Street Pups

This is the story of a fantasy fulfilled one weekend. After a month of dating, Jen, my new belle was still a refreshing change from previous women. Like all the others, she proclaimed she'd be honest and completely truthful. The others soon proved they couldn't live up to that facade when they behaved the way they thought I wanted from them instead of showing their true desires and character. One lied from the beginning. That caused her to resent me when I tried to support what she said she wanted which was the opposite of truth. She never could admit what she wanted, so her resentment grew until it broke us.

As far as I can tell, what Jen says is true even if sometimes delayed a bit without lies. Despite being "proper," she has a free spirit and admits what she considers play, fun, and fantasy. When her friends leaked that she enjoyed mooning strangers and friends, she casually admitted it. That and the admission were a surprise as I had yet to be gifted with that vision. She stopped me at second base until she felt we had a solid future. A couple of one-nighters had set her on that path.

One day, she said she wanted to cruise the real Woodstock. "Jim, can we take your old Lincoln convertible with four friends?" How could I refuse a simple request like that? The town was less than three hours from Long Island, so I made plans to spend a day there and a night camping.

Cruising crowded and busy Tinker Street mid day with the top down gave us plenty to see — including where the police station was. We turned back at the next small town, Bearsville, noted there were no beat cops on patrol and then my exhibitionist girlfriend got into her fantasy. Just before we reached the "greens" at town center, Jen pulled her crop top to her chin and held it up as she flashed locals and tourists. Her friends in the back squealed and pulled up their shirts displaying six shapely tits to everyone but me. Tinker Street is narrow and plagued with slow or double parked cars and cars leaping out of narrow side streets, so I had to stay alert. "Again," cried out Ali.

Jen and Bea joined the chant. Hoping for a better view than the surprised tourists' faces, I turned around in the Playhouse parking lot. This time, all three women stood on my seats, turned and pulled down their sport shorts fully displaying their bubble butts to everyone — BUT ME. We drove through the town with three pretty asses gleaming in the afternoon sun. At one point, we were stuck waiting for some dolt to recall how to park. While at a dead stop, someone ran to the car and pet both willing asses on the passenger side — Jen and Ali. Though Ali dropped to the seat, Jen wiggled her sexy ass for the guy and I watched him spread her crack and kiss her butt. She was bent so far, I'm sure he saw and maybe felt her pussy. She laughed and blushed. I felt cheated that he got there before me.

"Um, Jen, was this part of your fantasy, to show your pussy to a stranger and let him finger it?" When she sat, she casually admitted it was.

"Yes, Jim. I told you I like the taboos of mooning and showing off my privates. I've never asked a guy to help me before, but I trust you and hope this isn't too much for you. Let's do it again." She stared at my tented shorts, "Looks like you enjoyed it too. Are you into exhibiting too? You guys can take out your dicks and no one can really see unless you stand and wave it."

I said, "You guys can do what you want. Don't forget the cops may smile at the nude women, but lock us up." The women flashed their tits to cheers as we passed, then covered up all aglow. I drove the short distance to a forested camp area and parked the car.

Sunset came and we decided to try one of the new eateries and a new club as pedestrians. We took our time walking the narrow sidewalks and window shopping. The café and club were just past the "greens," a long walk. The girls danced modestly in the dim lights for the first hour. After a few drinks created an excuse to let loose, Jen was first to toss her hair and arms wildly, drawing attention with her movements and loose tits. Every time she raised her arms, her crop top lifted across her areolae with her stiff nipples barely capturing it. She tossed harder and bent more so her tits completely escaped for her enjoyment and that of all the stiff cocks surrounding us. Ali and Bea were less violent, yet happily flashed their tits too.

When a slow dance played, Jen especially threw her arms around my neck high enough to expose her stiff nipples. She grinned at me, "Is this too much or OK?" In answer, I slipped both hands into the back of her panties, rubbed her ass deeply, then pushed and held her shorts below her exposed ass. I smiled back at her.

"Is this too much or OK?" I asked. She sighed, leaned her head on my chest and turned us slowly to expose her pretty ass to more people and her friends. As we kissed deeply, I felt a hand tap me.

"May I cut in? You can slow dance with my lovely wife, Kath." I wasn't inclined to share Jen with a stranger, but she seemed to be happy to. She threw her arms around the taller man, crushing her bare tits against him. He looked at me, smiled, and pushed her panties down her ass just as I had them before turning her away.

His beautiful wife stood by me in her low cut, short, purple dress. It fit her small waist snugly, except her huge tits were barely contained. "Don't mind Ken. He'll feel her tits, ass and maybe her pussy — all the things he expects you to do with me. He wants to watch us and wants you to kiss me so he can kiss her for balance. Oh, and I'm commando with waxed lips. Dance with me?" I watched Ken with Jen. One hand teased her bare tit while the other rubbed her bare ass deep down between her legs. She kept raising it away from her pussy.

