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First Time for 19 Year Old Sailor

Was it really almost 50 yrs ago? Doesn't seem like it. I can
remember.....Nineteen years old and still a virgin. Now that's something you
don't want to get around to the rest of your shipmates. But hey, I was a little
drunk and looking for sympathy when the subject of "last piece" came up. I
was only temporarily assigned to the ship and wasn't really part of the group.
They let me tag along sometimes and that's why I was there when the subject
came up. So I told them I was a virgin. Got LOTS of sympathy. I'm just glad
it was a small bar. I didn't have a lot of laughter to run through getting out of
the place. It was about three weeks later when Bill came up to me on a
Saturday night and asked if I wanted to hit some bars. I was bored and , of
course, ever hopeful Miss Right would be out there and said OK. Since we
heading out on a cruise the following Monday, I figured I better get some
shore leave in before we shipped out. Bill jokingly said "Maybe we'll get you
laid tonight." Yeah, right. In a pigs eye.

We took off and headed down the 'strip' (every Navy town has one). I was
driving my relatively 'new' 68 Skylark; relative since it was 1973 and the car
was 'new' to me. Bill said "Fuck it, let's try someplace else. Someplace where
there aren't a lot of sailors ruining the place." Sounded good to me so I let him
lead the way. We drove around Newport quite a while with Bill giving
directions. I had a feeling he was looking for someplace in particular but
didn't really care. Finally he directed us into a parking lot and we went into
the adjacent bar. "Jesus, this place looks dead" I said. Bill told me to just wait
and we took a couple of seats at the bar. We had a couple of beers while the
place started to fill. Most of the newcomers were older women. At 19, any
'woman' is older; these looked to be over 30 with an occasional over 40
mixed in.

Very few men which made me wonder if Bill had picked a lesbian bar (I hate
that terminology). It was still kind of early and we were working on our third
beer ( I was, Bill was on 4 or 5) when Bill grabbed my arm, lifted it in the air,
turned to the mostly female population at the bar and said "I have a virgin
here, how much do I hear?" All I could think of was "How could I let myself
be embarrassed like this again?" I steeled myself to slink out amongst the
expected laughter when I noticed there wasn't any. Looking around, all I saw
was expectant and, in some cases, hungry looks. I grinned sheepishly at the
wolves and said nothing, just kept sipping my beer. Being 19 and not a
professional drinker, the beer started having its effect. I remember talking to a
lot of the women there (the beer relieved some of my inhibitions) but was not
'attacked' by any of them. The band started playing and I danced with the
women I was speaking with. During one dance, I noticed a new woman enter
the bar.

Beautiful! About 34, 5'6", brunette, and a body that would knock you socks
off. She was obviously a regular since she said hi to almost everyone there. I
didn't pay much attention to her since she looked so damn good. Figured my
chances, coupled with my inexperience and age, were nil (typical of ALL my
thinking about girls/women at that time). The woman I was dancing with saw
me looking and just smiled. After the dance was over, my partner excused
herself saying she had to talk with some friends. I went back to the bar and
talked a while with Bill. I noticed that my last dance partner was talking to
the brunette but I didn't think anything of it. Next thing I new I was being
tapped on the shoulder. Turning around I almost choked on my beer; it was
the brunette asking me if I wanted to dance. Nodding my affirmation (thank
God I didn't have to open my mouth and make a fool of myself) I followed
her out to the dance floor.

We spent the next few hours dancing and drinking until the bar closed. Bill
left with one of the women we had talked to earlier with the parting shot
"Give her hell!" Mary (the brunette) simply smiled at him and leered at me. I
figured she was only flirting and nothing would come of it. When it got down
to us and a few other clients, Mary asked if I would give her a ride home.
Sure, I was hoping but figured my typical luck would hold out and nothing
would happen. It didn't take long before I was totally lost. I kept following her
directions figuring "it's her house, she knows the way." Suddenly she said
"turn right here!" I turned the car onto a dirt road and quickly had to hit the
brakes. Before me were rows of corn stalks with no house in sight. She
reached over, turned off the ignition, and said "I understand your a virgin. I'd
like to do something about that." Now, a note of clarification on my virginity.
I had dated a girl during my senior year in high school and we got pretty
serious. Without going into detail on how it happened (another story,
perhaps?) we experimented our way into heavy petting, and graduated to
some mild oral sex (no orgasm this way, at least for me) and mutual
masturbation.

