Comforting Pete Ch. 02

I took off my work clothes and went to change in to something casual, but I couldn't get my mind off the breasts. I attached them in front of my naked body and spun them around like a bra. I looked down at the enormous tits hanging from my chest and felt the weight that came with them. I picked up a Black Bra and wrapped it around my chest. I felt instant relief when it held them in place. I found the matching Panties, which were of course a Thong, and pulled them up my legs. My dick began to stir and I reached down to tuck it in place. I looked at myself in the mirror and wished I had my makeup and my wig here.

I was hungry and was going into the kitchen to make something. I felt underdressed in just my lingerie, so I pulled a Black Babydoll with White Trim over my head. It was low cut and showed a lot of cleavage. I couldn't believe it, I had cleavage! Too bad Pete wasn't around to see. I made myself some dinner and when I went to sit down, the Babydoll rode up above my cheeks. I was sitting on a chair on my bare ass with just a Thong covering my hole. I felt so hot and my dick escaped its tuck and sprung into a huge erection in the front of my Panties.

I enjoyed my dinner while wearing my cute Lingerie, and for the first time I actually felt comfortable in the clothes. After I finished eating I sat on the couch to watch TV as I usually did. In this position I could really see my smooth shaved legs, and I wished I had a pair of heels on. My brain was really starting to transform. It made me excited, but also a little scared. I tried to focus on the TV and then a commercial came on for a Law Firm. They were trying to get people to sign up for a class action suit and at the end they said 'Call our Practice.' Practice, that word rang a bell in my mind. The Pete Dildo, he wanted me to practice!

I went in to my bedroom and saw it sitting on my bed, right where I had left it. My asshole was still a little sore, so that was out. I had blown him twice, but hadn't been able to take him all the way. Maybe that's what he meant about practice. I picked up the dildo and stroked it. It was heavier than I expected and felt real. I rubbed it for a little bit and built up the confidence to take it in my mouth. I was sitting on my mattress, decked out in lingerie, sucking a replica of my new boyfriend's dick. Those were words I never thought I'd say. I was getting into it, even though I felt a little silly. I was determined to take it into my throat, but started to gag. I finally was able to take it all the way when my phone beeped and buzzed loudly.

I looked at the phone, with the dildo still deep in my throat. It was a text from Pete, "Hey Buddy, what are you doing tomorrow night? I figured we could go to O'Malley's and try to pick up some chicks," he said.

I know we agreed to still be Best Buds during the week, but I basically have his dick in my mouth and he's asking John to hang out with him. I pulled the dildo out of my mouth and texted back, "Sure."

"Ok, I'll pick you up at 6," he said.

I was confused, ashamed, and a little embarrassed. I stripped out of my Jessica clothes and went back to the couch in my T-Shirt and Boxers to watch TV until it was time to go to sleep.

TUESDAY

I got home from work at 5:30pm, giving me half an hour before Pete was picking me up. I had worn a nice button down shirt and pants to work, so I didn't need to change to go out to the bar. We did this all the time. We would have some dinner, drinks, and try to pick up chicks. He would have success about half the time while I continued to bat 0.00. As 6pm approached I was a little nervous. We only had that quick goodbye on Sunday and hadn't really talked since. I didn't want things to be weird.

I was watching out my window and he was right on time. He gave his typical honk to let me know he was here and I went downstairs. He drove a 5 series BMW which put my ratty old car to shame. I opened the door and got it. He reached out his hand to shake mine, and for some reason I closed my eyes and leaned in as if to kiss him. I caught myself and stopped, shaking his hand instead. He didn't say anything and I hoped he didn't notice.

"What's up Dude," he said, "I feel like I haven't seen you in forever."

"Hey, what's up? How are things?" I asked, wondering if he would bring up the weekend.

Acting completely normal he said, "Same old. You hungry? I'm starving!"

"Yeah, I could eat," I said, getting more relaxed.

"Cool," he said, "I know it's a Tuesday night, but I have a feeling we'll meet some chicks tonight."

Meet some chicks? I thought to myself, that's the second time he's said that. Maybe he's serious about keeping things separate. I was totally calm by now and things were like the always were. "Perfect," I said, "Maybe I'll finally have some luck."

"I'll be your wingman," he said.

"Gee thanks," I said, sarcastically.

We got to the bar and he told me to find a table while he got the drinks. This was typical protocol. He would set up the tab and I would straighten out with him later. We liked this place because you could just grab a table, order whatever food you want at the bar and they would bring it to you. It was a cool place and we always had fun. What was odd about tonight was Pete was gone for an abnormally amount of time. When he finally came over he wasn't alone.

