Comforting Pete

Author's Note: Trying something a little different here. This is planned as a single story instead of one with multiple chapters. However if there is interest, this can evolve into future stories. Feedback and ratings are always appreciated.

FRIDAY

I'm heading to my best friend Pete's house on a Friday afternoon. I typically got off from work early on Fridays and he wanted me to come over. His live in girlfriend Jessica had just broken up with him and moved out abruptly. She was hot, but we never really got along. He was depressed and invited me over for some pizza, movies, and to help drink his sorrows away. We had been friends since high school and he always seemed to be the luckier one of us two. He was taller than me, made more money than me, owned his own home, and always did better with the ladies. I pulled into his driveway and walked up to his door. The door was ajar and I let myself in.

Closing the door behind me I said, "Hey, Dude, where are you?"

"Over here!" He yelled from his TV Room.

I've been in his house a hundred times. It was always clean and neat. Not this time. There were pizza boxes all over the floor and the sink was piled up with dishes. I walked in to the TV Room and saw Pete sitting on the couch nursing a beer. His hair was all messed up and he hadn't shaved in days. He was wearing and old t-shirt and shorts. This was not the Pete I knew. Even though it was just me coming over, he would at least make himself look presentable. He was taking this one hard.

"Dude, what the fuck?!" I said.

"Don't mess with me today, John, I didn't invite you over to break my balls," he said,

"This place is a mess and you look awful," I said.

"Thanks," he said sarcastically. "Jess used to keep the house clean."

"I get that, but you look like a hobo," I said.

"Fuck you," he said laughing. "Next time I'll put on a tux when you come over. Now grab a beer and take a seat," he said.

I walked back to the kitchen and took a beer from the fridge. I opened it and sat next to him on the couch.

"So you want to talk about it?" I asked.

"Not really," he said.

"She just picked up and left?" I asked.

"Yep, didn't even take all her stuff," he said.

"What did she say?" I asked.

"I thought I said I didn't want to talk about it," he said.

"Come on, at least give me the cliffs notes," I said.

"Fine," he began. "I noticed a few weeks ago that she had been going out with 'friends' a lot. I didn't mind as we had been seeing each other for over a year and were living together. I went out with my friends, why shouldn't she be able to go out with hers. Then she was never in the mood for sex. She was happy to sit on my face, but she wouldn't blow me anymore. Anytime I tried to fuck her, she would say she was too tired. Over the last few weeks she got off with my tongue and I had to go jerk off in the bathroom after."

"Damn Dude," I said, "And then what happened?"

"A week ago she spent the whole night out, didn't call, didn't text," he said. "When she finally came home she said she was too drunk to drive home and spent the night at her friend's house. I was mad, but then she said something like, 'You didn't want me drive drunk and hurt myself or someone else did you?' She always had her way of convincing me of things, and I let it go."

"She was really cheating, right?" I asked.

"Yeah, but I was too smitten to realize," he said. "Three days ago it happened again. She stayed out all night and when I confronted her she came clean. She had been fucking some dude for the last two months behind my back. We had a huge fight and she wasn't even sorry. The guy was moving out West and she wanted to go with him. I was really pissed and told her to get out. She said fine and that I could throw out all of her stuff. She was going to start a new life on the West Coast and leave her old one behind. She walked out the door and I haven't heard from her since."

"Sorry Dude, that sucks," I said.

"Yeah, I thought she was the one," he said.

"Wait, you don't think she..." I started to ask and then paused.

"What?" he asked.

"You don't think she came home after fucking the guy and made you eat her out do you?" I asked.

"What? No! Gross," he said. "Although..."

"You think?" I asked.

"I did notice she was extra wet and tasted a little funny the lately," he said.

"Holy shit," I said, "You ate her lover's cum out of her pussy?!"

He took a big swig from his beer.

"I don't think that will wash it out," I said laughing.

He punched me on the arm and said, "Fuck you, this isn't funny."

Continuing to break his balls I said, "How many 'the one' is that now?"

"Dick," he said, jokingly.

"Let me think," I said, "Jessica, Jennifer, Jill?"

"Fuck off," he said, "How about you? I don't see you ever have any action."

"I do ok for myself," I said. I was lying, and he knew it. Trying to deflect I said, "What is it with you and chicks and the letter J anyway?"

