Willing to do Anything Ch. 02

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

Recap: Nate has a debt to a dangerous man who has threatened his life. With nowhere to turn, he asks a former friend to help. Barry is rich and agreed to pay the debt if Nate would spend one year as a woman. He has a controlling fetish for getting partners to do things they would not normally do. To prove his commitment, Barry made Nate wear skimpy clothes and lipstick while giving him a blowjob. 

Chapter 2

Barry looked down to see me crying. He motioned for me to stand up while he tucked his penis back into his pants and fastened them. "That was very good, Nate. I didn't think you were going to be able to go through with it. I hope you can understand that most people would not have been able to do that, and I think this makes you very special."

I still had the taste of his cum in my mouth, and I was too embarrassed to say anything, so I meekly nodded along. He took out a handkerchief and whipped my mouth gently. It was the first kindness he had shown me, which made me feel a little bit better. 

Barry continued, "I know I can be demanding. I am not the person you once knew in high school anymore, but you should know that I reward equally as much as I demand. I can also ensure that I will follow through on my promises."

He walked back over to his desk and pulled out his chair to sit down. "Come sit down on my lap, Nate."

It was a weird request. I had not sat on someone's lap since I was probably 10 years old. Barry was quite a bit bigger than me and could easily hold my weight. I walked over, and he tapped his knee. I gently sat down on his leg, which felt firm and strong. Oddly, it felt more emasculating sitting on his lap than it did giving him a blow job. 

"That's a good girl, Nate. Now why don't you give me the number of your bookie, and I will arrange for him to come in tomorrow after your contract signing?"

I gave him the number. He called the bookie and told him to come to his office to collect the payment. I felt such shame listening to another man call and handle my mistakes. The bookie laughed on the phone when he told him he was calling on my behalf. I wanted to curl up into a ball and die. 

When Barry got off the phone, he softly brushed his hands on my face to try to calm me down. "Everything is going to be okay, Nate. Tomorrow we will start your new job, and you can get a fresh start with me as my girl. How does that sound?"

I actually felt reassured and comforted by his touch, but his words still felt so foreign. I was a man, and I don't think I will ever be ready to be anyone's girl. I didn't want to disrupt this after everything I had done, so I told him "That sounds nice". 

"That's great to hear from you. Nate, I would like your permission to touch you. You did a very difficult task today, and I want to reward you for it."

I didn't know what to do. I was on his lap, and all I wanted to do was leave, but I had to just keep going forward. "umm. Ok. I think so." 

"Such a good girl. Thank you, Nate. I think you will really like this."

Barry pulled my skirt up, completely revealing my bulging panties. He placed his hand over the bulge and separated my penis from my balls until my penis was flat against the panties pointing back up towards me. 

"Since you are going to be my girl for a year, I can't really call this your cock anymore, even if it is a cute one. Instead, this is going to be your clit from now on. One of the ways a woman receives pleasure is by rubbing her clit"

Barry began to grip my penis with his hand. He moved it upwards and downwards, making the soft fabric of the panties glide with his hand. After a little movement, it began to get hard.

He whispered into my ear as he continued to rub. "I am going to take good care of you, Nate. I promise to show you just how rewarding being my girl can be. How does this feel?"

"It feels... good. The panties are pretty soft."

"I need you to be more specific, Nate. What feels good?"

"It feels good when you umm... when you touch my uh..." I didn't want to call it what he did, but it was starting to feel really good, and I didn't want him to stop. 

"Touch your what, Nate?"

"My clit. Fine. My girl clit. It feels good when you rub my clit like that. Please don't stop."

"Good girl. You look so cute in your panties." He was very slow and meticulous. His grasp of my penis remained firm as he continued to stroke me through the panties. I moaned softly. 

I don't really know what came over me. I guess the whole ordeal had me in a very vulnerable state, and Barry's firm touch actually felt really good against the soft panties. I didn't want to like it, but it felt good, and I was losing my will. 

"Wait Barry." I tried to snap myself back. "I am not gay. This is wrong."

Barry looked me in the eyes while loosening his grip. He was just barely and softly running his fingers on my penis in a teasing motion. It's ok, Nate. It's just me and you here. I just think you are so cute in these panties. I want to please you and make you feel good. I want you to be my girl and to know you can trust me."

