Comforting Pete Ch. 03

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John reevaluates his weekend only arrangement.
10.7k words
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Part 3 of the 4 part series

Updated 07/14/2023
Created 07/07/2023
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WhyNotUs
WhyNotUs
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SATURDAY

I was having the most wonderful dream. I was on vacation with Pete in Las Vegas as Boyfriend and Girlfriend. We would walk around the casino with me wearing one of those skimpy dresses you see girls in Vegas wear. We hung out in our cabana by the pool with me in my bikini. Then we spent the night fucking on the balcony of our suite. I was starting to moan in my sleep and was startled awake by a pinch in my lower back.

I opened my eyes to see Pete staring into my eyes. He had my ankles on his shoulders and he had just penetrated me.

"Good morning Jess," he said.

"Good Mor-Oh My God," I screamed as he plunged himself all the way into me.

He started to fuck me hard with deep strokes. I was still groggy so I let him do all the work. I felt kind of slutty with my legs up in the air like that, but in this position he was hitting me in all right places. I started to moan and quietly saying, "Yes, Yes, Yes," as I was still coming out of my deep sleep. My breathing quickened and he started fucking me faster. I was getting close, but then he yelled out and came inside me.

He pulled out and rolled over next to me. We were both still breathing heavy and he asked, "How was that?"

"What a way to be woken up!" I said. "But..."

He looked down to see my rock hard erection sticking straight up. "Oh, I'm sorry, you didn't get to cum."

"That's ok, I guess its part of being the girl," I said.

"No it's not," he said, "In this relationship I want you to be as happy and as satisfied as me."

"Thanks," I said.

"How about this?" He began. "Why don't we take a shower together and I can finish taking care of you in there. I might need some help getting started again with your talented mouth though." He winked at me.

For some reason I licked my lips in anticipation. Did he really think I had a talented mouth? Is that the kind of skill I really want? "Ok," I said, "I was having the most amazing dream and could use a release."

"Was it a dream about me?" he asked, suggestively.

"Mm-hmm," I agreed.

He grabbed my hand to pull me off the bed and said, "That's so hot. Come on, tell me about it in the shower."

He turned on the shower to warm it up. I was already naked except for the Breast Forms. I unhooked them and took them off. They were able to get wet, but I needed to wash my entire body. We got in the shower and just enjoyed the hot water and steam for a minute. I looked down at his dick and it was still pretty soft. I dropped to my knees and gobbled it up. He let out a happy groan. The point of this was not to suck him to completion, but to get him hard enough to fuck my cum out of me. I bobbed my head up and down really quickly and that did the trick. When he was sufficiently hard I pulled my mouth off and kissed the tip.

I stood up facing him and he kissed me with his tongue, not caring that my lips were just wrapped around his cock. We made out for a bit and he pushed me against the wall. He lifted me up by my waist and held me up against the wall. He was so strong I wasn't afraid he was going to drop me. I went to wrap my legs around his hips and he stopped me for a second to line up his dick with my asshole.

"Ready?" He asked.

"Oh yeah Babe," I said, softly.

He pressed against my opening and pushed in. I wrapped my legs around him as he buried himself slowly in me.

I was exhaling quickly as I enjoyed my first shower fuck. I was impressed that he could hold me off the ground like this and still thrust back and forth so easily.

"Feeling good Jess?" He asked.

"Your dick feels so good. It feels so big!" I said.

"Maybe we should do it like this more often," he said.

"I'm your Girlfriend on the weekends and you can fuck me any way you want," I said, moaning.

"Tell me about your dream," he said.

"We were in Vegas," I began, but stopped to catch my breath.

He jabbed into me hard and said, "And were you John or Jessica?"

I couldn't believe he mentioned the name John with his dick all the way up my ass. Breathing heavy I said, "Jessica."

"What were we doing?" He asked.

"I was wearing a tiny dress around the Casino, they I was wearing a bikini in our cabana, and then you fucked me on the balcony of our suite," I said.

He pulled out his dick to the tip and thrusted back in hard. I screamed and he said, "That's awesome. "Is that something you want me to do? Take Jessica to Vegas?"

"Yesss," I said as he started to fuck me faster. Not sure if I was agreeing to his question or to the pleasure I was receiving.

"That might require more than a weekend," he said.

"Mmmmm," I moaned, getting close to cumming.

