The HitchhikersbyLucky Mann©
I was the typical, horny, eighteen-year-old back in the late sixties. It was a warm Spring Saturday evening in southern Michigan. My girlfriend and I had recently broken up, and I was looking for someone to take her place. Jim, my long time friend, and I had been riding around doing a whole lot of nothing that night, and it was getting late. We were about to head for my home, when we spotted them. We were completely surprised to see them hitch-hiking. They were two of the cutest girls either of us had ever seen. Girls like that just didn't hitch-hike.
Of course, we stopped and offered them a ride. They jumped into the back seat and thanked us for stopping. Jim was driving and the girl behind him, Sam (Samantha), was a little taller and slimmer than Karen, the girl behind me. Sam was about 5'7", slender, and had a nice set of 'C' tits. Karen, on the other hand, was about 5'5", nicely rounded but not too fat, and had a great set of 'D' tits. Sam said they had left eastern Ohio early that morning and were heading for California. They were sisters, and they had friends and family there that would take them in. "We don't have any money, but would really be thankful for any help you guys can give us."
I asked if they were hungry, and they said they were. Sam added that they needed a place to stay the night too. We headed for the local A&W burger joint where we ordered them dinner.
As they ate their meal, I asked, "How do you expect to get across country without any money?"
Sam and Karen looked at each other, smiled, and Sam matter-of-factly said, "Sex. We'll give sex for help."
After nearly gagging on my drink, I asked. "How old are you?"
After looking at each other, Sam replied, "We're eighteen. Karen just had her eighteenth birthday a few days ago." Jim and I looked at each other and grinned ear to ear. The gods had smiled upon us. I offered to put Sam and Karen up for the night at my place, feed them breakfast, and take them to the main highway in the morning.
The girls looked at each other, nodded, and Karen, somewhat shyly, said, "OK."
When the girls finished their meal, we headed toward my place, but not before Sam and I changed places. Sam now sat with Jim, and I got in back with Karen. Both girls slid up close to us and kissed our cheeks. Karen seemed to be following Sam's lead. She mirrored almost every move her older sister made.
By the time we got to my place, I had Karen's blouse partially open and was rubbing her tits through her bra. Her nipples were beginning to harden, as was my dick. Our tongues were exploring each others mouths. Sam, in the mean time, had leaned her back onto Jim and he had his arm over her shoulder. He had her right tit was in his hand.
Upon arriving at my place, we went inside, and had a soft drink. As we drank our sodas, we resumed petting. Karen still seemed to be following Sam's lead. Whenever Sam rubbed Jim's leg, Karen rubbed mine. When Sam unzipped Jim's pants, Karen unzipped mine. Sam began kissing and licking Jim's dick, and Karen did the same. When Sam took Jim's dick deeply into her mouth, Karen only took a couple of inches of me in. By that time, Jim and I had opened both their blouses and had their nipples fully erect. We were all ready to head to bed. Jim was the first to move. He stood, took Sam by the hand, and led her off the my spare bedroom. Sam looked at Karen, smiled, winked, and walked out of the living room with Jim. Karen returned her smile and nodded yes. I stood, took Karen's hands, pulled her up to me, hugged and kissed her. I then led her to my bed. Before laying down we again embraced. As I held her close to me, I reached down and squeezed both ass cheeks firmly. A soft moan came from her. Releasing my grip on her ass, I slowly removed her blouse and bra. Karen did indeed have a great set of tits, and she smiled when I told her so. Karen seemed nervous, and but she didn't try to stop my progress. Her hardened nipples stuck out like large pencil erasers. Her belly was smooth and just slightly rounded by just enough fat to make her soft. As I bent down to suck her nipples, I unbuttoned her jeans, lowered her zipper, and dropped her pants to the floor. She stepped out of them and stood before me in nothing but her white cotton panties.
I again hugged her close to me. Karen was noticeably shaking. I asked her, "Are you sure you want to do this?"
She said, "Yes! I've never done this before, but I really want to. Just be gentle with me and go ahead."
"You're a virgin then?" I asked.
"Yes, but please don't stop." She replied. With that we hugged tightly, and I began rubbing my hands up and down her back. My hands rubbed lower and lower until I had two hands full of ass. Karen seemed to be relaxing a little. I picked her up and gently laid her on my bed.
I quickly undressed and got into bed with her. I began stroking her tits and belly. When I started sucking on her nipples, she softly moaned. Pinching her nipples brought a little gasp from Karen. As I alternately sucked on each nipple, my hand found it way to her crotch. I began rubbing her bush through her panties. Occasionally, I'd reach down and slide a finger over her dampening panty covered slit. Her moans were getting louder, and she spread her legs just a little. She began to squirm under my hand on her pussy. Her panties became soaking wet with her juices. Pushing them aside, I soon had a finger slowly rubbing the length of her slit. Every time I touched Karen's clit she gave another gasp. She arched her back to raise her pussy up to my hand as I softly massaged her clit. I removed her panties and spread her legs enough for me to lay down between them. My face was only a few inches from her virgin pussy.
"What are you doing?" she asked. "Have you never had your pussy eaten?"
