Willing to do Anything Ch. 03

Disclaimer: All characters appearing in this story are fictional and are 18 or older.

Recap: Nate allowed Barry to reward him after he was forced to give a blow job. Barry rubbed Nate's 'clit' through his panties until he ejaculated. Afterwards they went to Nate's parents house, so he could come out as trans. Barry convinced his mom to dress him up in her clothes.

Barry later got Nate to come to his house and give him a lap dance with the promise of another clitty rubbing. Barry shot cum into the back of Nate's panties during the dance and then took him to the bedroom for another clit massage. Barry bent Nate over and rubbed his clit like a girl while also humping his ass with his cock. Nate again ejaculated into his panties for the second time. He laid on the bed in his mothers clothes, covered in both of their cum, wondering how he let this happen.

Chapter 3

Barry pressed his hand firmly against my ass, so I could feel how wet my panties were. He leaned over my tired body and whispered in my ear. "You are so fucking hot." He moved to lay behind me like he was going to spoon me and pulled my shoulder up to roll me on my side.

Barry pulled the covers over our heads and continued to rub my ass. He pushed the panties deep into my ass spreading the cum deep within me. I started to pull away, so he would stop and my ass could dry out. "You know Nate, it's normal for a girl to have cum in her pussy. I think you will get used to it." I winced in the dark and tried to remain silent hoping he would let me sleep.

He cuddled me until I fell asleep. He would caress my ass, then rub my penis a little, and run his hands along my stomach. I could feel his erection pressed against my ass hole. I knew he was naked again, and he would hump softly while we cuddled. Finally, he fell asleep letting me drift to sleep next to him.

I barely slept as I kept replaying the events of the day. I wrestled with the fact I had willingly degraded myself and allowed another man to stroke my penis. I liked it. He was strong and assertive, and he knows what he wants. I wanted to be like that but I couldn't possibly see myself as any sort of man after today. I wondered if I was becoming gay or how long it would be until Barry wanted to pop my cherry.

Barry got off when he made me uncomfortable. I know tomorrow he is going to make me be this girly boy in front of all his staff and eventually everyone I know I am his new toy. I'm nervous that I am going to be this sex puppet he can parade around and fuck silly whenever he is horny.

After a restless night Barry finally woke up and asked for me to go into the kitchen to make us some breakfast. Normally I might have been offended by him asking me to serve him but I would have agreed to anything to get up and get his cock off of my ass.

I got into the kitchen and started to make some sausage and eggs. While I was cooking facing the stove I suddenly felt his presence behind me. Barry put his hands on my hips and said "Good morning sexy". He then lifted my dress and put his hand on my penis. "Your clitty had a big day yesterday. I think she likes it when you wear panties."

"Barry. Please. I am trying to make you breakfast like you asked."

"It's ok, Nate. You are doing such a good job too. I am just happy today is all. I want you to be happy too. This is a big change for you and I really think you will enjoy your new life as a woman if you embrace it."

Barry rubbed my penis as he talked. I think he wants me to get used to him fondling me. I feel like a sex doll all dressed up for him to shoot his load into. Eventually he stopped rubbing me and sat down. I served breakfast and we ate in silence. I wondered if he was mad at me for not reacting to his touch.

"Nate. I have someone coming over today to help you get ready for your contract signing today. Do you remember Rachel?"

Oh my god! Fuck me. Rachel was my girlfriend in high school. Barry knew this. He was fucking with me! I haven't seen Rachel since I broke up with her when I moved away. I didn't want to have a long term relationship. Now any chance I have at rekindling that will doe when she sees me.

"How could you do that, Barry?"

"She is going to find out anyway, Nate. I just figured it would help of someone you know and has been intimate with could help you instead of a stranger."

"Barry, I don't..."

*Knock knock*

"Oh she is here. Sorry Nate. Stay here and I will let her in and help smooth this over."

"Wait, I..."

He got up and ran to the door before I could say anything. All I could do is wait and wonder how she might react when she sees me like this. I could hear him greeting her, and she sounded really excited to see him. He told her he needed her help with something sensitive and made her promise not to laugh and just be supportive. I could hear them starting to walk over. Fuck me...

