Comforting Pete meets Trophy Wife Ch. 03

Author's Note: This is a continuation of the crossover between Comforting Pete and Trophy Wife. You don't necessarily need to read all of the previous 11 chapters, but you might want to. I hear they're good ;)

FIFTH DAY IN VEGAS

I was the first to wakeup and when I looked to my left, I saw that the four of us had slept together in the bed in our Honeymoon Suite. Pete, Jim and Erica were all still sound asleep. I pulled the sheet back a bit to reveal my naked body. I peeked underneath to see the three of them were naked as well.

I quietly got out of bed and after taking care of my business in the bathroom, I put on a Satin Pink Robe and went into the living room. I sat on the couch and turned on Sportscenter. I may be a hot babe now, but my brain still loves sports. I had a feeling we would be betting some more today, so why not do some research while everyone was still sleeping. About twenty minutes later Erica came in wearing a Satin Black Robe.

"I hope you don't mind that I borrowed this," she said, "I didn't have anything else to put on."

"No problem," I said.

She pointed at the TV and said, "Ah Sportscenter. I miss sports sometimes, but between being a wife and a mom, there's hardly any time anymore. You'll find that out soon."

"I'm not so sure of that," I said, "I love it too much and so does Pete. I can't see ever giving it up."

"Ok," she said, "But I'm telling you I'm gonna be right. You're a wife now and he's gonna start talking about kids soon. You'll see."

"I don't know if we'll ever get to that point," I said.

"What do you mean?" She asked. "It's the natural progression of a relationship. Are you telling me you're not all in by now?"

"I'm not sure," I said.

"Look at you. You're a hottie. You can't tell me you still think about being a guy?" She asked.

"I hadn't really thought about it until this trip. It's pretty much the first time I got to fuck instead of being fucked. I got to fuck that hot hooker, you and even Pete," I said.

"You have looked in a mirror, right? You're Jessica, and that's who you were meant to be," she said.

"I guess I'm just confused," I said.

"So you're telling me you think you could back to being...wait, what was your name?" She asked.

I paused for a second and said "John."

"After all you've been through to become Jessica, the boobs, the blowjobs, and taking it up the ass, you really think you could be John again? You would really want that?" She asked.

"Maybe a 10% chance," I said, "Are you telling me you've never considered it?"

"Since the first time Jim made me cum with his dick up my ass I was sold. My life was horrible as Eric, and it's fucking awesome as Erica. Why would I ever want to go back?" She said.

"I'm happy you're happy, but I still have doubts," I said.

"Ok, how about this...we'll tell the boys we're having a girl's day. They can hang out and gamble all day. We'll get you some men's clothes and you can spend the day with me as John. I bet by the end of the day you'll be 100% in on Jessica, deal?" She offered.

"Deal," I said.

"Before we do that, we can't let our husbands down. They have gotten used to waking up a certain way," she said.

"Ok, we can start your experiment right after," I said.

"Wanna switch one more time?" She asked. "You wake up Jim and I'll wake up Pete."

"Fine, but double or nothing on that $10,000 from last night. When I make Jim cum first, we're even!" I said.

"Ok, but don't blame me if Pete is pissed when he finds out he owes $20,000!" She said.

"Race you!" I said.

I dropped my robe and started to run nakedly to the bed. Erica dropped hers and ran as well. I could see out of the corner of my eye that she had put her cage back on. I was first to reach the bed and pulled the sheet off of the guys. They were both lying back, completely naked, with bulging morning erections. The motion from the sheet didn't phase them and they stayed asleep.

Not wanting to wake them just yet, the two of us got on the bed slowly and positioned ourselves in between the other's husband's legs. We looked at each other and whispered 'One, Two, Three.' We opened our mouths and took the guys inside. I felt like I had the advantage, because Jim was smaller than Pete. I would be able to easily take him in my throat while Erica had to deal with a cock larger than she was used to.

Wanting to make Pete happy by winning his money back, I started Jim's blowjob by immediately deepthroating him. He must have been enjoying it because he awoke suddenly with a huge breath and put his hands in my hair. He started to moan and when I glanced over at Pete, he was still asleep. Erica must have been getting frustrated, because I felt the bed start to move as she was working Pete.