I was nervous and overwhelmed. "I don't know."

"Nate, your clit is really hard. Honestly, I think if you are going to be doing this for a year, you should at least try it out. I know this is really hard for you, but I will be here to help you. I really want to make you cum into these panties and I think you will like that. Will you please consider seeing how it goes?" 

"I... I'm not gay. Ok? But I guess I could try it again. This is just so... different. I'm scared."

Barry took his hand and placed it on the back of my head to reassure me. He gripped my penis again with his other hand and kept rubbing back and forth. It's OK, Nate. This is your first time having a man touch your clit. Its normal to be nervous. I promise its going to feel really good to cum like a girl."

Barry took one of my arms and guided me to wrap it around his neck. Then he took my other hand and guided it under my bra. "You should play with your nipple while I rub your clit"

The pleasure was beginning to build again as I rubbed my nipple while he stroked my penis. I was surprised that I had any enjoyment from my nipple at all. I had never touched them while having sex before.

Barry quickened his motion, and I began to involuntarily moan.

"Yes Nate. You are such a sexy girl right now. Your clit is so hard. I want you to cum in your panties. Be a good little girl and moan for me. Say, Barry, I want to cum in my panties like a good girl." 

Mmmmm, I moaned loudly. It was starting to feel really good. I really wanted to cum and I knew I was close. "MmmMmm. Oh Barry! I want to cum. I want to... Oh! I want to cum in my panties like a good... FUCK. OH. That feels so good. I want to cum in my panties like a good girl!!" 

I arched my back and exploded. The buildup was the most intense orgasm I had ever experienced. I convulsed on Barry's lap as my creamy white cum oozed through my panties. I panted out of breath as my penis continued to pulse. 

"So did you like that, Nate?"

I suddenly had clarity again. Here I was sitting on Barry's lap in slutty clothes and shooting my load like a whore. I was ashamed to admit that I had really liked it. There was an element of not being in control and surrendering myself to the idea that I could just let him pleasure me. I guess that's what a lot of women enjoy about sex with men. 

"Uhmm. I uhh. I guess I kind of liked it." 

"That is great to hear, Nate. I really liked it too. I want you to know that I will be pushing you to try and explore some things you are going to be uncomfortable with. I hope I can prove to you, like today, that you can trust me. As scary as this is, it can be fun too." 

"Barry I am not sure yet. I just really needed a fresh start and a second chance. I guess I am willing to at least try. I don't want to think about sucking your cock all the time and having people see me like this. I don't really have a choice. I don't know if I can trust you yet. We just started this crazy agreement, but maybe you're right, and one day I will be able to." 

"That's at least a start. I think you will make a lovely girl for a year. You should try to enjoy it as much as you can. This is such a turn-on for me, but I want to please you too." 

We sat in silence for a few moments before Barry suggested I change back into my clothes. I was relieved to take the poor-fitting clothes off. I was nervous that he would parade me around the office with cum dripping down my legs. 

Barry said that the rest of his day was open, and he suggested he could help me with a difficult task. He reminded me that since I was agreeing to become his girl for a year, there was going to be lots of public exposure. He has been a local celebrity since he flipped his crypto and started his business. He suggested he should escort me to my parents house so I could 'come out of the closet' before they found out later. 

I was devastated. I had only thought of all the embarrassing feelings that I would have to endure. He was right. I didn't have any time to waste since, very quickly, the world would see I was going to be a trans woman. The realization that every person I knew would now see me was suddenly sinking in. This was going to fucking suck. 

After I got dressed and cleaned up, Barry took me to his car. He had been to my parents house before, and they knew who he was. He insisted he could help with the awkward conversation. 

My mother's name is Sarah. She is a little shorter than me. She is thin and fairly average-sized for someone her age. My father's name is Mike, and he is taller than I am and overweight. He drinks his fair share of beer. They are a pretty standard American family. 

Barry and I stand outside their home, and he rings the doorbell. My heart pounds in my chest as I think of any way to get through this. My mom opens the door and smiles, since she is overjoyed to see me. 

