Blind Date Handjob

"I really think you're going to like this girl," Jean said. "She's like you, just looking for fun, nothing serious. She's not a slut or anything, but she's definitely horny. You might even get a little action."

Jean was referring to a girl named Amy she was trying to set me up with. It had been months since I'd been laid last and although part of me wanted to get back in the game, I was also a tad nervous about it. "I don't know," I told Jean. "Dates are always so uncomfortable. I'm not sure if I'm up for it."

"Just wait til you see the ass on this girl. You wouldn't forgive yourself for walking away from that. Beside, she's into all the same shit as you."

Jean wasn't kidding. After a few days of texting back and forth, Jean and arranged to go on a hiking date. I knew of an amazing swimming hole that was well off the beaten path. It seemed like a great place to take Amy, whom I'd learned was very into hiking and outdoorsy stuff.

I stopped by to pick her up early in the morning. I stood at her door anxiously waiting for over a minute before it opened, and when it did, I immediately knew I'd made a good decision. The girl was an absolute sex bomb. She was tall, maybe two inches shorter than me, and I'm six feet all. Her hair was long, straight, and dark brown. Her face was pale, and I believe she may have been Jewish. The loveliest part of the front of her body were her hips that swung out far from her slender stomach. I was never much of a breast man, which worked out fine because Amy's were small for the size of her body. For clothes she wore a teal tank top with skin-tight yoga pants and sandals. She was well kept, but didn't really have any noticeable make up on, which was good since we were going hiking.

However, judging by the clothes she wore, I'm not sure she really comprehended the difficulty of the route I was taking her on. I was about to suggest wearing something else, but I couldn't stomach the thought of no longer getting to see her phat ass in her slutty yoga pants.

When we got on the trail, it was abundantly clear that I'd made the right call. I told her to walk in front so she could set a pace she was comfortable with, but really I just wanted to watch her voluptuous ass jiggle from side to side. Conversation with her came very naturally. She was outgoing and had little shame, telling me things about herself I wouldn't have expected to hear on a first date. And she was keeping up just fine on the hike to boot. She seemed to really enjoy walking through the woods and searching for wildflowers. "Ooh, look at this pretty little one," she said as she bent completely over.

I glued my eyes to her ass. The material in her pants was so thin, that as it stretched out I could see right through it. Either she had on a super skimpy thong or nothing at all under her pants because when she bent over I could clearly she her bare ass through the yoga pants. This caused me to get an erection which was difficult to hide in the basketball shorts I was wearing. But Amy was oblivious to that situation, instead focusing on the flowers.

We walked along for another half hour before stopping for her lunch. I'd carried all the food in my backpack. The pack was heavy and caused me to drench my shirt in sweat. I took it off and threw it over a tree branch to air out. "That's what I'm talking about," Amy said. "You have a really nice body."

I blushed. "Thanks. Yeah, it's not feeling so great right know, though. My shoulders are a bit sore from lugging that backpack."

"Would you like a massage?" Amy said seductively.

"Seriously?"

"Sure. I've actually been taking a massage class, so I enjoy getting all the practice I can."

My heart, mind, and cock were all really loving the massage idea, but I wasn't without a few reservations. "That sounds great, but are you sure? I'm all sweaty and everything."

"Don't worry honey, you're not sweating, you're glistening."

Already leaning against a tree, Amy had me come over and take a seat in her lap. She deeply dug her fingertips into my shoulders. Then she moved them down my body, working out the kinks in every muscle in my back. While working on my lower back she gently blew icy breath on my shoulders. Her hands went lower and lower until they were under my briefs and on my pelvis. My cock was fully engorged. She rested her head on my shoulder and nibbled on my ear. "Relax," she whispered. "Let me pleasure you."

She grabbed my shorts and briefs by the waist band and fought to pull them down. I had to shift around and help her a bit. She didn't take them all the way off, but left them lying on top of my knees. My dick was shooting straight up in the air as Amy massaged the mound right above it and licked my ear. Then with her index finger she traced a line on the underside of my cock from the bottom all the way to the sensitive head.