A few seconds later I heard Pete gasp and he was awake too. Our husbands looked at each other and realized they had a different girl waking them up than usual. Pete's breathing was getting quicker and I was afraid I was going to lose the bet. I didn't want that to happen so I improvised. I took my finger and put it in my mouth, next to Jim's dick to moisten it. I slowly pulled my finger out and lifted my head up so I had my lips around his tip. I put my finger between his cheeks and teased his asshole. He let out a loud moan and simultaneously I quickly took him in my throat while jamming my finger up his ass.

"Oh My God!" Jim screamed as he came.

I had him so deep that his first shot went right down my throat. All I could feel was his dick getting harder and pulsing. I pulled back a little for his next blast and he coated my tongue. He continued to cum hard and I swallowed as fast as I could. After last night I was surprised how much he still had. When he finally stopped cumming I pulled off to see Erica still blowing Pete. It didn't take much longer before she swallowed his load.

She pulled off him and I put my hands in the air, screaming, "Victory!"

"What was that?" Pete asked, confused.

"I just got back the $10,000 I lost you last night!" I said, excitedly.

"No way! I love you!" Pete said, kissing me, not caring I had just blown his new buddy.

"Erica, I can't believe you let her win!" Jim said, jokingly.

"You cheated!" Erica said to me, "I saw you stick your finger up his ass!"

"Hey, the bet was whoever came first, we never stipulated how to make it happen!" I said.

"Whatever you say. So are you still 90% / 10%?" She asked.

"Maybe 91% / 9%," I said, giggling.

"What are you talking about?" Pete asked.

"Just girl talk," she said, "Do we still get to go jewelry shopping?"

The guys looked at each other and nodded. "Yeah," they said together.

"Cool!" Erica said. "Let's do that a little later though. Jessica and I are going to have a girl's day and you boys can hit the tables."

"Yeah, I'm gonna spend some time with Erica and we'll meet you guys for dinner," I said.

"Sounds good to me," Pete said.

"Yeah, you two have fun," Jim said.

"Great, Jim and I will go to our room and get ready. I'll come back up and get you Jess," Erica said.

"Perfect," I said.

Jim and Erica threw on some clothes from last night and went to their room. Pete and I showered together quickly with no time for any monkey business.

I came out to see a text from Erica: "Hey, don't get dressed, I'm bringing you some clothes."

I put on my robe and started playing with my phone. I didn't want to tell Pete what I had planned for the day just yet, but he was so anxious to get down to the casino he didn't ask me anything. He got dressed quickly and gave me a deep kiss.

"Don't get into too much trouble," he said.

"I should be saying that to you!" I said, jokingly.

"See you for dinner," he said.

"Good luck," I said.

I continued to look at my phone and checking some baseball stats until there was a knock at the door. Erica came in with a couple of shopping bags. She was wearing a short dress with flowers on it and her makeup was perfect.

"Hi John," she said.

Catching me off guard I shyly said, "Hi."

"What, you wanted to try being a guy again, so I'm gonna treat you like one. I guessed at your sizes, but if you remember guy's clothes are easier to pick," she said.

"Thanks, I was wondering what was taking you so long," I said.

"Ok, strip," she said.

I dropped my robe and stood there naked in front of Erica. My perfect C cup boobs were sticking out and other than my dick hanging down limply, there was no trace of manhood anywhere.

She gave me a catcall whistle and said, "Damn, with that body how can you not be 100% in?"

"Let's just see how today goes," I said.

"Alright. Let me show you what I got," she said.

She turned the bags upside down on the bed and a pile of clothes spilled out. There were Boxers, T-Shirts, Shorts, Socks, Sneakers, and a few hats.

"Pick whatever you want and we can return the rest," she said.

"Maybe you want to try some on and be Eric again," I said.

"That ship sailed years ago. I'm Erica. Just hearing my old name is weird. Now would you get dressed already, I'm hungry," she said.

I started with a pair of boxers and pulled them up my legs. I felt like something was missing and I took a few steps around the room.

"What's going on?" She asked.

"I'm not sure, these feel weird," I said.

"Of course they do. The underwear you're used wearing is a thong that rides up your crack. It's probably been months since you haven't worn one," she said.

"Oh yeah," I said.

Next was a pair of shorts. They were longer than the ones I had been wearing and I remembered that my guy shorts always reached my knees.

"How do they look?" I asked.

"They look great. They especially make your smoking hot legs pop!" She said with a smile.

I looked down to see my beautifully waxed legs showing from the knee down. No guy had legs like mine and they would most certainly have hair on them.

