First Deliberate Jack Off on a Person's Face

At the time of this story, I was renting the top floor of a house in suburban Vancouver. Some friends rented the basement suite and a woman named Jackie rented the main floor. Jackie was very overweight and from the moment we met, we disliked each other a lot (not that the two were related!). She thought that I was some kind of wild, party-hearty (true enough!) and I thought she was one of those people who think the world of themselves with no semblance of a reason.

It came to pass that the landlord sold the house and the new owners wanted to move in, so us tenants would have to move. On the day/night in question I was pretty much all packed up and it had been arranged that the friend would help me move to my new place the next day. They were out moving into their new place, so only Jackie and I were in the house.

Just after supper time, I heard someone coming up the stairs to my suite and then there was a knock on the door. I opened it and there stood Jackie, carrying a small box. At first I thought it was some kind of gift but then noticed it was actually a box of six condoms. I was just a little discombobulated and Jackie said something like, “Look, I want to get laid. We’ll never see each other again, so why don’t you help me use these up? Just because we don’t like each other doesn’t mean we can’t screw, right?” Despite her lack of physical appeal and the fact I really did dislike her, there was never any question I’d help her out. Supposedly LBJ once said of JFK, “That guy would fuck anything that walked, half that crawled, and most that creeped,” and I’m proud to say that could be my motto.

“OK, Jackie, I’m game. But if you want me to do this, you have to let me cum on your face. I’ve never done that and I’ve always wanted to,” I told her. She thought about it for a bit and then said that would be OK but I had to go down on her. I told her that sounded good and she said she’d be right back and went downstairs, tossing the box of rubbers on my bed (my suite had no separate bedroom, with my bed set up in one corner).

I took off my clothes and jacked myself to hardness, admiring the curvature of my frequently jerked cock. As usual for me, pre-cum made a quick appearance. Jackie came back up wearing a bathrobe, looked at my cock and said something like she really loved thick ones like that. She asked me to turn off the lights, so I did - there was still soft light from the early evening setting sun. She took off the robe and lay down on the bed. She had a lot of fat on her thighs and belly, her tits were smallish with big, hard nipples, and her cunt hair was sparse. 

I immediately got my face between her legs and ate her out. I love cunnilingus and decided to give her a good licking. I concentrated on her labia minora before turning my attention to her clit. She started humping it into my face and after a few minutes had a strong, moaning orgasm. I got up, put on a condom and knelt between her legs in the bed. I pushed my cock inside her and started a steady fuck, her legs splayed to the side. I stopped for a bit to suck her nipples and than went into overdrive, fucking Jackie hard and fast. She was exquisitely tight, so my cock felt great even encased in the rubber. One final thrust to the hilt and I blew a huge load. When I pulled out, there was an incredible amount of cum in the condom and I showed it to Jackie.

I rested about 30 seconds and rolled another condom down my still hard cock. I pulled her legs up and fucked her good until I could feel myself getting close. I withdrew my cock, moved up so that I was straddling her tits, tore off the condom, and started to jerk off slowly. My cock was nice and slick from pre-cum and cum and it felt so good as I slid my hand up and down my turgid shaft. I stopped myself from cumming several times - I was determined that my first facial would be a real blaster. I felt the familiar tingling at the base of my cock and sped up my stroke. When I rubbed my balls, I exploded! I shot four or five juicy spurts and left Jackie’s face dripping. I collapsed beside her on the bed.

After I’d rested maybe 15 minutes, Jackie reached over and gently grasped my meat. I got hard immediately and she slowly wanked me for a bit. She asked me to fuck her again, so I put on another rubber and put her on her hands and knees. I rammed her dog-style for a few minutes and when I got close, I again pulled out and removed the rubber. I spat on my hand, lubricated my cock, and jerked myself rapidly. I only got two pretty small spurts this time, but the first shot right into her hair while the second made a nice little pool on her back.

I was drained and happily fell asleep. Sometime later (it was now pitch black and quiet outside), I felt Jackie groping my cock and somewhat to my surprise got another erection. I put on another condom and started fucking her from behind again. Having nutted three times I was in no hurry to cum and gave her a long fuck. Finally, I pulled out, removed the condom, and got a bottle of lube from my bedside table. I sat on the side of the bed, gave her the lube and told her to give me a handjob. She greased me up and started a slow stroke. I could tell it wouldn’t be easy to cum again, so asked her to jerk me faster. She did and after a minute or so I came again, just a few drops of semen pulsing out over my cockhead. I couldn’t believe how powerful the orgasm felt even though my balls were pretty much empty.

I told her that four out of six condoms was all I’d be able to manage. She said that was OK, as she didn’t think she’d be able to walk tomorrow. With that, she went back downstairs and I went to sleep with a pretty raw cock.