Pursuing Debby

For as long as I can remember, visions and memories of Debby have always had a special place in my cranium and my heart. I first got to know her when she was hanging out with my sister. Back then, she was cute, but at that time, just in a plain sort of way. No one except her parents and my sister Sarah seemed to notice her or pay attention to her. After puberty came to Debby, it transformed this carefree young lady into an amazing beauty and instantly, she rose to the top of every boy's charts...including mine. Her beauty was very much like an aging fine wine, every year she would be better than the year before. She became an amazing woman almost overnight it seemed.

Me, I was a few years older than Debby, but like I said, I have always liked her. When she would come to my house to hang out with my sister, she just gave off good vibes and she had a special sort of attractiveness to her that drew me to her charming and mischievous smile. I inherently knew she would be a fine looking woman, but I had no idea how stunning she would become.

Her older brother Vinny was one of my closest friends and we grew up together, played ball together, went to school on the same bus, and I would always tell him,

"Vinny, one day, I am going to ask your sister out..."

He would look at me with this really stern look and then give me his standard line...

"Over my dead body...we are friends...you can't freakin' date my sister, besides, you're too old for her you freakin' Neanderthal."

I would laugh at his comments...but I knew, given one chance...just one opportunity, I would take my shot to be with Debby, just like every other red-blooded American boy would do. Debby was viewed as a trophy to practically every guy I knew and I was on the hunt for her despite our age difference and my friend status with Vinny.

Let me give you a mental picture and description of what Debbie was like. Jeez, where do I start? She was vivacious, friendly, clingy and fun to be around. She had a charming sensuous voice, a great laugh and intense smile...and she was stunningly beautiful with absolutely perfect shiny white teeth. She could have been a model. Despite her only flaw of being a little short due to family genetics, everything else of hers was off the charts. She had a beautiful face and her blue eyes could make you do anything. She possessed some long, curly, flowing blonde hair that reached down past her petite but athletic shoulders. Her waist was perfect and in the summer she would have on t-shirts that exposed her midriff and would allow you to see her cute belly button. Last of all, Debby always wore Jordache jeans that were so super tight and they totally accentuated her amazingly figure. Like I said, she could have easily been a model.

So, let's fast forward a few years...

After graduation, I joined the military and I basically left for a few years. The U.S. Army's constant training and their excessive running program did great things for my physique and it got me noticed with the ladies, but I was only interested in one lady...Debby. It was great to have some very toned and defined muscular arms and shoulders, but I was most proud of the six-pack I had developed from my five-hundred crunches and other core workouts I did every day. My duties and physical fitness regimen were paying huge dividends now and I too had gone through a male metamorphosis similar to what Debby had done a few years ago and I was hoping she would eventually notice me.

So, after being away for nearly three long years at Fort Benning, GA, I put in for some much needed vacation and when my commander approved my leave, I headed home for two solid weeks of fun and time off and hopefully, no, I prayed, that I would run into Debby and shock her with my new physique.

After coordinating a few things, I caught the post shuttle to the Atlanta airport and flew home to Philadelphia. I had prearranged with Andrew, my lifelong best friend, to pick me up at the international airport to bring me home. He agreed and soon we would meet again. It had been too long.

I arrived in Philadelphia on time and I quickly made my way through the concourse to get my luggage and get out of the damn overcrowded airport and on the road. As I rounded the bend to get my luggage off the carousel, there stood Andrew waiting for me. We gave each other great big bear hugs, but then he stood back and looked at me like I was a freak.

I looked at him like what was wrong

He cracked a smile and says "like whoa...dude...have you been taking steroids?" "How the fuck did you get so freakin' ripped?"

I smiled and replied..."Uncle Sam's fitness plan and some of my own craziness..."

He was clearly impressed but if I made that big an impact on my best buddy, I can't imagine what effect it would have on a special young lady.

