Jess loses her virginity during her first slumber party
Looking back at my years in high school there was really only one event that stands out to me as a good story. I was sixteen and my best friend Kaitlin invited me over for a sleepover. She was my best friend since grade school but I’ve never been able to sleep over at her house until that night. My mother was pretty anal growing up and it took me a while to convince her she could trust me. I feel stupid about it now, but prior to going to her house I called Kaitlin up and asked her what I was supposed to bring to wear. I had no clue whether or not you were supposed to wear pajamas.
“Jess, you’re so awkward”, was the response I was given.
Apparently you do. I tried on the pajamas I planned on wearing that night. I looked into the mirror, the tank top I had chosen was a little too flashy but my breasts weren’t all that big at the time and it was just going to be girls there. My bottoms were pink and showed off the cute little butt I used to have. I smiled at myself in the mirror. I have a cute smile that I think got me a lot of boyfriends later on in my life. I also had smooth brown hair back then that went down to my shoulders.
I got in the very backseat of our van with my bag. The thought came to me that I wouldn’t be able to masturbate that night. I had just learned how to masturbate that year and I had been doing it at least once a day. My mom wouldn’t be able to see my lap since I had a whole row of seats in front of me so I got a crazy idea. I stuck my hand inside my pants and started to touch myself. It felt good at first, but as I realized we’d be at Kaitlin’s house soon I needed to do more to make sure I got off in time. I lowered my pants and panties just a bit so my crotch would be exposed to the air. I really started getting into it then. My mom was talking to me about being respectful and asking me questions about what I would do in case of emergencies. I was able to answer them at first but as I got closer to my orgasm I wasn’t able to concentrate as much. Every time I had to respond to her I had to make sure she couldn’t hear the lust in my voice. We turned onto the street Kaitlin lived on; I was running out of time. I took a risk and slipped my other hand under my shirt and gave my breast a squeeze. That did it, I started moaning quietly and I came right as we pulled up. I swiftly took my hand out of my pussy, sucked my juices off and pulled my pants and panties up. I got out of the car and my mom left in a hurry to make it to some book club on time. I knocked on the door and Sarah answered. Sarah was Kaitlin’s cousin, they were both a few months older then I was. She was wearing short shorts and a tank top. I couldn’t help but notice her breasts because they looked like they were ready to pop out of her shirt. She caught me staring and laughed at me.
“You haven’t seen me in a while huh?” she said.
“No, guess I haven’t”
She led me to the T.V room where Kaitlin was sitting on the couch. She had pig tails that day that made her look a lot younger. That and her breasts were the smallest out of all of us. She had a bright green shirt on that really stood out because they matched her eyes beautifully. I don’t think she had even started wearing a training bra yet because her nipples were slightly noticeable.
“Where’s your mom?” I asked.
“Out of town”, she said. “What you didn’t know?”
I didn’t know, to be honest, nor did I care. I’ve been kept under so much constraint from my mom throughout my teenage years and I loved the freedom.
“So Kaitlin, what’s the plan?” Sarah asked.
My heart skipped a beat. Apparently Kaitlin had invited some boys over as well. I got hella nervous to say the least; I hadn’t had a boyfriend then and always got shy around boys. Luckily it was boys I didn’t know. They were Kaitlin’s neighbors, Tim and Jake, and they didn’t go to our school. Jake was 18 and Tim was 16, Kaitlin told us they were both pretty cute.
We sat around and watched TV until they arrived. My mind was going crazy thinking about what could possibly happen in the next few hours. It was nine o’clock when the doorbell rang. I answered the door and was greeted by two handsome boys. Tim had short blonde hair and some freckles, he looked a little shorter then I was. Jake on the other hand was at least 6 inches taller and was gorgeous. He had black hair that was just a little shorter than mine and pretty big muscles. He gave me a sexy smile and I couldn’t help but blush. I let them in and Kaitlin came and greeted them. We all gathered and went to Kaitlin’s room shortly after their arrival.
After making fun of the boys for a little bit we all started to get a bit flustered. Kaitlin suggested we play a game, since we all seemed kind of new at this Sarah suggested we should each take turns and choose someone whose clothes we wanted to take off. I probably wouldn’t have wanted to do anything this crazy any other day but I had gotten wet since we all sat down and started talking. I looked around and the only person who seemed more embarrassed about this then me was Tim.
