I took her anal virginity in a hotel room full of people. (m/f). | 2016

(This story is absolutely true. Any details I got wrong are just the fault of old memories).

We'll call her...M.

I'd known her for awhile, she was a friend of a friend. And we'd hung out a few times, but I knew she was a virgin. It didn't help that she lived about three hours away.

We'd made out once. She was short, especially compared to my 6' 2". She had longish dirty blonde hair and fantastic C cup breasts. She had a flat tummy and a nice bubble butt.

Also, from talking to her, I knew that she was submissive and very much into the idea of BDSM.

At any rate, I'd been near her place for a sci-fi convention, which we were having in a local hotel. Since there were a lot of friends coming three hours+ for the game, we chipped in and got a hotel room at the convention hotel, but we were all broke, and who was invited to stay in the room got a little out of hand.

Without inviting any questions, I said that M and I would sleep in one of the beds.

Hours later, we're all tired and gamed out. It's maybe 3am and there must be 7-9 of us crashed in this hotel room, every chair, every patch of floor, and both beds were covered in people.

I was just wearing a t-shirt and boxers, while M was wearing a t-shirt and cute little cotton panties.

We were spooning for awhile, but I don't think she suspected that anything would happen because...well, jeez, there were 7 other people in the room.

But I had other thoughts, and as we were spooning, each of us laying on our left sides, I let my left hand cup her left breast, and I started to kiss/nibble her neck as I rubbed my hard cock back and forth between her legs.

I knew she was a virgin, and she wasn't ready to lose her virginity, but that still left things we could do.

As I tweaked and tugged at her nipples, and sucked on her neck, she had to stay really quiet as I rubbed myself back and forth against the rapidly dampening gusset of her panties.

Finally, I'd had enough, and I wanted to feel flesh on flesh, so I slipped my cock through the flap in my boxers, and I pulled down the back of her panties. She was a bit stiff as I did that - not sure if I was going to try to take her virginity or not, but unable to ask or protest.

I whispered a quiet but firm, "Shhh..." in her ear (as if I was not inviting her input, this was happening), and then I grasped the base of my cock, and I started to rub my cock up and down over her tight, little puckered virgin asshole.

After a few minutes of that, I slid my fingers forward and put the tips of two fingers into her sopping wet cunt. That allowed me to use my palm to stop my cock from sliding forward into her cunt.

I rocked back and forth like that for a minute or two, and then I used my palm to hold my cock really steady as I pushed my hips forward and pulled her back onto me until I felt my cock start pushing into her incredibly tight little rosebud.

Finally, I felt the head slip past her sphincter and she whimpered almost imperceptibly (thankfully a friend of ours, P, snored really, really loudly).

I then paused while she adjusted to having a cock in her for the first time. I know that the humiliation of having this happen in a crowded room made it all the better for her.

When I thought she had adjusted enough, I slowly started pistoning my hips, sliding my cock in and out of her ass.

After so much work-up, I couldn't last for long ...I pulled her back onto me, held her there with my cock deep inside of her, and I emptied my cum in her ass as she shuddered beside me, her juices dripping down the inside of her thighs.

With my cock softening inside her and my hands cupping her breasts, I held her there to sleep in her own wet spot with my cum dripping out of her ass.

In time, I would take most of her 'firsts'... Virginity, first cock in her mouth, first to cum in all of her holes, first to collar her, etc., but that was many, many years ago.

She's happily married now, with kids, but I still check on her now and then to make sure that she still masturbates to the thought of my cock throbbing and emptying itself in her ass in a crowded hotel room.