Being Helpful Ch. 01 - Getting Married

The doctor's office had surprisingly nice carpet in the waiting room, I mean, for a doctor's office. I gave my name at the window, took a deep breath, sighed, and sat down. The burgundy overstuffed chairs were comfortable enough, at this, an uncomfortable moment for me.

"What am I doing here?" I asked myself.

Looking around, I guessed that this wasn't a typical doctor's office. Located in a converted Victorian mansion, the rugs, the paintings on the wall, the bookshelves looked to be filled with hardback novels from days long ago.

A tasteful sign on the wall asked people to silence their smart phones. I complied and looked around at the other people waiting. They were mostly women in their thirties and early forties and only a couple of young men.

I say "young" but really, I'm 55 and that makes me old. So, younger than me but not really young, I guess I should say!

All were professionally dressed and relatively affluent.

Mildly bored and certainly a bit nervous, my mind drifted back. Thirty-five or so years ago, before smart phones and before the internet, I met a girl at an ice cream shop. I'd graduated high school and was... naïve. Kate was a couple years older than me and much more mature, in many ways.

THE FIRST TIME:

At 18, I was a horny virgin. I remember watching Kate's ass as she walked from customer to customer. She liked to flirt with the old guys who came in for 25 cent unlimited coffee or tea. Sometimes she bent over in front of them and when she caught me watching, she'd wink and walk by me saying, "It's good to give the old guys a thrill!"

I guess she liked to flirt with the young guys like me, too!

Our first date brought us to the north end of Boston where we shared a cannoli and enjoyed the little shops that dot this little section of Boston. It was June but it was unseasonably hot. I'd just graduated high school and was getting ready for college. I was excited about leaving my home town and excited to be on my own for the first time in my life. It was only an hour away from home but at that age, that seemed like a long way away.

Kate had already gone to college for a year but quit. Her father, a devout and conservative religious zealot, insisted she attend a conservative Christian college in Georgia. She only lasted a year before leaving. She wouldn't tell me why.

Music played and we held hands while moving from booth to booth trying three different versions of lasagna, all were great! We ate two rounds of raw oysters on the half shell before settling down on a patch of grass with another round of cannolis as a parade ambled on by down Hanover Street.

She leaned in and slowly kissed me. The world around us stopped and went silent.

The music, the laughing children, the priests chatting with old men, the mafia bosses handing dollar bills to kids for donations, all of it ended as her lips parted slightly and my tongue met hers. The kiss wasn't one of those sloppy and aggressive kisses. It wasn't exactly shy either. It was perfect, sensual, and just what I needed. She gently placed her arms over my shoulders, and we disengaged, letting the earth began to spin again.

One of the mafia guys, bulging in his black, pin-striped suit, smiled down at me and winked and then gave another kid a five dollar bill, "Hey, that wasn't for you, Tony!!" he laughed as Tony put the bill on a money float passing by.

A little while later, Kate and I were seeing each other almost every day. Though only a year older than me, she seemed worldly and mature. She'd grown up in multiple states and even visited other countries. I hadn't even flown in a plane. I knew I was naïve and I knew I lacked experience. I worried that my lack of experience with women would be an issue for us. She seemed so experienced and so very confident. I'd dated a few girls in high school and we'd had some fun. My unfortunate experiences usually ended them getting fingered to orgasm, a kiss on my forehead, and their request to go home ... leaving me untouched and frustrated. It made me think of the Beatle's song, "Please, Please Me."

But not Kate. She planned a day for me on July 4th. She picked me up in her beat-up Chevy at 1 in the afternoon.

"Where are we going?" asking as I hopped in.

She smiled, "I packed a picnic basket and thought we'd go for a nature walk a couple of miles from here. Sound good?"

I nodded as she pulled away from the curb, the warm air blew back my long hair.

Small American flags adorned the suburban road. Little kids were lining up for a parade, waving their flags as we went by. The parade was due to start at 1:30 and we had just made it ahead of the parade route.

"Have you been to this woodland park?" she asked. I shook my head. "Well, I haven't either but I read about it in the newspaper. It's next to a prep school but the preppies are all home for the summer. Plus, everyone from town is at the parade. That leaves the whole town forest just for you and me!"

