Stephanie's Toy Ch. 05

Thank you for all of those who have waited so long for the next installment of this story! I hope that everyone will enjoy this chapter. As always, please send me any constructive criticism you have but please keep the negativity to yourselves. Enjoy :)

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"No, like this," Stephanie said taking the brush from my hand. She carefully painted the eye liner onto my face. "See?" she asked.

Stephanie and I were having a girls night. We had wine and chocolate and each other. What more could a girl ask for? We had spent most of the evening watching makeup tutorial online. We would watch a video and then try to recreate in on my face. I had gotten pretty good at applying makeup but I was nowhere near as good as Stephanie was. I looked at myself in the mirror.

"Wow," Stephanie said. "So pretty!"

"Thanks," I said. I poured us another glass of wine. We deserved this. The past few months had been a whirlwind for the both of us. Stephanie had continued to be successful at the office. She had managed another promotion. It had to have been a record of some sort. I spent years in that company and got nowhere. Stephanie had risen to corporate levels practically overnight.

As for me, I had just finished my sixth month on hormone replacement therapy. It was going well. My body now had the feminine figure I used to dream about. My hair was long, my hips were wide and I had developed breasts!. They were small but I liked them. I felt like they went well with my slender frame. I had also had some success at work. I had been promoted to assistant manager. I loved my job. I didn't think I would at first. Folding clothes all day and running a cash register didn't seem very exciting. But I loved the girls I worked with. Ariana and I had become good friends and Stephanie and I hung out with her often. There were several other girls who I was close to as well. I felt more loved and accepted than I ever had in my life. Stephanie had been right. Submerging myself in feminine culture had given me a whole new outlook on what it meant to be a woman.

There was a time in my life, not so long ago, where I thought of women purely in sexual terms. Even when I use to dress up as a woman, it was always a woman who was having sex. Now that I was becoming a woman, thing had changed. There is a lot more to being a woman than putting on pretty underwear and having sex. Stephanie was proud of me when I told her that.

"Brooke?" Stephanie was staring at me. I had been zoned out. "What are you thinking about, hun?"

"Oh, I was just thinking about how happy I am and how I would never be here if it wasn't for you."

"Awe, your so sweet," She said. She wrapped her arms around my neck and kissed my cheek. "I love you, bestie".

"I love you to," I said. "Common," I said , grabbing our bottle of wine. "Let's go watch a movie.

Stephanie and I curled up together on the couch and flipped through the television looking for something to watch. It really didn't matter to me what was on. I was just happy to be cuddling with my best friend. Eventually we landed on a cheesy 90's chick flick. Perfect for girls' night.

We laid there together for a while. It was perfect. Then Stephanie grabbed my boob. She did that a lot now.

"I just love your breasts. They are so cute!" she said.

"Thanks," I said. I liked them too.

By the end of the movie, the first bottle of wine was gone. I opened a new one. Stephanie was starting to get a little drunk. Stephanie tended to get a little feisty and a little horny when she was drunk.

"You are such a good little pet," She told me, while rubbing her hands down my body. "I'm so happy when you do what I tell you to. Get on your knees for me"

Mine and Stephanie's relationship had changed over the past few months. She was much warmer and affectionate to me. But she was still in charge. I obeyed her every command. Since she didn't have blackmail to hold over me anymore, Stephanie developed a system of punishments for when I disobeyed her. Her favorite thing to do was to spank me. I got spanked a lot. She also denied me privileges like hanging out with my friends or hanging out with her. And Since she had the job that paid most of our bills, she also took away my allowance when she felt I didn't deserve it. I felt a little like I was in high school but that was ok. I owed Stephanie my life

I slipped off the couch onto my knees in front of her. "Good girl," Stephanie told me. "Little girls like being on their knees, don't they?" Stephanie brushed the hair out of my face.

"Yes, ma'am," I answered. Stephanie loved it when I referred to her as "Ma'am, or Miss and occasionally "Mistress". She didn't force me to but I knew she liked it and it won me huge brownie points.

"Here, baby," Stephanie told me, slipping her underwear off. "Lick me."

I buried my face in her pussy. This was something that I could never have done as a man. Stephanie would barely touch me back then, except for our little games we played. I was happy for a peck on the cheek. Now we cuddled and kissed and held hands regularly. And she had me eat her out all the time.