Both being Catholic and in HS, the guilt, paranoia, and down right fear of
pregnancy kept us from going any further. The same guilt and paranoia
always infected our trysts and made them less enjoyable. I digress but it is
important to the story.... I was terrified! I wanted her so bad but my fear of
failure, self, etc. was almost overpowering. She slid over to my side (thank
God I didn't have bucket seats!), put her arms around my neck, and we started
kissing. The new moon, hanging low in the eastern sky, provided a pale
surrealistic light to the situation. She slid her tongue inside my mouth and
played with mine in a way that promised greater things to come. But still, I
was petrified. I knew this was it; it was finally going to happen. Technically I
new what to do (I'd seen pornos, read books, practiced by myself) but I was so
nervous I couldn't think what to do first. She broke the kiss and said "This
really IS your first time, huh?"

All I could do was nod. Couldn't even mention the little I had done in high
school. "Well, we'll just have to find something to do to calm you down", she
said. Right, got any phenobarbitol? I'm 19, finally gonna get laid, and she
thinks she can calm me down? Good luck. She again started kissing me, that
wonderful tongue playing intricate games in my mouth. Her hands
unbuttoned my shirt and started caressing my chest and occasionally
venturing down to my stomach and the start of my pants. My cock was
straining and almost screaming at me to get started. Tentatively I reached out
and cupped her breasts. She moaned, reached both arms behind me and
crushed herself against me. I almost passed out! This was too good to be true!
No begging or pleading, just someone who wanted it as much as I. Somehow
I got her shirt unbuttoned and began caressing her breasts. MAGNIFICENT!
She broke our embrace, reached behind and unsnapped her bra. She smiled at
me as her breasts tumbled free, grabbed my head from behind, and pulled me
down to those globes. I was lost in between them! I kissed and sucked her
tits, going from one to the other, slathering them with my tongue without
touching her nipples.

She lay back moaning, crushing my head to her breasts. Finally, I began
running my tongue around her nipples first in large circles which gradually
became smaller until my tongue was flicking across her nipple. Slowly, I
drew the nipple into my mouth and began to suck on it. The pressure of her
hands on my head increased and I tried to suck as much of her breast into my
mouth as I could. I went back and forth between those melons driving both of
us into a frenzy. By this time my dick was in extreme pain. I new I had to do
something to relieve the pressure but felt I needed to do more to please her. I
remembered one of my shipmates telling how he preferred cunnilingus before
entry to help excite the woman and reduce the amount of stroking required
for her to reach orgasm. And believe me, I was determined that she would
also reach orgasm. I began running my tongue down her chest to her stomach
and back to her breasts. I was curious if she wanted me or even would let me
go down on her. Taking her louder moans as an un-official endorsement, I
began to undue her pants. She lifted her ass and helped me pull her pants
down and off.

I began to go lower toward her cunt when she pulled my head away, looked
into my eyes, and asked "Do you know what you're doing?" Not wanting to
spoil the situation by saying something stupid I simply nodded. "I thought you
were a virgin?" she asked. I mumbled something about reading a lot and she
chuckled in a very sexy manner and said go ahead. I again lowered my head
to her stomach and continued running my tongue around the area,
occasionally dipping below into her panties and dramatically increasing her
moans. I grabbed her panties and slowly drew them off. She twisted in the
seat so that her head rested on the passenger side arm rest with her legs
spread on the seat (thanks mom for not letting me buy that sports car!).
Starting at her knees, I ran my tongue down her legs to where her cunt hairs
just started tickling my nose. Knowing that I should start at her clitoris
(thanks to "Everything You Wanted To Know About Sex But Were Afraid
To Ask"), and the general location, I used my tongue to explore until I found
it. I started flicking her clit with my tongue and sucking it into my mouth. She
arched her hips, grabbed my head, and crushed it against her cunt. Whatever I
lacked in experience I tried to make up for in effort.