Kate held my hand and carried a picnic basket in the other. We got to a narrow spot, and she went in front of me. I liked her ass in her tight jeans as she climbed a small slope in front of me. She wasn't skinny and she wasn't fat. She was somewhere in between. Her tits were a nice B-cup handful, with sensitive pink nipples, about the size of a nickel, that poked straight out when aroused.

She found a thicket of bushes and suddenly went off trail, "I think this will do. This looks like a great spot for a picnic!"

I looked around. It didn't look like a very nice spot to me. There were bushes all around and no view of anything. In the distance, I could hear the band playing as part of the parade and wondered what we were doing here in the woods in the middle of all this shrubbery.

But, I went with it and helped lay out a blanket and helped empty the basket she'd brought.

There was some red wine, apples, cheese, and crackers. After some of the wine, cheese, and crackers, I realized why we were so secluded.

Let me say it now, I am an idiot.

We kissed. My tongue reached into her mouth as I pulled her toward me. She lifted my shirt and played with my nipples. I unbuttoned her red checked blouse and she shrugged it off quickly.

I looked around. No one in sight, surrounded by bushes, hmmm, I wonder why? Yes, I am an idiot.

Reaching around behind her back, she unclasped her bra and those gorgeous breasts just popped into view. I wanted to hold them and suck those nipples. A breeze kicked up and the pink nubs hardened, sticking out a bit further than the eraser on a pencil.

Following my eyes, she knew what I liked and pulled me to her. We kissed some more and then I floated down her body to those wonderfully soft breasts. I licked and gently sucked her puckered nipples.

Kate stripped off her jeans and quickly slipped out of her panties. I followed suit and was half naked in a moment.

There was a noise on the path. I heard someone call for "Skippy!" It was a dog on the path with their owner not far behind. I was mortified. Kate grabbed the edge of the blanket and covered up in case they looked this way. The dog came in, ran around us, and then ran out. The owner walked right by without seeing us.

"Now where were we?" she asked seductively.

We snuggled again and I kissed and bit her neck. She pulled my pants down again and I was surprised that I was still rock hard. All of our previous sexual encounters always included me undressing her and playing with her, including fingering her to climax, she'd never reciprocated. Today, her hand wrapped around my cock, and it felt glorious.

She smiled from the look on my face and then kissed me again while rubbing my cock against her thigh.

"Feel good?" she asked while already knowing the answer.

It felt so good that I worried I'd ejaculate all over the place when clearly, she wanted my cock between her legs.

She lay on her back and spread her legs for me. I had my jeans still around my ankles because my sneakers were still on. I hopped between her legs anyway and she giggled as she grabbed my hips and guided me toward her.

This was my first time. I wanted it to be... special, but my hormones wanted it to be now, right now! In position, I looked down at her. Her eyes were closed as she awaited entry. God, her tits looked wonderful!

I pushed and went nowhere. She was dry and tight. I grabbed my cock and began rubbing the head along her pussy lips. She opened her eyes and enjoyed my rubbing stifling a groan. I rubbed several more times feeling her getting wet.

I was ready.

She was ready.

The mushroom head of my cock was poised at the entrance but there was a dog looking at me with a tennis ball in its mouth.

We covered up quickly and I decided that my first time was not going to be in the woods 8 feet from a walking path. The parade was over, it was a nice day, and people were coming to the nature park.

She drove back to my house where we had an afternoon cookout with my family. There had to be twenty people there. I helped Dad cook on the grill while Kate set the table and helped Mom be the host. It was Kate's first time at one of our family feasts and we were both enjoying it.

By eight pm, many had left but several others organized a plan to go to the fireworks at the lake about five miles away. Initially, I was interested but as I looked at my cute girlfriend, I came to another plan. If everyone went to the fireworks, we could be home alone.

Suddenly, I was a salesperson pushing and encouraging the fabulous town fireworks. "They were the best in this part of the state, couldn't be beat, loud but not too loud, fun and exciting... everyone should go!!"

Kate got into it as well and before we knew it, we were practically pushing people into their cars... and then, we stayed behind.

