“I’ll get over it,” I said. “But, really, you probably should just go – if you’re feeling that bad about being here.”
“I’ve already come.. I’ll go if you want but I’d rather stay now that I’m here? I really am sorry, what can I do to redeem myself?”
“What will you do?”
“Name it. Forgive me and let’s have a good time… tell me what you want and I’ll do it.”
“Okay, how about anal sex right now?”
“What? I’ve never done that.”
“If you forget my little faux pas and all will be cool, okay.”
“No way, You have too had anal sex? You’re lying,” I said. I was just confirming – I actually believed it was true, because I hadn’t had anal sex.
Well, I hadn’t had it per se. I got my head inside my High school girlfriend once and then she made me stop. After that it became a big desire. The times when I didn’t come when she came, which wasn’t often – one of the few situations where my high school girlfriend showed vulnerability and let go of control – was while coming. That was hot and usually set me off two. But when I could hold through, when possible, I’d pull out and rub my tip on her ass while I came on it.
My next girlfriend was waiting until marriage, so I enjoyed this type of ending often. She like to lay on her stomach with a toy while I came on her ass – never let me in there. I’d had a few years of ass teasing – only – so ass from Sheryl was over payment for her slip up.
“Swear to god, NEVER!”
“So you will?”
“We can try, no promises. It’s an adjustment to take you normally, seriously not sure.”
“Okay, fair deal,” I said. I was quickly getting back hard as soon as I realized the ass might be happening.
I was fully hard by the time I was back from rummaging around my room for something lubricant like – I found some lip balm is all.
My roommates were up and about – TV on – making noise outside the room. They were just decent enough of people to not confront me while I had company – but I knew there’d be an issue later. I’d wanted anal for years and was about to get it – so fuck the persnickety roommates.
“Jesus, you’re enormous,” she said as I sat next to her on my bed.”
“Um, you’ve seen me before – we just had sex ten minutes ago.”
“I’ve never seen you before you were about to put it in my ass.”
“Good point. Sit down on me.”
“You owe me a fabulous fucking weekend dude.”
We started with her sitting down on my lap – while I sat on the bed – she had nothing to hold onto so we went to my desk. held onto the shelves – turned on my desk light. My desk was right next to the door and just on the other side we listened to kitchen dishes clank, cupboards thumb – roommates were being louder on purpose – such bitches.
It seemed forever getting things going – she would sit down a little bit and then say “wait,” then try a bit more. If you’d done anal – you know the drill. My cock was at its penultimate hardness.
I was in her pretty good – she was over me – halfway or more – and we sat there in a holding pattern. She was quiet – I wasn’t sure where things would go from there but I was loving just sitting there – in her ass. A few of my roommate’s friends showed up – now there were at least four outside the door.
I would have been happy staying frozen with her all day like we were – her ass clenching around me was enough to keep me there – so I sat there and hoped only she’d not pull off me.
“You feel how hard you make me? Want to stop? Are we good?”
“Yes, as long as we stay still – it’s not hurting now. This is about the best I can do – not sure what you had in mind, but..”
“This is fine – amazing actually, can we do this all day?”
“You like this?”
“Do you feel how hard I am? I am dizzy over this. Are you good?”
“Yes, feeling better. You devirginized my ass – how about that? “
“I’m happy about it.”
“Naughty, huh? Your totally in my ass right now – kinda turning me on.”
I thanked god. Didn’t’ figure Sheryl or anyone would go to long with anything shoved up their ass if they weren’t turned on.
“She moved up and down a few times – tiny little bit.
“You want to stop?”
“No, just be still.”
Worked for me.Didn’t know if she’d get off on the activity like I was.
Oh my god the feel of her ass – no idea if the intermittent squeezes – contractions – were involuntary or her experimenting,
I started talking in her ear and reaching under her leg to rub her clit –
Then a roommate knocks on my door – obnoxiously – “Duncan – can you move your car?”’
We had four spots but two lanes.
“Can you just move it,” I said.
“You key’s aren’t in the bin.”
Fuck. my keys were on my night stand.
“Can we resume this position?”
“Yes, I need to use your bathroom first.”
I grabbed the keys and Sheryl threw on my robe. – handed the keys to him as Sheryl ran out to the bathroom directly across the hall. I was rock hard – didn’t give a fuck. Roommate paused for a moment – deciding whether to be a dick and make me move the car.
So, I wait back in my room.
“Nice guy,” Sheryl said as she came back in.
“He’s not my biggest fan.”
“You’re still hard.”
Sort of awkward silence ensued.
“I love your dick.”
“I love your ass.”
“It’s a bit much for my ass.”
“Okay, so you don’t want to resume where we left off? Thank you for doing it.”
“You can put it back in – but if you want to bang me – it can’t be there.”
“That’s fine just being in there.”
We ended up where we left off. I got her wet with the wetness of her pussy this time. Maybe a bit deeper this time. We didn’t move much – and just started talking.
I think she was ½ turned on by how into it I was – and have amused or curious about the situation – whatever her reasons – she began to enjoy the engagement
“You going to just keep your cock in my ass all?”
“I think so, yes.”
“You’re crazy. I’m crazy.”