So just as a preface I’m definitely not saying you should flash people, it’s kind of against their will and I’m not condoning that. I’m not condoning even what I did, just telling the story how it happened.
This takes place when I was younger. At this point I had been told by quite a few girls at school that I was hot. I don’t want to brag, but I was probably the most confident I’ve ever been at this time. Jennifer was my friend’s mom but was also my mom’s friend. She was a single mom and would do housekeeping on the side. Our families hadn’t been friends but maybe a year or two, but she was over once a week to clean and at least once a week to hang out.
A little before this I was hanging out with her daughter. Evelyn was the same age as me and a lesbian and so we were just best friends (she helped get me laid so much lol), but one night we got high and she said that her mom thought I was hot. She blurted out, “One night she told me, ‘I knew you were a lesbian because you don’t even look at Braden’s butt when he walks by.'” I was obviously super complimented but just laughed and said, “DON’T TELL ME THAT!” Again I kind of could tell I was hot at this point in my life, but having a woman twice my age think so was special. Although I fantasized about fucking Jennifer, she was both my mom’s friend and my friend’s mom so it was really easy to realize it was a terrible idea.
At the same time I started becoming an exhibitionist. I really get into wearing all different kinds of underwear, even more “exotic” ones and I just loved being shirtless. I actually ended up getting drunk and flashing my dick to a few girls at a party, but they seemed to really like it which just made me want to do it more. I was really into porn where the girls just walked around casually naked, and I wanted to do that and find a girl that did that. The combination of all these things in my life made it a fantasy to be naked in front of Jennifer, if for only a second. But me and her were almost never alone together. Jennifer was almost always with my mom or Evelyn except when she was cleaning which was almost always before I got out of school. But, for some reason one day, she was still there when I got home…
I quickly realized this was my opportunity to “prank” her, which at this time is what it felt like (a racy dare). I mean, I loved seeing naked hot girls, why wouldn’t she want to see a hot guy naked? She saw me come in and said hey and that she was almost done but still needed to do my room. I told her it was cool and I was going to take a shower. She acted like she shouldn’t be over with just me while I was showering, but I reminded her I totally did that a few times at her house and reminded her I would open the door when I was done. I hopped in the shower really fast even though I had just taken a shower that morning. The thought of what I was about to do was turning me on, and it only took me about 20 seconds to rub one out in the bathroom. Despite just getting off I still wanted to flash her. TBH at this point it was more exhilarating than a true turn-on, and in my head I thought it would be super funny. I got out of the shower and opened the door to my room leaving the door to the bathroom almost closed.
It didn’t take long at all for her to come back to my room. I was naked in the bathroom when I heard her come in and start to take the trash out of my basket. I opened the door the rest of the way into the room, stark naked with a grin on my face. She had my trash can in her hand emptying it into a bigger one, when she saw me coming in and looked up. The second she realized I was naked she dropped the trash can. The trash was already in the bag but the container dropped and made a thud. She covered her eyes up with her hand and blurted out, “OH MY GOD I’M SO SORRY!!!” She just stood there completely frozen with her eyes covered. This is not how I thought it would go at all. I really thought she was going giggle and just leave the room laughing, kind of like the girls at the party did. But she acted like she was legit in trouble. At this point I felt bad but I still thought she would totally like seeing me naked if she would just relax. My confidence was to the point of stupidity and I genuinely thought I just needed her to know I didn’t care.
I immediately blurted out without thinking much of it, “It’s okay it’s okay it’s okay.” I still was completely convinced despite the fact she acted the way she did that she would like to see me naked if she knew I was okay with it, so waited a split second and said, “You can uncover your eyes it’s okay.” She did but upon opening her eyes she immediately saw me naked again and covered them. She said, “BRADEN, YOU’RE STILL NAKED!” I just said, “It’s really okay!” kind of loudly and then said, “Like I don’t care if you see me naked *AT ALL*.”
Where I was standing she was completely between me and the door. I really started to feel like I was being creepy AF but she was five feet from the door and I was at the opposite end of the room, like why wasn’t she leaving if she didn’t like it? I really thought she would feel way better if she knew I’m just really into showing off, so I said, “Jennifer, it’s totally okay, like you don’t have to be ashamed.” She kind of took her hands off of her eyes for a moment, looked directly at my dick and said, “Wow, that’s your penis…” She covered her eyes again though now they were just flat as a board an inch or two in front of her face as if she was starting to relax. She might have just been making an exclamation but at the time I wanted to think she liked my dick so bad lol. I would have had a total boner but I couldn’t because I had just came. Instead it was just was hanging there looking quite a bit fuller than usual.
