Best Massage Ever...

This is a true story and it occurred in June of 2011. I had been seeing Sally for a few months and things were starting to get serious. I still hadn't given up seeing my casual sex partners because Sally and I hadn't made anything official yet however it was fairly obvious that I probably should have done so by this point. On this particular weekend Sally was going out of town for a work conference on the east coast and I'd be alone the whole weekend.

The weekend was quietly going by when on Saturday I got a IM on yahoo messenger from my friend Christina, it started like many of our conversations by her saying - "Hey Babe". Christina told me that she was house sitting and that she'd like me to come visit her this evening.

I'd been seeing Christina for about a year at this point. She was 56, I was 35. We had met on adult friend finder. Christina was very forward (which I like) and asked me to show her pics of my cock in our first chat. Things worked out well between us because I love eating pussy and many of the guys that Christina had seen didn't do that. My ex wife had really taught me to eat pussy like a pro about 14 years before I met Christina. I also loved seeing Christina because I didn't have to wear a condom, she had her tubes tied and was past menopause. I could cum in deep in her pussy which we both loved. Sometimes I would pull out and shoot my cum all over her tits, her ass, her stomach or sometimes in her pussy hair which I loved because it reminded me of late 1970s porn I'd seen when I was younger. We always had hot sex and did some kinky things too so it was very tempting anytime she wanted to get together.

I explained to Christina that I was getting pretty serious with someone and probably shouldn't come over. Christina said - "Well we don't have to do anything, we can just hang out". Then I said "How about we give each other massages, that would probably be ok right?" To which Christina replied - "Of course, massages are fine and that isn't cheating". So we decided that I'd come over at 9pm. I remember getting a really good and thorough shower, using peppermint Bronner's soap and getting myself clean and smelling good. It was a warm night so I put on some light shorts and a sweat shirt and started driving the 20 minutes to where Christina was house sitting.

After arriving I went to the door and Christina let me right in, after a hug and some small talk I went straight to the bedroom and took all of my clothes off including my boxer briefs. I'd had other massages before and I felt this would be no different. I laid down on the queen size bed, face down and waited for Christina to lock up the pets that she was there to watch.

Christina came into the room, I had my head down on a pillow and she straddled me around the waist. I didn't turn around to see what she was wearing, I assumed she was wearing what she answered the door in which was shorts and a tank top that showed off her amazing DD breasts. She started by lightly rubbing my shoulders and neck. She had nice long nails which she would run down my back in a very erotic way. Still nothing too crazy was happening, she was rubbing me up and down my spine and I was enjoying it not really expecting much else to happen. This went on for a bit and then she started to work her way down my back and she scooted down past my ass, straddling me at around my knees now. Then I remember feeling something warm and wet in the middle of my back, Christina was kissing and licking me there and moving farther down until she got to my ass. She started licking both of my ass cheeks which felt so good. Even though I knew I shouldn't be doing this I did nothing to stop her. Then I felt her tongue going up the crack of my ass very lightly. We had rimmed each other before but this seemed more intense this time.

Christina then changed position so that she was kneeling between my legs. She gently pushed my legs apart and ran her hands up both of my ass cheeks. She firmly pushed my ass cheeks apart and put her tongue right into my asshole. At this point I was so glad that I took a really good shower.

Christina was going up and down my ass with her tongue, plunging it deeply into my asshole while playing with my balls with a free hand. She would deeply tongue my asshole and then flick her tongue above and below it, spending lots of time licking my taint as well. This went on for a while it was driving me crazy. She was massaging my ass cheeks and keeping them spread wide the whole time. Then I looked back and realized that Christina was only wearing a thong, a white thong that had a wet spot from her wet pussy. She asked me to turn over and I did and she put my cock deep into her mouth, making me very wet. She was deep throating me and getting spit all over my cock and balls. I was so wet from her saliva, I was ready to slip right into her pussy. After Christina was satisfied that I was ready she stood up on the bed, bent over so that I could see her ass and seductively pulled down her thong. She then squatted over me and mounted me reverse cowgirl style. She aggressively grabbed my lower legs as she slammed her pussy down onto my cock, riding me very hard. I watched my cock go in and out of Christina's dripping pussy for a while. She was wet all over, her asshole was wet too so I put my thumb on it and rubbed it as she continued to slam down on my cock, both of us were breathing heavily and moaning in ecstasy. She started on her feet but eventually rode me on her knees, still very aggressively. It was so hot watching my cock fill her pussy, going in and out.

After a while I said - "let me fuck you from behind". Christina bent right over and put her ass up in the air. I entered her from behind and started pumping her. She was so wet so I decided to put my thumb deeper in her wet asshole, to the point it couldn't go farther which made her moan like crazy. I kept pounding her pussy from behind and Christina finally said - "I want you to cum in me tonight, I want it all deep in me". So I asked her to get into missionary position, she raised her legs up high as I slipped my hard, wet cock back into her pussy. Both her pussy and my cock were soaking wet by this point. I'm a sucker for missionary position and Christina had her legs on my shoulders. I was looking down and watching my cock go in and out of Christina and also was getting turned on by her trimmed pussy hair. Finally I couldn't take it anymore and I pushed my cock all the way into Christina and unleashed a massive load of cum, deep in her soaking pussy. I felt like I was cumming for 30 seconds or more. We stayed in that position trembling for a few minutes and I finally pulled my cock out, it was getting soft but it was still super wet. Christina started to stand up and I saw my cum dripping out of her pussy, it was going all over the sheets. Eventually we said good night and I went home with one of the best sex memories of my life.

Sunday went by fairly uneventful until Sally came home. She called me up to tell me all about her trip and then she asked me - "So what did you do? Were you a good boy, did you behave this weekend?" To which I replied - "Of course I did".