Kaitlin said she would choose first and then we would just continue in a circle. She smiled wickedly at me for a second and I panicked. I lucked out because she then averted her gaze to Tim. She sexily walked towards him and asked him to stand up. He seemed to be pretty brave at that moment. We all had our shoes and socks off already so all Tim had on was a shirt, shorts, and his underwear. She went straight for his shorts. I couldn’t help but stare at his small boner trying to break free from the thin cloth. She then removed his shirt and finally his underwear. His dick was the first I had ever seen. I discreetly moved my hand between my legs and started to rub myself. God, I was so wet.
Tim sat back down next to me and then Jake got up to pick someone to undress. Then the unexpected happened, he walked over to me. Out of us three girls I was the one he seemed to lust for, I felt so special. He extended his hand to help me get up. I smiled at him and we stood in the middle of the circle. As he started to remove my shirt I saw Tim approach Sarah and she willingly got up. My hard brown nipples were then revealed to everyone as Jake removed my bra. In the corner of my eye I noticed Tim had removed Sarah’s shirt and bra. She had tiny, but pointy, nipples that were of a much fairer tone then mine. She pulled Tim’s face towards her breasts and he started to suck on one of them. Jake was also looking at them while I did but then turned his attention back to me. He unbuttoned my pants and slid them down to the floor. As I lifted my feet out of them I could feel my wet lips rubbing against my panties. Kaitlin was sitting on the floor with her legs widely spread with one hand in her pants rubbing furiously while the other gently caressed her breasts. As Jake gently rubbed my pussy I watched Tim and Sarah. He was still sucking on her nipples but she was now stroking his dick. With her free hand she unbuttoned her shorts and they fell to the floor. I was shocked to see she wasn’t wearing any underwear. Tim seemed just as surprised and his hand quickly moved to her clit. She just held onto his dick and started moaning.
Jake’s hands slipped under the waistband of my panties and slid towards my butt. He cupped both my cheeks and pulled himself close. He moved his lips toward mine. Our lips touched and I moaned into his mouth. Our moment was temporarily broken as we both turned as we heard Sarah moaning loud. Tim now had her fully undressed and had his head between her legs. Every time his tongue flicked across her bald clit she would moan in ecstasy. I then felt my panties being pushed down my legs. There was a slight moment where the crotch of my panties stuck to my lips as he pulled them down. I looked down as his hand slid across my pubic mound. I wasn’t bald like Sarah was, he didn’t seem to mind. His fingers gently rubbed my clit as he moved his mouth back towards mine. We started to make out as his hand worked his magic on my body. I occasionally moaned into his mouth.
Kaitlin walked up behind him and started to unbutton his shirt. Sarah and Tim had been quiet for a while but then the moans started up again. She was riding his small dick for all it was worth, he big tits bouncing up and down. I started to have the thought whether or not I was ready to lose my virginity that night but it was interrupted as Jake moved his fingers from my clit to inside my vagina. My body froze as his fingers lightly touched the entrance to my wet hole. He was very gently with me as he slowly moved two fingers in. My mouth opened and my head tilted back. My own fingers weren’t nearly as big as his; I had never realized how tight I was. My eyes felt like they were rolling back into my head as his fingers rubbed against my g-spot. He slowly moved his fingers in and out of me, my eyes remained shut and my body gently rocked against his fingers. When he moved his thumb up to work my clit I opened my eyes to look at him. Kaitlin had gotten him naked except for his boxers. I moved my hand to his crotch to feel his manhood. He was so hard and much bigger then Tim was. I placed my hand inside and grasped him. The moment I did this his fingers started fucking me even harder. I started stroking him but I was starting to lose all control of my body as I approached my own climax. My pussy was dripping with sticky fluids and his hand was easily moving in and out now. He slapped my ass and worked my pussy hard with his fingers and I started to cum. I moved my mouth towards his and locked our lips together as I came. I moaned into his mouth and squeezed my legs together around his hands. I nearly fell but with his fingers still inside me he picked me up with his free hand and set me down on the couch where Sarah and Tim continued to fuck.