Kate leaned forward on the windowsill as she watched them leave. Her ass tantalizingly up in the air swaying to the music on the radio. My cock had been getting hard all afternoon as I thought of those tits, that ass, and my first pussy. I sidled along next to her to watch them drive away. My hand fell on her back and then slid onto that ass, stroking her as she wiggled it into me. Turning, she pressed into me and I enjoyed the feel of her pillows on my chest.

"Let's go downstairs!" she exclaimed with wide eyes.

Grabbing my hand, she giggled and led the way. Her shirt was off, and bra unclasped by the time we reached the bottom step. I pulled her to me and sucked on her neck and then down to her wonderful chest, not too big but not too small. Her sensitive nipples responded to my tongue and lips, hardening and protruding.

I kissed her stomach and pulled her jeans down while smelling her pussy juices, now only hidden by thin panties, which I practically ripped off her. She had a full brown bush and lay on the carpet right after stepping out of her panties.

Standing above her, I stripped down wanting to remember every detail, every feeling, every moment. She smiled as I pulled down my pants. It was her first good look at my cock.

"Nice cock," she said casually.

I was slightly embarrassed. None of my girlfriends had ever taken the time to even see it. Now, Kate looked up with hungry eyes filled with anticipation and desire.

I remembered to take off my sneakers, socks, and this time, my pants came all the way off.

"I'm new to this," I mumbled self conciously.

"It's okay. I've only done it a couple of times myself. Trust me, it feels good. We'll figure it out together!" she giggled.

"Well, I think I know what goes where..." I chuckled as I kneeled between her thighs.

She laughed and then added, "Just be gentle with me."

Her pussy looked like a target, pussy lips encircling a small hole. Gripping my cock, I rubbed it up and down along those lips and across her hooded clit. Up and down and back and forth. It was killing me to not jam it in.

She smiled at my awe over seeing her pussy so clearly and up close. "Put it in," she whispered. "I want to feel you inside me."

She made circles with her hands on her tits, around and around ending on her nipples where she gently pinched and pulled the little nubs. Her legs opened wider and she moaned slightly. Then her ankles reached around to my ass and pulled me into her.

"Now," she said. "I want it now, please."

I pressed in and felt the pressure as I pushed.

She looked at me and nodded in encouragement, "That's it."

I wanted to be a good lover. I wanted her to feel good. I wanted her to gush all over my cock like what I'd read in magazines. I wanted to do this right so we could do it again and again and again. It wasn't going in as easily as I expected.

"You're kind of thick. Be gentle with me," she said.

I backed off, rubbed the head up and down again. She was much wetter now. Pushing in again, I felt her pussy open more and then a slippery grip.

Her eyes went wider as my thickness slid in deeper. "Oh God, yes!" she groaned. "That is it, baby. That is it."

Some people say that it feels like a slippery, wet, velvet glove, but I've never felt a slippery, wet, velvet glove. I can only say that it felt like nothing else I'd ever felt before. It was warm and slick but in a single word, it felt... perfect. I already knew that I wanted to make it last and I would want it more often!

My mind was suddenly swimming. Nothing else in the world mattered, just my hard cock in her warm pussy!

I began pushing and pulling and she began to join me. Initially, our rhythm was lousy, but we were getting closer and closer to working together. It was almost all the way in and sliding more easily now.

She gripped my shoulders and squeezed saying, "Umm, go easy, big boy. I'm trying to get used to you!"

I kept up the motion getting deeper and deeper with each thrust. Her moans and groans encouraged me. I wasn't sure if I should go faster or slower or what, but I knew that I had to keep going. I didn't want that amazing feeling to stop, not ever.

The buildup to an orgasm was coming fast. I could feel it. I worried about cumming too soon. What if she didn't cum? Would she let me fuck her again? I had to hold out and make sure she came ... so we could do this again, and again, and again!

I silently cursed myself for not licking her pussy or getting a blow job. I just had to jump right in and now I was going to blow it all by being a shitty fuck whom she'd ditch in a heartbeat. What was I thinking?

I was losing control. My orgasm was coming and, try as I might, there was not a thing I could do about it. I thought of pulling out but just couldn't do it. It felt too fucking good!!

