By Tiffany Parker.
The following story is a work of fiction and is copyright property of the author. All characters are over the age of 18. Please don’t repost it without permission. But most importantly, I hope you enjoy reading it.
Seated at my vanity in my bedroom, I applied my makeup heavier than usual that evening. I was wearing the tight revealing red and white shell top and red skirt issued by our school’s athletic department. It was homecoming weekend, and I was looking forward to a wonderful evening.
I had grown up in rural Alabama and was raised to believe that men were men and women were women and all that entailed. At this time, I pursued typical female pursuits like cheerleading, makeup, dresses, and Junior League. It wasn’t until later, that I learned that there were many more depths of sexuality to explore. But this story is about the past.
I had turned 18 during the summer, was a cheerleader in my high school, a popular one at that, thanks to my social connections. I was dating one of the offensive lineman, a guy named Mitch, on the football team. He was tall at 6’3″, beefy at over 300 pounds, hairy, and had a huge cock which I was regularly sucking that fall. He was 19 and a fifth year senior as he wasn’t too bright and had been held back his freshman year. But he was sweet, considerate, and caring.
Meanwhile, I was still a technical virgin thanks to keeping chaste, while still offering up my mouth on a regular basis during the fall to satisfy his male urges. I knew that wouldn’t keep him happy forever, and I would need to up my game to keep my boyfriend satisfied.
I had promised him that we would have sex after the homecoming football game if the team won. The girls on the squad all provided these sort of inducements to the guys on the team to get them to play a little bit harder. The guys would run through walls if they knew it was going to help one of their friends get laid
Today, it was my turn to provide an inducement to my boyfriend. As I stood on the sidelines, that evening in my red and white shell top and red pleated skirt, I yelled until my cute frilly voice was hoarse.
I wanted the team to win, so I could finally have an excuse to have sex with my boyfriend. It sounds silly now, but at the time, I was protective of my virtue and thought men had to persuade or otherwise convince me to have sex with them, versus now when I engage in sex whenever I felt I would enjoy it.
My friend Danielle picked me up in her Chevrolet Cavalier to take me to the game. Daddy had given me the third degree about what I was doing over homecoming weekend. I had rolled my eyes and told him I was hanging out with Danielle after the game. He knew all about my boyfriend and disapproved thinking his daughter should be dating a man with a higher ambition than high school football. I rolled my eyes at that, there would be plenty of time to date other men in the future if I wanted.
“So tonight’s the big night right Tiffany?” Danielle asked, knowing full well about my plans with Mitch after the game.
“Oh my gosh, yes,” I responded, excited about what would happen later that evening. The thought of Mitch’s massive cock thrusting inside of me danced through my brain as I lost myself in thought dreaming about it.
“You’re going to love it Tiffany,” Danielle said.
“I can’t wait,” I sheepishly, but eagerly responded. şişli escort “I hope it’s everything I’ve dreamed of.”
Danielle flashed a knowing smile at me as we pulled up to the stadium.
As I jumped up and down that night doing our routines, feeling my perky D-cup breasts bounce in my pink sports bra, I was excited as our Indians were up 35-7 on our rival. Mitch had several pancake blocks of the other team’s defensive lineman, and my vaginal canal was damp at seeing my boyfriend so easily dominate the players on the other team. On the sidelines that evening, I had fantasies of him dominating me later that evening.
I had forgotten the school always scheduled a patsy on homecoming to ensure a victory on homecoming weekend that would make the students, alumni, and parents happy. Still though, I was excited to finally have my excuse to screw my boyfriend. Most of the Senior girls on the cheerleading squad had already lost their virginity, and I felt left behind. Tonight would be the evening that I caught up and finally found out what sex was all about.
After the final whistle, I rushed onto the field, like the rest of the cheerleaders and everyone else on the field. Jumping into Mitch’s sweaty arms, I whispered into his ear, “I want to feel every inch of you in me tonight,” as I pressed my pretty painted lips into the rough coarse lips on his grimy sweaty face.
The bright smile on Mitch’s face, when we broke our kiss, told me that I would be a very satisfied woman later that evening. Unfortunately, we had to break our embrace shortly thereafter as Mitch had to retreat to the locker room to change.
Making my way to the parking lot, I waited by his rusted out Dodge Ram pickup truck. It was a hand me down from his older brother, and Mitch was kind enough to drive me to school in it every day. The fact that I often sucked his dick on the way to school also helped I’m sure. But it saved me from taking the bus, so I was happy.
Standing there with my arms folded under my breasts, I impatiently waited for Mitch to return from the locker room so that I could finally lose virginity to him. Finally, after about a half hour, I spotted an unshowered Mitch making his way toward me and his truck wearing a sleeveless button up plaid shirt, blue jeans, and sneakers.
At that moment, I was never more turned on by his appearance than I was at that moment. Running up to him, I jumped in his arms and kissed him. Breathlessly, I begged him, “Please take me somewhere private. I need you”
Mitch didn’t miss a beat and quickly ushered me up into his lifted truck. I could never get into his lifted truck by myself with a boost. And it always felt good with his hands on my butt lifting me into his truck.
Instead of waiting patiently while Mitch drove, I rubbed up against him, kissed his cheek, and rubbed my dainty and manicured hands across his crotch. Mitch was a well hung man and I was so excited to feel him enter me that evening. The spankies of my cheerleader uniform were wet in anticipation of him fucking me.
Mitch parked in an open field about 10 miles outside of town. The night was clear and the stars were clearly evident in the sky. There was a slight chill in the air, but the weather was still very comfortable. He walked around the truck and escorted me out. I felt so into him at that moment. He was so kind and considerate, yet assertive.
After Mitch threw a blanket in the bed of his truck, he gently lifted me into the bed of the truck. I scooched myself into the bed of the truck, laying on the blanket, and motioned with my finger for Mitch to join me, which he gladly did.
