Josie Ch. 01: Not Quite a First Date

After things had fallen apart with Maria, I met Josie at an end of summer BBQ at my friend's house. When growing up, I had spent a lot of time at that house, and his parents were like a second family for me, so I was surprised when he had a female cousin there. She was a cousin that he had never even known he had until they had met when he did an online geneology search a few months before - her father being my friend's dad's younger half-brother. My friend's dad had never seen, or heard from, his father after he left his mom, and didn't know he had half-siblings. He thought his dad had died during the war and Japanese occupation of the Philippines.

Josie is extremely attractive and sexy in a super cute kind of way. She is a medium brown Filipina, short and petite, well rounded - even a bit chubby - in a way that just screams "cuddle me". She had a tall Scandinavian girl with her that day, her roommate - who we will call Suzie, because I honestly don't remember her name at this point. I found that the Scandinavian girl was cold - a true "ice princess" while Josie was fun to talk to - when I wasn't hanging out with her, I kept stealing glances toward Josie, where she sat with Suzie. After the BBQ, my friend's mom asked me if I liked the girl, and -thinking she was talking about Josie - I said that I thought she was very attractive, and seemed really nice.

"Do you want her number? I have her number, and she asked me to give it to you - because you kept looking at her when she was sitting over there with my niece. I don't think she was going to come with Josie today, but we told her that there would be a nice single military guy here, and she decided to come. I think she may be looking - you're still looking, aren't you? You haven't said anything about a girlfriend for a while - certainly not since things didn't work out with that Maria girl you were so stuck on a while ago."

I set up a date with the Scandinavian roommate, but when I went to Josie's apartment to pick her up, Suzie wasn't there, because she had to work late. Josie and I spent the next few hours waiting for her roommate to come home - every hour or so, we'd get another call, explaining that there was another delay, but she would be leaving soon. Josie and her young daughter didn't have any special plans that night, so we had some food, some wine, watched a Disney princess movie, played a bit with Josie's daughter, then cleaned her up and put her to bed.

"You don't have to read her a story, you know. It was nice of you to volunteer, but you've already been such a good sport about playing around and being goofy while you are waiting for Suzy."

"I actually love reading stories to kids. Watch - she'll love it." And she did love the story, as did Josie.

"You've been nicer to my daughter than any other guy I've dated - you're even better with her than her dad. Thanks for helping out."

"I don't mind. I actually enjoyed myself. Maybe I should have just asked you out from the get-go."

Josie blushed. "You don't want me. I'm divorced, and Suzie's so thin and cute - tall and blonde, and her chest is amazingly large for such a thin girl. All the guys think she's sexier than me. When we go out somewhere, she gets all the attention." I couldn't help but glance down at Josie's smaller, but perfectly perky breasts, and she may have noticed.

"You know, Josie, when I asked your aunt to help me get a date, I was asking about you, not Suzie. I guess she misunderstood, and I assumed that must mean you were already taken - then you started talking about your daughter, and I was certain that you weren't available."

"So you're saying that Suzie was your second choice?" Her eyes flashed playfully.

"No, not at all - and don't you dare tell her that!"

"But I was really your first choice? What do you think now?"

"I would love to date you, but it might be awkward at this point, you two being roommates and all."

"True enough, but circumstances change." She smiled.

There was a noise at the door and Suzie entered the apartment. "I can't believe that my boss kept me so late, and that guy your aunt set me up with probably left already and... Oh, hi." She said as she saw me sitting on the couch. "Let me just get cleaned up a bit, and we can still catch a late dinner - if you are still up for that."

"Sure," I said. "I've snacked a bit here, but didn't eat dinner yet."

"I'll be just a minute" Suzie said, ducking into the bathroom.

"Thanks for a great evening, wish you didn't have to spend it with a boring mom, instead of out with Suzie, getting wild with that sexy blonde girl." Josie told me.

"I'm not sure about that, I think you probably have a pretty wild side, yourself." I smiled and winked, and she grinned back as if I had figured out her secret.

"No, I'm just trying to be a good, Catholic girl." She said, smiling coyly.

"You ready to go?" Suzie asked, as she emerged, looking ready for a party.

"Sure." I replied. "See you later Josie, it's been fun." I said, and Josie hugged me and kissed my cheek. Despite the fact that it was obviously just a friendly hug, I was rock hard as soon as I felt her wonderful body against mine. As we separated, Josie glanced down at my crotch with a look of surprised amusement on her face.

