My first time was part nightmare, part exctasy.
This site is great because it not only provides maybe an outlet for a little fantasy, but also because it provides an outlet for some of us to shed any guilt or feelings of strangeness about some of our early experiences masterbating.
Here's my first time, and it's taken me a while to realize this was OK.
I was 12 years old and pretty innocent to the ways of masterbation. I had had wet dreams and touched my hard-ons a little before, but didn't quite realize what happens at the end of the journey. All the houses in the neighborhood where my family lived were packed in pretty close. Small yards, small driveways separating the houses. Well, one night I was walking past my older sister's room. Her door was open, but her lights were off which allowed me to catch a glimpse of what was going on in our neighbor's window directly across from my sister's room.
What I saw pulled me into my sister's room, pronto. The single lady that lived next to us, her bathroom was right across from my sister's room and I saw this lady coming out of the shower. I quickly shut my sister's door and feasted my eyes on the neighbor lady drying her wet naked body with a towel. I had never seen a real naked woman before. Real nipples, real pussy hair...mmm.
Without really making a choice to do it, I dropped my shorts and underware, got on my sister's bed on my knees and started stroking my pubescent dick as I continued to watch the nude woman. Of course by now, strong sensations were pulsing through my young penis. I wasn't going to stop this time. I don't think I could stop.
The naked lady finished her drying and left the bathroom and I sort of remember thinking about how I could get back to my room and continue to stroke myself without anybody noticing. As fate would have it, this is when my 16-year-old sister walks in and turns the light on.
She gasped and called out my name in horror and I started crying a little, but I still continued to stroke my penis. 'I'm sorry, I'm sorry,' I whimpered to her. 'I can't stop!' Seeing that I was even more upset and embarrassed than she was, she shut the door and said 'Ok, Ok, Ok...' in a soothing voice. I still continued caressing and stroking my small, but still hard cock.
(I learned later after this incident from my sister that she had been masterbating herself for years when she caught me, which makes sense to why she was so calm and did what happens next.)
She locked her door and stood near the bed. 'It's ok, Jamie, I'm not going to tell mom or dad. I won't tell anyone.' As I continued to masterbate on my sister's bed in full view of her, another wave of realization hit me. Still very embarrassed I started to cry again. 'I can't stop! I'm sorry, I can't stop!' I said again. (Which was true. I've thought about this for years, my body wouldn't let me stop. I think to this day if my mom or dad would've walked in, which would have been the ultimate horror for me, I wouldn't have been able to stop. I think it's amazing that human beings can get to this state.)
My sister reassured me again. 'Don't stop it's Ok. Is this your first time to do this?' I nodded as I stroked. She kept encouraging me and my embarrassment was subsiding more and my attention returned to the sensations that I was feeling. 'I'm not mad, but why are you in my room, Jamie?' I nodded my head towards the window. 'I saw our neighbor lady come out of the shower. She was naked.' My sister nodded. 'Yeah, she never closes the blinds. I've seen her naked lots of times.'
I groaned a little. My breathing got different. 'Does it feel good?' my sister asked. 'Yes, but it's also starting to hurt a little.' I still had oozes of pre-ejaculation dripping out of me, but I was rubbing myself raw. My sister saw that I was even bleeding a little.
'Here,' offered my sister, 'Hump my pillow. It will be softer on your weiner.' Without delay I straddled my sister's pillow and began to pump away. My sensations sky rocketed. I went faster and faster. I closed my eyes and kind of zoned out for little bit, my drive to cum overtaking my feelings of shame and embarrassment (which would return en force later).
I was not really aware of it then, but I know now after having discussions with my sister and just plain common sense, that seeing all this greatly aroused my sister as well. I think I was pretty close to coming when my sister spoke to me again, sort of breaking me out of my mastabatory trance.
'Jamie?' 'Huh?' I sort of moaned. 'I'm going to do something with you, but only once. Ok? We're only going to do this once.' I rose back up on my knees and continued to pump her pillow vertically. I didn't really catch on what she was talking about. Truth is, I think I was getting delirious at this point. I watched in shock as my sister took off her shirt. My eyes took in the sight of her belly skin and bra. Then she took off her shorts, revealing her tight panties. 'I'm going to do this with you. OK? But only once.'
I nodded. I was in total overload. I'm putting this mildly too. Keep in mind that the span of time from when I saw the naked lady up to my sister starting to disrobe was probably less than 10 minutes. She sat across from me on her bed. She then reached back and undid her bra. My sister was 16 at the time and she already had an ample breast size. I will never forget the sight of her nipples. They were thick, fleshly. They pointed out at me. She then spread her legs out so they went past me (still on my knees, pumping her pillow upward) then she scooted her ass forward so the rest of her body was inches in front of me.
I was pretty speechless. She said, 'I'm going to stroke myself in front of you too. But this will be the only time, OK?' I nodded, 'Ok.' She kept mentioning it a lot when we did this. (At the time, and for a while afterward, I thought she was saying this because she was acknowledging that we were doing something bad. I now realize she was saying this because it wasn't 'bad' but it was something that might not be healthy to do all the time together.)
