. She and Rikki pick out about twenty pairs of panties, mostly boy-short style, but also a couple of bikini style and thongs. We then move to the camisoles.

Rikki says, "Let's have a small and have him try it on." The sales lady finds a sheer yellow small one and gives it to Rikki.

Rikki turns to me, handing the camisole to me and saying, "Go put this on and when you do come out and find us so we can see the fit."

Taking the yellow camisole I reply, "Yes, Ms. Rikki" and turn and head to the fitting room. It only takes me a few minutes to slip into the yellow camisole, which fits but it is snug. After tucking it into my jeans I leave the fitting to find Rikki. Walking through the story with my secret exposed is getting me excited and my little cock is starting to get hard.

Rikki and the sales lady have moved on to the sleepwear area, nearly across the store from the fitting room. There are three other sales persons and half dozen customers in the store as I walk to Rikki and I felt all eyes were on me and my cock was getting harder.

As I approached Rikki looked up from the nighty she was looking at and smiled. The sales clerk looked and said, "The small fits although it is a little tight."

As I get to where the two are standing Rikki says, "I agree but I can't tell about the length. Jerry drop your jeans and let me have a look at the length." I start to protest and think that it is not worth it, so there in the middle of the store I unbuckle my pants and let them fall to the floor. As that happens there is no hiding my growing erection in the pink lacy panties.

The sales clerk smiles and in a loud voice says, "I think he is enjoying this. Look at how hard his little cock is!"

Ms Rikki replies, "I agree and will deal with it when we get home. The small will work. Jerry go get dressed while I get you some additional lingerie."

I return to the dressing room and get dressed and go find Rikki at the cash register with a pile of camisoles, panties, nighties and bras. I add the yellow camisole to the pile and pay the bill when it is all totaled. Taking the bags we leave the store and Rikki turns to me and says, "Take the bags to the car and meet me at Liza's Boutique we have some more shopping to do.

After putting the bags in the car I join Rikki in the next store. She has already picked out several pairs of what I think are slacks when I arrive. Turning to me she says, "Take this pair of pink slacks and try them on while I continue to shop. Make sure you come out so Ms Liza and I can see how they fit. You will also need to put these socks on so we get the full effect of the slacks," smiling as she finishes.

I get to the fitting room and try the pants and find out that they are tight fitting stretchy mid-calf capris pants. After putting the socks on I see why Mistress insisted that I put them on, as they are sheer pink anklets with a lace top. I slip my shoes back on and go to find Ms Rikki. What I don't realize is the capris are so tight that my panty line shows and there is an obvious bulge from cock that is getting hard again.

As I approach both Ms Rikki and Ms Liza are talking. Ms Liza is a very attractive woman in her mid-fifties I would guess with an extremely attractive, yet mature, figure. As I get close I hear Ms Liza say, "I agree he will make an attractive sissy. I can't wait until you get further in his training." Ms Rikki says, "I agree and the capris pants look sexy on him. Don't you agree, Jerry?"

"Yes Ms Rikki, I agree, but it is embarrassing wearing them out here in public. Since they seem to fit can I please go change back?" I respond.

Rikki says, "Jerry, why are you embarrassed? You look so sexy I will have trouble keeping my hand off you when we get home. Ms Liza is it OK if I have him wear these home?"

I start to say something in protest, but before I can, Ms Liza responds, "No problem at all, but I think we better look at some shoes that will look better than those loafers he has on." I realize that to protest would be futile.

Ms Rikki picks out a couple pairs of pants and then moves to look at some blouses. She holds one up to me and says, "This should fit, go put this on and bring your masculine clothes with you." I take the blouse which is plain white and head for the fitting room. After putting the blouse on I pick-up my clothes and start to leave the fitting room. As I walk by a mirror I realize the blouse is made of is sheer material and my pink camisole shows through. I blush as excitement from the potential embracement causes my cock to start to harden.

Leaving the changing area I find Ms Rikki and Ms Liza in the shoe area. Ms Liza has me sit down and checks my foot for the correct size. She then goes and picks out several pairs for me to try on. The first is a pair of bright yellow high heels. I slip my feet into them and stand up and start walking. Ms Liza turns to Rikki and says with a smile, "As easy as he is walking in those heels, I think he has had some practice." To which Rikki replies, "Yes that is all he is allowed around the apartment."

After trying on several more pairs, Ms Rikki settled on a pair of pink high heeled pumps with five inch heels and a pair of pink sandals with three inch heels, that I would wear home. So here I was an obvious male in a sheer blouse, stretchy capris pants, pink lacy anklet socks and pink heeled sandals walking out of the store with Ms Rikki.

As we walk to the car I am getting some strange looks. Ms Rikki walks up beside me and gives me a kiss saying, "You were so well behaved that I may have to reward you when we get home. Walk beside me as we go to the car." I walked next to Rikki and she moved close to me and started rub my ass through the capris. She got the reaction she was looking for as my cock starts to harden and the bulge became more obvious, as commented on by a couple of women we walked by.

After getting to the car and getting the last packages loaded we headed home. When we arrive Rikki told me to put all of my new clothes away and she would cook dinner. I finish putting the clothes away just as Rikki calls me to come to dinner. After we eat Rikki ask, "Did you enjoy this afternoon?"

After thinking for a moment I respond, "Yes Mistress, I enjoyed it a lot. There was just the right amount of humiliation and stimulation to keep me on edge. I fact I am getting hard now just thinking about it. I think I would enjoy doing this again at some time."

Rikki replies, "That is good to know. I need to study for a couple of hours then we can get you some relief before we go to bed. Clean up the dishes and kitchen and relax. I will call you when I am done studying."

After cleaning up I go to my room and get a quick shower and change into one of the sheer baby-doll nighties Mistress got this afternoon and the pink sandals before relaxing to watch some TV. About an hour and a half later Mistress calls me into her room where I find her naked laying on her back, legs spread playing with her pussy. As I enter she says, "Get between my legs and put your tongue to work!"

Crawling between her legs I start to lick her pussy and over the next forty-five minutes bring her to three orgasms. Pulling me up to her she kisses me and says, "Lay on your back it is my turn." Mistress starts stroking my cock and brings me to the edge several times before allowing me to cum in her hand. She brings the cum filled hand to my mouth and has me clean it. She then sends me off to bed.

This all occurred late in the winter or early spring and not much changed in our relationship over the next several months. I dressed as a female when at home and wore lingerie under my clothes when I was out. We would have a play session one night each week end. Mistress provided me with more female lead relationship information, some of it quite kinky.