Pittsburgh Bucket list


Pittsburgh Bucket list
The hotel phone was heavy in my hand as my mind raced back to my youth and the role that Jennie Rickard had played in it. Although the feeling was never mutual, Jennie was my first MAJOR crush. I hadn’t been in the Pittsburg area in over ten years and hadn’t spoken to Jenny for at least that long. A business trip had placed me on the outskirts of the inner-city and despite being married, I was having a hard time getting my mind off the thought that contacting Jenny would be a good idea.
From the time I was old enough to walk and well into my teenage years, my family would vacation every summer from our VERY rural Central Pennsylvania town, into the city of Pittsburgh to visit one of my father’s Navy buddies and his family. As luck would have it, my dads Navy buddy had two son’s, Steve who was my age and Brian who was 4 years older. Over the years, Steve and I became very close friends. We were however, about as opposite as two k**s could get. Steve was and still is a brutally handsome young man, charismatic, dark hair, olive skin, even at a young age, women swarmed to him. Me, on the other hand, I was quiet and reserved with no sort of “game” whatsoever where woman were involved.
The sound of the phone beeping in my hand due to its being off the hook too long brought me to attention. Throwing caution to the wind I pressed the tone button, reset the phone and dialed information. Within a few minutes I was chatting with Jennies father John Rickard. I was happy that he had remembered me, and he was more than happy to give me Jennie’s phone number. After some debate between the angel and devil within me, I found my fingers pressing the digits to Jennies phone. I was just about to hang up when a quiet questioning voice answered,
“Jennie Rickard?” I asked
“This is she, who is this”
“This is Grant….I used to visit in the summer”
The phone erupted,
“Grant!, Oh My God!, Is this really you, how are you?”
I was more than happy she remembered me. We chatted for awhile on the phone and I was surprised when she recommended a visit at the hotel.
“Give me about a half an hour and I should be there”
With that we hung up the phone and my mind went into to overdrive thinking of days gone by and the history or more like torture she had put me through over the years. The first time I saw Jennie, Steve and I were tasked with going to the Rickards to help Mr. Rickard move a new couch into the house. Jennie was the youngest of four by 6 years. Her parents were quite aged compared to mine. I was introduced to her mother and father who was glad to have the extra help. When the couch was placed in its spot on the living room floor, I heard the back door open followed by footsteps coming down the hallway to the living room. Jennie wore a one-piece bathing suit and mirrored sunglasses. Her sandy brown hair fell onto her bronze shoulders and at the time she was the most beautiful creature I had ever seen.
“Hey Steve, get conned into helping dad I see?” She smiled and Steve replied with a sense of annoyance.
“Who’s your friend?”
“This is Grant, his family is visiting for a few days”
Jennie pulled her sunglasses slightly down her nose, revealing her piercing chestnut brown eyes. She looked me up and down,
“You guys should come swim sometime”

It took me a few hours but I finally coaxed Steve into heading across the street to swim. I didn’t know it then but do now, a swimming pool is the greatest gateway to four play EVER. It wasn’t long before we would make her lay still and flat atop the water. With each of us positioned to one side, we would bend our knees and place one hand under her shoulder and the other firmly on her ass. We would then heave her violently into the air as high as we could. We would repeat that about a hundred times, with each hand on the ass getting a little more risky until a time here an there a finger would slip inside her suit. It wasn’t long before she was reciprocating with subtle touches beneath the water. In just a few short days I was in love. She was the first girl to show me any attention and the most beautiful girl to date that I had seen. We kept in touch through letters for a few months but eventually she stopped writing. The next two summers were more of the same until I found her and Steve making out at the back of an amusement park ride the night before I left for home. I was devastated.
The following summer I was shocked to find out when I arrived that Jennie had gotten pregnant and had given birth to a baby girl a few months before we arrived. I visited a few times during my stay, but the swimming shenanigans were over. With the baby’s daddy not playing a role and her parents holding her feet to the fire, it was her soul responsibility to raise this c***d. She was a mix of angry, embarrassed and depressed.
Two years later while attending Steve’s brothers Brian’s wedding, I was pleasantly surprised to see we were seated next to one another in the corner of the reception hall. She was thicker than the last time I saw her, but it suited her. We made small talk with the people around the table and dinner was served. While taking a bite of the entrée I felt Jennies left hand move to my inner thigh and eventually firmly gripped my cock. I almost choked on a piece of chicken. Looking at her, she smiled and playfully forked a green bean into her mouth. By the time the music started playing she had managed to get my zipper down and her hand was beneath my dress pants groping my bare cock. Most of the table party had gone to the dance floor when she released her grip,
“I’ll be right back”
She stood and exited the hall. In a few minutes she came back, leaned over and whispered,
“put your hand under the table”
She sat and I revealed my right hand beneath the table. I could feel her hand slinking its way to mine and could feel a silky texture surrounding her fingers. She released the item into my hand, stood up and walked to the dance floor. My thumb and forefinger began exploring the fabric. It was silky and upon rolling it over and over in my hand, I noticed it deposited a sticky wet substance onto both my fingers. Holy Shit, these were her panties! I looked to the dancefloor to see her peering at me like a predator. I stared back at her, released the panties from my grip and brought my wet fingers beneath my nose and inhaled her scent fully. Without hesitation I placed both fingers into my mouth as if I was eating an olive plucked from a dish. Her gaze went from Predator to Prey as this was not the reaction she had expected from the country boy bumpkin. The rest of the night was followed with intimate slow dancing, more fondling and teasing than I care to remember until eventually she had to be home to care for her toddler. That was the last time I had seen Jennie Rickard.
The ring from the phone awoke me from my thoughts,
“Hey, it’s me, I am on my way up”
“I will meet you at the elevator”
I put my jacket on and checked myself one more time in the mirror. This was a culmination of fifteen years of pent up frustration about to possibly come to fruition. When the elevator doors opened she greeted me with a huge tight hug.
“You look amazing” I said
“You too, Oh my god, you have a beard” as she said that her hands reached up and her fingers ran slowly over my face.
“It’s soft”
I blushed and changed the topic,
“What would you like to do, we could go out for a drink?”
She answered quickly,
“Or we could stay here”
“Stay here?, Yes, we could stay here”

