First Time Cuckold Situation



What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? North Carolina
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Retail manager
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 18
How many hookup stories have you here posted before? Few

First Time Cuckold Situation

How long ago did this hookup happen? 7 years ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

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? She was in her mid-forties, white, decent body, 38C tits, brown hair to her shoulders, and had a shaved pussy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met up with her on Craigslist when I was looking for some no strings fun. She told me that she was married and that her husband was in his late 50’s. She said he had trouble performing sexually, leaving her less than satisfied. She told me that she was clean and hadn’t slept with anyone other than her husband since they had gotten married. Because of his issues, he was giving her permission to play. She resorted to Craigslist because she didn’t know any other way to find a discrete hookup. We chatted back and forth for a couple of days (trying to feel her out and see if her story changed, etc). When we finally set up a time, she invited me to come to their house so that we wouldn’t have to worry about getting a hotel room. On the afternoon of the hookup, she messaged me the address. We set the time and I told her I’d have to stop for condoms on the way, but she told me not to bother unless I absolutely wanted to use them as she was unable to get pregnant and was totally clean.

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? When I arrived at her house, I knocked on the door. To my surprise, I was greeted at the door by her husband. I froze in shock until he extended his hand and greeted me by name. I hesitantly shook his hand and he invited me into the living room. He sat back in his recliner and I sat on the couch. He was watching a basketball game. After a couple minutes of awkward silence, she came from down the hall wearing only a black camisole and a black lacy thong. She climbed on the couch right against me and gave me a long, deep kiss as she squeezed my cock through my jeans. After the kiss, I saw her husband looking directly at us as she undid my jeans and pulled out my cock. She wasted no time before taking my cock in her mouth and sucking it hard and aggressively with her husband less than 10 feet away. I was in shock but it didn’t stop my cock from getting harder and harder. After about 10 minutes, she stopped sucking and told her husband we were heading to the bedroom. He told us to have fun and turned his attention back to the TV.

Once in the bedroom, I quickly got undressed and then stripped her naked. I ate her pussy and finger fucked her for about 5 minutes before she started cumming. That’s when she begged me to go ahead and fuck her. Her pussy was tight around my fingers so I couldn’t wait to bury my cock in it. I shoved my cock in her missionary and started fucking her hard and deep. She moaned loudly and was very verbal telling me how good it felt, fuck her harder, etc. After a few minutes, I could feel my balls tightening and knew that I was getting close following that amazing blowjob she had given me in the living room. I warned her and asked if she wanted me to pull out. She told me no…she wanted every drop deep inside her. So I pulled her legs up onto my shoulders, adjusted my angle, and started pounding her pussy like there was no tomorrow. With a loud grunt, I shoved my cock balls deep into her and unloaded 4 days worth of cum into her tight pussy. Spurt after spurt flowed into her sending her into another loud orgasm. It was a huge load because when I pulled out, it poured out and ran down her asshole. I laid on the bed next to her so that we could catch our breath when I noticed her husband standing in the doorway. He commented that she’s never cum like that for him. He climbed between her legs and started licking her cum-filled pussy. She closed her eyes with pleasure and reached over taking my cock in her hand and stroking it to keep it hard. That’s when he told me to put it back in her mouth for a bit. After he “cleaned her up” she climbed on top of me and he watched her bounce up and down fucking my cock until I unloaded inside her again. This time though, when she climbed off, he had dropped his pants and gotten his cock hard stroking it. As my cum began to drip out of her, he began fucking her doggie style while I recuperated…which didn’t take long because she sucked me some more while he was pounding her messy cunt. I heard him grunting as he finally shot a load into her. Then he pulled his pants up and told us to have fun…that halftime was over. He left the room as I got behind her and started fucking her from behind.

We kept at it for about another hour. Switching positions and taking little breaks here and there. I ended up cumming in her two more times before I left that night. The last load, I pumped deep inside her ass. We made out a bit before I left and she told me that she wanted me to come over again sometime. I said sure and she walked me to the door. As I was about to leave, her husband chimed in for me to come back anytime.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Her husband messaged me the next day and told me that I really wore her pussy out and how much she liked it and wanted more. He invited me over the next weekend…this time for a cookout before the fuckfest.

I hooked up with her several times over the next couple of months. Most of the time, he would watch us. Occasionally, he’d actually join us and we’d really give her a good pounding. It ended after I started dating someone seriously.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Just her husband…I would tell him the details on the occasions that he wasn’t around to watch/join

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Unprotected sex without risk of pregnancy or STD’s

What was the WORST thing about this hookup? It was a bit awkward at times because of her husband…especially when he would try and couldn’t perform

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Casual sex is awesome.

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

All things considered, how NEGATIVE was this experience? Not at all negative

You have a hookup story to share? Submit it here!