The Challenge
I was enjoying the last month of my summer vacation from college with my friends as we sat in the basement of my parent's house playing video games. Rob and Johnny were currently playing a video soccer game while Sammy and I watched, chowing down on pizza. I was distracted when my phone dinged, indicated I'd received a text message.
I looked at the message. It was from Vicky Carmichael, the girl I went out with last weekend. We did have a great time together... and she was easy enough to put out on the first date. She was beautiful and a great student and athlete... but she was one of a string of dates I'd been on over the past year. They all just seemed the same. The message said:
>Wanna hang out tonight?
I quickly typed a response.
>No... with my boys tonight.
She came back quickly.
>You know I can be a lot more fun than they can!
Before I could type a reply, she sent another text, this time a picture of her bra-covered breasts. Then another with her wearing sexy panties. While the pictures were sexy, I wasn't swayed. I was actually getting a little bored with college girls.
>Nah... sorry... really... I'm busy.
My text was followed by three more from her. The first was text
>I dunno... I'm really *REALLY* wanting you tonight.
And the other two were pictures... of her pushing her bra down and baring her breast, showing her tight, little nipple. And the other of her pulling her panties aside and separating her labia to show her wet, pink pussy. It almost made me give in... but this was so predictable. Pretty much every girl I dated followed the exact same formula. I went out with them and had a great time. Then we had sex and I'd blow their mind. Then they spent the next month or two trying to convince me to go out again, always... ALWAYS... sending sexy pictures to convince me. It was like clockwork.
"Damn, bro, who in the hell is texting you so much?" Sammy asked.
I was typing a response as I answered him. "It's that girl Vicky," I said. "I went out with her last weekend and she wants to go out again."
>Sorry, babe... maybe next weekend.
"Vicky Carmichael?" Rob asked.
"Yeah."
"Oh my God, dude! She's hot as fuck!" Rob practically drooled, grabbing my phone and thumbing through the pictures Vicky sent. "Holy fuck! Look at this one." Rob showed the pussy picture to Johnny.
"Damn! She's in my psych class," Johnny said. "I would kill to go out with her. I'll never look at her the same way again."
"Hello? And... you're here with us instead of hitting that?" Sammy asked, rightly questioning my sanity.
"Yeah... I'm just tired of these girls," I said. "They're just too easy. You know?"
"Oh... so now you've conquered girls?" Johnny laughed. "How many girls have you been with over the last year?"
"I don't know," I said, kind of counting in my head. "Maybe 25. Enough of them at least. I think what I need is a challenge."
"What kind of challenge?" Sammy asked.
"Girls are just too easy," I said. "It's like, you tell them you like their hair and you're set."
"I think you underestimate women, my man," Johnny laughed.
"That's the thing," I said. "I think what I need is a woman. Someone older."
"Ok... where are you going to find said woman?" Johnny asked.
"Well... it can't be that difficult," I said.
"I guess, older women... in their thirties... can be a little lonely and like it if a good looking guy takes an interest in them," Johnny said. "It's probably not even that much of a challenge."
"I think you watch way too much porn, Johnny," Sammy laughed.
"No, really," he replied.
"I suppose," I said. "It's probably more of a challenge to impress them... get your foot in the door. They know what they like and they're not fake."
"Well... I for one have seen way too many women online that would challenge that description," Rob said. "I'm just saying."
"So... just to make it interesting, she should be married," Sammy said.
"Seriously?" I asked, surprised that any of them would suggest that.
"Why not?" he said. "That's more of a challenge, isn't it? But she shouldn't be old and settled. Maybe one that's just... bored."
"A family member would be an extra challenge, you know," Johnny suggested. "Your sister is older and so very hot."
"Again, dude, you watch way too much porn," Sammy laughed and slapped Johnny's arm.
"No dude," I said. "That's not going to happen."
"What about.... your aunt?" Johnny smiled, deviously. "She's married... she's in the right age range... she's obvioiusly not happy in her marriage...."
"Dude! That so wrong! I mean... she's family," I said, shaking my head.
"Step-family," he said. "Step... not a blood relation. Besides you said you barely even know her."
I shook my head. "Let's just play, ok?" And we went back to our games and pizza. But my mind was elsewhere. My mind was contemplating the "what ifs".