Once they got into the kitchen I locked eyes with Rachel. "Nate. Oh my god" She whispered under her breath.

"Hi." That was all I could manage to get out. My face felt red. She was as beautiful as ever. I remembered how bad I wanted to get into her panties when we were in school. How ironic is it that the next time she would see me is wearing my own pair.

Barry interjected. "Rachel, Nate is going through some new experiences right now. He came to me for help to express himself and guidance as he explores his new sexual identity. He is committed to living his life as a woman from now on. I asked for your help because I think you may be able to help him as a friend to learn more about being a woman."

Rachel rushed over and embraced me. I could smell her perfume and my eyes watered as I remembered all the good times we had. "I'm so sorry Nate. I never knew you felt this way. Of course, I will be here for you."

A few awkward moments of silence passed as we hugged. She pulled away from me and really gave me a once over with her eyes. I wondered if she could smell the stench of cum from yesterday. "It's ok, Rachel. I um... I just kind of found out myself recently. There is no way you could have known. I am sorry you had to be surprised by all of this actually."

Barry interjected, "Sorry to interrupt this moment but I have a full schedule this morning and regretfully I have to leave. Rachel, Nate is going to be employed at my company starting this afternoon as a full time woman. I was hoping you would be able to take him for his first salon, waxing, and shopping experiences. I want to leave you my credit card, today is on me."

Rachel smiled at me and gladly accepted. Apparently she had no plans today and would love to catch up with me. I was nervous to have to spend my first day in public as a woman escorted by my ex-girlfriend.

"Great. Thank you so much Rachel. It was so great to see you this morning. Hopefully the three of us can catch up together soon. I am sure you and Nate have so much to talk about, so I will leave you to it."

Barry rushed out the door leaving me alone with Rachel. It was my first moments since I had agreed to do this 'woman for a year' deal where Barry was not here. I thought I would be glad to get away from that horny guy, but I was actually scared to have to go out in public without his support.

Rachel looked back at me after Barry left. "So Nate... Umm. Sorry. I don't really know how to do this so sorry if I am blunt. Can you maybe talk to me about why you want to be a woman? Sorry, it's just that we dated and I just never saw this coming."

Oh, Fuck. I had gotten off easy with my parents since they didn't really want to know. Damn it Barry, he should have known that Rachel would be more curious. Well, I figured I needed to figure this out anyway, since she won't be the only one to ask that. Try not to panic, I tell myself.

"I um... I guess I didn't really know myself very well. When I grew up I didn't really like sports or action like other boys. I never really considered how I felt really. Recently I uhh... Had some more feminine experiences like wearing these clothes and um... Some sexual ones. I guess it opened me up to a new side of me that I need to explore."

Rachel was a bit wide-eyed as I explained. "Oh my... So you and Barry are...?"

"Exploring" I didn't want to give any details about that. I still don't know how I feel about that.

"Well that explains the uhh... Musky smell"

"Oh God" I looked down and blushed. I was afraid that she would know. "I am so sorry Rachel. This is so embarrassing"

Rachel hugged and reassured me it was alright. "Well it's not like it's the first time I have smelled that. I remember many a time when I wondered people could smell your scent on me."

We continued to chat and catch up. I learned she was a real estate agent now and was in a serious relationship with her boyfriend. It was weird. She seemed to talk to me more like she did to her girl friends and less like she did when we were together. She told me how she met her boyfriend and what she liked about him. She asked me how I got in touch with Barry and how long I was in town. Oh my god, we were gossiping about boys. I wanted to crawl out of my skin, but this is my life now.

After we chatted for a while, she invited me to her car. She headed off toward town. I was nervous to ask her where we were going but I did so anyways. I gulped hard as she casually threw out that we were going to her favorite spa for facials, manicures, pedicures, and waxing.

"We are going all out since we have Barry's card" Rachel winked at me as we continued to drive. My mind raced as I wondered what fresh horrors I would experience today.

