I have been reading from this site for a long time now and wanted to contribute to the site.
I have always been a fan of Solo Touch and how people share their personal experiences to others.
This happened when I was 14 years old. I did not know how to masterbate in fact I did not even know there was such a thing. And as a kid I was very horny I had started cross-dressing and loved it.
I had two sisters, one was 17 that time and other was 21. My 21 year old sister was out of town so the story does not involve her. But I really started getting fascinated by women's clothes and that silky feeling. I always used to wait for the house to get empty and I would sneak into my sisters clothes. I just loved the feel of the underwear and the tightness of the bra. I had started to get very desperate to get into my sisters clothes. Once I had taken out clothes from the laundry and tried them in the bathroom.
I used to love these small transformations of mine but I never really looked at my sister in a different way. Many times I had worn panties and bra and my normal clothes on and walked around the house without anyone noticing. I remember I had blushed a lot. One day my friend properly taught me how to masterbate and I was pretty grossed out but that night I felt damn horny and gave it a try. The orgasm feeling was brilliant and I knew this was going to be a start of a new era.
Slowly to spice things up I started masterbating in my sister's underwear and I don't know why but I starting ejaculating on them. After I was done ejaculating on them I used to keep them back in the draw. I didn't know why I used to do that but my sister kind of ignored it I guess, well I thought she did. After two weeks of daily cum in her panties she one day came in my room with two to three panties in her hand and asked me what this was?
I was all confused as I was never ready for this, I felt stupid as I didn't think this through and I started blushing badly. Then she asked me again 'what does this supposed to do to me?' and I had nothing to say and started crying. She was disgusted and seeing me in tears she said 'oh my God, First you try girl's underwear and then cry, Wow you are actually a sissy' and then I stopped crying and like a good sister she came up to me and said 'its okay' and came and hugged me. I was wearing boxers that time and her boobs had touched me so I started getting a boner. She saw my boner and went like 'eww gross'. and she looked at me and said take it off and I obeyed.
My penis was fully erect and was standing at its peak. The whole idea of my sister seeing it was really awkward and she stared at it for a minute I guess. And then she said 'wow thats it? I never knew they could be so small also' and I was like 'you have seen before?'
She said 'duh! I am 17 I have seen many before'
I said 'well is this the smallest?'
she said 'well yea but don't worry its pretty cute'
She then came forward and held it and I felt very uncomfortable
She asked 'so you know what to do when its like this huh?'
And started moving my shaft up and down. I didn't know if I should cum or no but she started moving her hands faster and I yelled 'SLOWLY!!'
She smiled and put her face below my tip and said cum on my face. In two secs I came all over her face and she slowly waited for the last drop it was weird for me to do all of this but wow I felt awesome.
She took some tissues, handed me her panties and said 'these are for you and I can't wait to dress you up now'
End of part 1