Jill

Chapter1: Two Virgins' First Time

I grew up in the typical small town USA. My family owned the largest business in town, so we had a love/hate relationship with the entire community. When business was booming, everyone loved my family. When things slowed down, we were the plaque of the earth.

My great-grandfather established the business in 1920. He just left the army after spending 8 years serving with his good friend General John Pershing. During the war, he realized that advancements in technology would ultimately be the deciding factor to deter future wars or to end wars. So, this ideology was the premise behind the company he created.

Because of his connections with top military decision makers and his 'get it done' mentality, he was awarded several military contracts and the business flourished. During the company's first few years, our patriarch realized quickly that greed was a powerful force and could transform his business into a weapon of mass destruction. As a result, he did not want his future generations to lose sight of why he chose this business.

To prevent this 'evil transformation' from occurring, he wanted each family member who chose to enter the business to join a branch of the military for a minimum of 8 years. His logic was simple. It was enough time to gain leadership skills and to see first hand the issues that technology could alleviate. Thus, when the family member returned, he or she would be able to meet the challenges of the next generation.

This approach worked well for our family. We maintained our small town values and we were able to supply good paying jobs to many people from our community while keeping our great nation's military strong. I would be the fourth generation to follow great-grand dad's steps if I chose this path.

I was a senior in high school. I had dark haired and was 6 feet, 2 inches and weighed 168 pounds. It was during the mid-eighties and I looked good sporting my killer mullet.

I was not a jock; nor was I geek at school. I considered myself a friend to everyone but kind of shy. As a result, I wasn't a big ladies' man and considered myself the luckiest guy in the world when Jill said she would be my girlfriend.

Jill was just 4 feet, 11 inches and weighed 89 pounds. She had the '80's big hair and proudly showed off her 20 inch rat tail. Her body had not quite developed into a woman's yet. Her figure was 30A-24-32. To me; however, she was the world.

We had always been friends. When we were in 3rd Grade, she and her parents moved into our neighborhood. She lived a mere four houses from ours.

During these early years, her interests were with Barbie Dolls and playing house. My interests were fishing or lining up the next sports game with my friends. It seemed I was always on the go and she was content to play with her dolls.

Our relationship changed when we started junior high. There were dances, clubs and other social functions that our parents forced us to attend. Usually, Jill and I were the ones left sitting on the chairs while our classmates were dancing. So finally out of desperation one night during the last dance, I asked Jill if she would like to dance. Neither one of us had moved from our chairs all night. Thankfully, she said yes.

Jill was the first girl I danced with in Junior High School. Not long after the dance, I got one of the famous notes (that I am sure are still popular today). One of Jill's girlfriends handed me the letter. It was from Jill and asked if I would like to "Go with her."

I was elated and quickly found her and said, "Yes!" We were inseparable from that point on. Jill was into art, so I took more art classes and joined the Art Club at school. (I never really cared about art; I just wanted to be near her.) She would go fishing and hang out with me even though she would rather do something else.

From the very beginning, she told me she promised her mother she would remain a virgin until she was at least 18. I whole heartedly agreed for two reasons. First, I wanted a girl friend; and second, I was brought up to respect my elders' wishes. (Apparently, her mother's first time ended with a pregnancy and she wanted Jill to be out of high school before having a kid.) At such a young age, sex wasn't real high on my list of priorities.

Jill had a strong morale fiber that I shared with her. In her mind, she promised her mother to avoid all sexual contact which meant no blow jobs, hand jobs or anything beyond kissing. However, as our relationship grew, this promise we made to each other was more and more difficult to honor. We used to joke that "We were masters of our domain." Translation: We masturbated as soon as we returned home from our dates.

When it was only a few weeks from Jill's eighteenth birthday, we began to make preparations for the BIG DAY. As luck would have it, Jill's birthday fell on a Friday night. Friday nights were huge in our small town for "BRIDGE NIGHT."

I checked the community calendar and my parent's were hosting that night. I knew from experience that the 24 couples that played took a minimum of four hours to play, eat and socialize. The only thing left was to talk Jill's parents into attending instead of taking her out.

