I think Rock Hard is on to something here, I believe it is 90% mental! Just the whole taboo thing and watching your cock disapear into that ass is mind blowing! I love the whole slowness of anal penetration, no way can you even consider slamming it home like the movies, there is that communication with your partner that for me is so erotic, does it hurt? No, go a little further, ok stop for a second, you all right, yes, further....etc....very nice!
My first oral was while in school. There was a teacher that always wore short skirts and tight shirts. She was sexy with big tits and long thick legs. She gave extra lessons after school to any kids that wanted. I signed up for this and my day was a Tuesday. I signed up just to ogle at her for half an hour alone. She must have realised as during the second lesson she got a bit touchy feely and flirted alot. The next lesson she was sitting next to me and my eyes were fixated on her chest. Her hand moved over my cock and as she rubbed it asked if I liked what I saw. I replied very much and she placed my hand on her tits. I had no time to feel nervous and she proceeded to undo my pants and began licking and sucking on my hardened cock. Within 5 minutes maybe less with my fingers inside her dress playing with her nipples I came in her mouth. I was 16, but it was the greatest feeling, better than wanking. After a few weeks I got the courage to eat her out, with her help in directing me in the right thing to do. She went wild and that was a turn on. Pity she never let me fuck her until after I was done with school. First time anal I was 18. I had heard alot about it and from what I had seen it looked very pleasurable. I was at a friend's place but he wasn't home. I was alone with his mom and being attracted to her for the last 2 years I made a move in the kitchen. After making out and having her rub my cock I proceeded to eat her pussy out on her counter top. We moved to the floor where I got a bj, fucked her tits and pussy. As she stood up I pushed her against the table. Her ass was looking delicious and I proceeded to grind my growing cock against it my hands playing with her pussy. I found a bottle of cooking oil and began lubing my cock up. I slowly entered her ass while massaging her wet pussy. I inched in until my cock was fully in her ass. We fucked for 20 minutes in which period I stuffed her pussy with a cucumber. I was fucking her in both holes and she had an almighty orgasm. Her body eventually went limp from exhaustion and I continued pumping her ass till I came inside of her.
