I was 16 and in 10th grade. We had moved around a lot since my father was in the Military. He had retired a few years earlier and my parents decided to retire in Miami. We lived in West Kendall, a suburb, and I went to Sunset High School.
My first years in Miami I was a little shy and didn’t fit in. Most of the kids in school were Latin. Both my parents were of Russian ancestry. I was always quite a bit taller (and paler) than the other girls. I was already 5’8” when I started High School. Sometimes they’d make fun of me since I looked like a grown woman while they still looked like kids.
When I entered High School, I started coming out of my shell a little and had a somewhat rebellious phase, perhaps driven by teenage hormones. I started to embrace looking a little older, and started dressing very sexy and trying to act older. I started smoking because I thought it made me look older and sexy.
I started getting a little of a reputation as a bad girl at school because of how I dressed and wore makeup. It was totally undeserved though, since I was still a virgin. Not to say I wasn’t curious about sex, because I definitely was. I fantasized about it a lot! Masturbation had become a nighttime hobby.
My best friends were Fernanda, Isabel, and Alejandra. We always hung out together. When we’d go out, I could sometimes buy us cigarettes and alcohol without being carded.
Sometimes, we’d just go over to Isabel’s house and hang out. Her parents were divorced and she lived with her dad, Daniel. He was very good looking! It was Alejandra that first said it. We were hanging out on the back patio and Daniel had just come home from work. She said “Isa, your dad is hot!”
“Yeah he is” I chimed in.
Isa looked mortified and said “shut up you guys!”
We liked to go to her house cause Daniel was a “cool dad” and let us do whatever we wanted, and stay as late as we wanted. At the time, I thought he was so much older, but I think he was only in his late thirties.
Many times we would flirt with Daniel just to tease Isabel. She would get so mad and wag her finger and scold us in Spanish. I never knew what she was saying, but it was funny. Daniel would be so embarrassed he turned beet red.
One time I came up behind him and put my arms around him and gave him a big kiss on the cheek. We had fun seeing how long he walked around the house with my red lipstick on his cheek. We giggled uncontrollably.
As time went on, I’d catch him staring at me a lot. I liked the attention. I’d dress to show off my long slim legs just to make him stare at them.
One night we were all going to meet at Isa’s house and hang out. I got there right at 7pm as agreed, but only Daniel was there. He opened the door “Hi Courtney, come in”, he said, “Isa’s not here, she’s with her mom and should be here soon. You’re welcome to wait.”
He had a pool table in his living room and was drinking a beer, probably one of several, while making some pool shots by himself. I leaned against the table watching him. “Want to play a game” he asks.
“I don’t know how” I respond shyly.
“Not at all??….Do you know how to shoot?” he asks.
“No, never tried” I say.
He stands on the same side I’m at and demonstrates, “hold it like this, one hand on the table”, he makes a shot. “Here take the cue.”
I take it and hold it awkwardly. “Put your left hand on the table” he instructs.
I put my hand on the table and he gets behind me. He puts his arms around me and puts the cue in my hands the proper way.
He puts his hands on mine and we bend over the table a little. He guides me making a shot. “See, just like that.” He says. As a horny young girl, I’m acutely aware of how he’s touching me, and how the front of his jeans brushes my ass.
He puts his hand on my waist “Move over here, we’ll try another.” I’m excited by his touch. I’m really enjoying the attention he’s giving me.
We make a couple more shots like that, his front to my back. Then I try one on my own, completely missing the shot. He stands behind me still just barely touching, his hands on my waist. “How’s that?” I ask.
“You’ll get it, it takes practice.”
I notice he’s still holding me by the waist with both hands. Gently moving his hands up onto my bare skin. I’m wearing a crop top. My waist and tummy bare, as was the style at the time.
I think about trying another shot, but I don’t want to move. I can feel his breath slow and heavy on my neck. His lips almost touching it. He moves his right hand down onto my hip almost onto my ass. His body just barely touching mine.
I don’t know why I did it, it was like a primal instinct, I gently pressed my ass back a little against his crotch. Sensing this, he gently pulls my hips slightly back, pressing his bulge right between my ass cheeks. I bite my lip thinking of the fact that his penis is now only 4 layers of clothing away from my virgin vagina!
We stay like that for several seconds. Gently grinding a little against each other. Then he turns me around facing him. He holds me tight around the waist pulling me close. With my heels, we’re the same height. His lips so close to mine. I can feel his heavy breathing against my face. I can smell the beer on his breath.
Slowly his lips begin to touch mine. Gently, sensuously kissing. His lips guiding mine to copy his movements. His lips are soft and warm. He holds me tight against him. I can feel his bulge right against my mound. His kiss is electrifying. All I can think about is how his lips feel against mine. He slides his hands down to my ass and squeezes it firmly. Shyly, I slide my hand down to the front of his jeans. He slips his tongue into my mouth just a little. I softly feel his bulge, I can feel the outline of his penis through his jeans! It’s so firm, he must have an erection! It was the first time I’d ever felt a man’s penis!
