I [30F] think I took some Christmas night flirting a little too far but I want more from him [M]

Gotta use the throwaway for this! (First post so im sorry if this isnt great!)
My brother in laws cousin often joins our family Christmas activities, which is great, the more the merrier and all.

I always have a great conversation with Alex (let’s call him Alex) whenever I see him. He is pretty quiet, funny, but definitely not particularly forward. I think he is gorgeous as well, but I have always been in a relationship and I know that he is quite religious, so it’s never gone past a cheeky joke etc. Til’ last night.

This is my first Christmas single in almost a decade. I’m doing okay but it’s hit a little harder over the Holidays. Last night I spent Christmas with my sister, brother in law and both sides of their family. Alex was there, besides the younger kids/teens we are the only single ones. So my sister ensured we were sitting together which was great. We chatted almost the whole day, I don’t think until after dessert I noticed a button on my dress had come open (I am pretty well endowed in the chest department) and I noticed Alex had looked down a couple of times. Super quickly but enough to get my mind wandering a little. Feeling his leg pressed against mine at a crowded table and the dress button got me a little worked up.

He turned to me and said “I’m really sorry to hear about you and John, you guys seemed happy together” which wasn’t really the case and we got to talking about it, the table was emptying into the living room and the deck so we had a little more privacy. I mentioned wanting to get back out there but not having the confidence to jump in just yet.

I noticed his gaze flicker down to my cleavage again and when he realised I caught him he went bright red “sorry… your uh.. your button”

I like to think I played it off like I didn’t know and acted surprised as I popped the button back in, when I looked back up he was still red “I shouldn’t have been looking thats on me”

I jokingly said “to be honest its good to know I still have it” and smiled. Still red but he laughed it off. We chatted a little more but he got up to have a chat with the guys and I went to the living room with some of the others.

Later that evening we found ourselves alone in the kitchen…

“Are you checking to see if I have a button open again?” I asked, jokingly

“I’m so sorry, it was just a reflex, I’m normally so good at not gawking”

“You weren’t gawking!”

“i looked too many times, I’m normally more of a gentleman than that!”

“It doesn’t mean you’re not a gentleman, it was just a peek!”

“It was the look you caught, there have been way too many others and I finally got caught out”

“Today”

“Other days too”

I felt a rush, he had never said anything like this before and I have to admit I was almost proud? Like I had accomplished getting the good Catholic boy to look at my tits? I had to press more

“Which other days?”

“I don’t know, just other days as well”

“Alex have you been checking me out!?”

He went red but smiled a little as he poured his cup of tea, “well yeah, but you were with John so I didn’t exactly stare… not like I did today”

I laughed “should I ask if you liked it? Or will my ego be crushed?”

He looked up, and looked me right in the eye “I liked it… a lot”

I felt a little twinge between my legs… he looked so good and knowing he liked what he saw… I couldn’t help myself

i kept the eye contact with him… and unbuttoned the top button of my dress, then the next, which sat mid bra level and opened the material a little so he could see my cleavage and a little of my black bra with lace over it, it’s cut low so he got much more than he would have bargained for

“Fuck… what are you doing to me?” He said looking from me to my chest… not knowing wether to hold my stare or take in my tits…

“I don’t know but… I want you to look… is that OK?”

He nodded, and licked his lips… im not sure if he realised he had done it or not but I wanted him to touch me so badly but he wasn’t moving… just looking across the kitchen counter… so I walked around the counter to him, intentionally breathing a little heavier so he could see my tits rise and fall with eash breath

“Do you want to touch them?” i asked… looking up at him, moving closer in

He looked down and almost groaned “I really want to, but if anyone can walk in”

i stepped back… feeling a little rejected.. but I saw his pants and the bulge inside them… he saw me looking and he said “I really do want to…”

Probably for the best because a few seconds later my cousin walked in. Alex leant over the counter to hide himself and I opened the fridge door to get a drink out, buttoning one of the buttons and leaving the room.

When he left he gave me a hug, the same as everyone else but I ensured that I was pressed into him that extra bit more.

Im seeing him again next week and genuinely don’t know if I should take it further or if it was a mistake…

Source: reddit.com/r/gonewildstories/comments/zvhfvg/i_30f_think_i_took_some_christmas_night_flirting

34 comments

  4. Seems like you are both interested and consenting adults, sounds like green light go to me! Have fun and please write more about yourself. Anyone who reads this is going to want more!

  10. Why would it be a mistake? He said he really wanted to go further but he was worried about someone walking in. Just get a room. Easy.

  17. r/gonewholesomestories

    You two seem sweet on each other. Good luck and keep us in the loop!

  22. He’s probably a bit scared, does not mean he is’nt interested. I get that coming out of a breakup you might not feel 100%, but I’m sure that if you push him a bit more you will have a great time.

  23. A lot of how you describe Alex, is how I am. I’m shy, respectful etc but same thing happened to me at a Xmas Eve party a few nights ago. My cousins friend Jenna; who I find absolutely beautiful -slowly started bending over (and yes I was checking out the cleavage) She’d then look at me, and I could feel my face start to get red. Then she asked me to help her get stuff from her vehicle to bring in, here she was again rubbing her boobs on me that’s after she was bending over in the back of her car to grab stuff with yoga pants on bumping into me with her ass. She then started in with the flirting and yes, my pants start throbbing! While all this is going on, things race through my mind like when the hell is my Mom going to leave the party, should I go to the other Xmas Eve party, does Jenna really want me or just the attention?, should I start flirting back or just let her take the lead. Well, I said the hell with it, Jenna flirted again not much longer after I helped her gather her stuff from her car again making me blush. I looked at her and said hey I might be shy but you won’t last a second with me in bed. After a two drinking games and when everyone cleared out, we went into a spare bedroom in the basement. I was the dominant one in the bedroom where she liked me throwing her for one position to another. I thought it was going to be more of a one night stand, until she came over last night. Once again, she liked me tossing her around and being somewhat rough. Nothing too crazy when I say rough. If I could show you the scratches she left on my chest you’d know. Well sorry for the long story, my first time ever sharing on Reddit. Thanks everyone,I had to share my past two nights with someone.

  24. I would say that this could be fun, once or twice for sure. Tease him some, lead him along. Then conquer and dominate him. He’s already under your spell!

  26. I’m sure he would appreciate if you pursued things especially if he is a bit shy and religious as that could be holding him back and if you don’t make the most of the opportunity you may both regret it later.

  27. He didn’t realize he licked his lips. My wife calls me out for doing that sometimes.

  32. I just had a wet dream last night, about a close friend of mine who met me for dinner recently and the top 2 buttons of her shirt were undone.

    I tried not to look, but it was difficult not to when they’re staring me in the face all night! Feels so wrong cos she’s a childhood friend of mine but I had a crush on her for years as a teenager. If teenage me got to see what I saw that night, he’d probably have nutted in his pants.

    !updateme

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