I like younger women but I also **love** a good challenge. I started talking to her a few weeks ago She was very shy in the beginning but after a few days of texting, she tells me that she has a long time BF. They are very serious and live together. I assumed my chances were short. She is 24 years old, 5’5 long brown hair, doe eyes, and an amazing size 5 body. As we talk more, I realize that she is not happy with her BF. I am someone that she finds very attractive, but has never been with an older guy, but “Has daddy issues”. I am not overweight but not fit either. I am active, but I also am 37 and sit most of the day. I am the opposite of her BF who is 26, and works construction & hits the gym.
Category: gonewildstories
Squirting with Strangers watching [FM]
A few months ago I[F] was stretched and filled at a local adult novelty store while strangers watched.
I texted hi[M] jokingly with a naughty picture asking if I could leave work early that I could use the distraction. u/M_Cain replies to with “how about my cock as a distraction. Today.”
Already wet thinking about him fucking and filling me that week. My pussy throbbed harder as my excitement grew and I started to dripping out of my pussy lips and into my panties. I needed his thick cock stretching me again, it had been too long. I needed to touch, lick, suck and gag on his huge cock. I needed to have my mouth wrapped around him and my throat stretched from forcing his head down it. I needed to feel his hands grab my tits, ass, and hips again.
The Third and Final Part of That Ti[m]e We Got Drunk on Valentine’s Day and I [F]ucked My Lesbian Friend:
[Part One]([https://www.reddit.com/r/gonewildstories/comments/fej9ho/that_time_we_got_drunk_on_valentines_day_and_i/](https://www.reddit.com/r/gonewildstories/comments/fej9ho/that_time_we_got_drunk_on_valentines_day_and_i/)
[Part Two]([https://www.reddit.com/r/gonewildstories/comments/fffhe5/part_two_of_that_time_we_got_drunk_on_valentines/](https://www.reddit.com/r/gonewildstories/comments/fffhe5/part_two_of_that_time_we_got_drunk_on_valentines/)
Welcome to The Third and Final part of our story!
Anyhow, we proceeded back to the kitchen after disposing of the used condom and did some more damage to the Chinese food from earlier. We were both pretty ravenous and made a pretty hefty dent in the leftovers as we sat on the couch and talked about random stuff, work, mutual friends and what they were up to, recent events etc. It was all so very normal other than the fact that we were both naked and that I was keenly aware of the fact that Monica had a radish in her asshole. It was effecting her too and I could see her pussy was still soaked when she would move her legs, the glistening on the lips impossible to miss.
I was still pretty tipsy and my cock had never really gone limp since our last session as I was still incredibly turned on. Monica didn’t help matters by “accidentally” dripping some sweet and sour sauce on her breast and asking me to clean in off which I happily did with my tongue. I took the opportunity to suck and lick her pierced nipples as well which had her squirming but she pushed me back and said she wasn’t ready yet. I relented and played along as she chatted away pleasantly knowing exactly what effect she was having on me and enjoying it.
Keeping ourselves occupied on a business trip [MF]
I hear my phone buzz across the hotel room. Who could be texting me at this hour in another country? It was 11 PM and Jen has texted me “are you still up?” How did it get to this point?
Let’s rewind. Occasionally my job takes me out of town for projects. It can obviously get lonely in some random hotels in far off places. When I travel internationally, our company likes more than person to go on the trip. For this particular trip I was scheduled to go to a mid sized city in Mexico. My boss was going to go with me, but had to bail. Instead, he told me ask someone else in the office if they wanted to join me. I had become pretty close to this girl Jen, who was a few years older than me. Probably about 35 when at the time (I was 30). Jen is about 5’3” with dark hair and dark eyes. Her body was incredible! Skinny, toned legs with a tight round ass and decent tits. I would say a B cup, but very perky and round. Plus with her skinny figure they looked large.
I Tricked My Girlfriend Into Cheating Using a Fake Account [MF]
Please forgive me in advance. I am not much of a writer, but I have been sharing audio files of my girlfriend cheating on me and I have been getting a lot of questions about how it all started.
It started while we were in a long-distance relationship. Things were going great and we were extremely happy. We met here on Reddit, and we would spend hours talking here. One day I noticed a comment from some guy on one of her posts. It was nothing bad, not even flirtatious but she responded and they talked back and forth for a bit. It got me wondering and my head filled with stupid guy insecurity.
I got the smart idea to “test” her, so I set up a fake account and used it for almost two months to build up a decent history before anything. Around the same time I’d met up with a friend of mine from the military who was in town and I got a bunch of pics of him from his phone after borrowing it to transfer a movie he had. I had the idea to “borrow” his pics because of his looks. He’s a good looking guy build like a Grecian God and hung like a porn star.
