Wicked Wednesday 245 – Second Thoughts (Uncertainty of a Woman)

Lexi frowned at her reflection in the mirror. For the third time, she stripped down and hunted for a different outfit. Her body was Rubenesque and delightfully shaped in all the right places but she had a hard time seeing anything beyond a fat girl wishing she was skinnier. She ate right, she worked out, but she never felt like her body was good enough.

And now here she was, planning an outfit  for a date with the cute guy she’d met at the bookstore, unsure why or how he could be attracted to her. Second thoughts and self-doubt plagued her as she tried to get ready; she almost called him and cancelled, but a tiny voice in her head said no. She was going on a date with a handsome man named James and she was going to try to leave her insecurities behind. Alas, she knew all too well that was easier said then done. Finally she settled on a black 1950s style swing dress with bright red patent heels and the lipstick to match. If she was going to do this, she wanted to look as good as she could manage.

They met at the bookstore and James was, for a moment, awestruck at the woman in front of him. He’d found her attractive wearing jeans and a t-shirt, but she looked amazing and he told her so. She blushed heavily, unsure of how to respond, and mumbled a shy, “Thank you.” The pair headed to a small bistro down the street and as they walked along James noticed the looks Lexi received. He came to the conclusion that she really had no idea how gorgeous she was and his aim was to change that. Maybe not in one night, but he wanted more than just a night with the buxom brunette. He reached over and took her hand gently and Lexi gifted him a rare smile. She was still nervous, but figured that if he hadn’t run from her in the bookstore he wouldn’t run now.

The pair enjoyed a quiet dinner, chatting about  whatever topics came to mind. Lexi relaxed in front of James and he smiled at her subtle changes in behavior. Dinner over, they took a stroll along the boulevard. Lexi was still oblivious to the looks she received and James was oblivious to anything but her. So he took a deep breath and asked, “Come back to my place?”

That question caught Lexi completely off guard and she almost asked him why, until she saw the look on his face. Naked desire and it had to be for her. Her blush wasn’t quite so heavy this time, nor was she quite as shy when she agreed. She wondered just how far they would take things and she hoped that if they progressed into sex that he wouldn’t be disgusted by her body.

As they returned to his car, James grinned and pulled Lexi into a dark alley and wrapped his arms around  her, for a scorching kiss like she’d never had before. A tiny moan escaped from her mouth and she stepped closer to James, not having second thoughts just this moment. They made out like horny teenagers in the alley until James pulled away with a small groan. “I want you so bad, Lexi. But if you tell me no, I swear nothing you don’t want will happen.” Lexi somehow found the courage in her to give him a daring look and leaned forward to whisper in his ear. “Come and get me.”

James wanted to practically drag her back to his car and speed to his place. This woman, who seemed to have confidence come and go in waves had somehow gotten under his skin like no one else ever had. The way she looked, her smell, that sudden shyness that overtook her at a compliment, everything. On the drive over his hand rested gently on her thigh and for a moment Lexi cringed internally, afraid he might notice how fat her legs were and be repulsed by her size. The old doubts and fears were beginning to resurface again, despite the kisses in alleyway and his promise of not going any farther than she was comfortable.

They arrived at his apartment and James led her upstairs and poured a bottle of wine. Lexi kicked off her shoes. He handed her a glass of  wine, poured his own and they found themselves sitting at either end of the couch. “Put your feet in my lap gorgeous. I’ll give you a nice massage.”  Lexi took a sip of her wine and slowly, carefully readjusted so that she could do as he requested. “Lexi, it’s OK. Like I told you nothing will happen tonight unless you want it. You’re beautiful and don’t even know it, do you?” “No, I’m not,” Lexi mumbled between sips of wine. James’ hands which had been so artfully rubbing and caressing her feet, slowly moved up to her ankles and further to her calves. It took a moment, but Lexi relaxed into his touch and let herself really think about him finding her attractive and wanting her sexually. It made her almost giddy, especially given how much she wanted him.

Gradually James shifted positions so he was kneeling over her, his hands on her thighs under her dress. His hands slide to either side of her and leaned in for another searing kiss. Lexi hesitated for half a second giving him time to tease her lips with his tongue and then wrapped her arms around him, pulling him into her. She met him kiss for kiss and before long was squirming beneath him, wanting more, while trying to suppress her growing terror if her dress came off. At least she’d picked a matching bra and panty set in red satin. Lingerie was one of the few things that made her feel pretty. He reached behind her back and tugged lightly on her zipper. “I want to see all of you. May I?”  James looked steadily at her for a  long moment before she finally nodded her assent.

He peeled the dress down her body slowly stopping to kiss and nibble at her. The sight of her breasts encased in red satin nearly unmanned him, “I want you  like I’ve never wanted anyone else Lexi. Please say yes.” Her voice was a whisper, “Yes.”He stood, leading her to the bedroom, leaving her dress in a black puddle on the living room floor.

James touched and kissed her everywhere he could, trying to show her how gorgeous she was. He slid his fingers against the satin panties and slowly stripped her.There was the sound of a condom opening and then Lexi felt him inside her, moving slowly, trying to hold on to his control. She gasped, holding onto his shoulders, arching her hips, fears forgotten as her first orgasm of the night rolled over her. Muffling his own moans against her breasts James came as her pussy clenched around his dick. “I’ve got you beautiful.” And her kissed her quite thoroughly, a promise  of more.


If you missed last week’s Wicked Wednesday post, you can find it here.


11 thoughts on “Wicked Wednesday 245 – Second Thoughts (Uncertainty of a Woman)

  1. I love the body confidence you instil and the description of the outfit worn is gorgeous, and the adoration of your body is both right and confidence boosting to people like myself xx


  2. Oh the number of times I want to beat my heard on a wall because of body image. Barring the every woman is beautiful in her own way statement, it is like women have been trashed and torn apart to where they feel if they don’t have this perfect body that they crave then no one will ever want them. I’ll stop now before I reply with a blog sized answer.
    *climbs off my soap box and goes back to pushing the street broom with a tip of my hat*

    Fantastic post and how he helped her know she was desirable.

    Liked by 1 person

    1. The societal body issues that are forced on young girls and women are ridiculous. I could give you a blog sized answer in return honestly. I won’t though and I’m glad you enjoyed the post. 🙂


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