Never EVER had one like this before
I have a really good friend called Sarah. We are not and never have been attached, but somehow we are very close for all that. Sarah has had boyfriends (and two girlfriends!!) and I have had three girlfriends in my life. This happened after an exam in hospital.
I had been having trouble peeing. Not that I couldn't go, just that it took forever, and if I left it too long before going it hurt too. After weeks of putting it off, I finally went to the Doctors office. Sarah had come with me for moral support. The doctor listened and asked me a lot of stuff about my sex life. Then he drew some blood and said he was going to examine me internally. I had to lie on my left side with my knees drawn well up as he pushed his finger deep into my ass. I was as embarrassed as all hell. Then he said he needed to put an instrument in there and that I would feel very 'full'. It was awful and it hurt me a lot. The doctor smiled and said he didn't think there was anything serious going on. Then he asked me how long it had been since I had sex. I told him about six months. Then he asked me how often I masturbate. I lied and told him every day, but I don't think he believed me because he told me it would be a good idea to do it again soon. He told me he would call if the blood work showed anything unusual.
I walked home with Sarah, trying to ignore the greasy feeling around my ass. In my room I told Sarah what the doctor has asked me and I told her that I lied when he asked how many times I jack off. I've never been able to make myself cum on my own. I think its something to do with my religious nuts called parents. Anyway, I just can't go over the edge, and its not for want of trying. Sarah said that she thought that I was having trouble peeing because I get too full of cum! We laughed for a while and then she said 'Chris, if you really need to cum then, umm I don't mind helping. What would you like me to do.' I had never thought of Sarah in that way before and knew she was just doing this as a friend. I asked her if she would sit in a sexy way for me and let me look at her. She squirmed around in my chair for a while until her skirt rode up and she let her knees flop open giving me the sexiest glimpse of her panties. I was hard in a second and got my cock out and started to jack myself. Sarah was a total star, she opened her legs wider and then started to talk to me. 'You know, Chris, I rub my pussy every night, I love frigging myself off. Sometimes when I cum, my cunt feels like its electric...' and so she went on, getting dirtier and dirtier. I could feel myself getting close but I still couldn't go over. Sarah, by now was using language I never even thought she knew! In the end I told her that I didn't think I was gonna blow. She got up and knelt beside me. For a wonderful moment, I thought she was gonna suck me, but instead, she stroked up my leg and pushed her finger right into my ass. And I mean DEEP. Then she kinda rotated it around in there and I came like crazy. I shot one rope clear across the room and she just kept on fingering my ass the whole time. When I finished, she went to the bathroom and washed her hands before asking me to watch her. It was totally horny. Sarah lay on my bed, took her panties off and rubbed herself to a beautiful orgasm. I was kneeling on the bed watching her and I got hard again. Just before she came she just flicked her panties at me and I had my face in them in a moment. I think that's what made her cum. I came again too although nothing like the amount I shot earlier. It went on my bed, on Sarah's legs and even a few drops hit her pussy.
Since then we are still really good friends and we help each other cum from time to time.