When was the first time you fucked your own ass with something? I was 21 and housesitting for friends of my parents. I had the run of the house, and was sleeping in their bed in the master bedroom. I went snooping in the dresser, while I was horny, and found some stockings belonging to the lady of the house. I stripped down and put them on, having never done anything like that before, and then somehow, I got thinking what it would feel like to have something in my ass (again, having never even thought about it before). I also found their camcorder, so I got it ready, set it on the bed, grabbed one of her brushes, smeared a bit of vaseline on the handle, hit record, and tried it out. I could only slide it in a bit, but it felt so damn amazing, and I felt so sexy with those stocking on, fucking myself in the ass. I left the brush in there and jacked off, and I couldn't believe how much cum came out. I can't remember if I ever erased the tape I had in the camcorder. Eventually, when I was older, I started doing it somewhat regularly, and eventually doing it on cam for other guys.

Feels so good.

it feels so good. i had a buds cock head in me once. wow.

enjoy that nut!

the first time for me is when my wife bought a vibrator and put up my ass on vibrate and gave me a blow job at the same time man did I blow a wad of cum in her mouth that day..ever since then I been using it when I jerk off or my wife is giving me a blow or hand job...

Have been fuckinh my own ass since I was a teen. Love a butt plug or dildo between my bum cheeks . Feels so good and makes me cum harder. Always happy to oblige a nice warm cock between my tight cheeks anytime. Pm me guys. I'm northwest uk

Unbeknownst to my best friend, I was able to make myself a duplicate key to his parents house when he was in law school and still living at home (long story). Then, when his parents were on a trip to Mexico, with his older sister living in Minnesota and while he was at law school out of state, I was able to sneak into their house and walk around in the nude. Being bisexual, I had fantasies about my buddy AND his sister. So I masturbated all over the place! I purchased a 12" dildo that I inserted into my ass by squatting on it in their kitchen and foyer, using Crisco Shortening for lubricant. I managed to get about 9" up my ass (I measured the penetration). Needless to say I shot ropes and ropes of cum doing that!

Is anyone able to fuck their ass with their own cock? I can do it a little and if feels sooooo good.

Have you done it again since.

I was in my teens and I have no idea why I put a pencil with Vasoline in my butt. I just did it. Been a long time fan of my booty

Have used my finger a few times and have used a butt plug, kinda gets me feeling girlie lol, I wonder what a real cock would feel like?

Not tried it yet, but I think I will to see what its all about. you never know I may find someone to try with.

first time for me was with aunties dildo, she was on holls and i was sent round to water plants, as i have had a pantie interest i was looking in the dreser and found her dildo, whel being young t boy i decided to play

First thing other than my finger was also my aunties vibrator.
My uncle had a great collection of porn mags (mainly club and fiesta) stacked up in the bathroom and bedroom (aunt obviously didn't mind!). As such I was always busily wanking away when 15-18 on babysitting duties. When snooping around trying to find some more novelty wanking fodder I found my aunt's vibrators in her knicker drawer. Using baby cream as lube the big one found its way up my asshole, stretching it wide for the first time and helping me towards some more amazing orgasms. I always had a good search for some naked photos of her but unfortunately never found any!

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I need to learn how to do that