I've been inspired by stories on this GREAT site to share the following experience from many years ago. Unlike some of the stories I've read on here, this absolutely happened and is completely true. I would LOVE to hear stories from others about their 'first time'.
My first 'sexual experience' occurred about twenty years ago, when I was thirteen and a half. It came from out of the blue (no pun intended) when I was spending an afternoon at my cousin's house. She was sixteen and we weren't particularly close. She was pretty nerdy (and VERY smart, today she is quite a successful business woman working for a Tech. company) and not attractive by any means. She had long, scraggly hair, braces, and dorky glasses, and was pretty heavy - I would guess about 150-160 lbs. The only thing that I found half-way attractive about her was her breasts; they were VERY large for a girl her age.
In any event, she lived in the same town as me and my family, and I would see her and my aunt and uncle (she was an only child) pretty regularly. One day in the middle of the summer my mom and I drove over, and I was told I'd be spending the afternoon with Mary Ellen (my cousin) since my mom and my aunt would be going out shopping. It was a crappy day, raining and drizzling, so I resigned myself to the fact I'd be watching TV most of the day since my cousin usually holed up in her room, reading books and listening to music that I hated.
We got to my cousin's house and my aunt and my mom left pretty quickly. My cousin and I mumbled 'hello's' to each other and she headed upstairs, and I stayed in the living room and flipped on the TV. About ten minutes later the doorbell rang, and Mary Ellen came storming down the stairs to answer it. It turned out to be a friend of hers she had invited over (I didn't even know she had friends). I heard them in the foyer laughing and giggling, and then they passed through to the kitchen and I got a quick 'hello' from her friend (Lisa). Lisa was almost the exact opposite of Mary Ellen; thin, very small, almost non-existent breasts, very long straight brown hair and a pretty face. I also noticed she had on tight jeans and her ass looked great.
Right about the time I turned thirteen I had become VERY interested in girls, and after 'The Talk' from my dad and hearing things from kids at school, I had figured out what 'jerking off' was and had begun to do it just about every day. I had never, ever seen a girl nude, or even in underwear (except in my Mom's catalogue) but thought about it ALL the time (like all boys that age do).
There were lots of giggling and laughing coming from the kitchen for a few minutes, and then Lisa and Mary Ellen headed back upstairs. What was weird was that when they came through the living room they were looking at me and whispering, and as they went up the stairs they were laughing hysterically. I had no idea what they were up to, but just thought they were being stupid teenage girls.
I watched TV for another hour or so, and was getting bored, and every once in a while I heard more laughter from upstairs. My boredom was broken by the sound of footsteps and I heard Mary Ellen call me from the top of the stairs to come up to her room for a minute, she and Lisa wanted to ask me something. I was curious, and had nothing better to do, so I went on up. I walked into her room and Lisa was sitting in a chair looking at an album cover, and Mary Ellen sat on the edge of her bed. She asked if I wanted to play 'Truth or Dare' and I said I didn't know what that was or how to play (I didn't!). She said that's OK, we'll teach you and they told me the rules. It sounded stupid to me, but when Lisa stood up and I saw how nice her ass looked in her jeans I thought, what the heck I don't mind being in here with HER for a while.
So the game began. It started out with a bunch of lame 'truths', and I was getting bored, until Lisa asked Mary Ellen if she had ever French-kissed a boy. She blushed and said no, and then I took a 'dare' from Mary Ellen. She dared me to pull my pants down for ten seconds and show my underwear - it was then I knew things might get interesting. I had no problem doing it, so I stood up (I had been sitting on the floor) unbuttoned and unzipped my jeans and dropped them to the floor and stood there with my hands on my hips in my white underwear. I had no erection or anything, but I very distinctly remember the looks on each of their faces - wide eyed and mouths hanging open for a few seconds, and then leaning on each other and giggling and saying things like 'Oh my GOD!' When ten seconds was up I simply pulled my pants up and then it was Mary Ellen's turn. She took a dare, too.
After what she did to me, I dared her to pull up her blouse and show her 'tits' (that's actually what I called them). She balked at first, and after some gentle urging from Lisa she said she would. She sat on the edge of the bed and lifted her sweatshirt up under her chin. It's hard to describe how I felt. I'm sure other guys reading this remember the very first time they saw a pair of breasts in a bra. Mary Ellen's bra was white, with lace cups and wide straps - and by far the sexiest, hottest thing I had seen up until that point in my life. It was very tight, and the outlines of her nipples were visible, and it looked like she had pebbles on the tips of each breast. Her cleavage was deep, and I felt myself getting hard. Mary Ellen blushed deeply as she held up her sweatshirt, and seemed flustered when she finally dropped it.
