While you are categorizing First Time stories, file mine under "clumsy &
awkward!"

I was driving west on U.S.64 in northwestern Oklahoma, which is flat, dry, open
rangeland. It's the kind of road where every driver of every car you pass, and
there aren't many, waves at you. It's impolite not to. It was in the hot summer
and I was on my way back to a construction site where a strike had just ended.

The only things that block your view for a hundred miles besides the grain
elevators are highway overpasses, huge concrete federally-funded monsters built
to allow a one-lane dirt road pass over the paved road. They were the only shade
for as far as you could see, and under the one I was passing now, was a
red-haired girl in shorts, hitchhiking. Her last ride was just letting her out at
the exit.

I drove right by, thinking to myself, "The rule is, 'never pick up hitchhikers,'"
but as I passed her at full speed, I noticed she was very cute. She was only
about 5' or so and was carrying a backpack and didn't strike me as the least bit
threatening. I wanted to slam on the brakes and pick her up, but I thought it
would appear too much like I was stopping only because I saw she was attractive,
not because I was being neighborly like the rest of the western Oklahomans. Yes,
it was true, that was why I was thinking of stopping, but I didn't want it to
LOOK that way. So instead I drove by and looked for the next exit, where I
planned to turn around, go back and drive by again.

As it turned out, the next exit was two miles away, and I as I quickly calculated
that it would be five or six minutes before I could get back, it seemed very
unlikely that she would still be there. Surely one of these neighborly folks
would stop for a pretty girl before I got back.

But, no, she was still there when I came back by. I stopped and asked her how far
she was going. By now I was fantasizing that she would answer "all the way," but
she said, "San Diego."

As we drove the next 100 miles or so, we chatted. She was from Florida and her
name was Cheri, but she pronounced it "Cherry." She was on her way to San Diego
to meet her other friends who had migrated from Florida, including her boy
friend. She said she had been on the road for several days, thumbing it, and
really missed bathing somewhere besides in the rivers she passed along the way.
She looked as road-weary as she said. Her jeans and t-shirt were dirty and her
flaming red hair was ragged and unbrushed. She had spent the nights with friends
and relatives through the south, but beyond Arkansas, she hadn't known anyone.

My destination was a motel in Woodward, Oklahoma where all of the non-local
construction crew stayed. As we neared my turnoff, I told her this was as far
west as I went, but I would gladly let her stay in my motel tonight, where she
launder her clothes and have a hot shower, and oh by the way, sleep in a soft,
warm bed. And the next day, I would drive her as far as Albuquerque, New Mexico.
Cheri didn't hesitate to accept my offer.

Since the motel was home for weeks at a time, I usually asked for double beds, so
I would have someplace to stack the extra belongings I carried for long stays.
When I checked in this time, I was firm that I wanted a room with only one bed. .
. just in case.

Cheri was really travelling light. She had little more than the clothes on her
back, so she wanted to be sure to get them all washed while she had the chance. I
was 6'2" and over 200 pounds. Nothing I had was even close to a fit on her, so
she wrapped a towel around herself and headed for the motel laundry room. Wrapped
only in the towel, I stole glimpses of her as she bent over to gather her
clothes. Nice!

While she was out, I opened up the road atlas and realized Albuquerque was much
farther than I thought. It did adjoin Oklahoma, but not until passing through the
entire panhandle, which I had forgotten about in my eagerness to convince Cheri
to stay for the night. There was no way I was going to be able to drive that far
and return in time for work.

When Cheri returned, I confessed I would not be able to drive her all the way to
New Mexico. Her face fell. I told her that if she wanted, I would buy her a bus
ticket through to San Diego. Her face lit up. To me a bus trip that long would be
hell on earth, but compared to hitching across the southern desert in the summer,
I guess it sounded like heaven to Cheri.

For the rest of the evening, she was happy and very affectionate. We had dinner
at the motel, followed by a walk around the tiny park outside the motel and
wherever we went, she had her arm around my waist, talking nonstop, smiling up at
me. With the load of her trip off her mind, her personality showed itself; she
was charming, bubbly, and very outgoing.

As the sun set, we started to settle in for the night. I had let the possibility
of sex nearly (not completely!) leave my mind. Her companionship for the evening
had been wonderful, and if that was as far as it went, I had no complaints. We
both wanted to shower and she asked if it was OK if she went first, and I agreed,
OK, fine with me. She went into the shower and closed the door to change and came
out in a few minutes, in a towel again and began to brush her hair and put on
makeup. Never having lived with a woman, it didn't dawn on me that there was no
reason to put makeup on just before bed.