Dinner was okay, but there was no real spark with Suzie. Since it was already pretty late, we didn't do much more than have a few drinks while waiting for dinner, then eat, during which she expressed almost no interest in anything I had to say, ignoring every attempt I made to get her talking. There was no spark between us - certainly not the kind of easy, comfortable talking and joking that Josie and I had enjoyed earlier in the evening.

"You worked late today, I can take you home if you're tired, or we can stay out a bit more, maybe go to a club..."

"Taking me home will be fine." She said. "But don't think you're going to spend the night - or even come in. I know you probably expect something, especially after waiting so long for me. I hope that you will be satisfied with a stroke job." I was taken completely by surprise at this. It was so completely out of left field - the date had been terribly dull, with no chemistry between us. I wasn't even sure if I would get a good night kiss - or even want one.

"Uh... sure. That would be okay." I stammered out. Who'd turn down a handjob from a Nordic beauty like her? She reached over and started stroking my cock through my trousers during the drive back to her apartment. When I wa fully erect, she undid my zipper and belt, and fished out my cock.

"Oh, this is nice." She said, expressing actual interest for the first time on the entire date. She stroked my shaft with one hand and used the other to tickle my ball sack. "Pull into the back corner of the parking lot." She instructed me. "Away from the lights". I did as she instructed, and parked the car. She continued stroking my cock.

"Do you have some tissue or something?" she asked. "I don't think you want to make a mess."

"Uh... sure... I think I have..." I scrabbled around until I found the small tissue box I kept in the car, thinking how lucky it was that seasonal allergies caused my nose to run.

She continued stroking my cock masterfully, cupping my balls as I raised my ass off of the car seat, my thighs grinding into the steering wheel. It felt good - really good. She certainly knew what she was doing.

"Does it always take you this long?" She asked, looking a bit peeved. "I don't want to be out here all night."

"I don't know, sometimes after a few drinks it takes a while. Usually, women like it if I last a while." I tried to make a joke out of it.

She stroked for a few more minutes "This is taking too long." She stated. "What do you need me to do to get you off? Play with your nipples? Squeeze your balls? Finger your ass... Oh! I notice how you reacted to that suggestion. How's this?" She started jabbing a finger into my ass, not startying gently, and unlike Maria, Suzie had long fingernails, and they hurt.

"Careful." I grunted, "Those things are sharp!". She sighed and stroked my shaft faster, still working her finger into my anus, but being a bit more gentle about it. I wriggled around on the car seat, in pleasure, but also a bit uncomfortable. I wondered how it could be that Maria could get her whole fist and arm into my ass, but it was painful for Suzie to get just one finger into me.

A few minutes later, when I still hadn't cum, Suzie sighed in exasperation, muttered an "Oh well then." and sped up the pace of her stroking and clutched my cock in a death grip. I noticed her glancing at her watch, even as she stroked my cock, and knew that she was losing patience. I had had a few drinks, and as I had said, that sometimes made me last a long time, if she had stopped at any time, or even slowed down, I probably would have lost my erection, but she was a determined young lady. Probably wore down my sensitivity with all the masturbating I'd been doing since I first discovered self-pleasuring, way back in elementary school.

I know that it's wrong to think of one girl when you're with another, but, I guess I'm just a cad, because I thought of Josie, and how good it felt to have her hugging me. I imagined cupping her face in my hands and leaning down to kiss her, and then...

"Help me clean this mess up!" Suzie demanded, as my cum shot out of my cock and splattered on my dash board, her top, my trousers, and my shirt..

"I'm sorry, Suzie. I thought you wanted me to finish up." I apologized, embarrassed that I had got so caught up in my fantasy that I hadn't even realized that I was blowing my load until it was already happening.

"Into the tissues, not all over everything! Still, that was a nice amount, and you lasted pretty long, too. I bet you're a good fuck, even if you are a full day's work to stroke off." We used the whole box of tissues on her, leaving me with a mess on my shirt and trousers. I still tried to salvage my image as a gentleman, and walked her to the door.

"Well," she said, "I'm not happy with you right now, but I'm also not sure if I really want to miss the chance to be fucked by a guy who can stay hard for..." She checked her watch again "Well over an hour?" She pecked me on the cheek and told me "You can take me out again next week, a nice dinner, and then you'll come in and fuck me for the rest of the night. We'll let that stupid church girl listen to what it sounds like when a man pleases a real woman." Again, I wasn't sure what to say, but, as she turned and opened her door, I realized that I was being dismissed. She was certainly a bag of mixed messages, that Suzie.

