My Girlfriends' Sleepover
by Ariana
Copyright© 2025 by Ariana
True Story Sex Story: "My Girlfriends’ Sleepover" is a true story about the night I spent with my girlfriend, Judy. To our surprise, her brother returned home from college and informed us that he had just broken up with his girlfriend. This created an unexpected opportunity for me, as I have always had a crush on him. What can I do to catch his attention?
Caution: This True Story Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual True Story Masturbation Oral Sex .
I slowly realized that I was no longer asleep. I was in Judy’s bed, sleeping over at her house, and I felt utterly at peace. I sensed a hand gently caressing me and assumed my friend Judy had climbed into bed with me. I relaxed and pretended to be still fast asleep. The hand continued to caress me from my back down my hips and continued down my leg, then returned the inner thigh route to gently caress my vagina lips, then my butt, and my lower back. This caress continued over and over, with each caress lingering a little longer in my vagina area. I was enjoying the touch, and I have to say I was getting very much aroused.
I started to fantasize about Jason as the hand continued to caress me. Jason is Judy’s brother, who just returned home from college. Last night, I learned that he had broken up with his girlfriend and is now available. Judy has been trying to play matchmaker and has gone out of her way to promote me to her brother. Things got a bit out of hand when I confided my feelings to Judy. I smiled and told her that Jason could have his way with me anytime.
The hand gravitated more and more to my vagina and was caressing my clit and playing with my lips. I shifted my leg ever so slightly, creating just enough room to enhance access while maintaining the pretense of being asleep. I could feel Judy adjusting her position beside me. As she leaned in closer, the warmth of her body enveloped mine, filling the space between us with an electric energy that heightened the intimacy of the moment.
Next, I got a real surprise. I felt something significant and warm caressing my vagina lips. Something bigger than a finger. My first thought was that Judy must have retrieved one of her dildo toys that she had hidden from her parents’ prying eyes. I continued to lie there and could feel the toy sliding from my clit to the lower vagina opening. The head of the toy felt warm and soft. With each back-and-forth stroke, I lubricated it with my slippery love lubrication, and each passage allowed the toy to enter a little deeper as I became more aroused. Then the toy slid into my lubricated love canal about 2 or 3 inches and stopped moving while a hand caressed my breasts and long, hard nipples. I finally started thinking, is this Judy, or did Jason slip into bed with me? The hands on my breast feel too large for Judy, and that doesn’t feel like a toy in my pussy, so it must be Jason fucking me, I reasoned. I reached back and laid my hand on his hip as he began to take longer strokes. I knew it was Judy’s brother Jason, and the whole picture was suddenly clear. He was feeling so good in my pussy, and I was so turned on that I pulled him closer and said, “Jason, go ahead and fuck me. Don’t pull out now”, and that is what he did.
After about 5 minutes of Jason having his way with me, he pulled out, and I rotated on my back, thinking we were going into a missionary position. Instead, we had a great oral session where he gave me three climaxes, and then he moved into the missionary position, and I reached down and guided his cock into my hot receptacle, and our lips met for our first kiss. He kissed my pussy before my lips. I couldn’t help but grin as I reflected on the moment. It struck me as unusual that we had reached this level of intimacy without sharing a kiss first, something I expected to be part of the journey. As we reached our final, earth-shattering climax together, the intensity of the moment washed over us like a wave. The world outside faded away, leaving only the two of us entwined in our shared energy. Gradually, we began to slow down, savoring the lingering sensations and the warmth of each other’s bodies as they softened against one another. The room was filled with a sense of blissful calm, marking a profound connection that went beyond words. As his cock softened, it finally slipped out of my well fucked cunt, and as our kiss ended, we lay side by side with Jason’s arms around me, caressing in our afterglow.
12 Hours Earlier
Let’s take a moment to go back about 12 hours and dive into the story from that point. My name is Ariana, and I am an 18-year-old high school senior. I have long, natural blonde hair that shines under the sunlight, and my bluish-gray eyes often reflect the colors of the sky. Standing at 5 feet 5 inches tall and weighing 120 pounds, I have an hourglass figure with measurements of 36, -24, -36, which gives me a feminine silhouette. As I navigate my final year of high school, I find myself constantly exploring new experiences and shaping my future.
It’s Friday evening, and I’ve been invited to spend the night at my best friend Judy’s house. Judy is almost a mirror image of me, except she has light brown hair and hazel eyes, and she’s beautiful. We’ve ordered a pizza and have a new movie to watch if we feel like it. Judy’s parents have gone out for the evening, giving us the run of the house and plenty of privacy.
The delicious aroma of pepperoni and sausage pizza wafts through the air as the pizza finally arrives. Each of us eagerly grabs a chilled Coke from the fridge, the sound of the cans popping open echoing in the cozy kitchen. With steaming slices in hand, we make our way to the family room, where our prized possession —a large 24-inch color TV console —stands proudly in the corner.
Judy, with a glint of excitement in her eyes, carefully inserts the VCR tape into the player, the whirring sound of the mechanism drawing our attention. She presses the play button, and the opening credits begin to roll, casting flickering light across our faces. We settle onto the plush couches, the warmth of the pizza radiating in our hands, and attempt to immerse ourselves in the unfolding plot of the movie.
However, as the story line unfolds, its slow pace quickly draws our focus away. In between bites of gooey cheese and flavorful toppings, we find ourselves chatting animatedly about school events, dissecting the latest gossip about boys and who is rumored to be dating whom. Laughter fills the air as we share our opinions and stories, creating a lively atmosphere.
Eventually, the movie’s plot fades into the background. With a collective glance and knowing smiles, we decide to turn off the VCR and switch our attention to listening to music instead, filling the family room with our favorite tunes and forging memories that would last long after the pizza boxes were empty.
At around 9:00, Judy’s brother Jason walks in, says hello, and grabs a leftover piece of cold pizza. Jason is 20 years old and home for a short visit from Memphis State, where he is currently a sophomore. He has never given any indication that he was interested in me. I’ve had a secret crush on Jason ever since I first met him, but our relationship has always been friendly and casual. He played football in high school, and his physique still appears rock-hard. He has short brown hair and brown eyes and stands at 6’2”, weighing about 180 pounds, or at least that was his weight on the last football roster I saw.
Jason went over and sat down in an easy chair across from us, asking us what we were up to. Judy explained that we were trying to watch a movie, but it was boring, and that I was spending the night, so we were chatting and listening to music. Then Judy asked Jason why he wasn’t with Carroll on a Friday night. Jason said he and Carroll had broken up over a month ago, and he was on the rebound. That sure made my ears perk up. What could I do or say to catch his attention? For now, it was my one chance.
Jason spoke up, “Hey, I just remembered I have a bottle of rum that a friend bought for me. I’m going to make a drink. Would you like to liven up that Cola you’re drinking?” We both agreed that sounded great. Soon, Jason returned with his drink and poured some rum into our glasses.
When I first tasted the rum and Coke, I found it a bit strong, so I took my time sipping it. However, I must have been sipping quite quickly because it wasn’t long before Jason was handing Judy and me another fresh drink in a cold glass full of ice.
Judy and I decided to slip into our pajamas for a cozy night in. I chose a pair of vibrant aqua pajamas made from a luxuriously silky nylon fabric that felt soft against my skin. The pants were snug and sleek, accentuating my legs while allowing them to move freely. The top was a relaxed pullover T-shirt style featuring wide, comfortable straps that added to its laid-back charm. Judy’s outfit mirrored mine in style but in a gentle light pink hue, giving her a fresh and delicate look. Together, we wrapped ourselves in the warmth and comfort of our snug ensembles as we settled in for the evening.
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