Cumming of Age
With the help of my older sister, Jackie, and two of her boyfriends, I lost my virginity the weekend my folks went to Vegas. I was 17 at the time, and Jackie was a worldly 19. My mom and dad left bright and early one Friday, giving us each $50 and strict instructions to behave ourselves and not to get into any trouble.
As our folks pulled out of the driveway, Jackie looked at me and asked "What have you got planned for the weekend?" I shrugged and told her that I'd probably spend all my time in the pool. She gave me one of her sly, secretive smiles and told me that her concept of a good time would begin when Brad and Jeff arrived. I was out by the pool when Brad and Jeff arrived. I knew they were there because I heard Jackie take them into the family room and turn the stereo up full blast.
When I went to the kitchen for a glass of cold water, I could hear them downstairs laughing. I also caught a whiff of marijuana coming up through the floor vents. Moving quietly down the stairs, I paused at the top of the steps leading down to the basement. Jackie had left the door slightly ajar and I could hear them talking. "Jeff, you're bogarting that joint!" I heard Jackie say. I tip-toed down the stairs and peered cautiously through the crack in the door.
Brad was sitting on the couch watching Jackie dance with Jeff. The two of them were swaying together in the middle of the floor. As I watched, Jackie pressed herself against Jeff, and he kissed her. She wrapped her arms around his neck and ground her hips into his groin. Jeff took hold of the cheeks of her ass and pulled her closer. While he held her ass with his right hand, he ran his left one up her waist and cupped her right breast in his left. Jackie moaned as Jeff squeezed and fondled her tit. Suddenly Brad yelled, "Hey, you two! You let the doobie go out. Bring it over here and let me light it." Jackie pulled away from Jeff and strolled over to the couch, sitting next to Brad. "How about lighting me instead, Bradley?"
Brad reached out his hand and squeezed her tit. Jackie smiled at him and, reaching up, untied the top of her swimsuit. Brad took both breasts in his hands, pushed them together and ran his tongue back and forth from one hard nipple to the other. Jeff sauntered over, sank down next to Jackie and covered her mouth with his. I could see their tongues playing with one another. Brad slowly pulled down Jackie's bathing suit and ran his tongue over her belly. She kicked off the bottoms and spread her legs. Brad's head moved between her parted thighs, and Jeff lowered his head and started sucking on her nipples. I could feel my knees shaking, and I knew that I was getting really turned on. Jackie pushed her pussy into Brad's face and told him not to stop. Brad stood up suddenly and pulled his swimming trunks off. His stiffened cock stood straight out and, taking it in his hands, he looked at Jackie and told her he wanted to do more than just eat pussy. Jeff moved away as Brad sank back down on the couch and pulled Jackie on top of him. She straddled him and guided his cock to the mouth of her dripping pussy. They humped against one another as he sucked on her breasts. Then Jeff moved up behind Jackie and spread the cheeks of her ass. I closed the door as Jackie screamed out.
Upstairs, I stood at the kitchen sink and thought about the three of them down there fucking their brains out. Suddenly, Jeff walked in the kitchen stark naked. He stopped when he saw me but made no attempt to cover himself. He got a glass out of the cupboard and came over to the sink. Jeff filled the glass with water and turned to look at me. He watched me while he drank from the glass, taking in every detail of my body. "You must be Jackie's kid sister," he said. I laughed and told him that Jackie was only two years older than me. He smiled and said that he never would have guessed it. "Little sister, Jackie doesn't have any of the soft curves that you do."
Then he moved beside me and pressed his lips against mine and ran his tongue over them. I opened my mouth, and our tongues met. Sensing that I wasn't going to stop him, he smiled at me, pulled my suit down around my waist and cupped my breasts. "You have got one gorgeous body, babe." My nipples grew harder, and I trembled in anticipation. Trailing his tongue down my neck, he licked my breast and sucked a nipple into his mouth. He looked up at me and asked if I liked it. In answer, I pushed my tits together with my hands (as I had seen Brad do to Jackie) and asked him to lick them some more. His hands and mouth descended to my tits, and he proceeded to squeeze, fondle, suck, lick, pinch, and caress me for several minutes. Then he trailed his tongue down to my stomach and stopped at my swimsuit. I smiled down at him as he pulled it down slowly over my hips and thighs and let it fall around my ankles. I kicked it away and spread my legs slightly. Jeff lifted me up under the arms and sat me on the edge of the table. He sat in one of the chairs, pulled my legs over his shoulders and started licking the insides of my thighs.
I lay back on the table, and my legs fell open wider as his mouth got closer to my trembling twat. Suddenly, he flicked out his tongue and hit my clit. I cried out with pleasure, and he buried his face deeper in my pussy. "Eat me Jeff," I gasped. I pressed my pussy into his face, and he stuck his tongue up my hole. "Oh yes!" I cried. "That feels so good. Do it!" He continued eating me while I moved my hips back and forth across the table. Jeff stood up and, bending over, rubbed his face over my tits! He took his hard cock into his hands and guided it to my gaping hole. "What now, little sister?" he asked me. "Do you want this, baby?" I groaned and tried to lift my hips to take him into me, but he held me firmly, and I couldn't move. He took the head out and rubbed it over my clit, exciting me all the more. When I think he realized that I couldn't stand it any longer, he rammed his dick way up inside me. I could feel my hymen stretching and finally tearing, and then Jeff was driving his rod in and out of me with slow, sure strokes. I was in a frenzy at this point, and when Jeff took my swollen clit between his thumb and forefinger and squeezed it, I humped against him like a mad woman. "Fuck me!" I panted.
Suddenly I felt my orgasm burst over, and as my pussy muscles clenched in uncontrollable spasms, Jeff cried out and pulled his cock out of me. He rubbed it up and down as he shot his load all over my belly. I rubbed my fingers through his hot sperm and then stroked my tits with his cum. He lay on top of me and kissed my mouth. "Not bad for a virgin," he said. He grinned at me, and we both looked up when we heard Brad say, "I'll say not bad!" Jeff got up off me as Brad walked into the kitchen.
Before I knew what was happening, Brad rolled over on my stomach and entered me from the rear. He slapped me on the ass and told me to move my hips. He fucked me harder than Jeff had, and it hurt a little. Then, suddenly, he pulled apart the cheeks of my ass and plunged his dick up into my bowels. I screamed in agony and tried to pull away from him, but he held me firmly in place and fucked my ass. After the initial pain receded I realized that I liked it, and I started moving my hips against his. Brad drove his cock in and out of my ass, and we both came at the same time, Brad shooting his wad deep into me.
"Well, what have we here?" Jackie drawled from the doorway. "If you were going to lose it, you couldn't have chosen two better guys to lose it to, sweetie." Getting down on her hands and knees, she brought their two cock heads together and licked at them. "And I don't mind sharing either." With that, I got down on my knees and helped her lick and suck the guys back to attention. We spent the rest of the weekend in a wild fucking orgy.
We tried every position we could think of, and it was the best time i've ever had. Or... at least, one of the best times I've ever had... There've been too many since then to keep an accurate count anyway.