Bowlarama! Ch. 01

Welcome to another one of my stories! My ex-girlfriend said I should share some of these crazy stories with the world. At the time, I never bothered but now with the pandemic I have a lot more time on my hands, so...enjoy! I have changed the names to protect everyones privacy, but the rest of the story is 90% true and 10% filling in the blanks of minor details that I don't remember.

Tonight we will meet some new characters. This story took place right around the same time as "Happy to Help", around 2012 or so. I remember it happened in the Summer and I remember I lived in that same apartment (the first place I lived after the house in "She Sure Showed Us") but other than that, I don't remember exact timeframe.

Even though I had a ton of fun with Laura and Brynn (from "Happy to Help"), I wasn't exactly dating either of them. In fact, far from it, since they were dating each other. So I was still using a dating site and meeting some girls. I had actually hit somewhat of a dry spell but since I was having fun with Laura and Brynn (remember, in real life, "Happy to Help" was spread out over a few weeks, not one night) I didn't really mind the dry spell too much. Then, I met Jenny.

In hindsight, I probably should have been a little more serious with Jenny than I was. She was super cute, fun, smart, funny and generally low maintenance. But, she lived out in the suburbs and I was having way too much fun living the city life to be tied down in those days. Jenny was short and petite, probably 5'2'' or so, and skinny. She had a fantastic pair of C-cups, medium-length red hair and fair skin. Whatever the opposite of having a tan is, that was Jenny. Between her hot little body and her bright red hair, Jenny was definitely a head-turner.

We had been out for a happy hour, and also been on one proper date. We went back to my apartment after our proper date but we didn't go very far, just a little making out. I sensed she had a bit of a wild side but apparently she was not the type of girl for a quick hook up. That was fine though, I enjoyed spending time with her. We spoke a couple of days after our first actual date and she invited me out to the suburbs to go bowling with her and some of her coworkers. At first it seemed like this was a second date with no real shot at a hookup but then she mentioned that maybe we should head downtown afterwards. I told her that sounded great and we planned to bowl with her friends and then head back to my place in the city afterward. I wasn't totally sure if that meant she was planning to spend the night but I was hoping for the best!

The only real issue with this plan was that bowling takes forever, especially if you're with a group, and we weren't evening planning to start until after work. Plus, I was planning to drive so I would be bowling sober! I was excited to see Jenny, but not excited to bowl. Still, I put on my happiest face and I was glad I did. She was dressed to impress, coming straight from the office in tight jeans and a tank top that showed a decent amount of cleavage. I was trying to figure out if this outfit was work appropriate when I figured out she had on a blazer that made it ok in the office. Still, it was quite the "casual Friday" outfit!

Jenny greeted me with a kiss on the cheek, and introduced me to her coworkers. I was thinking it would be a much larger group than it actually was, but it turned out to only be about eight of us. We set up shop across two lanes, and bowled a few frames. I'm somewhat of a decent bowler, but I wouldn't say I actually understand the game very well. Mostly it was a social occasion and nobody was a particularly good bowler. Especially Jenny!

I hit a couple of lucky early shots and was doing decently, and Jenny decided to do a little trash talk. Mostly flirty banter, but I took advantage. About two turns in we were sitting alone while the other folks were taking their turns, and Jenny decided to up the ante with her trash talk, and suggest a bet.

"Ok, you're on!" I said.

"Alright, what are the stakes?" she asked me.

I wasn't really sure how far to push this, but since she had already planned to come to my house, I figured I could make it a sexy bet.

"How about...winner gets to pick out what the loser wears at my apartment tonight?" I suggested, with a grin.

The bet didn't specifically call for nudity but it's not like she had a lot of clothes with her. I noticed she hadn't brought an overnight bag but she did have what looked like it might have been her "big purse".

"Okay! You're on!" she said, grinning back at me.

Now I am not suggesting that Jenny threw the game, but I did notice she tossed a few more gutter balls after the bet then before. And each time she did, she'd turn and pretend like she was really bummed but then give me a wink. I liked where this was heading!

