I was making an extended drive and decided to see if I could find a rider on Craigslist to make the time go faster. I found a young girl going back home from a college break. Bailey was a cute little thing, just the sort I was attracted to...petite but perky and impish.
We talked about the differences in our generation's experiences in college. Of course that mostly meant sex. She was interested in the "hippie sexual revolution" and I was fascinated by this generation's casual attitude toward sexting and sending suggestive selfies around.
It seemed their attitude toward sex was that it was perfectly normal for girls to help guys with their sex drive with a hand job or blowjob... similar to a neck rub in my generation for a headache.
"Well....It must be nice to be young," I commented. "I guess I was just born too soon."
"I think we all just enjoy the ability to get the guys aroused, but then we can't just leave them hanging...so to speak. I always have my best sext photos available. You can never tell when you might want to show them to someone."
"Would you like to see what they look like and see if they're also exciting to someone from the sexual revolution?"
"Just you sitting here talking to me about it is pretty exciting, so I'd love to see your photos."
"Okay... I usually first send just a casual one to see if I'm their type since I'm so small. And then to give them some reference I show one of me next to my girlfriend. My tongue is the height of her nipples."
"Lots of guys just want to see big tits and ass, so I don't get too much interest. But if they're still interested, I show them more. These are from when I was shaved, but I'm not anymore."
"I figured since I'm so small, I didn't want guys who wanted little girls they can dominate and abuse. I wanted guys who would like to be with a woman who was her own person with her own ideas about sex."
"Wow! Bailey....those are definitely uninhibited."
"Well there is so much graphic stuff on the internet now that these are the equivalent of swim suit pictures. They don't really show anything sexual. Here are a couple more recent ones."
"I guess that is a generational difference. And just so you know...you have my perfect fantasy body, hair and all, and YES, those are exciting to me."
She giggle with a flirtatious look. "See. You found those exciting, and just the fact that they got you excited, gets me excited. My nipples get erect when I get excited, so it's hard to hide it."
I glanced over at her hard nipples poking out of her t-shirt.
"Here just feel how hard they get." And she took my hand and rubbed it over her nipple.
"Thanks for sharing. Yes they are erect, so I guess then it's erections all around." She looked over at the erection in my pants.
"Let me change positions", she said. "I want to be able to see you if we're both going to be excited together." She grabbed a couple quilts and a pillow and propped them in the console area so she was facing me, leaning back on the dash. Only someone under 5' could make that fit.
"And if you find my body exciting, you should be able to see it better. I don't want you to have to take you eyes very off the road, so now I'll be in your field of vision."
She lifted her leg to give me an open crotch view. "Well, you are definitely a vision." I replied.
"And this way you can feel my nipples better." She said as she took my hand and held it over her entire breast. I cupped her entire breast, squeezing and fondling it while I rolled my finger over her nipple.
"Ummmm, you definitely are not shy. Maybe it's just my generation, but I find this more exciting than looking at pictures." She giggled again and gave me that playful look.
"I like it too. That feels nice. But it would feel even better underneath my shirt."
I didn't need anymore encouragement than that. I slid my hand up under her shirt and cupped the softest yet firm little handful of tit God ever made.
"I want you to see them, too." She said as she pulled her top up. They bounced free and stood straight out from her little chest. Then she rubbed my hand tightly onto her breast.
"Emmmmm. That feels so yummy. Do they look better in person than in the photos?"
"Oh....they couldn't look any nicer." I said as I continued to fondle them to my hearts content.
"They might look nicer with NO top." She said as she pulled her top off. And she was right, they were glorious. The sun reflected off her bare breast highlighting the little body fuzz covering them.
As she and the car moved, they just jiggled in the most lovely fashion. Their full roundness was so evident, just calling out to be cupped and squeezed.
"Just look how erect my nipples are now." She said coyly as she pulled on the nipple. I immediately squeezed it between my fingers and twisted it while I gently pulled it.
"Oh...I just love it the way you play with them. God that feels great." I continued my joyous fondling of her breasts. Then, unexpectedly, she moved her hand over the obvious erection bulging in my pants.
"Would you like it if I played with you too?" My body jumped a little and I gasped.
"Oh... that is nice." I barely got out. She stroked up and down my cock, and then rolling her hand to cup my sack.
"I told you I wouldn't leave the boys hanging." Then she fully traced its outline again in my pants. My precum had already soaked through my jeans and left a wet spot.
Her fingers traced over it and she said, "I guess I'm not the only one who's wet." Then she pulled my hand into her crotch. And she was right again, her crotch was wet with her excitement.
I stroked up and down her crotch feeling the contour of her lips and pushing strongly into her crotch as her hips slightly rocked. She returned to stroking up and down my erection. So far she had taken all the initiative.
But she obviously wasn't going to reject any advances I made. I curled my fingers under the leg of her shorts and pulled them aside as I pressed against her wet panties.
She gave a slight moan and said, "Isn't this a nice way to pass the time on a long trip?"
"I can't think of anything better."
"Oh...I can." She said and undid her shorts and pulled them off.
"Just look how wet you've got me." She pressed her finger into her crotch and brought it up to circle my lips. I reached my tongue out and licked her tangly finger.
