I woke up the next day and in my early morning grogginess wondered if yesterday was just a dream. It was all so ‘Dear Penthouse’ (is that still a thing?) Getting caught in a secluded part of the woods by a woman while I was jerking off. To top it off she then proposed that we both meet up and do… what?
The scenarios kept running through my mind. Were we going to watch each other get ourselves off? Were we going to give each other instructions on how to touch ourselves to get off? Would we have free reign to bring the other person to orgasm? She never did say what she had in mind, I guess that’s what her plan was, to keep me guessing until we met up.
I had breakfast and then packed my bag for the hike. This time I was bringing some lube. I also packed a blanket and a few snacks and an extra water bottle, I guess I was trying to distract myself by thinking I was going for a picnic. I left the house, tossed the bag in the passenger seat, and drove off for my rendezvous in the woods.
During the whole time driving I was asking myself, ‘What did she have in mind?’, ‘What did she look like naked?’, ‘Was this going to end up with my face on a milk carton?’ That last one almost killed my mood, but I was determined to experience this … whatever it was, so I drove on.
Speaking of mood, I was pretty sure she was being honest when I asked her not to touch herself and she agreed. I wanted her to be craving it, to want it more than the day before, whatever ‘it’ was. I did the same thing and refrained from jerking off at home. I could have easily brought myself off before going to bed. I was very horny with my thoughts on what had happened the day before and what could happen today. I was looking forward to another explosive release in the forest and I was pretty sure she was too.
I arrived at the parking area at about the same time as yesterday and saw that I was the only one there. I got my things together, locked the car, and headed out on the trail to the spot without waiting for her to arrive in her car.
Just like yesterday, I didn’t want to ruin the mood or expectations with casual conversation. I wanted the excitement and expectation to build up as each of us walked alone to the same spot as yesterday. Each of us played out in our minds what was going to happen.
When I got there I brought out the blanket and spread it out on the same rock I was sitting on yesterday. I had a snack and some water while I waited for her. It wasn’t too long before I heard footsteps coming from the trail.
“I don’t know if I should be glad or disappointed that you didn’t start without me,” she said as she came into view.
“I didn’t know if you would show up so there was no need to start early,” I replied.
“I had every intention of showing up today but I was worried that you might have backed out, worried that your face was going to wind up on a milk carton,” she said.
“That’s … kind of funny,” I said.
“What, the potential of me being a serial killer?” she asked.
“No. On the way here I was thinking that one of the possible outcomes of today was my face ending up on a milk carton,” I told her.
“Hmm. Interesting coincidence,” she answered, “Regardless, after agreeing to your demand yesterday …”
“Demand!?” I said a little offended.
“Okay,” She rolled her eyes as she continued, “request; I was committed to showing up. Last night I was going crazy remembering you playing with yourself.”
“So, you didn’t touch yourself at home?” I asked.
“No, I didn’t. It was difficult, but it was the least I could do for you after watching your show without you knowing. It took a long time to fall asleep last night,” she added.
“It was never intended to be a show,” I said defensively, “It was only a show because you’re a Peeping Tom. Uh … what is the female version of the name ‘Tom’?”
“Irrelevant … so …” she clapped her hands and rubbed them together, “… let us see if we can release some of this pent-up frustration, shall we?”
“How do you want to do this?” I asked.
“I’ve been thinking about that long and hard, pun intended,” she said playfully, “Let’s set some ground rules first.”
“Okay. What do you have in mind?”
“First off, no touching each other. Second, we can do our own thing but we can also direct each other to do something.”
“Oh, a little dom, sub action?” I interjected.
“No, not like that … well … not exactly like that,” she clarified and then continued, “Third, we have to cum together.”
She paused for a moment, “That’s all I got. Is there anything you want to add?”
“Wait, as a woman, who can be multiple orgasms, you’re only going to cum once?” I said.
“Again, I thought about it long and hard,” her eyes drifted towards my crotch, “and again it’s the least I can do for you after watching your sh …,’ she paused a moment, “watching you,” she began again, “jerk off. Plus, it’s a bonus for me of having a big orgasm instead of a few smaller ones.”
“That’s very sporting of you.”
“I’m happy you think so,” she replied.
“If there’s nothing else then, let’s get started,” I said as I took off my jacket.
“I do like a man who’s eager,” she said as she started to do the same.
