A First Time

A First Time

1999

We "met" in an online chat room. With the username TexasRed, her profile said she was a woman, over 40, who lived in Dallas. I'll spare you the details, but suffice to say we hit it off and started chatting privately.

I sent a private message to TexasRed, mentioning that I found her comments about a favorite film of mine to be both insightful and funny.

Surprisingly, she replied back. She said she enjoyed the movie, especially the off-beat sex scene. People who didn't understand that "can suck my big ol' clit!"

And that, my friends, is how the conversation started with the woman who would one day be my wife.

Since I lived in Southern California, we chatted several times a day, effectively becoming "email pen pals." Email allowed us to share photos, which, while not a guarantee, reassured me that she was who she said she was. The first picture she sent was a portrait of a lovely redhead with a dazzling smile. Her green eyes were slitted as though partially taken over by the smile. I was smitten.

The second picture was taken at a costume party. A full body shot of the same woman, dressed in a harem outfit. Her dark nipples and thin patch of pubic hair were clearly visible through the gossamer bodice and gold metallic bikini bottoms. I was in love.

We soon discovered we had a lot in common. We were both happy in our chosen professions. We both loved obscure movies and classic rock. And we both felt trapped in terrible marriages.

Our exchanges were often quite graphic. I discovered I had a knack for what they called "sexting." That is, sexy messages sent by text. You share vivid descriptions with each other, spurring the imagination and encouraging masturbation.

Besides the sex talk, over time, we helped each other through the tough decisions and endless court battles. Eventually, we were both divorced and our conversations became about finally meeting face to face.

Neither of us had much money after our divorces, so casually hopping on a plane was out of the question. But now that we each lived alone, our phone calls got longer and more explicit. I could describe what I wanted to do to her sexy body and I could hear the whimpers and moans of her self-induced orgasm.

2003

One day, she surprised me by asking what I was doing over Valentine weekend. Her nephew was graduating college just an hour up the coast from where I lived, and her brother was footing the bill for her airline ticket and hotel room so she could be there to celebrate.

How could I refuse?

The graduation was on Friday the 14, but she was coming in on Thursday. We arranged to meet for dinner at a brand new, and highly rated, restaurant. The plan was to meet, talk, eat, drink, and see where it went from there.

That Thursday found me nervously driving up the twisting coastal road, wondering if I was making a big mistake. What if her photos were fake? Unlikely since by that time I had a half-dozen of her. What if she's one of those who is nice in small amounts, but an asshole in real life? What if I'm an asshole? What if we don't finish our salads before she calls it a night?

I will tell you now, none of those things happened.

I had chosen to dress up a bit in a dark grey suit with a lavender necktie, I arrived at the restaurant a bit early and waited in the bar. I ordered her favorite drink (One of many things we'd discussed over the years, it was a specialty drink that not every bar has in stock because it is quite expensive and rarely ordered. I had asked when I called in the reservation.) and had it waiting when she walked in.

She was perfect.

A straight-backed five-foot, five inches, she saw me immediately. She waved and (dare I say it) shrieked with delight. The maître d' didn't have a chance to greet her, and only smiled as she breezed past him and into my arms.

She was wearing a black dress that reached below her knees. Her chest and shoulders were draped in a large silk scarf with a bright red floral pattern. The red was repeated in the high-heeled shoes with a strap around her black-stocking-clad ankles.

She said my name. I said hers. And we kissed. Hard. A long deep kiss that, honestly, would still be going on to this day if the maître d' had not interrupted us.

"Excuse me. You're table is ready. Don't forget your drink."

She giggled again when she realized her drink was waiting and perfectly iced. She linked her arm in mine and we followed the maître d' to our table.

As we sat down, she removed the scarf to reveal the shoulders of her dress were covered in black sequins. The neckline curved downward to expose a single strand of pearls and her very inviting décolletage. She blushed as I stared, but then she turned to show me the back plunged to her waist.

"Wow."

She beamed. "Thank you."

I suppose I can skip most of the details of the dinner except to say our young server, Michelle, was exceptional. Age 20 and majoring in Food Service Management at the college, her wine recommendations were perfect and the food was excellent.

As we finished, we decide to skip desert. I ordered another cocktail for each of us. She grinned. "Oh boy, are you getting laid tonight."

I looked back up at Michelle. "Better change mine to coffee."

"I would say so," she laughed and walked away.