Kaitlin was on the floor where she had apparently removed her own pants; her legs were bent and spread while she was working her fingers in and out of her pussy. Jake looked into my eyes and then slowly pulled his fingers out of my pussy. Some cum stuck to his hand and he moved his fingers toward my mouth. I had tasted myself before but never had there been this much cum, still, I accepted his gift and sucked his fingers clean. I gave him a wicked smile as I yanked his boxers down to his knees. His cock sprang free; finally I’d be able to please him. I originally wanted to try giving him a hand job but with me lying down on the couch and his penis just above my face I had changed my mind. I lifted my head slightly and licked under the tip of his penis. He smiled but he then pushed the head down to my lips, he must have been too horny to be teased at this point. I parted my lips and let his head dip in slightly. I tilted my head and used my hand to get more of him in my mouth. His cum tasted so much better than my own. I was scared that I wouldn’t be able to fit him all in so I didn’t try right away. I did my best to swirl my tongue around his head and move his whole penis in and out. The rocking of the couch caused by Sarah and Tim really caused my head to bounce up and down around his cock. Their bodies were sitting directly by my head and I could smell Sarah’s wet cunt. Tim reached over and squeezed my nipples. Jake’s balls tightened and I got excited as I sensed he was about to cum. He stopped me however, I was disappointed but then he whispered into my ear he wanted to save his load for later.
Sarah then let out a loud moan and bucked her hips rapidly against Tim’s groin. She suddenly pushed hard against him and kept herself there as she orgasmed with him still inside her. After freezing for a moment she got up and off of him. Trails of her cum were still on his penis and he was still hard. Without even finishing Tim off, she walked over to Kaitlin, raised her to her feet, and pushed her onto the couch opposite us. Jake got up and followed her. Sarah slid Kaitlin’s panties down her legs then mounted her. Jake sat down next to Kaitlin and sucked on her precious tits. Sarah put her fingers inside Kaitlin and Kaitlin responded by doing the same to Sarah.
The sight of both my friends getting each other off while my recent lover played with their tits was too much for me. I started fingering myself. I looked down and saw that poor Tim was working his cock hard trying to get himself off, the scene in front of him probably had the same effect it had on me. I looked up however and saw his eyes, not looking at the orgy in front of him but down at me playing with myself. I grabbed his hand and placed it between my legs, and then placed my hand around his shaft. We momentarily stared into each other’s eyes as we masturbated each other before turning to watch our friends. I worked him as best as I could until he jizzed all over my hand. I brought my hand to my mouth and tasted him. He actually tasted pretty good. I ate the remaining cum on my hand and licked his penis clean. After cumming, Tim thanked me, closed his eyes, and then rested his head on my thighs. I started getting tired too and couldn’t help but close mine.
I was awoken by Jake. He smiled at me and gave me a kiss. I started worrying; did I really fall asleep before finishing anything with Jake? I looked at the clock, 3:30, Fuck!
“Don’t worry”, he said, “I didn’t let Kaitlin or Sarah have any of me”.
For the second time that night Jake made me feel special.
“Kaitlin has a pool, want to go swimming?”
I smiled at him, and then got up. Jake moved his brother’s head off of me. Tim’s fingers slid out of my vagina as I got up, his hand fell against the couch and some of my cum slid off his fingers onto the floor. Kaitlin and Sarah were sleeping on the floor, in a scissor position. Fuck I must of missed a lot. We went downstairs and then went outside. It was freezing outside.
“Don’t worry, I came down and turned on the water heater 15 minutes ago”, Jake told me.
He walked ahead of me towards the edge of the pool and then jumped in with a splash. I couldn’t help but stare at his ass the whole time. He called for me to follow him. I realize how stupid I must have looked thinking about it now but after he called me I ran to the deck and hopped in. My breasts bounced slightly as I ran. He brought me in between his arms and kissed me under the moonlight. He dove underwater and swam around, so I just started floating on my back, we both were in a playful mood I guess. He emerged from the water in between my legs. He slowly drifted until his mouth was barely grazing my pussy. He licked between the lips slowly; I couldn’t help but let out a moan. After a little bit of teasing to get me nice and wet he started licking my clit. Fuck, how was this boy so good? His hands emerged and held on to my waist to keep me from drifting. He then took my clit into his mouth and sucked on it gently while flicking his tongue across it. I was in complete ecstasy. My toes curled causing my legs to slowly dip into the water. My feet ended up touching his back but with his hands supporting me I continued to float. His mouth suddenly left my clit and he went back to teasing me. God how I wanted to cum, I had to keep my hands spread out otherwise my head would have submerged under the water. If we weren’t in that position I would have been working my clit so hard. He brought me on the verge of an orgasm one more time before stopping his oral gift all together. He let go of me and as my body moved back into an upright position I brought my hands to my clit. He watched me attempt to try and get myself off for a little bit, gave me a kiss and then swam towards the jacuzzi. I decided to follow him to see what he had in store for me.
