Comforting Pete Ch. 02

Author's Note: This was only going to be one chapter, but due to the overwhelming response, you twisted my arm. Writing erotic fiction is hard and a lot of work. Being a perfectionist I made sure to check for any typos and grammar errors. I also made sure not to use the same words over and over to describe the characters actions. A casual reader probably wouldn't notice, but it is important to me that a story flows well to the reader. I appreciate any feedback and an honest rating. I hope you continue to enjoy this storyline.

SUNDAY MORNING -- CONTINUED

I woke up again and looked at the clock. It was 10AM this time. I was sore and my head felt hot. I felt something wrapped around my chest and I brushed some hair out of my eyes to look. I realized I was still wearing a Blonde Wig. I threw the sheets off me and looked down. The first thing I noticed was that I was wearing a Bra, and then I looked lower and saw my morning hardon at full mast. My body felt a little sticky and wet. My memories came flooding back into my brain and I smiled.

"Holy Shit it wasn't a dream!" I said out loud to myself.

I said to myself, because I was alone in Pete's bed. He had made me cum once with his mouth and three times with his dick up my ass. I made him cum three times, once with my mouth and then he blew a huge load inside my ass last night. Then I woke him up with a blowjob this morning and he came down my throat again, during which I agreed to be his girlfriend. Following his orgasm this morning he remarked that it was way too early to get up and we should both go back to sleep. Apparently I took that advice better than him, because here I am waking up alone 3 hours later.

I agreed to be his girl, but now what? The sex was amazing and I've never felt like that before in my life. I told myself if was into this idea last night and I told him 'Yes' this morning, but now I'm having second thoughts.

"Where is he?" I said to myself again. I need to talk to him about this.

The door was closed and the sun was peeking through the blinds. I got out of bed and took off my Wig and my Bra. I'm pretty sure girls don't sleep with Bras on and I think know why. There were red marks all around my chest where the Bra was pressing into me. I looked around the room for my guy clothes and they were nowhere to be found. I kept looking and knew one thing for sure...I needed a shower!

I warmed up the shower and got in. The warm water felt great over my sore body. I stood still and let the water cascade down my body before finding a bottle of body wash and lathering up. It was an interesting feeling rubbing the liquid soap over my hairless body. When I reached my asshole my finger slid right in with no resistance. Pete had really done a number on me, but of course he did, his cock was huge! My finger felt some wetness and a little stickiness, from the remaining cum that hadn't leaked out onto his sheets throughout the night. I did my best to wash it out, but then figured what's the difference. I finished my shower and dried off.

I walked back into the bedroom naked and tried to come up with a plan. The door was still closed and even though he had seen me naked before, I didn't want to walk out that way. I went into the closet to ponder my options. His clothes were out, as nothing would ever fit me, and he expected me to be in full Jessica mode anyway. I was hungry and wanted to throw on something quick so we could have breakfast and talk. I hoped he was in the kitchen waiting for me.

I looked through her clothes for some type of t-shirt. The best I could find were Tank Tops. Most of them were short and the longest one I could find was Pink. I pulled it over my head and it just about covered my belly button. I found a pair of White Shorts that fit. The only thing was they were going to barely cover my butt. At this point I was starving, so I decided the outfit was fine. I didn't want to go commando in these shorts so I just took the first pair of Panties at the top of the drawer, a Pink Thong. The entire drawer was Thongs, so it didn't really matter. I got dressed and waked towards the door. At the last second I spotted the Blonde Wig on the bed and figured I should put it on to complete my look.

Pete was sitting at the kitchen table drinking coffee. He had gone out for bagels. Coffee and carbs were a perfect way to recover from the last 24 hours.

He stood up and kissed me on the lips, "Good Morning, Jessica," he said.

"Good Morning, Babe," I said, getting into character.

"You looked so cute sleeping with your Blonde Hair on the pillow I didn't want to wake you," he said.

"Yeah, I was wondering what happened after I woke up all alone," I said.

"Sorry about that, I wanted to get us some breakfast," he said, "It looks like you cleaned yourself up nicely."

"Thanks," I said, "I was actually trying to find John's clothes."

"Why would you want to do that?" He asked.

"Because..." I started to say before being interrupted.

