Watching Whenever



What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Boston
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Paramedic
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Voyeur, Stag-Vixen
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? 3

Watching Whenever

How long ago did this hookup happen? Ongoing

What was your relationship status at the time? Engaged/Married (open)

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For more than 3 years

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? I’ve been sharing my wife with my best friend for a number of years now. His wife has no idea, which makes it more intense. Over time, we eventually included another friend we trusted. He’d been divorced and over time my wife just seduced him. It took a while for him to get comfortable about being in the lifestyle with us, but it’s worked out great. As time went by, my wife hinted that she wanted to play with two of our other friends, but she didn’t want them to know I knew, or that I could hide and watch.

One friend was the husband of a friend of hers. My wife and he had actually dated years ago and she swore he still had a thing for her. We’ll just call him David. They had always flirted and my wife had told me that he often whispered things to her or would ask her if she remembered something from when they went out.

The other guy, Dennis, was a co-worker of hers, but I’d gotten to know him because we both fished a lot together and we both love sports. Dennis is in his early 30’s while my wife and I are in our late 40’s. They flirted and kidded a lot, but not to the same degree that she did with David.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My wife, Amy, instigated by flirting more with David first. If he whispered something to her, she’d whisper back. If he was coming over, she started wearing stuff that was a little more revealing. If I was out of sight, she started grabbing his crotch saying things like it had been a long time or would flash him her tits and ass. David was suckered right in. I’d find something to do to leave them alone for a few minutes to allow them to flirt and if Amy heard me coming back she always told him shhh with her finger to her lips. This went on for a while and then they started heavily sexting and exchanging pics. We got off knowing that he didn’t know that I often read the texts with her and helped her text him back.

Over time, the sexting got more graphic and she’d ask him things like how long had it been since she had sucked his cock? Or how did her blowjobs compare to his wife’s? He’d ask if his cock was bigger then mine and if she missed her fucking him. In the meantime, Amy started flirting more with Dennis at work. The kidding became more sexual and she joked that a young kid could never keep up with a sexually mature woman. He’d joke about putting it to the test.

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? Her first big move with David came one night while they were sexting. David’s wife was out and he kept saying he was lonely and that she should come over. She kidded what kind of an explanation would they give when his wife got home? They went back and forth for a while. My wife lied and said I was out too. He said maybe he should come over. She joked and laughed it off and then she said how would they explain it to me? He wanted to know where I was and she told me I was helping some guy from work move. A little while later, she told him I had called and that I would be late. She told him if he wanted that blowjob he should come over now. He wanted to know if she was serious? She said very! He said if she was he would come over. She said fine. My wife and I had previously agreed not in our bed. We planned for it to happen in our den. It was summer, so we turned off the AC and opened the windows so I could hear. I then went and hid in the yard.

When David got there, he asked about my car and she told him someone had picked me up. He then asked her if she was serious. She played cute and innocent and asked serious about what? He said you know, and she said giving you a blowjob? I won’t tell if you won’t. She led him to our den as I peeked from outside. She sat on the edge of a chair, unbuckled his belt, lowered his pants, and started to play with him. He was rock hard but so was I!! She finally took him in her mouth and he moaned and told her he had forgotten how good she was at it. She sucked him for a little while but it was obvious he wasn’t going to last. He told her he was going to cum and she let him know it was all right that he could cum in her mouth. Which he did. After they were done, he just couldn’t believe what had happened. She reminded him that it was their secret. I could barely contain myself. He tried to do more with her then, but she told him that was enough for tonight. He was disappointed but she told him she wasn’t sure exactly how long I would be. She also told him if he kept the secret it wouldn’t be his last one. He kissed her and left. I ran back in the house very excited and we ran to our bedroom and fucked like crazy, happy to add something new to our lifestyle. To watch is very exciting and to know he didn’t know I knew gave it more of a thrill.

With Dennis, it was a lot more straight forward. They’d been teasing and flirting with each other a lot. They both work in the operating room at a local hospital. After one extremely busy 3-11 shift, when they went to leave, he asked her if she wanted to get a drink and unwind, which was something they had done before. Given it was still hot and humid, she told him what she really wanted to do was going swimming. He wanted to know where and she told him she had a place. We live outside of the city and there are plenty places you can go – even if you have to sneak in. All they had were OR scrubs and he told her he had nothing to wear. She told him she didn’t either so they’d just have to go skinny dipping. Dennis asked her if she was for real and she said yes, she wanted to go. They found an isolated place, parked their cars, and she told me Dennis seemed a little unsure until she took everything off. At that point, he started to undress and she helped him. When his pants were off she told me she was surprised by his size and asked him what do we have here? Like with David she played with him but quickly knelt down to blow him. Unlike David, Dennis lasted longer. He didn’t cum and bent her over a nearby picnic table and proceeded to fuck her, saying he’d always wanted to do it. She told me they fucked for quite a while. Then, she told him she was running late and had to get going but to text her later. She was very excited when she got home and again, we fucked like crazy. Hearing about it wasn’t as much fun as watching, but it was still exciting. We had done it before, but not like this. This has been going on for a couple of years now. Both of them will take any opportunity they can to be with her. I’ve secretly watched both and also heard about it. At times, I’m the one who’s actually texting them. This has gone on a lot longer then intended, so we’ll submit some of our other adventures later.

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? Amy and I can’t believe how exciting this whole lifestyle is for us. Because 2 of our friends have no idea, I know they try to take advantage of every opportunity. I find reasons for them to come over so we continue to be friends as well.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Hoping or expecting it would lead to something more

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? We haven’t shared this part of our lifestyle with anybody.

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

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? It’s added another dimension to our lifestyle. I’ve always liked to share and watch, but the fact they think they’re sneaking makes it more thrilling for me.

What was the WORST thing about this hookup? Hard to find a way that long hookups can happen that I can watch. We don’t want the make it too obvious.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, both of us believe that it’s possible to have casual sex between consenting adults.

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

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

Anything else you want to add about this hookup? We now share with 4 different men in different ways. Not always easy to juggle that schedule!

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Again, we believe there’s nothing wrong with casual sex between consenting adults. Ironically, it happens more then most people will admit because of how society judges you.

What do you think about the Casual Sex Project? I think it’s great. I feel better about myself knowing there are others like us out there.

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