This story takes place is part fiction/fantasy and part a recollection of events that happened to me in the late 80's and early 90s. The places and names have been changed. The attitudes are representative of the prevailing attitudes in that time and place. All sex is between people above the age of 18.
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After the whirlwind events of the previous week, with me blowing a cop at work, blowing my boss after he discovered my blowing the cop on the surveillance tapes of the store and losing my anal virginity to my best friend, Derek, the next couple days were relatively calm. I had to work on the weekend, so I didn't get together with Derek and Constable LaValle didn't stop in while I was working either. However my outlook had changed: I now wondered with a lot of the people that I interacted with, if they were checking me out or just being friendly? I wasn't brave enough to be aggressive or to be more than mildly flirtatious but I was now more aware that other people had secrets too. I would catch looks from both men and women during our interactions and wonder if there was interest in their glances or double entendres in some of our conversations, thoughts that would never have occurred to me a couple weeks prior.
My new promotion didn't really change much at work: I still worked most of the late night shifts on my own and closed things up, but Skip did start asking for a little more input on inventory issues and teaching me some of the other parts of running the business. This meant coming in a little earlier, more often and being up in his little office with him, as was the case about 2 weeks after his discovery and my promotion. He was going through some numbers and the fuel totals weren't adding up and starting to get frustrated.
"God damn it! Why won't this stupid thing balance properly?" Skip, like many of his generation had grown up and learned book keeping by doing everything manually and entering it in ledgers. The transition of putting things on computer wasn't the easiest thing for him. I leaned forward to get a better look at his screen and noticed he had made a sign error, putting a "+" in place of a "-" in one of his cells, throwing the whole thing off. I was able to quickly correct this and he hugged me in relief.
As he grabbed me in his embrace, I was thrown off balance and my hand dropped to his thigh to try to maintain my balance. My hand found he was erect under his pants and so, without any prompting, I extricated myself from his arms and slid to my knees in front of him. Looking up at him with a smirk, I undid his zipper and reached in to free his member. It looked exactly as it had a couple weeks prior and remembering his taste, I quickly took him in my mouth.
He gave a quick gasp of surprise as his cock was enclosed in my mouth and I began to suck on it.
"Oh god you're so good..." His words of praise made me swell with pride. I wanted to make him feel good and swallow his salty treat... but a few seconds later he was pushing at me.
"Wait! We can't do this right now! Kathy is downstairs! If she came up and caught us..."
I was not to be denied: I hadn't sucked a cock in close to two weeks and I wanted his load. "Don't worry: I'll make you cum quick and you'll feel so much better. We'll hear if she comes up, but we'll be quick. You'll see." With that I wrapped my lips around him again and redoubled my efforts. He was worked up and probably hadn't cum since the last time I'd blown him, and in what seemed like no time at all, he was pulling my head to his hips as his cock spasmed and gave me a mouth full of his seed. I savored his taste for an instant then swallowed it down, and made sure to clean all his remnants off his deflating erection before tucking it back into his pants and doing them up. After he was all buttoned up, I got up off my knees and smiled at him.
"See? All better and no one's got a clue! Don't you feel better? I know I do with that wonderful load in me!" And with that we quickly finished what we were doing and went down into the store. Kathy smiled and chatted with when we got down there and I felt a flash of guilt, that I'd just blown her husband, and now we were all buddy-buddy, but then I remembered that Skip said she hated giving head. I also remembered how much cum he'd shot into my mouth and figured she wasn't having other sex with him that much either... and I wondered if SHE might be getting some on the side.
The following weekend, I was off for the first time in what felt like months, although it was less than one. Friday night, I was at a small house party with friends and I had way too much to drink. We had started watching a hockey game and playing some nickel ante cards, and as always on those occasions, the beer and whiskey were flowing freely. Before too long, I had overindulged and was falling sleep in a chair, when one of my friends, Jake, offered to take me home. I was in no shape to protest so a couple of the guys loaded me into Jake's car.
On the way to my apartment, it dawned on Jake that I was so far out of it that he was going to have to carry me up a couple flights of stairs and decided instead, to take me to his place, a house trailer he inherited from his mom when she passed away a couple years before. When we got there, he managed to half carry, half drag me to his couch, where he wrestled off my pants and shirt, leaving me there with a blanket. He then staggered off to his own bed.
Sometime in the middle of the night, I got up and staggered to the bathroom. I did my thing and in my drunken haze, instead of heading back to the living room, I stumbled into Jake's bedroom and crawled into bed with him. He didn't wake up and I went back to sleep. A few hours later, I remember being cold and pushed up against Jake, who was warm and had most the blankets. As I slowly moved beside him, to try and get warm, I felt something hard poking at my ass through my underwear.
Feeling that sensation popped me into awareness of my general situation: I was in someone's bed, I was cold, they were warm, they had a hard on. Thinking to myself that this was a no-lose kind of situation, I gently pressed myself against the hardness and moved my ass up and down a bit to rub him. Sure enough, I felt the erection surge a bit against me then press into me a bit. Being the half drunk flirt that I was, I rubbed my ass against the hardness more, and it pressed into me with more force. I wiggled my ass more and the hardness pushed more, until it back off for a second and I could feel movement behind me and the hardness was back, but more pronounced: he must have removed his underwear, so now all the separated his cock from me was my tighty-whiteys. I moved against the hard cock some more and soon a pair of hands reached around and ripped my underwear out of the way before the hard warmth of the cock was rubbing between my ass cheeks.
As Jake rubbed his cock up and down my crack, I was getting hornier and hornier. I finally spat on my fingers a bit, and rubbed the spit on my anus. Then I reached back, grabbed his erection and guided the head against my opening. In his haze, he had no finesse and once he felt an opening, he rammed his way in, as far as he could. It was a lot more painful than I had bargained for and vastly different from the controlled entry Derek had, several weeks previously. The second cock to go in my ass was a much different experience.