"I guess it's a coincidence," he said, "Or maybe I just like to be with people whose name start with the letter J, right John?"

"Now who's being the Dick?" I asked.

"It would be easier, wouldn't it?" He asked.

"What?" I asked.

"Giving up pussy and being with your best friend," he said.

"What?" I said, "I think all that sperm you ate has gone to your brain."

"Screw you," he said jokingly, "But seriously, you never get any pussy anyway. What would be the difference?"

"I get plenty," I said.

"Name three girls you've fucked," he said.

I hesitated. He knew there was only the one back in college. I stuttered and said "I...."

"Yeah, that's what I thought," he said. "There was only that chick Tara who was so drunk that you fucked her while she was basically passed out. If I'm wrong name another one."

"There was..."I paused, not being able to lie and come up with other names.

"That's what I thought," he said, "Just the one, barely."

"Thanks Dick," I said

"I bet you'd look cute as a girl," he said.

"Dude, what are you even talking about," I said, "You're not that drunk are you?"

"No, but if we were drunk, would it be something you'd think about? It seems like the only time you get lucky is when the other person is drunk," he said.

"Listen, Fucko, she wasn't that drunk and she said she loved it. The next day we decided we were better off as friends. As for this bullshit you're breaking my balls over, you need to cut it out!" I said.

He started laughing hysterically and said, "Thanks Dude, I just smiled for the first time in days."

I started to laugh too and he dropped the topic. We continued to drink beers and ordered a pizza. I helped clean the kitchen and picked up the garbage while we waited for the food. I knew he wasn't going to do it. After we ate we watched the latest John Wick movie.

As the movie was ending there was a moment of awkwardness. He put his hand on my thigh and rubbed it a bit. He said, "Thanks for coming over and helping clean up. It's nice to have someone around the house again."

I didn't react to where his hand was and said, "Happy to do it Buddy."

We made plans to go out to eat the next night and he walked me to the door and gave me a bro handshake.

Driving home I had the radio on, but my mind was full of my thoughts. What was that with him rubbing my leg? What was that nonsense that I'd look cute as a girl? Would it be easier to settle down with my best friend instead of constantly chasing after pussy that's not interested in me? Then I snapped out of it and decided I was thinking crazy. I blasted the radio and focused on the rest of my drive home.

SATURDAY

The next night we went to dinner as planned. We had a nice meal along with some drinks and then he invited me back to his house. We do this all the time, so it wasn't anything out of the ordinary. It was a hot night and when we got back to the house he suggested we go in the pool.

"Dude, that's a great idea, but I didn't bring a suit," I said.

"Yeah, and I don't think you'll fit into one of mine," he said.

"No problem, we can go in next time," I said.

"You can always go skinny dipping," he said laughing.

"Yeah, I don't think so," I said.

"Let me see if I can find you something," he said.

"Ok, I'm gonna hit the bathroom," I said.

I finished up in the bathroom and when I walked out he was standing in the hallway. He was wearing swim trunks and had taken his shirt off. That's not what caught my eye though, it was the red bikini on the hanger he was holding.

"Found you something that should fit," he said.

"What the fuck is that?" I asked.

"One of the bathing suits Jessica left behind," he said. "It looks just about your size."

"That's not a bathing suit, it's a bikini," I said, "You don't seriously want me to wear your ex girlfriend's bikini."

"Why not, you didn't want to skinny dip," he said, "You don't have to wear the top if you don't want to."

"Gee thanks," I said.

"Come on," he said, "We both want to go in the pool. You get dressed and I'll grab us some beers. Meet me in the pool."

He extended his arm to hand me the hanger. As a reflex I took it. He walked away and I didn't say anything. I figured what's the difference, I was going to be underwater most of the time anyway. I walked into the guest room and got undressed. As a goof I held up the bikini top to my chest and looked in the mirror. I laughed to myself before putting it on the bed. I pulled up the bottoms like they were a regular pair of underwear. He was right, they did fit, but my dick also started to stir. Was I getting turned on from wearing a bikini? Maybe it's just because I was pressed against the same material that's touched Jessica's pussy. I looked in the mirror and it looked like I was wearing a red speedo. I never had much body hair and being blonde, whatever hair I had was light. I had to admit I looked pretty good in the bikini bottoms.

