When I was 14 years old, I had my first sexual experience with another, and it was with my sister!
My sister is two years older than me, and I was always interested in her body, as far back as I can remember. She was always a 'big' girl, but not in a 'fat' way; she was just tall and really filled out, and like our mom, had big boobs. She also had a beautiful face.
I remember always trying to get a peek down her blouse or anything else I could see, but really never got a good look until I was about 13 years old.
She baby sat for a family that lived across the street from us and one time they went on a vacation and asked my sister to 'house sit' for them; to keep an eye on their house while they were gone. They had the nicest house on our block and the only one with a swimming pool!
One hot afternoon my sister asked me if I wanted to go with her and go in their pool, to which I enthusiastically agreed.
We got into our suits, grabbed towels and walked across the street. This was many years ago, and women wore single piece bathing suits then. We jumped in the pool and were having a great time.
Out of the blue, my sister tells me that she went 'skinny dipping' the last time she was there alone, and how much better it felt without her suit on. She then added 'I'm going to take mine off.. do you want to too?'
I couldn't believe my ears and immediately replied 'OK'! We slipped off our suits under the water and put them on the deck.
I could tell that she didn't want me to see anything, but her boobs were trying to float, and I got plenty of glimpses of her nipples as we swam and played for the next half hour or so. I had never seen her nipples before and they were a beautiful light pink with just a pea sized button in the middle.
I was also trying to see her crotch but she never came out of the water, but I could see a dark patch there, under the water.
As we swam naked together, I got an erection from seeing her and being free, I remember how good it felt and knowing that she couldn't see it and being that close to her.
I found out what my little penis was for the next year, after having a 'wet dream' one night. I remember it waking me up as I came for the first time, how good it felt as I turned on the light and examined the warm sticky mess in my underwear.
As I began to masturbate regularly, the thought of seeing my sister, or even better, her seeing me became a regular fantasy. I would also go through her dirty laundry and masturbate while smelling the stains on her panties.
I was fourteen (because I remember she was driving) and couldn't stand it anymore, I decided to 'pretend' I didn't know she was there, and let her catch me doing it!
Our parents both worked and didn't get home till a couple of hours after sis and I got home from school, and I got home before she did.
Our house was arranged so there was a hallway that turned at my bedroom door and then went to hers. And, my bed was right in front of my door, so that you were looking up my bed from the hall.
I left my door open so she would see just enough of my right side, with my undies pulled down and my movement. The thought of her catching me was making my heart and my young boner pound! I stopped myself short of orgasm several times before I heard the sound of her car coming up the driveway!
I heard the back door open... I closed my eyes as if I was unaware and kept masturbating. I heard her footsteps in the hall... would she see me? Would see stop? What would she do???
I was panting uncontrollably.. her footsteps stopped outside my door.. I knew she must be looking at me, but I kept my eyes closed, pretending I was alone..
The sound of my breathing and rubbing was the only sound for what seemed like a very long time, and I was getting close to cumming. The silence was then interrupted with 'feeling good?'
I pretended I was totally surprised and embarrassed, pulling my undies up over me, and acting like nothing was going on. Of course I couldn't slow my breathing or hide my now covered but throbbing penis.
She came into the room, sat on the side of the bed next to me, staring at the bulge and said 'It's OK, I know what boys do. You can keep doing it.. I want to see you do it'.
I lay motionless, then slowly stuck my hand down my shorts and slowly rubbed myself underneath my undies. In a more insistent tone she said 'Take it out, it's OK.. I want to see you do it'.
So I pushed my undies down again and, holding myself straight up, began to masturbate faster.
My eyes were wide open now, and watching her watch me intently. She sat silently staring at what I was doing. The only sounds again were my breathing and rubbing.
Her sitting right next to me watching me do it, was the most excited I had ever been in my life, so it was what seemed like less than a minute when my cum started flinging out in every direction, timed with my panting breaths and convulsing abdomen.
She leaned over and got a tissue from over my headboard and wiped me up, saying 'I'll bet that felt good!'. Then she just got up and left the room.
After that, I would 'let her catch me' on a regular basis, with her eventually 'helping me', which she seemed to really like doing and would just take over every time.
She never touched herself nor did I ever get to see anymore of her, but those were the best hand jobs of my life!
We're all grown up now and she's married, and has never said anything about it.