I sat on the bed, watching her from the rear. She caught my eyes in the mirror,
appreciating her body as she worked. Her glances back at me came closer and
closer together. Cheri realized I was not paying any attention to the guitar as I
played; my sole interest was her cute legs and bare back. Finally she stopped and
just stared right back at me in the mirror and asked, "What are you looking at?"

I smiled and replied, "You."

She cocked her head and gave me a little grin and said, "The shower is empty now,
you can take yours if you like." I stripped to my briefs, then passed behind her
putting both hands on her bare shoulders as I went by and showered. I came out
wearing only a towel too. I didn't want to have more clothes on than Cheri did.

When I opened the door, she was still standing at the mirror, and wearing only
her panties, was pulling her shirt down over her head, her bare chest exposed. My
eyes went right to her breasts; they were small but not flat, the kind we guys
classify as 'perky.' She had large nipples and they were standing up hard. I
thought, "Thank God for hotel air conditioning."

As stimulating as that view was, seeing her naked boobs bounce as she pulled the
shirt down was not the best part - the real excitement in my mind was the
realization that she had obviously waited until I opened the door to put her
shirt on. When I opened the door, I saw her first in the mirror again, posed with
her shirt over her head, looking back over her shoulder at the door. When she saw
me, she abruptly turned her head away from me as if not to notice me and then
started wrestling the shirt down over her head. She was waiting for me to exit,
in order to appear that she was innocently flashing me.

I missed the clue with her makeup, but I didn't miss her intent this time. When
she got her shirt down over her head, she smoothed it and looked at me staring at
her, enjoying the show. She smiled back at me and didn't say a word, but went
about walking back and forth in the room arranging things, turning the lights on
here, off there. I was not at all subtle about following her sexy little buns as
she walked away, leering at the bulge in her panties as she came toward me.

Finally she sat down on the edge of the bed and said, "Come here."

Gladly, I thought. As I approached her, she said, "I want to thank you for the
ride to San Diego," reached over and undid the towel. It fell to the floor,
leaving me nude in front of her. I had been in a semi-erect state watching her
walk around the room. When she put her hand on me and stripped my towel off, I
immediately reached full attention. Cheri took a fast look at my hardon, pointing
right at her face and slipped her own panties off, spread her legs and pulled me
forward. I resisted a moment. I was surprised by her quick action and I also
wanted to savor the view of her pussy. She was a true redhead and her pubic hair
was very fine and sparse, which allowed me to look openly at her bulging lips and
her slit until I let myself be drawn down against her. Having never been this
close to actual intercourse, I had no idea that maybe it would be a good idea to
have a little foreplay, or at least tease her with my prick a little before
penetration. I simply started trying to push it right in her.

Not that it mattered. Cheri was not attempting any physical foreplay either, she
was aiming to 'thank me' promptly! I put my hands on either side of her body,
held myself up above her and pressed against her pussy. I did know from locker
room sex education that when a woman was aroused, she got wet, and as I pressed
against her, Cheri was dry. I took this as a bad sign. Cheri pushed me back and
said, "wait," and put one finger in her mouth and ran it over her pussy lips,
"OK."

I pushed at her again. This time I did slide right inside her, and inside she was
indeed wet. I reveled at the way it felt to have my naked body against hers, my
dick inside her, and my balls pressed tight against her thighs.

Cheri began thrusting her pelvis back and forth against me. I had expected sex to
feel like masturbation, but I was unprepared for the way her vagina fit me like a
sleeve, that the whole of my penis would be stimulated at once as she worked me
in and out. I was immediately ready to come. I withdrew partway and stopped,
panting, "No, stop, wait." It was too late. My first time was less than a minute
old, and I popped, throbbing and gushing into her after about five strokes. I
opened my eyes and looked at Cheri. Her eyes were wide open. She said in
amazement, "Wow, you must not have had any in a long time." I could feel my face
turning red. I mumbled, "Yeah, it has been."

The next morning as I took her to the bus station, she confessed to me that she
was only 16. She had said she was 18. I wish now that I had confessed too, that I
was a virgin until last night, but my male pride kept me from admitting that a
16-year old girl was so much more experienced than I. If I had, maybe she would
have a fond memory too, of the night she had a 24-year old man's cherry.

I kissed her goodbye at the bus station. She said, "You've got to quit being so
nice to people." I didn't know what she meant by that, but it seemed like bad
advice. As the bus pulled out of the station, I could see her waving through the
window. I never saw or heard from Cheri again.