Jill set the plan into motion when she told her mom she wanted to go to the Art Museum in the city. A new exhibit opened Saturday at noon. She told her parents they would take her and then stay over night in her favorite hotel.

Her parents could never say "No" to her. I knew from passed conversations with them; they were not big art fans themselves. No matter what Jill's interests were, her family was supportive and found ways to incorporate them with their activities.

Now that Jill's birthday request was made and accepted by her parents, we started planning our first time together. After a few days, the "we" became "she" as Jill told me she wanted to surprise me with the intimate details of the big night. I knew she wanted everything to be perfect. So, with my part in the planning done, I started the big count down.

Finally, the big day arrived! Jill's parents left the house and walked over to my parents' bridge party. As they knocked on the door, I greeted them and promptly headed over to Jill's. I was so excited; I caught my self running the short distance to her house.

When I arrived, Jill smiled since she had been watching me through the window, blindfolded me and led me into the house. I considered my self fortunate to lay my eyes on her before the blindfold covered them. Jill was stunning in her faded denim jacket with the Cyndi Lauper concert T-shirt I bought her and matching miniskirt. Her hair looked awesome in her favorite scrunchy and she had braided a pink ribbon in her rat tail.

I wished I would have been better dressed. Jill was beyond hot and I was wearing my Letter Jacket, 501 Jeans, and an old Motley Crew T-shirt with of course my untied Nike high-tops. When I saw her, I wished I would have worn my new parachute pants or at the very least my red polo shirt.

After teasing with gentle rubs, soft kisses and seductive whispers as she guided me through the house, Jill had me sit down. From the familiar feel of her mattress, I knew it was her bed. After some scurrying around the room, she slowly took off the blindfold. She had transformed her room into a tropical beach setting.

I heard a CD playing ocean sounds with gentle waves and the occasional sea gull calling. She had luau themed decorations throughout her room. To top it off, pink scarves covered each lamp on either side of her bed to 'add ambiance.'

We kissed each other slowly. Our passion increased and so did the intensity of our kisses. Before long, our plans of a slow passionate love making session were gone. Our hormones took over and we tore each others' clothes off.

We had waited nearly five years for this and we could no longer wait. Within fifteen seconds, we were both completely naked. I marveled at Jill's cute peach fuzz covered muff and her rock hard erect nipples extending nearly an inch on her self described 'man boobs.' I was transfixed soaking in the beauty of my girlfriend as my cock throbbed with lust.

Jill was far more aggressive. She quickly pushed me down on her bed and jumped onto me as we hungrily kissed with our tongues waging war with each others'. We were possessed and wanted to experience everything all at once.

Jill knew what she wanted. She grabbed my hard seven inch cock, barely able to encompass its girth with her tiny hands and aligned it with her virgin lips. She quickly attempted to mount my beast.

Her efforts were not rewarded. Although she was dripping wet with anticipation, my girth was too much for her and my cock darted toward her cute ass. She quickly lifted her body off mine and took both hands to spread her sweet lips.

She once again lowered onto my meaty girth. This time she slowly sunk onto my shaft until the bulbous head was pressed against her tight slit. She took a quick breath and lowered herself with the poise and confidence of a pro.

I had never felt anything like the moist, slick, tight channel that gripped my raging cock. The feelings were so unique I was about to shoot my creamy load. I tried to think of anything other than the tight embrace her sweet pussy had on my sensitive cock.

Jill stopped momentarily when my throbbing crown reached her hymen. We both felt the protective barrier. I already was in heaven. The tight grip she had around my cock head was unlike anything I had ever felt. Jill felt full but hungered for more.

We urgently worked together trying to break the barrier that was preventing us from the ultimate fulfillment of our love. I held the base of my cock to assist; while Jill slowly pushed downward. She tried for several minutes to allow me access but it hurt and she was getting frustrated.

Eventually, she gave up on this approach and asked me to carefully try the missionary position. As we changed positioned, I was grateful for the momentary relief from the extreme pleasure. I was so close to erupting; but, I didn't want to say anything for fear I would ruin the mood.