"Um, did you get any pants? I don't know if these will work," I said, reluctantly.

"It's 120 degrees, there's no way you can wear pants," she said.

"Ok, these will have to do," I said.

Next I put on a T-Shirt. She had bought be a baggy one so it fit over my boobs. I had that weird feeling again and took some more steps around the room.

"What is it this time?" She asked.

"I'm not used to feeling the weight on my chest. It just doesn't feel right," I said.

"Well duh!" She said. "While your breasts aren't as big as mine, they need support. A bra is another thing you've been wearing everyday for months! Just say the word and you can put on your normal clothes and we can really have our girl's day."

"No, I've come this far. I want to keep going," I said.

"Ok, try on these sneakers. I got you a pair of Jordan Basketball High Tops," she said.

"Cool, those used to be my favorite," I said.

I sat down and pulled on my socks before tying my sneakers. I got up to take a few steps and tripped, almost falling over.

"Now what?" She asked.

"The sneakers feel weird," I said. "I don't know what's wrong with me."

"You're used to wearing shoes with some type of heel," she said, "That's what it is. Same as the underwear, you haven't worn basketball sneakers in forever and you forgot how to walk in them."

"This can't be this hard," I said, starting to get frustrated.

"That's what I've been trying to tell you. You are perfect as Jessica! Even thinking of going back to John is crazy!" She said.

"Erica, that's enough," I said, in a harsh tone.

"Fine, can you finish getting dressed already so we can get some food," she said.

I walked into the bathroom and reached for some makeup.

Erica grabbed my hand and said, "Um, John doesn't wear makeup."

"Oops, force of habit," I said.

I looked at myself in the mirror and saw my long blonde hair.

"Oh no, what am I going to do with my hair?" I asked.

"That's what the hats are for. We'll put it in a ponytail that will stick out the back. A lot of guys wear it like that," she said.

"Good idea," I said.

She took a hair tie and pulled my hair back. She put it through the back of the hat and it looked pretty good. Looking at my face it was so weird to see myself without makeup. I hadn't had any work on my face, but it still looked more feminine than masculine. I wondered if it was just in my mind. Anyway this was the best it was going to get and I was getting a little hungry too.

"Ok John are you ready?" She asked.

"Yeah," I said.

"Great, I bet you've never hung out with a girl as hot as me before," she said.

"Definitely not. Hopefully everyone will be looking at you instead of me," I said.

"Most certainly," she said, "Except there's one more thing."

"What's that?" I asked, confused.

"I don't think John would have a voice so soft and cute sounding," she said.

"Oh no," I said, in my girly voice.

"See what I mean," she said.

"How about this?" I asked, trying to sound manly but still sounding like a girl.

She shook her head.

"How about now?" I asked, getting a little deeper, but not much better.

"Not really," she said.

"I worked so hard in changing my voice to sound like Jessica that I forgot how to talk like John," I said in my now normal girl voice.

"I don't know what to tell you. How about you let me do most of the talking when we're around other people and the rest of the time just try your best," she said.

"Thanks, you're a good friend," I said.

She walked towards the door and I followed slowly. She was totally right, I wasn't used to not wearing a bra, thong, and some type of heel. It was the exact opposite from when I started to wear those things and felt uncomfortable. When I finally got to the door she was laughing.

"Doing ok there Pal?" She asked.

"Yeah, I'll get used to it again," I said.

"Come on Jess, let's go back inside so you can throw on a cute little dress and we'll be two hotties walking around the casino!" She said.

"It's John," I said, "Can we please just go eat."

We went down to the restaurant and I didn't speak when the waitress was around. I had Erica order for me and I tried to stop squirming in the booth so much. I can't believe I was thinking like this, but I really missed wearing a thong. We finished breakfast and walked towards the Blackjack tables.

I was still walking slowly and the weight of my breasts was making my back hurt. Now I was missing wearing a bra. What the hell am I doing? My life is so much better as Jessica. Why am I even thinking of being John again? Just then two hot blondes with huge tits walked by. My eyes locked on them and I stared at them until they were out of my sight.

Erica saw and asked, "See something you like?"

"Yeah, those girls were hot!" I said.

"Hotter than me?" She asked, with a fake sad face.

"Of course not," I said.

"Why don't you go talk to them?" She asked.

"I could never," I said.

"Why, because your boobs are almost as big as theirs," she said.

"No, because I could never get a girl that hot," I said.