We started with the manicure and pedicure. Rachel insisted that we should get an acrylic overlay. Since I didn't know how to take care of my nails, this would be strong and protective. It was hard for me to argue with her logic. They asked me for a color and I hesitated. That was a mistake. As soon as she could, Rachel told them to paint my fingers and toes a nice light pink since it will be easy to match when we go shopping.

Once they had finished both of our nails, Rachel gushed over how good they looked. She told me that Barry would love them and that I would get used to having longer finger nails.

Rachel led me to the other side of the spa where they did all the waxing. "Rachel. I have never done this before. I'm not sure I can handle it."

She pondered her answer for a few moments and then looked me square in the eyes. "Nate, Barry said you decided that you were going to fully commit to this experience. You can't just pick out the nice things girls do and ignore all the things we suffer through. Think of all the women you know who all have experienced something like this. It is going to suck, not going to lie. Be brave for me, be brave for Barry, and woman up."

Fuck. If I really was a trans woman that would have been inspiring. I didn't really have a way out of this without compromising the deal I was about to sign. "Okay".

Rachel smiled at me and turned to the attendant. "I am going to do a Brazilian today and a little touch up waxing on my lip. My friend here is going to need a full body session and I think he should do a heart attack." She turned back to me. "That will be a nice little surprise for Barry."

We were split up, and I was taken to the room where my specialist explained how it would all happen. I told her it was my first time and anything she could do to help me through it would be appreciated. She gave me a few Popsicle sticks to bite down on and told me it would suck but that faster is better.

She was an expert but that was nothing short of full on torture. They lathered just about my whole body is wax and time again pulled full strips of hair from my body. My eyes watered and I bit hard grunting with each and every pull until I was full on bawling. It felt like forever and I must have blacked out for parts of it. Finally, she ushered me over to the mirror while I was still fully naked.

I could barely walk as I just wanted to curl up and die. I had completely forgotten what Rachel had asked for until I looked down at pubic region. The specialist had trimmed my pubic hair nice and short and then waxed it until just a small heart was showing above my penis. I was completely bare everywhere else. She had even waxed my asshole which I might add was the worst experience of my life.

She explained to me that for 24-48 hours there was no sun, no swimming, no tight clothes, and no sex. I would have to moisturize, wash, and avoid heat. I was suddenly glad for my mom's dress and not the tight slutty outfit in Barry's office. At least this would get him off my back for 2 days.

Rachel was waiting for me back out front. "Oh you look so good! What do you think?"

I glared at her. "How do you do that? I seriously wanted to die the entire time"

"Oh honey. I wish I could hug you but that would definitely suck. Actually, the first time is the worst. That's why it's important to wax regularity so you become less sensitive and the hair comes out easier."

She scheduled us both for a couple weeks out. "We can be waxing buddies" She laughed but I hated her saying that. I wish I never had to do that again but I know Barry will say otherwise.

"Nate, you are such a trooper today. I saved the best for last though."

We went to the last stop and got signed up for us each to have a facial. Rachel explained how it cleans your face and helps prevent blemishes and makes your skin healthier. She also noted how she loves the massage and how good it feels after.

Once they got started I tried to relax. I could feel them doing the cleaning and exfoliating treatments. Then they massaged me which actually felt pretty good. They applied a mask and finished with a serum and moisturizer.

I was amazed about how smooth and shiny my face was after. I wish I could say I was relaxed but this was just a small moment of relief on what was a very jarring experience.

Rachel and I finally left the spa, and she drove us over to the mall. This was the first time I really noticed people staring. Rachel assured me it was ok, they might stare but they won't have the guts to do anything else.

We went to a lingerie store and Rachel picked me out a pair of granny panties to wear while my wax heals.

I got sized for a bra and Rachel helped me pick out an array of different panties, thongs, bras, teddies, garters, stockings, and hosiery. After we paid, Rachel rushed me into a dressing room. "Alright, Nate. Let's get you out of those dirty panties."

I protested to ask her to let me change alone, but she wasn't having it. Instead, she demanded that I take all my clothes off, so she could see how good a job they did on my wax. I was mortified. I didn't want her to see me all smooth and this girly little heart right above my dick. Now whenever she would think of me I was going to be a hairless sissy changing my soiled panties instead of her ex-boyfriend.

