June 5. 2022

This is the first entry for this new diary. I do have a regular daily diary, but this is my diary of sexual experiences. Just in case this is ever read by anyone in the future let me introduce myself. My name is Ashleigh or Ash. I am 16 years old and a virgin. I am 5 ft 10 inches tall around 165, very curvy, with 38 D tits. I come from an athletic family. I play softball on the varsity, as the catcher and power lift. We won state in both this past year.

My dad, Michael is a high school football and Powerlifting coach. He is the offensive line coach and offensive coordinator for the large high school. He went to a D1 university on a scholarship and played offensive line in college. He is a big man standing at a solid 6 ft 4 inches. About 260 pounds and well built. He works out daily with his players.

My mom, Jessica, is also an athlete in high school. She played Volleyball and was a cheerleader. She is an even 6 ft about 145 lbs. and curvy. She is an English teacher at the high school and a cheerleader coach. She is more slender than I am with a 36 D breast. She still does her workout and gymnastics.

I also have an older brother, Braden, and he is built like my dad. He is 20 and in his second year of University playing football at the same college mom and dad went to. He is 6 ft 4 and a bit heavier than Dad at 275 lbs. His coaches like him heavy and strong. He can lay someone out on the gridiron. Mom is a blonde, and dad and brother are both light brown-headed. I am a redhead like my grandmother used to be. 

That is my family. Well, the interesting part is coming. It is summer and school is out. Mom and dad both signed up for a teaching conference to keep up their continuing education. My brother Braeden was home between semesters. He likes to reconnect with his old classmates and buddies from high school. It is the first night with mom and dad gone. We are home. I am working part-time as a server at the pizza joint. I do it by choice. I like fashion and like my car. I get home around ten and find my brother and his best friend, Jared, there. They are drinking some beer and watching the game on TV. One team is playing another with a bat. I am kidding. The Rangers or hosting the Yankees.

I greet them both heading to my room to shower and change. I strip off my uniform and walk down the hall to the bathroom. I wrap a towel around me to do so. I can easily be seen from the living room if you turn and look. There are a couple of catcalls making me blush, but I do a turn on my tip toes before I continue to the bathroom. I spent some time there, shaving my legs and around my pussy. I like to keep it smooth. I pad back to my room in the same towel. My red hair is still wet and clinging to my back. More catcalls and another turn. 

In my room, I sit at my vanity and dry my hair, then pull it back into a ponytail. I slip on panties, shorts, and a tank top. No horrid bra. I go to get myself water, and a beer each for them. I join Braden and Jared in the living room and sit on one corner of the couch opposite the end from Jared. Braden is in the big recliner. We watch the game till the Rangers win. 

Braden starts to switch channels. “So what y'all want to watch now? Does anyone have a preference?”  He runs through the channels quickly. 

Jared looks at me and offers a suggestion. “Brae, let’s watch that movie we found the other night. I bet Ash will be shocked.” 

He grins at me. Brae looks at Jared, "I bet she will too. “ 

I roll my eyes at him and shake my head. I figured nothing would shock me with these two. Jared is almost like a brother. He played football with my brother. He is not as stocky but still built. He is 6 ft 2 around 180 I think. Short blond hair. I have had a crush on him for a while. 

I blush as the movie is called up. My eyes go wide. I was wrong about not being shocked. The movie starts with the younger sister at home alone. She is caught masturbating by her older brother and some of his friends. Soon it is free for all with her in the middle. I can’t help but look at them both and back to the screen. It is a hot scene. Kind of a fantasy of mine to be the center of attention of several guys. My nipples get stiff and push through my tank top. 

Licking my lips as I watch the movie. One hand drifts down and starts to play with my clit not thinking about it. I get distracted by movement and look up. They both have their impressive cocks out and stroking them. I can’t help but stare at them both. Jared is easily a good 7 inches but is thin. Brae on the other hand is dangerous. He is at least 9 inches thick. I look from one to the other and back. 