"Oh my goodness! What a surprise! Nate, and... Barry. Wow! Barry, it's been so many years! Come in. Come in." 

Mom brings us into the living room and has a small chat with Barry and Dad. They gush over Barry's fortune and reminisce over my high school memories. Mom brings in some drinks as we settle on the couches. 

Mom finally asks us, "What brings you boys over today? We are really glad to see you, but it's not everyday that a millionaire drops in."

I hesitated. Clearly, I was nervous as I tapped my foot and felt sweat building up. Barry wasn't making this easy on me, and I bet he was getting off on the whole thing. 

"I umm. I have something I need to tell you. It's hard to say. I am having a hard time with the words." Tears welled in my eyes as I looked them in the face, facing my new reality. 

My mom interjected. "Nate. Its ok. We love you. Whatever you have to say, we will support you and love you always." 

"I..." I choked up. I wiped the tears and resolved to keep going. "I have begun to question my uhh... my identity. I'm going to, um... I am going to start living as a woman." 

There was an uncomfortable awkwardness.  Barry broke the tension. "I know this is sudden, Mike and Sarah. You know that I am highly criticized for my open sexuality. Nate came to me for help expressing herself, and I am here today just to support her. I hope you will be able to do that too." 

Both my mom and dad stood up. I thought they were going to leave the room in silence and never talk to me again. They both moved forward toward me and wrapped me in an embrace. I cried as I felt their support for what was surely a sudden shock. They really did love me unconditionally. 

After we sobbed and worked through the feelings, my dad asked me if we could chat outside. Barry thought that was a great idea since he had something he wanted to talk to my mom about. I was nervous about what he was up to, but I had my own parents to handle. 

Dad walked me into the backyard and apologized for always pushing me towards conventional male activities. He had always pushed me to play or watch sports. I was never athletic or interested, so nothing ever materialized. He suddenly thought this was because I wanted to be a woman, and he was pushing me away from it. 

I hugged him and told him that he did nothing wrong. I explained that this is just me wanting to discover who I am and that I was thankful for his support. He promised to be there for me, even if he didn't understand. He said he was lucky to have the best son in the world and now gets to experience having the best daughter in the world. I was blown away by his unwavering loyalty to me, making me want to cry even more. 

When we walked into the house, my mom latched onto me and directed me over to her bedroom. I knew Barry was behind this, and I was nervous about what he had said to her. 

When we got into her bedroom, she smiled again and hugged me again. "Barry told me how you didn't feel comfortable coming over in your feminine clothes until we talked. He told me that if I helped you find something to wear, it would help us to see you as you really are." 

I protested. "No. Mom. That's really not necessary. I just wanted to talk." 

Oh, stop it, Nate. I want to. Can you please just let me do this for my new daughter?" 

"Ok." I gave in. I already put them through all of this, so I didn't really have anywhere to argue. 

"Go ahead and take off your clothes, hun." She motioned for me to undress. 

"Can I go to a bathroom or something? I don't really want to be naked in front of you." 

"Oh nonsense. It's just us girls here." She winked at me, obviously trying to make me more comfortable.

She didn't realize just how much I did not want to do this. Again, I complied since Barry had put me in a position where I would not be able to resist. I took off all my clothes but my underwear. 

Mom was rummaging through her drawers. She looked back to see me in my underwear. "Oh no, honey. We are going to get you some nice girl underwear that will be more comfortable for you. Go ahead and take those off."

I sighed. She wouldn't let me get away with anything. I took off my underwear and stood naked before she handed me a black pair of panties with a lacy trim and a matching bra. She urged me to put them on.

I stepped into the panties trying not to think of them as my mom's worn panties. They felt much more enjoyable than the slutty pair Barry made me wear. These had much more coverage and plenty of room to nestle my balls in. 

Mom went behind me to help me clasp the bra after she saw me struggle. "You will get used to these the more you wear them. There. I bet you feel much better now." 

"Yes. Thank you, mom." I watched as she ran back to her closet to find something else she could help with. 

"This should be perfect for you." She came out with a blue summer dress. It had straps wide enough to cover the bra and was loose enough to fit me. It would probably go down to about my knees. "Go ahead. Try it on." 

