A Straight Guy in Provincetown

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."

Five minutes later, we were slowly walking hand in hand and barefoot down the beach. The stars were shining and the moon was full. A few hundred yards down the beach, Ellen turned, wrapped her arms around my neck and kissed me. I rested my hands on her hips and kissed her back. I was encouraged when Ellen opened her mouth to my exploring tongue and playfully bit it.

We walked for half a mile, stopping to kiss and fondle each other every few minutes. Ellen groaned into my shoulder as I cupped her breast and tweaked her nipple. When I cupped her ass under her skirt and ground her pussy into my hard cock, she whispered, "Where are you taking me?"

"Home," was my reply as I gestured to the next home along the beach.

"Oh good, lets go."

When Ellen turned to run to the house, I reached for her arm. When she turned to face me again, I instructed her, "Strip."

"I can't. Not here."

"Right here, baby. Strip for me."

Ellen nervously looked along the beach and at the neighboring properties.

"There's no one around. Take off your clothes."

She stood five feet away from me. Looking me in the eye, she tossed me the sandals she'd been carrying. In one motion, she pulled her tee shirt from the waist of her skirt and over her head. The front clasp bra followed a few seconds later and Ellen handed me both garments. Reaching to her lower back, she unbuttoned her skirt, unzipped it and wiggled out of the skirt and panties.

Ellen stood proudly in front of me. She had firm B-Cup breasts topped with small brown nipples. She had a flat stomach and narrow waist. Her pussy was covered with a light peach fuzz bush.

"Your turn," she dared.

I handed her the clothes I was holding and quickly peeled my tee shirt off. Although I'm forty five, I'm in pretty great shape from years of hard exercise.

"Not bad," Ellen commented as she looked at my chest.

"I feel like such a piece of meat," I countered and we both laughed.

When I stepped out of my shorts and boxers, Ellen's jaw hung open. "Jesus, you are a piece of meat. Your dick is huge."

As if in a trance, Ellen approached and sunk to her knees in the sand before me. She sat back and stroked my eight inch cock with both hands. Looking up into my eyes, she said, "My husband says I can suck the chrome off a muffler."

With that, she opened her mouth and sucked in the first half of my cock. "Oh baby, I'll have to let your husband know he's right."

Giggling around my tool, Ellen reached around, hugged my ass and pulled another two inches into her mouth and down her throat. She started a slow, steady up and down motion taking more cock on each down stroke.

When her lips buried themselves in my pubic mound, Ellen snaked a finger into my ass crack and teased my rose. Her other hand massaged my balls and her mouth took my entire cock time and again.

"Baby, get ready, you're going to drink some cum."

A "MMMmmmm," escaped Ellen's lips. Her hands worked my asshole and balls and her mouth slide rapidly along my cock.

"Here it comes baby. Oh fuck, here it comes," I yelled as I exploded into Ellen's mouth. She gulped most of it, but pulled away when she choked and some sperm slide down her cheek.

Ellen jumped to her feet and ran to the house. When I finally found her, she was laying in the middle of my king size bed. I crawled onto the bed and grabbed Ellen's ankles. I spent a few minutes kissing and sucking her toes. I slowly and methodically worked my lips and tongue over her ankles and up Ellen's legs.

By the time I reached her spread thighs, I could smell the delicious aroma of her sex. Ellen was spread wide. Her pussy was pink, dripping and open. I kissed her pussy softly and listened to her purr.

When my tongue traced from her clit to asshole, Ellen bucked into my face. "Oh yes . . . oh fuck yesss . . . lick my fucking pussssyyy . . . yes . . ."

Ellen cringed as the first orgasm racked her body. As she calmed, I wrapped my lips around her clit and slid two fingers into her pussy. Her body exploded again, "FFFuuuccckkk . . . yyyeeesssssss!"

My dick was fully recharged, so I slid up Ellen's body and sank my dick into her open pussy. "Holy fucking shit! It's fucking huge! Fuck meeeee harrrd."

I fucked Ellen in a missionary position for ten minutes. Then I pulled her to the edge of the bed, stood in front of her spread pussy and jack hammered her. As I pounded her twat, I rubbed her clit with my thumb. "OOOhhhh yyyeeesss!"

When her climax finished, Ellen pulled me out and turned onto her knees. When I pushed into her pussy, she said, "Not there baby. I want you in my ass."