I kept sucking gently on her clit, my saliva mixing with her juices, until she
was soaked. Leaving her clit I moved down and began tonguing her vagina.
Taking a deep breath, I shoved my tongue as far into pussy as it would go.
She mashed my head against her moaning "Jesus, a natural pussy eater!"
Hearing that drove me wild! I began thrusting my tongue in and out with
short trips back up to her clit. I just couldn't get enough of it with her
moaning how good it felt and kept fucking her cunt with my tongue. Finally,
I'd had enough. Not that I couldn't continue doing that, I just couldn't take the
pressure on my cock. Breaking her iron-like grasp on my head, I pulled back
and began taking off my pants. She smiled at me and said "Now it's my turn."
"NO!" I almost screamed, "I couldn't take it!" She smiled knowingly at me
and laid back down on the seat again spreading her legs.

This was it. The moment of truth! I knelt between her legs and she reached
down and grabbed my cock. I almost died! Just having someone else besides
me touch my cock was fantastic. She stroked it back and forth a few times
muttering "it feels sooo nice!" Grabbing my cock, she pulled me towards her
and down to her pussy. Without letting go of my cock, she slowly worked it
into her pussy grabbing my ass with her other hand. I couldn't believe the
sensation! Rosie Palm and her five sisters NEVER felt like this! When she
had all of me in her, she let go of my cock, grabbed my ass with both hands,
and moved her hips up and down against me. At last I was fucking a woman!
I started getting carried away and thrust with all my strength against her, her
hands on my ass pulling me deeper into her pussy. I knew I couldn't take
much more of this.

Feeling an orgasm start, I shouted "STOP!" Too late, I started coming inside
her but held myself very still hoping I could control how much I came. She
looked up at me and asked "Did you come?" "A little", I replied. Smiling, she
stroked my cheek and asked "Do you want to stop?" I shook my head no and
started stroking my still hard cock inside her. Now I understood one of the
benefits of being 19, healthy, and incredibly horny: once just wasn’t going to
be enough! I also noticed that the first 'little' orgasm seemed to deaden the
sensations in my cock. Realizing I could now fuck her without worrying
about coming too fast, I went at it with a renewed gusto. She looked at me
and moaned "I don't believe it!" My ego soared! I was Tarzan dominating
Jane! I was the fulfillment of the male image! Marlboro Man look out! I'm
riding this mare to the sunset!

I kept up the pace, going in and out, as deep as I could, her writhing and
moaning driving me to animal passion that almost scared me. Her hips
thrusting back at me met my every stroke with equal, passionate force.
Suddenly, she grabbed me around the hips with her legs, and sinking her teeth
into my neck, began to come. Her vagina clamped down on my cock and I
could feel it pulsate in rhythm to her body convulsions as she became lost in
the throes of her orgasm. I couldn't believe that I had actually done that to a
woman. She held on to me long after the orgasm subsided, my cock still hard
inside her. Finally she relaxed her legs and let me pull out of her. I didn't want
to leave that warm, marvelous cavern but my arms were shaking from holding
myself up. I sat back on the seat with a silly grin on my face. She sat up, saw
the grin, and chuckled "Well, how was it?" Still grinning I replied "WOW, it's
a lot better than I thought!" She laughed and snuggled up to me, her breasts
pressing against my arm.

I lit a cigarette for both of us and we sat there in silence smoking. She
finished half of hers and snubbed it out. Leaning back against me, she started
stroking my thigh and said "Well, we can't go with you only having a little
orgasm. How about a big one?" I was shocked! My high school escapades
previously mentioned always ended with one orgasm no matter how good it
was. Now here was a woman asking if I wanted more. I don't think I can
relate the male ego boost that occurs even today upon hearing that! I looked at
her, nodded and said "I don't know if I can come again." She looked me in the
eye and said "Let me worry about that." Using both hands she gently forced
me back until my head lay on the driver's side armrest, my legs spread on the
seat. Being obviously of a vengeful nature, she began running her tongue
down my legs and around my stomach being careful to avoid my crotch. I
moaned and writhed under her ministrations, thrusting my hips involuntarily
into the air.

