I was 16 when my cherry was taken. I'd been dating John for a few weeks. I must admit, I
was really starting to develop strong feeling for him. I asked my Dad when would be the
right time to go farther with him. Dad just said that I would know when the time was
right. My 15 year old brother was also jealous that I was dating. I'd known for awhile he
liked peeking at me whenever he could get a chance. Sometimes I didn't even mind, it
may me feel attractive.
It was a Friday night, I'd came home after another wonderful date with John. We kissed
at the door when he dropped me off for the night. The kiss made me very wet.
I took a shower and fingered myself while thinking of John. I imagined him in the
shower with me, rubbing his hand over my pussy as he sucked on my nipples. Then
imagined his kiss from earlier, while he took me in the shower. As I climaxed it took
every bit of restraint that I had not to shout out and wake the family.
After the shower I put on a T-shirt and panties. I then cuddled up in bed, very happy and
feeling good after my date and shower.
I drifted off into a peaceful sleep, but was awakened a short time later.
I was in my bed, laying on my tummy with the right sided of my body slightly upwards
and my right hand under my pillow. My blanket covered most of my body, except for my
lower legs, ankles, and feet.
I was awakened by a curious sensation at my feet. It felt really good, but scared me at the same time. Somebody was in my room, and touching my feet. I remained quiet, but he continued to play with them. I was frozen in place by fear and at the same time, enjoying the feeling of his touch. At first he was just kissing each toe, but then he starting sucking on my big toes. This made me gasp as it sent chills throughout my entire body. I love everything about feet, especially when my own is being touched. This made me curious since I hadn’t told John about it yet.
My mystery man continued to suck on my big toes despite my soft moans. His hands
began to rub the arches of my feet. I gasped and moaned again as it felt so incredible. My panties was starting to get wet, my pussy was so turned on by all this footplay.
His hands pushed the blanket out of the way. Then they began to rub up the back sides of my legs while he kissed and licked the heels of my feet.
Whoever this person was, he was seriously turning me on, even after my earlier orgasm. I was still a virgin and wondered if I should really be doing this. But I was so horny, and he was so gentle, I wanted him.
He started to kiss the back of my heels and then my ankles. Meanwhile his hands was
rubbing over my inner thighs. Oh god I was so horny at this point, I spoke out and
moaned louder. No more pretending to be asleep.
"Oh yeah.. That feel so wonderful!" I said to the mystery man.
After speaking, he stopped all his actions for several minutes. I think I scared him, but
once I was silent he resumed again.
His hands now rubbed over my ass and he kissed all along my lower back.
I started to twist around and see who he was, but he applied pressure to my ass to keep me on my chest.
"Stay on your tummy" The voice spoke in a whisper I couldn’t recognize.
His right hand then slid under me, and under my shirt. His hand groped my right breast
and his fingers rubbed my nipple. It was so hard and felt so good with his hands rubbing over it.
"Oh.. Mmm... I love your touch!" I said to him.
"Don't worry, more touching is coming up" He again whispers silently to me.
I then felt his hands removing my panties. He slid them all the way down my legs and to
my feet. Once they was off of my feet, he took that chance to lick along the bottom arch
of each foot. The sensations was incredible, eventhough I felt so vulnerable in just a
"Oh god... That feels Great!!" I said while moaning softly to him.
I was so wet that I think he knew it too. He hands returned to my ass and rubbed over
them in a circulator motion. It felt much better than before with my panties out of the
way. What came next was a total surprise.
"Oh Shit!! Oh fuck!!" I yelled out in pleasure as I felt his hand rubbing over my pussy and
then my clit. This was the first time a guy had ever touched me there and it was far better
than anything I could ever do to myself. I felt like a fool for yelling out, and hoped that
the family didn’t hear it. He continued rubbing the outside of my pussy for about a
minute. But to me it was an eternity of pleasure. Before I knew it, I felt another burst of
great pleasure as he stuck his index finger inside of my pussy.
"Oh! Oh!!! Ohhhhhh GOOODDDDDDD!!!!!" I shouted out quietly into the pillow and I
instantly cam on his finger. The sensations of feeling something inside me that I wasn’t in control of felt so incredible, I couldn’t hold it. His finger instantly was covered in my
juice. When he pulled out his finger I heard him licking his finger. He must have liked
the taste because he continued to stick his finger in my pussy to get more juice and then
lick it clean again.
I was in heaven, and was hopeing it wasn’t over yet. A couple minutes later, I got my
wish as I felt his finger enter inside of me again, but this time with his middle finger as
well. This one still felt incredible, but also started to hurt. I moaned and cringed in pain
at the same time. He was unaware of my pain until he pulled out his fingers and saw
alittle blood on his hands.
"Sorry about that. I guess more fingers aren’t going to help now" He whispered to me.
I really wish I knew who my mystery man was, but I also didn’t want to ruin this
wonderful moment. His voice was still hard to figure out from the whispers, His body
was hidden by the darkness.
While I was busy trying to figure out who he was, I heard a zipper. My thoughts instantly
switched to what might be coming next. I then heard him slide off more of his cloths.
His hands rubbed my ass once more, then lifted it up into the air. I knew what was
coming and didn’t resist, instead I made sure my body remained in that position for him.
His hands then rubbed up my back side, traveling there way up my body. When they
reached my shoulders I thought he would stop, instead one hand reached around my neck.
He was so gentle and it felt so great, I didn’t worry about his actions, eventhough when
looking back he could’ve hurt me.
What happened next took me my total surprise as his hand came around to the front of my face then covered my mouth. I was scared and worried at this point, but then I felt his
manhood pressing against my pussy. I started to relax again which quickly changed the
moment the head of his cock started to enter me. The pain returned, and I was screaming out into his hand. Now I understood why his hand was over my mouth. To keep me from waking up the family as he started to push in.
