I never thought that I will get to have a cuckold experience, as a bull, especially since I am neither young, nor endowed, but it happened.

She is my, lets say friend, I have known for over 20 years. I had a serious crush on her in our 20's, but she was too good for me back then, and that is fair, even now, she is way out of my league. But, in our 30's, we became FWB, but not on a regular basis, only when she would feel it, so, sometimes, 10 times in a month, and sometimes once or twice a year. I was her spare, I got that, but I didn't mind.

She got in a serious relationship some five years ago, and we kind of stopped seeing each other, in any capacity, and, well, it had to happen at some point, so I didn't give it much thought. But, maybe a month ago, she called me, to grab a cup of coffee, and well, I thought here we go again, but no, it was awkward, it seemed like she was with holding something from me, and when I asked her if she would come to my place, she said no, and rushed off. Two days later, the exact same coffee date...

I was puzzled, so I did something we agreed never to do, I started texting her. It took some time, a few days, and I guess it was easier for her to tell me over text, than eye to eye. She mentioned her fiance, is into cuckolding. I understood, immediately, what was up, so I was the one to encourage it, so the three of us met, at dinner.

He looked like he is about to faint, and he looked like someone who would love to see his woman fucked by another man - a total fucking wimp. She was talking, how they thought of it, how it would be easier with someone she feels comfortable with, etc. I was the one lightening the mood, joking, and she joined me, but when we parted ways, I thought, no way in hell this is happening, he looked like he regretted thinking of it. Two days later, she called, and set up a date night at their place.

The look, size and location of his place, answered all of my questions on why she is engaged to him.

I thought it would be awkward, but as soon as me and her started kissing, it was like he wasn't even there. They didn't ask for a condom, and I didn't bring one, hoping that we can do raw, and we did. He didn't jerk off, he just watched, fully dressed. It was amazing, better than it ever was, she came, loudly, and in the end, we did it in the pile driver position, and when I was about to cum, I pulled out, and did something I did many times before, with her, came all over her pussy, because, she has the fattest pussy lips I ever saw.

I was still tossing the last drops out of my cock, when he got up, almost ran up to us, I pulled back, thinking, he is about to hit me, but no, he got on his knees, and started licking my cum off of her pussy.

I am far from a moral idol, but that felt sick, so I got into the shower.

We are meeting again, next weekend, when he gets back from his work trip. I feel conflicted, but I guess that my cock will do my thinking, like it always did, and that I will continue this ordeal, even though, I felt pretty pathetic after that night, me, the guy who always thought sex is everything. I think I found my boundary, but I want to see if I can push through it.

I've just turned 40 and think it's time to confess a 20+ year old sin.
My mom met a really nice guy when I was just a teenager and they got married. He was really nice and really good looking and 11 years younger than my mom. Over the years as my interest in boys increased, I began to get a crush on him and eventually began fantasizing about having sex with him. When I was 19, my mom had to spend 2 months setting up a new company office in Seattle and only came home every other weekend during that time. I had already been flirting with and teasing my stepdad, and decided this was the time to see how far I could take it. One night I came home from work and took a shower and deliberately forgot to get a towel. I stepped into the hallway and went to the linen closet which was in full view of the loungeroom where he was watching tv. He asked what I was doing and I said I forgot a towel. He said I should have yelled out and he would have brought me one. I cheekily asked if he would have dried me off too and he turned beet red. I put on a long t shirt and a skimpy pair of panties and joined him on the couch. Asking if I could put my feet over his lap, he agreed and as I stretched my legs out I made sure I "accidentally" kicked his groin, then sitting up quickly apologized and reached out as if by reflex and cupped his cock quickly, then drew away and apologized again. I could tell he was uncomfortable, and with small subtle movements of my legs I gradually felt him hardening. After a while his hardening became obvious and he asked me to sit up, so I lifted my knees to my chest, giving him full view of my barely covered crotch, then spun round into a sitting position. After seeing my crotch his cock was tenting and I decided it was now or never, so I looked at him and asked if he needed help with that and quickly added, mom will never know. He hesitated then said we couldn't and I replied that I wanted to and reached over and began rubbing his cock.
Within 2 minutes his cock was inside me and he pumped into me so fast and hard that he was ready to cum in a few short minutes. He asked if he was ok to cum in me and I said yes, and he poured his cum into my pussy. Almost immediately he began to regret what we had done and said we could never do it again.
About a year later, he and my mom went seperate ways as she moved to Seattle and within days he knocked on my door. My boyfriend answered the door and my ex stepdad came in and made some small talk, obviously wishing my bf was not there. I told him to come by and take me for coffee the next morning. When he arrived, I dragged him inside and we fucked for hours. He asked about my bf and I said I fucked around on him all the time and he had no clue about any of it.
And so led to a 2 year affair behind my bf's and eventual husband's back.