When Michelle brought the check, she said, "You two picked the right night to come in. Tomorrow is Valentine's Day and college graduation. We're completely booked." As I gave her my credit card, we shared that it was our first date. When she returned for a signature, Michelle said, "Since you didn't have dessert, I comped your appetizer. You guys are adorable. I hope the rest of your night goes well, and I look forward to serving you again."

I left a big tip.

While we waited for the valet in the chill of a February evening, I draped my suit jacket over her shoulders. She thanked me as she tugged it tight around her chest. She then proceeded to grab my shoulder for balance as she kicked off her heels. I picked them up for her.

She smiled at me. "You never mentioned if you like wearing women's clothes, but stay away from high heels. I love how my legs look, but they're a killer on my bunions."

I laughed and hugged her. "Noted."

As we got in the car and I asked for directions to her hotel, she announced that we had one stop to make on the way.

Following instructions, we pulled into the parking lot of a 24-hour drug store. She suggested I stay in the car, but I told her that was not the man my father raised, so we went in together.

It took her a few minutes to search the aisles until she smiled and picked up what she'd been looking for: a pale pink plastic bottle with a screw top. I glanced at the label. Vaginal lubricant.

"Did I mention you're getting laid tonight?"

She insisted on paying for it and within a few minutes, we were at her hotel. Though, motel is more accurate. A tiny place in need of paint. Her room was above the breezeway parking.

She noted my reaction. "I know, but the inside is clean and the bedding is fresh. You'll see."

She was correct. Not that I would have noticed if it wasn't.

The minute she'd closed and locked the door, she tossed my suit jacket and the scarf over a chair, then pulled me into a deep, passionate kiss. Her tongue seemed on fire as it licked around mine. I felt my dick getting hard.

My arms surrounded her and I caressed her back, exposed by the plunging dress. She reached down to grab my ass and pulled me tight against her stomach. "Oh, good. Hard already. No time to waste."

She stepped back and turned around. Lifting her thick curls off her neck, she tilted her head forward. "Unclip me, please?"

I carefully unhooked the neck of the dress, the started on the pearls. She stepped away.

"No no. First lesson. The pearls stay."

She walked to the bathroom door. "You'll be naked when I come out?"

"I promise."

In moments, I had removed every stitch of clothing. I turned the room temperature up a bit.

"You don't need to do that."

When I turned, my firm dick swung and bobbed in her direction.

Lit by the spill from the bathroom, she was completely nude except for the string of pearls and black stockings held in place by a matching garter belt. With one hand on her cocked hip, she looked like a scene from a titillating, pre-Hays Code movie, with stark lighting accentuating the curves and dips of a woman's body.

Her breasts were on the small side of perfect. They hung high, proudly showing off the erect nipples.

Her waist narrowed to a slight softness before widening out to strong hips that wanted to be grabbed and held tight.

The carefully trimmed pubic hair exactly matched the dark patch I had been jacking off to in the harem photo.

Forcing my eyes up to her face, I found a smirk that said she knew exactly what affect she was having. Her eyes were lasered in on my cock.

In three steps she was in front of me, cradling the shaft. "Someone is happy to see me." She dropped to her knees and leaned close. "And he's quite good looking." Opening her mouth wide, she exhaled a deep, warm, breath. I moaned and my cock jerked up. She caressed the top like she was petting a kitten. "Oh, did I scare you, baby? I'm sorry." She looked up at me with just her eyes. "I meant to do this."

Her mouth was around me in an instant. The fingers of one hand closed on my balls while the other wrapped around the base on my shaft. She was bobbing her head as she jacked my rod. A sound rumbled in her chest, like a hungry animal finally getting its prey.

I grabbed her hair. "Oh baby. Oh wow."

She let loose and smiled up at me. "I've dreamed about this for years."

"Me, too, baby. Get on the bed. Let me lick your pussy."

She was on her feet an instant. "Top or bottom?"

"First time? Bottom."

"Good call."

She grabbed my dick, and in an instant, she had me on the bed, face up. She leaned down once again, speaking to my cock. "We are going to have so much fun." She gave the tip a quick kiss, then straddled my chest facing me. With a soft gasp, she cradled her breasts, kneading and tugging them. When I reached for her hips, her hands moved down between her legs. Lifting up a bit, she slid her fingers between us, caressing her pussy. I shifted my hips and groaned. She looked over her shoulder at my rampant cock. "Patience, hon. I promised my pussy to his face first."

