My first and still most memorable masturbation experience with a girl happened shortly after my 14th birthday. A little background; my best friend from the time I was nine was Dave and he lived three blocks away. We did everything together, and I was over his house constantly (and he at mine). I was an only child, but Dave had a sister that was three and a half years older than us, Eileen. She was truly like a big sister to me, and from the first time we met we 'hit if off'. She was never mean to me, whereas other friends older brothers and sisters would treat Dave and me like 'little kids'.
Eileen was just a sweet girl, with a very dark complexion (the family is Italian), dark brown eyes and black, shoulder length curly (permed) hair. She had a great smile, cute laugh and a petite body. Interestingly enough, as I turned 13 and learned about sex and masturbation she at first was not the object of any of my fantasies since she was more of a friend than a 'hot girl'.
The day this incident occurred was a Friday evening, about 7:30. I remember it vividly. I had just finished working (at a local country club cleaning golf carts and doing other stuff around the course). A few days before I had broken up with the first girlfriend I ever had. We had started dating during the last month of school, and after three dates she told me she liked me but wanted to date other guys. I knew the real reason though; twice she had tried to initiate a 'makeout session' with me (once in the movies, once in her backyard after dark) and both times I had frozen and chickened out. Not because I didn't want to kiss her and touch her, but I didn't know HOW so I froze. I was devastated and really down in the dumps because I liked this girl (Sue) a lot and I thought she was very pretty. So I was in a depressed mood on my way home when I stopped at Dave's to see if he wanted to hang out for a while and maybe go down the street to Carvel to get an ice cream.
I dropped my bike on the side of the driveway, went up and knocked on the door. There were no cars in the driveway and it didn't look like anyone was home, but I figured I would check anyway. I was pleasantly surprised when Eileen answered and told me to come in. She said her dad had gotten tickets to a Cubs game from a guy at work and that Dave, her mom and dad had left a few hours before to go to the game. I was about to leave when Eileen said I could hang out for a while since she had nothing to do and wouldn't mind some company. It was nothing out of the ordinary since we had hung out before, just the two of us, watching TV sometimes, so I said sure. She told me she was watching a show in her room and told me she was going to grab some sodas and she would meet me there.
I went up the stairs and into her room and she came in a minute later with two bottles of Coke. I noticed now what I hadn't noticed before; I thought she was wearing a t shirt and shorts when she answered the door, but as she plopped herself on the bed I became aware she was wearing pyjamas, a shortish white nightshirt with a teddy bear on the front that slid quite far up on her thighs. She handed me the Coke and slid back on her bed, with her back up against the headboard. I was sitting on the left edge of the bed and took a sip of the soda, while out of the corner of my eye drinking in her long, smooth, beautiful tanned legs that seemed like they went on forever. Before my thoughts could turn perverted, she began to make small talk, and before I knew it I was spilling out my story about my 'girlfriend' and how we had broken up. At first I didn't tell her why, but then reluctantly shared with Eileen how I had chickened out about kissing Sue.
Eileen was SO easy to talk to, and she told me what a great guy I was and she wished all guys were so sensitive and cared about how girls felt. She told me if I was older or she was younger (she was 17 when this happened) that she would definitely date me. As she told me this, her hand came to rest on my thigh and it was like electricity going through me. After all these years, for some reason on this night I started to imagine Eileen sexually rather than just as a good friend. I noticed the scent of her perfume, and how the little dimple on her left cheek looked so sexy when she smiled. I observed all this while she went on talking (she LOVED to talk!) and then she shocked me when she said that she could teach me how to kiss so that I would feel more comfortable next time I was with a girl.
I didn't know what to say, and didn't say anything because I couldn't. I could feel myself blushing, and Eileen joked and laughed and said I was so cute that I blushed even when she said 'kiss'. She asked me again and said it wouldn't be serious or anything, but she could teach me the 'technique'. I looked at her, and could tell she was serious, and I just nodded my head yes. She scooched up on the bed to get closer to me and put her face next to mine. She then proceeded to tell me how girls like guys to start out slow and just peck their lips lightly, and then she showed me how. She put her hand on my chin and brought our faces together and our lips touched, and then we proceeded to lightly 'peck' for a minute. I was instantly aroused; my cock got harder than it ever had in my whole life to that point in less than 30 seconds. She asked me if I was OK and I smiled and said sure, I was fine, and then she said she was going to show me how to French kiss. This time she put both her hands behind the back of my head and put her lips on mine, and her tongue began to press against my lips. I instinctively opened them, and before I knew it our tongues were twirling together and my hands had naturally encircled her. We continued, for less than a minute, until she broke it off and sat back.
