I have had pity sex with my roommates father. He and I had had a very nice and friendly relationship, and his wife (my roommate mom) was always very welcoming. Her Dad and I flirted a bit, and his wife got a kick out of it. The flirting never went anywhere. Anyway, she became suddenly ill, and passed away very quickly and unexpectedly. About a year after her passing, my roommate and I went to her house for a visit. We talked for a long time, and we both thought it would be good for him to get out and meet some nice women. He said he already knew a few nice ones. When he said that, I swore he was slyly looking at me - and I had this immediate feeling or warmth and longing in all the right places. Nothing happened that visit. He came to school to see us one weekend. Roommate had a long afternoon lab class, so he asked me to go to lunch. It was a lot of fun talking -- and flirting again. He asked me up to his room, and I knew what he wanted. He offered me a drink and just blurted out that he had feelings for me, that he thought they were wrong, but he couldn't help it. I think the whiskey he gave me must have given me a little push -- I walked over to him and planted a huge kiss on his lips. Our tongues did a nice dance, and he cupped my butt and pulled me in real close. I could feel just how excited he was. We went to the couch, made out for a few more minutes during which time my blouse mysteriously flew off. He paid wonderful and masterful attention to my boobs and nipples, and I had a mini-orgasm. I unzipped him, pulled out his cock ( average, respectable, and on the thick side) and sucked him off. As I sucked on him, I wondered just how many other mouths he had been in. When he came and I swallowed his cum, he said it had been years since that had happened. I promised him I'd do it again if he ever wanted. It didn't take him long and he was hard again, and my slacks and panties were nowhere to be found -- I climbed on top of him, lowered myself onto his shaft and push my boobs in his face. We pumped and pumped and gyrated, and he came with an intense orgasm. The biggest surprise was next - he said he wanted to do something he used to love to do in college but his wife never liked - he got between my legs and ate me out like a pro, sucking out every bit of our combined juices he could get. We kissed and our combined tastes was wonderful, and he retained a little in his mouth and I took it in.
We had to clean up and leave to get my roommate, so we showered - and I gave him another blowjob in the shower.
We have gotten together several times when we can - he knows I see other guys my age, and I've encouraged him to find a nice companion closer to his age, but assured him that I loved every bit of his attention, and will have him as a lover for as long as he wants.