I saw my green bag on the carousel and I went over and snatched my only piece of luggage off the conveyor and then followed Andrew to the car parked in the temporary lot. Then, after dealing with some crazy city traffic, we made our way to the interstate and headed for home. We bullshitted and caught up for about an hour. We talked sports, school, what our friends were doing now, who was in college, who dropped out, who was doing drugs, and then we rounded the bend and started talking about girls...and then Andrew glanced over at me and gave me some intel on Debby.

"Wait until you see Debby! She can't get any more gorgeous, but like...she grew...Dan...like more like tall and her tits...like wow...man, they are so ripe for picking."

I simply replied "I would jump off a building to get in her bed..."

Andrew then chimes in and gives me a note of confidence..."well dude, with the way you changed, you have a much higher probability of making that happen than I do..."

Then he laughed and pointed at his slightly obese body and quipped "Body by Nintendo..."

We both laughed hard and continued to laugh and joke about that and other stupid things we had done or said over the years and we didn't realize how fast our time passed and by the time we stopped laughing and cracking up, we were just about home. Man, we sure had some stupid teen adventures, I thought to myself.

"Those were some crazy, but good years" I blurted out.

"Amen to that" came Andrews' reply.

We pulled in our large driveway and parked Andrew's beast of a car. I grabbed my stuff in the back of his car and went in to see my folks and my brother and my little sis. I had not seen any of my family for a while except for the pictures mom sent to me in her letters, so it was great to see everyone again. Andrew must have told them I was coming so they had an impromptu party going on at my house for me. I walked in and I could not believe how much everyone had grown up.

After greetings and hugs and punches in the arm, we all sat around the table picking at some foods my brother brought from the store and then there were a few special things my mom and my sister made just for me. I was great to be home and have some great Italian and Polish food. Then we started reminiscing about old times and eventually, the heat in the house forced us to move to the back deck where we could crack open a few beers. We all hung out for a few hours and then everyone slowly started saying their goodbyes and heading out after handshakes and more big hugs from me and the family. It was so amazing to see everyone again and hang out with everyone for a few hours.

As things were winding down, I wanted to talk with my sis, but she had disappeared. Somehow during all of the activity, she managed to slip out during my little welcome home party. It was just a few of us who sat there now. We lit the old tiki torches around the deck for old-time's sake and we just made small talk. Andrew was asking me if I was going to stay in the Army and my dad insisted that I reenlist because of the economy and lack of jobs in this area, and then there was mom. She wanted me to use my educational benefits to come home and go back to school. As they were all contemplating my future, my sister Sarah walked right up the stairs to the deck, with Debby in tow. I winked at my sister and then gave a long look at Debby. My jaw dropped...I couldn't believe how much she had grown up. I was so stunned by her beauty and other features that I nearly fell backwards from my high-backed deck chair. Then she came over and gave me an enormous welcome home hug, I could sense she had grown up a lot and her voluptuous tits poking into my ribs were the most obvious sign.

Mom and dad said their goodnights and left the deck in our care. I now sat there wishing I was alone with Debby, but I was still accompanied by Andrew, my brother Jason, and Sarah. We got back to telling more stories and despite Sarah and Debby still being minors, i.e., not 21 yet, we gave them each a beer and pretty soon, we all were feeling good and enjoying our reunion. We had such a good time talking again and enjoying the weather and I savored this precious time together. I was a little tired from my travels, but I outlasted everyone, except Debby. As the last party stragglers either headed to bed or walked home, it left Debby and me alone, finally. It was the moment I had waited for all night or should I say...all my life.

"I missed you" was the first phrase out of her pretty mouth when we were finally alone.

And I replied, "Me too, and do you know how long I have waited and restrained myself for this moment?"

"No, but tell me"...and then she laughed.

"For years, I have watched you grow up in front of me. I have ALWAYS liked you and at times, you were like a second sister to me. When you would come to my house, I wanted to get you alone in the worst way, but I knew I couldn't. But look at you know...Debby, you have matured into a stunningly beautiful woman and I know that you just had a birthday. With that, I pulled a small package from my utility shorts and gave it to her. She looked stunned.

