First Time Fucked in a Park Ch. 01

I was horny and browsing the Craigslist "casual encounters" section, when this ad caught my eye:

Married woman seeks discreet meeting in a local park. I don't quite want to cheat on my husband, but I'd like a guilt free way to spice up a love life that's gone a bit stale. So, I want to talk dirty to you and masturbate you until you cum. That's it. No sex, no reciprocation, and only I get to initiate physical contact, and decide if or how I might let you touch me.

If you can respect these limits, give me a thoughtful reply, stats, and a face pic or three. Dick pics or one liners go in the trash.

This sounded ... unique. Fun. So, after a few dozen emails and then some texts, per her instructions I put a small tube of lube, and a handkerchief for cleanup afterward, in my pocket.

I drove to the parking lot for our arranged meeting spot in a rural park nearby, then hiked a dirt trail rutted with rocks to an isolated place by a picnic bench. Several ancient live oak trees with branches nearly touching the ground screened the bench from the view of the trail nearby. Privacy was ensured even more by the meeting time we'd arranged, a Thursday afternoon at 2 pm, when the park was nearly deserted. There was a bit of an early fall nip in the air.

Five minutes after 2 pm, she still hadn't shown up, so I texted her: "Are you on your way?"

No response.

Great, I thought. Is she flaking out on me? I walked around the stand of oak trees to see if maybe she was nearby and I just hadn't spotted her, only to find a tall good looking guy with curly brown hair texting from his phone.

He gave me a guilty glance. "Um, were you looking for some privacy?"

"I guess not. I was supposed to meet some woman here, but I think she flaked out on me."

He narrowed his eyes. "Was she a married woman, by chance?"

I nodded.

"Wanting to meet up here for ... um ... you know ...?"

"Jacking me off."

"Fuck," he said. "I think she played both of us."

"I'm gonna give it a few more minutes, and if she doesn't text back or show ... time to bail." I started walking back to the bench area.

"Mind if I join you while you wait?"

I shrugged. "Suit yourself."

We walked to the bench and both sat on it, paging through stuff on our phones.

Five minutes later, I said, "Yeah, that fucker's not showing." I got up to leave.

"I got another idea."

I looked at him with raised eyebrows.

"How about ... um ... how do I say this?"

"What?"

"Maybe I can jack you off ... and then you can do the same to me."

"No way. I'm not gay."

"Me neither. I'm just horny and want to get off."

"Nah," I said. "It'd be kinda gross watching a guy do that to me."

"Um ... well ... maybe if ..."

" ... hmm?"

"How about I stand behind you and ... do it ... and since you couldn't see me, you could pretend it's the woman we waited for?"

"I'd still know. Your voice is way too deep."

"I'd be quiet. No talking."

I ran my hand through my hair, thinking it over. "I can't believe I'm about to do this ... look, if it feels too weird, I'm outta here."

"Sure."

"So ... how do we ..."

"We'll do it just like she described ... except not looking at each other. Or talking. Turn around."

I slowly did so.

"Put your hands on the bench ... like she said, no touching her without her permission."

I did that, too.

"Now close your eyes and imagine it's her. I'm gonna quit talking now."

I shut my eyes and imagined her the way she'd described herself - a short, big breasted MILF with a bit of a booty.

I felt his ... no, HER ... hands undoing my belt buckle. She slowly unzipped the fly, and her soft hands reached inside and sensually slid down my hips and along my inner thighs, teasing me, not quite touching my cock and balls. She ran her fingers back up my skin, nails gently scratching.

"Ummm ..." I murmured, getting a bit turned on despite myself at the unexpected gentleness. I felt myself stiffening. I opened my eyes, still in the moment, as her fingers reached the waistband of my black underwear then slid inside, one hand softly touching and then kneading my balls, the other hand rubbing just the cockhead, using the precum oozing out of the slit.

I slowed exhaled. "Mmm ... that feels good."

One of her hands must have felt the lube in my pocket. She gave my balls a little squeeze, then freed that hand from my underwear and reached into the pocket, removing the tube and the handkerchief and putting them on the bench in front of me. One handed, she popped open the cap on the lube. Then she hooked her thumbs over the waistband of my briefs and jeans and in one swift move she pulled both down to my knees, baring my skin to the slightly chilly air.

"Hey! That wasn't ..." I said. "You didn't say anything about pulling them off ... uh ... aaah" My protests trailed off as she reached around me and squeezed some lube onto her hands and started rubbing it onto my balls and cockhead. Her right hand twisted expertly on my cockhead ... he - I mean she - knew how to masturbate, how to make my cock feel good, like it was being massaged and clenched by a warm wet pussy. She slowly slid her hand down the shaft, which by now was getting hard, while I groaned with pleasure, arching my head back.

She stepped closer, her jeans rubbing against the bare skin on my butt, and starting planting light kisses on the side of my neck. I tried to twist my head away - that wasn't part of what I'd agreed to - but she persisted. It felt good, actually. Really good. Fuck it. I tilted my head sideways a bit to give her lips better access. She nibbled on an earlobe, which felt surprisingly sexy, then resumed kissing my neck while one of her hands stroked my cockhead and shaft. I was pumping into the motion, fucking her fist.