My body was getting goosebumps and I gripped him even tighter with my legs. He knew what was coming so he focused on the spot inside me he's gotten to know so well. I exploded all over his chest, finally achieving my orgasm I missed out on from my wakeup fuck.

He put me down and I was still tingling. "Thank you, that was great," I said, softly, still coming down from cumming so hard. Then I looked down and he was still hard. "Oh no, this time you didn't get to cum."

"That's ok," he said.

"No it's not. In this relationship I want you to be as happy and as satisfied as me," I said.

"Using my words, I love it!" He said. "So what are you going to do to rectify this issue?"

I dropped back to my knees and took him in my mouth again, not caring that it had just been inside my ass again. I sucked him deep, knowing this wouldn't take long. I took him in my throat and that sent him over the edge. He unloaded for the second time this morning, right down my gullet. I stood up and we washed each other.

We toweled off and he asked, "So what do you think about tonight?"

"What about it?" I asked.

"Remember last night I said I wanted to take you out to dinner," he said.

"Oh right," I said, "I don't know Babe."

"Come on it will be fun. We can spend the afternoon here and then I can take you to a Salon. I have a friend from work whose wife owns one. She'll take good care of you and get you ready," he said.

"Are you sure?" I asked. "I'd be nervous that everyone would be staring at me."

"They should be staring at my beautiful Girlfriend," he said, winking.

"Can I think about it a little more?" I asked.

"Sure it's only 11am. Why don't I make the appointment for 4pm and dinner for 6pm. We can always cancel," he said.

"Ok," I said.

He pulled on a t-shirt and a pair of boxers and said, "Why don't you get yourself ready and I'll make some breakfast."

I was a little jealous of how fast he was able to get dressed. Being a girl added a whole new level to getting ready.

"What should I wear?" I asked.

"How about a bikini? We can have breakfast on the patio and then we can enjoy the Jacuzzi and the pool for a bit," he said.

"Sounds good," I said.

He kissed me on lips and left the room. I picked up my breasts and wig and walked into my room where all my clothes and makeup were. I opened one of the drawers to look for a Bikini. Yes, there were so many Bikini options that there was an entire drawer dedicated to them.

There was a full assortment of colors, but before I even opened the drawer I knew what I was looking for. I pulled out a Pink Bikini that matched my favorite lipstick.

I hooked the breasts around my chest and put the Bikini top on over them. Both times I had worn one, I only had my little man boobs to fill it out. Now I had the real things, or at least what was closest to the real things, to enhance myself. I was totally limp down below and did my best to tuck myself. The bottoms were essentially a Thong and my butt swallowed up the back. I checked myself out in the mirror doing my best to see behind me. He was right, I did have an amazing ass!

I sat down at my makeup table and put my wig on. As I looked at myself in the mirror I wondered what they would do to me at a Salon. I had gotten pretty decent at applying makeup, but I'm sure a professional would do it perfectly. Maybe she could teach me some tricks. Did I want to learn more about putting on makeup? This is only supposed to be a weekend thing, right? No matter how much I resist I know he's gonna talk me into going out to dinner with him tonight, so I might as well just embrace it.

I brushed my cheeks to get a bit of a pinkish hue. I didn't bother with fake eyelashes, because I figured I was going to get my face wet in the pool anyway. I applied my Pink Lipstick and was ready for some breakfast. I found a pair of Pink Sandals that matched my outfit closely enough and I went to meet Pete in the backyard.

While I was getting ready he had made pancakes. He was a great at making breakfast and on the barbecue. His other cooking skills were lacking, but I guess that would be his Girlfriend's job. The table had large carafes of Coffee and Orange Juice with a vase of fresh flowers in the middle. He certainly was good at presentation. I sat down and poured myself some coffee and juice.

I tasted the pancakes and said, "Wow, these are great."

"Glad you like them," he said.

We were both hungry so we ate and weren't talking much.

"Oh," he broke the silence, "I spoke to Joan and she said 4pm at the Salon is perfect. It would just be her and her assistant, so you won't feel uncomfortable. Then I made a reservation at Mastro's for 6pm. I have a feeling you'll like that place."

Like that place? He knows that's my favorite restaurant on the planet! This was his way of convincing me and its working.

Deciding to keep up the act since Jessica has never been there I said, "Yeah, I heard they have an awesome Seafood Tower and their Bone-In Filet Mignon is off the charts!"

"Sounds like you want to go," he said, "So that works for you? 4pm Salon and 6pm Mastro's"

"Ok," I said.