When I was 18[F] and pregnant I let an older man fill me
To start, I’m not a slut or anything at all! I was told to post here. The guy who got me pregnant is now my husband (I’m 22 now) and the 41 year old was the 2nd guy I ever let have sex with me. The 41 yr old worked for my daddy since I was five or six years old. He always treated me really sweetly just like my daddy did. When I turned 17 he asked me out. I wasn’t attracted to him at all but he was so sweet and I felt safe with him. I knew he’d never see me naked or anything.
When I went to college I met my baby’s daddy. I was a virgin and felt funny about that being in college and everything. I was dating the 41 yr old and him. The 1st or second time I had sex with him I got pregnant. When I went to tell the 41 yr old that I had to stop seeing him because I was pregnant, he was SO sad. He asked if he could have sex with me and I felt so terrible I said yes. I didn’t like getting filled by him, but it made me so happy to see how excited he was after I made him so sad. It happened again when I was 4 months pregnant, then more and he offered to help me at home. I did tell my hubby a few months ago and he was really upset. So was I. I literally couldn’t stop crying. We’re doing much better now. I can talk more in DM’s but please be sweet and baby me. It’s scary to talk about and I respond best to being babied :)
[F] I lost my virginity to a fuccboi and loved every moment of it
I know virginity is just a concept and I didn’t really consider myself a virgin, but I was still very aware of the fact that I’d never had penetrative sex. In the past I think it was a mix of intense anxiety and also not knowing how to relax my pelvic muscles. However over the last few months I’ve been sexually frustrated, needed to get someone off my mind, and felt like I was ready to get fucked senseless now.
I went on a date with a fuccboi off of a dating app and even though I didn’t feel much connection over conversation, I felt helpless and needy whenever he had his arm around me and knew he would be attentive in bed. I happily went home with him and never told him that I’d never had penetrative sex. We fucked once (I was so relieved that it went in, and he kept commenting how tight I was, not knowing that it was a fresh untouched pussy) and then he went down on me and fucking stayed there until I came (first time orgasming with a partner also!) He was so amazed at how good my pussy tasted.
We ended up fucking so many times that night and I didn’t realize that I could be that loud in bed until he was pounding my pussy deep into his mattress and using his hand to either cover my mouth or shove my face into his pillow to shut me up.
SEX WITH A FATHER AND SON [FMM] [part 2]
After becoming Robert’s baby girl. He invited me over a weekday since both his wife and son would be out. To be honest I was scared of being caught by either of them. He had instructed me to wear no bra and panty and so I had done it that way.
I wore a purple sleeveless frock, which was barely gripping over my boobs. I had to adjust it several times before booking a cab…. I sat next to the cab driver and god knows how long he stared at my boobs before he started the engine. I knew my nipples were pointing out since the dress was of a thin material. I just smiled at him and we continued the trip…..at the end of the trip, he asked for my phone number but I said I already had a date.
Before getting out of the cab, I had to put the dildo Robert gave me at my party since he said he wanted to see me that way, the dildo hanging out of my pussy while I would be wet from it. I had kept it in the purse all along and thought of wearing it just seconds before I rang the doorbell because it was uncomfortable to sit wearing the dildo.
I asked my friend to seduce my husband. And I loved it! [MF]
This one night my husband and I were attending a cocktail party at an old friend’s house. A lot of people there we’ve known for years. One of them was my friend Kasie.
I’ve known Kasie since college. Some of the guys around campus referred to her as “Jugs”. She was a little bit taller than I (maybe 5’6″ or so) and just as skinny. But she had a gorgeous DD rack that I swear only got bigger after having a couple rugrats. Kasie had quite a bit of fun with plenty of guys in college, but found a man after a while to settle down with and start a family. Her marriage unfortunately ended a few months ago, and she was now trying to get out and move on with her life.
As the party was coming to a close, I found my husband outside on a patio chatting with an old friend of his. I had came around from the front yard as I had put some of our things in the car, and he didn’t realize I was by the side of the house eavesdropping.
Sexy wife gets seduced, then dominated (part 1) [MF]
The Wednesday rehearsal at Matt’s had gone OK, but when she went to her car Cindy discovered that it wouldn’t start. After a little tinkering they collectively decided that the best thing would be for Cindy to stay at John’s for the night (Matt had some guests over) and call the AA in the morning – she dropped me a text to let me know.
The band sat round John’s kitchen table drinking and laughing for some time – until Helen came down in her dressing gown and had a go at everyone – which killed the mood. She pronounced, sharply, to John that he would be sleeping on the sofa, then turned on her heel and disappeared upstairs before anyone could explain what was going on.
They chatted for a while longer, but the atmosphere had cooled and shortly thereafter Matt and Kenny got up to go, leaving John and Cindy at the table.
They sat and talked, John pouring Cindy a couple more drinks – noticing how drunk she was getting, and how more approachable she seemed. Predictably, they ended up talking about Helen – Cindy admitting that she felt a bit sorry for John, asking what it was that he had done wrong.