Pete had a pretty Blonde girl with him and they were holding three beers. "John, this is Janie," he introduced her.

"You and the letter J," I said and smiled.

"What's that?" she asked.

Pete gave me a look and said, "Nothing, just an inside joke."

"Oooh, tell me," she said.

Covering for my dumb comment I said, "It's not really a joke. It's just that everyone in Pete's life seems to have a name that starts with the letter J, his Mom, his Dad, his Sister, his Best Friend."

"Does that mean you're going to want me in your life?" She asked him, suggestively.

"We technically just met, but I like what I see so far," he said, liking that she was being so forward.

She smiled and sat down. Pete handed me my beer and I said, "So how did you guys meet?"

"She tried to steal the bartender away from me," he said, "You know how pretty girls try to get away with everything in bars."

"You think I'm pretty?" she asked Pete.

"You're hot!" I said, not knowing where those words came from, because I'm never able to talk to girls that way.

"He's right, you are hot!" Pete said.

"Aw, you guys are sweet," she said, blushing.

"She tried to steal your bartender and then what?" I asked.

"I got his attention and then she ducked under my arm and tried to order before me. I was tempted to just let her go in front of me, but when I saw how pretty she was I offered to pay for her order if she agreed to join us," he said.

"Your friend has a nice smile," she said.

"We started talking and she seemed cool enough so I invited her over," he said.

"It worked out perfectly," she said, "I usually come in with a bunch of girls on Thursdays, but tonight I was bored and decided to come solo."

"She agreed to join us for a beer and a burger and fries," he said, "That's what I got for you, by the way."

"A girl could never turn down a meal and a drink from such a handsome guy," she said.

"You certainly make the table brighter," he said, "Beats looking at my buddy the whole night!"

"Hey," I said.

"Don't be mean," she said, "He's kinda cute. I bet one of my friends will like him. Why don't you guys meet us here on Thursday?"

My face got red in embarrassment. Here was a pretty girl that thinks I'm cute, offering to set me up with one of her friends. Meanwhile my Best Friend who wants me to be his Girlfriend on the weekends is trying to pick up another girl. What have I gotten myself into? Do I want to finally meet a girl? Or am I jealous of Janie possibly hooking up with Pete? I've been silent for way too long and still don't know what to say.

Speaking for me, Pete says, "We'd love to meet you gals on Thursday. My bud is just a little shy."

She rubbed my arm and asked, "Oh, do I make you nervous?"

"N-n-no," I was able to get out.

"You're really adorable," she said, "Pete, you need to help out your buddy with his confidence. My friends are hot and he can probably get lucky with the one I'm thinking of."

"Speaking of getting lucky," Pete said, winking at Janie.

"Take it easy buster," she said giggling, "Let me have my dinner and a few more drinks and we'll see."

"So you think my buddy can hook up with one of your friends, but to use your own words, Handsome Pete has to work for it?" He asked her with a grin.

"Exactly," she said, continuing to giggle.

"Challenge Accepted!" He said confidently.

Our food came and the two of them continued to flirt with each other while I pretty much sat there and listened. About an hour into the evening Janie got up to go to the bathroom.

Pete leaned in and said, "Listen, I think I'm going to end up taking her home. Do you mind taking an Uber?"

"Yeah, no problem," I said.

"When she comes back just tell her you need to get up early for work and head out," he said.

"Ok," I said.

Janie came back to the table and I got up. "Leaving so soon?" she asked me.

"Yeah, unfortunately I have to go into work early tomorrow," I said, "But I'm leaving you in good hands."

"Oh I'm sure of that," she said. She kissed me on the cheek and said, "See you Thursday, right?"

She caught me by surprise with the kiss. It had been so long since I've had female contact that even a kiss on the cheek was exciting. I hesitated and finally said, "Sounds good, goodnight."

Pete gave me a slap high five and I took out my phone to book a ride home.

It was a short ride, but my mind was full of thoughts. On one hand I felt excited that Janie was going to introduce me to one of her friends, but on the other I was jealous of her. She was probably going home with my weekend boyfriend. Of course he would want her instead of me. She had real boobs and a real pussy to fuck. I was a dude, pretending to be a girl for him. Why am I considering that I want him more than a real girl of my own? I was really thinking like a girl now. Maybe it was all that sperm he's shot inside me already.