Stephanie's breath quickened and I felt her clit become engorged with my tongue. I had become good at eating pussy. Stephanie thought that it was essential that I learned.

"Oh yeah, baby," she sighed. "Such a good pet." I sucked on her clit. "MMM, baby," she cried. "You are such a good girl"

I loved hearing her say that. I loved being her "pet".

I started licking her faster. Stephanie's hips bucked. I felt her hands go to the back of my head and her legs closed on me. She cried out in ecstasy and her body shook as she came. I loved giving her pleasure.

After Stephanie had come down from her orgasm she invited me to rejoin her on the couch.

"Pull down your shorts," She commanded me. I did immediately. I sat on the couch beside her. I was wearing only panites and the chastity device that I had become accustomed to. My skin was soft and smooth, Cleanly shaven. Stephanie retrieved the key to the device and unlocked me. My little dick felt free. The cool air rushed across me, but it did not stir.

"What were you thinking about just now when you were eating me out?" Stephanie asked.

"Just how beautiful you were," I told her.

"And you didn't start to get hard?"

"No," I answered her.

"What about now?" she asked. Her fingers traced the outline of my limp dick. It felt good. But still my cock did not grow.

"No," I responded. Stephanie stood up. She stood in front of me and did a strip tease. She peeled off her top and took off her bra. Then she crawled into my lap and kissed me lightly on the lips.

"What about now?" she asked.

I was horny. I wanted her badly. I could feel the excitement in my stomach. But even with a sexy, young completely naked girl in my lap. I could not get hard. I felt blood rush to my genitals. Everything became more sensitive and I was horny. But there was no hint of an erection.

"No," I answered her again.

Stephanie looked at my limp dick and smiled.

"Perfect," she said. "I think it's time you stopped wearing this cage around. I don't think you need it anymore."

"Seriously!?"

"Seriously." Stephanie took the cock cage and key and dropped it into the trash can. I felt like I had just passed some huge test. Stephanie put her cloths back on came back to the couch.

"There's something I want to talk to you about.." She said. "Tomorrow I'm going on a date with a guy I've been talking to at work.

"Okay, great." I said. Stephanie went on a lot of dates. The jealousy never faded but I took solace in the fact that when she changed to a new guy I would still be her best friend.

"Brooke," She said. "I promised him I would introduce one of his friends to one of my friends.."

"No, Stephanie. We've talked about this. It doesn't matter how I look. I'm just not attracted to men!"

"You just haven't met the right one yet." Stephanie told me. "Listen, dating is a part of being a woman. It's fun and exciting and you need to get out there. I'm not saying you have to do anything with this guy. Just give him a chance is all."

"Stephanie .. I can't. You are the only person I'm attracted to. You know that." I pleaded with Stephanie.

"Brooke," She said. "You know I love you. You are my best friend, roommate, lover, but Brooke, I NEED a man. A real man who can make me feel like a woman. I need a man and you do to.

The conversation was over at the point. There was nothing I could say to convince her she was wrong.

+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++

They were picking us up at 5. We were going to see an early movie. Then go to eat. I did my makeup and hair and picked out a cute little dress to wear. I wasn't interested in this date but that was no reason to not look good.

The guys arrived at 5. Stephanie introduced me to her date. His name was Matthew. He was tall and attractive. He had a short beard and short brown hair. Matthew introduced me to his friend, Jake. I was stunned when I saw Jake. I KNEW him! We use to work together. My voice quivered when I said hello. He looked at me. I could see fire in his eyes. But no recognition. Thank god.

We drove to the movie, a romantic comedy. I didn't like it much. Stephanie and I sat in the middle, between the men. I was happy to have Stephanie for support, that is, until the middle of the movie when she and her date started making out. I felt Jake's hand touch my arm. He was sort of leaning towards me with his body. I could tell he wanted the same thing Matthew wanted. Not a chance.

The movie ended and we headed to dinner. Jake was near me constantly. It was exhausting. He opened my door and held my hand. He took my coat for me and pulled out my chair. It was actually very sweet but I was annoyed. To me it looked like he was trying to hard.

On the other side of the table, Stephanie and Matthew were having a great conversation. Stephanie clearly liked him. Her body language was easy to read. They flirted heavily. It made it sort of awkward to sit next to Jake. I could tell he wanted the same thing but I was not interested. I was happy when the food arrived. It was a good way to avoid conversation with my "Date".

