Mistake To Wait So Long

by PittCoupleN

What’s your gender? couple
How old are you? 50+
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Pittsburgh, PA, USA
Highest education received: Some college (not currently in college)
What’s your occupation? IT Administration
What’s your current relationship status? Married and playing with others together
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Primary attraction hetero but anything goes between the sheets
Any other term(s) that describe your sexuality or sexual identity? Both are attracted to those of the opposite sex, but are committed to pleasing partners and don’t get hung up on labels.
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 0

Mistake To Wait So Long

How long ago did this hookup happen? 3 years

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

How would you best classify this hookup? Group sex

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? By design, our new friend was very average in most ways. We sought out a person who was sane, pleasant and willing to respect our boundaries first time out. We sifted through lots of potentials on various adult dating and swinger sites, and finally found a good connection on Craigslist.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We’d been talking for many years of meeting couples to experiment with and push our boundaries. After a few false starts, mostly because my petty jealousy would trump my bi-curiosity when I contemplated the idea of my husband being with the women we met, my husband suggested we take the woman out of the equation for our first encounter and stick with something more in my comfort zone and decide how to proceed from there. After an exhaustive search, we agreed to meet a man at a bar near a hotel we’d booked a room at. It was made clear to all that I had ultimate veto power and could shut things down at any point. After meeting, we planned to separate with the understanding that if I wished to proceed we would text him our room number.

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? After meeting “K” and having a few drinks and confirming that he had represented himself accurately in our online encounters, we left and I decided it was time to follow through. There wasn’t a tremendous physical attraction to K but the excitement of the situation prevailed. We texted him as we arrived in our room and he arrived a few minutes later. The room we had booked was very nice and had a large whirlpool tub in it near the bed. My husband suggested we all climb in the tub as an icebreaker with our drinks. I was a bit surprised with my own comfort in peeling off my clothes in front of a stranger despite my nerves and entered the tub. After sipping our wine a bit and flirting I tested my husband’s resolve by beginning to make out with him. I sensed no hesitation or reluctance so I turned to K and began doing the same while I slipped my hand under the water and began touching his cock. My head was a bit fuzzy as this was the first man I’d ever touched in nearly 30 years besides my husband. My husband climbed out of the tub, dried off, then turned on the video camera he’d set up near the bed much earlier as our guest and I continued to explore each other with our mouths and hands. My feelings as we all climbed into bed are a bit hard to put into words, it was a mix of agitated nervousness and lusty excitement. My brain was buzzing but my body seemed to just kick into gear and I started performing oral on K. My husband’s head was a bit clearer and soon he began directing us to try as many of the things we’d talked about that he could remember. We tried various positions with me performing oral on one of them while the other fucked me, we tried double penetration various ways, but nothing blew my mind more than when K took me from behind while we spooned and my husband went down on me while K fucked me. The sheer eroticism and pleasure of cumming while being eaten and penetrated at the same time was mind-boggling. Eventually, K rolled me over on my back, pinned my legs back, and pounded me hard until he emptied deep inside me. Just when I thought things couldn’t get any crazier my husband took things over the top by licking me clean after K had rolled off before taking his sloppy seconds and adding to the mix in my belly. After we caught our breath, we decided to jump back into the tub to freshen up. I remember thinking how oddly normal things seemed as the three of us splashed around. After dried off, I slipped on a sheer black nightie top and we sipped another glass of wine as K and I sat on the couch and my husband in a chair across from us. For the life of me, I can’t even remember what we were talking about as I replayed what we’d just done in my head again and again. It wasn’t long before I’d worked myself up, and before I knew it I was sitting cowgirl in K’s lap as I bounced up and down on his dick. My husband had started the camera up again and retrieved a second, snapping away as K as I made our way to the bed again. K and I fucked much more passionately as we were no longer worried about “ticking all the boxes” and just enjoyed each other as my husband stepped to the sideline and took more pictures while he masturbated.