THURSDAY

The next two days were quiet. I hadn't heard from Pete and I hadn't played with any of my Jessica clothes either. Just after noon I finally heard from him.

"Hey Dude, we're still going to O'Malley's tonight to meet those girls, right?" He texted.

"If you want to," I texted back.

"Yeah, Janie had to go home shortly after you left so we didn't get to do anything. She told me she's off on Fridays so that's why she usually goes out on Thursdays," he said.

I smiled. It made me happy that he didn't hook up with Janie. "Ok," I typed, "Pick me up at 6?"

"You got it," he texted, "She's coming with that friend for you, maybe we'll both get lucky."

Feeling a little envious of Janie again I just said, "Cool."

Work flew by and I was in the same situation. My work clothes were fine to go out in and he picked me up at 6 on the dot. We found a table and this time we waited for the girls before we ordered anything. Janie was the first to show up and she greeted Pete with an opened lip kiss and me with a kiss on the cheek. I blushed again at the contact of her soft lips.

"Hey guys, what's up," she asked.

"Not much," Pete said, "Just waiting for you."

Janie had worn a short dress that showed some cleavage. It was different from her blouse and jeans she wore on Tuesday. Thursday was pickup night and everybody knew it. The entire bar seemed to take their looks up a notch.

"How's it going John," she asked, "My friends will be here in a bit. I think you'll really like Jennifer."

"Hey, another J," Pete said.

We all laughed and Pete and Janie went to order, leaving me to hold the table. My brain started to churn. I was about to meet a girl that Janie said would probably fool around with me and all I could think of is that Pete is with Janie. He's planning to take her home and fuck her tonight and I'm jealous. We're supposed to be two Best Buds out on the prowl, both of us on the verge of banging chicks and I wish I was the one he was going to take home. What a turn of events from a few weeks ago. What has he done to me?

Janie's four friends showed up and she walked over to greet them before bringing them over to meet us. She introduced us to Britney, Dana, Tina, and Jessica. Wow, Jessica was the prettiest of the four of them. Janie thought she'd like me? No way. I clammed up and just smiled and nodded. Pete was his normal charming self, basically speaking for me. The four girls walked to the bar and Janie stayed with us.

"So John, what do you think?" She asked me.

I stuttered, "Sheeee's gorgeous."

"I knew you'd like her," she said.

"Yeah, but..." I started to say.

Pete interrupted and said, "Looks like Johnny-boy is nervous."

Janie rubbed my and said, "Aw, that's so cute. There's no reason to be nervous. Jen is so nice and sweet. She just broke up with her boyfriend and is looking for a nice guy to have some fun with."

"Think you can handle that Buddy," Pete said, "I plan on taking Janie home tonight, and I you should try to get some action too."

Janie looked at Pete and in a seductive voice said, "Oh really?"

"Yeah, baby," he said, "You look so hot tonight we might be getting out of here sooner than you think!"

"Mmmm," she said.

"Why don't you grab Jennifer and bring her over so we can take care of my boy here and then we can go have our own fun," he said.

"I don't know," I said nervously.

"Come on Dude, grow a pair and talk to the pretty girl. It's not hard," he said to me.

Janie walked over and grabbed Jennifer. She was wearing a tiny dress too. There was no way I could talk to a girl like this, even if her good friend was setting us up. I took a swig from my beer and tried to relax.

"Jen let me better introduce you to John. He's Best Friends with Pete," Janie said.

Jen reached her hand out to shake mine. We did the typical light handshake between a boy and a girl. She smiled and said, "Hi."

I was so nervous, and in a high pitched voice I said, "Hi."

Janie and Pete laughed while Jen just looked at me. "Relax," Pete mouthed to me.

I smiled at her but wasn't able to say anything.

Pete tried to help me out and said, "So Jen, I hear you just got out of a relationship and are looking for someone to show you a good time."

Jen gave Janie a look and said, "You didn't have to tell them everything!"

Janie just shrugged and grinned.

I still couldn't come up with something clever to say, and decided I needed a breather. I was able to get out, "Who's ready for another round?"

Everyone said yes, and I got up to get us some more drinks. I took my time by the bar and tried to compose myself. Then I realized I can't carry 4 glasses. I told the bartender and he handed me a tray. I walked back to the table like I was a waiter holding the drinks.

Things progressed while I was away because Pete had his tongue in Janie's mouth and they were making out like crazy. Jen must have been bored because she was staring at her phone. I put the drinks on the table and they stopped kissing for a second. They each took a sip and began making out again.