The meal was good. We all had dessert and Stephanie and I had a glass of wine. The night was winding down. I was excited that it was almost over. Then Stephanie said "Would you guys like to come over to our place for a drink?" My heart sunk. Our dates agreed immediately.

We headed back to my house. Once we made it back Stephanie pulled me aside.

"Listen," she said. "I can tell your heart isn't into this but I need you to make an effort. Do you understand." I could tell this wasn't a friendly suggestion, it was an order.

"Yes, ma'am." I answered her.

"Good, I'm going to give you a mission. You must complete it or you will lose all privileges and your allowance for the two months. Do you understand?"

There was no use in arguing. I knew I had to do what she said. "Yes, ma'am," I answered.

"Good. Here is what you are going to do. You are going to make Jake feel like you want to be here. You are going to flirt and talk and laugh. After tonight you are going to go on two more dates with him. By yourself. If he doesn't ask you out again. You fail. Do you understand?"

My stomach was filled with dread. I nodded my head.

"This doesn't have to be bad you know, "Stephanie told me. "I've gone on lots of dates with guys I wasn't interested in. You don't have to be interested to enjoy a person's company or to let them do nice things for you. All I'm asking is that you give him a chance."

I nodded, put on my best fake smile and headed into the living room where the boys were waiting for us.

"Who wants to play a game?" Stephanie asked.

"What game?" Matthew answered first.

"Truth or Dare," Stephanie answered him.

The boys laughed. "A little childish don't you think?" Matthew made fun of Stephanie. She punched him on the arm.

"Shut up!" She told him. "You're just scared!"

They laughed and play fought and trash talked each other for a couple of minutes before we all agreed to play. We sat on the floor in a circle.

"Okay," Matthew said. "Stephanie goes first. Truth or Dare?"

"Dare," She said right away. She had a devilish grin on her face.

"I dare you to take your shirt off." Stephanie immediately took off her top. Her skin rose up in goose flesh. She still had her bra on.

Next it was Jake's turn. "Truth or Dare?" Stephanie asked him.

"Dare." He said.

Stephanie thought for a minute and then said "I dare you to take your shirt off."

Everyone laughed. "To easy," Jake said and pulled his shirt over his head. Jake's body was sculpted. He had a six pack and huge muscles in his arms and back. I was temporarily shocked. I hadn't expected that.

"Okay your turn Brooke. Truth or Dare." Jake asked me.

"Truth," I answered after a moment of thinking.

"Hmm..." Jake though. "What is your favorite feature on a guy?"

I thought a minute trying to come up with a great answered. "Eyes," I said.

"Wrong answer!" Stephanie said. "Try again."

I thought a minute. I was looking at Jake and my eyes kept being drawn to his abs so that what I said. "Abs". Apparently this was an acceptable answer because the game moved on.

We played for a while. And we drank. Everyone was brave and took dares, except me. Stephanie licked Jake's face. Matthew sucked Stephanie's Toe. Jake ate year old peanut butter. I told everyone what my favorite food was. Then Stephanie did a seductive dance, Matthew took off his pants, Jake did push ups while singing the star spangled banner and I told everyone about my first kiss. That was a mistake. I told everyone about a girl who I knew in highschool. She had just had her heart broken and we were talking. She was emotional and said I was sweet and kissed me. That was my first kiss. The boys were staring at me. I didn't realize why at first. Then it occurred to me. They thought I was a girl and that my first kiss was with another girl. They didn't know that at the time I was a 15 year old boy. Crap.

"So are you bi-sexual or something?" Matthew asked.

"Ummm," I tried to come up with a good answer. Really the answer was no. I wasn't Bi. I liked girls and not boys which made me ... Straight? or Lesbian? This was a confusing question. Of course I couldn't say either of those answers. I needed to make Jake like me and telling him that I was only into girls wouldn't help.

"Yes," I said. "I am."

I could see the boys imaginations running wild. Matthew was the next to speak up.

"Okay, Stephanie, your turn. Truth or Dare?"

"Dare," She said.