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? The next day I woke up a bit apprehensive that there would be some regret on my husband’s part, especially as I wrestled with the fact that the night finished with me and K screwing exclusively while my husband stroked off in a chair. There was no regret at all, and he was especially loving and attentive not only the next day but for some time afterward. We kind of let things sit and didn’t talk about specifics for a while as we let things settle. Eventually, my husband brought out the video and we watched it over drinks. It wasn’t until then that I realized how much of that evening was about me with K. Of the 5 or so hours of video about 3.5 to 4 were of me and K banging like two teenagers. I worried again that this would be an issue for my husband but he confided that he’d been watching the video almost every day and came to realize that he like watching me more than anything else we’d done and that it had opened his eyes to something about himself. We met K a few times after that, though each time it became less about the three of us and more about me and K, and to my surprise, my husband’s increasing interest and comfort servicing us both. The last few times we met, hubby had let go of all his inhibitions and he was enthusiastically pleasing K and me orally every chance he got. I even got into pushing him to see how far he’d go and had him under me as K took me doggy while he licked and had K pull out to cum in his mouth. I still have fond memories of K, but unfortunately, there is no future for us all as he eventually took a job out of state and there’s no longer an opportunity for future meetings. We have since tried to find another situation but the universe has conspired against us leading us to have only one regret … having waited so long to head down this path.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization, Discussed STI testing history, I had my tubes tied nearly 20 years ago after the birth of our last child, that and menopause took the pregnancy issue off the table. Initially, we all agreed to do the “responsible thing” and use condoms for STD prevention but after meeting K and feeling sufficiently comfortable that he’d represented himself and his situation honestly, I decided the risk was nominal at worst and decided to skip them and go with my preference for bareback.

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? Aside from K, my husband and myself only two other people know about this. I shared these experiences in general terms with a friend of ours who had confided in me that she and her husband were talking about swinging, and she relayed them to her husband.

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? The experience opened up a whole new level of intimacy and honesty between my husband and I. To realize that my husband is committed to our marriage and me on a level so deep that even sex with others can’t threaten it is hard to wrap my head around sometimes. There’s also quite a bit of video that we enjoy watching regularly that comes in a close second.

What was the WORST thing about this hookup? It caused us to realize how much time we’d lost putting off acting on our desires and how we’ll never get that lost time back. As a mid-fifties couple we’re now excluded from consideration by potential partners and try as we might, can’t seem to find a good match to continue down this amazing road. I sometimes lament the fact that I can’t turn back the clock to our early forties when we were still part of what is considered a desirable age, shake some sense into myself and start to build some more lasting and permanent relationships while we had the chance. Oh, the opportunities we, I really passed on back then because of some silly social pressure and foolish ideas … it hurts to think about it sometimes. There’s one particular guy I still think about and how my foolishness may have affected all our lives. He tried so hard to get in my pants, didn’t hide it from my husband who encouraged it and I wanted him sooo bad. I was just too stubborn and thought I was being noble, upright wife by saying no. I wonder, if I’d just listened and said yes how much happier would be all be today *sigh.*

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Absolutely! It crushed all my antiquated notions about the need for a committed relationship being necessary to have and enjoy sexual pleasure and the idea of mandatory monogamy being essential to a solid marriage just plain wrong.

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? I would caution against anyone using our experience(s) to act precipitously and assume these things work for everyone at all times. As positive as it’s been for us, we had a very mature and stable 33-year relationship built on a solid foundation. Although we wish we’d have acted sooner it’s not difficult to imagine that had we done this to soon, when we were younger and still struggling with the daily burdens of raising a family, things could’ve, almost certainly would’ve gone a different way.

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? “There’s a time and place for everything.” The idea of one size fits all marriage, mandatory monogamy for everyone, straight, gay, bi … obsolete ideas every one of them. Quit letting others tell you how to live, define you and dictate the course of your life.

What do you think about the Casual Sex Project? Fabulous! Hope to see it prosper.

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