“Sis, you might as well take the shorts off. We can see your pussy anyway.” He continues to stroke his cock slowly. Jared is doing the same and watching me intently. 

“Fine. No pictures or anything.” I lift my hips and wiggle out of my shorts and panties. I drop both to the floor, legs spread as I start to play with my clit again. There is moaning and it is from the girl on the screen. She is sucking her brother like she was hungry for it. Another one of the men in the movie is behind her, He is slamming into her over and over.

I lay back on the arm of the couch, going from watching the movie to watching them. My fingers moved quickly over my clit. I noticed my brother getting up. He drops his shorts onto the floor. He is naked from the waist down and kicks off his sneakers. He walks over to me with his cock in hand. He stops and presents his cock to me. I look up at him and blink. 

“Go ahead, Sis. Suck it. I know you want to. You want to be the girl in the movie.” He rubs my lips with his cock. 

He is not wrong. I swallow and part my lips. I know we are crossing a line but at the moment I don’t care. He pushes into my mouth. My lips wrapped around the fat head are stretched a bit. He is the largest cock I have come seen outside of porn. He pushes in till I gag and pull back. He keeps sliding his cock in and out of my mouth slowly. I am loving it. Brae takes hold of my ponytail and guides me onto his cock. My cheeks cave in as I suck while he pulls out. 

I feel my legs parted by another set of hands. I had forgotten about Jared being here. He spreads me wide and moves between my thighs. He moves my hand from my clit and attacks it with his mouth. I moan as his tongue slides up the length of my very moist pussy. My legs spread more giving him more access. He wraps his arms around my thighs as my hips come up to push into his mouth. I am between two hot college men and loving it. My inner slut is let loose. It does not take long and I cum all over Jared’s tongue and face. 

I am panting when Brae pulls from my mouth. “Let’s switch. I want between my sister’s thighs. Been looking forward to this” 

I hear the words. I am stunned that my brother has been wanting to fuck me. I don’t get a chance to respond before Jared is slipping his cock between my lips. He can get more in my mouth before I gag on him. He does not waste time and starts to fuck my mouth like it is the last time he will. 

Feeling hands on my legs, Brae lifts my legs and moves closer to me. My mouth is full so I can't say anything. My eyes go wide. He pushes forward and enters me for the first time. The line is crossed. I groan around Jared’s cock sliding in and out of my mouth. My pussy is being stretched. He stopped at one point and I thought he was in all the way. Again I was wrong. He slammed the rest of the way slamming through my virginity. I pull my head back letting Jared pop out and cried out. He hits my cervix, I think. My eyes clenched closed, “Oh oh oh damn. Damn. Please please don’t stop. Feels so good.” I could not help but beg for more.

My legs are held up by my brother and he does not disappoint me. He starts to move in me faster and harder. I have cock in my mouth as well. Both men are having their way with me and I am loving it. Braeden does not let up on me. He pounds me over and over. Jared does the same to my mouth. It is not long and my body tenses and I cum in an epic orgasm. My pussy is convulsing around the cock in me. It is something new for me, to orgasm around a cock in me. I feel the cock in my mouth swell. Jared does not pull out. He keeps a grip on my hair and erupts in my mouth. I have no choice but to swallow his cum going down my throat. It is a bit slimy and tastes weird. My first time swallowing. 

Jared pulls from my lips. I am breathing hard. He sits back, his cock going soft. Braeden is still thrusting into my pussy. My body arches. I am still in my orgasm. He slams in deep and leans over me. He is grunting. I can feel him erupt into my pussy. Only then do I realize he is bare in me. I am on the pill and hope it works. My pussy feels like it is rippling up and down the thick length of his cock, milking him. I love the feeling of cum flooding into me. We stay still like that for several moments, breathing hard.

Brae pulls from me and cum seeps from my flooded pussy. I lay there breathing hard, not believing what we just did. I let two men fuck me, one being my older brother. Will I do it again? Oh hell yeah. I took another shower and went to bed. I hope there is more to come. 

Ashleigh Madison