"Good night." I said to the door as it closed in front of me, then noticed that Josie was looking out her window and smiling at me. I gave her a little wave, and she pointed to my stained crotch and blew me a kiss, smiling and laughing. I smiled, too, thinking about how different Josie was from her sexy but cold roommate. When I got home, there was a message on my machine. It was Josie.

"Hi!" Josie's voice said. "Hope you made it home alright. Ialso hope you had as much fun being stranded with me and my daughter as we had with you. Since you're so good with kids, would you want to babysit my daughter tomorrow afternoon? Hope to hear from you soon - you know my number - it's the same as Suzie's. I'll be up for another hour if you want to call." I didn't have any plans for the next day, so I called. After confirming the babysitting plans, she started giving me a hard time about my date with Suzie. "It looked like you spilled something - was that at dinner, or in your car?" She laughed. "Did she give you the standard first date handjob in the parking lot? Now you see why everyone wants to go out with her - handjob on the first date, sex on the second, more sex after that - she's some kind of nympho and I just can't compete with that. Anyway, thanks for being good company for me and my daughter tonight, and do me a favor, and try not to be too loud when you're with Suzie next date, it's embarrassing when she wakes my kid up with her sex noises."

The next afternoon, I had a good time being the goofy guy babysitter for her daughter. Playing games with her and watching the inevitable Disney princess movie, then making her dinner before Josie returned. The only downside was Suzie, who thought I was there to get into her pants sooner than she had planned. It was obvious that she was both pleased by the thought that I couldn't; wait to have her, and upset that I wasn't following her schedule.

"If you put on another movie, you can come fuck me while she watches it. Make sure it's a long movie, if you're planning to last as long as you did last night." She told me. This Suzie was certainly different than most women I'd ever dated.

"I'm not here because of you, Suzie, I'm here because a friend asked me to watch her kid, and you just happen to live in the same apartment." I kept telling her, to which she'd agree sarcastically, and then stroll through the apartment in a different sexy outfit. Ironically, this was making her less and less attractive to me - like the many movies where the guy spends most of the film trying to get with the "good looking" girl who is shallow and heartless, and then in the final reel ends up realizing how awesomely attractive the girl is that he has had trapped in his "friend zone" for years.

Suzie also spent some time on the phone, which - and I really wasn't trying to overhear - was mostly about delaying the arrival of that night's date, until after I had left. I finally told her not to worry about it. "You're a gorgeous and sexy woman, Suzie, it's obvious that you have a lot of guys after you. We've only been on one date, it's not like we've made any plans to be exclusive."

"You are so practical. I like that. Must be because you are a soldier. The girl is still watching her movie - do you think you would come more quickly with fucking than you did last night? I will even give you a blowjob, to speed things along. " I hesitated, sorely tempted by the offer. "Here," she said, grabbing my hand and pulling it to her "Feel how wet I already am", she had my hand inside her skirt, rubbing it against her panties, which were soaked and warm. This was getting weirder and weirder. Was I in some kind of perverted Twilight Zone episode?

"Sorry, Suzie, I'd normally love to, but I'm watching a kid right now - I can't just sneak off and have sex with you." Even though I was tempted, and was just about to give in when the girl called out at a scary point in the movie. "Gotta go and do the babysitter thing. Sorry Suzie. Save it for your date tonight." I went back into the living room, and made sure everything was okay.

"Okay soldier boy, you are the one who is missing out!" Suzie fumed as she stormed into her bedroom, and didn't come out until her date arrived - she glared at me and rubbed up against him making it obvious that she was in heat. He was quite happy to skip their dinner plans and go straight to her bedroom with her when she asked him to.

Her sex-talk with her date was quite loud, even given the thinness of apartment walls. "Yes, put your big cock in my mouth and let me suck you!", "Yes, eat my pussy!", "Yes, fuck me with your big cock!".

I had to agree when my young charge observed that "Aunt Suzie gets loud when she plays with her friends. I hope she doesn't hurt herself." Yes, she got quite loud. And I guessed that some of it was for my benefit - to show me what I was missing. Yet oddly, it was more funny than arousing. It was still going on when Josie got home.

"I can't believe that she does that kind of thing with my daughter in the house!" Josie complained.

"Me neither." I agreed. "What do you say we three go over to my house? I've got some good kids movies, can make us dinner, and you can have a nice, quiet evening."

"That sounds good. You don't mind, do you?"

"As long as you pretend not to notice that my place needs a vacuuming and that there may be some clutter on the coffee table, we're good." I said, as I ushered her to the door.