Chapter 10
by doppledon
What happened on your worst date ever?
The Blind Date
"Well, like many bad dates it was a blind date. My friend had someone he liked and that someone had a friend. My friend needed to distract this friend as she was overly protective of her friend. His idea was to set me up with this overly protective friend so they could go on a date. Now, I've been on blind dates before, but usually we can at least text or talk for a bit and see if there is any compatibility there. You know. Describe ourselves and figure out if we'd enjoy each other's company" you describe the setting of the blind date.
"You two didn't get that chance I take it" she asks and you can feel her fingers on your thigh moving a little bit.
"Erm...no. It was very last minute. The overly protective friend, we'll just call her Jane, was throwing a fit about my friend and her friend going on a date that night. So I was to take Jane out on a date that night to allow them some undisturbed time together. Me, being the good wingman I am, said sure. Anything for you buddy. The work day passed and I prepared for the date. Just a dinner to start with. Who knew where the night might go you know. I get to the restaurant and wait, and wait, and wait. I sent a few texts asking if she was late and if she was ok. No replies. After forty five minutes I'm about to leave, but in walks my date" you continue your story.
"For a second I thought your worst date was going to be one where you were stood up" she says moving her hand a little higher on your thigh. You clear your throat a little trying not to get flustered as she presses some of your very specific buttons.
"Oh, I've had my fair share of being stood up. No, this date was much more unique then that" you say wrapping your arm around her.
"I should mention now that how someone looks usually doesn't phase me. I can be attracted to a personality just as much as how someone looks. Obviously I enjoy the company of beautiful women such as yourself, but ultimately it isn't some kind of deal breaker to me. That said..." you continue.
"She was...hit a few times with the ugly stick" she asks. Her hand is now almost touching your balls now. Making it really hard for you to concentrate.
"Um...yah. More like the ugly cudgel. She walked over to me and we did our introductions, and like most people I gave her a good once over. She was overweight by...a lot. She was wearing a sweat shirt with a stain on it, and sweat pants. To be fair though, the lighting wasn't helping her much. It was giving her upper lip a shadow that was not helping with the mustache she already had there" you describe. Nadene grabs tightly to your inner thigh as she starts laughing hard. After a few moments she finally regains control and you can see in her eyes she wants you to continue.
"I feel like a dick describing her that way, but...yah...mustache. Not like a man's mustache, but definitely noticeable. Again, I was ready for a fun night anyways. Worst case is we never talk again, and I saw it as a chance to make a friend. So anyways, introductions are done and I pull her chair out for her to sit. She thanks me, and I sit down and try getting a conversation going. I'm striking out. All she'll give me is one word answers basically. I usually can find something that people like talking about, but this woman was shutting all of it down. Waitress comes along to get us some drinks. Jane asks if I'm paying, I'm thinking uh oh, but say I am. Without skipping a beat she orders a 50 dollar bottle of wine" you continue.
"She didn't" Nadene says in surprise.
"Oh yes, she did. I don't know if she kind of knew I was just a distraction from her friend and wanted to make the most of it, but whatever her reasons were she certainly did that. Waitress comes back with the wine, pours us our glasses, and asks if we are ready to order. I get a steak, she gets lobster and steak. There went my spare funds for the month. I keep trying to get a conversation going though, with no luck. Literally couldn't get her to say more than three words at a time the entire dinner. Oh...almost forgot. She treated our waitress like crap. Raising her hand and snapping her fingers to get her attention, talking to her like she was an idiot, all the things where you see red flags shooting up into the air. People were looking, and I've never felt so embarrassed to be associated with someone" you continue. You suddenly feel an almost electric shock as Nadene's hand finally contacts your balls.
"Uh..." you start to look down.
"Continue the story please" she says smirking.
"Yes, well, uh, I zoomed through my steak trying to just get through the date faster. She had finished off all the wine at that point, but fortunately didn't order more...instead she ordered some 10 dollar bottle of craft beer. She wasn't drunk either. Like not even a little bit. So there was a deep relationship with **** there too, or at least it seemed that way. Anyways, at this point I'm just kind of done. She finishes her meal, orders a desert to go, I leave a good tip as an apology to the waitress, and we head out the door" you start to say as Nadene moves her hand over your cock to rub your other leg.
