My parents had three children, I was the youngest and only boy, my sister Sherry, the oldest, is six years older than me and my sister Jeannie is three years older than me. This is a true story about my sister Sherry’s best friend Diane. My sister and Diane have been friends as long as I can remember, she was like another sister.
Diane was a small girl for her age, and since I was six years younger than her, we were around the same size. I was a tall skinny kid. I had hair almost to my shoulders, so in the rural community I grew up in, people would say I was long haired hippy type.
Diane developed early and when her boobs filled in, they were enormous. Her D sized tits on that tiny 90-pound frame, with her small curvaceous figure made her breasts look even bigger. She was the stuff of teenaged boys’ wet dreams.
I would describe her body as petite but curvy. I don’t know what her measurements were, but she had a tiny waist, shapely hips, and a small round ass that I couldn’t keep my eyes off of, and did I mention her beautifully developed melons? She had long straight brunet hair and she always had an intoxicatingly sweet aroma. I don’t know if it was her, or if she just dressed in hot clothes, but I never saw her wear anything that didn’t radiate sex. She wore tight tee-shirts or tight sweaters, hip hugging pants or short shorts or skirts. She was just a hot girl.
She was my first crush, and I took every advantage to see her when she was at our house. She and Sherry would hold me down and tickle me, and I loved wrestling and play fighting with her, and she seemed to always oblige. She would try to hold my arms between her clinched together legs so I could work my arms into her crotch. I would “accidently” grope her boobs or grab her ass when we were rolling on the floor I couldn’t get enough of Diane.
When I was about twelve, the family was at the lake and Diane came with my sister. My mom and my sisters wore traditional one piece swimsuits, I had never seen a girl with her belly exposed, so when Diane walking to our boat in her red bikini, she instantly became the vision of sex to me and that moment is etched in my mind. Many times, I would have a boyhood jerk off session thinking of Diane in that red bikini.
In October of 1976, I was fourteen years old, my sister Sherry was getting married, and Diane was her maid of honor. My sister’s fiancé was from Dallas Texas, so the wedding was at a church in Dallas, a four-hour drive from my hometown in Oklahoma. Dad would drive my mom, Jeannie and me to the wedding, but at the last-minute Diane asked if she could ride with us. Dad was driving our 1969 Dodge Coronet 440 with my mother in the front passenger seat, Jeannie was behind her and Diane was behind my dad, I was in the middle between the two girls. I acted like I was upset to be stuck in the back between my sister and Diane, but I was in heaven to be beside Diane.
It was a boring ride and, on the drive down to Dallas Jeannie and Diane both fell asleep. I acted like I was asleep and softly leaned onto Diane. I let my hand slip onto her thigh, she didn’t wake up and I leaned in a bit more and was kind of groping her when Jeannie woke up and saw me. She made a big deal about it and embarrassed both of us, so Diane didn’t dare fall asleep again on the trip down. My middle sister has always had a knack for fucking things up, and shockingly she still does.
We attended the wedding, and everything went as planned and we were all in the car headed back to Oklahoma around 8 pm. It was dark, we were all tired and soon all the girls were asleep. My dad driving, and I was acting like I was asleep beside my heartthrob Diane. I leaned softly onto her shoulder and let my head rest on her shoulder. I slowly placed my hand on her thigh and let it slide between her legs. Diane shifted and her body slipped all the way against the side of the car’s backseat and her legs parted a little. “What a break” I thought, “and she didn’t even wake up”, and I let my body shift with her, so now my head was more to the front of her shoulder inches away from her massive tit. Needless to say, I was in heaven.
As I said, I was fourteen, and had never kissed a girl or even held her hand, so to be in the backseat with this stunning girl was a once in a lifetime chance, and I wasn’t going to let it pass me by. I slid my hand into Diane’s crotch, I could feel the heat through her denim jeans. I rubbed my finger into her crotch, and she shifted a bit more opening her legs even more. I continued to rub her pussy through her jeans and after I got used to that, I slid my hand up her belly and lifter her sweater and slid my hand inside.
I don’t know what I was thinking, I mean if she had woken up and realized what I was doing and made a big deal about it, I’m sure it would have been terrible. My mom was right there, my dad too. It would have probably been the most traumatizing thing to happen to me in my youth, and looking back now, I can’t believe I was willing to take that chance. But I was a kid in puberty and there was no way I was going to let this moment pass me by.
I slid my hand up Diane’s sweater to her left breast and slipped my head down to her right one. I fondled her breast through her bra and ran my finger across her nipple. She continued to sleep though I could feel her breathing hard. I could feel the heat of her body and felt beads of sweat between her breasts. I couldn’t believe how fortunate I was that she was such a heavy sleeper. I slipped my fingertips inside her thinly lined bra, her nipples were rock hard, but her breast was soft and full. I cupped my hand around her full breast and slid my whole hand inside her bra and massaged her massive tit. My dick was hard, and I could feel it oozing precum into my underwear making a cold wet spot in my crotch.
