by RandomGuy

Gender: Male
Age: 29
Race/ethnicity: Caucasian
Current location: Los Angeles
Highest education received: College degree (eg., BA, BS)
Occupation: Management
Relationship status: Single
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 1

To Cuck

How long ago did this hookup happen? 8 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Carol was 5’9″, 35ish, slender, redhead with freckles, green eyes, Dcup fakies, Waxed pussy and tone ass.

Had never met her before our encounter.

I suppose I felt she was smoking hot for her age

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had gone to a local bar since I had recently broken up with a girlfriend I had been seeing for over a month. One of my friends worked the bar and always hooked me up.

While watching something on tv I caught a glimplse of Carol sitting at the bar. Our eyes met. She was wearing a tight, skimpy outfit that screamed FUCK me! I decided what the hell and sat next to her, buying her a drink. She had been there for half an hour and said she was getting lonely. I asked her if she wanted attention? She said yes.

We chatted a bit but the vibes she was sending wasn’t to talk but to go elsewhere. I asked if she wanted to leave together. She said yes but had a condition. In my experience thats never a good thing. I asked what. She then tells me that she was at the bar SPECIFICALLY to have sex. And the reason why is because her husband and her wanted to try cucking. I had heard the term but didn’t know much about it so she explained. At first I was like “why?” Apparently her husband gets off on the idea of watching her having sex with other men and she gets sex with strangers out of it.

I told her I wasn’t into the weird stuff. She assured me it would just be sex between us and her husband would just watch. They already had a nearby hotel within walking distance ready. It sounded shady as shit to me. She looked around and reached down grabbing my cock, squeezed lightly and whispered that no holes were barred.

I was game.

We walked out the bar and across the street. The hotel was actually quite nice. Her husband Peter was waiting in the room. He greeted me and we talked a bit as Carol went into the bathroom. I asked him if he was really ok with the idea of this? He was really looking forward to it and said he got his jolly’s from the idea of watching Carol getting fucked. I asked if their were limits or anything? He said I could fuck her wherever and how ever. He preferred no condoms which  was a red flag for me. He showed me a fairly recent screening of hers. He asked if I was clean and I told him I was but didn’t have proof on me.

He said it was fine and said that he wanted to film and photo the event. I was ok with it as long as my face wasn’t in any of the images. He also asked to ignore him and just go for it and after I was done with her to dress and leave as he would want to fuck her afterwards.

I agreed though was still baffled at the idea. It was then that the bathroom door opened to reveal Carol in some sexy ass lingerie, thigh high stockings and high heels.My dick was throbbing. Peter got up and sat in the chair in the corner of the room.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Carol walked over towards me. I was about to stand but she told me to sit. She hovered over me and began to give me a lap dance. She sat in my lap facing me and kissed me deeply. I looked at her and could see she was looking at Peter who at this point had slipped his dick out and was jerking. I could see why she wanted more, it was pretty damn small.

I groped her ass as she continued. She stripped off her clothes and finished the dance with my face in between her D-cups. She then took off my shirt and got down and unzipped my pants freeing my hard cock. She smiled and began to suck then deep throat my dick. She looked again at Peter and smiled. He had also gotten undressed and was shooting on his camera. Thats about when it got weird.

Peter – “You like sucking that cock baby?”
Carol – “Mmmm I love it. Such a big thick cock! I can’t wait to get it in my pussy!”
Peter – “Do you like it more than mine?”
Carol – “Fuck yes, I always want this dick in me!”

I was pretty weirded out but the tone, but was enjoying myself so I ignored Peter all together. For the most part he would just get close up and jerk and respond to Carol.

I stood and laid Carol on the bed. Parting her legs I aimed my dick. She asked me to shove it in hard and fuck her rough.I did, and she was soaking wet, so it just slide right in. She moaned loudly (im sure the neighbors heard). “Oh fuck its so big! God damn I love it” She moaned. It did feed my ego quite a bit. I fucked her missionary rough like she asked. She told me to call her dirty whore which I did though I hoped this was as weird as it got.

We rolled over and she got on top. She did reverse cowgirl and leaned back with her legs spread so that Peter could see. After a few minutes of that she did regular cowgirl as I squeezed her nipples hard. She came hard with a shudder. She asked Peter to sit in the chair and we moved towards him. She placed her hands on the arm rest, leaning over him. She told him not to touch. She spread her ass and told me to fuck it.

I obliged. She had apparently lubed her ass in the bathroom cuz it went in well. It was fucking tight. I fucked Carol’s ass as her husband helplessly watched and recorded. It was so tight that I came hard filling it up. Carol turned and showed her husband another man’s cum dripping out of his wife’s asshole. He jerked ferociously as he took photo’s. He begged to cum in which she declined.

She laid me down and sucked my dick, staring me in the eye knowing that I knew it had just been in her ass. She sucked and licked it getting hard again. She got on top of me and inserted it back into her pussy. She rode my as I sat up. I kissed her deeply as I groped her ass. I looked at her husband desperately wanting to cum but not being able to. I asked why he couldn’t. She said that if he did, next time he couldn’t watch.

She came again a few minutes later. She begged for cum in her pussy as well as her ass. I put her in missionary and fucked her hard as she sucked my nipples. A minute later I burst into her pussy a load of cum. She came again as well. She wrapped around me tightly as my semen poured into her.

I needed a breather so I sat on the bed. I could tell Peter wanted her. She stood with my cum dripped from both her holes down her legs. She stepped on his dick with the high heels. He begged and pleaded to cum. She denied him again. She walked over and grabbed me saying she still had one more hole to fill.

She stood me right in front of him and played with my dick, getting it hard again. She looked at Peter saying, “I love his nice big dick. So much better than yours honey. I’m gonna suck this big….thick…dick! until he fills my mouth with cum!”

She began to deep throat me again, keeping her sexy green eyes looked on mine. Peter filmed as she played with my balls and pinched my nipples. I was pretty spent but the pure lust of this woman pushed me over the edge. Right before I came she pulled my dick out and jerked it, pointing it at her open mouth. I came hard filling her mouth and face with cum.

She looked at Peter, swirling it in her mouth so he and the camera could see saying “Mmm, nice thick cum!” She swallowed and smiled at me. She said she loved me and wanted to meet again for more.

Did you have an orgasm? Did your partner(s)? I came three time, she came atleast that many if not more

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No condoms. She was on the pill and showed clean history.

What were your REASONS for having this hookup? Big tits, redhead, smokin hot cougar!

Were alcohol or drugs involved? If so, how much? A few but not really anything serious

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I got dressed. They thanked me and we exchanged numbers. They offered I could watch them afterwards but declined. They started fucking as I left.

To whom did you talk about the hookup? How did they react? I told a few friends. Got some high fives.

Was this a consensual and/or wanted experience for you? For your partner? Yes

Do you regret this hookup? If so, why? It was weird but no

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best – Fucking a beautiful cougar. I did kinda get a thrill of fucking her in front of her husband. It was only the second time I had anal and she was the best!

Worst- it was pretty weird but I came to understand. I probably should have been less trusting leading up to it as you never know

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? I got a call from Carol a month later asking to meet up. She said that Peter was out of town and she had an itch. I agreed and we fucked on their bed as a camcorder filmed it for him later.

We fell out of touch after wards. Apparently she got into black guys and gang bangs afterwards.

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