I said it again, “You don’t have to cover your eyes, like you can look at me.” Her palms were held out tight but she slowly brought them down. She said with a very nervous voice, “Braden, why are you naked!?” Still having it in my head that this would all be fine once she wasn’t freaked out, I replied back, “I was changing. Look I’m sorry but I really really really don’t mind if you see me naked. It’s just a human body, and I honestly kind of like it.” With a voice that still sounded pretty freaked out she said, “What do you mean you like me seeing you naked!?” She said it like I had just grabbed her boob without her permission which took me by surprise. I saw no shame in either my body or finding her hot though, and I *knew* she found me attractive. On top of what Evelyn had said, I noticed she was starting to glance down at my abs and dick occasionally, only to catch herself and look up at me. Despite her anxious tone she was still standing there in front of me staring at my body, which was my indication everything was ultimately fine. My confidence grew and my voice got calmer and deeper. “Look I don’t want to have sex with you or do anything crazy, but” she cut me off and said, “This is crazy!” I continued and said, “Look, I DON’T want you to have sex with me, and I don’t even want you to touch me or for me to touch you.” I could tell tell hearing me say this was relieving, but she was still extremely tense. I continued talking, “I know this is weird but I just really like being naked, and I really live being naked around beautiful girls. I paused for a bit and said, “but that’s it, like I promise,” awaiting her reaction.
She had sat there the whole time listening to what I had to say. After I got done talking she took a very deliberate look at my middle-lower body and then looked back up: although teenage Braden definitely thought I had the best dick ever I realized quickly she was definitely way more into my abs. I remembered Evelyn said she said about my butt, and so to help break the tension I turned around and walked into the bathroom, letting her check out my booty. I grabbed the towel on the counter I was just using and started drying my hair off with it. I sort of did it sideways so she could check out my butt and watch my dick jiggle without me staring back, as I rubbed the towel over my head and face. When I pulled the towel away from my head, I saw her blatantly staring at my body and without words.
I quickly asked as if it was no big deal to do so if she thought I was hot. She said, “Braden, that’s not appropriate! I’m your friend’s mom.” I thought it was odd she said that and not that I was Evelyn’s friend, but either way I said back, “It’s okay if you don’t think so, like I would understand. I just want your *honest* opinion.” I thought I already knew, I just wanted to hear her say it so bad. This whole fantasy had gotten out of hand and this was exactly what tickled my exhibitionistic kink. She was staring pretty hard at my abs and dick now, and she said, “…I mean…If I was a girl your age I would be very interested in you,” in a very formal tone but still embarrassed. I replied back, “But do you find me hot *now*? Like you’re the hottest girl I know, I just want to know if you think I’m hot, too.” She scoffed at the idea of being the hottest girl I knew, but she didn’t outright object. She very sheepishly replied, “Yes, you’re very attractive.” as if relieved to say it, yet still guilty for thinking so.
At this point I felt like I needed to reassure her that what I said was true and that I genuinely wanted it to stop here. I asked her, “Would you do me a favor?” She looked up from my body to my eyes. I said, “I’ll put on some underwear, but I want you to go over there and pick out the pair you think is the absolute sexiest, like the ones you want to see on me most.” Her face *lit up*. You could just tell she was into it, but that she shouldn’t be and we shouldn’t be. I could tell she was about to tell me I was being inappropriate again so before she could I said, “I just want to know like what kind of underwear girls find hot, like what should a guy wear if he’s trying to be sexy?” She looked into my eyes, way deeper than she had the entire time she had been in the room. For the first time she was looking at me like the girls at the party did. She was looking at me like girls did when they wanted to hook up. She said, “You are *so* bad,” in a manner that almost admitted defeat and walked over to my dresser. She started shuffling through them, saying after while, “God, you have a lot of underwear!” I laughed and said, “I wasn’t joking, like it really is my thing.” She took a good while looking through all of them, which the sight of her going through my underwear was hot enough. She picked out one and kept it in her hand while still looking. She picked out another one and then threw them both down. One was a pair of bright yellow, super soft American Eagle microfiber trunks and the other were a pair of fancy string bikini briefs I bought to be wild/play soccer. I asked her, “Which ones do you like?” She replied, “Most girls really like the tight trunks like this and pointed at the AEs.” I replied back, “I wanna know what you like, do you like the bikinis?” She looked up into my eyes and nodded yes in a way as to admit it was kind of weird to have a thing them. I picked them up and said, “I do too, they’re some of my favorites.” and slid them on over me.