Thankfully I’m a bit OCD and had prepared most of the appetizers and sides Friday and burger and dogs are well....burgers and dogs. I set up pretty quickly and with about an hour until the start time I was making my signature Sangria. Nectar of the gods with a sneaky kick if you’re not ready for it. Anyway, Ben’s number shows up in my phone and I’m excited and terrified at the same time. He coming...he’s canceling....worse. He asked if he could bring a friend. A chaperone..a buffer. I’m crushed and screaming in frustration inside but manage to use my big gurl words and cheerily say “of course!”

My friends begin to arrive at the appointed time. If anyone cares, I was wearing denim overall shorts that I think do amazing things for my butt with a plain white tank top. Music, talking, laughing...etc then a knock at the door followed by Ben coming in with his friend. Flashback.....Ben is an adorable twink maybe an inch or two over my 5’6” with a hint of musculature but quite defined. I know from lastnight that his short black hair and eyebrows are the only hair he possesses. Oh, and he has a wonderful 6 inch cock that is perfect for sucking and fucking. Lol. He introduced his friend as Randy. He was similar in build to Ben but with shoulder length blondish hair in a ponytail and sweet looking brown eyes with eyelashes I’d kill for. He was a total cutie. Shy but charming at the same time.

The party went as they usually do. I flirted with Ben as I had yesterday but being a good hostess I didn’t have the chance to corner him like I did yesterday. The shocker was Randy. He managed to cop several feels on me as I was carrying trays or other items. I would put an extra swish in my walk to let him know I appreciated it. My sangria was a hit and most left feeling no pain leaving me alone with Ben and Randy and a tremendous amount of sexual tension in the air. The second time Randy had goosed me I knew I was getting fucked by someone that night so I slipped into my room and inserted one of my smaller plugs to keep me stretched just enough...

“Boys” I said, “one or both of you need to take me to my room and fuck me. Preferably both of you”. So that’s how I found myself naked in the middle of my bed with two sexy bois sucking, licking, and nibbling on my tender nipples while getting lube fingered into my ass and slowly stroked off at the same time. Ben rolls me over and slides into me slowly (thankfully because I’m still a bit sore from lastnight and this morning. COVID it’s been a while) Randy slid around and sat in front of me and I happily went to work in his dick. A bit bigger than Ben and barely within my ability to deep throat comfortably. A few minutes in that position and he switched to 69 me. Heaven! Ben is giving me long smooth strokes and rubbing my back. Randy’s mouth and tongue are everywhere. On my cock, my balls and inner thigh. Ben is speeding up and thrusting deeper I know he’s ready to cum. His cock pulsates inside me and his fingers dig deep into my hips I’m getting my third load in 2 days! A few moments later Randy succeeds in bringing me off and wanton cum whore I was that night I dove into his mouth with my tongue to share my cum. I decided to ride Randy’s cock and end up pulling it out of Bens mouth so I could sink it into my dripping hole. Dialated by My recent fuck and slick with cum and lube he slid right in consummating my first threesome. Ben put one more load of cum into my ass and I got to fuck Randy too before they had to leave.

Neither are relationship material but I’d love to have them over anytime. Sara.

Still drooling over and fantasizing about my dream crush lovergrl30. Haven't seen her on camfuze in a long while and my cock is going stir crazy because of it. :)

Need help! i'v this huge crush on my aunt and i dont know what to do! any advice on how to maybe get her to suck my cock or fuck??