"Well then I'm just going to have to investigate this further." I said as I moved my hand into her crotch and stroked up and down her wet panties, pressing them between her lips. Then I slipped my finger under her crotch and rubbed it over her wet lips, just glazing her clit.
She moaned as I moved my fingers around her pussy and butthole. Each rimmed with a little hair and wet beyond belief. Her hand renewed its fondling of my cock.
I moved my fingers all around her moist, tender privates and parted her lips with my fingers. Then I slowly pushed my finger between her lips. She moaned as it slid deeper and deeper into her.
When it was all the way in I slowly pulled it out and then re-inserted it a couple times before curling it and swirling it inside her.
"Oh, Yes. God! Now do you know why I have sext pictures? I just love the feel of fingers in my pussy." She said as she strongly stroked my cock.
"Then you'd probably like to feel of two fingers in your pussy," I replied as I quickly thrust a second finger into her. Then I pumped them in several times.
"Ohhhhh, " she moaned. "Let me take my panties off, and you keep doing that until I cum, and I'm going to give you the hand job of your life." She peeled her panties off and there was the cutest pussy my eyes ever beheld. Just so fuzzy and puffy, tiny and cute.
I just admired it for a second and then lightly I teased her with one finger and slowly slipped it in and out a few times. I enjoyed watching those cute, puffy lips being penetrated by my large fingers.
Then I followed it up with a second and thrust into her pussy as she gasped. Her little breasts were bouncing so delightfully. I could pick her hips up when my fingers went in she was so small.
Her whole body seemed to be bucking. Her hand left my cock and she reached under herself and inserted first one and then two fingers into her ass.
"Please, put a finger in my ass," she begged as she removed hers. Her asshole remained open after she removed her fingers, so I easily inserted my finger.
Her hand went over her pussy and she started to stroke her clitoris. She was moaning and thrashing. Her little body was bouncing around. I could see her moving towards her orgasm.
"Put a second finger in she pleaded." Everything was so slippery it too went in easily.
Her hand was going faster and faster so I started to really thrust my fingers into her ass. That seemed to be what she wanted. She was gasping with each thrust and then she arched her ass and let out a long scream.
I stopped my thrusting as her body stopped and just quivered. It was so exciting to watch that I came in my pants. I pulled my fingers out of her ass and watched as her ass muscles contracted and relaxed several times for each quiver.
Then she just laid there as I sped down the road. Slowly her eyes opened and she looked at me.
"Oh, you lovely, lovely man. God, did you make me cum. I can't remember the last time I came that hard. So many taboos and firsts really helped ramp up my excitement. I am going to give you the treat of your life, my friend."
"You were so exciting to watch, I came with you."
"Oh, that is so sweet that you'd cum just from giving me pleasure. WOW, maybe there is something special about your generation. But have no fears. I will get you harder than you've ever been in your life and you will shoot cum all over us."
Then she reached over and undid my pants and pulled my zipper down. Was there ever a sexier sound. She reached in and wrapped her hand around my semi limp cock. I just moaned. I don't think I have ever felt anything so pleasurable.
Now I had both hands on the steering wheel and my eyes on the road. I glanced down a couple times just to freeze this image into my mind for future reference. She moved my cum all over my cock so her hand slid effortlessly.
"Help me pull your pants down a little so you are completely free." She moved one leg over my lap so her cute little pussy and ass were right at my side. My hand was now cupping that cute little ass cheek.
God, I just loved watching her tiny, sexy body flex and jiggle as she repositioned us. Then she grabbed my cock and slowly began bringing it back to life. She had the happiest and determined look in her face, like she was really going to enjoy watching what she could do to me.
She definitely knew her way around a cock. It didn't take her long and she had me rock hard. Her hand would stroke and curl and pump and squeeze. When things got a little dry, she'd lean over and drool over my cock until it was slippery beyond imagination.
She would bring me right up to the edge and just as the first ejaculate would start, she'd clamp around the base of my cock to stop it. Then she'd build it up to another ejaculation and stop that one.
Some of my cum landed on her pussy, so I rubbed it into her stomach and pussy until they glistened. Then I could tell she was getting more excited and was really stroking me.
"OK, I think we're ready. You'd better pull over." She said as she began pumping faster. So I did and moved the seat back.
"They'll be no stopping this one. I want you to explode like you have never exploded before."
She was using both hands and had one cupped around my balls. She was going faster and faster. Then I felt her finger my asshole, a totally new experience for me. My hips were now moving as well.
I felt the pressure building like I have never before. She was really pumping now and I started to grunt as the first larger ejaculation shot out. I was amazed. It shot far enough to land in her hair. I'd never shot like that.
Then another one hit the other side of her face. I didn't feel like I had even begun yet when she drove her finger into my ass. Oh, my God. Other rope of cum landed on her chest and another and another.
I didn't think I'd ever stop. Finally they got less powerful and she pressed her finger on something that made me cum several more times. Then she worked her hands, just totally draining my cock, sack, and probably the next three months of cum.
I have never been so drained. I lay there exhausted watching her with a big smile, smearing my cum all over her body until it just glistened.
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