"Ahh...you remembered my birthday" as she unwrapped the box and kept smiling at me. She finally opened it to find a simple gold necklace that was delicate just like her.

She reached over and gave me a kiss on the cheek. I knew I had touched her with this small gift.

"So as we sit here tonight and you're now over 18 and free to make a lot more choices on your own, I am so glad you came over tonight. There is a lot I wanted to get off my chest with you."

Debby smiled that mischievous smile as she strained to put the necklace on...and once she had it on, she innocently whispered to me "...like what? What juicy stuff do you want to tell me Danny?"

I reached over and slowly grasped her delicate warm hands and placed them between my hands and I pulled her closer to me. I paused for a second, then I looked deeply into her beautiful blue eyes, and as sincere and honest as I could say it, I revealed my heart to her.

"For so long, I have waited to say this to you, and now that your eighteen and your overprotective brother Vinny is far away at school and can't punch me out for saying this to you or wanting to be with you...now...I, well I, um Debby, I wanted you so bad...I wanted to go out with you years ago, but our age difference would have put me in trouble with your parents, but that is all behind us now."

"She playfully snapped at me "Oh Mr. Bigshot...you have everything all planned out for me don't you...?"

"No" I responded. "Not planned, just something I have been dying to tell you for a long time. The age part was a big thing, plus the friendship I have with your brother and your parents. Well, it just wasn't right then."

Then she got serious..."So what are you really saying Daniel?"

I pulled her hands and put them on my heart, and revealed to her "I am back for two weeks as of today and I was hoping that maybe we could go out together. Perhaps have that date that has long eluded me...uh...us for so long.

She scooted her chair closer to me...then placed her head on me and simply whispered..."I think we can make that happen."

I put my arm around her, then lowered my head to her and gave her a passionate kiss, the first one that I could get away with and it was everything and more that I had ever thought and dreamt it would be with her.

When our lips met, it was special but our seating was a little awkward, so we got up and found the large deck chair and plopped down in it. But before she sat down, Debbie went around and capped all the tikki torches except one or two. It definitely set the mood for us.

She came over to the chair and curled up on me and we were back to kissing again. Her lips were so fine and her breath was like smelling and tasting the freshest summer strawberries. We embraced and kissed for about thirty minutes and got lost in just "us" time. I ran my fingers through her beautiful hair, traced her face with my finger and I kissed her for all I was worth. I had waited so long for this night, I hoped this moment would last all night.

I could sense the warmth of her voluptuous breasts pressing into me and I was beside myself. When she repositioned and opened a few buttons on her thin button-down shirt she was wearing, I knew my night was going to get even better. I gently guided my hand into her shirt and around her back and pulled her close to me. I didn't want to rush anything and I wanted her to know how much I cared for her. She was so warm and her skin was as soft and smooth, like that of a baby's skin. We kissed and held each other closely for a few more minutes until I let my hand wander and I found the front of her bra. I slid my hand under that lace fabric and seconds later, I was cupping one of Debby's fine C-cupped tits. Her breast felt so warm and inviting and her nipple was so stiff that it made me wonder what she was thinking.

She rolled on to my lap with her back on my legs and looked up at me and the stars overhead.

"Daniel, you look amazing and oh my god, you have muscles...everywhere!" as she squeezed my arm tightly and then ran her hand up and down my abs several time in a very approving manner.

"Looks like someone has been working out a lot...cause' I don't remember your muscles ever being this large."

Then I responded back...as I touched my finger to her cute little nose

"Army life has been good to me and my fitness is better than ever...but enough about me...Debby, you babe, you look like a supermodel and..."

"You are just so damn beautiful and you have a body straight outta' heaven and I can't believe that I am here sitting on my back deck with just you...and actually kissing you and enjoying a little make out time with you. I have waited so long for this."

She smiled at me again and then I stopped talking and we were back to kissing and petting again. I had my hand on her tit and I was massaging it as we progressed from passionate kisses to more heated French kisses. I wanted to talk more with her, but I wasn't stopping this action for anything.

