I was 23 at the time, in graduate school, and living in upstate New York. She was 51, smoking hot, slim, blonde, fake b-sized breasts, right around 5 feet, and tan (but not overly tan). I wasn’t actively seeking a cuckold experience, but was seeking a cougar. We met online through OKCupid, exchanged pictures, and set up a time to meet next week at a local bar for a few drinks before hand. The fact that I was her first cuckold was particularly exciting for her. I also texted with her husband throughout the week prior so he felt comfortable with everything and to talk about what I was going to do to his wife—he loved to hear about my plans and then used the texts to tease his wife. She never allowed her husband to come watch, however.
When she walked into the bar I was blown away. She was all dressed up in a short skirt, heels, a low-cut white t-shirt, and leopard print push up bra you could see through her shirt. I loved how she was dressing slutty just for me and not her husband. We teased each other, played footsies, and chatted while we had a drink. At first the conversation was very light since I was kind of nervous. I had been with older women, but wasn’t sure what to expect from a cuckold situation. By the end of the second drink, however, our conversation had naturally turned filthy, talking about how she would rather me drinking my cum and I would rather her be sitting on my face than on the stool. Needlessly to say, we exited the bar after our second drink and she followed me back to my apartment (she had a mini van which isn’t important until part II of this story).
We didn’t even make it through the door of my apartment before we started making out. My hands were running up and down her body, but before I could take off her clothes she asked if she could use my bathroom for a second. While she was in there, I took off my clothes and got on my bed. She came out a few minutes later in white stockings, and no bra. She asked me take some before photos of her body on my bed, which we had agreed to earlier.
After photos were complete, things got heavy fast. She started to suck my cock and rub my shaft. When my cock wasn’t in her mouth she was telling me how much bigger and younger I was than her husband, and how she wanted me to cum all over her face and show him. I got her up off her knees and threw her on my bed; she laughed excitingly at how strong I was and how she loved being tossed around by young men.
I slipped on a condom and went to pound town on her pussy. I was putting her in every position, but our favorite were cowgirl and doggy—I love to pull hair from behind and she got really into that too. I loved seeing her face reach climax and tits bounce in cowgirl. She kept squirting all over me, which only added to my desire to keep going.
At some point we switched over to an armless chair where she straddled me and grinded on my cock ball deep while we made out. Rocking back and forth, she kept whispering how she wanted wanted me to use her body and begging me to cum on her.
After about 30 minutes I could tell she was tiring and, to be honest, I was too. We were both drenched in sweat and the sheets were soaking. Her vagina was gaping and her ass was bright red from all the spanking. I told her to get on her knees and to deep throat me until I blew my load on her face. She happily obliged. I took of my condom and used her throat freely for a few minutes until I was about to cum. I told her to use her hands and keep her mouth opened.
With her face covered, I snapped a few pictures to send to her husband before she shoveled the cum in her mouth and played with it. We had a fun, relaxing, cold shower to cool down and shared a beer. We planned our next meeting in two weeks and she left after a quick peck.
Part II involves the van, so stay tuned!
Source: reddit.com/r/gonewildstories/comments/78w51b/my_first_cuckold_experience_part_i
My wife and I have a “normal “sex life…we both work stressful jobs with her as a nurse at Trauma Center and I am a firefighter. One night we were doing our cuddling on couch and getting ready for romantic time and she asked me had I ever fooled around and I told her no as we had been married 12 years and I was very satisfied plus I do believe in marriage is about sex with wife.
During our love making she asked me would I screw around if she gave me permission and I told her where we are going with this. She told me she had a female friend nurse who had a problem, “her husband has a very small penis and she wants to try a larger one and he wants to watch. My reply was so we are going to start swinging? She laughed No! I want to share your cock and no lovemaking involved but please just give her some big cock. I am almost 7 and thick and I have only seen a few erect penis’s in my life so I am not sure where I stood size wise. I told her,” I couldn’t believe she was thinking like this….was this about next time you get some strange cock?” She got out of bed and opened her phone and showed me a picture of both of them nude. She was hot but didn’t say that to my wife and he was athletic but I had to agree his was small and the picture had him with panties pulled half way down was different. I told her give me some time and I would let her kow!
About 2 weeks later I told her since she was working 3 night shifts in a row I would meet this couple but I wasn’t going to say if I would take care of his wife or not but I did let her know I didn’t want oral on me from him! My wife agreed and told me she would take with Karen.
The big night arrived and I went to their nice home and they were both polite. She told me my wife and her had been talking for weeks so her and her husband were both excited. She made it clear that there was to be no kissing and maybe a onetime only. This was about sex only. I was clumsy starting out as this was a new area to me plus I had only been with wife last 12 years. I asked her husband if this was OK with him. He told me he was excited that his wife could experience something new. We started out with foreplay and I got aroused and we made out like a new couple in heat. Her husband was watching while wearing a pair of bikini panties. I did notice there was not much in front like an erection. Karen asked if we can move to the bedroom and I told her yes! I undressed her slowly and her husband set on end of bed. Karen told her husband to take my jeans off. I was kind of worried about that but I was turned on and he pulled jeans off as I played with her breasts. Then she sits on bed and told him to pull my boxers down and he slowly did. Her words had to be humiliating to him because she told him that’s a man cock…she started off with oral describing how different I felt in her mouth. I was at the point of I cant complain but I knew if she kept on I was going to unload in her mouth. I got in the bed with her we began to play with each other and she tells me, “its time I get fucked….she was soaking wet and I still went slow but it took some time until I hit bottom and she squirted and again starting telling her husband what a real cock felt like. I took my time and finally she told me to fuck her hard. I finally came hard and left it in…wow it was great!
I rolled off beside her and she played with my cock as her husband began doing oral on her! She told me he was here for clean-up. I had done that to my wife but I just watched. He seemed to love it. I was getting horny and an erection was coming quickly…I started masturbating as she was squirting from his oral and this was one hot scene….they both stopped and I felt exposed as I wanted release very bad but wasn’t sure what wopuld be next. I told her can I cum. She told me yes but hold off just a minute and her husband stood up by the bed. She pulled his panties open and told me to blast your load on his weenie. He got closer till the head of mine was at the head of his and I came all over him!
We got dressed and went to living room and talked and we all thanked each other. She did ask maybe can we do this again and I told her I didn’t want his regular as my wife was damn good in bed but you can ask my wife and we can go from there. I left embarrassed but totally relieved sexually.
When I got home my wife wanted every detail and I told her and she got hot and went to bed immediately but I had to do oral and foreplay my cock was out of commission. I asked my wife if this was going to be a repeat because I actually preferred her in bed and maybe we could get more kinky if she wants…she smiled of course