Lifestyle Ch. 01: A Geek Beginning

Jan had her best friend, Marlene as an outlet for her talkative girl needs. I was satisfied with my radio hobby and other reading interests. And after we opened up to each other in the diner on the first date, we both had a new hobby: enjoying private time together. We found those times together more fun.

When Jan tasked me to find a private place, parking my car at a scenic overlook worked well enough for that date. However, it wasn't very comfortable.

My next choice was a picnic in a park. I managed to find a very secluded spot in a local park as our getaway for when we felt the need to be together in private. Although we were over 18, using our own bedrooms in our parent's houses were still off limits if our parents were home. Motel rooms cost too much with our limited incomes. So, we had to wait for our families to plan to be out of the house for some reason, and both of our own after-school jobs had to sync with those times.

The local park was the most reliable 'go to' place, when the urge struck, and the weather was right. We were lucky with relatively mild weather during the last month of our senior year for a few nice times in the park, huddled together under the blankets.

It was always a relief when the weather permitted us to pack some blankets and snacks, walk down the hiking trail, and duck off through the bushes. Going over a hundred yards around the hillside through the mountain laurel shrubs, we found our private open spot with a view of the valley. We laid together talking and started exploring with our hands. Sometimes we even enjoyed a bottle of wine when a friend from my job provided it.

A bottle of Boones Farm Strawberry Hill seemed a risqué addition to our not-yet-drinking-age picnics. And a bottle of Riunite Lambrusco was like adding a touch of sophistication.

High School Grads

The Saturday after our high school graduation was a bright sunny day, with temperatures in the high 70's, a perfect afternoon and evening for the park. With blankets, backpack picnic, and a bottle of wine, we excitedly headed to our secluded space and our now favorite sport: naked wrestling.

I spread out the blanket in the small clearing among the mountain laurel and sat back to open the wine. Jan took off her shoes and stood barefoot at the end of the blanket. She was dressed braless in a blue cropped tank-top tied Daisy Duke style in the front, with white shorts. She looked at me with a mischievous grin.

"Mom rented the movie "Flashdance" for our Thursday family movie evening. I don't think she knew what the description meant by exotic dancer. When I watched the movie, I thought the idea of being a stripper might be fun. Imagine the power of tormenting guys, just by getting naked."

Jan started swaying her hips as she untied the tank top knot between her 38-D's. She held the two loose ends of the material together covering those tits.

"Do you find it exciting watching me undress? How much would you pay to see me spread my hands?" She glanced down at my crotch and my obvious bulge. "I see 'he's' showing some interest in those tight jeans."

I reached down and adjusted my cock, straightening it down the right pantleg. I was now hard at the full seven inches, and the pants were feeling confining, my cock wanting to stand straight up.

"Well, I could buy you a drink." I lifted a tumbler of wine for her. "You'll need to let go of that material to take it."

"That might be enough." She spread her hands, dropping the top behind her, exposing those 38-D's and already hard nipples. She wrapped her hands under and around her tits, lifting them and pointing them at me. She brought her hands slowly to the tips, caressing the dark areolas and squeezing the nipples between her thumbs and first fingers. "Watch how I do it. This is how I want you to handle them. Slow and easy, not just grabbing my nipples."

"I can do that. Sit here beside me, and I'll show you."

"Not yet. This stripper's still on stage. And the rule is 'look, but don't touch'!"

Jan lowered her hands and unbuckled her belt. She continued to sway her hips, as if dancing to some silent music. She slowly lowered the zipper, then raised her hands to the back of her head, as she glanced coyly and down to the side. Her shorts were now spread open, giving a hint of the pubic hair at the top of her pussy. She spread her hands open, fingers wide and seductively bringing her hands to the sides of her face, then down along her tits, and along her ribs, staring seductively at me. She slid her thumbs in the top of her shorts and slowly pushed down, as she turned to the side, not yet allowing me to see her treasure.

Jan's shorts fell to her ankles. She stepped out of them and kicked them to the side, standing naked and sideways to me. She wrapped her left arm over her tits and put her right hand on her pussy before turning toward me.

"Is it worth a dollar for you to see the rest?"

I quickly pulled out my wallet and produced a dollar bill, holding it out to her.

"Toss it on the stage."

I dropped the dollar in front of her, and she raised her hands again to the back of her head, spreading her feet and rotating her hips. "Is this what you want, big guy?"

I stared at her freshly shaved pussy, with landing strip of reddish-brown pubic hair above it. "Oh, yes. We haven't been together for a week. And you shaved!"

"You know I had my period last week. And I thought you might like to see my pussy this way. But the show's not over. I want you to pay for a lap dance. Another dollar?"

"What's a lap dance?"

"You'll see. I read about it when I found one of dad's Penthouse magazines. But first ... the dollar."

I pulled out another dollar bill and dropped it in front of her.

"Now, lie down away from the backpack."

I laid down, and she dropped to her knees, straddling my right leg. She spread her legs open to the sides to press her pussy against my thigh. My cock seemed to have a mind of its own, straining against the denim material toward her open, bare, and exposed target.

Jan rocked her hips, rubbing her pussy on my thigh right over my straining cock! I could feel her wetness soaking my pantleg.

"Hmmm. Am I getting your attention?" she asked.

"I don't think I can wait much longer," I said, as I tried to buck my hips.

I reached for her tits, and she snarled, "I said 'no touching, or this stops now!"

"OK!" I replied as I quickly straightened my arms out to the sides.

"The song's not over yet," she said calmly and slyly, as she continued to slide her pussy over my cock trapped in my pants.