I opened my room which revealed a king sized bed, she took off her shoes and coat then laid on her stomach with her hands holding up her head like a c***d would during a kindergarten class book reading. I seated myself against the headboard and we began talking about the last ten years. She admitted that she knew I had gotten married and had a baby boy from Steve’s parents. I was surprised to hear that she had another c***d, a boy, was married and recently divorced. As the night waned, I wasn’t sure I had it in me to make a move. During a period of silence, I stared into her eyes and she began to blush,
“What?”, she said
“You’re still as beautiful as the day I first saw you”
She placed her face in her hands and laughed embarrassingly.
I moved slowly closer down the bed,
“I’m not sure what to do here, I’m really not”
Her face took a look of seriousness, she could see the apprehension all over my face,
“I am here aren’t I”
With that, I leaned over and kissed her as passionately as I have ever kissed anyone. As she rolled to her back, her right hand pulled me hard into her mouth, I could feel her fingernails digging firmly into the back of my head. The kiss lasted longer than either of us expected. We were both near out of breath when the kiss ended. In the heat of passion my hand began to work at her belt, then button on her jeans. She aided me at every turn until at last she was wearing nothing but a lacy black thong and a button-down silk shirt. With one tactical twitch of my fingers her bra was unhinged from the back and her beautiful tits relaxed beneath the white silk shirt. I paused a moment and took time to stare down upon her.
“Do you have any idea how many times I have thought about this”
Her look was wanting and her voice seductive,
“I am guessing more than a few”
My right hand went from her stomach up her shirt and caressed the underside of her left breast as my right knee gyrated between her legs into her pussy. I wanted to make her beg, I wanted her to feel the years of anguish she caused me. I could feel her untamed bush beneath her panties. My left hand slid under her chin, rubbing my thumb over her bottom lip. I could feel her hips pushing into my knee and with it the feeling of wetness escaping her panties. One by one I unbuttoned her shirt and threw it and her bra to the floor next to the bed. She was now completely naked above the waist. I took a moment to take it all in before releasing my knee from her bushy mound. Reaching down to her hips I pulled off the thong, grabbed her calves and spun her completely around the bed so that she was positioned in front of the headboard. Spreading her legs wide, I could see the frothy buildup exuding from her pussy and onto her inner thighs. Her pussy was as unmanicured as I had ever seen. Being an extremely primal being, this was not a deterrent, in fact when her scent reached my nostrils it was so intoxicating, I let out a guttural moan. I ran my fingers threw her thick bush, exploring the texture and wetness that laid within until I could stand it no longer. I needed to taste her, all of her. Placing my head aggressively within her pussy I began to indulge in her juices, spreading her lips apart and flicking rapidly at her clit. She began to buck furiously, screams tried to escape her mouth, but her lack of breathing caused it to sound like more of a guttural pant. Never had I engrossed myself in a pussy this wet, her first orgasm came quickly, her knees pinched my head and she screamed loud enough I was sure the front desk would be calling to throw me out of the room. When her thrashing calmed, I place one then two fingers deep inside her soaking hole. Wiggling them in rhythm as my tongue continued to lap her clit. I entered a third finger in her wide hole and she again began to squirm and writhe as another orgasmic wave took hold. She could take no more and pushed my head away to give her much needed air. As I raised above, I could see the white lather that had formed within her hairy bush. The bed sheet below her was wet to the mattress.
With a quake in her voice she asked
“What was that?”
Looking down at her my beard glistened with her juices,
“That?….That was the beginning”
Positioning myself at her entrance my cock had little trouble navigating threw the wetness into her gaping hole. She let out another moan and I pressed deep into her, bringing my head down to her mouth she kissed me fervently, inhaling deeply her own juices and fragrance. Picking up pace she urged me on,
“Don’t…. stop….Cum inside my pussy, I want your cum!”
Gripping her behind the neck, my body stiffened. I could feel the heat from my cum filling her up, stream after stream pulsating within her. Collapsing on top of her, she caressed the back of my head.

We fucked several more times that night and I have not seen her or had any contact in over 15 years. She was one of three girls that I had placed on my bucket list and now that chapter is over.

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