We started from the top down. We pulled off our shirts, she had the added task of taking off her sports bra. She had an amazing set of tits. I mean, I would have been pleased with whatever they looked like but I was a lucky man that day. The size and shape were exactly what I loved seeing and I commented on them.
“Those are fantastic.”
“They’re a matched set,” she said, grabbing both of them and squeezing them.
I sighed a bit and said, “That’s making it hard for me to obey rule number one.”
“I can see it’s not only hard for you but it’s making you hard,” she said as she nodded toward my crotch, “But I guess that’s the goal.”
Next came our jeans and underwear. She had trimmed public hair which I prefer more on a woman than her being fully shaved. I also trim my public hair, being fully shaved is a bit of a chore so I don’t do it, but I dislike having a full bush.
I was enthralled by her trimmed pussy so I was a little startled when she said, “I see you’ve laid out a blanket for us.”
“Yep,” I answered, “Might as well be comfortable. It’s not quite as warm as yesterday but I think we’ll be warm enough sitting here.”
“So thoughtful,” she said.
We sat beside each other, facing the sun. I was semi-erect when I sat down so I started by grabbing my cock and fondling it a little. I looked over at her and admired the shape of her breasts and her athletic body. She was truly beautiful, and the sight of her combined with my stroking made me fully erect in short order.
She started by running a hand down her stomach, pausing slightly over her clit, rubbing it lightly, then cupping her crotch, completely covering her pussy. She then continuing down her inner thighs and then back up to her pussy. She ran her fingers along her lips, top to bottom to top again, pausing on her clit to rub it in a circular motion.
I could feel my cock getting harder while watching her. I was stroking slowly, running my hand along the full length of my shaft, from the base to just over the tip of my cockhead and then back down to the base again.
I looked up at her face and noticed that she was looking at the cock in my hand. She then looked up and into my eyes. We stared into each other eyes for a few seconds while we played with ourselves. I adjusted my gaze down her body, I watched her breasts for a while, seeing them move slightly as she breathed, captivated by how perfect they looked.
I continued down her body towards her pussy. I could see that her fingertips were wet. Seeing her wet fingers reminded me that I brought lube, so I stopped, stood up, and went to my pack to retrieve it.
“Oh. That was unexpectedly sexy,” she said.
“What?” I asked.
“Seeing your cock bounce as you stood and walked, then watching your ass as you kneeled. Mmm. Delicious,” she said.
“Anything else you want to see while I’m up?” I asked teasingly.
“Now that you ask,” she said excitedly, “come and stand in front of me and keep stroking your cock like you were before.”
I walked over to stand in front of her with my cock pointing directly at her face. I grabbed my cock again and as before I ran my hand from base to just over my cockhead, slowly.
“Mmm, just like that,” she said.
“What do you like about that?” I asked.
“I love seeing your head emerge from your hand. Seeing the glans stretching as the head slowly exits your hand. Then watching it disappear into your hand again,” she paused and then added, “I guess that’s what my pussy sees when I’m fucking,” and smirked a little.
“Speaking of seeing pussies, I want to see yours. Spread your legs,” I told her.
She leaned back a bit, propping herself up with one arm behind her, and spreading her legs.
“Wider,” I told her.
She shuffled closer to the edge of the rock and spread her legs wider and leaned back again. I saw that her pussy was glistening now. She continued running her fingers along her pussy and rubbing her clit in a circular motion.
Then she started to penetrate herself with one finger. She slowly moved her finger in and out. Little by little she pushed it further and further into herself until she was taking the full length of her finger. I’m sure it was a little show for me because she was watching me watch her.
We continued like that for a minute or two, me stroking my cock directly at her, she was watching it and moving a finger in and out of her wet folds. I remembered that I had the lube in my hand so I stopped stroking to open the bottle and squeeze it out onto my shaft. I closed the bottle and tossed it onto the rock beside her.
“I don’t need that,” she said.
“Ya, I can see that,” I replied, “It wasn’t for you. I just needed to put it down where I could get to it again.”
I then spread the lube all over my cock and started stroking again. The sound of the lube as I ran my hand up and down the length of my shaft made a sexy, squishing sound. She too noticed the sound and said.
“I bet that’s what my pussy hears when I’m fucking.”
“Or jilling,” I added, “Let’s hear it.”
I stopped stroking so that I could listen to her finger moving in and out of her pussy. It wasn’t as loud as what was coming from my stroking but it was the same sexy, squishing sound.