I played with Diane’s tits and ran my mouth over it through her tight sweater. I kept wondering how I would explain that I was asleep and didn’t mean to have my hand up her sweater, it just happened? My head was spinning, and my cock was throbbing. I had never experienced anything like this before and I just kept going. I played with those beautiful tits for a while, and then I decided that I had to push my luck and get my hand inside her pants. If she woke up with my hand inside her pants, there would be no way to explain that, but at that point, my dick was doing all the thinking.
I slid my hand down her tight belly and let it rest at the waistband of her jeans for a while. I tried to force my hand inside, but they were too tight, there was no way my hand was going to fit in there. I needed to unbutton her jeans. I placed my hand over the button on her jeans and when I got the nerve up, I pulled it as softly as I could not to wake her, and they came undone, I was in luck. I didn’t know how I was going to explain that, or what I thought she would think when she woke up, but for now I just didn’t care. I slid my hand inside her pants and pushed the zipper down a little so I could get my entire hand inside the waistband of her panties.
I softly forced my finger to her pussy. I knew nothing about what I was doing, and had never seen a girls pussy except for magazine pictures, so I was just doing what I wanted, but I knew I was going to keep probing until I knew everything about her most private parts. I pushed my hand inside her panties, and I could feel the hot wet folds of her pussy on my fingertip. I slipped the tip of my middle finger into her moist hole and ran my finger in circles around its wet slick opening. Diane moaned a few times and I couldn’t believe my luck of her continuing to sleep through the entire event. I was so horny I can’t believe that I didn’t cum, but my shorts were dripping wet and I was glad it was dark, because I know I had an obvious wet spot.
I must have fondled her body for a couple of hours, it’s hard to say, but when I was done fingering her, I pulled my hand out of her panties and put my finger to my nostril and sniffed the musty smell of her pussy, then I had to lick the juice off. I had never smelled or tasted pussy before, but now that I knew what it was like, I wanted more. After I saw the lights of my hometown coming into view, I knew that the experience was over. I straightened up Diane’s bra and sweater the best I could. I sit up straight in the middle and acted like nothing happened. Diane woke up and sat up. She finished straightening up her sweater and pulled her bra into place, and then she realized that her pants were unbuttoned. She looked at me and said, “Gosh, that wedding cake must have made me fat, I can’t even keep my pants buttoned”. She never knew!! Good thing for me Diane didn’t wake up while I explored her body… or so I thought.
We arrived home around midnight, my mother said, “Diane, you should stay at our house tonight and Jerry can drive you home tomorrow”. “Are you sure?” Diane returned. “I can take you home tonight or tomorrow, it’s no trouble and either way is up to you.” my dad replied. “You can sleep in Sherry’s room, no trouble.” mom continued. “Well, if it’s no trouble, I’ll just stay the night.” She finished. I really didn’t mind either way because I knew that I was going to be masturbating to the thought of what I had been doing for the entire drive anyway. I mean, I had just climbed Everest as far as I was concerned, this night couldn’t get any better!
We all went in the house, my dad had me get Diane’s dress and bag with her makeup and shoes that she had worn for the wedding and bring it in the house. I took it to my sister’s room and passed Diane in the doorway. In the light of the room she looked flushed and she gave me a smile as she brushed against me in the doorway. “Thank you, Andy,” she said, and I turned to make my way to my room. I showered walked to my room. I heard the shower in my sister’s room as I walked by. I considered seeing if the door was open and seeing if I could spy on her but thought I had pressed my luck as far as would get away with tonight and went to bed.
I had only had time to start stroking my cock and fantasizing about the trip that I had just had with Diane, when I realized that my doorway open and I could make out a figure standing in the doorway. “SHIT!” I thought to myself and pulled the covers over my waist. “Damn, it’s mom, and she caught me jerking off,,,, AGAIN!” I finished my thought. “Mom?” I questioned into the darkness. The figure slowly and quietly stepped into the room and closed the door behind her as she sauntered to my bed.
I just knew that my mother was going to tell me how disappointed she was as my head started going through all the scenarios of what I would say. Then the figure put her knee on the bed and silently climbed onto my bed. IT WAS DIANE!!!
“Did you really think I was that heavy of a sleeper?” She giggled as she slipped under the covers and snuggled beside me. Our naked bodies were against each other and she crawled onto body. I felt her soft hand squeeze my raging hardon. I couldn’t believe this and was incapable to make words come out of my mouth. “She wasn’t sleeping, she was just faking it!”, my mind finally understood. I was in shock as Diane straddled my body and kissed me for the first time. It was my first real kiss, and she began to teach me how to kiss. She twisted her face on mine and forced her tongue in my mouth. I just did what she did and kissed her back I ran my tongue along hers and we kissed for a long kiss, while she moved her body over mine, her tiny waist rubbed against my swollen cock. It felt so good I never wanted it to end.