I don't exactly understand how bowling works with how many extra shots everyone gets. It's almost like soccer, where nobody knows exactly when the game ends. But even without extra shots, I was still way ahead of Jenny when the game started to wrap. She didn't seem to mind.

Soon enough, the game was finally over and sure enough, I had beaten Jenny pretty handily!

"Looks like we have a winner!" I said, grinning.

"I guess so!" she said, with a wink.

Clearly she was ok with her penalty!

Her coworkers were planning to head across the street to a bar for food and drinks, so I was relieved when Jenny declined and said that we had to get back to the city. Not that I minded, but I didn't want us to get back at midnight or worse, end up with Jenny taking a rain check for her city visit. So I played it cool and followed her lead, and soon enough we were in my car and headed to the city!

We got into my car, and headed toward the city. Normally that would have been about a 15-20 minute drive but there was a wreck so we were stuck in slow traffic for awhile. Thankfully it wasn't slow enough to completely stop us, and gave us some time to chat on the way.

Finally, Jenny brought up the bet.

"I always make good on my bets! What outfit do you have picked out for me?" she asked.

I cant imagine she didn't know what I was going to say but she wanted me to say it.

"Well, I think you look great with a smile. So, I was thinking a smile and nothing else. Unless maybe you want to keep those cute high heels on." I said.

She blushed a little, and grinned.

"Okay. You won the bet, after all!" she said, with a shrug.

As she said it, she unbuttoned her jeans and slid them down her hips. I nearly ran into the car in front of me.

"Eyes on the road, mister! You'll have plenty of time to stare later." she said.

She kept going. She slid all the way down in the seat and pulled her tank top over hear head. Then she reached behind her and unsnapped her bra. Then she picked her hips up off the seat and slid her panties off. She reached in the back seat, put all of her clothes back there and grabbed her blazer. She put it on, and was sitting in the passenger seat naked with just her blazer covering her up.

"I should probably keep this much on for now, I don't want to cause a car accident!" she said.

Of course, I was totally blown away but I was trying to play it cool. Both because she was, and of course I was still driving. Thankfully the traffic eased up a little bit and we started moving. But of course, being in a busy area downtown the four or five blocks between the exit and my apartment had traffic lights and were completely "stop and go", with plenty of pedestrian traffic around. Jenny was covered but not by much! And she was completely naked from the waist down.

Finally, at a traffic light I had a good opportunity to take a closer look. She had a thin landing strip and was keeping her blazer open just enough to give me a good look.

It felt like an hour but I am sure it was just a few minutes later than we pulled into the underground parking garage for my building. About two seconds after we pulled inside, she pulled the blazer off and tossed it into the back seat.

"Fair is fair!' she said.

I liked where this was heading.

I found a parking spot in the back. My building had a main set of elevators in the front of the building that went to the lobby but also had an extra elevator in the back that went straight into the garage. She may have remembered that from her first visit, since we went down the back elevator when I took her home. It was about 10pm so it was pretty unlikely anyone else would be in the back elevator, unless they pulled in at the exact time that we did. The only real risk was that we would hit the button for the elevator and it might have someone coming down.

"Are we pretty safe in the back elevator?" she asked.

"At this hour? Probably." I said.

I thought it was pretty unlikely that anyone would be around and super hot that she wanted to go up to my apartment naked. The back elevator didn't stop in the lobby, so that helped our chances. Still, I didn't want our security guard knocking on my door and interrupting the fun later. I used to keep an extra sportcoat in my car just in case I had an impromptu meeting at work, so I grabbed it. I figured I could still let her be naked unless the elevator stopped, in which case I'd just take off my sportcoat and throw it on her. She was small enough that my sportcoat would just about be a dress on her anyways.

It's worth mentioning a few things about the building. The building was mostly people in their 20's and was pretty laid back about parties and stuff. Almost every weekend there was a big, loud party somewhere in the building and I didn't think anyone would be particularly offended by a naked girl in the elevator or hallway. Also, there was a small pool area on the rooftop and it was a common joke that the security didn't hassle skinny dippers unless they caught you having sex up there. Just in case though, I had my blazer.

She put on her shoes, took a deep breath and opened the car door. She looked around a bit, didn't see anyone coming, and got out of the car. Naked.