I was just about to tell her to put a second finger into her pussy when she did that without me asking. The sexy, squishy sound became a little louder. Her head lulled back and her eyes closed a little when her second finger entered her pussy.
“It feels that good, eh?” I asked her.
“Yes, and it’s feeling better all the time,” she replied, “How about you?” she asked.
“I don’t mind stroking dry but the lube helped make it feel better,” I told her.
“You’re not getting close, are you?” she asked quickly.
“Nothing I can’t handle,” I reassured her and started stroking again.
I stopped stroking the full length and grabbed the base of my cock with my other hand and started to rub my cockhead with my lubed-up hand. That built up my excitement rather quickly so I couldn’t do that for long. I took both hands off for a bit to come down from the high of excitement and then started again with my lubed hand.
She was now thrusting her fingers deep into her pussy. I was fixated on her crotch, watching her fingers slide in and out of her. When I looked from her pussy up to her breasts, I noticed that her nipples appeared to be rock hard.
“Pinch your nipples,” I demanded.
She laid down on the rock and with her free hand, she caressed her left tit and moved her hand to pinch and pull the nipple a little. That made her moan a little.
I asked, “How about you? Are you getting close?”
“I’m pacing myself. I can do this all day,” she said confidently and seductively.
“A Steve Rogers fan I see,” I said.
“Yep. You saw how big he got after the serum treatment. I like to imagine that some parts of him got bigger than others,” she said with a gleam in her eye, she was most likely thinking of a naked Steve Rogers standing at attention.
“You might make me self-conscious,” I told her.
“You’ve got nothing to worry about. Your cock is great and Steve is just a fantasy,” she added.
That made my heart flutter a bit. I was hoping that she was as turned on looking at me as I was while I looked at her. I started stroking a bit faster and I cupped and pulled my balls a little. That caused my head to roll back and my eyes to close.
I told her, “I’m going to sit down beside you again,” and proceeded to do so. I leaned back a bit which made my cock stand straight out and just sat there for a bit, hoping that she’d enjoy the view. Like I said before, I believe that one of the sexiest images in the world is an erect cock sticking out from a man’s body and I hope she felt the same way.
As I had hoped she sat up a bit and looked at my stiff member.
“Oh boy. I’m kind of regretting rule number one. I’d love to touch that thing or put it in my mouth,” she said as she gazed at my cock.
“Is there anywhere else you’d like me to put it?” I asked with a sly smile.
“Mmm. You’re not making this easy” she replied. She sat up completely, picked up the bottle of lube, opened it, and squeezed some out, letting it drip onto my cockhead.
“Rub it in,” she commanded.
I used my fingers to rub it around my cockhead. She dripped a bit more onto the head and I worked it along the full length of my shaft and started stroking again.
“Faster,” she said.
I stroked faster.
“Faster,” she said again almost commanding me.
I sped up the speed of stroking and started groaning. The lube on my cock made my hand glide up and down easily. The feeling of my hand running along my shaft combined with her watching me was bringing me closer to cumming. My eyes closed, my head rolled back, and I started to breathe harder as I held back my orgasm, I didn’t want to break the third rule.
Thankfully she said, “Stop!”
I stopped stroking, taking my hands off my cock, taking deep breaths, and trying to regain control of my excitement.
“Oh, dear. How close did I bring you?” she asked in a seductive voice.
I didn’t answer but turned to look at her and said, “How mad would you have been if I broke the third rule?”
“I would have been miffed. We might have had to do this again another day,” she said with a little resentment in her voice.
“I don’t think you could hold back from touching yourself for that long?” I said to her.
“Oh, I would have brought myself right here,” she boldly said, “It’s just that I’m looking forward to cumming while I watch your cock and balls twitch when you shoot your cum. That will make my orgasm even better. I love watching men cum. There’s nothing sexier than a hard cock and I think it’s even more exciting watching it shoot cum.”
“We’re on the same wavelength. I’m looking forward to your body twitching and your breasts heaving and shaking. Oh man, I might lose my load just thinking about it.”
“Hands-free, eh?” she asked with a gleam in her eye.
“That would be a disappointment,” I told her, “It’s called a ruined orgasm for a reason.”
“I think I might be able to help you there,” she replied enticingly.
I was intrigued. I’d have to follow up on that thought later, now it was time to finish this … whatever it was.
“Your turn. I want you to finger yourself again” I instructed her.