Jen looked at me and said, "Can you believe these two, making out in the middle of the bar?"

I was staring at them and just said "Yeah," without even looking at Jen.

I kept staring at them unable to look away. I think I heard Jen say something, but I couldn't take my eyes off them. Here I was being setup with a hot chick that sounds like she's ready to go and I'm fantasizing that I'm her friend that's being kissed by my Best Friend. I was so jealous right now.

The lovebirds came up for air and Pete said, "We're gonna get out of here. You two will be ok without us, right?"

"Sure," Jen said.

I nodded and the two of them got up. Janie looked at Jen and said, "Text me later."

Jen nodded and it was just the two of us in the booth. "Do you not think I'm pretty?" Jen asked me.

I paused and was able to say, "No, I mean of course I do. You're very pretty."

"I wasn't sure because you've been staring at Janie," she said.

Little did she know I wasn't staring at Janie, I was pretending I was her.

"I'm sorry," I said, "I guess I didn't realize."

"Listen, I think you're cute and all, and Janie thought you'd be a sure thing, but I'm just not feeling it. I really need a rebound lay," she said.

"Oh," I said.

"That's all you have to say. I thought you'd at least try to convince me not to walk away. I was ready to go home with you but you're clearly not interested," she said.

I was still distracted by Pete taking another woman home and even though I had this hot girl throwing herself at me I was tongue tied. When I didn't say anything, she got up in a huff and went back to join her friends. I pulled out my phone and ordered an Uber. I was going home alone again.

During the cab ride all I could think about was Pete and Janie. Why was he with her when he could be with me instead? My thoughts made me hard and I started to rub my crotch in the back of the cab. I was so horny when I got home that I knew what I wanted to do. I had resisted wearing the Jessica clothes all week, but it was time to play again.

I stripped naked and got in the shower. My body hair had started to grow back and I shaved everything below my eyebrows. It was nice to feel silky smooth again. I dried off and went for my lingerie drawers. I say drawers plural, because I had so much now that I had to expand to a second drawer.

I put on the breast forms and Black Bra and I had boobs again. I skipped the Panties, because I wouldn't be wearing them long anyway. Rifling through my drawers, I settled on a skimpy Pink Babydoll that barely covered my cheeks. I put on the Blonde Wig and brushed on some makeup and my signature Pink Lipstick. I was only doing this for myself, but when I looked in the mirror, I was hot. My erection poked out from under the short Nightie. I laughed to myself, wondering if Jennifer would still want to fuck me if she could see me now.

I got on my bed and found my prize, my Pete Dildo. I stroked it up and down, pretending it was him. Then I took it in my mouth and gave it a sloppy suck, using a lot of saliva, knowing I had other plans for it. I could see the Pink Lipstick marks I was leaving on it and I smiled. When it seemed wet enough I pulled it out of my mouth.

I grabbed a tube of lube and coated my fingers. I reached down to my asshole and inserted my index finger. It had been almost a week since Pete fucked me and I was back to being tight again. I eased my finger deeper and I had goosebumps. One finger wasn't going to do it though. Pete's dick was huge, so his exact replica would be the same. I progressed in two fingers and then three. I hit my prostate and although I thought about cumming, I knew I wanted to cum with the dildo deep in my ass.

I raised my knees so my feet were flat on the bed. I took a deep breath and pushed the tip of the dildo against my rosebud. I had never done this before and didn't want to hurt myself. Pete pushing his dick into me was one thing, because he was in control. I was doing it to myself and from a different angle. I pressed a little harder and my asshole started to open. Good thing I stretched myself out with my fingers first. I was encouraged and pushed it in deeper. It felt so huge inside me and it wasn't even halfway. I had taken the real thing multiple times so I knew I could do it. I put my hand on the base and in one big push pressed it all the way inside me. I gasped as the balls rested against my ass.

With the Pete Dildo completely inside of me I waited and breathed. Then I clenched my hole and it started to slip out a bit. I put my hand against the base and pushed it back in. I repeated the process and enjoyed the feeling of it slowly moving inside me. When I was ready to be more adventurous I pulled it out to the tip and fucked myself deeply over and over. During these deep thrusts I was rubbing my prostate. I was getting the familiar tingles and was ready to cum. I found the right spot and started to hammer my prostate. I didn't last much longer and a came really hard, shooting my load straight up into the air and soaking my Babydoll.