"I know you had an awesome time last night and you told me this morning that I convinced you," he said.

"Yes, but I may have been saying that in the heat of the moment. You're right, those orgasms you gave me were awesome, but I don't know if I'm ready to be a girl 24/7," I said.

He looked at me disappointed and just said, "Oh."

"You're upset," I said.

"I woke up all excited, because I was happy to have a new Girlfriend so quickly," he said. "Let's talk about it. What are you concerned about?"

"For starters, I have a family and a job that know me as John. I don't think I can leave those things behind so quickly," I said.

"Ok, anything else you're worried about?" He asked.

"Also, I'm not gay," I said, "Maybe Bi after last night, but I still have it in the back of my mind that I will marry a girl and have a family."

"I understand the family and the work stuff. I don't think you should worry about labels. If we have a relationship I would be a guy and you would be my girl. As for marrying a woman, you have never had a relationship that lasted more than 5 minutes," he said.

"Don't be a dick," I said, "We're talking about some serious life changing stuff here."

"Sorry," he said, "What else do you want me to say? I thought this would be a perfect setup, Best Buds and Boyfriend and Girlfriend."

"What are you proposing?" I asked.

"How about this?" He offered. "Monday through Friday you'll be John. You go to work and live your life the way you have been this whole time. Fridays after work you come straight here. I'll give you a key and you'll change into Jessica mode. We'll spend the weekend together doing boyfriend and Girlfriend stuff. Sunday after dinner you can change back and go home."

"Interesting," I said, "Keep going."

"I'll move all of Jessica's clothes and makeup into the spare room. That will be your dressing room. You will of course sleep in my bed Friday and Saturday Nights. If there's anything else you want or need I have a credit card in Jessica's name to give you. You can order whatever you want online and have it shipped here," he said.

"So you really want me to be your 'Girlfriend' every weekend?" I asked. "What about John and Pete? What if either of them find a girl they want to be with?"

"I want you to be comfortable. Let's start with the weekend thing and see what happens. If we want it to be more than weekends, we'll discuss it. As for John and Pete, if we want to hang out during the week as Best Friends, let's do it. We won't even discuss Pete and Jessica during the week. To answer your last question, if either of us finds someone who we'd rather be with, we'll discuss it and go from there," he said.

"Wow, you've really thought this through," I said.

"Yeah, I think it would be great for both of us," he said.

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

"Of course," he said, "No pressure, but I'll tell you what. I have to do some work on my computer for a while. John's things are in the guest room and you know where Jessica's things are. Take your time and decide which clothes you want to come see me in. We'll either continue our day together as Pete and John or Pete and Jessica. Come get me when you're ready."

"Okay," I said.

Pete kissed me on the forehead and left the other room. He had convinced me again when he suggested a part time arrangement. I just didn't want to tell him right away and wanted to surprise him.

I walked back into the Master Bedroom and stripped down to my Pink Thong. I quickly found the matching Bra and wrapped it around my chest. It cupped the small man boobs I had, but mostly hung loose due to my lack of real breasts. Oh No Breasts! I thought to myself. If this relationship continues is he going to expect me to get some? It could be kind of fun and should enhance my sexual pleasure, but that would mean trouble at work and with my family. I started to breathe heavy, but then relaxed myself, because it would be a problem for the future. For right now I had to pick an outfit to blow him away and let him know I'd be happy to be his Girlfriend on the weekends.

I started to flip through the dresses, but figured I would save those for another day. I assumed we were just going to hang out around the house and wanted to find something simple. Then a Black Leather Mini Skirt caught my eye. If I saw a girl wearing that I would definitely check her out. I didn't see any zippers or buttons on it, so I pulled it up my legs like it was a pair of shorts. The only difference was there was no fabric in the middle and my hairless legs were rubbing against each other. Next I found a White Satin Blouse. I buttoned it up leaving the top two open, and letting my Pink Bra peek through. The Skirt was shorter than I realized, as it barely reached my knees. I never realized how feminine my face and body were. I could almost pass as a girl without makeup on. This worried me a little, but I also got a chill up and down my spine.

