I want to get this off my chest since I have told nobody about this encounter at all. Im both proud and disappointed that it happened.
TLDR: I had just had a bad breakup. Was friends on social media and started to casually chat after a suggestive post she made. One thing lead to another and we organized meeting up for me to eat her out. We did much more than that. We met up a few times and she was the best sex i’d ever had. Unfortunately despite it being made very clear at the beginning there were to be no feelings involved, to which she agreed it was for the best, she immediately developed them. She became increasingly frustrated I did not return her feelings. She has some problems and I had to end up blocking her after she sent very sketchy images of self harm to me.
Had my close friend and some of their family as friends on social media. I have met with them many times and they know me well to the point that i’m considered part of the family! The Aunt however was someone I only met about three times. She was in her early 40’s and was a little chubby and very flirty. When I joined them for Christmas a few years ago we played a little game that you would crank up and randomly pie someone. When shot it’s load all over her face (heh) she licked it off like a pro.
She made a post detailing how she was disappointed and out late a night. I commented to say be careful since obviously late night can be dangerous. At this point I had no thoughts about her at all and my comment was genuine. She messaged me seconds later asking why I cared so much. I told her how I was just making sure she was safe. After a few more normal messages I said goodnight. The next morning she messaged me saying how she had sex all night with a younger man (my age) and it blew her mind, she thought he was “the one” and loved every second of it. I was blown away by her just admitting this to me since we weren’t chatting long. I just sort of laughed it off but it stuck in my mind. I should have seen that as a red flag though. Later that day she was messaging me about how he broke her heart and didn’t want to have a relationship with her. She said she was extremely attracted to younger men and that older men her age were no fun. I was just kind of like “alright then”. I had broken up with my girlfriend about 3 months prior and had not had sex for about 9 months since we were long distance. So I was in a dry spell and not thinking with the correct head. I was never able to eat out my girlfriend so I had (unsuccessfully) tried to find a woman who would let me after the breakup. Seeing my chance I went ahead and let her know that I was looking to practice going down on a woman if she would let me. She acted shocked but loved the idea and agreed, but said we couldn’t go any further she was the Aunt of my friend. She offered to pick me up right then and there but I turned her down since it was extremely late and I was too nervous. What I had just offered and set up with my friend’s Aunt was wrong but so very hot.
The next day we met up and she admitted she was unsure if we would actually go through with it. I am not exactly a ladies man and can be a bit awkward when it comes to talking sometimes. But my actions on the other hand are not so awkward or shy. So I asked, and cupped her breasts firmly in the car. She smiled and started to drive us back to her place. The sexual tension was palpable. I’m sure I was trembling but im not sure if she noticed. We slipped into her home and put what little stuff we had down in the bedroom. I kept imagining what would happen if my friend happened to visit while I was here. What would I say? Once again she said she was unsure if we could actually do anything. I don’t know if this was to test me, or if she just genuinely thought we were too nervous and shouldn’t continue. I reached under her shirt and felt her breasts once again, fondling them as she stood there and closed her eyes. “We should get to the bedroom” she said with a smirk.
She got on the bed and undressed. Laying on her back she kept her legs closed until I got close. I gently opened her legs and saw her smooth shaved pussy. She covered her face and was saying how embarrassed she was that she was doing this with me. I gently kissed her thighs before lapping at her pussy. I couldn’t resist for long though and began to really eat her out with enthusiasm as my nervousness melted away. This was what I wanted and needed at the time and I did not care that it was my friend’s Aunt. She tasted so sweet, and I swallowed as much of her overflowing juices as I could. She didn’t hide behind her hands for long. She began to moan and play with my hair, goading me to keep going. She asked if I really hadn’t done this before! I don’t remember what I said because I was buried between her thighs. My hands were pressing into them as her juices coated my face. I was insatiable and in absolute heaven! My tongue was sore but I did not care. Pretty soon she grabbed my hair and came hard. I rode it out with her clit in my mouth. Honestly I could have eaten her out forever. She tasted amazing. When she finally came back to Earth she told me how nobody had made her cum before. I found that surprising but thanked her nonetheless.
Now I was obviously very very hard. She could tell and kept saying to herself how we shouldn’t do it. But before I could reply she was handing me a condom to put on. I undressed as quickly as I could and attempted to put it on. That was actually my first time putting on a condom so I was nervous haha. It ended up not really fitting so we grabbed another one that barely fit. Now I ate her out a little more before lining my cock up with her glistening cunt. She wrapped her arms around me and helped to guide me inside. I pushed in slow, watching her intense stare falter from the pleasure. She arched her head back as I pressed my pelvis into her, bottoming out in one slow push. She looked at me with a fire ill never forget. She mentioned wanting to kiss me multiple times, but I had made it clear that I wasn’t looking to kiss. I think of kissing as something I do with the people I am romantically interested in. I know it sounds weird but that is how it feels to me lol. So I put my head against her neck and bit softly, holding her wrists to the bed as I fucked her. It had been 9 months since the last time I had sex so my form wasn’t the best, but the raw lust and primal instinct I felt as I thrusted into her kept me going. I turned to the left where her closet was with a sliding mirrored door. I could see myself laying on top of her, legs wrapped around my back, as we made the bed rock. I continued to bite her neck, breathing hard as I focused on letting out all my pent up sexual frustration with this woman. The whole time she is just gasping for air and begging me to fuck her harder and harder. She came twice but I did not stop. I could feel her walls massaging my cock as she shuddered and spasmed. All it did was make me go faster.