With a wicked grin, she scooted up my chest, her pussy getting closer to my face. She lifted up, her stocking-covered knees on either side of my chin. The smell of her arousal was intoxicating.

"Second rule. Tongue only. No fingers until I say it's okay."

I was a bit confused. "What?"

"I'll explain when the time comes. Right now," she moved forward, the pussy of my dreams only inches from my mouth. "Right now I want your tongue in my pussy."

She lowered herself as I extended my tongue. I ran my tongue along the soft hair.

"Talk to me, baby. Like when we're on the phone. Make me cum with your words and your tongue."

"God, baby, your pussy is beautiful. And the scent," I buried my nose in the soft thatch and took a long, loud breath in. "A perfect musk rising from your excitement."

"Oh, yeah. That's it."

"Your lips are so thick and full. Your pussy wants me. It's been calling out to me from afar." I licked the warm wrinkles guarding her secrets. "Your pussy wants me. It's aching for my tongue."

She wrapped her fingers in my hair. "Yes, lick me. Taste me for the first time."

Using my tongue to tease the opening, I pressed my chin onto the clitoral hood, waking her delicate button in its nestled hiding place.

"Your secret flower is opening for me. I feel your hips pushing toward me. Your fragrance is enticing, drawing me in. Inviting me to..."

My tongue slid into her pussy. I licked deep inside, caressing the soft flesh at the back, then curling forward to reach the sensitive bumps at the entrance. Her hips shoved toward me as she let out a long moan. "Oooh yeeessss. More baby."

I pressed my tongue deeper, searching for that tell-tale glint of moisture to tell me she's ready for more.

"Faster, baby. Make me cum."

The soft hood at the front of her pussy slid back, revealing her swelling clit. "Look what I found. It looks like a sweet, innocent button. Is that what it is?"

"No!" She gasped. "Not innocent. Suck it!"

I kissed her clit softly. "Not innocent." I lick it with slow firm pressure the length of my tongue. "Not sweet." The tip of my tongue flicked her clit. She twitched and groaned. "It's a horny little thing. Selfish. Demanding. A sexy bitch that wants what she wants." I close my mouth around her clit, sucking it hard.

"Feel my tongue fucking you? Lashing your clit."

Her hips are fucking my mouth almost violently. Her voice is raspy with heat and lust.

"GOD YOU'RE MAKING ME CUM! OH GOD, YOU WONDERFUL... AHHHH!"

No spewing liquid or gushing cum, but her scream echoed through my ears, and probably the entire building. Her legs gave way and her cunt settled fully on my face. I let my tongue lightly lick her clit as it retreated to safety.

She rolled off me and flopped on the other pillow. "Oh, sweetie. That was all I hoped for. You wonderful man. If you suck my big ol' clit like that once a week, I'll stay with you forever."

"Only once a week?'

She snorted a laugh. She rolled over, draping an arm across my chest before lifting her head to kiss me, then lick my face. "You smell like my cunt."

"That's a good thing."

"Yes, it is. But that," She glanced toward the foot of the bed where my cock was sticking straight up, despite being neglected. "... is not." She quickly sat up and started caressing my cock. "Poor big boy. Don't worry. I didn't forget about you. In fact," she spun her legs off the bed and walked to the small table. I enjoyed the site of her ass wiggling as she took the few steps. She reached into the drug store bag and came out with the pink plastic bottle.

"Here's the thing." She was now talking directly to me instead of my dick. "I hit that 'Woman Thing' a bit earlier than most."

"Menopause?"

"Yes." She walked to the bed, unscrewing the cap from the bottle. "Ever since, I'm very dry. My OB/GYN says 'oh, it's perfectly normal,' but he's not trying to fuck me, is he?"

"I hope not."

"No. He's not." She shrugged. "His son the pediatrician might a be different story. Anyway, it hurts like crazy to put to put anything inside; fingers, dildo, a cock, even a tampon for God's sake. Though fortunately, my flow is so low that a napkin by itself does the job." She blinked at me. "Why am I telling you all this?"

"Because you know I'll stay with you forever and suck your big ol' clit at least TWICE a week."

"You serious?" She snickered. Then she studied my face before turning to my half-hard cock, but pointed at me. "He's serious."

"Hand me the bottle. I'll show you how serious I am."

With another glance at my dick, she cautiously handed me the bottle.

"Now lay down."