"Lead the way!" she said.

I walked us to the door leading to the elevator. I pressed the button and we waited for what felt like a long time but was probably 30 seconds or so. I noticed how hard her nipples were, and I'm sure her heart was pounding. The elevator doors opened, and thankfully nobody was inside already. We got inside and we made it just in time! No sooner did we get inside the elevator did we see headlights coming around the corner!

Her eyes lit up and I could tell this "could get caught and almost got caught" moment turned her on. I pressed the button for my floor, and we started moving.

"Well, I hope we're alone for this entire ride!" I said.

Of course, the odds anyone was headed up on the back elevator were slim but I could tell it was a turn on for her so I played into it.

"I hope so too!" she said, in a tone that suggested it might not ruin her night if we did run into someone.

We made it up to my floor without incident, but as soon as the door opened my heart (and I'm sure hers) jumped a little bit. We heard lots of voices!

I poked my head out, and it looked like the coast was clear. The building was shaped in a rectangle and it sounded like someone just around the corner was having a party. I motioned for her to get out and hurry up while the coast was clear, and she walked as fast as she could in her heels. My apartment was practically across from the elevator (in fact, it drove me crazy because it had an especially loud "ding" it made when it arrived) so we didn't have far to go. I got my key out as fast as I could, and opened the door. Apparently some people from the party were heading out because the ding seemed to attract attention. I got Jenny inside and out view just in time, again!

"Phew! That was close!" she said.

I could tell by the look on her face that running around my building naked was a big thrill for her.

"What, did you not want them to see your sexy little body?" I said, in a joking tone of voice.

She didn't say anything, she just stepped into me and kissed me, hard. Finally I got my hands on her. I rubbed my hands down her sides and could feel goosebumps on her skin. We kissed for a few minutes and I gave her ass a nice little squeeze. We broke off our kiss, and I lead her from the foyer area into the apartment.

"Normally, I'd be a gentleman and ask if I could take your coat but I guess in this case, I'll just offer you a glass of wine." I said, with a wink.

"A glass of wine would be lovely." she said.

We made our way into the kitchen and I was so distracted by her boobs that I could barely operate the corkscrew. Seriously, they were amazing. The people at the party around the corner who headed to the elevator just a few seconds too late had no idea how badly they missed out!

"Having a little trouble there?" she said.

"Yeah, something must have me distracted." I said, as if we didn't both know what it was.

"I wonder what could have you distracted." she said, almost in the voice of a phone sex operator.

"I guess we'll never know..." I said, as I reached out and gently tweaked one of her nipples.

She moaned softly as I did it. Her nipples were rock hard. Finally I managed to get the wine uncorked and poured us each a glass. She took her glass of wine in one hand, took my hand in her other and lead me into the living room. I was starting to understand that she was quite an exhibitionist and I was determined to make this evening memorable for her. So, I pressed my luck just a little bit.

"Shall we enjoy our wine on the balcony?" I asked.

That apartment was on the 9th floor and even though it overlooked an alley, you could see the highway we rode in on just about 150 yards away. It was fun to sit on the balcony at night and watch headlights of cars stream past in the distance. The building was somewhat old fashioned in its architecture and the balcony offered a fair amount of coverage. Still, Jenny was naked. If she sat down, she would be somewhat hidden from the other balconies and ground but if she stood up, you would be able to see her from every direction.

"Sure! I bet it has a great view!" she said.

Clearly she didn't mind me raising the ante.

"I think it will be the other balconies that have a great view!" I said, nodding toward her boobs.

She laughed, and headed out to the balcony. I followed.

She wasn't shy at all. My neighbors on both sides were either not home or not on their balcony, but there was a party about five or six balconies down. Jenny leaned right up on the railing. The balcony covered her completely up to about her navel, but everything above her navel was completely visible as she leaned against it. Her elbows were on the railing, which made her arms somewhat cover her boobs.

We chatted for a few minutes, and I rubbed her back with my hand. Finally, the people having a party down the hallway noticed us. They waved, and yelled something. We couldn't really hear them, but it was clear they noticed Jenny. She smiled and waved, but kept her non-waving hand on the railing so they couldn't really see her boobs, yet.