I sat at the makeup table and tried to copy what I did yesterday. I made sure to put on Pink Lipstick to match my Lingerie. I figured that would be a nice touch. I was almost ready to go see Pete when I realized I was barefoot. My feet were always small and dainty, so to no one's surprise, Jessica's shoes fit me as well as her clothes. I picked a short pair of Black Heels to try out. Of course I had never worn anything like this before so I did a couple laps around the room.

I walked down the hallway to the sound of my heels made me giggle. I always loved the click-click of heels, and I never dreamed the sound to be coming from my feet. Approaching the doorway of Pete's office, I stopped and posed for him. I don't think he saw me so I cleared my throat to get his attention.

"Hey, I'll just be one second," he said.

"No problem Babe," I said to him, trying to do my best girl voice.

He turned to look at me and said, "Holy Shit! You look amazing Jessica!"

"I thought you'd like it," I said.

"Those clothes were made for you," he said, "Look at your legs in that Mini Skirt! Give me a twirl and let me see the whole package."

I blushed and gave him a slow spin, stopping with my back to him so he could check out my ass in the tight skirt. Once I was facing him again for some reason I said, "Ta-da!"

I looked down to see he was rubbing his crotch. He said, "I can't believe you look so good. We are going to have so much fun together. You have me so hard right now."

"Oh," I said, startled.

He stood up and said, "I have to have you right now. Are you ready to feel good again?"

"Um, I guess so," I said.

He walked over to me and in an instant his tongue was in my mouth. We made out in the doorway to his office as his hands were all over my body. He started to walk forward while we kissed and I backed up slowly in my Heels. We reached the kitchen island and he spun me around.

"Put your hands on the counter and stick that ass out!" He told me.

I spread my legs and bent over, wiggling my ass at him. "How's that, Babe?" I asked.

"So hot," he said.

He reached around me to rub my little boobies through my Blouse and Bra while he was kissing my neck. Then he moved his hands to my ass and began to rub it. He lifted my Skirt up to expose my Pink Thong.

"Mmmm," he said, "My favorite color for my girl to wear and your crack is just swallowing up that Thong! I almost feel bad to pull it out of there, but I'm going to replace it with something nice and hard!"

I moaned as he pulled my Thong down to around my ankles. He pulled my cheeks apart and I felt something moist on my asshole. He must have had this planned and had lube ready for me.

"Ready, Babe?" He asked.

"Yeah, just go slow, you gave me a workout last night," I said.

"Don't worry," he said, "You're still wide open!"

I blushed again, happy that he couldn't see me. Then I panicked, was my asshole supposed to still be open? I hope he didn't do any permanent damage to my body. Maybe this wasn't a good idea. My thoughts were interrupted when I felt the head of his huge dick make contact with the edge of my hole and then he thrusted into me in one motion. His groin was pressed against me and he was balls deep inside of me.

"Oh My God," I screamed.

"Yeah Jess!" He screamed back.

He held himself deep inside of me and waited. Neither of us said anything and I felt like he hadn't moved in forever. I started to wiggle my ass to entice him and he still didn't react.

"Babe, would you please fuck me!" I begged.

"I thought you'd never ask," he said.

He pulled back slowly until just his tip was inside of me. He held still and I wiggled my ass again. Suddenly I felt him slap my ass hard and plunge back inside of me.

"Ohhhhhhhh," I moaned.

The slap stung, but it was probably the hottest thing that's ever happened to me.

"You like that Jess?" He asked.

"Yeahhhhh," I gasped, "Do whatever you want, spank me, fuck me hard, your dick feels amazing!"

That was all the encouragement he needed. He spanked my other cheek to even things up and started to fuck me like crazy. I was holding on tight to the counter to make sure I didn't fall over. His hands were on my hips and I thrusted my ass back at him until we got into a good rhythm. I looked down to see my heels and hard dick peeking out from under my Skirt. Was this going to be my life every weekend from now on? I was getting close to cumming and I reached for my dick to stroke it. Seeing what I was doing, Pete grabbed my hand and put it behind my back.

"Oh no," he said, "Cum from my dick up your ass not from jerking off!"

"Awww," I moaned in disappointment. I knew he was right though. Those orgasms he fucked out of me last night were ten times better than jerking off.