"Great, I'm so excited," he said.

"Me too," I said. I was more excited about dinner than whatever was going to happen at the Salon, but I knew it was a package deal. "Wait, did you say her name is Joan?"

"I know, another J," he said, laughing, "But this time it's just a coincidence."

We finished eating and spent some time in the hot tub and pool. By the time we were done it was only 1pm so Pete suggested we get changed and watch some baseball until it was time to leave. We showered in our own bathrooms and I was faced with getting ready again. I wasn't just getting dressed to hang out in the house, but to leave the house in girl's clothing for the first time ever.

I went with something simple, Black Bra and Thong and a White Dress. The dress had normal sized shoulder straps and showed off a little boob, but not too much. It had a black satin strip around the waist that mimicked a belt, a flowing white skirt that reached my knees. I applied the same basic makeup and put on a pair of white sandals.

When I got to the Family Room Pete was sitting on the couch drinking a beer and watching the game already. I felt like I hadn't had a beer in a while so I decided to grab one for myself. I sat down next to him and he didn't comment about my choice of wardrobe or my choice of drink. He was focused on the game and would occasionally make comments to me about what was happening. He was treating me like his Buddy while I was wearing this cute dress for him. It was kind of nice to be hanging out with him like this though.

The game ended and it was getting close to my appointment time.

"You ready to go?" he asked.

"Ok," I said, "Oh wait, don't I need to bring a change of clothes for tonight?"

"Nope, you're good, Joan will have everything you need," he said.

"Really?" I asked.

"Yeah, I gave her all your measurements, she's going to take good care of you," he said.

As had been my pattern, I reluctantly agreed and just went with it. I could already taste that Mastro's dinner and whatever was about to happen in the next two hours would be worth it.

Pete drove to the Salon and parked in front. He walked me in and introduced me to Joan and her assistant Ann.

"Ok Jess, these wonderful ladies will take care of you and I'll pick you up at Ten to Six for dinner," he said.

"You're not staying?" I asked nervously.

"No, let them do their thing," he said, "I have to go home and get dressed anyway."

He pecked me on the lips and walked out.

"Ok, let's get started," Joan said, "Pete told us about your, um, situation. Don't worry, we get girls like you all the time. There's nothing to be nervous or embarrassed about."

"Thanks," I said.

"Why don't you take off your dress and we can see what we're working with," Joan said.

I pulled the dress over my head to reveal my Black Bra and Panties.

"Wow Jessica, you have a great body," Ann said. "How long have you been wearing women's clothes?"

"Only a couple weeks now, this is my first time out of the house," I said.

"No way," Joan said, "Your body is so feminine."

"What exactly did Pete tell you about our relationship?" I asked.

"He told me he had a new Girlfriend with a little something extra and she wanted to be made over for dinner at fancy restaurant tonight," Joan said.

"So he didn't tell you this is only a weekend arrangement?" I asked. "I am a guy named John during the week."

"Oh, that's a shame, with the body you have and such a pretty face, you should have been a girl all along," Joan said. "Maybe once we're done here we can convince you to be Jessica all the time."

"I don't know about that, the weekend gig is working pretty well for me," I said.

"Ok," Joan said, "Pete wanted us to give you the full package for tonight."

"Whatever he wants is fine," I said, trusting his judgment.

"I see that you've shaved but there's some hair starting to grow back," Joan said.

"Yeah, it's kind of a pain in the ass to do," I said.

"That's convenient because the first step is a full body waxing," Joan said.

"I'll go get everything setup," Ann said.

"That sounds painful," I said to Joan.

"It won't be too bad, especially since you don't have much body hair right now," Joan said.

"Ok," I said.

"Get undressed and I'll take you in the back," Joan said.

I took off my Bra, Breasts and Panties. I had my dick tucked back, but when I took my Thong off it sprung into a mini erection. My face got red and I said, "Sorry."

"Don't be shy, it's just us girls," Joan said. "I see you have some little boobies going. Have you thought about getting them enhanced? Then you won't have to worry about those Breast Forms."

"Remember, this is just a weekend thing," I said, "I need to be able to go to work and face my family."

"Oh, yeah, right," she said, not believing me.

I walked into the back and Ann told me to lie down on the table. The warm wax felt kind of nice, but when she pulled the first strip off I yelped. She told me to relax and I would get used to it. She was right, as she continued to go down my body it didn't hurt as much. She waxed my pubic area and lifted my legs to do my ass.