I pulled it over my head, and mom helped to adjust it until it was fitted. 

Oh, that looks great. Just missing one thing." She rushed off to the bathroom and came running back with a tissue box. "It's ok to stuff your bra once in a while. I won't tell." She winked again and helped me stuff some tissue in my bra until it looked like I had some small breasts underneath the dress. 

Mom looked down at my hairy legs. Nate, you will have to learn to shave your body. There isn't any time today, but next time I expect to see this taken care of young lady." She chuckled to herself, proud of her comment.  

"I think your feet are a little too big for my shoes, but do you think this is at least better?"

"It is, mom, thanks. You don't have to do this. I can put on my clothes. I don't want to take yours." I reached for my clothes on the floor. 

Mom rushed over and grabbed them before I could do anything. "No. I won't let you have these. No daughter of mine will have to wear something she doesn't feel like herself in." 

Again with this trap Barry set for me. Now I would have to spend all evening in a dress with Barry and my parents. Fuck, how did he know she would do this? "Ok mom. I appreciate you. Should we join dad?"

"Oh. He is fine, Nate. Those boys can talk about anything. This is my girl time, and I won't let you rush me. I just want to give you a little makeup, and I think you will look so cute."

I wanted to groan. First Barry, and now my mom is calling me cute. She basically dragged me to her vanity and sat me in the mirror. She applied foundation, blush, mascara, eye liner, eye shadow, and lipstick. I was actually impressed at how my face was now distinctly more feminine. I wanted to claw it off, but she did a good job. 

She paraded me in front of the boys. She would say "Look how cute she is" and "I bet you didn't know she looked this good". Dad was trying his best to agree, but this was not something he wanted to discuss. 

Barry was very excited to see what Mom had done to me. I noticed he was shifting and crossing his legs quite a bit. That bastard. He was using my parents to have another freaky kink show in his pants.

I was red with embarrassment, but you couldn't tell under all of this makeup. I didn't want to admit it, but seeing Barry squirm with arousal kind of makes me feel pretty and special. I would never tell him this, though. 

Barry, mom, and dad made me sit through an entire evening where they tried their best to tell me how they were there for me. Mom gave me many tips and lessons on how to be a woman, while Barry kept encouraging her to share even more. Every time I tried to come up with a reason to leave, Barry would counter it. 

Finally, after so many hours of being subjected to this forced femininity, I was able to leave with Barry. I wanted to go home, but he kept insisting I could spend the night at his house. I was tired and exhausted, so I finally caved and agreed.

During the drive, he kept telling me how beautiful and sexy I looked. He told me how he had a hard on and how much he wanted me. He told me he wanted to have some more fun with his beautiful girl. 

His compliments actually began to turn me on, and I could feel another erection growing in my mother's panties. I was surprised that I was turned on by this and began to wonder if I had a praise kink. 

He placed his hand on my lap while he was driving, and he must have felt my erection because he looked over very excitedly. "Oh. What do we have here? Aren't you just a naughty girl? Why didn't you tell me your little clitty was all excited in mommy's panties?"

"Barry... I uh... It just kind of happened."

"That's ok, Nate. Let me ask you. Does my girl want me to give her another orgasm?" 

"I... Yes. I actually think I would like to have another one." 

"I just love how perfect you are, Nate. We were destined for this. Tell me what you want me to do to you."

"I want you to rub my... clit. Like you did earlier. I want you to rub by clit through my panties." 

"Very good girl, Nate. Very naughty girl. Well, I suppose there would be an opportunity to earn a reward."

"Barry. Please don't make me give you another blow job. I'm not ready." I pleaded. 

"That's ok, Nate. What I really want is for you to give me a lap dance. I want to cum and I want you to feel how hard you are making me." 

"I don't know Barry. I've never... danced like that."

"You don't have to, Nate. I think we can make each other happy tonight if you give it a try. Will you trust me?"

"I'll try." I wanted to see if him getting me off was going to be just as good as before. I was definitely horny again, so I guess I am going to have to try to give him a lap dance. 

He lifted my dress in the car while we were driving, exposing my panties. He teased my penis the whole drive to his house. He kept calling me his naughty little girl and explaining how he wanted me to be nice and excited for my dance.