2003: Computer Dating

2003: Computer Dating

It was 2003 and I was getting divorced. Lisa and I both knew that our marriage fizzled out for good around the turn of the century. We hadn't had sex in over two years. I guess I could have gone out and gotten some on the down low, but with work being busy and Lisa and I living under the same roof with our daughter, Samantha, I just didn't have the time. It was easier to take care of things myself.

Lisa and I separated, and then she moved to the other side of the country. Said she "needed some space." I didn't care that she abandoned me, but Sam took it hard.

So, at age 40, I was a single parent to a fragile 10 year old who just had her world turned upside down. Initially I focused all my energy on supporting Sam, but all of my friends, and even Lisa's parents, urged me to take care of myself as well. They told me I needed adult companionship.

Computer dating was the new thing back then, so with everyone telling me to "put myself out there" I gave it a try. I signed up for eHarmony and created my profile, then started searching. My first two dates were a disaster. The first woman spent twenty minutes ranting about what an asshole her ex-husband was. She didn't talk about anything else or ask me a single question. After I finished my cup of coffee I wasn't even nice about it - I just said "have a nice day" and left.

My second date was a mother of three young kids in the middle of a nasty custody battle. Her life was complicated. I felt sorry for her, but there was no way I was going to get involved in that. We had an interesting conversation and I told her I could give her the names of some lawyers if she needed it, but there was no second date.

Third Match: Janie

Janie was about my age and recently divorced. She had a 12-year-old daughter, lived nearby and was a successful professional. She looked attractive from her profile picture, but I wasn't getting my hopes up. After two terrible dates I was having doubts about eHarmony. Those profile pictures weren't always a good indicator, I had learned.

Janie and I had fun exchanging emails at first, then after about a week we decided to meet up for a beer. We chose a bar in the next town over, hoping not to run into anyone we knew. We arranged a strict half-hour first date, that way if it turned out to be a disaster we had an easy escape. If it turned out to be enjoyable we could always set up a second date. Win-win. We timed it to start right before Janie had to pick up her daughter from soccer practice, so we had an actual hard deadline.

We agreed to make it casual. I told Janie I'd be wearing jeans and a brown leather jacket, my head shaved clean like in my profile picture. She said she'd be wearing a white shirt and jean jacket, her dark hair tied back in a pony tail. I took a table in the back and waited.

After only a minute or two I saw Janie standing by the entrance, scanning the room. When our eyes met there was electricity. I saw her face light up and smile. I was smiling too, instantly attracted to her. She was even prettier than her profile picture.

Janie strode through the bar and walked right up to me, planting a kiss on my cheek before we even confirmed who we were.

"Hi Tommy," she said. "I'm Janie."

The 30 minutes flew by. We talked and laughed and listened. We barely finished our beers before she apologized she had to go. I paid the check and Janie walked out with me, stopping by my car.

"So," I said, "can I call you? I'd love to take you out again - without a time limit."

"I would love that," Janie said, smiling.

We stood facing each other awkwardly. Even though everyone had told me to go slow, I took a step toward Janie and wrapped my arms around her for a hug. To my relief, she draped her arms over my shoulders and leaned in.

"I had a really nice time," I said.

"Me too," she responded, her nose almost touching mine.

I leaned forward and gave her a kiss, holding my lips to hers for maybe two seconds.

I pulled back and looked at her, keeping my arms around her. "I liked that," Janie said.

I leaned in for another kiss, holding my lips to hers. When she wrapped her arms around me tighter I slipped my tongue out and in an instant we were making out like teenagers. Janie ground her leg against the hardon straining in my pants as we tasted one another. After a minute Janie pulled back.

"Gotta go get my kid," she said.

I sighed. "Yeah, you better. This has been a really good first date."

"Call me," Janie said as she turned and headed to her car.

Second Date

We had great banter by email all week. Janie had a warped sense of humor, just like me. Even better, she was frisky. Every message was suggestive. By the time Friday night rolled around I was super excited for our date. Sam was at a sleepover and Janie's ex had their daughter. We had no time limits and no responsibilities.

Janie looked beautiful. She wore a silky white shirt, jeans and sandals, casual but chic. She had dark eyes, full lips and round, high cheeks with just a touch of makeup. Her nails were red and shiny, just like her lips. Her dark hair flowed over her shoulders and she wore dangly, beaded earrings that framed her pretty face. She was lovely.