Somehow he started to fuck me faster and we were both moaning. Once I again I came first, after many thrusts pressing directly on my prostate. I shot my load all over the kitchen tile. My orgasm made my asshole spasm and I felt his dick grown even harder. He held himself deep inside of me and came too. He put both hands on my hips and pulled me forward and back, using the motions to finish his ejaculations. When he slipped out of me he spun me around and kissed me.

"That was amazing," he said, "I'm going to look forward to that every weekend."

I looked at him reluctantly, still not sure what I've agreed to, except my body felt so good from my orgasm that I still had tingles up and down my body. "Yeah, it was nice," I said.

"What are you thinking about doing for the rest of the day?" He asked.

"Actually I've been here all weekend and I'm a little tired. Do you mind if I head home? I have to be into work early tomorrow," I said.

He pecked me on the lips and said, "Of course Jessica, I'll see you again on Friday. Remember John's clothes are in the spare room, if you think he should be the one walking into his apartment."

"Thanks Babe," I said and started walking towards the bedroom.

I grabbed my T-shirt and Shorts from the guest room and brought them into the Master Bedroom. I pulled off my Wig and washed off my makeup. I put the Blouse and the Miniskirt in the hamper and went to take my Bra and Panties off. Then I remembered I came over wearing a Bikini under my regular clothes and didn't bring any boxers with me. I didn't want to go without underwear, so I put my John clothes over the Pink Lingerie.

I walked back to the front of the house and Pete was sitting on the couch watching TV. He stood up when he saw me and gave me a guy handshake.

"Take it easy Dude," he said, "Maybe we'll do dinner one night this week."

I was shocked at how fast he could act like things were normal again, but then again he wasn't the one getting fucked in the ass. "Yeah, Pal," I said, "I'll talk to you later."

I walked to my car and saw there was a bag on the front seat. Pete had left Jessica some more things. I drove home, but didn't look in the bag. I had enough Jessica time this weekend and I wanted to enjoy some John time. Carrying the bag inside, I noticed it was heavier than usual and I decided I would check it out tomorrow after work.

MONDAY

I thought about sleeping in the bra and panties, but then I remembered how uncomfortable that could be. Instead I wore my typical old t-shirt and boxers. I noticed a wet feeling in my shorts and realized I had leaked during the night. I thought I had cleaned myself up well, but

I guess there will always be some left over. How do real girls deal with this? I'd never find out, because even if there was someone to ask, I'd be too embarrassed to admit I let my Best Friend call me his Girlfriend and cum inside me.

I got up and took another shower to get ready for work. My day seemed to drag on and my mind kept going back to the events of the weekend. I was getting excited thinking about the huge bag waiting for me at home and when my day finally ended I sped home faster than usual.

Normally I would change into some around the house clothes, but instead I went right for the bag. I flipped it upside down on my bed and couldn't believe how much he left me. There was a rainbow of colors of Lingerie, Bras, Panties, Stockings and Garters. There were several Babydoll Nighties of varying length. Then there was a pair of fake breasts. Well that solved my earlier question, at least temporarily, he wanted me to wear these. I picked them up and was surprised by the weight. There were two side straps attached to them with hooks like a bra. I looked at the tag and to no surprise they were a 36C, just like all of the Bras in my new collection. Then it dawned on me, he went out and bought these special for me. There would be no reason for Jessica to have these, as she had real ones of her own. As reluctant as I have been to do this, he has been completely serious about it.

Since I had a Lingerie drawer now, I started to fold everything so I could put them away. As I picked up one of the Nighties I saw something flesh colored peeking out. In my haste to empty everything out of the bag I hadn't seen everything. I lifted the Babydoll to reveal a huge dildo, balls and all. It looked familiar for some reason and next to it was a note.

"Jessica, I wanted to give you some things to wear around the house during the week. I had such a great time over the weekend and can't wait to see you on Friday. I hope you like the breasts, they should fill out your bras nicely and complete your look. As for the dildo, I'm sure you recognize it. We had sent away for a kit and made an exact replica of my dick. I thought you might want to play with it and practice for our times together. XOXO Pete."

Holy shit! Did I really just recognize this dildo as being a replica of his dick? It's certainly been inside me enough times already it would be weird if I didn't recognize it. I shook my head and thought about how strange this whole thing is. I've never been attracted to men in my life and now I have a huge collection of Lingerie and a dildo to play with.