I was fully expecting to get jacked off, but the next thing I knew Amy's hands were working there way back up to my shoulders. She used a number of different techniques on my upper back until her hands finally started slithering down again once more towards my pelvis. She kissed the crease between my shoulders while I closed my eyes and breathed deep. I felt her left hand cup my tightened balls. She squeezed them like she was juicing a lemon. Then I felt her right hand gently caress my penis. She took it in her palm, and ran her hand up and down it like she was playing the flute. I tried to concentrate my breathing and meditate. I hadn't been touched that way by a woman in a while, and I really didn't want to ejaculate prematurely.

Having room to spare, Amy put her left hand on my cock also. She jerked me up and down with her left hand while using the right hand to sweetly pet the tip of my penis. While stroking me off, she bit, kissed, and sucked my neck. I kept my hands at my side and simply let her give me all these pleasures. "Does your body feel better," she whispered in my ear.

"Much better. Better than better."

"Good," Amy said as she took her hands off my cock. "Then we can have lunch and get moving again."

All and all she'd probably only jacked me off for about a minute, but it had felt like an eternity. I urged her to keep the massage going, but she would have none of it. She was hungry after all. We ate lunch at a spot with a great mountain lookout. We snuggled up next to each other on a Mexican blanket and had a normal conversation. Neither of us made any mention of the fact that just ten minutes prior Amy had been cranking my cock.

When we were done eating we just lay there and gazed into each other's eyes. Without a word spoken, we started to kiss. I put my left hand on the outside of her shirt over her breast, and she didn't object. My other hand was grasped in hers. With her hand in mine I lowered it down the front of my shorts, until it was resting on my hard cock. She stroked my little fellow just twice before removing it. Her hands were running up and down my body, but just not on the one place I wanted her focusing on more than any other.

During a lull in between kisses I asked, "Would you like a little desert?"

Amy looked at me coyly. "Why, what ever do you mean by that?"

"I think you know what I mean," I said as I put my finger on her lower lip. "Do you want to taste it?"

She sucked my finger teasingly. "Right now I'm full, but maybe later."

We kept hiking along. It was very difficult to concentrate on the trail ahead when all I could think about was having my dick down Amy's throat. I continued hiking behind her. She was going at a good clip, and didn't relent from letting her ass sway back and forth. Eventually that big ole ass got snagged by an errant branch. The branch took hold of her yoga pants, and as she tried to pull away, the pants ripped. This left a good sized hole right over her left butt cheek. She was upset about ripping the pants, but I was plenty happy about my new and improved view.

We got to our destination mid-afternoon. It was a beautiful swimming hole flush with crystal blue waters, and lined by tall conifers. Before hiking I hadn't mentioned to Amy that we might be swimming. "I hope you brought a bikini," I said.

"Are you kidding? We're in the forest," she said as she took off her top. She had nothing on underneath.

Next she peeled down her ripped yoga pants, revealing an itsy bitsy pink thong. Her back was to me and the view was sensational. The thong came down next, at which point she turned to face me. My eyes were drawn to the narrow landing strip above her pussy. She wanted to watch me as I undressed. She looked a little disappointed when she saw my cock wasn't yet hard for her.

We held hands and ran into the water together, both flopping in at the same time. The water was cold but not altogether unbearable. We swam around for a minute or two before winding up in the shallows in each other's arms. The water was only up to our knees, and the mid day sun felt great beating down on our shoulders. As we embraced, we kissed and explored each others' bodies. My hand wound up on her wet clam. I put my palm around it, and let my middle finger slide right down the crease. I slid it back and forth a couple times, just like I was running a credit card. Then right as she darted her tongue into my mouth, I inserted two fingers. The warmness of her tight snatch was in great juxtaposition to the cold, mountain water.