Meekly I undressed until she exploded "Oh my gosh Nate! That is so cute!" It was humiliating having my former girlfriend looking down at my cock and calling it cute. "Barry is just going to love your new look"

I quickly got changed into my new underwear and Rachel took me to look for some clothes for my first day. We settled on a loose skirt and a white blouse that wouldn't bother my skin too much. She also grabbed a pair of 3-4 inch black heels to go with it. Again I was rushed to change after paying. The skirt rested about 2 or 3 inches above my knees. It was different to have so much of my legs exposed. The blouse covered me well but it was obvious the center sagged from my lack of breasts.

I wobbled around the store in my heels as Rachel kept giving my advice on how to walk. She insisted I keep practicing as they would be common wear in an office environment.

We walked over to the salon and Rachel got the stylist right to work. They focused on extensions that would give me the girly yet professional look that I needed for the outfit. They styled it into an easy ponytail as to limit the amount of hair in my face.

Rachel and I also went to the beauty stores to shop for make up and to have mine done. I never realized how complicated all the layering and matching was. No wonder it seemed to take women hours to get ready. I would never remember it all but hopefully it would get easier as the year goes.

Once I stood in front of a full mirror in my new outfit, hair, and makeup I could swear that I looked just like a woman. Sure I was a bit mannish, but I wouldn't kick myself out of bed. Oh god. I realized that if I felt like that then surely every other man would have his eyes on me too.

The time had flown by and it was already time for Rachel to drop me off at the office. I thanked her profusely for everything she did. "That's what girlfriends are for". She was all in on this trans girl thing but at least I had someone I could call when I needed.

I wobbled into the office. All the staff who saw me yesterday didn't seem to notice I was the same person as before. I told them I had a meeting scheduled with Barry. They looked confused and said his schedule was for someone named Nate. "I'm... uhh... Ahem. I'm Nate." They looked at me wide-eyed and apologized. They ushered me to his office and I walked in.

"Holy fuck Nate! You look like... I don't know... Seventy grand at least!" I was crushed. There it was right in the open. I had basically sold my body, identity, my everything for a measly $70,000. "This is my lawyer" He motioned to the man beside him. "Lets go over it"

We went through the contract details. I can't remember everything but here are some of the things I recall.

- I can't tell anyone about the contract.

-I have to willingly live the entire year as a woman no exceptions.

-Barry can request sexual favors 3x per week. This includes hand jobs, blow jobs, anal sex and varied acts. Additional favors are welcome and rewarded.

-I can have relations with others. I must have them as a woman. I may not use my penis for oral or penetrative sex.

-I have included company housing with roommates, 3 women who are employed here.

-I have a salaried job here as secretary/attendant for the duration of the contract. The pay is $50,000 annually.

-I will receive a stipend of $2500 per month for clothes, makeup, perfume, and other needs. Barry will provide a list of any items at the beginning of the month he wants me to purchase and/or use. The remaining funds must be used on appropriate women's items only.

-There is a clause for funds toward permanent body modification such as breast augmentation. This is voluntary.

-Barry will ask me to go demeaning and uncomfortable things. I have a right to refuse but should do so with discretion. Abuse of this can lead to contract forfeiture.

-If I am unsure if something is a contract violation, I can ask the lawyer or Barry.

-Under no circumstance may I revert to my prior self or the contract is void.

-After 1 year the contract is fulfilled. The contract may he reinstated annually with the same or modified terms. A $70,000 payout for each subsequent completion will replace the initial debt.

-Neither party may terminate the contract without cause.

-A void of the contract by means of breaking any clauses aforementioned will result in a debt of $70,000 to Barry which will be legally backed.

-The first contract will be backdated to yesterday as per an agreement between both parties.

Nervously I signed away at the bottom line and Barry did so as well. It felt a hollow victory to have given so much. I was Barry's girl now both physically in appearance and legally. His millions had made him shrewd and cunning. I felt like even less than I was before I had come to him for help. Now I am basically a doll playing dress up. The worst thing was that nobody seemed to question it. Everyone was just fine watching me descend into my new girly life.