Losing my virginity

By | 24 October 2019

Losing my virginity at the age of fourtheen

Losing my virginity was a real bless when I was fourtheen years old. As a
fairly normal male, I’d been sexually active for quite some time, but that
friday evening was the first time someone else was involved physically!

I was a competitive swimmer, and I guess I was pretty good looking if
I believed what the girls said. I was big for my age at 6′ and 165 pounds,
and I developed early. I was well muscled and had just the start of a now
hairy chest. Being on swim-team kept me in excellent shape, and I always
wore nylon racing suits to the beach.

Janey was a college senior and she had a summer job as a life guard at
the county beach on the lake. Tall, blonde, built like a lifeguard is
supposed to be built, and in the red-and-white-stripped racing suit all the
guards wore, she was my adolescent dream come true. Having just broken up
with her boyfriend of four years, she was not overly friendly with the older
guys that she attracted. She said that she wanted some time to herself to
get her emotions straightened out.

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I had taken my Red Cross lifesaving course at the “Y” the previous
winter, and because I was qualified, Jane let me sub for her when she’d take
a break. We got to be good friends, and as the summer progressed, we became
pretty close. She would talk to me for hours as we sat together on the
oversized lifeguard stand. Mostly she talked about Simon, her ex-boyfriend,
and every so often I could catch a hint of arousal in her voice when she
told me of how much she loved him. One time, she was talking about she much
she missed being held by him, and I just put my arm around her shoulder and
hugged her to me quickly. I was surprised when she put her head on my
shoulder and sort of snuggled closer for a minute. Another time, we were
talking, and she let slip that Simon spent the night in her room from time
to time and I jumped at the chance to hear all about it. Janey was embarr-
assed that she’d said too much, but I told her that I wanted to hear all
it. She looked me right in the eye, in the middle of the afternoon on a
crowded beach, and asked me, right out in the open…..”are you a virgin?”
I dropped my eyes in embarrassment and nodded my head. I realized that I was
looking right at her nipples, and they were getting hard! She was excited
over the fact that I was a virgin, and I could tell from her reactions! I
must have blushed three hundred shades of crimson, both from the embarrass-
ment of her finding out and me seeing her reaction. “There’s nothing to be
ashamed of…….everyone is a virgin until they do it with someone else.”
she said putting her hand to the side of my face. “I was just about your age
when I lost mine.” I blinked at her and sort of stared and stammered “Will
you tell me about it?” “Not right here, right now, silly!” she sort of
purred…..”After we close down at sundown, meet me back here and I’ll try.”
Right after she said that I couldn’t stop thinking about losing my virginity.

It was about 4 o’clock, and I had to cut the lawn at home, so I assured
janey that I would indeed be back around 8. I rode my bicycle home and
proceeded to tend to my chores, and all the time trying not to think about
what I was going to hear that evening.

My parents had left the day before for a long weekend at the Girl Scout
camp, and taken my younger brother and sister with them. I was left to fend
for myself, but, under the watchful eye of Mrs Goyke (our neighborhoods
semi-official aunt/baby sitter/overseer/busybody. I think you know the type!)
I went over and told her that I was going to the movies with my friend from
the beach, and that I’d be home about ten. She said that if she didn’t see
lights on in the house by 10:30 she was going to call the cops and my folks
in that order…..Oh she was a wonderful lady, but didn’t know that I was
losing my virginity probably that night.

I went back to the house and got the timer off the coffee pot and
plugged my desk lamp into it and set it for 10:10, and went about my task of
trying to make myself as grown-up as I could for Janey. Around 7:30 I rode
back to the park, and went to the far guard-stand and waited.

About five minutes later I heard a car drive up into the now-deserted
beach lot. Glancing anxiously I spotted Janey. She was wearing a light
grey warm-up suit over a tank-top. As she came nearer, I could hear my own
heart pounding in me ears, and thought she’d hear it, too and think I was a
silly little kid. As she came up to me, she leaned over and kissed me on
the lips softly and said “I brought some special coffee in case it gets cool
later, and there’s a blanket in the car so we can sit on the beach.”

We climbed up onto the guard-stand, and she sat with her back to one
side and I sat with my back to the other. As the seat is only about three
feet long, this gave us just enough to be comfortable. The park lights were
on, but I had chosen the guard-stand furthest from the nearest light and it
was really quite dark.

Janey asked how it was that I could be out this late, and I explained
that earlier cautions I had taken for Mrs. Goyke. She just laughed and said
that I was a resourceful guy and she really liked that.
We started talking about just stuff in general, and then she asked me,
out of the blue, if I had ever seen a girl naked before! I stammered and
turned purple, and stuttered. She said “If you want me to be honest with
you tonite, you’ll have to be honest with me.” I agreed and told her about
playing “doctor” with a couple of the neighbor girls, and about looking
through the hole in the ladies dressing-room here at the beach, and about
looking through every girly magazine I could get my hands on. She laughed
a little and said that she’d guessed as much. Next she asked if I knew what
making love was all about. I answered that I’d taken Sex-Ed in scouts, and
had seen the animals at the farm, and had read some stories in this one mag-
azine, and I guessed I knew about it. (Right, sure I did!!) Next, came the
question that made me almost fall off the stand……”When you look at the
pictures or read the stories, do you masturbate…..do you jerk-off?”