"No! Will it hurt?" Karen was really naive.
"Not at all! You'll probably like it!" I told her.
"Ok. Just be gentle, please."
With that I resumed stroking her slit with my finger. When she again began moaning and lifting her pussy, I removed my finger and gave her one long lick from her asshole to her clit.
Karen began shuddering as I continued licking. My tongue began probing her virgin love hole. When I gently sucked her clit into my mouth, she grabbed the back of my head and tightly pulled my face into her drenched pussy.
I sucked harder. "Oh, oh, oh shit!" she yelled.
As she calmed down, I moved up beside her and resumed petting her pussy with my hand. An occasional finger would brush her asshole. I asked if that was her first orgasm.
She said, "No, but they weren't nearly that strong when I played with myself." I asked her, "Will Sam get worried if you keep yelling like that?"
She said they had a code word to use if she needed help. Karen said, "Sam told me it would probably hurt the first time, but that didn't hurt a bit."
"That's because we haven't popped your cherry yet, babe. That was only my tongue. It's my dick that'll pop you." I told her.
She looked away and said, "Oh."
I think she was embarrassed to be so ignorant about her own body. I turned her to face me and deeply kissed her. I told her, "It's ok. You're new, and you'll learn. We've got all night." Then, as an after-thought, I asked, "How old are you again?"
She smiled and cuddled closely, hesitated and said, "Eighteen! Please don't stop. I really want this."
"How old is Sam?" I asked.
"She's eighteen, but she's done this a bunch of times." As if on cue, I began hearing noise coming from my second bedroom. It sounded like Jim was riding Sam hard, and she was cuming loudly. After giving this new information about two seconds thought, I resumed petting Karen. Like most young men, I was not thinking with the head on my shoulders. All I knew was, I had a cute girl, naked on my bed, and she wanted to fuck. Karen again began to respond to my hand on her pussy. I sucked hard on her nipples as I spread her pussy lips and worked a finger into her virgin hole. She slowly began to spread her legs wider to give me better access. It wasn't long before I had a finger partially in her. It was soon joined by a second. I gently stroked her clit with my thumb. Karen's body knew what to do, even if she didn't. She was soon humping up to my hand with her legs spread as wide as she could get them. Keeping my fingers working inside her fresh pussy, I returned to laying between her legs. Just as she seemed to be about to cum again, I pulled my fingers from her pussy. I began sucking hard on her clit and tried to shove a wet finger into her asshole. I could only get it up to the first knuckle. "Yes!" she screamed, and I shoved the finger in her ass up to the second knuckle.
This time, as she calmed down, I pulled my finger from her ass but kept eating her pussy. She was soon ready to cum again and still hadn't been fucked. That was about to change.
As Karen resumed humping my face, I pulled away, and kissied my way up her body. I brought me dick to the opening of her virgin pussy. Slowly, I pushed the head my dick into her hole and held still for a brief time. She continued thrusting up, so I pushed in a little more. She was so tight, I felt like her pussy was trying to squeeze my cock back out. When I bumped into her hymen, she seemed to freeze.
I asked her if she wanted me to stop. I didn't need a rape charge.
Karen looked up and said, "No! I'm just scared." I kissed her and pulled back a bit. I took several short strokes that bumped into her hymen without going through. She was hugging me tightly but seemed to pull her pussy away every time I hit her hymen. I pulled back to where just the head of my dick was in her. "You sure?" I asked.
I hugged her tightly around the neck and shoulders to keep her from moving. I fully entered her with one swift stroke. I felt her hymen give way, and Karen yelled loudly just once. When I was fully buried in her, I held still. I wanted to give her a chance to get used to having a dick in her freshly opened fuck hole. After about a minute, I began slow, but full strokes. When she began to weakly return my strokes, I sped up a bit. I was soon giving her long hard strokes, and she was trying to return them. Her tight pussy soon had me ready to erupt. When I told her I was about to cum, she wrapped her legs around my waist and pulled me deeper into her.
"I can feel your cock pumping in me. It's warm. Are you cuming?" she said.
I told her, "Yes, baby. I'm cuming.
She smiled, but said nothing. In a few minutes, Karen lowered her legs, and I pulled my softening dick from her freshly fucked pussy. When I rolled off her, I noticed a small amount of blood had stained my sheets. A drop of cum was clinging to a lip of her pussy. We had cuddled a while, when Karen asked, "Why did you put a finger in my ass?"
My only reply was, "Did you like it?"
"It felt weird, but it was kind of exciting." She answered.
I said, "Since this a night of firsts, do you want to try a couple more new things?"
She said, "Sure, if you'll be gentle and tell me what to do."
I smiled at her and said, "I'll be gentle, but you'll have to help me get hard again. Get down there and kiss and lick my dick."
I really didn't need any help getting up, but I figured that was a good way to get her mouth on my dick.
She immediately turned around and began kissing and licking my dick. She seemed to like the mixture of my cum and her juices. Karen followed my instructions well. She only hesitated a second when I told her to put it in her mouth. She used her tongue well without being told. Karen was soon firmly sucking my dick deep into her mouth. Down her throat was next. She had some difficulty and gagged a few times until she learned to relax her throat muscles. In a short time, Karen was deep-throating me like a pro.