I moved back slightly as well (still on the very edge of the bed) and looked at Eileen now sitting cross legged smack in the middle of her bed. Her hands were palm down on each side, and I saw that her nightshirt was pulled up so much that the crotch of her panties were clearly visible. I tried to divert my eyes elsewhere but couldn't; I looked on for several seconds, and it must have been obvious to her where I was looking. She didn't close her legs, she told me quietly that I was a REALLY good kisser for my first time and that the girls were going to love making out with me. As I looked at her face I saw that SHE was looking at MY crotch, I was wearing worn cut offs and my erection was pretty evident.
Eileen laughed and said she was glad to see I was a normal guy and that I got excited by making out. I blushed some more, without saying anything. She was much bolder than me (I was a very shy kid, and still am introverted to this day) and said that if guys don't 'take care of themselves' when they get horny they get blue balls and could get a hernia (I didn't know it was a bunch of bull at the time). She then asked me if I ever 'did it' yet, and I told her I didn't know what she meant. She said, you know, jerk off. I didn't say anything for a full 10 seconds, then finally told her that yeah, sometimes I did.
She then leaned forward again and began kissing me, half up on her knees. Her right hand began to rub my thigh, and then she was rubbing my erection through my shorts. It took all my power not to ejaculate in my pants with her playing with my erection for a mere half a minute. She stopped kissing and rubbing me and sat back and told me she wanted to see me do it. I told her I didn't think so, that I would be embarrassed, and then without speaking she lay back on her bed, back against her headboard, and lifted her nightshirt up to just below her chest. Her panties were in full view; beautiful white cotton bikinis with pink edging and a sexy thin lace waistband. They were tight, and I could clearly see the cleft of her vagina. Her stomach was flat and tanned, and her hips were flared and rounded. She placed her free hand over her crotch and began to rub it up and down over her panties. 'This is what I was doing when you rang the doorbell before.' She giggled and smiled and kept at it, and then slowly lifted her nightshirt up and off, revealing her tits. They were small, very small (probably no more than 32A) and capped with small brown nipples that were quite erect. She lay there in nothing but her panties, smiling at me, and she asked me again to show her how I do it.
I was shy but not stupid, even at 14. My nervousness was replaced by my utter horniness, and I had my shorts and underpants down and off (in one move) in seconds and took my same place on the edge of the bed. I began to stroke myself while looking at Eileen, who was masturbating over her panties with one hand while playing with her little tits and nipples with her other. We continued, slowly, for several minutes, with her asking me if I was having fun and if it felt good to play with myself, if I thought she was pretty, etc. It was very casual and relaxed, not a quick, uptight session; a lot of that had to do with our close relationship and 'bond'. She then stopped what she was doing and sat forward. She leaned over again to kiss me, this time another extended 'French kiss' and she then gently pushed me onto my back. She lay next to me, propped up on her left elbow, and began to rub my chest and stomach through my t shirt. It seemed like an eternity, but she finally ran her finger up the length of my cock and then took it in her hand. She smiled down at me as she started to stroke me, and in seconds I felt my orgasm coming on. As she jerked me off I reached up and touched her left breast; it was warm, soft and tender to my touch. That was the trigger; I bucked my hips and began to ejaculate. The first two thick streams shot up onto my t shirt (I had to borrow one of Dave's to wear home later!). Several others spurted out just about my cock and all over my pubic hair and Eileen's wrist and fingers. She continued to slowly masturbate me until my orgasm subsided and I began to go soft. She grabbed a fistful of tissues from beside her bed and cleaned both of us up. She asked me how it felt, and about a dozen other questions about what it felt like for a guy to orgasm, and as she was talking she eased back on the bed and began to stroke herself again through her panties. As she became more aroused she went quiet, and her hand went inside. To my amazement, she then lifted her hips and pulled her panties down to her knees, exposing her rather hairy vagina to my view. I watched, mesmerized, for the next five minutes as she got herself off.
That was the first of three such incidents where we were together. We never had intercourse or oral, but we did mutually masturbate each other each time. She showed me how to tease and flick her clitoris and to pinch her nipples for pleasure. Later that summer she left for college, and while we still saw each other occasionally on holidays we never got back together again. I will never forget those times together though, and still after all these many years still fantasize about our times together.