I walked out to the backyard and Pete was already in the pool. He whistled at me and said, "Whoa, I knew that would fit! You look hot! Why don't you give me a spin so I can see that ass, darling!"

"Fuck you," I said, and I turned around, like I was going to walk inside, not realizing I was giving him what he asked for.

"Wow, your ass looks great, just like I thought it would," he said.

I turned back around and said, "Dude, cut it out or I'm going home."

"Just breaking your balls," he said. "Come in, the water's wonderful."

I walked closer and I could tell he was staring at me. "What?" I asked.

"It looks like you have some boobies going there, pal, maybe you want to go put on your top?" He said, laughing.

"That's it!" I said. "I'm going home!"

I turned around and walked back towards the house. I didn't hear him get out of the pool, but he slowly walked behind me and slapped my ass. Not expecting it, I jumped forward and yelped. As I turned around, he picked me up.

"Dude, what are you doing?" I asked.

"We said we were going to hang out in the pool," he said. He carried me to the edge and threw me in the pool. He jumped in beside me and said, "See, it's nice in here."

"Yeah, you're right," I said.

We both swam around a bit and I forgot I was wearing a girl's bathing suit.

"I love a night swim," he said, "Jessica and I used to come in with me all the time. And she wasn't shy about skinny dipping."

"Have you thought about who can replace her? There's gotta be a Jane, Janine, or Jodie out there for you," I said laughing.

"If I had to go for another J, it why not John?" he said and winked at me.

"Would you cut that shit out," I said, "Why would you want to go from a hottie like Jessica to me anyway?"

"I'm just fucking around," he said, "You know you're cute when you're mad."

"Whatever," I said, brushing it off. "Where's those beers you were talking about?"

He got out quick to grab us each a beer and he threw a couple basketballs into the pool. We started drinking and shooting hoops. He had a full size basketball hoop at the edge of the pool. He had the height setup where the rim was approximately 10' from the bottom of the pool. It was like we could shoot regulation hoops with half of our bodies underwater. As I've said before, Pete has me beat in a lot of areas, but basketball was not one of them. I would beat him almost every time we played and today was no different. I kept draining shots while most of his shots went clunk off the rim or the backboard. One of his shots missed so badly his ball went out of the pool and he had to go chase it.

He got out of the pool and I kept shooting. He retrieved his ball and was standing at the edge of the pool watching me shoot.

"What?" I asked.

"Nothing, just watching you," he said. "I like the way your little titties shake when you shoot and you have that cute little bulge in your bikini bottoms when you jump up out of the water."

"Dude, seriously, this is getting weird. I understand ball breaking, but I don't need the commentary about my body. Why are you checking me out anyway?" I asked.

He got back in the pool and handed me my beer.

"You know I'm just messing with you," he said, "I was surprised you actually put her bikini bottoms on and I've been so horny since she left."

"Well don't get any ideas, I'm not that kind of girl," I said sarcastically.

"Care to make it interesting?" He asked.

"Always," I said.

"I challenge you to a game of H-O-R-S-E," he said.

"You want to play me in basketball?" I asked.

"Yeah," he said, "You pick your stakes."

"Ok, when I win you cut out the comments about me looking like a girl or anything relating to that topic, forever."

"Deal, but when I win, you have to go inside and cover your little boobies with your bikini top and then come back in and give me a hand job," he said.

"Dude!" I screamed.

"What?" He asked. "I feel like that's a fair deal. You think you're so much better than me at basketball anyway. Why wouldn't you take the deal?"

"You really want me to jerk you off?" I asked. "Don't you want something else?"

"I used to fool around with Jessica in here all the time. I can really use a release. I can close my eyes and pretend you're her," he said.

"I don't know, this is getting really weird," I said.

"I'll sweeten the deal, we'll play J-O-H-N. That's 4 shots instead of 5, and since you think you can't lose this should be a no brainer," he said.

"Fine," I said, "But you better keep up you're end of the deal when I win."

"Scout's honor," he said. "I'll even let you go first."

I took the first shot and drilled it, nothing but net. He continued his bad performance and clanked one off the rim.

"That's J," I said.

"See you were worried for nothing," he said. "Your shot."