"Um, you've had me, more than once," she said.

"Yeah, but that's different," I said.

"How? You said I was hotter than them," she said.

"It's just...I mean...screw you," I said, frustrated.

"I guess I hit a nerve, huh," she said. "What would be the point of being John if you're not going to chase after hot girls? Jessica has a hot guy that takes care of her every need financially and sexually."

"I...I...I..." I stuttered, not knowing what to say.

Just then Pete and Jim walked up to us.

Pete said to Erica, "Hey, who's your friend? Where's Jessica?" Before she could answer he took a longer look at me and said, "Jess?"

"Yeah, it's me," I said.

"What are you doing? Why are you dressed like that?" He asked me.

I froze and Erica answered for me, saying, "She was a little confused, so we decided to try something."

"Confused about what?" He asked. "Is that what that 90% / 10% stuff was?"

I just looked at him, still speechless. Erica said, "Yeah, she was having some second thoughts and when I questioned how she wasn't 100% in, she told me she was 90%."

"Erica, while I appreciate you trying to help, this is between me and my wife," he said.

"Of course, we'll leave you two alone," she said.

Erica grabbed Jim's hand and they walked away.

"Sweetie can you please talk to me," he said, concerned.

"Can we go upstairs? I feel weird talking about this in the casino," I said.

He took my hand and we walked to the elevators. I was still walking slowly, because I was still uncomfortable in these clothes. Pete didn't rush me and we walked into the Honeymoon Suite. We sat down on the couch and Pete got a couple bottles of water.

"I'm worried about you," he said, "Can you tell me what's going on?"

I took a deep breath and started, "Pete, you're my best friend and the last six months have been amazing. I've completely changed my life for you and I've been so happy. Then this trip happened and I got to do some new things that have given me some doubts. I really enjoyed being able to fuck again. Believe me, what we do together is awesome and I don't know how I ever lived without it. It's just that sometimes I miss being John."

"You know I love you, right?" He asked.

"And I love you too," I said.

"Let me ask you a serious question though...Were you ever really happy as John?" He asked.

"I guess not," I said.

"And these experiences you're talking about, didn't you have them as Jessica?" He asked.

"Well yeah," I said.

"So wouldn't it make sense to be Jessica, continue the wonderful relationship we have, plus be able to experience other things?" He said.

"That makes sense," I said.

"Feel better now?" He asked.

"I'll feel a lot better once I get out of these clothes. I actually miss wearing a bra and a thong!" I said.

"Ha, see, how many times did I tell you you'd get used to them?" He said.

"You're always right!" I said and kissed him.

He stood up and took my hands. He pulled me off the couch and in an instant his lips were on mine and he was kissing me. I started to moan and he unsnapped the front of my shorts. He pulled them down along with my boxers and he untied my shoes and threw my socks across the room. Next he took off my hat and let my hair down. He reached into the collar of my T-Shirt and ripped it off like Hulk Hogan used to. I was completely naked and he took my hand and walked me over to the bathroom vanity. He quickly stripped off his clothes and stood behind me.

"Look at yourself," he said.

I looked at myself in the mirror and staring back at me was my long flowing blonde hair and my beautiful tits. I smiled.

"See, even without makeup you are so beautiful," he said.

"Yeah, I guess I am," I said.

"I can't believe that you were still 10% unsure," he said, seriously.

"I was just a little confused after yesterday," I said.

He reached around me and grabbed my boobs, gently stroking my nipples. I let out a soft moan.

He said, "Look at the amazing breasts you have and how they make you feel. It blows my mind that you're not completely happy."

"Please don't be upset with me," I pleaded.

He kissed my neck as he continued to rub my breasts. "I'm not upset with you, I'm upset with myself that I haven't fucked all the John out of you yet."

"Mmmmm," I moaned, from the pressure of his kisses and his fingers on my erect nipples.

"That's more like it," he said, "Do you realize that in all the craziness yesterday, it was the first day I hadn't fucked you since we've been together? Well, that's about to change! I'm gonna make sure I fuck you every day for the rest of our lives. In fact we have about three hours until we have to meet Jim and Erica for dinner, and I'm going to make sure there's no trace of John left!"

With that he took my hands and placed them on the vanity. I bent over as he spread my cheeks and thrusted all the way inside me. As he pushed fully into me, I rocked forward slightly onto my toes to ease his entry, but he grabbed my waist and pulled me back hard.