I cooked a nice Italian dinner and we drank almost two bottles of Chianti. We told stories about our lives and bad eHarmony experiences. We laughed. Janie's eyes sparkled. I was enthralled.

After dessert we moved from the kitchen to the living room and sat on the couch. I dimmed the lights and put on music. There was electricity in the air.

I put my arm around Janie and we kissed sweetly, our tongues exploring one another, our hands gliding over shoulders and backs. Just as I was about to slide my hand off her shoulder and down the front of her silk blouse, my phone rang. It was the landline I still had back then.

"Are you going to get that?" Janie asked, glancing over at the phone clanging on the end table.

"Nope," I responded, bringing my mouth back to hers.

Janie smiled, knowing that she had my full attention. It was like I had just passed a computer-dating test - will he or won't he pick up the phone while we're making out? I wasn't a jerk, so far. We kissed for a few seconds more, then my cell phone rang.

"Shit," I said.

"This can't be good," Janie said gloomily.

I looked at the caller ID. It was Alice, the mom who was hosting the sleepover.

"Shit," I said again.

I hit the green button and prepared for the worst. It turned out Sam was having a full-blown panic attack. Alice said she had been trying to calm her down but Sam was desperate to come home. When Alice put Sam on the phone she was bawling.

"It's OK, honey, it's OK," I said, looking apologetically at Janie, "I'll come get you."

Janie gave me a knowing nod -- she was a parent, too. After Janie helped me straighten up the house I scooped up my car keys, Janie grabbed her purse, and we went outside.

In my driveway I took Janie in my arms. "I'm so sorry," I said. "I hope this doesn't go on your list of bad eHarmony experiences. Do I get another chance?"

"Are you kidding?" Janie replied. "I think it's hot that you're a good Dad. If my ex was on a date and thought he had a chance of getting laid, our kid would be out of luck."

"Oh, so you think I thought I was going to get laid?" I laughed.

Janie rolled her eyes and kissed me. She ground her body against me, pressing into the erection I had been sporting all night.

"Yeah, I think you thought so," she laughed. "And you were probably right, too!" Then she reached down and gave my aching hardon a squeeze. "Give me a call later - I can help you out with this."

My heart was beating fast as she got in her car and left.

>>>

"Hello?" Janie answered. It was 11pm and Sam was finally asleep. I was lying back on my bed in just my boxers.

"Hi!" I said. "I hope it's not too late."

"No, I'm up. How's Sam?"

"She's OK," I said. "I'm really sorry about tonight - I had a really nice time with you. Can I get a do-over? I think I can get Sam's grandparents to take her next weekend."

"Sure," Janie laughed. "Carly's dad has her then so that should work out great."

"It's a date," I said. "I promise I'll make it up to you."

"OK. I'm going to hold you to that."

An awkward quiet ensued. I was thinking about her offer to "help out" when she squeezed my hardon in the driveway. I was pretty sure she was opening the door to phone sex, but I didn't want to overstep.

"So," Janie asked suggestively, breaking the silence, "how are you?"

Green light.

"Let's just say that I'm aching for you," I said, using my bedroom voice.

"Oh yeah?" Janie purred. "What exactly is aching?"

"Baby," I said, "you know exactly what's aching."

"What?" she giggled, playing dumb. "Tell me."

"My cock is hard as a rock for you," I growled.

"Yeah, you did feel pretty hard," she said, "and big too!"

"Really hard," I replied. "So, how exactly did you plan to help me out with it?"

"Anyway you wanted me too, sweetheart," she cooed.

"Any way?" I asked.

"Any," she confirmed. "Seriously, honey, I'll do anything to want. Just tell me."

"Oh, fuck," I wheezed. "That's so hot."

"And when I say 'anything,'" she said again, "I mean it. Anything."

"Would you get on your knees for me?"

"In a second," she said. "Tell me what else."

"Undo my belt?"

"Definitely. I'll unzip you and take your pants off too, if that's what you want."

I sighed. "Are you going to have those red fingernails I saw tonight?" She had a perfect manicure. I love painted nails. "And wear those big, dangly earrings for me too?"

"Uh-huh. You want me to wear the red lip gloss, too?"

"Fuck yes," I sighed.

"So, you got me all dolled up on my knees and your pants are off. What do you want me to do now?" she purred.

"Suck my cock baby. Suck it."

"Mmmm, I was hoping you'd say that. Are you jerking off right now?"

"Yeah," I moaned. I was lying back on my bed, my boxers around my knees, stroking myself.