"How can I refuse a beautiful woman offering me full access?" I twirled us closer to Jen helping the purple dress expose beautiful, toned legs. When next to them, I scooped her huge tits out of her dress. She and Jen smiled. I raised her short hem to her waist, felt her bare ass all over to confirm her claim, then cupped her pussy. Her mons was trimmed, but her lips were smooth. After tucking her hem under her waist, I spun her slowly so I could admire her gaping pussy, her pert ass, and swinging tits. She was a beauty. I kissed her nipple; Ken kissed Jen's. So I knew not to kiss Kate's pussy. I spun her again — into Ken — and took back my woman. "You do have a very beautiful wife, Ken. Honey, they're closing down. Ready to go?"

"Let's collect my friends." We found them slow dancing, half naked too. "Ken said they are up from the city too and are in the same camp area. Should we walk back with them?" That wasn't my plan, yet I agreed. "He also said they are disease free when I slapped his hand away from my pussy. I won't share that, at least not until after I share it with you, lover. Are you willing to share me if that's part of my fantasy?"

I sighed. "If we are safe and don't catch any STDs, I'm willing to try that. Is that your fantasy?"

"No. But I'm not willing to exclude it." We all adjusted our clothes and started our long walk back. I asked Ken if he got into my girl's pussy and said I saw him lick his fingers.

He dropped his head and nodded, "Just the tip. I was curious if she was just teasing us or enjoying exposing herself. You didn't finger my wife?" When I shook my head, we stopped at the "greens" and under a streetlight, he held up his wife's dress in front. "Here she is. Help yourself. I insist." Jen looked, smiled, and nodded at the beautiful, well-lit, hairless vulva. Taking my time, I felt the smooth labia before slipping two fingers deep into the wet pussy. A few squishy strokes made her eyes close and breathe hard. "Thank you for preparing her for me, or us, to share."

Jen shrugged. I sniffed and licked a finger as they all watched. Jen grabbed my hand and licked one of the fingers clean. "Mmm, more sweet than tart, the opposite of mine." Ken was about to confirm when he thought better.

"How would I know since you denied me access?" With all the sexual tension peaking, I dared to ask Jen a leading question after turning her toward me.

I whispered, "Have you ever been Dogging, Jen?" I trusted her to answer honestly.

"That's the British thing where people go to a dark car park, or doggie run, to watch other couples fuck in a car and can participate? Hmm. No, never did that or had more than one guy at a time. Why?"

"You're right about the watching or participating. But it isn't just about fucking. Each person decides how far they want to go. Some do sexual things inside their car with windows up; some open windows or doors or step out and service strangers while their mate watches." As I explained, I removed her crop top and tossed it on a bench. Rolling her stiff nipples, I added, "It can be staged in daylight in a semi private area, nearly always in front of a crowd. Often the couple goes merely to expose themselves with no sexual contact." I pushed her shorts and panties to her ankles and looked at the forming crowd as I helped her remove her shoes and clothes. Now naked and grinning, I had to admire her beauty, especially her elusive pussy.

Ken unzipped Kate's dress and hauled it over her head. In one step she was naked, smiling, and stunning. Abi pulled my shirt off and tossed it aside; I saw her top land on the bench too. Jen pushed my shorts down and Kate grabbed my rebounding cock as Jen removed my shoes and clothes. Eyes only for Jen, I moved against Jen while Kate aimed my cock at Jen's pussy. Once parked between her lips, she stripped Ken and sucked his long, thick cock. The others seemed to be naked, but my focus stayed on Jen, my naked beauty. Kate commented that twenty or more were watching us.

As I kissed Jen passionately, someone grabbed my cock and rubbed it along Jen's wet pussy. It turned out to be Ken who also slid a finger into Jen and got a full taste of her snatch. All I knew was my cock felt the heat of her sex. She gasped as I aligned and thrust my cock in her for the first time — as witnessed by many. After several slow thrusts, I felt Kate sucking Jen's nipple and sudden pulsing pressure on my cock. I doubted Jen's pc muscles could pressure me in that odd way. She gasped again. Kath moved behind me and as our friends and voyeurs watched, she rimmed and fingered my rear hole. As I rubbed Jen's clit, she shuddered in orgasm and triggered me to fill her pussy with hot cum. As I held my cock still inside her, I felt her warm spasms and another cock fill her ass with cum. Ken was behind her. Does that mean I get his wife's pretty ass?

"Well Jen, now you have been Dogging in a special way, on a public street. As a first timer, I guess that makes this a Street Puppying. Are you willing to do this again, Street Pup?"

"You bet my ass I am."

==== 6 hrs 2130 11/8/23 ==== 2066

11/6/23 seminal image: Dogging in Woodstock open park