Just then, a car pulls into the driveway. Daniel hears it, releases me and backs away. “I’m sorry!” he exclaims, a look of panic on his face. He hurries into the bathroom.
A few seconds later Isa opens the door and walks in. I greet her “Hi Isa”, smiling.
“Hi Courtney! Punctual as usual!”, We kiss on the cheek.
Daniel comes out of the bathroom. I’m relieved to see he made sure there was none of my lipstick on his lips. “Hi honey”, he says to Isa nervously.
The other girls arrive, and we hang out in the living room. Daniel brings us some chips and sodas. I notice whenever he comes in the room, he tries not to look at me. He looks visibly nervous.
I try to socialize with my friends, but much of the time all I can think about is how Isa’s dad kissed me and how I felt the shape of his penis.
It gets late and we decide to all go home. As we’re all leaving, Daniel looks at me a smiles nervously.
I go home and get ready for bed. I lay there remembering the kiss and how Daniel’s body felt against me. I start to explore my body, imagining it going further. I remember how his penis felt and fantasize about what it might look like. I enjoy a nice orgasm and fall asleep.
A few days later, we meet at Isa’s house and plan to go to the movies. Daniel drives us. We buy our tickets and stand around for a few minutes outside of the theater. One of Daniel’s coworkers sees him and walks up. They exchange greetings, then the guy says “Is this your wife?”, gesturing at me.
“Oh, no, that’s my daughter’s friend.”, Daniel replies. The girls giggle.
After the guy walks away, we decide to go in the theater. Isa says to me “come on Mom!” We all giggle. Daniel blushes. I wonder what the girls would think if they knew that he had kissed me!
In the theater, I sit next to Daniel. I fantasize that I’m his wife, and we’re taking our daughters to the movies. I sit as close to him as I can without making it look obvious. He moves his leg closer so our legs touch.
Once in a while, I’d move my leg a little, rubbing it against his. I looked down at his crotch. It was dark, but it looked tight like he had an erection! I didn’t pay too much attention to the movie. I just fantasized about him laying on top of me, making love to me. I looked up at his face and caught him looking down at my legs.
It made me feel really good to know that he wanted me. My teenage hormones were surging! He had become my new crush. The rest of the movie I just sat trying to think of how I was going to get alone with him.
The movie ends and we leave the theater and drive back to Isa’s house. We spend an hour talking about the movie in the living room. When it’s time to go, I conveniently forgot my jacket and left it on the couch. I drive home, happy my little plan was in action! I knew Isa spends the weekends at her mother’s house, and Daniel would be there alone all day the next day.
Next morning comes. I shave my legs and most of my pubes. I put on my sexiest pink lacy satin panties. A tight black lycra skirt. I wear a push up bra and VERY low cut croptop showing LOTS of cleavage. I look in the mirror and I feel very satisfied I look older and sexy. I also put on some of my mom’s perfume, and borrow her high heels.
I drive to Isa’s house and knock on the door. Daniel answers. Surprised to see me he says “Hi Courtney! Umm...Isa’s not home, she’s at her mother’s house.” “I know, I left my jacket here I think. Do you have it?” “Oh yes, it’s here, come on in” he says.
I go in and stand there as he looks for my jacket. “Want a beer?” he asks. “Sure”, I smile happily. Pleased my little plan is working. I watch him as he goes to the fridge. He’s wearing a t-shirt and shorts. He look so hot! He hands me the beer. “Make yourself at home”, he says.
I take the beer, brushing my hand over his. “Thank you” I say smiling flirtatiously. I stand super close to him...almost touching. With my heels on, we’re the same height. I can see he’s looking down at my boobs. I hope he can smell my perfume.
I have no idea what I’m doing, I just want him to touch me and kiss me like he did before. I look into his eyes innocently. He looks nervous. “I’m glad you’re here” he says. I smile shyly and give him a flirty look.
He moves slightly closer and puts his hand on my waist. I close my eyes and open my lips a little. I feel his warm lips touch mine. He pulls me tightly against him and kisses me passionately. I open my mouth slightly and he takes the invitation slipping his tongue into my mouth.
This time the kiss feels different. It feels sexual and erotic. His tongue explores mine sensuously. I can feel how strong he is holding me so tight. My breasts pressed against his chest. I can feel my nipples protruding against him.
He stops kissing me and takes me by the hand. He leads me to his bedroom and he gently pushes me towards his bed. I lay on my back on his bed. He lays next to me, his arm around me.
He kisses me a couple of times then goes down to my cleavage pressing his face between my boobs. My nipples protrude and throb even more. God...I want his mouth on them! He reaches down and slips his hand up my short skirt and squeezes my ass.
