Jerry becomes Jill Pt. 04a: Doctor

Jerry becomes Jill: Part 4a: Summer - School

This is the fourth part of my story about how I became Jill. Summer school continues with female hormones being introduced and a trip to the Doctor. Jill is looking forward to the month long break coming up at the end of the summer.

Spring quarter ended with a short break, we started into the summer quarter. Not much changed in our routine, but we were both looking forward to the nearly month long break that would happen at the end of the summer quarter. Mistress kept dropping hints about the break that kept me wondering what she had planned.

At breakfast on Saturday Mistress Rikki puts four unlabeled bottles of pills and the table and says, "A doctor friend of mine recommended that I have you start taking these pills. She assured me that they are perfectly safe for you. You will meet her in the near future. The pills will help feminize your body. You know I wouldn't do anything to permanently harm you. Are you OK with taking these?"

I think about this as I eat a little bit of my breakfast before responding, "Mistress, yes I trust you and I am enjoying you leading our relationship. If this is what you think we should do, then I will do as you wish."

"Thank you Jerry. Dr. Brown said that you should take two of each pill twice a day with food for the first week and then cut back to one of each pill twice a day after that. Dr. Brown will want to see you in a couple of weeks and I will make that appointment for us. Why don't you take the first eight pills now?" responded Mistress.

I take the pills and get on with my daily routine. I would learn latter that the two of the pills were to increase the female hormones in my body; one would reduce the testosterone and the fourth would stimulate breast development.

Our routine is pretty normal for the next three weeks although I think I am seeing some subtle changes in my body. At dinner, on Thursday night three weeks after starting the pills Mistress Rikki tells me that I have an appointment with Dr. Brown on Friday at 3:00. She goes on to say, "Your last class tomorrow is out at noon. Hurry home and get a shower and make sure your body is hairless. I will leave an outfit for you to wear on my bed. I will pick you up at 2:15 to go to the appointment."

I reply, "Yes Mistress I am looking forward to meeting Dr. Brown."

I get up the next morning and shave really well to save time after class. Class seems to drag by slowly, but it is finally time to go home and get ready. When I get home I strip off my clothes and jump in the shower and wash, making sure I am free of hair below my neck and then shave my face real close. I get out of the shower and rub my body with lotion before going into Mistress's room to get my outfit.

I return to my room and get dressed. First I slip into the pink thong panties Mistress left. For some reason this time my cock and balls seem to fit into the panty better. Next was a match A-cup bra. This is the first time she has had me wear a bra and I have trouble putting it on. Finally I hook it in front, spin it around my body and slip my arms in the straps.

This is followed by a pair of light pink sheer to the waist panty hose and hot pink lacy anklets. It is obvious Mistress is going for a very feminine look. Next came the sheer white blouse I wore home form the store several weeks ago, a pair of white capris pants and the pink heeled sandals. In one of the sandals was a note that read, "Use one of my perfumes and make sure you smell nice and comb your hair in a feminine style. I will be in to help with your make up when I get home." I followed Mistress's instructs and sat down to wait for here to get home.

Mistress Rikki got home and had a few minutes to adjust my looks. She styled my hair a little bit and then worked on my eye brows and added eye shadow and lipstick before saying, "Let's go." With that we walked out of the apartment and headed to the car. Fortunately being the middle of the afternoon there were not many people around. We walked by a couple of older women and they commented on my bra that was visible through the blouse and the bulge in the front of my tight capris pants.

The drive to Dr. Brown's office took about 15 minutes. Rikki was driving and pulled up in front of the office and we walked into the waiting room. Mistress Rikki went to the reception desk and checked us in with the nurse who was working there. After about five minutes the nurse came out and invited us back to an observation room. Once in the room she indicated for me to sit on the table as she looked me up and down and said, "Dr. Brown will be with you in a few minutes." We waited quietly waiting for Dr. Brown.

After a short wait Dr. Brown and the nurse came in and greetings were exchanged. Dr. Brown turned to the nurse and said, "Betty you can go ahead and go home for the day. Please make sure to lock the door on your way out." With that Betty turned and left and Dr. Brown turned back to me and said, "Jerry, I have an MD and I am also a trained psychologist and sex therapist. I specialize in sexual reassignment, feminization and female lead relationships. The pills you have been taking will soften your skin, feminize your figure, help with breast development, reduce hair growth, and reduce the size of your testicles among a few other minor issues. I will be monitoring your throughout this process. Today we will get some base line numbers including physical measurements and blood chemistry readings. Shall we get started? Please remove all of your clothes."

