The Challenge

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.

"Ok, listen," she said, grabbing the knot of the belt around her waist, and looking a little unsure of what she was going to do. "I need an honest opinion. So... just for a minute, be a man. Not my nephew. Just a man. Alright? Are you going to give me an honest opinion?"

I nodded. "Of course."

She untied the knot and opened her robe, showing me her body. Her breasts were even better than I ever hoped, nicely proportioned with hard nipples and very large areola. Her abdomen held a little fat, but it only made her more attractive to me. Her hips curved nicely, flowing into her long legs. Her panties were blue with a little silver pattern in them and the small patch made you want to see what it held in secret.

"Do I look... ok? I mean, for my age," she asked.

I couldn't look her in the eye. And it seemed like I took a long time to answer as I tried to memorize everything I could see. I nodded. "You're... you look amazing," I whispered.

"Really?" she smiled, obviously loving my response. "Does my body look... firm?" She grabbed her breasts and squeezed them for a moment, then slid them down to her stomach, pinching flesh there, too. "I mean, I know I'm not your age, but I think I can still hold my own. What do you think?"

"I... I think... you're incredible. Really."

"I like the way you're looking at me," she said softly. "And I like that you're hard," she giggled, looking down at the erection poking out from my robe. "Almost like you... I mean... it makes me feel... like a sexual... woman. You know what I mean, right?"

"Yeah... I know what you mean," I said, licking my lips. "And you're not wrong."

She tied her robe closed again, breaking the spell. "I just really... want something. I really... need something. But I'm like... held hostage." She walked over to me and kissed me on the forehead. "Thanks for listening to my rants. Sleep well. Love you." Then she grabbed her wine glass and headed towards the family room, leaving me dumbfounded... with an extreme hardon.

"Love you, too," I said softly and turned towards my bedroom on the other side of the house.

*****

The first chance I had to try things out was the Thursday after the week of flirting. As was normal, Aunt Emmanuelle moved into the family room in her little robe and full wine glass and I disappeared into my bedroom. After about an hour, I came back out and made my way to the staircase that led from the bedrooms to the family room.

I heard moaning at first and quickly realized it was coming from the TV. Aunt Emmanuelle was laying on the couch, which offered a view of the staircase and the TV. Her robe was opened and her legs were spread lewdly. One hand was between her legs, touching her pussy, the other at her breasts, teasing her nipples. I was frozen in place, just watching her slowly masturbate while the movie played. She wasn't in a rush and seemed to be just keeping herself excited.

I glanced at the TV and there was a man and woman having sex, the woman bent over the side of a bed, the man entering her from behind. The video cut from his cock slamming into her pussy, his hips slapping her ass, to her face contorting in pleasure as she moaned with every thrust. The music added an artsy feel to the whole scene.

The woman in the movie was definitely enjoying getting fucked. And Aunt Emmanuelle seemed to be enjoying watching it. Her fingers danced quickly and her body gyrated as pleasure flowed through her.

"Holy shit!" I whispered, barely loud enough that I even heard myself. I knew I could passively sit and watch her play with herself or I could be confident and daring enough to just walk in to the middle of her masturbation time. I chose the latter.

"Hey Aunt Emmanuelle!" I said as I finished walking down the stairs.

She jumped to cover herself up, pulling her robe tightly around her as she sat up, but neglected to turn off the movie. "Oh... wha... what are you doing here?"

Sounds from the movie, grunting and moaning as music played, played on as I walked into the middle of the room. "I saw you were up watching a movie and you said you wanted to get to know me better. I figured we could maybe watch a movie together."

"Um... I... I don't know, Vince," she said, obviously scared that she was caught.

I sat on the edge of the couch and turned my attention to the action on-screen. "What are you watching?"

"Oh my God... it's um... it's called 'Delta of Venus'," she said, grabbing the blanket from the back of the couch and pulling it over herself.

"Isn't that like... porn or something?" I asked, not taking my eyes off the screen. The duo on the screen had just finished the sex scene and the movie played on with them waking up the next morning.

"I like to think of it more as... um... as a romance story," she said.