Finally, after one tongue excursion down my thigh, she began tonguing my
balls. She went back and forth between them getting the hairs soaked with her
saliva. She suddenly stopped, looked up at me, and took my left testicle into
her mouth. She sucked on it softly and stroked it with her tongue. Letting it
slide sensuously out of her mouth, she repeated with the right testicle. She
went back and forth between them, sometimes using her mouth to 'fuck' my
balls, sliding them individually in and out, in and out. She stopped, and
taking a deep breath, took both balls into her mouth at the same time, gently
stuffing them in with her hands. The sensation was overpowering. My cock
felt more engorged with blood than ever before; bouncing up at the sky with
every beat of my heart. I squirmed repeatedly underneath her which seemed
to drive her into a heightened frenzy. She kept sucking on my balls like she
couldn't get enough, her eyes constantly open and watching my reactions.


Suddenly, she pulled back slightly and let my balls pop out of her mouth. She
began running her tongue up and down on the underside of my cock.
Occasionally she would wrap her lips as much as possible around the side of
my cock and suck it or stroke her lips up and down, pausing close to the head.
She opened her mouth and placed my cock inside on her tongue rubbing it all
around without closing her mouth. I'd only seen this done in porno movies
and experiencing it was almost unbearable. She grabbed my cock with her
hands and closed her mouth about the head, slowly sucking it in until she had
about half of it in her mouth. She kept it there, sucking on it like a popsickle,
her eyes glued to mine savoring my every reaction. She closed her eyes and
started stroking her head up and down on my straining cock, going deeper
and deeper with every stroke, until finally all of my cock was buried in her
mouth. She ground her face against my stomach, twisting her head back and
forth, then returning to fucking my cock with her mouth. This sure wasn't
going to take too long. Nothing in my previous experience could possibly
prepare me for this!

I could feel my balls swelling, getting ready to expel my juices. I grabbed her
head and twisted it up without removing my cock and told her I was going to
come. I thought she would pull away and let me come in the air like in high
school but I was wrong. I removed my hands from her head as she mumbled a
negative and increased her sucking up and down. Again I grabbed her head
and started helping her up and down on my cock. The pressure kept
increasing and increasing until suddenly, I began to come! She thrust her head
down on my cock, taking it as deep as before. I shot jet after jet of come into
her throat while she continued to bob her head up and down on my deeply
engulfed cock. It was like I couldn't stop coming and she couldn't get enough.
As the flow lessened, she pulled her head back and began running my still
spurting cock around her face. The muscles in my body were shaking from
my tensing them. Finally I stopped and she took my softening cock back into
her mouth, gently licking and sucking it. She used her fingers to wipe off her
face and sucked off the collected come.

We both fell asleep. I woke up about an hour later, saw the time, woke up
Mary and said "I've got to get back on board ship." We dressed and I took her
home. I laughed when it turned out her home was only three blocks away
from the bar. I asked her why we didn't go to her house and she said she didn't
want her husband catching us! I couldn't believe it! I asked her if we could get
together again and she smiled at me and said " Who knows? You can find me
at the bar." She kissed me tenderly and walked into her house..... I went back
to the bar after we got back into port about 2 months later but she never
showed up. I drove by her house but it was up for sale. Nobody at the bar
knew what had happened to her or when exactly she left. I'm happily married
now with a wife that fulfills my every fantasy and desire so I have no need to
look for another woman. Still, I guess you never forget your first experience,
especially one as wild as that one was. I hated waiting until I was 19 but in
hindsight, it was well worth it! The message? Don't discount older women.
Their capacity to please can be overwhelming and their capacity to give can
be bottomless. Thanks Mary, wherever you are. I'll never forget you.....

The End
11 comments

READERReport

2008-04-14 01:39:22
Loved your story...I also lost my virginity in the Navy.
You mentioned Newport....RI ?? I was there too for a while. Most of my years in Norfolk. I enjoyed it !!

READERReport

2007-04-02 22:37:19
Yes, a she-male true story. With a guy's first time and liking it, and then continueing his desire for more male fun.

READERReport

2007-02-25 17:50:18
I agreed with Dan Reader. I was thinking the same thing. I would love to read about a true story of a guy ending up with a she-male and getting into it.

READERReport

2007-01-04 23:02:12
bravo! bravo! this is one awesome awesome story

READERReport

2006-03-18 14:49:19
has it all, geat story,first times always remembered

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