I stand up and start undressing. As soon as I am naked Dr. Brown has me get on the scale and gets my weight. She then starts to get numerous measurements of my body such as the circumference of my calves, thighs, forearms, testicles and others. She then draws a number of vials of blood for testing. She then turns to Rikki and says now we need to measure his clit both soft and erect and asks her to help.

Rikki hold holds my soft cock straight out so Dr. Brown can get its length and circumference. Dr. Brown then says, "Jerry get up on the exam table and lay back and put your feet in the stir-ups. Rikki there is some warm oil on the counter would you mind getting Jerry hard." With that Rikki pours some oil on my cock and starts stroking it. It takes a little longer than normal for me to get hard, I wonder if that is an effect of the pills. Once Dr. Brown gets the measurement of my erect cock I am told to clean-up, get dressed and then come down the hall to Dr. Brown's office.

When I finish dressing I go find the office and Dr. Brown and Rikki are talking. After I take a seat Dr. Brown continues, "I think Jerry's changes are progressing nicely. I would suggest that you get electrolysis started to help with hair issues. He should massage his breasts manually 2 or 3 times a day for 10 minutes as I showed you earlier, Rikki. Then he should use the hydro-suction therapy machine twice a day for 30 minutes as well. You do the other things that I suggested as you see fit. Call on Monday and make an appointment for about 4 weeks so I can check on Jerry's progress."

She then adds, "I have a couple of other things before you go. Rikki have you decided on a feminine name for Jerry?"

"Yes," replies Mistress Rikki, "I thought I would go with Jill, what do you think, Sarah?"

"I think that is a great choice," responds Dr. Brown adding, "I think you should start using that name whenever you are out in public and Jill is dressed as a female and all the time in the home. It will help her get used to it and help reinforce her feminine side."

Mistress Rikki adds, "Yes Sarah, I think that is a good idea, what about you Jill?"

It takes me a short time before it registers that Mistress is talking to me. When it catches up to me I respond, "Yes, Mistress, I like that name, I hope I make you happy as Jill."

Dr. Brown, then interjects, "That is great. But now I have a surprise for the two of you." With that she reaches in the bottom drawer of her desk and pulls out a small pink box. Dr. Brown calls to come get the box and go open it in front of Mistress Rikki.

I retrieve the box and get on my knees in front of Mistress Rikki and proceed to open the box. Inside it is a plastic male chastity device kit. The kit contains several rings for around the base of the cock and two sleeves, one very short and the other longer. The sleeves have a number of threaded holes around the diameter and length. There is a plastic bag with about a dozen sharply pointed set screws and a wrench for them.

Mistress pulls out one of the tubes and looks at it as Dr. Brown says, "If you will have Jill bring it up here I will show you how to put it on. I know you said you do not have a problem with Jill playing with her clitty but this way you know she can't and beside it reinforces you control over all sexual activities."

Mistress Rikki hands the device to me and I go up to Dr. Brown who says, "Jill, slide your pants, hose and panties down so I can have access to your clitty. The set screws can be used to increase the punishment level, but we will not use them this time." After pulling everything down Dr. Brown takes my cock and feeds my balls through one the ring followed by my cock. She then slips the shorter control piece over my cock and locks it in place. It is obvious to me that any attempt at an erection will be painful. Dr. Brown then adds the plastic lock. As I pull my panties, hose and capris back up I realize am sealed in for I have no idea how long.

After thanking Dr. Brown for her help with the devise we stand and say our good byes. With the device in place there is an obvious bulge in the front of my capris pants. Looking at this Mistress walks over close beside me and stats rubbing my ass. As she does this she whispers in my ear, "At least with your cock trapped in the device the bulge in the front of your pants can't get any bigger!"

We get in the car, but instead of heading towards home we head in a different direction. As we go, Mistress reaches over and strokes my leg. After doing this for a few minutes she reaches up and unbuttons her blouse exposing her bra encasing her beautiful breasts before she reaches over and starts rubbing my leg again. My cock starts to harden trapped in its little cage and it starts to become painful.

"Mistress," I say, "What you are doing is making me get an erection and it is very uncomfortable."

She replies, "I know." "I am enjoying it," she says as she pulls into a parking lot next to a restaurant, with a sign that says, "Bitches Grill." She turns to me and says, "Come on, Jill. Let's have some dinner."

