After I graduated college I lived at home for a year while working at my first job. My sister was a freshman in college. She had her roommate visit over Thanksgiving break along with several other friends she had made. Something clicked between us. It was unspoken – I could just tell by the way she looked at me that she saw me as more than her college roommate’s brother, but as a possible sexual partner. An impression I did not get from any of the other friends of my sister there. Fortunately, the roommate was actually staying at our house. The other friends were either local or staying at other houses with local friends.
Not the first night, but the 2nd I dared to knock on the door of the guest room in which she was staying. She said, “Come in.” I entered and she seemed receptive (almost as though she was expecting me late at night). I sat on the bed and we talked for a while about innocuous things, and maybe 20 minutes later I moved in for a kiss. She willingly kissed back and got on top of me. She wore pajama pants and a T-shirt. She had an athletic build, thick yet muscular thighs and legs, small yet perky breasts and a firm ‘bubble butt.’ She let me take her top off and finger her. I took her pants off and she started stroking my penis. I don’t know why I thought to do this to this college freshman, but I put two fingers into her tight vaginal opening and my pink in her asshole. She did not resist. Instead she asked, “How many fingers do you have in my vagina and how many do you have in my anus?” I told her two in her vagina and one in her anus.
I started going down on her. She had brown, closely shorn pubic hair and tiny, little labia minora. She asked me if I had a condom. I had three in my pocket. I put one on, but she was so tight and with the desensitization of the rubber I couldn’t penetrate her. No problem. We removed the condom and she gave me a blowjob. It was pretty awesome head and when I orgasmed I said, “I’m going to cum.” She let me blast away in her mouth, swallowing all but the last two spurts of my ejaculation.
We kept in touch and she visited again over winter break. I actually had some lead time so I bought us theater tickets and made dinner reservations at a nearby restaurant. We did largely the same things sexually this second time she visited me (and my sister). I really liked this girl and I wanted to be in an exclusive relationship with her. I proposed just that over the phone one night. Sadly, but not so surprisingly, she was not willing to give up the free-wielding lifestyle college afforded her. I could understand that because she and my sister attended the same college I attended. And if I’m being honest, I was not exclusive the entire time I went to that school and enjoyed the free-wielding lifestyle very much myself. From that point on, we didn’t really talk over the phone. There was one other time, maybe a year later when she visited my sister. I did go out with the two of them and some of their other friends, but it was a purely platonic.
Source: reddit.com/r/gonewildstories/comments/lssx7z/my_tryst_with_sisters_f_college_roommate