"I dare you to make out with Brooke." Stephanie looked at me. This was an easy dare. We had made out dozens of times. She crawled across the floor to where I was sitting and placed her lips on mine. My hands went instinctively to her bare torso. I felt her tongue graze my lips. I open my mouth and met her in the middle. Stephanie pushed me onto my back and climbed ontop of me. My hands traced her spine, hers ran through my hair. This felt right. This was how things should be. I temporarily forgot about the men in the room. I cupped Stephanie's breast in my hand as she kissed me. We were locked in a deep embrace. We made out for several minutes before Stephanie ended the kiss and crawled back to her spot in the circle.

I could see Matthew's erection easily. He was only wearing boxers and they didn't leave much to the imagination. I looked over to Jake. He still had his pants on but I could see his excitement too. It made me feel good that these two enjoyed our show so much.

The game deteriorated pretty fast after that. Everyone finished their drinks. Matthew and Jake rose and said they should probably leave, I got the feeling they were looking for an invitation to stay. Stephanie, as if on cue, provided them with one.

"You two have had too much to drink tonight. Maybe you should stay..." She said.

The accepted right away.

It didn't take long for Matthew and Stephanie to make their way to Stephanie's bedroom.

"I'm getting tired." Stephanie said." Matthew, you can sleep in my bed if you want..."

Matthew got the hint and they headed down the hallway. I felt a familiar jealousy as I heard the door close.

Now I was alone in the living room with Jake. We sat in silence.

"Would you like to watch T.V. or something?" I asked him to break the tension.

"Sure," He said.

I climbed onto the couch and turned the T.V. on. Jake sat down beside me. Right beside me. Confidently, he put his arm around my shoulders. I felt a little awkward with his arm around me, but I didn't push him away. There was nothing on T.V. We sat and quietly flipped through the channels.

A new sound began to fill the living room. Heavy breathing, panting, a soft moan, then a louder one, a rhythmic wet pounding. Stephanie and Matthew were fucking. I pretended not to hear but the sounds grew louder and pretty soon it was all I could focus on. I felt myself start to grow aroused. Stephanie's voice carried into the living room.

"Oh yes," She moaned. "Harder, please" I heard her beg.

Jake was aroused too. I could see his cock growing again, under his pants. His grip on me became tighter. He pulled me close to him. He tried to play it cool but I knew what he wanted. I was terrified. I knew he wanted me to fuck him but I couldn't do that, not even if I wanted to. But on the other hand, if I turned him down he might not call me back. And I needed to go on two more dates with him to avoid being punished by Stephanie. I was going to have to give him something...

The sounds of sex grew louder and Jake decided he was tired of waiting. He made his move. He went in for a kiss. My first instinct was to pull away from him but I forced myself not to. Jake's lips found mine. He held me firmly and kissed me roughly. His lips parted mine I felt his tongue slip into my mouth. I accepted his advance and kissed him back. I focused on the sounds of Stephanie's pleasure. I found that this was easier if I focused on her. Jake took my acceptance of him as approval to go further. He pushed me down on the couch. He was much stronger than me. He unzipped my dress and pulled it down to my waist. My bra still covered my breasts but he did away with that quickly. Now our bare skin came together as he began to kiss me again.

His kisses were passionate. Despite myself, I began to feel attracted to him. I didn't know what it was. His muscles? His confidence? The way he was manhandling me? Maybe it was the fact that Stephanie had just cried out in a massive orgasm. Whatever it was I began to lose control of myself. Jake's hand cupped my bare breast. He pinched my nipple. I gasped. He covered my mouth with his. He had crawled between my legs and I wrapped my legs around his torso.

Jake began to work his way down my body. He secured my hands above my head with one muscular arm. I felt vulnerable and weak . He stopped kissing me on the lips and moved down to my neck. He spent a few minutes kissing me there. I felt a sharp pain as he bit me softly. Then he moved down further, to my shoulders and then my exposed breasts. He spent time on each of them, licking and kissing and biting them. I knew I was going to have bruises in the morning. He took each nipple into his mouth and massaged them with his tongue. Now I was the one moaning. This felt great. He buried his face into my breasts and then moved down to my abdomen.

His kisses were fiery. He took his time biting and kissing his way down my body. He was now below my belly button. Things were beginning to get dangerous now. He went further, I could feel his kisses just above my pubic area. I wanted him to keep going. My body ached for him. But it had to stop now.