Her face was sublime, and her eyes opened slowly. Those green eyes were unfocused and fluttered. Her breathing was hard, pink cheeks, and full lips parted slightly. She was liking this. I was okay. Her tits were bouncing up and down and I wanted to suck those pink nipples. She was meeting my every thrust, her legs encouraging and setting the pace. Then those green eyes squeezed shut tight and her head shook from side to side. She grunted, groaned, and moaned.

Any control that I thought I had, I lost. I started pounding as hard as I could. I no longer worried about anything. I no longer worried about cumming too soon because I was already cumming and nothing was going to stop it, nothing.

Gobs and gobs of cum shot up inside her as I pressed my cock up as deep as it would go. The pump in my balls exploded over and over again, and just kept pumping.

I pulled out and flopped next to her. We were exhausted.

She curled under my arm, her head on my chest, "Feel good?" she asked.

"Oh God, yes. Like nothing else ever," I mumbled. "Did it feel good to you?"

She smiled wistfully, eyes curling up to the side, smiling, "It felt wonderful."

My name was called and a plump, big-breasted nurse asked me to follow her to a room down the hall. We went through an old oak door to a room that reminded me of my old college apartment. As I sat down to wait again, my thoughts drifted back to my college years. The busty nurse handed me a cup. I knew what I had to do here. It wasn't to pee in the cup.

She smiled kindly, went to the door, turned back to me, "You can use your phone if you need, umm motivation," and then she was gone.

MOTIVATION:

I went to a college near our town. It was a basic place giving basic education. Kate continued to work at the ice cream store and became a shift supervisor. It was her second job, and she did it "just for fun," as she'd often say. With the additional income, she decided that she wanted to move out of her restrictive parent's house. They weren't too happy about her moving out and thought it was my idea. So, I got the brunt of the blame.

Call me old fashioned but I always felt odd with her paying for things, so by my sophomore year, I got a job and worked three full days a week in a clothing store. It wasn't fun but I felt better being able to pay for dinner every once in a while. With the extra money, we rented a condo at a ski resort.

There was too much on my plate that semester. I had a girlfriend, played sports, a 30 hour a week job, and schoolwork. My schoolwork suffered badly and I'm not sure that I actually cared. My fall semester was horrible and reflected my priorities. I almost flunked out. I didn't even realize it until my mother pointed it out to me.

"You've got to get your priorities straight, young man," she said. "Your schooling has to come first and then everything else. Look, I think Kate is great but if dating Kate is a distraction, maybe you should date a college girl. You know, someone who is motivated to do the same things as you. I know this much, these grades won't cut it. You're throwing your future away!"

Mom made great points and I felt a depression sink in. Kate noticed it right away, but I just couldn't tell her about what Mom had said. I just couldn't. It would hurt Kate too much.

"Why can't you tell me!" Kate yelled at me. "If we love each other, we can say anything to each other and work things out. Tell me!"

Kate made some great points, too. Taking a deep breath, I told her everything. It just rolled out one thing after another. I had a very bad semester. I almost flunked out. I told her that Mom said I had too many priorities and my grades were on the lowest rung of the priorities ladder. My schoolwork was suffering.

Then, I hesitated, but added truthfully that Kate might be too much of a distraction.

I waited for an explosion, but it didn't happen.

Instead, she said, "She's right. I'm too much of a distraction."

"Wait, I don't want to lose you!" I exclaimed.

"No, you're not going to lose me unless you continue to fuck up your classes! You keep flunking classes and I will get blamed by your family. That is not going to happen, not anymore! Listen mister, your schoolwork is now MY priority," she grinned.

I was confused.

"Let's go over your courses. Tell me about them," she said as she pulled up a chair from the kitchen table of her tiny apartment.

I told her about my spring courses, there was Advanced Mathematics, Programming II, Biology II, Statistics and Adolescent Psychology. It was the end of the first week of the semester and I had a bunch of chapters to read.

I said, "We should go make love now so I can get to reading." That was my priority, but she had other ideas.

She crossed her arms, "Write down what has to be done tonight on this note pad."

When I was done, she reviewed it and nodded. Then she took off her sweater revealing a tight T-shirt and no bra underneath. Perky tits whose nipples jutted out through the cotton. "Like what you see? You get to see more with each chapter and explanation you give me. No nooky until you're done with your bookies!" she laughed.

With that, she pulled out a People Magazine and began reading. I began reading and taking notes.