Van Life Sissy! Ch. 02

Story Info
Jenny goes for a hike in the park!
2.3k words
4.8
2.2k
6
Story does not have any tags

Part 2 of the 3 part series

Updated 03/16/2025
Created 03/14/2025
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

With Robert, the park maintenance man, satisfied and headed on about the business of his day, it was time for me to finish up my coffee and make some plans for the day.

I really do like Robert's regular morning visits. The anticipation of sucking his cock and swallowing his manly loads keeps my sissy motor running. I also really like knowing that I am the gurl that is keeping him satisfied. My being the sissy gurl he relies on for a regular release makes me feel more feminine and girly than any of the sexy outfits or makeup ever could.

As I was tidying up my camp, putting away my coffee pot, I was thinking that I could go for a hike. Just down the road from my site there was a trailhead with a map for the hiking loop along the foothills and back along the lake.

Of course, for a little sissy like me, the exciting part of this adventure is what to wear and who might see me in a girly outfit! I know I want to start with my hiking boots and pink lacy ruffle top socks! Oh and I will definitely give my legs a fresh shave. I thought pink panties with matching bra will work. Denim daisy duke shorts and white half shirt will top off the look.

As I was dressing I noticed that the low waistline of the shorts were definetly going to show off the tops of the lacy pink panties. I dont know why this situation ever concerns me anymore. I am sure, with the rest of my girly outfit, shaved legs and gereral sissy demeanor, no one is going to think for one second that I am wearing anything other than sexy panties. Sometimes I make myself laugh. I am never going to be viewed as a real man.

I locked up my van and headed off down the road to hike the loop. On my way down the road a motorhome was pulling in towards my camp. The gentleman driving gave me a wave as he passed. I was going to have a new neighbor when I returned it seemed. That could be fun!

As I approached the trailhead. I noticed a truck parked with a fisherman getting his gear from the back. We exchanged hellos as I passed. His deep gravely voice and tanned hairy forearms sent a little sissy shiver through me. When I had walked a short way further. I could not help but glance over my shoulder and sure enough he was still looking my way. He slyly turned his attention back to getting his fishing gear as i walked on. I figured he was probably going to be taking the trail down to the lake to do some fishing.

It was a beautiful sunny day. The hiking path meandered through the pine trees in the foothills of the mountains. I took the upper portion of the trail first. I wanted to return along the lake to see if I might run into that fisherman again.

When i reached the part of the trail that ran along the lake, I saw the fisherman up ahead. He was standing out on a little rock out cropping, casting his line out and reeling back in. He looked so masculine and hot with every motion.

As I walked near, He looked my way, smiled and said, "Well hello again!"

"Yes, Hello, we meet again," I said with a Smile. "Are you having any luck?"

"Not even a nibble," He said, along with a negative shake of the head.

"If I were a fish i would definitely give you a nibble," I said flirtingly

"What if you were NOT a fish?" He retorted with a smirk.

"I would probably still give you a nibble," I said with a huge grin.

I could tell from his body language that he was trying to get his fishing line reeled in and turning towards me to approach. I slowed my walk and was basically just walking in place waiting for him to reach the trail.

The man jumped off the rock and trotted over to the trail. He stuck his hand out and said, "Im Greg."

I put my little hand in his and replied, "Im Jenny, very nice to meet you Greg."

The contrast of his muscular hairy forearm next to my slender hairless arms, along with the way he gently shook my hand as if he was making sure he didnt hurt me, really put in perspective our differences. Greg was a real man and I am a sissy. I was there for his use, to pleasure him sexually if he desired. i was born to please men like Greg.

Greg was probably late forties in age. He was average height. He had very muscular calves and arms. He was wearing a ball cap, aqua blue fishing shirt and khaki colored cargo shorts. I was definitely into him.

Greg was looking me up and down and said he was about to give up on the fish and head back to the truck. "Would you like to walk back together?" He asked

"For Sure, that would be fun," I replied

As we walked and talked on our way down the trail, Greg was toting a small cooler and fishing pole. I would laugh at his jokes, smile and give him flirty touches to the arm. Greg would respond with his own flirty touches to the small of my back and hip as if he was guiding me along. His touches would graze my lacy panties where they perked out of the top of my shorts. I felt like I was foating along beside him. I was feeling feminine twinges running through my body like electricity. My walk becomes ultra feminine, My back arches a little more and I become hyper aware of the way my panties feel against my pulsing boi pussy. I know what my sissy duty is. Now it is time for me to give this man the pleasure and release that all men need.

"You know, I have a few beers in my cooler and there is a picnic table up here on the left," Greg said hopefully

"I like the way you think Greg," I playfully replied

As we approached a small trail heading off to the left, Greg guided me in that direction with his hand on the small of my back. Hidden in the trees we found a picnic table under a small metal cover. "Here we are," Greg said as he held my hand to help me up on the concrete patio.

Greg sat up on the table top and cracked open a can of beer and handed it to me. He then opened a beer for himself, he took a big swig, sighed and said, "What a beautiful day to be out here in nature."

Greg was sitting on the table top and I was standing in front of him. I took a sip of beer and moved in close to Greg to sit my beer down. I ran my hand across his hairy thigh as I moved back. I then felt Greg's arm wrap behind me and keep me in close. I rested my hand on his hairy thigh and leaned into him. Greg leaned into me and we kissed.

There I was, nuzzled up to this man. I was in between his legs, with hand on each of his hairy thighs, looking up and making out with him. The cool beer on each of our tongues added to the excitement. Greg tasted amazing and the anticipation of tasting more of him was driving my sissy hormones wild.

