Memories - A Catch
For a long time, Emily and I dated in secret, concerned about "coming out" to the office, concerned about what people would think about a 26 year old woman dating someone in their 30s. I had an established career and she was just starting hers.
Emily, worried about her reputation and her career, would go on "dates" with these guys because it was easier than saying no and easier than saying why.
Of course, somewhere in there, she learned about my dark fantasies and leaned into them.
I remember one "date night" she had with a client's son in particular. He was two years older than her, the type of guy that usually got girls like her. Strong, handsome, athletic, masculine.
It was going to be dinner and a play at the small theater we sometimes went to.
I didn't know who she was teasing more, me or him.
Her skirt was short, showing off her impossibly long legs in black nylons and heels. Her blouse was thin, sheer, tight, showing off her breasts.
Seeing her like that, I couldn't help but think about how I wanted to touch her. I tried and she said no. "I have a date tonight," she said, "I can't."
"A date?" I asked.
"Hmmm," she said. "He's cute...in that masculine kind of way. Think he'll like?"
"Like?"
"My outfit," she said, putting her hands on her hips, showing off her body."
"I...I mean...you look...great," I said. "Are you sure your skirt isn't too...too short?"
"No, it's perfect," she said.
"This...how long...I mean...this is like...like you're third...date...this month," I said.
She shrugged. "Saturday night is date night," she said. "Don't worry, next Saturday you're all mine."
"Promise?" I said.
She nodded. "I figure one out of four four you is the minimum, no?"
"I...I guess..."
Before she left for her "date," she kissed me. "You know I can't say no until we're out...publicly," she said.
"I...I know," I said.
She hugged me, reached for me. "You always get so excited before I go out," she said.
I swallowed, hard. "I...I like...I like seeing you so pretty...men...admiring you."
She whispered in my ear. "I know, love, I know...we might be late..."
"Emily," I said, "you...I mean...we..."
"Would you want to know?" she asked.
"I...I don't know," I said, looking down.
"You like the teasing, don't you?" she asked.
I swallowed hard. "Y...yes," I said, "especially with..."
"Masculine men?"
I nodded. "Yes," I said.
She walked over to me, towered over me in her heels. I reached for her legs, touched one of them gently through her nylons. "Masculine men because you're afraid they're going to steal me away from you?"
She was pushing buttons, half guessing, half knowing. "Yes," I said, mouth dry.
"Masculine men because as much as you know I like our special kind of sex, you’re afraid I miss what men do to me?"
"Yes," I said, "yes."
"You picture it, don't you? In your mind? What I'd do with a man?"
"O...often," I said.
"Tell me," she said.
"Tell you?"
"Tell me what you fantasize about when I'm on one of these dates. I wonder if what my pretty boyfriend fantasizes matches what I'm thinking about when I'm with a man."
"Emily," I moaned.
She pressed her knee forward so it rubbed against me. "They..."
"A man I'm on a date with?"
I nodded. "They...he...he's forward, direct, presses...confident..."
"Responding to my flirting? I mean, I have to flirt, right? I can't be rude to a client's son when I said I'd go on a date with him, right? I give that long eye contact and look away like I'm shy..." She mimics that.
"You...you'd play with your hair," I said, "reach...reach over...touch him..."
"All the signals a woman wants to sleep with her date."
"Yes," I said, breathing heavily. "And..."
"And?"
"And when...when he brings you home you invite him in for a drink..."
"My place is empty, of course, so I invite him in just to be polite. I want it to be a real date, not an obligation..."
"You...you went on the date because it was an obligation," I said, "but...but it's been so long..."
"Since I spent a romantic evening with a man instead of my pretty little boy."
"You...you didn't mean to lead him on but while you're getting the wine glasses, he's behind you, puts a hand on your waist, the other on your thigh."
"That's when I have to decide, isn't it? Do I deftly escape his hands and get the wine so we can have that drink and I can gently end the date...or do I reach behind me and touch his hand, just a gentle push, guiding it down so it moves to my ass..."
"He'd...he'd reach under that skirt..." I said, reaching for her.
"No," she shook her head, pushed my hand away, "I have a date tonight, remember. But you're right, he'd reach under my skirt and cup my ass, rubbing me through my nylons, his fingers going between my legs while his foot gently moved my heels apart."
"Legs spread, his hand would slip between your legs, rub you...the only thing separating his fingers from slipping inside you would be the hose and the thin satin of your thong."
"He'd realize how wet I was, how wet I am, as I think about it. A man's hand between my legs, his cock so close. My pretty boy at home fantasizing about the thing that was happening. Fantasizing about a real man taking me. I don't know where the point of no return would be, whether I already crossed it, whether it was too late. I know I shouldn't, I know it was just a polite date, but it's been so long since I've felt a man inside me. Real cock, hard, long, thick, the kind that lasts, that I don't have to worry about, the kind I don't have to manage. The kind I just enjoy knowing my pretty boyfriend is home in his pretty panties waiting to pamper me.