Getting hornier and hornier, Amy took my penis between her fingers. It was small and flaccid from the cold water. She began giving me a tug job, but my cock was numb from the cold water, and refused to grow. Trying something new, Amy took my entire package between both her hands and started kneading it like it was dough. I was sprung in no time, with my big salami pressed up against Amy's leg. She jacked me up and down as her tongue dashed in and out of my mouth. I continued sliding my fingers into her slot until she finally pulled my hand away. "Why don't you turn around for me," she said.

I obliged, and stood with my back facing her. She placed her hands on my shoulders and began to rub me down, working all the aches out of my body. It didn't take long before her hands reached my cock, the part of my body that needed the most loving. She let my shaft glide back and forth through her right hand as she reached between my legs and up towards my balls with the left. She gently tickled my balls while pleasuring my dick with her other hand. Then while I was in a state of complete bliss from getting cranked off in an idyllic swimming hole, Amy caught me off guard. She'd taken her hand off my balls and slid it up my ass. She tried to insert her finger in my cornhole, but I pulled away before she had the chance. "What's the matter?" she asked. "Afraid to try something new?"

"I'm not comfortable having anything crammed up my ass, not even a finger."

"I like having my ass played with," she responded. "I think you'd like it too if you were willing to give it a chance."

I once more declined, and she kept working my package for another minute before abruptly stopping. "I'm getting cold," she said. "Lets go lie in the hot sand."

Heeding her advice I set the blanket out on a nice sandy beach, and we both lay down, still completely naked. We cuddled up with her ass right up in my crotch. I gently reached around and toyed her clit with one hand, and her nipples with the other. Eventually we fell asleep in this very position.

I awoke to what was becoming the familiar feel of my dick being masturbated by Amy. From a full day of being teased a tremendous amount of cum had built up in my balls, and the head of my penis was so swollen it look like it might burst. I opened my eyes and made direct eye contact with Amy. "Do you like waking up to me jacking you off?" she asked, right before sliding her head down to lick my nipple.

"You stroke me so good, girl. I love it," I said running my hand through her hair. "But I think it's time you suck me."

With those words I tried to force her head off my nipple and down towards my big, pulsing, horny cock. Unfortunately she resisted. "Don't just assume you're gonna get your dick sucked today," she said. "That you have to work for."

She then spun around so and sat on my chest so that her ass was facing me. In this position she wrapped my cock up with two hands, and started pumping the thing like she was filling up a bike tire. As she shellacked my dick, she rhythmically bounced up and down, giving me a tremendous view of her ass cheeks rippling on my chest. "That's it girl," I said. "Crank that big dick. There you go. Really fucking crank it."

"Ooh, yeah?" she moaned. "You gonna cum for me baby? You got a load for me?"

"Pump it, babe. Fuck yeah!"

She kept furiously stroking me off with both hands, taking me right to the cusp before changing positions to put herself on all fours. With her ass right in front of my face, I finger banged her as she kept whacking my whale. Amy moaned loudly, and with her left hand she reached behind to put her hand on top of mine. She guided my fingers out of her cunt and put them on her anus. "That's the spot," she said, essentially giving me permission to ravage her phat ass with my fingers.

I'd never fingered a girl's asshole before, so I was conservative at first, slowly banging her with just one finger. Her body, including her glorious ass kept convulsing and shaking as I finger banged her. "Faster, deeper," she said.

I did as she said, and for her part she gripped my dick so hard I thought she might never let it go. I'd never had my knob polished like that before. Just about ready to finish, I stuck another finger in Amy's ass to see how fast that would get her to pump my cock. It had the desire effect, it not only did see start jacking my dick even faster, she got so caught up in the moment that she licked my engorged mushroom tip a couple times, just like she was trying to get to the center of a tootsie roll pop. But before she began to fully suck me off, she came to her senses, and took her tongue and hand off my cock. "Get on all fours," she said to me.