As Greg's tongue swirled around mine, I felt his hands exploring into the back of my shorts. With one of his hand inside the back of my shorts, Greg's other hand was cupping my ass cheek and his fingers crawling towards my quivering boi puss. My own hands seemed to have a mind of thier own. They were moving from his hairy legs to the growing bulge in his shorts and up under his shirt feeling his hairy chest and stomach.

I made quick work of the buttons on Greg's shirt and flung it open exposing his gloriously golden hairy chest. I buried my face in him, licking and kissing as my hands furiously worked on getting into Greg's shorts. The more his cock swelled and hardened the more difficult the button became to open. Greg leaned back resting on his arms. The head of his cock pushed its way above the band of his shorts. I freed the button and my hand grasped his hard rod.

The frantic noise and axienty in my head all instantly calmed. I kissed my way down his hairy stomach and took his rock hard cock into my mouth. A warmth and peace rushed into my body as Greg let out a little moan of approval. I held my mouth around his shaft for a few seconds, just just enjoying the moment.

Greg's cock was large, eight plus inches and had girth. The shape of Greg's cock fit so well with my mouth. It seemed as my mouth was designed to wrap his cock. I slowly moved my mouth up and down on the head of his hot meat. Then swirled my tongue around the flaring head of his beautiful member. I was licking his sexy shaft from balls to tip and back as we struggled to get his shorts and undeewear the rest of the way off.

I told Greg that, in my back pack, I had a towel to put on the wooden table to make it more comfortable for him to sit. Greg stood and dropped his shorts as I grabbed the towel and arranged it on the table. I also took the opportunity to get a tube of lubricant out and placed it on the table as well.

As I was spreading the towel on the table, I felt Greg's hands on my waist. He was behind me and his hands were now unsnapping my shorts as I pressed my body back into his. I could feel his hard cock against my back as i wiggled and writhed my body to help him lower my shorts below my hips. My shorts dropped to my ankles. Gregs hands were roaming my body and my hands reaching back to feel his. My face was nuzzled up under his scruffy beard. I felt his hand on my back pushing me forward onto the table. As my feet came off the ground Greg worked one side of my shorts over my hiking boots leaving my shorts dangling from the other ankle.

My upper body rested on the table as Greg physically moved my legs where he wanted them. My legs were spread and my body was ready for his use. I felt my hole tingle and twitch as I heard the snap sound of the lube cap opening. I felt Greg move my panties aside. I jumped a little as the cool lube hit my hole and his fingers easily worked into me. I felt the tip of his cock pressing against my throbbing hole. I relaxed my entire body and his rock hard cock pushed through. He then easily slid all the way inside of me. I could feel his pubic hair tickling against my smooth sissy skin.

This man, I had just met 20 minutes ago has his hot cock burried in my little pink hairless boi pussy. I lived for these moments. I was in sissy bliss as Greg pushed his cock in and out. I writhed in rhythm asjusting my body so that the head of his cock would glance off my P spot with each push.

Greg continued fucking me into a femmed out stupor. I had one foot on the ground and the other leg lifted up with a foot on the bench. I was pushing back into each of Greg's thrusts. Our bodies were slapping together. Greg was grunting and thusting. My clitty was flopping in my panties and dripping cum.

Greg's fucking grew more aggressive. He was slamming into me when he grasped my shoulder with one hand and my hip with the other. Greg's grip tightened. He pulled my body hard back towards him and grunted the words, "Im Cumming!" with three or four more thrusts he was unloading deep inside Me as He barked, "Thats a good sissy, take that cum!"

"Oh Greg! Oh God! Soak my pussy. I feel your cum so deep inside me!" I moaned in a thankful tone.

With heavy breathing, Greg's grip on me loosened as his ram rod slid out of me. I fell forward and rested my entire weight on the picnic table. Greg was leaning on the table as well and I could feel his hairy legs against my smooth shaved body.

"Dang Jenny, that was hot," Greg said as he was catching his breath.

"Oh my god I needed that," I mumbled from my contented position on the table.

Seeing that Greg was gathering his clothes and getting himself dressed and together, I got up and started to do the same. My legs were quivering and the occasional dribble of cum would stream down my inner thigh. I used my towel to take care of that and adjusted my panties back up over my girly hips.

"You have a damn fine ass Jenny," Greg exclaimed as he watched me adjusting my panties.

I just wiggled my ass around, smiled and batted my eyes at Greg in response.

Greg and I sat another few minutes finished our beers, laughed and lamented at how our days had turned out. Of course Greg had planned on fishing and ended up fucking a sissy. I had to pretend that my hike turned out differently than I planned. But I knew that I had set out to find a man to fuck me, found Greg and reeled him in!

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymous9 days ago

Oh, Jenny, you are my dream girl, just the type of babe i need, the story was hot and sexy, 5 stars! Thank You Jenny!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Sissies Love Truckers Ch. 02 After Jenny’s trucker rendezvous, the fun continues!in Transgender & Crossdressers
Ride it Like You Stole it Amy feminizes her brother and turns him out for money.in Transgender & Crossdressers
Lunch Break Quicky A stranger fucks Kristy's ass on his lunch break.in Transgender & Crossdressers
Unlearned Lesson Boy bumps into an old 'friend'. She wants to catch up...in Transgender & Crossdressers
Preparing Me for Him My man waited so long for me to accept my destiny.in Transgender & Crossdressers
More Stories