"Think about your cock in my mouth while you jerk off. I'd be on my knees, licking it, sucking it. I'm pretty good, you know. I'd looking up at you, my red lips on, my head going back and forth. Want me to rub your balls?"

"Oh, FUCK, I'm gonna cum!" I shouted.

"Cum for me!" Janie urged. "You want to cum in my mouth?"

"Aaarrrrgghhhh!!!" I wailed, cum spurting onto my belly.

Janie giggled. "That was easy. It's been a while, huh?"

"Oh, my God!" I wheezed. "That was fucking amazing."

"Next time we'll do it for real," Janie said.

"Wow," was all I could say.

"I'll see you next weekend," she purred, then hung up.

Third Date

We emailed all week. I hardly got any work done. By the time Friday rolled around I was bouncing in my office chair, buzzing with anticipation. Sam's grandmother picked her up after school, and on my way home from work I stopped at the market for the fixings for a gourmet dinner.

Janie arrived right at 6pm. She was dressed exactly as I asked - manicured nails and shiny red gloss on her full lips. Her dark eyes were highlighted with just a touch of blue shadow and her long, dark hair was woven into a French braid that hung down her back. Loose wisps of hair dangled around her pretty face, along with big, silver hoop earrings.

She wore a grey skirt that stopped around mid-thigh and a black, low-cut V-neck sweater made from an incredibly soft, thin fabric. She said it was cashmere. Black leather ankle boots rounded out the outfit.

"Wow," I said, holding the door open for her, my eyes scanning up and down. "You look amazing."

She smiled and gave a shrug, as if it was nothing. "It's what you asked for, right?"

"Um, yeah," I replied. "You look sexy as hell."

"Anything for you, sugar," she purred as she breezed past me into the living room.

I poured her a glass of wine and we chatted as I grilled swordfish. My dinner came out great and the conversation flowed, talking about our week, laughing about nothing, not even mentioning our kids or our exes. After dinner I suggested we take our wine into the living room.

"Living room?" she asked.

"If that's OK with you," I responded.

"If you want," she shrugged. "Or we could just move this party up to your bedroom. We both know we're going to end up there."

>>>

I took Janie's glass of wine and set in on the dresser, then took her in my arms and kissed her. We stood in my bedroom, making out, wrapped in each other's arms. I moved my hand up over her soft shirt as we kissed. She moaned into my mouth as I massaged her breasts. They were beautiful - full and firm. I slid my hand under her sweater and around her back, spreading my palm over her smooth skin. When I unsnapped her bra she raised her arms. I pulled her top up and over her head, and threw it on the bed along with her bra. I leaned back and scanned her naked front. Her tits were very sexy, each one a handful of soft, firm flesh standing out from her chest, capped by hard brown nipples.

I gently walked her backward and lowered her down on her back on my bed. I kneeled next to her and feasted on those luscious mounds, licking and kissing, squeezing and sucking her nipples into my mouth. Janie held my head with one hand and with the other she reached between my legs and grasped my aching hardon through my slacks.

While I was lavishing her chest Janie pulled my head up to her face and mashed her lips against mine, her tongue swirling in my mouth. With both hands she went to work on my pants and rolled me over onto my back. She kneeled over me, a wild look in her eyes, her tits glistening with my saliva.

"How do you want me?" she asked.

"How about we pick up where we left off with that phone call," I suggested.

"I love that idea," Janie smiled and pushed my pants down my legs. She shoved my underwear down and took my hard cock in her pretty hands. "You have a nice cock," she purred, then dropped her head down and sucked me into her mouth.

I let out a sigh. It had been years since I got a good blowjob.

"Mmmm," Janie moaned as she bobbed up and down on my shaft. She fisted the base and brought a hand to my balls, pumping her head, jerking and rubbing. She moved like a well-oiled machine, easily taking more than half my length into her warm, wet mouth on each stroke, her hands working my cock and balls.

Janie pulled off and sat up, looking into my eyes as she fondled me in her dainty hands. "You taste good," she cooed. "If there's anything you want me to do, just tell me, OK?"

"Just keep sucking baby," I ordered. It was clear she wanted me to take charge, and I was happy to oblige.

She dropped her head back down obediently and resumed sucking and jerking me off. "Lick my balls!" I commanded and Janie instantly moved down between my thighs, tonguing each of my nuts wetly and sucking them into her mouth. She rolled my balls around with her tongue and licked them until they were dripping wet. The whole time she was jerking my rod with both hands, working hard to please me.