We get out of the car and walk into the restaurant. The hostess greats Mistress by name and takes us to a table. I look around the restaurant and quickly realize that most of the customers are females or TV/TS. After we order Mistress excuses herself to go to the restroom.

When she returns it is obvious she has removed he bra as her nipples are plainly visible poking through her blouse. She slides in the booth over next to me and starts stroking my leg. As I look at her I notice that her blouse is still unbuttoned and she has it bunched open so I can see one of her incredibly beautiful breasts. With all this stimulation my cock is trying to get hard again and I start squirming.

"You going to need to learn to better control that little thing of yours or we will need to put the screws in," says Mistress Rikki with a chuckle.

After finishing the meal we head for home. As soon as we get there Mistress tells me to go to my room and remove my blouse and capris and then return to the living room. When I get back to the living room, Mistress has removed all of her clothes and is sitting in one of the chairs. Her legs are spread wide and one hand is on her left breast twisting and pulling on her nipple while her other hand is playing with her obviously wet pussy.

Mistress Rikki looks up and seeing me standing there starring at her says, "Jill I need your face buried in my pussy. I need some relief!"

I hurry over to Mistress and crawl between her widely spread legs and start liking up some of her sweet juices from her thighs and the lips of her pussy. Then I go to light tongue strokes on her pussy which is raising her frustration level. Rikki grabs the back of my head with both hands, pulling my face into her pussy while saying, "Quit teasing me and make me come!"

I start to lick, suck and nip at her clit and bring her to her first orgasm in a few minutes. She reaches and holds my head there as I keep working on her pussy and she has another orgasm a short time later. All the time I am doing this I am suffering with my cock trying to get hard in its little plastic cage. After worshiping her pussy for more than ninety minutes and bringing Mistress to several orgasms, she pushes me away.

She looks at me and says, "Thank you Jill, that was enjoyable. Now go to bed and do your breast exercises and I will see you in the morning."

This is the first time I have gotten Mistress the relief she needed and she has not reciprocated. I go to bed frustrated and do my breast exercises. Unable to get to sleep I tried to get some relief, but there is no way to get the required stimulation in my chastity devise. Finally after midnight I fall asleep.

I get up Saturday morning and get to work on my choirs. Mistress gets up mid-morning and comes out in a sexy night gown. She looks at me as I vacuum the living room and says, "Jill, you did a very good job yesterday and last night but now things are back to normal. I am going to spend the day studying here in the apartment. Do what you need to do."

I respond, "Thank you Mistress, but I could use some relief."

Mistress replies, "I am sure you could and we will see about that later, but for now I would like some bacon and French toast for breakfast."

"Very good Mistress," I say turning off the vacuum and heading into the kitchen. After taking care of breakfast I return to my cleaning followed by some studying. Mistress finishes breakfast and goes to her bedroom. When she emerges a few minute later she is fully made up with her hair pulled into a ponytail. She has black high heels on with black sheer-to-the-waist panty hose and a black sheer bra. She returns to studying while visually teasing me throughout the day.

After dinner that evening we settle down to watch a movie. This one is about a female dominating a sissy and introducing him to anal sex play. After the movie Mistress has me provide her with an orgasm orally. When I finish she says go to your room and take your clothes off and I will be in shortly.

I am sitting on the edge of the bed when Mistress comes in and removes the chastity device. She sends me to the shower with instructions not to play with myself. When I come out Mistress has me lay on the bed and secures my hands together to the headboard and my ankles spread-eagle to the corners at the foot of the bed.

She then sits down next to me and puts some oil on my cock and starts to stroke it slowly bring me close to the relief I want and need. But just as she gets close she stops and lets me calm down, before starting again. She does this once, twice, three ... she finally quits after bringing me to the edge for the seventh time and stands up to leave.

I beg, "Mistress please let me come, I need it so bad. Please, please I beg of you!"

Mistress turns and looks at me saying, "Jill, I know you want to cum but not to night. Consider this part of your training. Call me when that thing shrivels up and I can get the device back on you." She then leaves me with my erection standing in the air.

About an hour later my cock finally softens and I call Mistress. She locks me back in chastity and releases me from the bed, giving me a hug and a kiss in the process.

Life pretty much goes back to normal, school during the week, house chores on Saturday morning and a movie Saturday evening followed by a sex session. That first week she leaves me locked up until the next Saturday before I get any relief, although she lets me out to wash every other day. The movies are tending to get a little kinkier with some including anal play and two that introduced sissy-sissy bisexuality.

To be continued...