My sister then began stroking her clit through her panties. I could see her wetness seeping through the cotton. Her tits started heaving and a weird and arousing look graced her face. I pumped the pillow harder. I started grunting. I was starting to feel the welling and rising of my cum load. But also my penis really started to hurt. My sister must have seen a grimace of pain on my face in between her moans. 'Are you OK?'
'My weiner really hurts,' I said. 'Let me see,' my sister asked. 'But I can't stop!' I pleaded. 'You don't have to stop, but let me see it just for a second.' By now my pain was just as sharp as my pleasure, so I dropped the pillow to show my sister my dick. I was horrified to see blood stains on her white pillow. There were little blood marks on my penis where it had been rubbed raw. In fact my penis was a mess. Shades of purple and red. It was bigger than I had ever seen it.
My sister must have seen the panic in my face. 'Oh... Jamie, it's Ok. it's alright.' I felt a flush of tears. 'It's going to be OK. I'm going to help you do this, Alright?' I said Ok. She wanted the pillow, so I gave it to her and she doubled it over and put it behind her back. Then she slid off her panties and moved back so I was kneeling again inches away from her vaginal hold. The smell of her flooded the room. I had never smelled a woman before. I think her odour alone was responsible for my dick growing another grade harder.
'You watch me a little, watch my pussy,' my sister instructed. PUSSY. I had never heard my sister say it before. It shocked me that she called her own that. My sister is a brunette, so her pussy hair was dark and thick. She stroked her pussy and the put a couple fingers far into her vagina and then pulled them out. 'I'm going to touch your weiner a little, is that alright?' she asked. I nodded.
She reached out with the hand she had been playing with herself and stroked my boner. It was electric. I started to spasm with her touch. Also it was smooth. Her pussy juice was just the lubricant my poor penis needed.
My sister squished her hand back into pussy and then smeared more of her juice up and down my boner. Finally, the welling rose and rose, I started grunting and spasming and then super-white semen blew out of the top of my penis. My sister rose up and grasped both of my hands as I continued to shudder and shake. I saw black dots for a moment. So much intense pleasure and then and intense pain. My first mastabatory ejaculation is still the most powerful one I can remember.
After I calmed down a little I just started apologizing to my sister. I was almost in tears again. I had made a mess of her bed. I didn't know how we were going to hide it. She consoled me. Told me not to worry, she'd take care of it. 'I still have to finish myself,' My sister said after I had calmed down. 'Will you help me?' she asked. I looked at my sister's blooming and naked body, it was absolutely beautiful.
I said I would, but I started feeling massive guilt coming on me, chasing my erotic feelings I had at that moment. 'How do I help?' I asked. My sister laid down flat on the bed. 'Here, lay to the side of me and suck my nipples.' So I laid to the side of her and began sucking her nipple. I could feel I was getting a boner again. My sister started to moan and move her hips in weird ways. I looked to her face and saw her eyes were closed.
'That's it. Keep sucking my nipple.' I could tell without looking she was playing with her clit and everywhere in her pussy. Then she started saying really intense things.
(I have huge wood just remembering as I'm typing.)
She said, 'Suck my tits, Jamie. Milk me, Milk me, brother...' Her breathing was getting out of control and she was writhing and bucking her hips up and down. Truth is I was scared. I was aroused and mortified. Her smell was driving me mad. Then her whole body tensed and seemed to lock up. I stopped sucking on her. I got off the bed quickly. I really didn't understand it then, but my sister was having an intense orgasm.
I started to put my clothes on. Shame was creeping on me. I think my sister sensed it. Before I left her she said, 'Don't worry about this, Ok. I'm not going to tell anyone and this is the only time we'll do this.' I think I muffled an Ok before I crept out of her room.
My sister tried to bring this up a few months later to see if I was Ok. I didn't want to talk about it. So she dropped it. We functioned normally as brother and sister the rest of our childhoods and into our adulthoods. Our parents and our youngest brother never knew about 'our evening,' and my sister and I agreed they never will. One Christmas break, when I came home from college I was ready to have a frank chat with my sister about what we had done together. She said she was sorry if she and pushed me in a direction I didn't want to go, but I told her that there was no need. By that time I had made peace with the whole thing and dropped the guilt of masterbation and embraced our 'event' as a special one-time memory. She said she had never regretted it, but just didn't want it to effect our relationship. She's married now and has a kid and I'm in a serious relationship, but we've vowed never to tell anyone else about our masterbation together. I plan to call my sister to look at this story on Solo Touch. I'm sure she'll masterbate her pussy after she reads it, just like I'm going to shamelessly whack off when I get done writing.
I'd be real interested in hearing other true accounts of brother's and sister's doing this sort of stuff. I'm sure it happens all the time, given the nature of the relationship and the timeframe that sibling's are together.
P.S. Sis, I'll always cherish the night I 'Milked' you!