A few times I did actually feel the tip of my cock brush against her cervix. This is important soon. I have a huge fetish for creampies. Not the ones where the guy cums like 1 inch in and lets it run out for the camera. I mean the ones where a guy is balls deep and cumming as hard as he can with the intention of filling a woman’s womb (hence my username). I could tell I was getting close, and she told me she had already came twice but needed me to cum too. I didn’t know it at the time and chocked it up to having great endurance, but I had death grip from masturbating so much. Because of that my orgasm snuck up on me, and I pushed as deep as I could inside of her as I held her down and exploded. I could feel myself throbbing and pulsing my seed inside of her velvety depths. After what felt like ages we finally uncurled and I could pull myself out. The condom had been torn clean off so that it was only on the bottom half of my penis. Thats what I get for wearing one that barely fit. I was coming to my senses and she was in heaven. I had an amazing time but said we needed to go the store and get some Plan B since the condom broke. She was very nonchalant about it and said its all gonna be ok. She said she loved my cock and that nobody had made her cum 3 times in a row, if at all. I liked the compliment but was still worried that I had accidentally knocked up my friends Aunt. I did find it hot deep down but reality and my post nut clarity was kicking in. We drove to a nearby pharmacy and she went ahead and bought it herself. I decided that I should go home and made an excuse. Later that night after dropping me off she messaged saying she used the Plan B and had an amazing time. I don’t remember what I said but I thanked her as well.
We met up one more time and I got to have her sit on my face as I ate her out. She grinded against my face and I was covered in her juices. She also gave me a rather lackluster blowjob and I didnt finish, but I didn’t mind since my ex was terrible at them so I never expect to cum. We didn’t use a condom this time and she rode me cowgirl and reverse cowgirl which was amazing. She had medium sized boobs that I had in my hands whenever I could! When shed lean over me I took her nipples into my mouth and played with them. We ended up doing it doggy style and I was very careful about sensing my oncoming orgasm. I watched myself in the mirror as I fucked her. We were both very sweaty but couldn’t stop. When I got close I pulled out in time and came all over her ass. After that we sort of cuddled and spooned. I was grinding my semi hard cock against her ass. Funny enough the tv was on playing Godzilla 1998. From there we got dressed and she dropped me off at my house and we called it a night.
Now from the beginning I had made it clear at least a million times. She even confirmed it. There were to be no feelings involved whatsoever. This was just for the carnal pleasure (and for me to get better at giving oral). I would not have gone through with hooking up if I knew she would fall for me as hard as she did. She needed my messages and attention all the time, and would become upset if I took more than a few seconds to respond. She was always waiting with her phone in her hand constantly. I brought it up to her that this was a problem and she admitted she couldn’t help but fall for me. She wanted me to kiss her and love her and go on dates. While it is a cute thought, it was not what I had signed up for and I did not want to be in a romantic relationship with my friends Aunt. Because of her I do have a thing for milfs and older women, but she was showing so many red flags that there was no way I would agree to be with her. She ranted about all guys being the same and only wanting sex, why does nobody want to be with her, she should end her life and rid the world of her. The whole shebang. I felt really bad and tried to explain how we set rules at the start before we even met up, and that she can continue to try and find somebody else. I read all her long rants and really honestly tried to give advice. She had clearly been betrayed a lot in the past and was insecure. It got to the point where she somehow actually send me an image of her wrists saying I caused her to do this. I left a long message detailing everything about how I tried to listen and be a friend when nobody else would. How its not a crime for me to not have feelings for her like she has for me, etc etc. We blocked each other after that.
A month later she texted me apologizing and saying shed like to put it behind us, but I didn’t really receive that text since I had blocked her on everything. Now a few years later I got a new phone and transferred my contacts over. I was in a new relationship but saw her name pop up and felt bad. I left her a message saying id like to put it all behind us if possible. She responded saying why am I messaging her now and to delete her number, so I did. Now about a week ago from today she messaged me again asking why I texted her now. I repeated that I just wanted to put it behind us, which was probably naive of me to think. She IMMEDIATELY reverted to how she was before. She had said something like “I just got home. Why did you message me now?” to which I answered her question, and then said welcome home. She said “you sent that to the wrong person asshole”. So we blocked each other again. I tried. She was still the best sex ive ever had though.
Source: reddit.com/r/gonewildstories/comments/gt96x0/i_m22_slept_with_my_friends_aunt