By the time I got there he was already sitting inside waiting for me. Water was dripping down my breasts and thighs, I felt so sexy. I walked down the small steps and sat next to him. I grabbed his cock and stroked him as we made out. The thought of his cum shooting out underwater turned me on so much. I used my other hand to gently rub his balls and moved my mouth to his neck, lightly giving him kisses. He actually let out soft moans; I loved this boy so much. His balls tightened and he stopped me again. I guessed what he wanted. I slid down to the standing part of the Jacuzzi, turned around, and waited for him to join me. He pressed his body up against me, his cock sitting between my legs. He reached down and grabbed his penis. The head touched the entrance of my vagina. I looked into his eyes as he slowly moved forward. The head went in and I smiled at him. His hands grasped my butt cheeks and he gave them a squeeze. He then moved more of himself into me. I felt his cock slowly spread me open. I actually had to move my legs apart slightly as he started to get in deeper. Once he was in me, his hands dropped down to my thighs. He told me to hold on so I wrapped my arms around his neck and shoulders. He then got a good hold of me and lifted my thighs up from the ground. His cock was able to get deeper into me from this position, I smiled to show him I liked where this was going. He put his tongue back in my mouth and started to fuck me. It almost felt like he was lifting me a bit then dropping me back down on his shaft. We started to get into a rhythm. I didn’t want him doing all the work so I wrapped my legs around his thighs and tried to ride him as best as I could. I moaned for him and he spanked my butt lightly when it rose above the water. At one point he moved his hands back to my butt cheeks as he held me up. He continued to fuck me but spread my ass cheeks at the same time.
When he told me he was about to cum I just didn’t want it to end yet. I squeezed my legs tightly around him and pulled myself toward him to stop his humping. He looked at me confused and I gave him a dirty look. I unhooked myself from him and stepped away. I then turned around and got back up onto the seating section with my knees. I started to crawl out of the pool with my arms and knees. Water dripped down my ass as I showed it to him. I stopped crawling when my hands were on the cement, outside of the pool, and my knees were at the edge of the seating area. I turned back to look at him. He walked forwards and placed his cock back between my legs where it belonged. He used his hand to guide it in. It felt so hot, my pussy was still underwater with his cock moving in and out of me but my ass was just above the surface for him to see. He fucked me hard, our bodies making a slapping noise every time they touched. He was amazing at getting his cock to come just centimeters away from exiting my pussy before sending it back in. On one of his cock’s retreats, however, it didn’t come back. He told me to sit tight and wait. I heard him leave the jacuzzi; now what was my lover up to?
A humming sound came from all around the jacuzzi. Before I could even guess what it was, the jacuzzis’ jets initiated and the one on our side was right on my clit. I started going wild. I arched my back and moaned so loud. He splashed back into the jacuzzi and quickly got into place. He rammed his dick into me hard and fucked me for all I was worth. Each thrust of his hips sent my waist forward, decreasing the distance between the jet and my clit. After several thrusts my clit was literally right on the jet. I used my hands to pull on my nipples. My orgasm quickly built up, this was too much for me. I came so hard all over his cock and my pussy tightened around him. This sent him over the edge as well. He came inside me and fucked me until he completely emptied his load inside me. I slowly started to crawl all the way out of the jacuzzi to relieve my sensitive clit from the pleasure of the jet. He came out with me and we lied on the pool deck with him still on top of me. I felt our cum spill out of me, down my thighs, and onto the pool deck. After our breathing slowed he helped me get up. When we got inside he had towels prepared for us at the door and he wrapped me in one. We walked over to the living room couch and he lied down on his back. Before lying down with him, I opened up his towel and then opened mine. I got on top of him so my breasts gently set on his chest and his limp dick was pressed against my clit. I gave him one kiss before we fell asleep together.