"Nice baby," I praised. "That's enough ball sucking for now, though. Suck my cock some more." Again, she didn't have to be told twice. Janie went back to my rod and sucked urgently, her mouth and hands sliding frantically over my cock, driving me toward climax.

"I'm gonnna cum soon," I warned. "I want to cum in your mouth!"

"Ummpppff!" Janie squealed around my fat cock, excited to fulfill my desires. She sucked harder and looked up at me eagerly, urging me with her eyes to flood her mouth.

"Oh, Fuck Yeah, baby!" I wailed. I grabbed her head and thrust my hips as my cock exploded. The first blast sprayed all over the inside of her mouth, coating her tongue and teeth and gums with my sperm. Janie squealed in delight as I shot again and again. Her tongue washed over the head of my spurting shaft and she milked me with her hands, trying to squeeze every drop of semen from my balls.

When I was just about finished Janie closed her eyes and swallowed, bringing a big smile to her face. She opened her eyes and looked at me blissfully, licking her lips.

"That was wonderful," she gushed, licking a glob of semen from her thumb. "I love sucking your cock. I'll do that whenever you want."

I shook my head and chuckled. "I think I might want that a lot."

When I caught my breath I pushed Janie onto her back on the bed. I grabbed her by the knees and pulled her toward me, then reached under her skirt and found a pair of black lace panties that I pulled down her legs and over her boots. I pushed her skirt up to her waist and took in the sight of her lying back on my bed. She was naked but for her skirt and boots, her tits rising from her chest with every breath, her freshly waxed pussy framed between her smooth, open thighs.

I pushed her knees out wide and dipped my face between her legs. I painted a long, slow lick up along her wet slit and slid a finger inside her. Janie moaned as I took her clit between my lips, sucking and licking as I pumped my middle finger into her juicy cunt. It had been years since I had a delicious pussy to feast on and I ate her ravenously, holding her ass in my hands, mashing my face into her wetness, my tongue exploring every fold. Within minutes I had her writhing orgasmically on the bed as she thrust her gash into my face. Before she even caught her breath I climbed on top of her and slammed my renewed erection deep inside her and began fucking her with long, powerful strokes. I was like a demon, a man possessed, years of pent-up frustration suddenly released, my first good sex of the 21^st century.

When we were done we lay side by side, panting, contemplating the fantastic pleasure we had just experienced.

"That was great!" Janie gushed, "You were like an animal. I love that!"

"That was amazing," I agreed. Janie ended up sleeping over and we fucked and sucked all night long in every position imaginable. I fucked her from behind, she rode me from above, we fucked sideways on the bed and even in the shower. We sixty-nined until she was shaking in orgasm and I was pumping yet another load into her sucking mouth.

In the morning Janie had to go meet with a client, but she came back later in the day and we did it all over again into Sunday morning.

The Concert

A few weeks later I got tickets to a concert at a small club about 30 minutes away. The music was great. We had a few drinks and danced every song. Janie had sexy moves, looking into my eyes as she swung her shoulders and rolled her hips. By the time the concert ended I was dying to rip her clothes off and make love to her.

"Take me home," she cooed into my ear as we left the club, my arm around her waist. When we got in the car I leaned over to kiss her and we spent a good while making out before I started the engine. I put on a CD and put the car in gear as Janie sat back in her seat.

After driving for a few minutes I looked over at Janie and gave her a smile. She gave me a look that seemed to say "I'll do anything you want." Without saying a word, my eyes locked on the road, I unbuttoned my pants, lowered my zipper and pulled out my hard cock. I glanced over at Janie and saw her looking down at my lap, biting her lip. I grasped the back of her neck in my right hand and pushed her head down into my lap.

"It's a 25-minute ride, baby," I said assertively. "I don't want to cum until we're pulling into my driveway, got that?"

"Mmmmpppff," Janie replied enthusiastically, my hard cock already filling her mouth. Over the next 20 minutes Janie gave me a masterpiece road blowjob, her head bobbing in my lap as we sped down the highway. She sucked me slowly and rubbed my balls gently. She edged me, her tongue sliding along the head of my shaft as her manicured fingers tickled the base. She rested her head on my thigh and looked up at me as her tongue painted little licks up and down and over the head of my hard, throbbing cock. She held back, making sure not to bring me off until it was time. She was following my directions to the letter.