She did. I sat up next to her and poured a small amount of lubricant on my hands.

"Relax."

She made a show of taking a deep breath as I rubbed my palms together to warm up the lube.

"Oh, smart boy."

I smiled, then gently rubbed one hand across her mons, pressing into her pubic hair.

"That's not what needs..."

"Hush."

Surprisingly, she did.

I moved my hand lower, pressing more firmly. "Just concentrate on my hands. Enjoy the feeling. Tell me if there is the slightest discomfort.

"Now you do sound like my OB/GYN," she mumbled.

"Sh."

"Did you just sush me?"

"And I will do it again if you don't follow directions."

She opened her mouth to object, but I poured a stream of lube directly onto her labia and started rubbing it in.

"Oh."

My hands moved slowly, gently. My fingers slipped between the lips and across the opening to the vagina. I added a little more directly to my fingertips, moving them inside in small circles. My thumb grazed her clit.

"Mmm. Better."

I brought my fingers out and poured a large dollop onto two fingertips. Trying to keep them from rubbing off at the entrance, I eased them deep into her. Her body tightened.

"You ok?"

"Um, yeah. That wasn't pain, baby."

I gently spread the lube in a circle as far in as I could reach. Her hips started moving up and down in time with my slow strokes.

"God, baby, I haven't felt this good in years."

"I'm glad. How about we try..." I eased the fingers back out, letting them drag over her clit.

"AH. Yes."

Spreading her lips with my fingers, I poured a few drops of lube onto her clit. I reached up and took her right hand and moved the two middle fingers directly over her clit.

"Try that, sweety."

She closed her eyes, then started to rub her clit with the two fingers. Tentatively, then firmer.

"Oh. Oh, my."

I rested one hand on top of hers. "Shall we try inside?"

"Uh huh."

Our hands slid together. When our fingers reached the opening, I stopped moving and let her continue inside.

"God," she said quietly.

I returned to rubbing her clit, pressing it in small circles as I watched her fingers go deeper.

"Oh God. So nice." She started moving her fingers a little faster. I matched the speed on her clit. She sped up more as her hips joined the action.

I smiled, though I noticed her eyes were closed. "There you go, baby. You're doing it."

"We're doing it. Bring your fingers down here. I need more."

She slipped her hand out. I laid my two middle fingers on top of hers. All four fingers eased back in, stretching the sides of her pussy.

"Oh, my poor cunt. She has missed this."

Letting her set the tempo, we gradually sped up. Her hips were bucking and our fingers were going in and out faster and faster.

"Yes. We're fucking our fingers. My god, I can't... so good."

Her hips bucked, then froze as she had a quiet orgasm. We slid our hands out. I let mine rest on her clit. She licked hers.

"This is why I buy that brand. No taste." She smiled and settled back. "That was nice."

"Yes, it was nice."

She caught my tone. "What?"

"I know this is only our first time, but it seemed like your other one was much bigger."

"It's like that, sometimes."

"I understand, but..." I knelt between her legs, holding the bottle of lube near my dick. "What do you think of...?"

A smile crept across her face. "I think I'd like that. But, let me."

She took the bottle and poured a portion on her palm before rubbing them together.

"Oh, smart girl."

She snorted.

Both hands surrounded my dick, which immediately reacted by swelling with blood.

"Oh you like that do you? Let's try this." She cupped the head of my cock and rocked it in a twisting motion, dragging her lubed palm over the sensitive ridge. My stomach muscles tightened as I grunted. She looked at me. "You like that, too, huh?" Then back to my dick. "Maybe a bit more?" With one hand still twisting the head, the other began sliding up and down my shaft, spreading a thick layer of lube.

"Sweety," I put my hand over hers, my breath very heavy. "The idea is not to make me cum."

"What?" She looked at my cock, now fully erect and throbbing. "Oh, yeah."

She quickly threw one leg over, her black stockings caressing my hips. "Probably better if I control how things go."

"Agreed."

She reached between her legs and held my cock at the mouth of her gaping cunt. She closed her eyes and began to lower herself. I felt her pussy open up around my cock. I could barely breath, much less talk.

"God, baby, you're beautiful."

My hips twitched as she tickled my balls.

I reached up to caress her breasts with hands still slick with lube.

She opened her eyes, a bit surprised. "Oh wow. Never tried lube on my titties before." She closed her eyes again. "I could get used to this." She continued to descend on my cock.