My stepmom's sister, Emmanuelle, came to live with us about a month ago. Her husband, Stuart, had surprised her one day and told her that he thought he was gay. They were now contemplating divorce and she was living apart from him in order to think and consider her options. Obviously, living with a gay husband would put a big crimp in their marriage.
I hadn't even met Aunt Emmanuelle until she moved in. She was hot... with a killer body... and was a couple years younger than my step-mom. She worked during the day and then after dinner watched movies most of the night with a glass of wine. Every night before bed, I saw her come out of her bedroom in a silky robe, with little to nothing on underneath. She'd pour herself glass of wine and then head into the family room, which was set apart from the bedrooms in our little split-level house.
I usually had no idea how late she stayed up or what she watched, but my imagination was rampant as you can imagine, and I had many orgasms to my sexual fantasies involving her. So when Johnny brought her up I was... almost... committed to the challenge outright. It wouldn't take much to make me fully committed.
*****
I spent the next week open to the idea of fucking Emmanuelle and flirted with her. At first I just simply complimented her... the way she dressed for work... her hair... how she looked in her robe at night. I spent a lot of time just trying to be near her and talk to her... and I made sure she saw me looking at her... as a sexual woman.
While she was at work, I occasionally texted her, sometime complimentary messages, sometimes flirty messages. And she responded favorably to them, sometimes even flirting back.
Stuart must have really ignored her, because she ate up my compliments and loved how I showed my appreciation. She blushed... played with her hair... played with her clothes... touched my arm and shoulder... did everything that told me she loved being complimented.
Late in the week, I texted her and asked her about her outfit and she sent me a picture of herself. When I responded complimenting her sexy hose-covered legs, she sent me an even racier picture, seated in her chair, looking down as if I was kneeling before her, with her holding her skirt up a little, giving me a nice shot of her legs and a little glimpse of her pale blue panties.
When I complimented her one night while she was wearing her robe and pouring a glass of wine, she really blushed. "Even late at night just wearing a robe," I said, "you look amazing."
"Oh, stop," she said. "But thank you," she smiled and looked down, embarrassed. "I probably look fat in this robe. But it's comfortable." She adjusted the robe tighter around her body, emphasizing her cleavage even more.
"No... I really mean it," I said. I was probably looking at her rather lewdly, although that wasn't my intent. "You don't look fat at all. You're very beautiful... and... damn sexy, if I can say that. Stuart's definitely an idiot. I can't believe anyone would leave you. I know I couldn't even let you out of my sight if I was with you."
As the week wore on, I started waking up and using the shower while she was getting ready for work. The house only had 2 showers, one in my parent's bathroom, and one in the hallway for the other 3 bedrooms. So, while she was getting out of the bathroom, I was waiting to go in, wearing my own robe. We would run into each other in the hallway, and usually have a laugh as we tried to get past each other.
As the week wore on, I started tying my robe looser and looser, until I didn't even tie it at all... and I was naked underneath. I didn't exactly know if the robe would open much, if she'd see anything, or if she'd even want to. But I was hoping she'd see me in a more sexual light. Could I ever convince her to want me... sexually?
And then on Saturday night, she was kind of depressed as we talked in the kitchen.
"You know, just when you think things are perfect, something like this happens," she said, taking a drink of wine. She shook her head and looked down as she set the glass on the counter as if she were reliving her last conversation with Stuart. "I just feel so... unattractive. I mean, what do you think?"
"You're... beautiful. And smoking hot!" I said, laughing a little to lighten the mood.
She smiled at me. "Thank you. You shouldn't be looking at me like that, though." She tightened her robe around her. "But I mean... it's just the two of us... so... hypothetically... would I turn you on? My ass is firm... I work out... What do you think?"
She turned away from me and raised the back of her robe up to expose her ass.
"I mean, I'm sure you've seen the rear ends of women your age. It's not that bad, is it?"
Her ass looked incredible. Her G-string panties left so much flesh available to my eyes and the little string that delved between her cheeks led my eyes towards her pussy. "No! No, not at all!" I said. "You seriously look incredible."
She dropped her robe to cover her ass and then faced me again. "Am I just old and used up, then? What would make a man turn gay by being with me?"
Damn... Stuart really messed with her head. "You're not old and used up! Stuart's a complete idiot! I say you're better off without him if he can't appreciate you."
She smiled. "You're such a good boy... you're just saying that..."
"No... I mean it," I said sincerely.