I could feel her tension lighten up a bit when I put them on. The bikinis I bought were “package-enhancing” and so they gave my the biggest bulge known to man with a giant dickprint. I said, “What do you think?” She said, “I really like those kind,” keeping her enthusiasm reserved while staring at my junk. I said, “I’m always afraid they are going to show off my dick too much.” I immediately asked a question I was curious about: “Do you like it when you can see a guy’s dick through his sweatpants and stuff?” She recoiled a bit as if I had gone too far to ask. I said again, “You don’t have to answer,” and she quietly replied back, “I really like it but not all girls do.” I took the opportunity to go even further, and pulled out some thin joggers I had, putting them on over the bikini briefs. The combination was not one I had normally done. Despite my exhibitionism I was more into being naked than showing off my junk, and the combination of these two resulted in a huge bulge that stuck out almost comically far but that Jennifer seemed by all accounts to enjoy quite a bit.
Now that I had pants on she was way more relaxed. Sensing her relaxation I stepped closer to her, still shirtless. She couldn’t take her eyes off my abs and as I moved closer it made it harder to choose between them and my face. She looked up at me as I finally got too close, looking deep into my eyes like she was pleading with me not to. I kind of think now she was horny as hell by this point and I might have honestly been able to do whatever I wanted to her, but I was completely oblivious to this, finding more than enough joy in what had just transpired. I stopped a few feet from her to show her she could trust me. I said to her, “I want you to do something for me, okay?” She asked what in a voice that was nervous yet totally compliant. I replied, “I think you’re super hot, and it would be the biggest turn on in the world to me if you came into my room after cleaning and just picked out a pair of underwear for me the next day. Then you can go around all day knowing I’m thinking about you, and it can just be our little thing.” She got really embarrassed by this, but the smile she had burst from her face finally. She looked at me with a look like she was nervous for this to be a continuing thing, but she said, “I can do that.” I also said, “Also if you happen to see me naked or in my underwear it’s okay, right?” She didn’t say anything but was staring me straight in the eyes as if she wouldn’t complain if it happened again. After that it was slightly awkward. I kind of didn’t know what to say for once, and she told me she was done after she finished in my room so she pretty much immediately left.
The next week I came home and she was still there. I came in and she said that she hadn’t done my room yet, and I told her I would be in there. She came in about 2 minutes later and while she was tidying up my room, I went ahead and got in the shower. I don’t know what she did while I was in there but she was still out there when I got out. This time I had a huge boner though which made her go, “Oh My God Braden you have an erection!” I covered up with a towel but said, “Sorry, I’m just going to put on some underwear really quick,” and went over to my dresser. I took off my towel and let my boner stick straight out for a second until I put on my underwear, and noticed Jennifer staring right at my rock-hard dick with no desire to look elsewhere. I slipped on some boxer briefs and pushed my dick to one side, facing towards her so she could look if she wanted. Again she relaxed more when I had on underwear, but not for long until I asked, “Do you think I have a big dick?” She got embarrassed as hell at this question and said, “BRADEN!” I replied back, “Sorry I’m just curious, like how would I know if I did?” in a somewhat oblivious tone. She replied back pretty matter-of-factly, “I’m pretty sure you know the answer to that question already” as if she could tell I was being naive. I replied back, “I think I know what that means,” and waited for her to reply, but she went back to cleaning as to not have to answer the question.
From there I have to say things honestly got a lot more vanilla. The same thing would play out pretty much every week for a few months, with her watching me change, get in the shower, talk to me while taking a shower, etc. I never did anything like jerk off in front of her, but I noticed she definitely got downright excited to see me pop a boner. I was already about to graduate high school when this happened and so within a few months I moved to college. We all still hang out and have a good time, and the older I get the more I’m just shocked that neither her nor I got weird afterward in front of anyone else or tipped anyone off to what happened. I mellowed out big time on random nudity and realized I’m way more into being naked around my girlfriend than I am showing my dick to drunk college girls, and I still have a huge fantasy about having sex with Jennifer that feels completely forbidden.
Source: reddit.com/r/gonewildstories/comments/pplyk3/i_m_flashed_my_friends_fmomhousekeeper_right
How long ago was this? If you still talk to her you should ask her to go [anywhere] with you. If she says yes, she’s interested. Let the “date” play out and then escalate accordingly from there.
Wow. What a story. You are an excellent writer. Combine that with your package, you can be the dream guy for many women ♥️