I raised my right knee, pressing my thigh and cock into her to get a better feel of her crotch rubbing me.

Jan dropped down placing a hand on either side of my shoulders, brushing her nipples against my shirt. She slid up and down on my leg, rubbing and pressing her clit on me, her nipples barely brushing against my shirt, as she smiled looking down at me. She was enjoying my torment, as she rubbed herself with increasing excitement.

"Can you feel my pussy, big guy?" she teased. "How do I know you really want it, if I don't see any more dollars?" she asked shyly.

I only lasted a few more seconds. My cock with a mind of its own, suddenly erupting with blasts of cum inside my pants! "AGGGHHH!" I moaned.

Jan felt my hips bucking against her and the wetness of the mess spreading in my pants, and she laughed. She rolled off to my right, lying beside me. She propped herself up on one elbow and reached to the side of the blanket to pick up her tumbler of wine.

"Well, I guess he really did want it," she said as she chuckled.

I collapsed back on the blanket, feeling spent. "That wasn't fair. I could have put on a condom to catch this mess. Now my pants are going to be sticky when we leave." I began unbuckling my belt to attend to the mess inside.

"I didn't want to ruin the show. And I enjoyed it. It's your fault if you can't control it." She sat there smirking at me as she took sips of wine.

I cleaned as much of the cum as I could with napkins and laid out my pants to dry, as Jan watched. Then she shifted to lean her head against the backpack and spread her legs. "It was exciting turning you on. But now I need to orgasm. I want you to get busy and explore my shaved pussy, until you're ready again to fuck me."

"I can do that," I said. And we enjoyed the rest of the evening, fucking and cumming until I couldn't get it up anymore.

Community College

After a summer of fun in the park, we started community college. And a determined Jan decided to study more about her new favorite hobby.

She was talking to a co-worker at the diner about sex and some of her experiences with me. So, her co-worker loaned her a book, "The Joy of Sex". And Jan started practicing ... on me. I found this out when we were on one date in the park.

It was a warm Saturday evening, and the sun was going down. As usual, I spread out our picnic blanket, and Jan opened her backpack of light snacks. It was one of those times I managed to acquire a bottle of wine, so I poured two tumblers of wine and handed one to her.

Jan took a sip, then said, "I read in 'The Joy of Sex' there's a sensitive spot under your balls I might stimulate with my tongue. Take off your pants. I want to find it."

"Just like that? 'Take off your pants!' What about you? We usually start by undressing each other."

"You've seen me naked before. And will it really matter if I'm down between your legs sucking under your balls?"

"Well, when you put it that way ..." So, I took off my pants and laid back.

Jan crawled down between my spread legs and grabbed my hardening cock. It was beginning to stiffen as I thought about what might be coming. She held it out of her way and ducked her head down. When she tried to reach with her tongue further down, she said, "This isn't very comfortable. Maybe if you were sitting in a chair."

"Wait a minute." I rolled the extra blanket I brought and propped it under me to raise my ass. "There. Is that better?"

She laid down again and raised her chin to the best angle. "Yea, it will do."

She explored by sucking one of my balls into her mouth. Grasping my cock in her hand, she also stroked it, as I looked down at her. Seeing her in that position excited me even faster than usual. I felt my ball slip from her lips, as she moved her open mouth further down and between them. Her tongue running around the underside of my balls was very different, and my cock stiffened and began jerking in response.

"I think you've found it," I said.

Jan stopped there and focused her mouth and tongue on that spot. Feeling her wet tongue flicking back and forth over the spot was incredible. It was far better than when she found the best spot on the side of my neck to suck! My cock was feeling it and straining as it hardened like never before. I started to breathe faster, and she seemed to notice.

"Mmmm." I heard her moan, as if savoring the tight skin. She started sucking that spot, like she did on the side of my neck when she wanted to mark me with a hickie.

She stroked my rock-hard cock. And the wet sucking noises she made added to visual and tactile sensory overload. It took less than a minute and I felt like I was about to explode.

"I'm going to cum!" I warned.

Jan stroked faster as she picked her head up to look at the end of my cock.

My first shot erupted, the cum splashing against her mouth. She turned away and the second shot hit the side of her face, and a third shot landed in her hair. She let go of my cock, and got up on her knees, the cum sliding from her chin and dripping to her blouse.

"Yuck!" she said. "This is a mess. Hand me some napkins."

"Here ..." I handed her the napkin, and used one to catch the rest of the drips from my cock. "We usually use condoms... I tried to warn you, but you didn't stop."

"That was faster than you've ever cum before!"

"I think you found the right spot! It was definitely different."

As she finished wiping the mess from her face, she said, "Don't cum on my face, again. I don't like this."

"You held my cock in your hand. And you aimed it!"

She sat back beside me. "I wanted to watch it come out. I didn't expect you to shoot it out that hard so soon. Lesson learned."

"What else have you read about?" I asked.

She retrieved her tumbler of wine for another sip. "We're going to try some of the other positions I've read about later. You can put your pants back on now. After that cum shot to my face, you'll need to seduce me."

I was enjoying the new interest of hers. And as I said before, I can take her directive tone, when I also get what I want.

I learned if she had a particularly fast, intense orgasm, she would quickly say: "Ok. That was it. You can get off me now." So, I learned her body, controlling her build-up until I achieved my own. I realized by anticipating her change of tone, she was almost training me. I could handle it, and her. I learned to manage both of our expectations.

Over those next two years in community college, Jan's sarcasm and controlling nature didn't diminish. She did dramatically improve and refine her flirting methods, as we continued to have fun together. On the other hand, I only marginally improved my social skills. I was still a geek.