I reach down and feel the front of his shorts. The material is much thinner than his jeans were and I can REALLY feel the outline of his penis this time. He definitely has an erection!
He pulls down my crop top a little exposing my nipples. He takes them into his mouth and gently sucks them passionately. It makes me feel drunk with lust! I squeeze his dick a little harder.
He reaches up my skirt again this time between my legs. I hold my breath as he starts to rub and caress my pussy. It’s the first time I’ve ever been touched like this! I start breathing again suddenly, panting and moaning a little. I can feel him thrusting his penis against my hand as I squeeze it.
We fondle each other for a couple of minutes. God it feels amazing! “I want you” he whispers to me. “I want you too” I whisper breathlessly. He wraps his fingers around the strap of my lacy panties and starts to pull them off. I lift my butt so they slip right off. He slides down and lifts my legs spreading them.
He kisses my inner thighs slowly and gently, each time getting closer and closer to my slit. I breath slow and deep, it makes me crazy with lust! Finally, he slowly runs his tongue up my moist slit. All the way to my clitoris. I feel the most erotic sensation I’ve ever felt in my life! It’s way better than any time I’ve ever touched myself.
I can’t help but let out a moan and pant a little. He does it again. It already feels like I’m gonna cum! He spreads my labia with his fingers and starts licking my clit in fast little motions. He knows just the spot! It’s right where I usually touch myself.
I start cumming right away, digging my nails into his wrist. He keeps licking and licking as I cum, until I start breathing hard. He stops, “Did you cum?” “Yes” I answer giggling a little breathlessly. “That was quick”, he says.
He slides up next to me and takes off his shorts and underwear, then pulls off his t-shirt. I see his completely naked body. He has a beautiful body. So sexy! I run my hand over his big chest. His honey tanned skin is so hot! I look down at his erect penis. I take it in my hand and stroke it gently. I’m afraid to scratch him with my long nails. As I touch him, I can feel him getting even harder!
Since he licked me, I think he probably wants me to return the favor. I slide down and hold his penis gently. I shyly wrap my lips around the head and slurp a little. He moans. It tastes salty. I take it deeper in my mouth and slide it in and out. I have no idea what I’m doing, but he seems to like it. I take it as deep as I can but I gag a little. His head swells in my mouth. As I suck it softly, I run my fingers over his hairy stomach and chest. God he’s sexy!
I love having his beautiful penis in my mouth. It’s so erotic knowing I’m giving him so much pleasure. I reach down and run my finger between my labia. I’m so wet!
He stops me and guides me to lay on my back. He pulls off my top and skirt. He goes to get on top of me between my legs. OMG, this is it. He’s going to have sex with me! I’m nervous as hell, but I want him.
He slides the head of his penis up and down between my slimy labia. “Wait” he says. He gets off me and started rummaging desperately through his bedside drawer. He finds a condom, tears it open and puts it on.
He gets back on top of me and starts maneuvering his head between my labia again. I pant heavily with anticipation. He starts to slide his penis into me. It hurts. “Ow ow”, “slowly” I beg. He pulls it back out and puts just the head back in.
“You okay baby”, we whispers. “Yes yes”, I nod nervously. He slides just the head in several time. I try hard to relax. He slides it slowly all the way in. It stings, but I force myself not to complain. I moan a little and dig my nails into his back. “Fuck you’re tight” he whispers in my ear.
He starts to slide it in and out slowly. It still stings, but I want him anyway. It feels so hot having this naked man on top of me, his dick in me. I want to enjoy this so bad. It does feel good. I try to ignore the pain. I moan and move my hips up and down slowly. He starts to thrust a little harder, moaning.
After about a minute, the pain mostly goes away and it just feels really REALLY good. It feels like I could maybe cum again. Just then, he start grunting and thrusting hard. I can feel his penis getting harder and thicker inside me. I think he’s gonna cum! He thrusts it deep. It hurts again, but I just want him to cum. He finishes, breathing hard.
He lays on top of me for a few minutes. We make out passionately. It felt so good making out with him laying between my legs.
Finally, he lifts himself up off me, and slides his penis out. It’s covered with blood, and there’s a little blood on my vagina. He gasps a little.
“Were you a virgin?” he asks, his eyes big.
“Yes” I reply shyly.
He sits up and sits on the edge of the bed facing away from me.
“Courtney”… he pauses for a moment. “How old are you?”
“Almost seventeen”, I answer meekly.
He appears to wince at my answer.
“I...I...don’t know…..I thought you were older….you’re just so....mature and sexy” the sound of regret in his voice.
“We shouldn’t have done this….I’m...I’m sorry.” he says. “Please...PLEASE, no one can know this happened”
I put my hand on his shoulder. “Don’t worry...I wanted it too….I won’t tell anyone.”
I never did. I stayed friends with Isa and her dad, but he never touched me again.
To this day, I remember it fondly as the most erotic experience of my life!