June 2009
I remember when I first started fantasizing about older men. It was the summer before college and I had just turned 18. I was visiting my friend Lacy's luxurious beach house, situated along the Florida coast. It had everything: sprawling beds, views of the beach, a pool, and a hot hub. Lacy and I spent two weeks skipping along the boardwalk, eating sno-cones and tanning along the beach. We had the time of our lives. Lacy's parents gave us free-range of the house—we could stay up late, entertain boys (oh, the hot tub!), and even raid the liquor cabinet from time-to-time. There wasn't a day we returned to the house without sand in our flip-flops, hair, and bathing suits!
One late night after retiring to one of the lovely guest rooms, I couldn't sleep (not an uncommon occurrence for me, even these days). It was past 2am. I put on my silk robe and slid past the door, hearing Lacy's brother Evan snoring in the next room. I descended the stairs, making sure to stay quiet as to not wake my friend and her parents. One I reached the first floor, I clumsily made my way towards the cabinets, anxious for a glass of water. I filled my glass with ice and water as quietly as I could, then made my way towards the gracious and breath-taking view of the beach afforded to us by the large windows.
I swirled my manicured finger around the top of the glass, taking in the view of the waves crashing along the Florida shore. I began to get lost in my thoughts, daydreaming about the events of that night.
Lacy and I had brought two guys home. They were alright, I figured. The one I was interested in, Shawn, had cuddled with me in the hot tub. He and his friend were both visiting with their family. He was into interesting stuff, I guess—surfing, music, skateboarding. We had kissed that night, but as I thought about it I remembered how passionless and forced it seemed. I sighed. I hadn't had much experience with guys, but that wasn't for lack of trying. I never seemed to be too attracted to boys my own age, but this wasn't something I would realize until that summer.
My thoughts were quickly interrupted by the sound of shuffling feet in the kitchen. I turned around, expecting to see Lacy in her flowing nightgown. Instead, I was greeted by the disheveled image of Lacy's father, Greg, standing in the kitchen in only his boxer briefs. It took a moment before he noticed me standing by the window.
"Oh, hey!..." he exclaimed, eventually trailing off when he realized he had entered the kitchen in only his boxer briefs.
"Hey, Mr. Richardson," I said quietly, trying my damnedest not to stare towards the direction of his crotch. I fiddled with my bathrobe and looked up at him.
"What are you doing up at this hour?" he asked. I watched his eyes dart to my chest then quickly back to my eyes.
"I can't sleep," I said, sighing. I was visibly blushing at this point.
"Me either," he said, turning to look out the window at the crashing waves.
There was an uncomfortable silence at this point. I could feel myself growing slightly aroused as I smelled his aftershave. This was a sensation that I hadn't experienced before—at least not with this level of intensity. I fiddled with my robe some more, untying it and tying it again. Greg was so close I could hear his slow breath and see the fog accumulating on the glass as he exhaled.
I looked down, slowly, before I realized what I was doing. As Greg was absorbing the view, I sneaked a view at him in his boxer briefs. What I saw there I will never forget. He was hard as a rock, bulging against his tight briefs. I couldn't bring myself to look away. I took it all in: his huge cock, the smell of his aftershave, and the fact that we were all alone. I couldn't stop staring!
Suddenly, Greg cleared his throat and I was jolted out of my daydream. He had noticed me staring and had turned to face me. I looked up into his green eyes, nervous and fidgeting with my bathrobe again. He was much taller than me: 6'3", at least.
I felt myself grow hot under his towering gaze, thinking thoughts I'd never thought before in my 18 years. I saw his eyes move from my eyes to my chest and then all the way down to my toes and back again. I grew even hotter as he took me in.
"You're very beautiful, Emily," he said quietly, blushing as he uttered my name. I smiled as my eyes darted back to his huge bulge.
"And you, Mr. Richardson..." I said sheepishly, again unable to tear my gaze from the outline his cock made in his boxer briefs.
"Call me Greg," he said softly, his eyes still trained on my breasts.
"Yes, I'm sorry, Greg..." I trailed off, unable to think of something to fill in the sexually-charged silence.
"I should... I should get to bed. We should both get to bed. It's near 3am..." he said, looking around. His eyes eventually scanned the stairs, no doubt worried his wife might come downstairs to find him dangerously close to his daughter's virginal 18-year-old friend. Not to mention the fact that he was only in his boxer briefs and sporting a monstrous hard on!
I nodded in agreement, walking to the stairs. I began to climb, aware that he was directly behind me with a full view of my ass. I swung my hips back and forth deliberately as I made my way up the stairs. As we finally reached the landing, he turned towards me to say goodnight. His cock (I was still staring!) had grown even harder during our climb. I felt myself grow wet as I took in the view again. His eyes were still on my chest and I could see him tremble with what I hoped was desire.
I stared up at him, finally fully realizing the sexual tension between us. This was nothing I had ever felt while with boys my own age. He was strikingly handsome with intense green eyes, brown hair and a commanding presence. I shifted my weight, suddenly nervous with anticipation and arousal.
"Goodnight, Emily," he murmured, seemingly as nervous as I was. I smiled as he turned and hurried back into his room and shut the door behind him. I stood there for a moment, shocked at the poignant and frank encounter with my friend's father. At this point, I was trembling with a fervent desire that was entirely foreign to me. Quickly, I turned on my heel and returned to the guest bedroom.
I collapsed on my bed in a heap, replaying the somewhat innocent yet sexy moment I had just shared with Greg. I laid my head on the pillow, I suddenly realized how wet I was. I blushed at this realization, even though there was no one in the room with me.
Gradually, I moved my hands down towards my thighs. I wasn't very sexually experienced and hadn't masturbated but once or twice. Yet this seemed primal, natural. I grabbed my thighs, even more aware of how wet and worked up I was. I moved my hands toward my panties and grabbed the elastic at the top. My hands found their way to the top of my pussy and I noticed that the lips were slightly swollen and very wet, heightening the sensory experience of my fingers gliding along them.
I worked my way to my clit, pink and swollen with desire. I began to rub it, my thoughts centered directly on Greg and the humongous bulge in his boxer briefs. I was so wet you could hear my fingers gliding along my clit. I felt myself moving closer to orgasm. The more I thought about Greg, the more I trembled with longing.
I shoved a finger in my pussy and used my thumb to rub my swollen clit. My entire body was shaking! I fucked my pussy with my finger vigorously, my pussy stretching with each thrust. I was breathing heavily. My back arched, and suddenly I felt an unfamiliar wave of euphoria, my pussy clenching erratically, my thighs shaking. Oh Greg, I thought, and hastily covered my mouth as I began to let out inescapable moans.
And as quickly as my orgasm arrived, it ended. I sat up in a daze, suddenly aware that I just had my very first orgasm.
I slept soundly that night. But the events of that night were nothing compared for what was in store for me the next day.
*********
The next morning, I awoke with a start, remembering all that had transpired the night before. I smiled sleepily as I recalled Mr. Richardson, standing next to the window bathed in moonlight, his cock pressing against the seams of his boxer briefs.
After my shower, I got dressed slowly, picking an outfit that was slightly more revealing and bright. I chose my white skirt, flip flops and my bright blue tank top, which gave the viewer a nice look at my blossoming cleavage. I spent extra time on my make-up that morning, applying mascara and lip gloss instead of my usual blush and chapstick.