"Oh," she said when she spread my cheeks.

"What?" I asked, panicked.

"Someone's been naughty," she said, giggling.

My face turned beet red from the embarrassment. I stuttered like I've never stuttered before, "It's...I mean...I...don't..."

"Relax my dear, we've all done it. Pete is a big guy so I'm sure he's big where it counts. You should be honored he picked you to do that with," Ann said.

"Yeah, I guess," finally stringing together some words. "Can you just finish please? I'm getting a little uncomfortable in this position."

"No problem sweetie," she said.

She finished waxing me and then coated my entire body in lotion. The cold cream felt amazing on my newly bare skin. She handed me a robe and directed me to sit in a chair.

"I can see from your lips that you are a fan of Pink. Let's go with that," Ann said.

"For what?" I asked.

"Your nails, silly," Ann said. "The next step is a manicure and a pedicure."

"But I have to go into work Monday," I said, panicked.

"Don't worry, we'll send you home with a bottle of Nail Polish Remover. You can take it off whenever you want," Ann said.

"Ok," I said.

Ann proceeded to paint my fingernails and toenails in a bright shade of Pink. My fingers looked so weird it's like they weren't even mine. She had me sit still while everything dried and then she escorted me to the front to see Joan.

I sat in a new chair and Joan said, "Why don't you take your wig off so I can see your natural hair?"

I agreed and once it was off I said, "I don't think there's much you can do. I probably need it or else I'll look silly."

"Nonsense, I'm an expert with these things," Joan said. "What do you think about being a brunette instead of a blonde?"

"I've hair brown hair all my life, so it's fine with me," I said, "But Pete might have been counting on me as a blonde."

"He told me to do whatever I felt was necessary, so I wouldn't worry about him," Joan said.

"Ok, as long as he won't be upset," I said.

Joan took a brush and styled my hair a bit. "Is it ok if I cut it a bit?" Joan asked.

"Not really, I can't look too different for work on Monday," I said.

"Alright, I'll figure it out. Is gel and hairspray ok?" Joan asked.

"Yes, of course," I said.

"Spin your chair around and let me do my magic," Joan said.

She walked away and came back with what looked to be a bunch of fake hair.

"What's that?" I asked.

"Hair extensions," Joan said, "They clip in and look amazing. Then you can take them off as you please."

"That should be ok," I said.

Joan held some up to my head until she found some that matched my natural color. The next process took a while. She would attach some hair, brush it, and repeat. I was facing away from the mirror so I couldn't really see what she was doing. She had a blow dryer going and I felt gel being rubbed into my scalp. I could tell she was a perfectionist which wasn't the worst thing. When she finally spun me around I was shocked.

My new hair was about the same length as my wig, which was fine with me. I could feel it on my ears and it just about reached my shoulders. There was hair on my forehead as she had given me bangs. Joan said it was called a Bob.

"What do you think?" She asked.

"It looks b..b...beautiful," I stammered.

"Glad you're happy with it," she said.

"B...B...But how can I get it back to normal for work?" I asked nervously.

"Would you stop worrying about work, and focus on how you look for tonight," she said.

"Alright," I said reluctantly.

"The extensions will come right out and the gel and hairspray can be washed out in the shower. I'll even give you my number and if you have trouble, I'll come to you and take care of it. Sound good?" She said.

I exhaled and said, "Thanks."

"Now let's work on your makeup. You look cute with the way you did it on your own, but I'm gonna make you look hot! Spin around away from the mirror so you can be surprised when I'm done," she said.

"Do you mind telling me what you're doing as your doing it so I can learn?" I asked.

"Of course," she said, "That a girl!"

She started brushing my cheeks with blush and then moved up to my eyes. She attached some false eyelashes, longer than the ones I had been using. She told me these would make my eyes pop and would give me some to take home. She brushed my eyelids with mascara and showed me how to do it correctly.

"I see you like Pink Lipstick, but I was thinking we'd try something different to go with your dress," she said.

"You're the boss," I said.

She opened a tube of bright Red Lipstick and applied it to my lips. She spun me around and I got the first glimpse of myself with my makeup done by a professional. She was right, I looked hot! Much better than they way I was doing it myself. My cheeks, my eyes, all the way down to my lips, all looked perfect. She was correct that this color lipstick looked great on me. I hadn't seen my dress yet, but if it matches my lips, Pete will be very happy.

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