Karen lifted her head off me just long enough to ask, "Is this a blow-job?"
"Yeah baby, and you're doing great!"
She quickly went back to taking me down her throat.
"I'm about to cum, baby! Swallow it if you can." I told her.
She started to pull off, but a very gentle touch to the back of her head prompted her to stay where she was. She pulled my cock out of her throat, but kept it deep in her mouth. As I began cuming, she sucked even harder until she had taken my whole load in her mouth. As she sucked the last drop from my dick, she sat up, grinned, and swallowed twice. "How'd I do?" she asked.
"Absolutely great baby! You may be a natural cocksucker." I replied. "But, we're not done yet."
With a big grin, she laid back down and asked, "What more can we do?"
"You liked my finger up you ass didn't you?" I asked.
She grinned and nodded affirmatively.
"Well I'm going to fuck you in that sweet virgin ass too."
This little gal must have been made for fucking. Her only response was, "Cool, but be gentle."
I again began petting her pussy, but this time only to get her juices flowing for her ass. Time after time, I took my finger out of her pussy and rubbed it around her asshole and tried to push my finger in. Her asshole was just too tight and dry.
It was then that I remembered my ex-girlfriend had left some baby oil in my night stand. She had used it while jacking me off. I quickly retrieved it and put a generous amount on my hand. I then applied it to Karen's asshole. I soon had a finger all the way in her ass. She began to wiggle her butt as I stroked my finger in and out of her virgin ass. When she said, "Oooh, that's nice." I put a second finger in. As I worked two fingers in her ass, I began to stretch her open. My fingers were soon smoothly moving in and out of her ass.
I pulled my fingers out of her ass and got between her legs again. I lifted her legs nearly to her chest and had her hold them there. With a little more baby oil applied to my dick, I put its head at her virgin asshole's rosebud. With a gentle push her spincter opened, and my dick's head popped into her ass. Karen's eyes sprang wide open, but she said nothing. I told her we could do it in one swift shove or an inch at a time. Both would probably hurt a bit.
She said, "I'd rather get it over with quickly."
I pulled out and applied a little more oil to my dick. I again placed my dick at her rosebud and pushed gently. This time, as my head popped into her asshole, I gave her a strong thrust. With one quick stroke, I buried my dick deep in her ass.
Karen screamed louder than she did when her pussy's cherry had been popped, but again only once. She made no further cries.
After staying buried in her ass without moving for nearly a minute, I pulled back to where only my cock's head was still in her asshole. Without hesitation, I pushed fully back in. Karen grunted. Slowly stroking in and out of her ass, I soon noticed her asshole was loosening up. She was beginning to rock with me. I reached down and fingered her pussy and clit. That really got her going again. Damn, she had a tight hot asshole. It was a good thing I had already cum twice. Even so, it didn't take long before we were both about ready to cum again. I began slamming into her harder and harder.
Karen was pulling her legs up higher and yelling. "Yes! Fuck me! Fuck my ass! More! Harder! I'm cuuuuming!" As I slammed into her as hard as I could, I shot my wad deep into her bowels. I pulled out of Karen's asshole with a pop and we laid snuggled together.
As we relaxed, we cuddle for a while before falling asleep. I was awoken Sunday morning by Karen sucking my dick. When I was fully erect, I asked if she wanted to get fucked again. She said she did but her pussy was too sore. "Can you do my ass again?" she asked.
I patted her butt and had her lay face down next to me. I reached for the baby oil and began rubbing her ass cheeks. She quickly spread her legs, and I applied a squirt of oil directly to her asshole. When I inserted a finger, I found she was still just a little slippery from night before. When she began raising her ass to me, I had her get on her knees with her shoulders still on the bed. I spread her knees wide apart. That put her asshole in the perfect position to be invaded again. Getting on my knees behind her, I aimed my dick at her asshole. She quivered when my dick touched her. Again, with one shove, I buried myself in Karen's ass. She moaned and pushed back. We were soon fucking like two dogs in heat. I reached under her, firmly grabbed both tits, and used them like handles to pull her back to me. She was matching every stroke I gave her with an opposite push. I grabbed her hips and hammered into her ass with all the power I had. She was grunting and groaning with every stroke. When I reached up and pinched her nipples, she reached back and began fingering her clit. As she shuddered to a climax I began to cum as well. With one final, full length, ram, I dumped my load deep in her bowels.
A short time later, we showered, and I made breakfast for the four of us. Sam said I must have popped Karen's cherry twice because she had heard two screams.
Karen said, "Yeah, but one of the cherries was in my ass."
Sam's eyes popped wide open. She appeared shocked and could only say, "Wow!"
After breakfast, Jim and I tried to talk the girls into staying for a while. They said they really appreciated everything we had done for them, but they needed to get to California.
Karen smiled broadly and said, "Yeah, everything."
Jim and I then took the girls to the nearest super highway and wished them well.
When we talked about our experiences, Jim said Sam was a good piece of ass and gave great head, but she wouldn't let him touch her asshole. I still don't know if he believed me when I told him what I had done with Karen that night.