This is a follow-up story about my rendezvous with secretary of my ex’s dad. The first time we fucked it was in the stairwell of her apartment. This was when I lived in Brazil about 15 years ago. She was about 12 years older than I was and wasn’t really my type, but her comfortableness with sex and the fact that she’d get fired in an instant if we got caught made me even more turned on. My girlfriend at the time was very pretty and our relationship/sex was good, but the risk with the secretary was too powerful.
One evening, secretary has a small gathering at her apartment and she invites me. In hindsight the awkwardness of the party should have been a warning sign of things to come. I didn’t know anyone there and being that my Portuguese was only mediocre at this point, so I was lost a lot of the time while everyone else was laughing and conversing. But I knew there’d be a good pay off if I waited it out. By the end of the evening only a couple of her friends remained. As the drinks flowed she started to show more affection with me, lightly touching me and sitting close. The final friends, a couple about my age, got the hint and left. We immediately tear into each other, but she stops and says she wants to change. She returns wearing a black teddy. It doesn’t take long before I’ve got it pulled down and am sucking away at her puffy tits. She starts in again with the dirty talk, “You dirty bastard, you want to fuck me?”, stuff like that. She turns off the lights and we’re touching and sucking each other in the darkness for a while.
I should give a little detail that will be important later. It was a very warm and muggy Brazilian summer night and she doesn’t have AC, so the window of her apartment bedroom is WIDE open. Her room faced a courtyard of sorts where all other bedrooms of the many adjoining apartments faced each other.
So, back to the fucking… we’re missionary style and I’ve got her wrists pinned down as I’m driving my cock into her while I’m swearing profusely from the drilling and the heat of the night. She was very fun and so self assured, talking and joking between the moaning. She then says to me in the dark, “I want you to fuck me in the ass.” “In the ass?,” I say a little shocked. I’ve never done anal at this point and really never really been interested in it. She can sense my trepidation, so she chuckles and says something like she’ll help. She turns over on her stomach and crouches back on her haunches so her ass is right on my cock. She then reaches back and takes my dick and guides it in the darkness to her hole. Honestly, I couldn’t tell what hole I was in because it felt pretty loose like her pussy. I ask if I’m in the right spot and she replies with the loudest moan I ever heard, or would ever hear since. I freeze up for a second realizing the window is wide open and she’s going for it no-holds-barred. She’s pushing back and sliding up and down my dick, screaming and moaning, while all I’m doing is frozen in embarrassment and disbelief. As she’s moaning, I could hear her echo off the buildings across the way, imagining that school children and grandmother’s are being awoken by the debaucherous sounds of the apartment complex slut. I’m fully expecting to hear someone shout at her to shut up, but that doesn’t happen and she continues to wail loudly with every rock of her ass on my shaft. Although my dick is enjoying the ride, my self-consciousness kills the buzz and all I can think about is getting her to stop as quickly as possible. I decide to go double time so I can finish and still leave her satisfied. The downside of this plan is that as I increased my thrusts, her yelping gets louder and louder. I’m sort of in a panic now, but I couldn’t stop. After some deep, deep pumps, I finally pull out and blow my wad all over her lower back and shoot it up to her hair. I collapse on the bed next to her and she makes some jokes about the hair gel I’ve given her. She seemed pretty pleased with the encounter as she’s kissing me and in really good spirits. Me, on the other hand, am now feeling just as awkward as I did during the party.
There’s a post script to the awkwardness of the evening. After we’re done, I get dressed and head out. Our sexcapades probably lasted around 2 hours or so. Well, I head to the bus stop and find the youngish couple also there waiting to take a bus. The three of us are the only ones there, so I have no place to hide. It’s pretty obvious that I’d been fucking their friend, but they don’t say anything and I don’t explain why I’m only now going home. More awkward chit chat for what seems like forever before the bus arrives and I head out. My first anal experience was certainly memorable, but not in the ways that I thought it would be.
Source: reddit.com/r/gonewildstories/comments/g5c0eo/my_m_first_very_awkward_anal_experience_with_my