Ellen hunched her back as I lined my dick head up with Ellen's rose. "Go slow baby. Go real slow until I adjust."

Over the next few minutes, I worked my cock up Ellen's asshole. She was so tight. With four inches buried in her, I stopped and let her rest. When she appeared more comfortable, I started to saw in and out, pushing more meat into her with each thrust.

While I sodomized her, Ellen fingered her pussy and rubbed her cunt. Ellen came again with a piercing scream. Then she reached back and massaged my balls. "Cum. Cum you bastard. Cum in my asshole."

I grabbed Ellen hips and banged her. "Here it cummmms. Here it cummms, you fucking slut." I finished for the night by pumping Ellen's asshole full of cum.

Present summer – Saturday Morning

Luckily, I don't need a great deal of sleep. Ellen and I fell asleep around 3am. She was groggy and a little pissed when my alarm went off two hours later at the usual 5am.

I dropped her off at her B&B, promised to touch base with her later and drove further down Front Street to my office. Most of my Provincetown friends think I'm a hard drinking, rich, hetro playboy. In truth, I work very hard.

Since taking over my grandfather's company, I have added twelve commercial properties to our portfolio. In addition, we manage another sixty properties on the Cape.

What's the old saying? "I work hard and I play hard."

I was on my third pot of coffee at 10:30 and needed a break. As it was Saturday morning and the office was empty, I went out on the buildings front porch. I brought my laptop, a few files and coffee, but I mostly daydreamed as I watched the tourist's parade through the street.

"I should be mad that you kept my girlfriend out all night."

I looked up to see Sally standing at the picket fence in front of my office building.

"If I offer you a cup of coffee, can we be friends again?"

Sally chuckled as she pushed through the gate and walked up the brick sidewalk. She looked like a MILF, dressed in a light summer dress. Her red hair hung over her shoulders and framed a pretty smile. I great deal of cleavage showed over the top of her dress and athletic thighs dropped below the hem.

I offered Sally a seat. After returning with a second cup and fresh pot of coffee, Sally and I sat and talked about Cape Cod and Provincetown.

After a while, she said, "You know, she's not a slut."

"Sally, I never said Ellen was a slut. She's a nice lady and we had a fun time."

Sally shook her head, "We're both pissed at our husbands and talked about fooling around while we were here. I was serious, but never thought Ellen had it in her."

"Hey, I don't kiss and tell. I never said we fooled around."

"You didn't have too. When she made it into the room this morning, she reeked of sex, she was sweaty and was walking bow legged. If that wasn't enough of a clue, right before she passed out, she said, 'I've never been fucked so hard.'"

Not knowing what to say, I kept quite.

Sally let out a frustrating laugh. "We've always been super competitive, but in a friendly way. I'm going to have to think of something to one-up Ellen."

Sally stood from her chair and walked into the office. I took my time following. I walked to the kitchenette and dropped off the pot of coffee and cups. My staff's area was empty and when I walked into my office, Sally was sitting naked on my leather couch.

She was leaning against the arm of the couch and her legs were tucked under her and to the side. Most people look better with clothes on, but not Sally. She looked spectacular. Her tits were easily a DD, but were round and stood out. They are capped with large aureole and one inch thick nipples.

Her stomach is taut and she has a cute belly pierce. Between her thighs is a shaved pussy.

"What do you think, Christopher? Will a nooner in your office, one-up Ellen?"

Standing in front of Sally, I stripped off my shirt, shorts and topsiders.

"Holy God! Your dick is huge."

In reality, my cock was only half hard. Sally excited the hell out of me, but last evening workout with Ellen had me worn out.

I retreated to the armchair in the corner. "Before you can one-up Ellen, you're going to have to get me hard."

Sally flew across the office and dropped to her knees between my legs. She slurped my rod onto her mouth with the enthusiasm of a teenager. She pumped my base, sucked the head and licked the sides. "Your dick feels so good in my mouth."

Her mouth felt so good sliding around on my cock, that I leaned my head back and selfishly enjoyed the blowjob. Without complaining, Sally sucked and deep throated my dick for fifteen minutes.

I was so engrossed in Sally's oral talents, that I didn't hear Mike, my 60 year old handyman, rummaging around in the outer office. We were all shocked when he stuck his head into the office and started, "Christopher, I'll see you on...oh shit."