Pushing my lips into his as he mounted my petite body, I felt waves of pleasure radiate through me as his meaty hands tenderly manipulated my body. Within two minutes Mitch had me undressed and naked in the bed of the truck. Shortly thereafter, he was naked too and pointing his girthy male member at my slick hole.
Looking up at the stars that enchanted evening, I struggled to find a more romantic way to lose my virginity. I was with a man I loved, the stars were sparkling in the sky, and he looked down upon me like I was the most important thing in his world.
Working quickly, Mitch quickly raised my shell top over my head, revealing my large breasts constrained tightly in my sports bra. I gasped in both relief and pleasure, as Mitch freed my twin girls from their tight home. My nipples were erect from the thought of the pleasure he would provide me that evening.
Pulling my damp spankies down my thin thighs, Mitch went to work eating out my slick hole. I screamed out in pleasure, thankful for the privacy that the large open field provided us. I had my first ever orgasm provided by a man right then and there as he licked my clit as I looked up at the stars. It was heavenly.
Mitch, sensing that he had brought me to orgasm, removed his expert tongue from my clit and replaced it with his already erect girthy cock toward my nether regions. I looked up at him, desperate for it inside of me. “Please fuck me with every inch of your manhood,” I breathlessly breathed out.
Bringing the head of his girthy cock toward my slick hole, he slipped in like a hot knife through butter. I gasped out in pain at first at him breaking my hymen. Mitch was kind enough to make sure I was okay before going forward. I nodded and begged him to go on. His subsequent thrusts quickly turned to pleasure, as I stared up at the stars, as he thrusted in and out of me, as I dug my nails into his back.
Later, I felt like an inadequate sexual partner for Mitch as I recalled laying there writhing as he thrusted in and out of me. Had I been more experienced, I would have been more engaged with him, but I just moaned out in pleasure from the sexual pleasure that he provided me.
Mitch wasn’t a virgin at this point of his life and had staying power. As I writhed and gasped beneath him as he thrusted into me over and over again. Already having orgasmed once, I was on the verge of my second as Mitch continued pumping into me. I could feel my breasts flop with each thrust. It was heavenly, I was so happy to have an experienced boyfriend who could handle me so well.
My whole body was convulsing in pleasure from his cock. I was already looking forward to our next go around. I had already decided that vaginal intercourse was about to become the most prominent feature of Mitch and mine’s relationship.
As I orgasmed for a second time that evening, the constrictions of my vaginal canal around his massive cock caused him to orgasm as he cried out in pleasure, as I felt him shoot hot semen into me. It felt wonderful.
A couple of months back, my mother had furtively taken me to get a birth control prescription when I had confided in her that I may be sexually active soon. She understood where I was coming from, while Daddy couldn’t think of me as anything but his little girl.
As Mitch pulled his now withering member out of me, I felt a feeling of emptiness inside my vagina and yearned for another go around with him. Pressing my taut naked body up against his, I pressed my lips into his kissing him.
Breaking the kiss, I breathed out, “That was wonderful. You were great. I can’t wait until we do this again.”
“You were amazing too sweetie,” Mitch said.
We laid there cuddling and looking up at the stars for a long time after that.
My yearning for another round with Mitch had to wait as I was due home in time for my curfew. Reluctantly I redressed in my cheerleader outfit, as Mitch put his jeans and shirt back on.
After helping me into his truck once again, Mitch started his truck and drove me home. I cuddled up against him the whole drive home rubbing his masculine chest through his shirt and his penis through his shorts. I could feel his virile seed leaking out into my spankies.
Driving through our town shortly before Midnight, everything was eerily quiet. I had already blown past my 11 pm curfew. Daddy was sure to be mad at me. But he would get over it, like he always did.
Stopping a half a block shy of the house, Mitch had my Daddy on his mind as well.
“You want to walk from here?” he asked. “Your Dad won’t see my truck.”
Sighing, I said, “No drive to the front of the house. Daddy will be even more mad knowing you let me off to walk alone in the dark.”
Nodding, Mitch drove the last block to the front of the house. The drapes were shut, so I pressed into him, kissing him hard, and thanking him for a wonderful evening.
Jumping down from the truck, I walked toward the front door, swishing my skirt back and forth more than was necessary, both to tease him and out of my new found confidence in the experience I had gained that evening.
Arriving at the door, I took a deep breath before turning the key and letting myself in. I found Daddy there watching late night television and having a bottle of Bud Light, like he usually did on Saturday.
“You missed your curfew Tiffany,” Daddy said, with the best scowl he could manage.
“I know Daddy,” I pleaded. “I’m so sorry. It won’t happen again,” I said knowing I had said the same thing the last time I had missed my curfew. It usually worked. But not tonight.
“And where were you tonight young lady?” Daddy asked in a knowing tone. From my unruly blonde hair, smeared makeup, and crumpled clothes, it was obvious I hadn’t been with Danielle. Maybe he did see me getting out of Mitch’s truck.
Smiling while remembering my evening with Mitch, I walked over to Daddy, gave him a hug, and said, “I’m not going to lie to you Daddy. I need to get to bed. I’m so tired.”
Turning around, I walked away and up to my bedroom, and changed into a t-shirt and shorts and climbed into bed. Laying in bed, I reminisced fondly about having sex with Mitch barely an hour earlier, while touching myself.
Falling asleep that night, I had fond dreams all evening about becoming a woman. The next day, I came crashing back down to Earth as Daddy grounded me for a month. Mom was eventually able to get him to relent after two weeks, but it was still so worth it. I wouldn’t trade the experience of that evening for anything.
I hope you enjoyed this story. I appreciate any comments or feedback that you have. – Tiffany