“NO!, No I don’t jerk off, that sick, for queers!” My adolescent ego
blossomed in incredulity. “Only homo’s jerk-off” I said proudly. “Wrong-O”
she answered with a big grin on her face. “I jerk-off and I’m not a homo or
a queer.” I stared blankly, stunned. “But you’re a girl, er a lady, you
CAN’T jerk-off!” And with that she proceeded to explain that women can, and
often do “jerk-off” when there’s not a man around to satisfy their sexual
needs, but it’s not really jerking-off like men do it. “How would you know
how men do it?” I asked. Janey went on to explain that she and Simon (Oh ya
him again) would do it to each other sometimes in bed. I asked how women
did it, and she tried to explain. Verbage couldn’t get her point across as
well as she wanted so she dropped her hands to her lap, and demonstrated for
me, through her warm-up pants. I watched as she slowly rubbed between her
legs, and I imagined her fuzzy crack with the pink lips in the center. And
I watched. I watched as she slid her left hand inside her jacket and pulled
at her nipples through her t-shirt. I watched as her right hand pressed the
material of her pants into her pussy and heard her breathing deepen. I saw
the moisture soak through her pants, and heard her gasp slightly as her
fingers pressed against her clit. I was mesmerized by her actions, and my
own hand fell to my lap as I started rubbing my now rock-hard 14 year old
cock through me shorts. Her left hand was squeezing her right breast, roll-
ing the nipple between her fingers, and she sort of slid her hips down on
seat. Her eyes were half closed and she was purring like a kitten when she
slid her hand up to the waistband of her sweatpants and pulled the string
that secured them. Janey ran her hand inside her pants, and I could both
see and hear as her fingers slid across her clit and into her hole. She just
sort of gasped and started panting like a sprinter. My own hand went inside
my shorts, and I grasped my tool, sliding my fist up and down its length.
Watching her hand under her pants move faster, and hearing the almost animal
sounds she made between gasps was bringing me to a place I had never been.
I realized that even after my protestations about jerking-off, here I was
with cock-in-hand pounding my pecker in front of a girl! That thought made
me slowdown just in time to witness Janey start to shake and quiver. She
threw her head back and hissed through clenched teeth “YES, OH GOD, YESSS!”
I watched slack-jawed as she slowly calmed down and opened her eyes. She
was smiling at me and she just sort of glowed.

“So, jerking-off is just for queers and homos, huh?” she chided as she
pulled her hand out of her pants and raised her fingers to her lips. Stop-
ping, she moved her right hand toward my face, and in the night air I got my
first wonderful smell of a woman. “Taste it…” she said. Entranced by the
musky aroma, I tentatively, then with more vigor licked her fingers clean.
Janey’s other hand started rubbing the bulge in my shorts, and she asked “Do
you mind if I jerk you off?” All I could muster was to shake my head. She
unsnapped and unzipped my shorts and slid her hand inside, encircling my now
bone hard and throbbing cock. Slowly, she stroked me up and down, the warmth
of her hand causing me to groan out loud. Her other hand tugged at the
waistband of my shorts and I lifted my hips to let her pull them down a bit.
With my cock free in the night air, I slid lower on the seat, and she en-
circled my rod with both hands. “Tell me when you’re going to shoot-off, I
have a surprise for you.” she whispered huskily. As her hands continued to
slowly stroke, Janey lowered her head towards my lap. As my hips started to
match her rhythm, I croaked “I’m gonna shoot!” and with those words, she
lowered her mouth and engulfed my cock. Talk about cumming until your nuts
collapse! As I came in her mouth, she sucked and swallowed and sucked some

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As I calmed down, and my tool began to shrink, Janey raised her head,
smiled and said “Why don’t we get down from here before we fall off and
injure something we may need later.” Later, did she really say later I
thought with growing anticipation. We climbed off the guard-tower and, with
me trying to act cool while holding up my shorts with one hand, spread the
blanket on a little point near the beach. “Go back to the car and get the
thermos and the other blanket.” Janey said, and I was off like a flash. As I
returned, I caught sight of Janey putting her warm-up top back on, and as I
sat down I realized that she had taken off her t-shirt and pants and was
sitting there in her panties sitting with her back against the tree. I
handed her the blanket and she placed it around her shoulders letting it
flow around her like a cape. “You have a lesson to learn, young man, one
that every man should know” she said softly motioning me to lay down between
her legs. My face was about even with her ankles as she reached for the top
of her panties and pulled them down. My eyes must have looked like two tea
cups and I know my mouth was hanging open. I was laying not two feet from
the first real post-pubescent pussy I had ever seen. She spread her legs and
feet a bit and said softly, “Get comfortable and make sure you can see.”
With that Janey proceeded to give me the first anatomy lesson to which I
ever really paid attention, pointing out the terrain and explaining what
each part did, and which was most sensitive. I learned about the clitoris,
vulva, major and minor labia (sounded to me like constellations, and I said
so) and, ta-da, the vagina. Pussy, cunt, beaver, snatch, hair-pie and the
others were not in the vocabulary that night, as I got acquainted with the
finer points of a woman’s sexuality. As she continued with the explanation
she took my hand and let me feel each part. I pressed my index finger along
her clitoris and felt the tip. I traced the edges of both the labia major
and the labia minor. And I even slid my finger into her vagina, where it was
wet and warm and wet! As she spoke, I realized that janey was starting to
breath harder, and as I slid my finger into her vagina the second time, she
gasped and shuddered a little.