I was shaking. "I...Emily..."
"I don't know if I'll be late, love, don't wait up for my call..."
"Are you...what if he...what if he does that?"
"Guess I'll have to see how the date goes...while you're at home wondering if I'm being good or bad."
"God, Emily..."
"Good or bad?"
"Good or bad?"
"Do you want me to be good or bad?"
"I...I don't know," I said.
"Then don't answer...don't know," she said, "just imagine. Be here, wondering if I'm being a bad girl."
Emily stood in front of the full-length mirror in our bedroom, turning slowly from side to side. The new date was set for Saturday night—another “polite” one, she’d called it, with the nephew of one of her biggest clients. Tall, confident, the kind of guy who played rugby on weekends and filled out a suit like it was custom-made for him. She’d agreed to go after weeks of gentle pressure from her boss. “It’s just dinner and drinks,” she’d told me with that teasing smile. “Nothing more… unless I want it to be.”
ReplyDeleteI sat on the edge of the bed, watching her deliberate over her clothes, my heart already hammering.
“What do you think, baby?” she asked, holding up two options. One was a sleek black cocktail dress, short, tight, with a deep V-neck that would showcase her breasts and a hem that barely reached mid-thigh. The other was a deep emerald green number, equally short but with a slit up the side that would flash a lot of leg when she walked. “I want to look… approachable. But not desperate.”
“You always look incredible,” I murmured, my voice already thick.
She laughed softly and stepped closer, still in just her bra and panties. “Flatterer. But I need your honest opinion. Should I go classy… or should I make sure he notices me?” Her fingers traced the hem of the green dress. “I was thinking about wearing stockings tonight. Real ones. With a suspender belts. Not the pantyhose I usually wear on these dates. Something… delicate. Expensive. The kind that feels silky when a hand slides up my thigh.”
My breath caught. She noticed, of course.
“Mmm. You like that idea, don’t you?” She turned back to the mirror, holding the black dress against her body. “The question is… if I wear them, and he finds out… will he take it as an invitation? You know how men are. They see suspenders and they think ‘she dressed for sex.’ Like I want his fingers tracing the straps, snapping them against my skin while he pushes my dress up in the back of his car… or on my couch.”
She glanced at me over her shoulder, eyes sparkling with mischief. “What do you think, love? Would a man like him, strong hands, used to getting what he wants, see the stockings and just assume I’m hoping he’ll fuck me?”
I swallowed hard, shifting on the bed as my cock strained against my pants. “He… he might. Especially if you’re flirting the way you do. Touching his arm. Laughing at his jokes. Crossing your legs so the slit rides up and he catches a glimpse of the lace tops…”
Emily smiled, clearly pleased with my reaction. She stepped into the black dress and shimmied it up her long legs, then turned so I could zip her up. The fabric clung to her like a second skin. She smoothed it down, then reached into her drawer and pulled out a beautiful black suspender belt with delicate lace and matching sheer stockings.
“Help me put these on?” she asked sweetly, sitting on the edge of the bed beside me.
ReplyDeleteMy hands trembled as I rolled the first stocking up her leg, feeling the heat of her skin. She lifted her foot onto my lap, letting me attach the suspender clips. The contrast of the dark bands against her pale thighs was devastating.
“Imagine if he sees these,” she whispered, her voice low and intimate. “We’re at dinner, maybe his hand finds its way under the table. He feels the clip… the strap… and knows I’m wearing them for a reason. That I chose something that’s easy to take off. Or easy to push aside.”
She stood up and did a slow turn, the dress short enough that if she bent even slightly, the tops of the stockings would show. “Do you think he’ll try to kiss me goodnight? Or will he just pull me inside when we get back to my place, slide his hand straight up my thigh and groan when he realises how wet the idea of being with a real man has already made me?”
I reached for her, but she gently pushed my hand away, just like last time.
“Not yet, baby. I have a date tonight, remember? But you can think about it while I’m gone. Think about me sitting across from him, legs crossed, the suspenders tight against my skin. Wondering if I’ll let him find out. Wondering if, when he does, I’ll spread my legs just a little wider and whisper that it’s been too long since I’ve had a proper fucking.”
She leaned down, her breasts brushing against my chest, and kissed me softly on the lips.
“Be good while I’m out,” she murmured, her breath warm against my ear. “And when I get home… if I’m late… you can help me out of these stockings and kiss every mark they left on my thighs. Whether they’re still pristine… or not.”
Emily grabbed her heels—the strappy black ones that made her tower over me even more—and blew me a kiss from the doorway.
“Love you,” she said with a wink. “Don’t wait up… but you probably will anyway, won’t you?”
The door clicked shut behind her, leaving me alone with the image of her in those stockings, wondering exactly how the night would end.