"Lost my place" you say distracted as she moves her hand back to your cock and rubs it a little.
"You'd just left the restaurant" Nadene chuckles.
"Right, so we'd just left the restaurant and Jane turns to me and asks if I want to go back to her place. She explained she would rather just get to the sex" you say. Nadene's hand hasn't left your cock.
"Well I can certainly understand that part" Nadene purrs. "So did you go have sex with her" Nadene asks giving your cock a couple squeezes before her hand disappears.
"Um...no. I told her I didn't really feel like we connected and that it was best if we just ended the night right there" you stated.
"How did she react to it" Nadene asked.
"Um...well...she negatively compared me to her dildo at home...loudly. There were a few other choice words and she winged her take home desert at me, which I thankfully ducked under. I think it was pretty likely she knew I was a distraction, and didn't really act like that normally. Likely she just used the date as an excuse to spend someone else's money, or maybe she just didn't know how to talk with guys maybe. Either way it was a terrible date and I no longer do blind dates unless we can figure out if there is any interest between us first. Text, call, face to face, whatever" you say.
"You're a very interesting person Davin" Nadene says placing her hand back on your thigh. You're too distracted by her hand to really form a good response to that so you just wait for her to elaborate.
"You just described a date where someone took advantage of you, yet you still kind of defended them in the end" she says running her finger along the length of your shaft. Causing you to suppress a moan.
"Seems like I'd be pretty easy to be abused if you word it that way" you chuckle.
"Maybe, but don't lose that part of yourself. It may be exploitable if you aren't careful, but it also lets you connect with people. It's actually kind of attractive. Take us for example. You noticed I was in some sort of trouble and offered your help. We have talked before, but I wouldn't have considered us at the stage of helping each other out in life changing decisions phase" she says using air quotes. "You could have just left me on my own, but you recognized something was bothering me and offered to help" she added and then took a sip from her drink.
"I could just be trying to take advantage of you" you counter.
"That would imply I didn't want to be taken advantage of by you" she chuckles.
"Well, I did have some hints during my story that you wouldn't mind being taken advantage of later" you say in a flirty way.
"Ahh...yah, I'm kind of a lightweight with **** and it tends to make me...um...excited" she giggles.
"Is it just the **** that is making you excited" you ask.
"Mmmm...I wouldn't say the only thing. The idea of sex with someone new isn't something I've thought of for a while, and thinking about it with you...I'm finding myself...well..." she pauses trying to think of the right word.
"Excited" you finish for her.
"Yah, I guess that's the best word for it" she chuckled.
"On a scale of one to ten how excited are you right now" you smirk and run a finger up her leg all the way to the waistband of her pants. You dip your finger just barely under her waistband to slide your finger along to top of her panties causing her to let out a moan.
"TEN...mmmm...a ten, definitely at a ten" she almost shouts.
"Should I crank it up to eleven" you ask pushing your hand under her panties and stroking her pubic hair once you find it. She puts her hand on your wrist and you think for a moment she's going to stop you, but instead she pushes your wrist down guiding your hand deeper. Your fingers sink deeper and you can feel the heat building as you get closer. Your middle finger slides over her clit and down her labia. She tenses up and slaps a hand to her mouth to stifle her moan. You notice immediately that she is soaking wet. You rub up and down her slit a few times and then pull your hand out. Looking at her she seems almost in a trance as she watches you bring your finger to your mouth and suck off her juices.
She watches what you do with your finger, but when you pull your finger out she's still staring at your lips.
"Want a taste" you ask as you lean forward to kiss her. Before even a full second of kissing passes her tongue is trying to get into your mouth. You part your lips and let her tongue in. You've felt some enthusiastic kisses before, but she's definitely a contender for the top spot. You pull back from the kiss making her pout a little, but you bring your mouth close to her ear.
"Should we go back to my place" you whisper to her.
Does she want to go to your place?
The Perfect Gentleman
A perfect gentleman is subjective.
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