Cindy was my best friend’s sister, and we had
gone to Sunday School together for years. I had noticed
that she was a pretty girl with long brown hair and
very large breasts, especially for a 18 year old.
But she was a shy and quiet little loner who also
seemed devoutly religious. I didn’t know her very well.
So, imagine my surprise when I came in from school one
day and my mom asked me if I would like to take Cindy
to a movie. As mom explained it, she and Cindy’s mom
were talking that morning, and they decided that I
could help Cindy come out of her shell.
Looking back on it now, I can’t believe our mothers
were that stupid. But they really did have no idea what
was going to happen. Of course I said I’d do it.
Nothing much happened at the show that night. We held
hands, and talked. I had never seen Cindy talk as much
as she did that night. I knew she was into me, and I
made up my mind that night to split her cherry.
We went out several more times over the next few weeks.
We would sit together in church, and then she’d spend
the afternoons at my house. My room was a converted
garage, and you had to go outside to get to the main
house. It was the perfect place to take Cindy when my
parents settled in for their Sunday afternoon naps.
We would always start out kissing, with me telling her
how beautiful she was. Cindy loved the kissing and
really ate up the compliments. One Sunday afternoon in
my room I felt her breasts through her clothes. Cindy
protested, but she didn’t stop me. As I felt her Cindy,
she talked on and on about how she was “pure” and
planned to be a virgin for her wedding night. I didn’t
laugh — just kept agreeing and kissing her as I
unbuttoned her blouse and unsnapped her bra.
Suddenly she realized that her creamy white breasts
were exposed. Her cheeks flushed and she clutched at
her clothes. But I just looked into her eyes and told
her those breasts were the most beautiful things I had
ever seen and that I felt honored to see them. Cindy
slowly relaxed as I toyed with a nipple, and she
finally let her blouse slide away. I kept reassuring
her about how much I loved and respected her, and how
she didn’t have to be afraid of me.
The next Sunday we were back in my room, and it didn’t
take me long to have Cindy’s blouse off again. By now I
had realized that I could do just about anything I
wanted to her as long as I was calm and gentle and kept
looking into her eyes and reassuring her that I loved
her and wouldn’t do anything to hurt her.
I heard her breath quicken as my tongue flicked across
her nipple, and I slowly eased my hand up her skirt.
Cindy gave me a concerned look, but she calmed again as
I reassured her and I ran my hand along the inside of
her thigh. I told her she needed to trust me, and she
started insisting that she did. Later on I persuaded
her that she would be more comfortable without her
pantyhose, and she took those off herself.
I didn’t go any farther that day, and we talked for a
long time about how important it was for us to trust
each other, and how I respected her decision to remain
a virgin until she was married. Her big innocent eyes
sparkled with anticipation when I reminded her that she
would be a virgin until she had had a penis in her
vagina. Nothing short of that could take away her
Yeah, I know, I was full of crap. Actually I was pretty
evil, deliberately lying to an innocent young girl to
trick her into trusting me with her most precious
possession, when all I really wanted to do was to take
it from her. But, a hard-on has no conscience, and I
definitely had a hard-on then.
I did it the next week. With all the groundwork I had
laid it was almost too easy. I got her blouse, bra and
underwear off in short order, and I laid it on thick as
I played with her tits and clit. She came a couple of
times, and was just lying there was all juiced up and
relaxed when I realized that all I had to do was get my
dick out and roll over on her. I decided to go for it.
I reached down with one hand and freed my penis, then
locked Cindy in a big deep kiss and rolled over between
her legs. She was so shocked that she just laid there
with big eyes as I positioned myself at the entrance of
the vagina. Big tears started welling up in Cindy’s
eyes, but I kissed them away. Before she could gather
her composure to speak, I pushed forward gentle but
firm, until I felt Cindy’s hymen give way. Oh, she was
tight, and the way her body quivered with her quiet
sobs only excited me more.
After a few minutes Cindy started to whine, but I
warned her that my parents might hear her through the
wall and come out and catch us. I asked her if she
wanted that, and struggled to stifle her sobs. As I
felt my moment coming and started banging into her
faster, she whined that she didn’t want to get
pregnant. I looked Cindy in the eyes one more time and,
as I sprayed her insides with a mighty load of stick
cum, I looked her in the eyes and promised her I
wouldn’t get her pregnant.
Cindy cried off and on the rest of the afternoon and
evening, and I was afraid she would give us away. But
she never did.
We used condoms after that. I fucked Cindy every Sunday
after that. One time, I even persuaded her to let me
fuck her in the ass because she was on her period.
After that we drifted apart and I have only seen her
once or twice since then.
I still think back sometimes about how sweet it was
lying between those virgin thighs, of how it felt when
Cindy’s hymen stretched and finally snapped under the
weight of my penis. I will never forget the wonderful
way her freshly de-virginized pussy winced and squirmed
as she sobbed, or the waves of sensation that swept
over me as I pounded that freshly de-virginized hole
and filled her innocent body with my sperm.
That day it was great to be me. But it probably kinda
sucked for her.