"Ok. Well... we can watch this if you want," I said, sitting back on the couch and making myself more comfortable. I was wearing a t-shirt and a thin pair of pajama shorts. The action I'd seen on the couch got me far more excited than the action on the TV, so I was a little hard. "I don't think I've seen this one."

"Are you sure you want to watch this?" she asked. She was hoping I'd just leave her alone again. "I mean... this isn't a movie you'd probably ever watch. And... this is kind of... weird. It'll probably make us both uncomfortable. And it's pretty far along."

"Nah... it'll be fine. How bad could it be?" I asked, confidently.

"Ok... suit yourself," she said hesitantly.

We sat and watched the movie, and it didn't take long for another sex scene to start. I could feel myself getting harder and had to adjust my cock a little.

She must have seen me. "I uh... hope you don't get any ideas," she said.

"What do you mean?" I asked, feigning innocence.

"You know... the movie... me." I looked at her and tried to look innocent. I was just a guy watching a movie with his aunt, right?

I turned my attention back to the movie and we watched for several minutes more before the action got pretty heavy.

"Have you ever... you know... watched porn?" she asked. "I mean... you are a guy so I suppose you have."

"Yeah... I do sometimes. You?"

"Sometimes," she said. "Especially after Stuart, you know, came out. I just... you know... sometimes need... something... and I can't with my husband and can't with someone else because I'm married. It's hard. I'm kinda trapped."

"I can imagine. You know... you look like that woman," I said, changing the subject and indicating the actress in the show.

"No... you think so?" she asked, surprised that I'd compared her to someone like that.

"Yeah... I mean, she's beautiful," I said. "Older women are sexy."

"Wow... I never thought I'd hear someone your age say something like that," she said, genuinely surprised. "You really think so or are you just saying that?"

"Yeah, I really think so. An older woman that is smart and sophistocated and knows what she wants," I said. "There's nothing more sexy."

"Uh huh... come on," she doubted.

"No, I'm serious," I said. "You're beautiful. The most beautiful woman I know at least."

"Come on."

"I'm sorry... but that's what I think," I said, almost apologizing for my opinion.

She looked at me a moment with a little smirk on her face. It was like she thought she knew what I was doing. "This isn't funny, Vince."

"I'm not trying to be funny," I said, trying to sound innocent again.

"Vince... I'm flattered and all... but it's never going to happen," she said. "I'm married."

"I know," I said. "I just... I hate to see you so... needy."

"Ok," she said, putting her hands up in front of her. "I dunno... I don't know if we should be watching this. It feels kinda wrong. I shouldn't be watching this with my nephew. Especially this kind of movie."

"It's ok... really," I said. "It's just a movie and it's nice to... to spend time with you."

"I like spending time with you, too," she said. "I'm having a great time. You're absolutely certain you're ok with this?"

"Yeah, of course," I said.

"I just feels so... dirty," she said, putting her hands under the covers again and pulling them up to her shoulders.

I smiled. "I think that sometimes feeling dirty is fun."

"Alright," she said, sitting back into the couch again. "We'll just watch it."

The movie changed into yet another sex scene. This time, the man came up to her in public, grabbed her and kissed her, as if she were exactly what he need to live.

"Oh my! That's uh..." she said, sounding a little stunned.

"It is pretty hot," I agreed.

"Wow... she is really into that guy," she said, her voice sounding a little far off like it was really affecting her. "Look how forward he is. He just... assumes."

"Is that something women like?" I asked.

"Yeah... very," she said, almost breathlessly. "Just watching them... kiss... it's so..."

"Passionate and raw," I said. I could feel my cock getting harder, tenting my shorts.

"Yeah... and she actually looks like she's turned on," she said. "That's good acting."

"Have you... ever been kissed like that before?" I asked her. I felt movement on the couch from her, but couldn't quite tell what it was.

"Well... maybe... but it's been a long time," she said sounding sad. "I mean... I should have seen it coming. Stuart hasn't touched me in a long time."

I nodded. "Yeah. That's too bad. I mean... everyone needs intimacy. At least I think so." I grabbed the edge of the blanket and slid underneath it, covering my body with it similar to her.

"Make yourself comfortable I guess," she said. She didn't sound mad, just... surprised.