The game progressed from there, with everyone flashing various pieces of underwear but no one going so far as to dare any nudity. This was interspersed with questions about who else we had seen naked and how much they had done sexually (none of us had seen or done ANYTHING, except Lisa had seen her twelve-year-old cousin naked when he was getting changed at their house a few months before). The talk was beyond what I believe any of us had ever verbalized to anyone else, but obviously something we had all thought about (what teenagers don't?) and looking back on it (as I have many times in my life) we were all just a horny bunch of kids. Finally the 'truth' question about masturbation came up: I asked Mary Ellen if she ever 'played with herself'. That set off another round of giggling and laughing between the girls before she finally composed herself and said that yes, sometimes she did! Of course Lisa asked me next (and I said yes, almost every day) and Mary Ellen asked Lisa, and she said yes once in a while. Then we asked each other when and where we had done it last (I said last night in bed, Lisa said two days ago in HER bed, and Mary Ellen said she had done it about a week ago in the shower). I was completely boned at this point, and it was obvious what the next round of truth/dare would be - and it was my turn.
Mary Ellen dared me, very specifically, to take off my pants and underwear completely and stand in front of her and Lisa and 'whack it'. Even though I was very, very horny and hard, I was scared and nervous too. I told them I didn't think so because I was afraid our moms would be home soon. They gave me a hard time and said they wouldn't be home for hours, and kept egging me on. We went back and forth for a good ten minutes, and they finally convinced me to do it.
They sat on the edge of the bed, and I stood in front of them. My hands were shaking as I took off my jeans, and my boner was obvious in my underpants. The girls both got silent when they saw it, and were blatantly staring. I was REALLY nervous, and told them I didn't think I wanted to. They kept urging me to, saying come on, chicken, etc. So finally I said I would, but they had to take off their clothes too. They of course protested at that, and we went through another round of back-and-forth (me in my underwear the whole time, no less). We were all agitated and horny and curious, and scared and nervous too. Finally we came to an 'agreement'. They would strip to their underwear, and if/when they did I had to jerk off in front of them.
It was my turn to sit on the bed as they stood up. They were both laughing nervously and giggling and leaning all over each other, until finally Lisa lifted up her tshirt and took it off. She had very small breasts, practically non-existent, and wore a little pink bra (more like a training bra) with a little white silk bow in the front. She was skinny and had a smooth, flat stomach. Her jeans rode low and were tight, and she was braver than MaryEllen and unbuttoned them and took them off. I had seen her panties before during the game (white cotton bikini, very tight, with yellow and purple flowers on them) but seeing her now standing there in just them and her bra was almost too much for me. Since she and I were both now in our underwear, Mary Ellen was the 'odd man out' and without any further urging she took off her sweatshirt and then removed her pants. Her panties were more of a girdle type (briefs I guess) and her belly was round and prominent, but her tits were gorgeous.
The laughing and giggling continued, and they pulled me off the bed and sat down and started shouting that it was 'my turn'. At that point I was so horny I didn't care who was there, I had to jerk off. I pulled my underwear down and my cock sprung up and back against my stomach (I was a fit, somewhat muscular thirteen-year-old as I wrestled and played football since the age of nine). I kicked my underpants aside and 'posed' a mere few feet from the girls, proudly displaying my erect cock. They were quiet, staring at me (again) seeing a real penis for the first time in their lives. Lisa had her hands folded in her lap, Mary Ellen was leaning back slightly with her palms down on the bed (I remember all this like it was yesterday). I took hold of my cock with my right hand and started to rub, not thinking about making the experience last; I was horny and wanted to come. As I stroked my cock they both remained quiet. I clearly remember noticing how both girls' nipples were hard and visible through their bras. As I jerked I moaned a little (I couldn't help it...) and as I looked down at Mary Ellen saw that she had sat forward slightly, her left hand still on the bed but her right now pushed down between her thighs. I heard her let out a loud sigh, and her hand was moving up and down ever so slightly along the length of the crotch of her panties, her legs spread slightly. Lisa didn't notice as she was mesmerized by me stroking, and as I locked in on Mary Ellen quietly rubbing her crotch it sent me over the edge. I announced (in a shaky, somewhat loud voice) that I was about 'to shoot' and I stepped in front of Lisa and my hand was moving in a blur on my cock. I began to come, and come, and come some more. It was an absolutely unbelievable feeling. One blob of cum hit Lisa on the thigh, and she jerked back and said 'ewwww' and the rest landed on the bedspread next to her and on the floor. I made quite a mess.
As I came down from my 'cum high' I realized what I had done, and was very embarrassed. Lisa had got up to wipe her leg off, and I quickly went to the bathroom to find a washcloth to clean everything up. When I came back Mary Ellen was still on the bed, hand between her legs, not overtly masturbating but obviously still touching herself through her underpants. I wanted to get out of there, so I grabbed my pants and underwear and headed downstairs, where I dressed and got a glass of water. Lisa and Mary Ellen stayed upstairs for another hour and then came down and didn't say a word to me. To this day I wonder if they masturbated after I left, and have fantasized many, many times about what it would have been like if we had all gotten naked.