She did as she was told and spread her lips apart and held them like that for a bit, kind of showing off for me, then she stuck two fingers into her pussy.
I picked up the lube bottle and said, “Pull them out. I’m going to put lube on them.”
She pulled them out and I squeezed a generous amount onto them. She began to stick them back into herself, pausing before entering to rub some on her clit, and then continued to plunge her two fingers into her pussy.
“Mmmm,” she sighed and closed her eyes. Her head tilted to the side and she left her fingers deep in her pussy for a bit.
“I didn’t tell you to stop,” I said, “Keep going.”
She started to move her fingers in and out of herself in a continuous motion slowly increasing in speed. The sounds of her fingers sliding into her pussy were so sexy, it kept me hard but I grabbed my cock again and started stroking slowly.
“Rub your clit” I said.
She pulled her fingers out and ran her fingers over her clit in a circular motion. She then alternated from fingering herself, thrusting her fingers in and out of her wet pussy a few times and then extracting them to rub her clit. Eventually, she started fingering herself with one hand and rubbing her clit with the other. Both hands moved faster and faster. Her breathing became deeper and heavier.
“Grab my tits!” she blurted out.
“But … the first rule,” I said.
“Fuck the first rule. Grab my tits!” she said insistently.
I kneeled on the blanket and with my free hand, I reached over and grabbed her breast closest to me. She moaned as a caressed them.
“Oh yes! That’s the stuff,” she said as her eyes closed.
What incredible breasts she has. I kind of lost myself in the moment of grabbing her tit, feeling her smooth skin in my hand, the soft, fullness of her breast, the texture as I rubbed my fingertips around her areola a few times, her firm nipple as I rubbed and tugged it.
I then did the same thing to the other breast, giving it a gentle squeeze and ending with a tug of her nipple. I moved my hand across her chest back to the other breast. I was lost in the moment, it was so sexy. Two naked people in the forest playing with themselves, coming closer and closer to orgasm.
She was moaning loudly now. Her fingers slid in and out of her pussy, the fingers on her other hand rubbing and gently patting her clit. Her breathing was getting heavier now. I decided to push her boundaries a little and bent over and put my mouth over a nipple and sucked it.
Her eyes shot open and she gasped. I shifted my gaze to look into her eyes and saw that she was looking into mine. Then she silently mouthed, “I’m close.”
I didn’t want to break the third rule, so I released her nipple from my mouth, sat back, and started stroking faster. I started breathing faster as I watched her fingers move faster in and out of her pussy, feeling my hand move up and down my cock.
We started to match speed and intensity in masturbating, our breathing getting heavier, and our hands moving in rhythm. As I stroked down my shaft her fingers plunged into her pussy. As I stroked up, her fingers moved out.
I looked up along her body, lingering on her breasts, watching them rise and fall as her chest heaved, I was mesmerized by their motion. I noticed she was looking at me, trying to look into my eyes so I adjusted my gaze to look into hers. We locked eyes. Each of us saw the pleasure build in the other face, watching our faces slowly change expressions to ones of pure bliss.
“I’m going to cum” I announced.
Her fingers moved faster so that she could reach climax when I did and then suddenly, I orgasmed. Just like yesterday, my cum shot out from my cock and landed in the dirt. I grunted as I shot another load and started gasping as the pleasure overcame me. Beside me, I heard her almost squeal as she started to cum.
I looked over at her, to watch her body react to the waves of pleasure washing over her. Her eyes were closed, her mouth was opened as she breathed hard, gasping, her body shuddered as her legs closed tight, squeezing her hand and fingers in her pussy.
As her body was shaking from her ongoing orgasm her breasts shook. Watching them shake and jiggle brought me another wave of pleasure and I shot one more load onto the ground.
We both sat there for a few moments, panting, recovering from our orgasms. I looked at her and she at me. Our chests rose and fell with each breath and I couldn’t help myself. I reached over and cupped the back of her head with my free hand and kissed her. She didn’t pull away from me which I took as a good sign. We kissed passionately for a few moments. When we stopped kissing we put our foreheads together, still trying to catch our breath.
“You really broke the first rule there,” she replied.
“I didn’t hear you complaining. In fact, I believe I heard the opposite of a complaint,” I said teasingly.
“You got me there. What do you say to going back to my place and break the first rule some more?” she asked.
“That’s music to my ears,” I said to her as I kissed her again.