“Now you’ll learn about cunnilingus.” she said in a husky low voice and
she explained that a man could give a woman great pleasure with his mouth.
“Just like the pleasure I gave you before.” Ahh, fellatio. I followed the
directions she gave, both spoken and otherwise, and after Janey had cum, er
…reached orgasm, twice more I looked up at her. In the light of a three-
quarter moon I could see that she’d been pinching and squeezing her breasts
as I ate her.

Laying on my stomach, my cock….er, penis….my VERY hard cock had
just about dug a furrow in the dirt through the blanket, and I was a little
embarrassed when she told me to sit up. I never had fastened my shorts, and
the tent I made in my underwear wagged like a flag in the moonlight. “You
look like you’re about ready for your next lesson” Janey said with a smile.
“Slide your shorts off, and sit here between my legs.” I did as instructed
and as I inched closer to her she unzipped her top, put her legs over the
tops of mine with one on either side of my waist, my legs under hers and
around her butt. She reached down and pulled off my t-shirt and put her
arms around me, hugging us closer together. I was keenly aware of two things
at that moment: her bare breasts were pressing against my bare chest, and
my very hard fourteen year old cock was pressing against her bare pussy with
only the thickness of a pair of jockey shorts in the way! I almost came
right then.

Then, Janey took my face in her hands and kissed my full on the lips,
softly at first, then with more passion, and finally our tongues fought a
duel. As she leaned back slightly, our first kiss broken after only a few
moments, she said “Now you are about to become a man!” She slid her hips up
as close as she could to my cock, and rubbed her pussy slowly against the
underside of my shaft. She reached between us and pulled the front of my
jockey shorts down and tucked them under my balls. My cock literally ached
as she touched it. Pressing it down she rubbed the head against her clit
and then around the opening of her vagina getting it all wet and slippery
with her juices. She raised her hips up an inch or so and I felt the most
exquisitely warm, soft, exciting feeling I’d ever felt as my erect penis sank
slowly into her very wet, very warm, very wonderful vagina. I pressed for-
ward and she pressed forward and I was all the way inside her! “Just be
still and feel what it’s like.” she whispered. The muscles in her vagina
slowly rippled around me and I gasped in both astonishment and excitement.
“Aren’t I supposed to do anything?” I asked sheepishly. “No, not right now.
later maybe, but this is all for you to experience and enjoy. I’ll teach
you what to do when we do this again, later.” she said. She’d said “later”
again, I almost came right then from the thought. Janey pushed against me
and I lay down on my back with her still sitting on my cock. Drawing her
legs under her I was introduced to the classic “female-superior” position in
a matter of seconds. “A woman can adjust the angles and depth and speed in
this position, and it’s easier for me to reach orgasm this way. It’s been
so long since I’ve had a man inside me, I want to make this first one last.
You tell me if you’re gonna shoot-off…er, cum, and I’ll slow down.” Well
I wasn’t going to say anything then, but I’d jerked off three times in the
shower just thinking about her, and I had cum again on the guard-stand. I
may have been a virgin, but I had had the edge taken off a bit, so I didn’t
have to worry about being too quick on the trigger. Janey rode my cock for
what seemed like a fifteen minutes. She’d twist and turn and pump and gasp
and then she’d start cumming. She came five times, before I started to lose
total control over my balls. “I’m gonna shoot soon” I moaned, and she just
ground down against me getting me as deep as possible. Shoot I did, and cum
and squirt and moan and groan and cum some more. I heard Janey sobbing “YES
Yes, yes” above me as she shook and spasmed, the walls of her cunt milking
milking my cock over and over this was really the best way of losing my virginity.

She finally collapsed on my chest and we hugged and kissed and she
cried against my shoulder. I asked if I’d dome something to upset her and
she sort of laughed and said “No, silly, I’m crying because I’m so happy!
Thank you so much.”

“I didn’t do anything to be thanked for.” I said, and she just snuggled
closer and whispered “You may never know how much you’ve done for me

We spent the rest of the night on that blanket beside the lake. Janey
took her time and taught me how to make love to a woman, and she taught me
how to fuck a woman when she wanted to be fucked, but most of all she taught
me the difference. I will never forget our first night together, because
it was also our last. She wrote me a beautiful letter before she left the
next Monday for Chicago to start her new job. In it, along with a picture,
she wrote that she was sorry to have not told me about leaving, but that she
thought it best this way. And that I would make some young lady very happy
when the time came for me to teach her what I had learned.

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