How did U' lost your anal virginity ?

[SexSlave1972]

I was wondering how people lost their anal virginity ?
In what age, for whom ?
So U' can be guy, girl, TS - doesn't matter if U' have had cock up in your ass. No dildo's etc. maybe strap-on will do with another person.
Tell about it. No need to be long story etc.

All this came from 1 post in thread "Wich shemale will u bottom for ?"

Yasmin Lee in a fucking heartbeat. I would let her fuck my virgin ass until i screamed like a little bitch. And I was wondering he could choose someone who has a smaller cock :fuckin:

My story:
Yes, I didn't lost my anal virginity for TS, it was a guy couple whom I found via magazine's ad. We changed letters and I wanted to be a bit submissive in our act. Year was 1994 and I did go to their summer cottage, at age 22. I didn't have any other up my ass than my (at that time ex) girlfriend's finger before that.. and I really liked prostate rub so I wanted to try real cock up there. I was pretty bi-courious at that time (now I know that I'm bi 50-50 for cock or pussy). We went to sauna and I did try first time suck a cock there. After that into cottage where we get into bed and we start act. The liked to tie me up, and they did with bathrobe belt. Fingered me a bit and I was at 69 pos. under that another giving him a rim-job when another did just crab my feet at his shoulders and stick his cock at one push inside me. It did hurt a lot but I kind of liked it. Cladly he wasn't that well endowed, just about nice 6" and around 1,2" girth. He fucked me rough, no mercy at all.. They did try even DP me when I was riding another (not the virginity taker) guy's cock.. he was clearly bigger around 7-71/2 and more like 1,5-1,7" thick. I didn't work I was too tight then. They both did fuck me twice that evening. That wirginity taker tryed to fuck me at morning but I was way too sour for that. Needed to take my first cum load's in my mouth that morning for the guy's 'cause ass was "no can do" - state.

That was my story about loosing my anal virginity.

[LovinThaTSLadiez]

I lost mine to a TS escort when I was 26. When she first put it in, it hurt a bit but then immediately started feeling GREAT! She fucked me nice and slow and then started stroking my cock. It felt even better than I thought it would. Her cock wasn't huge, because had it been, I don't think I would have been able to bottom. She was maybe 6 or 6 and a half inches and not that big around. It was just right.

[Turlington]

Prostate exam

[Telemaque]

Thanks for sharing your experience, Sexslave, that sounded pretty hot :)

I lost mine a couple of years ago with my girlfriend. She was pretty open, and pretty quickly after we started dating she suggested the idea of toying with my ass. For my birthday she got me a strap-on dildo, and I got my first experience being fucked in the ass. While the whole thing was pretty exciting, I must admit I didn't like it that much, and I believe there are two reasons for this:
1. It was my first time, so she didn't want to get something too big. I though it was a bit too small... would have liked something a bit bigger.
2. The fact that she couldn't really "enjoy it" bothered me, as she was only inserting a piece of plastic in there.

So now, I'd like to try with something bigger, and something "human", and since I'm not into men, that leaves me with only one option :)

[Rusty Eldora]

Lost it to my first Tgirl TS Pamela in Seattle http://www.erostranssexuals.com/files/403093.htm
http://tumview.com/tspamelaseattle

The start of a fun journey

[Jericho]

This one time...In Prison Camp! :hide-1:

[maxpower]

This one time...In Prison Camp! :hide-1:


Was a flute involved?

[eddymunster90]

I had been teased and fingered by some TS lovers, but the first true anal was my TS girlfriend over 10 years ago. She was timid to try at first cause she considered herself a true bottom, but after that loved it.

[joanne_sven]

How he goes to the hill.

[joanne_sven]

This is how it happens.

[SexSlave1972]

And If U' actually don't have anything to share, get the fuck out of commenting this thread.

[CarlaFan]

I was playing with this guy who more top than anything. I had some strawberry flavored stuff I was rubbing on his cock. When he said "it's strawberry?, tell me how it taste." And shoved my head down over his cock where I willing took as much as could. Before this point, I remember thinking I wouldn't really enjoy a guy grabbing the back of head while going down on him; not like I did when I was going down on girl. But it felt really good to let go and him take charge of me. He took outside on his balcony in (he lived in area with neighbors located everywhere). I was kind of turned on and shaking of thought that somebody might see out there in the middle of night. He had grab the rail in front of me with one foot up on the rail to my side. I surprised that I really enjoyed and it didn't hurt. Maybe that was because of all that strawberry lube, LOL. But as I taking it, I was starring at the house in front of me across the street, thinking that somebody could easily see us from inside. But I'm sure I was paranoid since the houses were dark. But it still turned me on thinking they could.

[jonnie64]

My girlfriend with a strap-on!!!

[robertlouis]

Prostate exam

The same lol, a colonoscopy.

When it comes to sex, I haven't and I won't.

[MitziMore]

Though I've had boyfriends since I was fourteen, all I had ever done was give them blow jobs and get felt up and fingered. That is, until college! My sophomore year I lost my anal virginity at spring break. I was hanging out with a few guys I had just met and we all had been drinking. I was smooth shaven everywhere and dressed in ripped cut offs, a tight t-shirt and new red thong undies.
This one big, very drunk college boy escorted me back to my motel room where I sucked his cock. It was, at the time, the biggest I had ever seen! I was super nervous, but when he undid my shorts and pushed the strap of my thong to one side I just melted! I was on my hands and knees, butt in the air, in a flash. With a ton of KY, he managed to pop that monster in me and I nearly fainted! It hurt SO much! I admit it, I cried like a little girl. But, afterward, I was really proud I had taken him. That was my first time.:party:

[bulldogtuck]

Sasha Ligaya took my anal virginity.

Jennifer Justice was No. 2 but the first one to get me off while bottoming.