As I regained control, I placed my pre-cum oozing rod at her now red swollen lips. She quickly grabbed my cock and re-positioned it because I was heading "toward her pee hole."

Once we stopped laughing and my aim was corrected, I gently pushed my blood engorged beast into her tight tunnel until I felt the barrier. When I reached her stubborn ring, I looked into Jill's eyes for some sort of sign she was ready. Sensing my hesitation, she told me she was going to count to three and then "do it." Then, she quickly whispered, "One, two, thr...."

As she counted, I pulled back slightly. When she started with "three," I lunged forward and ripped past the tight barrier until I hit another wall. Jill cried out, "Ugggh!" and I froze. I wasn't expecting to hit another wall and I hit it with such force I felt my rock hard cock bend. I winched in pain momentarily. Thankfully, the pain I experienced was nothing compared to the incredible tight feeling of having my thick stick buried in Jill. Still, I worried I might have hurt her.

We waited in this position for a long moment. The whole time, the amazing sensations that reverberated through my cock caused me to be on the verge of cumming. The wet, tight, slippery grip was the most incredible thing I had ever felt. As I looked at Jill, her eyes were winced close as if in agonizing pain. A tear welled in one eye. My emotions were torn between extreme sexual bliss and an overwhelming concern for my true love.

Slowly, her pain ridden expression disappeared. She brightly smiled and opened her eyes. As this transformation took place, Jill adjusted to my girth, playfully started rotating her hips and mouthed "OK" and nodded for me to continue.

I took one slow stroke. The sheer pleasure I felt surrounding my cock took me to a new sense of euphoria. As I hit the back of her tight pussy, my toes curled, my vision blurred and I shot string after string of my boiling cum deep into Jill's depths. I lay there shaking on top of her for a few minutes. As Jill hugged me tight, she wrapped her legs around my ass and told me over and over how much she loved me. As I recovered from this mother of all ejaculations, Jill asked me to lie next to her.

I thought she wanted to snuggle like we had thousands of times in the past. Jill had other ideas and quickly assumed her original position. She strattled my waste and grabbed my still hard cum covered cock with lust filled determination, positioned the beast at her entrance and slammed down on my meat.

Jill sawed up and down on my pole with a purpose. The feelings were just as incredible as the moments before. This time, I was able to hold off for about a minute before I shot another sabot into her savory pussy.

Hell bent on achieving her first glorious "O", Jill refused to stop. She was really riding me and even with my inexperience, I could sense she was getting close. Her movements were becoming hurried and her breathing quickened. Then, with an extremely hard thrust down, she ground my cock into the back wall of her pussy. An inch of my cock was still exposed. As she ground, I watched my creamy cum leak from her pussy.

The creamy white globs freckled with bits of blood made me more determined to reward Jill with her own orgasm. I met her grinds. We quickened our pace and the grinding action turned into outright thrusts.

Finally, we met each other thrusts in unison. We had found our rhythm. I bucked and she bounced and then it happened. My cock drove in the last inch to its hilt as I froze with fear. Jill screamed with pleasure, ground her tight muff to a halt on straining meat, bent at her waist and bear hugged me as she finally experienced her own magical orgasm.

She froze with her pussy muscles involuntarily gripping and releasing my throbbing cock. These movements sent me over the edge one more time. I felt the girth of my cock expand to what felt like the largest it had ever before. I couldn't hold it any longer and I shot another creamy load.

This set Jill into round two of her orgasmic display. She felt the splatter of three streams of my hot cum coating her pussy walls. She pulled my hair and screamed she was cumming. I grabbed her waste as we rolled in unison.

Now on top, I rammed my cock repeatedly into her contracting cunt. I was a man possessed. Pounding Jill's tight pussy was all I could think about until I felt that feeling again boiling in my balls. I shot one time...exhausted...fulfilled.

As we both recovered lying side by side, we kissed, smiled and talked about the beautiful love we had made. She looked deep in thought and giggled. As she did, our combined cum started to stream from her red swollen lips. With each giggle, a new glob of cum dribbled from her sore lips. Without a word, she dipped her fingers into our combined juices, brought the mix to her lips and tasted it. Then, as if it were the most natural thing in the world, she kissed me with her tongue darting searching for mine.

