Thanks to Sally, a Literotica reader and friend. She emailed me a basic outline of her recent vacation to Provincetown, Cape Cod. Sally and her friend, Ellen, were good MILF's while visiting this quant vacation get-a-way. This is a story of what might have been. . . a story that Sally wished happened.
Thanks to Karen – the hair lady, for her editing skills.
Present summer – Sunday Morning
"It is going to be another beautiful day on Cape Cod," I thought to myself as I looked out at the calm waters of Provincetown harbor. It was 7am and I was sitting in an Adirondack chair on the second floor balcony off my master bedroom suite.
Life couldn't get much better. I had a steaming cup of coffee in one hand and a thirty four year old, married teacher from Worchester, on her knee's, between my legs, deep throating my thick eight inch cock.
As I looked between my spread legs, all I could see is a mass of red hair as her head slowly bobbed up and down on my rod. Her lips are wrapped tight and easily slid from my cock head to the base.
Sally had waked me ninety minutes earlier by sucking my cock. After getting me hard, she straddled my waist and guided my tool into her tight wet cunt. "Oh, Jesus. I'm going to miss this," she moaned as my dick bottomed out.
I had pulled her forward and aggressively sucked a massive nipple into my mouth. I bit her rubbery nub as she rode my tool. "So . . . fucking . . . good," Sally whimpered into the morning air.
After riding her to two powerful orgasms, I rolled Sally onto her back. I held her spread legs in the crook of his arms and power fucked her married pussy. Sweat was pouring down my chest and onto Sally's flat belly as we both approached orgasms. "Grab my balls baby."
Sally reached for my swinging sack and massaged my balls. Her touch was electric.
"I'm getting close baby. Your pussy feels so good."
"Just fuck me. Fuck me hard."
I pounded her juicy twat for a few more minutes.
When her cunt spasm around my dick, she bellowed, "Oh, I'm cumming again. Keep . . . fucking . . . meeee . . . hard."
"Me too, baby. Here I cum." I continued to stroke her as I dumped another load of cum into her hole.
We rested for a few minutes, until I finally said, "The coffee is on an automatic timer and is ready. Can you go to the kitchen and grab the pot and two cups? Meet me on the balcony."
Sally kissed my lips and rolled off the king size bed. I watched her cute little ass swing back and forth as she left the bedroom and walked naked down the hall.
My friends kid me and say, I'm the only straight person in Provincetown. Some days, I
think they're right. On a typical evening, gay and lesbian couples walk hand-in-hand up Commercial Street, the main drag. A fat, transvestite magician in a short tuxedo-style dress invites passers-by to his show. A butch looking comedian from San Francisco promises to make you laugh if you come to her 9pm performance.
To be sure, I'm not the only straight person. There are plenty of couples and families that come to Provincetown for the art galleries, food and entertainment. However, at times, I think I'm the only straight single guy within twenty miles of this seaside town.
My name is Christopher. I'm a forty five year old male and I've lived in Provincetown for nineteen years.
My grandfather was gay. He married in the 30's and had three daughters with my grandmother. He was also a successful New Haven, CT lawyer and part-time professor at Yale law school. When his true sexuality surfaced, he quietly divorced and relocated in Provincetown.
I didn't know I had a grandfather. He was a family secret. When I was fourteen, I was snooping through my Mom's closet and stumbled into a shoebox filled with unopened cards and letters addressed to me. It turned out my grandfather wrote me once a month for the previous fourteen years.
It took a while for me to gather the courage, but using the return address on the envelopes he sent, I wrote him back. My grandfather and I wrote weekly for the next few years.
When I was sixteen, I told my parents that I wanted to go to our lake front home in Vermont for a weekend alone. Instead, I drove to Cape Cod to meet my grandfather. We had a great four days together which was the start of our special friendship.
When he died ten years later, our entire family was shocked to learn that my grandfather left me his bayside home in P-Town. He also made me the chairman and owner of a real-estate holding company. The company owned seventeen commercial properties in the downtown Provincetown area and was worth over fifty million dollars. His only stipulation was that I continue to provide for my grandmother, Mom and aunts.
Nineteen years earlier –
I was unsure if I wanted to live in the gay vacationland of the northeast. However, as I was young and filthy rich, I decided to give it a try. I moved to Provincetown in the summer of 1986.
On the first Friday night in my new home town, I was sitting at Ross' Grill and Bar on Whales Wharf. It was very crowded and filled with gay and lesbian couples and groups. I introduced myself to Ernest, a fabulously gay bartender as Tommy Lowe's grandson and Ernest introduced me to the few regulars in the bar.