They were definitely hoping for a flash. Aside from smiling and waving, Jenny more or less ignored them until we realized one of the girls at the party was offering a flash in return. Jenny seemed to like the idea, and she stood straight up, giving them a great look at her boobs. They all cheered, and one of the girls at their party lifted up her shirt and flashed us her boobs. Jenny stood there sticking her chest out for a minute, and then we headed inside.

I could tell that flashing her boobs at the other balcony was a big turn on for Jenny.

"I didn't expect that you were such a naughty little exhibitionist." I said, as I rubbed my hands down her arms, to her waist.

"Who, me?" she said, innocently.

"Yes, you!" I said.

"I have no idea what you're talking about." she said, clearly enjoying my hands on her.

"Ok, how about a second bet?" I said, and her eyes lit up a bit.

"What did you have in mind?" she asked.

"If this is totally turning you on, you will have to come on another naughty exhibitionistic adventure with me. If not, I will let you have your clothes back." I said.

"And just how would you prove if I am turned on?" she asked.

I didn't say anything. I just reached my hand down to her pussy, and she was dripping wet. I slid a finger in, and she instantly moaned as I found her clit and worked a little circle or two around it. I wiggled my finger on her clit, and she fell forward into my arms, moaning.

"I guess I won the bet?" I asked.

"I guess so. What do I have to do?" she asked back.

"We'll see...but in the meantime, I think we have both waited long enough tonight!" I said, and lead her toward the bedroom.

She grabbed at my shirt right away, and I helped her pull it over my head. We got right down to business. She dropped to her knees right away and started working my belt buckle. She pulled my pants and boxers right down, and my dick sprang out from its confinement and nearly hit her in the face. She clearly liked what she saw, as she took it deep in her mouth. She was doing a great job, but after all that buildup I didn't need much warming up. I let her go for a minute or so, and could feel my dick throbbing. I stood her up, and put her down on the bed. I climbed right on top of her, and she spread her legs wide open for me.

She didn't need to ask me twice, I slid my cock right inside her, and she moaned with pleasure. It only took a few seconds for us to settle into a nice rhythm together and her pussy felt great! She pulled me closer to her, and whispered in my ear.

"I was wondering how long you were going to make me wait for you to fuck me." she whispered, in between moans.

"I promise it's worth the wait!" I said back.

I pushed my knees up and started pushing in at a deeper angle, and it worked its magic in no time. She started moaning much deeper, and much harder. Finally she screamed out that she was about to cum.

Normally I'd tease her a little more but I decided to just let her have this one, and I kept at it. Another 15-20 seconds and she screamed out that she was cumming. I arched my back to hit her clit better, and she exploded in orgasm. I was still holding strong, so I let up and gave her a minute to catch her breath.

"Wow...that was exactly what I needed. Are you close?" she said, with a huge smile on her face.

"Oh yeah!" I said.

She grabbed my dick and climbed on top of me, sliding me into her again. However amazing her tits looked before, they looked even better from this angle! Just watching her on top of me, rubbing her nipples in her hands, was almost enough to get me there but she started moaning and I figured if I could hold out a few more minutes and let her cum again, that would be better for both of us. It was.

She rode me for a couple of minutes, and I could tell she was close.

"Are you close?" I asked.

"Oh yeah! You?" she answered.

"Oh yeah!" I said.

And I totally let go, and I was close in no time. The sound of me getting close seemed to put her over the edge because within another few seconds we we were both getting there. Normally I hate cumming hate with a condom on but I wasn't about to stop my momentum at that point! We both moaned out in orgasm, and I came super hard. I think I came first but I was able to keep going through my orgasm for her, and she wasn't far behind.

She collapsed on top of me in a sweaty mess, and snuggled up to me. We probably could have gone one more time, but why bother? We both came pretty hard and it was getting late. I remembered that she didn't have any clothes with her, so I offered her a T-shirt to sleep in but she just smiled and said she always sleeps naked. I smiled, and figured I could get used to having her around. Not long after that, we drifted off to sleep.