His manhood pushed into me a inch at a time. I had no idea how big it was. All I knew
was that he was stretching my virgin pussy and tearing out my hymen. The pain was so
bad, I had tears coming out of my eyes.
Once he was all the way inside of me, he leaned down and whispered into my ear.
"I’m sorry about all the pain, it was the only way" He said and then kissed my ear before
leaning back up. As the pain started to pass, I began to relax. He pulled his hand away
from my mouth and rubbed it over my right breast. He could feel my hard nipple and
knew I wanted to continue.
He then started to thrust very slowly. Pulling almost all the way out and then back into
me again. There was still pain at first, but it was soon replaced with pleasure. His thrusts was slow and gentle, each time it would hurt less. And the more I wanted him to
continue. His cock started to go faster as I softly moaned for him. His cock felt so good inside of me, that even with slight pain, I was in heaven. This was even better than anything I had imagined.
"Give me more.. Oh yes..This is great" I said to him.
His thrusts then began to go even faster. My whole body was now on fire with a passion
that cant be described. His hands rubbed my back and shoulders as his manhood
continued to pound. I couldn’t believe it all. I was being pounded by a unknown male,
from behind, in my own bedroom, and he took my cherry on top of all that! Was it really
John, or was it my father or brother?? Or some lucky robber?? I didn’t know and didn’t
care at this point. My body was lost in lust. My toes curled from the excitement. I bent
my lower legs back to try and rub them against his body. I think he liked the idea,
because I felt one of his hands reaching back and rubbing my foot. This increased my
arousal even more, I felt my body getting so close to a climax now. He too was pounding
me very hard, and his breathing was so deep I could hear it in the darkness. It was so
incredible I pushed my face into my pillow to muffle my loud moans.
"Oh God... Oh Oh OH!!... " I said while trying to fight off my orgasm.
It was so intense I didn’t want it to end, but as he keep pounding me so hard and fast, I
couldn’t hold back anymore. Then I had the most amazing orgasm yet.
"Oh Fuck..Im cumming... YES YES YESSSSSS!! I yelled out, muffled by the pillow.
My entire body was in a state of ecstasy as his cock continued thrusting into me. My
pussy tightened up around is cock even more has I enjoyed every moment of my orgasm.
At this point I was waiting for him to cum, but he kept thrusting and breathing hard. My
own moans just couldn’t stop it was so incredible. I could’ve never imagined it would
feel this good.
As my body climbed back down, His cock was still stimulating me. Almost like I hadn’t
climaxed at all. This was so amazing, That I was glad it wasn’t over yet. His hand's
fingers slid inbetween all my toes at once. As his fingers spread my toes apart, it felt so
intense. I quickly began to build back up again. My body was squirming around as he
continued to thrust. I was so loving it.
"Oh yes.. I love being a woman! I so do!" I said to him.
"Oh your a woman now? If you are how do you feel about having cum inside you pussy?"
He question to me in whispers.
As he pounded into me, I thought about it. I loved his cock, loved his thrusts. I would
love feeling his cum inside me too wouldn't I?
As my body became more and more aroused again by his continued hard pounding. I
loved the idea more and more. At first it sounded disgusting, or worse, could get me
pregnant. But now with my body ready to climax again, I loved the idea of feeling his
cum in me. I wanted it... I was ready to become a woman. If that meant having his baby, I
no longer cared. I wanted to feel everything that a real woman does, and that’s exactly
what I was ready for.
"Yes! Yes! I do want it" I said to him.
"Mmmm.. you'll get it then" He said back to me while his cock pounded even harder than
before. Each thrust would go all the way into my pussy, and then out to where only the
tip remained inside of me. He lowered his chest on to my back. His cock felt so incredible going so fast. My body again was totally on fire and ready to feel another climax. He felt like a animal as he pounded away. I couldn’t believe I was already going to repeat that amazing orgasm I had just moment ago. And yet, I was very eager to feel it again.
"Oh yes.. I’m so close! I’m ready! OH YES.. I want your cum!" I said to my mystery man.
Then I felt it. His cock became very hard, and then warm fluid filled my pussy. The
sensation was so incredible, It pushed me over the edge. I began cumming with him.
"Yess.. Yessssss...YESSS!!" I said as he filled me up. I once again enjoyed a state of
ecstasy and this time knowing he was too.
I could feel each shot as it filled up my pussy with hot cum. I had no idea it would feel
that good to have a man cum in you.
I never wanted it to end, I moaned and loved every moment of his orgasm, and my own
kept going until his was done. My God! I thought to myself as my entire body was alive
like never before. I loved being a woman. I felt like I was reborn into a new reality.
I was breathing so hard afterwards, and my body was so sensitive to even the slightest
"Incredible" I whispered to him softly.
When he was done with his last rope and started to soften, he slide his manhood out of
me. Instantly I felt less complete, yet full of something new.
Before I could turn around to see him, he managed to slip back on his cloths and head out the door. He must have just pushed his cloths down to his ankles and then quickly pulled them back up as I was laying there enjoy the afterglow.
The guys that took my virginity just vanished into the night. And all I have to remember
him by is my memory and a pussy full of cum. If it was John, wouldn’t he have told me
at the end and then cuddled? Who was the wonderful lover that just took my virginity!!.
As I look back, I regret nothing, It was a wonder experience, I would gladly do it again,
I had to find out who did it, my curiosity was to much. Who was my first lover! I started
my own investigation right away, but without many clues to go by, I had to improvise and
use some unique techniques to eliminate the suspects one by one.