As I was sipping my second scotch on the rocks, Ernest asked, "You're straight, right?"
I laughed and answered, "I suppose I stand out here, like a gay guy would at a Marine Corp convention."
Ernest squealed in laughter, reached across the bar and shook my hand. "Christopher, you're going to get along just fine."
Then he leaned across the bar and whispered, "If you're looking to get laid tonight, there's a cute married lady at the other end of the bar. She's pissed her husband isn't coming on vacation until tomorrow and is horny as hell."
When I raised an eyebrow, Ernest continued, "The straight women on the prowl will tell a gay bartender anything and she just wants to get fucked hard. Good luck." Ernest winked and then skipped away.
I walked to the other end of the bar. The woman was cute. She was in her mid-thirties, had a very pretty face and an average body. Her hair was shoulder length and black, her eyes were dark brown and she had a bright white smile. Her C-cup breasts were covered by a scoop neck tee shirt and she wears a knee length tan shorts.
I nodded to Ernest and shouted, "Another scotch please," then turned to the woman. "I'm Christopher. Ernest says we're the only straight people in here tonight. I figured there is safety in numbers, so I wanted to introduce myself."
She smiled and then giggled. "Hi Christopher, I'm Lori."
"Can I offer you another glass of wine?"
Lori and I talked for the next ninety minutes and shared three rounds of drinks. She was a wicked flirt. She touched my arm and thigh and there was a little twinkle in her eye. At 11pm she said, "I need to get going Christopher. Will you walk me to my car?" She invited.
I settled our bill and arm in arm we walked to her car on the far end of the pier. Ernest was right. Lori just wanted to get fucked. She pulled off her shorts as she climbed into the back of her Ford Explorer. I climbed in behind her, shut the door and pulled my shorts to my knees.
Lori lay on the bench seat. One leg was draped over the seat and the other was on the floor. The light from the street lamp shone through the window. I could see the dark trimmed outline of her bush as I drove my eight inch cock into her dripping pussy and started a hard urgent fuck. I was young and inexperienced. I came in two minutes. I never got completely soft and continued to pound her until I was fully hard again.
"Turn over baby. Get on your knees."
Lori struggled to turn over in the confined space. She finally climbed onto her hands and knees and offered me her pussy again. I drove into her from behind for fifteen more minutes. After cumming in her pussy for the second time, I pulled my shorts up. Patting Lori on the ass, I said, "Thanks baby that was great."
I went back to the bar long enough for Ernest to palm the fifty dollar bill as we shook hands.
The next evening I waved to Ernest as I walked into the bar. He motioned me to a corner. "There's an older married lady at the end of the bar. She's fifty, but has a killer body. Good luck."
Four hours later, I left June's hotel room. She had sperm on her breath and dripping from her stretched pussy and asshole.
Ernest was right, I was going to get along just fine in Provincetown.
Present summer, Friday night –
I walked into the Front Street Grill at 9pm. I shook hands with a few locals as I made my way to the bar. Lady Di, a 300 lb, tattooed, lesbian bartender had my scotch ready when I got to the bar. "There are two married bitches at the table in the corner. They've been here for a while and I think they're getting bored. If you hurry, you might have a chance."
"Thanks baby." I handed her a generous tip and kissed her cheek.
As I approached the women's table, I began, "Lady Di, the bartender is feeling sorry for you. She says that her dike friends have been trying to hit on you all night. She thought you might like a change and have a straight single guy hit on you for awhile."
When the women smiled and laughed, I reached out my hand. "I'm Christopher."
"Hi Christopher, I'm Sally," said the cute redhead, "And this is my friend Ellen." She nodded to a tall, thin blond. "Are you really straight?"
"I am. When I die, they're going to stuff me and put me on display in the local museum." We laughed together and I continued, "Are you having fun in P-town?"
"We arrived this afternoon," said Ellen. "Our asshole husbands have been golfing in North Carolina for the last six days. This morning, they extended their vacation until Sunday, so we decided to come to Cape Cod."
"They're probably screwing some bimbos," Sally chimed in a slightly drunken slur.
"Let's not start that again," Ellen begged. "We've been bitching about our husbands all night. Now that we've found a cute local guy, let's talk about things to do in the area."
We talked and drank for a few hours with Sally becoming more and more quite. "I've hit a wall guys. I need to go to bed."
"Would you mind if I treated tonight?"
"That would be really sweet." Ellen leaned in and kissed my cheek.
I paid the bill and walked the girls to their B&B. As we arrived, Ellen admitted, "I'm getting a second wind. Could I walk Sally to our room and then do something with you?"
"I'll wait here."
Ellen winked and said, "Give me five minutes."