I smiled, knowing I had him. I drilled my next shot and he missed. He had J-O and I was halfway home. I missed my next shot which was ok, he still had to make his and I had to miss to get my first letter. Somehow that happened and I had J. I took a sip of my beer to refocus, which probably wasn't the best idea. It happened again and we were tied at J-O.

He winked at me and said, "Getting nervous?"

"No way, you were lucky on those two. You better not miss again, because once I'm in control, you're toast."

He missed and I drilled my shot. He proceeded to miss and he had J-O-H. One more and I could be done with his nonsense. I was so arrogant that I went for a crazy deep shot to put him away and missed. He made his next one and I missed again. I didn't know what was going on. We both had J-O-H and it should never have been this close.

"Next one wins," he said, "Let me try that deep shot you just missed."

He stepped back and chucked up a shot. From where I was standing it looked like it was way off. I smiled as the ball hit the backboard hard. I had another chance to put him away, so I thought. The ball hit the fiberglass backboard at just the right angle that it bounced off the front rim and dropped through the net.

"Get the fuck out of here," I said, "There's no way you hit that!"

He shrugged his shoulders and said, "Your shot."

I knew I had to make my shot. There was no way I was going to give my best friend a hand job while wearing his ex girlfriend's bikini. I walked over to the spot and took a deep breath. I put up my shot and exhaled. It was right on, I knew I had drilled it. I would live to fight another day. All of a sudden a gust of wind blew and it moved the ball to the side. The wind blew so hard the ball missed the hoop completely and landed outside the pool.

"Whoa, did you miss on purpose so you would lose?" He asked, laughing.

"Screw you," I said, "That doesn't count. You saw the wind take it."

"All I know is that you missed and lost the game. Looks like you have a wardrobe adjustment to make," he said.

"You can't really expect me to do that," I said.

"That was the bet and you lost," he said.

"Come on, double or nothing," I said.

"What would double be? Two hand jobs?" He asked.

"No, you come up with something else," I asked.

"Fine, since you're being a baby about it I'll make it easy for you. A standard foul shot, straight on, a shot you've made a million times. Make it and we're even," he said.

"Ok, and what do you get if I miss?" I asked.

"Well I expect you to get me off wearing the full red bikini, and...," he said and paused.

"Just come up with something," I said.

"Ok, I've been lonely sleeping in my huge bed, so if you miss, I get my hand job and you have to put on one of Jessica's babydoll nighties, panties, and perfume, and sleep next to me tonight."

"Seriously?" I asked, a little stunned.

"Yeah, I was going to pretend you were her while you were jerking me off, and I can pretend you're her in bed. No funny business, I promise," he said.

"Fine, just let me make the shot and we can be done with this nonsense," I said.

"Go ahead," he said.

I got in position. He was right, I've made this shot a million times. I felt the wind kick up again and instead of repeating my mistake I waited for it to calm down. The wind stopped and I raised my arms getting ready to shoot. I released the ball and right away I knew it didn't feel right. The ball hit the left side of the rim and rolled around before dropping into the water. I can't believe I missed again. Now what, I thought to myself.

"Double or nothing, one more time," I said.

"No way," he said, "You lost, fair and square, twice!"

"But..." I stammered.

"No buts," he said, in a stern voice.

I was stuck, and felt like I had no choice. I got out of the pool and wrapped a towel around my waist. I walked into the house and into the guestroom. The red bikini top was staring at me as I walked in. I was really going to do this. Is there such a thing as a bad hand job? Maybe I can make it so bad for him that he finally leaves me alone. I picked up the bikini top and after a few seconds of fiddling with it I got it on. He was right about my little man breasts. I could feel them being held snugly by the bikini. My dick started to stir again and I tried to clear my head.

I walked back out to the pool and was greeted with a whistle again.

"Damn girl, you fill that out nicely!" He said.

"Enough," I said, "Can we just get this over with already."

"Eager aren't we," he said suggestively.

I got back in the pool and I noticed his swim trunks were on the pool deck. He was naked in the pool waiting for me. I still can't believe I had gotten myself into this mess. I decided I would just pretend I was jerking myself off and not think about it too much. Then he started talking and that idea was gone.

"I was serious, you really look great in your bikini," he said.

I really wish he would stop calling it MY bikini. "Thanks, I guess," I said.

"Are you ready?" He asked.

"Ready as I'll ever be," I said.