Diane rolled off me and pulled me on top of her. She pulled my face to hers and continued to kiss me, her long hair cascaded around our heads like a waterfall, her perfume was intoxicating, and the taste of her mouth was like honey. Diane held my head firmly with both hands and pushed my face down her neck and directed me to her chest. I alternated between her breasts kissing and licking the entire time. Her nipples were small and tight and I sucked and bit at them with my lips as well as licking them with my tongue. She loosened her grasp on my head and now with just one hand on the back of my head she guided me to her pleasure spots as she had me fill her desires. I was just a fourteen-year-old boy, but Diane continued to tutor her young lover.
I felt as if I was in a dream, my head was swimming with euphoria. I had never been so intoxicated with raw sexual desire, and even though I have had some very good moments with some very good partners, I have never had an experience like this one. Diane was the director and I was merely an actor that took all direction from her, and she dominated me with her sexual desires.
Diane was laying on her back with me on top of her petite body. The room was dark, but it was light enough to see her with her head drawn back into the pillow, her chin was the only part of her face I could make out. Her massive youthful melons flattened out and spread widely, with my face pushed into her bellybutton, I kissed and licked her obediently. She continued to control my every movement. Diane had me by the hair, not too rough, but firm enough to let me know that she had full authority. She pushed my face into her open crotch and my nose was buried into her pubic hair and she thrust her pelvic bone into my face. My mouth was positioned over her pussy, and she spread her legs further as she drove my face into exposed muff. As she used my face to pleasure herself with, I felt the moist slit of her vagina at my lips, so I kissed her pussy lips the same way I she had kissed me.
Diane was writhing and her tiny body continued pressing her dripping wet box against my face, her breathing was intense and could see her firm belly convulsing and her massive breasts flailing in her spasms of agonizing pleasure. I timidly pushed my tongue into the opening and was rewarded with an animalistic moan from Diane as she slipped into ecstasy. I sucked the tasty juice from her dripping honeypot and pushed my tongue deeper into her moist recess, her body bucked and jerked, so much, I had to grip her small waist and hold on to keep her pussy on my tongue.
I started licking and running my tongue across and then into her juicy slit. Whenever she gripped me and jerked, I did that more. I didn’t know what I was doing, but I knew that she was loving it and that is all I wanted. My every desire was to pleasure her, and I never wanted it to stop. Diane released my head and gripped a fistful of bedsheets with both hands. She ground her pussy into my face and rocked her small hips as I continued to explore her pussy with my mouth. Her luscious juice was covering my face and I licked her like candy as she began to moan, then her body went stiff and she through her head back. Her body twitched every time I moved my tongue. Diane relaxed and stared at the ceiling while she caught her breath. She pulled my head from her lap. I kissed my way up to her belly and then up to her beautiful tits. I loved her boobs and spent a few moments squeezing and playing with them, pushing them together and alternating between her nipples. Our faces met and we kissed, sharing her succulent cum that was dripping from my lips.
She felt my pulsing hardon pressing on her inner thigh as we kissed. We explored each other’s young bodies, and after a few minutes of intense probing and petting she was ready for more. She pulled me up to kiss her and I felt her hand on my throbbing member, her soft hand guided it skillfully into her sopping wet snatch. She was so wet that I slid in easily and she pulled my hips into her. Diane let out a soft purr in my ear as I sank my stiff rod to the hilt. She was tight, but well lubed and her pussy gripped me firmly as began to thrust inside her. Her hips rocked and she thrust into me as I pounded into her. I had never felt so excited in my young life.
Diane started to moan, and I could tell that she was in a pleasureful orgasm. I was ecstatic that I was giving her such pleasure. I had masturbated enough, that I knew I was about to cum, but this orgasm was different. It started in my stomach and then it felt like a jolt of electricity shooting through my groin into my cock, then as I exploded a massive load in Diane’s pussy, a series of electric shocks went throughout my body. My dick pulsed jet after jet of cum inside her, it felt so good I wanted to go deeper and stay inside her. I couldn’t maintain my own weight and I collapsed on Diane’s demure frame trying to regain my senses. I could feel my heartbeat in the head of my cock as I held it inside Diane’s snug snatch, the warmth of her body heating my pleasure.
We lay there collecting our thought and catching our breath. I was still inside her but as my cock began to soften, I felt it slip out of her and felt the rush of my hot cum pour out of her onto my bed. I shifted my weight so that my hundred-pound body wasn’t smushing her little ninety-pound figure. I kissed her deeply and fondled her body for the next hour. We never got to sleep that night, and we made love twice more before the morning light began to creep through my window, and we both knew that Diane had to sneak back to my sister’s bedroom. Diane kissed me, then stared into my eyes and smiled, she slipped out of my bed and quickly put my sister’s robe on, and she was out the door.
I didn’t see Diane again for almost a year. She got married to this looser, Donny, had three kids and then divorced within a few years. She would get together with my sister when they were both in town, she might give me a smile and a wink, our little secret, but we never spoke of the night we had together and I know she didn’t tell my sister, I guess maybe she felt like she had taken advantage of an underaged kid and I was a little embarrassed about the way I had fondled her and felt her up when I thought she was asleep, I really don’t know, it was almost like it never happened, but I know I will never forget it. I think about it often and it still turns me on, I guess you never forget your first time.