It struck me as an odd request, but I did as I was told. I felt very vulnerable having my ass up in the air like that, and hoped she wouldn't try to finger me again. I was pleasantly surprised when she started licking my sweaty balls from behind. While she pressed her tongue against my scrotum, she reached around my thigh and grabbed my big, dangling cock. "I'm going to milk you like a cow," she said while taking a break from french kissing my ball sack.

She tugged on my dick, alternating between both hands like she genuinely was milking a cow. "I grew up on a farm," she said.

"You gonna drink my milk?" I asked.

"Maybe," she said, "But I want to taste something else first."

Without warning she put her tongue right in my ass and started rimming me. It tickled like hell, and for as satisfying as it was too have a sex goddess cleaning out my asshole on a first date, I wasn't comfortable with it, so I pulled away. Amy just laughed, then tackled me down. Lying side by side we kissed an engaged in mutual masturbation. She wrapped her leg around me and brought me in close. My rock hard dick was pressed right up against her hot snatch. With her slender fingers, Amy rubbed me down, continuously putting the edge of my cock on the precipice of her opening, but not quite inside. My balls were getting tighter and tighter to the point where they couldn't hold any more cum.

Acting fast, I rolled over and positioned myself so I was straddling Amy. She immediately put her hand back on my cock and stroked furiously. She knew what was about to happen.

We were making strong eye contact, and she winked at me. That did it. I erupted like a volcano. My first squirt shot about two feet over Amy's head. The next one drenched her face and breasts. It was like I was peeing semen. For the life of me I couldn't stop cumming. I was drenching every inch of Amy's torso. I was grunting loudly, and Amy started laughing hysterically. "Holy shit!" she said between cackles. "I really got you off. I've never seen someone cum like that before."

And it still wasn't over. I kept squirting and squirting. While still spouting, I climbed off Amy and crawled next to her face. I put my still hard member right on her lips. "Will you suck it for me?" I asked.

She jerked my dick a bit while keeping it on her lips, then moved it away. In this time I shot a good sized load on her cheek. After removing my cock, I had one more spurt that landed on Amy's shoulder. Seconds later I rolled over and passed out.

I awoke to Amy straddling me. She had her tiny pink thong and tank top back on. "We should get moving," she said.

She gently stroked me as I lay there coming to. Slowly I got up, in more ways than one, and then got dressed. Amy didn't bother putting her pants back on, instead throwing them in her backpack. "Don't worry," she said. "You can walk behind me."

I'm sure the scenery on the trail was very beautiful, but I didn't really notice it. I watched Amy's ass as it bounced up and down, and would even spank it lightly now and again. Amy liked it.

Nearing the end of the trail I couldn't resist grabbing two handfuls of that fleshy, pale ass. Amy stopped walking. I knelt down and gently bit her right butt cheek. I planted sweet kisses on it. Then I pushed her thong to the side and stuck a finger in her ass. She let me finger her about twenty seconds before grabbing my hair and pulling me up. Her lips soon found their way to my neck, and her hand found its way to my dick. Under my shorts she slid her hand all over my dick. I pulled my shorts down, and as soon as I did Amy walked off laughing. "Now you're just getting greedy," she said.

That was the last action I got on the trail. I drove her home as we laughed, and talked about what it crazy day it had been. Of course we did all this while she softly stroked me. "My wrist is going to be sore tomorrow," Amy said.

I laughed. "My ass might be sore tomorrow."

"You prude!" Amy said jokingly. "You know you liked having your ass kissed."

By the end of the drive Amy was no longer whacking me off, but she did keep my package tucked away in her warm hand. We pulled up in front of her house. I put my dick away and walked her to the door. As I hugged her and went in to give her a kiss goodbye, she pulled down my shorts. She lay the palm of her hand on my cock, and gave me a sloppy, wet kiss. I instantly got hard, and Amy pulled my shorts back up to create a massive tent. "Can I see you again?" I asked.

"Hmm...I don't know," Amy said. "You're kind of greedy, but I had fun playing with you and your little friend. Why don't you come over Thursday. I could use someone to practice massage on. Who knows, I might even massage you with my mouth." She winked and walked inside.