Then she sat up and repositioned herself on me so that she was above me and had her legs straddled over mine and as we embraced again and kissed each other repeatedly, she started to move even closer and slowly grind her pelvis on me and it was making me oh so horny.

She looked down at me and then whispered... "Do you think you can get me a blanket...it is getting a little chilly out here?"

I didn't feel like it was that cold, but I didn't want to stop this night, so I quietly slipped into the house and a minutes later I had two large blankets she could put around herself to keep warm.

She took the largest blanket and wrapped it around her back and then she said something to me that changed my life...

"Daniel, do you by chance have a condom on you?"

I was stunned at her request...but I said, "Yes" and she smiled her mischievous smile...

Debby looked at me and whispered "Has your family gone to bed?"

"Yes" I responded again

And just to reassure her it was okay... "Everything was dark in the house when I went in for the blankets, so, yeah, we have the deck all to ourselves for the rest of the night."

"Okay, then..."she said...

Then she leaned into me and cooed into my ear "I too have waited for this night forever and I can't tell you how many nights I have gone to bed thinking of you"

And then she whispered ever so softly to me "...so much that it makes me very, very wet..."

"Did you know that you have that kind of effect on me Daniel?"

I replied "I didn't know that...but I know how you feel."

"I have gone to bed myself many times hugging my pillow and just wishing it was your sweet body."

With my last sentence, we were back to kissing again, but Debby now had a plan churning in her head.

She slipped her flats off, then raised up slightly and just like that...she had her sweats off and then she was back on my lap adjusting her hips and legs to get in the perfect position for what we were about to do.

Then she removed her white cotton panties...and the little nymph had the nerve to swing them in front of me like a prize before folding them quickly and laying them in between her folded sweatpants.

I reached around knowing where this was going and gave her ass the tiniest spanking and then I groped it a little and I heard her moan a little.

Then it was mine turn.

It took a little more work, but I got my sneakers off and then let my jeans fall to the floor and then I shed my boxers too.

We were semi-naked from the waist down on my back deck facing the woods and it was a warm night with just a sliver of the moon shining above us.

Then she asked me to put the condom on.

I reached into my jeans and brought it out but she took it and helped to rip it open and then she took her velvety hands which were shaking a little and she gently placed the condom on the tip of my cock and then awkwardly worked it all the way down on my cock while slowly giving me a small hand job or perhaps she just wanted to know how large I was...but she was soon going to find out anyway.

I couldn't believe that I was about to make love to my dream girl on my own back deck.

With my cock fully erect and shrouded now in its pink raincoat, Debby inched forward slowly.

We continued to kiss as she lifted her magnificent bottom, then gently took my cock and positioned it perfectly at the very moist opening to her pussy.

She repositioned and shifted again and just like that...I felt my rock hard cock slide up and into her very wet but tight pussy. It was wonderful. I slowly eased up, going deeper and deeper into my lover. She aided the situation by making slight adjustments while nibbling at my neck, ear and running her hands up and down my chest. Oh my god, she was so tight and I thought I would come right then and there...

We slowed things down a bit and went back to kissing as she slowly rocked her hips on me in a gentle rocking horse maneuver. I put my hands up her shirt and firmly massaged both of her tits now. She pulled the blanket up and over us and with the cover of darkness on us, I slowly undid all of her buttons and then I unclasped her bra and pulled it off of her. I lowered my lips to suck on both of her massive C-cupped titties. I loved the taste of her enticing perfume and the softness of her skin as it melted into my mouth. Her tits were the finest tits I had ever put my mouth on. I kissed them and licked them and sucked on them...and I was watching her go a little crazy as I fondled her over and over again.

Again, she started to moan slightly as I kissed, massaged, and licked her lovely orbs.

I was going to remember this night for the rest of my life.

I was now deep up into Debby and we were making some amazing love on my back deck and we were both loving every minute of our time together.

She started doing circles on my lap and grinding her pussy into me and her breathing was heavy and she was making me feel like a stud...as she welcomed me into her world.