I thought the whole thing was extremely erotic; but, the thought of tasting my own cum made we want to puke. Jill was sexy and I knew she wanted us to experience everything. My slow start gradually transformed into a hot make out session.

As we kissed, Jill repositioned herself on top of me as our hands travelled over the other's body. I tweaked Jill's nipples; while she traced her fingernails around my chest. My cock twitched and began to get hard as Jill ground her leaking twat onto me. Without laying a hand on my cock, she somehow was able to squeeze my straining beast into her hot tight box and she rode me slowly.

The sensations were just as powerful as the first time. I felt like I would cum any minute. Jill seemed to understand this as she took the lead in our love making dance. When she felt me tense up, she slowed. I began to understand what she was doing and talked to her about what I felt and how her movements affected me.

She would grind her spot with the head of my cock and I was in heaven. She would push down hard and it would nearly send her over the edge to another blistering climax. As we worked together, we each learned something about pleasuring the other.

Finally, the slow sensual pace became more hurried and deliberate. Both of us were near another mind blowing experience and we both wanted to cum. I grabbed Jill by the waste and thrust up as she came crashing down on me.

We had a perfect rhythm and we put all of our combined energies into fucking hard. We both wanted this. As my cock and her pussy slammed together, we became one. When we heard the sharp slaps of our bodies echoing across the room, we both smiled at the lewd noise that caused such pleasure. Our breathing was rapid and the pungent scent of sex was thick.

With a final thrust, we froze and looked deep into each others eyes. The white hot cum boiled from my balls deep into Jill's clenching pussy. Her inner walls were gripping and releasing my throbbing prick. We had achieved orgasmic bliss together and drifted off to sleep with my hard cock still inside my sweet Jill.

We awoke to the sound of Jill's parents returning from my parents' card party. Jill kissed me quickly and pulled her body away from me as she quickly darted around the room looking for her clothes. Cum flowed rather freely from her treasure box and I snickered.

This was not the thing to do. She quickly swatted me and told me to jump out her window. Still buck assed naked, I managed to open the window and leaped out as she threw my clothes at me.

It had to be around 11 PM or later. It was dark and I knew I would be able to sneak away without any issue. So, I slowly began to dress as Jill frantically transformed her room from the ocean side love shack back to a bedroom.

If I didn't see it with my own eyes, I wouldn't have believed it. She pulled the pink scarves off the lamps and jumped into bed just as her parents knocked on her bedroom door. She quietly answered and they came in to find their birthday girl in bed.

Her mother gave her a kiss. Stopped and stared at the open window. Her dad made a comment about the stuffy smell in the room. They both looked at each other with a knowing glance, wished their daughter a Happy Birthday and left.

When the door was closed, Jill jumped out of bed and ran to the window. She looked around and I popped up from the bushes. She said her parents knew what happened by the look in their eyes but were pretty cool with how they handled the situation.

When Jill mentioned her mom, I immediately thought about her parents' situation. Somehow Jill read my mind and said her mother started her on birth control a few months before her birthday. So, she was safe.

(I found out later that was why she was giggling earlier. She thought her mother's foresight had been right on the money when I shot my first load after such a short time. Her mother had a long talk with her about how she lost her virginity to her father. He came quickly and 9 months later Jill arrived. Her mom didn't want Jill, or me, to have to deal with that sort of a situation. She made it clear she loved Jill but she knew her daughter and wasn't sure she could cope with a child.)

Jill gave me a quick kiss and told me to take a shower when I got home because we 'reeked of sex'. We exchanged our "I love you's" and I walked home slowly while I finished dressing and savored all the memories we made.

As I reflected on her parents' intrusion, I knew I had to make myself available to them so they could have their "chat" with me. They were the most open parents a kid could have. Jill was used to it. I was constantly embarrassed by their forward questions. I knew both of them would want to talk with me about this. So, I figured I had better do something with them soon so they could have the opportunity to talk with me.