"Yes," I said. "Mmm, don't stop."

She stepped away from me a bit so her jeans were no longer rubbing my bare butt, then I heard the whisper of leather on leather and a soft clink of metal.

Was he - I mean she - undoing her belt? I felt her wriggling around behind me, and suddenly her jeans rubbed against my skin as she pulled them off.

"No," I said. "Stop. I didn't agree ..."

She stopped kissing my neck. Her hand released my hard cock, and I thought I heard her try to pull her jeans back up.

"I didn't mean ... fuck, don't stop rubbing it ..."

A long pause. I thought about turning around to see the look on ... her ... face, but I didn't want to spoil the image of her in my head.

She sort of hugged me as she reached around me for the lube on the table. She took my right hand in hers, squirted lube on my hand, then slowly pulled my arm behind my back until it was touching her stiffening cock. Clit? Call it that. It was hot to my touch, the feel of the skin a familiar sensation - I'd jacked off often enough - but a slightly softer texture than mine.

She put her left hand on my shaft again and waited, the palm of her right hand hot as it held my right wrist.

I guess it's OK, I thought. It's just masturbating, except better, because I'll have a - girl's - hand getting me off.

I began lubing up her clit. Fair's fair, I thought. I agreed to jack her off too, after all.

She yanked my jeans down further, down to my ankles, resumed masturbating me with her left hand, while her right hand guided my hand up and down her clit's shaft.

We fell into a rhythm, both sensually stroking each other's shafts in time, up together and down in unison. She began pressing soft kisses all around my neck, left side, back, right side, as we both stroked and squeezed and humped into each other's hands.

She pressed up against me, and started thrusting so hard that my fist encasing her shaft was driven against my butt cheeks, her cockhead rubbing inside the cleft with each stroke.

It suddenly occurred to me - I'd somehow acquiesced in letting a stranger pull down my pants to my ankles, rub my cock, and get his dick - her clit? - in between my butt cheeks. How did I get coaxed into this?

Worse yet, it felt sexy. It felt really good. I was so turned on that I didn't protest when she pressed her clit forward and guided my hand so her clithead was rubbing against my hole. Or ... was she even guiding my hand? Was I the instigator rubbing it against my hole because it felt really sexy? It made my dick so hard. I was close to cumming. Or were we doing it together, and were both responsible?

Her clit against my hole must have felt good, because she took control, kicking my legs farther apart, as far as the jeans bunched around my ankles would allow. She grabbed my neck and pushed my head down against the rough wood of the bench. She took my hand off her clit and put it back on the bench so both hands were braced there as her clithead began bucking against my hole, ramming for entry past my tight sphincter.

"Please," I said. "Please n - mmmph." I grunted with pain midprotest as the pressure built on my asshole, her body thrusting and pushing trying to get inside me, and I wasn't sure she'd heard a "no", maybe all she'd heard was "please ... please" ...

I should have stopped her there, but I'd ceded control and was in no position to physically stop her. I was completely off balance bent over the table, with her hand on my neck and my ankles tied up from the jeans bunched around them, the pressure building on my hole ...

Her cockhead broke through my assring and ohmygod it hurt, a blinding pain, but I felt helpless to stop it, to say no, and maybe I didn't really want to say no, but either way I shut my eyes and took it, let her fuck me, let her shaft slide deeper and deeper inside me with each thrust.

She pounded into me, wordlessly fucking me like I was her bitch, roughly using my body like it was hers for the taking, or perhaps as if I offered it a gift for her pleasure - I didn't know what she was thinking because of our oath of silence.

She reached down and grabbed my left leg, pulled the jeans off it and lifted my knee up onto the table, spreading my ass wider, her cock slamming a bit further inside as she buried her shaft in me balls deep.

She was gasping for breath and grunting with pleasure, I was moaning with pain but also a bit of pleasure mixed in with it, finally admitting to myself I liked getting fucked by her.

"Fuck me," I heard myself say. "Cum in me."

"Ummmrrh" she grunted as she came. "Uhhr," she said as she shot more cum inside me. She kept making strangled noises as she kept cumming, until she was resting on my back and her cock gradually softened and slid out. She kissed my neck and breathed hotly into my ear, still panting to catch her breath, as I felt some of her hot cum trickle out of my sore hole.

She wordlessly took my cock in her hand, and with expert motions, twisting and rubbing while stroking the underside of my cock with her thumb, got me hard again with just a few strokes. I felt the cum boiling up out of my balls. A few strokes later I grunted and shot my load onto the bench top under me.

I felt the postorgasm sleepiness creep over me. Laying there with her cum inside me and my cum cooling on the wood pressing against my belly, I groggily wondered if I would see her again, or if she would wordlessly zip up when she'd recovered and walk out of my life ... or whether I'd want to be thoroughly sullied like this ever again, with her or anyone else.

It groggily occurred to me that the ad that had got me to this moment might have been fake, that the person lying on top of me might have lured me in with smooth lies. Or perhaps, details notwithstanding, the core was true - I had gotten the orgasm that had been promised, and more.

She kissed my neck and squeezed my ass, then gave me several playful spanks, and despite my warring head casting doubts, my heart leaped.