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I fuck my wife’s supervisor at the Christmas party
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Sorry for the long set up, skip to the **** for the action.

My wife is a teacher and we just attended a Christmas party at her elementary supervisor’s house. There was about 20 of us, the house was massive and decorated like it could be in a Christmas magazine, but the party was stuffy and formal not like our usual drunkfests with her younger colleagues. As I was talking with her coworkers I seemed to hit it off with her new supervisor Jackie. She is around 55 married and a little heavier but has a pretty face. Her husband is a stereotypical nerdy IT guy and doesn’t have much of a personality but judging on the house does well financially. As the evening went on Jackie and I kept finding our way back to conversation together, I told my wife that I think she was flirting with me. My wife said that it was impossible because Jackie is a miserable woman who hates everyone. I told her that I am pretty sure that she is into me, since we swing anyway my wife laughed and gave me the green light to flirt back to see where it goes.

Again Jackie found her way back to where I was and we started talking. She noticed my drink was empty and offered me refill my glass, I winked to my wife as me and Jackie walked out of sight, my wife just rolled her eyes and laughed at me. Jackie poured a glass of wine, I asked if she had anything harder. She pulled down a bottle of rum and offered a shot, I told her only if she does one too. She said she hasn’t done shots since her college party days that she used to be wild. I poured 2 shots and said let’s see what trouble we can get into too. Both of us took one and I quick poured each of us another shot, those went right down too. We joined the group back in the living room. I told my wife what happened and she was in disbelief. A little while later Jackie found me and whispered if I wanted another shot? We headed back to the kitchen and took 2 more each. At this time I was tipsy and could tell she was too. I complimented her house and she asked if I wanted a tour. We went up a set of stairs and her husband was standing there, he asked what was going on and she snapped to him that she is showing me the house and for him to go back down and entertain the guests.

He hesitated but agreed, the upstairs was a long hallway with many doors she excused herself to the bathroom but said the game room is at the end of the hall. I opened the door in the middle of the large room was a pool table, there were vintage arcade machines lining the walls. Multiple pinball, pac man, frogger all sorts of full size machines!! Jackie entered the room and shut the door, her shirt was not buttoned all the way up like before, she asked how I like the games. I told her they were nice, she said that her husband spends more time playing with them than her, she looked away embarrassed. I took my chance and said he was a fool, that she seemed like fun as I walked up close to her. She looked up at me, I asked if she was ready for that trouble from before, she nodded yes and we began to kiss.


It was surprisingly passionate with no awkwardness at all. I ran my hands along her breast and ass as we continued kissing. I gently bit her neck and her ear, Jackie started to breath very heavy, she grabbed my cock through my pants, it’s was already fully erected. She went to the door and locked it, as she came back to me she was pulling her top off letting her plump round breasts fall, they sagged but her nipples were huge, which is a turn on for me. I took one in my mouth and she fought off a moan while trying to keep quiet from the guests downstairs. I unbuckled my belt and dropped my pants, she went to her knees pulling my cock out of my underwear. Her eyes lit up, I am blessed to be around 8” and thick. She took as much of me in her mouth as the could, jerking my shaft as she sucked feverishly. Every once in a while she would take my balls in her mouth and jerk me hard. This 55 year woman acted like she was cock starved and trying to fill up!!

She told me she needs to feel me in her, she stood up, lifted her modest floor length skirt and bent over the pool table presenting her big round ass. I gave her a slap and ran my hand along her hairy soaking wet pussy, she was absolutely ready. I eased in a few inches at a time, each little push I could hear her gasp until I was all the way in. Once in she slowed for a bit to get used to the stretch, she told me that I am much larger than her husband. That only made me even harder, I began to slide in and out, watching my cock get covered in her cum. After a few more pumps her legs buckled and she came hard and eased herself to the floor. Jackie rolled over to her back and spread her legs for me, her sopping wet swollen vagina waiting to be impaled again. This time I wasn’t as gentle forcing my way into her slit. I held her legs up and rhythmically slammed her pussy, my balls slapping her ass each time. Jackie’s eye rolled back in her head as her whole body shook from the orgasm. As I could feel myself getting close Jackie wrapped her legs around me and begged me to fill her with cum. I thrusted hard and blew a huge load deep in her, falling onto her body to catch my breath.

A few seconds passed and we came back to reality that there was a whole party downstairs. We cleaned ourselves up but before we left that room we kissed some more. She told me she has never been with another man in 35 years. The other guests were pretty spread out and we only were gone for about 20 minutes so nobody but my wife suspected anything. I filled her in on all the details of what just happened but she didn’t believe me. She couldn’t believe that the miserable distant woman would behave in that way. To prove it I made sure we were the last to leave, when Jackie’s husband excused himself, I thanked her for a fun night. She played it off in front of my wife, but then I said we should fuck again sometime. Her face immediately turned red with shock and embarrassment, my wife said it’s fine and told her she knew. Jackie apologized but said her husband will be away for a few days next week, so she will be alone. We hugged and then left, my wife the whole ride home was amazed that I was able to pull that off, she even gave her permission for me to go back this week!!

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Thank you, I feel like the set up explains how we got there and you can picture it, but I know some people just want the actual sex.

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Well my wife and I are in the lifestyle so I would have no issues with it. That situation was not discussed and we don’t know the inter workings of their marriage.

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9 months ago